<?xml version="1.0" encoding="UTF-8"?>
<bmdb xmlns="http://www.bmdb.ca">
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:07:14 UTC</creation_date>
  <update_date>2020-04-16 20:38:15 UTC</update_date>
  <accession>BMDB0000001</accession>
  <secondary_accessions>
    <accession>BMDB00001</accession>
  </secondary_accessions>
  <name>1-Methylhistidine</name>
  <description>1-Methylhistidine, also known as 1-mhis, belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 1-Methylhistidine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 1-Methylhistidine exists in all living organisms, ranging from bacteria to humans. 1-Methylhistidine participates in a number of enzymatic reactions, within cattle. In particular, 1-Methylhistidine and beta-alanine can be converted into anserine through its interaction with the enzyme carnosine synthase 1. In addition, beta-Alanine and 1-methylhistidine can be biosynthesized from anserine; which is mediated by the enzyme cytosolic non-specific dipeptidase. In cattle, 1-methylhistidine is involved in the metabolic pathway called the histidine metabolism pathway. 1-Methylhistidine has been found to be associated with several diseases known as eosinophilic esophagitis, early preeclampsia, and obesity; also 1-methylhistidine has been linked to several inborn metabolic disorders including maple syrup urine disease and propionic acidemia.</description>
  <synonyms>
    <synonym>(2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid</synonym>
    <synonym>Pi-methylhistidine</synonym>
    <synonym>(2S)-2-Amino-3-(1-methyl-1H-imidazol-4-yl)propanoate</synonym>
    <synonym>1 Methylhistidine</synonym>
    <synonym>1-Methyl histidine</synonym>
    <synonym>1-Methyl-histidine</synonym>
    <synonym>1-Methyl-L-histidine</synonym>
    <synonym>1-MHis</synonym>
    <synonym>1-N-Methyl-L-histidine</synonym>
    <synonym>L-1-Methylhistidine</synonym>
    <synonym>N1-Methyl-L-histidine</synonym>
    <synonym>1-Methylhistidine dihydrochloride</synonym>
    <synonym>1-Methylhistidine</synonym>
  </synonyms>
  <chemical_formula>C7H11N3O2</chemical_formula>
  <average_molecular_weight>169.1811</average_molecular_weight>
  <monisotopic_moleculate_weight>169.085126611</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid</iupac_name>
  <traditional_iupac>1 methylhistidine</traditional_iupac>
  <cas_registry_number>332-80-9</cas_registry_number>
  <smiles>CN1C=NC(C[C@H](N)C(O)=O)=C1</smiles>
  <inchi>InChI=1S/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1</inchi>
  <inchikey>BRMWTNUJHUMWMS-LURJTMIESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Histidine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolyl carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Histidine or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazolyl carboxylic acid derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-histidine derivative</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>249</value>
      <source>http://download.cappchem.com/data/Properties-of-Amino-Acids.pdf</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>169.1811</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>169.085126611</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C=NC(C[C@H](N)C(O)=O)=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H11N3O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H11N3O2/c1-10-3-5(9-4-10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BRMWTNUJHUMWMS-LURJTMIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>81.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37237</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>14+/-2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2-12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>van der Drift SGA, Houweling M, Schonewille JT, Tielens AGM, Jorritsma R: Protein and fat mobilization and associations with serum beta-hydroxybutyrate concentrations in dairy cows. J Dairy Sci. 2012 Sep;95(9):4911-4920. doi: 10.3168/jds.2011-4771.</reference_text>
          <pubmed_id>22916895</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>25+/-5</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>35+/-8</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>35+/-9</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>19+/-4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01152</kegg_id>
  <foodb_id>FDB093588</foodb_id>
  <chemspider_id>83153</chemspider_id>
  <drugbank_id>DB04151</drugbank_id>
  <pdbe_id/>
  <chebi_id>50599</chebi_id>
  <pubchem_compound_id>92105</pubchem_compound_id>
  <meta_cyc_id/>
  <wikipedia_id>Methylhistidine</wikipedia_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>3741</metlin_id>
  <synthesis_reference>Jain, Rahul; Cohen, Louis A. Regiospecific alkylation of histidine and histamine at N-1 (t).Tetrahedron  (1996),  52(15),  5363-70.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:07:15 UTC</creation_date>
  <update_date>2020-03-18 17:35:17 UTC</update_date>
  <accession>BMDB0000002</accession>
  <secondary_accessions>
    <accession>BMDB00002</accession>
  </secondary_accessions>
  <name>1,3-Diaminopropane</name>
  <description/>
  <synonyms>
    <synonym>1,3-Propanediamine</synonym>
    <synonym>1,3-Propylenediamine</synonym>
    <synonym>Propane-1,3-diamine</synonym>
    <synonym>tn</synonym>
    <synonym>Trimethylenediamine</synonym>
    <synonym>1,3-diamino-N-Propane</synonym>
    <synonym>1,3-Trimethylenediamine</synonym>
    <synonym>3-Aminopropylamine</synonym>
    <synonym>a,W-Propanediamine</synonym>
    <synonym>Trimethylenediamine hydrochloride</synonym>
    <synonym>Trimethylenediamine dihydrochloride</synonym>
    <synonym>1,3-Diaminepropane</synonym>
    <synonym>1,3-Diaminopropane</synonym>
  </synonyms>
  <chemical_formula>C3H10N2</chemical_formula>
  <average_molecular_weight>74.1249</average_molecular_weight>
  <monisotopic_moleculate_weight>74.08439833</monisotopic_moleculate_weight>
  <iupac_name>propane-1,3-diamine</iupac_name>
  <traditional_iupac>α,ω-propanediamine</traditional_iupac>
  <cas_registry_number>109-76-2</cas_registry_number>
  <smiles>NCCCN</smiles>
  <inchi>InChI=1S/C3H10N2/c4-2-1-3-5/h1-5H2</inchi>
  <inchikey>XFNJVJPLKCPIBV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>Monoalkylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>alkane-alpha,omega-diamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-12 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.43</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>propane-1,3-diamine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>74.1249</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>74.08439833</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCN</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H10N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H10N2/c4-2-1-3-5/h1-5H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XFNJVJPLKCPIBV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>52.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>22.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445976</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00986</kegg_id>
  <foodb_id>FDB031131</foodb_id>
  <chemspider_id>415</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>15725</chebi_id>
  <pubchem_compound_id>428</pubchem_compound_id>
  <meta_cyc_id>CPD-313</meta_cyc_id>
  <wikipedia_id>1,3-Diaminopropane</wikipedia_id>
  <knapsack_id>C00007404</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00127</protein_accession>
      <name>Deoxyhypusine synthase</name>
      <uniprot_id>Q6EWQ6</uniprot_id>
      <gene_name>DHPS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:07:17 UTC</creation_date>
  <update_date>2020-03-18 18:11:41 UTC</update_date>
  <accession>BMDB0000005</accession>
  <secondary_accessions>
    <accession>BMDB00005</accession>
  </secondary_accessions>
  <name>2-Ketobutyric acid</name>
  <description>2-Ketobutyric acid, also known as 2-ketobutyric acid or a-oxo-N-butyrate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Ketobutyric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 2-Ketobutyric acid exists in all living species, ranging from bacteria to humans. 2-Ketobutyric acid participates in a number of enzymatic reactions, within cattle. In particular, 2-Ketobutyric acid can be biosynthesized from L-threonine; which is mediated by the enzyme L-serine dehydratase/l-threonine deaminase. In addition, 2-Ketobutyric acid and coenzyme A can be converted into propionyl-CoA through its interaction with the enzyme branched-chain alpha-keto dehydrogenase complex. In cattle, 2-ketobutyric acid is involved in the metabolic pathway called the threonine and 2-ketobutyric acid degradation pathway.</description>
  <synonyms>
    <synonym>2-Ketobutanoic acid</synonym>
    <synonym>2-Oxobutyric acid</synonym>
    <synonym>3-Methyl pyruvic acid</synonym>
    <synonym>alpha-Ketobutyrate</synonym>
    <synonym>alpha-Ketobutyric acid</synonym>
    <synonym>alpha-oxo-N-Butyric acid</synonym>
    <synonym>2-Oxobutyrate</synonym>
    <synonym>2-Oxobutanoic acid</synonym>
    <synonym>2-Ketobutanoate</synonym>
    <synonym>3-Methyl pyruvate</synonym>
    <synonym>a-Ketobutyrate</synonym>
    <synonym>a-Ketobutyric acid</synonym>
    <synonym>Α-ketobutyrate</synonym>
    <synonym>Α-ketobutyric acid</synonym>
    <synonym>a-oxo-N-Butyrate</synonym>
    <synonym>a-oxo-N-Butyric acid</synonym>
    <synonym>alpha-oxo-N-Butyrate</synonym>
    <synonym>Α-oxo-N-butyrate</synonym>
    <synonym>Α-oxo-N-butyric acid</synonym>
    <synonym>2-Oxobutanoate</synonym>
    <synonym>2-Ketobutyrate</synonym>
    <synonym>2-oxo-Butanoate</synonym>
    <synonym>2-oxo-Butanoic acid</synonym>
    <synonym>2-oxo-Butyrate</synonym>
    <synonym>2-oxo-Butyric acid</synonym>
    <synonym>2-oxo-N-Butyrate</synonym>
    <synonym>2-oxo-N-Butyric acid</synonym>
    <synonym>3-Methylpyruvate</synonym>
    <synonym>3-Methylpyruvic acid</synonym>
    <synonym>a-Keto-N-butyrate</synonym>
    <synonym>a-Keto-N-butyric acid</synonym>
    <synonym>a-Oxobutyrate</synonym>
    <synonym>a-Oxobutyric acid</synonym>
    <synonym>alpha-Keto-N-butyrate</synonym>
    <synonym>alpha-Keto-N-butyric acid</synonym>
    <synonym>alpha-Ketobutric acid</synonym>
    <synonym>alpha-Oxobutyrate</synonym>
    <synonym>alpha-Oxobutyric acid</synonym>
    <synonym>Methyl-pyruvate</synonym>
    <synonym>Methyl-pyruvic acid</synonym>
    <synonym>Propionyl-formate</synonym>
    <synonym>Propionyl-formic acid</synonym>
    <synonym>alpha-Ketobutyric acid, sodium salt</synonym>
    <synonym>2-Ketobutyric acid</synonym>
  </synonyms>
  <chemical_formula>C4H6O3</chemical_formula>
  <average_molecular_weight>102.0886</average_molecular_weight>
  <monisotopic_moleculate_weight>102.031694058</monisotopic_moleculate_weight>
  <iupac_name>2-oxobutanoic acid</iupac_name>
  <traditional_iupac>2-oxobutanoic acid</traditional_iupac>
  <cas_registry_number>600-18-0</cas_registry_number>
  <smiles>CCC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)</inchi>
  <inchikey>TYEYBOSBBBHJIV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Short-chain keto acids and derivatives</sub_class>
    <direct_parent>Short-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain keto acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>Oxo fatty acids</external_descriptor>
      <external_descriptor>Oxo fatty acids</external_descriptor>
      <external_descriptor>short-chain fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>33 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>119 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-oxobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>102.0886</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>102.031694058</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H6O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>TYEYBOSBBBHJIV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>22.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Homocysteine Degradation</name>
      <smpdb_id>SMP0087201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Selenoamino Acid Metabolism</name>
      <smpdb_id>SMP0087161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Threonine and 2-Oxobutanoate Degradation</name>
      <smpdb_id>SMP0087262</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30944</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37238</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00109</kegg_id>
  <drugbank_id>DB04553</drugbank_id>
  <foodb_id>FDB030356</foodb_id>
  <chemspider_id>57</chemspider_id>
  <pubchem_compound_id>58</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30831</chebi_id>
  <knapsack_id>C00019675</knapsack_id>
  <meta_cyc_id>2-OXOBUTANOATE</meta_cyc_id>
  <wikipedia_id>Alpha-Ketobutyric_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33889</bigg_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00088</protein_accession>
      <name>L-serine dehydratase</name>
      <uniprot_id>Q0VCW4</uniprot_id>
      <gene_name>SDS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00818</protein_accession>
      <name>Cystathionine gamma-lyase</name>
      <uniprot_id>Q58DW2</uniprot_id>
      <gene_name>CTH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:07:18 UTC</creation_date>
  <update_date>2020-04-16 17:52:03 UTC</update_date>
  <accession>BMDB0000008</accession>
  <secondary_accessions>
    <accession>BMDB00008</accession>
  </secondary_accessions>
  <name>2-Hydroxybutyric acid</name>
  <description>2-Hydroxybutyric acid, also known as alpha-hydroxybutyrate or 2-hydroxybutanoate, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. 2-Hydroxybutyric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 2-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. 2-Hydroxybutyric acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(S)-2-Hydroxybutanoic acid</synonym>
    <synonym>2-Hydroxybutyrate</synonym>
    <synonym>2-Hydroxybutyric acid</synonym>
    <synonym>L-2-Hydroxybutanoic acid</synonym>
    <synonym>L-2-Hydroxybutyric acid</synonym>
    <synonym>L-alpha-Hydroxybutanoic acid</synonym>
    <synonym>L-alpha-Hydroxybutyric acid</synonym>
    <synonym>(S)-2-Hydroxybutanoate</synonym>
    <synonym>L-2-Hydroxybutanoate</synonym>
    <synonym>L-2-Hydroxybutyrate</synonym>
    <synonym>L-a-Hydroxybutanoate</synonym>
    <synonym>L-a-Hydroxybutanoic acid</synonym>
    <synonym>L-alpha-Hydroxybutanoate</synonym>
    <synonym>L-Α-hydroxybutanoate</synonym>
    <synonym>L-Α-hydroxybutanoic acid</synonym>
    <synonym>L-a-Hydroxybutyrate</synonym>
    <synonym>L-a-Hydroxybutyric acid</synonym>
    <synonym>L-alpha-Hydroxybutyrate</synonym>
    <synonym>L-Α-hydroxybutyrate</synonym>
    <synonym>L-Α-hydroxybutyric acid</synonym>
    <synonym>(S)-2-Hydroxybutyrate</synonym>
    <synonym>2-Hydroxybutanoate</synonym>
    <synonym>(+)-2-Hydroxy-n-butyric acid</synonym>
    <synonym>(+)-2-Hydroxybutanoic acid</synonym>
    <synonym>(+)-2-Hydroxybutyric acid</synonym>
    <synonym>(+)-alpha-Hydroxybutyric acid</synonym>
    <synonym>(+)-α-Hydroxybutyric acid</synonym>
    <synonym>(2S)-2-Hydroxybutanoic acid</synonym>
    <synonym>(S)-(+)-2-Hydroxybutanoic acid</synonym>
    <synonym>(S)-2-Hydroxybutyric acid</synonym>
    <synonym>2-Hydroxybutanoic acid</synonym>
    <synonym>alpha-Hydroxy-n-butyric acid</synonym>
    <synonym>alpha-Hydroxybutanoic acid</synonym>
    <synonym>alpha-Hydroxybutyric acid</synonym>
    <synonym>α-Hydroxy-n-butyric acid</synonym>
    <synonym>α-Hydroxybutanoic acid</synonym>
    <synonym>α-Hydroxybutyric acid</synonym>
  </synonyms>
  <chemical_formula>C4H8O3</chemical_formula>
  <average_molecular_weight>104.105</average_molecular_weight>
  <monisotopic_moleculate_weight>104.047344118</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-hydroxybutanoic acid</iupac_name>
  <traditional_iupac>(S)-2-hydroxybutyric acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC[C@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1</inchi>
  <inchikey>AFENDNXGAFYKQO-VKHMYHEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Alpha hydroxy acids and derivatives</sub_class>
    <direct_parent>Alpha hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxybutyric acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>44.2 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.051</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-hydroxybutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>104.105</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>104.047344118</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC[C@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AFENDNXGAFYKQO-VKHMYHEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>23.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1250182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1250183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1250184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1365478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1365479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1365480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448546</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by GC-TOF/MS</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
          <pubmed_id>29197344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in beef muscle (longissimus dorsi).</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB021867</foodb_id>
  <kegg_id>C05984</kegg_id>
  <chemspider_id>389701</chemspider_id>
  <chebi_id>50613</chebi_id>
  <pubchem_compound_id>440864</pubchem_compound_id>
  <pdbe_id/>
  <meta_cyc_id>CPD-3564</meta_cyc_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <wikipedia_id>2-Hydroxybutyric_acid</wikipedia_id>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Carlier, J. P.; Henry, C.; Lorin, V.; Rouffignat, K. Conversion of DL-threonine, D-threonine and 2-oxobutyrate into propionate and 2-hydroxybutyrate by Fusobacterium species. Letters in Applied Microbiology  (1997),  25(5),  371-374.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
      <pubmed_id>29197344</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:16:26 UTC</creation_date>
  <update_date>2020-03-18 18:11:46 UTC</update_date>
  <accession>BMDB0000010</accession>
  <secondary_accessions>
    <accession>BMDB00010</accession>
  </secondary_accessions>
  <name>2-Methoxyestrone</name>
  <description>2-Methoxyestrone belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 2-methoxyestrone is considered to be a steroid lipid molecule. 2-Methoxyestrone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 2-Methoxyestrone exists in all living organisms, ranging from bacteria to humans. 2-Methoxyestrone and S-adenosylhomocysteine can be biosynthesized from S-adenosylmethionine and 2-hydroxyestrone; which is mediated by the enzyme catechol O-methyltransferase. In cattle, 2-methoxyestrone is involved in the metabolic pathway called the estrone metabolism pathway.</description>
  <synonyms>
    <synonym>2-(8S,9S,13S,14S)-3-Hydroxy-2-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one</synonym>
    <synonym>2-Hydroxyestrone 2-methyl ether</synonym>
    <synonym>2-Methoxy-17-oxoestra-1,3,5(10)-trien-3-ol</synonym>
    <synonym>2-Methoxy-3-hydroxyestra-1,3,5(10)-trien-17-one</synonym>
    <synonym>3-Hydroxy-2-methoxy-estra-1,3,5(10)-trien-17-one</synonym>
    <synonym>3-Hydroxy-2-methoxyestra-1,3,5(10)-trien-17-one</synonym>
    <synonym>Methoxy-estrone</synonym>
  </synonyms>
  <chemical_formula>C19H24O3</chemical_formula>
  <average_molecular_weight>300.3921</average_molecular_weight>
  <monisotopic_moleculate_weight>300.172544634</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,15S)-5-hydroxy-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one</iupac_name>
  <traditional_iupac>(1S,10R,11S,15S)-5-hydroxy-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one</traditional_iupac>
  <cas_registry_number>362-08-3</cas_registry_number>
  <smiles>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3</smiles>
  <inchi>InChI=1S/C19H24O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,20H,3-8H2,1-2H3/t12-,13+,15-,19-/m0/s1</inchi>
  <inchikey>WHEUWNKSCXYKBU-QPWUGHHJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17-oxo steroid</external_descriptor>
      <external_descriptor>3-hydroxy steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>alicyclic ketone</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>187.0 - 189.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,15S)-5-hydroxy-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>300.3921</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>300.172544634</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H24O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H24O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,20H,3-8H2,1-2H3/t12-,13+,15-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WHEUWNKSCXYKBU-QPWUGHHJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>46.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>85.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>919</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363543</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.00167</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS in Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C05299</kegg_id>
  <foodb_id>FDB021868</foodb_id>
  <chemspider_id>389515</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>1189</chebi_id>
  <pubchem_compound_id>440624</pubchem_compound_id>
  <meta_cyc_id/>
  <wikipedia_id>2-Methoxyestrone</wikipedia_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>2578</metlin_id>
  <synthesis_reference>Stoelwinder, Johannes; Moers, Nicolaas Elisabeth Cornelis. Process for the preparation 2-substituted derivatives of estrone and estradiol.PCT Int. Appl.  (2006), 40 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:16:28 UTC</creation_date>
  <update_date>2020-03-18 18:11:48 UTC</update_date>
  <accession>BMDB0000011</accession>
  <secondary_accessions>
    <accession>BMDB00011</accession>
  </secondary_accessions>
  <name>(R)-3-Hydroxybutyric acid</name>
  <description>(R)-3-Hydroxybutyric acid, also known as (R)-3-hydroxybutanoate or 3-D-hydroxybutyrate, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom (R)-3-Hydroxybutyric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule (R)-3-Hydroxybutyric acid exists in all living organisms, ranging from bacteria to humans (R)-3-Hydroxybutyric acid can be converted into acetoacetic acid; which is catalyzed by the enzyme (r)-3-hydroxybutyric acid dehydrogenase, mitochondrial. In cattle, (R)-3-hydroxybutyric acid is involved in the metabolic pathway called the ketone body metabolism pathway.</description>
  <synonyms>
    <synonym>(R)-(-)-beta-Hydroxybutyric acid</synonym>
    <synonym>(R)-3-Hydroxybutanoic acid</synonym>
    <synonym>3-D-Hydroxybutyric acid</synonym>
    <synonym>D-3-Hydroxybutyric acid</synonym>
    <synonym>D-beta-Hydroxybutyric acid</synonym>
    <synonym>(R)-(-)-b-Hydroxybutyrate</synonym>
    <synonym>(R)-(-)-b-Hydroxybutyric acid</synonym>
    <synonym>(R)-(-)-beta-Hydroxybutyrate</synonym>
    <synonym>(R)-(-)-Β-hydroxybutyrate</synonym>
    <synonym>(R)-(-)-Β-hydroxybutyric acid</synonym>
    <synonym>(R)-3-Hydroxybutanoate</synonym>
    <synonym>3-D-Hydroxybutyrate</synonym>
    <synonym>D-3-Hydroxybutyrate</synonym>
    <synonym>D-b-Hydroxybutyrate</synonym>
    <synonym>D-b-Hydroxybutyric acid</synonym>
    <synonym>D-beta-Hydroxybutyrate</synonym>
    <synonym>D-Β-hydroxybutyrate</synonym>
    <synonym>D-Β-hydroxybutyric acid</synonym>
    <synonym>(R)-3-Hydroxybutyrate</synonym>
    <synonym>3-delta-Hydroxybutyrate</synonym>
    <synonym>3-delta-Hydroxybutyric acid</synonym>
    <synonym>BHIB</synonym>
    <synonym>D-(-)-3-Hydroxybutyrate</synonym>
    <synonym>delta-(-)-3-Hydroxybutyrate</synonym>
    <synonym>delta-3-Hydroxybutyrate</synonym>
    <synonym>delta-3-Hydroxybutyric acid</synonym>
    <synonym>delta-beta-Hydroxybutyrate</synonym>
    <synonym>3R-Hydroxy-butanoate</synonym>
    <synonym>(R)-3-Hydroxybutyric acid</synonym>
    <synonym>(-)-3-Hydroxy-n-butyric acid</synonym>
    <synonym>(-)-3-Hydroxybutyric acid</synonym>
    <synonym>(3R)-3-Hydroxybutanoic acid</synonym>
    <synonym>(3R)-3-Hydroxybutyric acid</synonym>
    <synonym>(3R)-Hydroxybutyrate</synonym>
    <synonym>(R)-(-)-3-Hydroxybutyric acid</synonym>
    <synonym>(R)-beta-Hydroxybutanoic acid</synonym>
    <synonym>(R)-beta-Hydroxybutyric acid</synonym>
    <synonym>(R)-β-Hydroxybutanoic acid</synonym>
    <synonym>(R)-β-Hydroxybutyric acid</synonym>
    <synonym>3-Hydroxy-n-butyric acid</synonym>
    <synonym>3-Hydroxybutanoic acid</synonym>
    <synonym>3-Hydroxybutyric acid</synonym>
    <synonym>3R-Hydroxybutanoic acid</synonym>
    <synonym>D-(-)-3-Hydroxybutanoic acid</synonym>
    <synonym>D-(-)-3-Hydroxybutyric acid</synonym>
    <synonym>D-(-)-beta-Hydroxybutyric acid</synonym>
    <synonym>D-(-)-β-Hydroxybutyric acid</synonym>
    <synonym>beta-Hydroxy-n-butyric acid</synonym>
    <synonym>beta-Hydroxybutanoic acid</synonym>
    <synonym>beta-Hydroxybutyric acid</synonym>
    <synonym>β-Hydroxy-n-butyric acid</synonym>
    <synonym>β-Hydroxybutanoic acid</synonym>
    <synonym>β-Hydroxybutyric acid</synonym>
  </synonyms>
  <chemical_formula>C4H8O3</chemical_formula>
  <average_molecular_weight>104.1045</average_molecular_weight>
  <monisotopic_moleculate_weight>104.047344122</monisotopic_moleculate_weight>
  <iupac_name>(3R)-3-hydroxybutanoic acid</iupac_name>
  <traditional_iupac>(-)-3-hydroxybutyric acid</traditional_iupac>
  <cas_registry_number>625-72-9</cas_registry_number>
  <smiles>C[C@@H](O)CC(O)=O</smiles>
  <inchi>InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1</inchi>
  <inchikey>WHBMMWSBFZVSSR-GSVOUGTGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Beta hydroxy acids and derivatives</sub_class>
    <direct_parent>Beta hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hydroxybutyric acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
      <external_descriptor>ketone body</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>49 - 50 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R)-3-hydroxybutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>104.1045</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>104.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WHBMMWSBFZVSSR-GSVOUGTGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>23.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ketone Body Metabolism</name>
      <smpdb_id>SMP0087202</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>2010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440114</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01089</kegg_id>
  <foodb_id>FDB021869</foodb_id>
  <chemspider_id>83181</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>17066</chebi_id>
  <pubchem_compound_id>92135</pubchem_compound_id>
  <meta_cyc_id>CPD-335</meta_cyc_id>
  <wikipedia_id>Beta-Hydroxybutyric_acid</wikipedia_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>36784</bigg_id>
  <metlin_id/>
  <synthesis_reference>Le Sann, Christine; Munoz, Dulce M.; Saunders, Natalie; Simpson, Thomas J.; Smith, David I.; Soulas, Florilene; Watts, Paul; Willis, Christine L.  Assembly intermediates in polyketide biosynthesis: enantioselective syntheses of b-hydroxycarbonyl compounds. Org Biomol Chem. 2005 May 7;3(9):1719-28. Epub 2005 Mar 31. Pubmed: 15858656</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01009</protein_accession>
      <name>3-hydroxybutyrate dehydrogenase type 2</name>
      <uniprot_id>Q3T046</uniprot_id>
      <gene_name>BDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01010</protein_accession>
      <name>D-beta-hydroxybutyrate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q02337</uniprot_id>
      <gene_name>BDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:25 UTC</creation_date>
  <update_date>2020-04-16 20:37:18 UTC</update_date>
  <accession>BMDB0000012</accession>
  <secondary_accessions>
    <accession>BMDB00012</accession>
  </secondary_accessions>
  <name>Deoxyuridine</name>
  <description/>
  <synonyms>
    <synonym>2-Deoxyuridine</synonym>
    <synonym>dU</synonym>
    <synonym>2'-Deoxyuridine</synonym>
    <synonym>1-(2-Deoxy-beta-D-erythro-pentofuranosyl)-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>1-(2-Deoxy-beta-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>1-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>1-(2-Deoxy-beta-delta-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>1-(2-Deoxy-D-erythro-pentofuranosyl)uracil</synonym>
    <synonym>1-(2-Deoxy-delta-erythro-pentofuranosyl)uracil</synonym>
    <synonym>2'-Desoxyuridine</synonym>
    <synonym>Deoxyribose uracil</synonym>
    <synonym>Desoxyuridine</synonym>
    <synonym>Uracil deoxyriboside</synonym>
    <synonym>Uracil desoxyuridine</synonym>
    <synonym>(beta 1-(2-Deoxyribopyranosyl))thymidine</synonym>
    <synonym>Deoxyuridine</synonym>
  </synonyms>
  <chemical_formula>C9H12N2O5</chemical_formula>
  <average_molecular_weight>228.202</average_molecular_weight>
  <monisotopic_moleculate_weight>228.074621504</monisotopic_moleculate_weight>
  <iupac_name>1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione</iupac_name>
  <traditional_iupac>2'-deoxyuridine</traditional_iupac>
  <cas_registry_number>951-78-0</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](C[C@@H]1O)N1C=CC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1</inchi>
  <inchikey>MXHRCPNRJAMMIM-SHYZEUOFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleosides</class>
    <sub_class>Pyrimidine 2'-deoxyribonucleosides</sub_class>
    <direct_parent>Pyrimidine 2'-deoxyribonucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxyribonucleosides</external_descriptor>
      <external_descriptor>pyrimidine 2'-deoxyribonucleoside</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>167 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.51</value>
      <source>BALZARINI,JM ET AL. (1989)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>228.202</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>228.074621504</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](C[C@@H]1O)N1C=CC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H12N2O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MXHRCPNRJAMMIM-SHYZEUOFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>99.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>921</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449647</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00526</kegg_id>
  <drugbank_id>DB02256</drugbank_id>
  <foodb_id>FDB021870</foodb_id>
  <chemspider_id>13118</chemspider_id>
  <pubchem_compound_id>13712</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16450</chebi_id>
  <meta_cyc_id>DEOXYURIDINE</meta_cyc_id>
  <knapsack_id>C00019697</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35251</bigg_id>
  <wikipedia_id>Deoxyuridine</wikipedia_id>
  <metlin_id>5086</metlin_id>
  <synthesis_reference>Huang, Haoqiang; Chu, Chung K. A practical synthesis of 2'-deoxyuridine from uridine. Synthetic Communications  (1990),  20(7),  1039-46.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:27 UTC</creation_date>
  <update_date>2020-04-15 20:47:36 UTC</update_date>
  <accession>BMDB0000014</accession>
  <secondary_accessions>
    <accession>BMDB00014</accession>
  </secondary_accessions>
  <name>Deoxycytidine</name>
  <description>2'-Deoxycytidine, also known as dC, belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. 2'-Deoxycytidine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 2'-Deoxycytidine exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>4-Amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one</synonym>
    <synonym>dC</synonym>
    <synonym>DCYD</synonym>
    <synonym>2'-Deoxycytidine</synonym>
    <synonym>1-(2-Deoxy-b-D-ribofuranosyl)cytosine</synonym>
    <synonym>1-(2-Deoxy-beta-D-erythro-pentofuranosyl)-cytosine</synonym>
    <synonym>1-(2-Deoxy-beta-D-ribofuranosyl)cytosine</synonym>
    <synonym>1-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-cytosine</synonym>
    <synonym>1-(2-Deoxy-beta-delta-ribofuranosyl)cytosine</synonym>
    <synonym>2-Deoxy-cytidine</synonym>
    <synonym>4-Amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone</synonym>
    <synonym>4-Amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone</synonym>
    <synonym>4-Amino-1-(2-deoxy-beta-delta-erythro-pentofuranosyl)-2(1H)-pyrimidinone</synonym>
    <synonym>Cytosine deoxyribonucleoside</synonym>
    <synonym>Cytosine deoxyriboside</synonym>
    <synonym>Deoxy-cytidine</synonym>
    <synonym>Deoxyribose cytidine</synonym>
    <synonym>Desoxycytidine</synonym>
    <synonym>Deoxyribonucleoside, cytosine</synonym>
    <synonym>Deoxyriboside, cytosine</synonym>
    <synonym>Deoxycytidine</synonym>
  </synonyms>
  <chemical_formula>C9H13N3O4</chemical_formula>
  <average_molecular_weight>227.2172</average_molecular_weight>
  <monisotopic_moleculate_weight>227.090605919</monisotopic_moleculate_weight>
  <iupac_name>4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one</iupac_name>
  <traditional_iupac>2'-deoxycytidine</traditional_iupac>
  <cas_registry_number>951-77-9</cas_registry_number>
  <smiles>NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](CO)O1</smiles>
  <inchi>InChI=1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m0/s1</inchi>
  <inchikey>CKTSBUTUHBMZGZ-SHYZEUOFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleosides</class>
    <sub_class>Pyrimidine 2'-deoxyribonucleosides</sub_class>
    <direct_parent>Pyrimidine 2'-deoxyribonucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxyribonucleosides</external_descriptor>
      <external_descriptor>pyrimidine 2'-deoxyribonucleoside</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>207 - 210 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>870 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.77</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>227.2172</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>227.090605919</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](CO)O1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13N3O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CKTSBUTUHBMZGZ-SHYZEUOFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>108.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>53.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>922</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437550</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB02594</drugbank_id>
  <chemspider_id>13117</chemspider_id>
  <kegg_id>C00881</kegg_id>
  <foodb_id>FDB021871</foodb_id>
  <pubchem_compound_id>13711</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15698</chebi_id>
  <meta_cyc_id>DEOXYCYTIDINE</meta_cyc_id>
  <wikipedia_id>Deoxycytidine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>36280</bigg_id>
  <metlin_id>3367</metlin_id>
  <synthesis_reference>Fox, Jack F.; Yung, Naishun; Wempen, Iris; Hoffer, Max. Pyrimidine nucleosides. XII. Direct synthesis of 2'-deoxycytidine and its a-anomer. Journal of the American Chemical Society  (1961),  83  4066-50.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00863</protein_accession>
      <name>Deoxycytidine kinase</name>
      <uniprot_id>Q3MHR2</uniprot_id>
      <gene_name>DCK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:28 UTC</creation_date>
  <update_date>2020-04-15 20:47:36 UTC</update_date>
  <accession>BMDB0000015</accession>
  <secondary_accessions>
    <accession>BMDB00015</accession>
  </secondary_accessions>
  <name>Cortexolone</name>
  <description/>
  <synonyms>
    <synonym>11-Desoxy-17-hydroxycorticosterone</synonym>
    <synonym>Cortodoxone</synonym>
    <synonym>Reichstein substance S</synonym>
    <synonym>Substance S, reichstein's</synonym>
    <synonym>11 Deoxycortisol</synonym>
    <synonym>11 Desoxycortisol</synonym>
    <synonym>11 Desoxycortisone</synonym>
    <synonym>S, Reichstein's substance</synonym>
    <synonym>11-Desoxycortisol</synonym>
    <synonym>11-Desoxycortisone</synonym>
    <synonym>Reichsteins substance S</synonym>
    <synonym>11-Deoxycortisol</synonym>
    <synonym>SK&amp;F 3050</synonym>
    <synonym>Reichstein's substance S</synonym>
    <synonym>11-Deoxy-17-hydroxycorticosterone</synonym>
    <synonym>11-Deoxyhydrocortisone</synonym>
    <synonym>11-Desoxyhydrocortisone</synonym>
    <synonym>17,21-Dihydroxy-4-pregnene-3,20-dione</synonym>
    <synonym>17,21-Dihydroxypregn-4-ene-3,20-dione</synonym>
    <synonym>17,21-Dihydroxyprogesterone</synonym>
    <synonym>17-Hydroxy-11-deoxycorticosterone</synonym>
    <synonym>17alpha-Hydroxycortexone</synonym>
    <synonym>20-Dione 17,21-dihydroxypregn-4-ene-3</synonym>
    <synonym>4-Pregnene-17alpha,21-diol-3,20-dione</synonym>
    <synonym>Compound S</synonym>
    <synonym>11-Deoxy-17-hydrocorticosterone</synonym>
    <synonym>11-Deoxycortisone</synonym>
    <synonym>11-Desoxy-17α-hydroxycorticosterone</synonym>
    <synonym>11-Desoxy-17alpha-hydroxycorticosterone</synonym>
    <synonym>17,21-Dihydroxypregn-4-en-3,20-dione</synonym>
    <synonym>17Α,21-dihydroxy-4-pregnen-3,20-dione</synonym>
    <synonym>17Α,21-dihydroxypregn-4-ene-3,20-dione</synonym>
    <synonym>17Α,21-dihydroxyprogesterone</synonym>
    <synonym>17Α-hydroxycortexone</synonym>
    <synonym>4-Pregnen-17α,21-diol-3,20-dione</synonym>
    <synonym>4-Pregnene-17α,21-diol-3,20-dione</synonym>
    <synonym>17alpha,21-Dihydroxy-4-pregnen-3,20-dione</synonym>
    <synonym>17alpha,21-Dihydroxypregn-4-ene-3,20-dione</synonym>
    <synonym>17alpha,21-Dihydroxyprogesterone</synonym>
    <synonym>4-Pregnen-17alpha,21-diol-3,20-dione</synonym>
    <synonym>Cortexolone</synonym>
  </synonyms>
  <chemical_formula>C21H30O4</chemical_formula>
  <average_molecular_weight>346.4605</average_molecular_weight>
  <monisotopic_moleculate_weight>346.214409448</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</traditional_iupac>
  <cas_registry_number>152-58-9</cas_registry_number>
  <smiles>[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1</inchi>
  <inchikey>WHBHBVVOGNECLV-OBQKJFGGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
      <external_descriptor>Glucocorticoids</external_descriptor>
      <external_descriptor>deoxycortisol</external_descriptor>
      <external_descriptor>glucocorticoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>346.4605</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>346.214409448</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H30O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WHBHBVVOGNECLV-OBQKJFGGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>95.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1304458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1304459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1304460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1419007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1419008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1419009</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C05488</kegg_id>
  <drugbank_id/>
  <chemspider_id>389582</chemspider_id>
  <foodb_id>FDB021872</foodb_id>
  <pdbe_id/>
  <chebi_id>28324</chebi_id>
  <pubchem_compound_id>440707</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Cortexolone</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>45914</bigg_id>
  <metlin_id>5088</metlin_id>
  <synthesis_reference>Luu, Duc Huy.  New method for the synthesis of Reichstein's compound S from pregnene.    Tap Chi Duoc Hoc  (2002),   (9),  23-25. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:29 UTC</creation_date>
  <update_date>2020-04-15 20:47:37 UTC</update_date>
  <accession>BMDB0000016</accession>
  <secondary_accessions>
    <accession>BMDB00016</accession>
  </secondary_accessions>
  <name>Deoxycorticosterone</name>
  <description>Deoxycorticosterone, also known as Deoxycorticosterone or deoxycorticosterone, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, deoxycorticosterone is considered to be a steroid lipid molecule. Deoxycorticosterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Deoxycorticosterone exists in all living organisms, ranging from bacteria to humans. Deoxycorticosterone participates in a number of enzymatic reactions, within cattle. In particular, Deoxycorticosterone can be converted into corticosterone through the action of the enzyme cytochrome P450 11B1. In addition, Deoxycorticosterone can be biosynthesized from 21-hydroxypregnenolone; which is catalyzed by the enzyme 3-beta-HSD 1. In cattle, deoxycorticosterone is involved in the metabolic pathway called the steroidogenesis pathway. Deoxycorticosterone is a potentially toxic compound.</description>
  <synonyms>
    <synonym>21-Hydroxy-4-pregnene-3,20-dione</synonym>
    <synonym>21-Hydroxyprogesterone</synonym>
    <synonym>4-Pregnen-21-ol-3,20-dione</synonym>
    <synonym>Cortexone</synonym>
    <synonym>DESOXYCORTICOSTERONE</synonym>
    <synonym>Desoxycortone</synonym>
    <synonym>DOC</synonym>
    <synonym>Kendall's desoxy compound b</synonym>
    <synonym>Reichstein's substance Q</synonym>
    <synonym>11-Dehydroxycorticosterone</synonym>
    <synonym>11-Deoxy-corticosterone</synonym>
    <synonym>11-Deoxycorticosterone</synonym>
    <synonym>11-Desoxycorticosterone</synonym>
    <synonym>21-Hydroxy-3,20-dioxopregn-4-ene</synonym>
    <synonym>21-Hydroxy-D4-pregnane-3,20-dione</synonym>
    <synonym>21-Hydroxy-D4-pregnene-3,20-dione</synonym>
    <synonym>21-Hydroxy-pregn-4-ene-3,20-dione</synonym>
    <synonym>21-Hydroxy-progesterone</synonym>
    <synonym>21-Hydroxypregn-4-ene-3,20-dione</synonym>
    <synonym>D4-Pregnene-21-ol-3,20-dione</synonym>
    <synonym>Deoxycortone</synonym>
    <synonym>Doca</synonym>
    <synonym>11-Decorticosterone</synonym>
    <synonym>21 Hydroxyprogesterone</synonym>
    <synonym>11 Decorticosterone</synonym>
    <synonym>21 Hydroxy 4 pregnene 3,20 dione</synonym>
    <synonym>Deoxycorticosterone</synonym>
  </synonyms>
  <chemical_formula>C21H30O3</chemical_formula>
  <average_molecular_weight>330.4611</average_molecular_weight>
  <monisotopic_moleculate_weight>330.219494826</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</traditional_iupac>
  <cas_registry_number>64-85-7</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1</inchi>
  <inchikey>ZESRJSPZRDMNHY-YFWFAHHUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>20-oxo steroid</external_descriptor>
      <external_descriptor>21-hydroxy steroid</external_descriptor>
      <external_descriptor>3-oxo Delta(4)-steroid</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
      <external_descriptor>Mineralocorticoids</external_descriptor>
      <external_descriptor>Pregnane and derivatives [Fig]</external_descriptor>
      <external_descriptor>mineralocorticoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>141 - 142 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0595 mg/mL at 37 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.88</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>330.4611</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>330.219494826</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H30O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZESRJSPZRDMNHY-YFWFAHHUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>94.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroidogenesis</name>
      <smpdb_id>SMP0087238</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>924</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03205</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB006404</foodb_id>
  <chemspider_id>5932</chemspider_id>
  <chebi_id>16973</chebi_id>
  <pubchem_compound_id>6166</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>41397</bigg_id>
  <wikipedia_id>Desoxycorticosterone</wikipedia_id>
  <metlin_id>5089</metlin_id>
  <meta_cyc_id>11-DEOXYCORTICOSTERONE</meta_cyc_id>
  <synthesis_reference>Mattox V R; Goodrich J E; Vrieze W D  Synthesis of C-21 glucosiduronates of cortisone and related corticosteroids.    Biochemistry  (1969),  8(3),  1188-99.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:30 UTC</creation_date>
  <update_date>2020-04-15 22:12:57 UTC</update_date>
  <accession>BMDB0000017</accession>
  <secondary_accessions>
    <accession>BMDB00017</accession>
  </secondary_accessions>
  <name>4-Pyridoxic acid</name>
  <description>4-4-4-pyridoxic acid, also known as 4-4-pyridoxic acid, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. 4-4-4-pyridoxic acid exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. 4-4-4-pyridoxic acid exists in all living organisms, ranging from bacteria to humans. 4-4-4-pyridoxic acid can be biosynthesized from pyridoxal; which is catalyzed by the enzyme aldehyde oxidase. In cattle, 4-4-pyridoxic acid is involved in the metabolic pathway called the vitamin B6 metabolism pathway.</description>
  <synonyms>
    <synonym>2-Methyl-3-hydroxy-4-carboxy-5-hydroxymethylpyridine</synonym>
    <synonym>3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinic acid</synonym>
    <synonym>4-Pyridoxate</synonym>
    <synonym>4-Pyridoxinecarboxylic acid</synonym>
    <synonym>4-Pyridoxinic acid</synonym>
    <synonym>4-Pyridoxylic acid</synonym>
    <synonym>Pyridoxic acid</synonym>
    <synonym>3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinate</synonym>
    <synonym>4-Pyridoxinecarboxylate</synonym>
    <synonym>4-Pyridoxinate</synonym>
    <synonym>4-Pyridoxylate</synonym>
    <synonym>Pyridoxate</synonym>
    <synonym>3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylate</synonym>
    <synonym>3-Hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridinecarboxylic acid</synonym>
    <synonym>3-Hydroxy-5-(hydroxymethyl)-2-methyl-isonicotinate</synonym>
    <synonym>3-Hydroxy-5-(hydroxymethyl)-2-methyl-isonicotinic acid</synonym>
    <synonym>3-Hydroxy-5-hydroxymethyl-2-methyl-isonicotinate</synonym>
    <synonym>3-Hydroxy-5-hydroxymethyl-2-methyl-isonicotinic acid</synonym>
    <synonym>3-Hydroxy-5-hydroxymethyl-2-methyl-isonicotinsaeure</synonym>
    <synonym>4-Pyridoxinsaeure</synonym>
    <synonym>4 Pyridoxinic acid</synonym>
    <synonym>Pyridoxinecarboxylic acid</synonym>
    <synonym>4 Pyridoxylic acid</synonym>
    <synonym>4 Pyridoxic acid</synonym>
  </synonyms>
  <chemical_formula>C8H9NO4</chemical_formula>
  <average_molecular_weight>183.1614</average_molecular_weight>
  <monisotopic_moleculate_weight>183.053157781</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxylic acid</iupac_name>
  <traditional_iupac>pyridoxic acid</traditional_iupac>
  <cas_registry_number>82-82-6</cas_registry_number>
  <smiles>CC1=NC=C(CO)C(C(O)=O)=C1O</smiles>
  <inchi>InChI=1S/C8H9NO4/c1-4-7(11)6(8(12)13)5(3-10)2-9-4/h2,10-11H,3H2,1H3,(H,12,13)</inchi>
  <inchikey>HXACOUQIXZGNBF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyridinecarboxylic acids and derivatives</sub_class>
    <direct_parent>Pyridinecarboxylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyridines</alternative_parent>
      <alternative_parent>Methylpyridines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyridine</substituent>
      <substituent>Methylpyridine</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyridine carboxylic acid</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>hydroxymethylpyridine</external_descriptor>
      <external_descriptor>methylpyridines</external_descriptor>
      <external_descriptor>monohydroxypyridine</external_descriptor>
      <external_descriptor>vitamin B6</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>247 - 248 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>183.1614</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>183.053157781</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=NC=C(CO)C(C(O)=O)=C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H9NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H9NO4/c1-4-7(11)6(8(12)13)5(3-10)2-9-4/h2,10-11H,3H2,1H3,(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HXACOUQIXZGNBF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>90.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>44.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Vitamin B6 Metabolism</name>
      <smpdb_id>SMP0087240</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451897</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00847</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB021874</foodb_id>
  <chemspider_id>6467</chemspider_id>
  <chebi_id>17405</chebi_id>
  <pubchem_compound_id>6723</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>36190</bigg_id>
  <wikipedia_id/>
  <metlin_id>239</metlin_id>
  <meta_cyc_id>CPD-1112</meta_cyc_id>
  <synthesis_reference>Senkuma, Masahiko; Imada, Katsumi; Sato, Masatada. Preparation of 4-pyridoxic acid. Jpn. Kokai Tokkyo Koho  (1992),  2 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:31 UTC</creation_date>
  <update_date>2020-04-16 20:37:19 UTC</update_date>
  <accession>BMDB0000019</accession>
  <secondary_accessions>
    <accession>BMDB00019</accession>
  </secondary_accessions>
  <name>Alpha-ketoisovaleric acid</name>
  <description/>
  <synonyms>
    <synonym>2-Keto-3-methylbutyric acid</synonym>
    <synonym>2-Ketoisovaleric acid</synonym>
    <synonym>2-Ketovaline</synonym>
    <synonym>2-oxo-3-Methylbutanoic acid</synonym>
    <synonym>2-oxo-3-Methylbutyric acid</synonym>
    <synonym>2-Oxoisovaleric acid</synonym>
    <synonym>3-Methyl-2-oxobutanoate</synonym>
    <synonym>3-Methyl-2-oxobutyric acid</synonym>
    <synonym>alpha-Keto-isovaleric acid</synonym>
    <synonym>alpha-Ketovaline</synonym>
    <synonym>alpha-oxo-beta-Methylbutyricacid</synonym>
    <synonym>alpha-Oxoisovaleric acid</synonym>
    <synonym>Dimethylpyruvic acid</synonym>
    <synonym>Isopropylglyoxylic acid</synonym>
    <synonym>2-oxo-3-Methylbutanoate</synonym>
    <synonym>2-Oxoisovalerate</synonym>
    <synonym>2-Oxoisopentanoate</synonym>
    <synonym>2-Keto-3-methylbutyrate</synonym>
    <synonym>2-Ketoisovalerate</synonym>
    <synonym>2-oxo-3-Methylbutyrate</synonym>
    <synonym>3-Methyl-2-oxobutanoic acid</synonym>
    <synonym>3-Methyl-2-oxobutyrate</synonym>
    <synonym>a-Keto-isovalerate</synonym>
    <synonym>a-Keto-isovaleric acid</synonym>
    <synonym>alpha-Keto-isovalerate</synonym>
    <synonym>Α-keto-isovalerate</synonym>
    <synonym>Α-keto-isovaleric acid</synonym>
    <synonym>a-Ketovaline</synonym>
    <synonym>Α-ketovaline</synonym>
    <synonym>a-oxo-b-Methylbutyricacid</synonym>
    <synonym>Α-oxo-β-methylbutyricacid</synonym>
    <synonym>a-Oxoisovalerate</synonym>
    <synonym>a-Oxoisovaleric acid</synonym>
    <synonym>alpha-Oxoisovalerate</synonym>
    <synonym>Α-oxoisovalerate</synonym>
    <synonym>Α-oxoisovaleric acid</synonym>
    <synonym>Dimethylpyruvate</synonym>
    <synonym>Isopropylglyoxylate</synonym>
    <synonym>2-Oxoisopentanoic acid</synonym>
    <synonym>a-Ketoisovalerate</synonym>
    <synonym>a-Ketoisovaleric acid</synonym>
    <synonym>alpha-Ketoisovalerate</synonym>
    <synonym>Α-ketoisovalerate</synonym>
    <synonym>Α-ketoisovaleric acid</synonym>
    <synonym>2-Ketoisvaleric acid</synonym>
    <synonym>2-oxo-3-Methyl-butyrate</synonym>
    <synonym>3-Methyl-2-oxo-butanoate</synonym>
    <synonym>3-Methyl-2-oxo-butanoic acid</synonym>
    <synonym>3-Methyl-2-oxo-butyrate</synonym>
    <synonym>3-Methyl-2-oxo-butyric acid</synonym>
    <synonym>3-Methyl-2-oxobutinoate</synonym>
    <synonym>3-Methyl-2-oxobutinoic acid</synonym>
    <synonym>a-Keto-b-methylbutyrate</synonym>
    <synonym>a-Keto-b-methylbutyric acid</synonym>
    <synonym>a-oxo-b-Methylbutyrate</synonym>
    <synonym>a-oxo-b-Methylbutyric acid</synonym>
    <synonym>alpha-Keto-beta-methylbutyrate</synonym>
    <synonym>alpha-Keto-beta-methylbutyric acid</synonym>
    <synonym>alpha-oxo-beta-Methylbutyrate</synonym>
    <synonym>alpha-oxo-beta-Methylbutyric acid</synonym>
    <synonym>Ketovaline</synonym>
    <synonym>alpha-Ketoisopentanoic acid</synonym>
    <synonym>alpha-Ketoisovaleric acid</synonym>
  </synonyms>
  <chemical_formula>C5H8O3</chemical_formula>
  <average_molecular_weight>116.1152</average_molecular_weight>
  <monisotopic_moleculate_weight>116.047344122</monisotopic_moleculate_weight>
  <iupac_name>3-methyl-2-oxobutanoic acid</iupac_name>
  <traditional_iupac>α-ketoisovalerate</traditional_iupac>
  <cas_registry_number>759-05-7</cas_registry_number>
  <smiles>CC(C)C(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)</inchi>
  <inchikey>QHKABHOOEWYVLI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Short-chain keto acids and derivatives</sub_class>
    <direct_parent>Short-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain keto acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>Branched fatty acids</external_descriptor>
      <external_descriptor>Branched fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>31.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-methyl-2-oxobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>116.1152</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>116.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)C(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QHKABHOOEWYVLI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>27.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438656</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.38 +/- 0.09</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.45 +/- 0.09</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.26 +/- 0.10</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.29 +/- 0.10</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB04074</drugbank_id>
  <chemspider_id>48</chemspider_id>
  <pubchem_compound_id>49</pubchem_compound_id>
  <kegg_id>C00141</kegg_id>
  <foodb_id>FDB012250</foodb_id>
  <pdbe_id/>
  <chebi_id>16530</chebi_id>
  <meta_cyc_id>2-KETO-ISOVALERATE</meta_cyc_id>
  <knapsack_id>C00007623</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34011</bigg_id>
  <wikipedia_id>Alpha-Ketoisovaleric acid</wikipedia_id>
  <metlin_id>5091</metlin_id>
  <synthesis_reference>Pirrung, Michael C.; Ha, Hyun Joon; Holmes, Christopher P. Purification and inhibition of spinach a,b-dihydroxyacid dehydratase . Journal of Organic Chemistry  (1989),  54(7),  1543-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00637</protein_accession>
      <name>2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial</name>
      <uniprot_id>P11178</uniprot_id>
      <gene_name>BCKDHA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00638</protein_accession>
      <name>2-oxoisovalerate dehydrogenase subunit beta, mitochondrial</name>
      <uniprot_id>P21839</uniprot_id>
      <gene_name>BCKDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:32 UTC</creation_date>
  <update_date>2020-04-15 22:08:14 UTC</update_date>
  <accession>BMDB0000020</accession>
  <secondary_accessions>
    <accession>BMDB00020</accession>
  </secondary_accessions>
  <name>p-Hydroxyphenylacetic acid</name>
  <description>4-Hydroxyphenylacetic acid, also known as (p-hydroxyphenyl)acetate or 4-hydroxybenzeneacetate, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. 4-Hydroxyphenylacetic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 4-Hydroxyphenylacetic acid exists in all living species, ranging from bacteria to humans. 4-Hydroxyphenylacetic acid is a potentially toxic compound. 4-Hydroxyphenylacetic acid has been found to be associated with several diseases known as lung cancer, crohn's disease, spina bifida, and epilepsy; also 4-hydroxyphenylacetic acid has been linked to the inborn metabolic disorders including phenylketonuria.</description>
  <synonyms>
    <synonym>(p-Hydroxyphenyl)acetic acid</synonym>
    <synonym>4-Carboxymethylphenol</synonym>
    <synonym>4-Hydroxybenzeneacetic acid</synonym>
    <synonym>4-Hydroxyphenylacetate</synonym>
    <synonym>4-Hydroxyphenylacetic acid</synonym>
    <synonym>(p-Hydroxyphenyl)acetate</synonym>
    <synonym>4-Hydroxybenzeneacetate</synonym>
    <synonym>p-Hydroxyphenylacetate</synonym>
    <synonym>(4-Hydroxy-phenyl)-acetate</synonym>
    <synonym>(4-Hydroxy-phenyl)-acetic acid</synonym>
    <synonym>(4-Hydroxy-phenyl)-essigsaeure</synonym>
    <synonym>(4-Hydroxyphenyl)acetate</synonym>
    <synonym>(4-Hydroxyphenyl)acetic acid</synonym>
    <synonym>(p-Hydroxyphenyl)-acetate</synonym>
    <synonym>(p-Hydroxyphenyl)-acetic acid</synonym>
    <synonym>4-Hydroxy-benzeneacetate</synonym>
    <synonym>4-Hydroxy-benzeneacetic acid</synonym>
    <synonym>4-Hydroxyphenyl-acetic acid</synonym>
    <synonym>Parahydroxy phenylacetate</synonym>
    <synonym>Parahydroxy phenylacetic acid</synonym>
    <synonym>Parahydroxyphenylacetate</synonym>
    <synonym>Para-hydroxyphenylacetic acid</synonym>
    <synonym>p-Hydroxyphenylacetic acid</synonym>
  </synonyms>
  <chemical_formula>C8H8O3</chemical_formula>
  <average_molecular_weight>152.1473</average_molecular_weight>
  <monisotopic_moleculate_weight>152.047344122</monisotopic_moleculate_weight>
  <iupac_name>2-(4-hydroxyphenyl)acetic acid</iupac_name>
  <traditional_iupac>4-hydroxyphenylacetic acid</traditional_iupac>
  <cas_registry_number>156-38-7</cas_registry_number>
  <smiles>OC(=O)CC1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)</inchi>
  <inchikey>XQXPVVBIMDBYFF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>1-hydroxy-2-unsubstituted benzenoids</sub_class>
    <direct_parent>1-hydroxy-2-unsubstituted benzenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>monocarboxylic acid</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>148 - 150 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>60.7 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.75</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(4-hydroxyphenyl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>152.1473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>152.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC1=CC=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XQXPVVBIMDBYFF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449841</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>78510  +/- 12590</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>O'Grady L, Doherty ML, Mulligan FJ: Subacute ruminal acidosis (SARA) in grazing Irish dairy cows. Vet J. 2008 Apr;176(1):44-9. doi: 10.1016/j.tvjl.2007.12.017. Epub 2008 Mar 6.</reference_text>
          <pubmed_id>18328751</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00642</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB010534</foodb_id>
  <chemspider_id>124</chemspider_id>
  <chebi_id>18101</chebi_id>
  <pubchem_compound_id>127</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id>573</phenol_explorer_compound_id>
  <knapsack_id/>
  <bigg_id>35599</bigg_id>
  <wikipedia_id>4-hydroxyphenylacetic_acid</wikipedia_id>
  <metlin_id>130</metlin_id>
  <meta_cyc_id>4-HYDROXYPHENYLACETATE</meta_cyc_id>
  <synthesis_reference>Qiao, Xi-long; Tian, Hui; Li, Wen; Zhao, Xiu-yun; Zhang, Jin-fang.  Study of 4-hydroxyphenylacetic acid synthesis from glyoxalic acid.    Hebei Gongye Keji  (2005),  22(5),  264-266.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:33 UTC</creation_date>
  <update_date>2020-04-15 22:36:41 UTC</update_date>
  <accession>BMDB0000021</accession>
  <secondary_accessions>
    <accession>BMDB00021</accession>
  </secondary_accessions>
  <name>Iodotyrosine</name>
  <description>Iodotyrosine, also known as MIT or IYR, belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Iodotyrosine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Iodotyrosine exists in all living organisms, ranging from bacteria to humans. In cattle, iodotyrosine is involved in the metabolic pathway called thyroid hormone synthesis pathway.</description>
  <synonyms>
    <synonym>(2S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoic acid</synonym>
    <synonym>3-IODO-tyrosine</synonym>
    <synonym>MIT</synonym>
    <synonym>(2S)-2-Amino-3-(4-hydroxy-3-iodophenyl)propanoate</synonym>
    <synonym>3-Iodo-4-hydroxyphenylalanine</synonym>
    <synonym>3-Iodo-L-tyrosine</synonym>
    <synonym>3-Iodotyrosine</synonym>
    <synonym>3-Monoiodo-L-tyrosine</synonym>
    <synonym>4-Hydroxy-3-iodophenylalanine</synonym>
    <synonym>IYR</synonym>
    <synonym>L-Tyrosine-3-iodo</synonym>
    <synonym>Monoiodotyrosine</synonym>
  </synonyms>
  <chemical_formula>C9H10INO3</chemical_formula>
  <average_molecular_weight>307.0851</average_molecular_weight>
  <monisotopic_moleculate_weight>306.970536611</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid</iupac_name>
  <traditional_iupac>iodotyrosine</traditional_iupac>
  <cas_registry_number>70-78-0</cas_registry_number>
  <smiles>N[C@@H](CC1=CC=C(O)C(I)=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C9H10INO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1</inchi>
  <inchikey>UQTZMGFTRHFAAM-ZETCQYMHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Tyrosine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aryl iodides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Iodobenzenes</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>O-iodophenols</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organoiodides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalanine and derivatives</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>2-halophenol</substituent>
      <substituent>2-iodophenol</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Aryl iodide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Iodobenzene</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organoiodide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Tyrosine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-tyrosine derivative</external_descriptor>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>monoiodotyrosine</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>205 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>3 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>307.0851</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>306.970536611</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CC1=CC=C(O)C(I)=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10INO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10INO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UQTZMGFTRHFAAM-ZETCQYMHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>83.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Thyroid Hormone Synthesis</name>
      <smpdb_id>SMP0087269</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>37</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>38</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>263550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>263551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>263552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>283479</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB01758</drugbank_id>
  <foodb_id>FDB021875</foodb_id>
  <kegg_id>C02515</kegg_id>
  <pubchem_compound_id>439744</pubchem_compound_id>
  <chemspider_id>388804</chemspider_id>
  <pdbe_id/>
  <chebi_id>27847</chebi_id>
  <meta_cyc_id>CPD-12288</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>39998</bigg_id>
  <wikipedia_id>3-Iodotyrosine</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Hillmann, Gunther; Hillmann-Elies, Anneliese.  Synthesis of 3-iodo-L-tyrosine.    Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie  (1956),  305  177-81.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:35 UTC</creation_date>
  <update_date>2020-04-16 20:37:19 UTC</update_date>
  <accession>BMDB0000022</accession>
  <secondary_accessions>
    <accession>BMDB00022</accession>
  </secondary_accessions>
  <name>3-Methoxytyramine</name>
  <description>3-3-3-methoxytyramine, also known as 3-O-methyldopamine, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 3-3-3-methoxytyramine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 3-3-3-methoxytyramine exists in all living organisms, ranging from bacteria to humans. 3-3-3-methoxytyramine participates in a number of enzymatic reactions, within cattle. In particular, 3-3-3-methoxytyramine can be converted into homovanillin through its interaction with the enzyme amine oxidase [flavin-containing] a. In addition, 3-3-3-methoxytyramine and pyrocatechol can be biosynthesized from dopamine and guaiacol through the action of the enzyme catechol O-methyltransferase. In cattle, 3-3-methoxytyramine is involved in the metabolic pathway called the tyrosine metabolism pathway. 3-3-3-methoxytyramine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>3-Methoxy-4-hydroxyphenylethyl amine</synonym>
    <synonym>3-O-Methyldopamine</synonym>
    <synonym>4-(2-Amino-ethyl)-2-methoxy-phenol</synonym>
    <synonym>4-(2-Aminoethyl)-2-methoxy-phenol</synonym>
    <synonym>4-(2-Aminoethyl)-2-methoxyphenol</synonym>
    <synonym>5-(2-Aminoethyl)guaiacol</synonym>
    <synonym>Methoxytyramine</synonym>
    <synonym>3-Methoxytyramine hydrochloride</synonym>
  </synonyms>
  <chemical_formula>C9H13NO2</chemical_formula>
  <average_molecular_weight>167.205</average_molecular_weight>
  <monisotopic_moleculate_weight>167.094628665</monisotopic_moleculate_weight>
  <iupac_name>4-(2-aminoethyl)-2-methoxyphenol</iupac_name>
  <traditional_iupac>methoxytyramine</traditional_iupac>
  <cas_registry_number>554-52-9</cas_registry_number>
  <smiles>COC1=C(O)C=CC(CCN)=C1</smiles>
  <inchi>InChI=1S/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3</inchi>
  <inchikey>DIVQKHQLANKJQO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Methoxyphenols</sub_class>
    <direct_parent>Methoxyphenols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>2-arylethylamines</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenethylamines</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>2-arylethylamine</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Amine</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenethylamine</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>methoxybenzene</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>logp</kind>
      <value>-0.08</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-(2-aminoethyl)-2-methoxyphenol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>167.205</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>167.094628665</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=C(O)C=CC(CCN)=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DIVQKHQLANKJQO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>55.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>39</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>40</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>41</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451979</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>1606</chemspider_id>
  <kegg_id>C05587</kegg_id>
  <foodb_id>FDB021876</foodb_id>
  <pubchem_compound_id>1669</pubchem_compound_id>
  <chebi_id>742324</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <knapsack_id>C00042132</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>3-Methoxytyramine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>46076</bigg_id>
  <metlin_id>5094</metlin_id>
  <synthesis_reference>Kametani, Tetsuji; Takano, Seiichi; Karibe, Etsuo.  Syntheses of heterocyclic compounds. LXXXVII. Simplified synthesis of 3-methoxy-4-hydroxy- and 3-methoxy-4-tosyloxyphenethylamine.    Yakugaku Zasshi  (1963),  83(11),  1035-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:36 UTC</creation_date>
  <update_date>2020-03-18 18:12:11 UTC</update_date>
  <accession>BMDB0000023</accession>
  <secondary_accessions>
    <accession>BMDB00023</accession>
  </secondary_accessions>
  <name>(S)-3-Hydroxyisobutyric acid</name>
  <description/>
  <synonyms>
    <synonym>(S)-3-Hydroxy-2-methylpropanoic acid</synonym>
    <synonym>(S)-3-Hydroxy-2-methylpropionic acid</synonym>
    <synonym>(S)-3-Hydroxy-2-methylpropanoate</synonym>
    <synonym>(S)-3-Hydroxy-2-methylpropionate</synonym>
    <synonym>(S)-3-Hydroxyisobutyrate</synonym>
    <synonym>2-Methyl-L-(+)-hydracrylate</synonym>
    <synonym>2-Methyl-L-(+)-hydracrylic acid</synonym>
    <synonym>3-Hydroxy(iso)butyric acid</synonym>
    <synonym>3-Hydroxy-2-methyl-(S)-propanoate</synonym>
    <synonym>3-Hydroxy-2-methyl-(S)-propanoic acid</synonym>
    <synonym>3-Hydroxy-2-methylpropanoate</synonym>
    <synonym>3-Hydroxy-2-methylpropanoic acid</synonym>
    <synonym>3-Hydroxy-isobutyrate</synonym>
    <synonym>3-Hydroxyisobutyrate</synonym>
    <synonym>3-Hydroxyisobutyric acid</synonym>
    <synonym>(2S)-3-Hydroxy-2-methylpropanoic acid</synonym>
    <synonym>(2S)-3-Hydroxy-2-methylpropionic acid</synonym>
    <synonym>(S)-beta-Hydroxyisobutyric acid</synonym>
    <synonym>(S)-Β-hydroxyisobutyric acid</synonym>
    <synonym>(±)-3-hydroxy-2-methylpropanoic acid</synonym>
    <synonym>(±)-3-hydroxy-2-methylpropionic acid</synonym>
    <synonym>2-(Hydroxymethyl)propanoic acid</synonym>
    <synonym>2-(Hydroxymethyl)propionic acid</synonym>
    <synonym>2-Methyl-3-hydroxypropanoic acid</synonym>
    <synonym>2-Methyl-3-hydroxypropionic acid</synonym>
    <synonym>3-HIBA</synonym>
    <synonym>3-Hydroxy-2-methylpropionic acid</synonym>
    <synonym>DL-3-Hydroxyisobutyric acid</synonym>
    <synonym>L-(+)-beta-Hydroxyisobutyric acid</synonym>
    <synonym>L-(+)-Β-hydroxyisobutyric acid</synonym>
    <synonym>beta-Hydroxyisobutyric acid</synonym>
    <synonym>Β-hydroxyisobutyric acid</synonym>
    <synonym>3-Hydroxy-2-isobutyrate</synonym>
    <synonym>3-Hydroxy-2-isobutyric acid</synonym>
    <synonym>(S)-3-Hydroxyisobutyric acid</synonym>
  </synonyms>
  <chemical_formula>C4H8O3</chemical_formula>
  <average_molecular_weight>104.1045</average_molecular_weight>
  <monisotopic_moleculate_weight>104.047344122</monisotopic_moleculate_weight>
  <iupac_name>(2S)-3-hydroxy-2-methylpropanoic acid</iupac_name>
  <traditional_iupac>(S)-3-hydroxyisobutyric acid</traditional_iupac>
  <cas_registry_number>2068-83-9</cas_registry_number>
  <smiles>C[C@@H](CO)C(O)=O</smiles>
  <inchi>InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1</inchi>
  <inchikey>DBXBTMSZEOQQDU-VKHMYHEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Beta hydroxy acids and derivatives</sub_class>
    <direct_parent>Beta hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hydroxyisobutyric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-3-hydroxy-2-methylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>104.1045</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>104.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](CO)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DBXBTMSZEOQQDU-VKHMYHEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>23.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>42</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>43</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>44</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181130</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>389707</chemspider_id>
  <kegg_id>C06001</kegg_id>
  <foodb_id>FDB021877</foodb_id>
  <pubchem_compound_id>440873</pubchem_compound_id>
  <chebi_id>37373</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>37034</bigg_id>
  <metlin_id>483</metlin_id>
  <synthesis_reference>Robison, Robert S.; Doremus, Michael G.L-(+)-b-Hydroxyisobutyric acid by fermentation. U.S.  (1986),   5 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00549</protein_accession>
      <name>3-hydroxyisobutyryl-CoA hydrolase, mitochondrial</name>
      <uniprot_id>Q2HJ73</uniprot_id>
      <gene_name>HIBCH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00550</protein_accession>
      <name>3-hydroxyisobutyrate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q2HJD7</uniprot_id>
      <gene_name>HIBADH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:37 UTC</creation_date>
  <update_date>2020-04-16 17:53:00 UTC</update_date>
  <accession>BMDB0000024</accession>
  <secondary_accessions>
    <accession>BMDB00024</accession>
  </secondary_accessions>
  <name>3-O-Sulfogalactosylceramide (d18:1/24:0)</name>
  <description/>
  <synonyms>
    <synonym>3-O-Sulphogalactosylceramide (D18:1/24:0)</synonym>
  </synonyms>
  <chemical_formula>C48H93NO11S</chemical_formula>
  <average_molecular_weight>892.33</average_molecular_weight>
  <monisotopic_moleculate_weight>891.646933993</monisotopic_moleculate_weight>
  <iupac_name>[(2R,5S,6R)-3,5-dihydroxy-2-{[(2S,3R,4E)-3-hydroxy-2-tetracosanamidooctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid</iupac_name>
  <traditional_iupac>C24 sulfatide</traditional_iupac>
  <cas_registry_number>151122-71-3</cas_registry_number>
  <smiles>[H][C@@](CO[C@@H]1O[C@H](CO)[C@H](O)C(OS(O)(=O)=O)C1O)(NC(=O)CCCCCCCCCCCCCCCCCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCC</smiles>
  <inchi>InChI=1S/C48H93NO11S/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2)40-58-48-46(54)47(60-61(55,56)57)45(53)43(39-50)59-48/h35,37,41-43,45-48,50-51,53-54H,3-34,36,38-40H2,1-2H3,(H,49,52)(H,55,56,57)/b37-35+/t41-,42+,43+,45-,46?,47?,48+/m0/s1</inchi>
  <inchikey>MEAZTWJVOWHKJM-YQTIZROBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Methoxyphenols</sub_class>
    <direct_parent>Methoxyphenols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>2-arylethylamines</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenethylamines</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>2-arylethylamine</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Amine</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenethylamine</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>methoxybenzene</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>10.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(2R,5S,6R)-3,5-dihydroxy-2-{[(2S,3R,4E)-3-hydroxy-2-tetracosanamidooctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxidanesulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>892.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>891.646933993</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](CO[C@@H]1O[C@H](CO)[C@H](O)C(OS(O)(=O)=O)C1O)(NC(=O)CCCCCCCCCCCCCCCCCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C48H93NO11S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C48H93NO11S/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2)40-58-48-46(54)47(60-61(55,56)57)45(53)43(39-50)59-48/h35,37,41-43,45-48,50-51,53-54H,3-34,36,38-40H2,1-2H3,(H,49,52)(H,55,56,57)/b37-35+/t41-,42+,43+,45-,46?,47?,48+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MEAZTWJVOWHKJM-YQTIZROBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>192.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>244.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>111.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <kegg_id/>
  <drugbank_id/>
  <chemspider_id>24823255</chemspider_id>
  <pdbe_id/>
  <chebi_id/>
  <pubchem_compound_id>24779585</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Hakomori, Senichiro; Ishimoda, Taiko; Nakamura, Kiyoshi.  Separation and characterization of two sulfatides of brain.    Journal of Biochemistry (Tokyo, Japan)  (1962),  52  468-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00080</protein_accession>
      <name>Galactosylceramide sulfotransferase</name>
      <uniprot_id>A6QNK1</uniprot_id>
      <gene_name>GAL3ST1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00081</protein_accession>
      <name>Arylsulfatase A</name>
      <uniprot_id>Q08DD1</uniprot_id>
      <gene_name>ARSA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:38 UTC</creation_date>
  <update_date>2020-04-14 22:46:08 UTC</update_date>
  <accession>BMDB0000026</accession>
  <secondary_accessions>
    <accession>BMDB00026</accession>
  </secondary_accessions>
  <name>Ureidopropionic acid</name>
  <description/>
  <synonyms>
    <synonym>3-[(Aminocarbonyl)amino]propanoic acid</synonym>
    <synonym>3-Ureidopropanoate</synonym>
    <synonym>3-Ureidopropanoic acid</synonym>
    <synonym>3-Ureidopropionate</synonym>
    <synonym>3-Ureidopropionic acid</synonym>
    <synonym>beta-Ureidopropionic acid</synonym>
    <synonym>N-(AMINOCARBONYL)-BETA-alanine</synonym>
    <synonym>Ureidopropanoic acid</synonym>
    <synonym>N-Carbamoyl-beta-alanine</synonym>
    <synonym>3-[(Aminocarbonyl)amino]propanoate</synonym>
    <synonym>b-Ureidopropionate</synonym>
    <synonym>b-Ureidopropionic acid</synonym>
    <synonym>beta-Ureidopropionate</synonym>
    <synonym>Β-ureidopropionate</synonym>
    <synonym>Β-ureidopropionic acid</synonym>
    <synonym>N-(AMINOCARBONYL)-b-alanine</synonym>
    <synonym>N-(AMINOCARBONYL)-β-alanine</synonym>
    <synonym>Ureidopropanoate</synonym>
    <synonym>N-Carbamoyl-b-alanine</synonym>
    <synonym>N-Carbamoyl-β-alanine</synonym>
    <synonym>Ureidopropionate</synonym>
    <synonym>3-(carbamoylamino)Propanoate</synonym>
    <synonym>3-(carbamoylamino)Propanoic acid</synonym>
    <synonym>3-ureido-Propionate</synonym>
    <synonym>Carbamoyl-b-ala-OH</synonym>
    <synonym>Carbamoyl-beta-ala-OH</synonym>
    <synonym>N-(Aminocarbonyl)-'b-alanine</synonym>
    <synonym>N-Carbamyl-b-alanine</synonym>
    <synonym>N-Carbamyl-beta-alanine</synonym>
    <synonym>Ion(-1) OF N-carbamoyl-beta-alanine</synonym>
    <synonym>Carbamoyl-beta-alanine</synonym>
    <synonym>Carbamoyl-β-alanine</synonym>
    <synonym>Carbamyl beta-alanine</synonym>
    <synonym>Carbamyl β-alanine</synonym>
    <synonym>beta-Ureidopropanoic acid</synonym>
    <synonym>β-Ureidopropanoic acid</synonym>
  </synonyms>
  <chemical_formula>C4H8N2O3</chemical_formula>
  <average_molecular_weight>132.1179</average_molecular_weight>
  <monisotopic_moleculate_weight>132.053492132</monisotopic_moleculate_weight>
  <iupac_name>3-(carbamoylamino)propanoic acid</iupac_name>
  <traditional_iupac>ureidopropionic acid</traditional_iupac>
  <cas_registry_number>462-88-4</cas_registry_number>
  <smiles>NC(=O)NCCC(O)=O</smiles>
  <inchi>InChI=1S/C4H8N2O3/c5-4(9)6-2-1-3(7)8/h1-2H2,(H,7,8)(H3,5,6,9)</inchi>
  <inchikey>JSJWCHRYRHKBBW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as ureas. Ureas are compounds containing two amine groups joined by a carbonyl (C=O) functional group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic carbonic acids and derivatives</class>
    <sub_class>Ureas</sub_class>
    <direct_parent>Ureas</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Urea</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>beta-alanine derivative</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>170 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>20.9 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(carbamoylamino)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.1179</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.053492132</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)NCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8N2O3/c5-4(9)6-2-1-3(7)8/h1-2H2,(H,7,8)(H3,5,6,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JSJWCHRYRHKBBW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10368</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>45</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>47</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288871</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451947</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>109</chemspider_id>
  <kegg_id>C02642</kegg_id>
  <foodb_id>FDB030466</foodb_id>
  <pubchem_compound_id>111</pubchem_compound_id>
  <chebi_id>18261</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id>3-UREIDO-PROPIONATE</meta_cyc_id>
  <wikipedia_id>3-Ureidopropionic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>w-Ureido carboxylic acids.    (1962),     3 pp.  GB  913713  19621228  CAN 58:72975  AN 1963:72975</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:39 UTC</creation_date>
  <update_date>2020-04-14 22:48:23 UTC</update_date>
  <accession>BMDB0000027</accession>
  <secondary_accessions>
    <accession>BMDB0000787</accession>
    <accession>BMDB00027</accession>
    <accession>BMDB00787</accession>
  </secondary_accessions>
  <name>Tetrahydrobiopterin</name>
  <description/>
  <synonyms>
    <synonym>(-)-(6R)-2-Amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone</synonym>
    <synonym>(6R)-L-Erythro-5,6,7,8-tetrahydrobiopterin</synonym>
    <synonym>(6R)-L-Erythro-tetrahydrobiopterin</synonym>
    <synonym>2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinone</synonym>
    <synonym>5,6,7,8-Tetrahydrobiopterin</synonym>
    <synonym>6R-5,6,7,8-Tetrahydrobiopterin</synonym>
    <synonym>6R-BH4</synonym>
    <synonym>6R-L-5,6,7,8-Tetrahydrobiopterin</synonym>
    <synonym>R-THBP</synonym>
    <synonym>Sapropterina</synonym>
    <synonym>Sapropterinum</synonym>
    <synonym>Tetrahydrobiopterin</synonym>
    <synonym>5,6,7,8-erythro-Tetrahydrobiopterin</synonym>
    <synonym>5,6,7,8-tetrahydro-L-Erythrobiopterin</synonym>
    <synonym>5,6,7,8-Tetrahydrobiopterin, (S-(r*,s*))-isomer</synonym>
    <synonym>5,6,7,8-Tetrahydrodictyopterin</synonym>
    <synonym>6R-L-erythro-5,6,7,8-Tetrahydrobiopterin</synonym>
    <synonym>BPH4</synonym>
    <synonym>D-threo-Tetrahydrobiopterin</synonym>
    <synonym>THBP</synonym>
    <synonym>Kuvan</synonym>
    <synonym>Phenylalanine hydroxylase cofactor</synonym>
    <synonym>Sapropterin dihydrochloride</synonym>
    <synonym>tetrahydro-6-Biopterin</synonym>
    <synonym>2',4',5'-Trihydroxybutyrophenone</synonym>
    <synonym>Sapropterin</synonym>
    <synonym>Trihydroxybutyrophenone</synonym>
    <synonym>1-Butanone, 1-(2,4,5-trihydroxyphenyl)</synonym>
    <synonym>2,4,5-Trihydroxybutyrophenone</synonym>
    <synonym>(6R)-5,6,7,8-Tetrahydro-L-biopterin</synonym>
    <synonym>(6R)-5,6,7,8-Tetrahydrobiopterin</synonym>
    <synonym>(6R)-Tetrahydrobiopterin</synonym>
    <synonym>2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone</synonym>
    <synonym>6R-Tetrahydro-L-biopterin</synonym>
    <synonym>6beta-5,6,7,8-Tetrahydro-L-biopterin</synonym>
    <synonym>6β-5,6,7,8-Tetrahydro-L-biopterin</synonym>
    <synonym>L-erythro-Tetrahydrobiopterin</synonym>
    <synonym>(6R)-2-Amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-4(1H)-pteridinone</synonym>
  </synonyms>
  <chemical_formula>C9H15N5O3</chemical_formula>
  <average_molecular_weight>241.2471</average_molecular_weight>
  <monisotopic_moleculate_weight>241.117489371</monisotopic_moleculate_weight>
  <iupac_name>(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one</iupac_name>
  <traditional_iupac>tetrahydrobiopterin</traditional_iupac>
  <cas_registry_number>27070-47-9</cas_registry_number>
  <smiles>[H][C@@]1(CNC2=C(N1)C(=O)N=C(N)N2)[C@@H](O)[C@H](C)O</smiles>
  <inchi>InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1</inchi>
  <inchikey>FNKQXYHWGSIFBK-RPDRRWSUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Biopterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>1,3-aminoalcohols</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>1,2-diol</substituent>
      <substituent>1,3-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Biopterin</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>5,6,7,8-tetrahydrobiopterin</external_descriptor>
      <external_descriptor>Coenzymes</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>250 - 255 °C (hydrochloride salt)</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,5,6,7,8-hexahydropteridin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>241.2471</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>241.117489371</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CNC2=C(N1)C(=O)N=C(N)N2)[C@@H](O)[C@H](C)O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H15N5O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FNKQXYHWGSIFBK-RPDRRWSUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>132</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ion Channels and Their Functional Role in Vascular Endothelium</name>
      <smpdb_id>SMP0108207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pterine Biosynthesis</name>
      <smpdb_id>SMP0087250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>35145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>47846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32080</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB00360</drugbank_id>
  <foodb_id>FDB021880</foodb_id>
  <chemspider_id>40270</chemspider_id>
  <pubchem_compound_id>44257</pubchem_compound_id>
  <kegg_id>C00272</kegg_id>
  <pdbe_id/>
  <chebi_id>59560</chebi_id>
  <knapsack_id>C00018229</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD-14053</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Tetrahydrobiopterin</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Steven S. Gross, "Blocking utilization of tetrahydrobiopterin to block induction of nitric oxide synthesis." U.S. Patent US5502050, issued October, 1984.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00022</protein_accession>
      <name>Nitric oxide synthase, endothelial</name>
      <uniprot_id>P29473</uniprot_id>
      <gene_name>NOS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00069</protein_accession>
      <name>Nitric oxide synthase, inducible</name>
      <uniprot_id>Q27995</uniprot_id>
      <gene_name>NOS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00379</protein_accession>
      <name>Sepiapterin reductase</name>
      <uniprot_id>Q17QK8</uniprot_id>
      <gene_name>SPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00388</protein_accession>
      <name>Tyrosine 3-monooxygenase</name>
      <uniprot_id>P17289</uniprot_id>
      <gene_name>TH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00389</protein_accession>
      <name>Phenylalanine-4-hydroxylase</name>
      <uniprot_id>Q2KIH7</uniprot_id>
      <gene_name>PAH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00557</protein_accession>
      <name>Inducible nitric oxid synthase</name>
      <uniprot_id>Q6ZXD5</uniprot_id>
      <gene_name>iNOS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:40 UTC</creation_date>
  <update_date>2020-04-15 20:47:38 UTC</update_date>
  <accession>BMDB0000030</accession>
  <secondary_accessions>
    <accession>BMDB00030</accession>
  </secondary_accessions>
  <name>Biotin</name>
  <description>Biotin, also known as D-biotin or biotin ratiopharm, belongs to the class of organic compounds known as biotin and derivatives. These are organic compounds containing a ureido (tetrahydroimidizalone) ring fused with a tetrahydrothiophene ring. Biotin is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Biotin exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Biotin exists in all living species, ranging from bacteria to humans. In cattle, biotin is involved in the metabolic pathway called the biotin metabolism pathway. Biotin is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acid</synonym>
    <synonym>(3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valeric acid</synonym>
    <synonym>5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoic acid</synonym>
    <synonym>Biotina</synonym>
    <synonym>Biotine</synonym>
    <synonym>Biotinum</synonym>
    <synonym>cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acid</synonym>
    <synonym>cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acid</synonym>
    <synonym>cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valeric acid</synonym>
    <synonym>Coenzyme R</synonym>
    <synonym>D-(+)-Biotin</synonym>
    <synonym>D-Biotin</synonym>
    <synonym>Vitamin b7</synonym>
    <synonym>Vitamin H</synonym>
    <synonym>Bioepiderm</synonym>
    <synonym>(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valerate</synonym>
    <synonym>(3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valerate</synonym>
    <synonym>5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoate</synonym>
    <synonym>cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valerate</synonym>
    <synonym>cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valerate</synonym>
    <synonym>cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valerate</synonym>
    <synonym>(+)-Biotin</synonym>
    <synonym>-(+)-Biotin</synonym>
    <synonym>1SWK</synonym>
    <synonym>1SWN</synonym>
    <synonym>1SWR</synonym>
    <synonym>Biodermatin</synonym>
    <synonym>Bios H</synonym>
    <synonym>Bios II</synonym>
    <synonym>D(+)-Biotin</synonym>
    <synonym>D-Biotin factor S</synonym>
    <synonym>delta-(+)-Biotin</synonym>
    <synonym>delta-Biotin</synonym>
    <synonym>delta-Biotin factor S</synonym>
    <synonym>Factor S</synonym>
    <synonym>Factor S (vitamin)</synonym>
    <synonym>Hexahydro-2-oxo-1H-thieno(3,4-D)imidazole-4-pentanoate</synonym>
    <synonym>Hexahydro-2-oxo-1H-thieno(3,4-D)imidazole-4-pentanoic acid</synonym>
    <synonym>Hexahydro-2-oxo-[3as-(3aa,4b,6aa)]-1H-thieno[3,4-D]imidazole-4-pentanoate</synonym>
    <synonym>Hexahydro-2-oxo-[3as-(3aa,4b,6aa)]-1H-thieno[3,4-D]imidazole-4-pentanoic acid</synonym>
    <synonym>Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1H-thieno[3,4-D]imidazole-4-pentanoate</synonym>
    <synonym>Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1H-thieno[3,4-D]imidazole-4-pentanoic acid</synonym>
    <synonym>Lutavit H2</synonym>
    <synonym>Meribin</synonym>
    <synonym>Rovimix H 2</synonym>
    <synonym>Vitamin-H</synonym>
    <synonym>Biotin hermes brand</synonym>
    <synonym>Biotin roche brand</synonym>
    <synonym>Biotin simons brand</synonym>
    <synonym>Biotin strathmann brand</synonym>
    <synonym>Biotin ziethen brand</synonym>
    <synonym>Biotin ratiopharm</synonym>
    <synonym>Roche brand OF biotin</synonym>
    <synonym>Roche, biotine</synonym>
    <synonym>E+b pharma brand OF biotin</synonym>
    <synonym>Medobiotin</synonym>
    <synonym>Biokur</synonym>
    <synonym>Biotinratiopharm</synonym>
    <synonym>Gelfert, biotin</synonym>
    <synonym>Hermes brand OF biotin</synonym>
    <synonym>Hermes, biotin</synonym>
    <synonym>Medopharm brand OF biotin</synonym>
    <synonym>Ratiopharm brand OF biotin</synonym>
    <synonym>Biocur brand OF biotin</synonym>
    <synonym>Biotin dermapharm brand</synonym>
    <synonym>Biotine roche</synonym>
    <synonym>Deacura</synonym>
    <synonym>Dermapharm brand OF biotin</synonym>
    <synonym>Gabunat</synonym>
    <synonym>Medebiotin</synonym>
    <synonym>Rombellin</synonym>
    <synonym>Ziethen brand OF biotin</synonym>
    <synonym>Biotin biocur brand</synonym>
    <synonym>Biotin gelfert</synonym>
    <synonym>Biotin hermes</synonym>
    <synonym>Biotin medopharm brand</synonym>
    <synonym>Biotin ratiopharm brand</synonym>
    <synonym>Biotin-ratiopharm</synonym>
    <synonym>H, Vitamin</synonym>
    <synonym>Medea brand OF biotin sodium salt</synonym>
    <synonym>Simons brand OF biotin</synonym>
    <synonym>Strathmann brand OF biotin</synonym>
  </synonyms>
  <chemical_formula>C10H16N2O3S</chemical_formula>
  <average_molecular_weight>244.311</average_molecular_weight>
  <monisotopic_moleculate_weight>244.088163078</monisotopic_moleculate_weight>
  <iupac_name>5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid</iupac_name>
  <traditional_iupac>5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>58-85-5</cas_registry_number>
  <smiles>[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2</smiles>
  <inchi>InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1</inchi>
  <inchikey>YBJHBAHKTGYVGT-ZKWXMUAHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as biotin and derivatives. These are organic compounds containing a ureido (tetrahydroimidizalone) ring fused with a tetrahydrothiophene ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Biotin and derivatives</class>
    <sub_class/>
    <direct_parent>Biotin and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylthioethers</alternative_parent>
      <alternative_parent>Heterocyclic fatty acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolines</alternative_parent>
      <alternative_parent>Imidazolyl carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Isoureas</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
      <alternative_parent>Thiolanes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-imidazoline</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Biotin</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Heterocyclic fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazolyl carboxylic acid derivative</substituent>
      <substituent>Isourea</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Thia fatty acid</substituent>
      <substituent>Thioether</substituent>
      <substituent>Thiolane</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Water-soluble vitamins</external_descriptor>
      <external_descriptor>biotins</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>232 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.22 mg/mL at 25 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>244.311</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>244.088163078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H16N2O3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YBJHBAHKTGYVGT-ZKWXMUAHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>78.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Biotin Metabolism</name>
      <smpdb_id>SMP0087183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>LPS and Citrate Signaling and Inflammation</name>
      <smpdb_id>SMP0120946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Threonine and 2-Oxobutanoate Degradation</name>
      <smpdb_id>SMP0087262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439629</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.041</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.080 +/- 0.003</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.097 +/- 0.004</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.090 +/- 0.003</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.090 +/- 0.002</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.086</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.041</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.082</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.078</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.082</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.082</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.064</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.041</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00120</kegg_id>
  <drugbank_id>DB00121</drugbank_id>
  <chemspider_id>149962</chemspider_id>
  <pubchem_compound_id>171548</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15956</chebi_id>
  <foodb_id>FDB014510</foodb_id>
  <meta_cyc_id>BIOTIN</meta_cyc_id>
  <knapsack_id>C00000756</knapsack_id>
  <wikipedia_id>Biotin</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33931</bigg_id>
  <metlin_id>243</metlin_id>
  <synthesis_reference>Corey, E. J.; Mehrotra, Mukund M.  A simple and enantioselective synthesis of (+)-biotin.  Tetrahedron Letters  (1988),  29(1),  57-60.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00204</protein_accession>
      <name>Acetyl-CoA carboxylase 1</name>
      <uniprot_id>Q9TTS3</uniprot_id>
      <gene_name>ACACA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00615</protein_accession>
      <name>Pyruvate carboxylase, mitochondrial</name>
      <uniprot_id>Q29RK2</uniprot_id>
      <gene_name>PC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00822</protein_accession>
      <name>Pyruvate carboxylase</name>
      <uniprot_id>Q861T5</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02007</protein_accession>
      <name>PCCA protein</name>
      <uniprot_id>A4FV90</uniprot_id>
      <gene_name>PCCA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02008</protein_accession>
      <name>Acetyl-CoA carboxylase, type beta</name>
      <uniprot_id>Q50I03</uniprot_id>
      <gene_name>acacb</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02009</protein_accession>
      <name>Acetyl-CoA carboxylase, type beta</name>
      <uniprot_id>Q50I04</uniprot_id>
      <gene_name>acacb</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:41 UTC</creation_date>
  <update_date>2020-04-16 20:37:34 UTC</update_date>
  <accession>BMDB0000031</accession>
  <secondary_accessions>
    <accession>BMDB00031</accession>
  </secondary_accessions>
  <name>Androsterone</name>
  <description/>
  <synonyms>
    <synonym>(3alpha,5alpha)-3-Hydroxyandrostan-17-one</synonym>
    <synonym>3-Epihydroxyetioallocholan-17-one</synonym>
    <synonym>3alpha-Hydroxy-5alpha-androstan-17-one</synonym>
    <synonym>3alpha-Hydroxyetioallocholan-17-one</synonym>
    <synonym>5alpha-Androstane-3alpha-ol-17-one</synonym>
    <synonym>5alpha-Androsterone</synonym>
    <synonym>Androkinine</synonym>
    <synonym>Androtine</synonym>
    <synonym>cis-Androsterone</synonym>
    <synonym>(3a,5a)-3-Hydroxyandrostan-17-one</synonym>
    <synonym>(3Α,5α)-3-hydroxyandrostan-17-one</synonym>
    <synonym>3a-Hydroxy-5a-androstan-17-one</synonym>
    <synonym>3Α-hydroxy-5α-androstan-17-one</synonym>
    <synonym>3a-Hydroxyetioallocholan-17-one</synonym>
    <synonym>3Α-hydroxyetioallocholan-17-one</synonym>
    <synonym>5a-Androstane-3a-ol-17-one</synonym>
    <synonym>5Α-androstane-3α-ol-17-one</synonym>
    <synonym>5a-Androsterone</synonym>
    <synonym>5Α-androsterone</synonym>
    <synonym>3-alpha-Hydroxy-5-alpha-androstan-17-one</synonym>
    <synonym>3 alpha Hydroxy 5 alpha androstan 17 one</synonym>
    <synonym>5 alpha Androstan 3 alpha ol 17 one</synonym>
    <synonym>5 alpha-Androstan-3 alpha-ol-17-one</synonym>
    <synonym>Epiandrosterone</synonym>
    <synonym>3-alpha-Hydroxy-17-androstanone</synonym>
    <synonym>3-alpha-Hydroxy-5-alpha-androstane-17-one</synonym>
    <synonym>3-alpha-Hydroxy-5alpha-androstan-17-one</synonym>
    <synonym>3-alpha-Hydroxyetioallocholan-17-one</synonym>
    <synonym>3-Hydroxy-(3-alpha,5-alpha)-androstan-17-one</synonym>
    <synonym>3-Hydroxyandrostan-17-one</synonym>
    <synonym>3alpha-Hydroxy-17-androstanone</synonym>
    <synonym>5-alpha-Androstan-3-alpha-ol-17-one</synonym>
    <synonym>5-alpha-Androstane-3alpha-ol-17-one</synonym>
    <synonym>5-alpha-Androsterone</synonym>
    <synonym>Androstanon-3-alpha-ol-17-one</synonym>
    <synonym>Atromide ici</synonym>
    <synonym>3Α-hydroxy-17-androstanone</synonym>
    <synonym>3Α-hydroxy-5α-androstane-17-one</synonym>
    <synonym>5Α-androstan-17-one-3α-ol</synonym>
    <synonym>5Α-androstan-3α-ol-17-one</synonym>
    <synonym>3alpha-Hydroxy-5alpha-androstane-17-one</synonym>
    <synonym>5alpha-Androstan-17-one-3alpha-ol</synonym>
    <synonym>5alpha-Androstan-3alpha-ol-17-one</synonym>
    <synonym>Androsterone</synonym>
  </synonyms>
  <chemical_formula>C19H30O2</chemical_formula>
  <average_molecular_weight>290.4403</average_molecular_weight>
  <monisotopic_moleculate_weight>290.224580204</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</iupac_name>
  <traditional_iupac>(1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</traditional_iupac>
  <cas_registry_number>53-41-8</cas_registry_number>
  <smiles>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1</inchi>
  <inchikey>QGXBDMJGAMFCBF-HLUDHZFRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17-oxo steroid</external_descriptor>
      <external_descriptor>3alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>Androstane and derivatives</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>androstanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>290.4403</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>290.224580204</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H30O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QGXBDMJGAMFCBF-HLUDHZFRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>83.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118940</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00523</kegg_id>
  <drugbank_id/>
  <chemspider_id>5668</chemspider_id>
  <foodb_id>FDB021881</foodb_id>
  <pdbe_id/>
  <chebi_id>16032</chebi_id>
  <pubchem_compound_id>5879</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Androsterone</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35244</bigg_id>
  <metlin_id>2797</metlin_id>
  <synthesis_reference>Marker, Russell E. Androsterone. Journal of the American Chemical Society (1935), 57 1755-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:43 UTC</creation_date>
  <update_date>2020-04-16 20:37:43 UTC</update_date>
  <accession>BMDB0000032</accession>
  <secondary_accessions>
    <accession>BMDB00032</accession>
  </secondary_accessions>
  <name>7-Dehydrocholesterol</name>
  <description/>
  <synonyms>
    <synonym>(3beta)-Cholesta-5,7-dien-3-ol</synonym>
    <synonym>5,7-Cholestadien-3-beta-ol</synonym>
    <synonym>5,7-Cholestadien-3beta-ol</synonym>
    <synonym>Provitamin D3</synonym>
    <synonym>Cholesta-5,7-dien-3beta-ol</synonym>
    <synonym>(3b)-Cholesta-5,7-dien-3-ol</synonym>
    <synonym>(3Β)-cholesta-5,7-dien-3-ol</synonym>
    <synonym>5,7-Cholestadien-3-b-ol</synonym>
    <synonym>5,7-Cholestadien-3-β-ol</synonym>
    <synonym>5,7-Cholestadien-3b-ol</synonym>
    <synonym>5,7-Cholestadien-3β-ol</synonym>
    <synonym>Cholesta-5,7-dien-3b-ol</synonym>
    <synonym>Cholesta-5,7-dien-3β-ol</synonym>
    <synonym>(-)-7-Dehydrocholesterol</synonym>
    <synonym>10,13-Dimethyl-17-(6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol</synonym>
    <synonym>17-(1,5-Dimethylhexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol</synonym>
    <synonym>5,7-Cholestandien-3-ol</synonym>
    <synonym>5,7-Cholestandien-3beta-ol</synonym>
    <synonym>7,8-Dehydro-cholesterol</synonym>
    <synonym>7,8-Didehydrocholesterol</synonym>
    <synonym>7-Dehydro-cholesterol</synonym>
    <synonym>7-Dehydrocholesterin</synonym>
    <synonym>7DHC</synonym>
    <synonym>Cholesta-5,7-dien-3 beta -ol</synonym>
    <synonym>Cholesta-5,7-dien-3-beta-ol</synonym>
    <synonym>Cholesta-5,7-dien-3-ol</synonym>
    <synonym>Dehydrocholesterin</synonym>
    <synonym>Dehydrocholesterol</synonym>
    <synonym>Delta5,7-Cholestadien-3beta-ol</synonym>
    <synonym>Delta5,7-Cholesterol</synonym>
    <synonym>Delta7-Cholesterol</synonym>
    <synonym>Provitamin-D3</synonym>
    <synonym>Provitamin D(3)</synonym>
    <synonym>Cholesta-5,7-dien-3 beta-ol</synonym>
    <synonym>7-Dehydrocholesterol, (3beta,10alpha)-isomer</synonym>
    <synonym>7-Dehydrocholesterol, (3beta,9beta,10alpha)-isomer</synonym>
    <synonym>7-DHC</synonym>
    <synonym>7-Dehydrocholesterol, (3alpha)-isomer</synonym>
    <synonym>7-Dehydrocholesterol, (3beta,9beta)-isomer</synonym>
  </synonyms>
  <chemical_formula>C27H44O</chemical_formula>
  <average_molecular_weight>384.6377</average_molecular_weight>
  <monisotopic_moleculate_weight>384.33921603</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol</iupac_name>
  <traditional_iupac>(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol</traditional_iupac>
  <cas_registry_number>434-16-2</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</smiles>
  <inchi>InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>UCTLRSWJYQTBFZ-DDPQNLDTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxy delta-7-steroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Delta-7-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxy-delta-7-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Delta-7-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3beta-sterol</external_descriptor>
      <external_descriptor>Cholestane and derivatives</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>Vitamin D3 and derivatives</external_descriptor>
      <external_descriptor>cholestanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>384.6377</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>384.33921603</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H44O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UCTLRSWJYQTBFZ-DDPQNLDTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>121.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>50.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>53</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330108</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id/>
  <kegg_id>C01164</kegg_id>
  <foodb_id>FDB021882</foodb_id>
  <pubchem_compound_id>439423</pubchem_compound_id>
  <chebi_id>17759</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <knapsack_id>C00023747</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>7-Dehydrocholesterol</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>William G. Dauben, Jerome F. Eastham, and Robert A. Micheli   A new method for the preparation of 7-dehydrocholesterol. Journal of the American Chemical Society (1951), 73 4496.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00910</protein_accession>
      <name>7-dehydrocholesterol reductase</name>
      <uniprot_id>Q5E9J5</uniprot_id>
      <gene_name>DHCR7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:44 UTC</creation_date>
  <update_date>2020-04-16 20:38:16 UTC</update_date>
  <accession>BMDB0000033</accession>
  <secondary_accessions>
    <accession>BMDB00033</accession>
  </secondary_accessions>
  <name>Carnosine</name>
  <description>Carnosine, also known as b-alanylhistidine or ignotine, belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. Carnosine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Carnosine exists in all living species, ranging from bacteria to humans. Carnosine is a potentially toxic compound. Carnosine has been found to be associated with several diseases known as eosinophilic esophagitis, crohn's disease, ulcerative colitis, and alzheimer's disease; also carnosine has been linked to the inborn metabolic disorders including carnosinuria.</description>
  <synonyms>
    <synonym>Nalpha-(beta-alanyl)-L-histidine</synonym>
    <synonym>Nalpha-(b-alanyl)-L-histidine</synonym>
    <synonym>Nalpha-(β-alanyl)-L-histidine</synonym>
    <synonym>b-Alanyl-L-histidine</synonym>
    <synonym>b-Alanylhistidine</synonym>
    <synonym>beta-Alanyl-L-histidine</synonym>
    <synonym>beta-Alanylhistidine</synonym>
    <synonym>Ignotine</synonym>
    <synonym>Karnozin</synonym>
    <synonym>Karnozzn</synonym>
    <synonym>L-Carnosine</synonym>
    <synonym>N-(3-Aminopropanoyl)histidine</synonym>
    <synonym>N-(b-Alanyl)-L-histidine</synonym>
    <synonym>N-b-Alanyl-L-histidine</synonym>
    <synonym>N-beta-Alanyl-L-histidine</synonym>
    <synonym>Sevitin</synonym>
    <synonym>Carnosine, (D-his)-isomer</synonym>
    <synonym>Hydrochloride, carnosine</synonym>
    <synonym>L Carnosine</synonym>
    <synonym>Carnosine hydrochloride</synonym>
    <synonym>beta Alanylhistidine</synonym>
  </synonyms>
  <chemical_formula>C9H14N4O3</chemical_formula>
  <average_molecular_weight>226.2325</average_molecular_weight>
  <monisotopic_moleculate_weight>226.106590334</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-(3-aminopropanamido)-3-(1H-imidazol-5-yl)propanoic acid</iupac_name>
  <traditional_iupac>β-alanyl-L-histidine</traditional_iupac>
  <cas_registry_number>305-84-0</cas_registry_number>
  <smiles>NCCC(=O)N[C@@H](CC1=CN=CN1)C(O)=O</smiles>
  <inchi>InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1</inchi>
  <inchikey>CQOVPNPJLQNMDC-ZETCQYMHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Peptidomimetics</class>
    <sub_class>Hybrid peptides</sub_class>
    <direct_parent>Hybrid peptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Histidine and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolyl carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Histidine or derivatives</substituent>
      <substituent>Hybrid peptide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazolyl carboxylic acid derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dipeptide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>253 - 256 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>384 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-(3-aminopropanamido)-3-(1H-imidazol-5-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>226.2325</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>226.106590334</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCC(=O)N[C@@H](CC1=CN=CN1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H14N4O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CQOVPNPJLQNMDC-ZETCQYMHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>121.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>55.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>54</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>55</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>56</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2605</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>30+/-12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>15-20</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>393+/-130</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>22085+/-4859</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.48 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.50 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.46 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.46 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1802.96 +/- 87.68</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>2187.41 +/- 125.15</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>89.36+/-4.06</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>4.73+/-0.48</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>2492.74 +/- 320.38</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>3.96+/-0.64</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>4.46+/-0.43</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>3447.54 +/- 171.14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1715-3619</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>9900</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>433-701</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>9690-13658</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.47 +/- 0.24</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.47 +/- 0.24</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>21958+/-3048</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>12+/-3</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00386</kegg_id>
  <drugbank_id>DB11695</drugbank_id>
  <foodb_id>FDB012937</foodb_id>
  <chemspider_id>388363</chemspider_id>
  <pubchem_compound_id>439224</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15727</chebi_id>
  <knapsack_id/>
  <meta_cyc_id>CARNOSINE</meta_cyc_id>
  <wikipedia_id>Carnosine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>1800369</bigg_id>
  <metlin_id>38</metlin_id>
  <synthesis_reference>Vezenkov, L.; Yanachkov, O. Synthesis of carnosine by trimethylsilyl protection. Dokladi na Bulgarskata Akademiya na Naukite (1991), 44(8), 53-6</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:45 UTC</creation_date>
  <update_date>2020-04-16 17:52:04 UTC</update_date>
  <accession>BMDB0000034</accession>
  <secondary_accessions>
    <accession>BMDB00034</accession>
  </secondary_accessions>
  <name>Adenine</name>
  <description>Adenine is a purine base. Adenine is found in both DNA and RNA. Adenine is a fundamental component of adenine nucleotides. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose; it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions.</description>
  <synonyms>
    <synonym>6-Aminopurine</synonym>
    <synonym>A</synonym>
    <synonym>Ade</synonym>
    <synonym>Adenin</synonym>
    <synonym>Leucon</synonym>
    <synonym>1,6-Dihydro-6-iminopurine</synonym>
    <synonym>1H-Purin-6-amine</synonym>
    <synonym>1H-Purine-6-amine</synonym>
    <synonym>3,6-Dihydro-6-iminopurine</synonym>
    <synonym>6-Amino-1H-purine</synonym>
    <synonym>6-Amino-3H-purine</synonym>
    <synonym>6-Amino-7H-purine</synonym>
    <synonym>6-Amino-9H-purine</synonym>
    <synonym>6-Amino-purine</synonym>
    <synonym>9H-Purin-6-amine</synonym>
    <synonym>9H-Purin-6-yl-amin</synonym>
    <synonym>9H-Purin-6-ylamine</synonym>
    <synonym>9H-Purine-6-amine</synonym>
    <synonym>Adeninimine</synonym>
    <synonym>Vitamin b4</synonym>
    <synonym>Vitamin b 4</synonym>
    <synonym>4, Vitamin b</synonym>
    <synonym>b 4, Vitamin</synonym>
  </synonyms>
  <chemical_formula>C5H5N5</chemical_formula>
  <average_molecular_weight>135.1267</average_molecular_weight>
  <monisotopic_moleculate_weight>135.054495185</monisotopic_moleculate_weight>
  <iupac_name>7H-purin-6-amine</iupac_name>
  <traditional_iupac>vitamin B4</traditional_iupac>
  <cas_registry_number>73-24-5</cas_registry_number>
  <smiles>NC1=C2NC=NC2=NC=N1</smiles>
  <inchi>InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)</inchi>
  <inchikey>GFFGJBXGBJISGV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>6-aminopurines</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>6-aminopurines</external_descriptor>
      <external_descriptor>a ring</external_descriptor>
      <external_descriptor>purine nucleobase</external_descriptor>
      <external_descriptor>purines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>360 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1.03 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.09</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>7H-purin-6-amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>135.1267</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>135.054495185</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=C2NC=NC2=NC=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H5N5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GFFGJBXGBJISGV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>57</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>58</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>59</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447776</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by NMR</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
          <pubmed_id>23182357</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
          <pubmed_id>23182357</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in beef muscle (longissimus dorsi).</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00147</kegg_id>
  <drugbank_id>DB00173</drugbank_id>
  <foodb_id>FDB012266</foodb_id>
  <chemspider_id>185</chemspider_id>
  <pubchem_compound_id>190</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16708</chebi_id>
  <knapsack_id>C00001490</knapsack_id>
  <meta_cyc_id>ADENINE</meta_cyc_id>
  <wikipedia_id>Adenine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34039</bigg_id>
  <metlin_id>85</metlin_id>
  <synthesis_reference>Baddiley, J.; Lythgoe, B.; Todd, A. R. Synthesis of purine nucleosides. II. A new and convenient synthesis of adenine. Journal of the Chemical Society (1943), 386-7.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
      <pubmed_id>23182357</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00108</protein_accession>
      <name>Adenine phosphoribosyltransferase</name>
      <uniprot_id>Q56JW4</uniprot_id>
      <gene_name>APRT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00618</protein_accession>
      <name>D-aspartate oxidase</name>
      <uniprot_id>P31228</uniprot_id>
      <gene_name>DDO</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01342</protein_accession>
      <name>P2Y purinoceptor 1</name>
      <uniprot_id>P48042</uniprot_id>
      <gene_name>P2RY1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01343</protein_accession>
      <name>Solute carrier family 25 (Mitochondrial carrier</name>
      <uniprot_id>Q3ZC05</uniprot_id>
      <gene_name>SLC25A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:46 UTC</creation_date>
  <update_date>2020-04-16 20:40:31 UTC</update_date>
  <accession>BMDB0000036</accession>
  <secondary_accessions>
    <accession>BMDB00036</accession>
  </secondary_accessions>
  <name>Taurocholic acid</name>
  <description/>
  <synonyms>
    <synonym>3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid 24-taurine</synonym>
    <synonym>Cholic acid taurine conjugate</synonym>
    <synonym>Choloyl-taurine</synonym>
    <synonym>Cholyltaurine</synonym>
    <synonym>N-Choloyltaurine</synonym>
    <synonym>Taurocholate</synonym>
    <synonym>3a,7a,12a-Trihydroxy-5b-cholanate 24-taurine</synonym>
    <synonym>3a,7a,12a-Trihydroxy-5b-cholanic acid 24-taurine</synonym>
    <synonym>3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate 24-taurine</synonym>
    <synonym>3Α,7α,12α-trihydroxy-5β-cholanate 24-taurine</synonym>
    <synonym>3Α,7α,12α-trihydroxy-5β-cholanic acid 24-taurine</synonym>
    <synonym>Cholate taurine conjugate</synonym>
    <synonym>Cholic acid taurine conjugic acid</synonym>
    <synonym>Cholaic acid</synonym>
    <synonym>Cholaate</synonym>
    <synonym>Taurine cholate</synonym>
    <synonym>Taurocholic acid, (7 beta)-isomer</synonym>
    <synonym>Taurocholic acid, (5 alpha)-isomer</synonym>
  </synonyms>
  <chemical_formula>C26H45NO7S</chemical_formula>
  <average_molecular_weight>515.703</average_molecular_weight>
  <monisotopic_moleculate_weight>515.291673489</monisotopic_moleculate_weight>
  <iupac_name>2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid</iupac_name>
  <traditional_iupac>2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid</traditional_iupac>
  <cas_registry_number>81-24-3</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1</inchi>
  <inchikey>WBWWGRHZICKQGZ-HZAMXZRMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Alkanesulfonic acids</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonic acids</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sulfonyls</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkanesulfonic acid</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sulfonyl</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Taurine conjugates</external_descriptor>
      <external_descriptor>amino sulfonic acid</external_descriptor>
      <external_descriptor>bile acid taurine conjugate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-0.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.053</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>515.703</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>515.291673489</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H45NO7S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WBWWGRHZICKQGZ-HZAMXZRMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>144.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>132.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>57.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>82386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>82387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>82388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>143730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>143731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>143732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447291</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05122</kegg_id>
  <drugbank_id>DB04348</drugbank_id>
  <chemspider_id>6423</chemspider_id>
  <foodb_id>FDB012335</foodb_id>
  <pdbe_id/>
  <chebi_id>28865</chebi_id>
  <pubchem_compound_id>6675</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Taurocholic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>45150</bigg_id>
  <metlin_id>5104</metlin_id>
  <synthesis_reference>Schersten, Tore; Bjorntorp, Per; Ekdahi, Per H.; Bjorkerud, Soren.  Synthesis of taurocholic and glycocholic acids by preparations of human liver.  II.  An analysis of the stimulating effect of the L fraction.    Biochimica et Biophysica Acta, General Subjects  (1967),  141(1),  155-63. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:48 UTC</creation_date>
  <update_date>2020-04-16 20:38:16 UTC</update_date>
  <accession>BMDB0000037</accession>
  <secondary_accessions>
    <accession>BMDB00037</accession>
  </secondary_accessions>
  <name>Aldosterone</name>
  <description>Aldosterone, also known as aldocorten or delta-aldosterone, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Aldosterone exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Aldosterone exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>(+)-Aldosterone</synonym>
    <synonym>(11beta)-11,21-Dihydroxy-3,20-dioxopregn-4-en-18-al</synonym>
    <synonym>11beta,21-Dihydroxy-3,20-dioxo-4-pregnen-18-al</synonym>
    <synonym>(11b)-11,21-Dihydroxy-3,20-dioxopregn-4-en-18-al</synonym>
    <synonym>(11Β)-11,21-dihydroxy-3,20-dioxopregn-4-en-18-al</synonym>
    <synonym>11b,21-Dihydroxy-3,20-dioxo-4-pregnen-18-al</synonym>
    <synonym>11Β,21-dihydroxy-3,20-dioxo-4-pregnen-18-al</synonym>
    <synonym>Aldosterone, (+-)-isomer</synonym>
    <synonym>Aldosterone, (11 beta,17 alpha)-isomer</synonym>
    <synonym>11beta,21-Dihydroxy-3,20-diketo-4-pregnen-18-al</synonym>
    <synonym>11beta,21-Dihydroxy-3,20-diketopregn-4-ene-18-al</synonym>
    <synonym>11beta,21-Dihydroxypregn-4-ene-3,18,20-trione</synonym>
    <synonym>11Β,21-dihydroxy-3,20-diketo-4-pregnen-18-al</synonym>
    <synonym>11Β,21-dihydroxy-3,20-diketopregn-4-ene-18-al</synonym>
    <synonym>11Β,21-dihydroxypregn-4-ene-3,18,20-trione</synonym>
    <synonym>18-Formyl-11beta,21-dihydroxy-4-pregnene-3,20-dione</synonym>
    <synonym>18-Formyl-11β,21-dihydroxy-4-pregnene-3,20-dione</synonym>
    <synonym>18-Oxocorticosterone</synonym>
    <synonym>Aldosterone</synonym>
  </synonyms>
  <chemical_formula>C21H28O5</chemical_formula>
  <average_molecular_weight>360.444</average_molecular_weight>
  <monisotopic_moleculate_weight>360.193674006</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-15-carbaldehyde</iupac_name>
  <traditional_iupac>(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-15-carbaldehyde</traditional_iupac>
  <cas_registry_number>52-39-1</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](C(=O)CO)[C@]1(C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C)C=O</smiles>
  <inchi>InChI=1S/C21H28O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,11,14-17,19,22,25H,2-7,9-10H2,1H3/t14-,15-,16+,17-,19+,20-,21+/m0/s1</inchi>
  <inchikey>PQSUYGKTWSAVDQ-ZVIOFETBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>11-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Aldehydes</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>11-beta-hydroxysteroid</substituent>
      <substituent>11-hydroxysteroid</substituent>
      <substituent>18-oxosteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>11beta-hydroxy steroid</external_descriptor>
      <external_descriptor>18-oxo steroid</external_descriptor>
      <external_descriptor>20-oxo steroid</external_descriptor>
      <external_descriptor>21-hydroxy steroid</external_descriptor>
      <external_descriptor>3-oxo steroid</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
      <external_descriptor>C21-steroid hormone</external_descriptor>
      <external_descriptor>Mineralocorticoids</external_descriptor>
      <external_descriptor>Pregnane and derivatives [Fig]</external_descriptor>
      <external_descriptor>mineralocorticoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>166.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0512 mg/mL at 37 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.08</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-15-carbaldehyde</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>360.444</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>360.193674006</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](C(=O)CO)[C@]1(C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C)C=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H28O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H28O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,11,14-17,19,22,25H,2-7,9-10H2,1H3/t14-,15-,16+,17-,19+,20-,21+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PQSUYGKTWSAVDQ-ZVIOFETBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>91.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>96.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Angiotensin Metabolism</name>
      <smpdb_id>SMP0119379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Kidney Function</name>
      <smpdb_id>SMP0119376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroidogenesis</name>
      <smpdb_id>SMP0087238</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451377</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB04630</drugbank_id>
  <chemspider_id>5633</chemspider_id>
  <pdbe_id/>
  <pubchem_compound_id>5839</pubchem_compound_id>
  <kegg_id>C01780</kegg_id>
  <chebi_id>27584</chebi_id>
  <knapsack_id/>
  <meta_cyc_id>ALDOSTERONE</meta_cyc_id>
  <wikipedia_id>Aldosterone</wikipedia_id>
  <foodb_id>FDB021883</foodb_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Bear, Brian R.; Parnes, Jason S.; Shea, Kenneth J.  Progress toward the Total Synthesis of (+)-Aldosterone: Synthesis of the A-D Rings.    Organic Letters  (2003),  5(10),  1613-1616.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01608</protein_accession>
      <name>Prostaglandin E2 receptor EP4 subtype</name>
      <uniprot_id>Q8MJ08</uniprot_id>
      <gene_name>PTGER4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01980</protein_accession>
      <name>Natriuretic peptides B</name>
      <uniprot_id>P13204</uniprot_id>
      <gene_name>NPPB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:49 UTC</creation_date>
  <update_date>2020-03-18 18:12:37 UTC</update_date>
  <accession>BMDB0000038</accession>
  <secondary_accessions>
    <accession>BMDB00038</accession>
  </secondary_accessions>
  <name>Dihydrobiopterin</name>
  <description/>
  <synonyms>
    <synonym>7,8-DIHYDROBIOPTERIN</synonym>
    <synonym>L-Erythro-Q-dihydrobiopterin</synonym>
    <synonym>Q-BH2</synonym>
    <synonym>Quinonoid dihydrobiopterin</synonym>
    <synonym>L-Erythro-7,8-dihydrobiopterin</synonym>
    <synonym>L-Erythro-dihydrobiopterin</synonym>
    <synonym>7,8-Dihydro-L-biopterin</synonym>
    <synonym>BH2</synonym>
    <synonym>Dihydrobiopterin</synonym>
  </synonyms>
  <chemical_formula>C9H13N5O3</chemical_formula>
  <average_molecular_weight>239.2312</average_molecular_weight>
  <monisotopic_moleculate_weight>239.101839307</monisotopic_moleculate_weight>
  <iupac_name>2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,7,8-tetrahydropteridin-4-one</iupac_name>
  <traditional_iupac>dihydrobiopterin</traditional_iupac>
  <cas_registry_number>6779-87-9</cas_registry_number>
  <smiles>C[C@H](O)[C@H](O)C1=NC2=C(NC1)NC(N)=NC2=O</smiles>
  <inchi>InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,6,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,6-/m0/s1</inchi>
  <inchikey>FEMXZDUTFRTWPE-DZSWIPIPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Biopterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Ketimines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Biopterin</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imine</substituent>
      <substituent>Ketimine</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>7,8-dihydrobiopterin</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,7,8-tetrahydropteridin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>239.2312</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>239.101839307</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](O)[C@H](O)C1=NC2=C(NC1)NC(N)=NC2=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13N5O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,6,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FEMXZDUTFRTWPE-DZSWIPIPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>132.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pterine Biosynthesis</name>
      <smpdb_id>SMP0087250</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448549</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB04400</drugbank_id>
  <chemspider_id>106382</chemspider_id>
  <pubchem_compound_id>119055</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id>C02953</kegg_id>
  <chebi_id>43029</chebi_id>
  <foodb_id>FDB021884</foodb_id>
  <meta_cyc_id>CPD-15159</meta_cyc_id>
  <wikipedia_id>Dihydrobiopterin</wikipedia_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Gal E M. Synthesis and quantitative aspects of dihydrobiopterin control of cerebral serotonin levels.    Advances in experimental medicine and biology  (1981),  133 197-206.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00379</protein_accession>
      <name>Sepiapterin reductase</name>
      <uniprot_id>Q17QK8</uniprot_id>
      <gene_name>SPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:50 UTC</creation_date>
  <update_date>2020-04-16 20:40:28 UTC</update_date>
  <accession>BMDB0000039</accession>
  <secondary_accessions>
    <accession>BMDB00039</accession>
  </secondary_accessions>
  <name>Butyric acid</name>
  <description>Butyric acid, also known as butyrate or butanoic acid, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Butyric acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Butyric acid exists in all living species, ranging from bacteria to humans. Butyric acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Butanoic acid</synonym>
    <synonym>1-Butyric acid</synonym>
    <synonym>1-Propanecarboxylic acid</synonym>
    <synonym>4:0</synonym>
    <synonym>Acide butanoique</synonym>
    <synonym>Acide butyrique</synonym>
    <synonym>Butanic acid</synonym>
    <synonym>Butanoate</synonym>
    <synonym>Butanoic acid</synonym>
    <synonym>Butoic acid</synonym>
    <synonym>Buttersaeure</synonym>
    <synonym>C4:0</synonym>
    <synonym>CH3-[CH2]2-COOH</synonym>
    <synonym>Ethylacetic acid</synonym>
    <synonym>N-Butanoic acid</synonym>
    <synonym>N-Butyric acid</synonym>
    <synonym>Propanecarboxylic acid</synonym>
    <synonym>Propylformic acid</synonym>
    <synonym>Butyrate</synonym>
    <synonym>1-Butanoate</synonym>
    <synonym>1-Butyrate</synonym>
    <synonym>1-Propanecarboxylate</synonym>
    <synonym>Butanate</synonym>
    <synonym>Butoate</synonym>
    <synonym>Ethylacetate</synonym>
    <synonym>N-Butanoate</synonym>
    <synonym>N-Butyrate</synonym>
    <synonym>Propanecarboxylate</synonym>
    <synonym>Propylformate</synonym>
    <synonym>Honey robber</synonym>
    <synonym>Kyselina maselna</synonym>
    <synonym>Butyrate, magnesium</synonym>
    <synonym>Magnesium butyrate</synonym>
    <synonym>Acid, butyric</synonym>
    <synonym>Butyrate, sodium</synonym>
    <synonym>Dibutyrate, magnesium</synonym>
    <synonym>Magnesium dibutyrate</synonym>
    <synonym>Sodium butyrate</synonym>
    <synonym>Acid, butanoic</synonym>
    <synonym>Butyric acid magnesium salt</synonym>
    <synonym>Butyric acid, sodium salt</synonym>
    <synonym>FA(4:0)</synonym>
    <synonym>Butyric acid</synonym>
  </synonyms>
  <chemical_formula>C4H8O2</chemical_formula>
  <average_molecular_weight>88.1051</average_molecular_weight>
  <monisotopic_moleculate_weight>88.0524295</monisotopic_moleculate_weight>
  <iupac_name>butanoic acid</iupac_name>
  <traditional_iupac>butyric acid</traditional_iupac>
  <cas_registry_number>107-92-6</cas_registry_number>
  <smiles>CCCC(O)=O</smiles>
  <inchi>InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)</inchi>
  <inchikey>FERIUCNNQQJTOY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Straight chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Saturated fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>short-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-5.7 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>60.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.79</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>88.1051</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>88.0524295</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FERIUCNNQQJTOY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>21.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Butyrate Metabolism</name>
      <smpdb_id>SMP0087185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>66</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>67</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>68</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437339</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>37 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>34.9 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>24 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>33 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>37 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>41 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>52.55 +/- 6.31</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk from a Danish Holstein herd by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>42 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>56.75 +/- 5.46</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised whole milk (3.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21.84 +/- 3.36</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised semi skimmed milk (1.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20.16 +/- 5.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised skimmed milk (0.1% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
          <pubmed_id>1779072</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>46.08 +/- 0.72</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31780.262 +/- 12485.103</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
          <pubmed_id>16899705</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>44.606 +/- 0.76</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Catrienus De Jong Herman T. Badings. Determination of free fatty acids in milk and cheese procedures for extraction, clean up, and capillary gas chromatographic analysis. Journal of High Resolution Chromatography Volume 13, Issue 2, 1990</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>43.93 +/- 16.09</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from Danish Holstein-Friesian (n = 456) and Jersey cows (n = 436)</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
          <pubmed_id>23182357</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
          <pubmed_id>14168161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6923.55</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5675.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35.91 +/- 16.47</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1135.00808</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2724.0194</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17138.641 +/- 2724.0225</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1135.00808</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16798.139 +/- 2837.523</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13393.0953</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14641.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12485.09</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>This is a duplicate concentration of concentration_id 8156, unpexported by An Chi on Aug 20, 2018</comment>
      <references>
        <reference>
          <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.9 (0.7 - 1.2)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.8 (0.6 - 1.1)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29.22 +/- 5.72</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.2 (0.8 - 2.4)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.6 (2.4 - 9.6)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>7000-13000</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>10519-17242</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>689</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>642</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>19300</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>7970</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>25848+/-9273</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hanne Christine Bertram, Niels Bastian Kristensen, Mogens Vestergaard, SÃ¸ren Krogh Jensen, Jakob Sehested, Niels Christian Nielsen, Anders Malmendal. Metabolic characterization of rumen epithelial tissue from dairy calves fed different starter diets using 1H NMR spectroscopy. Livestock Science (2008) 120:127-134   doi: 10.1016/j.livsci.2008.05.001</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>9386.24 +/- 1366.99</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>8100</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>8030</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>15130</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>9380</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>8100 +/- 1350</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>8103 +/- 1631</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>15131 +/- 2957</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>9386 +/- 1367</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00246</kegg_id>
  <chemspider_id>259</chemspider_id>
  <drugbank_id>DB03568</drugbank_id>
  <foodb_id>FDB031031</foodb_id>
  <pubchem_compound_id>264</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30772</chebi_id>
  <meta_cyc_id>BUTYRIC_ACID</meta_cyc_id>
  <knapsack_id>C00001180</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34376</bigg_id>
  <wikipedia_id>Butyric_acid</wikipedia_id>
  <metlin_id>107</metlin_id>
  <synthesis_reference>Shan, Zhiping.  Preparation of butyric acid by hydrogenation of maleic anhydride. U.S. Pat. Appl. Publ.  (2008),     6pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
      <pubmed_id>16899705</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
      <pubmed_id>1779072</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
      <pubmed_id>23182357</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.</reference_text>
      <pubmed_id>20855010</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
      <pubmed_id>14168161</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26.</reference_text>
      <pubmed_id>27236769</pubmed_id>
    </reference>
    <reference>
      <reference_text>van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.</reference_text>
      <pubmed_id>28219465</pubmed_id>
    </reference>
    <reference>
      <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
    </reference>
    <reference>
      <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:51 UTC</creation_date>
  <update_date>2020-04-16 20:38:55 UTC</update_date>
  <accession>BMDB0000042</accession>
  <secondary_accessions>
    <accession>BMDB00042</accession>
  </secondary_accessions>
  <name>Acetic acid</name>
  <description>Acetic acid, also known as glacial acetate or vinegar, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Acetic acid is a drug which is used to treat infections in the ear canal. Acetic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Acetic acid exists in all living species, ranging from bacteria to humans. Acetic acid has been found to be associated with several diseases known as colorectal cancer, gout, and perillyl alcohol administration for cancer treatment; also acetic acid has been linked to several inborn metabolic disorders including celiac disease and phenylketonuria.</description>
  <synonyms>
    <synonym>Acide acetique</synonym>
    <synonym>AcOH</synonym>
    <synonym>CH3-COOH</synonym>
    <synonym>CH3CO2H</synonym>
    <synonym>e 260</synonym>
    <synonym>e-260</synonym>
    <synonym>e260</synonym>
    <synonym>Essigsaeure</synonym>
    <synonym>Ethanoic acid</synonym>
    <synonym>Ethoic acid</synonym>
    <synonym>Ethylic acid</synonym>
    <synonym>HOAc</synonym>
    <synonym>INS no. 260</synonym>
    <synonym>MeCO2h</synonym>
    <synonym>MeCOOH</synonym>
    <synonym>Methanecarboxylic acid</synonym>
    <synonym>Glacial acetic acid</synonym>
    <synonym>Acetasol</synonym>
    <synonym>Ethanoate</synonym>
    <synonym>Ethoate</synonym>
    <synonym>Ethylate</synonym>
    <synonym>Methanecarboxylate</synonym>
    <synonym>Glacial acetate</synonym>
    <synonym>Acetate</synonym>
    <synonym>Kyselina octova</synonym>
    <synonym>Vinegar</synonym>
    <synonym>Vinegar acid</synonym>
    <synonym>Acid, acetic</synonym>
    <synonym>Acetic acid glacial</synonym>
    <synonym>Acid glacial, acetic</synonym>
    <synonym>Acid, glacial acetic</synonym>
    <synonym>Acetic acid, glacial</synonym>
    <synonym>Glacial, acetic acid</synonym>
  </synonyms>
  <chemical_formula>C2H4O2</chemical_formula>
  <average_molecular_weight>60.052</average_molecular_weight>
  <monisotopic_moleculate_weight>60.021129372</monisotopic_moleculate_weight>
  <iupac_name>acetic acid</iupac_name>
  <traditional_iupac>acetic acid</traditional_iupac>
  <cas_registry_number>64-19-7</cas_registry_number>
  <smiles>CC(O)=O</smiles>
  <inchi>InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)</inchi>
  <inchikey>QTBSBXVTEAMEQO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Carboxylic acids</sub_class>
    <direct_parent>Carboxylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Saturated fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>16.6 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.17</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>60.052</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>60.021129372</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H4O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QTBSBXVTEAMEQO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>12.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>5.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ethanol Degradation</name>
      <smpdb_id>SMP0087192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>69</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>71</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437116</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>403+/-199</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1500-2400</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS</comment>
      <references>
        <reference>
          <reference_text>Raun BM, Kristensen NB: Metabolic effects of feeding ethanol or propanol to postpartum transition Holstein cows. J Dairy Sci. 2011 May;94(5):2566-80. doi: 10.3168/jds.2010-3999.</reference_text>
          <pubmed_id>21524548</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>920-1040</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Boehringer Mannheim F-kit for acetate</comment>
      <references>
        <reference>
          <reference_text>Sato H, Matsumoto M, Hanasaka S: Relations between plasma acetate, 3-hydroxybutyrate, FFA, glucose levels and energy nutrition in lactating dairy cows. J Vet Med Sci. 1999 May;61(5):447-51. doi: 10.1292/jvms.61.447.</reference_text>
          <pubmed_id>10379932</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>201+/-91</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>188+/-31</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>135.52 +/- 1.49</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Catrienus De Jong Herman T. Badings. Determination of free fatty acids in milk and cheese procedures for extraction, clean up, and capillary gas chromatographic analysis. Journal of High Resolution Chromatography Volume 13, Issue 2, 1990</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>108 - 701</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>38 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13 - 37</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13 - 37</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>37 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>46 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>33 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>43 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14 - 35</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>97.08 +/- 3.88</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Catrienus De Jong Herman T. Badings. Determination of free fatty acids in milk and cheese procedures for extraction, clean up, and capillary gas chromatographic analysis. Journal of High Resolution Chromatography Volume 13, Issue 2, 1990</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>41.47 +/- 10.17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from 20 healthy Holstein Friesian dairy cows </comment>
      <references>
        <reference>
          <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
          <pubmed_id>23738862</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from Danish Holstein-Friesian (n = 456) and Jersey cows (n = 436)</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
          <pubmed_id>23182357</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>47.88 +/- 12.36</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.8 (2.6 - 7.7)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.7 (2.8 - 7.6)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9.6 (2.6 - 23)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>71.81 +/- 41.67</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>95 (11 - 199)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>111.28 +/- 14.21</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>5.17+/-1.07</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>7.29+/-1.47</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>3.19+/-0.75</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>4.44+/-0.95</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>252.43 +/- 27.85</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>261.32 +/- 30.52</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>274.35 +/- 13.29</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>97-291</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>97-133</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>41000-81000</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>48146-62076</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>43800</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>41400</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>56500</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>47600</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>37264+/-7582</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hanne Christine Bertram, Niels Bastian Kristensen, Mogens Vestergaard, SÃ¸ren Krogh Jensen, Jakob Sehested, Niels Christian Nielsen, Anders Malmendal. Metabolic characterization of rumen epithelial tissue from dairy calves fed different starter diets using 1H NMR spectroscopy. Livestock Science (2008) 120:127-134   doi: 10.1016/j.livsci.2008.05.001</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>60087.08 +/- 5781.35</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>56300</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>54600</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>64270</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>60100</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>56350 +/- 7280</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>54620 +/- 7940</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>64280 +/- 6040</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>60100 +/- 5800</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>219+/-52</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>88+/-19</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein.</comment>
      <references>
        <reference>
          <reference_text>Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17.</reference_text>
          <pubmed_id>22059599</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB03166</drugbank_id>
  <kegg_id>C00033</kegg_id>
  <chemspider_id>171</chemspider_id>
  <pubchem_compound_id>176</pubchem_compound_id>
  <foodb_id>FDB019725</foodb_id>
  <pdbe_id/>
  <chebi_id>15366</chebi_id>
  <knapsack_id>C00001176</knapsack_id>
  <meta_cyc_id>ACET</meta_cyc_id>
  <wikipedia_id>Acetic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33590</bigg_id>
  <metlin_id>3206</metlin_id>
  <synthesis_reference>Law, David John. Process for the preparation of carboxylic acids and/or derivatives thereof.  PCT Int. Appl.  (2007), 14pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
      <pubmed_id>23182357</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
      <pubmed_id>23738862</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00367</protein_accession>
      <name>Acyl-CoA synthetase short-chain family member 3, mitochondrial</name>
      <uniprot_id>A7MB45</uniprot_id>
      <gene_name>ACSS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00529</protein_accession>
      <name>Acetylcholinesterase</name>
      <uniprot_id>P23795</uniprot_id>
      <gene_name>ACHE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00938</protein_accession>
      <name>Putative N-acetylglucosamine-6-phosphate deacetylase</name>
      <uniprot_id>A7MBC0</uniprot_id>
      <gene_name>AMDHD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00943</protein_accession>
      <name>Platelet-activating factor acetylhydrolase 2, cytoplasmic</name>
      <uniprot_id>P79106</uniprot_id>
      <gene_name>PAFAH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00944</protein_accession>
      <name>Platelet-activating factor acetylhydrolase</name>
      <uniprot_id>Q28017</uniprot_id>
      <gene_name>PLA2G7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00945</protein_accession>
      <name>Platelet-activating factor acetylhydrolase IB subunit gamma</name>
      <uniprot_id>Q29460</uniprot_id>
      <gene_name>PAFAH1B3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00946</protein_accession>
      <name>Serum paraoxonase/arylesterase 2</name>
      <uniprot_id>Q58DS7</uniprot_id>
      <gene_name>PON2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00947</protein_accession>
      <name>Platelet-activating factor acetylhydrolase IB subunit beta</name>
      <uniprot_id>P68401</uniprot_id>
      <gene_name>PAFAH1B2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00948</protein_accession>
      <name>N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase</name>
      <uniprot_id>A6QQ24</uniprot_id>
      <gene_name>PIGL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:53 UTC</creation_date>
  <update_date>2020-04-16 20:40:44 UTC</update_date>
  <accession>BMDB0000043</accession>
  <secondary_accessions>
    <accession>BMDB00043</accession>
  </secondary_accessions>
  <name>Betaine</name>
  <description>Betaine, also known as Bet or acidin pepsin, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Betaine exists as a solid, possibly soluble (in water), and a moderately acidic compound (based on its pKa) molecule. Betaine exists in all eukaryotes, ranging from yeast to humans. Betaine participates in a number of enzymatic reactions, within cattle. In particular, Betaine can be biosynthesized from betaine aldehyde; which is catalyzed by the enzyme Alpha-aminoadipic semialdehyde dehydrogenase. In addition, Betaine and homocysteine can be converted into dimethylglycine and L-methionine; which is catalyzed by the enzyme betaine--homocysteine S-methyltransferase 1. In cattle, betaine is involved in the metabolic pathway called the betaine metabolism pathway.</description>
  <synonyms>
    <synonym>(Trimethylammoniumyl)acetate</synonym>
    <synonym>1-Carboxy-N,N,N-trimethylmethanaminium inner salt</synonym>
    <synonym>2-N,N,N-Trimethylammonio acetate</synonym>
    <synonym>Abromine</synonym>
    <synonym>Acidol</synonym>
    <synonym>Bet</synonym>
    <synonym>N,N,N-Trimethylammonioacetate</synonym>
    <synonym>N,N,N-Trimethylglycine</synonym>
    <synonym>Trimethylaminoacetate</synonym>
    <synonym>Trimethylammonioacetate</synonym>
    <synonym>Trimethylglycine</synonym>
    <synonym>Trimethylglycocoll</synonym>
    <synonym>Glycine betaine</synonym>
    <synonym>Cystadane</synonym>
    <synonym>(Trimethylammoniumyl)acetic acid</synonym>
    <synonym>2-N,N,N-Trimethylammonio acetic acid</synonym>
    <synonym>N,N,N-Trimethylammonioacetic acid</synonym>
    <synonym>Trimethylaminoacetic acid</synonym>
    <synonym>Trimethylammonioacetic acid</synonym>
    <synonym>(Carboxymethyl)trimethylammonium hydroxide inner salt</synonym>
    <synonym>(Trimethylammonio)acetate</synonym>
    <synonym>1-Carboxy-N,N,N-trimethyl-methanaminium</synonym>
    <synonym>1-Carboxy-N,N,N-trimethyl-methanaminium hydroxide</synonym>
    <synonym>a-Earleine</synonym>
    <synonym>alpha-Earleine</synonym>
    <synonym>Aminocoat</synonym>
    <synonym>Betafin</synonym>
    <synonym>Betafin BCR</synonym>
    <synonym>Betafin BP</synonym>
    <synonym>Ektasolve ee</synonym>
    <synonym>FinnStim</synonym>
    <synonym>Glycocoll betaine</synonym>
    <synonym>Glycylbetaine</synonym>
    <synonym>Greenstim</synonym>
    <synonym>Loramine amb 13</synonym>
    <synonym>Loramine amb-13</synonym>
    <synonym>Lycine</synonym>
    <synonym>Oxyneurine</synonym>
    <synonym>Rubrine C</synonym>
    <synonym>Trimethylbetaine glycine</synonym>
    <synonym>Acidin pepsin</synonym>
    <synonym>Beaufour brand OF betaine citrate</synonym>
    <synonym>Byk brand OF betaine phosphate</synonym>
    <synonym>Fournier brand OF betaine ascorbate and hydrate</synonym>
    <synonym>Hydrochloride, betaine</synonym>
    <synonym>Logeais brand OF betaine cyclobutyrate</synonym>
    <synonym>Novobetaine</synonym>
    <synonym>Betaine hydrochloride</synonym>
    <synonym>Betaine orphan brand</synonym>
    <synonym>Boizot brand OF betaine aspartate</synonym>
    <synonym>C.B.B.</synonym>
    <synonym>Citrate de bétaïne upsa</synonym>
    <synonym>Scorbo-bétaïne</synonym>
    <synonym>Stea-16</synonym>
    <synonym>Stea16</synonym>
    <synonym>Acidin-pepsin</synonym>
    <synonym>Citrate de bétaïne beaufour</synonym>
    <synonym>Orphan brand OF betaine</synonym>
    <synonym>Scorbo bétaïne</synonym>
    <synonym>AcidinPepsin</synonym>
    <synonym>Betaine, glycine</synonym>
    <synonym>Hepastyl</synonym>
    <synonym>Scorbobétaïne</synonym>
    <synonym>UPSA brand OF betaine citrate</synonym>
    <synonym>Stea 16</synonym>
    <synonym>Betaine</synonym>
  </synonyms>
  <chemical_formula>C5H11NO2</chemical_formula>
  <average_molecular_weight>117.1463</average_molecular_weight>
  <monisotopic_moleculate_weight>117.078978601</monisotopic_moleculate_weight>
  <iupac_name>2-(trimethylazaniumyl)acetate</iupac_name>
  <traditional_iupac>(trimethylammonio)acetate</traditional_iupac>
  <cas_registry_number>107-43-7</cas_registry_number>
  <smiles>C[N+](C)(C)CC([O-])=O</smiles>
  <inchi>InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3</inchi>
  <inchikey>KWIUHFFTVRNATP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a methylated methyl acceptor</external_descriptor>
      <external_descriptor>amino-acid betaine</external_descriptor>
      <external_descriptor>glycine derivative</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>293 - 301 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>611.0 mg/mL at 19 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(trimethylazaniumyl)acetate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>117.1463</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>117.078978601</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)CC([O-])=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H11NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KWIUHFFTVRNATP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>52.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>72</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>73</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>74</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447324</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in lactating Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>13.7-25.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Artegoitia VM, Middleton JL, Harte FM, Campagna SR, de Veth MJ: Choline and choline metabolite patterns and associations in blood and milk during lactation in dairy cows. PLoS One. 2014 Aug 26;9(8):e103412. doi: 10.1371/journal.pone.0103412. eCollection 2014.</reference_text>
          <pubmed_id>25157578</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>169+/-31</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>358+/-93</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>1321+/-351</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>459 - 1410</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>73 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>81 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>79 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>71 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>72.22 +/- 16.17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>64.41 +/- 31.44</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>90.15 +/- 25.33</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1477-1826</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>315.07 +/- 23.69</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>345.85 +/- 38.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>375.31 +/- 38.29</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>292-487</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>456.74 +/- 30.58</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>590</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>67-111</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2-17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>15+/-40</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>1139+/-246</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>564+/-134</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00719</kegg_id>
  <drugbank_id>DB06756</drugbank_id>
  <foodb_id>FDB009020</foodb_id>
  <chemspider_id>242</chemspider_id>
  <pubchem_compound_id>247</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17750</chebi_id>
  <knapsack_id>C00007291</knapsack_id>
  <meta_cyc_id>BETAINE</meta_cyc_id>
  <wikipedia_id>Trimethylglycine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35786</bigg_id>
  <metlin_id>287</metlin_id>
  <synthesis_reference>Mu, Yun; Guo, Xiao-hui.  Improved process for preparation of betaine.    Huaxue Yu Shengwu Gongcheng  (2005),  22(7),  48-49.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:54 UTC</creation_date>
  <update_date>2020-04-16 20:39:48 UTC</update_date>
  <accession>BMDB0000044</accession>
  <secondary_accessions>
    <accession>BMDB00044</accession>
    <accession>BMDB0014273</accession>
    <accession>BMDB14273</accession>
  </secondary_accessions>
  <name>Ascorbic acid</name>
  <description>Ascorbic acid, also known as ascorbate, belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. Ascorbic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dopamine and ascorbic acid can be converted into norepinephrine and dehydroascorbic acid through the action of the enzyme dopamine beta-hydroxylase. In cattle, ascorbic acid is involved in the metabolic pathway called the tyrosine metabolism pathway.</description>
  <synonyms>
    <synonym>Acide ascorbique</synonym>
    <synonym>Acido ascorbico</synonym>
    <synonym>Acidum ascorbicum</synonym>
    <synonym>Acidum ascorbinicum</synonym>
    <synonym>Ascoltin</synonym>
    <synonym>Ascorbicap</synonym>
    <synonym>Ascorbinsaeure</synonym>
    <synonym>e 300</synonym>
    <synonym>e-300</synonym>
    <synonym>e300</synonym>
    <synonym>L-(+)-Ascorbic acid</synonym>
    <synonym>L-Ascorbate</synonym>
    <synonym>Vitamin C</synonym>
    <synonym>Monodehydroascorbate radical</synonym>
    <synonym>Ascorbate radical</synonym>
    <synonym>Semidehydroascorbic acid</synonym>
    <synonym>ASCOR</synonym>
    <synonym>L-(+)-Ascorbate</synonym>
    <synonym>L-Ascorbic acid</synonym>
    <synonym>Monodehydroascorbic acid radical</synonym>
    <synonym>Ascorbic acid radical</synonym>
    <synonym>Semidehydroascorbate</synonym>
    <synonym>Ascorbate</synonym>
    <synonym>(+)-Ascorbate</synonym>
    <synonym>(+)-Ascorbic acid</synonym>
    <synonym>(+)-Sodium L-ascorbate</synonym>
    <synonym>3-keto-L-Gulofuranolactone</synonym>
    <synonym>3-oxo-L-Gulofuranolactone</synonym>
    <synonym>Adenex</synonym>
    <synonym>Allercorb</synonym>
    <synonym>Antiscorbic vitamin</synonym>
    <synonym>Antiscorbutic vitamin</synonym>
    <synonym>arco-Cee</synonym>
    <synonym>Ascor-b.i.d.</synonym>
    <synonym>Ascorb</synonym>
    <synonym>Ascorbajen</synonym>
    <synonym>Ascorbicab</synonym>
    <synonym>Ascorbicin</synonym>
    <synonym>Ascorbin</synonym>
    <synonym>Ascorbutina</synonym>
    <synonym>Ascorin</synonym>
    <synonym>Ascorteal</synonym>
    <synonym>Ascorvit</synonym>
    <synonym>C-Level</synonym>
    <synonym>C-Long</synonym>
    <synonym>C-Quin</synonym>
    <synonym>C-Span</synonym>
    <synonym>C-Vimin</synonym>
    <synonym>Cantan</synonym>
    <synonym>Cantaxin</synonym>
    <synonym>Catavin C</synonym>
    <synonym>Ce lent</synonym>
    <synonym>Ce-mi-lin</synonym>
    <synonym>Ce-vi-sol</synonym>
    <synonym>Cebicure</synonym>
    <synonym>Cebid</synonym>
    <synonym>Cebion</synonym>
    <synonym>Cebione</synonym>
    <synonym>Cecon</synonym>
    <synonym>Cee-caps TD</synonym>
    <synonym>Cee-vite</synonym>
    <synonym>Cegiolan</synonym>
    <synonym>Ceglion</synonym>
    <synonym>Ceklin</synonym>
    <synonym>Celaskon</synonym>
    <synonym>Celin</synonym>
    <synonym>Cell C</synonym>
    <synonym>Cemagyl</synonym>
    <synonym>Cemill</synonym>
    <synonym>Cenetone</synonym>
    <synonym>Cenolate</synonym>
    <synonym>Cereon</synonym>
    <synonym>Cergona</synonym>
    <synonym>Cescorbat</synonym>
    <synonym>Cetamid</synonym>
    <synonym>Cetane</synonym>
    <synonym>Cetane-caps TC</synonym>
    <synonym>Cetane-caps TD</synonym>
    <synonym>Cetebe</synonym>
    <synonym>Cetemican</synonym>
    <synonym>Cevalin</synonym>
    <synonym>Cevatine</synonym>
    <synonym>Cevex</synonym>
    <synonym>Cevi-bid</synonym>
    <synonym>Cevimin</synonym>
    <synonym>Cevital</synonym>
    <synonym>Cevitamate</synonym>
    <synonym>Cevitamic acid</synonym>
    <synonym>Cevitamin</synonym>
    <synonym>Cevitan</synonym>
    <synonym>Cevitex</synonym>
    <synonym>Cewin</synonym>
    <synonym>Chewcee</synonym>
    <synonym>Ciamin</synonym>
    <synonym>Cipca</synonym>
    <synonym>Citriscorb</synonym>
    <synonym>Citrovit</synonym>
    <synonym>Colascor</synonym>
    <synonym>Concemin</synonym>
    <synonym>Davitamon C</synonym>
    <synonym>Dora-C-500</synonym>
    <synonym>Duoscorb</synonym>
    <synonym>Ferrous ascorbate</synonym>
    <synonym>gamma-Lactone L-threo-hex-2-enonate</synonym>
    <synonym>gamma-Lactone L-threo-hex-2-enonic acid</synonym>
    <synonym>HiCee</synonym>
    <synonym>Hybrin</synonym>
    <synonym>ido-C</synonym>
    <synonym>Juvamine</synonym>
    <synonym>Kangbingfeng</synonym>
    <synonym>Kyselina askorbova</synonym>
    <synonym>L(+)-Ascorbate</synonym>
    <synonym>L(+)-Ascorbic acid</synonym>
    <synonym>L-3-Ketothreohexuronic acid lactone</synonym>
    <synonym>L-Lyxoascorbate</synonym>
    <synonym>L-Lyxoascorbic acid</synonym>
    <synonym>L-threo-Ascorbic acid</synonym>
    <synonym>L-Xyloascorbate</synonym>
    <synonym>L-Xyloascorbic acid</synonym>
    <synonym>Laroscorbine</synonym>
    <synonym>Lemascorb</synonym>
    <synonym>Liqui-cee</synonym>
    <synonym>Meri-c</synonym>
    <synonym>Natrascorb</synonym>
    <synonym>Natrascorb injectable</synonym>
    <synonym>Planavit C</synonym>
    <synonym>Proscorbin</synonym>
    <synonym>Redoxon</synonym>
    <synonym>Ribena</synonym>
    <synonym>Ronotec 100</synonym>
    <synonym>Rontex 100</synonym>
    <synonym>Roscorbic</synonym>
    <synonym>Rovimix C</synonym>
    <synonym>Scorbacid</synonym>
    <synonym>Scorbu C</synonym>
    <synonym>Scorbu-C</synonym>
    <synonym>Secorbate</synonym>
    <synonym>Sodascorbate</synonym>
    <synonym>Suncoat VC 40</synonym>
    <synonym>Testascorbic</synonym>
    <synonym>VASC</synonym>
    <synonym>Vicelat</synonym>
    <synonym>Vicin</synonym>
    <synonym>Vicomin C</synonym>
    <synonym>Viforcit</synonym>
    <synonym>Viscorin</synonym>
    <synonym>Viscorin 100m</synonym>
    <synonym>Vitace</synonym>
    <synonym>Vitacee</synonym>
    <synonym>Vitacimin</synonym>
    <synonym>Vitacin</synonym>
    <synonym>Vitamisin</synonym>
    <synonym>Vitascorbol</synonym>
    <synonym>Xitix</synonym>
    <synonym>L Ascorbic acid</synonym>
    <synonym>Acid, ascorbic</synonym>
    <synonym>Ascorbate, ferrous</synonym>
    <synonym>Ascorbate, sodium</synonym>
    <synonym>Magnesium ascorbate</synonym>
    <synonym>Magnesium ascorbicum</synonym>
    <synonym>Magnesium di-L-ascorbate</synonym>
    <synonym>Di-L-ascorbate, magnesium</synonym>
    <synonym>Ascorbic acid, monosodium salt</synonym>
    <synonym>Magnesium di L ascorbate</synonym>
    <synonym>Magnorbin</synonym>
    <synonym>Sodium ascorbate</synonym>
    <synonym>Acid, L-ascorbic</synonym>
    <synonym>Ascorbate, magnesium</synonym>
    <synonym>ASCORBIC ACID</synonym>
  </synonyms>
  <chemical_formula>C6H8O6</chemical_formula>
  <average_molecular_weight>176.1241</average_molecular_weight>
  <monisotopic_moleculate_weight>176.032087988</monisotopic_moleculate_weight>
  <iupac_name>(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one</iupac_name>
  <traditional_iupac>vitamin C</traditional_iupac>
  <cas_registry_number>50-81-7</cas_registry_number>
  <smiles>[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO</smiles>
  <inchi>InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1</inchi>
  <inchikey>CIWBSHSKHKDKBQ-JLAZNSOCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Dihydrofurans</class>
    <sub_class>Furanones</sub_class>
    <direct_parent>Butenolides</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Enediols</alternative_parent>
      <alternative_parent>Enoate esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>2-furanone</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha,beta-unsaturated carboxylic ester</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Enediol</substituent>
      <substituent>Enoate ester</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Water-soluble vitamins</external_descriptor>
      <external_descriptor>ascorbic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5R)-5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-2,5-dihydrofuran-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>176.1241</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>176.032087988</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H8O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H8O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-10H,1H2/t2-,5+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CIWBSHSKHKDKBQ-JLAZNSOCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>107.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>106278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>106279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>106280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>172965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>172966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>172967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99529</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>8-18</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>HPLC with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Padilla L., T.Matsui Y.Kamiya M.Kamiya M.Tanaka H.Yano. 2006. Heat stress decreases plasma vitamin C concentration in lactating cows. Livestock Science. 101(1–3):300-304</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>11+/-3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>880+/-257</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>22.711 +/- 1.419</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized whole milk</comment>
      <references>
        <reference>
          <reference_text>Bilic N: Assay for both ascorbic and dehydroascorbic acid in dairy foods by high-performance liquid chromatography using precolumn derivatization with methoxy- and ethoxy-1,2-phenylenediamine. J Chromatogr. 1991 May 10;543(2):367-74.</reference_text>
          <pubmed_id>1880195</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>33.499 +/- 1.703</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Bilic N: Assay for both ascorbic and dehydroascorbic acid in dairy foods by high-performance liquid chromatography using precolumn derivatization with methoxy- and ethoxy-1,2-phenylenediamine. J Chromatogr. 1991 May 10;543(2):367-74.</reference_text>
          <pubmed_id>1880195</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>53.371</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>153.301</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Sampled during March</comment>
      <references>
        <reference>
          <reference_text>Int. Dairy Journal 4 (1994) 161-172</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>34.7 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>39 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>34.0 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.2 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>53.371 - 55.643</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>62.229 - 129.852</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Weiss WP, Hogan JS, Smith KL: Changes in vitamin C concentrations in plasma and milk from dairy cows after an intramammary infusion of Escherichia coli. J Dairy Sci. 2004 Jan;87(1):32-7. doi: 10.3168/jds.S0022-0302(04)73138-0.</reference_text>
          <pubmed_id>14765807</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>56.778</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>68.134</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>56.778</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>62.456</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>56.778</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>73.812</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>73.812</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>85.167</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>62.456</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>56.778</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>62.456</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11.356</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11.356</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>73.812</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>73.812</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>73.812</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>68.134</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>68.134</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>68.134</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>1576+/-363</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01041</kegg_id>
  <drugbank_id>DB00126</drugbank_id>
  <foodb_id>FDB001224</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>54670067</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>29073</chebi_id>
  <knapsack_id>C00001179</knapsack_id>
  <wikipedia_id>Ascorbic_Acid</wikipedia_id>
  <meta_cyc_id>ASCORBATE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Bilic N: Assay for both ascorbic and dehydroascorbic acid in dairy foods by high-performance liquid chromatography using precolumn derivatization with methoxy- and ethoxy-1,2-phenylenediamine. J Chromatogr. 1991 May 10;543(2):367-74.</reference_text>
      <pubmed_id>1880195</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
      <pubmed_id>22081685</pubmed_id>
    </reference>
    <reference>
      <reference_text>Weiss WP, Hogan JS, Smith KL: Changes in vitamin C concentrations in plasma and milk from dairy cows after an intramammary infusion of Escherichia coli. J Dairy Sci. 2004 Jan;87(1):32-7. doi: 10.3168/jds.S0022-0302(04)73138-0.</reference_text>
      <pubmed_id>14765807</pubmed_id>
    </reference>
    <reference>
      <reference_text>Int. Dairy Journal 4 (1994) 161-172</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:55 UTC</creation_date>
  <update_date>2020-04-15 20:47:40 UTC</update_date>
  <accession>BMDB0000045</accession>
  <secondary_accessions>
    <accession>BMDB00045</accession>
  </secondary_accessions>
  <name>Adenosine monophosphate</name>
  <description>Adenosine monophosphate, also known as adenylic acid or AMP, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Adenosine monophosphate is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Adenosine monophosphate exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Adenosine monophosphate exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>5'-Adenosine monophosphate</synonym>
    <synonym>5'-Adenylic acid</synonym>
    <synonym>5'-AMP</synonym>
    <synonym>5'-O-Phosphonoadenosine</synonym>
    <synonym>Adenosine 5'-(dihydrogen phosphate)</synonym>
    <synonym>Adenosine 5'-phosphate</synonym>
    <synonym>Adenosine phosphate</synonym>
    <synonym>Adenosine-5'-monophosphoric acid</synonym>
    <synonym>Adenosine-5'p</synonym>
    <synonym>Adenosini phosphas</synonym>
    <synonym>Adenylate</synonym>
    <synonym>Adenylic acid</synonym>
    <synonym>Ado5'p</synonym>
    <synonym>AMP</synonym>
    <synonym>Fosfato de adenosina</synonym>
    <synonym>pA</synonym>
    <synonym>PAdo</synonym>
    <synonym>Phosphate d'adenosine</synonym>
    <synonym>Adenosine 5'-monophosphate</synonym>
    <synonym>Adenyl</synonym>
    <synonym>5'-Adenosine monophosphoric acid</synonym>
    <synonym>5'-Adenylate</synonym>
    <synonym>Adenosine 5'-(dihydrogen phosphoric acid)</synonym>
    <synonym>Adenosine 5'-phosphoric acid</synonym>
    <synonym>Adenosine phosphoric acid</synonym>
    <synonym>Adenosine-5'-monophosphate</synonym>
    <synonym>Phosphoric acid d'adenosine</synonym>
    <synonym>Adenosine 5'-monophosphoric acid</synonym>
    <synonym>Adenosine monophosphoric acid</synonym>
    <synonym>Adenosine 5'-phosphorate</synonym>
    <synonym>Adenosine-5'-monophosphorate</synonym>
    <synonym>Adenosine-5-monophosphorate</synonym>
    <synonym>Adenosine-5-monophosphoric acid</synonym>
    <synonym>Adenosine-monophosphate</synonym>
    <synonym>Adenosine-phosphate</synonym>
    <synonym>Adenovite</synonym>
    <synonym>Cardiomone</synonym>
    <synonym>Lycedan</synonym>
    <synonym>Muscle adenylate</synonym>
    <synonym>Muscle adenylic acid</synonym>
    <synonym>My-b-den</synonym>
    <synonym>My-beta-den</synonym>
    <synonym>Phosaden</synonym>
    <synonym>Phosphaden</synonym>
    <synonym>Phosphentaside</synonym>
    <synonym>5'-Phosphate, adenosine</synonym>
    <synonym>Acid, 2'-adenylic</synonym>
    <synonym>2'-Adenylic acid</synonym>
    <synonym>Adenosine 3' phosphate</synonym>
    <synonym>Disodium, adenosine phosphate</synonym>
    <synonym>Phosphate dipotassium, adenosine</synonym>
    <synonym>Adenosine 2'-phosphate</synonym>
    <synonym>Adenosine 5' phosphate</synonym>
    <synonym>Adenosine phosphate dipotassium</synonym>
    <synonym>Dipotassium, adenosine phosphate</synonym>
    <synonym>2' Adenylic acid</synonym>
    <synonym>5' Adenylic acid</synonym>
    <synonym>Acid, 5'-adenylic</synonym>
    <synonym>Adenosine 3'-phosphate</synonym>
    <synonym>monoPhosphate, 2'-adenosine</synonym>
    <synonym>Phosphate disodium, adenosine</synonym>
    <synonym>2' Adenosine monophosphate</synonym>
    <synonym>2'-AMP</synonym>
    <synonym>2'-Adenosine monophosphate</synonym>
    <synonym>Adenosine 2' phosphate</synonym>
    <synonym>Adenosine phosphate disodium</synonym>
  </synonyms>
  <chemical_formula>C10H14N5O7P</chemical_formula>
  <average_molecular_weight>347.2212</average_molecular_weight>
  <monisotopic_moleculate_weight>347.063084339</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>adenylate</traditional_iupac>
  <cas_registry_number>61-19-8</cas_registry_number>
  <smiles>NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1</smiles>
  <inchi>InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>UDMBCSSLTHHNCD-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ribonucleotides</external_descriptor>
      <external_descriptor>adenosine 5'-phosphate</external_descriptor>
      <external_descriptor>purine ribonucleoside 5'-monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>195 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>10 mg/mL at 20 °C</value>
      <source>BEILSTEIN</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>347.2212</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>347.063084339</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H14N5O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UDMBCSSLTHHNCD-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>186.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>74.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Butyrate Metabolism</name>
      <smpdb_id>SMP0087185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ethanol Degradation</name>
      <smpdb_id>SMP0087192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pantothenate and CoA Biosynthesis</name>
      <smpdb_id>SMP0087207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylacetate Metabolism</name>
      <smpdb_id>SMP0087208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Alanine</name>
      <smpdb_id>SMP0119369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Arginine</name>
      <smpdb_id>SMP0119383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Asparagine</name>
      <smpdb_id>SMP0119385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Aspartic Acid</name>
      <smpdb_id>SMP0119386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Cysteine</name>
      <smpdb_id>SMP0119388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Glutamic Acid</name>
      <smpdb_id>SMP0119390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Glutamine</name>
      <smpdb_id>SMP0119389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Glycine</name>
      <smpdb_id>SMP0119391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Histidine</name>
      <smpdb_id>SMP0119392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Isoleucine</name>
      <smpdb_id>SMP0119393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Leucine</name>
      <smpdb_id>SMP0119403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Lysine</name>
      <smpdb_id>SMP0119404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Methionine</name>
      <smpdb_id>SMP0119405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Phenylalanine</name>
      <smpdb_id>SMP0119406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Proline</name>
      <smpdb_id>SMP0119407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Serine</name>
      <smpdb_id>SMP0119409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Threonine</name>
      <smpdb_id>SMP0119410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Tryptophan</name>
      <smpdb_id>SMP0119414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Tyrosine</name>
      <smpdb_id>SMP0119416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Valine</name>
      <smpdb_id>SMP0119417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Riboflavin Metabolism</name>
      <smpdb_id>SMP0087211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Selenoamino Acid Metabolism</name>
      <smpdb_id>SMP0087161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Thiamine Metabolism</name>
      <smpdb_id>SMP0087212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ubiquitin–Proteasome Pathway</name>
      <smpdb_id>SMP0120929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181199</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15.800 - 80.300</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44.</reference_text>
          <pubmed_id>7196410</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00020</kegg_id>
  <drugbank_id>DB00131</drugbank_id>
  <chemspider_id>5858</chemspider_id>
  <foodb_id>FDB030677</foodb_id>
  <pdbe_id/>
  <chebi_id>16027</chebi_id>
  <pubchem_compound_id>6083</pubchem_compound_id>
  <meta_cyc_id>AMP</meta_cyc_id>
  <knapsack_id>C00019347</knapsack_id>
  <wikipedia_id>Adenylic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33534</bigg_id>
  <metlin_id>5111</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44.</reference_text>
      <pubmed_id>7196410</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00195</protein_accession>
      <name>3'(2'),5'-bisphosphate nucleotidase 1</name>
      <uniprot_id>Q3ZCK3</uniprot_id>
      <gene_name>BPNT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00443</protein_accession>
      <name>Poly(A)-specific ribonuclease PARN</name>
      <uniprot_id>P69341</uniprot_id>
      <gene_name>PARN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00584</protein_accession>
      <name>GTP:AMP phosphotransferase mitochondrial</name>
      <uniprot_id>P08760</uniprot_id>
      <gene_name>AK3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01335</protein_accession>
      <name>Prostaglandin D2 receptor</name>
      <uniprot_id>A5D7K8</uniprot_id>
      <gene_name>PTGDR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01340</protein_accession>
      <name>Prostacyclin receptor</name>
      <uniprot_id>P79393</uniprot_id>
      <gene_name>PTGIR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01608</protein_accession>
      <name>Prostaglandin E2 receptor EP4 subtype</name>
      <uniprot_id>Q8MJ08</uniprot_id>
      <gene_name>PTGER4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01610</protein_accession>
      <name>Prostaglandin E2 receptor EP3 subtype</name>
      <uniprot_id>P34979</uniprot_id>
      <gene_name>PTGER3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01636</protein_accession>
      <name>Vasopressin V2 receptor</name>
      <uniprot_id>P48044</uniprot_id>
      <gene_name>AVPR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01815</protein_accession>
      <name>Melanocyte-stimulating hormone receptor</name>
      <uniprot_id>P47798</uniprot_id>
      <gene_name>MC1R</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01816</protein_accession>
      <name>Pituitary adenylate cyclase-activating polypeptide type I receptor</name>
      <uniprot_id>Q29627</uniprot_id>
      <gene_name>ADCYAP1R1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01817</protein_accession>
      <name>Alpha-2A adrenergic receptor</name>
      <uniprot_id>Q28838</uniprot_id>
      <gene_name>ADRA2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01818</protein_accession>
      <name>Muscarinic acetylcholine receptor M2</name>
      <uniprot_id>P41985</uniprot_id>
      <gene_name>CHRM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01819</protein_accession>
      <name>Alpha-2B adrenergic receptor</name>
      <uniprot_id>O77700</uniprot_id>
      <gene_name>ADRA2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01820</protein_accession>
      <name>Muscarinic acetylcholine receptor M3</name>
      <uniprot_id>P41984</uniprot_id>
      <gene_name>CHRM3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01821</protein_accession>
      <name>Lutropin-choriogonadotropic hormone receptor</name>
      <uniprot_id>Q28005</uniprot_id>
      <gene_name>LHCGR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01822</protein_accession>
      <name>Thyrotropin receptor</name>
      <uniprot_id>Q27987</uniprot_id>
      <gene_name>TSHR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01823</protein_accession>
      <name>Adrenocorticotropic hormone receptor</name>
      <uniprot_id>P34974</uniprot_id>
      <gene_name>MC2R</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01824</protein_accession>
      <name>Follicle-stimulating hormone receptor</name>
      <uniprot_id>P35376</uniprot_id>
      <gene_name>FSHR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01825</protein_accession>
      <name>Muscarinic acetylcholine receptor M4</name>
      <uniprot_id>P41986</uniprot_id>
      <gene_name>CHRM4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01826</protein_accession>
      <name>Pituitary adenylate cyclase-activating polypeptide receptor</name>
      <uniprot_id>Q9TRE3</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01827</protein_accession>
      <name>Melanocortin receptor 5</name>
      <uniprot_id>P56451</uniprot_id>
      <gene_name>MC5R</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01828</protein_accession>
      <name>Melatonin receptor type 1A</name>
      <uniprot_id>O02769</uniprot_id>
      <gene_name>MTNR1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:56 UTC</creation_date>
  <update_date>2020-04-16 20:37:40 UTC</update_date>
  <accession>BMDB0000048</accession>
  <secondary_accessions>
    <accession>BMDB00048</accession>
  </secondary_accessions>
  <name>Melibiose</name>
  <description>Melibiose, also known as isomaltose, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Melibiose is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Melibiose exists in all living species, ranging from bacteria to humans. Melibiose participates in a number of enzymatic reactions, within cattle. In particular, Melibiose and D-galactose can be biosynthesized from Alpha-lactose; which is mediated by the enzyme Alpha-galactosidase a. In addition, Melibiose can be converted into D-galactose through its interaction with the enzyme Alpha-galactosidase a. In cattle, melibiose is involved in the metabolic pathway called the galactose metabolism pathway.</description>
  <synonyms>
    <synonym>6-O-alpha-D-Galactopyranosyl-D-glucose</synonym>
    <synonym>6-O-alpha-D-Galactopyranosyl-alpha-D-glucopyranose</synonym>
    <synonym>6-O-Α-D-galactopyranosyl-D-glucose</synonym>
    <synonym>6-O-Α-D-galactopyranosyl-α-D-glucopyranose</synonym>
    <synonym>D-(+)-Melibiose</synonym>
    <synonym>D-Melibiose</synonym>
    <synonym>alpha-D-Melibiose</synonym>
    <synonym>alpha-Melibiose</synonym>
    <synonym>Α-D-melibiose</synonym>
    <synonym>Α-melibiose</synonym>
    <synonym>Melibiose</synonym>
  </synonyms>
  <chemical_formula>C12H22O11</chemical_formula>
  <average_molecular_weight>342.2965</average_molecular_weight>
  <monisotopic_moleculate_weight>342.116211546</monisotopic_moleculate_weight>
  <iupac_name>(2S,3R,4S,5S,6R)-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>(2S,3R,4S,5S,6R)-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol</traditional_iupac>
  <cas_registry_number>13299-20-2</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](OC[C@H]2O[C@H](O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5+,6-,7+,8+,9-,10-,11+,12+/m1/s1</inchi>
  <inchikey>DLRVVLDZNNYCBX-CQHUIXDMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>O-glycosyl compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Disaccharides</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>84 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3R,4S,5S,6R)-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>342.2965</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>342.116211546</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](OC[C@H]2O[C@H](O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H22O11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5+,6-,7+,8+,9-,10-,11+,12+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DLRVVLDZNNYCBX-CQHUIXDMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>189.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2048</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <chemspider_id/>
  <foodb_id/>
  <pdbe_id/>
  <chebi_id/>
  <pubchem_compound_id>6602503</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Melibiose</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Pictet, Ame; Vogel, Hans.  The synthesis of melibiose.  Helvetica Chimica Acta  (1927),  10  280.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:58 UTC</creation_date>
  <update_date>2020-04-16 17:52:06 UTC</update_date>
  <accession>BMDB0000050</accession>
  <secondary_accessions>
    <accession>BMDB00050</accession>
  </secondary_accessions>
  <name>Adenosine</name>
  <description>Adenosine, also known as adenocard or ade-rib, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Adenosine is a drug which is used as an initial treatment for the termination of paroxysmal supraventricular tachycardia (pvst), including that associated with accessory bypass tracts, and is a drug of choice for terminating stable, narrow-complex supraventricular tachycardias (svt). also used as an adjunct to thallous chloride ti 201 myocardial perfusion scintigraphy (thallium stress test) in patients who are unable to exercise adequately, as well as an adjunct to vagal maneuvers and clinical assessment to establish a specific diagnosis of undefined, stable, narrow-complex svt. Adenosine exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Adenosine exists in all living species, ranging from bacteria to humans. Adenosine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2R,3R,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol</synonym>
    <synonym>6-Amino-9-beta-D-ribofuranosyl-9H-purine</synonym>
    <synonym>9-beta-D-Ribofuranosidoadenine</synonym>
    <synonym>9-beta-D-Ribofuranosyl-9H-purin-6-amine</synonym>
    <synonym>Ade-rib</synonym>
    <synonym>Adenine deoxyribonucleoside</synonym>
    <synonym>Adenocard</synonym>
    <synonym>Adenocor</synonym>
    <synonym>Adenoscan</synonym>
    <synonym>Adenosin</synonym>
    <synonym>Adenyldeoxyriboside</synonym>
    <synonym>Ado</synonym>
    <synonym>beta-D-Adenosine</synonym>
    <synonym>Deoxyadenosine</synonym>
    <synonym>Desoxyadenosine</synonym>
    <synonym>6-Amino-9-b-D-ribofuranosyl-9H-purine</synonym>
    <synonym>6-Amino-9-β-D-ribofuranosyl-9H-purine</synonym>
    <synonym>9-b-D-Ribofuranosidoadenine</synonym>
    <synonym>9-Β-D-ribofuranosidoadenine</synonym>
    <synonym>9-b-D-Ribofuranosyl-9H-purin-6-amine</synonym>
    <synonym>9-Β-D-ribofuranosyl-9H-purin-6-amine</synonym>
    <synonym>b-D-Adenosine</synonym>
    <synonym>Β-D-adenosine</synonym>
    <synonym>1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-D-ribofuranose</synonym>
    <synonym>1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-delta-ribofuranose</synonym>
    <synonym>6-Amino-9beta-D-ribofuranosyl-9H-purine</synonym>
    <synonym>6-Amino-9beta-delta-ribofuranosyl-9H-purine</synonym>
    <synonym>9-beta-D-Arabinofuranosyladenine</synonym>
    <synonym>9-beta-D-Ribofuranosyladenine</synonym>
    <synonym>9-beta-delta-Arabinofuranosyladenine</synonym>
    <synonym>9-beta-delta-Ribofuranosidoadenine</synonym>
    <synonym>9-beta-delta-Ribofuranosyl-9H-purin-6-amine</synonym>
    <synonym>9-beta-delta-Ribofuranosyladenine</synonym>
    <synonym>9beta-D-Ribofuranosyl-9H-purin-6-amine</synonym>
    <synonym>9beta-D-Ribofuranosyladenine</synonym>
    <synonym>9beta-delta-Ribofuranosyl-9H-purin-6-amine</synonym>
    <synonym>9beta-delta-Ribofuranosyladenine</synonym>
    <synonym>Adenine nucleoside</synonym>
    <synonym>Adenine riboside</synonym>
    <synonym>Adenine-9beta-D-ribofuranoside</synonym>
    <synonym>Adenine-9beta-delta-ribofuranoside</synonym>
    <synonym>beta-Adenosine</synonym>
    <synonym>beta-delta-Adenosine</synonym>
    <synonym>Boniton</synonym>
    <synonym>Myocol</synonym>
    <synonym>Nucleocardyl</synonym>
    <synonym>Sandesin</synonym>
  </synonyms>
  <chemical_formula>C10H13N5O4</chemical_formula>
  <average_molecular_weight>267.2413</average_molecular_weight>
  <monisotopic_moleculate_weight>267.096753929</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol</iupac_name>
  <traditional_iupac>adenosine</traditional_iupac>
  <cas_registry_number>58-61-7</cas_registry_number>
  <smiles>NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1</smiles>
  <inchi>InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>OIRDTQYFTABQOQ-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleosides</class>
    <sub_class/>
    <direct_parent>Purine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleoside</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ribonucleosides</external_descriptor>
      <external_descriptor>adenosines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>235.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>37 mg/mL</value>
      <source>Human Metabolome Project</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.05</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>267.2413</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>267.096753929</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H13N5O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OIRDTQYFTABQOQ-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>139.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>63.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2a and Adenosine</name>
      <smpdb_id>SMP0108174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2b and Adenosine</name>
      <smpdb_id>SMP0108178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Selenoamino Acid Metabolism</name>
      <smpdb_id>SMP0087161</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>81</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>82</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>83</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179656</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68.</reference_text>
          <pubmed_id>11242448</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in beef muscle (longissimus dorsi).</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>150+/-114</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>54923</chemspider_id>
  <drugbank_id>DB00640</drugbank_id>
  <pubchem_compound_id>60961</pubchem_compound_id>
  <foodb_id>FDB003554</foodb_id>
  <kegg_id>C00212</kegg_id>
  <chebi_id>16335</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00007444</knapsack_id>
  <meta_cyc_id>ADENOSINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34273</bigg_id>
  <wikipedia_id>Adenosine</wikipedia_id>
  <metlin_id>86</metlin_id>
  <synthesis_reference>Liao, Ben-ren; Yuan, Zhen-wen.  Synthesis of adenosine from inosine.    Huaxue Shiji  (2006),  28(10),  633-634.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52.</reference_text>
      <pubmed_id>1897275</pubmed_id>
    </reference>
    <reference>
      <reference_text>Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68.</reference_text>
      <pubmed_id>11242448</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00837</protein_accession>
      <name>Adenosylhomocysteinase</name>
      <uniprot_id>A5PKK6</uniprot_id>
      <gene_name>AHCYL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00838</protein_accession>
      <name>Adenosylhomocysteinase</name>
      <uniprot_id>A6QLP2</uniprot_id>
      <gene_name>AHCYL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00839</protein_accession>
      <name>Adenosine deaminase</name>
      <uniprot_id>P56658</uniprot_id>
      <gene_name>ADA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02088</protein_accession>
      <name>Adenosine A3 receptor</name>
      <uniprot_id>Q0VC81</uniprot_id>
      <gene_name>ADORA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02089</protein_accession>
      <name>Adenosine receptor A2b</name>
      <uniprot_id>Q1LZD0</uniprot_id>
      <gene_name>ADORA2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02090</protein_accession>
      <name>Cleavage and polyadenylation specificity factor subunit 5</name>
      <uniprot_id>Q3ZCA2</uniprot_id>
      <gene_name>NUDT21</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02091</protein_accession>
      <name>Adenosine receptor A1</name>
      <uniprot_id>P28190</uniprot_id>
      <gene_name>ADORA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:18:59 UTC</creation_date>
  <update_date>2020-04-15 20:47:41 UTC</update_date>
  <accession>BMDB0000051</accession>
  <secondary_accessions>
    <accession>BMDB00051</accession>
  </secondary_accessions>
  <name>Ammonia</name>
  <description/>
  <synonyms>
    <synonym>[NH3]</synonym>
    <synonym>Ammoniac</synonym>
    <synonym>Ammoniak</synonym>
    <synonym>Amoniaco</synonym>
    <synonym>NH3</synonym>
    <synonym>R-717</synonym>
    <synonym>Spirit OF hartshorn</synonym>
    <synonym>Ammonia anhydrous</synonym>
    <synonym>Ammonia inhalant</synonym>
    <synonym>Ammonia solution strong</synonym>
    <synonym>Ammonia water</synonym>
    <synonym>Liquid ammonia</synonym>
    <synonym>Am-fol</synonym>
    <synonym>Ammonia (CONC 20% or greater)</synonym>
    <synonym>Ammonia gas</synonym>
    <synonym>Ammonia solution</synonym>
    <synonym>Ammonia solution strong (NF)</synonym>
    <synonym>Ammonia water (JP15)</synonym>
    <synonym>Ammoniacum gummi</synonym>
    <synonym>Ammoniak kconzentrierter</synonym>
    <synonym>Ammoniakgas</synonym>
    <synonym>Ammonium ion</synonym>
    <synonym>Anhydrous ammonia</synonym>
    <synonym>Aromatic ammonia vaporole</synonym>
    <synonym>Azane</synonym>
    <synonym>NH(3)</synonym>
    <synonym>Nitro-sil</synonym>
    <synonym>Primaeres amin</synonym>
    <synonym>Sekundaeres amin</synonym>
    <synonym>Tertiaeres amin</synonym>
  </synonyms>
  <chemical_formula>H3N</chemical_formula>
  <average_molecular_weight>17.0305</average_molecular_weight>
  <monisotopic_moleculate_weight>17.026549101</monisotopic_moleculate_weight>
  <iupac_name>ammonia</iupac_name>
  <traditional_iupac>ammonia</traditional_iupac>
  <cas_registry_number>7664-41-7</cas_registry_number>
  <smiles>N</smiles>
  <inchi>InChI=1S/H3N/h1H3</inchi>
  <inchikey>QGZKDVFQNNGYKY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Homogeneous other non-metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous other non-metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous other non metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>azane</external_descriptor>
      <external_descriptor>mononuclear parent hydride</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-77.7 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>482 mg/mL at 24 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>ammonia</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>17.0305</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>17.026549101</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>H3N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/H3N/h1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QGZKDVFQNNGYKY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>13.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>15.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>D-Arginine and D-Ornithine Metabolism</name>
      <smpdb_id>SMP0087190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glucose-Alanine Cycle</name>
      <smpdb_id>SMP0087221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Homocysteine Degradation</name>
      <smpdb_id>SMP0087201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Selenoamino Acid Metabolism</name>
      <smpdb_id>SMP0087161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Threonine and 2-Oxobutanoate Degradation</name>
      <smpdb_id>SMP0087262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin B6 Metabolism</name>
      <smpdb_id>SMP0087240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22651</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00014</kegg_id>
  <drugbank_id>DBMET01482</drugbank_id>
  <foodb_id>FDB003908</foodb_id>
  <chemspider_id>217</chemspider_id>
  <pubchem_compound_id>222</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16134</chebi_id>
  <knapsack_id>C00007267</knapsack_id>
  <wikipedia_id>Ammonia</wikipedia_id>
  <meta_cyc_id>AMMONIA</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>3189</metlin_id>
  <synthesis_reference>Mohr, Rudolf.  Ammonia separation from offgas obtained from melamine synthesis.    U.S.  (1971),     5 pp.  CODEN: USXXAM  US  3555784  19710119  CAN 77:50902  AN 1972:450902</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP02163</protein_accession>
      <name>Ammonium transporter Rh type A</name>
      <uniprot_id>Q9GKN7</uniprot_id>
      <gene_name>RHAG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02164</protein_accession>
      <name>Ammonium transporter Rh type B</name>
      <uniprot_id>Q95M77</uniprot_id>
      <gene_name>RHBG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02165</protein_accession>
      <name>Ammonium transporter Rh type C</name>
      <uniprot_id>Q2T9S6</uniprot_id>
      <gene_name>RHCG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:00 UTC</creation_date>
  <update_date>2020-04-15 22:08:19 UTC</update_date>
  <accession>BMDB0000052</accession>
  <secondary_accessions>
    <accession>BMDB00052</accession>
  </secondary_accessions>
  <name>Argininosuccinic acid</name>
  <description/>
  <synonyms>
    <synonym>2-(Nomega-L-arginino)succinate</synonym>
    <synonym>L-Argininosuccinate</synonym>
    <synonym>L-Argininosuccinic acid</synonym>
    <synonym>L-Arginosuccinic acid</synonym>
    <synonym>2-(Nomega-L-arginino)succinic acid</synonym>
    <synonym>L-Arginosuccinate</synonym>
    <synonym>Argininosuccinate</synonym>
    <synonym>2-(N(Omega)-L-arginine)succinate</synonym>
    <synonym>2-(N(Omega)-L-arginine)succinic acid</synonym>
    <synonym>2-(N(Omega)-L-arginino)succinate</synonym>
    <synonym>2-(N(Omega)-L-arginino)succinic acid</synonym>
    <synonym>2-(Nw-l-arginino)butanedioate</synonym>
    <synonym>2-(Nw-l-arginino)butanedioic acid</synonym>
    <synonym>Arginosuccinate</synonym>
    <synonym>Arginosuccinic acid</synonym>
    <synonym>ASA</synonym>
    <synonym>N(Omega)-(L-arginino)succinate</synonym>
    <synonym>N(Omega)-(L-arginino)succinic acid</synonym>
    <synonym>N-(((4-Amino-4-carboxybutyl)amino)iminomethyl)-L-aspartate</synonym>
    <synonym>N-(((4-Amino-4-carboxybutyl)amino)iminomethyl)-L-aspartic acid</synonym>
    <synonym>N-(L-Arginino) succinate</synonym>
    <synonym>N-(L-Arginino) succinic acid</synonym>
    <synonym>N-(L-Arginino)succinate</synonym>
    <synonym>N-(L-Arginino)succinic acid</synonym>
    <synonym>N-[(4-Amino-4-carboxybutyl)amidino]-L-aspartate</synonym>
    <synonym>N-[(4-Amino-4-carboxybutyl)amidino]-L-aspartic acid</synonym>
    <synonym>N-[[(4-Amino-4-carboxybutyl)amino]iminomethyl]-L-aspartate</synonym>
    <synonym>N-[[(4-Amino-4-carboxybutyl)amino]iminomethyl]-L-aspartic acid</synonym>
    <synonym>Acid, argininosuccinic</synonym>
    <synonym>N-(4-Amino-4-carboxybutyl)amidino-L-aspartic acid</synonym>
  </synonyms>
  <chemical_formula>C10H18N4O6</chemical_formula>
  <average_molecular_weight>290.2731</average_molecular_weight>
  <monisotopic_moleculate_weight>290.122634328</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-{N'-[(4S)-4-amino-4-carboxybutyl]carbamimidamido}butanedioic acid</iupac_name>
  <traditional_iupac>argininosuccinic acid</traditional_iupac>
  <cas_registry_number>2387-71-5</cas_registry_number>
  <smiles>N[C@@H](CCCNC(=N)N[C@@H](CC(O)=O)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C10H18N4O6/c11-5(8(17)18)2-1-3-13-10(12)14-6(9(19)20)4-7(15)16/h5-6H,1-4,11H2,(H,15,16)(H,17,18)(H,19,20)(H3,12,13,14)/t5-,6-/m0/s1</inchi>
  <inchikey>KDZOASGQNOPSCU-WDSKDSINSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Aspartic acid and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Guanidines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Aspartic acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Other amino acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>12.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-{N'-[(4S)-4-amino-4-carboxybutyl]carbamimidamido}butanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>290.2731</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>290.122634328</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCCNC(=N)N[C@@H](CC(O)=O)C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H18N4O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H18N4O6/c11-5(8(17)18)2-1-3-13-10(12)14-6(9(19)20)4-7(15)16/h5-6H,1-4,11H2,(H,15,16)(H,17,18)(H,19,20)(H3,12,13,14)/t5-,6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KDZOASGQNOPSCU-WDSKDSINSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>185.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>75.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>27.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>858</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437142</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03406</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB021885</foodb_id>
  <chemspider_id>16059</chemspider_id>
  <pubchem_compound_id>16950</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15682</chebi_id>
  <knapsack_id>C00019688</knapsack_id>
  <wikipedia_id>Argininosuccinic acid</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>41790</bigg_id>
  <metlin_id>5115</metlin_id>
  <synthesis_reference>Hagino, Koji; Nakanishi, Toshihide.  Fermentative production of L-arginosuccinic acid.    Jpn. Kokai Tokkyo Koho  (1980),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00237</protein_accession>
      <name>Argininosuccinate synthase</name>
      <uniprot_id>P14568</uniprot_id>
      <gene_name>ASS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00238</protein_accession>
      <name>Argininosuccinate lyase</name>
      <uniprot_id>Q3SZJ0</uniprot_id>
      <gene_name>ASL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:01 UTC</creation_date>
  <update_date>2020-04-16 17:53:50 UTC</update_date>
  <accession>BMDB0000053</accession>
  <secondary_accessions>
    <accession>BMDB00053</accession>
  </secondary_accessions>
  <name>Androstenedione</name>
  <description>Androstenedione, also known as fecundin, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, androstenedione is considered to be a steroid lipid molecule. Androstenedione exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Androstenedione exists in all living organisms, ranging from bacteria to humans. Androstenedione participates in a number of enzymatic reactions, within cattle. In particular, Androstenedione can be converted into androstanedione through its interaction with the enzyme 3-oxo-5-alpha-steroid 4-dehydrogenase 1. In addition, Androstenedione can be converted into 19-hydroxyandrost-4-ene-3,17-dione through the action of the enzyme cytochrome P450 19A1. In cattle, androstenedione is involved in the metabolic pathway called the androstenedione metabolism pathway. Androstenedione is a potentially toxic compound.</description>
  <synonyms>
    <synonym>4-Androstene-3,17-dione</synonym>
    <synonym>4-ANDROSTENE-3-17-dione</synonym>
    <synonym>delta(4)-Androsten-3,17-dione</synonym>
    <synonym>delta(4)-Androstene-3,17-dione</synonym>
    <synonym>Δ(4)-Androsten-3,17-dione</synonym>
    <synonym>Δ(4)-Androstene-3,17-dione</synonym>
    <synonym>(4)-Androsten-3,17-dione</synonym>
    <synonym>17-Ketotestosterone</synonym>
    <synonym>3,17-Dioxoandrost-4-ene</synonym>
    <synonym>4-Androsten-3,17-dione</synonym>
    <synonym>4-Androstenedione</synonym>
    <synonym>Androst-4-ene-3,17-dione</synonym>
    <synonym>Androstendione</synonym>
    <synonym>D4-Androstene-3,17-dione</synonym>
    <synonym>delta4-Androstenedione</synonym>
    <synonym>Fecundin</synonym>
    <synonym>delta 4 Androstenedione</synonym>
    <synonym>delta-4-Androstenedione</synonym>
    <synonym>4 Androstene 3,17 dione</synonym>
    <synonym>Androstenedione</synonym>
    <synonym>delta4-Androstene-3,17-dione</synonym>
    <synonym>Δ4-Androstene-3,17-dione</synonym>
  </synonyms>
  <chemical_formula>C19H26O2</chemical_formula>
  <average_molecular_weight>286.4085</average_molecular_weight>
  <monisotopic_moleculate_weight>286.193280076</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione</iupac_name>
  <traditional_iupac>(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione</traditional_iupac>
  <cas_registry_number>63-05-8</cas_registry_number>
  <smiles>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1</inchi>
  <inchikey>AEMFNILZOJDQLW-QAGGRKNESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17-oxo steroid</external_descriptor>
      <external_descriptor>3-oxo Delta(4)-steroid</external_descriptor>
      <external_descriptor>Androgens</external_descriptor>
      <external_descriptor>Androstane and derivatives</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>androstane</external_descriptor>
      <external_descriptor>androstanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>170 - 173 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0578 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.75</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>286.4085</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>286.193280076</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H26O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AEMFNILZOJDQLW-QAGGRKNESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>34.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>83.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Androstenedione Metabolism</name>
      <smpdb_id>SMP0087271</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>85</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>86</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449118</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>&lt;0.000545</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS in Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00186 +/- 0.000354</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Half-skim, commercial</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637.</reference_text>
          <pubmed_id>17852390</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00103 +/- 0.000302</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>commercial skim milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637.</reference_text>
          <pubmed_id>17852390</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00326 +/- 0.000946</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole, commercial</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637.</reference_text>
          <pubmed_id>17852390</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00147</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial half-s</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00101</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00306</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB01536</drugbank_id>
  <chemspider_id>5898</chemspider_id>
  <kegg_id>C00280</kegg_id>
  <foodb_id>FDB030678</foodb_id>
  <pubchem_compound_id>6128</pubchem_compound_id>
  <chebi_id>16422</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>ANDROST4ENE</meta_cyc_id>
  <knapsack_id>C00003644</knapsack_id>
  <wikipedia_id>Androstenedione</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>2210012</bigg_id>
  <metlin_id>2795</metlin_id>
  <synthesis_reference>Egorova, Olga V.; Gulevskaya, Seraphima A.; Puntus, Irina F.; Filonov, Andrey E.; Donova, Marina V.  Production of androstenedione using mutants of Mycobacterium sp.    Journal of Chemical Technology and Biotechnology  (2002),  77(2),  141-147.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637.</reference_text>
      <pubmed_id>17852390</pubmed_id>
    </reference>
    <reference>
      <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
      <pubmed_id>18412364</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:02 UTC</creation_date>
  <update_date>2020-04-16 22:58:49 UTC</update_date>
  <accession>BMDB0000054</accession>
  <secondary_accessions>
    <accession>BMDB00054</accession>
  </secondary_accessions>
  <name>Bilirubin</name>
  <description>Bilirubin belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. Bilirubin is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Bilirubin exists in all living species, ranging from bacteria to humans. In cattle, bilirubin is involved in the metabolic pathway called the porphyrin metabolism pathway. Bilirubin is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acid</synonym>
    <synonym>2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid</synonym>
    <synonym>2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid</synonym>
    <synonym>8,12-Bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbiladiene-ac-1,19(21H,24H)-dione</synonym>
    <synonym>Bilirubin(Z,Z)</synonym>
    <synonym>Bilirubin-ixalpha</synonym>
    <synonym>1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionate</synonym>
    <synonym>2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoate</synonym>
    <synonym>2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoate</synonym>
    <synonym>Bilirubin ixalpha</synonym>
    <synonym>(4Z,15Z)-Bilirubin ixa</synonym>
    <synonym>(Z,Z)-Bilirubin ixa</synonym>
    <synonym>1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionate</synonym>
    <synonym>1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionic acid</synonym>
    <synonym>3-(2-((3-(2-Carboxyethyl)-4-methyl-5-((3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoate</synonym>
    <synonym>3-(2-((3-(2-Carboxyethyl)-4-methyl-5-((3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoic acid</synonym>
    <synonym>3-(2-((3-(2-Carboxyethyl)-4-methyl-5-[(Z)-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl)methyl)-4-methyl-5-[(Z)-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene</synonym>
    <synonym>3-[2-[[3-(2-Carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoate</synonym>
    <synonym>3-[2-[[3-(2-Carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid</synonym>
    <synonym>3-[2-[[3-(2-Carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoate</synonym>
    <synonym>3-[2-[[3-(2-Carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid</synonym>
    <synonym>Bilirubin IX-alpha</synonym>
    <synonym>Cholerythrin</synonym>
    <synonym>Hematoidin</synonym>
    <synonym>Bilirubin IX alpha</synonym>
  </synonyms>
  <chemical_formula>C33H36N4O6</chemical_formula>
  <average_molecular_weight>584.6621</average_molecular_weight>
  <monisotopic_moleculate_weight>584.263484904</monisotopic_moleculate_weight>
  <iupac_name>3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid</iupac_name>
  <traditional_iupac>bilirubin</traditional_iupac>
  <cas_registry_number>635-65-4</cas_registry_number>
  <smiles>CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1</smiles>
  <inchi>InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-</inchi>
  <inchikey>BPYKTIZUTYGOLE-IFADSCNNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Bilirubins</sub_class>
    <direct_parent>Bilirubins</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrrolines</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Bilirubin skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Pyrroline</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>biladienes</external_descriptor>
      <external_descriptor>dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>0.009 mg/mL at 25 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>584.6621</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>584.263484904</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C33H36N4O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BPYKTIZUTYGOLE-IFADSCNNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>164.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>168.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>66.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>58590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>58591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>58592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>114546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>114547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>114548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1114</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2.52</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Dacos Chemistry Analyzer in Hereford cows</comment>
      <references>
        <reference>
          <reference_text>Early RJ, McBride BW, Ball RO: Growth and metabolism in somatotropin-treated steers: I. Growth, serum chemistry and carcass weights. J Anim Sci. 1990 Dec;68(12):4134-43. doi: 10.2527/1990.68124134x.</reference_text>
          <pubmed_id>2286555</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00486</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB021886</foodb_id>
  <chemspider_id>4444055</chemspider_id>
  <pubchem_compound_id>5280352</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16990</chebi_id>
  <knapsack_id>C00029828</knapsack_id>
  <wikipedia_id>Bilirubin</wikipedia_id>
  <meta_cyc_id>BILIRUBIN</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35117</bigg_id>
  <metlin_id>81</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00102</protein_accession>
      <name>Prostaglandin-H2 D-isomerase</name>
      <uniprot_id>O02853</uniprot_id>
      <gene_name>PTGDS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00585</protein_accession>
      <name>Flavin reductase</name>
      <uniprot_id>P52556</uniprot_id>
      <gene_name>BLVRB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01241</protein_accession>
      <name>Glutathione S-transferase theta-1</name>
      <uniprot_id>Q2NL00</uniprot_id>
      <gene_name>GSTT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01929</protein_accession>
      <name>Alpha-fetoprotein</name>
      <uniprot_id>Q3SZ57</uniprot_id>
      <gene_name>AFP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02601</protein_accession>
      <name>Fatty acid-binding protein, liver</name>
      <uniprot_id>P80425</uniprot_id>
      <gene_name>FABP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:03 UTC</creation_date>
  <update_date>2020-04-15 22:32:00 UTC</update_date>
  <accession>BMDB0000055</accession>
  <secondary_accessions>
    <accession>BMDB00055</accession>
  </secondary_accessions>
  <name>Cellobiose</name>
  <description/>
  <synonyms>
    <synonym>1-beta-D-Glucopyranosyl-4-beta-D-glucopyranose</synonym>
    <synonym>4-O-beta-D-Glucopyranosyl-beta-D-glucopyranose</synonym>
    <synonym>beta-D-GLC-(1-&gt;4)-beta-D-GLC</synonym>
    <synonym>beta-D-GLCP-(1-&gt;4)-beta-D-GLCP</synonym>
    <synonym>beta-D-Glucosyl-(1-&gt;4)-beta-D-glucose</synonym>
    <synonym>GLCB1-4GLCB</synonym>
    <synonym>Glcbeta1-4glcbeta</synonym>
    <synonym>1-b-D-Glucopyranosyl-4-b-D-glucopyranose</synonym>
    <synonym>1-Β-D-glucopyranosyl-4-β-D-glucopyranose</synonym>
    <synonym>4-O-b-D-Glucopyranosyl-b-D-glucopyranose</synonym>
    <synonym>4-O-Β-D-glucopyranosyl-β-D-glucopyranose</synonym>
    <synonym>b-D-GLC-(1-&gt;4)-b-D-GLC</synonym>
    <synonym>Β-D-GLC-(1-&gt;4)-β-D-GLC</synonym>
    <synonym>b-D-GLCP-(1-&gt;4)-b-D-GLCP</synonym>
    <synonym>Β-D-GLCP-(1-&gt;4)-β-D-GLCP</synonym>
    <synonym>b-D-Glucosyl-(1-&gt;4)-b-D-glucose</synonym>
    <synonym>Β-D-glucosyl-(1-&gt;4)-β-D-glucose</synonym>
    <synonym>4-(b-D-Glucosido)-D-glucose</synonym>
    <synonym>4-(b-delta-Glucosido)-delta-glucose</synonym>
    <synonym>4-(beta-D-Glucosido)-D-glucose</synonym>
    <synonym>4-(beta-delta-Glucosido)-delta-glucose</synonym>
    <synonym>4-beta-D-Glucopyranosyl-D-glucopyranose</synonym>
    <synonym>4-beta-delta-Glucopyranosyl-delta-glucopyranose</synonym>
    <synonym>4-O-b-D-Glucopyranosyl-D-glucose</synonym>
    <synonym>4-O-beta-D-Glucopyranosyl-D-glucose</synonym>
    <synonym>4-O-beta-delta-Glucopyranosyl-delta-glucose</synonym>
    <synonym>Cellose</synonym>
    <synonym>D-(+)-Cellobiose</synonym>
    <synonym>D-Cellobiose</synonym>
    <synonym>D-Glucosyl-b-(1-&gt;4)-D-glucose</synonym>
    <synonym>D-Glucosyl-beta-(1-4)-D-glucose</synonym>
    <synonym>D-Glucosyl-beta-(1-&gt;4)-D-glucose</synonym>
    <synonym>delta-(+)-Cellobiose</synonym>
    <synonym>delta-Cellobiose</synonym>
    <synonym>delta-Glucosyl-beta-(1-4)-delta-glucose</synonym>
    <synonym>delta-Glucosyl-beta-(1-&gt;4)-delta-glucose</synonym>
    <synonym>4 O beta D Glucopyranosyl D glucopyranose</synonym>
    <synonym>4-O-beta-D-Glucopyranosyl-D-glucopyranose</synonym>
    <synonym>b-Cellobiose</synonym>
    <synonym>Β-cellobiose</synonym>
    <synonym>CELLOBIOSE</synonym>
  </synonyms>
  <chemical_formula>C12H22O11</chemical_formula>
  <average_molecular_weight>342.2965</average_molecular_weight>
  <monisotopic_moleculate_weight>342.116211546</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>β-cellobiose</traditional_iupac>
  <cas_registry_number>528-50-7</cas_registry_number>
  <smiles>OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8-,9-,10-,11-,12+/m1/s1</inchi>
  <inchikey>GUBGYTABKSRVRQ-QRZGKKJRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>O-glycosyl compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Disaccharides</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>cellobiose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>229 - 230 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>111.0 mg/mL at 15 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>342.2965</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>342.116211546</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H22O11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8-,9-,10-,11-,12+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GUBGYTABKSRVRQ-QRZGKKJRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>189.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>944</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>87</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>89</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181979</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C06422</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB007497</foodb_id>
  <chemspider_id>10261</chemspider_id>
  <pubchem_compound_id>10712</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>36217</chebi_id>
  <meta_cyc_id/>
  <knapsack_id>C00001134</knapsack_id>
  <wikipedia_id>Cellobiose</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>3480</metlin_id>
  <synthesis_reference>Machida, Makoto; Hosokawa, Koji.  Enzymic preparation of cellooligosaccharide with cellulase.    Jpn. Kokai Tokkyo Koho  (2006),     20pp.  CODEN: JKXXAF  JP  2006204294  A  20060810  CAN 145:187210  AN 2006:786561</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:05 UTC</creation_date>
  <update_date>2020-04-16 20:38:17 UTC</update_date>
  <accession>BMDB0000056</accession>
  <secondary_accessions>
    <accession>BMDB00056</accession>
  </secondary_accessions>
  <name>Beta-Alanine</name>
  <description/>
  <synonyms>
    <synonym>3-Aminopropanoic acid</synonym>
    <synonym>3-Aminopropionic acid</synonym>
    <synonym>BAla</synonym>
    <synonym>beta-Aminopropionic acid</synonym>
    <synonym>H-beta-Ala-OH</synonym>
    <synonym>Omega-aminopropionic acid</synonym>
    <synonym>3-Aminopropanoate</synonym>
    <synonym>Abufene</synonym>
    <synonym>3-Aminopropionate</synonym>
    <synonym>b-Aminopropionate</synonym>
    <synonym>b-Aminopropionic acid</synonym>
    <synonym>beta-Aminopropionate</synonym>
    <synonym>Β-aminopropionate</synonym>
    <synonym>Β-aminopropionic acid</synonym>
    <synonym>H-b-Ala-OH</synonym>
    <synonym>H-Β-ala-OH</synonym>
    <synonym>Omega-aminopropionate</synonym>
    <synonym>b-Alanine</synonym>
    <synonym>Β-alanine</synonym>
    <synonym>2-Carboxyethylamine</synonym>
    <synonym>3-Amino-propanoate</synonym>
    <synonym>3-Amino-propanoic acid</synonym>
    <synonym>b-Aminopropanoate</synonym>
    <synonym>b-Aminopropanoic acid</synonym>
    <synonym>beta Alanine</synonym>
    <synonym>beta-Aminopropanoate</synonym>
    <synonym>beta-Aminopropanoic acid</synonym>
    <synonym>3 Aminopropionic acid</synonym>
  </synonyms>
  <chemical_formula>C3H7NO2</chemical_formula>
  <average_molecular_weight>89.0932</average_molecular_weight>
  <monisotopic_moleculate_weight>89.047678473</monisotopic_moleculate_weight>
  <iupac_name>3-aminopropanoic acid</iupac_name>
  <traditional_iupac>β alanine</traditional_iupac>
  <cas_registry_number>107-95-9</cas_registry_number>
  <smiles>NCCC(O)=O</smiles>
  <inchi>InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)</inchi>
  <inchikey>UCMIRNVEIXFBKS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Beta amino acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>beta-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>200 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>545.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.05</value>
      <source>TSAI,RS ET AL. (1991)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-aminopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>89.0932</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>89.047678473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UCMIRNVEIXFBKS-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>20.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>90</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>91</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37270</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>8+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>8.8-9.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>750+/-137</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>149+/-57</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>84-155</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>3-33</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>72+/-38</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>122+/-37</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>48+/-13</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00099</kegg_id>
  <drugbank_id>DB03107</drugbank_id>
  <foodb_id>FDB002253</foodb_id>
  <chemspider_id>234</chemspider_id>
  <pubchem_compound_id>239</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16958</chebi_id>
  <meta_cyc_id>B-ALANINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001333</knapsack_id>
  <bigg_id>33848</bigg_id>
  <wikipedia_id>Beta-Alanine</wikipedia_id>
  <metlin_id>5119</metlin_id>
  <synthesis_reference>Buc, Saul R.; Ford, Jared H.; Wise, E. C. Improved synthesis of b-alanine. Journal of the American Chemical Society (1945), 67 92-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:06 UTC</creation_date>
  <update_date>2020-04-15 20:47:42 UTC</update_date>
  <accession>BMDB0000058</accession>
  <secondary_accessions>
    <accession>BMDB00058</accession>
  </secondary_accessions>
  <name>Cyclic AMP</name>
  <description>3',5'-Cyclic AMP, also known as cyclic AMP or camp, belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group. 3',5'-Cyclic AMP exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. 3',5'-Cyclic AMP exists in all living species, ranging from bacteria to humans. In cattle, 3',5'-cyclic AMP is involved in the metabolic pathway called the lysophosphatidic Acid LPA6 signalling pathway.</description>
  <synonyms>
    <synonym>Adenosine 3',5'-cyclic monophosphate</synonym>
    <synonym>Adenosine 3',5'-cyclic phosphate</synonym>
    <synonym>Adenosine 3',5'-phosphate</synonym>
    <synonym>ADENOSINE-3',5'-cyclic-monophosphATE</synonym>
    <synonym>CAMP</synonym>
    <synonym>Cyclic adenylic acid</synonym>
    <synonym>Adenosine 3',5'-cyclic monophosphoric acid</synonym>
    <synonym>Adenosine 3',5'-cyclic phosphoric acid</synonym>
    <synonym>Adenosine 3',5'-phosphoric acid</synonym>
    <synonym>ADENOSINE-3',5'-cyclic-monophosphoric acid</synonym>
    <synonym>Cyclic adenylate</synonym>
    <synonym>3'5'-Cyclic AMP</synonym>
    <synonym>6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-D][1,3,2]dioxaphosphinine-2,7-diol 2-oxide</synonym>
    <synonym>Acrasin</synonym>
    <synonym>Adenosine 3',5'-cyclophosphate</synonym>
    <synonym>Adenosine 3',5'-monophosphate</synonym>
    <synonym>Adenosine 3,5'-cyclic monophosphorate</synonym>
    <synonym>Adenosine 3,5'-cyclic monophosphoric acid</synonym>
    <synonym>Adenosine cyclic monophosphate</synonym>
    <synonym>Adenosine cyclic-monophosphate</synonym>
    <synonym>Adenosine-cyclic-phosphate</synonym>
    <synonym>Adenosine-cyclic-phosphoric-acid</synonym>
    <synonym>Cyclic 3',5'-adenylate</synonym>
    <synonym>Cyclic 3',5'-adenylic acid</synonym>
    <synonym>Cyclic 3',5'-AMP</synonym>
    <synonym>Cyclic adenosine 3',5'-phosphate</synonym>
    <synonym>3',5'-monoPhosphate, adenosine cyclic</synonym>
    <synonym>Cyclic AMP, disodium salt</synonym>
    <synonym>Cyclic AMP, monopotassium salt</synonym>
    <synonym>Cyclic AMP, sodium salt</synonym>
    <synonym>AMP, Cyclic</synonym>
    <synonym>Adenosine cyclic 3',5' monophosphate</synonym>
    <synonym>Adenosine cyclic-3',5'-monophosphate</synonym>
    <synonym>Cyclic AMP, (R)-isomer</synonym>
    <synonym>Cyclic AMP, monosodium salt</synonym>
    <synonym>Adenosine cyclic 3',5'-monophosphate</synonym>
    <synonym>monoPhosphate, adenosine cyclic</synonym>
    <synonym>Adenosine cyclic 3,5 monophosphate</synonym>
    <synonym>Cyclic 3',5'-monophosphate, adenosine</synonym>
    <synonym>Cyclic AMP, monoammonium salt</synonym>
    <synonym>Cyclic monophosphate, adenosine</synonym>
    <synonym>Cyclic-3',5'-monophosphate, adenosine</synonym>
    <synonym>Cyclic AMP</synonym>
  </synonyms>
  <chemical_formula>C10H12N5O6P</chemical_formula>
  <average_molecular_weight>329.2059</average_molecular_weight>
  <monisotopic_moleculate_weight>329.052519653</monisotopic_moleculate_weight>
  <iupac_name>(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one</iupac_name>
  <traditional_iupac>(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2,7-dihydroxy-tetrahydro-4H-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one</traditional_iupac>
  <cas_registry_number>60-92-4</cas_registry_number>
  <smiles>[H][C@@]12COP(O)(=O)O[C@@]1([H])[C@@H](O)[C@@H](O2)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>IVOMOUWHDPKRLL-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Cyclic purine nucleotides</sub_class>
    <direct_parent>3',5'-cyclic purine nucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic phosphoric acids and derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3',5'-cyclic purine ribonucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3',5'-Cyclic nuclcleotides</external_descriptor>
      <external_descriptor>3',5'-cyclic purine nucleotide</external_descriptor>
      <external_descriptor>adenyl ribonucleotide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>219 - 220 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>4 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.96</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>329.2059</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>329.052519653</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12COP(O)(=O)O[C@@]1([H])[C@@H](O)[C@@H](O2)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N5O6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IVOMOUWHDPKRLL-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>154.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>70.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Activation of cAMP-dependent protein kinase, PKA</name>
      <smpdb_id>SMP0108201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Corticotropin Activation of Cortisol Production</name>
      <smpdb_id>SMP0108167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dopamine Activation of Neurological Reward System</name>
      <smpdb_id>SMP0107994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 4 and Serotonin</name>
      <smpdb_id>SMP0108169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 6 and Serotonin</name>
      <smpdb_id>SMP0108172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 7 and Serotonin</name>
      <smpdb_id>SMP0108170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>GnRH Signaling Pathway</name>
      <smpdb_id>SMP0120925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2a and Adenosine</name>
      <smpdb_id>SMP0108174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2b and Adenosine</name>
      <smpdb_id>SMP0108178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through FSH Receptor and Follicle Stimulating Hormone</name>
      <smpdb_id>SMP0108183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Histamine H2 Receptor and Histamine</name>
      <smpdb_id>SMP0107995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through LHCGR Receptor and Luteinizing Hormone/Choriogonadotropin</name>
      <smpdb_id>SMP0108184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through PGD2 receptor and Prostaglandin D2</name>
      <smpdb_id>SMP0107997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Prostacyclin Receptor and Prostacyclin</name>
      <smpdb_id>SMP0107998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ion Channels and Their Functional Role in Vascular Endothelium</name>
      <smpdb_id>SMP0108207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA1 Signalling</name>
      <smpdb_id>SMP0108191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA2 Signalling</name>
      <smpdb_id>SMP0108193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA3 Signalling</name>
      <smpdb_id>SMP0108194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA4 Signalling</name>
      <smpdb_id>SMP0108196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA5 Signalling</name>
      <smpdb_id>SMP0108198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA6 Signalling</name>
      <smpdb_id>SMP0108199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vasopressin Regulation of Water Homeostasis</name>
      <smpdb_id>SMP0108181</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>94</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2704</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179135</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00575</kegg_id>
  <drugbank_id>DB02527</drugbank_id>
  <foodb_id>FDB030763</foodb_id>
  <chemspider_id>5851</chemspider_id>
  <pubchem_compound_id>6076</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17489</chebi_id>
  <meta_cyc_id>CAMP</meta_cyc_id>
  <knapsack_id>C00001497</knapsack_id>
  <wikipedia_id>Cyclic_AMP</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>1484809</bigg_id>
  <metlin_id>5120</metlin_id>
  <synthesis_reference>Genieser, H. G.; Butt, E.; Bottin, U.; Dostmann, W.; Jastorff, B. Synthesis of the 3',5'-cyclic phosphates from unprotected nucleosides. Synthesis  (1989),   (1),  53-4.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00807</protein_accession>
      <name>cAMP-dependent protein kinase type II-alpha regulatory subunit</name>
      <uniprot_id>P00515</uniprot_id>
      <gene_name>PRKAR2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00808</protein_accession>
      <name>cAMP-dependent protein kinase inhibitor alpha</name>
      <uniprot_id>Q3SX13</uniprot_id>
      <gene_name>PKIA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00809</protein_accession>
      <name>cAMP-dependent protein kinase type I-alpha regulatory subunit</name>
      <uniprot_id>P00514</uniprot_id>
      <gene_name>PRKAR1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00810</protein_accession>
      <name>cAMP-dependent protein kinase type II-beta regulatory subunit</name>
      <uniprot_id>P31322</uniprot_id>
      <gene_name>PRKAR2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01335</protein_accession>
      <name>Prostaglandin D2 receptor</name>
      <uniprot_id>A5D7K8</uniprot_id>
      <gene_name>PTGDR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01589</protein_accession>
      <name>Cyclic AMP-responsive element-binding protein 1</name>
      <uniprot_id>P27925</uniprot_id>
      <gene_name>CREB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01986</protein_accession>
      <name>Cyclic AMP-responsive element-binding protein 3-like protein 3</name>
      <uniprot_id>Q3SYZ3</uniprot_id>
      <gene_name>CREB3L3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01987</protein_accession>
      <name>CAMP responsive element binding protein-like 1</name>
      <uniprot_id>Q3KUS1</uniprot_id>
      <gene_name>CREBL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01988</protein_accession>
      <name>G-protein coupled bile acid receptor 1</name>
      <uniprot_id>Q862A9</uniprot_id>
      <gene_name>GPBAR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01989</protein_accession>
      <name>Cyclic AMP-dependent transcription factor ATF-1</name>
      <uniprot_id>Q08DA8</uniprot_id>
      <gene_name>ATF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01990</protein_accession>
      <name>cAMP-responsive element modulator</name>
      <uniprot_id>Q1LZH5</uniprot_id>
      <gene_name>CREM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01991</protein_accession>
      <name>Cyclic nucleotide-gated olfactory channel</name>
      <uniprot_id>Q03041</uniprot_id>
      <gene_name>CNGA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01992</protein_accession>
      <name>Cyclic AMP-dependent transcription factor ATF-3</name>
      <uniprot_id>Q2KII1</uniprot_id>
      <gene_name>ATF3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01993</protein_accession>
      <name>Cyclic AMP-dependent transcription factor ATF-4</name>
      <uniprot_id>Q3ZCH6</uniprot_id>
      <gene_name>ATF4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01994</protein_accession>
      <name>Cyclic AMP-responsive element-binding protein 3</name>
      <uniprot_id>Q8SQ19</uniprot_id>
      <gene_name>CREB3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01995</protein_accession>
      <name>Cyclic nucleotide-gated cation channel beta-1</name>
      <uniprot_id>Q28181</uniprot_id>
      <gene_name>CNGB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01996</protein_accession>
      <name>Cisplatin resistance-associated overexpressed protein</name>
      <uniprot_id>Q3SX41</uniprot_id>
      <gene_name>CROP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01997</protein_accession>
      <name>Agouti-signaling protein</name>
      <uniprot_id>Q29414</uniprot_id>
      <gene_name>ASIP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01998</protein_accession>
      <name>CREB-regulated transcription coactivator 2</name>
      <uniprot_id>Q08E26</uniprot_id>
      <gene_name>CRTC2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01999</protein_accession>
      <name>cAMP responsive element binding protein 1 isoform A</name>
      <uniprot_id>Q0V7N6</uniprot_id>
      <gene_name>CREB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:07 UTC</creation_date>
  <update_date>2020-04-15 22:32:00 UTC</update_date>
  <accession>BMDB0000060</accession>
  <secondary_accessions>
    <accession>BMDB00060</accession>
  </secondary_accessions>
  <name>Acetoacetic acid</name>
  <description>Acetoacetic acid, also known as 3-oxobutyrate or 3-oxobutanoic acid, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. Acetoacetic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Acetoacetic acid exists in all living species, ranging from bacteria to humans. Acetoacetic acid is a potentially toxic compound. Acetoacetic acid has been found to be associated with several diseases known as ketoacidosis, irritable bowel syndrome, anoxia, and diabetes mellitus type 2; also acetoacetic acid has been linked to the inborn metabolic disorders including glucose transporter type 1 deficiency syndrome.</description>
  <synonyms>
    <synonym>3-Ketobutanoic acid</synonym>
    <synonym>3-Ketobutyric acid</synonym>
    <synonym>3-Oxobutanoic acid</synonym>
    <synonym>3-Oxobutyric acid</synonym>
    <synonym>beta-Ketobutyric acid</synonym>
    <synonym>3-Ketobutanoate</synonym>
    <synonym>3-Ketobutyrate</synonym>
    <synonym>3-Oxobutanoate</synonym>
    <synonym>3-Oxobutyrate</synonym>
    <synonym>b-Ketobutyrate</synonym>
    <synonym>b-Ketobutyric acid</synonym>
    <synonym>beta-Ketobutyrate</synonym>
    <synonym>Β-ketobutyrate</synonym>
    <synonym>Β-ketobutyric acid</synonym>
    <synonym>Acetoacetate</synonym>
    <synonym>3-oxo-Butanoate</synonym>
    <synonym>3-oxo-Butanoic acid</synonym>
    <synonym>Diacetate</synonym>
    <synonym>Diacetic acid</synonym>
    <synonym>Acetoacetic acid, sodium salt</synonym>
    <synonym>Acetoacetic acid, calcium salt</synonym>
    <synonym>Acetoacetic acid, lithium salt</synonym>
    <synonym>Oxobutyrate</synonym>
    <synonym>Sodium acetoacetate</synonym>
  </synonyms>
  <chemical_formula>C4H6O3</chemical_formula>
  <average_molecular_weight>102.0886</average_molecular_weight>
  <monisotopic_moleculate_weight>102.031694058</monisotopic_moleculate_weight>
  <iupac_name>3-oxobutanoic acid</iupac_name>
  <traditional_iupac>acetoacetic acid</traditional_iupac>
  <cas_registry_number>541-50-4</cas_registry_number>
  <smiles>CC(=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)</inchi>
  <inchikey>WDJHALXBUFZDSR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Short-chain keto acids and derivatives</sub_class>
    <direct_parent>Short-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-dicarbonyl compounds</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Beta-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Beta-keto acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain keto acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>Oxo fatty acids</external_descriptor>
      <external_descriptor>Oxo fatty acids</external_descriptor>
      <external_descriptor>ketone body</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>36.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000 mg/mL at 20 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.0015</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-oxobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>102.0886</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>102.031694058</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H6O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WDJHALXBUFZDSR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>22.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Butyrate Metabolism</name>
      <smpdb_id>SMP0087185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ketone Body Metabolism</name>
      <smpdb_id>SMP0087202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>96</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>97</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>98</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451991</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in lactating Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 54 Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
          <pubmed_id>23394630</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Charolais cows.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4 - 14</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>40 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Enjalbert F, Nicot MC, Bayourthe C, Moncoulon R: Ketone bodies in milk and blood of dairy cows: relationship between concentrations and utilization for detection of subclinical ketosis. J Dairy Sci. 2001 Mar;84(3):583-9. doi: 10.3168/jds.S0022-0302(01)74511-0.</reference_text>
          <pubmed_id>11286410</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from 20 healthy Holstein Friesian dairy cows </comment>
      <references>
        <reference>
          <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
          <pubmed_id>23738862</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB01762</drugbank_id>
  <foodb_id>FDB021801</foodb_id>
  <kegg_id>C00164</kegg_id>
  <pubchem_compound_id>96</pubchem_compound_id>
  <chemspider_id>94</chemspider_id>
  <pdbe_id/>
  <chebi_id>15344</chebi_id>
  <meta_cyc_id>3-KETOBUTYRATE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007458</knapsack_id>
  <bigg_id>1485291</bigg_id>
  <wikipedia_id>Acetoacetic_acid</wikipedia_id>
  <metlin_id>276</metlin_id>
  <synthesis_reference>Lopez-Soriano, F. J.; Argiles, J. M.  A simple method for the preparation of acetoacetate.  Analytical Letters  (1985),  18(B5),  589-92.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Enjalbert F, Nicot MC, Bayourthe C, Moncoulon R: Ketone bodies in milk and blood of dairy cows: relationship between concentrations and utilization for detection of subclinical ketosis. J Dairy Sci. 2001 Mar;84(3):583-9. doi: 10.3168/jds.S0022-0302(01)74511-0.</reference_text>
      <pubmed_id>11286410</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
      <pubmed_id>23738862</pubmed_id>
    </reference>
    <reference>
      <reference_text>Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26.</reference_text>
      <pubmed_id>27236769</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00427</protein_accession>
      <name>Fumarylacetoacetase</name>
      <uniprot_id>A5PKH3</uniprot_id>
      <gene_name>FAH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00595</protein_accession>
      <name>Hydroxyacid-oxoacid transhydrogenase, mitochondrial</name>
      <uniprot_id>A6QP15</uniprot_id>
      <gene_name>ADHFE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01009</protein_accession>
      <name>3-hydroxybutyrate dehydrogenase type 2</name>
      <uniprot_id>Q3T046</uniprot_id>
      <gene_name>BDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01010</protein_accession>
      <name>D-beta-hydroxybutyrate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q02337</uniprot_id>
      <gene_name>BDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01139</protein_accession>
      <name>Hydroxymethylglutaryl-CoA lyase, mitochondrial</name>
      <uniprot_id>Q29448</uniprot_id>
      <gene_name>HMGCL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:08 UTC</creation_date>
  <update_date>2020-04-15 22:13:02 UTC</update_date>
  <accession>BMDB0000061</accession>
  <secondary_accessions>
    <accession>BMDB00061</accession>
  </secondary_accessions>
  <name>Adenosine 3',5'-diphosphate</name>
  <description/>
  <synonyms>
    <synonym>3'-Phosphoadenylate</synonym>
    <synonym>Adenosine 3',5'-bisphosphate</synonym>
    <synonym>PAP</synonym>
    <synonym>Phosphoadenosine phosphate</synonym>
    <synonym>3'-Phosphoadenylic acid</synonym>
    <synonym>Adenosine 3',5'-bisphosphoric acid</synonym>
    <synonym>Phosphoadenosine phosphoric acid</synonym>
    <synonym>Adenosine 3',5'-diphosphoric acid</synonym>
    <synonym>3'-Phosphoryl-AMP</synonym>
    <synonym>3,5-ADP</synonym>
    <synonym>3,5-Diphosphoadenosine</synonym>
    <synonym>3-Phosphoadenosine 5-phosphate</synonym>
    <synonym>5-(Dihydrogen phosphate) 3-adenylate</synonym>
    <synonym>5-(Dihydrogen phosphate)3'-adenylic acid</synonym>
    <synonym>Adenosine 3,5-bis</synonym>
    <synonym>Adenosine 3,5-bisphosphate</synonym>
    <synonym>Adenosine 3'-phosphate-5'-phosphate, disodium salt</synonym>
    <synonym>3'-Phosphoadenosine 5'-phosphate</synonym>
    <synonym>Adenosine 3'-phosphate-5'-phosphate, monosodium salt</synonym>
    <synonym>3',5'-ADP</synonym>
    <synonym>Adenosine 3'-phosphate-5'-phosphate</synonym>
  </synonyms>
  <chemical_formula>C10H15N5O10P2</chemical_formula>
  <average_molecular_weight>427.2011</average_molecular_weight>
  <monisotopic_moleculate_weight>427.029414749</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>adenosine 3',5'-bisphosphate</traditional_iupac>
  <cas_registry_number>1053-73-2</cas_registry_number>
  <smiles>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O</smiles>
  <inchi>InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>WHTCPDAXWFLDIH-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside 3',5'-bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside 3',5'-bisphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>adenosine bisphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>614.5 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>427.2011</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>427.029414749</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H15N5O10P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WHTCPDAXWFLDIH-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>232.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sulfate/Sulfite Metabolism</name>
      <smpdb_id>SMP0087216</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30604</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00054</kegg_id>
  <drugbank_id>DB01812</drugbank_id>
  <chemspider_id>140102</chemspider_id>
  <foodb_id>FDB030650</foodb_id>
  <pdbe_id/>
  <chebi_id>17985</chebi_id>
  <pubchem_compound_id>159296</pubchem_compound_id>
  <knapsack_id>C00019352</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>33684</bigg_id>
  <metlin_id/>
  <synthesis_reference>Tsunako, Mitsutomo; Kotone, Akira.  Preparation of nucleoside-2',5'- and 3',5'-diphosphoric acids.    Jpn. Kokai Tokkyo Koho  (1991),     13 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00080</protein_accession>
      <name>Galactosylceramide sulfotransferase</name>
      <uniprot_id>A6QNK1</uniprot_id>
      <gene_name>GAL3ST1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00195</protein_accession>
      <name>3'(2'),5'-bisphosphate nucleotidase 1</name>
      <uniprot_id>Q3ZCK3</uniprot_id>
      <gene_name>BPNT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00375</protein_accession>
      <name>Protein-tyrosine sulfotransferase 2</name>
      <uniprot_id>Q3SYY2</uniprot_id>
      <gene_name>TPST2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00376</protein_accession>
      <name>Sulfotransferase 1A1</name>
      <uniprot_id>P50227</uniprot_id>
      <gene_name>SULT1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00377</protein_accession>
      <name>Bifunctional heparan sulfate N-deacetylase/N-sulfotransferase 2</name>
      <uniprot_id>O97583</uniprot_id>
      <gene_name>NDST2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00378</protein_accession>
      <name>Estrogen sulfotransferase</name>
      <uniprot_id>P19217</uniprot_id>
      <gene_name>SULT1E1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:09 UTC</creation_date>
  <update_date>2020-04-16 21:05:25 UTC</update_date>
  <accession>BMDB0000062</accession>
  <secondary_accessions>
    <accession>BMDB00062</accession>
  </secondary_accessions>
  <name>L-Carnitine</name>
  <description>L-Carnitine, also known as carnitine d-form, belongs to the class of organic compounds known as carnitines. These are organic compounds containing the quaternary ammonium compound carnitine. L-Carnitine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). L-Carnitine participates in a number of enzymatic reactions, within cattle. In particular, Propionyl-CoA and L-carnitine can be converted into propionylcarnitine through its interaction with the enzyme carnitine O-acetyltransferase. In addition, Acetyl-CoA and L-carnitine can be converted into L-acetylcarnitine through its interaction with the enzyme carnitine O-acetyltransferase. In cattle, L-carnitine is involved in the metabolic pathway called the oxidation OF branched-chain fatty acids pathway.</description>
  <synonyms>
    <synonym>(-)-Carnitine</synonym>
    <synonym>(-)-L-Carnitine</synonym>
    <synonym>3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium hydroxide, inner salt</synonym>
    <synonym>Carnicor</synonym>
    <synonym>Carnitene</synonym>
    <synonym>Carnitine</synonym>
    <synonym>Carnitor</synonym>
    <synonym>Karnitin</synonym>
    <synonym>Levocarnitine</synonym>
    <synonym>Vitamin BT</synonym>
    <synonym>L-gamma-Trimethyl-beta-hydroxybutyrobetaine</synonym>
    <synonym>(R)-Carnitine</synonym>
    <synonym>L-g-Trimethyl-b-hydroxybutyrobetaine</synonym>
    <synonym>L-Γ-trimethyl-β-hydroxybutyrobetaine</synonym>
    <synonym>(-)-(R)-3-Hydroxy-4-(trimethylammonio)butyrate</synonym>
    <synonym>(R)-(3-Carboxy-2-hydroxypropyl)trimethylammonium hydroxide</synonym>
    <synonym>(S)-Carnitine</synonym>
    <synonym>1-Carnitine</synonym>
    <synonym>3-Carboxy-2-hydroxy-N,N,N-trimethyl-1-propanaminium</synonym>
    <synonym>3-Hydroxy-4-trimethylammoniobutanoate</synonym>
    <synonym>3-Hydroxy-4-trimethylammoniobutanoic acid</synonym>
    <synonym>Bicarnesine</synonym>
    <synonym>Carniking</synonym>
    <synonym>Carniking 50</synonym>
    <synonym>Carnilean</synonym>
    <synonym>Carnipass</synonym>
    <synonym>Carnipass 20</synonym>
    <synonym>D-Carnitine</synonym>
    <synonym>delta-Carnitine</synonym>
    <synonym>DL-Carnitine</synonym>
    <synonym>gamma-Trimethyl-ammonium-beta-hydroxybutirate</synonym>
    <synonym>gamma-Trimethyl-beta-hydroxybutyrobetaine</synonym>
    <synonym>gamma-Trimethyl-hydroxybutyrobetaine</synonym>
    <synonym>L-(-)-Carnitine</synonym>
    <synonym>Levocarnitina</synonym>
    <synonym>Levocarnitinum</synonym>
    <synonym>R-(-)-3-Hydroxy-4-trimethylaminobutyrate</synonym>
    <synonym>L Carnitine</synonym>
    <synonym>L-Carnitine</synonym>
  </synonyms>
  <chemical_formula>C7H15NO3</chemical_formula>
  <average_molecular_weight>161.1989</average_molecular_weight>
  <monisotopic_moleculate_weight>161.105193351</monisotopic_moleculate_weight>
  <iupac_name>(3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>L-carnitine</traditional_iupac>
  <cas_registry_number>541-15-1</cas_registry_number>
  <smiles>C[N+](C)(C)C[C@H](O)CC([O-])=O</smiles>
  <inchi>InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m1/s1</inchi>
  <inchikey>PHIQHXFUZVPYII-ZCFIWIBFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as carnitines. These are organic compounds containing the quaternary ammonium compound carnitine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Quaternary ammonium salts</sub_class>
    <direct_parent>Carnitines</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Carnitine</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>carnitine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R)-3-hydroxy-4-(trimethylazaniumyl)butanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>161.1989</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>161.105193351</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)C[C@H](O)CC([O-])=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H15NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3/t6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PHIQHXFUZVPYII-ZCFIWIBFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>63.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4924</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448139</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1.29 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by DFI-MS/MS (P180) 1 week after parturition</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>7+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2.54 +/- 0.51</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by DFI-MS/MS (P180) 4 week after parturition</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3.14 +/- 0.66</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by DFI-MS/MS (P180) 4 week before parturition</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>6.12 +/- 21.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by ESI-MS/MS in male Charolais x German Holstein</comment>
      <references>
        <reference>
          <reference_text>Widmann P, Reverter A, Weikard R, Suhre K, Hammon HM, Albrecht E, Kuehn C: Systems biology analysis merging phenotype, metabolomic and genomic data identifies Non-SMC Condensin I Complex, Subunit G (NCAPG) and cellular maintenance processes as major contributors to genetic variability in bovine feed efficiency. PLoS One. 2015 Apr 15;10(4):e0124574. doi: 10.1371/journal.pone.0124574. eCollection 2015.</reference_text>
          <pubmed_id>25875852</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by electrospray ionization tandem mass spectrometry with the Biocrates AbsoluteIDQ in male Charolais and Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Weikard R, Altmaier E, Suhre K, Weinberger KM, Hammon HM, Albrecht E, Setoguchi K, Takasuga A, Kuhn C: Metabolomic profiles indicate distinct physiological pathways affected by two loci with major divergent effect on Bos taurus growth and lipid deposition. Physiol Genomics. 2010 Oct;42A(2):79-88. doi: 10.1152/physiolgenomics.00120.2010. Epub 2010 Jul 20.</reference_text>
          <pubmed_id>20647382</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>22+/-6</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>1856+/-424</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>346</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>61 +/- 6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>68 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>68 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>62 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>81.36 +/- 20.84</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>72.7 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>77 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>79 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>67 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>85.71 +/- 17.08</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from 20 healthy Holstein Friesian dairy cows </comment>
      <references>
        <reference>
          <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
          <pubmed_id>23738862</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 milk samples from Swedish Red cows </comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>75.91 +/- 18.17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>317-437</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1022.66 +/- 63.87</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1072.83 +/- 69.97</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>791-1143</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>829.28 +/- 38.28</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>2600</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>983.18 +/- 45.99</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>3+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>1751+/-337</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>20+/-6</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00318</kegg_id>
  <drugbank_id>DB00583</drugbank_id>
  <chemspider_id>2006614</chemspider_id>
  <foodb_id>FDB000571</foodb_id>
  <pdbe_id/>
  <chebi_id>16347</chebi_id>
  <pubchem_compound_id>10917</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id>CARNITINE</meta_cyc_id>
  <wikipedia_id>Carnitine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34600</bigg_id>
  <metlin_id>52</metlin_id>
  <synthesis_reference> Bols, Mikael; Lundt, Inge; Pedersen, Christian. Simple synthesis of (R)-carnitine from D-galactono-1,4-lactone. Tetrahedron (1992), 48(2), 319-24.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
      <pubmed_id>23738862</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00244</protein_accession>
      <name>Peroxisomal carnitine O-octanoyltransferase</name>
      <uniprot_id>O19094</uniprot_id>
      <gene_name>CROT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00245</protein_accession>
      <name>Carnitine O-palmitoyltransferase 1, muscle isoform</name>
      <uniprot_id>Q58DK1</uniprot_id>
      <gene_name>CPT1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00246</protein_accession>
      <name>Carnitine O-palmitoyltransferase 2, mitochondrial</name>
      <uniprot_id>Q2KJB7</uniprot_id>
      <gene_name>CPT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01571</protein_accession>
      <name>Solute carrier family 22 member 16</name>
      <uniprot_id>Q17QN9</uniprot_id>
      <gene_name>SLC22A16</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:10 UTC</creation_date>
  <update_date>2020-04-16 20:40:44 UTC</update_date>
  <accession>BMDB0000063</accession>
  <secondary_accessions>
    <accession>BMDB00063</accession>
  </secondary_accessions>
  <name>Cortisol</name>
  <description/>
  <synonyms>
    <synonym>(11beta)-11,17,21-Trihydroxypregn-4-ene-3,20-dione</synonym>
    <synonym>11beta,17alpha,21-Trihydroxy-4-pregnene-3,20-dione</synonym>
    <synonym>11beta-Hydrocortisone</synonym>
    <synonym>17-Hydroxycorticosterone</synonym>
    <synonym>4-Pregnen-11beta,17alpha,21-triol-3,20-dione</synonym>
    <synonym>Hidrocortisona</synonym>
    <synonym>Hydrocortisone</synonym>
    <synonym>Hydrocortisonum</synonym>
    <synonym>Kendall's compound F</synonym>
    <synonym>Reichstein's substance m</synonym>
    <synonym>HC</synonym>
    <synonym>Acticort</synonym>
    <synonym>Anusol HC</synonym>
    <synonym>Colocort</synonym>
    <synonym>Cortef</synonym>
    <synonym>Hytone</synonym>
    <synonym>Plenadren</synonym>
    <synonym>(11b)-11,17,21-Trihydroxypregn-4-ene-3,20-dione</synonym>
    <synonym>(11Β)-11,17,21-trihydroxypregn-4-ene-3,20-dione</synonym>
    <synonym>11b,17a,21-Trihydroxy-4-pregnene-3,20-dione</synonym>
    <synonym>11Β,17α,21-trihydroxy-4-pregnene-3,20-dione</synonym>
    <synonym>11b-Hydrocortisone</synonym>
    <synonym>11Β-hydrocortisone</synonym>
    <synonym>4-Pregnen-11b,17a,21-triol-3,20-dione</synonym>
    <synonym>4-Pregnen-11β,17α,21-triol-3,20-dione</synonym>
    <synonym>11beta-Hydroxycortisone</synonym>
    <synonym>17alpha-Hydroxycorticosterone</synonym>
    <synonym>Anti-inflammatory hormone</synonym>
    <synonym>Dihydrocostisone</synonym>
    <synonym>Hydrocorticosterone</synonym>
    <synonym>Hydrocortisone acetate</synonym>
    <synonym>Hydrocortisone alcohol</synonym>
    <synonym>Hydrocortisone base</synonym>
    <synonym>Hydrocortisone butyrate</synonym>
    <synonym>Hydrocortisone free alcohol</synonym>
    <synonym>Hydrocortisone sodium phosphate</synonym>
    <synonym>Hydrocortisone valerate</synonym>
    <synonym>Hydroxycortisone</synonym>
    <synonym>Idrocortisone</synonym>
    <synonym>Balneol-HC</synonym>
    <synonym>CORTRIL</synonym>
    <synonym>Cetacort</synonym>
    <synonym>Cort-dome</synonym>
    <synonym>Flexicort</synonym>
    <synonym>Hi-cor</synonym>
    <synonym>Hydrocortisone in absorbase</synonym>
    <synonym>Nogenic HC</synonym>
    <synonym>Aeroseb-HC</synonym>
    <synonym>Ala-cort</synonym>
    <synonym>Ala-scalp</synonym>
    <synonym>Penecort</synonym>
    <synonym>Texacort</synonym>
    <synonym>H-Cort</synonym>
    <synonym>HYDROCORTONE</synonym>
    <synonym>Ophthocort</synonym>
    <synonym>Terra-cortril</synonym>
    <synonym>Cor-oticin</synonym>
    <synonym>Nutracort</synonym>
    <synonym>Cortifoam</synonym>
    <synonym>Glycort</synonym>
    <synonym>HC #1</synonym>
    <synonym>HC #4</synonym>
    <synonym>Proctocort</synonym>
    <synonym>Anucort-HC</synonym>
    <synonym>Cortenema</synonym>
    <synonym>Dermacort</synonym>
    <synonym>Micort-HC</synonym>
    <synonym>Synacort</synonym>
    <synonym>U-cort</synonym>
    <synonym>Eldecort</synonym>
    <synonym>Epicort</synonym>
    <synonym>neo-Cortef</synonym>
    <synonym>Stie-cort</synonym>
    <synonym>Anusol-HC</synonym>
    <synonym>Beta-HC</synonym>
    <synonym>hydro-RX</synonym>
    <synonym>Locoid</synonym>
    <synonym>b-HC</synonym>
    <synonym>β-HC</synonym>
    <synonym>11-beta-Hydrocortisone</synonym>
    <synonym>11-beta-Hydroxycortisone</synonym>
    <synonym>11-Hydrocortisone</synonym>
    <synonym>11a-Hydroxycorticosterone</synonym>
    <synonym>11alpha-Hydroxycorticosterone</synonym>
    <synonym>11b,17,21-Trihydroxyprogesterone</synonym>
    <synonym>11b-Hydroxycortisone</synonym>
    <synonym>11beta,17,21-Trihydroxyprogesterone</synonym>
    <synonym>17a-Hydroxycorticosterone</synonym>
    <synonym>4-Pregnene-11alpha,21-triol 3,20-dione</synonym>
    <synonym>4-Pregnene-11b,17a,21-triol-3,20-dione</synonym>
    <synonym>Aeroseb HC</synonym>
    <synonym>Alacort</synonym>
    <synonym>Algicirtis</synonym>
    <synonym>Alphaderm</synonym>
    <synonym>Amberin</synonym>
    <synonym>Anflam</synonym>
    <synonym>Aquacort</synonym>
    <synonym>Aquanil HC</synonym>
    <synonym>Barseb HC</synonym>
    <synonym>Basan-corti</synonym>
    <synonym>CaldeCORT spray</synonym>
    <synonym>Chronocort</synonym>
    <synonym>Clear aid</synonym>
    <synonym>Cleiton</synonym>
    <synonym>Cobadex</synonym>
    <synonym>Compound F</synonym>
    <synonym>Cor-tar-quin</synonym>
    <synonym>Cort-quin</synonym>
    <synonym>Cortanal</synonym>
    <synonym>Cortesal</synonym>
    <synonym>Corticreme</synonym>
    <synonym>Cortifan</synonym>
    <synonym>Cortiment</synonym>
    <synonym>Cortisol alcohol</synonym>
    <synonym>Cortisolonum</synonym>
    <synonym>Cortisporin</synonym>
    <synonym>Cortisporin otico</synonym>
    <synonym>Cortispray</synonym>
    <synonym>Cortizol</synonym>
    <synonym>Cortolotion</synonym>
    <synonym>Cortonema</synonym>
    <synonym>Cortoxide</synonym>
    <synonym>Cremesone</synonym>
    <synonym>Cremicort-H</synonym>
    <synonym>Cutisol</synonym>
    <synonym>Delacort</synonym>
    <synonym>Derm-aid</synonym>
    <synonym>Dermil</synonym>
    <synonym>Dermolate</synonym>
    <synonym>Dioderm</synonym>
    <synonym>Dome-cort</synonym>
    <synonym>Domolene-HC</synonym>
    <synonym>Drotic</synonym>
    <synonym>Ef corlin</synonym>
    <synonym>Efcorbin</synonym>
    <synonym>Efcortelan</synonym>
    <synonym>Efcortelin</synonym>
    <synonym>Eldercort</synonym>
    <synonym>Epiderm H</synonym>
    <synonym>Esiderm H</synonym>
    <synonym>Evacort</synonym>
    <synonym>Ficortril</synonym>
    <synonym>Fiocortril</synonym>
    <synonym>Foille insetti</synonym>
    <synonym>Genacort</synonym>
    <synonym>gyno-Cortisone</synonym>
    <synonym>Heb cort</synonym>
    <synonym>Heb-cort</synonym>
    <synonym>Hidalone</synonym>
    <synonym>hidro-Colisona</synonym>
    <synonym>Hycort</synonym>
    <synonym>Hycortol</synonym>
    <synonym>Hycortole</synonym>
    <synonym>Hydracort</synonym>
    <synonym>Hydrasson</synonym>
    <synonym>hydro-Adreson</synonym>
    <synonym>hydro-Colisona</synonym>
    <synonym>Hydrocort</synonym>
    <synonym>Hydrocortal</synonym>
    <synonym>Hydrocortistab</synonym>
    <synonym>Hydrocortisyl</synonym>
    <synonym>Hydroskin</synonym>
    <synonym>Hysone</synonym>
    <synonym>Hytisone</synonym>
    <synonym>Hytone lotion</synonym>
    <synonym>Incortin-H</synonym>
    <synonym>Incortin-hydrogen</synonym>
    <synonym>Komed HC</synonym>
    <synonym>Kyypakkaus</synonym>
    <synonym>Lacticare HC</synonym>
    <synonym>Lacticare-HC</synonym>
    <synonym>Lactisona</synonym>
    <synonym>Lubricort</synonym>
    <synonym>Maintasone</synonym>
    <synonym>Medicort</synonym>
    <synonym>Meusicort</synonym>
    <synonym>Mildison</synonym>
    <synonym>Milliderm</synonym>
    <synonym>neo-Cort-dome</synonym>
    <synonym>Neosporin-H ear</synonym>
    <synonym>Nystaform-HC</synonym>
    <synonym>Optef</synonym>
    <synonym>Otalgine</synonym>
    <synonym>Otic-neo-cort-dome</synonym>
    <synonym>Otobiotic</synonym>
    <synonym>Otocort</synonym>
    <synonym>Otosone-F</synonym>
    <synonym>Pediotic suspension</synonym>
    <synonym>Permicort</synonym>
    <synonym>Polcort H</synonym>
    <synonym>Preparation H hydrocortisone cream</synonym>
    <synonym>Prepcort</synonym>
    <synonym>Prestwick_265</synonym>
    <synonym>Prevex HC</synonym>
    <synonym>Proctofoam</synonym>
    <synonym>Protocort</synonym>
    <synonym>Racet</synonym>
    <synonym>Rectoid</synonym>
    <synonym>Remederm HC</synonym>
    <synonym>Sanatison</synonym>
    <synonym>Scalpicin capilar</synonym>
    <synonym>Schericur</synonym>
    <synonym>Scheroson F</synonym>
    <synonym>Sigmacort</synonym>
    <synonym>Signef</synonym>
    <synonym>Stiefcorcil</synonym>
    <synonym>Systral hydrocort</synonym>
    <synonym>Tarcortin</synonym>
    <synonym>Timocort</synonym>
    <synonym>Topicort</synonym>
    <synonym>Transderma H</synonym>
    <synonym>Traumaide</synonym>
    <synonym>Uniderm</synonym>
    <synonym>Vioform-hydrocortisone</synonym>
    <synonym>VoSol HC</synonym>
    <synonym>Vytone</synonym>
    <synonym>Zenoxone</synonym>
    <synonym>11-Epicortisol</synonym>
    <synonym>Hydrocortisone, (11 alpha)-isomer</synonym>
    <synonym>Hydrocortisone, (9 beta,10 alpha,11 alpha)-isomer</synonym>
    <synonym>11 Epicortisol</synonym>
    <synonym>Cortifair</synonym>
    <synonym>Epicortisol</synonym>
  </synonyms>
  <chemical_formula>C21H30O5</chemical_formula>
  <average_molecular_weight>362.4599</average_molecular_weight>
  <monisotopic_moleculate_weight>362.20932407</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</traditional_iupac>
  <cas_registry_number>50-23-7</cas_registry_number>
  <smiles>[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1</inchi>
  <inchikey>JYGXADMDTFJGBT-VWUMJDOOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>11-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>11-beta-hydroxysteroid</substituent>
      <substituent>11-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>11beta-hydroxy steroid</external_descriptor>
      <external_descriptor>17alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>20-oxo steroid</external_descriptor>
      <external_descriptor>21-hydroxy steroid</external_descriptor>
      <external_descriptor>3-oxo steroid</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
      <external_descriptor>C21-steroid</external_descriptor>
      <external_descriptor>Glucocorticoids</external_descriptor>
      <external_descriptor>Pregnane and derivatives [Fig]</external_descriptor>
      <external_descriptor>glucocorticoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>362.4599</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>362.20932407</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H30O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JYGXADMDTFJGBT-VWUMJDOOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>97.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>40476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>68817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>68818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>68819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>126936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>126937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>126938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443924</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451420</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB00741</drugbank_id>
  <chemspider_id/>
  <foodb_id/>
  <pubchem_compound_id>5754</pubchem_compound_id>
  <kegg_id>C00735</kegg_id>
  <pdbe_id/>
  <chebi_id>17650</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Hydrocortisone</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Hanson, Frederick R.; Mann, Kingsley M.; Nielson, Eldon D.; Anderson, Hugh V.; Brunner, Mari P.; Karnemaat, John N.; Colingsworth, Donald R.; Haines, Wm. J. Microbiological transformations of steroids. VIII. Preparation of 17a-hydroxycorticosterone. Journ</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:12 UTC</creation_date>
  <update_date>2020-04-16 20:39:49 UTC</update_date>
  <accession>BMDB0000064</accession>
  <secondary_accessions>
    <accession>BMDB00064</accession>
  </secondary_accessions>
  <name>Creatine</name>
  <description>Creatine, also known as cosmocair C 100 or krebiozon, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Creatine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Creatine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Creatine exists in all living organisms, ranging from bacteria to humans. Creatine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>((Amino(imino)methyl)(methyl)amino)acetic acid</synonym>
    <synonym>(alpha-Methylguanido)acetic acid</synonym>
    <synonym>(N-Methylcarbamimidamido)acetic acid</synonym>
    <synonym>alpha-Methylguanidino acetic acid</synonym>
    <synonym>Creatin</synonym>
    <synonym>Kreatin</synonym>
    <synonym>Methylglycocyamine</synonym>
    <synonym>N-(Aminoiminomethyl)-N-methylglycine</synonym>
    <synonym>N-[(e)-AMINO(imino)methyl]-N-methylglycine</synonym>
    <synonym>N-Amidinosarcosine</synonym>
    <synonym>N-Carbamimidoyl-N-methylglycine</synonym>
    <synonym>N-Methyl-N-guanylglycine</synonym>
    <synonym>((Amino(imino)methyl)(methyl)amino)acetate</synonym>
    <synonym>(a-Methylguanido)acetate</synonym>
    <synonym>(a-Methylguanido)acetic acid</synonym>
    <synonym>(alpha-Methylguanido)acetate</synonym>
    <synonym>(Α-methylguanido)acetate</synonym>
    <synonym>(Α-methylguanido)acetic acid</synonym>
    <synonym>(N-Methylcarbamimidamido)acetate</synonym>
    <synonym>a-Methylguanidino acetate</synonym>
    <synonym>a-Methylguanidino acetic acid</synonym>
    <synonym>alpha-Methylguanidino acetate</synonym>
    <synonym>Α-methylguanidino acetate</synonym>
    <synonym>Α-methylguanidino acetic acid</synonym>
    <synonym>Cosmocair C 100</synonym>
    <synonym>Creatine hydrate</synonym>
    <synonym>Krebiozon</synonym>
    <synonym>Methylguanidoacetate</synonym>
    <synonym>Methylguanidoacetic acid</synonym>
    <synonym>N-(Aminoiminomethyl)-N-methyl-glycine</synonym>
    <synonym>Phosphagen</synonym>
    <synonym>[[Amino(imino)methyl](methyl)amino]acetate</synonym>
    <synonym>[[Amino(imino)methyl](methyl)amino]acetic acid</synonym>
  </synonyms>
  <chemical_formula>C4H9N3O2</chemical_formula>
  <average_molecular_weight>131.1332</average_molecular_weight>
  <monisotopic_moleculate_weight>131.069476547</monisotopic_moleculate_weight>
  <iupac_name>2-(N-methylcarbamimidamido)acetic acid</iupac_name>
  <traditional_iupac>creatine</traditional_iupac>
  <cas_registry_number>57-00-1</cas_registry_number>
  <smiles>CN(CC(O)=O)C(N)=N</smiles>
  <inchi>InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)</inchi>
  <inchikey>CVSVTCORWBXHQV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Guanidines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>glycine derivative</external_descriptor>
      <external_descriptor>guanidines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>303 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>13.3 mg/mL at 18 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>12.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(N-methylcarbamimidamido)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>131.1332</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>131.069476547</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN(CC(O)=O)C(N)=N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H9N3O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CVSVTCORWBXHQV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>90.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2737</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in lactating Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>189.883-542.197</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by procedure of Folin and Wu (1919)</comment>
      <references>
        <reference>
          <reference_text>Arthur K. Anderson, Howard E. Gayley, Avery D. Pratt. Studies on the Chemical Composition of Bovine Blood. J. Dairy Science (1930) 13(4):336-348   doi: 10.3168/jds.S0022-0302(30)93530-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>196+/-28</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>1321+/-464</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>4672+/-438</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>491 +/- 40</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>537 +/- 30</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>534 +/- 16</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>510 +/- 42</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>432.95 +/- 84.67</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>427.70 +/- 115.63</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from Danish Holstein-Friesian (n = 456) and Jersey cows (n = 436)</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
          <pubmed_id>23182357</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>436.42 +/- 79.99</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>10147.92 +/- 171.42</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>6.10+/-2.67</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>91.98+/-5.88</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>86.62+/-4.69</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>83.85+/-4.34</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in beef muscle (longissimus dorsi).</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>7262-10319</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>21000</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>7752.34 +/- 490.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>8768.14 +/- 196.21</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>8769.99 +/- 413.59</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1040-1520</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>19488-27111</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2-15</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>3+/-4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hanne Christine Bertram, Niels Bastian Kristensen, Mogens Vestergaard, SÃ¸ren Krogh Jensen, Jakob Sehested, Niels Christian Nielsen, Anders Malmendal. Metabolic characterization of rumen epithelial tissue from dairy calves fed different starter diets using 1H NMR spectroscopy. Livestock Science (2008) 120:127-134   doi: 10.1016/j.livsci.2008.05.001</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>4755+/-306</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>7553+/-1850</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00300</kegg_id>
  <drugbank_id>DB00148</drugbank_id>
  <chemspider_id>566</chemspider_id>
  <foodb_id>FDB005403</foodb_id>
  <pdbe_id/>
  <chebi_id>16919</chebi_id>
  <pubchem_compound_id>586</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id>CREATINE</meta_cyc_id>
  <wikipedia_id>Creatine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34543</bigg_id>
  <metlin_id>7</metlin_id>
  <synthesis_reference>Thalhammer, Franz; Gastner, Thomas.  Preparation of creatine, creatine monohydrate and guanidinoacetic acid.    Ger. Offen.  (2007),     5pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
      <pubmed_id>23182357</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
      <pubmed_id>25599412</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00255</protein_accession>
      <name>Creatine kinase S-type, mitochondrial</name>
      <uniprot_id>Q3ZBP1</uniprot_id>
      <gene_name>CKMT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00256</protein_accession>
      <name>Creatine kinase B-type</name>
      <uniprot_id>Q5EA61</uniprot_id>
      <gene_name>CKB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00257</protein_accession>
      <name>Creatine kinase U-type, mitochondrial</name>
      <uniprot_id>Q9TTK8</uniprot_id>
      <gene_name>CKMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00258</protein_accession>
      <name>Creatine kinase M-type</name>
      <uniprot_id>Q9XSC6</uniprot_id>
      <gene_name>CKM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00412</protein_accession>
      <name>Guanidinoacetate N-methyltransferase</name>
      <uniprot_id>Q2TBQ3</uniprot_id>
      <gene_name>GAMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01895</protein_accession>
      <name>DNA-binding protein inhibitor ID-3</name>
      <uniprot_id>Q5E981</uniprot_id>
      <gene_name>ID3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01896</protein_accession>
      <name>Sodium- and chloride-dependent creatine transporter 1</name>
      <uniprot_id>O18875</uniprot_id>
      <gene_name>SLC6A8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:13 UTC</creation_date>
  <update_date>2020-04-15 20:47:42 UTC</update_date>
  <accession>BMDB0000067</accession>
  <secondary_accessions>
    <accession>BMDB00067</accession>
  </secondary_accessions>
  <name>Cholesterol</name>
  <description>Cholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Cholesterol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cholesterol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(3beta,14beta,17alpha)-Cholest-5-en-3-ol</synonym>
    <synonym>Cholest-5-en-3beta-ol</synonym>
    <synonym>Cholesterin</synonym>
    <synonym>(3b,14b,17a)-Cholest-5-en-3-ol</synonym>
    <synonym>(3Β,14β,17α)-cholest-5-en-3-ol</synonym>
    <synonym>Cholest-5-en-3b-ol</synonym>
    <synonym>Cholest-5-en-3β-ol</synonym>
    <synonym>(3Β)-cholest-5-en-3-ol</synonym>
    <synonym>(3beta)-Cholest-5-en-3-ol</synonym>
    <synonym>3Β-hydroxycholest-5-ene</synonym>
    <synonym>3beta-Hydroxycholest-5-ene</synonym>
    <synonym>5:6-Cholesten-3β-ol</synonym>
    <synonym>5:6-Cholesten-3beta-ol</synonym>
    <synonym>(-)-Cholesterol</synonym>
    <synonym>Cholesterine</synonym>
    <synonym>Cholesterol base H</synonym>
    <synonym>Cholesteryl alcohol</synonym>
    <synonym>Cholestrin</synonym>
    <synonym>Cholestrol</synonym>
    <synonym>Cordulan</synonym>
    <synonym>Dastar</synonym>
    <synonym>Dusoline</synonym>
    <synonym>Dusoran</synonym>
    <synonym>Dythol</synonym>
    <synonym>Fancol CH</synonym>
    <synonym>Hydrocerin</synonym>
    <synonym>Kathro</synonym>
    <synonym>Lanol</synonym>
    <synonym>Super hartolan</synonym>
    <synonym>Tegolan</synonym>
    <synonym>Cholesterol</synonym>
  </synonyms>
  <chemical_formula>C27H46O</chemical_formula>
  <average_molecular_weight>386.6535</average_molecular_weight>
  <monisotopic_moleculate_weight>386.354866094</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol</iupac_name>
  <traditional_iupac>(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol</traditional_iupac>
  <cas_registry_number>57-88-5</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</smiles>
  <inchi>InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>HVYWMOMLDIMFJA-DPAQBDIFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3beta-sterol</external_descriptor>
      <external_descriptor>Cholestane and derivatives</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>cholestane</external_descriptor>
      <external_descriptor>cholestanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>386.6535</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>386.354866094</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H46O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HVYWMOMLDIMFJA-DPAQBDIFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>120.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>50.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>34576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>48925</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3341.493 +/- 370.616</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Spectrometry (Autoanalyzer/BT3000 Plus)</comment>
      <references>
        <reference>
          <reference_text>Abdullah BASOGLU, Nuri BASPINAR, Alparslan COSKUN. NMR-based metabolomic evaluation in dairy cows with displaced abomasum. Turk J Vet Anim Sci (2014) 38(3):325-330</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3290</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Dacos Chemistry Analyzer in Hereford cows</comment>
      <references>
        <reference>
          <reference_text>Early RJ, McBride BW, Ball RO: Growth and metabolism in somatotropin-treated steers: I. Growth, serum chemistry and carcass weights. J Anim Sci. 1990 Dec;68(12):4134-43. doi: 10.2527/1990.68124134x.</reference_text>
          <pubmed_id>2286555</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>775.888</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by infra-red spectroscopy and silieic acid columns</comment>
      <references>
        <reference>
          <reference_text>Arthur K. Anderson, Howard E. Gayley, Avery D. Pratt. Studies on the Chemical Composition of Bovine Blood. J. Dairy Science (1930) 13(4):336-348   doi: 10.3168/jds.S0022-0302(30)93530-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>5560534.173</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1200 ml pomegranate peel extract/cow per day</comment>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>4189797.842</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>400 ml pomegranate peel extract/cow per day</comment>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>4138071.943</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>800 ml pomegranate peel extract/cow per day</comment>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>5431219.425</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>No pomegranate peel extract added</comment>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>129.315</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>362.0813</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>103.452</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>103.452</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>129.315</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>155.178</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>155.178</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>362.0813</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>206.904</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>206.904</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>206.904</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>206.904</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>206.904</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>77.589</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>89.744</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>77.589</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>258.629</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>258.629</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>362.0813</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>362.0813</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>362.0813</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>362.0813</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>101.383</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>defatted milk/saponified</comment>
      <references>
        <reference>
          <reference_text>Shi Y, Zhang JH, Shi D, Jiang M, Zhu YX, Mei SR, Zhou YK, Dai K, Lu B: Selective solid-phase extraction of cholesterol using molecularly imprinted polymers and its application in different biological samples. J Pharm Biomed Anal. 2006 Nov 16;42(5):549-55. doi: 10.1016/j.jpba.2006.05.022. Epub 2006 Jul 21.</reference_text>
          <pubmed_id>16859856</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
          <pubmed_id>1779072</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hanne Christine Bertram, Niels Bastian Kristensen, Mogens Vestergaard, SÃ¸ren Krogh Jensen, Jakob Sehested, Niels Christian Nielsen, Anders Malmendal. Metabolic characterization of rumen epithelial tissue from dairy calves fed different starter diets using 1H NMR spectroscopy. Livestock Science (2008) 120:127-134   doi: 10.1016/j.livsci.2008.05.001</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00187</kegg_id>
  <drugbank_id>DB04540</drugbank_id>
  <foodb_id>FDB013269</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>5997</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16113</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00003648</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Cholesterol</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id>CHOLESTEROL</meta_cyc_id>
  <synthesis_reference>Zhu, Yongming; Qin, Liena; Liu, Rui.  Simple method for synthesis cholesterol from Diosgenin.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2006),  9 pp. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Shi Y, Zhang JH, Shi D, Jiang M, Zhu YX, Mei SR, Zhou YK, Dai K, Lu B: Selective solid-phase extraction of cholesterol using molecularly imprinted polymers and its application in different biological samples. J Pharm Biomed Anal. 2006 Nov 16;42(5):549-55. doi: 10.1016/j.jpba.2006.05.022. Epub 2006 Jul 21.</reference_text>
      <pubmed_id>16859856</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
      <pubmed_id>1779072</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00053</protein_accession>
      <name>Cholesterol side-chain cleavage enzyme, mitochondrial</name>
      <uniprot_id>P00189</uniprot_id>
      <gene_name>CYP11A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00910</protein_accession>
      <name>7-dehydrocholesterol reductase</name>
      <uniprot_id>Q5E9J5</uniprot_id>
      <gene_name>DHCR7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01500</protein_accession>
      <name>Translocator protein</name>
      <uniprot_id>P30535</uniprot_id>
      <gene_name>TSPO</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01586</protein_accession>
      <name>Bile acid receptor</name>
      <uniprot_id>Q3SZL0</uniprot_id>
      <gene_name>NR1H4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02125</protein_accession>
      <name>Apolipoprotein A-I</name>
      <uniprot_id>P15497</uniprot_id>
      <gene_name>APOA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02126</protein_accession>
      <name>SCARB1 protein</name>
      <uniprot_id>A4IFC6</uniprot_id>
      <gene_name>SCARB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02127</protein_accession>
      <name>Cystic fibrosis transmembrane conductance regulator</name>
      <uniprot_id>Q9TSX2</uniprot_id>
      <gene_name>CFTR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02128</protein_accession>
      <name>Sterol regulatory element-binding protein cleavage-activating protein</name>
      <uniprot_id>A6QM06</uniprot_id>
      <gene_name>SCAP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02129</protein_accession>
      <name>StAR-related lipid transfer protein 5</name>
      <uniprot_id>A1A4M6</uniprot_id>
      <gene_name>STARD5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02130</protein_accession>
      <name>APOM protein</name>
      <uniprot_id>Q3ZBQ9</uniprot_id>
      <gene_name>APOM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02131</protein_accession>
      <name>Steroidogenic acute regulatory protein, mitochondrial</name>
      <uniprot_id>Q28918</uniprot_id>
      <gene_name>STAR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02132</protein_accession>
      <name>Apolipoprotein E</name>
      <uniprot_id>Q0ZCB4</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02133</protein_accession>
      <name>Apolipoprotein E</name>
      <uniprot_id>A7YWR0</uniprot_id>
      <gene_name>APOE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02134</protein_accession>
      <name>Scavenger receptor class B member 1</name>
      <uniprot_id>O18824</uniprot_id>
      <gene_name>SCARB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02135</protein_accession>
      <name>Na(+)/H(+) exchange regulatory cofactor NHE-RF3</name>
      <uniprot_id>Q3T0X8</uniprot_id>
      <gene_name>PDZK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:14 UTC</creation_date>
  <update_date>2020-04-16 20:40:45 UTC</update_date>
  <accession>BMDB0000068</accession>
  <secondary_accessions>
    <accession>BMDB00068</accession>
  </secondary_accessions>
  <name>Epinephrine</name>
  <description>Epinephrinee, also known as epinephrinee or epinephrine, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Epinephrinee exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Epinephrinee exists in all living organisms, ranging from bacteria to humans. Epinephrinee participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and epinephrinee can be biosynthesized from S-adenosylmethionine and norepinephrinee through its interaction with the enzyme phenylethanolamine N-methyltransferase. In addition, Epinephrinee can be converted into 3,4-dihydroxymandelaldehyde and methylamine; which is catalyzed by the enzyme amine oxidase [flavin-containing] a. In cattle, epinephrinee is involved in the metabolic pathway called the tyrosine metabolism pathway.</description>
  <synonyms>
    <synonym>(-)-(R)-Epinephrine</synonym>
    <synonym>(-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol</synonym>
    <synonym>(-)-Adrenaline</synonym>
    <synonym>(R)-(-)-Adrenaline</synonym>
    <synonym>(R)-(-)-Adnephrine</synonym>
    <synonym>(R)-(-)-Epinephrine</synonym>
    <synonym>(R)-(-)-Epirenamine</synonym>
    <synonym>4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol</synonym>
    <synonym>Adrenalin</synonym>
    <synonym>Adrenaline</synonym>
    <synonym>Epinefrina</synonym>
    <synonym>Epinephrin</synonym>
    <synonym>Epinephrinum</synonym>
    <synonym>Epipen</synonym>
    <synonym>Epipen JR</synonym>
    <synonym>L-Adrenaline</synonym>
    <synonym>Levoepinephrine</synonym>
    <synonym>Primatene</synonym>
    <synonym>Auvi-Q</synonym>
    <synonym>(-)-3,4-Dihydroxy-a-((methylamino)methyl)benzyl alcohol</synonym>
    <synonym>(-)-3,4-Dihydroxy-α-((methylamino)methyl)benzyl alcohol</synonym>
    <synonym>(-)-3,4-Dihydroxy-a-[(methylamino)methyl]-benzyl alcohol</synonym>
    <synonym>(-)-3,4-Dihydroxy-a-[2-(methylamino)ethyl]benzyl alcohol</synonym>
    <synonym>(-)-3,4-Dihydroxy-alpha-[(methylamino)methyl]-benzyl alcohol</synonym>
    <synonym>(-)-3,4-Dihydroxy-alpha-[2-(methylamino)ethyl]benzyl alcohol</synonym>
    <synonym>(-)-Epinephrine</synonym>
    <synonym>(R)-4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol</synonym>
    <synonym>(R)-Adrenaline</synonym>
    <synonym>(R)-Epinephrine</synonym>
    <synonym>Adnephrine</synonym>
    <synonym>Adrenal</synonym>
    <synonym>Adrenine</synonym>
    <synonym>Adrin</synonym>
    <synonym>Ana-kit</synonym>
    <synonym>Bosmin</synonym>
    <synonym>Bronkaid mist</synonym>
    <synonym>Chelafrin</synonym>
    <synonym>Epifrin</synonym>
    <synonym>Epiglaufrin</synonym>
    <synonym>Epinephran</synonym>
    <synonym>Epirenan</synonym>
    <synonym>Eppy</synonym>
    <synonym>Exadrin</synonym>
    <synonym>Glauposine</synonym>
    <synonym>Hemisine</synonym>
    <synonym>Hemostasin</synonym>
    <synonym>Hemostatin</synonym>
    <synonym>Hypernephrin</synonym>
    <synonym>Isoptoepinal</synonym>
    <synonym>L-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol</synonym>
    <synonym>L-Epinephrine</synonym>
    <synonym>L-Epirenamine</synonym>
    <synonym>L-Methylaminoethanolcatechol</synonym>
    <synonym>Levorenen</synonym>
    <synonym>Levorenin</synonym>
    <synonym>Levorenine</synonym>
    <synonym>Levoreninum</synonym>
    <synonym>Lyodrin</synonym>
    <synonym>Methylarterenol</synonym>
    <synonym>Mucidrina</synonym>
    <synonym>Nephridine</synonym>
    <synonym>Nieraline</synonym>
    <synonym>Paranephrin</synonym>
    <synonym>Primatene mist</synonym>
    <synonym>R-(-)-Epinephrine</synonym>
    <synonym>Renaglandin</synonym>
    <synonym>Renaleptine</synonym>
    <synonym>Renalina</synonym>
    <synonym>Renoform</synonym>
    <synonym>Renostypticin</synonym>
    <synonym>Renostyptin</synonym>
    <synonym>Scurenaline</synonym>
    <synonym>Simplene</synonym>
    <synonym>Styptirenal</synonym>
    <synonym>Supracapsulin</synonym>
    <synonym>Supranephrane</synonym>
    <synonym>Suprarenaline</synonym>
    <synonym>Suprarenin</synonym>
    <synonym>Surrenine</synonym>
    <synonym>Sus-phrine</synonym>
    <synonym>Takamina</synonym>
    <synonym>Vasoconstrictine</synonym>
    <synonym>Vasotonin</synonym>
    <synonym>4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol</synonym>
    <synonym>Epinephrine bitartrate</synonym>
    <synonym>Epinephrine hydrogen tartrate</synonym>
    <synonym>Lyophrin</synonym>
    <synonym>Adrenaline bitartrate</synonym>
    <synonym>Adrenaline hydrochloride</synonym>
    <synonym>Epinephrine acetate</synonym>
    <synonym>Allergan brand OF adrenaline hydrochloride</synonym>
    <synonym>Epitrate</synonym>
    <synonym>Acetate, epinephrine</synonym>
    <synonym>Adrenaline acid tartrate</synonym>
    <synonym>Epinephrine hydrochloride</synonym>
    <synonym>Medihaler-epi</synonym>
  </synonyms>
  <chemical_formula>C9H13NO3</chemical_formula>
  <average_molecular_weight>183.2044</average_molecular_weight>
  <monisotopic_moleculate_weight>183.089543287</monisotopic_moleculate_weight>
  <iupac_name>4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol</iupac_name>
  <traditional_iupac>epinephrine</traditional_iupac>
  <cas_registry_number>51-43-4</cas_registry_number>
  <smiles>CNC[C@H](O)C1=CC(O)=C(O)C=C1</smiles>
  <inchi>InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1</inchi>
  <inchikey>UCTWMZQNUQWSLP-VIFPVBQESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Benzenediols</sub_class>
    <direct_parent>Catechols</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Catechol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Adrenalines</external_descriptor>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>adrenaline</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>211.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.18 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.37</value>
      <source>HANSCH,C &amp; LEO,AJ (1985)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>183.2044</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>183.089543287</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CNC[C@H](O)C1=CC(O)=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UCTWMZQNUQWSLP-VIFPVBQESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>72.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>49.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436640</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00788</kegg_id>
  <drugbank_id>DB00668</drugbank_id>
  <foodb_id>FDB021889</foodb_id>
  <chemspider_id>5611</chemspider_id>
  <pubchem_compound_id>5816</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28918</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00029643</knapsack_id>
  <bigg_id>35997</bigg_id>
  <wikipedia_id>Epinephrine</wikipedia_id>
  <metlin_id>5127</metlin_id>
  <meta_cyc_id>L-EPINEPHRINE</meta_cyc_id>
  <synthesis_reference>Singer, Robert A.; Carreira, Erick M. An in situ procedure for catalytic, enantioselective acetate aldol addition. Application to the synthesis of (R)-(-)-epinephrine. Tetrahedron Letters (1997), 38(6), 927-930.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00010</protein_accession>
      <name>Cytochrome P450 11B1, mitochondrial</name>
      <uniprot_id>P15150</uniprot_id>
      <gene_name>CYP11B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00053</protein_accession>
      <name>Cholesterol side-chain cleavage enzyme, mitochondrial</name>
      <uniprot_id>P00189</uniprot_id>
      <gene_name>CYP11A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01608</protein_accession>
      <name>Prostaglandin E2 receptor EP4 subtype</name>
      <uniprot_id>Q8MJ08</uniprot_id>
      <gene_name>PTGER4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01816</protein_accession>
      <name>Pituitary adenylate cyclase-activating polypeptide type I receptor</name>
      <uniprot_id>Q29627</uniprot_id>
      <gene_name>ADCYAP1R1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02578</protein_accession>
      <name>Beta-2 adrenergic receptor</name>
      <uniprot_id>Q28044</uniprot_id>
      <gene_name>ADRB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02579</protein_accession>
      <name>Beta-1 adrenergic receptor</name>
      <uniprot_id>Q9TT96</uniprot_id>
      <gene_name>ADRB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02675</protein_accession>
      <name>Steroidogenic factor 1</name>
      <uniprot_id>Q04752</uniprot_id>
      <gene_name>NR5A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:15 UTC</creation_date>
  <update_date>2020-04-15 22:13:05 UTC</update_date>
  <accession>BMDB0000070</accession>
  <secondary_accessions>
    <accession>BMDB00070</accession>
  </secondary_accessions>
  <name>Pipecolic acid</name>
  <description>DL-Pipecolic acid, also known as pipecolinate or homoproline, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). DL-Pipecolic acid exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. DL-Pipecolic acid exists in all living species, ranging from bacteria to humans. DL-Pipecolic acid has been found to be associated with several diseases known as malaria, schizophrenia, rhizomelic chondrodysplasia punctata, and perillyl alcohol administration for cancer treatment; also dl-pipecolic acid has been linked to the inborn metabolic disorders including adrenoleukodystrophy.</description>
  <synonyms>
    <synonym>2-Piperidinecarboxylic acid</synonym>
    <synonym>Homoproline</synonym>
    <synonym>Pipecolinic acid</synonym>
    <synonym>2-Piperidinecarboxylate</synonym>
    <synonym>Pipecolinate</synonym>
    <synonym>Pipecolate</synonym>
    <synonym>()-Piperidine-2-carboxylic acid</synonym>
    <synonym>(+/-)-2-piperidinecarboxylate</synonym>
    <synonym>(+/-)-2-piperidinecarboxylic acid</synonym>
    <synonym>(+/-)-pipecolate</synonym>
    <synonym>(+/-)-pipecolic acid</synonym>
    <synonym>(+/-)-pipecolinate</synonym>
    <synonym>(+/-)-pipecolinic acid</synonym>
    <synonym>(.+/-.)-2-piperidinecarboxylic acid</synonym>
    <synonym>(RS)-2-Piperidinecarboxylate</synonym>
    <synonym>(RS)-2-Piperidinecarboxylic acid</synonym>
    <synonym>.alpha.-pipecolinic acid</synonym>
    <synonym>2-Carboxypiperidine</synonym>
    <synonym>2-Pipecolinic acid</synonym>
    <synonym>2-Piperidinylcarboxylic acid</synonym>
    <synonym>a-Pipecolinate</synonym>
    <synonym>a-Pipecolinic acid</synonym>
    <synonym>Acide pipecolique</synonym>
    <synonym>Acide piperidine-carboxylique-2</synonym>
    <synonym>alpha-Pipecolinate</synonym>
    <synonym>alpha-Pipecolinic acid</synonym>
    <synonym>Dihydrobaikiane</synonym>
    <synonym>DL-2-Piperidinecarboxylate</synonym>
    <synonym>DL-2-Piperidinecarboxylic acid</synonym>
    <synonym>DL-Homoproline</synonym>
    <synonym>DL-Pipecolate</synonym>
    <synonym>DL-Pipecolic acid</synonym>
    <synonym>DL-Pipecolinate</synonym>
    <synonym>DL-Pipecolinic acid</synonym>
    <synonym>Hexahydro-2-picolinate</synonym>
    <synonym>Hexahydro-2-picolinic acid</synonym>
    <synonym>Hexahydropicolinate</synonym>
    <synonym>Hexahydropicolinic acid</synonym>
    <synonym>Pipecolic acid free base</synonym>
    <synonym>Piperidine-2-carboxylic acid</synonym>
    <synonym>Piperolinate</synonym>
    <synonym>Piperolinic acid</synonym>
    <synonym>L-Pipecolic acid</synonym>
    <synonym>Pipecolic acid, (R)-isomer</synonym>
    <synonym>Pipecolic acid, ion (1-)</synonym>
    <synonym>Pipecolic acid, monopotassium salt</synonym>
    <synonym>Pipecolic acid hydrochloride, (+-)-isomer</synonym>
    <synonym>Pipecolic acid, (S)-isomer</synonym>
    <synonym>Pipecolic acid, 14C-labeled CPD, (+,-)-isomer</synonym>
    <synonym>Homopipecolic acid</synonym>
    <synonym>Pipecolic acid, (+,-)-isomer</synonym>
    <synonym>Pipecolic acid, ion(1-), (+,-)-isomer</synonym>
    <synonym>Pipecolic acid, ion(1-), (S)-isomer</synonym>
    <synonym>Piperidine-2-carboxylate</synonym>
    <synonym>Pipecolic acid</synonym>
  </synonyms>
  <chemical_formula>C6H11NO2</chemical_formula>
  <average_molecular_weight>129.157</average_molecular_weight>
  <monisotopic_moleculate_weight>129.078978601</monisotopic_moleculate_weight>
  <iupac_name>piperidine-2-carboxylic acid</iupac_name>
  <traditional_iupac>(+,-)-pipecolic acid</traditional_iupac>
  <cas_registry_number>535-75-1</cas_registry_number>
  <smiles>OC(=O)C1CCCCN1</smiles>
  <inchi>InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)</inchi>
  <inchikey>HXEACLLIILLPRG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Piperidinecarboxylic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Piperidine</substituent>
      <substituent>Piperidinecarboxylic acid</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>piperidinemonocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>264 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>314 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.31</value>
      <source>TSAI,RS ET AL. (1991)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>piperidine-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>129.157</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>129.078978601</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1CCCCN1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H11NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HXEACLLIILLPRG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>49.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451913</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00408</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB000545</foodb_id>
  <pubchem_compound_id>849</pubchem_compound_id>
  <chemspider_id>826</chemspider_id>
  <pdbe_id/>
  <chebi_id>17964</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001387</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Pipecolic_acid</wikipedia_id>
  <metlin_id>50</metlin_id>
  <synthesis_reference>Asher, Vikram; Becu, Christian; Anteunis, Marc J. O.; Callens, Roland.  New synthesis of pipecolic acid and analogs.    Tetrahedron Letters  (1981),  22(2),  141-4.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:16 UTC</creation_date>
  <update_date>2020-04-15 20:47:43 UTC</update_date>
  <accession>BMDB0000071</accession>
  <secondary_accessions>
    <accession>BMDB00071</accession>
  </secondary_accessions>
  <name>Deoxyinosine</name>
  <description/>
  <synonyms>
    <synonym>9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-9H-purin-6-ol</synonym>
    <synonym>9-(2-Deoxy-b-D-erythro-pentofuranosyl)-9H-purin-6-ol</synonym>
    <synonym>9-(2-Deoxy-β-D-erythro-pentofuranosyl)-9H-purin-6-ol</synonym>
    <synonym>2'-Deoxyinosine</synonym>
    <synonym>2-Deoxy-inosine</synonym>
    <synonym>9-(2-Deoxy-b-D-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one</synonym>
    <synonym>9-(2-Deoxy-b-D-erythro-pentofuranosyl)-hypoxanthine</synonym>
    <synonym>9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-hypoxanthine</synonym>
    <synonym>9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one</synonym>
    <synonym>9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-hypoxanthine</synonym>
    <synonym>D-Ino</synonym>
    <synonym>delta-Ino</synonym>
    <synonym>DInosine</synonym>
    <synonym>Deoxyribose-inosine</synonym>
    <synonym>Deoxyinosine</synonym>
  </synonyms>
  <chemical_formula>C10H12N4O4</chemical_formula>
  <average_molecular_weight>252.23</average_molecular_weight>
  <monisotopic_moleculate_weight>252.085854882</monisotopic_moleculate_weight>
  <iupac_name>9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-ol</iupac_name>
  <traditional_iupac>2'-deoxy-inosine</traditional_iupac>
  <cas_registry_number>890-38-0</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O</smiles>
  <inchi>InChI=1S/C10H12N4O4/c15-2-6-5(16)1-7(18-6)14-4-13-8-9(14)11-3-12-10(8)17/h3-7,15-16H,1-2H2,(H,11,12,17)/t5-,6+,7+/m0/s1</inchi>
  <inchikey>VGONTNSXDCQUGY-RRKCRQDMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleosides</class>
    <sub_class>Purine 2'-deoxyribonucleosides</sub_class>
    <direct_parent>Purine 2'-deoxyribonucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine 2'-deoxyribonucleoside</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>purine 2'-deoxyribonucleoside</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>250 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.71</value>
      <source>FORD,H ET AL. (1991)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>252.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>252.085854882</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CNC2=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N4O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N4O4/c15-2-6-5(16)1-7(18-6)14-4-13-8-9(14)11-3-12-10(8)17/h3-7,15-16H,1-2H2,(H,11,12,17)/t5-,6+,7+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VGONTNSXDCQUGY-RRKCRQDMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>58.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4931</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05512</kegg_id>
  <drugbank_id>DB02380</drugbank_id>
  <foodb_id>FDB012323</foodb_id>
  <chemspider_id>58569</chemspider_id>
  <pubchem_compound_id>65058</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28997</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>45942</bigg_id>
  <wikipedia_id/>
  <metlin_id>3383</metlin_id>
  <meta_cyc_id>DEOXYINOSINE</meta_cyc_id>
  <synthesis_reference>Robins, Morris J.; Basom, Gerald L. Nucleic Acid Related Compounds. 8. Direct Conversion of 2′-Deoxyinosine to 6-Chloropurine 2′-Deoxyriboside and Selected 6-Substituted Deoxynucleosides and Their Evaluation As Substrates of Adenosine Deaminase.  Canadian Journal of Chemistry, 1973, 51(19): 3161-3169, https://doi.org/10.1139/v73-471</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:17 UTC</creation_date>
  <update_date>2020-04-14 22:46:18 UTC</update_date>
  <accession>BMDB0000072</accession>
  <secondary_accessions>
    <accession>BMDB00072</accession>
  </secondary_accessions>
  <name>cis-Aconitic acid</name>
  <description>cis-Aconitic acid, also known as cis-aconitate or acid, acontic, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. cis-Aconitic acid exists as a solid, possibly soluble (in water), and a moderately acidic compound (based on its pKa) molecule. cis-Aconitic acid exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>(Z)-1-Propene-1,2,3-tricarboxylic acid</synonym>
    <synonym>cis-1-Propene-1,2,3-tricarboxylic acid</synonym>
    <synonym>(Z)-1-Propene-1,2,3-tricarboxylate</synonym>
    <synonym>cis-1-Propene-1,2,3-tricarboxylate</synonym>
    <synonym>cis-Aconitate</synonym>
    <synonym>(1Z)-1-Propene-1,2,3-tricarboxylate</synonym>
    <synonym>(1Z)-1-Propene-1,2,3-tricarboxylic acid</synonym>
    <synonym>(Z)-Aconitate</synonym>
    <synonym>(Z)-Aconitic acid</synonym>
    <synonym>1-cis-2,3-Propenetricarboxylate</synonym>
    <synonym>1-cis-2,3-Propenetricarboxylic acid</synonym>
    <synonym>1-Propene-1,2,3-tricarboxylate</synonym>
    <synonym>1-Propene-1,2,3-tricarboxylic acid</synonym>
    <synonym>cis-Aconate</synonym>
    <synonym>cis-Aconic acid</synonym>
    <synonym>cis-Oxaloacetate</synonym>
    <synonym>cis-Oxaloacetic acid</synonym>
    <synonym>Acid, citridic</synonym>
    <synonym>Acid, citridinic</synonym>
    <synonym>Aconitic acid</synonym>
    <synonym>Acontic acid</synonym>
    <synonym>Adonic acid</synonym>
    <synonym>Achilleic acid</synonym>
    <synonym>Acid, acontic</synonym>
    <synonym>Acid, equisetic</synonym>
    <synonym>Citridinic acid</synonym>
    <synonym>Acid, achilleic</synonym>
    <synonym>Aconitate</synonym>
    <synonym>Citridic acid</synonym>
    <synonym>Pyrocitric acid</synonym>
    <synonym>Acid, aconitic</synonym>
    <synonym>Acid, adonic</synonym>
    <synonym>Acid, carboxyglutaconic</synonym>
    <synonym>Acid, pyrocitric</synonym>
    <synonym>Carboxyglutaconic acid</synonym>
    <synonym>Equisetic acid</synonym>
  </synonyms>
  <chemical_formula>C6H6O6</chemical_formula>
  <average_molecular_weight>174.1082</average_molecular_weight>
  <monisotopic_moleculate_weight>174.016437924</monisotopic_moleculate_weight>
  <iupac_name>(1Z)-prop-1-ene-1,2,3-tricarboxylic acid</iupac_name>
  <traditional_iupac>cis-aconitic acid</traditional_iupac>
  <cas_registry_number>585-84-2</cas_registry_number>
  <smiles>OC(=O)C\C(=C\C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1-</inchi>
  <inchikey>GTZCVFVGUGFEME-IWQZZHSRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Tricarboxylic acids and derivatives</sub_class>
    <direct_parent>Tricarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aconitic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>125 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>400.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1Z)-prop-1-ene-1,2,3-tricarboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>174.1082</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>174.016437924</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C\C(=C\C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H6O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GTZCVFVGUGFEME-IWQZZHSRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>111.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437118</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>73 - 157</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>22 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>22 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>26 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35.13 +/- 6.74</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32.12 +/- 3.51</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35.20 +/- 4.97</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00417</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB008306</foodb_id>
  <chemspider_id>558863</chemspider_id>
  <pubchem_compound_id>643757</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>32805</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001177</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Citric acid cycle</wikipedia_id>
  <metlin_id>5130</metlin_id>
  <meta_cyc_id>CIS-ACONITATE</meta_cyc_id>
  <synthesis_reference>Gutierrez, Eddie N.; Lamberti, Vincent.  cis and trans Aconitic acids and their salts. U.S.  (1978), 16 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:18 UTC</creation_date>
  <update_date>2020-04-16 20:39:50 UTC</update_date>
  <accession>BMDB0000073</accession>
  <secondary_accessions>
    <accession>BMDB00073</accession>
  </secondary_accessions>
  <name>Dopamine</name>
  <description>Dopamine, also known as 3-hydroxytyramine or deoxyepinephrine, belongs to the class of organic compounds known as catecholamines and derivatives. Catecholamines and derivatives are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution. Dopamine is a drug which is used for the correction of hemodynamic imbalances present in the shock syndrome due to myocardial infarction, trauma, endotoxic septicemia, open-heart surgery, renal failure, and chronic cardiac decompensation as in congestive failure. Dopamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Dopamine exists in all living organisms, ranging from bacteria to humans. Dopamine participates in a number of enzymatic reactions, within cattle. In particular, Dopamine can be converted into dopamine; which is catalyzed by the enzyme D(1a) dopamine receptor. In addition, Dopamine can be converted into dopamine through its interaction with the enzyme D(1a) dopamine receptor. In cattle, dopamine is involved in the metabolic pathway called the dopamine activation OF neurological reward system pathway. Dopamine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2-(3,4-Dihydroxyphenyl)ethylamine</synonym>
    <synonym>3,4-Dihydroxyphenethylamine</synonym>
    <synonym>3-Hydroxytyramine</synonym>
    <synonym>4-(2-Aminoethyl)-1,2-benzenediol</synonym>
    <synonym>4-(2-Aminoethyl)benzene-1,2-diol</synonym>
    <synonym>4-(2-Aminoethyl)catechol</synonym>
    <synonym>4-(2-Aminoethyl)pyrocatechol</synonym>
    <synonym>Deoxyepinephrine</synonym>
    <synonym>Dopamina</synonym>
    <synonym>Dopaminum</synonym>
    <synonym>Hydroxytyramin</synonym>
    <synonym>Medopa</synonym>
    <synonym>3,4-Dihydroxyphenylethylamine</synonym>
    <synonym>4-(2-Aminoethyl)-pyrocatechol</synonym>
    <synonym>a-(3,4-Dihydroxyphenyl)-b-aminoethane</synonym>
    <synonym>alpha-(3,4-Dihydroxyphenyl)-beta-aminoethane</synonym>
    <synonym>Dopamin</synonym>
    <synonym>Dopastat</synonym>
    <synonym>Dophamine</synonym>
    <synonym>Dynatra</synonym>
    <synonym>Hydroxytyramine</synonym>
    <synonym>Intropin</synonym>
    <synonym>Oxytyramine</synonym>
    <synonym>Revivan</synonym>
    <synonym>3,4 Dihydroxyphenethylamine</synonym>
    <synonym>Hydrochloride, dopamine</synonym>
    <synonym>Dopamine hydrochloride</synonym>
  </synonyms>
  <chemical_formula>C8H11NO2</chemical_formula>
  <average_molecular_weight>153.1784</average_molecular_weight>
  <monisotopic_moleculate_weight>153.078978601</monisotopic_moleculate_weight>
  <iupac_name>4-(2-aminoethyl)benzene-1,2-diol</iupac_name>
  <traditional_iupac>dopamine</traditional_iupac>
  <cas_registry_number>62-31-7</cas_registry_number>
  <smiles>NCCC1=CC(O)=C(O)C=C1</smiles>
  <inchi>InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2</inchi>
  <inchikey>VYFYYTLLBUKUHU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as catecholamines and derivatives. Catecholamines and derivatives are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Benzenediols</sub_class>
    <direct_parent>Catecholamines and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>2-arylethylamines</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenethylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>2-arylethylamine</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Catecholamine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenethylamine</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>Dopamine</external_descriptor>
      <external_descriptor>Tyramine derivatives</external_descriptor>
      <external_descriptor>catecholamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>128 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>535 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.98</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-(2-aminoethyl)benzene-1,2-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>153.1784</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>153.078978601</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCC1=CC(O)=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H11NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VYFYYTLLBUKUHU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Dopamine Activation of Neurological Reward System</name>
      <smpdb_id>SMP0107994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436587</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>2+/-2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by UPLC-Q-TOF MS E</comment>
      <references>
        <reference>
          <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
          <pubmed_id>28342601</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C03758</kegg_id>
  <drugbank_id>DB00988</drugbank_id>
  <foodb_id>FDB012163</foodb_id>
  <chemspider_id>661</chemspider_id>
  <pubchem_compound_id>681</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18243</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001408</knapsack_id>
  <bigg_id>42467</bigg_id>
  <wikipedia_id>Dopamine</wikipedia_id>
  <metlin_id>64</metlin_id>
  <meta_cyc_id>DOPAMINE</meta_cyc_id>
  <synthesis_reference>Klaus Schoellkopf, Rudolf Albrecht, Manfred Lehmann, Gertrud Schroeder, "Novel dopamine derivatives, processes for their preparation, and their use as medicinal agents." U.S. Patent US4958026, issued February, 1972.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
      <pubmed_id>28342601</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00655</protein_accession>
      <name>Dopamine beta-hydroxylase</name>
      <uniprot_id>P15101</uniprot_id>
      <gene_name>DBH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00936</protein_accession>
      <name>Aromatic-L-amino-acid decarboxylase</name>
      <uniprot_id>P27718</uniprot_id>
      <gene_name>DDC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01811</protein_accession>
      <name>Synaptic vesicular amine transporter</name>
      <uniprot_id>Q27963</uniprot_id>
      <gene_name>SLC18A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02688</protein_accession>
      <name>Sodium-dependent dopamine transporter</name>
      <uniprot_id>P27922</uniprot_id>
      <gene_name>SLC6A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02689</protein_accession>
      <name>D(2) dopamine receptor</name>
      <uniprot_id>P20288</uniprot_id>
      <gene_name>DRD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02690</protein_accession>
      <name>Neuron specific gene family member 1</name>
      <uniprot_id>Q08DZ1</uniprot_id>
      <gene_name>NSG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02691</protein_accession>
      <name>D5 dopamine receptor protein</name>
      <uniprot_id>Q28919</uniprot_id>
      <gene_name>D5 dopamine receptor</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02692</protein_accession>
      <name>GTP-binding protein alpha O1 subunit, GO alpha O1 subunit</name>
      <uniprot_id>Q9TSC8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02693</protein_accession>
      <name>Calcyon neuron-specific vesicular protein</name>
      <uniprot_id>Q0VCJ9</uniprot_id>
      <gene_name>CALY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02694</protein_accession>
      <name>Dopamine receptor D4</name>
      <uniprot_id>Q8WNT0</uniprot_id>
      <gene_name>DRD4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02695</protein_accession>
      <name>Neuron-specific protein family member 2</name>
      <uniprot_id>Q0VCZ0</uniprot_id>
      <gene_name>NSG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02696</protein_accession>
      <name>D(1B) dopamine receptor</name>
      <uniprot_id>Q95137</uniprot_id>
      <gene_name>DRD5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02697</protein_accession>
      <name>D(1A) dopamine receptor</name>
      <uniprot_id>Q95136</uniprot_id>
      <gene_name>DRD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:20 UTC</creation_date>
  <update_date>2020-04-15 22:13:05 UTC</update_date>
  <accession>BMDB0000076</accession>
  <secondary_accessions>
    <accession>BMDB00076</accession>
  </secondary_accessions>
  <name>Dihydrouracil</name>
  <description>Dihydrouracil belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Dihydrouracil exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Dihydrouracil exists in all living organisms, ranging from bacteria to humans. Dihydrouracil is a potentially toxic compound. Dihydrouracil has been found to be associated with several diseases known as liver disease, colorectal cancer, hypertension, and cerebral infarction; also dihydrouracil has been linked to the inborn metabolic disorders including dihydropyrimidine dehydrogenase deficiency.</description>
  <synonyms>
    <synonym>2,4-Dioxotetrahydropyrimidine</synonym>
    <synonym>5,6-Dihydro-2,4-dihydroxypyrimidine</synonym>
    <synonym>Dihydro-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>DIHYDROPYRIMIDINE-2,4(1H,3H)-dione</synonym>
    <synonym>Dihydrouracile</synonym>
    <synonym>Hydrouracil</synonym>
    <synonym>5,6-Dihydro-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>5,6-Dihydrouracil</synonym>
    <synonym>Dihydro-pyrimidine-2,4-dione</synonym>
  </synonyms>
  <chemical_formula>C4H6N2O2</chemical_formula>
  <average_molecular_weight>114.1026</average_molecular_weight>
  <monisotopic_moleculate_weight>114.042927446</monisotopic_moleculate_weight>
  <iupac_name>1,3-diazinane-2,4-dione</iupac_name>
  <traditional_iupac>dihydrouracil</traditional_iupac>
  <cas_registry_number>504-07-4</cas_registry_number>
  <smiles>O=C1CCNC(=O)N1</smiles>
  <inchi>InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)</inchi>
  <inchikey>OIVLITBTBDPEFK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazines</class>
    <sub_class>Pyrimidines and pyrimidine derivatives</sub_class>
    <direct_parent>Pyrimidones</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Diazinanes</alternative_parent>
      <alternative_parent>Dicarboximides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl ureas</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-diazinane</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonic acid derivative</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboximide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl urea</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
      <substituent>Ureide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a base derivative</external_descriptor>
      <external_descriptor>a pyrimidine-related compound</external_descriptor>
      <external_descriptor>pyrimidone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>279 - 281 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1,3-diazinane-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>114.1026</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>114.042927446</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O=C1CCNC(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H6N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H6N2O2/c7-3-1-2-5-4(8)6-3/h1-2H2,(H2,5,6,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OIVLITBTBDPEFK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>58.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451880</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00429</kegg_id>
  <drugbank_id>DB01849</drugbank_id>
  <foodb_id>FDB030556</foodb_id>
  <chemspider_id>629</chemspider_id>
  <pubchem_compound_id>649</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15901</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>34956</bigg_id>
  <wikipedia_id>Dihydrouracil</wikipedia_id>
  <metlin_id>285</metlin_id>
  <meta_cyc_id>DI-H-URACIL</meta_cyc_id>
  <synthesis_reference>Bhat, K. S.; Rao, A. S.  Synthesis of uracil, 6-methyluracil and some dihydrouracils.    Organic Preparations and Procedures International  (1983),  15(5),  303-13.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00689</protein_accession>
      <name>Dihydropyrimidine dehydrogenase [NADP+]</name>
      <uniprot_id>Q28007</uniprot_id>
      <gene_name>DPYD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:22 UTC</creation_date>
  <update_date>2020-04-16 17:50:59 UTC</update_date>
  <accession>BMDB0000077</accession>
  <secondary_accessions>
    <accession>BMDB00077</accession>
  </secondary_accessions>
  <name>Dehydroepiandrosterone</name>
  <description>Dehydroepiandrosterone, also known as 5-androsten-3b-ol-17-one or diandron, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, dehydroepiandrosterone is considered to be a steroid lipid molecule. Dehydroepiandrosterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Dehydroepiandrosterone participates in a number of enzymatic reactions, within cattle. In particular, Dehydroepiandrosterone can be biosynthesized from 17a-hydroxypregnenolone through its interaction with the enzyme steroid 17-alpha-hydroxylase/17,20 lyase. In addition, Dehydroepiandrosterone can be converted into androstenedione through the action of the enzyme 3-beta-HSD 1. In cattle, dehydroepiandrosterone is involved in the metabolic pathway called the androgen and estrogen metabolism pathway. Dehydroepiandrosterone is a potentially toxic compound. Dehydroepiandrosterone has been found to be associated with several diseases known as rheumatoid arthritis, antley-bixler syndrome with genital anomalies and disordered steroidogenesis, adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency, and adrenal insufficiency, congenital, with 46,xy sex reversal, partial or complete; also dehydroepiandrosterone has been linked to the inborn metabolic disorders including 21-hydroxylase deficiency.</description>
  <synonyms>
    <synonym>3-BETA-HYDROXY-5-androsten-17-one</synonym>
    <synonym>3beta-Hydroxyandrost-5-en-17-one</synonym>
    <synonym>Dehydroisoandrosterone</synonym>
    <synonym>DHA</synonym>
    <synonym>DHEA</synonym>
    <synonym>Intrarosa</synonym>
    <synonym>Prasterone</synonym>
    <synonym>Biolaif</synonym>
    <synonym>3-b-HYDROXY-5-androsten-17-one</synonym>
    <synonym>3-Β-hydroxy-5-androsten-17-one</synonym>
    <synonym>3b-Hydroxyandrost-5-en-17-one</synonym>
    <synonym>3Β-hydroxyandrost-5-en-17-one</synonym>
    <synonym>(+)-Dehydroisoandrosterone</synonym>
    <synonym>(3-beta)-3-Hydroxyandrost-5-en-17-one</synonym>
    <synonym>(3beta)-3-Hydroxy-androst-5-en-17-one</synonym>
    <synonym>(3beta,16alpha)-3,16-Dihydroxy-androst-5-en-17-one</synonym>
    <synonym>17-Chetovis</synonym>
    <synonym>17-Hormoforin</synonym>
    <synonym>3-beta-Hydroxyandrost-5-en-17-one</synonym>
    <synonym>3b-Hydroxy-D5-androsten-17-one</synonym>
    <synonym>3beta-Hydroxy-5-androsten-17-one</synonym>
    <synonym>3beta-Hydroxy-androst-5-en-17-one</synonym>
    <synonym>3beta-Hydroxy-D5-androsten-17-one</synonym>
    <synonym>5,6-Dehydroisoandrosterone</synonym>
    <synonym>5,6-Didehydroisoandrosterone</synonym>
    <synonym>5-Androsten-3-beta-ol-17-one</synonym>
    <synonym>5-Androsten-3b-ol-17-one</synonym>
    <synonym>5-Androsten-3beta-ol-17-one</synonym>
    <synonym>5-Dehydro-epiandrosterone</synonym>
    <synonym>5-Dehydroepiandrosterone</synonym>
    <synonym>Andrestenol</synonym>
    <synonym>Androst-5-ene-3b-ol-17-one</synonym>
    <synonym>Androst-5-ene-3beta-ol-17-one</synonym>
    <synonym>Androsten-3beta-ol-17-one</synonym>
    <synonym>Androstenolone</synonym>
    <synonym>Astenile</synonym>
    <synonym>D5-Androsten-3b-ol-17-one</synonym>
    <synonym>D5-Androsten-3beta-ol-17-one</synonym>
    <synonym>Deandros</synonym>
    <synonym>Dehydro-epi-androsterone</synonym>
    <synonym>Diandron</synonym>
    <synonym>Diandrone</synonym>
    <synonym>Hydroxyandrostenone</synonym>
    <synonym>Prasterona</synonym>
    <synonym>Prasteronum</synonym>
    <synonym>Prestara</synonym>
    <synonym>Psicosterone</synonym>
    <synonym>trans-Dehydroandrosterone</synonym>
    <synonym>Prasterone, 3 alpha-isomer</synonym>
    <synonym>5 Androsten 3 beta hydroxy 17 one</synonym>
    <synonym>5-Androsten-3-beta-hydroxy-17-one</synonym>
    <synonym>5 Androsten 3 ol 17 one</synonym>
    <synonym>Prasterone, 3 alpha isomer</synonym>
    <synonym>5-Androsten-3-ol-17-one</synonym>
    <synonym>EM-760Dehydroandrosterone</synonym>
  </synonyms>
  <chemical_formula>C19H28O2</chemical_formula>
  <average_molecular_weight>288.4244</average_molecular_weight>
  <monisotopic_moleculate_weight>288.20893014</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one</iupac_name>
  <traditional_iupac>(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one</traditional_iupac>
  <cas_registry_number>53-43-0</cas_registry_number>
  <smiles>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1</inchi>
  <inchikey>FMGSKLZLMKYGDP-USOAJAOKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17-oxo steroid</external_descriptor>
      <external_descriptor>3beta-hydroxy steroid</external_descriptor>
      <external_descriptor>Androgens</external_descriptor>
      <external_descriptor>Androstane and derivatives</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>androstanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>288.4244</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>288.20893014</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H28O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FMGSKLZLMKYGDP-USOAJAOKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>43119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>43120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>43121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>43989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>43990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>43991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>111114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>111115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>111116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451379</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>&lt;0.000884</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS in Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.00052</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000183 +/- 0.00006241</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Half-Skim (commercial)</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637.</reference_text>
          <pubmed_id>17852390</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000118 +/- 0.00004299</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>commercial skim milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637.</reference_text>
          <pubmed_id>17852390</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000227 +/- 0.00007766</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk (commercial)</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637.</reference_text>
          <pubmed_id>17852390</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000199</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial half skim milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000142</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000415</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01227</kegg_id>
  <drugbank_id>DB01708</drugbank_id>
  <foodb_id>FDB021808</foodb_id>
  <chemspider_id>8036443</chemspider_id>
  <pubchem_compound_id>5881</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28689</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>37131</bigg_id>
  <wikipedia_id>Dehydroepiandrosterone</wikipedia_id>
  <metlin_id>5133</metlin_id>
  <meta_cyc_id>3-BETA-HYDROXYANDROST-5-EN-17-ONE</meta_cyc_id>
  <synthesis_reference>Nguyen Xuan Cuong; Nguyen Van Dan.  Synthesis of dehydroepiandrosterone (DHA) from 16-dehydropregnenolone acetate (DPA).    Tap Chi Duoc Hoc  (1983),   (4),  12-14.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637.</reference_text>
      <pubmed_id>17852390</pubmed_id>
    </reference>
    <reference>
      <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
      <pubmed_id>18412364</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:23 UTC</creation_date>
  <update_date>2020-04-16 20:37:21 UTC</update_date>
  <accession>BMDB0000078</accession>
  <secondary_accessions>
    <accession>BMDB00078</accession>
  </secondary_accessions>
  <name>Cysteinylglycine</name>
  <description/>
  <synonyms>
    <synonym>CG</synonym>
    <synonym>Cys-gly</synonym>
    <synonym>N-L-Cysteinylglycine</synonym>
    <synonym>L-Cysteinylglycine</synonym>
    <synonym>N-Cysteinyl glycine</synonym>
    <synonym>N-Cysteinyl-glycine</synonym>
    <synonym>N-L-Cysteinyl-glycine</synonym>
    <synonym>Cysteinyl-glycine</synonym>
    <synonym>C-g Dipeptide</synonym>
    <synonym>CG Dipeptide</synonym>
    <synonym>Cysteine glycine dipeptide</synonym>
    <synonym>Cysteine-glycine dipeptide</synonym>
    <synonym>L-Cys-gly</synonym>
    <synonym>N-Cysteinylglycine</synonym>
    <synonym>Cysteinylglycine</synonym>
  </synonyms>
  <chemical_formula>C5H10N2O3S</chemical_formula>
  <average_molecular_weight>178.21</average_molecular_weight>
  <monisotopic_moleculate_weight>178.041212886</monisotopic_moleculate_weight>
  <iupac_name>2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid</iupac_name>
  <traditional_iupac>Cys-Gly</traditional_iupac>
  <cas_registry_number>19246-18-5</cas_registry_number>
  <smiles>N[C@@H](CS)C(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C5H10N2O3S/c6-3(2-11)5(10)7-1-4(8)9/h3,11H,1-2,6H2,(H,7,10)(H,8,9)/t3-/m0/s1</inchi>
  <inchikey>ZUKPVRWZDMRIEO-VKHMYHEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Dipeptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cysteine and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-dipeptide</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Cysteine or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dipeptide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>178.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>178.041212886</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CS)C(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10N2O3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10N2O3S/c6-3(2-11)5(10)7-1-4(8)9/h3,11H,1-2,6H2,(H,7,10)(H,8,9)/t3-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZUKPVRWZDMRIEO-VKHMYHEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glutathione Metabolism</name>
      <smpdb_id>SMP0087167</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448164</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01419</kegg_id>
  <pubchem_compound_id>439498</pubchem_compound_id>
  <chemspider_id>388596</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB021891</foodb_id>
  <pdbe_id/>
  <chebi_id>4047</chebi_id>
  <meta_cyc_id>CYS-GLY</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>1445980</bigg_id>
  <wikipedia_id/>
  <metlin_id>5134</metlin_id>
  <synthesis_reference>Holleman, James W.  Synthesis of glutathione and cysteinylglycine by soluble enzymes of rat liver.    Compt. rend.  (1954),  238  1360-1.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:24 UTC</creation_date>
  <update_date>2020-04-14 22:46:19 UTC</update_date>
  <accession>BMDB0000079</accession>
  <secondary_accessions>
    <accession>BMDB00079</accession>
  </secondary_accessions>
  <name>Dihydrothymine</name>
  <description>Dihydrothymine belongs to the class of organic compounds known as hydropyrimidines. Hydropyrimidines are compounds containing a hydrogenated pyrimidine ring (i.e. containing less than the maximum number of double bonds.). Dihydrothymine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydrothymine exists in all living organisms, ranging from bacteria to humans. Dihydrothymine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>5,6-Dihydro-5-methyluracil</synonym>
    <synonym>5-Methyl-5,6-dihydrouracil</synonym>
    <synonym>5,6-Dihydrothymine</synonym>
    <synonym>5-Methyl-hydrouracil</synonym>
    <synonym>5-Methyldihydropyrimidine-2,4(1H,3H)-dione</synonym>
    <synonym>Dihydro-5-methyl-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>5-Methyldihydrouracil</synonym>
    <synonym>5,6-Dihydrothymine, (S)-isomer</synonym>
  </synonyms>
  <chemical_formula>C5H8N2O2</chemical_formula>
  <average_molecular_weight>128.1292</average_molecular_weight>
  <monisotopic_moleculate_weight>128.05857751</monisotopic_moleculate_weight>
  <iupac_name>5-methyl-1,3-diazinane-2,4-dione</iupac_name>
  <traditional_iupac>dihydrothymine</traditional_iupac>
  <cas_registry_number>696-04-8</cas_registry_number>
  <smiles>CC1CNC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C5H8N2O2/c1-3-2-6-5(9)7-4(3)8/h3H,2H2,1H3,(H2,6,7,8,9)</inchi>
  <inchikey>NBAKTGXDIBVZOO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydropyrimidines. Hydropyrimidines are compounds containing a hydrogenated pyrimidine ring (i.e. containing less than the maximum number of double bonds.).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazines</class>
    <sub_class>Pyrimidines and pyrimidine derivatives</sub_class>
    <direct_parent>Hydropyrimidines</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>5,6-dihydropyrimidine</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a base derivative</external_descriptor>
      <external_descriptor>a pyrimidine-related compound</external_descriptor>
      <external_descriptor>pyrimidone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-methyl-1,3-diazinane-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>128.1292</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>128.05857751</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1CNC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8N2O2/c1-3-2-6-5(9)7-4(3)8/h3H,2H2,1H3,(H2,6,7,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NBAKTGXDIBVZOO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>58.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30988</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348399</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00906</kegg_id>
  <foodb_id>FDB030555</foodb_id>
  <drugbank_id/>
  <chemspider_id>84456</chemspider_id>
  <pubchem_compound_id>93556</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>27468</chebi_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Dihydrothymine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>36347</bigg_id>
  <metlin_id>5135</metlin_id>
  <synthesis_reference>Yamane, Tetsuo; Wyluda, Benjamin J.; Shulman, Robert G.  Dihydrothymine from ultraviolet-irradiated DNA.    Proceedings of the National Academy of Sciences of the United States of America  (1967),  58(2),  439-42.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:26 UTC</creation_date>
  <update_date>2020-04-15 20:47:44 UTC</update_date>
  <accession>BMDB0000082</accession>
  <secondary_accessions>
    <accession>BMDB00082</accession>
  </secondary_accessions>
  <name>Cytidine triphosphate</name>
  <description/>
  <synonyms>
    <synonym>5'-CTP</synonym>
    <synonym>Cytidine 5'-triphosphate</synonym>
    <synonym>CYTIDINE-5'-triphosphATE</synonym>
    <synonym>H4CTP</synonym>
    <synonym>Cytidine 5'-triphosphoric acid</synonym>
    <synonym>CYTIDINE-5'-triphosphoric acid</synonym>
    <synonym>Cytidine triphosphoric acid</synonym>
    <synonym>5'-(Tetrahydrogen triphosphate) cytidine</synonym>
    <synonym>CTP</synonym>
    <synonym>Cytidine 3'-triphosphate</synonym>
    <synonym>Cytidine 5'-(tetrahydrogen triphosphate)</synonym>
    <synonym>Cytidine 5-prime-triphosphate</synonym>
    <synonym>Cytidine mono</synonym>
    <synonym>Cytidine mono(tetrahydrogen triphosphate) (ester)</synonym>
    <synonym>Deoxycytosine triphosphate</synonym>
    <synonym>Triphosphate, cytidine</synonym>
    <synonym>CRPPP</synonym>
    <synonym>Magnesium CTP</synonym>
    <synonym>MG CTP</synonym>
  </synonyms>
  <chemical_formula>C9H16N3O14P3</chemical_formula>
  <average_molecular_weight>483.1563</average_molecular_weight>
  <monisotopic_moleculate_weight>482.984511771</monisotopic_moleculate_weight>
  <iupac_name>({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</iupac_name>
  <traditional_iupac>CTP</traditional_iupac>
  <cas_registry_number>65-47-4</cas_registry_number>
  <smiles>NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1</inchi>
  <inchikey>PCDQPRRSZKQHHS-XVFCMESISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Coenzymes</external_descriptor>
      <external_descriptor>Ribonucleotides</external_descriptor>
      <external_descriptor>cytidine 5'-phosphate</external_descriptor>
      <external_descriptor>pyrimidine ribonucleoside 5'-triphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>215 - 218 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.076</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>483.1563</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>482.984511771</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H16N3O14P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PCDQPRRSZKQHHS-XVFCMESISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>268.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>87.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis</name>
      <smpdb_id>SMP0072032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:0)</name>
      <smpdb_id>SMP0077151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:0)</name>
      <smpdb_id>SMP0077153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:0)</name>
      <smpdb_id>SMP0077171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:0)</name>
      <smpdb_id>SMP0077173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077267</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077268</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077269</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077270</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077271</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077272</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077273</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077274</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077275</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077276</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077277</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077278</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077279</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077280</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077281</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077282</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077283</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077284</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077285</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077286</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077287</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077288</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077289</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077290</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077291</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077292</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077293</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077294</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077295</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077296</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077297</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077298</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:0)</name>
      <smpdb_id>SMP0077299</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077300</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077301</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077302</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077303</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077304</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077305</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077306</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077307</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077308</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077309</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:0)</name>
      <smpdb_id>SMP0077310</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077311</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:0)</name>
      <smpdb_id>SMP0077312</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077313</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077314</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077315</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077316</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077317</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077318</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077319</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077320</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077321</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077322</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077323</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077324</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077325</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077326</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077327</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077328</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077329</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077330</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077331</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077332</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077333</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077334</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077335</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077336</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077337</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077338</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077339</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077340</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077341</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077342</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077343</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077344</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077345</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077346</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077347</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077348</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077349</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077350</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077351</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077353</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077367</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077368</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077377</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077378</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077385</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077386</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077387</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077389</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077390</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077391</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077393</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077396</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077398</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077399</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077400</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077401</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077404</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077421</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077424</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077425</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077452</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077488</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077491</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077492</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077494</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077495</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077496</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077497</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077498</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077499</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077501</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077502</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077503</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077521</smpdb_id>
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      <smpdb_id>SMP0077522</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077523</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077524</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077525</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077526</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077595</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077596</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077597</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077598</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077599</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077600</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077601</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077602</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077603</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077604</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077605</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077606</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077607</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077608</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077609</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077610</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077611</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077612</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077613</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077614</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077615</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077616</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077617</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077618</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077619</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077620</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077621</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077622</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077625</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077627</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077629</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077638</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077639</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077645</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077649</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077650</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077651</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077652</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077653</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077654</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077655</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077656</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077657</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077658</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077659</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077660</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077661</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077662</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077663</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077664</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077665</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077666</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077681</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077682</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077688</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077689</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077690</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077691</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077692</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077700</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077701</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077702</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077703</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077704</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077707</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077723</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077724</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077725</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077731</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077732</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077733</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077734</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077735</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077736</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077741</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077742</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077743</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077744</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077745</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077746</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077747</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077748</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077749</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077750</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077751</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077752</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077753</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077754</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077755</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077756</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077757</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077758</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077760</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077761</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077762</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077763</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077764</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077765</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077766</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077767</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077768</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077771</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077772</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077773</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077775</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077778</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077793</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077798</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077801</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077802</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077803</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077804</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077805</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077806</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077809</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077810</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077811</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077812</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077813</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077814</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077815</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077816</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077817</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077818</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077819</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077820</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077821</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077822</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077823</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077824</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077825</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077826</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077827</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077828</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077830</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077831</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077832</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077833</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077837</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077840</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077841</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077842</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077843</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077844</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077845</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077846</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077847</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077848</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077849</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077850</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077852</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077853</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077854</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077855</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077856</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077857</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077863</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077895</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077900</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077901</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077902</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077903</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077904</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077905</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077906</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077908</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077909</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077910</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077911</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077912</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077913</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077914</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077915</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077916</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077917</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077918</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077919</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077920</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077921</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077922</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077923</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077924</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077925</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077926</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077927</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077928</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077929</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077930</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077931</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077932</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077933</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077934</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077935</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077936</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077937</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077938</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077939</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077940</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077941</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077942</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077943</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077944</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077945</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077946</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077947</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077948</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077951</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077983</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078122</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078123</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078124</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078125</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078126</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/16:0)</name>
      <smpdb_id>SMP0078130</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078131</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:0)</name>
      <smpdb_id>SMP0078132</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078133</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078134</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078135</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078136</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078137</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078138</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078141</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078145</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078150</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078151</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078152</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078153</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078154</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078155</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078156</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078157</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078159</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078160</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078161</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078162</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078163</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078164</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078170</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078171</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078172</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078173</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078174</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078180</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078181</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078182</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078184</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078187</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078191</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078193</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078195</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078197</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078199</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078200</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078201</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078202</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078203</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078205</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078206</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078207</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078213</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078214</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078215</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078216</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078217</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078218</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:0)</name>
      <smpdb_id>SMP0078219</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078220</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078221</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078223</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078224</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078225</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078226</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078233</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078234</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078235</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078243</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078244</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078245</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078246</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078252</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078253</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078254</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078255</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078256</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078257</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078258</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078259</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078260</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078262</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078263</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078264</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078265</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078266</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078267</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078268</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078269</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078270</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078271</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078272</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078273</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078274</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078275</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078276</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078277</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078278</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078279</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078280</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078281</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078282</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078283</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078284</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078285</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078286</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078287</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078289</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078290</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078292</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078293</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078295</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078297</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078298</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078299</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078300</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078301</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078302</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078303</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078304</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078305</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078306</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078307</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078308</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078309</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078310</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078311</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078312</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078313</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078314</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078315</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078316</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078317</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078318</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078319</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078320</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078321</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078322</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078323</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078324</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078325</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078326</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078327</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078328</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078329</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078330</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078331</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078332</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078333</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078334</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078338</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078348</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078350</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078351</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078352</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078353</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078354</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078355</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078357</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078360</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078361</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078362</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078363</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078364</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078365</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078366</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078367</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078368</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078370</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078371</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078372</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078373</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078374</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078375</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078376</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078384</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078385</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078386</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078388</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078389</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078390</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078391</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078392</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078393</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078394</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078395</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078396</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078397</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078398</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078399</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078400</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078406</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078407</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078408</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078416</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078419</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078420</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078421</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078422</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078423</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078424</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078425</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078426</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078427</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078428</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078429</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078430</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078431</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078432</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078433</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078434</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078435</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078436</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078437</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078438</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078439</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078440</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078443</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078444</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078445</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078446</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078447</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078448</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078457</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078458</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078460</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078461</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078462</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078463</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078464</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078465</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078466</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078467</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078468</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078469</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078470</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078471</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078472</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078473</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078474</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078475</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078476</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078477</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078478</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078479</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078480</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078481</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078482</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078483</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078484</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078485</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078486</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078487</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078488</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078489</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078490</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078491</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078492</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078493</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078494</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078495</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078496</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078497</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078498</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078499</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078500</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078501</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078502</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078503</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078504</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078505</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078506</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078507</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078508</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078509</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078510</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078511</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078512</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078514</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078516</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078517</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078518</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078519</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078520</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078521</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078522</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078523</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078524</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078525</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078526</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078527</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078528</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078601</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078602</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078603</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078604</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078605</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078606</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078607</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078608</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078609</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078610</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078611</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078612</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078613</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078614</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078615</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078616</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078617</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078618</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078619</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078620</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078621</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078622</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078623</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078624</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078625</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078626</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078627</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078628</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078629</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078630</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078631</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078632</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078633</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078634</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078635</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078636</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078637</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078638</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078639</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078640</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078641</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078642</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078643</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078644</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078645</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078647</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078648</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078649</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078650</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078651</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078652</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078653</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078654</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078655</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078656</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078657</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078658</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078659</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078660</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078661</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078662</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078663</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078664</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078665</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078666</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078667</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078668</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078669</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078670</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078671</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078672</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078673</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078674</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078675</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078676</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078677</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078678</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078679</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078680</smpdb_id>
      <kegg_map_id/>
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      <smpdb_id>SMP0078681</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078688</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078692</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078693</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078694</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078699</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078700</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078701</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078702</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078706</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078707</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078708</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078709</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078755</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078756</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078757</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078758</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078762</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078840</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078841</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078842</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078843</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078844</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078845</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078846</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078847</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078848</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078849</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078850</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078851</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078852</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078853</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078854</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078855</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078857</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078858</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078859</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078861</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078862</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078864</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078867</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078870</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078875</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078876</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078877</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078878</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078885</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078887</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078888</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078890</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078914</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079139</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079140</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079141</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079142</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079143</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079144</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079145</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079146</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079147</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079148</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079149</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079150</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0079152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079170</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079171</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079175</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079176</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079180</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079181</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079185</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079186</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079187</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079189</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079197</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079199</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079204</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079205</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079209</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079210</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079211</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079212</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079213</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079214</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079215</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079216</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079217</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079218</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079219</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079220</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079221</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079222</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079223</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079224</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079225</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079226</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079227</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079228</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079229</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079230</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079231</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079232</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079233</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079234</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079235</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079237</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079238</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079239</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079240</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079241</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079242</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079243</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079244</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079245</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079249</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079250</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079251</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079252</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079253</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079254</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079255</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079256</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079257</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079258</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079259</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079260</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079261</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079262</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079263</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079264</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079265</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079266</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079267</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079268</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079269</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079270</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079271</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079272</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079273</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079274</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079275</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079276</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079277</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079278</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079279</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079280</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079281</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079282</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079283</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079284</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079285</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079286</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079287</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079288</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079289</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079290</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079291</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079292</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079293</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079295</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079296</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079297</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079298</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079299</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079300</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079301</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079302</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079303</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079304</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079305</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079306</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079307</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079308</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079309</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079310</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079311</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079312</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079313</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079314</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079315</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079316</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079321</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079326</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079357</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079427</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079428</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079429</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079430</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079431</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079432</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079433</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079434</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079435</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079436</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079437</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079438</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079439</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079440</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079441</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079442</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079443</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079444</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079445</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079449</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079454</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079463</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079464</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079465</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079466</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079467</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079468</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079469</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079470</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079471</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079472</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079473</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079474</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079475</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079476</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079477</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079478</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079479</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079480</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079481</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079482</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079484</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079485</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079486</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079488</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079489</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079490</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079491</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079492</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079493</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079494</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079495</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079496</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079497</smpdb_id>
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      <smpdb_id>SMP0079498</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079499</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079500</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079501</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079502</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079503</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079504</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079505</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079506</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079507</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079508</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079510</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079511</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079512</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079513</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079515</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079516</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079534</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079535</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079536</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079563</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079564</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079565</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079570</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079572</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079573</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079578</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079579</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079580</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079581</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079582</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079583</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079584</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079585</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079586</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079587</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079588</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0079603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0079604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079647</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079650</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079651</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079652</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079653</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079654</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079656</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079657</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079658</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079659</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079660</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079661</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079662</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079664</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079666</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079667</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079668</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079693</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079694</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079704</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079706</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079707</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079708</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079709</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079713</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079714</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079719</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079761</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079762</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079782</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079784</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079788</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079789</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079795</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079796</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079798</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079799</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079800</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <smpdb_id>SMP0079851</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079981</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080000</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080008</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080009</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080010</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080013</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080014</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0080015</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080016</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080017</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0080018</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0080019</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080020</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0080021</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080022</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080023</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080024</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080025</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080026</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080027</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080028</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080029</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080030</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080031</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080032</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080033</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080034</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080035</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080038</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080039</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080040</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080042</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080043</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080044</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080045</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080046</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080236</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080237</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080238</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080239</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080365</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080371</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080381</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080409</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080410</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080412</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080414</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080422</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pantothenate and CoA Biosynthesis</name>
      <smpdb_id>SMP0087207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis</name>
      <smpdb_id>SMP0072037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:0)</name>
      <smpdb_id>SMP0080430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0080431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/15:0)</name>
      <smpdb_id>SMP0080432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:0)</name>
      <smpdb_id>SMP0080433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0080434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:0)</name>
      <smpdb_id>SMP0080435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0080436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0080437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:0)</name>
      <smpdb_id>SMP0080442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0080443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:0)</name>
      <smpdb_id>SMP0080450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0080451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:0)</name>
      <smpdb_id>SMP0080457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0080458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0080459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0080460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0080461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/15:0)</name>
      <smpdb_id>SMP0080487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:0)</name>
      <smpdb_id>SMP0080488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0080489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:0)</name>
      <smpdb_id>SMP0080490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0080491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0080492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:0)</name>
      <smpdb_id>SMP0080497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0080498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:0)</name>
      <smpdb_id>SMP0080505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0080506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:0)</name>
      <smpdb_id>SMP0080512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0080513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:0)</name>
      <smpdb_id>SMP0080514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0080515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:0)</name>
      <smpdb_id>SMP0080516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0080517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0080518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:0)</name>
      <smpdb_id>SMP0080523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0080524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:0)</name>
      <smpdb_id>SMP0080531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0080532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:0)</name>
      <smpdb_id>SMP0080538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0080539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:0)</name>
      <smpdb_id>SMP0080565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0080566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0080567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:0)</name>
      <smpdb_id>SMP0080572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0080573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:0)</name>
      <smpdb_id>SMP0080580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0080581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:0)</name>
      <smpdb_id>SMP0080587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0080588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0080595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:0)</name>
      <smpdb_id>SMP0080712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0080713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:0)</name>
      <smpdb_id>SMP0080720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0080721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:0)</name>
      <smpdb_id>SMP0080727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0080728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0080765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0080772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:0)</name>
      <smpdb_id>SMP0080820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0080821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:0)</name>
      <smpdb_id>SMP0080827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0080828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0080835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:0)</name>
      <smpdb_id>SMP0080864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0080865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis</name>
      <smpdb_id>SMP0072048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:0)</name>
      <smpdb_id>SMP0082233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0082234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/15:0)</name>
      <smpdb_id>SMP0082235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:0)</name>
      <smpdb_id>SMP0082236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0082237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:0)</name>
      <smpdb_id>SMP0082238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0082239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0082240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:0)</name>
      <smpdb_id>SMP0082245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0082246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:0)</name>
      <smpdb_id>SMP0082253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0082254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:0)</name>
      <smpdb_id>SMP0082260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0082261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0082262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0082263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0082264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/15:0)</name>
      <smpdb_id>SMP0082290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:0)</name>
      <smpdb_id>SMP0082291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0082292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:0)</name>
      <smpdb_id>SMP0082293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0082294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0082295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:0)</name>
      <smpdb_id>SMP0082300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0082301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:0)</name>
      <smpdb_id>SMP0082308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0082309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:0)</name>
      <smpdb_id>SMP0082315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0082316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:0)</name>
      <smpdb_id>SMP0082317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0082318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:0)</name>
      <smpdb_id>SMP0082319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0082320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0082321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:0)</name>
      <smpdb_id>SMP0082326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0082327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:0)</name>
      <smpdb_id>SMP0082334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0082335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:0)</name>
      <smpdb_id>SMP0082341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0082342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:0)</name>
      <smpdb_id>SMP0082368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0082369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0082370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:0)</name>
      <smpdb_id>SMP0082375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0082376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:0)</name>
      <smpdb_id>SMP0082383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0082384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:0)</name>
      <smpdb_id>SMP0082390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0082391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0082398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:0)</name>
      <smpdb_id>SMP0082520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0082521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:0)</name>
      <smpdb_id>SMP0082528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0082529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:0)</name>
      <smpdb_id>SMP0082535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0082536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0082574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0082581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:0)</name>
      <smpdb_id>SMP0082629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0082630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:0)</name>
      <smpdb_id>SMP0082636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0082637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0082644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:0)</name>
      <smpdb_id>SMP0082671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0082672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181547</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00063</kegg_id>
  <foodb_id>FDB030748</foodb_id>
  <drugbank_id>DB02431</drugbank_id>
  <chemspider_id>5941</chemspider_id>
  <pubchem_compound_id>6176</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17677</chebi_id>
  <knapsack_id>C00019639</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Cytidine triphosphate</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33710</bigg_id>
  <metlin_id>5136</metlin_id>
  <synthesis_reference>Simon, Ethan S.; Bednarski, Mark D.; Whitesides, George M. Synthesis of CMP-NeuAc from N-acetylglucosamine: generation of CTP from CMP using adenylate kinase. Journal of the American Chemical Society (1988), 110(21), 7159-63.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:27 UTC</creation_date>
  <update_date>2020-04-15 20:47:44 UTC</update_date>
  <accession>BMDB0000085</accession>
  <secondary_accessions>
    <accession>BMDB00085</accession>
  </secondary_accessions>
  <name>Deoxyguanosine</name>
  <description/>
  <synonyms>
    <synonym>2-Amino-9-(2-deoxy-9-beta-D-ribofuranosyl)-9H-purin-6-ol</synonym>
    <synonym>9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-guanine</synonym>
    <synonym>dG</synonym>
    <synonym>Guanine deoxy nucleoside</synonym>
    <synonym>2'-Deoxyguanosine</synonym>
    <synonym>2-Amino-9-(2-deoxy-9-b-D-ribofuranosyl)-9H-purin-6-ol</synonym>
    <synonym>2-Amino-9-(2-deoxy-9-β-D-ribofuranosyl)-9H-purin-6-ol</synonym>
    <synonym>9-(2-Deoxy-b-D-erythro-pentofuranosyl)-guanine</synonym>
    <synonym>9-(2-Deoxy-β-D-erythro-pentofuranosyl)-guanine</synonym>
    <synonym>2'-Deoxy-guanosine</synonym>
    <synonym>2-Deoxyguanosine</synonym>
    <synonym>9-(2-Deoxy-b-D-erythro-pentofuranosyl)guanine</synonym>
    <synonym>9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-guanine</synonym>
    <synonym>9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)guanine</synonym>
    <synonym>Desoxyguanosine</synonym>
    <synonym>Guanine deoxyriboside</synonym>
    <synonym>Deoxyguanosine</synonym>
  </synonyms>
  <chemical_formula>C10H13N5O4</chemical_formula>
  <average_molecular_weight>267.2413</average_molecular_weight>
  <monisotopic_moleculate_weight>267.096753929</monisotopic_moleculate_weight>
  <iupac_name>2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one</iupac_name>
  <traditional_iupac>2-deoxyguanosine</traditional_iupac>
  <cas_registry_number>961-07-9</cas_registry_number>
  <smiles>NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1</smiles>
  <inchi>InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1</inchi>
  <inchikey>YKBGVTZYEHREMT-KVQBGUIXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleosides</class>
    <sub_class>Purine 2'-deoxyribonucleosides</sub_class>
    <direct_parent>Purine 2'-deoxyribonucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine 2'-deoxyribonucleoside</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxyribonucleosides</external_descriptor>
      <external_descriptor>purine 2'-deoxyribonucleoside</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>300 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.3</value>
      <source>BALZARINI,JM ET AL. (1989)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>267.2413</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>267.096753929</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H13N5O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YKBGVTZYEHREMT-KVQBGUIXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>134.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>63.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2796</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437562</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00330</kegg_id>
  <pubchem_compound_id>187790</pubchem_compound_id>
  <chemspider_id>163230</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB012064</foodb_id>
  <pdbe_id/>
  <chebi_id>17172</chebi_id>
  <meta_cyc_id>DEOXYGUANOSINE</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>34637</bigg_id>
  <wikipedia_id>Deoxyguanosine</wikipedia_id>
  <metlin_id>3395</metlin_id>
  <synthesis_reference>Noguchi, Toshitada; Hamamoto, Tomoki; Okuyama, Kiyoshi; Shibuya, Susumu.  Process for producing 2'-deoxyguanosine.   PCT Int. Appl.  (2003), 31 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:28 UTC</creation_date>
  <update_date>2020-04-16 20:37:21 UTC</update_date>
  <accession>BMDB0000086</accession>
  <secondary_accessions>
    <accession>BMDB00086</accession>
  </secondary_accessions>
  <name>Glycerophosphocholine</name>
  <description>Glycerophosphocholine, also known as GPC or choline alfoscerate, belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position. Glycerophosphocholine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Glycerophosphocholine exists in all living species, ranging from bacteria to humans. Glycerophosphocholine participates in a number of enzymatic reactions, within cattle. In particular, Glycerophosphocholine can be biosynthesized from 11-cis-retinol and PC(24:1(15Z)/15:0); which is mediated by the enzyme lecithin retinol acyltransferase. In addition, Retinyl ester and glycerophosphocholine can be biosynthesized from vitamin a and PC(24:1(15Z)/15:0) through its interaction with the enzyme lecithin retinol acyltransferase. In cattle, glycerophosphocholine is involved in the metabolic pathway called the retinol metabolism pathway.</description>
  <synonyms>
    <synonym>2-[[(2,3-Dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium inner salt</synonym>
    <synonym>a-Glycerophosphorylcholine</synonym>
    <synonym>a-Glycerylphosphorylcholine</synonym>
    <synonym>alpha-Glycerophosphorylcholine</synonym>
    <synonym>alpha-Glycerylphosphorylcholine</synonym>
    <synonym>Choline alfoscerate</synonym>
    <synonym>Choline glycerophosphate</synonym>
    <synonym>Glycerol 3-phosphocholine</synonym>
    <synonym>Glycerol phosphorylcholine</synonym>
    <synonym>Glycerol-3-phosphatidylcholine</synonym>
    <synonym>Glycerophosphatidylcholine</synonym>
    <synonym>Glycerophosphorylcholine</synonym>
    <synonym>GPC</synonym>
    <synonym>GPCho</synonym>
    <synonym>Hydrogen glycerophosphate choline</synonym>
    <synonym>L-alpha-Glycerophosphocholine</synonym>
    <synonym>L-alpha-Glycerophosphorylcholine</synonym>
    <synonym>L-alpha-Glycerylphosphorylcholine</synonym>
    <synonym>L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner salt</synonym>
    <synonym>sn-glycero-3-Phosphocholine</synonym>
    <synonym>Alfoscerate, choline</synonym>
    <synonym>Choline alphoscerate</synonym>
    <synonym>Glycerophosphate, choline</synonym>
    <synonym>Alphoscerate, choline</synonym>
    <synonym>L alpha Glycerylphosphorylcholine</synonym>
    <synonym>3-Phosphocholine, glycerol</synonym>
    <synonym>Glycerol 3 phosphocholine</synonym>
    <synonym>Glycerylphosphorylcholine</synonym>
    <synonym>Cereton</synonym>
    <synonym>Cholicerin</synonym>
    <synonym>Cholitiline</synonym>
    <synonym>Delecit</synonym>
    <synonym>Gliatilin</synonym>
    <synonym>Glycerol 3-phosphorylcholine</synonym>
    <synonym>Glycerophosphocholine</synonym>
    <synonym>Glycerophosphoric acid choline ester</synonym>
    <synonym>Glyceryl 3-phosphorylcholine</synonym>
    <synonym>Glycerylphosphocholine</synonym>
    <synonym>L-alpha-GPC</synonym>
    <synonym>L-α-GPC</synonym>
    <synonym>L-α-Glycerophosphocholine</synonym>
    <synonym>L-α-Glycerophosphorylcholine</synonym>
    <synonym>L-α-Glycerylphosphorylcholine</synonym>
    <synonym>O-(sn-glycero-3-Phosphoryl)-choline</synonym>
    <synonym>sn-glycero-3-Phosphorylcholine</synonym>
    <synonym>α-Glycerophosphorylcholine</synonym>
    <synonym>α-Glycerylphosphorylcholine</synonym>
  </synonyms>
  <chemical_formula>C8H20NO6P</chemical_formula>
  <average_molecular_weight>257.2213</average_molecular_weight>
  <monisotopic_moleculate_weight>257.102823889</monisotopic_moleculate_weight>
  <iupac_name>(2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium</iupac_name>
  <traditional_iupac>Alpha-GPC</traditional_iupac>
  <cas_registry_number/>
  <smiles>C[N+](C)(C)CCOP([O-])(=O)OC[C@@H](O)CO</smiles>
  <inchi>InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/t8-/m0/s1</inchi>
  <inchikey>SUHOQUVVVLNYQR-QMMMGPOBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerophospholipids</class>
    <sub_class>Glycerophosphocholines</sub_class>
    <direct_parent>Glycerophosphocholines</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Dialkyl phosphates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phosphocholines</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Dialkyl phosphate</substituent>
      <substituent>Glycero-3-phosphocholine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphocholine</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>142.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2-{[(2S)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>257.2213</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>257.102823889</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)CCOP([O-])(=O)OC[C@@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H20NO6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/t8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SUHOQUVVVLNYQR-QMMMGPOBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>99.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Retinol Metabolism</name>
      <smpdb_id>SMP0087260</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339384</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>10833+/-1521</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>284 - 1460</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>395 - 1217</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>532.34 +/- 107.89</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>669 +/- 53</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>659 +/- 8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>646 +/- 21</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>705 +/- 45</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>531.67 +/- 240.19</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 54 Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
          <pubmed_id>23394630</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>617.18 +/- 83.87</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>702+/-121</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id/>
  <pubchem_compound_id>71920</pubchem_compound_id>
  <chemspider_id/>
  <drugbank_id/>
  <foodb_id/>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Alpha-GPC</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Evans, Christopher Thomas; McCague, Raymond; Tyrrell, Nicholas David.  Preparation of phospholipid-intermediate glycerophosphocholine by a crystallization process.    PCT Int. Appl.  (1993),     8 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
      <pubmed_id>23394630</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
      <pubmed_id>28342601</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00783</protein_accession>
      <name>Cytosolic phospholipase A2</name>
      <uniprot_id>A4IFJ5</uniprot_id>
      <gene_name>PLA2G4A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:29 UTC</creation_date>
  <update_date>2020-04-15 22:22:30 UTC</update_date>
  <accession>BMDB0000087</accession>
  <secondary_accessions>
    <accession>BMDB00087</accession>
  </secondary_accessions>
  <name>Dimethylamine</name>
  <description>Dimethylamine, also known as DMA or HNME2, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Dimethylamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Dimethylamine exists in all living organisms, ranging from bacteria to humans. Dimethylamine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>DMA</synonym>
    <synonym>HNMe2</synonym>
    <synonym>Me2nh</synonym>
    <synonym>N,N-Dimethylamine</synonym>
    <synonym>(CH3)2nh</synonym>
    <synonym>Dimethylamine anhydrous</synonym>
    <synonym>Dimethylamine anhydrous (dot)</synonym>
    <synonym>Dimethylamine aqueous solution</synonym>
    <synonym>Dimethylamine hydrobromide</synonym>
    <synonym>Dimethylamine solution</synonym>
    <synonym>N-Methyl-methanamine</synonym>
    <synonym>N-Methylmethanamine</synonym>
    <synonym>N-Methylmethanamine (acd/name 4.0)</synonym>
    <synonym>Dimethylamine nitrate</synonym>
    <synonym>Dimethylamine perchlorate</synonym>
    <synonym>Dimethylamine sulfate</synonym>
    <synonym>Dimethylamine hydrochloride</synonym>
    <synonym>Dimethylamine phosphate (3:1)</synonym>
    <synonym>Dimethylamine, conjugate acid</synonym>
    <synonym>Dimethylammonium chloride</synonym>
    <synonym>Dimethylamine sulfate (1:1)</synonym>
    <synonym>Dimethylammonium formate</synonym>
    <synonym>Dimethylamine monosulfate</synonym>
  </synonyms>
  <chemical_formula>C2H7N</chemical_formula>
  <average_molecular_weight>45.0837</average_molecular_weight>
  <monisotopic_moleculate_weight>45.057849229</monisotopic_moleculate_weight>
  <iupac_name>dimethylamine</iupac_name>
  <traditional_iupac>dimethylamine</traditional_iupac>
  <cas_registry_number>124-40-3</cas_registry_number>
  <smiles>CNC</smiles>
  <inchi>InChI=1S/C2H7N/c1-3-2/h3H,1-2H3</inchi>
  <inchikey>ROSDSFDQCJNGOL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>Dialkylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary aliphatic amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>methylamines</external_descriptor>
      <external_descriptor>secondary aliphatic amine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-92.2 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1630 mg/mL at 40 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.38</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>dimethylamine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>45.0837</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>45.057849229</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CNC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H7N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H7N/c1-3-2/h3H,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ROSDSFDQCJNGOL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>12.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>14.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>5.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310545</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 54 Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
          <pubmed_id>23394630</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Charolais cows.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9.95 +/- 1.96</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9.40 +/- 2.30</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 54 Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
          <pubmed_id>23394630</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14.60 +/- 2.77</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>7.59</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>29.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>33.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>4.36</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>21.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>47.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>51.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>9.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>22 +/- 6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>47 +/- 45</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>52 +/- 31</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>10 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00543</kegg_id>
  <foodb_id>FDB012589</foodb_id>
  <drugbank_id/>
  <chemspider_id>654</chemspider_id>
  <pubchem_compound_id>674</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17170</chebi_id>
  <knapsack_id/>
  <meta_cyc_id>DIMETHYLAMINE</meta_cyc_id>
  <wikipedia_id>Dimethylamine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>3758</metlin_id>
  <synthesis_reference>Zones, Stacey I.; Burton, Allen W.  Production of methylamine and dimethylamine using STI zeolite catalysts. U.S. Pat. Appl. Publ.  (2007),  6pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
      <pubmed_id>23394630</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00611</protein_accession>
      <name>N(G),N(G)-dimethylarginine dimethylaminohydrolase 2</name>
      <uniprot_id>Q3SX44</uniprot_id>
      <gene_name>DDAH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00612</protein_accession>
      <name>N(G),N(G)-dimethylarginine dimethylaminohydrolase 1</name>
      <uniprot_id>P56965</uniprot_id>
      <gene_name>DDAH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:30 UTC</creation_date>
  <update_date>2020-04-15 20:47:45 UTC</update_date>
  <accession>BMDB0000089</accession>
  <secondary_accessions>
    <accession>BMDB00089</accession>
  </secondary_accessions>
  <name>Cytidine</name>
  <description>Cytarabine, also known as cytosar or aracytine, belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. Cytarabine is a drug which is used for the treatment of acute non-lymphocytic leukemia, acute lymphocytic leukemia and blast phase of chronic myelocytic leukemia. Cytarabine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Cytarabine exists in all living species, ranging from bacteria to humans. Cytarabine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-beta-D-Arabinofuranosylcytosine</synonym>
    <synonym>4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone</synonym>
    <synonym>Ara-C</synonym>
    <synonym>Arabinocytosine</synonym>
    <synonym>Arabinoside C</synonym>
    <synonym>Citarabina</synonym>
    <synonym>Cytarabinum</synonym>
    <synonym>Cytosine arabinoside</synonym>
    <synonym>Cytosine-1-beta-D-arabinofuranoside</synonym>
    <synonym>Cytosine-beta-D-arabinofuranoside</synonym>
    <synonym>Depocyt</synonym>
    <synonym>1-b-D-Arabinofuranosylcytosine</synonym>
    <synonym>1-Β-D-arabinofuranosylcytosine</synonym>
    <synonym>4-Amino-1-b-D-arabinofuranosyl-2(1H)-pyrimidinone</synonym>
    <synonym>4-Amino-1-β-D-arabinofuranosyl-2(1H)-pyrimidinone</synonym>
    <synonym>Cytosine-1-b-D-arabinofuranoside</synonym>
    <synonym>Cytosine-1-β-D-arabinofuranoside</synonym>
    <synonym>Cytosine-b-D-arabinofuranoside</synonym>
    <synonym>Cytosine-β-D-arabinofuranoside</synonym>
    <synonym>(beta-D-Arabinofuranosyl)cytosine</synonym>
    <synonym>1-Arabinofuranosylcytosine</synonym>
    <synonym>1-beta -D-Arabinofaranosylcytosine</synonym>
    <synonym>1-beta -D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone</synonym>
    <synonym>1-beta -D-Arabinofuranosylcytosine</synonym>
    <synonym>1-beta-D-Arabinofaranosylcytosine</synonym>
    <synonym>1-beta-D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone</synonym>
    <synonym>1-beta-D-Arabinofuranosyl-cytosine</synonym>
    <synonym>1-beta-D-Arabinofuranosylcytosine, cytosine arabinoside</synonym>
    <synonym>1-beta-D-Arabinosyl-cytosine</synonym>
    <synonym>1-beta-D-Arabinosylcytosine</synonym>
    <synonym>1beta -Arabinofuranasylcytosine</synonym>
    <synonym>1beta -D-Arabinofuranosylcytosine</synonym>
    <synonym>1beta -D-Arabinosylcytosine</synonym>
    <synonym>1beta-Arabinofuranasylcytosine</synonym>
    <synonym>1beta-D-Arabinofuranosylcytosine</synonym>
    <synonym>1beta-D-Arabinosylcytosine</synonym>
    <synonym>2(1H)-Pyrimidinone, 4-amino-1- -D-arabinofuranosyl</synonym>
    <synonym>4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin</synonym>
    <synonym>4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidine</synonym>
    <synonym>4-Amino-1-b-D-arabinofuranosyl-2-(1H)-pyrimidinone</synonym>
    <synonym>4-Amino-1-beta-D-arabinofuranosylpyrimidin-2(1H)-one</synonym>
    <synonym>Alexan</synonym>
    <synonym>Arabinocytidine</synonym>
    <synonym>Arabinofuranosylcytosine</synonym>
    <synonym>Arabinosylcytosine</synonym>
    <synonym>Arabitin</synonym>
    <synonym>AraC</synonym>
    <synonym>Aracytidine</synonym>
    <synonym>Aracytin</synonym>
    <synonym>Aracytine</synonym>
    <synonym>Arafcyt</synonym>
    <synonym>beta -Arabinosylcytosine</synonym>
    <synonym>beta -Cytosine arabinoside</synonym>
    <synonym>beta -D-Arabinosylcytosine</synonym>
    <synonym>beta-Ara c</synonym>
    <synonym>beta-Arabinosylcytosine</synonym>
    <synonym>beta-Cytosine arabinoside</synonym>
    <synonym>beta-D-Arabinosylcytosine</synonym>
    <synonym>Cytarabin</synonym>
    <synonym>Cytarabina</synonym>
    <synonym>Cytarabine liposome injection</synonym>
    <synonym>Cytarabinoside</synonym>
    <synonym>Cytonal</synonym>
    <synonym>Cytosar</synonym>
    <synonym>Cytosar-u</synonym>
    <synonym>Cytosine 1-beta-D-arabinofuranoside</synonym>
    <synonym>Cytosine arabinofuranoside</synonym>
    <synonym>Cytosine arabinose</synonym>
    <synonym>Cytosine beta-D-arabinofuranoside</synonym>
    <synonym>Cytosine beta-D-arabinoside</synonym>
    <synonym>Cytosine, beta -D-arabinoside</synonym>
    <synonym>Cytosine, beta-D-arabinoside</synonym>
    <synonym>Cytosine-1-beta-D-arabinofuranoside hydrochloride</synonym>
    <synonym>Cytosine-beta -arabinoside</synonym>
    <synonym>Cytosine-beta -D-arabinofuranoside</synonym>
    <synonym>Cytosine-beta-arabinoside</synonym>
    <synonym>Cytosinearabinoside</synonym>
    <synonym>Depocyte</synonym>
    <synonym>Erpalfa</synonym>
    <synonym>Iretin</synonym>
    <synonym>Spongocytidine</synonym>
    <synonym>Tarabine</synonym>
    <synonym>Udicil</synonym>
    <synonym>Arabinoside, cytosine</synonym>
    <synonym>CytosarU</synonym>
    <synonym>Hydrochloride, cytarabine</synonym>
    <synonym>Cytarabine hydrochloride</synonym>
    <synonym>Cytosar u</synonym>
    <synonym>Ara C</synonym>
    <synonym>beta Ara C</synonym>
    <synonym>Cytarabine</synonym>
  </synonyms>
  <chemical_formula>C9H13N3O5</chemical_formula>
  <average_molecular_weight>243.2166</average_molecular_weight>
  <monisotopic_moleculate_weight>243.085520541</monisotopic_moleculate_weight>
  <iupac_name>4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one</iupac_name>
  <traditional_iupac>cytarabine</traditional_iupac>
  <cas_registry_number>147-94-4</cas_registry_number>
  <smiles>NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1</inchi>
  <inchikey>UHDGCWIWMRVCDJ-CCXZUQQUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleosides</class>
    <sub_class/>
    <direct_parent>Pyrimidine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine nucleoside</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>beta-D-arabinoside</external_descriptor>
      <external_descriptor>monosaccharide derivative</external_descriptor>
      <external_descriptor>pyrimidine nucleoside</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>230.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.51</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.062</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>243.2166</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>243.085520541</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13N3O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UHDGCWIWMRVCDJ-CCXZUQQUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>128.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>40570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445921</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445922</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445924</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447206</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.4 - 11.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68.</reference_text>
          <pubmed_id>11242448</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB00987</drugbank_id>
  <chemspider_id>6017</chemspider_id>
  <pubchem_compound_id>6253</pubchem_compound_id>
  <foodb_id>FDB001216</foodb_id>
  <chebi_id>28680</chebi_id>
  <kegg_id>C02961</kegg_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Cytarabine</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Qu, Guirong; Yang, Xining; Shen, Yanhong; Dong, Chunhong; Guo, Haiming; Wang, Xiuqiang; Wang, Dongchao.  Synthesis of cytidine.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2007),  11pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00580</protein_accession>
      <name>Activation-induced cytidine deaminase</name>
      <uniprot_id>Q2PT36</uniprot_id>
      <gene_name>AICDA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00583</protein_accession>
      <name>Uridine-cytidine kinase 1</name>
      <uniprot_id>Q0P5A4</uniprot_id>
      <gene_name>UCK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:32 UTC</creation_date>
  <update_date>2020-04-15 22:13:07 UTC</update_date>
  <accession>BMDB0000092</accession>
  <secondary_accessions>
    <accession>BMDB00092</accession>
  </secondary_accessions>
  <name>Dimethylglycine</name>
  <description>Dimethylglycine, also known as N-methylsarcosine, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Dimethylglycine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Dimethylglycine exists in all living organisms, ranging from bacteria to humans. Dimethylglycine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(Dimethylamino)acetic acid</synonym>
    <synonym>2-(Dimethylamino)acetic acid</synonym>
    <synonym>N,N-Dimethylaminoacetic acid</synonym>
    <synonym>N-Methylsarcosine</synonym>
    <synonym>(Dimethylamino)acetate</synonym>
    <synonym>2-(Dimethylamino)acetate</synonym>
    <synonym>N,N-Dimethylaminoacetate</synonym>
    <synonym>N,N-Dimethylglycine</synonym>
    <synonym>N-Methylsarcosine N,N-dimethyl-glycine</synonym>
    <synonym>Dimethylglycine, monopotassium salt</synonym>
    <synonym>Dimethylglycine, sodium salt</synonym>
    <synonym>Dimethylglycine, calcium salt</synonym>
    <synonym>Dimethylglycine monohydrochloride</synonym>
    <synonym>2-(N,N-Dimethylamino)acetic acid</synonym>
    <synonym>DMG</synonym>
    <synonym>Dimethylglycine</synonym>
  </synonyms>
  <chemical_formula>C4H9NO2</chemical_formula>
  <average_molecular_weight>103.1198</average_molecular_weight>
  <monisotopic_moleculate_weight>103.063328537</monisotopic_moleculate_weight>
  <iupac_name>2-(dimethylamino)acetic acid</iupac_name>
  <traditional_iupac>dimethylglycine</traditional_iupac>
  <cas_registry_number>1118-68-9</cas_registry_number>
  <smiles>CN(C)CC(O)=O</smiles>
  <inchi>InChI=1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)</inchi>
  <inchikey>FFDGPVCHZBVARC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-methyl-amino acid</external_descriptor>
      <external_descriptor>N-methylglycines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>185.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.91</value>
      <source>TSAI,RS ET AL. (1991)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(dimethylamino)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>103.1198</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>103.063328537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN(C)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H9NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FFDGPVCHZBVARC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>26.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445984</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by UPLC-Q-TOF MS E</comment>
      <references>
        <reference>
          <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
          <pubmed_id>28342601</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01026</kegg_id>
  <foodb_id>FDB021893</foodb_id>
  <drugbank_id>DB02083</drugbank_id>
  <chemspider_id>653</chemspider_id>
  <pubchem_compound_id>673</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17724</chebi_id>
  <knapsack_id/>
  <meta_cyc_id>DIMETHYL-GLYCINE</meta_cyc_id>
  <wikipedia_id>Dimethylglycine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>36652</bigg_id>
  <metlin_id>277</metlin_id>
  <synthesis_reference>Lai, Mei-Chin; Wang, Chia-Chi; Chuang, Ming-Jen; Wu, Yen-Chi; Lee, Yu-Chien. Effects of substrate and potassium on the betaine-synthesizing enzyme glycine sarcosine dimethylglycine N-methyltransferase from a halophilic methanoarchaeon Methanohalophilus portucalensis. Res Microbiol. 2006 Dec;157(10):948-55. Epub 2006 Oct 26. Pubmed: 17098399</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
    <reference>
      <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
      <pubmed_id>28342601</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01057</protein_accession>
      <name>Betaine--homocysteine S-methyltransferase 1</name>
      <uniprot_id>Q5I597</uniprot_id>
      <gene_name>BHMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:33 UTC</creation_date>
  <update_date>2020-04-15 20:47:46 UTC</update_date>
  <accession>BMDB0000094</accession>
  <secondary_accessions>
    <accession>BMDB00094</accession>
  </secondary_accessions>
  <name>Citric acid</name>
  <description>Citric acid, also known as citrate or citronensaeure, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Citric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Citric acid exists in all living species, ranging from bacteria to humans. Citric acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2-Hydroxy-1,2,3-propanetricarboxylic acid</synonym>
    <synonym>2-Hydroxytricarballylic acid</synonym>
    <synonym>3-Carboxy-3-hydroxypentane-1,5-dioic acid</synonym>
    <synonym>Citronensaeure</synonym>
    <synonym>e330</synonym>
    <synonym>H3Cit</synonym>
    <synonym>Anhydrous citric acid</synonym>
    <synonym>Citric acid anhydrous</synonym>
    <synonym>2-Hydroxy-1,2,3-propanetricarboxylate</synonym>
    <synonym>2-Hydroxytricarballylate</synonym>
    <synonym>3-Carboxy-3-hydroxypentane-1,5-dioate</synonym>
    <synonym>Anhydrous citrate</synonym>
    <synonym>Citrate anhydrous</synonym>
    <synonym>Citrate</synonym>
    <synonym>Aciletten</synonym>
    <synonym>beta-Hydroxytricarballylate</synonym>
    <synonym>beta-Hydroxytricarballylic acid</synonym>
    <synonym>Chemfill</synonym>
    <synonym>Citraclean</synonym>
    <synonym>Citretten</synonym>
    <synonym>Citro</synonym>
    <synonym>e 330</synonym>
    <synonym>Hydrocerol a</synonym>
    <synonym>Kyselina citronova</synonym>
    <synonym>Suby g</synonym>
    <synonym>Uro-trainer</synonym>
    <synonym>Acid monohydrate, citric</synonym>
    <synonym>Monohydrate, citric acid</synonym>
    <synonym>Citric acid, anhydrous</synonym>
    <synonym>Citric acid monohydrate</synonym>
    <synonym>Uralyt u</synonym>
  </synonyms>
  <chemical_formula>C6H8O7</chemical_formula>
  <average_molecular_weight>192.1235</average_molecular_weight>
  <monisotopic_moleculate_weight>192.02700261</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxypropane-1,2,3-tricarboxylic acid</iupac_name>
  <traditional_iupac>citric acid</traditional_iupac>
  <cas_registry_number>77-92-9</cas_registry_number>
  <smiles>OC(=O)CC(O)(CC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)</inchi>
  <inchikey>KRKNYBCHXYNGOX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Tricarboxylic acids and derivatives</sub_class>
    <direct_parent>Tricarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>tricarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>153 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>592.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.64</value>
      <source>AVDEEF,A (1997)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxypropane-1,2,3-tricarboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>192.1235</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>192.02700261</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC(O)(CC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H8O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KRKNYBCHXYNGOX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>132.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Succinate Signalling</name>
      <smpdb_id>SMP0120941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2847</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437371</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3026 - 9854</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3692 - 7435</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8432.0762 +/- 260.249</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9004.625 +/- 468.449</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8180</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
          <pubmed_id>2760296</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9108.724 +/- 260.249</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9316.924 +/- 156.150</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9681.273 +/- 156.150</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3719 - 5776</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5099 +/- 409</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5219 +/- 168</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4793 +/- 260</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5808 +/- 643</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8380</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9110</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4602.04 +/- 617.46</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6620 - 12900</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk, range over first 90 day in lactation</comment>
      <references>
        <reference>
          <reference_text>Tsioulpas A, Grandison AS, Lewis MJ: Changes in physical properties of bovine milk from the colostrum period to early lactation. J Dairy Sci. 2007 Nov;90(11):5012-7. doi: 10.3168/jds.2007-0192.</reference_text>
          <pubmed_id>17954740</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4453.36 +/- 225.49</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 54 Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
          <pubmed_id>23394630</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from Danish Holstein-Friesian (n = 456) and Jersey cows (n = 436)</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
          <pubmed_id>23182357</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4595.41 +/- 448.18</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00158</kegg_id>
  <foodb_id>FDB030735</foodb_id>
  <drugbank_id>DB04272</drugbank_id>
  <chemspider_id>305</chemspider_id>
  <pubchem_compound_id>311</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30769</chebi_id>
  <knapsack_id>C00007619</knapsack_id>
  <meta_cyc_id>CIT</meta_cyc_id>
  <wikipedia_id>Citric_Acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34080</bigg_id>
  <metlin_id>124</metlin_id>
  <synthesis_reference>Evans, D. W. S. Hydrolysis of ethyl methylenecitrate [5,5-bis(ethoxycarbonylmethyl)-1,3-dioxolan-4-one] and an attempted synthesis of agaric acid. Journal of the Chemical Society (1959), 1313-14.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
      <pubmed_id>2760296</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
      <pubmed_id>11132867</pubmed_id>
    </reference>
    <reference>
      <reference_text>Tsioulpas A, Grandison AS, Lewis MJ: Changes in physical properties of bovine milk from the colostrum period to early lactation. J Dairy Sci. 2007 Nov;90(11):5012-7. doi: 10.3168/jds.2007-0192.</reference_text>
      <pubmed_id>17954740</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
      <pubmed_id>23040012</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
      <pubmed_id>23182357</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
      <pubmed_id>23394630</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00175</protein_accession>
      <name>ATP-citrate synthase</name>
      <uniprot_id>Q32PF2</uniprot_id>
      <gene_name>ACLY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00362</protein_accession>
      <name>Citrate synthase, mitochondrial</name>
      <uniprot_id>Q29RK1</uniprot_id>
      <gene_name>CS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00479</protein_accession>
      <name>6-phosphofructokinase, liver type</name>
      <uniprot_id>A1A4J1</uniprot_id>
      <gene_name>PFKL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00681</protein_accession>
      <name>Cytoplasmic aconitate hydratase</name>
      <uniprot_id>Q0VCU1</uniprot_id>
      <gene_name>ACO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00687</protein_accession>
      <name>Aconitate hydratase, mitochondrial</name>
      <uniprot_id>P20004</uniprot_id>
      <gene_name>ACO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02161</protein_accession>
      <name>Tricarboxylate transport protein, mitochondrial</name>
      <uniprot_id>P79110</uniprot_id>
      <gene_name>SLC25A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:34 UTC</creation_date>
  <update_date>2020-04-15 20:47:46 UTC</update_date>
  <accession>BMDB0000095</accession>
  <secondary_accessions>
    <accession>BMDB00095</accession>
  </secondary_accessions>
  <name>Cytidine monophosphate</name>
  <description>Cytidine monophosphate, also known as CMP or cytidylic acid, belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. Cytidine monophosphate exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Cytidine monophosphate exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>CMP</synonym>
    <synonym>Cytidine-5'-monophosphate</synonym>
    <synonym>Cytidylate</synonym>
    <synonym>Cytidylic acid</synonym>
    <synonym>pC</synonym>
    <synonym>Cytidine-5'-monophosphoric acid</synonym>
    <synonym>Cytidine monophosphoric acid</synonym>
    <synonym>Cytidine 5'-monophosphate</synonym>
    <synonym>Cytidine 5'-monophosphoric acid</synonym>
    <synonym>5'-CMP</synonym>
    <synonym>5-Cytidylate</synonym>
    <synonym>5-Cytidylic acid</synonym>
    <synonym>Cytidine 5'-monophosphorate</synonym>
    <synonym>Cytidine 5'-phosphate</synonym>
    <synonym>Cytidine 5'-phosphorate</synonym>
    <synonym>Cytidine 5'-phosphoric acid</synonym>
    <synonym>Cytidine mono(dihydrogen phosphate)</synonym>
    <synonym>Acid, cytidylic</synonym>
    <synonym>monoPhosphate, cytidine</synonym>
    <synonym>5’-CMP</synonym>
    <synonym>Cytidine 5’-monophosphate</synonym>
    <synonym>Cytidine 5’-monophosphoric acid</synonym>
    <synonym>Cytidine 5’-phosphate</synonym>
    <synonym>Cytidine 5’-phosphoric acid</synonym>
    <synonym>Cytidine monophosphate</synonym>
    <synonym>Cytosine 5'-monophosphate</synonym>
    <synonym>Cytosine 5’-monophosphate</synonym>
  </synonyms>
  <chemical_formula>C9H14N3O8P</chemical_formula>
  <average_molecular_weight>323.1965</average_molecular_weight>
  <monisotopic_moleculate_weight>323.051850951</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>cytidine monophosphate</traditional_iupac>
  <cas_registry_number>63-37-6</cas_registry_number>
  <smiles>NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1</inchi>
  <inchikey>IERHLVCPSMICTF-XVFCMESISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group  linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine ribonucleotides</sub_class>
    <direct_parent>Pyrimidine ribonucleoside monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ribonucleotides</external_descriptor>
      <external_descriptor>cytidine 5'-phosphate</external_descriptor>
      <external_descriptor>pyrimidine ribonucleoside 5'-monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>233 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>323.1965</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>323.051850951</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H14N3O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IERHLVCPSMICTF-XVFCMESISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>175.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>65.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Cardiolipin Biosynthesis</name>
      <smpdb_id>SMP0072032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:0)</name>
      <smpdb_id>SMP0077151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:0)</name>
      <smpdb_id>SMP0077153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:0)</name>
      <smpdb_id>SMP0077171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:0)</name>
      <smpdb_id>SMP0077173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077190</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077198</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077199</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077200</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077201</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077205</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077206</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077207</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077208</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077209</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077210</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077211</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077213</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077214</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077215</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077216</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077217</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077218</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077219</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077220</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077221</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077222</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077223</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077224</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077225</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077226</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077227</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077228</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077229</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077230</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077231</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077232</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077233</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077234</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077235</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077237</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077238</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077239</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077240</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077241</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077242</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077243</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077244</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077245</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077246</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077247</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077248</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077249</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077250</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077251</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077252</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077256</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077257</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077258</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077259</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077265</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077266</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077267</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077268</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077273</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077274</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077275</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077276</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077277</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077278</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077279</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077280</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077281</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077282</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077283</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077284</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077285</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077286</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077287</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077288</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077289</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077290</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077291</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077292</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077294</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077295</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077296</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077297</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077298</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:0)</name>
      <smpdb_id>SMP0077299</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077300</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077301</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077302</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077303</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077304</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077305</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077306</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077307</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077308</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077309</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:0)</name>
      <smpdb_id>SMP0077310</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077311</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:0)</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077313</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077314</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077315</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077316</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077317</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077318</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077319</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077320</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077321</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077322</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077323</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077324</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077325</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077326</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077327</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077328</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077329</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077330</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077331</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077332</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077333</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077334</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077335</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077337</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077338</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077339</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077340</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077341</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077342</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077343</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077344</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077345</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077346</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077347</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077348</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077349</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077350</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077351</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077352</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077353</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077354</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077355</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077356</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077357</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077359</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077360</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077361</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077363</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077364</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077365</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077366</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077367</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077368</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077369</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077370</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077371</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077372</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077373</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077374</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077375</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077376</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077377</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077378</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077379</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077380</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077381</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077382</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077383</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077384</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077385</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077386</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077387</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077388</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077389</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077390</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077391</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077392</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077394</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077395</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077396</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077400</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077402</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077403</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077404</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077405</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077406</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077407</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077408</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077409</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077410</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077411</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077412</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077413</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077414</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077415</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077416</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077417</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077418</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077419</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077420</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077421</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077422</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077423</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077424</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077425</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077426</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077427</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077428</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077429</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077430</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077431</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077432</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077433</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077434</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077435</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077436</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077437</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077438</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077439</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077440</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077441</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077442</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077443</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077444</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077445</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077446</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077447</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077448</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077449</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077450</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077451</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077452</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077453</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077454</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077455</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077456</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077457</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077458</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077459</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077460</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077461</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077462</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077463</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077464</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077465</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077466</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077467</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077468</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077469</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077470</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077471</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077472</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077473</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077474</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077475</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077476</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077477</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077478</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077479</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077480</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077481</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077482</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077494</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077495</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077496</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077498</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077499</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077500</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077501</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077502</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077503</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077504</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077505</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077506</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077508</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077509</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077510</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077511</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077512</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077513</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077514</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077515</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077516</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077517</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077518</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077519</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077520</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077521</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077522</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077523</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077524</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077525</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077526</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077600</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077601</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077602</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077603</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077604</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077605</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077606</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077607</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077608</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077609</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077610</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077611</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077612</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077613</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077614</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077615</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077616</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077617</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077618</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077619</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077620</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077621</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077622</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077623</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077624</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077625</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077626</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077627</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077628</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077629</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077630</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077635</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077636</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077637</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077638</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077639</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077640</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077641</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077645</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077646</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077649</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077650</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077651</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077652</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077653</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077654</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077655</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077656</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077657</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077658</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077659</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077660</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077661</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077662</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077663</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077664</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077667</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077670</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077690</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077724</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077733</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077734</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077735</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077741</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077742</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077743</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077744</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077745</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077746</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077747</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077748</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077749</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077750</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077751</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077752</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077753</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077754</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077755</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077756</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077757</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077758</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077759</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077760</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077761</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077762</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077763</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077764</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077765</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077766</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077767</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077768</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077769</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077770</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077771</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077772</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077773</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077774</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077775</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077776</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077777</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077778</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077779</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077780</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077781</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077782</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077783</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077784</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077785</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077791</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077793</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077797</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077798</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077801</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077802</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077803</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077804</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077805</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077806</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077807</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077808</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077809</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077810</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077811</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077812</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077813</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077814</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077815</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077816</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077817</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077818</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077819</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077820</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077822</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077824</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077825</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077826</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077827</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077828</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077829</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077830</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077831</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077832</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077833</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077834</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077835</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077836</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077837</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077839</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077840</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077841</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077842</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077843</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077845</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077846</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077847</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077848</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077850</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077851</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077852</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077853</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077854</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077855</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077857</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077858</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077863</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077864</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077891</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077892</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077894</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077895</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077898</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077900</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077901</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077902</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077903</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077904</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077905</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077906</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077907</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077908</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077909</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077910</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077911</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077912</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077913</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077914</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077915</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077916</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077917</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077918</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077919</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077920</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077921</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077922</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077923</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077924</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077925</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077926</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077927</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077928</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077929</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077930</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077932</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077933</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077934</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077935</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077936</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077937</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077938</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077939</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077940</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077941</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077942</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077943</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077944</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077945</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077946</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077947</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077948</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077949</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077950</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077951</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077952</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077953</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077954</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077955</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077956</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077958</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077960</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077985</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/16:0)</name>
      <smpdb_id>SMP0078130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:0)</name>
      <smpdb_id>SMP0078132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078215</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078216</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:0)</name>
      <smpdb_id>SMP0078219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078223</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078225</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078233</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078234</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078235</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078245</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078252</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078253</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078254</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078255</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078256</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078257</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078258</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078262</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078264</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078265</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078266</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078267</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078268</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078270</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078272</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078273</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078274</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078275</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078276</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078277</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078279</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078280</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078281</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078282</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078283</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078284</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078287</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078288</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078289</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078290</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078293</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078294</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078295</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078296</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078297</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078298</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078299</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078300</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078301</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078302</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078303</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078304</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078305</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078306</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078307</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078308</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078309</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078310</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078311</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078312</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078313</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078314</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078315</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078316</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078317</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078318</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078319</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078320</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078321</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078322</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078323</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078324</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078325</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078326</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078327</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078328</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078329</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078330</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078331</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078332</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078333</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078334</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078336</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078337</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078338</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078342</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078343</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078348</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078350</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078351</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078352</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078353</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078354</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078355</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078356</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078357</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078358</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078359</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078360</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078361</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078362</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078363</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078364</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078365</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078366</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078367</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078368</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078369</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078370</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078371</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078372</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078373</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078374</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078375</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078376</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078377</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078378</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078379</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078380</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078381</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078382</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078386</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078388</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078389</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078390</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078391</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078393</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078394</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078395</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078396</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078397</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078398</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078399</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078400</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078406</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078407</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078408</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078421</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078422</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078423</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078424</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078425</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078426</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078427</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078428</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078429</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078430</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078431</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078432</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078433</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078434</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078435</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078436</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078437</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078438</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078439</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078440</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078441</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078442</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078443</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078444</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078445</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078446</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078447</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078448</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078449</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078450</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078451</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078452</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078453</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078454</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078455</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078457</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078458</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078459</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078460</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078462</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078463</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078464</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078465</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078466</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078467</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078468</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078469</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078470</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078471</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078472</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078473</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078474</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078475</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078476</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078478</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078479</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078480</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078481</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078482</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078483</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078484</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078485</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078486</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078487</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078488</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078489</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078490</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078491</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078492</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078493</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078494</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078495</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078496</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078498</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078499</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078500</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078501</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078502</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078503</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078504</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078506</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078507</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078508</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078509</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078510</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078516</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078517</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078518</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078519</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078520</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078521</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078530</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078531</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078532</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078533</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078534</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078605</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078606</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078607</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078608</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078609</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078610</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078612</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078614</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078615</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078616</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078617</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078618</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078619</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078620</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078621</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078622</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078623</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078624</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078625</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078626</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078627</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078628</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078629</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078630</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078631</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078632</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078633</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078634</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078635</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078636</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078637</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078638</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078639</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078640</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078641</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078642</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078644</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078654</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078656</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078657</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078658</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078659</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078660</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078661</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078662</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078664</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078665</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078666</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078667</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078668</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078669</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078670</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078671</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078672</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078673</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078674</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078675</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078676</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078677</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078678</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078679</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078680</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078681</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078682</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078683</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078684</smpdb_id>
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      <smpdb_id>SMP0078685</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078767</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078768</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078769</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078770</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078771</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078772</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078773</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078774</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078775</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078776</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078777</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078778</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078779</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078780</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078781</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078782</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078783</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078784</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078785</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078786</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078787</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078788</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078789</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078790</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078792</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078794</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078795</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078796</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078797</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078798</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078800</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078802</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078804</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078805</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078806</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078807</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078808</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078809</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078810</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078811</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078812</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078813</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078814</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078815</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078816</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078817</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078818</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078819</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078820</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078821</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078822</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078823</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078824</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078825</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078826</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078828</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078830</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078831</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078832</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078834</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078835</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078840</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078841</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078842</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078843</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078844</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078845</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078846</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078848</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078849</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078850</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078851</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078852</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078853</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078854</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078855</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078856</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078858</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078859</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078860</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078861</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078862</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078864</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078870</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078875</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078876</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078877</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078878</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078879</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078885</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078890</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078917</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078918</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078919</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078920</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <smpdb_id>SMP0078992</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079140</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079141</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079142</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079143</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079144</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079145</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079146</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079147</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079148</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079149</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079150</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0079152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079159</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079166</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079169</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079171</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079174</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079175</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079176</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079178</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079179</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079180</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079181</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079184</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079185</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079186</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079187</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079190</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079191</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079192</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079193</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079194</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079195</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079196</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079197</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079198</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079199</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079200</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079201</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079202</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079203</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079204</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079205</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079206</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079207</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079208</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079209</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079210</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079211</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079212</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079214</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079215</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079216</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079217</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079218</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079219</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079220</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079221</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079222</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079223</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079224</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079225</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079226</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079227</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079228</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079229</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079230</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079231</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079232</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079233</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079234</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079235</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079236</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079237</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079238</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079239</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079240</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079241</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079242</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079243</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079244</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079245</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079246</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079247</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079248</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079249</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079250</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079251</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079252</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079253</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079254</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079255</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079256</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079257</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079258</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079259</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079260</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079261</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079262</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079263</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079264</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079265</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079266</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079267</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079268</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079269</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079270</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079271</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079272</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079273</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079274</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079275</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079276</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079277</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079278</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079279</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079280</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079281</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079282</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079283</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079284</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079285</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079286</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079287</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079288</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079289</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079290</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079291</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079297</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079299</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079300</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079305</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079306</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079431</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079432</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079433</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079434</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079435</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079436</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079437</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079438</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079440</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079441</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079442</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079443</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079444</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079445</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079448</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079449</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079450</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079451</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079454</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079464</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079465</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079466</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079467</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079468</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079469</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079470</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079474</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079475</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079477</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079478</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079479</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079481</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079482</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079485</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079486</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079488</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079489</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079490</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079491</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079492</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079493</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079494</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079495</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079496</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079497</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079498</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079499</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079500</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079502</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079503</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079504</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079505</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079506</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079507</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079508</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079509</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079510</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079511</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079512</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079513</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079514</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079515</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079516</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079519</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079520</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079521</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079522</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079523</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079527</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079531</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079533</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079534</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079535</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079536</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079537</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079538</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079549</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079562</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079563</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079564</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079565</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079566</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079567</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079568</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079570</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079572</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079573</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079574</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079575</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079576</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079584</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079585</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079586</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079587</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079588</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079589</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079590</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0079603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0079604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079650</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079651</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079656</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079659</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079664</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079714</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079717</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079761</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079762</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079785</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079789</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079852</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080044</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080116</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080119</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080120</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080228</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080232</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080235</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080237</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080238</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080239</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080240</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080241</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080242</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080244</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080246</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080250</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080251</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080252</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080262</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080263</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080287</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080288</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080298</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080299</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pantothenate and CoA Biosynthesis</name>
      <smpdb_id>SMP0087207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis</name>
      <smpdb_id>SMP0072037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:0)</name>
      <smpdb_id>SMP0080430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0080431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/15:0)</name>
      <smpdb_id>SMP0080432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:0)</name>
      <smpdb_id>SMP0080433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0080434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:0)</name>
      <smpdb_id>SMP0080435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0080436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0080437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:0)</name>
      <smpdb_id>SMP0080442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0080443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:0)</name>
      <smpdb_id>SMP0080450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0080451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:0)</name>
      <smpdb_id>SMP0080457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0080458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0080459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0080460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0080461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/15:0)</name>
      <smpdb_id>SMP0080487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:0)</name>
      <smpdb_id>SMP0080488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0080489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:0)</name>
      <smpdb_id>SMP0080490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0080491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0080492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:0)</name>
      <smpdb_id>SMP0080497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0080498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:0)</name>
      <smpdb_id>SMP0080505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0080506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:0)</name>
      <smpdb_id>SMP0080512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0080513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:0)</name>
      <smpdb_id>SMP0080514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0080515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:0)</name>
      <smpdb_id>SMP0080516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0080517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0080518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:0)</name>
      <smpdb_id>SMP0080523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0080524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:0)</name>
      <smpdb_id>SMP0080531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0080532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:0)</name>
      <smpdb_id>SMP0080538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0080539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:0)</name>
      <smpdb_id>SMP0080565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0080566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0080567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:0)</name>
      <smpdb_id>SMP0080572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0080573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:0)</name>
      <smpdb_id>SMP0080580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0080581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:0)</name>
      <smpdb_id>SMP0080587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0080588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0080595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:0)</name>
      <smpdb_id>SMP0080712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0080713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:0)</name>
      <smpdb_id>SMP0080720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0080721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:0)</name>
      <smpdb_id>SMP0080727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0080728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0080765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0080772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:0)</name>
      <smpdb_id>SMP0080820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0080821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:0)</name>
      <smpdb_id>SMP0080827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0080828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0080835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:0)</name>
      <smpdb_id>SMP0080864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0080865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis</name>
      <smpdb_id>SMP0072048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:0)</name>
      <smpdb_id>SMP0082233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0082234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/15:0)</name>
      <smpdb_id>SMP0082235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:0)</name>
      <smpdb_id>SMP0082236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0082237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:0)</name>
      <smpdb_id>SMP0082238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0082239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0082240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:0)</name>
      <smpdb_id>SMP0082245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0082246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:0)</name>
      <smpdb_id>SMP0082253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0082254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:0)</name>
      <smpdb_id>SMP0082260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0082261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0082262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0082263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0082264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/15:0)</name>
      <smpdb_id>SMP0082290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:0)</name>
      <smpdb_id>SMP0082291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0082292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:0)</name>
      <smpdb_id>SMP0082293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0082294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0082295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:0)</name>
      <smpdb_id>SMP0082300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0082301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:0)</name>
      <smpdb_id>SMP0082308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0082309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:0)</name>
      <smpdb_id>SMP0082315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0082316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:0)</name>
      <smpdb_id>SMP0082317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0082318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:0)</name>
      <smpdb_id>SMP0082319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0082320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0082321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:0)</name>
      <smpdb_id>SMP0082326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0082327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:0)</name>
      <smpdb_id>SMP0082334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0082335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:0)</name>
      <smpdb_id>SMP0082341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0082342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:0)</name>
      <smpdb_id>SMP0082368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0082369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0082370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:0)</name>
      <smpdb_id>SMP0082375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0082376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:0)</name>
      <smpdb_id>SMP0082383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0082384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:0)</name>
      <smpdb_id>SMP0082390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0082391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0082398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:0)</name>
      <smpdb_id>SMP0082520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0082521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:0)</name>
      <smpdb_id>SMP0082528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0082529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:0)</name>
      <smpdb_id>SMP0082535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0082536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0082574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0082581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:0)</name>
      <smpdb_id>SMP0082629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0082630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:0)</name>
      <smpdb_id>SMP0082636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0082637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0082644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:0)</name>
      <smpdb_id>SMP0082671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0082672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylinositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Plasmalogen Synthesis</name>
      <smpdb_id>SMP0087264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2858</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448137</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw whole milk</comment>
      <references>
        <reference>
          <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
          <pubmed_id>6539345</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12.300 - 86.800</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44.</reference_text>
          <pubmed_id>7196410</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00055</kegg_id>
  <chemspider_id>5901</chemspider_id>
  <drugbank_id>DB03403</drugbank_id>
  <foodb_id>FDB030736</foodb_id>
  <chebi_id>17361</chebi_id>
  <pubchem_compound_id>6131</pubchem_compound_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id>CMP</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33689</bigg_id>
  <wikipedia_id>Cytidine monophosphate</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Zhou, Jingkang.  Method for preparing cytidine 5'-monophosphate.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2005), 12 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:35 UTC</creation_date>
  <update_date>2020-04-16 20:40:36 UTC</update_date>
  <accession>BMDB0000097</accession>
  <secondary_accessions>
    <accession>BMDB00097</accession>
  </secondary_accessions>
  <name>Choline</name>
  <description>Choline, also known as bilineurine or choline ion, belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation. Choline is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Choline exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Choline exists in all living species, ranging from bacteria to humans. Choline participates in a number of enzymatic reactions, within cattle. In particular, Choline can be biosynthesized from acetylcholine; which is mediated by the enzyme acetylcholinesterase. In addition, Choline can be converted into acetylcholine; which is catalyzed by the enzyme choline O-acetyltransferase. In cattle, choline is involved in the metabolic pathway called phospholipid biosynthesis pathway.</description>
  <synonyms>
    <synonym>Bilineurine</synonym>
    <synonym>CHOLINE ion</synonym>
    <synonym>N,N,N-Trimethylethanol-ammonium</synonym>
    <synonym>N-Trimethylethanolamine</synonym>
    <synonym>Trimethylethanolamine</synonym>
    <synonym>Choline cation</synonym>
    <synonym>(2-Hydroxyethyl)trimethyl ammonium</synonym>
    <synonym>(2-Hydroxyethyl)trimethylammonium</synonym>
    <synonym>(beta-Hydroxyethyl)trimethylammonium</synonym>
    <synonym>2-Hydroxy-N,N,N-trimethyl-ethanaminium</synonym>
    <synonym>2-Hydroxy-N,N,N-trimethylethanaminium</synonym>
    <synonym>Biocolina</synonym>
    <synonym>Biocoline</synonym>
    <synonym>Cholinum</synonym>
    <synonym>Hepacholine</synonym>
    <synonym>Hormocline</synonym>
    <synonym>Lipotril</synonym>
    <synonym>N,N,N-Trimethylethanolammonium</synonym>
    <synonym>Neocolina</synonym>
    <synonym>Paresan</synonym>
    <synonym>Choline O-sulfate</synonym>
    <synonym>Citrate, choline</synonym>
    <synonym>Fagine</synonym>
    <synonym>Hydroxide, choline</synonym>
    <synonym>Vidine</synonym>
    <synonym>Bursine</synonym>
    <synonym>Chloride, choline</synonym>
    <synonym>Choline chloride</synonym>
    <synonym>Choline citrate</synonym>
    <synonym>Bitartrate, choline</synonym>
    <synonym>Choline bitartrate</synonym>
    <synonym>Choline hydroxide</synonym>
    <synonym>Choline O sulfate</synonym>
    <synonym>O-Sulfate, choline</synonym>
  </synonyms>
  <chemical_formula>C5H14NO</chemical_formula>
  <average_molecular_weight>104.1708</average_molecular_weight>
  <monisotopic_moleculate_weight>104.107539075</monisotopic_moleculate_weight>
  <iupac_name>(2-hydroxyethyl)trimethylazanium</iupac_name>
  <traditional_iupac>choline</traditional_iupac>
  <cas_registry_number>62-49-7</cas_registry_number>
  <smiles>C[N+](C)(C)CCO</smiles>
  <inchi>InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1</inchi>
  <inchikey>OEYIOHPDSNJKLS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Quaternary ammonium salts</sub_class>
    <direct_parent>Cholines</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkanolamine</substituent>
      <substituent>Amine</substituent>
      <substituent>Choline</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Pesticides</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>cholines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>302 - 303 °C (chloride salt)</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2-hydroxyethyl)trimethylazanium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>104.1708</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>104.107539075</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)CCO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H14NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OEYIOHPDSNJKLS-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis</name>
      <smpdb_id>SMP0072037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:0)</name>
      <smpdb_id>SMP0080430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0080431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/15:0)</name>
      <smpdb_id>SMP0080432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:0)</name>
      <smpdb_id>SMP0080433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0080434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:0)</name>
      <smpdb_id>SMP0080435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0080436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0080437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:0)</name>
      <smpdb_id>SMP0080442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0080443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:0)</name>
      <smpdb_id>SMP0080450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0080451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:0)</name>
      <smpdb_id>SMP0080457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0080458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0080459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0080460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0080461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/15:0)</name>
      <smpdb_id>SMP0080487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:0)</name>
      <smpdb_id>SMP0080488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0080489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:0)</name>
      <smpdb_id>SMP0080490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0080491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0080492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:0)</name>
      <smpdb_id>SMP0080497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0080498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:0)</name>
      <smpdb_id>SMP0080505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0080506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:0)</name>
      <smpdb_id>SMP0080512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0080513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:0)</name>
      <smpdb_id>SMP0080514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0080515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:0)</name>
      <smpdb_id>SMP0080516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0080517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0080518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:0)</name>
      <smpdb_id>SMP0080523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0080524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:0)</name>
      <smpdb_id>SMP0080531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0080532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:0)</name>
      <smpdb_id>SMP0080538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0080539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:0)</name>
      <smpdb_id>SMP0080565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0080566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0080567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:0)</name>
      <smpdb_id>SMP0080572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0080573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:0)</name>
      <smpdb_id>SMP0080580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0080581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:0)</name>
      <smpdb_id>SMP0080587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0080588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0080595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:0)</name>
      <smpdb_id>SMP0080712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0080713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:0)</name>
      <smpdb_id>SMP0080720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0080721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:0)</name>
      <smpdb_id>SMP0080727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0080728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0080765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0080772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:0)</name>
      <smpdb_id>SMP0080820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0080821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:0)</name>
      <smpdb_id>SMP0080827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0080828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0080835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:0)</name>
      <smpdb_id>SMP0080864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0080865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis</name>
      <smpdb_id>SMP0072048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:0)</name>
      <smpdb_id>SMP0082233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0082234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/15:0)</name>
      <smpdb_id>SMP0082235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:0)</name>
      <smpdb_id>SMP0082236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0082237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:0)</name>
      <smpdb_id>SMP0082238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0082239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0082240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:0)</name>
      <smpdb_id>SMP0082245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0082246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:0)</name>
      <smpdb_id>SMP0082253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0082254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:0)</name>
      <smpdb_id>SMP0082260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0082261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0082262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0082263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0082264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/15:0)</name>
      <smpdb_id>SMP0082290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:0)</name>
      <smpdb_id>SMP0082291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0082292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:0)</name>
      <smpdb_id>SMP0082293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0082294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0082295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:0)</name>
      <smpdb_id>SMP0082300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0082301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:0)</name>
      <smpdb_id>SMP0082308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0082309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:0)</name>
      <smpdb_id>SMP0082315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0082316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:0)</name>
      <smpdb_id>SMP0082317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0082318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:0)</name>
      <smpdb_id>SMP0082319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0082320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0082321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:0)</name>
      <smpdb_id>SMP0082326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0082327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:0)</name>
      <smpdb_id>SMP0082334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0082335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:0)</name>
      <smpdb_id>SMP0082341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0082342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:0)</name>
      <smpdb_id>SMP0082368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0082369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0082370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:0)</name>
      <smpdb_id>SMP0082375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0082376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:0)</name>
      <smpdb_id>SMP0082383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0082384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:0)</name>
      <smpdb_id>SMP0082390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0082391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0082398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:0)</name>
      <smpdb_id>SMP0082520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0082521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:0)</name>
      <smpdb_id>SMP0082528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0082529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:0)</name>
      <smpdb_id>SMP0082535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0082536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0082574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0082581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:0)</name>
      <smpdb_id>SMP0082629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0082630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:0)</name>
      <smpdb_id>SMP0082636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0082637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0082644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:0)</name>
      <smpdb_id>SMP0082671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0082672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1140</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in lactating Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3.75-4.45</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Artegoitia VM, Middleton JL, Harte FM, Campagna SR, de Veth MJ: Choline and choline metabolite patterns and associations in blood and milk during lactation in dairy cows. PLoS One. 2014 Aug 26;9(8):e103412. doi: 10.1371/journal.pone.0103412. eCollection 2014.</reference_text>
          <pubmed_id>25157578</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>20+/-4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>345+/-109</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>15+/-7</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>150 - 997</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>152 - 479</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>106.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Zeisel SH, Char D, Sheard NF: Choline, phosphatidylcholine and sphingomyelin in human and bovine milk and infant formulas. J Nutr. 1986 Jan;116(1):50-8. doi: 10.1093/jn/116.1.50.</reference_text>
          <pubmed_id>3944656</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>180 - 479</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>206 +/- 14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>242 +/- 10</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>235 +/- 8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>214 +/- 17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>298.26 +/- 146.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>310.54 +/- 77.69</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from 20 healthy Holstein Friesian dairy cows </comment>
      <references>
        <reference>
          <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
          <pubmed_id>23738862</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>214.22 +/- 58.37</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>34-153</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>107.79 +/- 4.65</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>118.5 +/- 13.32</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>125.57 +/- 11.43</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>71-137</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>76.73 +/- 5.28</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>10-125</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>4-40</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>14.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>16.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>19.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>17.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>105+/-59</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>17.54 +/- 6.66</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>13.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>16.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>24.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>17.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>13 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>17 +/- 6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>25 +/- 13</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>18 +/- 7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>15+/-6</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>177+/-71</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00114</kegg_id>
  <drugbank_id>DB00122</drugbank_id>
  <foodb_id>FDB000710</foodb_id>
  <chemspider_id>299</chemspider_id>
  <pubchem_compound_id>305</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15354</chebi_id>
  <knapsack_id>C00007298</knapsack_id>
  <meta_cyc_id>CHOLINE</meta_cyc_id>
  <wikipedia_id>Choline</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33910</bigg_id>
  <metlin_id>56</metlin_id>
  <synthesis_reference>Hasegawa, Yoichi; Hyoda, Shunji; Sawada, Hirotoshi; Baba, Masakatsu.  Preparation of high-purity organic carboxylic acid choline salts and choline.    Jpn. Kokai Tokkyo Koho  (1999),     9 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Zeisel SH, Char D, Sheard NF: Choline, phosphatidylcholine and sphingomyelin in human and bovine milk and infant formulas. J Nutr. 1986 Jan;116(1):50-8. doi: 10.1093/jn/116.1.50.</reference_text>
      <pubmed_id>3944656</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
      <pubmed_id>23738862</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00529</protein_accession>
      <name>Acetylcholinesterase</name>
      <uniprot_id>P23795</uniprot_id>
      <gene_name>ACHE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00834</protein_accession>
      <name>Phospholipase D3</name>
      <uniprot_id>Q2KJJ8</uniprot_id>
      <gene_name>PLD3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00835</protein_accession>
      <name>Cholinesterase</name>
      <uniprot_id>P32749</uniprot_id>
      <gene_name>BCHE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00836</protein_accession>
      <name>Phospholipase D2</name>
      <uniprot_id>Q0V8L6</uniprot_id>
      <gene_name>PLD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01355</protein_accession>
      <name>Solute carrier family 22 member 1</name>
      <uniprot_id>A7MBE0</uniprot_id>
      <gene_name>SLC22A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02082</protein_accession>
      <name>Choline transporter-like protein 2</name>
      <uniprot_id>A5D7H3</uniprot_id>
      <gene_name>SLC44A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02083</protein_accession>
      <name>Choline transporter-like protein 4</name>
      <uniprot_id>A3KMY4</uniprot_id>
      <gene_name>SLC44A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02084</protein_accession>
      <name>Choline transporter-like protein 3</name>
      <uniprot_id>A5PK40</uniprot_id>
      <gene_name>SLC44A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02085</protein_accession>
      <name>Sodium-coupled neutral amino acid transporter 2</name>
      <uniprot_id>A2VE31</uniprot_id>
      <gene_name>SLC38A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02086</protein_accession>
      <name>Solute carrier family 5 (Choline transporter), member 7</name>
      <uniprot_id>Q2KI26</uniprot_id>
      <gene_name>SLC5A7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:36 UTC</creation_date>
  <update_date>2020-04-15 22:31:49 UTC</update_date>
  <accession>BMDB0000098</accession>
  <secondary_accessions>
    <accession>BMDB00098</accession>
  </secondary_accessions>
  <name>D-Xylose</name>
  <description>D-D-d-xylose, also known as d-xylose or d-xylose, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. D-D-d-xylose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-D-d-xylose exists in all living species, ranging from bacteria to humans. In cattle, D-d-xylose is involved in the metabolic pathway called the nucleotide sugars metabolism pathway. D-D-d-xylose is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(3R,4S,5R)-Tetrahydro-2H-pyran-2,3,4,5-tetrol</synonym>
    <synonym>D-(+)-Xylose</synonym>
    <synonym>D-Xylopentose</synonym>
    <synonym>Wood sugar</synonym>
    <synonym>Xylo-pfan</synonym>
    <synonym>D-Xylo-pentose</synonym>
    <synonym>Xylomed</synonym>
    <synonym>Xylose</synonym>
    <synonym>Xyloside</synonym>
    <synonym>Xylopyranose</synonym>
    <synonym>D Xylose</synonym>
    <synonym>D-Xylopyranose</synonym>
    <synonym>Aldehydo-D-xylose</synonym>
    <synonym>D-Xylose</synonym>
  </synonyms>
  <chemical_formula>C5H10O5</chemical_formula>
  <average_molecular_weight>150.1299</average_molecular_weight>
  <monisotopic_moleculate_weight>150.05282343</monisotopic_moleculate_weight>
  <iupac_name>(3R,4S,5R)-oxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>d-xylose</traditional_iupac>
  <cas_registry_number>58-86-6</cas_registry_number>
  <smiles>O[C@@H]1COC(O)[C@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1</inchi>
  <inchikey>SRBFZHDQGSBBOR-IOVATXLUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Aldoses</external_descriptor>
      <external_descriptor>D-xylose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>90.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>555.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4S,5R)-oxane-2,3,4,5-tetrol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>150.1299</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>150.05282343</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]1COC(O)[C@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SRBFZHDQGSBBOR-IOVATXLUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>90.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>29.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369246</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00181</kegg_id>
  <chemspider_id>119104</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB005944</foodb_id>
  <chebi_id>53455</chebi_id>
  <pubchem_compound_id>135191</pubchem_compound_id>
  <pdbe_id/>
  <knapsack_id>C00007290</knapsack_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>34162</bigg_id>
  <wikipedia_id>Xylose</wikipedia_id>
  <metlin_id>314</metlin_id>
  <synthesis_reference>Lavarack, B. P.; Griffin, G.; Rodman, D.  Optimizing the autohydrolysis of bagasse to extract D-xylose.    Proceedings of the Conference of the Australian Society of Sugar Cane Technologists  (1999),  21st  394-400.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00383</protein_accession>
      <name>Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase</name>
      <uniprot_id>Q148L6</uniprot_id>
      <gene_name>DHDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01874</protein_accession>
      <name>Sodium/myo-inositol cotransporter 2</name>
      <uniprot_id>Q3ZC26</uniprot_id>
      <gene_name>SLC5A11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:37 UTC</creation_date>
  <update_date>2020-04-15 21:34:55 UTC</update_date>
  <accession>BMDB0000099</accession>
  <secondary_accessions>
    <accession>BMDB00099</accession>
  </secondary_accessions>
  <name>L-Cystathionine</name>
  <description>L-Cystathionine belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated. L-Cystathionine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Cystathionine exists in all living species, ranging from bacteria to humans. L-Cystathionine is a potentially toxic compound. L-Cystathionine has been found to be associated with several diseases known as autism, alzheimer's disease, eosinophilic esophagitis, and crohn's disease; also l-cystathionine has been linked to the inborn metabolic disorders including vitamin B12 deficiency.</description>
  <synonyms>
    <synonym>(R)-S-(2-Amino-2-carboxyethyl)-L-homocysteine</synonym>
    <synonym>L-(+)-Cystathionine</synonym>
    <synonym>S-(beta-Amino-beta-carboxyethyl)homocysteine</synonym>
    <synonym>S-(b-Amino-b-carboxyethyl)homocysteine</synonym>
    <synonym>S-(Β-amino-β-carboxyethyl)homocysteine</synonym>
    <synonym>Cystathionine</synonym>
    <synonym>S-[(2R)-2-Amino-2-carboxyethyl]-L-homocysteine</synonym>
    <synonym>[R-(R*,s*)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-butanoate</synonym>
    <synonym>[R-(R*,s*)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-butanoic acid</synonym>
  </synonyms>
  <chemical_formula>C7H14N2O4S</chemical_formula>
  <average_molecular_weight>222.262</average_molecular_weight>
  <monisotopic_moleculate_weight>222.067427636</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanoic acid</iupac_name>
  <traditional_iupac>L-cystathionine</traditional_iupac>
  <cas_registry_number>56-88-2</cas_registry_number>
  <smiles>N[C@@H](CCSC[C@H](N)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1</inchi>
  <inchikey>ILRYLPWNYFXEMH-WHFBIAKZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-cysteine-S-conjugates</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylthioethers</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>L-cysteine-s-conjugate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thia fatty acid</substituent>
      <substituent>Thioether</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>cystathionine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>312 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>22 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-4.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>222.262</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>222.067427636</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCSC[C@H](N)C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H14N2O4S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ILRYLPWNYFXEMH-WHFBIAKZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>126.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Homocysteine Degradation</name>
      <smpdb_id>SMP0087201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2871</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445899</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02291</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB001976</foodb_id>
  <chemspider_id>388392</chemspider_id>
  <pubchem_compound_id>439258</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17482</chebi_id>
  <knapsack_id>C00007498</knapsack_id>
  <meta_cyc_id>CYSTATHIONINE</meta_cyc_id>
  <wikipedia_id>Cystathionine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>39523</bigg_id>
  <metlin_id>39</metlin_id>
  <synthesis_reference>Yamagata, Shuzo; Akamatsu, Tsuyoshi; Iwama, Tomonori. Immobilization of Saccharomyces cerevisiae cystathionine gamma-lyase and application of the product to cystathionine synthesis.    Applied and Environmental Microbiology  (2004), 70(6),  3766-3768.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00818</protein_accession>
      <name>Cystathionine gamma-lyase</name>
      <uniprot_id>Q58DW2</uniprot_id>
      <gene_name>CTH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:38 UTC</creation_date>
  <update_date>2020-04-15 20:47:47 UTC</update_date>
  <accession>BMDB0000101</accession>
  <secondary_accessions>
    <accession>BMDB00101</accession>
  </secondary_accessions>
  <name>Deoxyadenosine</name>
  <description>Deoxyadenosine, also known as dA, belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2. Deoxyadenosine exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Deoxyadenosine exists in all living species, ranging from bacteria to humans. Deoxyadenosine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol</synonym>
    <synonym>5-(6-AMINO-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-ol</synonym>
    <synonym>9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenine</synonym>
    <synonym>9-(2-Deoxy-beta-D-ribofuranosyl)-9H-purin-6-amine</synonym>
    <synonym>Adenine deoxyribonucleoside</synonym>
    <synonym>Adenyldeoxyriboside</synonym>
    <synonym>dA</synonym>
    <synonym>2'-Deoxyadenosine</synonym>
    <synonym>9-(2-Deoxy-b-D-erythro-pentofuranosyl)adenine</synonym>
    <synonym>9-(2-Deoxy-β-D-erythro-pentofuranosyl)adenine</synonym>
    <synonym>9-(2-Deoxy-b-D-ribofuranosyl)-9H-purin-6-amine</synonym>
    <synonym>9-(2-Deoxy-β-D-ribofuranosyl)-9H-purin-6-amine</synonym>
    <synonym>1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-b-D-ribofuranose</synonym>
    <synonym>1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-beta-D-ribofuranose</synonym>
    <synonym>1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-beta-delta-ribofuranose</synonym>
    <synonym>2-Deoxyadenosine</synonym>
    <synonym>9-(2-Deoxy-b-D-erythro-pentofuranosyl)-9H-purin-6-amine</synonym>
    <synonym>9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-9H-purin-6-amine</synonym>
    <synonym>9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-9H-purin-6-amine</synonym>
    <synonym>9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)adenine</synonym>
    <synonym>9-(2-Deoxy-beta-delta-ribofuranosyl)-9H-purin-6-amine</synonym>
    <synonym>Adenine deoxyribose</synonym>
    <synonym>Adenine-9 2-deoxy-b-D-erythro-pentofuranoside</synonym>
    <synonym>Adenine-9 2-deoxy-beta-D-erythro-pentofuranoside</synonym>
    <synonym>Adenine-9 2-deoxy-beta-delta-erythro-pentofuranoside</synonym>
    <synonym>Desoxyadenosine</synonym>
    <synonym>Deoxyadenosine</synonym>
  </synonyms>
  <chemical_formula>C10H13N5O3</chemical_formula>
  <average_molecular_weight>251.2419</average_molecular_weight>
  <monisotopic_moleculate_weight>251.101839307</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol</iupac_name>
  <traditional_iupac>2-deoxyadenosine</traditional_iupac>
  <cas_registry_number>958-09-8</cas_registry_number>
  <smiles>NC1=C2N=CN([C@H]3C[C@H](O)[C@@H](CO)O3)C2=NC=N1</smiles>
  <inchi>InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1</inchi>
  <inchikey>OLXZPDWKRNYJJZ-RRKCRQDMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleosides</class>
    <sub_class>Purine 2'-deoxyribonucleosides</sub_class>
    <direct_parent>Purine 2'-deoxyribonucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine 2'-deoxyribonucleoside</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxyribonucleosides</external_descriptor>
      <external_descriptor>purine 2'-deoxyribonucleoside</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>189 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.55</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>251.2419</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>251.101839307</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=C2N=CN([C@H]3C[C@H](O)[C@@H](CO)O3)C2=NC=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H13N5O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OLXZPDWKRNYJJZ-RRKCRQDMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>119.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>61.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179858</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449648</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.</reference_text>
          <pubmed_id>20855010</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00559</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB021894</foodb_id>
  <chemspider_id>13135</chemspider_id>
  <pubchem_compound_id>13730</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17256</chebi_id>
  <knapsack_id>C00019281</knapsack_id>
  <meta_cyc_id>DEOXYADENOSINE</meta_cyc_id>
  <wikipedia_id>Deoxyadenosine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35352</bigg_id>
  <metlin_id>3382</metlin_id>
  <synthesis_reference>Anderson, Charles D.; Goodman, Leon; Baker, B. R. Potential anticancer agents. XIX. Synthesis of 2-deoxyadenosine. Journal of the American Chemical Society (1959), 81 3967-74.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.</reference_text>
      <pubmed_id>20855010</pubmed_id>
    </reference>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:40 UTC</creation_date>
  <update_date>2020-04-16 20:40:29 UTC</update_date>
  <accession>BMDB0000107</accession>
  <secondary_accessions>
    <accession>BMDB00107</accession>
  </secondary_accessions>
  <name>Galactitol</name>
  <description>Galactitol, also known as dulcitol or melampyrit, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. Galactitol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Galactitol exists in all living organisms, ranging from bacteria to humans. Galactitol can be biosynthesized from D-galactose; which is mediated by the enzyme aldose reductase. In cattle, galactitol is involved in the metabolic pathway called the galactose metabolism pathway. Galactitol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2R,3S,4R,5S)-Hexane-1,2,3,4,5,6-hexol</synonym>
    <synonym>D-Dulcitol</synonym>
    <synonym>D-Galactitol</synonym>
    <synonym>Dulcitol</synonym>
    <synonym>Dulcose</synonym>
    <synonym>Euonymit</synonym>
    <synonym>L-Galactitol</synonym>
    <synonym>Melampyrin</synonym>
    <synonym>Melampyrit</synonym>
    <synonym>Ambap5938</synonym>
    <synonym>Dulcite</synonym>
    <synonym>Hexitol</synonym>
    <synonym>Melampyrite</synonym>
    <synonym>Melampyrum</synonym>
    <synonym>Meso-galactitol</synonym>
  </synonyms>
  <chemical_formula>C6H14O6</chemical_formula>
  <average_molecular_weight>182.1718</average_molecular_weight>
  <monisotopic_moleculate_weight>182.07903818</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol</iupac_name>
  <traditional_iupac>galactitol</traditional_iupac>
  <cas_registry_number>608-66-2</cas_registry_number>
  <smiles>OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO</smiles>
  <inchi>InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6-</inchi>
  <inchikey>FBPFZTCFMRRESA-GUCUJZIJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar alcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sugar alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>hexitol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>189.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>31,0 mg/mL at 15 °C</value>
      <source>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>182.1718</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>182.07903818</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H14O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FBPFZTCFMRRESA-GUCUJZIJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>121.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326328</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01697</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB006453</foodb_id>
  <chemspider_id>11357</chemspider_id>
  <pubchem_compound_id>11850</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16813</chebi_id>
  <knapsack_id>C00001160</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Galactitol</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>38183</bigg_id>
  <metlin_id>5148</metlin_id>
  <synthesis_reference>Muniruzzaman, Syed; Itoh, Hiromichi; Yoshino, Akira; Katayama, Takeshi; Izumori, Ken.  Biotransformation of lactose to galactitol.    Journal of Fermentation and Bioengineering  (1994),  77(1),  32-5.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:41 UTC</creation_date>
  <update_date>2020-04-16 20:40:45 UTC</update_date>
  <accession>BMDB0000108</accession>
  <secondary_accessions>
    <accession>BMDB00108</accession>
  </secondary_accessions>
  <name>Ethanol</name>
  <description>Ethanol, also known as alcohol or 1-hydroxyethane, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). Ethanol is a drug which is used for therapeutic neurolysis of nerves or ganglia for the relief of intractable chronic pain in such conditions as inoperable cancer and trigeminal neuralgia (tic douloureux), in patients for whom neurosurgical procedures are contraindicated. Ethanol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Ethanol exists in all living species, ranging from bacteria to humans. Ethanol participates in a number of enzymatic reactions, within cattle. In particular, Ethanol can be converted into acetaldehyde; which is catalyzed by the enzyme alcohol dehydrogenase 1B. In addition, Ethanol can be converted into acetaldehyde through the action of the enzyme cytochrome P450 2E1. In cattle, ethanol is involved in the metabolic pathway called the ethanol degradation pathway. Ethanol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Hydroxyethane</synonym>
    <synonym>[CH2Me(OH)]</synonym>
    <synonym>[OEtH]</synonym>
    <synonym>Alcohol</synonym>
    <synonym>Alcohol etilico</synonym>
    <synonym>Alcool ethylique</synonym>
    <synonym>Alkohol</synonym>
    <synonym>Aethanol</synonym>
    <synonym>Aethylalkohol</synonym>
    <synonym>C2H5OH</synonym>
    <synonym>Dehydrated ethanol</synonym>
    <synonym>Etanol</synonym>
    <synonym>Ethyl alcohol</synonym>
    <synonym>EtOH</synonym>
    <synonym>Hydroxyethane</synonym>
    <synonym>Methylcarbinol</synonym>
    <synonym>Spiritus vini</synonym>
    <synonym>Anhydrous ethanol</synonym>
    <synonym>Absolute alcohol</synonym>
    <synonym>Absolute ethanol</synonym>
    <synonym>Absolute ethyl alcohol</synonym>
    <synonym>Alcare hand degermer</synonym>
    <synonym>Alcohols</synonym>
    <synonym>Alcool etilico</synonym>
    <synonym>Algrain</synonym>
    <synonym>Alkoholu etylowego</synonym>
    <synonym>Anhydrol</synonym>
    <synonym>Anhydrous alcohol</synonym>
    <synonym>Cologne spirit</synonym>
    <synonym>Cologne spirits</synonym>
    <synonym>Dehydrated alcohol</synonym>
    <synonym>Denatured alcohol</synonym>
    <synonym>Denatured ethanol</synonym>
    <synonym>Desinfektol el</synonym>
    <synonym>Diluted alcohol</synonym>
    <synonym>Distilled spirits</synonym>
    <synonym>Ethanol 200 proof</synonym>
    <synonym>Ethanol solution</synonym>
    <synonym>Ethicap</synonym>
    <synonym>Ethyl alc</synonym>
    <synonym>Ethyl alcohol anhydrous</synonym>
    <synonym>Ethyl alcohol in alcoholic beverages</synonym>
    <synonym>Ethyl alcohol usp</synonym>
    <synonym>Ethyl hydrate</synonym>
    <synonym>Ethyl hydroxide</synonym>
    <synonym>Fermentation alcohol</synonym>
    <synonym>Grain alcohol</synonym>
    <synonym>Hinetoless</synonym>
    <synonym>Infinity pure</synonym>
    <synonym>Jaysol</synonym>
    <synonym>Jaysol S</synonym>
    <synonym>Lux</synonym>
    <synonym>Molasses alcohol</synonym>
    <synonym>Potato alcohol</synonym>
    <synonym>Punctilious ethyl alcohol</synonym>
    <synonym>Pyro</synonym>
    <synonym>Silent spirit</synonym>
    <synonym>Spirit</synonym>
    <synonym>Spirits OF wine</synonym>
    <synonym>Spirt</synonym>
    <synonym>Synasol</synonym>
    <synonym>Tecsol</synonym>
    <synonym>Tecsol C</synonym>
    <synonym>Thanol</synonym>
    <synonym>Undenatured ethanol</synonym>
    <synonym>Alcohol, absolute</synonym>
    <synonym>Alcohol, ethyl</synonym>
    <synonym>Alcohol, grain</synonym>
  </synonyms>
  <chemical_formula>C2H6O</chemical_formula>
  <average_molecular_weight>46.0684</average_molecular_weight>
  <monisotopic_moleculate_weight>46.041864814</monisotopic_moleculate_weight>
  <iupac_name>ethanol</iupac_name>
  <traditional_iupac>ethyl alcohol</traditional_iupac>
  <cas_registry_number>64-17-5</cas_registry_number>
  <smiles>CCO</smiles>
  <inchi>InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3</inchi>
  <inchikey>LFQSCWFLJHTTHZ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Primary alcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a primary alcohol</external_descriptor>
      <external_descriptor>a short-chain alcohol</external_descriptor>
      <external_descriptor>alkyl alcohol</external_descriptor>
      <external_descriptor>ethanols</external_descriptor>
      <external_descriptor>primary alcohol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-114.1 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.31</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>16.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>ethanol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>46.0684</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>46.041864814</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H6O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H6O/c1-2-3/h3H,2H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LFQSCWFLJHTTHZ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>13.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>5.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ethanol Degradation</name>
      <smpdb_id>SMP0087192</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4986</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>8+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3-68</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS</comment>
      <references>
        <reference>
          <reference_text>Raun BM, Kristensen NB: Metabolic effects of feeding ethanol or propanol to postpartum transition Holstein cows. J Dairy Sci. 2011 May;94(5):2566-80. doi: 10.3168/jds.2010-3999.</reference_text>
          <pubmed_id>21524548</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>2065+/-985</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>299+/-182</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.71 +/- 9.92</concentration_value>
      <concentration_units>mg/100g dry matter content</concentration_units>
      <comment>Italian raw milk</comment>
      <references>
        <reference>
          <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.94 +/- 5.8</concentration_value>
      <concentration_units>mg/100g dry matter content</concentration_units>
      <comment>Slovenian raw milk</comment>
      <references>
        <reference>
          <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0418 +/- 0.0250</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>In raw milk samples for diets based on grass silage</comment>
      <references>
        <reference>
          <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
          <pubmed_id>12463694</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.406 +/- 0.449</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>In raw milk samples for diets based on maize silage</comment>
      <references>
        <reference>
          <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
          <pubmed_id>12463694</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.769 +/- 0.891</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>In raw milk samples for diets based on hay</comment>
      <references>
        <reference>
          <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
          <pubmed_id>12463694</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>160</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>43-69</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>3-170</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>176</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>203</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>341</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>131</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>600-3200</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS</comment>
      <references>
        <reference>
          <reference_text>Raun BM, Kristensen NB: Metabolic effects of feeding ethanol or propanol to postpartum transition Holstein cows. J Dairy Sci. 2011 May;94(5):2566-80. doi: 10.3168/jds.2010-3999.</reference_text>
          <pubmed_id>21524548</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>556+/-450</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>202.41 +/- 55.52</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>241.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>355.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>425.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>202.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>241 +/- 96</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>355 +/- 148</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>425 +/- 259</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>202 +/- 55</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>246+/-172</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>125+/-111</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00469</kegg_id>
  <drugbank_id>DB00898</drugbank_id>
  <foodb_id>FDB000753</foodb_id>
  <chemspider_id>682</chemspider_id>
  <pubchem_compound_id>702</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16236</chebi_id>
  <knapsack_id>C00019560</knapsack_id>
  <meta_cyc_id>ETOH</meta_cyc_id>
  <wikipedia_id>Ethanol</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35062</bigg_id>
  <metlin_id>3203</metlin_id>
  <synthesis_reference>Lashley, David.  Process for producing an alcoholic sugar cane juice beverage.    U.S.  (1988),     3 pp.  CODEN: USXXAM  US  4784859  A  19881115  CAN 110:113222  AN 1989:113222</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
      <pubmed_id>12463694</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:42 UTC</creation_date>
  <update_date>2020-04-16 20:40:37 UTC</update_date>
  <accession>BMDB0000112</accession>
  <secondary_accessions>
    <accession>BMDB00112</accession>
  </secondary_accessions>
  <name>Gamma-Aminobutyric acid</name>
  <description>Gamma-Aminobutyric acid, also known as gaba or g-amino-butanoate, belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. Gamma-Aminobutyric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Gamma-Aminobutyric acid exists in all living species, ranging from bacteria to humans. Gamma-Aminobutyric acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>4-Aminobutanoic acid</synonym>
    <synonym>4-Aminobutyric acid</synonym>
    <synonym>4Abu</synonym>
    <synonym>GABA</synonym>
    <synonym>GAMMA-AMINO-butanoIC ACID</synonym>
    <synonym>gamma-Amino-N-butyric acid</synonym>
    <synonym>gamma-Aminobutanoic acid</synonym>
    <synonym>gamma-Aminobuttersaeure</synonym>
    <synonym>Omega-aminobutyric acid</synonym>
    <synonym>Piperidic acid</synonym>
    <synonym>Piperidinic acid</synonym>
    <synonym>4-Aminobutyrate</synonym>
    <synonym>Gammalon</synonym>
    <synonym>4-Aminobutanoate</synonym>
    <synonym>g-AMINO-butanoate</synonym>
    <synonym>g-AMINO-butanoic acid</synonym>
    <synonym>gamma-AMINO-butanoate</synonym>
    <synonym>Γ-amino-butanoate</synonym>
    <synonym>Γ-amino-butanoic acid</synonym>
    <synonym>g-Amino-N-butyrate</synonym>
    <synonym>g-Amino-N-butyric acid</synonym>
    <synonym>gamma-Amino-N-butyrate</synonym>
    <synonym>Γ-amino-N-butyrate</synonym>
    <synonym>Γ-amino-N-butyric acid</synonym>
    <synonym>g-Aminobutanoate</synonym>
    <synonym>g-Aminobutanoic acid</synonym>
    <synonym>gamma-Aminobutanoate</synonym>
    <synonym>Γ-aminobutanoate</synonym>
    <synonym>Γ-aminobutanoic acid</synonym>
    <synonym>g-Aminobuttersaeure</synonym>
    <synonym>Γ-aminobuttersaeure</synonym>
    <synonym>Omega-aminobutyrate</synonym>
    <synonym>Piperidate</synonym>
    <synonym>Piperidinate</synonym>
    <synonym>g-Aminobutyrate</synonym>
    <synonym>g-Aminobutyric acid</synonym>
    <synonym>gamma-Aminobutyrate</synonym>
    <synonym>Γ-aminobutyrate</synonym>
    <synonym>Γ-aminobutyric acid</synonym>
    <synonym>3-Carboxypropylamine</synonym>
    <synonym>Aminalon</synonym>
    <synonym>Gaballon</synonym>
    <synonym>Gamarex</synonym>
    <synonym>gamma Aminobutyrate</synonym>
    <synonym>gamma Aminobutyric acid</synonym>
    <synonym>Gammalone</synonym>
    <synonym>Gammar</synonym>
    <synonym>Gammasol</synonym>
    <synonym>Mielogen</synonym>
    <synonym>Mielomade</synonym>
    <synonym>W-Aminobutyrate</synonym>
    <synonym>W-Aminobutyric acid</synonym>
    <synonym>gamma-Aminobutyric acid, calcium salt (2:1)</synonym>
    <synonym>gamma-Aminobutyric acid, hydrochloride</synonym>
    <synonym>gamma-Aminobutyric acid, zinc salt (2:1)</synonym>
    <synonym>4 Aminobutanoic acid</synonym>
    <synonym>4 Aminobutyric acid</synonym>
    <synonym>Lithium gaba</synonym>
    <synonym>gamma Aminobutyric acid, monolithium salt</synonym>
    <synonym>gamma Aminobutyric acid, monosodium salt</synonym>
    <synonym>gamma-Aminobutyric acid, monolithium salt</synonym>
    <synonym>gamma-Aminobutyric acid, monosodium salt</synonym>
    <synonym>Acid, hydrochloride gamma-aminobutyric</synonym>
    <synonym>Aminalone</synonym>
    <synonym>GABA, lithium</synonym>
    <synonym>Hydrochloride gamma-aminobutyric acid</synonym>
    <synonym>gamma Aminobutyric acid, hydrochloride</synonym>
    <synonym>4-Amino-butanoate</synonym>
    <synonym>gamma-Aminobutyric acid</synonym>
  </synonyms>
  <chemical_formula>C4H9NO2</chemical_formula>
  <average_molecular_weight>103.1198</average_molecular_weight>
  <monisotopic_moleculate_weight>103.063328537</monisotopic_moleculate_weight>
  <iupac_name>4-aminobutanoic acid</iupac_name>
  <traditional_iupac>gamma(amino)-butyric acid</traditional_iupac>
  <cas_registry_number>56-12-2</cas_registry_number>
  <smiles>NCCCC(O)=O</smiles>
  <inchi>InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)</inchi>
  <inchikey>BTCSSZJGUNDROE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Gamma amino acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Gamma amino acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>gamma-amino acid</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>203 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1300.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.17</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-aminobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>103.1198</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>103.063328537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H9NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BTCSSZJGUNDROE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29921</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2881</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2882</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20691</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>75.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>86.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>103.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>66.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>76 +/- 12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>87 +/- 14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>103 +/- 33</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>66 +/- 13</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00334</kegg_id>
  <drugbank_id>DB02530</drugbank_id>
  <foodb_id>FDB030489</foodb_id>
  <chemspider_id>116</chemspider_id>
  <pubchem_compound_id>119</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16865</chebi_id>
  <knapsack_id>C00001337</knapsack_id>
  <meta_cyc_id>4-AMINO-BUTYRATE</meta_cyc_id>
  <wikipedia_id>Gamma-Aminobutyric_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34652</bigg_id>
  <metlin_id/>
  <synthesis_reference>Minoshima, Ryoichi.  Preparation of gamma-aminobutyric acid with unripened beans.    PCT Int. Appl.  (2007),     25pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00596</protein_accession>
      <name>4-aminobutyrate aminotransferase, mitochondrial</name>
      <uniprot_id>Q9BGI0</uniprot_id>
      <gene_name>ABAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00862</protein_accession>
      <name>Glutamate decarboxylase 1</name>
      <uniprot_id>Q0VCA1</uniprot_id>
      <gene_name>GAD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00950</protein_accession>
      <name>Gamma-aminobutyric acid receptor-associated protein-like 2</name>
      <uniprot_id>P60519</uniprot_id>
      <gene_name>GABARAPL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01671</protein_accession>
      <name>Gamma-aminobutyric acid (GABA) A receptor, beta 3</name>
      <uniprot_id>A1L501</uniprot_id>
      <gene_name>GABRB3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01723</protein_accession>
      <name>Gamma-aminobutyric acid (GABA) A receptor, delta</name>
      <uniprot_id>A2VE38</uniprot_id>
      <gene_name>GABRD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01836</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit beta-2</name>
      <uniprot_id>P0C2W5</uniprot_id>
      <gene_name>GABRB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01837</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit pi</name>
      <uniprot_id>Q5EA06</uniprot_id>
      <gene_name>GABRP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01852</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit alpha-5</name>
      <uniprot_id>Q08E50</uniprot_id>
      <gene_name>GABRA5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01853</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit beta-1</name>
      <uniprot_id>P08220</uniprot_id>
      <gene_name>GABRB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01857</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit alpha-4</name>
      <uniprot_id>P20237</uniprot_id>
      <gene_name>GABRA4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01858</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit gamma-2</name>
      <uniprot_id>P22300</uniprot_id>
      <gene_name>GABRG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01864</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit alpha-3</name>
      <uniprot_id>P10064</uniprot_id>
      <gene_name>GABRA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01865</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit alpha-2</name>
      <uniprot_id>P10063</uniprot_id>
      <gene_name>GABRA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01869</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit rho-2</name>
      <uniprot_id>Q0II76</uniprot_id>
      <gene_name>GABRR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01871</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit alpha-1</name>
      <uniprot_id>P08219</uniprot_id>
      <gene_name>GABRA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02104</protein_accession>
      <name>Lin-7 homolog C</name>
      <uniprot_id>Q0P5F3</uniprot_id>
      <gene_name>LIN7C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02105</protein_accession>
      <name>Lin-7 homolog B</name>
      <uniprot_id>Q2KIB6</uniprot_id>
      <gene_name>LIN7B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02106</protein_accession>
      <name>Lin-7 homolog A</name>
      <uniprot_id>Q32LM6</uniprot_id>
      <gene_name>LIN7A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02177</protein_accession>
      <name>Gamma-aminobutyric acid receptor-associated protein</name>
      <uniprot_id>Q9GJW7</uniprot_id>
      <gene_name>GABARAP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02178</protein_accession>
      <name>Gamma-aminobutyric acid receptor-associated protein-like 1</name>
      <uniprot_id>Q8HYB6</uniprot_id>
      <gene_name>GABARAPL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02179</protein_accession>
      <name>Acyl-CoA-binding protein</name>
      <uniprot_id>P07107</uniprot_id>
      <gene_name>DBI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02180</protein_accession>
      <name>Sodium- and chloride-dependent GABA transporter 2</name>
      <uniprot_id>A5PJX7</uniprot_id>
      <gene_name>SLC6A13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:43 UTC</creation_date>
  <update_date>2020-04-15 22:13:08 UTC</update_date>
  <accession>BMDB0000114</accession>
  <secondary_accessions>
    <accession>BMDB00114</accession>
  </secondary_accessions>
  <name>Glycerylphosphorylethanolamine</name>
  <description>Glycerylphosphorylethanolamine, also known as glycerylphosphorylethanolamine, belongs to the class of organic compounds known as organic phosphoramides. These are organic compounds containing the phosphoric acid amide functional group. Glycerylphosphorylethanolamine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Glycerylphosphorylethanolamine exists in all living organisms, ranging from bacteria to humans. Glycerylphosphorylethanolamine can be converted into glycerol 3-phosphate and ethanolamine through the action of the enzyme glycerophosphodiester phosphodiesterase 1. In cattle, glycerylphosphorylethanolamine is involved in the metabolic pathway called phospholipid biosynthesis pathway.</description>
  <synonyms>
    <synonym>2-Aminoethyl ester 1-glycerophosphoric acid</synonym>
    <synonym>a-Glycerophosphorylethanolamine</synonym>
    <synonym>alpha-Glycerophosphorylethanolamine</synonym>
    <synonym>Glycerol 3-phosphoethanolamine</synonym>
    <synonym>Glycerol 3-phosphorylethanolamine</synonym>
    <synonym>Glycerophosphoethanolamine</synonym>
    <synonym>Glycerophosphorylethanolamine</synonym>
    <synonym>Glyceryl-3-phosphorylethanolamine</synonym>
    <synonym>GPEA</synonym>
  </synonyms>
  <chemical_formula>C5H14NO6P</chemical_formula>
  <average_molecular_weight>215.1415</average_molecular_weight>
  <monisotopic_moleculate_weight>215.055873697</monisotopic_moleculate_weight>
  <iupac_name>[(2,3-dihydroxypropyl)(2-hydroxyethyl)amino]phosphonic acid</iupac_name>
  <traditional_iupac>GPEA</traditional_iupac>
  <cas_registry_number/>
  <smiles>OCCN(CC(O)CO)P(O)(O)=O</smiles>
  <inchi>InChI=1S/C5H14NO6P/c7-2-1-6(13(10,11)12)3-5(9)4-8/h5,7-9H,1-4H2,(H2,10,11,12)</inchi>
  <inchikey>FRMZOWIQVCBEAC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as organic phosphoramides. These are organic compounds containing the phosphoric acid amide functional group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic phosphoric acids and derivatives</class>
    <sub_class>Organic phosphoramides</sub_class>
    <direct_parent>Organic phosphoramides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkanolamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkanolamine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid amide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(2,3-dihydroxypropyl)(2-hydroxyethyl)amino]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>215.1415</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>215.055873697</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCCN(CC(O)CO)P(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H14NO6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H14NO6P/c7-2-1-6(13(10,11)12)3-5(9)4-8/h5,7-9H,1-4H2,(H2,10,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FRMZOWIQVCBEAC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>121.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>44.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33019</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB021895</foodb_id>
  <drugbank_id/>
  <chemspider_id/>
  <pubchem_compound_id>22833510</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <chebi_id>134287</chebi_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Tronconi, Giovanni.  Process for the chromatographic isolation of 1-(a)-glycerylphosphorylcholine and of L-(a)-glycerylphosphorylethanolamine.    PCT Int. Appl.  (1990),     18 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:44 UTC</creation_date>
  <update_date>2020-04-16 20:39:12 UTC</update_date>
  <accession>BMDB0000115</accession>
  <secondary_accessions>
    <accession>BMDB00115</accession>
  </secondary_accessions>
  <name>Glycolic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Hydroxyacetic acid</synonym>
    <synonym>2-Hydroxyethanoic acid</synonym>
    <synonym>alpha-Hydroxyacetic acid</synonym>
    <synonym>Glycollic acid</synonym>
    <synonym>HOCH2COOH</synonym>
    <synonym>Hydroxyacetic acid</synonym>
    <synonym>Hydroxyethanoic acid</synonym>
    <synonym>2-Hydroxyacetate</synonym>
    <synonym>2-Hydroxyethanoate</synonym>
    <synonym>a-Hydroxyacetate</synonym>
    <synonym>a-Hydroxyacetic acid</synonym>
    <synonym>alpha-Hydroxyacetate</synonym>
    <synonym>Α-hydroxyacetate</synonym>
    <synonym>Α-hydroxyacetic acid</synonym>
    <synonym>Glycollate</synonym>
    <synonym>Hydroxyacetate</synonym>
    <synonym>Hydroxyethanoate</synonym>
    <synonym>Glycolate</synonym>
    <synonym>Glycocide</synonym>
    <synonym>GlyPure</synonym>
    <synonym>GlyPure 70</synonym>
    <synonym>Sodium glycolate</synonym>
    <synonym>Glycolic acid, 2-(14)C-labeled</synonym>
    <synonym>Glycolic acid, 1-(14)C-labeled</synonym>
    <synonym>Glycolic acid, potassium salt</synonym>
    <synonym>Glycolic acid, monopotassium salt</synonym>
    <synonym>Glycolic acid, calcium salt</synonym>
    <synonym>Glycolic acid, monoammonium salt</synonym>
    <synonym>Glycolic acid, monolithium salt</synonym>
    <synonym>Glycolic acid, monosodium salt</synonym>
    <synonym>Potassium glycolate</synonym>
  </synonyms>
  <chemical_formula>C2H4O3</chemical_formula>
  <average_molecular_weight>76.0514</average_molecular_weight>
  <monisotopic_moleculate_weight>76.016043994</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxyacetic acid</iupac_name>
  <traditional_iupac>glycolic acid</traditional_iupac>
  <cas_registry_number>79-14-1</cas_registry_number>
  <smiles>OCC(O)=O</smiles>
  <inchi>InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)</inchi>
  <inchikey>AEMRFAOFKBGASW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Alpha hydroxy acids and derivatives</sub_class>
    <direct_parent>Alpha hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>primary alcohol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>75 - 80 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.11</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxyacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>76.0514</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>76.016043994</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H4O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AEMRFAOFKBGASW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>14.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>6.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437682</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C03547</kegg_id>
  <foodb_id>FDB003298</foodb_id>
  <drugbank_id>DB03085</drugbank_id>
  <chemspider_id>737</chemspider_id>
  <pubchem_compound_id>757</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <chebi_id>17497</chebi_id>
  <knapsack_id>C00007461</knapsack_id>
  <meta_cyc_id>GLYCOLLATE</meta_cyc_id>
  <bigg_id>34090</bigg_id>
  <wikipedia_id>Glycolic_acid</wikipedia_id>
  <metlin_id>3219</metlin_id>
  <synthesis_reference>Witzemann, Edgar J. Preparation of glycollic acid.  Journal of the American Chemical Society  (1917),  39  109-12.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00090</protein_accession>
      <name>Phosphoglycolate phosphatase</name>
      <uniprot_id>Q2T9S4</uniprot_id>
      <gene_name>PGP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:45 UTC</creation_date>
  <update_date>2020-04-16 20:40:34 UTC</update_date>
  <accession>BMDB0000118</accession>
  <secondary_accessions>
    <accession>BMDB00118</accession>
  </secondary_accessions>
  <name>Homovanillic acid</name>
  <description>Homovanillic acid, also known as vanillacetate or homovanillate, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Homovanillic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Homovanillic acid exists in all living species, ranging from bacteria to humans. Homovanillic acid participates in a number of enzymatic reactions, within cattle. In particular, Homovanillic acid can be biosynthesized from homovanillin; which is catalyzed by the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In addition, Homovanillic acid and pyrocatechol can be biosynthesized from 3,4-dihydroxybenzeneacetic acid and guaiacol through its interaction with the enzyme catechol O-methyltransferase. In cattle, homovanillic acid is involved in the metabolic pathway called the tyrosine metabolism pathway. Homovanillic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(4-Hydroxy-3-methoxyphenyl)acetic acid</synonym>
    <synonym>3-Methoxy-4-hydroxyphenylacetate</synonym>
    <synonym>3-Methoxy-4-hydroxyphenylacetic acid</synonym>
    <synonym>4-Hydroxy-3-methoxybenzeneacetic acid</synonym>
    <synonym>HVA</synonym>
    <synonym>Vanillacetic acid</synonym>
    <synonym>(4-Hydroxy-3-methoxyphenyl)acetate</synonym>
    <synonym>4-Hydroxy-3-methoxybenzeneacetate</synonym>
    <synonym>Vanillacetate</synonym>
    <synonym>Homovanillate</synonym>
    <synonym>3-Methoxy-4-hydroxy-phenylacetic acid</synonym>
    <synonym>4-Hydroxy 3-methoxyphenylacetic acid</synonym>
    <synonym>4-Hydroxy-3-methoxyphenylacetic acid</synonym>
    <synonym>Homovanilate</synonym>
    <synonym>Homovanilic acid</synonym>
    <synonym>Homovanillinic acid</synonym>
    <synonym>Vanilacetate</synonym>
    <synonym>Vanilacetic acid</synonym>
    <synonym>3 Methoxy 4 hydroxyphenylacetic acid</synonym>
    <synonym>Acid, 3-methoxy-4-hydroxyphenylacetic</synonym>
    <synonym>Acid, 4-hydroxy-3-methoxyphenylacetic</synonym>
    <synonym>4 Hydroxy 3 methoxyphenylacetic acid</synonym>
    <synonym>Acid, homovanillic</synonym>
    <synonym>3'-Methoxy-4'-hydroxyphenylacetic acid</synonym>
    <synonym>3’-methoxy-4’-hydroxyphenylacetic acid</synonym>
    <synonym>Homovanillic acid</synonym>
  </synonyms>
  <chemical_formula>C9H10O4</chemical_formula>
  <average_molecular_weight>182.1733</average_molecular_weight>
  <monisotopic_moleculate_weight>182.057908808</monisotopic_moleculate_weight>
  <iupac_name>2-(4-hydroxy-3-methoxyphenyl)acetic acid</iupac_name>
  <traditional_iupac>homovanillic acid</traditional_iupac>
  <cas_registry_number>306-08-1</cas_registry_number>
  <smiles>COC1=CC(CC(O)=O)=CC=C1O</smiles>
  <inchi>InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)</inchi>
  <inchikey>QRMZSPFSDQBLIX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Methoxyphenols</sub_class>
    <direct_parent>Methoxyphenols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>monocarboxylic acid</external_descriptor>
      <external_descriptor>monomethoxybenzene</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>138 - 140 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>17 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.33</value>
      <source>LAHANN,TR ET AL. (1989)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(4-hydroxy-3-methoxyphenyl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>182.1733</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>182.057908808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC(CC(O)=O)=CC=C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QRMZSPFSDQBLIX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37301</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fermented milk, by capillary electrophoresis-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
          <pubmed_id>26686724</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C05582</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB001783</foodb_id>
  <chemspider_id>1675</chemspider_id>
  <pubchem_compound_id>1738</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>545959</chebi_id>
  <phenol_explorer_compound_id>574</phenol_explorer_compound_id>
  <knapsack_id>C00029504</knapsack_id>
  <meta_cyc_id>CPD-7651</meta_cyc_id>
  <wikipedia_id>Homovanillic_acid</wikipedia_id>
  <bigg_id>46066</bigg_id>
  <metlin_id>971</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
      <pubmed_id>26686724</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:46 UTC</creation_date>
  <update_date>2020-04-15 20:47:48 UTC</update_date>
  <accession>BMDB0000119</accession>
  <secondary_accessions>
    <accession>BMDB00119</accession>
  </secondary_accessions>
  <name>Glyoxylic acid</name>
  <description>Glyoxylic acid, also known as glyoxylic acid or glyoxylic acid, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Glyoxylic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Glyoxylic acid exists in all living species, ranging from bacteria to humans. L-Alanine and glyoxylic acid can be converted into glycine and pyruvic acid; which is catalyzed by the enzyme serine--pyruvate aminotransferase. In cattle, glyoxylic acid is involved in the metabolic pathway called the alanine metabolism pathway. Glyoxylic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>alpha-Ketoacetic acid</synonym>
    <synonym>Formylformic acid</synonym>
    <synonym>Glyoxalate</synonym>
    <synonym>Glyoxalsaeure</synonym>
    <synonym>Glyoxylate</synonym>
    <synonym>Glyoxylsaeure</synonym>
    <synonym>Oxalaldehydic acid</synonym>
    <synonym>Oxoethanoic acid</synonym>
    <synonym>a-Ketoacetate</synonym>
    <synonym>a-Ketoacetic acid</synonym>
    <synonym>alpha-Ketoacetate</synonym>
    <synonym>Α-ketoacetate</synonym>
    <synonym>Α-ketoacetic acid</synonym>
    <synonym>Formylformate</synonym>
    <synonym>Glyoxalic acid</synonym>
    <synonym>Oxalaldehydate</synonym>
    <synonym>Oxoethanoate</synonym>
    <synonym>Oxoacetate</synonym>
    <synonym>Oxoacetic acid</synonym>
    <synonym>Glyoxylic acid, 2-(14)C-labeled</synonym>
    <synonym>Glyoxylic acid, sodium salt</synonym>
    <synonym>Glyoxylic acid, sodium salt, 2-(14)C-labeled</synonym>
    <synonym>Glyoxylic acid, 14c2-labeled</synonym>
    <synonym>Glyoxylic acid, calcium salt</synonym>
    <synonym>Glyoxylic acid, sodium salt, 14C-labeled</synonym>
  </synonyms>
  <chemical_formula>C2H2O3</chemical_formula>
  <average_molecular_weight>74.0355</average_molecular_weight>
  <monisotopic_moleculate_weight>74.00039393</monisotopic_moleculate_weight>
  <iupac_name>2-oxoacetic acid</iupac_name>
  <traditional_iupac>glyoxylic acid</traditional_iupac>
  <cas_registry_number>298-12-4</cas_registry_number>
  <smiles>OC(=O)C=O</smiles>
  <inchi>InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)</inchi>
  <inchikey>HHLFWLYXYJOTON-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Carboxylic acids</sub_class>
    <direct_parent>Carboxylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Short-chain aldehydes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain aldehyde</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>aldehydic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-93 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-oxoacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>74.0355</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>74.00039393</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HHLFWLYXYJOTON-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>13.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>5.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437685</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00048</kegg_id>
  <drugbank_id>DB04343</drugbank_id>
  <foodb_id>FDB007244</foodb_id>
  <chemspider_id>740</chemspider_id>
  <pubchem_compound_id>760</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16891</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001186</knapsack_id>
  <meta_cyc_id>GLYOX</meta_cyc_id>
  <wikipedia_id>Glyoxylic_acid</wikipedia_id>
  <bigg_id>33659</bigg_id>
  <metlin_id>3213</metlin_id>
  <synthesis_reference>Jie, Yuanping; Song, Zhen.  Method for preparing glyoxylic acid.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2007), 5pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00665</protein_accession>
      <name>Peptidyl-glycine alpha-amidating monooxygenase</name>
      <uniprot_id>P10731</uniprot_id>
      <gene_name>PAM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00793</protein_accession>
      <name>Alanine--glyoxylate aminotransferase 2, mitochondrial</name>
      <uniprot_id>Q17QF0</uniprot_id>
      <gene_name>AGXT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:48 UTC</creation_date>
  <update_date>2020-04-15 22:13:10 UTC</update_date>
  <accession>BMDB0000121</accession>
  <secondary_accessions>
    <accession>BMDB00121</accession>
  </secondary_accessions>
  <name>Folic acid</name>
  <description>Folic acid, also known as folate or vitamin m, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Folic acid is a drug which is used for treatment of folic acid deficiency, megaloblastic anemia and in anemias of nutritional supplements, pregnancy, infancy, or childhood. Folic acid exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Folic acid exists in all living species, ranging from bacteria to humans. Folic acid participates in a number of enzymatic reactions, within cattle. In particular, Folic acid can be biosynthesized from dihydrofolic acid through its interaction with the enzyme dihydrofolate reductase. In addition, Folic acid can be converted into folic acid; which is catalyzed by the enzyme proton-coupled folate transporter. In cattle, folic acid is involved in the metabolic pathway called the folate metabolism pathway. Folic acid is a potentially toxic compound. Folic acid has been found to be associated with several diseases known as dimethylglycine dehydrogenase deficiency, bladder infections, fibromyalgia, and hereditary folate malabsorption; also folic acid has been linked to the inborn metabolic disorders including folate deficiency.</description>
  <synonyms>
    <synonym>Folate</synonym>
    <synonym>Folsaeure</synonym>
    <synonym>N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamic acid</synonym>
    <synonym>N-Pteroyl-L-glutamic acid</synonym>
    <synonym>PGA</synonym>
    <synonym>PteGlu</synonym>
    <synonym>Pteroyl-L-glutamic acid</synonym>
    <synonym>Pteroyl-L-monoglutamic acid</synonym>
    <synonym>Pteroylglutamic acid</synonym>
    <synonym>Vitamin BC</synonym>
    <synonym>Vitamin m</synonym>
    <synonym>Folicet</synonym>
    <synonym>N-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)carbonyl]-L-glutamate</synonym>
    <synonym>N-Pteroyl-L-glutamate</synonym>
    <synonym>Pteroyl-L-glutamate</synonym>
    <synonym>Pteroyl-L-monoglutamate</synonym>
    <synonym>Pteroylglutamate</synonym>
    <synonym>Acifolic</synonym>
    <synonym>Cytofol</synonym>
    <synonym>Dosfolat b activ</synonym>
    <synonym>Folacid</synonym>
    <synonym>Folacin</synonym>
    <synonym>Folbal</synonym>
    <synonym>Folcidin</synonym>
    <synonym>Foldine</synonym>
    <synonym>Folettes</synonym>
    <synonym>Foliamin</synonym>
    <synonym>Folipac</synonym>
    <synonym>Folsan</synonym>
    <synonym>Folsaure</synonym>
    <synonym>Folsav</synonym>
    <synonym>Folvite</synonym>
    <synonym>Incafolic</synonym>
    <synonym>Liver lactobacillus casei factor</synonym>
    <synonym>Millafol</synonym>
    <synonym>N-(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid</synonym>
    <synonym>N-[4-[[(2-Amino-3,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid</synonym>
    <synonym>Pteroylmonoglutamic acid</synonym>
    <synonym>Vitamin be</synonym>
    <synonym>Folic acid, (DL)-isomer</synonym>
    <synonym>Folic acid, sodium salt</synonym>
    <synonym>Folic acid, (D)-isomer</synonym>
    <synonym>Folic acid, monosodium salt</synonym>
    <synonym>Folic acid, potassium salt</synonym>
    <synonym>b9, Vitamin</synonym>
    <synonym>Folic acid, calcium salt (1:1)</synonym>
    <synonym>Folic acid, monopotassium salt</synonym>
    <synonym>Vitamin b9</synonym>
  </synonyms>
  <chemical_formula>C19H19N7O6</chemical_formula>
  <average_molecular_weight>441.3975</average_molecular_weight>
  <monisotopic_moleculate_weight>441.139681375</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</iupac_name>
  <traditional_iupac>folate</traditional_iupac>
  <cas_registry_number>59-30-3</cas_registry_number>
  <smiles>NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=CN=C2N1</smiles>
  <inchi>InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1</inchi>
  <inchikey>OVBPIULPVIDEAO-LBPRGKRZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Methoxyphenols</sub_class>
    <direct_parent>Methoxyphenols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>monocarboxylic acid</external_descriptor>
      <external_descriptor>monomethoxybenzene</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>250 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0016 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>441.3975</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>441.139681375</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=CN=C2N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H19N7O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t12-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OVBPIULPVIDEAO-LBPRGKRZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>208.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>111.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>42.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451198</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>NRC. 1989. Recommended Dietary Allowances.  10th ed. Natl. Acad. Press, Washington, DC.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.136</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.136</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.261</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.261</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.174</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Samples taken in March</comment>
      <references>
        <reference>
          <reference_text>Int. Dairy Journal 4 (1994) 161-172</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.136</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.109</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.132</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.109</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.249</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.249</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.249</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.087 +/- 0.004</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.083 +/- 0.001</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.09 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.09 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00504</kegg_id>
  <drugbank_id>DB00158</drugbank_id>
  <foodb_id>FDB014504</foodb_id>
  <chemspider_id>5815</chemspider_id>
  <pubchem_compound_id>6037</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>27470</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001539</knapsack_id>
  <meta_cyc_id>CPD-12826</meta_cyc_id>
  <wikipedia_id>Folic_Acid</wikipedia_id>
  <bigg_id>35180</bigg_id>
  <metlin_id>246</metlin_id>
  <synthesis_reference>Piper, James R.; McCaleb, George S.; Montgomery, John A. Synthesis of 10-propargylfolic acid from 2-amino-6-(bromomethyl)-4(1H)-pteridinone. Journal of Heterocyclic Chemistry (1987), 24(1), 279-82.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Int. Dairy Journal 4 (1994) 161-172</reference_text>
    </reference>
    <reference>
      <reference_text>NRC. 1989. Recommended Dietary Allowances.  10th ed. Natl. Acad. Press, Washington, DC.</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01956</protein_accession>
      <name>Solute carrier family 19 (Folate transporter), member 1</name>
      <uniprot_id>Q17QC9</uniprot_id>
      <gene_name>SLC19A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01957</protein_accession>
      <name>SLC19A3 protein</name>
      <uniprot_id>A7E352</uniprot_id>
      <gene_name>SLC19A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01958</protein_accession>
      <name>Solute carrier family 19 member 1</name>
      <uniprot_id>Q0V8L3</uniprot_id>
      <gene_name>SLC19A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01959</protein_accession>
      <name>Folate receptor 2 (Fetal)</name>
      <uniprot_id>Q0VCN9</uniprot_id>
      <gene_name>FOLR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01960</protein_accession>
      <name>Folate receptor alpha</name>
      <uniprot_id>P02702</uniprot_id>
      <gene_name>FOLR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:49 UTC</creation_date>
  <update_date>2020-04-16 20:40:46 UTC</update_date>
  <accession>BMDB0000122</accession>
  <secondary_accessions>
    <accession>BMDB00122</accession>
  </secondary_accessions>
  <name>D-Glucose</name>
  <description>D-Glucose, also known as D-GLC or cerelose, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. D-Glucose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Glucose exists in all living species, ranging from bacteria to humans. In cattle, D-glucose is involved in the metabolic pathway called the starch and sucrose metabolism pathway. D-Glucose is a potentially toxic compound. D-Glucose has been found to be associated with several diseases known as hypoglycemia, familial neonatal, donohue syndrome, and pregnancy; also d-glucose has been linked to several inborn metabolic disorders including 3-methyl-crotonyl-glycinuria and growth hormone deficiency.</description>
  <synonyms>
    <synonym>D-GLC</synonym>
    <synonym>D-GLCP</synonym>
    <synonym>Dextrose</synonym>
    <synonym>GLC-OH</synonym>
    <synonym>Glucose</synonym>
    <synonym>Grape sugar</synonym>
    <synonym>D-Glucopyranose</synonym>
    <synonym>Purified glucose</synonym>
    <synonym>Roferose ST</synonym>
    <synonym>(+)-Glucose</synonym>
    <synonym>Anhydrous dextrose</synonym>
    <synonym>Cerelose</synonym>
    <synonym>Cerelose 2001</synonym>
    <synonym>Clearsweet 95</synonym>
    <synonym>Clintose L</synonym>
    <synonym>Corn sugar</synonym>
    <synonym>CPC Hydrate</synonym>
    <synonym>D(+)-Glucose</synonym>
    <synonym>Dextropur</synonym>
    <synonym>Dextrosol</synonym>
    <synonym>Glucodin</synonym>
    <synonym>Glucolin</synonym>
    <synonym>Goldsugar</synonym>
    <synonym>Meritose</synonym>
    <synonym>Staleydex 111</synonym>
    <synonym>Staleydex 95m</synonym>
    <synonym>Tabfine 097(HS)</synonym>
    <synonym>Vadex</synonym>
    <synonym>D Glucose</synonym>
    <synonym>Glucose, (DL)-isomer</synonym>
    <synonym>Glucose, (L)-isomer</synonym>
    <synonym>Glucose, (beta-D)-isomer</synonym>
    <synonym>Glucose monohydrate</synonym>
    <synonym>Glucose, (alpha-D)-isomer</synonym>
    <synonym>L Glucose</synonym>
    <synonym>L-Glucose</synonym>
    <synonym>Dextrose, anhydrous</synonym>
    <synonym>Monohydrate, glucose</synonym>
  </synonyms>
  <chemical_formula>C6H12O6</chemical_formula>
  <average_molecular_weight>180.1559</average_molecular_weight>
  <monisotopic_moleculate_weight>180.063388116</monisotopic_moleculate_weight>
  <iupac_name>(3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>glucose</traditional_iupac>
  <cas_registry_number>2280-44-6</cas_registry_number>
  <smiles>[H]C1(O)O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O</smiles>
  <inchi>InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6?/m1/s1</inchi>
  <inchikey>WQZGKKKJIJFFOK-GASJEMHNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Aldoses</external_descriptor>
      <external_descriptor>D-glucose</external_descriptor>
      <external_descriptor>glucopyranose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>146 - 150 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1200.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.24</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>180.1559</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>180.063388116</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]C1(O)O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WQZGKKKJIJFFOK-GASJEMHNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>110.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glucose-Alanine Cycle</name>
      <smpdb_id>SMP0087221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Growth Hormone Signaling Pathway </name>
      <smpdb_id>SMP0120923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Insulin Signalling</name>
      <smpdb_id>SMP0108189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Degradation</name>
      <smpdb_id>SMP0087253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pancreas Function</name>
      <smpdb_id>SMP0119380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37304</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2941.896 +/- 253.114</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Spectrometry (Autoanalyzer/BT3000 Plus)</comment>
      <references>
        <reference>
          <reference_text>Abdullah BASOGLU, Nuri BASPINAR, Alparslan COSKUN. NMR-based metabolomic evaluation in dairy cows with displaced abomasum. Turk J Vet Anim Sci (2014) 38(3):325-330</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>5550</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Dacos Chemistry Analyzer in Hereford cows</comment>
      <references>
        <reference>
          <reference_text>Early RJ, McBride BW, Ball RO: Growth and metabolism in somatotropin-treated steers: I. Growth, serum chemistry and carcass weights. J Anim Sci. 1990 Dec;68(12):4134-43. doi: 10.2527/1990.68124134x.</reference_text>
          <pubmed_id>2286555</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by LC-MS and NMR in Angus-Hereford cows.</comment>
      <references>
        <reference>
          <reference_text>Aich P, Babiuk LA, Potter AA, Griebel P: Biomarkers for prediction of bovine respiratory disease outcome. OMICS. 2009 Jun;13(3):199-209. doi: 10.1089/omi.2009.0012.</reference_text>
          <pubmed_id>19275474</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3840-4610</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Cobas c311 chemistry analyzer</comment>
      <references>
        <reference>
          <reference_text>Consolo NRB, Munro JC, Bourgon SL, Karrow NA, Fredeen AH, Martell JE, Montanholi YR: Associations of Blood Analysis with Feed Efficiency and Developmental Stage in Grass-Fed Beef Heifers. Animals (Basel). 2018 Aug 2;8(8). pii: ani8080133. doi: 10.3390/ani8080133.</reference_text>
          <pubmed_id>30072590</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>4196.365 +/- 505.118</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Trinder (1969) method</comment>
      <references>
        <reference>
          <reference_text>C. R. E. Cogginsa and A. C. Field. Diurnal variation in the chemical composition of plasma from lactating beef cows on three dietary energy intakes. J. agric. Sri., Camb. (1976), 86, 595-602</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2800-4600</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Randox GL364 kit</comment>
      <references>
        <reference>
          <reference_text>Hernandez-Castellano LE, Hernandez LL, Weaver S, Bruckmaier RM: Increased serum serotonin improves parturient calcium homeostasis in dairy cows. J Dairy Sci. 2017 Feb;100(2):1580-1587. doi: 10.3168/jds.2016-11638. Epub 2016 Dec 14.</reference_text>
          <pubmed_id>27988124</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2150-2180</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Cobas c311/501 chemistry analyzer</comment>
      <references>
        <reference>
          <reference_text>Macdonald AGC, Bourgon SL, Palme R, Miller SP, Montanholi YR: Evaluation of blood metabolites reflects presence or absence of liver abscesses in beef cattle. Vet Rec Open. 2017 Apr 1;4(1):e000170. doi: 10.1136/vetreco-2016-000170. eCollection 2017.</reference_text>
          <pubmed_id>28890789</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3962+/-443</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3290-4070</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Membrane-immobilized enzyme with YSI 7100 MBS select biochemistry analyzer</comment>
      <references>
        <reference>
          <reference_text>Raun BM, Kristensen NB: Metabolic effects of feeding ethanol or propanol to postpartum transition Holstein cows. J Dairy Sci. 2011 May;94(5):2566-80. doi: 10.3168/jds.2010-3999.</reference_text>
          <pubmed_id>21524548</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>4013.191</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1200 ml pomegranate peel extract/cow per day</comment>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3807.813</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>400 ml pomegranate peel extract/cow per day</comment>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>4213.0177</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>800 ml pomegranate peel extract/cow per day</comment>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3560-3680</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Glucose-B test kit (Wako Pure Chemical)</comment>
      <references>
        <reference>
          <reference_text>Sato H, Matsumoto M, Hanasaka S: Relations between plasma acetate, 3-hydroxybutyrate, FFA, glucose levels and energy nutrition in lactating dairy cows. J Vet Med Sci. 1999 May;61(5):447-51. doi: 10.1292/jvms.61.447.</reference_text>
          <pubmed_id>10379932</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2600-3870</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Glucose OSR6222 with Beckman-Olympus AU 600 chemistry analyzer</comment>
      <references>
        <reference>
          <reference_text>Liker B.,  L. Bačar-Huskić,  M. Knežević,  V. Rupić,  N. Vranešić,  Ž. Romić,  D. Grbeša,  D. Mačešić,  J. Leto,  Z. Antunović,  Ž. Krnić. 2005. Blood metabolites and haematological indices of pregnant beef cows fed rumen-protected methionine. J. Anim. Feed Sci. 14(4):625–638</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 24 male 17-22-month-old Charolais beef cattles.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>80098+/-14629</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>536+/-259</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>76 - 662</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>62.723</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>376</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
          <pubmed_id>2760296</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>723</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Rulquin H, Verite R: Effects of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 1. Diets based on corn silage. J Dairy Sci. 1998 Dec;81(12):3239-47. doi: 10.3168/jds.S0022-0302(98)75888-6.</reference_text>
          <pubmed_id>9891269</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>540</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>548</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>340.62 +/- 65.95</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>288 +/- 32</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>261 +/- 29</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>277.537 (122.116-421.857)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized whole milk</comment>
      <references>
        <reference>
          <reference_text>Esperanza Troyano, Mar Villamiel, Agustin Olano, Jesus Sanz, and Isabel Martinez-Castro. Monosaccharides and myo-Inositol in Commercial Milks. J. Agric. Food Chem., 1996, 44 (3), pp 815–817</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>235 +/- 49</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>250 +/- 41</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>80-150</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Faulkner, A., Chaiybutr, N., Peaker, M., Carrick, D. I. and Kuhn, N. J. Metabolic significance of milk glucose. J. Dairy Res. 1981, 48, 51-56</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>932.526 +/- 68.274</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>No milk type was specified in the literature. Assume it was raw milk.</comment>
      <references>
        <reference>
          <reference_text>RAJAN SHARMA YUDHISHTHIR S RAJPUT POONAM GAURAV DOGRA SUDHIR K TOMAR.  Estimation of sugars in milk by HPLC and its application in detection of adulteration of milk with soymilk. International Journal of Dairy Technology, 2009, 62(4):514-519</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>139.879 +/- 3.886</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Tommaso R.I. Cataldi, Massimiliano Angelotti, Giuliana Bianco. Determination of mono- and disaccharides in milk and milk products by high-performance anion-exchange chromatography with pulsed amperometric detection. Analytica Chimica Acta 485 (2003) 43–49</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>250 +/- 41</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>288 +/- 32</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>261 +/- 29</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1137.903</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk, multiparous</comment>
      <references>
        <reference>
          <reference_text>Lehloenya KV, Stein DR, Allen DT, Selk GE, Jones DA, Aleman MM, Rehberger TG, Mertz KJ, Spicer LJ: Effects of feeding yeast and propionibacteria to dairy cows on milk yield and components, and reproduction*. J Anim Physiol Anim Nutr (Berl). 2008 Apr;92(2):190-202. doi: 10.1111/j.1439-0396.2007.00726.x.</reference_text>
          <pubmed_id>18336416</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1187.859</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk, primiparous</comment>
      <references>
        <reference>
          <reference_text>Lehloenya KV, Stein DR, Allen DT, Selk GE, Jones DA, Aleman MM, Rehberger TG, Mertz KJ, Spicer LJ: Effects of feeding yeast and propionibacteria to dairy cows on milk yield and components, and reproduction*. J Anim Physiol Anim Nutr (Berl). 2008 Apr;92(2):190-202. doi: 10.1111/j.1439-0396.2007.00726.x.</reference_text>
          <pubmed_id>18336416</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>235 +/- 49</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>387.43 +/- 91.21</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>331.24 +/- 84.17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>6.31+/-0.85</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>6.00+/-2.47</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>5.64+/-2.87</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>5.59+/-2.35</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>3300</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>66-1138</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>400</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>580</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>4-18</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS</comment>
      <references>
        <reference>
          <reference_text>Raun BM, Kristensen NB: Metabolic effects of feeding ethanol or propanol to postpartum transition Holstein cows. J Dairy Sci. 2011 May;94(5):2566-80. doi: 10.3168/jds.2010-3999.</reference_text>
          <pubmed_id>21524548</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>720</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2090</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>400</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>15934+/-11188</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>520.41 +/- 94.97</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>763.813 +/- 751.731</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>750</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1100</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2430</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>520</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>523 +/- 130</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>996 +/- 334</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1806 +/- 1305</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>549 +/- 97</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>549 +/- 97</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR and GC-MS</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>754+/-403</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>149+/-66</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00031</kegg_id>
  <foodb_id>FDB093715</foodb_id>
  <drugbank_id/>
  <chemspider_id>5589</chemspider_id>
  <pubchem_compound_id>5793</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <chebi_id>4167</chebi_id>
  <knapsack_id>C00001122</knapsack_id>
  <meta_cyc_id>D-Glucose</meta_cyc_id>
  <bigg_id>33582</bigg_id>
  <wikipedia_id>Glucose</wikipedia_id>
  <metlin_id>133</metlin_id>
  <synthesis_reference>Li, Dalin; Ruan, Yi; Song, Wen; Wang, Yongjun.  Improved process for producing glucose.  Faming Zhuanli Shenqing Gongkai Shuomingshu  (2003),     4 pp</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
      <pubmed_id>2760296</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hurtaud C, Rulquin H, Verite R: Effects of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 1. Diets based on corn silage. J Dairy Sci. 1998 Dec;81(12):3239-47. doi: 10.3168/jds.S0022-0302(98)75888-6.</reference_text>
      <pubmed_id>9891269</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
      <pubmed_id>11132867</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lehloenya KV, Stein DR, Allen DT, Selk GE, Jones DA, Aleman MM, Rehberger TG, Mertz KJ, Spicer LJ: Effects of feeding yeast and propionibacteria to dairy cows on milk yield and components, and reproduction*. J Anim Physiol Anim Nutr (Berl). 2008 Apr;92(2):190-202. doi: 10.1111/j.1439-0396.2007.00726.x.</reference_text>
      <pubmed_id>18336416</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00131</protein_accession>
      <name>Glucosylceramidase</name>
      <uniprot_id>Q2KHZ8</uniprot_id>
      <gene_name>GBA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00179</protein_accession>
      <name>YES1 protein</name>
      <uniprot_id>A7MB57</uniprot_id>
      <gene_name>YES1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00604</protein_accession>
      <name>Beta-1,4-galactosyltransferase 1</name>
      <uniprot_id>P08037</uniprot_id>
      <gene_name>B4GALT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00912</protein_accession>
      <name>Hexokinase-1</name>
      <uniprot_id>P27595</uniprot_id>
      <gene_name>HK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00913</protein_accession>
      <name>Kininogen-2</name>
      <uniprot_id>P01045</uniprot_id>
      <gene_name>KNG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00914</protein_accession>
      <name>Alpha-1,3-mannosyl-glycoprotein 4-beta-N-acetylglucosaminyltransferase A</name>
      <uniprot_id>O77836</uniprot_id>
      <gene_name>MGAT4A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00915</protein_accession>
      <name>Phosphatidylinositol 3-kinase regulatory subunit alpha</name>
      <uniprot_id>P23727</uniprot_id>
      <gene_name>PIK3R1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00916</protein_accession>
      <name>AMP-activated protein kinase gamma subunit</name>
      <uniprot_id>Q4G3U3</uniprot_id>
      <gene_name>PRKAG3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00917</protein_accession>
      <name>RAC-alpha serine/threonine-protein kinase</name>
      <uniprot_id>Q01314</uniprot_id>
      <gene_name>AKT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00918</protein_accession>
      <name>Kininogen-1</name>
      <uniprot_id>P01044</uniprot_id>
      <gene_name>KNG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01330</protein_accession>
      <name>Myosin-Ic</name>
      <uniprot_id>Q27966</uniprot_id>
      <gene_name>MYO1C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01617</protein_accession>
      <name>Collectin-43</name>
      <uniprot_id>P42916</uniprot_id>
      <gene_name>CL43</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01874</protein_accession>
      <name>Sodium/myo-inositol cotransporter 2</name>
      <uniprot_id>Q3ZC26</uniprot_id>
      <gene_name>SLC5A11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01883</protein_accession>
      <name>Peroxisome proliferator-activated receptor gamma</name>
      <uniprot_id>O18971</uniprot_id>
      <gene_name>PPARG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02025</protein_accession>
      <name>Solute carrier family 2, facilitated glucose transporter member 4</name>
      <uniprot_id>Q27994</uniprot_id>
      <gene_name>SLC2A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02034</protein_accession>
      <name>Solute carrier family 2, facilitated glucose transporter member 1</name>
      <uniprot_id>P27674</uniprot_id>
      <gene_name>SLC2A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02036</protein_accession>
      <name>Solute carrier family 2, facilitated glucose transporter member 8</name>
      <uniprot_id>P58354</uniprot_id>
      <gene_name>SLC2A8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02044</protein_accession>
      <name>P2Y purinoceptor 14</name>
      <uniprot_id>Q3SX17</uniprot_id>
      <gene_name>P2RY14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02051</protein_accession>
      <name>Solute carrier family 2, facilitated glucose transporter member 12</name>
      <uniprot_id>Q5J316</uniprot_id>
      <gene_name>SLC2A12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02056</protein_accession>
      <name>Solute carrier family 2, facilitated glucose transporter member 3</name>
      <uniprot_id>P58352</uniprot_id>
      <gene_name>SLC2A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02075</protein_accession>
      <name>Solute carrier family 2, facilitated glucose transporter member 5</name>
      <uniprot_id>P58353</uniprot_id>
      <gene_name>SLC2A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02145</protein_accession>
      <name>Angiopoietin-related protein 4</name>
      <uniprot_id>Q2KJ51</uniprot_id>
      <gene_name>ANGPTL4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02146</protein_accession>
      <name>Sorbin and SH3 domain containing 1</name>
      <uniprot_id>Q0VCF1</uniprot_id>
      <gene_name>SORBS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02147</protein_accession>
      <name>Islet amyloid polypeptide</name>
      <uniprot_id>Q28207</uniprot_id>
      <gene_name>IAPP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02148</protein_accession>
      <name>Solute carrier family 2 (Facilitated glucose transporter), member 1</name>
      <uniprot_id>A1L519</uniprot_id>
      <gene_name>SLC2A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02149</protein_accession>
      <name>Putative sodium-glucose cotransporter</name>
      <uniprot_id>Q9TTR6</uniprot_id>
      <gene_name>sglt1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02150</protein_accession>
      <name>Chromogranin-A</name>
      <uniprot_id>P05059</uniprot_id>
      <gene_name>CHGA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02151</protein_accession>
      <name>Solute carrier family 2 (Facilitated glucose transporter), member 3</name>
      <uniprot_id>A2VDL2</uniprot_id>
      <gene_name>SLC2A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02152</protein_accession>
      <name>Solute carrier family 2 (Facilitated glucose transporter), member 6</name>
      <uniprot_id>A1L502</uniprot_id>
      <gene_name>SLC2A6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02153</protein_accession>
      <name>Glucagon</name>
      <uniprot_id>P01272</uniprot_id>
      <gene_name>GCG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02154</protein_accession>
      <name>Solute carrier family 5 member 1</name>
      <uniprot_id>A5HNF2</uniprot_id>
      <gene_name>SLC5A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02155</protein_accession>
      <name>Hypoxia-inducible factor 1 alpha</name>
      <uniprot_id>Q9XTA5</uniprot_id>
      <gene_name>HIF1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02156</protein_accession>
      <name>Interleukin 1-beta</name>
      <uniprot_id>Q5MAC0</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02157</protein_accession>
      <name>Na+/glucose cotransporter</name>
      <uniprot_id>Q8MKB7</uniprot_id>
      <gene_name>SGLT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02158</protein_accession>
      <name>Sodium-dependent glucose transporter SGLT-I</name>
      <uniprot_id>Q95JG8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02159</protein_accession>
      <name>Kruppel-like factor 15</name>
      <uniprot_id>Q6UNK6</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:50 UTC</creation_date>
  <update_date>2020-04-16 20:39:52 UTC</update_date>
  <accession>BMDB0000123</accession>
  <secondary_accessions>
    <accession>BMDB00123</accession>
  </secondary_accessions>
  <name>Glycine</name>
  <description>Glycine, also known as Gly or aminoessigsaeure, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Glycine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Glycine exists in all living species, ranging from bacteria to humans. Glycine is a potentially toxic compound. Glycine has been found to be associated with several diseases known as crohn's disease, leukemia, phosphoserine aminotransferase deficiency, and hyperglycinemia, lactic acidosis, and seizures; also glycine has been linked to the inborn metabolic disorders including n-acetylglutamate synthetase deficiency.</description>
  <synonyms>
    <synonym>Aminoacetic acid</synonym>
    <synonym>Aminoessigsaeure</synonym>
    <synonym>Aminoethanoic acid</synonym>
    <synonym>G</synonym>
    <synonym>Gly</synonym>
    <synonym>Glycin</synonym>
    <synonym>Glycocoll</synonym>
    <synonym>Glykokoll</synonym>
    <synonym>Glyzin</synonym>
    <synonym>H2N-CH2-COOH</synonym>
    <synonym>Hgly</synonym>
    <synonym>Leimzucker</synonym>
    <synonym>Aminoacetate</synonym>
    <synonym>Aminoethanoate</synonym>
    <synonym>2-Aminoacetate</synonym>
    <synonym>2-Aminoacetic acid</synonym>
    <synonym>Aciport</synonym>
    <synonym>Amino-acetate</synonym>
    <synonym>Amino-acetic acid</synonym>
    <synonym>Glicoamin</synonym>
    <synonym>Glycolixir</synonym>
    <synonym>Glycosthene</synonym>
    <synonym>Gyn-hydralin</synonym>
    <synonym>Padil</synonym>
    <synonym>Glycine carbonate (1:1), monosodium salt</synonym>
    <synonym>Glycine carbonate (2:1), monopotassium salt</synonym>
    <synonym>Glycine sulfate (3:1)</synonym>
    <synonym>Glycine, monoammonium salt</synonym>
    <synonym>Glycine, monosodium salt</synonym>
    <synonym>Glycine, sodium hydrogen carbonate</synonym>
    <synonym>Monoammonium salt glycine</synonym>
    <synonym>Calcium salt glycine</synonym>
    <synonym>Glycine hydrochloride (2:1)</synonym>
    <synonym>Glycine phosphate (1:1)</synonym>
    <synonym>Glycine, monopotasssium salt</synonym>
    <synonym>Monopotasssium salt glycine</synonym>
    <synonym>Monosodium salt glycine</synonym>
    <synonym>Glycine carbonate (2:1), monolithium salt</synonym>
    <synonym>Glycine carbonate (2:1), monosodium salt</synonym>
    <synonym>Glycine hydrochloride</synonym>
    <synonym>Glycine, copper salt</synonym>
    <synonym>Hydrochloride, glycine</synonym>
    <synonym>Salt glycine, monoammonium</synonym>
    <synonym>Acid, aminoacetic</synonym>
    <synonym>Cobalt salt glycine</synonym>
    <synonym>Copper salt glycine</synonym>
    <synonym>Glycine phosphate</synonym>
    <synonym>Glycine, calcium salt</synonym>
    <synonym>Glycine, calcium salt (2:1)</synonym>
    <synonym>Glycine, cobalt salt</synonym>
    <synonym>Phosphate, glycine</synonym>
    <synonym>Salt glycine, monosodium</synonym>
  </synonyms>
  <chemical_formula>C2H5NO2</chemical_formula>
  <average_molecular_weight>75.0666</average_molecular_weight>
  <monisotopic_moleculate_weight>75.032028409</monisotopic_moleculate_weight>
  <iupac_name>2-aminoacetic acid</iupac_name>
  <traditional_iupac>glycine</traditional_iupac>
  <cas_registry_number>56-40-6</cas_registry_number>
  <smiles>NCC(O)=O</smiles>
  <inchi>InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)</inchi>
  <inchikey>DHMQDGOQFOQNFH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Amino acids</external_descriptor>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>alpha-amino acid</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
      <external_descriptor>serine family amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>262.2 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>249.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.21</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-aminoacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>75.0666</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>75.032028409</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H5NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DHMQDGOQFOQNFH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>6.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutathione Metabolism</name>
      <smpdb_id>SMP0087167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Glycine</name>
      <smpdb_id>SMP0119391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2924</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2922</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13998</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>287</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>326.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>162-185</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in Holstein and Red-Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Imhasly S, Naegeli H, Baumann S, von Bergen M, Luch A, Jungnickel H, Potratz S, Gerspach C: Metabolomic biomarkers correlating with hepatic lipidosis in dairy cows. BMC Vet Res. 2014 Jun 2;10:122. doi: 10.1186/1746-6148-10-122.</reference_text>
          <pubmed_id>24888604</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>513-760</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>398+/-65</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>405-428</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>3201+/-499</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>576+/-215</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>33 - 1100</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>163 - 855</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>33 - 1109</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>68 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>77 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>65 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>72 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9591.483</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9591.483</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9458.268</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9458.268</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9325.0527</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9325.0527</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9325.0527</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>342-570</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>368.34 +/- 26.45</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>379.36 +/- 32.68</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>402.07 +/- 29.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>551.88 +/- 18.61</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1068-1336</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>50-696</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>80-220</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>105</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>158</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>150</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>104</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hanne Christine Bertram, Niels Bastian Kristensen, Mogens Vestergaard, SÃ¸ren Krogh Jensen, Jakob Sehested, Niels Christian Nielsen, Anders Malmendal. Metabolic characterization of rumen epithelial tissue from dairy calves fed different starter diets using 1H NMR spectroscopy. Livestock Science (2008) 120:127-134   doi: 10.1016/j.livsci.2008.05.001</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>974+/-315</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>119.75 +/- 24.37</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>129 +/- 17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>130</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>165 +/- 55</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>177.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>168 +/- 70</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>189.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>113 +/- 27</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>119.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>113 +/- 27</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR, GC-MS and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>538+/-147</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>930-1250</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By paper chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Brown-Woodman PD, White IG: Amino acid composition of semen and the secretions of the male reproductive tract. Aust J Biol Sci. 1974 Aug;27(4):415-22. doi: 10.1071/bi9740415.</reference_text>
          <pubmed_id>4429492</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>1247+/-251</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein.</comment>
      <references>
        <reference>
          <reference_text>Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17.</reference_text>
          <pubmed_id>22059599</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00037</kegg_id>
  <drugbank_id>DB00145</drugbank_id>
  <foodb_id>FDB000484</foodb_id>
  <chemspider_id>730</chemspider_id>
  <pubchem_compound_id>750</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15428</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001361</knapsack_id>
  <meta_cyc_id>GLY</meta_cyc_id>
  <wikipedia_id>Glycine</wikipedia_id>
  <bigg_id>33610</bigg_id>
  <metlin_id>20</metlin_id>
  <synthesis_reference>Anslow, Winston K.; King, Harold. Synthesis of glycine. Journal of the Chemical Society (1929), 2163-6.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00083</protein_accession>
      <name>Serine hydroxymethyltransferase, mitochondrial</name>
      <uniprot_id>Q3SZ20</uniprot_id>
      <gene_name>SHMT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00087</protein_accession>
      <name>Serine hydroxymethyltransferase, cytosolic</name>
      <uniprot_id>Q5E9P9</uniprot_id>
      <gene_name>SHMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00197</protein_accession>
      <name>Glutathione synthetase</name>
      <uniprot_id>Q5EAC2</uniprot_id>
      <gene_name>GSS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00366</protein_accession>
      <name>2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial</name>
      <uniprot_id>Q0P5L8</uniprot_id>
      <gene_name>GCAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00556</protein_accession>
      <name>Glycine amidinotransferase, mitochondrial</name>
      <uniprot_id>Q2HJ74</uniprot_id>
      <gene_name>GATM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00600</protein_accession>
      <name>Trifunctional purine biosynthetic protein adenosine-3</name>
      <uniprot_id>Q59A32</uniprot_id>
      <gene_name>GART</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00624</protein_accession>
      <name>5-aminolevulinate synthase, nonspecific, mitochondrial</name>
      <uniprot_id>A6QLI6</uniprot_id>
      <gene_name>ALAS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00629</protein_accession>
      <name>5-aminolevulinate synthase, erythroid-specific, mitochondrial</name>
      <uniprot_id>Q3ZC31</uniprot_id>
      <gene_name>ALAS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00793</protein_accession>
      <name>Alanine--glyoxylate aminotransferase 2, mitochondrial</name>
      <uniprot_id>Q17QF0</uniprot_id>
      <gene_name>AGXT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00895</protein_accession>
      <name>Peroxisomal sarcosine oxidase</name>
      <uniprot_id>Q29RU9</uniprot_id>
      <gene_name>PIPOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00955</protein_accession>
      <name>Arylacetyl-CoA N-acyltransferase</name>
      <uniprot_id>O77512</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00956</protein_accession>
      <name>Glycine N-acyltransferase</name>
      <uniprot_id>Q2KIR7</uniprot_id>
      <gene_name>GLYAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01848</protein_accession>
      <name>Glycine receptor subunit alpha-1</name>
      <uniprot_id>P57695</uniprot_id>
      <gene_name>GLRA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01867</protein_accession>
      <name>Glycine receptor subunit beta</name>
      <uniprot_id>Q9GJS9</uniprot_id>
      <gene_name>GLRB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02092</protein_accession>
      <name>Sodium-coupled neutral amino acid transporter 5</name>
      <uniprot_id>Q5E9S9</uniprot_id>
      <gene_name>SLC38A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02107</protein_accession>
      <name>Sodium- and chloride-dependent glycine transporter 1</name>
      <uniprot_id>Q28039</uniprot_id>
      <gene_name>SLC6A9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02239</protein_accession>
      <name>Glycine receptor alpha 3</name>
      <uniprot_id>Q6WRF9</uniprot_id>
      <gene_name>GLRA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02240</protein_accession>
      <name>N-arachidonyl glycine receptor</name>
      <uniprot_id>Q3T0E9</uniprot_id>
      <gene_name>GPR18</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02241</protein_accession>
      <name>Transporter</name>
      <uniprot_id>Q27999</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02242</protein_accession>
      <name>Adaptin ear-binding coat-associated protein 1</name>
      <uniprot_id>Q3T093</uniprot_id>
      <gene_name>NECAP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:51 UTC</creation_date>
  <update_date>2020-04-15 22:05:46 UTC</update_date>
  <accession>BMDB0000124</accession>
  <secondary_accessions>
    <accession>BMDB00124</accession>
  </secondary_accessions>
  <name>Fructose 6-phosphate</name>
  <description>Fructose 6-phosphate, also known as neuberg ester or D-fructose-6-p, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Fructose 6-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Fructose 6-phosphate exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>D-Fructose 6-phosphate</synonym>
    <synonym>D-Fructose 6-phosphoric acid</synonym>
    <synonym>Fructose-6-phosphate</synonym>
    <synonym>Neuberg ester</synonym>
    <synonym>Fructose-6-phosphoric acid</synonym>
    <synonym>Fructose 6-phosphoric acid</synonym>
    <synonym>D-Fructose 6-phosphorate</synonym>
    <synonym>D-Fructose-6-p</synonym>
    <synonym>D-Fructose-6-phosphate</synonym>
    <synonym>FPC</synonym>
    <synonym>Fru-6-p</synonym>
    <synonym>Fructose-6-p</synonym>
    <synonym>Fructose-6P</synonym>
    <synonym>Fructose-6-phosphate, (alpha-D)-isomer</synonym>
    <synonym>Fructose-6-phosphate, (beta-D)-isomer</synonym>
    <synonym>Fructose-6-phosphate, disodium salt, (D)-isomer</synonym>
    <synonym>Fructose-6-phosphate, (D)-isomer</synonym>
    <synonym>Fructose-6-phosphate, 1-(14)C-labeled, (D)-isomer</synonym>
    <synonym>Fructose-6-phosphate, 2-(14)C-labeled, (D)-isomer</synonym>
    <synonym>Fructose-6-phosphate, barium (1:1) salt, (D)-isomer</synonym>
    <synonym>Fructose-6-phosphate, barium salt, (D)-isomer</synonym>
    <synonym>Fructose-6-phosphate, sodium salt, (D)-isomer</synonym>
    <synonym>Fructose-6-phosphate, calcium salt, (D)-isomer</synonym>
    <synonym>Fructose-6-phosphate, magnesium (1:1) salt, (D)-isomer</synonym>
    <synonym>Fructose-6-phosphate, sodium salt</synonym>
  </synonyms>
  <chemical_formula>C6H13O9P</chemical_formula>
  <average_molecular_weight>260.1358</average_molecular_weight>
  <monisotopic_moleculate_weight>260.029718526</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>D-fructose 6-phosphate</traditional_iupac>
  <cas_registry_number>643-13-0</cas_registry_number>
  <smiles>OCC(=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h4-7,9-11H,1-2H2,(H2,12,13,14)/t4-,5-,6-/m1/s1</inchi>
  <inchikey>GSXOAOHZAIYLCY-HSUXUTPPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Acyloins</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyloin</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hexose phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D-fructose 6-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>911 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>260.1358</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>260.029718526</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h4-7,9-11H,1-2H2,(H2,12,13,14)/t4-,5-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GSXOAOHZAIYLCY-HSUXUTPPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>164.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>48.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37306</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00085</kegg_id>
  <drugbank_id>DB04493</drugbank_id>
  <foodb_id>FDB021896</foodb_id>
  <chemspider_id>62713</chemspider_id>
  <pubchem_compound_id>69507</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15946</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-15709</meta_cyc_id>
  <wikipedia_id>Fructose 6-phosphate</wikipedia_id>
  <bigg_id>33795</bigg_id>
  <metlin_id>5159</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00103</protein_accession>
      <name>Transaldolase</name>
      <uniprot_id>Q2TBL6</uniprot_id>
      <gene_name>TALDO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00104</protein_accession>
      <name>Transaldolase</name>
      <uniprot_id>Q58DR3</uniprot_id>
      <gene_name>TALDO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00140</protein_accession>
      <name>6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 1</name>
      <uniprot_id>P49872</uniprot_id>
      <gene_name>PFKFB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00150</protein_accession>
      <name>Fructose-1,6-bisphosphatase isozyme 2</name>
      <uniprot_id>Q2KJJ9</uniprot_id>
      <gene_name>FBP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00155</protein_accession>
      <name>6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 3</name>
      <uniprot_id>Q28901</uniprot_id>
      <gene_name>PFKFB3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00162</protein_accession>
      <name>6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 2</name>
      <uniprot_id>P26285</uniprot_id>
      <gene_name>PFKFB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00176</protein_accession>
      <name>Fructose-1,6-bisphosphatase 1</name>
      <uniprot_id>Q3SZB7</uniprot_id>
      <gene_name>FBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00479</protein_accession>
      <name>6-phosphofructokinase, liver type</name>
      <uniprot_id>A1A4J1</uniprot_id>
      <gene_name>PFKL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00523</protein_accession>
      <name>6-phosphofructokinase, muscle type</name>
      <uniprot_id>Q0IIG5</uniprot_id>
      <gene_name>PFKM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00827</protein_accession>
      <name>Glucosamine--fructose-6-phosphate aminotransferase [isomerizing] 2</name>
      <uniprot_id>Q08DQ2</uniprot_id>
      <gene_name>GFPT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01129</protein_accession>
      <name>Probable fructose-2,6-bisphosphatase TIGAR</name>
      <uniprot_id>Q1JQA7</uniprot_id>
      <gene_name>TIGAR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:52 UTC</creation_date>
  <update_date>2020-04-16 20:38:56 UTC</update_date>
  <accession>BMDB0000125</accession>
  <secondary_accessions>
    <accession>BMDB00125</accession>
  </secondary_accessions>
  <name>Glutathione</name>
  <description/>
  <synonyms>
    <synonym>5-L-Glutamyl-L-cysteinylglycine</synonym>
    <synonym>gamma-L-Glutamyl-L-cysteinyl-glycine</synonym>
    <synonym>Glutathione-SH</synonym>
    <synonym>GSH</synonym>
    <synonym>N-(N-gamma-L-Glutamyl-L-cysteinyl)glycine</synonym>
    <synonym>Reduced glutathione</synonym>
    <synonym>Poly(gamma-glutamylcysteine)glycine</synonym>
    <synonym>(gamma-Glutamylcysteine)N-glycine</synonym>
    <synonym>Tathion</synonym>
    <synonym>g-L-Glutamyl-L-cysteinyl-glycine</synonym>
    <synonym>Γ-L-glutamyl-L-cysteinyl-glycine</synonym>
    <synonym>N-(N-g-L-Glutamyl-L-cysteinyl)glycine</synonym>
    <synonym>N-(N-Γ-L-glutamyl-L-cysteinyl)glycine</synonym>
    <synonym>Poly(g-glutamylcysteine)glycine</synonym>
    <synonym>Poly(γ-glutamylcysteine)glycine</synonym>
    <synonym>(g-Glutamylcysteine)N-glycine</synonym>
    <synonym>(Γ-glutamylcysteine)N-glycine</synonym>
    <synonym>Agifutol S</synonym>
    <synonym>Bakezyme RX</synonym>
    <synonym>Copren</synonym>
    <synonym>Deltathione</synonym>
    <synonym>gamma-Glutamylcysteinylglycine</synonym>
    <synonym>gamma-L-Glutamyl-L-cysteinylglycine</synonym>
    <synonym>Glutathion</synonym>
    <synonym>Glutathione red</synonym>
    <synonym>Glutathione reduced</synonym>
    <synonym>Glutatiol</synonym>
    <synonym>Glutatione</synonym>
    <synonym>Glutide</synonym>
    <synonym>Glutinal</synonym>
    <synonym>Isethion</synonym>
    <synonym>L-g-Glutamyl-L-cysteinyl-glycine</synonym>
    <synonym>L-gamma-Glutamyl-L-cysteinyl-glycine</synonym>
    <synonym>L-gamma-Glutamyl-L-cysteinylglycine</synonym>
    <synonym>L-Glutamyl-L-cysteinylglycine</synonym>
    <synonym>L-Glutathione</synonym>
    <synonym>L-Glutathione reduce</synonym>
    <synonym>Ledac</synonym>
    <synonym>Neuthion</synonym>
    <synonym>Red. glutathione</synonym>
    <synonym>Tathione</synonym>
    <synonym>Triptide</synonym>
    <synonym>Glutathione, reduced</synonym>
    <synonym>gamma L Glu L cys gly</synonym>
    <synonym>gamma-L-Glu-L-cys-gly</synonym>
    <synonym>gamma L Glutamyl L cysteinylglycine</synonym>
  </synonyms>
  <chemical_formula>C10H17N3O6S</chemical_formula>
  <average_molecular_weight>307.323</average_molecular_weight>
  <monisotopic_moleculate_weight>307.083805981</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid</iupac_name>
  <traditional_iupac>glutathione</traditional_iupac>
  <cas_registry_number>70-18-8</cas_registry_number>
  <smiles>N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1</inchi>
  <inchikey>RWSXRVCMGQZWBV-WDSKDSINSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Peptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Alpha peptide</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Coenzymes</external_descriptor>
      <external_descriptor>L-cysteine derivative</external_descriptor>
      <external_descriptor>thiol</external_descriptor>
      <external_descriptor>tripeptide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>195 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>292.5 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>307.323</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>307.083805981</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H17N3O6S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RWSXRVCMGQZWBV-WDSKDSINSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>158.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>69.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutathione Metabolism</name>
      <smpdb_id>SMP0087167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvaldehyde Degradation</name>
      <smpdb_id>SMP0087210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30368</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179877</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>892+/-472</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>226+/-51</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>769-775</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>162+/-46</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>1453+/-257</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00051</kegg_id>
  <drugbank_id>DB00143</drugbank_id>
  <foodb_id>FDB001498</foodb_id>
  <chemspider_id>111188</chemspider_id>
  <pubchem_compound_id>124886</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16856</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001518</knapsack_id>
  <meta_cyc_id>GLUTATHIONE</meta_cyc_id>
  <wikipedia_id>Glutathione</wikipedia_id>
  <bigg_id>33669</bigg_id>
  <metlin_id>44</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00117</protein_accession>
      <name>S-formylglutathione hydrolase</name>
      <uniprot_id>Q08E20</uniprot_id>
      <gene_name>ESD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00197</protein_accession>
      <name>Glutathione synthetase</name>
      <uniprot_id>Q5EAC2</uniprot_id>
      <gene_name>GSS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00541</protein_accession>
      <name>Phospholipid hydroperoxide glutathione peroxidase, mitochondrial</name>
      <uniprot_id>Q9N2J2</uniprot_id>
      <gene_name>GPX4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00542</protein_accession>
      <name>Glutathione peroxidase 3</name>
      <uniprot_id>P37141</uniprot_id>
      <gene_name>GPX3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00544</protein_accession>
      <name>Glutathione peroxidase 1</name>
      <uniprot_id>P00435</uniprot_id>
      <gene_name>GPX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00602</protein_accession>
      <name>Carbonyl reductase [NADPH] 1</name>
      <uniprot_id>Q3SZD7</uniprot_id>
      <gene_name>CBR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01078</protein_accession>
      <name>Leukotriene C4 synthase</name>
      <uniprot_id>Q2NKS0</uniprot_id>
      <gene_name>LTC4S</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01241</protein_accession>
      <name>Glutathione S-transferase theta-1</name>
      <uniprot_id>Q2NL00</uniprot_id>
      <gene_name>GSTT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01257</protein_accession>
      <name>Microsomal glutathione S-transferase 3</name>
      <uniprot_id>Q3T100</uniprot_id>
      <gene_name>MGST3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01258</protein_accession>
      <name>Glutathione S-transferase</name>
      <uniprot_id>Q32L24</uniprot_id>
      <gene_name>GSTA4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01259</protein_accession>
      <name>Microsomal glutathione S-transferase 1</name>
      <uniprot_id>Q64L89</uniprot_id>
      <gene_name>MGST1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01260</protein_accession>
      <name>Glutathione S-transferase Mu 1</name>
      <uniprot_id>Q9N0V4</uniprot_id>
      <gene_name>GSTM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01261</protein_accession>
      <name>Hydroxyacylglutathione hydrolase, mitochondrial</name>
      <uniprot_id>Q3B7M2</uniprot_id>
      <gene_name>HAGH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01262</protein_accession>
      <name>4-HYDROXYNONENAL metabolizing glutathione S-transferase</name>
      <uniprot_id>Q9TQX5</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01263</protein_accession>
      <name>Glutathione S-transferase A4</name>
      <uniprot_id>Q5E9G0</uniprot_id>
      <gene_name>GSTA4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01264</protein_accession>
      <name>Glutathione S-transferase mu 3 (Brain)</name>
      <uniprot_id>Q2KIV8</uniprot_id>
      <gene_name>GSTM3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01265</protein_accession>
      <name>Glutathione S-transferase</name>
      <uniprot_id>Q1JQ90</uniprot_id>
      <gene_name>GSTA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01266</protein_accession>
      <name>Glutathione peroxidase 7</name>
      <uniprot_id>A6QLY2</uniprot_id>
      <gene_name>GPX7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01267</protein_accession>
      <name>Glutathione S-transferase</name>
      <uniprot_id>Q9TRQ0</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01268</protein_accession>
      <name>Glutathione S-transferase</name>
      <uniprot_id>A5PJE0</uniprot_id>
      <gene_name>GSTA5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01269</protein_accession>
      <name>Glutathione S-transferase P</name>
      <uniprot_id>P28801</uniprot_id>
      <gene_name>GSTP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01270</protein_accession>
      <name>Microsomal glutathione S-transferase 2</name>
      <uniprot_id>Q2KJG4</uniprot_id>
      <gene_name>MGST2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01271</protein_accession>
      <name>Glutathione S-transferase omega 1</name>
      <uniprot_id>Q0VCE1</uniprot_id>
      <gene_name>GSTO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01272</protein_accession>
      <name>Probable glutathione peroxidase 8</name>
      <uniprot_id>Q2NL01</uniprot_id>
      <gene_name>GPX8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01273</protein_accession>
      <name>Thioredoxin domain-containing protein 12</name>
      <uniprot_id>Q5E936</uniprot_id>
      <gene_name>TXNDC12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01274</protein_accession>
      <name>Glutathione S-transferase mu 4</name>
      <uniprot_id>A1A4L7</uniprot_id>
      <gene_name>GSTM4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01275</protein_accession>
      <name>Glutathione S-transferase A2</name>
      <uniprot_id>O18879</uniprot_id>
      <gene_name>GSTA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01276</protein_accession>
      <name>Glutathione S-transferase A1</name>
      <uniprot_id>Q28035</uniprot_id>
      <gene_name>GSTA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02087</protein_accession>
      <name>Multidrug resistance-associated protein 1</name>
      <uniprot_id>Q8HXQ5</uniprot_id>
      <gene_name>ABCC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02681</protein_accession>
      <name>GSTM2 protein</name>
      <uniprot_id>A5PKM0</uniprot_id>
      <gene_name>GSTM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02682</protein_accession>
      <name>GSTM1 protein</name>
      <uniprot_id>A4IFG0</uniprot_id>
      <gene_name>GSTM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:54 UTC</creation_date>
  <update_date>2020-04-14 22:46:29 UTC</update_date>
  <accession>BMDB0000126</accession>
  <secondary_accessions>
    <accession>BMDB00126</accession>
  </secondary_accessions>
  <name>Glycerol 3-phosphate</name>
  <description>Glycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in the brain and skeletal muscle cells of mammals (wikipedia).</description>
  <synonyms>
    <synonym>(R)-Glycerol 1-phosphate</synonym>
    <synonym>D-(Glycerol 1-phosphate)</synonym>
    <synonym>D-Glycerol 1-phosphate</synonym>
    <synonym>Glycerol-3-phosphate</synonym>
    <synonym>Glycerophosphoric acid</synonym>
    <synonym>L-(Glycerol 3-phosphate)</synonym>
    <synonym>Phosphoric acid mono-((R)-2,3-dihydroxy-propyl) ester</synonym>
    <synonym>Phosphorsaeure-mono-((R)-2,3-dihydroxy-propylester)</synonym>
    <synonym>sn-GLYCEROL-3-phosphATE</synonym>
    <synonym>sn-Gro-1-p</synonym>
    <synonym>(R)-Glycerol 1-phosphoric acid</synonym>
    <synonym>D-(Glycerol 1-phosphoric acid)</synonym>
    <synonym>D-Glycerol 1-phosphoric acid</synonym>
    <synonym>Glycerol-3-phosphoric acid</synonym>
    <synonym>Glycerophosphate</synonym>
    <synonym>L-(Glycerol 3-phosphoric acid)</synonym>
    <synonym>Phosphate mono-((R)-2,3-dihydroxy-propyl) ester</synonym>
    <synonym>sn-GLYCEROL-3-phosphoric acid</synonym>
    <synonym>Glycerol 3-phosphoric acid</synonym>
    <synonym>1-(Dihydrogen phosphate) glycerol</synonym>
    <synonym>1-Glycerophosphate</synonym>
    <synonym>1-Glycerophosphorate</synonym>
    <synonym>1-Glycerophosphoric acid</synonym>
    <synonym>3-Glycerophosphate</synonym>
    <synonym>a-Glycerophosphate</synonym>
    <synonym>a-Glycerophosphorate</synonym>
    <synonym>a-Glycerophosphoric acid</synonym>
    <synonym>a-Phosphoglycerol</synonym>
    <synonym>alpha-Glycerophosphate</synonym>
    <synonym>alpha-Glycerophosphorate</synonym>
    <synonym>alpha-Glycerophosphoric acid</synonym>
    <synonym>alpha-Phosphoglycerol</synonym>
    <synonym>Dihydrogen a-glycerophosphate</synonym>
    <synonym>DL-a-Glycerol phosphate</synonym>
    <synonym>DL-a-Glycerophosphate</synonym>
    <synonym>DL-a-Glycerophosphorate</synonym>
    <synonym>DL-a-Glycerophosphoric acid</synonym>
    <synonym>DL-a-Glyceryl phosphate</synonym>
    <synonym>DL-alpha-Glycerol phosphate</synonym>
    <synonym>DL-alpha-Glycerophosphate</synonym>
    <synonym>DL-alpha-Glycerophosphorate</synonym>
    <synonym>DL-alpha-Glycerophosphoric acid</synonym>
    <synonym>DL-alpha-Glyceryl phosphate</synonym>
    <synonym>DL-Glycerol 1-phosphate</synonym>
    <synonym>DL-Glycerol 3-phosphate</synonym>
    <synonym>Glycerol 1-phosphate</synonym>
    <synonym>Glycerol a-phosphate</synonym>
    <synonym>Glycerol monophosphate</synonym>
    <synonym>Glycerophosphorate</synonym>
    <synonym>Glycerophosphoric acid I</synonym>
    <synonym>Glyceryl phosphate</synonym>
    <synonym>sn-Glycerol 3-phosphate</synonym>
    <synonym>1-Phosphoglycerol</synonym>
    <synonym>alpha-Glycerophosphoric acid, (DL)-isomer</synonym>
    <synonym>alpha-Glycerophosphoric acid, (R)-isomer</synonym>
    <synonym>alpha-Glycerophosphoric acid, (S)-isomer</synonym>
    <synonym>alpha-Glycerophosphoric acid, 1,2,3-propanetriol-1-(18)O,3-(dihydrogen phosphate)-labeled</synonym>
    <synonym>alpha-Glycerophosphoric acid, 1,2,3-propanetriol-2-(18)O,3-(dihydrogen phosphate)-labeled</synonym>
    <synonym>alpha-Glycerophosphoric acid, fe salt</synonym>
    <synonym>alpha-Glycerophosphoric acid, fe(+3) salt (3:2)</synonym>
    <synonym>alpha-Glycerophosphoric acid, calcium salt</synonym>
    <synonym>alpha-Glycerophosphoric acid, disodium salt</synonym>
    <synonym>alpha-Glycerophosphoric acid, disodium salt (+-)-isomer</synonym>
    <synonym>alpha-Glycerophosphoric acid, disodium salt hexahydrate(+-)-isomer</synonym>
    <synonym>alpha-Glycerophosphoric acid, monocalcium salt</synonym>
    <synonym>alpha-Glycerophosphoric acid, monocalcium salt (S)-isomer</synonym>
    <synonym>alpha-Glycerophosphoric acid, monomagnesium salt</synonym>
    <synonym>alpha-Glycerophosphoric acid, sodium salt</synonym>
    <synonym>Disodium glycerophosphate</synonym>
    <synonym>Sodium glycerophosphate</synonym>
  </synonyms>
  <chemical_formula>C3H9O6P</chemical_formula>
  <average_molecular_weight>172.0737</average_molecular_weight>
  <monisotopic_moleculate_weight>172.013674532</monisotopic_moleculate_weight>
  <iupac_name>[(2R)-2,3-dihydroxypropoxy]phosphonic acid</iupac_name>
  <traditional_iupac>3-phosphoglycerol</traditional_iupac>
  <cas_registry_number>57-03-4</cas_registry_number>
  <smiles>OC[C@@H](O)COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1</inchi>
  <inchikey>AWUCVROLDVIAJX-GSVOUGTGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycerophosphates. Glycerophosphates are compounds containing a glycerol linked to a phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerophospholipids</class>
    <sub_class>Glycerophosphates</sub_class>
    <direct_parent>Glycerophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sn-glycerol-3-phosphate</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>glycerol 1-phosphate</external_descriptor>
      <external_descriptor>sn-glycerol 3-phosphates</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>102 - 104 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(2R)-2,3-dihydroxypropoxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>172.0737</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>172.013674532</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H9O6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AWUCVROLDVIAJX-GSVOUGTGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>107.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Cardiolipin Biosynthesis</name>
      <smpdb_id>SMP0072032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:0)</name>
      <smpdb_id>SMP0077151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:0)</name>
      <smpdb_id>SMP0077153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:0)</name>
      <smpdb_id>SMP0077171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:0)</name>
      <smpdb_id>SMP0077173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077217</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077218</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077219</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077220</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077221</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077222</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077223</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077224</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077225</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077226</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077227</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077228</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077229</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077230</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077231</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077232</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077233</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077234</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077235</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077237</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077238</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077239</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077240</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077241</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077242</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077243</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077244</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077245</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077246</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077247</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077248</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077249</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077250</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077251</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077252</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077253</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077254</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077255</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077256</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077257</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077258</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077259</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077260</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077261</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077262</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077263</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077264</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077265</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077266</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077267</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077268</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077269</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077270</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077271</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077272</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077273</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077274</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077275</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077276</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077277</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077278</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077279</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077280</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077281</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077282</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077283</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077284</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077285</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077286</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077287</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077288</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077289</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077290</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077291</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077292</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077293</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077294</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077295</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077296</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077297</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077298</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:0)</name>
      <smpdb_id>SMP0077299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:0)</name>
      <smpdb_id>SMP0077310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:0)</name>
      <smpdb_id>SMP0077312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077318</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077330</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077332</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077334</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077336</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077339</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077340</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077341</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077343</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077350</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077351</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077365</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077366</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077367</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077368</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077369</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077375</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077377</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077378</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077379</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077381</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077386</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077388</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077389</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077390</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077391</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077392</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077393</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077394</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077395</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077396</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077397</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077398</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077399</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077400</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077401</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077404</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077405</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077406</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077407</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077411</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077412</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077413</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077421</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077422</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077423</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077424</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077425</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077430</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077431</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077432</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077433</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077434</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077435</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077437</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077438</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077439</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077440</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077441</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077442</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077443</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077444</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077445</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077446</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077447</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077448</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077449</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077450</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077451</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077452</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077453</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077454</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077455</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077456</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077457</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077458</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077459</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077460</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077461</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077462</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077463</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077464</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077465</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077481</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077482</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077483</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077484</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077485</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077486</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077487</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077488</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077489</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077490</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077491</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077492</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077493</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077494</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077495</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077496</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077497</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077498</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077499</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077500</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077501</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077502</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077503</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077505</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077507</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077509</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077510</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077511</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077514</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077515</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077516</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077519</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077520</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077522</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077523</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077524</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077525</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077526</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077527</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077528</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077529</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077530</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077531</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077532</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077533</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077534</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077536</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077537</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077538</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077541</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077542</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077549</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077550</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077551</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077552</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077553</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077554</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077555</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077556</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077557</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077558</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077559</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077560</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077561</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077562</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077563</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077564</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077565</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077566</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077567</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077569</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077599</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077600</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077601</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077602</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077603</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077604</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077605</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077607</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077608</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077609</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077612</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077613</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077621</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077622</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077695</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077696</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077697</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077699</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077700</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077701</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077702</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077703</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077704</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077705</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077706</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077707</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077708</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077709</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077710</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077711</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077712</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077713</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077714</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077715</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077716</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077717</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077718</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077719</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077720</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077722</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077723</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077724</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077725</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077726</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077727</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077728</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077729</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077730</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077731</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077732</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077733</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077734</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077735</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077736</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077737</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077740</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077741</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077742</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077743</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077744</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077745</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077746</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077747</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077748</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077749</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077750</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077751</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077752</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077753</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077754</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077755</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077756</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077760</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077761</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077762</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077763</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077765</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077766</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077767</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077768</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077769</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077771</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077772</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077773</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077774</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077775</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077776</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077777</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077778</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077780</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077781</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077783</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077784</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077785</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077786</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077787</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077790</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077791</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077792</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077793</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077794</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077795</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077796</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077797</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077798</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077801</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077802</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077803</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077804</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077805</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077806</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077808</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077809</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077810</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077811</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077812</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077813</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077814</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077815</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077816</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077817</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077825</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077829</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077835</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077836</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077837</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077841</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077842</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077843</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077844</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077845</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077846</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077847</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077850</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077851</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077852</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077853</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077854</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077855</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077856</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077857</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077858</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077859</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077860</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077861</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077862</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077863</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077864</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077865</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077866</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077867</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077868</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077869</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077870</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077871</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077872</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077873</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077874</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077875</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077876</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077877</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077878</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077879</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077880</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077881</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077882</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077883</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077884</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077885</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077886</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077887</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077888</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077889</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077890</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077891</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077892</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077893</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077894</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077895</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077897</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077900</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077901</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077902</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077903</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077904</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077905</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077906</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077908</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077909</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077910</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077911</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077912</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077916</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077924</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077932</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077933</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077934</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077935</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077936</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077937</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077938</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077939</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077940</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077941</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077942</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077943</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077944</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077947</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077948</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077950</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077951</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077952</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078155</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078156</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078157</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078158</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078159</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078160</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078161</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078162</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078163</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078164</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078165</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078166</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078167</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078168</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078169</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078170</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078171</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078172</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078173</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078174</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078177</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078178</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078179</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078180</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078181</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078182</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078191</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078193</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078194</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078195</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078196</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078197</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078198</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078199</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078200</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078201</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078202</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078203</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078204</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078205</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078206</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078207</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078208</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078209</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078210</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078211</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078212</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078213</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078214</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078215</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078216</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078217</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078218</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:0)</name>
      <smpdb_id>SMP0078219</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078220</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078221</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078222</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078223</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078224</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078225</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078226</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078227</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078228</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078229</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078231</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078233</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078234</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078235</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078242</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078243</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078244</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078245</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078246</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078247</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078248</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078249</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078250</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078251</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078252</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078253</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078254</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078255</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078256</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078257</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078258</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078259</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078260</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078261</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078262</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078263</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078264</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078265</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078266</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078267</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078268</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078269</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078270</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078271</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078272</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078273</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078274</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078275</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078276</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078277</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078278</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078279</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078280</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078281</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078282</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078283</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078284</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078285</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078286</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078287</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078288</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078289</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078290</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078291</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078292</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078293</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078294</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078295</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078296</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078297</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078298</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078299</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078300</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078301</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078302</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078303</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078304</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078305</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078306</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078307</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078308</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078309</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078310</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078311</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078312</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078313</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078314</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078315</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078316</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078317</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078319</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078323</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078324</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078325</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078326</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078327</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078328</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078329</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078330</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078331</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078332</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078333</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078334</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078335</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078336</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078337</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078338</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078339</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078340</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078341</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078342</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078343</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078344</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078345</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078346</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078347</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078348</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078349</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078350</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078351</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078352</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078353</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078354</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078355</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078356</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078357</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078358</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078359</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078360</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078361</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078362</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078363</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078364</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078365</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078366</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078367</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078368</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078369</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078370</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078371</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078372</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078373</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078374</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078375</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078376</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078377</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078378</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078379</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078380</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078381</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078382</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078383</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078384</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078385</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078386</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078387</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078388</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078389</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078392</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078393</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078394</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078395</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078397</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078398</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078399</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078400</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078401</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078402</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078403</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078404</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078405</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078406</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078407</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078408</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078409</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078410</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078411</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078412</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078413</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078414</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078415</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078416</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078417</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078418</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078419</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078420</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078421</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078422</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078423</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078424</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078425</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078426</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078427</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078428</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078429</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078430</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078431</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078432</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078433</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078434</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078435</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078436</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078437</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078438</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078439</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078440</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078441</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078442</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078443</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078444</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078445</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078446</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078447</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078448</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078449</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078450</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078451</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078452</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078453</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078454</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078455</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078456</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078457</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078458</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078459</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078460</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078461</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078462</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078463</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078464</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078465</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078466</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078467</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078468</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078469</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078470</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078471</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078473</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078474</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078475</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078478</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078480</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078481</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078482</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078483</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078484</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078485</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078486</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078487</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078488</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078489</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078490</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078491</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078492</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078493</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078494</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078495</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078496</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078497</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078498</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078499</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078500</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078501</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078502</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078503</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078504</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078505</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078506</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078507</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078508</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078509</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078530</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078531</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078535</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078536</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078537</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078538</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078541</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078628</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078713</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078714</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078715</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078716</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078717</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078718</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078719</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078720</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078721</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078722</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078723</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078724</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078725</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078726</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078727</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078728</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078729</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078730</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078731</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078732</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078733</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078734</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078735</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078736</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078737</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078738</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078739</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078740</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078741</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078742</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078743</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078744</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078745</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078746</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078747</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078748</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078749</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078750</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078751</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078752</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078753</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078754</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078755</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078756</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078757</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078758</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078759</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078760</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078761</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078762</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078763</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078764</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078765</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078766</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078768</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078769</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078772</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078774</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078777</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078778</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078779</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078787</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078788</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078789</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078790</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078792</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078793</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078794</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078795</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078796</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078797</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078798</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078799</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078800</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078801</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078802</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078803</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078804</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078805</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078806</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078807</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078808</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078809</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078810</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078811</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078812</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078813</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078814</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078815</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078816</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078817</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078818</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078819</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078820</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078821</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078822</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078823</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078824</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078825</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078826</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078830</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078832</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078834</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078840</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078842</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078844</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078852</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078853</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078854</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078855</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078859</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078860</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078861</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078862</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078863</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078864</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078865</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078866</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078869</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078870</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078872</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078873</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078874</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078875</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078876</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078877</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078878</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078879</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078880</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078881</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078882</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078883</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078884</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078885</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078887</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078888</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078889</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078890</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078891</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078892</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078917</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079082</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079085</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079090</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0079091</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079092</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079093</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079094</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079095</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079096</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079097</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079098</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079099</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079100</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079101</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079102</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079103</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079104</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079106</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079113</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079121</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079122</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079123</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079124</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079126</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079130</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079131</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079132</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079134</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079142</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079143</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079144</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079147</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079148</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079149</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079151</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0079152</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079153</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079154</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079155</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079156</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079157</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079158</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079159</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079160</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079173</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079176</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079180</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079216</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079217</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079218</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079219</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079220</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079221</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079225</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079226</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079231</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079315</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079316</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079453</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079454</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079455</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079456</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079457</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079458</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079459</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079460</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079461</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079462</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079463</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079464</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079465</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079466</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079467</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079468</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079469</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079470</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079471</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079472</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079473</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079474</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079475</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079476</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079477</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079478</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079479</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079480</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079481</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079482</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079483</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079484</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079485</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079486</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079487</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079488</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079489</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079490</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079491</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079492</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079493</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079494</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079495</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079496</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079497</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079498</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079499</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079500</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079501</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079502</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079503</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079504</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079505</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079506</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079507</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079508</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079509</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079510</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079511</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079512</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079513</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079514</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079515</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079516</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079517</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079518</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079519</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079520</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079521</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079522</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079523</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079524</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079525</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079526</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079527</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079528</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079529</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079530</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079531</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079532</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079533</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079534</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079535</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079536</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079537</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079538</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079539</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079540</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079541</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079542</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079543</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079544</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079545</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079546</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079547</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079548</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079549</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079550</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079551</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079552</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079553</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079554</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079555</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079556</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079557</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079558</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079559</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079560</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079562</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079563</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079564</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079565</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079566</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079567</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079568</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079569</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079570</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079571</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079572</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079573</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079574</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079575</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079576</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079577</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079578</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079579</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079580</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079581</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079582</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079583</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079584</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079585</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079586</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079588</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079590</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079591</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079592</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079593</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079594</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079595</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079596</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079597</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079598</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079599</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079600</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079601</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079602</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0079603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0079604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079673</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079679</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079739</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079743</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079744</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079748</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079749</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079750</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079751</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079754</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079755</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079756</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079757</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079758</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079760</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079761</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079762</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079763</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079764</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079765</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079766</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079767</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079771</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079772</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079773</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079779</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079784</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079797</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079798</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079800</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079803</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079804</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079807</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080003</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080004</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080005</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080006</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080007</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080008</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080009</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080010</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080011</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080012</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080013</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080014</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0080015</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080016</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080017</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0080018</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0080019</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080020</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0080021</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080022</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080023</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080024</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080025</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080026</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080029</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080030</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080031</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080032</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080033</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080034</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080039</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080043</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080044</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080045</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080046</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080051</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080052</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080053</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080054</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080055</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080056</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080060</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080061</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080065</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0080066</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080067</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080068</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080069</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080199</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080200</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080201</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080202</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080203</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080204</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080205</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080206</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080210</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080236</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080237</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080238</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080239</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080240</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080241</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080242</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080246</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080247</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080248</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080249</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080250</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080251</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080252</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080253</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080258</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080259</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080260</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080261</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080262</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis</name>
      <smpdb_id>SMP0071338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/10:0)</name>
      <smpdb_id>SMP0108241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/12:0)</name>
      <smpdb_id>SMP0108483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/13:0)</name>
      <smpdb_id>SMP0108481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/14:0)</name>
      <smpdb_id>SMP0108477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/15:0)</name>
      <smpdb_id>SMP0108517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/16:0)</name>
      <smpdb_id>SMP0108480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/17:0)</name>
      <smpdb_id>SMP0108472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/18:0)</name>
      <smpdb_id>SMP0108485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/19:0)</name>
      <smpdb_id>SMP0108526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/8:0)</name>
      <smpdb_id>SMP0108478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-13:0)</name>
      <smpdb_id>SMP0108541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-15:0)</name>
      <smpdb_id>SMP0108542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-17:0)</name>
      <smpdb_id>SMP0108543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-21:0)</name>
      <smpdb_id>SMP0108544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-25:0)</name>
      <smpdb_id>SMP0108545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-12:0)</name>
      <smpdb_id>SMP0108546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-13:0)</name>
      <smpdb_id>SMP0108547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-14:0)</name>
      <smpdb_id>SMP0108548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-15:0)</name>
      <smpdb_id>SMP0108549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-16:0)</name>
      <smpdb_id>SMP0108550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-17:0)</name>
      <smpdb_id>SMP0108551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-18:0)</name>
      <smpdb_id>SMP0108552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-19:0)</name>
      <smpdb_id>SMP0108553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-20:0)</name>
      <smpdb_id>SMP0108554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-21:0)</name>
      <smpdb_id>SMP0108555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-22:0)</name>
      <smpdb_id>SMP0108556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-24:0)</name>
      <smpdb_id>SMP0108557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/12:0)</name>
      <smpdb_id>SMP0108470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/13:0)</name>
      <smpdb_id>SMP0108512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/14:0)</name>
      <smpdb_id>SMP0108445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/15:0)</name>
      <smpdb_id>SMP0108471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0108558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0108559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0108560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0108561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0108562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0108563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0108564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0108565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0108566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0108567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0108568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0108569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0108570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0108571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0108572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0108573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0108574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/13:0)</name>
      <smpdb_id>SMP0108460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/15:0)</name>
      <smpdb_id>SMP0108469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/16:0)</name>
      <smpdb_id>SMP0108463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/8:0)</name>
      <smpdb_id>SMP0108451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0108575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0108576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0108577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0108578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0108579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0108580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0108581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0108582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0108583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0108584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0108585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0108586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0108587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0108588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0108589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0108590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0108591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/13:0)</name>
      <smpdb_id>SMP0108534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/14:0)</name>
      <smpdb_id>SMP0108525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/15:0)</name>
      <smpdb_id>SMP0108522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/17:0)</name>
      <smpdb_id>SMP0108488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/18:0)</name>
      <smpdb_id>SMP0108489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/19:0)</name>
      <smpdb_id>SMP0108447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0108592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0108593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0108594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0108595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0108596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0108597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0108598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0108599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0108600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0108601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0108602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0108603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0108604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0108605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0108606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0108607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0108608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/15:0)</name>
      <smpdb_id>SMP0108476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/17:0)</name>
      <smpdb_id>SMP0108461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/18:0)</name>
      <smpdb_id>SMP0108523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/8:0)</name>
      <smpdb_id>SMP0108494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0108609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0108610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0108611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0108612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0108613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0108614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0108615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0108616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0108617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0108618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0108619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0108620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0108621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0108622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0108623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0108624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0108625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/12:0)</name>
      <smpdb_id>SMP0108479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/14:0)</name>
      <smpdb_id>SMP0108468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/15:0)</name>
      <smpdb_id>SMP0108507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/16:0)</name>
      <smpdb_id>SMP0108467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/17:0)</name>
      <smpdb_id>SMP0108458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/18:0)</name>
      <smpdb_id>SMP0108518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/8:0)</name>
      <smpdb_id>SMP0108504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0108626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0108627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0108628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0108629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0108630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0108631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0108632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0108633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0108634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0108635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0108636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0108637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0108638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0108639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0108640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0108641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0108642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/12:0)</name>
      <smpdb_id>SMP0108465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/13:0)</name>
      <smpdb_id>SMP0108456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/17:0)</name>
      <smpdb_id>SMP0108506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0108643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0108644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0108645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0108646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0108647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0108648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0108649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0108650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0108651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0108652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0108653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0108654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0108655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0108656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0108657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0108658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0108659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/12:0)</name>
      <smpdb_id>SMP0108495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/13:0)</name>
      <smpdb_id>SMP0108492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/17:0)</name>
      <smpdb_id>SMP0108452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/18:0)</name>
      <smpdb_id>SMP0108448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/19:0)</name>
      <smpdb_id>SMP0108503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/8:0)</name>
      <smpdb_id>SMP0108466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0108660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0108661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0108662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0108663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0108664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0108665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0108666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0108667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0108668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0108669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0108670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0108671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0108672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0108673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0108674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0108675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0108676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/12:0)</name>
      <smpdb_id>SMP0108511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/13:0)</name>
      <smpdb_id>SMP0108473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/15:0)</name>
      <smpdb_id>SMP0108533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/16:0)</name>
      <smpdb_id>SMP0108496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/17:0)</name>
      <smpdb_id>SMP0108521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/19:0)</name>
      <smpdb_id>SMP0108514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0108677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0108678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0108679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-21:0)</name>
      <smpdb_id>SMP0108680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-25:0)</name>
      <smpdb_id>SMP0108681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0108682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0108683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0108684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0108685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0108686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0108687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0108688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0108689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-20:0)</name>
      <smpdb_id>SMP0108690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-21:0)</name>
      <smpdb_id>SMP0108691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-22:0)</name>
      <smpdb_id>SMP0108692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-24:0)</name>
      <smpdb_id>SMP0108693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-13:0)</name>
      <smpdb_id>SMP0108694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-15:0)</name>
      <smpdb_id>SMP0108695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-17:0)</name>
      <smpdb_id>SMP0108696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0108697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0108698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-12:0)</name>
      <smpdb_id>SMP0108699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-13:0)</name>
      <smpdb_id>SMP0108700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-14:0)</name>
      <smpdb_id>SMP0108701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-15:0)</name>
      <smpdb_id>SMP0108702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-16:0)</name>
      <smpdb_id>SMP0108703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-17:0)</name>
      <smpdb_id>SMP0108704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-18:0)</name>
      <smpdb_id>SMP0108705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0108706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0108707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0108708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0108709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0108710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0108711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0108712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0108713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0108714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0108715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0108716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0108717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0108718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0108719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0108720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0108721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0108722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0108723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0108724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0108725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0108726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0108727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0108728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0108729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0108730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0108731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0108732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0108733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0108734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0108735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0108736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0108737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0108738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0108739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0108740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0108741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0108742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0108743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0108744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/17:0)</name>
      <smpdb_id>SMP0108457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/8:0)</name>
      <smpdb_id>SMP0108519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0108745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0108746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0108747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0108748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0108749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0108750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0108751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0108752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0108753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0108754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0108755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0108756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0108757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0108759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0111848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0108761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0108763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0108765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0108767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0108768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0108770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0108772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0108774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0108775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0108777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0108778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0108779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0108780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0108781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0108782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0108783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0108784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0108785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0108786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0108787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0108788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0108789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0108790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0108791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0108792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0108793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0108794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0108795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0108796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0108797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0108798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0108799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0108800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0108801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0108802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0108803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0108804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0108805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0108806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0108807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0108808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0108809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0108810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0108811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0108812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0108813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0108814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0108815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0108816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0108817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0108818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0108819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0108820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0108821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0108822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0108823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0108824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0108825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0108826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0108827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0108828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0108829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0108830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0108831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0108832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0108833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0108834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0108835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0108836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0108837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0108838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0108839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0108840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0108841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0108842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0108843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0108844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0108845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0108846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0108847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0108848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0108849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0108850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0108851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0108852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0108853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0108854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0108855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0108856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0108857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0108858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0108859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0108860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0108861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0108862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0108863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0108864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0108865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0108866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0108867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0108868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0108869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0108870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0108871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0108872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0108873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0108874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0108875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0108876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0108877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0108878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0108879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0108880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0108881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0108882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0108883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0108884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0108885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0108886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0108887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0108888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0108889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0108890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0108891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0108892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0108893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0108894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0108895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0108896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0108897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0108898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0108899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0108900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0108901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0108902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0108903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0108904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0108905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0108906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0108907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0108908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0108909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0108910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0108911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0108912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/a-25:0)</name>
      <smpdb_id>SMP0108913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0108914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0108915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0108916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/a-25:0)</name>
      <smpdb_id>SMP0108917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0108918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0108919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-24:0/a-25:0)</name>
      <smpdb_id>SMP0108920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0108921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(12:0/12:0/12:0)</name>
      <smpdb_id>SMP0108243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/14:0)</name>
      <smpdb_id>SMP0072652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/14:1(9Z))</name>
      <smpdb_id>SMP0072653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/15:0)</name>
      <smpdb_id>SMP0072654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/16:0)</name>
      <smpdb_id>SMP0072655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/16:1(9Z))</name>
      <smpdb_id>SMP0072656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:0)</name>
      <smpdb_id>SMP0072657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:1(11Z))</name>
      <smpdb_id>SMP0072658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:1(9Z))</name>
      <smpdb_id>SMP0072659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:0)</name>
      <smpdb_id>SMP0072664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:1(11Z))</name>
      <smpdb_id>SMP0072665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:0)</name>
      <smpdb_id>SMP0072672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:1(13Z))</name>
      <smpdb_id>SMP0072673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/24:0)</name>
      <smpdb_id>SMP0072679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/24:1(15Z))</name>
      <smpdb_id>SMP0072680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0072681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0072682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0072683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0072684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0072685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/15:0)</name>
      <smpdb_id>SMP0072709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/16:0)</name>
      <smpdb_id>SMP0072710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/16:1(9Z))</name>
      <smpdb_id>SMP0072711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:0)</name>
      <smpdb_id>SMP0072712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:1(11Z))</name>
      <smpdb_id>SMP0072713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:1(9Z))</name>
      <smpdb_id>SMP0072714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:0)</name>
      <smpdb_id>SMP0072719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:1(11Z))</name>
      <smpdb_id>SMP0072720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:0)</name>
      <smpdb_id>SMP0072727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:1(13Z))</name>
      <smpdb_id>SMP0072728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/24:0)</name>
      <smpdb_id>SMP0072734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/24:1(15Z))</name>
      <smpdb_id>SMP0072735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/16:0)</name>
      <smpdb_id>SMP0072736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0072737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:0)</name>
      <smpdb_id>SMP0072738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0072739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0072740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:0)</name>
      <smpdb_id>SMP0072745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0072746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:0)</name>
      <smpdb_id>SMP0072753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0072754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/24:0)</name>
      <smpdb_id>SMP0072760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0072761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0072762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0072763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:0)</name>
      <smpdb_id>SMP0072787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0072788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0072789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:0)</name>
      <smpdb_id>SMP0072794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0072795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:0)</name>
      <smpdb_id>SMP0072802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0072803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/24:0)</name>
      <smpdb_id>SMP0072809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0072810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0072817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0072825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0072832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0072860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0072868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0072875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0072880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0072888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0072895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0072899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0072907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0072914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0072917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0072925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0072932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:0)</name>
      <smpdb_id>SMP0072934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0072935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:0)</name>
      <smpdb_id>SMP0072942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0072943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/24:0)</name>
      <smpdb_id>SMP0072949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0072950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0072958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0072965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0072973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0072980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0072987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0072994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:0)</name>
      <smpdb_id>SMP0073042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0073043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/24:0)</name>
      <smpdb_id>SMP0073049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0073050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0073057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:0/24:0)</name>
      <smpdb_id>SMP0073084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0073085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0073087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0073088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0073089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/15:0)</name>
      <smpdb_id>SMP0073115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/16:0)</name>
      <smpdb_id>SMP0073116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/16:1(9Z))</name>
      <smpdb_id>SMP0073117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:0)</name>
      <smpdb_id>SMP0073118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:1(11Z))</name>
      <smpdb_id>SMP0073119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:1(9Z))</name>
      <smpdb_id>SMP0073120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:0)</name>
      <smpdb_id>SMP0073125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:1(11Z))</name>
      <smpdb_id>SMP0073126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:0)</name>
      <smpdb_id>SMP0073133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:1(13Z))</name>
      <smpdb_id>SMP0073134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/24:0)</name>
      <smpdb_id>SMP0073140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/24:1(15Z))</name>
      <smpdb_id>SMP0073141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/16:0)</name>
      <smpdb_id>SMP0073142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:0)</name>
      <smpdb_id>SMP0073144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:0)</name>
      <smpdb_id>SMP0073151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:0)</name>
      <smpdb_id>SMP0073159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/24:0)</name>
      <smpdb_id>SMP0073166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0073193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0073194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0073195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:0)</name>
      <smpdb_id>SMP0073200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0073201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:0)</name>
      <smpdb_id>SMP0073208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0073209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/24:0)</name>
      <smpdb_id>SMP0073215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0073216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0073223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:0)</name>
      <smpdb_id>SMP0073340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0073341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:0)</name>
      <smpdb_id>SMP0073348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0073349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/24:0)</name>
      <smpdb_id>SMP0073355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0073356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0073393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0073400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:0)</name>
      <smpdb_id>SMP0073448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0073449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/24:0)</name>
      <smpdb_id>SMP0073455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0073456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0073463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/24:0/24:0)</name>
      <smpdb_id>SMP0073490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0073491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/15:0)</name>
      <smpdb_id>SMP0073493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/16:0)</name>
      <smpdb_id>SMP0073494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/16:1(9Z))</name>
      <smpdb_id>SMP0073495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:0)</name>
      <smpdb_id>SMP0073496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:1(11Z))</name>
      <smpdb_id>SMP0073497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:1(9Z))</name>
      <smpdb_id>SMP0073498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:0)</name>
      <smpdb_id>SMP0073503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:1(11Z))</name>
      <smpdb_id>SMP0073504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:0)</name>
      <smpdb_id>SMP0073511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:1(13Z))</name>
      <smpdb_id>SMP0073512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/24:0)</name>
      <smpdb_id>SMP0073518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/24:1(15Z))</name>
      <smpdb_id>SMP0073519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/16:0)</name>
      <smpdb_id>SMP0073520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:0)</name>
      <smpdb_id>SMP0073522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:0)</name>
      <smpdb_id>SMP0073529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:0)</name>
      <smpdb_id>SMP0073537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/24:0)</name>
      <smpdb_id>SMP0073544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:0)</name>
      <smpdb_id>SMP0073571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0073572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0073573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:0)</name>
      <smpdb_id>SMP0073578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0073579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:0)</name>
      <smpdb_id>SMP0073586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0073587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/24:0)</name>
      <smpdb_id>SMP0073593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0073594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0073601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:0)</name>
      <smpdb_id>SMP0073718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0073719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:0)</name>
      <smpdb_id>SMP0073726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0073727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/24:0)</name>
      <smpdb_id>SMP0073733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0073734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0073771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0073778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:0)</name>
      <smpdb_id>SMP0073826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0073827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/24:0)</name>
      <smpdb_id>SMP0073833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0073834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0073841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/24:0/24:0)</name>
      <smpdb_id>SMP0073868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0073869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:0)</name>
      <smpdb_id>SMP0073871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:0)</name>
      <smpdb_id>SMP0073873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:0)</name>
      <smpdb_id>SMP0073880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:0)</name>
      <smpdb_id>SMP0073888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/24:0)</name>
      <smpdb_id>SMP0073895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:0)</name>
      <smpdb_id>SMP0073922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0073923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0073924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:0)</name>
      <smpdb_id>SMP0073929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0073930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:0)</name>
      <smpdb_id>SMP0073937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0073938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/24:0)</name>
      <smpdb_id>SMP0073944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0073945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0073952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:0)</name>
      <smpdb_id>SMP0074069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:0)</name>
      <smpdb_id>SMP0074077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/24:0)</name>
      <smpdb_id>SMP0074084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0074122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0074129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:0)</name>
      <smpdb_id>SMP0074177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0074178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/24:0)</name>
      <smpdb_id>SMP0074184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0074185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0074192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:0/24:0)</name>
      <smpdb_id>SMP0074219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0074220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0074222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0074223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0074247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0074248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0074249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:0)</name>
      <smpdb_id>SMP0074254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0074255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:0)</name>
      <smpdb_id>SMP0074262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0074263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/24:0)</name>
      <smpdb_id>SMP0074269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0074270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0074277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:0)</name>
      <smpdb_id>SMP0074394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:0)</name>
      <smpdb_id>SMP0074402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/24:0)</name>
      <smpdb_id>SMP0074409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0074447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0074454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:0)</name>
      <smpdb_id>SMP0074502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0074503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/24:0)</name>
      <smpdb_id>SMP0074509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0074510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0074517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/24:0/24:0)</name>
      <smpdb_id>SMP0074544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0074545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:0)</name>
      <smpdb_id>SMP0074547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0074548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0074549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:0)</name>
      <smpdb_id>SMP0074554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0074555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:0)</name>
      <smpdb_id>SMP0074562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0074563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/24:0)</name>
      <smpdb_id>SMP0074569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0074570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0074577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:0)</name>
      <smpdb_id>SMP0074695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:0)</name>
      <smpdb_id>SMP0074703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/24:0)</name>
      <smpdb_id>SMP0074710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0074748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0074756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:0)</name>
      <smpdb_id>SMP0074804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0074805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/24:0)</name>
      <smpdb_id>SMP0074811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0074812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0074819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/24:0/24:0)</name>
      <smpdb_id>SMP0074846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0074847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0074855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:0)</name>
      <smpdb_id>SMP0074972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:0)</name>
      <smpdb_id>SMP0074980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/24:0)</name>
      <smpdb_id>SMP0074988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0075126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0075127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0075131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0075139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0075146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0075148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0075380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0076011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0076012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0076020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0076027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:0)</name>
      <smpdb_id>SMP0076029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0076030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:0)</name>
      <smpdb_id>SMP0076037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0076038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/24:0)</name>
      <smpdb_id>SMP0076044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0076045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0076053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0076060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/20:0)</name>
      <smpdb_id>SMP0108262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/21:0)</name>
      <smpdb_id>SMP0108257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/22:0)</name>
      <smpdb_id>SMP0108278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/a-21:0)</name>
      <smpdb_id>SMP0108922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/a-25:0)</name>
      <smpdb_id>SMP0108923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-21:0)</name>
      <smpdb_id>SMP0108924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-22:0)</name>
      <smpdb_id>SMP0108925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-24:0)</name>
      <smpdb_id>SMP0108926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/21:0)</name>
      <smpdb_id>SMP0108277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/22:0)</name>
      <smpdb_id>SMP0108311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0108927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0108928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0108929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0108930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0108931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0108932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0108933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/10:0)</name>
      <smpdb_id>SMP0108328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/12:0)</name>
      <smpdb_id>SMP0108244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/13:0)</name>
      <smpdb_id>SMP0108317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/14:0)</name>
      <smpdb_id>SMP0108266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/15:0)</name>
      <smpdb_id>SMP0108275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/16:0)</name>
      <smpdb_id>SMP0108332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/17:0)</name>
      <smpdb_id>SMP0108292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/18:0)</name>
      <smpdb_id>SMP0108327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/21:0)</name>
      <smpdb_id>SMP0108305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/22:0)</name>
      <smpdb_id>SMP0108316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/8:0)</name>
      <smpdb_id>SMP0108301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0108934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0108935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0108936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0108937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0108938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0108939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0108940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0108941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0108942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0108943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0108944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0108945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0108946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0108947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0108948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0108949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0108950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/10:0)</name>
      <smpdb_id>SMP0108279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/12:0)</name>
      <smpdb_id>SMP0108261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/13:0)</name>
      <smpdb_id>SMP0108286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/14:0)</name>
      <smpdb_id>SMP0108255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/15:0)</name>
      <smpdb_id>SMP0108252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/16:0)</name>
      <smpdb_id>SMP0108299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/17:0)</name>
      <smpdb_id>SMP0108308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/18:0)</name>
      <smpdb_id>SMP0108282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/22:0)</name>
      <smpdb_id>SMP0108265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/8:0)</name>
      <smpdb_id>SMP0108319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0108951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0108952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0108953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0108954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0108955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0108956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0108957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0108958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0108959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0108960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0108961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0108962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0108963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0108964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0108965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0108966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0108967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0108968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/13:0)</name>
      <smpdb_id>SMP0108969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/14:0)</name>
      <smpdb_id>SMP0108970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/15:0)</name>
      <smpdb_id>SMP0108971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/16:0)</name>
      <smpdb_id>SMP0108972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/17:0)</name>
      <smpdb_id>SMP0108973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/18:0)</name>
      <smpdb_id>SMP0108974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/8:0)</name>
      <smpdb_id>SMP0108975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-13:0)</name>
      <smpdb_id>SMP0108976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-15:0)</name>
      <smpdb_id>SMP0108977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-17:0)</name>
      <smpdb_id>SMP0108978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0108979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0108980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0108981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0108982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0108983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0108984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0108985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0108986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0108987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0108988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0108989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0108990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0108991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0108992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/12:0)</name>
      <smpdb_id>SMP0108993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/13:0)</name>
      <smpdb_id>SMP0108994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/14:0)</name>
      <smpdb_id>SMP0108995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/15:0)</name>
      <smpdb_id>SMP0108996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/16:0)</name>
      <smpdb_id>SMP0108997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/17:0)</name>
      <smpdb_id>SMP0108998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/18:0)</name>
      <smpdb_id>SMP0108999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/8:0)</name>
      <smpdb_id>SMP0109000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-13:0)</name>
      <smpdb_id>SMP0109001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-15:0)</name>
      <smpdb_id>SMP0109002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-17:0)</name>
      <smpdb_id>SMP0109003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0109021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0109022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0109023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0109024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0109025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0109026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0109027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/8:0)</name>
      <smpdb_id>SMP0109028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0109029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0109030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0109031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0109032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0109033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0109034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0109035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0109036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0109037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0109038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-19:0)</name>
      <smpdb_id>SMP0109039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0109043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0109044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0109045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0109046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0109047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0109048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0109049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/8:0)</name>
      <smpdb_id>SMP0109050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0109051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0109052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0109053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0109054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0109055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0109056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0109057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0109058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0109059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0109060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-19:0)</name>
      <smpdb_id>SMP0109061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0109064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0109065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0109066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0109067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0109068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0109069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0109070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/8:0)</name>
      <smpdb_id>SMP0109071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0109072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0109073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0109074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0109075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0109076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0109078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0109079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0109080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0109081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0109082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-19:0)</name>
      <smpdb_id>SMP0109083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/10:0)</name>
      <smpdb_id>SMP0108330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/14:0)</name>
      <smpdb_id>SMP0108290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/17:0)</name>
      <smpdb_id>SMP0108312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/19:0)</name>
      <smpdb_id>SMP0108270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/21:0)</name>
      <smpdb_id>SMP0108300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/22:0)</name>
      <smpdb_id>SMP0108259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/10:0)</name>
      <smpdb_id>SMP0108320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/12:0)</name>
      <smpdb_id>SMP0108331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/13:0)</name>
      <smpdb_id>SMP0108318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/16:0)</name>
      <smpdb_id>SMP0108293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/17:0)</name>
      <smpdb_id>SMP0108304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/18:0)</name>
      <smpdb_id>SMP0108297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/19:0)</name>
      <smpdb_id>SMP0108288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/21:0)</name>
      <smpdb_id>SMP0108322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/22:0)</name>
      <smpdb_id>SMP0108314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/8:0)</name>
      <smpdb_id>SMP0108263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/10:0)</name>
      <smpdb_id>SMP0108256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/13:0)</name>
      <smpdb_id>SMP0108326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/15:0)</name>
      <smpdb_id>SMP0108250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/16:0)</name>
      <smpdb_id>SMP0108247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/21:0)</name>
      <smpdb_id>SMP0108313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/22:0)</name>
      <smpdb_id>SMP0108283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/8:0)</name>
      <smpdb_id>SMP0108276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/12:0)</name>
      <smpdb_id>SMP0108248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/13:0)</name>
      <smpdb_id>SMP0108295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/19:0)</name>
      <smpdb_id>SMP0108249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/21:0)</name>
      <smpdb_id>SMP0108271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/10:0)</name>
      <smpdb_id>SMP0108267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/12:0)</name>
      <smpdb_id>SMP0108324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/17:0)</name>
      <smpdb_id>SMP0108284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/21:0)</name>
      <smpdb_id>SMP0108306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/10:0)</name>
      <smpdb_id>SMP0108274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/19:0)</name>
      <smpdb_id>SMP0108269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/21:0)</name>
      <smpdb_id>SMP0108251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/13:0)</name>
      <smpdb_id>SMP0108289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/14:0)</name>
      <smpdb_id>SMP0108253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/16:0)</name>
      <smpdb_id>SMP0108302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/17:0)</name>
      <smpdb_id>SMP0108254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/19:0)</name>
      <smpdb_id>SMP0108264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/21:0)</name>
      <smpdb_id>SMP0108281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/22:0)</name>
      <smpdb_id>SMP0108294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/8:0)</name>
      <smpdb_id>SMP0108296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/10:0)</name>
      <smpdb_id>SMP0108315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/13:0)</name>
      <smpdb_id>SMP0108307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/17:0)</name>
      <smpdb_id>SMP0108273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/21:0)</name>
      <smpdb_id>SMP0108323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/8:0)</name>
      <smpdb_id>SMP0108287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/13:0)</name>
      <smpdb_id>SMP0108291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/15:0)</name>
      <smpdb_id>SMP0108272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/18:0)</name>
      <smpdb_id>SMP0108258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0109204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0109205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0109206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0109207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0109208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0109209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0109210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0109211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0109212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0109213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/10:0)</name>
      <smpdb_id>SMP0108309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/12:0)</name>
      <smpdb_id>SMP0108333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/13:0)</name>
      <smpdb_id>SMP0108329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/17:0)</name>
      <smpdb_id>SMP0108303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/19:0)</name>
      <smpdb_id>SMP0108321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:0)</name>
      <smpdb_id>SMP0076182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0076183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/21:0)</name>
      <smpdb_id>SMP0108390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:0)</name>
      <smpdb_id>SMP0076190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0076191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/24:0)</name>
      <smpdb_id>SMP0076197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0076198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/8:0)</name>
      <smpdb_id>SMP0108268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-13:0)</name>
      <smpdb_id>SMP0109214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-15:0)</name>
      <smpdb_id>SMP0109215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-17:0)</name>
      <smpdb_id>SMP0109216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0109217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0109218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-12:0)</name>
      <smpdb_id>SMP0109219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-13:0)</name>
      <smpdb_id>SMP0109220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-14:0)</name>
      <smpdb_id>SMP0109221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-15:0)</name>
      <smpdb_id>SMP0109222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-16:0)</name>
      <smpdb_id>SMP0109223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-17:0)</name>
      <smpdb_id>SMP0109224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-18:0)</name>
      <smpdb_id>SMP0109225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0109226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0109227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0109228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0109229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0109230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0076206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0076213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/21:0)</name>
      <smpdb_id>SMP0108389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/22:0)</name>
      <smpdb_id>SMP0108370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0109231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0109232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0109233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0109234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0109235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0109236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0109237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0109238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0109239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0109240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0109241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0109242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0109243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0109244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0109245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0109246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0109247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:0)</name>
      <smpdb_id>SMP0076290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/24:0)</name>
      <smpdb_id>SMP0076297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/24:0/24:0)</name>
      <smpdb_id>SMP0076332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/10:0)</name>
      <smpdb_id>SMP0108298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/14:0)</name>
      <smpdb_id>SMP0108246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/15:0)</name>
      <smpdb_id>SMP0108285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/16:0)</name>
      <smpdb_id>SMP0108280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/19:0)</name>
      <smpdb_id>SMP0108310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/21:0)</name>
      <smpdb_id>SMP0108245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/22:0)</name>
      <smpdb_id>SMP0108260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/8:0)</name>
      <smpdb_id>SMP0108325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0109330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0109370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0109371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0109372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0109373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0109374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0109375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0109376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0109377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0109378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0109379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0109380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0109381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0109382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0109383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0109384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0109385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0109386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0109387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0109388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0109389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0109390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0109391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0109392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0109393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0109394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0109395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0109396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0109397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0109398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0109400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0109401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0109402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0109403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0109404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0109405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0109406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0109407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0109408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0109409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0109410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0109411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0109412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0109413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0109414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0109415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0109416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0109417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0109418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0109419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0109420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0109421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0109422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0109423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0109424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0109425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0109426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0076342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0076349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/10:0)</name>
      <smpdb_id>SMP0108335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/12:0)</name>
      <smpdb_id>SMP0108363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/13:0)</name>
      <smpdb_id>SMP0108339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/17:0)</name>
      <smpdb_id>SMP0108349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/18:0)</name>
      <smpdb_id>SMP0108337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/22:0)</name>
      <smpdb_id>SMP0108367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/12:0)</name>
      <smpdb_id>SMP0108361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/13:0)</name>
      <smpdb_id>SMP0108351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/14:0)</name>
      <smpdb_id>SMP0108344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/15:0)</name>
      <smpdb_id>SMP0108371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/16:0)</name>
      <smpdb_id>SMP0108383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/18:0)</name>
      <smpdb_id>SMP0108387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/22:0)</name>
      <smpdb_id>SMP0108366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0109440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/13:0)</name>
      <smpdb_id>SMP0108368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/16:0)</name>
      <smpdb_id>SMP0108380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/17:0)</name>
      <smpdb_id>SMP0108345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/18:0)</name>
      <smpdb_id>SMP0108341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/22:0)</name>
      <smpdb_id>SMP0108388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/10:0)</name>
      <smpdb_id>SMP0108347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/13:0)</name>
      <smpdb_id>SMP0108342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/14:0)</name>
      <smpdb_id>SMP0108338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/16:0)</name>
      <smpdb_id>SMP0108346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/17:0)</name>
      <smpdb_id>SMP0108352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/18:0)</name>
      <smpdb_id>SMP0108386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/22:0)</name>
      <smpdb_id>SMP0108334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/8:0)</name>
      <smpdb_id>SMP0108365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/10:0)</name>
      <smpdb_id>SMP0108372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/13:0)</name>
      <smpdb_id>SMP0108358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/14:0)</name>
      <smpdb_id>SMP0108375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/15:0)</name>
      <smpdb_id>SMP0108348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/17:0)</name>
      <smpdb_id>SMP0108384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/18:0)</name>
      <smpdb_id>SMP0108369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/22:0)</name>
      <smpdb_id>SMP0108392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/8:0)</name>
      <smpdb_id>SMP0108354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/10:0)</name>
      <smpdb_id>SMP0108350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/15:0)</name>
      <smpdb_id>SMP0108355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/16:0)</name>
      <smpdb_id>SMP0108381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/17:0)</name>
      <smpdb_id>SMP0108364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/18:0)</name>
      <smpdb_id>SMP0108356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/22:0)</name>
      <smpdb_id>SMP0108385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/12:0)</name>
      <smpdb_id>SMP0108376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/17:0)</name>
      <smpdb_id>SMP0108393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/8:0)</name>
      <smpdb_id>SMP0108377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/17:0)</name>
      <smpdb_id>SMP0108396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/18:0)</name>
      <smpdb_id>SMP0108399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/10:0)</name>
      <smpdb_id>SMP0108340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/12:0)</name>
      <smpdb_id>SMP0108374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/13:0)</name>
      <smpdb_id>SMP0108336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/14:0)</name>
      <smpdb_id>SMP0108373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/15:0)</name>
      <smpdb_id>SMP0108382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/16:0)</name>
      <smpdb_id>SMP0108391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/17:0)</name>
      <smpdb_id>SMP0108397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/18:0)</name>
      <smpdb_id>SMP0108398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/22:0)</name>
      <smpdb_id>SMP0108400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/8:0)</name>
      <smpdb_id>SMP0108343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0109556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0109557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0109558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0109559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0109560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0109561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0109562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0109563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0109564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0109565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0109566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0109567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0109568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0109569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0109570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0109571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0109572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/17:0)</name>
      <smpdb_id>SMP0108395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/18:0)</name>
      <smpdb_id>SMP0108394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/22:0)</name>
      <smpdb_id>SMP0108401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/10:0)</name>
      <smpdb_id>SMP0108360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/12:0)</name>
      <smpdb_id>SMP0108357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/13:0)</name>
      <smpdb_id>SMP0108353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/16:0)</name>
      <smpdb_id>SMP0108359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/18:0)</name>
      <smpdb_id>SMP0108378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/22:0)</name>
      <smpdb_id>SMP0108362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/8:0)</name>
      <smpdb_id>SMP0108379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0109694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0109695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0109696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0109697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0109698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0109699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0109700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0109701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0109702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0109703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0109704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0109705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0109706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0109707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0109708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0109709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0109710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0109711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0109712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0109713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0109714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0109715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0109716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0109717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0109718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0109719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0109720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0109721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0109722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0109723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0109724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0109725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0109726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0109727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0109728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0109729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0109730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0109731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0109732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0109733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0109734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0109735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0109736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0109737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0109738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0109739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0109740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0109741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0109742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0109743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0109744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0109745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0109746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0109747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0109748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0109749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/10:0)</name>
      <smpdb_id>SMP0108437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/12:0)</name>
      <smpdb_id>SMP0108408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/13:0)</name>
      <smpdb_id>SMP0108423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/12:0)</name>
      <smpdb_id>SMP0108405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/13:0)</name>
      <smpdb_id>SMP0108403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/14:0)</name>
      <smpdb_id>SMP0108414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/15:0)</name>
      <smpdb_id>SMP0108426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/18:0)</name>
      <smpdb_id>SMP0108407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/8:0)</name>
      <smpdb_id>SMP0108420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0109763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/13:0)</name>
      <smpdb_id>SMP0108436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/15:0)</name>
      <smpdb_id>SMP0108428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/16:0)</name>
      <smpdb_id>SMP0108430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/17:0)</name>
      <smpdb_id>SMP0108419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/18:0)</name>
      <smpdb_id>SMP0108413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/8:0)</name>
      <smpdb_id>SMP0108411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/10:0)</name>
      <smpdb_id>SMP0108440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/13:0)</name>
      <smpdb_id>SMP0108422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/10:0)</name>
      <smpdb_id>SMP0108425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/8:0)</name>
      <smpdb_id>SMP0108410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/10:0)</name>
      <smpdb_id>SMP0108404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/12:0)</name>
      <smpdb_id>SMP0108406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/10:0)</name>
      <smpdb_id>SMP0108439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/12:0)</name>
      <smpdb_id>SMP0108402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/14:0)</name>
      <smpdb_id>SMP0108415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/15:0)</name>
      <smpdb_id>SMP0108434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/16:0)</name>
      <smpdb_id>SMP0108412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/17:0)</name>
      <smpdb_id>SMP0108431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/8:0)</name>
      <smpdb_id>SMP0108409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/10:0)</name>
      <smpdb_id>SMP0108421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/17:0)</name>
      <smpdb_id>SMP0108417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/8:0)</name>
      <smpdb_id>SMP0108432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/10:0)</name>
      <smpdb_id>SMP0108424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/12:0)</name>
      <smpdb_id>SMP0108435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/13:0)</name>
      <smpdb_id>SMP0108433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/17:0)</name>
      <smpdb_id>SMP0108438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:0)</name>
      <smpdb_id>SMP0076986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/24:0)</name>
      <smpdb_id>SMP0076993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/8:0)</name>
      <smpdb_id>SMP0108441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0077001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/24:0/24:0)</name>
      <smpdb_id>SMP0077028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/10:0)</name>
      <smpdb_id>SMP0108416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/14:0)</name>
      <smpdb_id>SMP0108418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/16:0)</name>
      <smpdb_id>SMP0108427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/8:0)</name>
      <smpdb_id>SMP0108429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0108540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0077031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0077037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:0/24:0/24:0)</name>
      <smpdb_id>SMP0077147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:1(15Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/10:0)</name>
      <smpdb_id>SMP0108443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/12:0)</name>
      <smpdb_id>SMP0108502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/16:0)</name>
      <smpdb_id>SMP0108450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/18:0)</name>
      <smpdb_id>SMP0108535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0110069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0110070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/12:0)</name>
      <smpdb_id>SMP0108459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/13:0)</name>
      <smpdb_id>SMP0108498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/14:0)</name>
      <smpdb_id>SMP0108462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/15:0)</name>
      <smpdb_id>SMP0108442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/17:0)</name>
      <smpdb_id>SMP0108464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/19:0)</name>
      <smpdb_id>SMP0108499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0110086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0110087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/10:0)</name>
      <smpdb_id>SMP0108455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/12:0)</name>
      <smpdb_id>SMP0108475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/14:0)</name>
      <smpdb_id>SMP0108532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/15:0)</name>
      <smpdb_id>SMP0108529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/17:0)</name>
      <smpdb_id>SMP0108491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/18:0)</name>
      <smpdb_id>SMP0108510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0110103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0110104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/12:0)</name>
      <smpdb_id>SMP0108486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/15:0)</name>
      <smpdb_id>SMP0108528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/17:0)</name>
      <smpdb_id>SMP0108505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0110120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0110121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/13:0)</name>
      <smpdb_id>SMP0108513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/14:0)</name>
      <smpdb_id>SMP0108449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/15:0)</name>
      <smpdb_id>SMP0108493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/16:0)</name>
      <smpdb_id>SMP0108500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/18:0)</name>
      <smpdb_id>SMP0108474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/19:0)</name>
      <smpdb_id>SMP0108446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0110137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0110138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/12:0)</name>
      <smpdb_id>SMP0108516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/16:0)</name>
      <smpdb_id>SMP0108530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/17:0)</name>
      <smpdb_id>SMP0108509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0110154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0110155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/13:0)</name>
      <smpdb_id>SMP0108524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/15:0)</name>
      <smpdb_id>SMP0108501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/17:0)</name>
      <smpdb_id>SMP0108453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/18:0)</name>
      <smpdb_id>SMP0108520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0110171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0110172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/10:0)</name>
      <smpdb_id>SMP0108482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/12:0)</name>
      <smpdb_id>SMP0108444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/14:0)</name>
      <smpdb_id>SMP0108497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/15:0)</name>
      <smpdb_id>SMP0108487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/17:0)</name>
      <smpdb_id>SMP0108484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/18:0)</name>
      <smpdb_id>SMP0108531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/19:0)</name>
      <smpdb_id>SMP0108538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0110185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0110186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0110187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0110188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0110189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0110190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0110191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0110192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0110193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0110194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0110195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-20:0)</name>
      <smpdb_id>SMP0110196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/12:0)</name>
      <smpdb_id>SMP0108508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/13:0)</name>
      <smpdb_id>SMP0108539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/14:0)</name>
      <smpdb_id>SMP0108515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/15:0)</name>
      <smpdb_id>SMP0108454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/16:0)</name>
      <smpdb_id>SMP0108490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/17:0)</name>
      <smpdb_id>SMP0108527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/18:0)</name>
      <smpdb_id>SMP0108537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/19:0)</name>
      <smpdb_id>SMP0108536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/8:0)</name>
      <smpdb_id>SMP0108242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0110197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0110198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0110199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0110200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0110201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0110202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0110203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0110204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0110205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0110206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0110207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0110208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0110209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0110210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0110211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0110212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0110213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0110217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0110218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0110223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0110233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0110234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0110248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0110249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0110262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0110263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0110264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0110265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0110266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0110267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0110268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0110269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0110270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0110271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0110272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0110273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0110274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0110275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/12:0)</name>
      <smpdb_id>SMP0110367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/13:0)</name>
      <smpdb_id>SMP0110368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/14:0)</name>
      <smpdb_id>SMP0110369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/15:0)</name>
      <smpdb_id>SMP0110370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/16:0)</name>
      <smpdb_id>SMP0110371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/17:0)</name>
      <smpdb_id>SMP0110372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/18:0)</name>
      <smpdb_id>SMP0110373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0110377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/13:0)</name>
      <smpdb_id>SMP0110390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/14:0)</name>
      <smpdb_id>SMP0110391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/15:0)</name>
      <smpdb_id>SMP0110392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/16:0)</name>
      <smpdb_id>SMP0110393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/17:0)</name>
      <smpdb_id>SMP0110394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/18:0)</name>
      <smpdb_id>SMP0110395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0110399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/14:0)</name>
      <smpdb_id>SMP0110412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/15:0)</name>
      <smpdb_id>SMP0110413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/16:0)</name>
      <smpdb_id>SMP0110414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/17:0)</name>
      <smpdb_id>SMP0110415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/18:0)</name>
      <smpdb_id>SMP0110416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0110420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/15:0)</name>
      <smpdb_id>SMP0110433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/16:0)</name>
      <smpdb_id>SMP0110434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/17:0)</name>
      <smpdb_id>SMP0110435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/18:0)</name>
      <smpdb_id>SMP0110436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0110440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/16:0)</name>
      <smpdb_id>SMP0110453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/17:0)</name>
      <smpdb_id>SMP0110454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/18:0)</name>
      <smpdb_id>SMP0110455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0110459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/17:0)</name>
      <smpdb_id>SMP0110472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/18:0)</name>
      <smpdb_id>SMP0110473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0110477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/18:0)</name>
      <smpdb_id>SMP0110490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0110494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0110510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0110524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0110538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0110551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/13:0)</name>
      <smpdb_id>SMP0110552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/14:0)</name>
      <smpdb_id>SMP0110553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/15:0)</name>
      <smpdb_id>SMP0110554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/16:0)</name>
      <smpdb_id>SMP0110555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/17:0)</name>
      <smpdb_id>SMP0110556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/18:0)</name>
      <smpdb_id>SMP0110557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-13:0)</name>
      <smpdb_id>SMP0110558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-15:0)</name>
      <smpdb_id>SMP0110559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-17:0)</name>
      <smpdb_id>SMP0110560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0110561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0110562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0110563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0110564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0110565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0110566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0110567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0110568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0110569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0110570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0110571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0110572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0110573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0110574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/a-13:0)</name>
      <smpdb_id>SMP0110630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/12:0)</name>
      <smpdb_id>SMP0110667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/13:0)</name>
      <smpdb_id>SMP0110668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/14:0)</name>
      <smpdb_id>SMP0110669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/15:0)</name>
      <smpdb_id>SMP0110670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/16:0)</name>
      <smpdb_id>SMP0110671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/17:0)</name>
      <smpdb_id>SMP0110672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/18:0)</name>
      <smpdb_id>SMP0110673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/13:0)</name>
      <smpdb_id>SMP0110689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/14:0)</name>
      <smpdb_id>SMP0110690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/15:0)</name>
      <smpdb_id>SMP0110691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/16:0)</name>
      <smpdb_id>SMP0110692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/17:0)</name>
      <smpdb_id>SMP0110693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/18:0)</name>
      <smpdb_id>SMP0110694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/14:0)</name>
      <smpdb_id>SMP0110710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/15:0)</name>
      <smpdb_id>SMP0110711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/16:0)</name>
      <smpdb_id>SMP0110712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/17:0)</name>
      <smpdb_id>SMP0110713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/18:0)</name>
      <smpdb_id>SMP0110714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/15:0)</name>
      <smpdb_id>SMP0110730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/16:0)</name>
      <smpdb_id>SMP0110731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/17:0)</name>
      <smpdb_id>SMP0110732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/18:0)</name>
      <smpdb_id>SMP0110733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/16:0)</name>
      <smpdb_id>SMP0110749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/17:0)</name>
      <smpdb_id>SMP0110750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/18:0)</name>
      <smpdb_id>SMP0110751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/17:0)</name>
      <smpdb_id>SMP0110767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/18:0)</name>
      <smpdb_id>SMP0110768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/18:0)</name>
      <smpdb_id>SMP0110784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0110807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/10:0)</name>
      <smpdb_id>SMP0110842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/12:0)</name>
      <smpdb_id>SMP0110843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/13:0)</name>
      <smpdb_id>SMP0110844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/14:0)</name>
      <smpdb_id>SMP0110845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/15:0)</name>
      <smpdb_id>SMP0110846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/16:0)</name>
      <smpdb_id>SMP0110847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/17:0)</name>
      <smpdb_id>SMP0110848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/18:0)</name>
      <smpdb_id>SMP0110849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-13:0)</name>
      <smpdb_id>SMP0110850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-15:0)</name>
      <smpdb_id>SMP0110851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-17:0)</name>
      <smpdb_id>SMP0110852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0110952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0110953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0110954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0110955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0110956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0110957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0110958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0110959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0110960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0110961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0110962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0110963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0110964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0110965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0110966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0110967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0110968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0110972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0110973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0110974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0110975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0110976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0110977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0110978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0110979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0110980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0110981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0110982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0110983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0110984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0110985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0110986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0110987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0110988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0110991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0110992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0110993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0110994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0110995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0110996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0110997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0110998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0110999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0111000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0111001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0111002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0111003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0111004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0111005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0111006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0111007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/12:0)</name>
      <smpdb_id>SMP0111009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/13:0)</name>
      <smpdb_id>SMP0111010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/14:0)</name>
      <smpdb_id>SMP0111011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/15:0)</name>
      <smpdb_id>SMP0111012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/16:0)</name>
      <smpdb_id>SMP0111013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/17:0)</name>
      <smpdb_id>SMP0111014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/18:0)</name>
      <smpdb_id>SMP0111015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/19:0)</name>
      <smpdb_id>SMP0111016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0111027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0111028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0111029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/13:0)</name>
      <smpdb_id>SMP0111031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/14:0)</name>
      <smpdb_id>SMP0111032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/15:0)</name>
      <smpdb_id>SMP0111033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/16:0)</name>
      <smpdb_id>SMP0111034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/17:0)</name>
      <smpdb_id>SMP0111035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/18:0)</name>
      <smpdb_id>SMP0111036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/19:0)</name>
      <smpdb_id>SMP0111037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0111048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0111049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0111050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/14:0)</name>
      <smpdb_id>SMP0111052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/15:0)</name>
      <smpdb_id>SMP0111053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/16:0)</name>
      <smpdb_id>SMP0111054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/17:0)</name>
      <smpdb_id>SMP0111055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/18:0)</name>
      <smpdb_id>SMP0111056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/19:0)</name>
      <smpdb_id>SMP0111057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0111068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0111069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0111070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/15:0)</name>
      <smpdb_id>SMP0111072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/16:0)</name>
      <smpdb_id>SMP0111073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/17:0)</name>
      <smpdb_id>SMP0111074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/18:0)</name>
      <smpdb_id>SMP0111075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/19:0)</name>
      <smpdb_id>SMP0111076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0111087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0111088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0111089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/16:0)</name>
      <smpdb_id>SMP0111091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/17:0)</name>
      <smpdb_id>SMP0111092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/18:0)</name>
      <smpdb_id>SMP0111093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/19:0)</name>
      <smpdb_id>SMP0111094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0111105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0111106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0111107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/17:0)</name>
      <smpdb_id>SMP0111109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/18:0)</name>
      <smpdb_id>SMP0111110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/19:0)</name>
      <smpdb_id>SMP0111111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0111122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0111123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0111124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/18:0)</name>
      <smpdb_id>SMP0111126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/19:0)</name>
      <smpdb_id>SMP0111127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0111138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0111139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0111140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/19:0)</name>
      <smpdb_id>SMP0111142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0111143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0111144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0111145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0111146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0111147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0111148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0111149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0111150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0111151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0111152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0111153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0111164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0111165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0111166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0111177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0111178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0111179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0111189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0111190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0111191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0111200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0111201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0111202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0111210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0111211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0111212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0111219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0111220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0111221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0111227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0111228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0111229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0111234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0111235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0111236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0111240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0111241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0111242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0111245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0111246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0111247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/12:0)</name>
      <smpdb_id>SMP0111249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/13:0)</name>
      <smpdb_id>SMP0111250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/14:0)</name>
      <smpdb_id>SMP0111251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/15:0)</name>
      <smpdb_id>SMP0111252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/16:0)</name>
      <smpdb_id>SMP0111253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/17:0)</name>
      <smpdb_id>SMP0111254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/18:0)</name>
      <smpdb_id>SMP0111255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-13:0)</name>
      <smpdb_id>SMP0111256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-15:0)</name>
      <smpdb_id>SMP0111257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-17:0)</name>
      <smpdb_id>SMP0111258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-12:0)</name>
      <smpdb_id>SMP0111259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-13:0)</name>
      <smpdb_id>SMP0111260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-14:0)</name>
      <smpdb_id>SMP0111261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-15:0)</name>
      <smpdb_id>SMP0111262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-16:0)</name>
      <smpdb_id>SMP0111263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-17:0)</name>
      <smpdb_id>SMP0111264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-18:0)</name>
      <smpdb_id>SMP0111265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0111266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0111267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0111268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0111269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0111270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0111271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0111272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/12:0)</name>
      <smpdb_id>SMP0111276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/13:0)</name>
      <smpdb_id>SMP0111277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/14:0)</name>
      <smpdb_id>SMP0111278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/15:0)</name>
      <smpdb_id>SMP0111279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/16:0)</name>
      <smpdb_id>SMP0111280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/17:0)</name>
      <smpdb_id>SMP0111281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/18:0)</name>
      <smpdb_id>SMP0111282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0111293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/13:0)</name>
      <smpdb_id>SMP0111295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/14:0)</name>
      <smpdb_id>SMP0111296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/15:0)</name>
      <smpdb_id>SMP0111297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/16:0)</name>
      <smpdb_id>SMP0111298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/17:0)</name>
      <smpdb_id>SMP0111299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/18:0)</name>
      <smpdb_id>SMP0111300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0111311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/14:0)</name>
      <smpdb_id>SMP0111313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/15:0)</name>
      <smpdb_id>SMP0111314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/16:0)</name>
      <smpdb_id>SMP0111315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/17:0)</name>
      <smpdb_id>SMP0111316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/18:0)</name>
      <smpdb_id>SMP0111317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0111328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/15:0)</name>
      <smpdb_id>SMP0111330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/16:0)</name>
      <smpdb_id>SMP0111331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/17:0)</name>
      <smpdb_id>SMP0111332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/18:0)</name>
      <smpdb_id>SMP0111333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0111344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/16:0)</name>
      <smpdb_id>SMP0111346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/17:0)</name>
      <smpdb_id>SMP0111347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/18:0)</name>
      <smpdb_id>SMP0111348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0111359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/17:0)</name>
      <smpdb_id>SMP0111361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/18:0)</name>
      <smpdb_id>SMP0111362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0111373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/18:0)</name>
      <smpdb_id>SMP0111375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0111386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0111398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0111409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0111419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0111428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0111436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0111443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0111449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0111454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0111458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0111461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0111463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0111464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0111465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0111466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0111467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0111468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0111469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0111470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0111471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0111472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0111473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0111474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0111475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0111476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0111477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0111478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0111479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0111480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0111481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0111482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/12:0)</name>
      <smpdb_id>SMP0111486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/13:0)</name>
      <smpdb_id>SMP0111487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/14:0)</name>
      <smpdb_id>SMP0111488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/15:0)</name>
      <smpdb_id>SMP0111489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/16:0)</name>
      <smpdb_id>SMP0111490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/17:0)</name>
      <smpdb_id>SMP0111491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/18:0)</name>
      <smpdb_id>SMP0111492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/13:0)</name>
      <smpdb_id>SMP0111504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/14:0)</name>
      <smpdb_id>SMP0111505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/15:0)</name>
      <smpdb_id>SMP0111506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/16:0)</name>
      <smpdb_id>SMP0111507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/17:0)</name>
      <smpdb_id>SMP0111508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/18:0)</name>
      <smpdb_id>SMP0111509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/14:0)</name>
      <smpdb_id>SMP0111521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/15:0)</name>
      <smpdb_id>SMP0111522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/16:0)</name>
      <smpdb_id>SMP0111523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/17:0)</name>
      <smpdb_id>SMP0111524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/18:0)</name>
      <smpdb_id>SMP0111525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/15:0)</name>
      <smpdb_id>SMP0111537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/16:0)</name>
      <smpdb_id>SMP0111538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/17:0)</name>
      <smpdb_id>SMP0111539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/18:0)</name>
      <smpdb_id>SMP0111540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/16:0)</name>
      <smpdb_id>SMP0111552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/17:0)</name>
      <smpdb_id>SMP0111553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/18:0)</name>
      <smpdb_id>SMP0111554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/17:0)</name>
      <smpdb_id>SMP0111566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/18:0)</name>
      <smpdb_id>SMP0111567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/18:0)</name>
      <smpdb_id>SMP0111579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0111656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0111657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0111658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0111659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0111660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0111661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0111662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0111663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0111664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0111665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0111666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0111667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0111668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0111669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0111670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0111671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0111672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/12:0)</name>
      <smpdb_id>SMP0111676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/13:0)</name>
      <smpdb_id>SMP0111677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/14:0)</name>
      <smpdb_id>SMP0111678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/15:0)</name>
      <smpdb_id>SMP0111679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/16:0)</name>
      <smpdb_id>SMP0111680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/17:0)</name>
      <smpdb_id>SMP0111681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/18:0)</name>
      <smpdb_id>SMP0111682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/13:0)</name>
      <smpdb_id>SMP0111693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/14:0)</name>
      <smpdb_id>SMP0111694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/15:0)</name>
      <smpdb_id>SMP0111695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/16:0)</name>
      <smpdb_id>SMP0111696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/17:0)</name>
      <smpdb_id>SMP0111697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/18:0)</name>
      <smpdb_id>SMP0111698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/14:0)</name>
      <smpdb_id>SMP0111709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/15:0)</name>
      <smpdb_id>SMP0111710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/16:0)</name>
      <smpdb_id>SMP0111711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/17:0)</name>
      <smpdb_id>SMP0111712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/18:0)</name>
      <smpdb_id>SMP0111713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/15:0)</name>
      <smpdb_id>SMP0111724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/16:0)</name>
      <smpdb_id>SMP0111725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/17:0)</name>
      <smpdb_id>SMP0111726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/18:0)</name>
      <smpdb_id>SMP0111727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/16:0)</name>
      <smpdb_id>SMP0111738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/17:0)</name>
      <smpdb_id>SMP0111739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/18:0)</name>
      <smpdb_id>SMP0111740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/17:0)</name>
      <smpdb_id>SMP0111751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/18:0)</name>
      <smpdb_id>SMP0111752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/18:0)</name>
      <smpdb_id>SMP0111763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0111829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0111830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0111831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0111832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0111833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0111834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0111835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0111836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0111837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0111838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0111839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0111840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0111841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0111842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0111843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0111844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0111845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerol Phosphate Shuttle</name>
      <smpdb_id>SMP0087199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Electron Transport Chain</name>
      <smpdb_id>SMP0087261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2988</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179331</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>80</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>97</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00093</kegg_id>
  <drugbank_id>DB02515</drugbank_id>
  <foodb_id>FDB031180</foodb_id>
  <chemspider_id>388308</chemspider_id>
  <pubchem_compound_id>439162</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15978</chebi_id>
  <knapsack_id>C00007288</knapsack_id>
  <wikipedia_id>Glycerol 3-phosphate</wikipedia_id>
  <meta_cyc_id>GLYCEROL-3P</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>137383</bigg_id>
  <metlin_id>5161</metlin_id>
  <synthesis_reference>Rios-Mercadillo, Victor M.; Whitesides, George M. Enzymic synthesis of sn-glycerol 3-phosphate. Journal of the American Chemical Society (1979), 101(19), 5828-9.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
      <pubmed_id>11132867</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
      <pubmed_id>28342601</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00078</protein_accession>
      <name>CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase, mitochondrial</name>
      <uniprot_id>Q2KJ28</uniprot_id>
      <gene_name>PGS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00092</protein_accession>
      <name>Glycerol-3-phosphate dehydrogenase, mitochondrial</name>
      <uniprot_id>A6QLU1</uniprot_id>
      <gene_name>GPD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00496</protein_accession>
      <name>Glycerophosphodiester phosphodiesterase 1</name>
      <uniprot_id>Q3T0T0</uniprot_id>
      <gene_name>GDE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00930</protein_accession>
      <name>Glycerol kinase</name>
      <uniprot_id>Q0IID9</uniprot_id>
      <gene_name>GK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00931</protein_accession>
      <name>Glycerol-3-phosphate dehydrogenase [NAD+], cytoplasmic</name>
      <uniprot_id>Q5EA88</uniprot_id>
      <gene_name>GPD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00932</protein_accession>
      <name>Glycerol-3-phosphate acyltransferase 4</name>
      <uniprot_id>A3FPG8</uniprot_id>
      <gene_name>AGPAT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00933</protein_accession>
      <name>Putative glycerol kinase 5</name>
      <uniprot_id>Q08D86</uniprot_id>
      <gene_name>GK5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00934</protein_accession>
      <name>Glycerol-3-phosphate acyltransferase 1, mitochondrial</name>
      <uniprot_id>Q5GJ77</uniprot_id>
      <gene_name>GPAM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:55 UTC</creation_date>
  <update_date>2020-04-15 22:13:11 UTC</update_date>
  <accession>BMDB0000127</accession>
  <secondary_accessions>
    <accession>BMDB00127</accession>
  </secondary_accessions>
  <name>D-Glucuronic acid</name>
  <description>D-Glucuronic acid, also known as glcaa or D-glucuronate, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. D-Glucuronic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Glucuronic acid exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>GlcAa</synonym>
    <synonym>GlcAalpha</synonym>
    <synonym>D-Glucuronate</synonym>
    <synonym>alpha-D-Glucopyranuronic acid</synonym>
    <synonym>alpha-D-Glucuronic acid</synonym>
    <synonym>alpha-delta-Glucopyranuronic acid</synonym>
    <synonym>alpha-delta-Glucuronic acid</synonym>
    <synonym>D-(+)-Glucuronate</synonym>
    <synonym>D-(+)-Glucuronic acid</synonym>
    <synonym>delta-(+)-Glucuronate</synonym>
    <synonym>delta-(+)-Glucuronic acid</synonym>
    <synonym>delta-Glucuronate</synonym>
    <synonym>GCU</synonym>
    <synonym>Glucosiduronate</synonym>
    <synonym>Glucosiduronic acid</synonym>
    <synonym>Glucuronate</synonym>
    <synonym>Glucuronic acid</synonym>
  </synonyms>
  <chemical_formula>C6H10O7</chemical_formula>
  <average_molecular_weight>194.1394</average_molecular_weight>
  <monisotopic_moleculate_weight>194.042652674</monisotopic_moleculate_weight>
  <iupac_name>(2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>glucuronic acid</traditional_iupac>
  <cas_registry_number>6556-12-3</cas_registry_number>
  <smiles>O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1</inchi>
  <inchikey>AEMOLEFTQBMNLQ-WAXACMCWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Glucuronic acid derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glucuronic acid or derivatives</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D-glucopyranuronic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>143 - 144 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>485 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.57</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>194.1394</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>194.042652674</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AEMOLEFTQBMNLQ-WAXACMCWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>127.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367272</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00191</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB021897</foodb_id>
  <chemspider_id>392615</chemspider_id>
  <pubchem_compound_id>444791</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>42717</chebi_id>
  <knapsack_id>C00001123</knapsack_id>
  <wikipedia_id>Glucuronic acid</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>34196</bigg_id>
  <metlin_id>161</metlin_id>
  <synthesis_reference>Hamayasu, Kenichi; Tadokoro, Hiroki; Kishino, Eriko; Ito, Tetsuya; Fujita, Koki; Hara, Kozo.  Preparation of glucuronic acid and/or glucuronolactone from sucrose.    PCT Int. Appl.  (2006),  21pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00373</protein_accession>
      <name>Dermatan-sulfate epimerase</name>
      <uniprot_id>P0C2H4</uniprot_id>
      <gene_name>DSE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00424</protein_accession>
      <name>Hyaluronidase-2</name>
      <uniprot_id>Q8SQG8</uniprot_id>
      <gene_name>HYAL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00425</protein_accession>
      <name>Hyaluronidase-1</name>
      <uniprot_id>Q5E985</uniprot_id>
      <gene_name>HYAL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00426</protein_accession>
      <name>Inositol oxygenase</name>
      <uniprot_id>A7MBE4</uniprot_id>
      <gene_name>MIOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:56 UTC</creation_date>
  <update_date>2020-04-15 22:13:11 UTC</update_date>
  <accession>BMDB0000128</accession>
  <secondary_accessions>
    <accession>BMDB00128</accession>
  </secondary_accessions>
  <name>Guanidoacetic acid</name>
  <description>Guanidoacetic acid, also known as guanidoacetic acid or Guanidoacetic acid, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Guanidoacetic acid is possibly soluble (in water) and a very strong basic compound (based on its pKa). Guanidoacetic acid exists in all living organisms, ranging from bacteria to humans. Guanidoacetic acid participates in a number of enzymatic reactions, within cattle. In particular, Guanidoacetic acid and orotidylic acid can be biosynthesized from glycine and L-arginine through the action of the enzyme glycine amidinotransferase, mitochondrial. In addition, Guanidoacetic acid and S-adenosylhomocysteine can be converted into S-adenosylmethionine and creatine; which is mediated by the enzyme guanidoacetic acid N-methyltransferase. In cattle, guanidoacetic acid is involved in the metabolic pathway called the glycine and serine metabolism pathway. Guanidoacetic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>Glycocyamine</synonym>
    <synonym>Guanidinoacetate</synonym>
    <synonym>N-(Carbamimidoyl)glycine</synonym>
    <synonym>N-[Amino(imino)methyl]glycine</synonym>
    <synonym>N-Amidinoglycine</synonym>
    <synonym>Guanidinoacetic acid</synonym>
    <synonym>Guanidoacetate</synonym>
    <synonym>(Carboxymethyl)-guanidine</synonym>
    <synonym>2-[[Amino(imino)methyl]amino]acetate</synonym>
    <synonym>2-[[Amino(imino)methyl]amino]acetic acid</synonym>
    <synonym>a-Guanidinoacetate</synonym>
    <synonym>a-Guanidinoacetic acid</synonym>
    <synonym>alpha-Guanidinoacetate</synonym>
    <synonym>alpha-Guanidinoacetic acid</synonym>
    <synonym>b-Guanidinoacetate</synonym>
    <synonym>b-Guanidinoacetic acid</synonym>
    <synonym>beta-Guanidinoacetate</synonym>
    <synonym>beta-Guanidinoacetic acid</synonym>
    <synonym>Betacyamine</synonym>
    <synonym>Betasyamine</synonym>
    <synonym>Guanidineacetate</synonym>
    <synonym>Guanidineacetic acid</synonym>
    <synonym>Guanidylacetate</synonym>
    <synonym>Guanidylacetic acid</synonym>
    <synonym>Guanyl glycine</synonym>
    <synonym>N-Amidino-glycine</synonym>
    <synonym>[(Aminoiminomethyl)amino]-acetate</synonym>
    <synonym>[(Aminoiminomethyl)amino]-acetic acid</synonym>
    <synonym>Glycocyamine, 2-(14)C-labeled</synonym>
    <synonym>Glycocyamine, ion (1-)</synonym>
    <synonym>Glycocyamine monohydrochloride</synonym>
  </synonyms>
  <chemical_formula>C3H7N3O2</chemical_formula>
  <average_molecular_weight>117.1066</average_molecular_weight>
  <monisotopic_moleculate_weight>117.053826483</monisotopic_moleculate_weight>
  <iupac_name>2-carbamimidamidoacetic acid</iupac_name>
  <traditional_iupac>glycocyamine</traditional_iupac>
  <cas_registry_number>352-97-6</cas_registry_number>
  <smiles>NC(=N)NCC(O)=O</smiles>
  <inchi>InChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6)</inchi>
  <inchikey>BPMFZUMJYQTVII-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Guanidines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-amidino-amino acid</external_descriptor>
      <external_descriptor>glycine derivative</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>3.6 mg/mL at 15 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>12.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-carbamimidamidoacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>117.1066</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>117.053826483</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=N)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7N3O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BPMFZUMJYQTVII-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>99.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>36.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451885</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00581</kegg_id>
  <drugbank_id>DB02751</drugbank_id>
  <foodb_id>FDB005417</foodb_id>
  <chemspider_id>743</chemspider_id>
  <pubchem_compound_id>763</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16344</chebi_id>
  <knapsack_id/>
  <wikipedia_id>Glycocyamine</wikipedia_id>
  <meta_cyc_id>GUANIDOACETIC_ACID</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>1594816</bigg_id>
  <metlin_id>5163</metlin_id>
  <synthesis_reference>Thalhammer, Franz; Gastner, Thomas.  Preparation of creatine, creatine monohydrate and guanidinoacetic acid. Ger. Offen.  (2007),  5pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00412</protein_accession>
      <name>Guanidinoacetate N-methyltransferase</name>
      <uniprot_id>Q2TBQ3</uniprot_id>
      <gene_name>GAMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00556</protein_accession>
      <name>Glycine amidinotransferase, mitochondrial</name>
      <uniprot_id>Q2HJ74</uniprot_id>
      <gene_name>GATM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:57 UTC</creation_date>
  <update_date>2020-04-16 20:36:57 UTC</update_date>
  <accession>BMDB0000130</accession>
  <secondary_accessions>
    <accession>BMDB00130</accession>
  </secondary_accessions>
  <name>Homogentisic acid</name>
  <description>Homogentisic acid, also known as homogentisate or acid, homogentisic, belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position. Homogentisic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Homogentisic acid exists in all living organisms, ranging from bacteria to humans. Homogentisic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2,5-Dihydroxyphenylacetic acid</synonym>
    <synonym>2-(3,6-DIHYDROXYPHENYL)acetIC ACID</synonym>
    <synonym>2,5-Dihydroxyphenylacetate</synonym>
    <synonym>2-(3,6-DIHYDROXYPHENYL)acetate</synonym>
    <synonym>Homogentisate</synonym>
    <synonym>(2,5-Dihydroxyphenyl)-acetate</synonym>
    <synonym>(2,5-Dihydroxyphenyl)-acetic acid</synonym>
    <synonym>2,5-Dihydroxy-a-toluate</synonym>
    <synonym>2,5-Dihydroxy-a-toluic acid</synonym>
    <synonym>2,5-Dihydroxy-alpha-toluate</synonym>
    <synonym>2,5-Dihydroxy-alpha-toluic acid</synonym>
    <synonym>2,5-Dihydroxy-benzeneacetate</synonym>
    <synonym>2,5-Dihydroxy-benzeneacetic acid</synonym>
    <synonym>Alcapton</synonym>
    <synonym>Homogentisate acid</synonym>
    <synonym>Homogentisinate</synonym>
    <synonym>Homogentisinic acid</synonym>
    <synonym>Melanic acid</synonym>
    <synonym>Acid, homogentisic</synonym>
  </synonyms>
  <chemical_formula>C8H8O4</chemical_formula>
  <average_molecular_weight>168.1467</average_molecular_weight>
  <monisotopic_moleculate_weight>168.042258744</monisotopic_moleculate_weight>
  <iupac_name>2-(2,5-dihydroxyphenyl)acetic acid</iupac_name>
  <traditional_iupac>homogentisic acid</traditional_iupac>
  <cas_registry_number>451-13-8</cas_registry_number>
  <smiles>OC(=O)CC1=C(O)C=CC(O)=C1</smiles>
  <inchi>InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)</inchi>
  <inchikey>IGMNYECMUMZDDF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Phenylacetic acids</sub_class>
    <direct_parent>2(hydroxyphenyl)acetic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroquinones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>2(hydroxyphenyl)acetic acid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroquinone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dihydroxyphenylacetic acid</external_descriptor>
      <external_descriptor>hydroquinones</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>153 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>850 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.86</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-5.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(2,5-dihydroxyphenyl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>168.1467</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>168.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC1=C(O)C=CC(O)=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IGMNYECMUMZDDF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3084</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00544</kegg_id>
  <drugbank_id>DB08327</drugbank_id>
  <foodb_id>FDB030907</foodb_id>
  <chemspider_id>759</chemspider_id>
  <pubchem_compound_id>780</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>44747</chebi_id>
  <knapsack_id>C00007309</knapsack_id>
  <wikipedia_id>Homogentisic_acid</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>1485308</bigg_id>
  <metlin_id>331</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00684</protein_accession>
      <name>4-hydroxyphenylpyruvate dioxygenase</name>
      <uniprot_id>Q5EA20</uniprot_id>
      <gene_name>HPD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:58 UTC</creation_date>
  <update_date>2020-04-16 20:39:53 UTC</update_date>
  <accession>BMDB0000131</accession>
  <secondary_accessions>
    <accession>BMDB00131</accession>
  </secondary_accessions>
  <name>Glycerol</name>
  <description>Glycerol, also known as glycerin or glycyl alcohol, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. Glycerol exists as a liquid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Glycerol exists in all living species, ranging from bacteria to humans. In cattle, glycerol is involved in the metabolic pathway called phospholipid biosynthesis pathway. Glycerol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1,2,3-Propanetriol</synonym>
    <synonym>1,2,3-Trihydroxypropane</synonym>
    <synonym>Glycerin</synonym>
    <synonym>Glycerine</synonym>
    <synonym>Glyceritol</synonym>
    <synonym>Glycerolum</synonym>
    <synonym>Glycyl alcohol</synonym>
    <synonym>Glyzerin</synonym>
    <synonym>Gro</synonym>
    <synonym>Oelsuess</synonym>
    <synonym>Propanetriol</synonym>
    <synonym>Trihydroxypropane</synonym>
    <synonym>Concentrated glycerin</synonym>
    <synonym>Glycerin, concentrated</synonym>
    <synonym>Bulbold</synonym>
    <synonym>Cristal</synonym>
    <synonym>e 422</synonym>
    <synonym>Emery 916</synonym>
    <synonym>Glyceol opthalgan</synonym>
    <synonym>Glyrol</synonym>
    <synonym>Glysanin</synonym>
    <synonym>IFP</synonym>
    <synonym>Incorporation factor</synonym>
    <synonym>Mackstat H 66</synonym>
    <synonym>Osmoglyn</synonym>
    <synonym>Pricerine 9091</synonym>
    <synonym>RG-S</synonym>
    <synonym>Tryhydroxypropane</synonym>
    <synonym>2,5-Dihydroxyphenylacetic acid</synonym>
    <synonym>2-(3,6-DIHYDROXYPHENYL)acetIC ACID</synonym>
    <synonym>2,5-Dihydroxyphenylacetate</synonym>
    <synonym>2-(3,6-DIHYDROXYPHENYL)acetate</synonym>
    <synonym>Homogentisate</synonym>
    <synonym>(2,5-Dihydroxyphenyl)-acetate</synonym>
    <synonym>(2,5-Dihydroxyphenyl)-acetic acid</synonym>
    <synonym>2,5-Dihydroxy-a-toluate</synonym>
    <synonym>2,5-Dihydroxy-a-toluic acid</synonym>
    <synonym>2,5-Dihydroxy-alpha-toluate</synonym>
    <synonym>2,5-Dihydroxy-alpha-toluic acid</synonym>
    <synonym>2,5-Dihydroxy-benzeneacetate</synonym>
    <synonym>2,5-Dihydroxy-benzeneacetic acid</synonym>
    <synonym>Alcapton</synonym>
    <synonym>Homogentisate acid</synonym>
    <synonym>Homogentisinate</synonym>
    <synonym>Homogentisinic acid</synonym>
    <synonym>Melanic acid</synonym>
    <synonym>Acid, homogentisic</synonym>
    <synonym>GlcAa</synonym>
    <synonym>GlcAalpha</synonym>
    <synonym>D-Glucuronate</synonym>
    <synonym>alpha-D-Glucopyranuronic acid</synonym>
    <synonym>alpha-D-Glucuronic acid</synonym>
    <synonym>alpha-delta-Glucopyranuronic acid</synonym>
    <synonym>alpha-delta-Glucuronic acid</synonym>
    <synonym>D-(+)-Glucuronate</synonym>
    <synonym>D-(+)-Glucuronic acid</synonym>
    <synonym>delta-(+)-Glucuronate</synonym>
    <synonym>delta-(+)-Glucuronic acid</synonym>
    <synonym>delta-Glucuronate</synonym>
    <synonym>GCU</synonym>
    <synonym>Glucosiduronate</synonym>
    <synonym>Glucosiduronic acid</synonym>
    <synonym>Glucuronate</synonym>
    <synonym>Glucuronic acid</synonym>
    <synonym>(2E)-2-Butenedioic acid</synonym>
    <synonym>(e)-2-Butenedioic acid</synonym>
    <synonym>e297</synonym>
    <synonym>Fumarsaeure</synonym>
    <synonym>trans-1,2-Ethylenedicarboxylic acid</synonym>
    <synonym>trans-But-2-enedioic acid</synonym>
    <synonym>trans-Butenedioic acid</synonym>
    <synonym>(2E)-2-Butenedioate</synonym>
    <synonym>(e)-2-Butenedioate</synonym>
    <synonym>trans-1,2-Ethylenedicarboxylate</synonym>
    <synonym>trans-But-2-enedioate</synonym>
    <synonym>trans-Butenedioate</synonym>
    <synonym>Fumarate</synonym>
    <synonym>(2E)-But-2-enedioate</synonym>
    <synonym>(2E)-But-2-enedioic acid</synonym>
    <synonym>2-(e)-Butenedioate</synonym>
    <synonym>2-(e)-Butenedioic acid</synonym>
    <synonym>Allomaleate</synonym>
    <synonym>Allomaleic acid</synonym>
    <synonym>Boletate</synonym>
    <synonym>Boletic acid</synonym>
    <synonym>FC 33</synonym>
    <synonym>Lichenate</synonym>
    <synonym>Lichenic acid</synonym>
    <synonym>Sodium fumarate</synonym>
    <synonym>trans-2-Butenedioate</synonym>
    <synonym>trans-2-Butenedioic acid</synonym>
    <synonym>Furamag</synonym>
    <synonym>Ammonium fumarate</synonym>
    <synonym>Magnesium fumarate</synonym>
    <synonym>Mafusol</synonym>
  </synonyms>
  <chemical_formula>C3H8O3</chemical_formula>
  <average_molecular_weight>92.0938</average_molecular_weight>
  <monisotopic_moleculate_weight>92.047344122</monisotopic_moleculate_weight>
  <iupac_name>propane-1,2,3-triol</iupac_name>
  <traditional_iupac>glycerol</traditional_iupac>
  <cas_registry_number>56-81-5</cas_registry_number>
  <smiles>OCC(O)CO</smiles>
  <inchi>InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2</inchi>
  <inchikey>PEDCQBHIVMGVHV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar alcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sugar alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Glycerols</external_descriptor>
      <external_descriptor>a sugar alcohol</external_descriptor>
      <external_descriptor>alditol</external_descriptor>
      <external_descriptor>triol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>20 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.76</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>propane-1,2,3-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>92.0938</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>92.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PEDCQBHIVMGVHV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>20.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37312</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>314+/-38</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>6219+/-1151</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>328+/-210</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1401.6 +/- 53.77</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1515.35 +/- 117.81</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1732.09 +/- 101.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>833-1833</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>2300</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>903.03 +/- 70.49</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>392-528</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>200-310</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>99.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>148</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>170</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>93.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>685+/-231</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>144.04 +/- 54.94</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>157.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>236</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>265.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>144</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>158 +/- 11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>236 +/- 61</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>265 +/- 71</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>144 +/- 55</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>326+/-174</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>380+/-112</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00116</kegg_id>
  <chemspider_id/>
  <foodb_id>FDB000756</foodb_id>
  <drugbank_id>DB09462</drugbank_id>
  <pubchem_compound_id>753</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17754</chebi_id>
  <meta_cyc_id>GLYCEROL</meta_cyc_id>
  <knapsack_id>C00001163</knapsack_id>
  <wikipedia_id>Glycerol</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Yang, Yifang.  Purification of glycerol.  Faming Zhuanli Shenqing Gongkai Shuomingshu  (2007), 3pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
      <pubmed_id>29197344</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00930</protein_accession>
      <name>Glycerol kinase</name>
      <uniprot_id>Q0IID9</uniprot_id>
      <gene_name>GK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00933</protein_accession>
      <name>Putative glycerol kinase 5</name>
      <uniprot_id>Q08D86</uniprot_id>
      <gene_name>GK5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01064</protein_accession>
      <name>Diacylglycerol kinase alpha</name>
      <uniprot_id>A0JN54</uniprot_id>
      <gene_name>DGKA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01279</protein_accession>
      <name>Monoacylglycerol lipase ABHD6</name>
      <uniprot_id>Q1LZ86</uniprot_id>
      <gene_name>ABHD6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01280</protein_accession>
      <name>Hormone-sensitive lipase</name>
      <uniprot_id>P16386</uniprot_id>
      <gene_name>LIPE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01281</protein_accession>
      <name>Monoacylglycerol lipase ABHD12</name>
      <uniprot_id>Q08DW9</uniprot_id>
      <gene_name>ABHD12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:19:59 UTC</creation_date>
  <update_date>2020-04-16 20:39:53 UTC</update_date>
  <accession>BMDB0000132</accession>
  <secondary_accessions>
    <accession>BMDB00132</accession>
  </secondary_accessions>
  <name>Guanine</name>
  <description>Guanine, also known as G or mearlmaid aa, belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring. Guanine exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Guanine exists in all living species, ranging from bacteria to humans. Guanine has been found to be associated with several diseases known as colorectal cancer, alzheimer's disease, lewy body disease, and frontotemporal dementia; also guanine has been linked to the inborn metabolic disorders including lesch-nyhan syndrome.</description>
  <synonyms>
    <synonym>2-Amino-6-hydroxypurine</synonym>
    <synonym>2-Amino-6-oxopurine</synonym>
    <synonym>G</synonym>
    <synonym>Gua</synonym>
    <synonym>2-Amino-1,7-dihydro-6H-purin-6-one</synonym>
    <synonym>2-Amino-1,9-dihydro-6H-purin-6-one</synonym>
    <synonym>2-Amino-1,9-dihydro-purin-6-one</synonym>
    <synonym>2-Amino-3,7-dihydro-6H-purin-6-one</synonym>
    <synonym>2-Amino-6-hydroxy-1H-purine</synonym>
    <synonym>2-Amino-6-purinol</synonym>
    <synonym>2-Amino-hypoxanthine</synonym>
    <synonym>2-Aminohypoxanthine</synonym>
    <synonym>6-Hydroxy-2-aminopurine</synonym>
    <synonym>C.I. natural white 1</synonym>
    <synonym>CI natural white 1</synonym>
    <synonym>Dew pearl</synonym>
    <synonym>Guanin</synonym>
    <synonym>Guanine enol</synonym>
    <synonym>GUN</synonym>
    <synonym>Mearlmaid</synonym>
    <synonym>Mearlmaid aa</synonym>
    <synonym>Natural pearl essence</synonym>
    <synonym>Natural white 1</synonym>
    <synonym>Naturon</synonym>
    <synonym>Pathocidin</synonym>
    <synonym>Pearl essence</synonym>
    <synonym>Stella polaris</synonym>
  </synonyms>
  <chemical_formula>C5H5N5O</chemical_formula>
  <average_molecular_weight>151.1261</average_molecular_weight>
  <monisotopic_moleculate_weight>151.049409807</monisotopic_moleculate_weight>
  <iupac_name>2-amino-6,7-dihydro-3H-purin-6-one</iupac_name>
  <traditional_iupac>2-aminohypoxanthine</traditional_iupac>
  <cas_registry_number>73-40-5</cas_registry_number>
  <smiles>NC1=NC(=O)C2=C(N1)N=CN2</smiles>
  <inchi>InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)</inchi>
  <inchikey>UYTPUPDQBNUYGX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Purines and purine derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Purine</substituent>
      <substituent>Pyrimidine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-aminopurines</external_descriptor>
      <external_descriptor>a purine</external_descriptor>
      <external_descriptor>a purine base</external_descriptor>
      <external_descriptor>oxopurine</external_descriptor>
      <external_descriptor>purine nucleobase</external_descriptor>
      <external_descriptor>purines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>360 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>2.08 mg/mL at 37 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.91</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-6,7-dihydro-3H-purin-6-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>151.1261</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>151.049409807</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=C(N1)N=CN2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H5N5O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UYTPUPDQBNUYGX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>96.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440048</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw whole milk</comment>
      <references>
        <reference>
          <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
          <pubmed_id>6539345</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00242</kegg_id>
  <drugbank_id>DB02377</drugbank_id>
  <foodb_id>FDB004222</foodb_id>
  <chemspider_id>744</chemspider_id>
  <pubchem_compound_id>764</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16235</chebi_id>
  <knapsack_id>C00001501</knapsack_id>
  <wikipedia_id>Guanine</wikipedia_id>
  <meta_cyc_id>GUANINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34363</bigg_id>
  <metlin_id>315</metlin_id>
  <synthesis_reference>Xiao, Xuhua; Ma, Weiyong.  One-pot synthesis of guanine.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2007),     10pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
      <pubmed_id>6539345</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00440</protein_accession>
      <name>Hypoxanthine-guanine phosphoribosyltransferase</name>
      <uniprot_id>Q3SZ18</uniprot_id>
      <gene_name>HPRT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02183</protein_accession>
      <name>Guanine nucleotide-binding protein G(t) subunit alpha-1</name>
      <uniprot_id>P04695</uniprot_id>
      <gene_name>GNAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02184</protein_accession>
      <name>Guanine nucleotide-binding protein G(t) subunit alpha-3</name>
      <uniprot_id>P0C7Q4</uniprot_id>
      <gene_name>GNAT3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02185</protein_accession>
      <name>Guanine nucleotide-binding protein G(I)/G(S)/G(O) subunit gamma-11</name>
      <uniprot_id>Q5E9F0</uniprot_id>
      <gene_name>GNG11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02186</protein_accession>
      <name>Guanine nucleotide-binding protein G(t) subunit alpha-2</name>
      <uniprot_id>P04696</uniprot_id>
      <gene_name>GNAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02187</protein_accession>
      <name>Guanine nucleotide binding protein-like 2 (Nucleolar)</name>
      <uniprot_id>Q2YDL0</uniprot_id>
      <gene_name>GNL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02188</protein_accession>
      <name>Guanine nucleotide-binding protein subunit alpha-11</name>
      <uniprot_id>P38409</uniprot_id>
      <gene_name>GNA11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02189</protein_accession>
      <name>Guanine nucleotide binding protein (G protein), alpha inhibiting activity polypeptide 3</name>
      <uniprot_id>Q3ZCA7</uniprot_id>
      <gene_name>GNAI3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02190</protein_accession>
      <name>Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-2</name>
      <uniprot_id>P11017</uniprot_id>
      <gene_name>GNB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02191</protein_accession>
      <name>Guanine nucleotide-binding protein subunit alpha-14</name>
      <uniprot_id>P38408</uniprot_id>
      <gene_name>GNA14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02192</protein_accession>
      <name>Guanine nucleotide-binding protein G(I)/G(S)/G(O) subunit gamma-12</name>
      <uniprot_id>Q28024</uniprot_id>
      <gene_name>GNG12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02193</protein_accession>
      <name>Guanine nucleotide-binding protein G(s) subunit alpha isoforms short</name>
      <uniprot_id>P04896</uniprot_id>
      <gene_name>GNAS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02194</protein_accession>
      <name>Guanine nucleotide-binding protein G(i), alpha-1 subunit</name>
      <uniprot_id>P63097</uniprot_id>
      <gene_name>GNAI1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02195</protein_accession>
      <name>Guanine nucleotide binding protein alpha subunit</name>
      <uniprot_id>Q6U8D6</uniprot_id>
      <gene_name>Gnas</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02196</protein_accession>
      <name>Guanine nucleotide-binding protein G(I)/G(S)/G(O) subunit gamma-3</name>
      <uniprot_id>P63214</uniprot_id>
      <gene_name>GNG3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02197</protein_accession>
      <name>Guanine nucleotide-binding protein, beta-1 subunit</name>
      <uniprot_id>A7E3V7</uniprot_id>
      <gene_name>GNB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02198</protein_accession>
      <name>Guanine nucleotide-binding protein-like 3-like protein</name>
      <uniprot_id>Q3T0J9</uniprot_id>
      <gene_name>GNL3L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02199</protein_accession>
      <name>Guanine nucleotide-binding protein G(T) subunit gamma-T1</name>
      <uniprot_id>P02698</uniprot_id>
      <gene_name>GNGT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02200</protein_accession>
      <name>Guanine nucleotide-binding protein G(o) subunit alpha</name>
      <uniprot_id>P08239</uniprot_id>
      <gene_name>GNAO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02201</protein_accession>
      <name>Guanine nucleotide-binding protein G(I)/G(S)/G(O) subunit gamma-T2</name>
      <uniprot_id>P50154</uniprot_id>
      <gene_name>GNGT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02202</protein_accession>
      <name>Guanine nucleotide-binding protein G(I)/G(S)/G(O) subunit gamma-5</name>
      <uniprot_id>P63217</uniprot_id>
      <gene_name>GNG5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02203</protein_accession>
      <name>Guanine nucleotide-binding protein G(I)/G(S)/G(O) subunit gamma-2</name>
      <uniprot_id>P63212</uniprot_id>
      <gene_name>GNG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02204</protein_accession>
      <name>Target of rapamycin complex subunit LST8</name>
      <uniprot_id>Q17QU5</uniprot_id>
      <gene_name>MLST8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02205</protein_accession>
      <name>Guanine nucleotide-binding protein Gq</name>
      <uniprot_id>Q4JM29</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02206</protein_accession>
      <name>Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-1</name>
      <uniprot_id>P62871</uniprot_id>
      <gene_name>GNB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02207</protein_accession>
      <name>Guanine nucleotide binding protein-like 2 (Nucleolar)</name>
      <uniprot_id>Q1JP69</uniprot_id>
      <gene_name>GNL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02208</protein_accession>
      <name>Guanine nucleotide-binding protein G(I)/G(S)/G(O) subunit gamma-7</name>
      <uniprot_id>P30671</uniprot_id>
      <gene_name>GNG7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:00 UTC</creation_date>
  <update_date>2020-04-14 22:46:32 UTC</update_date>
  <accession>BMDB0000133</accession>
  <secondary_accessions>
    <accession>BMDB00133</accession>
  </secondary_accessions>
  <name>Guanosine</name>
  <description>Guanosine, also known as G or 2-amino-inosine, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Guanosine exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Guanosine exists in all living species, ranging from bacteria to humans. In cattle, guanosine is involved in a couple of metabolic pathways, which include the intracellular signalling through adenosine receptor A2A and adenosine pathway and the intracellular signalling through adenosine receptor A2B and adenosine pathway. Guanosine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2(3H)-Imino-9-beta-D-ribofuranosyl-9H-purin-6(1H)-one</synonym>
    <synonym>2-Amino-1,9-dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one</synonym>
    <synonym>2-Amino-9-beta-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one</synonym>
    <synonym>9-beta-D-Ribofuranosyl-guanine</synonym>
    <synonym>G</synonym>
    <synonym>Guanine riboside</synonym>
    <synonym>Guanine-9-beta-D-ribofuranoside</synonym>
    <synonym>Guanosin</synonym>
    <synonym>Guo</synonym>
    <synonym>2(3H)-Imino-9-b-D-ribofuranosyl-9H-purin-6(1H)-one</synonym>
    <synonym>2(3H)-Imino-9-β-D-ribofuranosyl-9H-purin-6(1H)-one</synonym>
    <synonym>2-Amino-1,9-dihydro-9-b-D-ribofuranosyl-6H-purin-6-one</synonym>
    <synonym>2-Amino-1,9-dihydro-9-β-D-ribofuranosyl-6H-purin-6-one</synonym>
    <synonym>2-Amino-9-b-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one</synonym>
    <synonym>2-Amino-9-β-D-ribofuranosyl-1,9-dihydro-6H-purin-6-one</synonym>
    <synonym>9-b-D-Ribofuranosyl-guanine</synonym>
    <synonym>9-Β-D-ribofuranosyl-guanine</synonym>
    <synonym>Guanine-9-b-D-ribofuranoside</synonym>
    <synonym>Guanine-9-β-D-ribofuranoside</synonym>
    <synonym>2-Amino-1,9-dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one</synonym>
    <synonym>2-Amino-inosine</synonym>
    <synonym>9-beta-delta-Ribofuranosyl-guanine</synonym>
    <synonym>b-D-Ribofuranoside guanine-9</synonym>
    <synonym>beta-delta-Ribofuranoside guanine-9</synonym>
    <synonym>Ribonucleoside</synonym>
    <synonym>Vernine</synonym>
  </synonyms>
  <chemical_formula>C10H13N5O5</chemical_formula>
  <average_molecular_weight>283.2407</average_molecular_weight>
  <monisotopic_moleculate_weight>283.091668551</monisotopic_moleculate_weight>
  <iupac_name>2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one</iupac_name>
  <traditional_iupac>guanosine</traditional_iupac>
  <cas_registry_number>118-00-3</cas_registry_number>
  <smiles>NC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1</smiles>
  <inchi>InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1</inchi>
  <inchikey>NYHBQMYGNKIUIF-UUOKFMHZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleosides</class>
    <sub_class/>
    <direct_parent>Purine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Purines and purine derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleoside</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ribonucleosides</external_descriptor>
      <external_descriptor>guanosines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>239 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.7 mg/mL at 18 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.9</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>283.2407</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>283.091668551</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H13N5O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NYHBQMYGNKIUIF-UUOKFMHZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>155.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>64.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3027</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.830 +/- 0.320</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52.</reference_text>
          <pubmed_id>1897275</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68.</reference_text>
          <pubmed_id>11242448</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <pubchem_compound_id>6802</pubchem_compound_id>
  <kegg_id>C00387</kegg_id>
  <chemspider_id>6544</chemspider_id>
  <drugbank_id>DB02857</drugbank_id>
  <pdbe_id/>
  <chebi_id>16750</chebi_id>
  <knapsack_id>C00019679</knapsack_id>
  <meta_cyc_id>GUANOSINE</meta_cyc_id>
  <wikipedia_id>Guanosine</wikipedia_id>
  <foodb_id>FDB003632</foodb_id>
  <phenol_explorer_compound_id/>
  <bigg_id>51567</bigg_id>
  <metlin_id>87</metlin_id>
  <synthesis_reference>Tang, Shengrong; Huang, Weihong; Hou, Zuorong.  Process of guanosine production by fermentation.    Gongye Weishengwu  (1998),  28(4),  11-16.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52.</reference_text>
      <pubmed_id>1897275</pubmed_id>
    </reference>
    <reference>
      <reference_text>Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68.</reference_text>
      <pubmed_id>11242448</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00149</protein_accession>
      <name>Cytosolic purine 5'-nucleotidase</name>
      <uniprot_id>O46411</uniprot_id>
      <gene_name>NT5C2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00159</protein_accession>
      <name>5'-nucleotidase</name>
      <uniprot_id>Q05927</uniprot_id>
      <gene_name>NT5E</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01085</protein_accession>
      <name>DNA-directed RNA polymerase</name>
      <uniprot_id>A6QLS0</uniprot_id>
      <gene_name>POLR1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01086</protein_accession>
      <name>Ribonucleoside-diphosphate reductase</name>
      <uniprot_id>Q32LP1</uniprot_id>
      <gene_name>RRM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01087</protein_accession>
      <name>DNA-directed RNA polymerase</name>
      <uniprot_id>A5PJW8</uniprot_id>
      <gene_name>POLR2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02547</protein_accession>
      <name>RpB2</name>
      <uniprot_id>B2WTN5</uniprot_id>
      <gene_name>rpB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:01 UTC</creation_date>
  <update_date>2020-04-16 20:38:57 UTC</update_date>
  <accession>BMDB0000134</accession>
  <secondary_accessions>
    <accession>BMDB00134</accession>
  </secondary_accessions>
  <name>Fumaric acid</name>
  <description>Fumaric acid, also known as fumarate or E297, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Fumaric acid exists as a solid, possibly soluble (in water), and a weakly acidic compound (based on its pKa) molecule. Fumaric acid exists in all living species, ranging from bacteria to humans. Fumaric acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2E)-2-Butenedioic acid</synonym>
    <synonym>(e)-2-Butenedioic acid</synonym>
    <synonym>e297</synonym>
    <synonym>Fumarsaeure</synonym>
    <synonym>trans-1,2-Ethylenedicarboxylic acid</synonym>
    <synonym>trans-But-2-enedioic acid</synonym>
    <synonym>trans-Butenedioic acid</synonym>
    <synonym>(2E)-2-Butenedioate</synonym>
    <synonym>(e)-2-Butenedioate</synonym>
    <synonym>trans-1,2-Ethylenedicarboxylate</synonym>
    <synonym>trans-But-2-enedioate</synonym>
    <synonym>trans-Butenedioate</synonym>
    <synonym>Fumarate</synonym>
    <synonym>(2E)-But-2-enedioate</synonym>
    <synonym>(2E)-But-2-enedioic acid</synonym>
    <synonym>2-(e)-Butenedioate</synonym>
    <synonym>2-(e)-Butenedioic acid</synonym>
    <synonym>Allomaleate</synonym>
    <synonym>Allomaleic acid</synonym>
    <synonym>Boletate</synonym>
    <synonym>Boletic acid</synonym>
    <synonym>FC 33</synonym>
    <synonym>Lichenate</synonym>
    <synonym>Lichenic acid</synonym>
    <synonym>trans-2-Butenedioate</synonym>
    <synonym>trans-2-Butenedioic acid</synonym>
    <synonym>Furamag</synonym>
    <synonym>Mafusol</synonym>
    <synonym>Fumaric acid</synonym>
  </synonyms>
  <chemical_formula>C4H4O4</chemical_formula>
  <average_molecular_weight>116.0722</average_molecular_weight>
  <monisotopic_moleculate_weight>116.010958616</monisotopic_moleculate_weight>
  <iupac_name>(2E)-but-2-enedioic acid</iupac_name>
  <traditional_iupac>fumaric acid</traditional_iupac>
  <cas_registry_number>110-17-8</cas_registry_number>
  <smiles>OC(=O)\C=C\C(O)=O</smiles>
  <inchi>InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+</inchi>
  <inchikey>VZCYOOQTPOCHFL-OWOJBTEDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Dicarboxylic acids and derivatives</sub_class>
    <direct_parent>Dicarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>butenedioic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>549 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>7.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.46</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.041</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-but-2-enedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>116.0722</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>116.010958616</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)\C=C\C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H4O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VZCYOOQTPOCHFL-OWOJBTEDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>24.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Electron Transport Chain</name>
      <smpdb_id>SMP0087261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37314</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1.2+/-0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>299+/-55</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>141+/-64</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11.63 +/- 3.65</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2 - 81</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7 - 23</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10 - 23</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11.20 +/- 4.36</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12.54 +/- 2.98</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 54 Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
          <pubmed_id>23394630</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from Danish Holstein-Friesian (n = 456) and Jersey cows (n = 436)</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
          <pubmed_id>23182357</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>36-208</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>107.37 +/- 14.42</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>123.02 +/- 19.31</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>160.89 +/- 17.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>73-178</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>140</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>84.76 +/- 11.89</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>37-49</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>19-315</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>5.82</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1.42</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>6.44</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1.64</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>18+/-7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>8.75 +/- 3.84</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>11.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>11.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>7.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>7.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>11.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>11.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>8.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>8.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>11 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>8 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>12 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>9 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>220+/-76</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>27+/-8</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00122</kegg_id>
  <drugbank_id>DB01677</drugbank_id>
  <foodb_id>FDB003291</foodb_id>
  <chemspider_id>10197150</chemspider_id>
  <pubchem_compound_id>444972</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18012</chebi_id>
  <knapsack_id>C00001183</knapsack_id>
  <wikipedia_id>Fumaric_Acid</wikipedia_id>
  <meta_cyc_id>FUM</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33938</bigg_id>
  <metlin_id>3242</metlin_id>
  <synthesis_reference>Dong, Changsheng; Ma, Xinming.  Method for preparation of fumaric acid from the tail gas acid spray solution from oxidation of phthalic anhydride.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2007),  5pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
      <pubmed_id>23182357</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
      <pubmed_id>23394630</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:03 UTC</creation_date>
  <update_date>2020-04-15 22:13:13 UTC</update_date>
  <accession>BMDB0000138</accession>
  <secondary_accessions>
    <accession>BMDB00138</accession>
  </secondary_accessions>
  <name>Glycocholic acid</name>
  <description>Glycocholic acid, also known as glycocholate or N-choloyl-glycine, belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton. Glycocholic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Glycocholic acid has been found to be associated with several diseases known as crohn's disease, hepatobiliary diseases, cystic fibrosis, and portal vein obstruction; also glycocholic acid has been linked to the inborn metabolic disorders including celiac disease.</description>
  <synonyms>
    <synonym>Glycocholate</synonym>
    <synonym>3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycine</synonym>
    <synonym>3a,7a,12a-Trihydroxy-5b-cholanic acid-24-glycine</synonym>
    <synonym>3a,7a,12a-Trihydroxy-N-(carboxymethyl)-5b-cholan-24-amide</synonym>
    <synonym>Cholylglycine</synonym>
    <synonym>Glycine cholate</synonym>
    <synonym>Glycoreductodehydrocholic acid</synonym>
    <synonym>Glycylcholate</synonym>
    <synonym>Glycylcholic acid</synonym>
    <synonym>N-(Carboxymethyl)-3a,7a,12a-trihydroxy-5b-cholan-24-amide</synonym>
    <synonym>N-Choloyl-glycine</synonym>
    <synonym>N-Choloylglycine</synonym>
    <synonym>Glycocholic acid, sodium salt</synonym>
    <synonym>Glycocholate sodium</synonym>
  </synonyms>
  <chemical_formula>C26H43NO6</chemical_formula>
  <average_molecular_weight>465.6227</average_molecular_weight>
  <monisotopic_moleculate_weight>465.309038113</monisotopic_moleculate_weight>
  <iupac_name>2-[(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid</iupac_name>
  <traditional_iupac>[(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15?,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1</inchi>
  <inchikey>RFDAIACWWDREDC-MZMBZMQMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Glycinated bile acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Trihydroxy bile acids, alcohols and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycinated bile acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>170 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0033 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.65</value>
      <source>RODA,A ET AL. (1990)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>465.6227</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>465.309038113</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H43NO6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15?,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RFDAIACWWDREDC-MZMBZMQMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>127.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>123.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>53.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347319</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By GC-TOFMS and UPLC-QTOFMS</comment>
      <references>
        <reference>
          <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
          <pubmed_id>27999311</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB012346</foodb_id>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <pubchem_compound_id>23617285</pubchem_compound_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Glycocholic acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Cortese, Frank; Bauman, Louis.  A synthesis of conjugated bile acids. I. Glycocholic acid.  Journal of the American Chemical Society  (1935),  57  1393-5.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
      <pubmed_id>27999311</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:04 UTC</creation_date>
  <update_date>2020-04-14 22:46:35 UTC</update_date>
  <accession>BMDB0000139</accession>
  <secondary_accessions>
    <accession>BMDB00139</accession>
  </secondary_accessions>
  <name>Glyceric acid</name>
  <description>Glyceric acid, also known as glycerate or D-groa, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Glyceric acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Glyceric acid exists in all living species, ranging from bacteria to humans. Glyceric acid is a potentially toxic compound. Glyceric acid has been found to be associated with several diseases known as irritable bowel syndrome, ulcerative colitis, and eosinophilic esophagitis; also glyceric acid has been linked to several inborn metabolic disorders including primary hyperoxaluria and primary hyperoxaluria II.</description>
  <synonyms>
    <synonym>alpha,beta-Hydroxypropionic acid</synonym>
    <synonym>D-GroA</synonym>
    <synonym>R-Glyceric acid</synonym>
    <synonym>Glycerate</synonym>
    <synonym>(R)-Glycerate</synonym>
    <synonym>a,b-Hydroxypropionate</synonym>
    <synonym>a,b-Hydroxypropionic acid</synonym>
    <synonym>alpha,beta-Hydroxypropionate</synonym>
    <synonym>R-Glycerate</synonym>
    <synonym>(R)-Glyceric acid</synonym>
    <synonym>D-Glycerate</synonym>
    <synonym>D-Glyceric acid</synonym>
    <synonym>(2R)-2,3-Dihydroxypropanoic acid</synonym>
    <synonym>(R)-2,3-Dihydroxypropanoic acid</synonym>
    <synonym>D-2,3-Dihydroxypropanoic acid</synonym>
  </synonyms>
  <chemical_formula>C3H6O4</chemical_formula>
  <average_molecular_weight>106.0773</average_molecular_weight>
  <monisotopic_moleculate_weight>106.02660868</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2,3-dihydroxypropanoic acid</iupac_name>
  <traditional_iupac>glycerate</traditional_iupac>
  <cas_registry_number>473-81-4</cas_registry_number>
  <smiles>OC[C@@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m1/s1</inchi>
  <inchikey>RBNPOMFGQQGHHO-UWTATZPHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glyceric_acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sugar acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>glyceric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2,3-dihydroxypropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>106.0773</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>106.02660868</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H6O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RBNPOMFGQQGHHO-UWTATZPHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>20.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439228</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By GC-MS and LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Characterization of the biochemical variability of bovine milk using metabolomics</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB012242</foodb_id>
  <kegg_id>C00258</kegg_id>
  <pubchem_compound_id>439194</pubchem_compound_id>
  <chemspider_id>388334</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>32398</chebi_id>
  <knapsack_id>C00001185</knapsack_id>
  <meta_cyc_id>GLYCERATE</meta_cyc_id>
  <wikipedia_id>Glyceric acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34424</bigg_id>
  <metlin_id>280</metlin_id>
  <synthesis_reference>Kyriacou, Demetrios; Tougas, Terrence P.  Preparation of glyceric acid by anodic oxidation of glycerol at a silver oxide electrode.    Journal of Organic Chemistry  (1987),  52(11),  2318-19.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
    <reference>
      <reference_text>Characterization of the biochemical variability of bovine milk using metabolomics</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:05 UTC</creation_date>
  <update_date>2020-03-13 16:19:03 UTC</update_date>
  <accession>BMDB0000140</accession>
  <secondary_accessions>
    <accession>BMDB00140</accession>
  </secondary_accessions>
  <name>Glucosylceramide</name>
  <description/>
  <synonyms>
    <synonym>beta-GalCer</synonym>
    <synonym>Galbeta-cer(D18:1/24:0)</synonym>
    <synonym>GalCer(D18:1/24:0)</synonym>
    <synonym>b-GalCer</synonym>
    <synonym>Β-galcer</synonym>
    <synonym>b-D-Galactosyl-N-(tetracosanoyl)sphingosine</synonym>
    <synonym>β-D-galactosyl-N-(tetracosanoyl)sphingosine</synonym>
    <synonym>Kerasin</synonym>
    <synonym>Cerasine</synonym>
    <synonym>beta-D-Galactosyl-N-(N-acyl)-D-sphingosine</synonym>
  </synonyms>
  <chemical_formula>C48H93NO8</chemical_formula>
  <average_molecular_weight>812.2539</average_molecular_weight>
  <monisotopic_moleculate_weight>811.690118957</monisotopic_moleculate_weight>
  <iupac_name>N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracosanimidic acid</iupac_name>
  <traditional_iupac>glucosylceramide</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H]\C(CCCCCCCCCCCCC)=C(\[H])[C@@]([H])(O)[C@]([H])(CO[C@]1([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O)N=C(O)CCCCCCCCCCCCCCCCCCCCCCC</smiles>
  <inchi>InChI=1S/C48H93NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(40-56-48-47(55)46(54)45(53)43(39-50)57-48)42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,41-43,45-48,50-51,53-55H,3-34,36,38-40H2,1-2H3,(H,49,52)/b37-35+/t41-,42+,43+,45-,46-,47+,48+/m0/s1</inchi>
  <inchikey>POQRWMRXUOPCLD-HIIAJUEOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17-oxo steroid</external_descriptor>
      <external_descriptor>3-hydroxy steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>Estrane and derivatives</external_descriptor>
      <external_descriptor>Estrogens</external_descriptor>
      <external_descriptor>estrane</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>9.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>13.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[(2S,3R,4E)-3-hydroxy-1-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-4-en-2-yl]tetracosanimidic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>812.2539</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>811.690118957</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]\C(CCCCCCCCCCCCC)=C(\[H])[C@@]([H])(O)[C@]([H])(CO[C@]1([H])O[C@]([H])(CO)[C@]([H])(O)[C@]([H])(O)[C@@]1([H])O)N=C(O)CCCCCCCCCCCCCCCCCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C48H93NO8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C48H93NO8/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-44(52)49-41(40-56-48-47(55)46(54)45(53)43(39-50)57-48)42(51)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,41-43,45-48,50-51,53-55H,3-34,36,38-40H2,1-2H3,(H,49,52)/b37-35+/t41-,42+,43+,45-,46-,47+,48+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>POQRWMRXUOPCLD-HIIAJUEOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>152.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>235.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>104.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <kegg_id/>
  <pubchem_compound_id>6452860</pubchem_compound_id>
  <chemspider_id/>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>75186</chebi_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Glucocerebroside</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Hazama, Kazuhiko; Kinoshita, Mikio; Onishi, Masao; Ono, Jisaburo.  Glucosylceramide fractions from plant and cereals as colon cancer inhibitors and health foods.    Jpn. Kokai Tokkyo Koho  (2005),     11 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:06 UTC</creation_date>
  <update_date>2020-04-16 20:38:57 UTC</update_date>
  <accession>BMDB0000142</accession>
  <secondary_accessions>
    <accession>BMDB00142</accession>
  </secondary_accessions>
  <name>Formic acid</name>
  <description>Formic acid, also known as formate or ameisensaeure, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Formic acid exists as a liquid, possibly soluble (in water), and a weakly acidic compound (based on its pKa) molecule. Formic acid exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>Acide formique</synonym>
    <synonym>Ameisensaeure</synonym>
    <synonym>Aminic acid</synonym>
    <synonym>Bilorin</synonym>
    <synonym>Formylic acid</synonym>
    <synonym>H-COOH</synonym>
    <synonym>HCO2H</synonym>
    <synonym>HCOOH</synonym>
    <synonym>Hydrogen carboxylic acid</synonym>
    <synonym>Methanoic acid</synonym>
    <synonym>Methoic acid</synonym>
    <synonym>Aminate</synonym>
    <synonym>Formylate</synonym>
    <synonym>Hydrogen carboxylate</synonym>
    <synonym>Methanoate</synonym>
    <synonym>Methoate</synonym>
    <synonym>Formate</synonym>
    <synonym>Add-F</synonym>
    <synonym>Ameisensaure</synonym>
    <synonym>Collo-bueglatt</synonym>
    <synonym>Collo-didax</synonym>
    <synonym>Formira</synonym>
    <synonym>Formisoton</synonym>
    <synonym>Methanoic acid monomer</synonym>
    <synonym>Myrmicyl</synonym>
    <synonym>Sodium formate</synonym>
    <synonym>Sybest</synonym>
    <synonym>Wonderbond hardener m 600l</synonym>
    <synonym>Calcium formate</synonym>
    <synonym>Cobalt(II) formate dihydrate</synonym>
    <synonym>Formic acid, aluminum salt</synonym>
    <synonym>Formic acid, copper salt</synonym>
    <synonym>Formic acid, cromium (+3) salt</synonym>
    <synonym>Lithium formate</synonym>
    <synonym>Ammonium formate</synonym>
    <synonym>Formic acid, ammonium (4:1) salt</synonym>
    <synonym>Formic acid, ammonium salt</synonym>
    <synonym>Formic acid, calcium salt</synonym>
    <synonym>Formic acid, copper (+2) salt</synonym>
    <synonym>Formic acid, lead (+2) salt</synonym>
    <synonym>Formic acid, lead salt</synonym>
    <synonym>Formic acid, nickel salt</synonym>
    <synonym>Formic acid, potassium salt</synonym>
    <synonym>Formic acid, strontium salt</synonym>
    <synonym>Mafusol</synonym>
    <synonym>Ammonium tetraformate</synonym>
    <synonym>Formic acid, 14C-labeled</synonym>
    <synonym>Formic acid, cobalt (+2) salt</synonym>
    <synonym>Formic acid, copper, ammonium salt</synonym>
    <synonym>Formic acid, sodium salt</synonym>
    <synonym>Formic acid, sodium salt, 14C-labeled</synonym>
    <synonym>Formic acid, ammonium (2:1) salt</synonym>
    <synonym>Formic acid, cadmium salt</synonym>
    <synonym>Formic acid, cesium salt</synonym>
    <synonym>Formic acid, copper, nickel salt</synonym>
    <synonym>Formic acid, cromium (+3), sodium (4:1:1) salt</synonym>
    <synonym>Formic acid, lithium salt</synonym>
    <synonym>Formic acid, magnesium salt</synonym>
    <synonym>Formic acid, nickel (+2) salt</synonym>
    <synonym>Formic acid, rubidium salt</synonym>
    <synonym>Formic acid, sodium salt, 13C-labeled</synonym>
    <synonym>Formic acid, thallium (+1) salt</synonym>
    <synonym>Formic acid, zinc salt</synonym>
    <synonym>Nickel formate dihydrate</synonym>
    <synonym>Aluminum formate</synonym>
    <synonym>Potassium formate</synonym>
    <synonym>Strontium formate</synonym>
    <synonym>Lead formate</synonym>
    <synonym>Nickel formate</synonym>
    <synonym>Chromic formate</synonym>
    <synonym>Cobaltous formate</synonym>
    <synonym>Cupric formate</synonym>
    <synonym>Magnesium formate</synonym>
    <synonym>Zinc formate</synonym>
  </synonyms>
  <chemical_formula>CH2O2</chemical_formula>
  <average_molecular_weight>46.0254</average_molecular_weight>
  <monisotopic_moleculate_weight>46.005479308</monisotopic_moleculate_weight>
  <iupac_name>formic acid</iupac_name>
  <traditional_iupac>formic acid</traditional_iupac>
  <cas_registry_number>64-18-6</cas_registry_number>
  <smiles>OC=O</smiles>
  <inchi>InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)</inchi>
  <inchikey>BDAGIHXWWSANSR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Carboxylic acids</sub_class>
    <direct_parent>Carboxylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Saturated fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>8.4 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.54</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>formic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>46.0254</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>46.005479308</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>CH2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BDAGIHXWWSANSR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>8.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>3.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androstenedione Metabolism</name>
      <smpdb_id>SMP0087271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pterine Biosynthesis</name>
      <smpdb_id>SMP0087250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18151</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 54 Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
          <pubmed_id>23394630</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>78+/-12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>1686+/-209</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>533+/-316</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15.9 (3.3 - 24)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>117.40 +/- 1.66</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12.9 (1.9 - 28)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17.7 (4.3 - 46)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>160 (103 - 380)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15.6 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>116.44 +/- 1.93</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>115.20 +/- 2.75</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>110</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>160 +/- 46</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>60-655</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>110-123</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>337</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>320</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>258</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>321</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>20+/-4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>159.7 +/- 45.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>162.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>158.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>275.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>159.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>163 +/- 33</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>160 +/- 45</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>276 +/- 104</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>723+/-184</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>823+/-240</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein.</comment>
      <references>
        <reference>
          <reference_text>Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17.</reference_text>
          <pubmed_id>22059599</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00058</kegg_id>
  <chemspider_id/>
  <drugbank_id>DB01942</drugbank_id>
  <foodb_id>FDB012804</foodb_id>
  <pdbe_id/>
  <chebi_id>30751</chebi_id>
  <pubchem_compound_id>284</pubchem_compound_id>
  <knapsack_id>C00001182</knapsack_id>
  <meta_cyc_id>FORMATE</meta_cyc_id>
  <wikipedia_id>Formic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Finholt, Albert E.; Jacobson, Eugene C. The reduction of carbon dioxide to formic acid with lithium aluminum hydride. Journal of the American Chemical Society (1952), 74 3943-4.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00014</protein_accession>
      <name>Lanosterol 14-alpha demethylase</name>
      <uniprot_id>Q4PJW3</uniprot_id>
      <gene_name>CYP51A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00117</protein_accession>
      <name>S-formylglutathione hydrolase</name>
      <uniprot_id>Q08E20</uniprot_id>
      <gene_name>ESD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00118</protein_accession>
      <name>Monofunctional C1-tetrahydrofolate synthase, mitochondrial</name>
      <uniprot_id>Q0VCR7</uniprot_id>
      <gene_name>MTHFD1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01347</protein_accession>
      <name>Solute carrier family 26, member 6</name>
      <uniprot_id>Q08DQ8</uniprot_id>
      <gene_name>SLC26A6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:07 UTC</creation_date>
  <update_date>2020-04-15 22:13:14 UTC</update_date>
  <accession>BMDB0000143</accession>
  <secondary_accessions>
    <accession>BMDB00143</accession>
  </secondary_accessions>
  <name>D-Galactose</name>
  <description>D-Galactose, also known as alpha-D-gal or alpha D-galactose, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. D-Galactose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Galactose exists in all living species, ranging from bacteria to humans. D-Galactose participates in a number of enzymatic reactions, within cattle. In particular, D-Galactose and sorbitol can be converted into melibiitol through its interaction with the enzyme Alpha-galactosidase a. In addition, D-Galactose and D-mannose can be converted into epimelibiose through its interaction with the enzyme Alpha-galactosidase a. In cattle, D-galactose is involved in the metabolic pathway called the galactose metabolism pathway. D-Galactose is a potentially toxic compound. D-Galactose has been found to be associated with several diseases known as eosinophilic esophagitis, patent ductus venosus, and colorectal cancer; also d-galactose has been linked to several inborn metabolic disorders including galactose-1-phosphate uridyltransferase deficiency and galactosemia type 1.</description>
  <synonyms>
    <synonym>ALPHA D-GALACTOSE</synonym>
    <synonym>alpha-D-Gal</synonym>
    <synonym>Gal-alpha</synonym>
    <synonym>alpha-D-Galactose</synonym>
    <synonym>a D-GALACTOSE</synonym>
    <synonym>Α D-galactose</synonym>
    <synonym>a-D-Gal</synonym>
    <synonym>Α-D-gal</synonym>
    <synonym>Gal-a</synonym>
    <synonym>Gal-α</synonym>
    <synonym>a-D-Galactose</synonym>
    <synonym>Α-D-galactose</synonym>
    <synonym>(+)-Galactose</synonym>
    <synonym>5Abp</synonym>
    <synonym>8Abp</synonym>
    <synonym>alpha-D-Galactopyranose</synonym>
    <synonym>D-(+)-Galactose</synonym>
    <synonym>D-Hexose</synonym>
    <synonym>GAL</synonym>
    <synonym>Galactose</synonym>
    <synonym>Galactose (NF)</synonym>
    <synonym>GLA</synonym>
    <synonym>GLC</synonym>
    <synonym>Hexose</synonym>
    <synonym>SHU 508 a</synonym>
    <synonym>SH-TA-508</synonym>
    <synonym>SHU 508</synonym>
    <synonym>Levovist</synonym>
    <synonym>SHU-508</synonym>
  </synonyms>
  <chemical_formula>C6H12O6</chemical_formula>
  <average_molecular_weight>180.1559</average_molecular_weight>
  <monisotopic_moleculate_weight>180.063388116</monisotopic_moleculate_weight>
  <iupac_name>(2S,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>galactose</traditional_iupac>
  <cas_registry_number>59-23-4</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5-,6+/m1/s1</inchi>
  <inchikey>WQZGKKKJIJFFOK-PHYPRBDBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D-galactopyranose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>170 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>683.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>180.1559</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>180.063388116</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5-,6+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WQZGKKKJIJFFOK-PHYPRBDBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>110.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Degradation</name>
      <smpdb_id>SMP0087253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102626</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>730.39 +/- 277.50</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>500 - 1700</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1200 - 1760</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>67719.0879 +/- 8881.192</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk collected 0-2 days before parturition</comment>
      <references>
        <reference>
          <reference_text>Nakamura T, Kawase H, Kimura K, Watanabe Y, Ohtani M, Arai I, Urashima T: Concentrations of sialyloligosaccharides in bovine colostrum and milk during the prepartum and early lactation. J Dairy Sci. 2003 Apr;86(4):1315-20. doi: 10.3168/jds.S0022-0302(03)73715-1.</reference_text>
          <pubmed_id>12741556</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>443</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
          <pubmed_id>2760296</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>300 +/- 18</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>334 +/- 15</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>318 +/- 19</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>310 +/- 39</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>416.306 (216.479-494.0166)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized whole milk</comment>
      <references>
        <reference>
          <reference_text>Esperanza Troyano, Mar Villamiel, Agustin Olano, Jesus Sanz, and Isabel Martinez-Castro. Monosaccharides and myo-Inositol in Commercial Milks. J. Agric. Food Chem., 1996, 44 (3), pp 815–817</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>901.88 +/- 624.82</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>190-260</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Faulkner, A., Chaiybutr, N., Peaker, M., Carrick, D. I. and Kuhn, N. J. Metabolic significance of milk glucose. J. Dairy Res. 1981, 48, 51-56</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>932.526 +/- 68.274</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>No milk type was specified in the literature. Assume it was raw milk.</comment>
      <references>
        <reference>
          <reference_text>RAJAN SHARMA YUDHISHTHIR S RAJPUT POONAM GAURAV DOGRA SUDHIR K TOMAR.  Estimation of sugars in milk by HPLC and its application in detection of adulteration of milk with soymilk. International Journal of Dairy Technology, 2009, 62(4):514-519</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>224.250 +/- 4.996</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Tommaso R.I. Cataldi, Massimiliano Angelotti, Giuliana Bianco. Determination of mono- and disaccharides in milk and milk products by high-performance anion-exchange chromatography with pulsed amperometric detection. Analytica Chimica Acta 485 (2003) 43–49</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>310 +/- 39</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>300 +/- 18</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>334 +/- 15</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>318 +/- 19</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1023.29 +/- 936.59</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>763.813 +/- 751.731</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00984</kegg_id>
  <chemspider_id/>
  <drugbank_id/>
  <foodb_id>FDB021787</foodb_id>
  <pdbe_id/>
  <chebi_id>28061</chebi_id>
  <pubchem_compound_id>439357</pubchem_compound_id>
  <knapsack_id>C00001119</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Galactose</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Avigad, Gad. Synthesis of D-galactose-6-t and D-galactosides-6-t. Carbohydrate Research (1967), 3(4), 430-4.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
      <pubmed_id>2760296</pubmed_id>
    </reference>
    <reference>
      <reference_text>Nakamura T, Kawase H, Kimura K, Watanabe Y, Ohtani M, Arai I, Urashima T: Concentrations of sialyloligosaccharides in bovine colostrum and milk during the prepartum and early lactation. J Dairy Sci. 2003 Apr;86(4):1315-20. doi: 10.3168/jds.S0022-0302(03)73715-1.</reference_text>
      <pubmed_id>12741556</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00538</protein_accession>
      <name>Galactokinase</name>
      <uniprot_id>A6H768</uniprot_id>
      <gene_name>GALK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01616</protein_accession>
      <name>Collectin-12</name>
      <uniprot_id>A6QP79</uniprot_id>
      <gene_name>COLEC12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01617</protein_accession>
      <name>Collectin-43</name>
      <uniprot_id>P42916</uniprot_id>
      <gene_name>CL43</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01618</protein_accession>
      <name>Apolipoprotein C-III</name>
      <uniprot_id>P19035</uniprot_id>
      <gene_name>APOC3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:08 UTC</creation_date>
  <update_date>2020-04-15 22:13:14 UTC</update_date>
  <accession>BMDB0000145</accession>
  <secondary_accessions>
    <accession>BMDB00145</accession>
  </secondary_accessions>
  <name>Estrone</name>
  <description>Estrone, also known as folliculin or estrovarin, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, estrone is considered to be a steroid lipid molecule. Estrone is a drug which is used for management of perimenopausal and postmenopausal symptoms. Estrone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Estrone exists in all living organisms, ranging from bacteria to humans. Estrone participates in a number of enzymatic reactions, within cattle. In particular, Estrone and phosphoadenosine phosphosulfate can be converted into estrone sulfate and adenosine 3',5'-diphosphate through the action of the enzyme estrogen sulfotransferase. In addition, Estrone can be converted into 2-hydroxyestrone; which is mediated by the enzyme cytochrome P450 1A1. In cattle, estrone is involved in the metabolic pathway called the estrone metabolism pathway. Estrone is a potentially toxic compound.</description>
  <synonyms>
    <synonym>3-Hydroxy-1,3,5(10)-estratrien-17-one</synonym>
    <synonym>Follicular hormone</synonym>
    <synonym>Folliculin</synonym>
    <synonym>Oestrone</synonym>
    <synonym>(+)-Estrone</synonym>
    <synonym>1,3,5(10)-Estratrien-3-ol-17-one</synonym>
    <synonym>3-Hydroxy-17-keto-estra-1,3,5-triene</synonym>
    <synonym>3-Hydroxyestra-1,3,5(10)-trien-17-one</synonym>
    <synonym>3-Hydroxyestra-1,3,5(10)-triene-17-one</synonym>
    <synonym>3-Hydroxyoestra-1,3,5(10)-trien-17-one</synonym>
    <synonym>D1,3,5(10)-Estratrien-3-ol-17-one</synonym>
    <synonym>Estrone, (+-)-isomer</synonym>
    <synonym>Hyrex brand OF estrone</synonym>
    <synonym>Estrone, (9 beta)-isomer</synonym>
    <synonym>Estrovarin</synonym>
    <synonym>Kestrone</synonym>
    <synonym>Wehgen</synonym>
    <synonym>Estrone, (8 alpha)-isomer</synonym>
    <synonym>Hauck brand OF estrone</synonym>
    <synonym>Unigen</synonym>
    <synonym>Vortech brand OF estrone</synonym>
  </synonyms>
  <chemical_formula>C18H22O2</chemical_formula>
  <average_molecular_weight>270.3661</average_molecular_weight>
  <monisotopic_moleculate_weight>270.161979948</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one</iupac_name>
  <traditional_iupac>(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one</traditional_iupac>
  <cas_registry_number>53-16-7</cas_registry_number>
  <smiles>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</smiles>
  <inchi>InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1</inchi>
  <inchikey>DNXHEGUUPJUMQT-CBZIJGRNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17-oxo steroid</external_descriptor>
      <external_descriptor>3-hydroxy steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>Estrane and derivatives</external_descriptor>
      <external_descriptor>Estrogens</external_descriptor>
      <external_descriptor>estrane</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>258 - 260 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.03 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.13</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-5.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>270.3661</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>270.161979948</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H22O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DNXHEGUUPJUMQT-CBZIJGRNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Androstenedione Metabolism</name>
      <smpdb_id>SMP0087271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sulfate/Sulfite Metabolism</name>
      <smpdb_id>SMP0087216</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>246066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>246067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>246068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>266010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>266011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>266012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1167</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.000269</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.0018</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS in Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00003699 +/- 0.000003699</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>commercial skim milk</comment>
      <references>
        <reference>
          <reference_text>Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3.</reference_text>
          <pubmed_id>512140</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000125 +/- 0.000009986</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial whole milk</comment>
      <references>
        <reference>
          <reference_text>Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3.</reference_text>
          <pubmed_id>512140</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00003366 - 0.00007471</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Unprocessed skim milk</comment>
      <references>
        <reference>
          <reference_text>Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3.</reference_text>
          <pubmed_id>512140</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000206</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Unprocessed whole milk</comment>
      <references>
        <reference>
          <reference_text>Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3.</reference_text>
          <pubmed_id>512140</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0000155</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized milk with 1% fat</comment>
      <references>
        <reference>
          <reference_text>Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947.</reference_text>
          <pubmed_id>20494161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0000211</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized milk with 2% fat</comment>
      <references>
        <reference>
          <reference_text>Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947.</reference_text>
          <pubmed_id>20494161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0000755</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized half and half</comment>
      <references>
        <reference>
          <reference_text>Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947.</reference_text>
          <pubmed_id>20494161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0000100</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized skim milk</comment>
      <references>
        <reference>
          <reference_text>Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947.</reference_text>
          <pubmed_id>20494161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0000292</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized whole milk</comment>
      <references>
        <reference>
          <reference_text>Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947.</reference_text>
          <pubmed_id>20494161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00008507 +/- 0.00001110</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk with 0% fat</comment>
      <references>
        <reference>
          <reference_text>Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024.  Epub 2010 May 25.</reference_text>
          <pubmed_id>20541211</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00008877 +/- 0.000007397</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk with 0% fat</comment>
      <references>
        <reference>
          <reference_text>Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024.  Epub 2010 May 25.</reference_text>
          <pubmed_id>20541211</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000118 +/- 0.000003699</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial whole milk with 3.3.% fat</comment>
      <references>
        <reference>
          <reference_text>Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024.  Epub 2010 May 25.</reference_text>
          <pubmed_id>20541211</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000137</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial whole milk with 3.3.% fat</comment>
      <references>
        <reference>
          <reference_text>Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024.  Epub 2010 May 25.</reference_text>
          <pubmed_id>20541211</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000163</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Organic, Commercial, whole 3.3% fat</comment>
      <references>
        <reference>
          <reference_text>Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024.  Epub 2010 May 25.</reference_text>
          <pubmed_id>20541211</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000248 +/- 0.000007397</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Organic, Commercial, whole 3.3% fat</comment>
      <references>
        <reference>
          <reference_text>Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024.  Epub 2010 May 25.</reference_text>
          <pubmed_id>20541211</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00002922 +/- 0.000002589</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Holstein. From first trimester of pregnancy</comment>
      <references>
        <reference>
          <reference_text>Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e.</reference_text>
          <pubmed_id>17177502</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00167 +/- 0.000244</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Holstein. From second trimester of pregnancy</comment>
      <references>
        <reference>
          <reference_text>Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e.</reference_text>
          <pubmed_id>17177502</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00468 +/- 0.000141</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Holstein. From third trimester of pregnancy</comment>
      <references>
        <reference>
          <reference_text>Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e.</reference_text>
          <pubmed_id>17177502</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000565 +/- 0.000222</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial whole milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637.</reference_text>
          <pubmed_id>17852390</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000522</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Half skim milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000766</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000692</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00186 - 0.00209</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk, range from both high equol and low equol milk - high = diet of mainly red clover</comment>
      <references>
        <reference>
          <reference_text>Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31.</reference_text>
          <pubmed_id>19679050</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00468</kegg_id>
  <chemspider_id>5660</chemspider_id>
  <drugbank_id>DB00655</drugbank_id>
  <foodb_id>FDB012798</foodb_id>
  <pdbe_id/>
  <chebi_id>17263</chebi_id>
  <pubchem_compound_id>5870</pubchem_compound_id>
  <knapsack_id>C00003663</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Estrone</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35059</bigg_id>
  <metlin_id>264</metlin_id>
  <synthesis_reference>Kocovsky, Paved; Baines, Richard S.  Synthesis of estrone via a thallium(III)-mediated fragmentation of a 19-hydroxyandrost-5-ene precursor. Tetrahedron Letters  (1993),  34(38),  6139-40.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3.</reference_text>
      <pubmed_id>512140</pubmed_id>
    </reference>
    <reference>
      <reference_text>Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e.</reference_text>
      <pubmed_id>17177502</pubmed_id>
    </reference>
    <reference>
      <reference_text>Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637.</reference_text>
      <pubmed_id>17852390</pubmed_id>
    </reference>
    <reference>
      <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
      <pubmed_id>18412364</pubmed_id>
    </reference>
    <reference>
      <reference_text>Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31.</reference_text>
      <pubmed_id>19679050</pubmed_id>
    </reference>
    <reference>
      <reference_text>Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947.</reference_text>
      <pubmed_id>20494161</pubmed_id>
    </reference>
    <reference>
      <reference_text>Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024.  Epub 2010 May 25.</reference_text>
      <pubmed_id>20541211</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00378</protein_accession>
      <name>Estrogen sulfotransferase</name>
      <uniprot_id>P19217</uniprot_id>
      <gene_name>SULT1E1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00606</protein_accession>
      <name>Hydroxysteroid 17-beta dehydrogenase 6</name>
      <uniprot_id>Q3T001</uniprot_id>
      <gene_name>HSD17B6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00927</protein_accession>
      <name>Estradiol 17-beta-dehydrogenase 12</name>
      <uniprot_id>Q5E9H7</uniprot_id>
      <gene_name>HSD17B12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:09 UTC</creation_date>
  <update_date>2020-04-16 20:39:54 UTC</update_date>
  <accession>BMDB0000148</accession>
  <secondary_accessions>
    <accession>BMDB00148</accession>
  </secondary_accessions>
  <name>L-Glutamic acid</name>
  <description>L-Glutamic acid, also known as glutamate or acide glutamique, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Glutamic acid exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Glutamic acid exists in all living species, ranging from bacteria to humans. L-Glutamic acid participates in a number of enzymatic reactions, within cattle. In particular, N5-Formyl-THF and L-glutamic acid can be converted into tetrahydrofolic acid and N-formyl-L-glutamic acid; which is mediated by the enzyme formimidoyltransferase-cyclodeaminase. In addition, Tetrahydrofolic acid and L-glutamic acid can be converted into tetrahydrofolyl-[glu](2); which is catalyzed by the enzyme folylpolyglutamate synthase. In cattle, L-glutamic acid is involved in the metabolic pathway called the folate metabolism pathway. L-Glutamic acid is a potentially toxic compound. L-Glutamic acid has been found to be associated with several diseases known as irritable bowel syndrome, periodontal disease, ulcerative colitis, and diverticular disease; also l-glutamic acid has been linked to the inborn metabolic disorders including rett syndrome.</description>
  <synonyms>
    <synonym>(S)-2-Aminopentanedioic acid</synonym>
    <synonym>(S)-Glutamic acid</synonym>
    <synonym>Acide glutamique</synonym>
    <synonym>Acido glutamico</synonym>
    <synonym>Acidum glutamicum</synonym>
    <synonym>E</synonym>
    <synonym>Glu</synonym>
    <synonym>Glutamate</synonym>
    <synonym>GLUTAMIC ACID</synonym>
    <synonym>L-Glu</synonym>
    <synonym>L-Glutaminic acid</synonym>
    <synonym>L-Glutaminsaeure</synonym>
    <synonym>(S)-2-Aminopentanedioate</synonym>
    <synonym>(S)-Glutamate</synonym>
    <synonym>L-Glutaminate</synonym>
    <synonym>L-Glutamate</synonym>
    <synonym>(2S)-2-Aminopentanedioate</synonym>
    <synonym>(2S)-2-Aminopentanedioic acid</synonym>
    <synonym>(S)-(+)-Glutamate</synonym>
    <synonym>(S)-(+)-Glutamic acid</synonym>
    <synonym>1-Amino-propane-1,3-dicarboxylate</synonym>
    <synonym>1-Amino-propane-1,3-dicarboxylic acid</synonym>
    <synonym>1-Aminopropane-1,3-dicarboxylate</synonym>
    <synonym>1-Aminopropane-1,3-dicarboxylic acid</synonym>
    <synonym>2-Aminoglutarate</synonym>
    <synonym>2-Aminoglutaric acid</synonym>
    <synonym>2-Aminopentanedioate</synonym>
    <synonym>2-Aminopentanedioic acid</synonym>
    <synonym>a-Aminoglutarate</synonym>
    <synonym>a-Aminoglutaric acid</synonym>
    <synonym>a-Glutamate</synonym>
    <synonym>a-Glutamic acid</synonym>
    <synonym>Aciglut</synonym>
    <synonym>alpha-Aminoglutarate</synonym>
    <synonym>alpha-Aminoglutaric acid</synonym>
    <synonym>alpha-Glutamate</synonym>
    <synonym>alpha-Glutamic acid</synonym>
    <synonym>Aminoglutarate</synonym>
    <synonym>Aminoglutaric acid</synonym>
    <synonym>Glt</synonym>
    <synonym>Glusate</synonym>
    <synonym>Glut</synonym>
    <synonym>Glutacid</synonym>
    <synonym>Glutamicol</synonym>
    <synonym>Glutamidex</synonym>
    <synonym>Glutaminate</synonym>
    <synonym>Glutaminic acid</synonym>
    <synonym>Glutaminol</synonym>
    <synonym>Glutaton</synonym>
    <synonym>L-(+)-Glutamate</synonym>
    <synonym>L-(+)-Glutamic acid</synonym>
    <synonym>L-a-Aminoglutarate</synonym>
    <synonym>L-a-Aminoglutaric acid</synonym>
    <synonym>L-alpha-Aminoglutarate</synonym>
    <synonym>L-alpha-Aminoglutaric acid</synonym>
    <synonym>D Glutamate</synonym>
    <synonym>Glutamate, potassium</synonym>
    <synonym>Glutamic acid, (D)-isomer</synonym>
    <synonym>L Glutamic acid</synonym>
    <synonym>D-Glutamate</synonym>
    <synonym>L Glutamate</synonym>
    <synonym>Aluminum L glutamate</synonym>
    <synonym>Aluminum L-glutamate</synonym>
    <synonym>L-Glutamate, aluminum</synonym>
    <synonym>Potassium glutamate</synonym>
    <synonym>2-Acetamido-2-deoxy-D-glucose</synonym>
    <synonym>D-GlcNAc</synonym>
    <synonym>N-Acetyl-D-glucosamine</synonym>
    <synonym>N-Acetylchitosamine</synonym>
    <synonym>N Acetyl D glucosamine</synonym>
    <synonym>2 Acetamido 2 deoxy D glucose</synonym>
    <synonym>2 Acetamido 2 deoxyglucose</synonym>
    <synonym>2-Acetamido-2-deoxyglucose</synonym>
    <synonym>Acetylglucosamine</synonym>
    <synonym>3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oylglycine</synonym>
    <synonym>N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine</synonym>
    <synonym>N-Choloylglycine</synonym>
    <synonym>3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycine</synonym>
    <synonym>3Α,7α,12α-trihydroxy-5β-cholan-24-oylglycine</synonym>
    <synonym>N-[(3a,5b,7a,12a)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine</synonym>
    <synonym>N-[(3Α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine</synonym>
    <synonym>Glycocholate</synonym>
    <synonym>Glycine cholate</synonym>
    <synonym>Glycocholic acid, sodium salt</synonym>
    <synonym>Cholylglycine</synonym>
    <synonym>Glycocholate sodium</synonym>
    <synonym>3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid-24-glycine</synonym>
    <synonym>3alpha,7alpha,12alpha-Trihydroxy-N-(carboxymethyl)-5beta-cholan-24-amide</synonym>
    <synonym>3Α,7α,12α-trihydroxy-5β-cholanic acid-24-glycine</synonym>
    <synonym>3Α,7α,12α-trihydroxy-N-(carboxymethyl)-5β-cholan-24-amide</synonym>
    <synonym>Glycoreductodehydrocholic acid</synonym>
    <synonym>Glycylcholate</synonym>
    <synonym>Glycylcholic acid</synonym>
    <synonym>N-(Carboxymethyl)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-amide</synonym>
    <synonym>N-(Carboxymethyl)-3α,7α,12α-trihydroxy-5β-cholan-24-amide</synonym>
    <synonym>N-Choloyl-glycine</synonym>
    <synonym>3-Hydroxy-1,3,5(10)-estratrien-17-one</synonym>
    <synonym>Follicular hormone</synonym>
    <synonym>Folliculin</synonym>
    <synonym>Oestrone</synonym>
    <synonym>(+)-Estrone</synonym>
    <synonym>1,3,5(10)-Estratrien-3-ol-17-one</synonym>
    <synonym>3-Hydroxy-17-keto-estra-1,3,5-triene</synonym>
    <synonym>3-Hydroxyestra-1,3,5(10)-trien-17-one</synonym>
    <synonym>3-Hydroxyestra-1,3,5(10)-triene-17-one</synonym>
    <synonym>3-Hydroxyoestra-1,3,5(10)-trien-17-one</synonym>
    <synonym>D1,3,5(10)-Estratrien-3-ol-17-one</synonym>
    <synonym>Estrone, (+-)-isomer</synonym>
    <synonym>Hyrex brand OF estrone</synonym>
    <synonym>Estrone, (9 beta)-isomer</synonym>
    <synonym>Estrovarin</synonym>
    <synonym>Kestrone</synonym>
    <synonym>Wehgen</synonym>
    <synonym>Estrone, (8 alpha)-isomer</synonym>
    <synonym>Hauck brand OF estrone</synonym>
    <synonym>Unigen</synonym>
    <synonym>Vortech brand OF estrone</synonym>
    <synonym>alpha,beta-Hydroxypropionic acid</synonym>
    <synonym>D-GroA</synonym>
    <synonym>R-Glyceric acid</synonym>
    <synonym>Glycerate</synonym>
    <synonym>(R)-Glycerate</synonym>
    <synonym>a,b-Hydroxypropionate</synonym>
    <synonym>a,b-Hydroxypropionic acid</synonym>
    <synonym>alpha,beta-Hydroxypropionate</synonym>
    <synonym>Α,β-hydroxypropionate</synonym>
    <synonym>Α,β-hydroxypropionic acid</synonym>
    <synonym>R-Glycerate</synonym>
    <synonym>(R)-Glyceric acid</synonym>
    <synonym>D-Glycerate</synonym>
    <synonym>D-Glyceric acid</synonym>
    <synonym>(2R)-2,3-Dihydroxypropanoic acid</synonym>
    <synonym>(R)-2,3-Dihydroxypropanoic acid</synonym>
    <synonym>D-2,3-Dihydroxypropanoic acid</synonym>
    <synonym>1-Amino-2-hydroxyethane</synonym>
    <synonym>2-Amino-1-ethanol</synonym>
    <synonym>2-Amino-ethanol</synonym>
    <synonym>2-Aminoethan-1-ol</synonym>
    <synonym>2-Aminoethyl alcohol</synonym>
    <synonym>2-Hydroxyethylamine</synonym>
    <synonym>Aethanolamin</synonym>
    <synonym>Aminoethanol</synonym>
    <synonym>beta-Aminoethanol</synonym>
    <synonym>beta-Aminoethyl alcohol</synonym>
    <synonym>beta-Ethanolamine</synonym>
    <synonym>beta-Hydroxyethylamine</synonym>
    <synonym>Colamine</synonym>
    <synonym>ETA</synonym>
    <synonym>Glycinol</synonym>
    <synonym>Hea</synonym>
    <synonym>MEA</synonym>
    <synonym>MONOETHANOLAMINE</synonym>
    <synonym>b-Aminoethanol</synonym>
    <synonym>Β-aminoethanol</synonym>
    <synonym>b-Aminoethyl alcohol</synonym>
    <synonym>Β-aminoethyl alcohol</synonym>
    <synonym>b-Ethanolamine</synonym>
    <synonym>Β-ethanolamine</synonym>
    <synonym>b-Hydroxyethylamine</synonym>
    <synonym>Β-hydroxyethylamine</synonym>
    <synonym>2-Aminoethanol</synonym>
    <synonym>2-Ethanolamine</synonym>
    <synonym>2-Hydroxyethanamine</synonym>
    <synonym>Envision conditioner PDD 9020</synonym>
    <synonym>Ethylolamine</synonym>
    <synonym>H-Glycinol</synonym>
    <synonym>Monoaethanolamin</synonym>
    <synonym>Olamine</synonym>
    <synonym>2 Aminoethanol</synonym>
    <synonym>(3R,4S,5R)-5-[(1R)-1-Carboxy-2,2-difluoro-1-(phosphonooxy)ethoxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylate</synonym>
    <synonym>(1S)-2-[(3-O-b-D-Glucopyranosyl-b-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoate</synonym>
    <synonym>(1S)-2-[(3-O-b-D-Glucopyranosyl-b-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoic acid</synonym>
    <synonym>(1S)-2-[(3-O-beta-D-Glucopyranosyl-beta-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoic acid</synonym>
    <synonym>(1S)-2-[(3-O-Β-D-glucopyranosyl-β-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoate</synonym>
    <synonym>(1S)-2-[(3-O-Β-D-glucopyranosyl-β-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoic acid</synonym>
  </synonyms>
  <chemical_formula>C5H9NO4</chemical_formula>
  <average_molecular_weight>147.1293</average_molecular_weight>
  <monisotopic_moleculate_weight>147.053157781</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-aminopentanedioic acid</iupac_name>
  <traditional_iupac>L-glutamic acid</traditional_iupac>
  <cas_registry_number>56-86-0</cas_registry_number>
  <smiles>N[C@@H](CCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1</inchi>
  <inchikey>WHUUTDBJXJRKMK-VKHMYHEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Glutamic acid and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Amino acids</external_descriptor>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>glutamic acid</external_descriptor>
      <external_descriptor>glutamine family amino acid</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>8.57 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.69</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-aminopentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>147.1293</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>147.053157781</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H9NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WHUUTDBJXJRKMK-VKHMYHEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>100.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glucose-Alanine Cycle</name>
      <smpdb_id>SMP0087221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutathione Metabolism</name>
      <smpdb_id>SMP0087167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Malate-Aspartate Shuttle</name>
      <smpdb_id>SMP0087204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Glutamic Acid</name>
      <smpdb_id>SMP0119390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>368</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3076</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 24 male 17-22-month-old Charolais beef cattles.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>85.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1909 +/- 659</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Abdullah BASOGLU, Nuri BASPINAR, Alparslan COSKUN. NMR-based metabolomic evaluation in dairy cows with displaced abomasum. Turk J Vet Anim Sci (2014) 38(3):325-330</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>193-202</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>299.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>174-198</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>92+/-19</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>35-39</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>6122-7999</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By HPLC with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Miles ED, McBride BW, Jia Y, Liao SF, Boling JA, Bridges PJ, Matthews JC: Glutamine synthetase and alanine transaminase expression are decreased in livers of aged vs. young beef cows and GS can be upregulated by 17beta-estradiol implants. J Anim Sci. 2015 Sep;93(9):4500-9. doi: 10.2527/jas.2015-9294.</reference_text>
          <pubmed_id>26440349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>4092+/-928</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>425+/-180</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>196.16 +/- 64.07</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>44 - 693</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>270 - 740</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>297 +/- 8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>260 +/- 11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>303 +/- 9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>257 +/- 25</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>188.62 +/- 77.08</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>259 +/- 10</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>263 +/- 15</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>260 +/- 23</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>271 +/- 21</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>190.87 +/- 67.63</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>47577.199</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>47577.199</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>47577.199</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>47577.199</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>46217.851</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>46217.851</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>46217.851</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from 20 healthy Holstein Friesian dairy cows </comment>
      <references>
        <reference>
          <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
          <pubmed_id>23738862</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>229.91 +/- 25.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>241.62 +/- 45.32</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>196-510</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>393.05 +/- 31.17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1.69+/-0.21</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>9.83+/-1.55</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>8.38+/-0.64</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>9.21+/-0.74</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>489.03 +/- 20.47</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>910</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>80-104</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>134-942</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>380 +/- 59</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>490 +/- 92</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>517 +/- 115</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>333 +/- 12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>333 +/- 12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>238-887</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>179-448</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>342</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>442</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>425</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>317</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1702+/-471</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>379.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>490.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>516.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>361.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>541+/-234</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>1950-2430</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By paper chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Brown-Woodman PD, White IG: Amino acid composition of semen and the secretions of the male reproductive tract. Aust J Biol Sci. 1974 Aug;27(4):415-22. doi: 10.1071/bi9740415.</reference_text>
          <pubmed_id>4429492</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>3270+/-702</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00025</kegg_id>
  <chemspider_id/>
  <drugbank_id>DB00142</drugbank_id>
  <foodb_id>FDB012535</foodb_id>
  <pdbe_id/>
  <chebi_id>16015</chebi_id>
  <pubchem_compound_id>33032</pubchem_compound_id>
  <knapsack_id>C00001358</knapsack_id>
  <meta_cyc_id>GLT</meta_cyc_id>
  <wikipedia_id>L-Glutamic_Acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Horner, L.; Gross, A. Tertiary phosphines. IV. Use of phosphine imines in causing the introduction of primary amino groups. Liebigs Ann. Chem. (1955), 591 117-34.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
      <pubmed_id>23738862</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00148</protein_accession>
      <name>Glutamine synthetase</name>
      <uniprot_id>P15103</uniprot_id>
      <gene_name>GLUL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00169</protein_accession>
      <name>Folylpolyglutamate synthase, mitochondrial</name>
      <uniprot_id>A6H751</uniprot_id>
      <gene_name>FPGS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00197</protein_accession>
      <name>Glutathione synthetase</name>
      <uniprot_id>Q5EAC2</uniprot_id>
      <gene_name>GSS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00226</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>A4IFQ7</uniprot_id>
      <gene_name>BCAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00227</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase, mitochondrial</name>
      <uniprot_id>Q5EA40</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00228</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>Q0V8J6</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00229</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>Q5E9U7</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00239</protein_accession>
      <name>Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial</name>
      <uniprot_id>Q5E9N4</uniprot_id>
      <gene_name>AADAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00563</protein_accession>
      <name>Asparagine synthetase [glutamine-hydrolyzing]</name>
      <uniprot_id>Q1LZA3</uniprot_id>
      <gene_name>ASNS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00566</protein_accession>
      <name>Aspartyl aminopeptidase</name>
      <uniprot_id>Q2HJH1</uniprot_id>
      <gene_name>DNPEP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00567</protein_accession>
      <name>Aspartate aminotransferase, cytoplasmic</name>
      <uniprot_id>P33097</uniprot_id>
      <gene_name>GOT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00569</protein_accession>
      <name>Aspartate aminotransferase, mitochondrial</name>
      <uniprot_id>P12344</uniprot_id>
      <gene_name>GOT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00571</protein_accession>
      <name>Putative aspartate aminotransferase, cytoplasmic 2</name>
      <uniprot_id>Q2T9S8</uniprot_id>
      <gene_name>GOT1L1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00572</protein_accession>
      <name>Glutamyl aminopeptidase</name>
      <uniprot_id>Q32LQ0</uniprot_id>
      <gene_name>ENPEP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00596</protein_accession>
      <name>4-aminobutyrate aminotransferase, mitochondrial</name>
      <uniprot_id>Q9BGI0</uniprot_id>
      <gene_name>ABAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00631</protein_accession>
      <name>Alpha-aminoadipic semialdehyde synthase, mitochondrial</name>
      <uniprot_id>A8E657</uniprot_id>
      <gene_name>AASS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00632</protein_accession>
      <name>Probable saccharopine dehydrogenase</name>
      <uniprot_id>Q3T067</uniprot_id>
      <gene_name>SCCPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00827</protein_accession>
      <name>Glucosamine--fructose-6-phosphate aminotransferase [isomerizing] 2</name>
      <uniprot_id>Q08DQ2</uniprot_id>
      <gene_name>GFPT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00850</protein_accession>
      <name>Glutamyl-tRNA(Gln) amidotransferase subunit A homolog</name>
      <uniprot_id>Q29RP9</uniprot_id>
      <gene_name>QRSL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00852</protein_accession>
      <name>Glutamine-dependent NAD(+) synthetase</name>
      <uniprot_id>Q3ZBF0</uniprot_id>
      <gene_name>NADSYN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00855</protein_accession>
      <name>Phosphoserine aminotransferase</name>
      <uniprot_id>A6QR28</uniprot_id>
      <gene_name>PSAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00856</protein_accession>
      <name>Glutamate dehydrogenase 1, mitochondrial</name>
      <uniprot_id>P00366</uniprot_id>
      <gene_name>GLUD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00857</protein_accession>
      <name>5-oxoprolinase</name>
      <uniprot_id>Q75WB5</uniprot_id>
      <gene_name>OPLAH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00858</protein_accession>
      <name>Alanine aminotransferase 1</name>
      <uniprot_id>A4IFH5</uniprot_id>
      <gene_name>GPT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00859</protein_accession>
      <name>Tyrosine aminotransferase</name>
      <uniprot_id>Q58CZ9</uniprot_id>
      <gene_name>TAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00860</protein_accession>
      <name>Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial</name>
      <uniprot_id>A7YWE4</uniprot_id>
      <gene_name>ALDH4A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00861</protein_accession>
      <name>Kynurenine--oxoglutarate transaminase 3</name>
      <uniprot_id>Q0P5G4</uniprot_id>
      <gene_name>CCBL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00862</protein_accession>
      <name>Glutamate decarboxylase 1</name>
      <uniprot_id>Q0VCA1</uniprot_id>
      <gene_name>GAD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02099</protein_accession>
      <name>PRA1 family protein 3</name>
      <uniprot_id>Q5E9M1</uniprot_id>
      <gene_name>ARL6IP5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02100</protein_accession>
      <name>SLC1A6 protein</name>
      <uniprot_id>A6H774</uniprot_id>
      <gene_name>SLC1A6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02101</protein_accession>
      <name>Solute carrier family 1 member 2</name>
      <uniprot_id>A5HSH1</uniprot_id>
      <gene_name>SLC1A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:11 UTC</creation_date>
  <update_date>2020-04-16 20:39:54 UTC</update_date>
  <accession>BMDB0000149</accession>
  <secondary_accessions>
    <accession>BMDB00149</accession>
  </secondary_accessions>
  <name>Ethanolamine</name>
  <description>Ethanolamine, also known as aminoethanol or glycinol, belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Ethanolamine exists as a liquid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Ethanolamine exists in all living species, ranging from bacteria to humans. Ethanolamine is a potentially toxic compound. Ethanolamine has been found to be associated with several diseases known as perillyl alcohol administration for cancer treatment, irritable bowel syndrome, and ulcerative colitis; also ethanolamine has been linked to several inborn metabolic disorders including propionic acidemia and maple syrup urine disease.</description>
  <synonyms>
    <synonym>1-Amino-2-hydroxyethane</synonym>
    <synonym>2-Amino-1-ethanol</synonym>
    <synonym>2-Amino-ethanol</synonym>
    <synonym>2-Aminoethan-1-ol</synonym>
    <synonym>2-Aminoethyl alcohol</synonym>
    <synonym>2-Hydroxyethylamine</synonym>
    <synonym>Aethanolamin</synonym>
    <synonym>Aminoethanol</synonym>
    <synonym>beta-Aminoethanol</synonym>
    <synonym>beta-Aminoethyl alcohol</synonym>
    <synonym>beta-Ethanolamine</synonym>
    <synonym>beta-Hydroxyethylamine</synonym>
    <synonym>Colamine</synonym>
    <synonym>ETA</synonym>
    <synonym>Glycinol</synonym>
    <synonym>Hea</synonym>
    <synonym>MEA</synonym>
    <synonym>MONOETHANOLAMINE</synonym>
    <synonym>b-Aminoethanol</synonym>
    <synonym>Β-aminoethanol</synonym>
    <synonym>b-Aminoethyl alcohol</synonym>
    <synonym>Β-aminoethyl alcohol</synonym>
    <synonym>b-Ethanolamine</synonym>
    <synonym>Β-ethanolamine</synonym>
    <synonym>b-Hydroxyethylamine</synonym>
    <synonym>Β-hydroxyethylamine</synonym>
    <synonym>2-Aminoethanol</synonym>
    <synonym>2-Ethanolamine</synonym>
    <synonym>2-Hydroxyethanamine</synonym>
    <synonym>Envision conditioner PDD 9020</synonym>
    <synonym>Ethylolamine</synonym>
    <synonym>H-Glycinol</synonym>
    <synonym>Monoaethanolamin</synonym>
    <synonym>Olamine</synonym>
    <synonym>2 Aminoethanol</synonym>
  </synonyms>
  <chemical_formula>C2H7NO</chemical_formula>
  <average_molecular_weight>61.0831</average_molecular_weight>
  <monisotopic_moleculate_weight>61.052763851</monisotopic_moleculate_weight>
  <iupac_name>2-aminoethan-1-ol</iupac_name>
  <traditional_iupac>ethanolamine</traditional_iupac>
  <cas_registry_number>141-43-5</cas_registry_number>
  <smiles>NCCO</smiles>
  <inchi>InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2</inchi>
  <inchikey>HZAXFHJVJLSVMW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>1,2-aminoalcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>ethanolamines</external_descriptor>
      <external_descriptor>primary alcohol</external_descriptor>
      <external_descriptor>primary amine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>10.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.31</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-aminoethan-1-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>61.0831</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>61.052763851</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H7NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HZAXFHJVJLSVMW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>46.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>16.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>6.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis</name>
      <smpdb_id>SMP0072037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:0)</name>
      <smpdb_id>SMP0080430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0080431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/15:0)</name>
      <smpdb_id>SMP0080432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:0)</name>
      <smpdb_id>SMP0080433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0080434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:0)</name>
      <smpdb_id>SMP0080435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0080436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0080437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:0)</name>
      <smpdb_id>SMP0080442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0080443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:0)</name>
      <smpdb_id>SMP0080450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0080451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:0)</name>
      <smpdb_id>SMP0080457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0080458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0080459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0080460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0080461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/15:0)</name>
      <smpdb_id>SMP0080487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:0)</name>
      <smpdb_id>SMP0080488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0080489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:0)</name>
      <smpdb_id>SMP0080490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0080491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0080492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:0)</name>
      <smpdb_id>SMP0080497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0080498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:0)</name>
      <smpdb_id>SMP0080505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0080506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:0)</name>
      <smpdb_id>SMP0080512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0080513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:0)</name>
      <smpdb_id>SMP0080514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0080515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:0)</name>
      <smpdb_id>SMP0080516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0080517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0080518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:0)</name>
      <smpdb_id>SMP0080523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0080524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:0)</name>
      <smpdb_id>SMP0080531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0080532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:0)</name>
      <smpdb_id>SMP0080538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0080539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:0)</name>
      <smpdb_id>SMP0080565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0080566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0080567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:0)</name>
      <smpdb_id>SMP0080572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0080573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:0)</name>
      <smpdb_id>SMP0080580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0080581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:0)</name>
      <smpdb_id>SMP0080587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0080588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0080595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:0)</name>
      <smpdb_id>SMP0080712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0080713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:0)</name>
      <smpdb_id>SMP0080720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0080721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:0)</name>
      <smpdb_id>SMP0080727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0080728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0080765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0080772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:0)</name>
      <smpdb_id>SMP0080820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0080821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:0)</name>
      <smpdb_id>SMP0080827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0080828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0080835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:0)</name>
      <smpdb_id>SMP0080864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0080865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis</name>
      <smpdb_id>SMP0072048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:0)</name>
      <smpdb_id>SMP0082233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0082234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/15:0)</name>
      <smpdb_id>SMP0082235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:0)</name>
      <smpdb_id>SMP0082236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0082237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:0)</name>
      <smpdb_id>SMP0082238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0082239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0082240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:0)</name>
      <smpdb_id>SMP0082245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0082246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:0)</name>
      <smpdb_id>SMP0082253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0082254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:0)</name>
      <smpdb_id>SMP0082260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0082261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0082262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0082263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0082264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/15:0)</name>
      <smpdb_id>SMP0082290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:0)</name>
      <smpdb_id>SMP0082291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0082292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:0)</name>
      <smpdb_id>SMP0082293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0082294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0082295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:0)</name>
      <smpdb_id>SMP0082300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0082301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:0)</name>
      <smpdb_id>SMP0082308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0082309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:0)</name>
      <smpdb_id>SMP0082315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0082316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:0)</name>
      <smpdb_id>SMP0082317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0082318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:0)</name>
      <smpdb_id>SMP0082319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0082320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0082321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:0)</name>
      <smpdb_id>SMP0082326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0082327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:0)</name>
      <smpdb_id>SMP0082334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0082335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:0)</name>
      <smpdb_id>SMP0082341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0082342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:0)</name>
      <smpdb_id>SMP0082368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0082369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0082370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:0)</name>
      <smpdb_id>SMP0082375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0082376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:0)</name>
      <smpdb_id>SMP0082383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0082384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:0)</name>
      <smpdb_id>SMP0082390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0082391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0082398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:0)</name>
      <smpdb_id>SMP0082520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0082521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:0)</name>
      <smpdb_id>SMP0082528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0082529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:0)</name>
      <smpdb_id>SMP0082535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0082536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0082574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0082581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:0)</name>
      <smpdb_id>SMP0082629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0082630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:0)</name>
      <smpdb_id>SMP0082636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0082637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0082644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:0)</name>
      <smpdb_id>SMP0082671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0082672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446120</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>84.09 +/- 27.64</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>323</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>53 +/- 15</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>66 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>66 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>62 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>125.81 +/- 39.77</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>116.79 +/- 23.05</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00189</kegg_id>
  <chemspider_id>13835336</chemspider_id>
  <drugbank_id>DB03994</drugbank_id>
  <foodb_id>FDB030851</foodb_id>
  <pdbe_id/>
  <chebi_id>16000</chebi_id>
  <pubchem_compound_id>700</pubchem_compound_id>
  <knapsack_id>C00007279</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Ethanolamine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34189</bigg_id>
  <metlin_id>3207</metlin_id>
  <synthesis_reference>Soucaille, Philippe.  Ethanolamine production by fermentation of genetically modified Escherichia coli.    PCT Int. Appl.  (2007),     23pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00177</protein_accession>
      <name>Ectonucleotide pyrophosphatase/phosphodiesterase family member 2</name>
      <uniprot_id>A1A4K5</uniprot_id>
      <gene_name>ENPP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:12 UTC</creation_date>
  <update_date>2020-03-13 16:19:07 UTC</update_date>
  <accession>BMDB0000150</accession>
  <secondary_accessions>
    <accession>BMDB00150</accession>
  </secondary_accessions>
  <name>Gluconolactone</name>
  <description>Gluconolactone, also known as GDL (gluconate) or gluconolactone, belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group. Gluconolactone exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Gluconolactone exists in all living organisms, ranging from bacteria to humans. Gluconolactone participates in a number of enzymatic reactions, within cattle. In particular, Gluconolactone and nadph can be biosynthesized from Beta-D-glucose 6-phosphate and nadp through the action of the enzyme glucose-6-phosphate 1-dehydrogenase. In addition, Gluconolactone and water can be converted into 6-phosphogluconic acid; which is mediated by the enzyme 6-phosphogluconolactonase. In cattle, gluconolactone is involved in the metabolic pathway called the pentose phosphate pathway.</description>
  <synonyms>
    <synonym>(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one</synonym>
    <synonym>1,5-D-Gluconolactone</synonym>
    <synonym>1,5-Gluconolactone</synonym>
    <synonym>D-Aldonolactone</synonym>
    <synonym>D-Gluconic acid delta-lactone</synonym>
    <synonym>D-Gluconic acid lactone</synonym>
    <synonym>D-Gluconolactone</synonym>
    <synonym>D-Threo-aldono-1,5-lactone</synonym>
    <synonym>delta-D-Gluconolactone</synonym>
    <synonym>delta-Gluconolactone</synonym>
    <synonym>Glucarolactone</synonym>
    <synonym>Gluconic acid lactone</synonym>
    <synonym>Gluconic delta-lactone</synonym>
    <synonym>Gluconic lactone</synonym>
    <synonym>D-Gluconate delta-lactone</synonym>
    <synonym>D-Gluconate δ-lactone</synonym>
    <synonym>D-Gluconic acid δ-lactone</synonym>
    <synonym>D-Gluconate lactone</synonym>
    <synonym>Δ-D-gluconolactone</synonym>
    <synonym>Δ-gluconolactone</synonym>
    <synonym>Gluconate lactone</synonym>
    <synonym>Gluconic δ-lactone</synonym>
    <synonym>1,5-delta-Gluconolactone</synonym>
    <synonym>3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one</synonym>
    <synonym>beta-Glucono-1,5-lactone</synonym>
    <synonym>D(+)-Gluconic acid gamma-lactone</synonym>
    <synonym>D-(+)-Gluconic acid D-lactone</synonym>
    <synonym>D-(+)-Gluconic acid-delta lactone</synonym>
    <synonym>D-delta-Gluconolactone</synonym>
    <synonym>D-Gluconic acid 1,5-lactone</synonym>
    <synonym>D-Gluconic acid D-lactone</synonym>
    <synonym>D-Gluconic acid-1,5-lactone</synonym>
    <synonym>D-Gluconic acid-delta-lactone</synonym>
    <synonym>D-Gluconic delta-lactone</synonym>
    <synonym>D-Glucono-1,5-lactone</synonym>
    <synonym>D-Glucono-D-lactone</synonym>
    <synonym>delta-(+)-Gluconic acid D-lactone</synonym>
    <synonym>delta-(+)-Gluconic acid-delta lactone</synonym>
    <synonym>delta-Aldonolactone</synonym>
    <synonym>delta-delta-Gluconolactone</synonym>
    <synonym>delta-Gluconic acid 1,5-lactone</synonym>
    <synonym>delta-Gluconic acid D-lactone</synonym>
    <synonym>delta-Gluconic acid delta-lactone</synonym>
    <synonym>delta-Gluconic acid lactone</synonym>
    <synonym>delta-Gluconic acid-1,5-lactone</synonym>
    <synonym>delta-Gluconic acid-delta-lactone</synonym>
    <synonym>delta-Gluconic delta-lactone</synonym>
    <synonym>delta-Glucono-1,5-lactone</synonym>
    <synonym>delta-Glucono-delta-lactone</synonym>
    <synonym>Fujiglucon</synonym>
    <synonym>gamma-Gluconolactone</synonym>
    <synonym>Gluconate, lactone</synonym>
    <synonym>Glucono 1,5-lactone</synonym>
    <synonym>Glucono delta lactone</synonym>
    <synonym>Glucono delta-lactone</synonym>
    <synonym>Glucono gamma-lactone</synonym>
    <synonym>GDL (Gluconate)</synonym>
    <synonym>Gulonic acid gamma-lactone</synonym>
    <synonym>Glucono-delta-lactone</synonym>
  </synonyms>
  <chemical_formula>C6H10O6</chemical_formula>
  <average_molecular_weight>178.14</average_molecular_weight>
  <monisotopic_moleculate_weight>178.047738052</monisotopic_moleculate_weight>
  <iupac_name>(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one</iupac_name>
  <traditional_iupac>gluconolactone</traditional_iupac>
  <cas_registry_number>90-80-2</cas_registry_number>
  <smiles>OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1</inchi>
  <inchikey>PHOQVHQSTUBQQK-SQOUGZDYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Gluconolactones</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Delta valerolactones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Delta valerolactone</substituent>
      <substituent>Delta_valerolactone</substituent>
      <substituent>Gluconolactone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aldono-1,5-lactone</external_descriptor>
      <external_descriptor>gluconolactone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>151 - 155 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>590.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>178.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>178.047738052</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PHOQVHQSTUBQQK-SQOUGZDYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>107.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271442</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00198</kegg_id>
  <chemspider_id>6760</chemspider_id>
  <drugbank_id>DB04564</drugbank_id>
  <foodb_id>FDB001245</foodb_id>
  <pdbe_id/>
  <chebi_id>16217</chebi_id>
  <pubchem_compound_id>7027</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Gluconolactone</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>353</metlin_id>
  <synthesis_reference>Chu, Lijia.  Technology for industrial production of d-gluconolactone. Shipin Kexue (Beijing, China)  (1985),  66  13-14.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:13 UTC</creation_date>
  <update_date>2020-04-16 20:39:14 UTC</update_date>
  <accession>BMDB0000151</accession>
  <secondary_accessions>
    <accession>BMDB00151</accession>
  </secondary_accessions>
  <name>Estradiol</name>
  <description>Beta-Beta-beta-estradiol, also known as beta-beta-estradiol or beta-beta-estradiol, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, Beta-beta-estradiol is considered to be a steroid lipid molecule. Beta-Beta-beta-estradiol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Beta-Beta-beta-estradiol exists in all living organisms, ranging from bacteria to humans. In cattle, Beta-beta-estradiol is involved in the metabolic pathway called the androgen and estrogen metabolism pathway. Beta-Beta-beta-estradiol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(17beta)-Estra-1,3,5(10)-triene-3,17-diol</synonym>
    <synonym>17beta Oestradiol</synonym>
    <synonym>17beta-Estra-1,3,5(10)-triene-3,17-diol</synonym>
    <synonym>17beta-Oestradiol</synonym>
    <synonym>beta-Estradiol</synonym>
    <synonym>cis-Estradiol</synonym>
    <synonym>Estradiol-17beta</synonym>
    <synonym>Climara</synonym>
    <synonym>Divigel</synonym>
    <synonym>Estrace</synonym>
    <synonym>Estraderm</synonym>
    <synonym>Estrasorb</synonym>
    <synonym>Estring</synonym>
    <synonym>Estrogel</synonym>
    <synonym>Innofem</synonym>
    <synonym>Vagifem</synonym>
    <synonym>Vivelle</synonym>
    <synonym>(17b)-Estra-1,3,5(10)-triene-3,17-diol</synonym>
    <synonym>(17Β)-estra-1,3,5(10)-triene-3,17-diol</synonym>
    <synonym>17b Oestradiol</synonym>
    <synonym>17Β oestradiol</synonym>
    <synonym>17b-Estra-1,3,5(10)-triene-3,17-diol</synonym>
    <synonym>17Β-estra-1,3,5(10)-triene-3,17-diol</synonym>
    <synonym>17b-Oestradiol</synonym>
    <synonym>17Β-oestradiol</synonym>
    <synonym>b-Estradiol</synonym>
    <synonym>Β-estradiol</synonym>
    <synonym>Estradiol-17b</synonym>
    <synonym>Estradiol-17β</synonym>
    <synonym>(+)-3,17b-Estradiol</synonym>
    <synonym>13b-Methyl-1,3,5(10)-gonatriene-3,17b-ol</synonym>
    <synonym>17b-Estradiol</synonym>
    <synonym>3,17-Epidihydroxyestratriene</synonym>
    <synonym>3,17b-Dihydroxyestra-1,3,5(10)-triene</synonym>
    <synonym>3,17b-Estradiol</synonym>
    <synonym>Aerodiol</synonym>
    <synonym>Agofollin</synonym>
    <synonym>Altrad</synonym>
    <synonym>Amnestrogen</synonym>
    <synonym>Aquadiol</synonym>
    <synonym>Bardiol</synonym>
    <synonym>Climaderm</synonym>
    <synonym>Compudose</synonym>
    <synonym>Corpagen</synonym>
    <synonym>D-Estradiol</synonym>
    <synonym>D-Oestradiol</synonym>
    <synonym>delta-Estradiol</synonym>
    <synonym>delta-Oestradiol</synonym>
    <synonym>Dermestril</synonym>
    <synonym>Dihydro-theelin</synonym>
    <synonym>Dihydrofollicular hormone</synonym>
    <synonym>Dihydrofolliculin</synonym>
    <synonym>Dihydromenformon</synonym>
    <synonym>Dihydrotheelin</synonym>
    <synonym>Dihydroxyestrin</synonym>
    <synonym>Dimenformon</synonym>
    <synonym>Diogyn</synonym>
    <synonym>Diogynets</synonym>
    <synonym>Encore</synonym>
    <synonym>Epiestriol 50</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,17b-diol</synonym>
    <synonym>Estraderm TTS</synonym>
    <synonym>Estradiol-17-beta</synonym>
    <synonym>Estradot</synonym>
    <synonym>Estraldine</synonym>
    <synonym>Estring vaginal ring</synonym>
    <synonym>Estroclim</synonym>
    <synonym>Estroclim 50</synonym>
    <synonym>Estrogel HBF</synonym>
    <synonym>Estrovite</synonym>
    <synonym>Evorel</synonym>
    <synonym>Femestral</synonym>
    <synonym>Femogen</synonym>
    <synonym>Follicyclin</synonym>
    <synonym>Gelestra</synonym>
    <synonym>Ginosedol</synonym>
    <synonym>Gynergon</synonym>
    <synonym>Gynoestryl</synonym>
    <synonym>Lamdiol</synonym>
    <synonym>Macrodiol</synonym>
    <synonym>Menorest</synonym>
    <synonym>Nordicol</synonym>
    <synonym>Oesclim</synonym>
    <synonym>Oestergon</synonym>
    <synonym>Oestra-1,3,5(10)-triene-3,17b-diol</synonym>
    <synonym>Oestradiol</synonym>
    <synonym>Oestrogel</synonym>
    <synonym>Oestroglandol</synonym>
    <synonym>Ovahormon</synonym>
    <synonym>Ovasterol</synonym>
    <synonym>Ovastevol</synonym>
    <synonym>Ovocyclin</synonym>
    <synonym>Ovocylin</synonym>
    <synonym>Perlatanol</synonym>
    <synonym>Primofol</synonym>
    <synonym>Profoliol</synonym>
    <synonym>Profoliol b</synonym>
    <synonym>Progynon</synonym>
    <synonym>Progynon DH</synonym>
    <synonym>Sandrena 1</synonym>
    <synonym>Syndiol</synonym>
    <synonym>Systen</synonym>
    <synonym>Zumenon</synonym>
    <synonym>Estradiol hemihydrate, (17 alpha)-isomer</synonym>
    <synonym>Estradiol, (-)-isomer</synonym>
    <synonym>Estradiol, monosodium salt</synonym>
    <synonym>Estradiol-17 beta</synonym>
    <synonym>17 beta Oestradiol</synonym>
    <synonym>17 beta-Estradiol</synonym>
    <synonym>Estradiol 17 beta</synonym>
    <synonym>Estradiol monohydrate</synonym>
    <synonym>Estradiol orion brand</synonym>
    <synonym>Estradiol, (17-alpha)-isomer</synonym>
    <synonym>Estradiol, sodium salt</synonym>
    <synonym>17 beta Estradiol</synonym>
    <synonym>Estradiol hemihydrate</synonym>
    <synonym>Estradiol, (+-)-isomer</synonym>
    <synonym>Estradiol, (16 alpha,17 alpha)-isomer</synonym>
    <synonym>Estradiol-17 alpha</synonym>
    <synonym>Orion brand OF estradiol</synonym>
    <synonym>17 beta-Oestradiol</synonym>
    <synonym>Estradiol 17 alpha</synonym>
    <synonym>Estradiol 17beta</synonym>
    <synonym>Estradiol anhydrous</synonym>
    <synonym>Estradiol, (16 alpha,17 beta)-isomer</synonym>
    <synonym>Estradiol, (8 alpha,17 beta)-(+-)-isomer</synonym>
    <synonym>Estradiol, (8 alpha,17 beta)-isomer</synonym>
    <synonym>Estradiol, (9 beta,17 alpha)-isomer</synonym>
    <synonym>Estradiol, (9 beta,17 beta)-isomer</synonym>
    <synonym>Novartis pharmaceuticals brand OF estradiol</synonym>
    <synonym>Progynova</synonym>
    <synonym>Estradiol valeriante</synonym>
    <synonym>Estradiol valerate</synonym>
    <synonym>Delestrogen</synonym>
    <synonym>Progynon depot</synonym>
    <synonym>Progynon-depot</synonym>
    <synonym>Estradiol</synonym>
  </synonyms>
  <chemical_formula>C18H24O2</chemical_formula>
  <average_molecular_weight>272.382</average_molecular_weight>
  <monisotopic_moleculate_weight>272.177630012</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol</iupac_name>
  <traditional_iupac>(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol</traditional_iupac>
  <cas_registry_number>50-28-2</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</smiles>
  <inchi>InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1</inchi>
  <inchikey>VOXZDWNPVJITMN-ZBRFXRBCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17beta-hydroxy steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>Estrane and derivatives</external_descriptor>
      <external_descriptor>Estrogens</external_descriptor>
      <external_descriptor>estradiol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>178.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0036 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.01</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>272.382</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>272.177630012</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H24O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VOXZDWNPVJITMN-ZBRFXRBCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>847</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449070</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00001285 +/- 0.000005874</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>commercial skim milk</comment>
      <references>
        <reference>
          <reference_text>Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3.</reference_text>
          <pubmed_id>512140</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00002350 +/- 0.000004</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial whole milk</comment>
      <references>
        <reference>
          <reference_text>Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3.</reference_text>
          <pubmed_id>512140</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00001836 - 0.00003304</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Unprocessed skim milk</comment>
      <references>
        <reference>
          <reference_text>Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3.</reference_text>
          <pubmed_id>512140</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00003781 - 0.00005287</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Unprocessed whole milk</comment>
      <references>
        <reference>
          <reference_text>Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3.</reference_text>
          <pubmed_id>512140</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00000220</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized milk with 1% fat</comment>
      <references>
        <reference>
          <reference_text>Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947.</reference_text>
          <pubmed_id>20494161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00000330</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized milk with 2% fat</comment>
      <references>
        <reference>
          <reference_text>Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947.</reference_text>
          <pubmed_id>20494161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00000698</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized half and half</comment>
      <references>
        <reference>
          <reference_text>Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947.</reference_text>
          <pubmed_id>20494161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00000147</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized skim milk</comment>
      <references>
        <reference>
          <reference_text>Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947.</reference_text>
          <pubmed_id>20494161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00000400</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized whole milk</comment>
      <references>
        <reference>
          <reference_text>Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947.</reference_text>
          <pubmed_id>20494161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000121 +/- 0.0000257</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Holstein. From first trimester of pregnancy</comment>
      <references>
        <reference>
          <reference_text>Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e.</reference_text>
          <pubmed_id>17177502</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00006829 +/- 0.0000007343</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw. milk. Holstein. From first trimester of pregnancy</comment>
      <references>
        <reference>
          <reference_text>Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e.</reference_text>
          <pubmed_id>17177502</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000189 +/- 0.000009913</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Holstein. From second trimester of pregnancy</comment>
      <references>
        <reference>
          <reference_text>Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e.</reference_text>
          <pubmed_id>17177502</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000308 +/- 0.00001469</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Holstein. From second trimester of pregnancy</comment>
      <references>
        <reference>
          <reference_text>Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e.</reference_text>
          <pubmed_id>17177502</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000188 +/- 0.000005507</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Holstein. From third trimester of pregnancy</comment>
      <references>
        <reference>
          <reference_text>Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e.</reference_text>
          <pubmed_id>17177502</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00118 +/- 0.000128</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Holstein. From third trimester of pregnancy</comment>
      <references>
        <reference>
          <reference_text>Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e.</reference_text>
          <pubmed_id>17177502</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00008444 +/- 0.00004626</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk (commercial)</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637.</reference_text>
          <pubmed_id>17852390</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0000477</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Half skim milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0000600</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0000496</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000220 - 0.000237</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk, range from both high equol and low equol milk - high = diet of mainly red clover</comment>
      <references>
        <reference>
          <reference_text>Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31.</reference_text>
          <pubmed_id>19679050</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00951</kegg_id>
  <chemspider_id>5554</chemspider_id>
  <drugbank_id>DB00783</drugbank_id>
  <foodb_id>FDB000362</foodb_id>
  <pubchem_compound_id>5757</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16469</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Estradiol</wikipedia_id>
  <bigg_id>36456</bigg_id>
  <metlin_id>263</metlin_id>
  <synthesis_reference>Vasiljeva, L. L.; Demin, P. M.; Kochev, D. M.; Lapitskaya, M. A.; Pivnitskya, K. K.  New synthesis of estradiol from androsta-1,4-diene-3,17-dione.    Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya)  (1999),  48(3),  593-595.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3.</reference_text>
      <pubmed_id>512140</pubmed_id>
    </reference>
    <reference>
      <reference_text>Malekinejad H, Scherpenisse P, Bergwerff AA: Naturally occurring estrogens in processed milk and in raw milk (from gestated cows). J Agric Food Chem. 2006 Dec 27;54(26):9785-91. doi: 10.1021/jf061972e.</reference_text>
      <pubmed_id>17177502</pubmed_id>
    </reference>
    <reference>
      <reference_text>Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637.</reference_text>
      <pubmed_id>17852390</pubmed_id>
    </reference>
    <reference>
      <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
      <pubmed_id>18412364</pubmed_id>
    </reference>
    <reference>
      <reference_text>Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31.</reference_text>
      <pubmed_id>19679050</pubmed_id>
    </reference>
    <reference>
      <reference_text>Pape-Zambito DA, Roberts RF, Kensinger RS: Estrone and 17beta-estradiol concentrations in pasteurized-homogenized milk and commercial dairy products. J Dairy Sci. 2010 Jun;93(6):2533-40. doi: 10.3168/jds.2009-2947.</reference_text>
      <pubmed_id>20494161</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00606</protein_accession>
      <name>Hydroxysteroid 17-beta dehydrogenase 6</name>
      <uniprot_id>Q3T001</uniprot_id>
      <gene_name>HSD17B6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00927</protein_accession>
      <name>Estradiol 17-beta-dehydrogenase 12</name>
      <uniprot_id>Q5E9H7</uniprot_id>
      <gene_name>HSD17B12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02169</protein_accession>
      <name>Estrogen receptor</name>
      <uniprot_id>P49884</uniprot_id>
      <gene_name>ESR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02170</protein_accession>
      <name>Calcium-activated potassium channel subunit beta-1</name>
      <uniprot_id>Q28067</uniprot_id>
      <gene_name>KCNMB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:14 UTC</creation_date>
  <update_date>2020-03-13 16:19:08 UTC</update_date>
  <accession>BMDB0000152</accession>
  <secondary_accessions>
    <accession>BMDB00152</accession>
  </secondary_accessions>
  <name>Gentisic acid</name>
  <description/>
  <synonyms>
    <synonym>2,5-Dihydroxybenzoate</synonym>
    <synonym>5-Hydroxysalicylic acid</synonym>
    <synonym>Gentisate</synonym>
    <synonym>Hydroquinonecarboxylic acid</synonym>
    <synonym>2,5-Dihydroxybenzoic acid</synonym>
    <synonym>5-Hydroxysalicylate</synonym>
    <synonym>Hydroquinonecarboxylate</synonym>
    <synonym>2,5-Dioxybenzoate</synonym>
    <synonym>2,5-Dioxybenzoic acid</synonym>
    <synonym>3,6-Dihydroxybenzoate</synonym>
    <synonym>3,6-Dihydroxybenzoic acid</synonym>
    <synonym>5-Hydroxy-salicylate</synonym>
    <synonym>5-Hydroxy-salicylic acid</synonym>
    <synonym>Carboxyhydroquinone</synonym>
    <synonym>Dihydroxybenzoicacid</synonym>
    <synonym>Gensigen</synonym>
    <synonym>Gensigon</synonym>
    <synonym>Gentisinate</synonym>
    <synonym>Gentisinic acid</synonym>
    <synonym>2,5-Dihydroxybenzoic acid, monosodium salt</synonym>
    <synonym>Lithium 2,5-dihydroxybenzoate</synonym>
    <synonym>Gentisic acid</synonym>
  </synonyms>
  <chemical_formula>C7H6O4</chemical_formula>
  <average_molecular_weight>154.121</average_molecular_weight>
  <monisotopic_moleculate_weight>154.026608673</monisotopic_moleculate_weight>
  <iupac_name>2,5-dihydroxybenzoic acid</iupac_name>
  <traditional_iupac>2,5-dihydroxybenzoic acid</traditional_iupac>
  <cas_registry_number>490-79-9</cas_registry_number>
  <smiles>OC(=O)C1=C(O)C=CC(O)=C1</smiles>
  <inchi>InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)</inchi>
  <inchikey>WXTMDXOMEHJXQO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>Hydroxybenzoic acid derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroquinones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Salicylic acids</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dihydroxybenzoic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroquinone</substituent>
      <substituent>Hydroxybenzoic acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Salicylic acid</substituent>
      <substituent>Salicylic acid or derivatives</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dihydroxybenzoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>199.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>5.0 mg/mL at 5 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.74</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-5.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,5-dihydroxybenzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>154.121</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>154.026608673</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1=C(O)C=CC(O)=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H6O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WXTMDXOMEHJXQO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>241120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>241121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>241122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>243175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>243176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>243177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373678</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00628</kegg_id>
  <chemspider_id>3350</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB000844</foodb_id>
  <pubchem_compound_id>3469</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17189</chebi_id>
  <phenol_explorer_compound_id>416</phenol_explorer_compound_id>
  <meta_cyc_id>CPD-633</meta_cyc_id>
  <knapsack_id>C00002648</knapsack_id>
  <wikipedia_id>Gentisic_acid</wikipedia_id>
  <bigg_id/>
  <metlin_id>618</metlin_id>
  <synthesis_reference>Morris, Steward G. Preparation of gentisic acid and its fatty alcohol esters.Journal of the American Chemical Society (1949), 71 2056-7</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:15 UTC</creation_date>
  <update_date>2020-04-15 22:35:07 UTC</update_date>
  <accession>BMDB0000153</accession>
  <secondary_accessions>
    <accession>BMDB00153</accession>
  </secondary_accessions>
  <name>Estriol</name>
  <description>Estriol, also known as 16a,17b-estriol or ovestin, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, estriol is considered to be a steroid lipid molecule. Estriol is a drug which is used as a test to determine the general health of an unborn fetus. Estriol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Estriol participates in a number of enzymatic reactions, within cattle. In particular, Estriol can be biosynthesized from 16a-hydroxyestrone; which is mediated by the enzyme estradiol 17-beta-dehydrogenase 1. In addition, Estriol can be biosynthesized from estradiol; which is mediated by the enzyme cytochrome P450 3A5. In cattle, estriol is involved in the metabolic pathway called the estrone metabolism pathway. Estriol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol</synonym>
    <synonym>1,3,5(10)-Estratriene-3,16-alpha,17beta-triol</synonym>
    <synonym>16alpha,17beta-Estriol</synonym>
    <synonym>16alpha-Hydroxyestradiol</synonym>
    <synonym>3,16alpha,17beta-Trihydroxy-Delta(1,3,5)-estratriene</synonym>
    <synonym>Deuslon-a</synonym>
    <synonym>Estriel</synonym>
    <synonym>Oestriol</synonym>
    <synonym>Trihydroxyestrin</synonym>
    <synonym>(16a,17b)-Estra-1,3,5(10)-triene-3,16,17-triol</synonym>
    <synonym>(16Α,17β)-estra-1,3,5(10)-triene-3,16,17-triol</synonym>
    <synonym>1,3,5(10)-Estratriene-3,16-a,17b-triol</synonym>
    <synonym>1,3,5(10)-Estratriene-3,16-α,17β-triol</synonym>
    <synonym>16a,17b-Estriol</synonym>
    <synonym>16Α,17β-estriol</synonym>
    <synonym>16a-Hydroxyestradiol</synonym>
    <synonym>16Α-hydroxyestradiol</synonym>
    <synonym>3,16a,17b-Trihydroxy-delta(1,3,5)-estratriene</synonym>
    <synonym>3,16Α,17β-trihydroxy-δ(1,3,5)-estratriene</synonym>
    <synonym>3,16a,17b-Trihydroxy-δ(1,3,5)-estratriene</synonym>
    <synonym>13b-Methyl-1,3,5(10)-gonatriene-3,16a,17b-triol</synonym>
    <synonym>16-alpha,17-beta-Estriol</synonym>
    <synonym>16-alpha,17-beta-Oestriol</synonym>
    <synonym>16-alpha-Hydroxyestradiol</synonym>
    <synonym>16a-Estriol</synonym>
    <synonym>16alpha,17beta-Oestriol</synonym>
    <synonym>16alpha-Hydroxy-17beta-estradiol</synonym>
    <synonym>16alpha-Hydroxyoestradiol</synonym>
    <synonym>3,16a,17b-Estriol</synonym>
    <synonym>3,16a,17b-Trihydroxyestra-1,3,5(10)-triene</synonym>
    <synonym>3,16alpha,17beta-Trihydroxy-1,3,5(10)-estratriene</synonym>
    <synonym>3,16alpha,17beta-Trihydroxyestra-1,3,5(10)-triene</synonym>
    <synonym>Aacifemine</synonym>
    <synonym>Colpogyn</synonym>
    <synonym>Colpovister</synonym>
    <synonym>Destriol</synonym>
    <synonym>Deuslon a</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,16a,17b-triol</synonym>
    <synonym>Estratriol</synonym>
    <synonym>Follicular hormone hydrate</synonym>
    <synonym>Gynasan</synonym>
    <synonym>Hemostyptanon</synonym>
    <synonym>Holin V</synonym>
    <synonym>Hormomed</synonym>
    <synonym>Incurin</synonym>
    <synonym>Klimax e</synonym>
    <synonym>Klimoral</synonym>
    <synonym>Oekolp</synonym>
    <synonym>Oestratriol</synonym>
    <synonym>Oestriolum</synonym>
    <synonym>Orestin</synonym>
    <synonym>Orgastyptin</synonym>
    <synonym>Ortho-gynest</synonym>
    <synonym>Ovesterin</synonym>
    <synonym>Ovestin</synonym>
    <synonym>Ovestinon</synonym>
    <synonym>Ovestrion</synonym>
    <synonym>Ovo-vinces</synonym>
    <synonym>Theelol</synonym>
    <synonym>Tridestrin</synonym>
    <synonym>Triovex</synonym>
    <synonym>16-alpha-Hydroxy-estradiol</synonym>
    <synonym>(16beta,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol</synonym>
    <synonym>16beta Hydroxy estradiol</synonym>
    <synonym>16beta-Hydroxy-estradiol</synonym>
    <synonym>Epiestriol</synonym>
    <synonym>16 alpha Hydroxy estradiol</synonym>
    <synonym>16alpha,17beta Estriol</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,16beta,17beta-triol</synonym>
  </synonyms>
  <chemical_formula>C18H24O3</chemical_formula>
  <average_molecular_weight>288.3814</average_molecular_weight>
  <monisotopic_moleculate_weight>288.172544634</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol</iupac_name>
  <traditional_iupac>(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol</traditional_iupac>
  <cas_registry_number>50-27-1</cas_registry_number>
  <smiles>[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</smiles>
  <inchi>InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1</inchi>
  <inchikey>PROQIPRRNZUXQM-ZXXIGWHRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>16-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>16-alpha-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>16alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>17beta-hydroxy steroid</external_descriptor>
      <external_descriptor>3-hydroxy steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>Estrane and derivatives</external_descriptor>
      <external_descriptor>Estrogens</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>282 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.45</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>288.3814</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>288.172544634</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H24O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PROQIPRRNZUXQM-ZXXIGWHRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>81.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439748</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00002843 +/- 0.00001</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>commercial skim milk</comment>
      <references>
        <reference>
          <reference_text>Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3.</reference_text>
          <pubmed_id>512140</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00003121 +/- 0.000006935</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial whole milk</comment>
      <references>
        <reference>
          <reference_text>Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3.</reference_text>
          <pubmed_id>512140</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C05141</kegg_id>
  <chemspider_id>5553</chemspider_id>
  <drugbank_id>DB04573</drugbank_id>
  <foodb_id>FDB006781</foodb_id>
  <pubchem_compound_id>5756</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>27974</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>ESTRIOL</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Estriol</wikipedia_id>
  <bigg_id>45207</bigg_id>
  <metlin_id>2581</metlin_id>
  <synthesis_reference>Leeds, Norma S.; Fukushima, David K.; Gallagher, T. F.  Studies of steroid ring D epoxides of enol acetates; a new synthesis of estriol and of androstane-3b,16a,17b-triol.    Journal of the American Chemical Society  (1954),  76  2943-8.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Wolford ST, Argoudelis CJ: Measurement of estrogens in cow's milk, human milk, and dairy products. J Dairy Sci. 1979 Sep;62(9):1458-63. doi: 10.3168/jds.S0022-0302(79)83446-3.</reference_text>
      <pubmed_id>512140</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:16 UTC</creation_date>
  <update_date>2020-04-14 22:46:40 UTC</update_date>
  <accession>BMDB0000156</accession>
  <secondary_accessions>
    <accession>BMDB00156</accession>
  </secondary_accessions>
  <name>L-Malic acid</name>
  <description>(S)-Malic acid, also known as malate or L-apple acid, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom (S)-Malic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule (S)-Malic acid exists in all eukaryotes, ranging from yeast to humans.</description>
  <synonyms>
    <synonym>(-)-L-Malic acid</synonym>
    <synonym>(S)-(-)-Hydroxysuccinic acid</synonym>
    <synonym>L-2-Hydroxybutanedioic acid</synonym>
    <synonym>L-Apple acid</synonym>
    <synonym>Malate</synonym>
    <synonym>Malic acid</synonym>
    <synonym>S-2-Hydroxybutanedioic acid</synonym>
    <synonym>L-Malate</synonym>
    <synonym>(-)-L-Malate</synonym>
    <synonym>(S)-(-)-Hydroxysuccinate</synonym>
    <synonym>L-2-Hydroxybutanedioate</synonym>
    <synonym>S-2-Hydroxybutanedioate</synonym>
    <synonym>(-)-(S)-Malate</synonym>
    <synonym>(-)-(S)-Malic acid</synonym>
    <synonym>(-)-Hydroxysuccinate</synonym>
    <synonym>(-)-Hydroxysuccinic acid</synonym>
    <synonym>(-)-Malic acid</synonym>
    <synonym>(2S)-2-Hydroxybutanedioate</synonym>
    <synonym>(2S)-2-Hydroxybutanedioic acid</synonym>
    <synonym>(S)-Hydroxy-butanedioate</synonym>
    <synonym>(S)-Hydroxy-butanedioic acid</synonym>
    <synonym>(S)-Hydroxybutanedioate</synonym>
    <synonym>(S)-Hydroxybutanedioic acid</synonym>
    <synonym>(S)-Malic acid</synonym>
    <synonym>Apple acid</synonym>
    <synonym>L-(-)-Malic acid</synonym>
    <synonym>L-Hydroxybutanedioate</synonym>
    <synonym>L-Hydroxybutanedioic acid</synonym>
    <synonym>L-Hydroxysuccinate</synonym>
    <synonym>L-Hydroxysuccinic acid</synonym>
    <synonym>S-(-)-Malate</synonym>
    <synonym>S-(-)-Malic acid</synonym>
    <synonym>(S)-Malate</synonym>
    <synonym>L-Malic acid</synonym>
    <synonym>(2S)-2-Hydroxysuccinic acid</synonym>
    <synonym>(2S)-Malic acid</synonym>
    <synonym>(S)-2-Hydroxysuccinic acid</synonym>
    <synonym>2-Hydroxybutanedioic acid</synonym>
    <synonym>2-Hydroxyethane-1,2-dicarboxylic acid</synonym>
    <synonym>2-Hydroxysuccinic acid</synonym>
    <synonym>Deoxytetraric acid</synonym>
    <synonym>Hydroxybutanedioic acid</synonym>
    <synonym>Hydroxysuccinic acid</synonym>
    <synonym>Monohydroxybutanedioic acid</synonym>
    <synonym>alpha-Hydroxysuccinic acid</synonym>
    <synonym>α-Hydroxysuccinic acid</synonym>
  </synonyms>
  <chemical_formula>C4H6O5</chemical_formula>
  <average_molecular_weight>134.0874</average_molecular_weight>
  <monisotopic_moleculate_weight>134.021523302</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-hydroxybutanedioic acid</iupac_name>
  <traditional_iupac>(-)-malic acid</traditional_iupac>
  <cas_registry_number>97-67-6</cas_registry_number>
  <smiles>O[C@@H](CC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1</inchi>
  <inchikey>BJEPYKJPYRNKOW-REOHCLBHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Beta hydroxy acids and derivatives</sub_class>
    <direct_parent>Beta hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>malic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>107 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-hydroxybutanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>134.0874</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>134.021523302</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H](CC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H6O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BJEPYKJPYRNKOW-REOHCLBHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>24.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>2008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37326</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by GC-TOF/MS</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
          <pubmed_id>29197344</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00149</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB012047</foodb_id>
  <chemspider_id>193317</chemspider_id>
  <pubchem_compound_id>222656</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30797</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>MAL</meta_cyc_id>
  <knapsack_id>C00001192</knapsack_id>
  <wikipedia_id>Malic acid</wikipedia_id>
  <bigg_id>34045</bigg_id>
  <metlin_id/>
  <synthesis_reference>McKenzie, Alex.; Plenderleith, H. J.; Walker, Nellie. Optical activation of racemic acid by d-malic acid. Journal of the Chemical Society, Transactions (1923), 123 2875-80.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
      <pubmed_id>29197344</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:17 UTC</creation_date>
  <update_date>2020-04-16 20:38:22 UTC</update_date>
  <accession>BMDB0000157</accession>
  <secondary_accessions>
    <accession>BMDB00157</accession>
  </secondary_accessions>
  <name>Hypoxanthine</name>
  <description>Hypoxanthine, also known as purine-6-ol or Hyp, belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. Hypoxanthine exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Hypoxanthine exists in all living species, ranging from bacteria to humans. Hypoxanthine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>6(1H)-Purinone</synonym>
    <synonym>6-Oxopurine</synonym>
    <synonym>9H-Purin-6(1H)-one</synonym>
    <synonym>Hyp</synonym>
    <synonym>Purin-6(1H)-one</synonym>
    <synonym>Purine-6-ol</synonym>
    <synonym>1,7-Dihydro-6H-purin-6-one</synonym>
    <synonym>1,7-Dihydro-6H-purine-6-one</synonym>
    <synonym>1H,7H-Hypoxanthine</synonym>
    <synonym>3H-Purin-6-ol</synonym>
    <synonym>4-Hydroxy-1H-purine</synonym>
    <synonym>6-Hydroxy-1H-purine</synonym>
    <synonym>6-Hydroxypurine</synonym>
    <synonym>7H-Purin-6-ol</synonym>
    <synonym>9H-Purin-6-ol</synonym>
    <synonym>Hypoxanthine enol</synonym>
    <synonym>Purin-6(3H)-one</synonym>
    <synonym>Purin-6-ol</synonym>
    <synonym>Sarcine</synonym>
    <synonym>Sarkin</synonym>
    <synonym>Sarkine</synonym>
  </synonyms>
  <chemical_formula>C5H4N4O</chemical_formula>
  <average_molecular_weight>136.1115</average_molecular_weight>
  <monisotopic_moleculate_weight>136.03851077</monisotopic_moleculate_weight>
  <iupac_name>7H-purin-6-ol</iupac_name>
  <traditional_iupac>6-hydroxypurine</traditional_iupac>
  <cas_registry_number>68-94-0</cas_registry_number>
  <smiles>OC1=NC=NC2=C1NC=N2</smiles>
  <inchi>InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)</inchi>
  <inchikey>FDGQSTZJBFJUBT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Hypoxanthines</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Purine alkaloids</external_descriptor>
      <external_descriptor>a purine base</external_descriptor>
      <external_descriptor>a purine-related compound</external_descriptor>
      <external_descriptor>nucleobase analogue</external_descriptor>
      <external_descriptor>oxopurine</external_descriptor>
      <external_descriptor>purine nucleobase</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>150 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.7 mg/mL</value>
      <source>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.11</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.048</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>7H-purin-6-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>136.1115</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>136.03851077</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC1=NC=NC2=C1NC=N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H4N4O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FDGQSTZJBFJUBT-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3151</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>1227+/-156</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw whole milk</comment>
      <references>
        <reference>
          <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
          <pubmed_id>6539345</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1159.7 +/- 135.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1254.6 +/- 88.57</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1497.99 +/- 57.51</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in beef muscle (longissimus dorsi).</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>678.18 +/- 58.48</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>80 +/- 24</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>90 +/- 49</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>205 +/- 61</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>63 +/- 25</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>63 +/- 25</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR and GC-MS</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>103-150</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>134</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>219</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>220</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>87.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>753+/-191</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>52.27 +/- 24.11</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>76.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>85.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>205</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>52.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>176+/-66</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00262</kegg_id>
  <chemspider_id>768</chemspider_id>
  <drugbank_id>DB04076</drugbank_id>
  <foodb_id>FDB003949</foodb_id>
  <pubchem_compound_id>790</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17368</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>HYPOXANTHINE</meta_cyc_id>
  <knapsack_id>C00001502</knapsack_id>
  <wikipedia_id>Hypoxanthine</wikipedia_id>
  <bigg_id>34434</bigg_id>
  <metlin_id>83</metlin_id>
  <synthesis_reference>Shaw, Elliott.New synthesis of the purines adenine, hypoxanthine, xanthine, and isoguanine. Journal of Biological Chemistry (1950), 185 439-47.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
      <pubmed_id>6539345</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00440</protein_accession>
      <name>Hypoxanthine-guanine phosphoribosyltransferase</name>
      <uniprot_id>Q3SZ18</uniprot_id>
      <gene_name>HPRT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00603</protein_accession>
      <name>Xanthine dehydrogenase/oxidase</name>
      <uniprot_id>P80457</uniprot_id>
      <gene_name>XDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:19 UTC</creation_date>
  <update_date>2020-04-16 20:38:57 UTC</update_date>
  <accession>BMDB0000158</accession>
  <secondary_accessions>
    <accession>BMDB00158</accession>
  </secondary_accessions>
  <name>L-Tyrosine</name>
  <description>L-Tyrosine, also known as (S)-tyrosine or para tyrosine, belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Tyrosine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Tyrosine exists in all living species, ranging from bacteria to humans. L-Tyrosine participates in a number of enzymatic reactions, within cattle. In particular, L-Tyrosine and oxoglutaric acid can be converted into 4-hydroxyphenylpyruvic acid and L-glutamic acid; which is mediated by the enzyme tyrosine aminotransferase. In addition, L-Tyrosine can be converted into tyramine through its interaction with the enzyme aromatic-L-amino-acid decarboxylase. In cattle, L-tyrosine is involved in a couple of metabolic pathways, which include thyroid hormone synthesis pathway and the tyrosine metabolism pathway. L-Tyrosine is a potentially toxic compound. L-Tyrosine has been found to be associated with several diseases known as irritable bowel syndrome, frontotemporal dementia, obesity, and leukemia; also l-tyrosine has been linked to the inborn metabolic disorders including hypermethioninemia.</description>
  <synonyms>
    <synonym>(-)-alpha-Amino-p-hydroxyhydrocinnamic acid</synonym>
    <synonym>(2S)-2-Amino-3-(4-hydroxyphenyl)propanoic acid</synonym>
    <synonym>(S)-(-)-Tyrosine</synonym>
    <synonym>(S)-2-Amino-3-(p-hydroxyphenyl)propionic acid</synonym>
    <synonym>(S)-3-(p-Hydroxyphenyl)alanine</synonym>
    <synonym>(S)-alpha-Amino-4-hydroxybenzenepropanoic acid</synonym>
    <synonym>(S)-Tyrosine</synonym>
    <synonym>4-Hydroxy-L-phenylalanine</synonym>
    <synonym>L-Tyrosin</synonym>
    <synonym>Tyr</synonym>
    <synonym>TYROSINE</synonym>
    <synonym>Y</synonym>
    <synonym>(-)-a-Amino-p-hydroxyhydrocinnamate</synonym>
    <synonym>(-)-a-Amino-p-hydroxyhydrocinnamic acid</synonym>
    <synonym>(-)-alpha-Amino-p-hydroxyhydrocinnamate</synonym>
    <synonym>(-)-Α-amino-p-hydroxyhydrocinnamate</synonym>
    <synonym>(-)-Α-amino-p-hydroxyhydrocinnamic acid</synonym>
    <synonym>(2S)-2-Amino-3-(4-hydroxyphenyl)propanoate</synonym>
    <synonym>(S)-2-Amino-3-(p-hydroxyphenyl)propionate</synonym>
    <synonym>(S)-a-Amino-4-hydroxybenzenepropanoate</synonym>
    <synonym>(S)-a-Amino-4-hydroxybenzenepropanoic acid</synonym>
    <synonym>(S)-alpha-Amino-4-hydroxybenzenepropanoate</synonym>
    <synonym>(S)-Α-amino-4-hydroxybenzenepropanoate</synonym>
    <synonym>(S)-Α-amino-4-hydroxybenzenepropanoic acid</synonym>
    <synonym>(S)-a-Amino-4-hydroxy-benzenepropanoate</synonym>
    <synonym>(S)-a-Amino-4-hydroxy-benzenepropanoic acid</synonym>
    <synonym>(S)-alpha-Amino-4-hydroxy-benzenepropanoate</synonym>
    <synonym>(S)-alpha-Amino-4-hydroxy-benzenepropanoic acid</synonym>
    <synonym>2-Amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoate</synonym>
    <synonym>2-Amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoic acid</synonym>
    <synonym>3-(4-Hydroxyphenyl)-L-alanine</synonym>
    <synonym>Benzenepropanoate</synonym>
    <synonym>Benzenepropanoic acid</synonym>
    <synonym>L-p-Tyrosine</synonym>
    <synonym>p-Tyrosine</synonym>
    <synonym>L Tyrosine</synonym>
    <synonym>Tyrosine, L-isomer</synonym>
    <synonym>Tyrosine, L isomer</synonym>
    <synonym>Para tyrosine</synonym>
    <synonym>Para-tyrosine</synonym>
  </synonyms>
  <chemical_formula>C9H11NO3</chemical_formula>
  <average_molecular_weight>181.1885</average_molecular_weight>
  <monisotopic_moleculate_weight>181.073893223</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid</iupac_name>
  <traditional_iupac>L-tyrosine</traditional_iupac>
  <cas_registry_number>60-18-4</cas_registry_number>
  <smiles>N[C@@H](CC1=CC=C(O)C=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1</inchi>
  <inchikey>OUYCCCASQSFEME-QMMMGPOBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Tyrosine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalanine and derivatives</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Tyrosine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>erythrose 4-phosphate/phosphoenolpyruvate family amino acid</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
      <external_descriptor>tyrosine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>343 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.479 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.26</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>181.1885</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>181.073893223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CC1=CC=C(O)C=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OUYCCCASQSFEME-QMMMGPOBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>83.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Tyrosine</name>
      <smpdb_id>SMP0119416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Thyroid Hormone Synthesis</name>
      <smpdb_id>SMP0087269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3176</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 24 male 17-22-month-old Charolais beef cattles.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>47.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>69.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>68-75</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>47-60</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>25-42</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Sadri H, von Soosten D, Meyer U, Kluess J, Danicke S, Saremi B, Sauerwein H: Plasma amino acids and metabolic profiling of dairy cows in response to a bolus duodenal infusion of leucine. PLoS One. 2017 Apr 28;12(4):e0176647. doi: 10.1371/journal.pone.0176647. eCollection 2017.</reference_text>
          <pubmed_id>28453535</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>91+/-10</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>40-44</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>84+/-27</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>54+/-14</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.71 +/- 0.96</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.6 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2 - 11</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from Simmental cows during late lactation</comment>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
          <pubmed_id>23931703</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.8 +/- 2.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from Brown Swiss cows during late lactation</comment>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
          <pubmed_id>23931703</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>This is a duplicate concentration of concentration_id 8079, unpexported by An Chi on Aug 20, 2018</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.6 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.30 +/- 0.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.4 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.3 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.11 +/- 1.97</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.65 +/- 2.51</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8278.671</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8278.671</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8278.671</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8278.671</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8278.671</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8278.671</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8278.671</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>251.11 +/- 17.54</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>44-269</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>48.4 +/- 4.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>530</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>81.35 +/- 11.06</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>97.9 +/- 13.13</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>31-41</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>82-422</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>35 +/- 13</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>50 +/- 24</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>61 +/- 21</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>49 +/- 12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>49 +/- 12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR, GC-MS and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>68-471</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>36</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>49.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>60.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>42.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>26-77</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>41.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>52.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>50.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>46.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>8 - 12</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wadud S, Onodera R, Or-Rashid MM, Amin MR: Determination of histidine and related compounds in rumen fluid by liquid chromatography. J AOAC Int. 2000 Jan-Feb;83(1):8-15.</reference_text>
          <pubmed_id>10692998</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>295+/-136</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>42.17 +/- 8.29</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>52+/-10</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>43+/-9</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein.</comment>
      <references>
        <reference>
          <reference_text>Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17.</reference_text>
          <pubmed_id>22059599</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00082</kegg_id>
  <chemspider_id>5833</chemspider_id>
  <drugbank_id>DB00135</drugbank_id>
  <foodb_id>FDB000446</foodb_id>
  <pubchem_compound_id>6057</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17895</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>TYR</meta_cyc_id>
  <knapsack_id>C00001397</knapsack_id>
  <wikipedia_id>Tyrosine</wikipedia_id>
  <bigg_id>33785</bigg_id>
  <metlin_id>34</metlin_id>
  <synthesis_reference>Enei, Hitoshi; Matsui, Hiroshi; Yamashita, Koichi; Okumura, Shinji; Yamada, Hideaki. Microbiological synthesis of L-tyrosine and 3,4-dihydroxyphenyl-L-alanine. I. Distribution of tyrosine phenol lyase in microorganisms. Agricultural and Biological Chemist  1972, 36:11, 1861-1868, DOI: 10.1080/00021369.1972.10860505</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
      <pubmed_id>23931703</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00144</protein_accession>
      <name>Dual specificity protein phosphatase 14</name>
      <uniprot_id>Q17QM8</uniprot_id>
      <gene_name>DUSP14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00160</protein_accession>
      <name>Dual specificity protein phosphatase 26</name>
      <uniprot_id>Q17QJ3</uniprot_id>
      <gene_name>DUSP26</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00167</protein_accession>
      <name>Dual specificity phosphatase DUPD1</name>
      <uniprot_id>P0C591</uniprot_id>
      <gene_name>DUPD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00181</protein_accession>
      <name>Dual specificity protein phosphatase 10</name>
      <uniprot_id>Q0IID7</uniprot_id>
      <gene_name>DUSP10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00187</protein_accession>
      <name>Dual specificity protein phosphatase 18</name>
      <uniprot_id>Q5BIP9</uniprot_id>
      <gene_name>DUSP18</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00190</protein_accession>
      <name>Putative tyrosine-protein phosphatase auxilin</name>
      <uniprot_id>Q27974</uniprot_id>
      <gene_name>DNAJC6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00194</protein_accession>
      <name>Eyes absent homolog 2</name>
      <uniprot_id>Q58DB6</uniprot_id>
      <gene_name>EYA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00206</protein_accession>
      <name>Dual specificity protein phosphatase 6</name>
      <uniprot_id>Q2KJ36</uniprot_id>
      <gene_name>DUSP6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00375</protein_accession>
      <name>Protein-tyrosine sulfotransferase 2</name>
      <uniprot_id>Q3SYY2</uniprot_id>
      <gene_name>TPST2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00388</protein_accession>
      <name>Tyrosine 3-monooxygenase</name>
      <uniprot_id>P17289</uniprot_id>
      <gene_name>TH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00389</protein_accession>
      <name>Phenylalanine-4-hydroxylase</name>
      <uniprot_id>Q2KIH7</uniprot_id>
      <gene_name>PAH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00505</protein_accession>
      <name>Tubulin--tyrosine ligase</name>
      <uniprot_id>P38584</uniprot_id>
      <gene_name>TTL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00662</protein_accession>
      <name>Tyrosinase</name>
      <uniprot_id>Q8MIU0</uniprot_id>
      <gene_name>TYR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00859</protein_accession>
      <name>Tyrosine aminotransferase</name>
      <uniprot_id>Q58CZ9</uniprot_id>
      <gene_name>TAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00915</protein_accession>
      <name>Phosphatidylinositol 3-kinase regulatory subunit alpha</name>
      <uniprot_id>P23727</uniprot_id>
      <gene_name>PIK3R1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01006</protein_accession>
      <name>Protein tyrosine phosphatase type IVA 3</name>
      <uniprot_id>A2VDT1</uniprot_id>
      <gene_name>PTP4A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01230</protein_accession>
      <name>Phosphatidylinositol 3-kinase regulatory subunit beta</name>
      <uniprot_id>P23726</uniprot_id>
      <gene_name>PIK3R2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01231</protein_accession>
      <name>Tyrosine-protein phosphatase non-receptor type substrate 1</name>
      <uniprot_id>O46631</uniprot_id>
      <gene_name>SIRPA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01232</protein_accession>
      <name>Tyrosyl-tRNA synthetase, cytoplasmic</name>
      <uniprot_id>Q29465</uniprot_id>
      <gene_name>YARS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01233</protein_accession>
      <name>M-phase inducer phosphatase 1</name>
      <uniprot_id>A7MBD1</uniprot_id>
      <gene_name>CDC25A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01234</protein_accession>
      <name>Reelin</name>
      <uniprot_id>Q9N117</uniprot_id>
      <gene_name>RELN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01235</protein_accession>
      <name>Receptor-type tyrosine-protein phosphatase F</name>
      <uniprot_id>A7MBJ4</uniprot_id>
      <gene_name>PTPRF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01236</protein_accession>
      <name>Low molecular weight phosphotyrosine protein phosphatase</name>
      <uniprot_id>P11064</uniprot_id>
      <gene_name>ACP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01237</protein_accession>
      <name>Myotubularin</name>
      <uniprot_id>A6QLT4</uniprot_id>
      <gene_name>MTM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01238</protein_accession>
      <name>Phosphatidylinositol 3-kinase regulatory subunit gamma</name>
      <uniprot_id>O46404</uniprot_id>
      <gene_name>PIK3R3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01239</protein_accession>
      <name>M-phase inducer phosphatase 3</name>
      <uniprot_id>A5D7P0</uniprot_id>
      <gene_name>CDC25C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01355</protein_accession>
      <name>Solute carrier family 22 member 1</name>
      <uniprot_id>A7MBE0</uniprot_id>
      <gene_name>SLC22A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02586</protein_accession>
      <name>Contactin-1</name>
      <uniprot_id>Q28106</uniprot_id>
      <gene_name>CNTN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02587</protein_accession>
      <name>GDNF family receptor alpha-2</name>
      <uniprot_id>Q5E9X0</uniprot_id>
      <gene_name>GFRA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02588</protein_accession>
      <name>Ephrin-A1</name>
      <uniprot_id>Q3ZC64</uniprot_id>
      <gene_name>EFNA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02589</protein_accession>
      <name>Interferon-alpha/beta receptor alpha chain</name>
      <uniprot_id>Q04790</uniprot_id>
      <gene_name>IFNAR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02590</protein_accession>
      <name>B-cell antigen receptor complex-associated protein alpha chain</name>
      <uniprot_id>P40293</uniprot_id>
      <gene_name>CD79A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02591</protein_accession>
      <name>Glucocorticoid modulatory element-binding protein 1</name>
      <uniprot_id>Q2HJ87</uniprot_id>
      <gene_name>GMEB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02592</protein_accession>
      <name>Interferon-alpha/beta receptor beta chain</name>
      <uniprot_id>Q95141</uniprot_id>
      <gene_name>IFNAR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02593</protein_accession>
      <name>Angiopoietin-1</name>
      <uniprot_id>O18920</uniprot_id>
      <gene_name>ANGPT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02594</protein_accession>
      <name>General transcription factor II-I</name>
      <uniprot_id>A7MB80</uniprot_id>
      <gene_name>GTF2I</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02595</protein_accession>
      <name>Suppressor of cytokine signaling 3</name>
      <uniprot_id>Q9BEG9</uniprot_id>
      <gene_name>SOCS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02596</protein_accession>
      <name>Scavenger receptor cysteine-rich type 1 protein M130</name>
      <uniprot_id>P85521</uniprot_id>
      <gene_name>CD163</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02597</protein_accession>
      <name>TYRO protein tyrosine kinase-binding protein</name>
      <uniprot_id>Q95J79</uniprot_id>
      <gene_name>TYROBP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02598</protein_accession>
      <name>Caveolin-2</name>
      <uniprot_id>Q66WT7</uniprot_id>
      <gene_name>CAV2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02599</protein_accession>
      <name>Cytokine-inducible SH2-containing protein</name>
      <uniprot_id>Q2HJ53</uniprot_id>
      <gene_name>CISH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02600</protein_accession>
      <name>Proto-oncogene vav</name>
      <uniprot_id>Q08DN7</uniprot_id>
      <gene_name>VAV1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:20 UTC</creation_date>
  <update_date>2020-04-16 20:38:58 UTC</update_date>
  <accession>BMDB0000159</accession>
  <secondary_accessions>
    <accession>BMDB00159</accession>
  </secondary_accessions>
  <name>L-Phenylalanine</name>
  <description>L-Phenylalanine, also known as F or endorphenyl, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Phenylalanine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Phenylalanine exists in all living species, ranging from bacteria to humans. L-Phenylalanine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(S)-2-Amino-3-phenylpropionic acid</synonym>
    <synonym>(S)-alpha-Amino-beta-phenylpropionic acid</synonym>
    <synonym>3-Phenyl-L-alanine</synonym>
    <synonym>beta-Phenyl-L-alanine</synonym>
    <synonym>F</synonym>
    <synonym>Phe</synonym>
    <synonym>PHENYLALANINE</synonym>
    <synonym>(S)-2-Amino-3-phenylpropionate</synonym>
    <synonym>(S)-a-Amino-b-phenylpropionate</synonym>
    <synonym>(S)-a-Amino-b-phenylpropionic acid</synonym>
    <synonym>(S)-alpha-Amino-beta-phenylpropionate</synonym>
    <synonym>(S)-Α-amino-β-phenylpropionate</synonym>
    <synonym>(S)-Α-amino-β-phenylpropionic acid</synonym>
    <synonym>b-Phenyl-L-alanine</synonym>
    <synonym>Β-phenyl-L-alanine</synonym>
    <synonym>(-)-beta-Phenylalanine</synonym>
    <synonym>(L)-Phenylalanine</synonym>
    <synonym>(S)-(-)-Phenylalanine</synonym>
    <synonym>(S)-2-Amino-3-phenylpropanoate</synonym>
    <synonym>(S)-2-Amino-3-phenylpropanoic acid</synonym>
    <synonym>(S)-alpha-Amino-benzenepropanoate</synonym>
    <synonym>(S)-alpha-Amino-benzenepropanoic acid</synonym>
    <synonym>(S)-alpha-Aminobenzenepropanoate</synonym>
    <synonym>(S)-alpha-Aminobenzenepropanoic acid</synonym>
    <synonym>(S)-alpha-Aminohydrocinnamate</synonym>
    <synonym>(S)-alpha-Aminohydrocinnamic acid</synonym>
    <synonym>(S)-Phenylalanine</synonym>
    <synonym>alpha-Aminohydrocinnamate</synonym>
    <synonym>alpha-Aminohydrocinnamic acid</synonym>
    <synonym>beta-Phenyl-alpha-alanine</synonym>
    <synonym>beta-Phenylalanine</synonym>
    <synonym>L-2-Amino-3-phenylpropionate</synonym>
    <synonym>L-2-Amino-3-phenylpropionic acid</synonym>
    <synonym>Phenyl-alanine</synonym>
    <synonym>Phenylalamine</synonym>
    <synonym>L-Isomer phenylalanine</synonym>
    <synonym>Phenylalanine, L isomer</synonym>
    <synonym>Phenylalanine, L-isomer</synonym>
    <synonym>Endorphenyl</synonym>
    <synonym>(6S)-Tetrahydrofolate</synonym>
    <synonym>(6S)-Tetrahydrofolic acid</synonym>
    <synonym>(6S)-THFA</synonym>
    <synonym>5,6,7,8-Tetrahydrofolate</synonym>
    <synonym>Tetrahydrofolate</synonym>
    <synonym>THF</synonym>
    <synonym>5,6,7,8-Tetrahydrofolic acid</synonym>
  </synonyms>
  <chemical_formula>C9H11NO2</chemical_formula>
  <average_molecular_weight>165.1891</average_molecular_weight>
  <monisotopic_moleculate_weight>165.078978601</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-phenylpropanoic acid</iupac_name>
  <traditional_iupac>L-phenylalanine</traditional_iupac>
  <cas_registry_number>63-91-2</cas_registry_number>
  <smiles>N[C@@H](CC1=CC=CC=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1</inchi>
  <inchikey>COLNVLDHVKWLRT-QMMMGPOBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Phenylalanine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>erythrose 4-phosphate/phosphoenolpyruvate family amino acid</external_descriptor>
      <external_descriptor>phenylalanine</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>283 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>26.9 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.38</value>
      <source>AVDEEF,A (1997)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-phenylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>165.1891</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>165.078978601</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CC1=CC=CC=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>COLNVLDHVKWLRT-QMMMGPOBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Phenylalanine</name>
      <smpdb_id>SMP0119406</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3212</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 24 male 17-22-month-old Charolais beef cattles.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>47.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>50.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>65-75</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>44-58</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>71+/-7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>45-48</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>138+/-22</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>55+/-12</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10896.603</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10896.603</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10896.603</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10896.603</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10291.236</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10291.236</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10291.236</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2 - 10</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.7 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.9 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.9 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.99 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.4 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from Simmental cows during late lactation</comment>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
          <pubmed_id>23931703</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>105.7 +/- 18.05</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>242.58 +/- 15.65</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>51-258</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>54.02 +/- 3.36</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>240</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in beef muscle (longissimus dorsi).</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>80.81 +/- 10.96</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>36-48</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>103-496</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>36 +/- 13</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>64 +/- 17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>65 +/- 20</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>34 +/- 17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>34 +/- 17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR, GC-MS and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>31-80</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>35.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>64.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>77.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>28.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>17 - 29</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wadud S, Onodera R, Or-Rashid MM, Amin MR: Determination of histidine and related compounds in rumen fluid by liquid chromatography. J AOAC Int. 2000 Jan-Feb;83(1):8-15.</reference_text>
          <pubmed_id>10692998</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>310+/-129</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>35.37 +/- 13.73</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>58+/-10</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>56+/-12</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00079</kegg_id>
  <chemspider_id>5910</chemspider_id>
  <drugbank_id>DB00120</drugbank_id>
  <foodb_id>FDB004940</foodb_id>
  <pubchem_compound_id>6140</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17295</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>PHE</meta_cyc_id>
  <knapsack_id>C00001386</knapsack_id>
  <wikipedia_id>Phenylalanine</wikipedia_id>
  <bigg_id>33775</bigg_id>
  <metlin_id>28</metlin_id>
  <synthesis_reference>Zhou, Hua; Zhong, Yao; Sun, Guanghai; Wei, Ping.  Preparation of L-phenylalanine by an aqueous two-phase system.  Huaxue Fanying Gongcheng Yu Gongyi  (2006),  22(2),  146-150.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
      <pubmed_id>23931703</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00389</protein_accession>
      <name>Phenylalanine-4-hydroxylase</name>
      <uniprot_id>Q2KIH7</uniprot_id>
      <gene_name>PAH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01278</protein_accession>
      <name>GTP cyclohydrolase 1 feedback regulatory protein</name>
      <uniprot_id>Q32L41</uniprot_id>
      <gene_name>GCHFR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02160</protein_accession>
      <name>Blood-brain barrier large neutral amino acid transporter</name>
      <uniprot_id>Q9TU26</uniprot_id>
      <gene_name>LAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:21 UTC</creation_date>
  <update_date>2020-04-16 20:38:58 UTC</update_date>
  <accession>BMDB0000161</accession>
  <secondary_accessions>
    <accession>BMDB00161</accession>
  </secondary_accessions>
  <name>L-Alanine</name>
  <description>L-Alanine, also known as (S)-alanine or L-alpha-alanine, belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Alanine is a drug which is used for protein synthesis. L-Alanine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Alanine exists in all living species, ranging from bacteria to humans. L-Alanine is a potentially toxic compound. L-Alanine has been found to be associated with several diseases known as eosinophilic esophagitis, late-onset preeclampsia, autism, and perillyl alcohol administration for cancer treatment; also l-alanine has been linked to the inborn metabolic disorders including glucagon deficiency.</description>
  <synonyms>
    <synonym>(2S)-2-Aminopropanoic acid</synonym>
    <synonym>(S)-2-Aminopropanoic acid</synonym>
    <synonym>(S)-Alanine</synonym>
    <synonym>A</synonym>
    <synonym>Ala</synonym>
    <synonym>ALANINE</synonym>
    <synonym>L-2-Aminopropionic acid</synonym>
    <synonym>L-Alanin</synonym>
    <synonym>L-alpha-Alanine</synonym>
    <synonym>(2S)-2-Aminopropanoate</synonym>
    <synonym>(S)-2-Aminopropanoate</synonym>
    <synonym>L-2-Aminopropionate</synonym>
    <synonym>L-a-Alanine</synonym>
    <synonym>L-Α-alanine</synonym>
    <synonym>(S)-(+)-Alanine</synonym>
    <synonym>(S)-2-Amino-propanoate</synonym>
    <synonym>(S)-2-Amino-propanoic acid</synonym>
    <synonym>2-Aminopropanoate</synonym>
    <synonym>2-Aminopropanoic acid</synonym>
    <synonym>2-Aminopropionate</synonym>
    <synonym>2-Aminopropionic acid</synonym>
    <synonym>2-Ammoniopropanoate</synonym>
    <synonym>2-Ammoniopropanoic acid</synonym>
    <synonym>a-Alanine</synonym>
    <synonym>a-Aminopropionate</synonym>
    <synonym>a-Aminopropionic acid</synonym>
    <synonym>alpha-Alanine</synonym>
    <synonym>alpha-Aminopropanoate</synonym>
    <synonym>alpha-Aminopropanoic acid</synonym>
    <synonym>alpha-Aminopropionate</synonym>
    <synonym>alpha-Aminopropionic acid</synonym>
    <synonym>L-(+)-Alanine</synonym>
    <synonym>L-2-Aminopropanoate</synonym>
    <synonym>L-2-Aminopropanoic acid</synonym>
    <synonym>L-a-Aminopropionate</synonym>
    <synonym>L-a-Aminopropionic acid</synonym>
    <synonym>L-alpha-Aminopropionate</synonym>
    <synonym>L-alpha-Aminopropionic acid</synonym>
    <synonym>Abufène</synonym>
    <synonym>Alanine doms-adrian brand</synonym>
    <synonym>Alanine, L-isomer</synonym>
    <synonym>Doms-adrian brand OF alanine</synonym>
    <synonym>Doms adrian brand OF alanine</synonym>
    <synonym>L-Isomer alanine</synonym>
    <synonym>Alanine, L isomer</synonym>
    <synonym>L Alanine</synonym>
  </synonyms>
  <chemical_formula>C3H7NO2</chemical_formula>
  <average_molecular_weight>89.0932</average_molecular_weight>
  <monisotopic_moleculate_weight>89.047678473</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-aminopropanoic acid</iupac_name>
  <traditional_iupac>L-alanine</traditional_iupac>
  <cas_registry_number>56-41-7</cas_registry_number>
  <smiles>C[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1</inchi>
  <inchikey>QNAYBMKLOCPYGJ-REOHCLBHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alanine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alanine or derivatives</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>alanine</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
      <external_descriptor>pyruvate family amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>300 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>204 mg/mL</value>
      <source>Human Metabolome Project</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.85</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-aminopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>89.0932</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>89.047678473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QNAYBMKLOCPYGJ-REOHCLBHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>20.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glucose-Alanine Cycle</name>
      <smpdb_id>SMP0087221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutathione Metabolism</name>
      <smpdb_id>SMP0087167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Alanine</name>
      <smpdb_id>SMP0119369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Selenoamino Acid Metabolism</name>
      <smpdb_id>SMP0087161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445528</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 24 male 17-22-month-old Charolais beef cattles.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>188.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1343 +/- 402</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Abdullah BASOGLU, Nuri BASPINAR, Alparslan COSKUN. NMR-based metabolomic evaluation in dairy cows with displaced abomasum. Turk J Vet Anim Sci (2014) 38(3):325-330</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 54 Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
          <pubmed_id>23394630</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>162-179</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>160.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>151-222</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>162-212</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Sadri H, von Soosten D, Meyer U, Kluess J, Danicke S, Saremi B, Sauerwein H: Plasma amino acids and metabolic profiling of dairy cows in response to a bolus duodenal infusion of leucine. PLoS One. 2017 Apr 28;12(4):e0176647. doi: 10.1371/journal.pone.0176647. eCollection 2017.</reference_text>
          <pubmed_id>28453535</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>187-206</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>240+/-30</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>2366-3515</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By HPLC with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Miles ED, McBride BW, Jia Y, Liao SF, Boling JA, Bridges PJ, Matthews JC: Glutamine synthetase and alanine transaminase expression are decreased in livers of aged vs. young beef cows and GS can be upregulated by 17beta-estradiol implants. J Anim Sci. 2015 Sep;93(9):4500-9. doi: 10.2527/jas.2015-9294.</reference_text>
          <pubmed_id>26440349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>1388+/-276</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>1465+/-272</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29.20 +/- 5.91</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29 - 78</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9 - 91</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13469.0414</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13469.0414</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13469.0414</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13469.0414</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12346.621</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12346.621</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12346.621</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>33 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>33 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>34 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27.45 +/- 5.67</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23.82 +/- 5.36</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from 20 healthy Holstein Friesian dairy cows </comment>
      <references>
        <reference>
          <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
          <pubmed_id>23738862</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1087.79 +/- 32.71</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1147.17 +/- 64.08</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1163.71 +/- 86.55</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1237.91 +/- 72.51</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1055-1310</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>22.79+/-1.78</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>26.34+/-2.26</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>16.28+/-2.20</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>18.95+/-1.63</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>2300</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>167-239</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1916-3173</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>244 +/- 40</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>314 +/- 84</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>441 +/- 74</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>220 +/- 51</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>220 +/- 51</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR and GC-MS</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>83-799</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>135-315</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>212</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>397</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>415</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>197</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>234.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>323.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1060+/-484</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>480.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>212.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>212.13 +/- 47.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>1472+/-278</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>880-1200</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By paper chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Brown-Woodman PD, White IG: Amino acid composition of semen and the secretions of the male reproductive tract. Aust J Biol Sci. 1974 Aug;27(4):415-22. doi: 10.1071/bi9740415.</reference_text>
          <pubmed_id>4429492</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>1400+/-294</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein.</comment>
      <references>
        <reference>
          <reference_text>Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17.</reference_text>
          <pubmed_id>22059599</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00041</kegg_id>
  <chemspider_id>5735</chemspider_id>
  <drugbank_id>DB00160</drugbank_id>
  <foodb_id>FDB000556</foodb_id>
  <pubchem_compound_id>5950</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16977</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>ALPHA-ALANINE</meta_cyc_id>
  <knapsack_id>C00001332</knapsack_id>
  <wikipedia_id>Alanine</wikipedia_id>
  <bigg_id>33629</bigg_id>
  <metlin_id/>
  <synthesis_reference>Chibata I; Kakimoto T; Kato J Enzymatic production of L-alanine by Pseudomonas dacunhae. Applied microbiology (1965), 13(5), 638-45.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
      <pubmed_id>23738862</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
      <pubmed_id>25599412</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00539</protein_accession>
      <name>Selenocysteine lyase</name>
      <uniprot_id>A2VDS1</uniprot_id>
      <gene_name>SCLY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00793</protein_accession>
      <name>Alanine--glyoxylate aminotransferase 2, mitochondrial</name>
      <uniprot_id>Q17QF0</uniprot_id>
      <gene_name>AGXT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00858</protein_accession>
      <name>Alanine aminotransferase 1</name>
      <uniprot_id>A4IFH5</uniprot_id>
      <gene_name>GPT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00911</protein_accession>
      <name>Nuclear inhibitor of protein phosphatase 1</name>
      <uniprot_id>Q28147</uniprot_id>
      <gene_name>PPP1R8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02092</protein_accession>
      <name>Sodium-coupled neutral amino acid transporter 5</name>
      <uniprot_id>Q5E9S9</uniprot_id>
      <gene_name>SLC38A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:22 UTC</creation_date>
  <update_date>2020-04-16 20:38:59 UTC</update_date>
  <accession>BMDB0000162</accession>
  <secondary_accessions>
    <accession>BMDB00162</accession>
  </secondary_accessions>
  <name>L-Proline</name>
  <description>L-Proline, also known as L-prolin, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Proline exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Proline exists in all living species, ranging from bacteria to humans. L-Proline is a potentially toxic compound. L-Proline has been found to be associated with several diseases known as rheumatoid arthritis, perillyl alcohol administration for cancer treatment, colorectal cancer, and pregnancy; also l-proline has been linked to the inborn metabolic disorders including iminoglycinuria.</description>
  <synonyms>
    <synonym>(-)-(S)-Proline</synonym>
    <synonym>(-)-2-Pyrrolidinecarboxylic acid</synonym>
    <synonym>(-)-Proline</synonym>
    <synonym>(2S)-Pyrrolidine-2-carboxylic acid</synonym>
    <synonym>(S)-2-Carboxypyrrolidine</synonym>
    <synonym>(S)-2-Pyrrolidinecarboxylic acid</synonym>
    <synonym>(S)-Pyrrolidine-2-carboxylic acid</synonym>
    <synonym>2-Pyrrolidinecarboxylic acid</synonym>
    <synonym>L-(-)-Proline</synonym>
    <synonym>L-alpha-Pyrrolidinecarboxylic acid</synonym>
    <synonym>L-Prolin</synonym>
    <synonym>L-Pyrrolidine-2-carboxylic acid</synonym>
    <synonym>P</synonym>
    <synonym>Prolina</synonym>
    <synonym>PROLINE</synonym>
    <synonym>Prolinum</synonym>
    <synonym>(-)-2-Pyrrolidinecarboxylate</synonym>
    <synonym>(2S)-Pyrrolidine-2-carboxylate</synonym>
    <synonym>(S)-2-Pyrrolidinecarboxylate</synonym>
    <synonym>(S)-Pyrrolidine-2-carboxylate</synonym>
    <synonym>2-Pyrrolidinecarboxylate</synonym>
    <synonym>L-a-Pyrrolidinecarboxylate</synonym>
    <synonym>L-a-Pyrrolidinecarboxylic acid</synonym>
    <synonym>L-alpha-Pyrrolidinecarboxylate</synonym>
    <synonym>L-Α-pyrrolidinecarboxylate</synonym>
    <synonym>L-Α-pyrrolidinecarboxylic acid</synonym>
    <synonym>L-Pyrrolidine-2-carboxylate</synonym>
    <synonym>(S)-(-)-Proline</synonym>
    <synonym>(S)-(-)-Pyrrolidine-2-carboxylate</synonym>
    <synonym>(S)-(-)-Pyrrolidine-2-carboxylic acid</synonym>
    <synonym>(S)-2-Pyrralidinecarboxylate</synonym>
    <synonym>(S)-2-Pyrralidinecarboxylic acid</synonym>
    <synonym>(S)-Proline</synonym>
    <synonym>L Proline</synonym>
  </synonyms>
  <chemical_formula>C5H9NO2</chemical_formula>
  <average_molecular_weight>115.1305</average_molecular_weight>
  <monisotopic_moleculate_weight>115.063328537</monisotopic_moleculate_weight>
  <iupac_name>(2S)-pyrrolidine-2-carboxylic acid</iupac_name>
  <traditional_iupac>L-proline</traditional_iupac>
  <cas_registry_number>147-85-3</cas_registry_number>
  <smiles>OC(=O)[C@@H]1CCCN1</smiles>
  <inchi>InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1</inchi>
  <inchikey>ONIBWKKTOPOVIA-BYPYZUCNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Proline and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrrolidine carboxylic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Proline or derivatives</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidine carboxylic acid</substituent>
      <substituent>Pyrrolidine carboxylic acid or derivatives</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>glutamine family amino acid</external_descriptor>
      <external_descriptor>proline</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>221 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>162.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.54</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>11.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-pyrrolidine-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>115.1305</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>115.063328537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)[C@@H]1CCCN1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H9NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ONIBWKKTOPOVIA-BYPYZUCNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>49.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Proline</name>
      <smpdb_id>SMP0119407</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3249</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>45.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>84-110</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>45-68</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Sadri H, von Soosten D, Meyer U, Kluess J, Danicke S, Saremi B, Sauerwein H: Plasma amino acids and metabolic profiling of dairy cows in response to a bolus duodenal infusion of leucine. PLoS One. 2017 Apr 28;12(4):e0176647. doi: 10.1371/journal.pone.0176647. eCollection 2017.</reference_text>
          <pubmed_id>28453535</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>103+/-15</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>72-78</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>352+/-67</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>174+/-59</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>82.350 +/- 29.96</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11 - 47</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29531.705</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29531.705</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29531.705</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29531.705</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28663.126</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28663.126</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28663.126</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19.2 +/-  5.6 </concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from Brown Swiss cows during early lactation</comment>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
          <pubmed_id>23931703</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29.0 +/- 9.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from Simmental cows during early lactation</comment>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
          <pubmed_id>23931703</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>55.55 +/- 12.68</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>60.57 +/- 15.15</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>5.95+/-1.89</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>6.67+/-2.85</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>5.12+/-1.46</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>5.59+/-1.45</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>240-365</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>158 +/- 33</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>220 +/- 31</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>173 +/- 29</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>159.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>158 +/- 24</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>220.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>158 +/- 24</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR, GC-MS and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>173.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>154.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>240-1275</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>50-174</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>117</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>165</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>141</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>130</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>834+/-377</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>154.56 +/- 24.18</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>203+/-60</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>191+/-40</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00148</kegg_id>
  <drugbank_id>DB00172</drugbank_id>
  <foodb_id>FDB000570</foodb_id>
  <chemspider_id>128566</chemspider_id>
  <pubchem_compound_id>145742</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17203</chebi_id>
  <meta_cyc_id>PRO</meta_cyc_id>
  <knapsack_id>C00001388</knapsack_id>
  <wikipedia_id>L-proline</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34042</bigg_id>
  <metlin_id>29</metlin_id>
  <synthesis_reference>Itoh, Tamio. Synthesis of L-proline from L-glutamine. Bulletin of the Chemical Society of Japan (1963), 36(1), 25-9</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
      <pubmed_id>23931703</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00499</protein_accession>
      <name>Cytosol aminopeptidase</name>
      <uniprot_id>P00727</uniprot_id>
      <gene_name>LAP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00641</protein_accession>
      <name>Xaa-Pro aminopeptidase 1</name>
      <uniprot_id>Q1JPJ2</uniprot_id>
      <gene_name>XPNPEP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00668</protein_accession>
      <name>Prolyl 4-hydroxylase subunit alpha-1</name>
      <uniprot_id>Q1RMU3</uniprot_id>
      <gene_name>P4HA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00691</protein_accession>
      <name>Prolyl 4-hydroxylase subunit alpha-3</name>
      <uniprot_id>Q75UG4</uniprot_id>
      <gene_name>P4HA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00873</protein_accession>
      <name>Probable proline dehydrogenase 2</name>
      <uniprot_id>A6QQ74</uniprot_id>
      <gene_name>PRODH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00924</protein_accession>
      <name>Probable proline racemase</name>
      <uniprot_id>Q3SX04</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01016</protein_accession>
      <name>Pyrroline-5-carboxylate reductase 3</name>
      <uniprot_id>Q58D08</uniprot_id>
      <gene_name>PYCRL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01018</protein_accession>
      <name>Pyrroline-5-carboxylate reductase 2</name>
      <uniprot_id>Q17QJ7</uniprot_id>
      <gene_name>PYCR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01024</protein_accession>
      <name>Pyrroline-5-carboxylate reductase 1, mitochondrial</name>
      <uniprot_id>Q58DT4</uniprot_id>
      <gene_name>PYCR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01254</protein_accession>
      <name>Cathepsin Z</name>
      <uniprot_id>P05689</uniprot_id>
      <gene_name>CTSZ</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:24 UTC</creation_date>
  <update_date>2020-04-15 22:27:26 UTC</update_date>
  <accession>BMDB0000163</accession>
  <secondary_accessions>
    <accession>BMDB00163</accession>
  </secondary_accessions>
  <name>D-Maltose</name>
  <description>Maltose, also known as alpha-malt sugar or cextromaltose, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Maltose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Maltose exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>4-O-alpha-D-Glucopyranosyl-alpha-D-mannopyranose</synonym>
    <synonym>4-O-a-D-Glucopyranosyl-a-D-mannopyranose</synonym>
    <synonym>4-O-Α-D-glucopyranosyl-α-D-mannopyranose</synonym>
    <synonym>1-alpha-D-Glucopyranosyl-4-alpha-D-glucopyranose</synonym>
    <synonym>1-alpha-delta-Glucopyranosyl-4-alpha-delta-glucopyranose</synonym>
    <synonym>4-(alpha-D-Glucopyranosido)-alpha-glucopyranose</synonym>
    <synonym>4-(alpha-D-Glucosido)-D-glucose</synonym>
    <synonym>4-(alpha-delta-Glucopyranosido)-alpha-glucopyranose</synonym>
    <synonym>4-(alpha-delta-Glucosido)-delta-glucose</synonym>
    <synonym>4-O-a-D-Glucopyranosyl-D-glucose</synonym>
    <synonym>4-O-alpha-D-Glucopyranosyl-D-glucopyranose</synonym>
    <synonym>4-O-alpha-D-Glucopyranosyl-D-glucose</synonym>
    <synonym>4-O-alpha-delta-Glucopyranosyl-delta-glucopyranose</synonym>
    <synonym>4-O-alpha-delta-Glucopyranosyl-delta-glucose</synonym>
    <synonym>Advantose 100</synonym>
    <synonym>alpha-D-GLCP-(1-&gt;4)-D-GLCP</synonym>
    <synonym>alpha-D-Glucopyranosyl-(1-&gt;4)-D-glucopyranose</synonym>
    <synonym>alpha-D-Glucopyranosyl-(1-&gt;4)-D-glucose</synonym>
    <synonym>alpha-delta-GLCP-(1-&gt;4)-delta-GLCP</synonym>
    <synonym>alpha-delta-Glucopyranosyl-(1-&gt;4)-delta-glucopyranose</synonym>
    <synonym>alpha-delta-Glucopyranosyl-(1-&gt;4)-delta-glucose</synonym>
    <synonym>alpha-Malt sugar</synonym>
    <synonym>Cextromaltose</synonym>
    <synonym>D-(+)-Maltose</synonym>
    <synonym>delta-(+)-Maltose</synonym>
    <synonym>delta-Maltose</synonym>
    <synonym>Finetose</synonym>
    <synonym>Finetose F</synonym>
    <synonym>Madoros</synonym>
    <synonym>Malt sugar</synonym>
    <synonym>Maltobiose</synonym>
    <synonym>Maltodiose</synonym>
    <synonym>Maltos</synonym>
    <synonym>Maltose</synonym>
    <synonym>Maltose HH</synonym>
    <synonym>Maltose HHH</synonym>
    <synonym>Maltose solution</synonym>
    <synonym>Malzzucker</synonym>
    <synonym>Martos-10</synonym>
    <synonym>Sunmalt</synonym>
    <synonym>Sunmalt S</synonym>
  </synonyms>
  <chemical_formula>C12H22O11</chemical_formula>
  <average_molecular_weight>342.2965</average_molecular_weight>
  <monisotopic_moleculate_weight>342.116211546</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol</traditional_iupac>
  <cas_registry_number>69-79-4</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@H](O)[C@@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8+,9-,10-,11+,12-/m1/s1</inchi>
  <inchikey>GUBGYTABKSRVRQ-DKBJLJRDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>O-glycosyl compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Disaccharides</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>alpha-D-glucosyl-(1-&gt;4)-D-mannopyranose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>102 - 103 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>780.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>342.2965</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>342.116211546</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@H](O)[C@@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H22O11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8+,9-,10-,11+,12-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GUBGYTABKSRVRQ-DKBJLJRDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>189.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343011</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00208</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB001193</foodb_id>
  <chemspider_id>9166684</chemspider_id>
  <pubchem_compound_id>10991489</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>47937</chebi_id>
  <meta_cyc_id/>
  <knapsack_id>C00001140</knapsack_id>
  <wikipedia_id>Maltose</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34261</bigg_id>
  <metlin_id>413</metlin_id>
  <synthesis_reference>Pedersen, Sven; Vang Hendriksen, Hanne.  Method for production of maltose and/or enzymatically modified starch.    PCT Int. Appl.  (2001),     99 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01617</protein_accession>
      <name>Collectin-43</name>
      <uniprot_id>P42916</uniprot_id>
      <gene_name>CL43</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02052</protein_accession>
      <name>Pulmonary surfactant-associated protein D</name>
      <uniprot_id>P35246</uniprot_id>
      <gene_name>SFTPD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:25 UTC</creation_date>
  <update_date>2020-03-13 16:19:13 UTC</update_date>
  <accession>BMDB0000164</accession>
  <secondary_accessions>
    <accession>BMDB00164</accession>
  </secondary_accessions>
  <name>Methylamine</name>
  <description>Methylamine, also known as aminomethane or methanamine, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Methylamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Methylamine exists in all living organisms, ranging from bacteria to humans. 3,4-Dihydroxymandelaldehyde and methylamine can be biosynthesized from epinephrine through its interaction with the enzyme amine oxidase [flavin-containing] a. In cattle, methylamine is involved in the metabolic pathway called the tyrosine metabolism pathway. Methylamine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>Aminomethane</synonym>
    <synonym>CH3-NH2</synonym>
    <synonym>MeNH2</synonym>
    <synonym>Methanamine</synonym>
    <synonym>MMA</synonym>
    <synonym>Monomethylamine</synonym>
    <synonym>Anhydrous methylamine</synonym>
    <synonym>Carbinamine</synonym>
    <synonym>Imizin</synonym>
    <synonym>Mercurialin</synonym>
    <synonym>Methyl group</synonym>
    <synonym>Methyl OF gamma-N-methylasparagine</synonym>
    <synonym>Methylamine anhydrous</synonym>
    <synonym>Methylamine aqueous solution</synonym>
    <synonym>Methylamine solution</synonym>
    <synonym>Methylamine solutions</synonym>
    <synonym>Methylaminen</synonym>
    <synonym>Metilamine</synonym>
    <synonym>Metyloamina</synonym>
    <synonym>N-Methylamine</synonym>
    <synonym>NMA</synonym>
    <synonym>NME</synonym>
    <synonym>Methylamine ion (1-)</synonym>
    <synonym>Methylamine nitrate</synonym>
    <synonym>Methylamine perchlorate</synonym>
    <synonym>Methylamine sulfate (1:1)</synonym>
    <synonym>Methylamine sulfate (2:1)</synonym>
    <synonym>Methylamine, 13C-labeled</synonym>
    <synonym>Methylamine, 14C-labeled</synonym>
    <synonym>Methylamine, 15N-labeled</synonym>
    <synonym>Methylamine hydrobromide</synonym>
    <synonym>Methylamine hydrochloride, 14C-labeled</synonym>
    <synonym>Methylamine, cesium salt</synonym>
    <synonym>Methylamine, monopotassium salt</synonym>
    <synonym>Methylammonium</synonym>
    <synonym>Methylammonium ion</synonym>
    <synonym>Methylamine hydroiodide</synonym>
    <synonym>Methylamine, monosodium salt</synonym>
    <synonym>Methylamine bisulfite</synonym>
    <synonym>Methylamine hydride</synonym>
    <synonym>Methylamine hydrochloride</synonym>
    <synonym>Methylamine hydrofluoride</synonym>
    <synonym>Methylamine hydrogen cyanide</synonym>
    <synonym>Monomethylammonium ion</synonym>
  </synonyms>
  <chemical_formula>CH5N</chemical_formula>
  <average_molecular_weight>31.0571</average_molecular_weight>
  <monisotopic_moleculate_weight>31.042199165</monisotopic_moleculate_weight>
  <iupac_name>methanamine</iupac_name>
  <traditional_iupac>methylamine</traditional_iupac>
  <cas_registry_number>74-89-5</cas_registry_number>
  <smiles>CN</smiles>
  <inchi>InChI=1S/CH5N/c1-2/h2H2,1H3</inchi>
  <inchikey>BAVYZALUXZFZLV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>Monoalkylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>methylamines</external_descriptor>
      <external_descriptor>one-carbon compound</external_descriptor>
      <external_descriptor>primary aliphatic amine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-93.4 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1080 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.57</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>methanamine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>31.0571</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>31.042199165</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>CH5N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/CH5N/c1-2/h2H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BAVYZALUXZFZLV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>26.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>9.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>3.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270092</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Charolais cows.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>181-2390</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>4-49</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>132+/-116</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00218</kegg_id>
  <drugbank_id>DB01828</drugbank_id>
  <foodb_id>FDB003958</foodb_id>
  <chemspider_id>6089</chemspider_id>
  <pubchem_compound_id>6329</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16830</chebi_id>
  <meta_cyc_id>METHYLAMINE</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Methylamine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>1800349</bigg_id>
  <metlin_id>3767</metlin_id>
  <synthesis_reference>Denham, William S.; Knapp, Lionel F. The preparation of methylamine from ammonium methyl sulfate. Journal of the Chemical Society, Transactions (1920), 117 236-47.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:26 UTC</creation_date>
  <update_date>2020-04-16 20:38:59 UTC</update_date>
  <accession>BMDB0000167</accession>
  <secondary_accessions>
    <accession>BMDB00167</accession>
  </secondary_accessions>
  <name>L-Threonine</name>
  <description>L-Threonine, also known as (2S)-threonine or L threonine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-Threonine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Threonine exists in all living species, ranging from bacteria to humans. L-Threonine is a potentially toxic compound. L-Threonine has been found to be associated with several diseases known as crohn's disease, rheumatoid arthritis, eosinophilic esophagitis, and heart failure; also l-threonine has been linked to the inborn metabolic disorders including fumarase deficiency.</description>
  <synonyms>
    <synonym>(2S)-Threonine</synonym>
    <synonym>(2S,3R)-(-)-Threonine</synonym>
    <synonym>(2S,3R)-2-Amino-3-hydroxybutanoic acid</synonym>
    <synonym>2-Amino-3-hydroxybutyric acid</synonym>
    <synonym>L-(-)-Threonine</synonym>
    <synonym>L-2-Amino-3-hydroxybutyric acid</synonym>
    <synonym>L-alpha-Amino-beta-hydroxybutyric acid</synonym>
    <synonym>L-Threonin</synonym>
    <synonym>T</synonym>
    <synonym>Thr</synonym>
    <synonym>THREONINE</synonym>
    <synonym>(2S,3R)-2-Amino-3-hydroxybutanoate</synonym>
    <synonym>2-Amino-3-hydroxybutyrate</synonym>
    <synonym>L-2-Amino-3-hydroxybutyrate</synonym>
    <synonym>L-a-Amino-b-hydroxybutyrate</synonym>
    <synonym>L-a-Amino-b-hydroxybutyric acid</synonym>
    <synonym>L-alpha-Amino-beta-hydroxybutyrate</synonym>
    <synonym>L-Α-amino-β-hydroxybutyrate</synonym>
    <synonym>L-Α-amino-β-hydroxybutyric acid</synonym>
    <synonym>(2S,3R)-2-Amino-3-hydroxybutyrate</synonym>
    <synonym>(2S,3R)-2-Amino-3-hydroxybutyric acid</synonym>
    <synonym>(R-(R*,s*))-2-amino-3-hydroxybutanoate</synonym>
    <synonym>(R-(R*,s*))-2-amino-3-hydroxybutanoic acid</synonym>
    <synonym>(S)-Threonine</synonym>
    <synonym>2-Amino-3-hydroxybutanoate</synonym>
    <synonym>2-Amino-3-hydroxybutanoic acid</synonym>
    <synonym>Threonin</synonym>
    <synonym>[R-(R*,s*)]-2-amino-3-hydroxy-butanoate</synonym>
    <synonym>[R-(R*,s*)]-2-amino-3-hydroxy-butanoic acid</synonym>
    <synonym>[R-(R*,s*)]-2-amino-3-hydroxybutanoate</synonym>
    <synonym>[R-(R*,s*)]-2-amino-3-hydroxybutanoic acid</synonym>
    <synonym>L Threonine</synonym>
  </synonyms>
  <chemical_formula>C4H9NO3</chemical_formula>
  <average_molecular_weight>119.1192</average_molecular_weight>
  <monisotopic_moleculate_weight>119.058243159</monisotopic_moleculate_weight>
  <iupac_name>(2S,3R)-2-amino-3-hydroxybutanoic acid</iupac_name>
  <traditional_iupac>L-threonine</traditional_iupac>
  <cas_registry_number>72-19-5</cas_registry_number>
  <smiles>C[C@@H](O)[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1</inchi>
  <inchikey>AYFVYJQAPQTCCC-GBXIJSLDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>aspartate family amino acid</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
      <external_descriptor>threonine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>256 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>97.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.94</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3R)-2-amino-3-hydroxybutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>119.1192</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>119.058243159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](O)[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H9NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AYFVYJQAPQTCCC-GBXIJSLDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>83.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>26.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Protein Synthesis: Threonine</name>
      <smpdb_id>SMP0119410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Threonine and 2-Oxobutanoate Degradation</name>
      <smpdb_id>SMP0087262</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178482</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>51.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>78.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>58-76</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>71-110</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>72-79</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>74+/-12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>377+/-95</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>194+/-80</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1 - 46</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12592.428</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12592.428</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12592.428</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12592.428</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12592.428</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12592.428</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12592.428</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.57+/-0.28</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.69+/-0.31</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.69+/-0.27</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.64+/-0.27</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>193-468</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>28 +/- 7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>35 +/- 22</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>41 +/- 29</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>25 +/- 8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>25 +/- 8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by GC-MS and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>53-153</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>29.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>36.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>41.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>23.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>113.5 (37.0 - 190.0)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>This concentration measured after 1 hour of feeding.; The three amino acids (AA), threonine, methionine and Lysine were administered intraruminally in mixtures at dosages of 100, 200, 300, and 400 mmol of each,together with polyethylene glycol (PEG) as a liquid marker.  </comment>
      <references>
        <reference>
          <reference_text>Volden H, Velle W, Harstad OM, Aulie A, Sjaastad OV: Apparent ruminal degradation and rumen escape of lysine, methionine, and threonine administered intraruminally in mixtures to high-yielding cows. J Anim Sci. 1998 Apr;76(4):1232-40.</reference_text>
          <pubmed_id>9581948</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>658+/-301</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>24.45 +/- 7.32</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>193+/-32</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>140</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Sexton TJ, Amann RP, Flipse RJ: Free amino acids and protein in rete testis fluid, vas deferens plasma, accessory sex gland fluid, and seminal plasma of the conscious bull. J Dairy Sci. 1971 Mar;54(3):412-6. doi: 10.3168/jds.s0022-0302(71)85854-x.</reference_text>
          <pubmed_id>5096119</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>232+/-51</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00188</kegg_id>
  <drugbank_id>DB00156</drugbank_id>
  <foodb_id>FDB011999</foodb_id>
  <chemspider_id>6051</chemspider_id>
  <pubchem_compound_id>6288</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16857</chebi_id>
  <meta_cyc_id/>
  <knapsack_id>C00001394</knapsack_id>
  <wikipedia_id>Threonine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34186</bigg_id>
  <metlin_id>32</metlin_id>
  <synthesis_reference>Fujita, Chuzo; Nara, Takashi; Samejima, Hirotoshi; Kinoshita, Shukuo. L-Threonine fermentation. I. Microbial conversion of L-homoserine to L-threonine. Nippon Nogei Kagaku Kaishi (1965), 39(6), 2</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00088</protein_accession>
      <name>L-serine dehydratase</name>
      <uniprot_id>Q0VCW4</uniprot_id>
      <gene_name>SDS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00384</protein_accession>
      <name>Probable threonyl-tRNA synthetase 2, cytoplasmic</name>
      <uniprot_id>A6QNM8</uniprot_id>
      <gene_name>TARSL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00385</protein_accession>
      <name>L-threonine 3-dehydrogenase, mitochondrial</name>
      <uniprot_id>Q2KIR8</uniprot_id>
      <gene_name>TDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00386</protein_accession>
      <name>Threonyl-tRNA synthetase, cytoplasmic</name>
      <uniprot_id>Q3ZBV8</uniprot_id>
      <gene_name>TARS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:27 UTC</creation_date>
  <update_date>2020-04-16 20:39:00 UTC</update_date>
  <accession>BMDB0000168</accession>
  <secondary_accessions>
    <accession>BMDB00168</accession>
  </secondary_accessions>
  <name>L-Asparagine</name>
  <description>L-Asparagine, also known as Asn or aspartamic acid, belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Asparagine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. L-Asparagine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Asparagine exists in all living species, ranging from bacteria to humans. L-Asparagine is a potentially toxic compound. L-Asparagine has been found to be associated with several diseases known as pregnancy, cystic fibrosis, gout, and leukemia; also l-asparagine has been linked to the inborn metabolic disorders including celiac disease.</description>
  <synonyms>
    <synonym>(2S)-2,4-Diamino-4-oxobutanoic acid</synonym>
    <synonym>(2S)-2-Amino-3-carbamoylpropanoic acid</synonym>
    <synonym>(S)-2-Amino-3-carbamoylpropanoic acid</synonym>
    <synonym>(S)-Asparagine</synonym>
    <synonym>2-Aminosuccinamic acid</synonym>
    <synonym>alpha-Aminosuccinamic acid</synonym>
    <synonym>Asn</synonym>
    <synonym>ASPARAGINE</synonym>
    <synonym>Aspartamic acid</synonym>
    <synonym>L-2-Aminosuccinamic acid</synonym>
    <synonym>L-Asparagin</synonym>
    <synonym>L-Aspartic acid beta-amide</synonym>
    <synonym>N</synonym>
    <synonym>(2S)-2,4-Diamino-4-oxobutanoate</synonym>
    <synonym>(2S)-2-Amino-3-carbamoylpropanoate</synonym>
    <synonym>(S)-2-Amino-3-carbamoylpropanoate</synonym>
    <synonym>2-Aminosuccinamate</synonym>
    <synonym>a-Aminosuccinamate</synonym>
    <synonym>a-Aminosuccinamic acid</synonym>
    <synonym>alpha-Aminosuccinamate</synonym>
    <synonym>Α-aminosuccinamate</synonym>
    <synonym>Α-aminosuccinamic acid</synonym>
    <synonym>Aspartamate</synonym>
    <synonym>L-2-Aminosuccinamate</synonym>
    <synonym>L-Aspartate b-amide</synonym>
    <synonym>L-Aspartate beta-amide</synonym>
    <synonym>L-Aspartate β-amide</synonym>
    <synonym>L-Aspartic acid b-amide</synonym>
    <synonym>L-Aspartic acid β-amide</synonym>
    <synonym>(-)-Asparagine</synonym>
    <synonym>(S)-2,4-Diamino-4-oxobutanoate</synonym>
    <synonym>(S)-2,4-Diamino-4-oxobutanoic acid</synonym>
    <synonym>Agedoite</synonym>
    <synonym>alpha Amminosuccinamate</synonym>
    <synonym>alpha Amminosuccinamic acid</synonym>
    <synonym>Altheine</synonym>
    <synonym>Asparagine acid</synonym>
    <synonym>Asparamide</synonym>
    <synonym>Aspartic acid amide</synonym>
    <synonym>Aspartic acid b-amide</synonym>
    <synonym>Aspartic acid beta amide</synonym>
    <synonym>b2,4-(S)-Diamino-4-oxo-utanoate</synonym>
    <synonym>b2,4-(S)-Diamino-4-oxo-utanoic acid</synonym>
    <synonym>Crystal VI</synonym>
    <synonym>L-2,4-Diamino-4-oxobutanoate</synonym>
    <synonym>L-2,4-Diamino-4-oxobutanoic acid</synonym>
    <synonym>L-Aspartamine</synonym>
    <synonym>L-b-Asparagine</synonym>
    <synonym>L-beta-Asparagine</synonym>
  </synonyms>
  <chemical_formula>C4H8N2O3</chemical_formula>
  <average_molecular_weight>132.1179</average_molecular_weight>
  <monisotopic_moleculate_weight>132.053492132</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-carbamoylpropanoic acid</iupac_name>
  <traditional_iupac>L-asparagine</traditional_iupac>
  <cas_registry_number>70-47-3</cas_registry_number>
  <smiles>N[C@@H](CC(N)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1</inchi>
  <inchikey>DCXYFEDJOCDNAF-REOHCLBHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Asparagine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Fatty amides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Asparagine or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>asparagine</external_descriptor>
      <external_descriptor>aspartate family amino acid</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>234 - 235 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>29.4 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.82</value>
      <source>CHMELIK,J ET AL. (1991)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-carbamoylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.1179</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.053492132</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CC(N)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DCXYFEDJOCDNAF-REOHCLBHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>106.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Asparagine</name>
      <smpdb_id>SMP0119385</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30882</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31046</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>27.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>22-27</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>25.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>20-33</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Sadri H, von Soosten D, Meyer U, Kluess J, Danicke S, Saremi B, Sauerwein H: Plasma amino acids and metabolic profiling of dairy cows in response to a bolus duodenal infusion of leucine. PLoS One. 2017 Apr 28;12(4):e0176647. doi: 10.1371/journal.pone.0176647. eCollection 2017.</reference_text>
          <pubmed_id>28453535</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>34-40</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>25+/-4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>169+/-37</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>40+/-12</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.6 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.5 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.5 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.3 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>106-225</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>46+/-17</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>48+/-11</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00152</kegg_id>
  <drugbank_id>DB00174</drugbank_id>
  <foodb_id>FDB000787</foodb_id>
  <chemspider_id>6031</chemspider_id>
  <pubchem_compound_id>6267</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17196</chebi_id>
  <meta_cyc_id>ASN</meta_cyc_id>
  <knapsack_id>C00001341</knapsack_id>
  <wikipedia_id>Asparagine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34055</bigg_id>
  <metlin_id>14</metlin_id>
  <synthesis_reference>Wang, Fangda.  Preparation of L-b-asparagine.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2005),     8 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00563</protein_accession>
      <name>Asparagine synthetase [glutamine-hydrolyzing]</name>
      <uniprot_id>Q1LZA3</uniprot_id>
      <gene_name>ASNS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00565</protein_accession>
      <name>L-asparaginase</name>
      <uniprot_id>Q32LE5</uniprot_id>
      <gene_name>ASRGL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00840</protein_accession>
      <name>Asparaginyl-tRNA synthetase, cytoplasmic</name>
      <uniprot_id>Q2KJG3</uniprot_id>
      <gene_name>NARS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00841</protein_accession>
      <name>Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit DAD1</name>
      <uniprot_id>Q5E9C2</uniprot_id>
      <gene_name>DAD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00842</protein_accession>
      <name>Dolichyl-diphosphooligosaccharide--protein glycosyltransferase 48 kDa subunit</name>
      <uniprot_id>A6QPY0</uniprot_id>
      <gene_name>DDOST</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00843</protein_accession>
      <name>Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit 2</name>
      <uniprot_id>Q3SZI6</uniprot_id>
      <gene_name>RPN2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00844</protein_accession>
      <name>Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit STT3A</name>
      <uniprot_id>Q2KJI2</uniprot_id>
      <gene_name>STT3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02092</protein_accession>
      <name>Sodium-coupled neutral amino acid transporter 5</name>
      <uniprot_id>Q5E9S9</uniprot_id>
      <gene_name>SLC38A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:28 UTC</creation_date>
  <update_date>2020-04-16 17:53:05 UTC</update_date>
  <accession>BMDB0000169</accession>
  <secondary_accessions>
    <accession>BMDB00169</accession>
  </secondary_accessions>
  <name>D-Mannose</name>
  <description>D-Mannose, also known as mannopyranose or carubinose, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. D-Mannose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Mannose exists in all living species, ranging from bacteria to humans. D-Mannose can be converted into mannose 6-phosphate; which is mediated by the enzyme hexokinase-1. In cattle, D-mannose is involved in the metabolic pathway called the fructose and mannose degradation pathway.</description>
  <synonyms>
    <synonym>Carubinose</synonym>
    <synonym>Mannopyranose</synonym>
    <synonym>Seminose</synonym>
    <synonym>Mannose</synonym>
    <synonym>D-Mannopyranose</synonym>
    <synonym>(+)-Mannose</synonym>
    <synonym>(+-)-Mannose</synonym>
    <synonym>D(+)-Mannose</synonym>
    <synonym>DL-Mannose</synonym>
    <synonym>Mannopyranoside</synonym>
    <synonym>D Mannose</synonym>
  </synonyms>
  <chemical_formula>C6H12O6</chemical_formula>
  <average_molecular_weight>180.1559</average_molecular_weight>
  <monisotopic_moleculate_weight>180.063388116</monisotopic_moleculate_weight>
  <iupac_name>(3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>β-glucose</traditional_iupac>
  <cas_registry_number>530-26-7</cas_registry_number>
  <smiles>OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6?/m1/s1</inchi>
  <inchikey>WQZGKKKJIJFFOK-QTVWNMPRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Aldoses</external_descriptor>
      <external_descriptor>D-aldohexose</external_descriptor>
      <external_descriptor>D-mannose</external_descriptor>
      <external_descriptor>mannopyranose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>132 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>713.0 mg/mL at 17 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3S,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>180.1559</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>180.063388116</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5+,6?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WQZGKKKJIJFFOK-QTVWNMPRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>110.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447486</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in beef muscle (longissimus dorsi).</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>91 +/- 49</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>159 +/- 83</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>211 +/- 86</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>125 +/- 25</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>125 +/- 25</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by GC-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>91.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>159.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>210.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>123.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>763.813 +/- 751.731</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>91.62 +/- 25.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00159</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB001202</foodb_id>
  <chemspider_id>17893</chemspider_id>
  <pubchem_compound_id>18950</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>4208</chebi_id>
  <knapsack_id>C00001126</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>MANNOSE</meta_cyc_id>
  <bigg_id>34085</bigg_id>
  <wikipedia_id>Mannose</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Sowden, John C.; Fischer, Hermann O. L. Condensation of nitromethane with D- and L-arabinose: preparation of L-glucose and L-mannose. Journal of the American Chemical Society (1947), 69 1963-5.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
      <pubmed_id>27999311</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00234</protein_accession>
      <name>Tissue-type plasminogen activator</name>
      <uniprot_id>Q28198</uniprot_id>
      <gene_name>PLAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01617</protein_accession>
      <name>Collectin-43</name>
      <uniprot_id>P42916</uniprot_id>
      <gene_name>CL43</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01897</protein_accession>
      <name>Insulin-like growth factor receptor type 2</name>
      <uniprot_id>Q95M44</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01898</protein_accession>
      <name>Basigin</name>
      <uniprot_id>Q865R3</uniprot_id>
      <gene_name>BSG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01899</protein_accession>
      <name>Cation-dependent mannose-6-phosphate receptor</name>
      <uniprot_id>P11456</uniprot_id>
      <gene_name>M6PR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01900</protein_accession>
      <name>Collectin-11</name>
      <uniprot_id>Q17QH6</uniprot_id>
      <gene_name>COLEC11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01901</protein_accession>
      <name>Collectin-46</name>
      <uniprot_id>Q8MHZ9</uniprot_id>
      <gene_name>CL46</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01902</protein_accession>
      <name>Lectin mannose binding 1</name>
      <uniprot_id>Q8MJ82</uniprot_id>
      <gene_name>lman1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01903</protein_accession>
      <name>Mannan-binding lectin A</name>
      <uniprot_id>Q5I2B0</uniprot_id>
      <gene_name>MBL-A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01904</protein_accession>
      <name>F-box only protein 6</name>
      <uniprot_id>Q3SX24</uniprot_id>
      <gene_name>FBXO6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01905</protein_accession>
      <name>Mannose receptor</name>
      <uniprot_id>Q7M2U1</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01906</protein_accession>
      <name>Mannose 6 phosphate receptor binding protein 1</name>
      <uniprot_id>Q3SX32</uniprot_id>
      <gene_name>M6PRBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01907</protein_accession>
      <name>Similar to mannose-6-phosphate/insulin-like growth factor II receptor</name>
      <uniprot_id>Q862E4</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01908</protein_accession>
      <name>Conglutinin</name>
      <uniprot_id>P23805</uniprot_id>
      <gene_name>CGN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01909</protein_accession>
      <name>Acrosin</name>
      <uniprot_id>P79343</uniprot_id>
      <gene_name>bovine proacrosine</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01910</protein_accession>
      <name>Mannose-binding protein C</name>
      <uniprot_id>O02659</uniprot_id>
      <gene_name>MBL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01911</protein_accession>
      <name>Cation-independent mannose-6-phosphate receptor</name>
      <uniprot_id>P08169</uniprot_id>
      <gene_name>IGF2R</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:30 UTC</creation_date>
  <update_date>2020-04-16 20:39:00 UTC</update_date>
  <accession>BMDB0000172</accession>
  <secondary_accessions>
    <accession>BMDB00172</accession>
  </secondary_accessions>
  <name>L-Isoleucine</name>
  <description>L-Isoleucine, also known as I, belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Thus, L-isoleucine is considered to be a fatty acid lipid molecule. L-Isoleucine exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. L-Isoleucine exists in all living species, ranging from bacteria to humans. L-Isoleucine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2S,3S)-2-Amino-3-methylpentanoic acid</synonym>
    <synonym>2-Amino-3-methylvaleric acid</synonym>
    <synonym>alpha-Amino-beta-methylvaleric acid</synonym>
    <synonym>I</synonym>
    <synonym>Ile</synonym>
    <synonym>ISOLEUCINE</synonym>
    <synonym>(2S,3S)-2-Amino-3-methylpentanoate</synonym>
    <synonym>2-Amino-3-methylvalerate</synonym>
    <synonym>a-Amino-b-methylvalerate</synonym>
    <synonym>a-Amino-b-methylvaleric acid</synonym>
    <synonym>alpha-Amino-beta-methylvalerate</synonym>
    <synonym>Α-amino-β-methylvalerate</synonym>
    <synonym>Α-amino-β-methylvaleric acid</synonym>
    <synonym>(2S,3S)-2-Amino-3-methyl-pentanoate</synonym>
    <synonym>(2S,3S)-2-Amino-3-methyl-pentanoic acid</synonym>
    <synonym>(2S,3S)-a-Amino-b-methyl-N-valerate</synonym>
    <synonym>(2S,3S)-a-Amino-b-methyl-N-valeric acid</synonym>
    <synonym>(2S,3S)-a-Amino-b-methylvalerate</synonym>
    <synonym>(2S,3S)-a-Amino-b-methylvaleric acid</synonym>
    <synonym>(2S,3S)-Alph-amino-beta-methylvalerate</synonym>
    <synonym>(2S,3S)-Alph-amino-beta-methylvaleric acid</synonym>
    <synonym>(2S,3S)-alpha-Amino-beta-merthyl-N-valerate</synonym>
    <synonym>(2S,3S)-alpha-Amino-beta-merthyl-N-valeric acid</synonym>
    <synonym>(2S,3S)-alpha-Amino-beta-merthylvalerate</synonym>
    <synonym>(2S,3S)-alpha-Amino-beta-merthylvaleric acid</synonym>
    <synonym>(2S,3S)-alpha-Amino-beta-methyl-N-valerate</synonym>
    <synonym>(2S,3S)-alpha-Amino-beta-methyl-N-valeric acid</synonym>
    <synonym>(2S,3S)-alpha-Amino-beta-methylvalerate</synonym>
    <synonym>(2S,3S)-alpha-Amino-beta-methylvaleric acid</synonym>
    <synonym>(S)-Isoleucine</synonym>
    <synonym>(S,S)-Isoleucine</synonym>
    <synonym>2-Amino-3-methylpentanoate</synonym>
    <synonym>2-Amino-3-methylpentanoic acid</synonym>
    <synonym>2S,3S-Isoleucine</synonym>
    <synonym>Erythro-L-isoleucine</synonym>
    <synonym>Iso-leucine</synonym>
    <synonym>L-(+)-Isoleucine</synonym>
    <synonym>L-Ile</synonym>
    <synonym>[S-(R*,r*)]-2-amino-3-methylpentanoate</synonym>
    <synonym>[S-(R*,r*)]-2-amino-3-methylpentanoic acid</synonym>
    <synonym>Isoleucine, L-isomer</synonym>
    <synonym>Alloisoleucine</synonym>
    <synonym>Isoleucine, L isomer</synonym>
    <synonym>L-Isomer isoleucine</synonym>
    <synonym>2S-Amino-3S-methylpentanoate</synonym>
    <synonym>L-Isoleucine</synonym>
  </synonyms>
  <chemical_formula>C6H13NO2</chemical_formula>
  <average_molecular_weight>131.1729</average_molecular_weight>
  <monisotopic_moleculate_weight>131.094628665</monisotopic_moleculate_weight>
  <iupac_name>(2S,3S)-2-amino-3-methylpentanoic acid</iupac_name>
  <traditional_iupac>L-isoleucine</traditional_iupac>
  <cas_registry_number>73-32-5</cas_registry_number>
  <smiles>CC[C@H](C)[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1</inchi>
  <inchikey>AGPKZVBTJJNPAG-WHFBIAKZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Isoleucine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isoleucine or derivatives</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>aspartate family amino acid</external_descriptor>
      <external_descriptor>isoleucine</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>285.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>35 mg/mL</value>
      <source>Human Metabolome Project</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.7</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3S)-2-amino-3-methylpentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>131.1729</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>131.094628665</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC[C@H](C)[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AGPKZVBTJJNPAG-WHFBIAKZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Protein Synthesis: Isoleucine</name>
      <smpdb_id>SMP0119393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178772</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 24 male 17-22-month-old Charolais beef cattles.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>71.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>76-101</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>72.05</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>101-122</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>63-118</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Sadri H, von Soosten D, Meyer U, Kluess J, Danicke S, Saremi B, Sauerwein H: Plasma amino acids and metabolic profiling of dairy cows in response to a bolus duodenal infusion of leucine. PLoS One. 2017 Apr 28;12(4):e0176647. doi: 10.1371/journal.pone.0176647. eCollection 2017.</reference_text>
          <pubmed_id>28453535</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>95-103</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>153+/-14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>178+/-29</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>107+/-22</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.15 +/- 1.64</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3 - 14</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2 - 13</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.9 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.5 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.5 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15247.0518</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15247.0518</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15247.0518</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15247.0518</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15247.0518</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15247.0518</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15247.0518</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>This is a duplicate concentration of concentration_id 8086, unpexported by An Chi on Aug 20, 2018</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.33 +/- 1.74</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.4 +/- 0.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.2 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.9 +/- 0.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.7 +/- 0.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.20 +/- 1.53</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from Danish Holstein-Friesian (n = 456) and Jersey cows (n = 436)</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
          <pubmed_id>23182357</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>215.92 +/- 14.82</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>43-231</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>46.75 +/- 3.37</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>387.77+/-50.25</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>2.36+/-0.38</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.64+/-0.07</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.97+/-0.12</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>370</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>72.44 +/- 10.27</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>85.7 +/- 14.97</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>5-11</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>160-588</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>151.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>266.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>182.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>173.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>123-1210</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>137 +/- 40</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>235 +/- 62</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>183 +/- 74</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>147 +/- 42</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>147 +/- 42</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR, GC-MS and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>48-144</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hanne Christine Bertram, Niels Bastian Kristensen, Mogens Vestergaard, SÃ¸ren Krogh Jensen, Jakob Sehested, Niels Christian Nielsen, Anders Malmendal. Metabolic characterization of rumen epithelial tissue from dairy calves fed different starter diets using 1H NMR spectroscopy. Livestock Science (2008) 120:127-134   doi: 10.1016/j.livsci.2008.05.001</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>124</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>222</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>148</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>144</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>556+/-127</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>173.85 +/- 19.76</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>116+/-23</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>30</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Sexton TJ, Amann RP, Flipse RJ: Free amino acids and protein in rete testis fluid, vas deferens plasma, accessory sex gland fluid, and seminal plasma of the conscious bull. J Dairy Sci. 1971 Mar;54(3):412-6. doi: 10.3168/jds.s0022-0302(71)85854-x.</reference_text>
          <pubmed_id>5096119</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>79+/-14</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00407</kegg_id>
  <drugbank_id>DB00167</drugbank_id>
  <foodb_id>FDB012397</foodb_id>
  <chemspider_id>6067</chemspider_id>
  <pubchem_compound_id>6306</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17191</chebi_id>
  <knapsack_id>C00001374</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>ILE</meta_cyc_id>
  <bigg_id>34887</bigg_id>
  <wikipedia_id>Isoleucine</wikipedia_id>
  <metlin_id>5193</metlin_id>
  <synthesis_reference>Marvel, C. S. L-Isoleucine. Organic Syntheses (1941), 21 60-4.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
      <pubmed_id>23182357</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00226</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>A4IFQ7</uniprot_id>
      <gene_name>BCAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00227</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase, mitochondrial</name>
      <uniprot_id>Q5EA40</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00228</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>Q0V8J6</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00229</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>Q5E9U7</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:31 UTC</creation_date>
  <update_date>2020-04-16 20:37:45 UTC</update_date>
  <accession>BMDB0000174</accession>
  <secondary_accessions>
    <accession>BMDB00174</accession>
  </secondary_accessions>
  <name>L-Fucose</name>
  <description>L-Fucose, also known as L-rha or 6-deoxymannose, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. L-Fucose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. L-Fucose exists in all living organisms, ranging from bacteria to humans. L-Fucose can be converted into fucose 1-phosphate; which is mediated by the enzyme L-fucose kinase. In cattle, L-fucose is involved in the metabolic pathway called the fructose and mannose degradation pathway.</description>
  <synonyms>
    <synonym>6-Deoxy-L-galactose</synonym>
    <synonym>(-)-Fucose</synonym>
    <synonym>(-)-L-Fucose</synonym>
    <synonym>6-Deoxy-L-galactopyranose</synonym>
    <synonym>6-Desoxygalactose</synonym>
    <synonym>6-Methyloxane-2,3,4,5-tetrol</synonym>
    <synonym>6-Methyltetrahydropyran-2,3,4,5-tetraol</synonym>
    <synonym>Fucose</synonym>
    <synonym>Isodulcit</synonym>
    <synonym>L-(-)-Fucose</synonym>
    <synonym>L-Fucopyranose</synonym>
    <synonym>L-Galactomethylose</synonym>
    <synonym>Rhodeose</synonym>
    <synonym>alpha Fucose</synonym>
    <synonym>alpha-Fucose</synonym>
    <synonym>Deoxygalactose</synonym>
  </synonyms>
  <chemical_formula>C6H12O5</chemical_formula>
  <average_molecular_weight>164.1565</average_molecular_weight>
  <monisotopic_moleculate_weight>164.068473494</monisotopic_moleculate_weight>
  <iupac_name>(3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>L-fucose</traditional_iupac>
  <cas_registry_number>87-96-7</cas_registry_number>
  <smiles>[H][C@@]1(C)OC([H])(O)[C@@]([H])(O)[C@]([H])(O)[C@]1([H])O</smiles>
  <inchi>InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1</inchi>
  <inchikey>SHZGCJCMOBCMKK-DHVFOXMCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxy sugars</external_descriptor>
      <external_descriptor>L-fucose</external_descriptor>
      <external_descriptor>fucopyranose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>140 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>985 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>164.1565</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>164.068473494</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(C)OC([H])(O)[C@@]([H])(O)[C@]([H])(O)[C@]1([H])O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SHZGCJCMOBCMKK-DHVFOXMCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>90.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326376</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27.79 +/- 13.14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35 +/- 9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23 +/- 11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21.03 +/- 14.33</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35 +/- 9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23 +/- 11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15.36 +/- 7.37</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>763.813 +/- 751.731</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01019</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB020543</foodb_id>
  <chemspider_id>16190</chemspider_id>
  <pubchem_compound_id>17106</pubchem_compound_id>
  <pdbe_id>1AH1</pdbe_id>
  <chebi_id>2181</chebi_id>
  <meta_cyc_id>L-FUCOSE</meta_cyc_id>
  <knapsack_id>C00035100</knapsack_id>
  <wikipedia_id>Fucose</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>36636</bigg_id>
  <metlin_id>268</metlin_id>
  <synthesis_reference>Xu, Zuhong; Zhao, Zengqin; Zhang, Quanbin; Niu, Xizhen; Zhang, Hong; Li, Zhien.  Method for preparing L-fucose from laminaria japonica.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2005),     8 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00633</protein_accession>
      <name>Beta-1,3-N-acetylglucosaminyltransferase lunatic fringe</name>
      <uniprot_id>Q2KJ92</uniprot_id>
      <gene_name>LFNG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00634</protein_accession>
      <name>Tissue alpha-L-fucosidase</name>
      <uniprot_id>Q2KIM0</uniprot_id>
      <gene_name>FUCA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01616</protein_accession>
      <name>Collectin-12</name>
      <uniprot_id>A6QP79</uniprot_id>
      <gene_name>COLEC12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01617</protein_accession>
      <name>Collectin-43</name>
      <uniprot_id>P42916</uniprot_id>
      <gene_name>CL43</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01900</protein_accession>
      <name>Collectin-11</name>
      <uniprot_id>Q17QH6</uniprot_id>
      <gene_name>COLEC11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01908</protein_accession>
      <name>Conglutinin</name>
      <uniprot_id>P23805</uniprot_id>
      <gene_name>CGN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01909</protein_accession>
      <name>Acrosin</name>
      <uniprot_id>P79343</uniprot_id>
      <gene_name>bovine proacrosine</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:32 UTC</creation_date>
  <update_date>2020-04-16 20:39:01 UTC</update_date>
  <accession>BMDB0000175</accession>
  <secondary_accessions>
    <accession>BMDB00175</accession>
  </secondary_accessions>
  <name>Inosinic acid</name>
  <description>Inosinic acid, also known as 5'-inosinate or 5'-imp, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Inosinic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Inosinic acid exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>2'-Inosine-5'-monophosphate</synonym>
    <synonym>5'-IMP</synonym>
    <synonym>5'-Inosinate</synonym>
    <synonym>5'-Inosine monophosphate</synonym>
    <synonym>5'-Inosinic acid</synonym>
    <synonym>Hypoxanthosine 5'-monophosphate</synonym>
    <synonym>Inosine 5'-monophosphate</synonym>
    <synonym>Inosine 5'-phosphate</synonym>
    <synonym>Inosine monophosphate</synonym>
    <synonym>Ribosylhypoxanthine monophosphate</synonym>
    <synonym>2'-Inosine-5'-monophosphoric acid</synonym>
    <synonym>5'-Inosine monophosphoric acid</synonym>
    <synonym>Hypoxanthosine 5'-monophosphoric acid</synonym>
    <synonym>Inosine 5'-monophosphoric acid</synonym>
    <synonym>Inosine 5'-phosphoric acid</synonym>
    <synonym>Inosine monophosphoric acid</synonym>
    <synonym>Ribosylhypoxanthine monophosphoric acid</synonym>
    <synonym>Inosinate</synonym>
    <synonym>IMP</synonym>
    <synonym>Inosine-5'-monophosphate</synonym>
    <synonym>Inosinic acids</synonym>
    <synonym>Inosinate, sodium</synonym>
    <synonym>monoPhosphate, inosine</synonym>
    <synonym>monoPhosphate, ribosylhypoxanthine</synonym>
    <synonym>Sodium inosinate</synonym>
    <synonym>Acid, inosinic</synonym>
    <synonym>Acids, inosinic</synonym>
  </synonyms>
  <chemical_formula>C10H13N4O8P</chemical_formula>
  <average_molecular_weight>348.206</average_molecular_weight>
  <monisotopic_moleculate_weight>348.047099924</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>inosine-5'-monophosphate</traditional_iupac>
  <cas_registry_number>131-99-7</cas_registry_number>
  <smiles>O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CNC2=O</smiles>
  <inchi>InChI=1S/C10H13N4O8P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>GRSZFWQUAKGDAV-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>inosine phosphate</external_descriptor>
      <external_descriptor>purine ribonucleoside 5'-monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>348.206</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>348.047099924</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CNC2=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H13N4O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H13N4O8P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GRSZFWQUAKGDAV-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>175.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4858</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448024</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>34+/-27</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>15+/-11</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>40-8977</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>460</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>31-59</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>124+/-136</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>97+/-19</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00130</kegg_id>
  <drugbank_id>DB04566</drugbank_id>
  <foodb_id>FDB021901</foodb_id>
  <chemspider_id>8264</chemspider_id>
  <pubchem_compound_id>8582</pubchem_compound_id>
  <chebi_id>17202</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>IMP</meta_cyc_id>
  <knapsack_id>C00007224</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33960</bigg_id>
  <wikipedia_id>Inosinic_acid</wikipedia_id>
  <metlin_id>5196</metlin_id>
  <synthesis_reference>Park, Yeong Hun; Cho, Gwang Myeong; Baek, Min Ji; Hong, Guk Gi; Lee, Jin Nam.  Method for preparing 5'-inosinic acid by using microbe capable of over-expressing purC gene.  Repub. Korea  (2007),  7pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00432</protein_accession>
      <name>GMP reductase 2</name>
      <uniprot_id>Q32L93</uniprot_id>
      <gene_name>GMPR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00999</protein_accession>
      <name>GMP reductase</name>
      <uniprot_id>Q08DA2</uniprot_id>
      <gene_name>GMPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01002</protein_accession>
      <name>Inosine-5'-monophosphate dehydrogenase 2</name>
      <uniprot_id>Q3SWY3</uniprot_id>
      <gene_name>IMPDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01003</protein_accession>
      <name>Inosine-5'-monophosphate dehydrogenase</name>
      <uniprot_id>A0JNA3</uniprot_id>
      <gene_name>IMPDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:33 UTC</creation_date>
  <update_date>2020-04-16 17:51:04 UTC</update_date>
  <accession>BMDB0000176</accession>
  <secondary_accessions>
    <accession>BMDB00176</accession>
  </secondary_accessions>
  <name>Maleic acid</name>
  <description>Fumaric acid, also known as fumarate or E297, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Fumaric acid exists as a solid, possibly soluble (in water), and a weakly acidic compound (based on its pKa) molecule. Fumaric acid exists in all living species, ranging from bacteria to humans. Fumaric acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(Z)-2-Butenedioic acid</synonym>
    <synonym>(Z)-Butenedioic acid</synonym>
    <synonym>cis-1,2-Ethylenedicarboxylic acid</synonym>
    <synonym>cis-But-2-enedioic acid</synonym>
    <synonym>cis-Butenedioic acid</synonym>
    <synonym>H2Male</synonym>
    <synonym>Toxilic acid</synonym>
    <synonym>Maleate</synonym>
    <synonym>(Z)-2-Butenedioate</synonym>
    <synonym>(Z)-Butenedioate</synonym>
    <synonym>cis-1,2-Ethylenedicarboxylate</synonym>
    <synonym>cis-But-2-enedioate</synonym>
    <synonym>cis-Butenedioate</synonym>
    <synonym>Toxilate</synonym>
    <synonym>(2Z)-2-Butenedioate</synonym>
    <synonym>(2Z)-2-Butenedioic acid</synonym>
    <synonym>(2Z)-But-2-enedioate</synonym>
    <synonym>(2Z)-But-2-enedioic acid</synonym>
    <synonym>(2Z)-Butene-2-dioate</synonym>
    <synonym>(2Z)-Butene-2-dioic acid</synonym>
    <synonym>2-Butenedioate</synonym>
    <synonym>2-Butenedioic acid</synonym>
    <synonym>cis-2-Butenedioate</synonym>
    <synonym>cis-2-Butenedioic acid</synonym>
    <synonym>Kyselina maleinova</synonym>
    <synonym>MAE</synonym>
    <synonym>Maleinic acid</synonym>
    <synonym>Malenic acid</synonym>
    <synonym>Malezid CM</synonym>
    <synonym>Scotchbond multipurpose etchant</synonym>
    <synonym>Maleic acid, disodium salt</synonym>
    <synonym>Maleic acid, monocopper (2+) salt</synonym>
    <synonym>Maleic acid, potassium salt</synonym>
    <synonym>Maleic acid, sodium salt</synonym>
    <synonym>Sodium maleate</synonym>
    <synonym>Hydrogen maleate</synonym>
    <synonym>Maleic acid, ammonium salt</synonym>
    <synonym>Maleic acid, calcium salt</synonym>
    <synonym>Maleic acid, iron salt</synonym>
    <synonym>Maleic acid, neodymium salt</synonym>
    <synonym>Maleic acid, dipotassium salt</synonym>
    <synonym>Maleic acid, monoammonium salt</synonym>
    <synonym>Maleic acid, monosodium salt</synonym>
  </synonyms>
  <chemical_formula>C4H4O4</chemical_formula>
  <average_molecular_weight>116.0722</average_molecular_weight>
  <monisotopic_moleculate_weight>116.010958616</monisotopic_moleculate_weight>
  <iupac_name>(2Z)-but-2-enedioic acid</iupac_name>
  <traditional_iupac>maleic acid</traditional_iupac>
  <cas_registry_number>110-16-7</cas_registry_number>
  <smiles>OC(=O)\C=C/C(O)=O</smiles>
  <inchi>InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-</inchi>
  <inchikey>VZCYOOQTPOCHFL-UPHRSURJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Dicarboxylic acids and derivatives</sub_class>
    <direct_parent>Dicarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>butenedioic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>130.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>441 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.48</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.041</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2Z)-but-2-enedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>116.0722</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>116.010958616</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)\C=C/C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H4O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VZCYOOQTPOCHFL-UPHRSURJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>24.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439264</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01384</kegg_id>
  <drugbank_id>DB04299</drugbank_id>
  <foodb_id>FDB008113</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>444266</pubchem_compound_id>
  <chebi_id>18300</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>MALEATE</meta_cyc_id>
  <knapsack_id>C00007417</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Maleic_acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Dethloff, Christian; Barbarino, Sergio.  Process temperature optimization in the manufacture of maleic acid by the hydrolysis of maleic anhydride.    Eur. Pat. Appl.  (1998),     7 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:34 UTC</creation_date>
  <update_date>2020-04-16 20:39:01 UTC</update_date>
  <accession>BMDB0000177</accession>
  <secondary_accessions>
    <accession>BMDB00177</accession>
  </secondary_accessions>
  <name>L-Histidine</name>
  <description>L-Histidine, also known as H, belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Histidine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Histidine exists in all living species, ranging from bacteria to humans. L-Histidine participates in a number of enzymatic reactions, within cattle. In particular, beta-Alanine and L-histidine can be biosynthesized from carnosine; which is catalyzed by the enzyme Beta-ala-his dipeptidase. Furthermore, L-Histidine and beta-alanine can be converted into carnosine through the action of the enzyme carnosine synthase 1. Finally, beta-Alanine and L-histidine can be biosynthesized from carnosine through the action of the enzyme Beta-ala-his dipeptidase. In cattle, L-histidine is involved in a couple of metabolic pathways, which include the histidine metabolism pathway and the beta-alanine metabolism pathway. L-Histidine is a potentially toxic compound. L-Histidine has been found to be associated with several diseases known as autosomal dominant polycystic kidney disease, perillyl alcohol administration for cancer treatment, pyridoxamine 5-prime-phosphate oxidase deficiency, and epilepsy; also l-histidine has been linked to the inborn metabolic disorders including maple syrup urine disease.</description>
  <synonyms>
    <synonym>(S)-4-(2-Amino-2-carboxyethyl)imidazole</synonym>
    <synonym>(S)-alpha-Amino-1H-imidazole-4-propanoic acid</synonym>
    <synonym>(S)-alpha-Amino-1H-imidazole-4-propionic acid</synonym>
    <synonym>H</synonym>
    <synonym>His</synonym>
    <synonym>HISTIDINE</synonym>
    <synonym>L-(-)-Histidine</synonym>
    <synonym>L-Histidin</synonym>
    <synonym>(S)-a-Amino-1H-imidazole-4-propanoate</synonym>
    <synonym>(S)-a-Amino-1H-imidazole-4-propanoic acid</synonym>
    <synonym>(S)-alpha-Amino-1H-imidazole-4-propanoate</synonym>
    <synonym>(S)-Α-amino-1H-imidazole-4-propanoate</synonym>
    <synonym>(S)-Α-amino-1H-imidazole-4-propanoic acid</synonym>
    <synonym>(S)-a-Amino-1H-imidazole-4-propionate</synonym>
    <synonym>(S)-a-Amino-1H-imidazole-4-propionic acid</synonym>
    <synonym>(S)-alpha-Amino-1H-imidazole-4-propionate</synonym>
    <synonym>(S)-Α-amino-1H-imidazole-4-propionate</synonym>
    <synonym>(S)-Α-amino-1H-imidazole-4-propionic acid</synonym>
    <synonym>(S)-1H-Imidazole-4-alanine</synonym>
    <synonym>(S)-2-Amino-3-(4-imidazolyl)propionsaeure</synonym>
    <synonym>(S)-Histidine</synonym>
    <synonym>(S)1H-Imidazole-4-alanine</synonym>
    <synonym>3-(1H-Imidazol-4-yl)-L-alanine</synonym>
    <synonym>Amino-1H-imidazole-4-propanoate</synonym>
    <synonym>Amino-1H-imidazole-4-propanoic acid</synonym>
    <synonym>Amino-4-imidazoleproprionate</synonym>
    <synonym>Amino-4-imidazoleproprionic acid</synonym>
    <synonym>Glyoxaline-5-alanine</synonym>
    <synonym>Histidine, L isomer</synonym>
    <synonym>Histidine, L-isomer</synonym>
    <synonym>L-Isomer histidine</synonym>
    <synonym>L-Histidine</synonym>
  </synonyms>
  <chemical_formula>C6H9N3O2</chemical_formula>
  <average_molecular_weight>155.1546</average_molecular_weight>
  <monisotopic_moleculate_weight>155.069476547</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid</iupac_name>
  <traditional_iupac>L-histidine</traditional_iupac>
  <cas_registry_number>71-00-1</cas_registry_number>
  <smiles>N[C@@H](CC1=CN=CN1)C(O)=O</smiles>
  <inchi>InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1</inchi>
  <inchikey>HNDVDQJCIGZPNO-YFKPBYRVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Histidine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolyl carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Histidine or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazolyl carboxylic acid derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>histidine</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>287 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>45.6 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.32</value>
      <source>CHMELIK,J ET AL. (1991)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>155.1546</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>155.069476547</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CC1=CN=CN1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H9N3O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HNDVDQJCIGZPNO-YFKPBYRVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Histidine</name>
      <smpdb_id>SMP0119392</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3368</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3372</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>74-84</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>91.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>76-93</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>52.3-54.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>78+/-10</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>382+/-67</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>75+/-18</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.1 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.2 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>134-281</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>58-484</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>43 +/- 9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>55 +/- 14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>29 +/- 11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>32 +/- 10</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>29.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>35.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>24.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>31.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>16.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wadud S, Onodera R, Or-Rashid MM, Amin MR: Determination of histidine and related compounds in rumen fluid by liquid chromatography. J AOAC Int. 2000 Jan-Feb;83(1):8-15.</reference_text>
          <pubmed_id>10692998</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>47.98 +/- 15.77</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>44+/-28</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>42.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>55.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>28.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>48</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>85+/-20</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>20</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Sexton TJ, Amann RP, Flipse RJ: Free amino acids and protein in rete testis fluid, vas deferens plasma, accessory sex gland fluid, and seminal plasma of the conscious bull. J Dairy Sci. 1971 Mar;54(3):412-6. doi: 10.3168/jds.s0022-0302(71)85854-x.</reference_text>
          <pubmed_id>5096119</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>61+/-13</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00135</kegg_id>
  <drugbank_id>DB00117</drugbank_id>
  <foodb_id>FDB011856</foodb_id>
  <chemspider_id>6038</chemspider_id>
  <pubchem_compound_id>6274</pubchem_compound_id>
  <chebi_id>15971</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>HIS</meta_cyc_id>
  <knapsack_id>C00001363</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33985</bigg_id>
  <wikipedia_id>L-histidine</wikipedia_id>
  <metlin_id>21</metlin_id>
  <synthesis_reference>Aurelio Luigi; Brownlee Robert T C; Hughes Andrew B  A novel synthesis of N-methyl asparagine, arginine, histidine, and tryptophan.    Organic letters  (2002),  4(21),  3767-9.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00561</protein_accession>
      <name>Histidine decarboxylase</name>
      <uniprot_id>Q5EA83</uniprot_id>
      <gene_name>HDC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01130</protein_accession>
      <name>Histidine triad nucleotide-binding protein 2</name>
      <uniprot_id>Q8SQ21</uniprot_id>
      <gene_name>HINT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01131</protein_accession>
      <name>Histidine ammonia-lyase</name>
      <uniprot_id>A7YWP4</uniprot_id>
      <gene_name>HAL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01132</protein_accession>
      <name>Histidine triad nucleotide-binding protein 3</name>
      <uniprot_id>Q2YDJ4</uniprot_id>
      <gene_name>HINT3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01133</protein_accession>
      <name>Presenilins-associated rhomboid-like protein, mitochondrial</name>
      <uniprot_id>Q2KHV4</uniprot_id>
      <gene_name>PARL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01134</protein_accession>
      <name>Histidine triad nucleotide-binding protein 1</name>
      <uniprot_id>P62958</uniprot_id>
      <gene_name>HINT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01135</protein_accession>
      <name>Histidyl-tRNA synthetase, cytoplasmic</name>
      <uniprot_id>Q2KI84</uniprot_id>
      <gene_name>HARS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01136</protein_accession>
      <name>Probable histidyl-tRNA synthetase, mitochondrial</name>
      <uniprot_id>A5D7V9</uniprot_id>
      <gene_name>HARS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02092</protein_accession>
      <name>Sodium-coupled neutral amino acid transporter 5</name>
      <uniprot_id>Q5E9S9</uniprot_id>
      <gene_name>SLC38A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02094</protein_accession>
      <name>Na+ and H+ coupled amino acid transport system N1</name>
      <uniprot_id>Q866Q8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02095</protein_accession>
      <name>SLC38A3 protein</name>
      <uniprot_id>Q3MHG9</uniprot_id>
      <gene_name>SLC38A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02097</protein_accession>
      <name>Solute carrier family 38 member 3</name>
      <uniprot_id>B0LSH5</uniprot_id>
      <gene_name>SLC38A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02098</protein_accession>
      <name>Solute carrier family 38, member 3</name>
      <uniprot_id>Q5BIN7</uniprot_id>
      <gene_name>SLC38A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02581</protein_accession>
      <name>Histidine triad nucleotide binding protein 1</name>
      <uniprot_id>A1XEA3</uniprot_id>
      <gene_name>HINT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:35 UTC</creation_date>
  <update_date>2020-04-16 20:39:42 UTC</update_date>
  <accession>BMDB0000181</accession>
  <secondary_accessions>
    <accession>BMDB00181</accession>
  </secondary_accessions>
  <name>L-Dopa</name>
  <description>L-Dopa, also known as l-dopa or l-dopa, belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Dopa is a drug which is used for the treatment of idiopathic parkinson's disease (paralysis agitans), postencephalitic parkinsonism, symptomatic parkinsonism which may follow injury to the nervous system by carbon monoxide intoxication, and manganese intoxication. L-Dopa exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Dopa exists in all living organisms, ranging from bacteria to humans. L-Dopa participates in a number of enzymatic reactions, within cattle. In particular, L-Dopa and tetrahydrobiopterin can be converted into dopamine and 4a-hydroxytetrahydrobiopterin through the action of the enzyme aromatic-L-amino-acid decarboxylase. In addition, L-Dopa can be converted into dopaquinone through its interaction with the enzyme tyrosinase. In cattle, L-dopa is involved in the metabolic pathway called the tyrosine metabolism pathway. L-Dopa is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(-)-3-(3,4-Dihydroxyphenyl)-L-alanine</synonym>
    <synonym>(-)-Dopa</synonym>
    <synonym>3,4-Dihydroxy-L-phenylalanine</synonym>
    <synonym>3,4-DIHYDROXYPHENYLALANINE</synonym>
    <synonym>3-Hydroxy-L-tyrosine</synonym>
    <synonym>beta-(3,4-Dihydroxyphenyl)-L-alanine</synonym>
    <synonym>beta-(3,4-Dihydroxyphenyl)alanine</synonym>
    <synonym>Dihydroxy-L-phenylalanine</synonym>
    <synonym>Dopar</synonym>
    <synonym>L-beta-(3,4-Dihydroxyphenyl)alanine</synonym>
    <synonym>Levodopa</synonym>
    <synonym>Levodopum</synonym>
    <synonym>b-(3,4-Dihydroxyphenyl)-L-alanine</synonym>
    <synonym>Β-(3,4-dihydroxyphenyl)-L-alanine</synonym>
    <synonym>b-(3,4-Dihydroxyphenyl)alanine</synonym>
    <synonym>Β-(3,4-dihydroxyphenyl)alanine</synonym>
    <synonym>L-b-(3,4-Dihydroxyphenyl)alanine</synonym>
    <synonym>L-Β-(3,4-dihydroxyphenyl)alanine</synonym>
    <synonym>(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoate</synonym>
    <synonym>(2S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid</synonym>
    <synonym>3,4-Dihydroxyphenyl-L-alanine</synonym>
    <synonym>3-(3,4-Dihydroxyphenyl)-L-alanine</synonym>
    <synonym>b-(3,4-Dihydroxyphenyl)-a-L-alanine</synonym>
    <synonym>Bendopa</synonym>
    <synonym>beta-(3,4-Dihydroxyphenyl)-alpha-L-alanine</synonym>
    <synonym>Cidandopa</synonym>
    <synonym>Dihydroxyphenylalanine</synonym>
    <synonym>Dopaflex</synonym>
    <synonym>Dopaidan</synonym>
    <synonym>Dopal</synonym>
    <synonym>Dopalina</synonym>
    <synonym>Doparkine</synonym>
    <synonym>Doparl</synonym>
    <synonym>Dopasol</synonym>
    <synonym>Dopaston</synonym>
    <synonym>Dopastone</synonym>
    <synonym>Dopastral</synonym>
    <synonym>Dopicar</synonym>
    <synonym>Doprin</synonym>
    <synonym>Eldopal</synonym>
    <synonym>Eldopar</synonym>
    <synonym>Eldopatec</synonym>
    <synonym>Eurodopa</synonym>
    <synonym>Helfo-dopa</synonym>
    <synonym>Insulamina</synonym>
    <synonym>L-(-)-Dopa</synonym>
    <synonym>L-3-(3,4-Dihydroxyphenyl)-alanine</synonym>
    <synonym>L-4-5-Dihydroxyphenylalanine</synonym>
    <synonym>L-b-(3,4-Dihydroxyphenyl)-a-alanine</synonym>
    <synonym>L-beta-(3,4-Dihydroxyphenyl)-alpha-alanine</synonym>
    <synonym>L-Dihydroxyphenylalanine</synonym>
    <synonym>Laradopa</synonym>
    <synonym>Larodopa</synonym>
    <synonym>Ledopa</synonym>
    <synonym>Levedopa</synonym>
    <synonym>Levopa</synonym>
    <synonym>Maipedopa</synonym>
    <synonym>Parda</synonym>
    <synonym>Pardopa</synonym>
    <synonym>Prodopa</synonym>
    <synonym>Syndopa</synonym>
    <synonym>Veldopa</synonym>
    <synonym>Weldopa</synonym>
    <synonym>3 Hydroxy L tyrosine</synonym>
    <synonym>Roche brand OF levodopa</synonym>
    <synonym>L 3,4 Dihydroxyphenylalanine</synonym>
    <synonym>L-3,4-Dihydroxyphenylalanine</synonym>
    <synonym>Medphano brand OF levodopa</synonym>
    <synonym>L Dopa</synonym>
    <synonym>Roberts brand OF levodopa</synonym>
  </synonyms>
  <chemical_formula>C9H11NO4</chemical_formula>
  <average_molecular_weight>197.1879</average_molecular_weight>
  <monisotopic_moleculate_weight>197.068807845</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid</iupac_name>
  <traditional_iupac>levodopa</traditional_iupac>
  <cas_registry_number>59-92-7</cas_registry_number>
  <smiles>N[C@@H](CC1=CC=C(O)C(O)=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1</inchi>
  <inchikey>WTDRDQBEARUVNC-LURJTMIESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Tyrosine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Catechols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalanine and derivatives</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Catechol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Tyrosine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>L-tyrosine derivative</external_descriptor>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>dopa</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>285 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>5.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.39</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>197.1879</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>197.068807845</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CC1=CC=C(O)C(O)=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WTDRDQBEARUVNC-LURJTMIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>103.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>49.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277254</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00355</kegg_id>
  <drugbank_id>DB01235</drugbank_id>
  <foodb_id>FDB000567</foodb_id>
  <chemspider_id>5824</chemspider_id>
  <pubchem_compound_id>6047</pubchem_compound_id>
  <chebi_id>15765</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>L-DIHYDROXY-PHENYLALANINE</meta_cyc_id>
  <knapsack_id>C00001357</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34719</bigg_id>
  <wikipedia_id>Levodopa</wikipedia_id>
  <metlin_id>42</metlin_id>
  <synthesis_reference>Haneda, Katsuji; Watanabe, Shiro; Takeda, Isao. Synthesis ofL-3,4-dihydroxyphenylalanine from L-tyrosine by microorganisms. Applied Microbiology (1971), 22(4), 721-2.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00388</protein_accession>
      <name>Tyrosine 3-monooxygenase</name>
      <uniprot_id>P17289</uniprot_id>
      <gene_name>TH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00662</protein_accession>
      <name>Tyrosinase</name>
      <uniprot_id>Q8MIU0</uniprot_id>
      <gene_name>TYR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00936</protein_accession>
      <name>Aromatic-L-amino-acid decarboxylase</name>
      <uniprot_id>P27718</uniprot_id>
      <gene_name>DDC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:37 UTC</creation_date>
  <update_date>2020-04-16 20:39:02 UTC</update_date>
  <accession>BMDB0000182</accession>
  <secondary_accessions>
    <accession>BMDB00182</accession>
  </secondary_accessions>
  <name>L-Lysine</name>
  <description>L-Lysine, also known as (S)-lysine or L-lysin, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-Lysine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Lysine exists in all living species, ranging from bacteria to humans. In cattle, L-lysine is involved in the metabolic pathway called the biotin metabolism pathway. L-Lysine is a potentially toxic compound. L-Lysine has been found to be associated with several diseases known as citrullinemia type ii, neonatal-onset, autism, and leukemia; also l-lysine has been linked to several inborn metabolic disorders including histidinemia and fumarase deficiency.</description>
  <synonyms>
    <synonym>(S)-2,6-Diaminohexanoic acid</synonym>
    <synonym>(S)-alpha,epsilon-Diaminocaproic acid</synonym>
    <synonym>(S)-Lysine</synonym>
    <synonym>6-Ammonio-L-norleucine</synonym>
    <synonym>K</synonym>
    <synonym>L-2,6-Diaminocaproic acid</synonym>
    <synonym>L-Lysin</synonym>
    <synonym>Lys</synonym>
    <synonym>Lysina</synonym>
    <synonym>Lysine</synonym>
    <synonym>Lysine acid</synonym>
    <synonym>Lysinum</synonym>
    <synonym>2,6-Diaminohexanoic acid</synonym>
    <synonym>(S)-2,6-Diaminohexanoate</synonym>
    <synonym>(S)-a,epsilon-Diaminocaproate</synonym>
    <synonym>(S)-a,epsilon-Diaminocaproic acid</synonym>
    <synonym>(S)-alpha,epsilon-Diaminocaproate</synonym>
    <synonym>(S)-Α,epsilon-diaminocaproate</synonym>
    <synonym>(S)-Α,epsilon-diaminocaproic acid</synonym>
    <synonym>L-2,6-Diaminocaproate</synonym>
    <synonym>2,6-Diaminohexanoate</synonym>
    <synonym>(+)-S-Lysine</synonym>
    <synonym>(S)-2,6-Diamino-hexanoate</synonym>
    <synonym>(S)-2,6-Diamino-hexanoic acid</synonym>
    <synonym>(S)-a,e-Diaminocaproate</synonym>
    <synonym>(S)-a,e-Diaminocaproic acid</synonym>
    <synonym>6-Amino-aminutrin</synonym>
    <synonym>6-Amino-L-norleucine</synonym>
    <synonym>a-Lysine</synonym>
    <synonym>alpha-Lysine</synonym>
    <synonym>Aminutrin</synonym>
    <synonym>H-Lys-OH</synonym>
    <synonym>L-(+)-Lysine</synonym>
    <synonym>L-2,6-Diainohexanoate</synonym>
    <synonym>L-2,6-Diainohexanoic acid</synonym>
    <synonym>L-Lys</synonym>
    <synonym>Acetate, lysine</synonym>
    <synonym>Enisyl</synonym>
    <synonym>Lysine hydrochloride</synonym>
    <synonym>L Lysine</synonym>
    <synonym>Lysine acetate</synonym>
  </synonyms>
  <chemical_formula>C6H14N2O2</chemical_formula>
  <average_molecular_weight>146.1876</average_molecular_weight>
  <monisotopic_moleculate_weight>146.105527702</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2,6-diaminohexanoic acid</iupac_name>
  <traditional_iupac>L-lysine</traditional_iupac>
  <cas_registry_number>56-87-1</cas_registry_number>
  <smiles>NCCCC[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1</inchi>
  <inchikey>KDXKERNSBIXSRK-YFKPBYRVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>aspartate family amino acid</external_descriptor>
      <external_descriptor>lysine</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>224.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.05</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2,6-diaminohexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>146.1876</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>146.105527702</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCC[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H14N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KDXKERNSBIXSRK-YFKPBYRVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>89.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Biotin Metabolism</name>
      <smpdb_id>SMP0087183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Lysine</name>
      <smpdb_id>SMP0119404</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3432</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>63.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>94-121</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>45.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>152-192</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>58-92</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Sadri H, von Soosten D, Meyer U, Kluess J, Danicke S, Saremi B, Sauerwein H: Plasma amino acids and metabolic profiling of dairy cows in response to a bolus duodenal infusion of leucine. PLoS One. 2017 Apr 28;12(4):e0176647. doi: 10.1371/journal.pone.0176647. eCollection 2017.</reference_text>
          <pubmed_id>28453535</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>60-68</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>88+/-15</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>115+/-33</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>59+/-18</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7 - 102</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>26 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>22 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27.2 +/-  23.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from Simmental cows during late lactation</comment>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
          <pubmed_id>23931703</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21205.629</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21205.629</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21205.629</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21205.629</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21205.629</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21205.629</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21205.629</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18 +/- 9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>24 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>306-745</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>118.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>163.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>231.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>117.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>91-1095</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>122 +/- 26</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>165 +/- 30</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>232 +/- 67</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>177 +/- 79</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>177 +/- 79</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR, GC-MS and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>85-329</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>135 (46.0 - 224)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>This concentration measured after 1 hour of feeding.; The three amino acids (AA), threonine, methionine and Lysine were administered intraruminally in mixtures at dosages of 100, 200, 300, and 400 mmol of each,together with polyethylene glycol (PEG) as a liquid marker.  </comment>
      <references>
        <reference>
          <reference_text>Volden H, Velle W, Harstad OM, Aulie A, Sjaastad OV: Apparent ruminal degradation and rumen escape of lysine, methionine, and threonine administered intraruminally in mixtures to high-yielding cows. J Anim Sci. 1998 Apr;76(4):1232-40.</reference_text>
          <pubmed_id>9581948</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>105</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>125</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>197</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>116</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>117.91 +/- 31.79</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2085+/-869</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>66+/-19</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>120-200</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By paper chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Brown-Woodman PD, White IG: Amino acid composition of semen and the secretions of the male reproductive tract. Aust J Biol Sci. 1974 Aug;27(4):415-22. doi: 10.1071/bi9740415.</reference_text>
          <pubmed_id>4429492</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>40</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Sexton TJ, Amann RP, Flipse RJ: Free amino acids and protein in rete testis fluid, vas deferens plasma, accessory sex gland fluid, and seminal plasma of the conscious bull. J Dairy Sci. 1971 Mar;54(3):412-6. doi: 10.3168/jds.s0022-0302(71)85854-x.</reference_text>
          <pubmed_id>5096119</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>64+/-15</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein.</comment>
      <references>
        <reference>
          <reference_text>Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17.</reference_text>
          <pubmed_id>22059599</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00047</kegg_id>
  <drugbank_id>DB00123</drugbank_id>
  <foodb_id>FDB000474</foodb_id>
  <chemspider_id>5747</chemspider_id>
  <pubchem_compound_id>5962</pubchem_compound_id>
  <chebi_id>18019</chebi_id>
  <pdbe_id>LYS</pdbe_id>
  <meta_cyc_id>LYS</meta_cyc_id>
  <knapsack_id>C00001378</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33655</bigg_id>
  <wikipedia_id>Lysine</wikipedia_id>
  <metlin_id>5200</metlin_id>
  <synthesis_reference>Rothstein, Morton. DL-Lysine-6-C14 and DL-a-aminoadipic acid-6-C14. Biochemical Preparations (1961), 8 85-8.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
      <pubmed_id>23931703</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00395</protein_accession>
      <name>Histone-lysine N-methyltransferase SUV39H2</name>
      <uniprot_id>Q32PH7</uniprot_id>
      <gene_name>SUV39H2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00398</protein_accession>
      <name>Histone-lysine N-methyltransferase SETD8</name>
      <uniprot_id>Q2YDJ8</uniprot_id>
      <gene_name>SETD8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00400</protein_accession>
      <name>Putative histone-lysine N-methyltransferase PRDM6</name>
      <uniprot_id>A6QPM3</uniprot_id>
      <gene_name>PRDM6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00402</protein_accession>
      <name>EHMT1 protein</name>
      <uniprot_id>A5PK11</uniprot_id>
      <gene_name>EHMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00417</protein_accession>
      <name>Histone-lysine N-methyltransferase SUV39H1</name>
      <uniprot_id>Q2NL30</uniprot_id>
      <gene_name>SUV39H1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00418</protein_accession>
      <name>Histone-lysine N-methyltransferase EZH1</name>
      <uniprot_id>A7E2Z2</uniprot_id>
      <gene_name>EZH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00419</protein_accession>
      <name>Histone-lysine N-methyltransferase SUV420H1</name>
      <uniprot_id>Q29RP8</uniprot_id>
      <gene_name>SUV420H1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00422</protein_accession>
      <name>Histone-lysine N-methyltransferase SETMAR</name>
      <uniprot_id>Q0VD24</uniprot_id>
      <gene_name>SETMAR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00552</protein_accession>
      <name>Carboxypeptidase E</name>
      <uniprot_id>P04836</uniprot_id>
      <gene_name>CPE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00554</protein_accession>
      <name>Carboxypeptidase B</name>
      <uniprot_id>P00732</uniprot_id>
      <gene_name>CPB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00631</protein_accession>
      <name>Alpha-aminoadipic semialdehyde synthase, mitochondrial</name>
      <uniprot_id>A8E657</uniprot_id>
      <gene_name>AASS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00658</protein_accession>
      <name>Lysyl oxidase homolog 1</name>
      <uniprot_id>Q95L39</uniprot_id>
      <gene_name>LOXL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00659</protein_accession>
      <name>Protein-lysine 6-oxidase</name>
      <uniprot_id>P33072</uniprot_id>
      <gene_name>LOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00660</protein_accession>
      <name>Lysyl oxidase homolog 4</name>
      <uniprot_id>Q8MJ24</uniprot_id>
      <gene_name>LOXL4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00682</protein_accession>
      <name>Procollagen-lysine,2-oxoglutarate 5-dioxygenase 1</name>
      <uniprot_id>O77588</uniprot_id>
      <gene_name>PLOD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00966</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 E3</name>
      <uniprot_id>Q2T9X7</uniprot_id>
      <gene_name>UBE2E3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00967</protein_accession>
      <name>Ubiquitin/ISG15-conjugating enzyme E2 L6</name>
      <uniprot_id>A5PJC4</uniprot_id>
      <gene_name>UBE2L6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00968</protein_accession>
      <name>NEDD8-conjugating enzyme UBE2F</name>
      <uniprot_id>Q1RMW1</uniprot_id>
      <gene_name>UBE2F</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00969</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 L3</name>
      <uniprot_id>Q3MHP1</uniprot_id>
      <gene_name>UBE2L3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00970</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 N</name>
      <uniprot_id>Q0P5K3</uniprot_id>
      <gene_name>UBE2N</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00971</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 D3</name>
      <uniprot_id>Q3ZCF7</uniprot_id>
      <gene_name>UBE2D3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00972</protein_accession>
      <name>NEDD8-conjugating enzyme Ubc12</name>
      <uniprot_id>A3KN22</uniprot_id>
      <gene_name>UBE2M</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00973</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 H</name>
      <uniprot_id>Q32LN1</uniprot_id>
      <gene_name>UBE2H</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00974</protein_accession>
      <name>Carboxypeptidase N catalytic chain</name>
      <uniprot_id>Q2KJ83</uniprot_id>
      <gene_name>CPN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00975</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 C</name>
      <uniprot_id>Q32PA5</uniprot_id>
      <gene_name>UBE2C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00976</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 Q2</name>
      <uniprot_id>Q32L27</uniprot_id>
      <gene_name>UBE2Q2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00977</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 B</name>
      <uniprot_id>Q32P99</uniprot_id>
      <gene_name>UBE2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00978</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 D2</name>
      <uniprot_id>Q1RMX2</uniprot_id>
      <gene_name>UBE2D2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00979</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 J2</name>
      <uniprot_id>Q2TA03</uniprot_id>
      <gene_name>UBE2J2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00980</protein_accession>
      <name>Lysyl-tRNA synthetase</name>
      <uniprot_id>Q3T0N2</uniprot_id>
      <gene_name>KARS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00981</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 G2</name>
      <uniprot_id>Q17QG5</uniprot_id>
      <gene_name>UBE2G2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00982</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 D1</name>
      <uniprot_id>Q2TA10</uniprot_id>
      <gene_name>UBE2D1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00983</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 T</name>
      <uniprot_id>Q32LD2</uniprot_id>
      <gene_name>UBE2T</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00984</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 K</name>
      <uniprot_id>P61085</uniprot_id>
      <gene_name>UBE2K</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00985</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 S</name>
      <uniprot_id>Q1RML1</uniprot_id>
      <gene_name>UBE2S</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01380</protein_accession>
      <name>Histidine-rich glycoprotein</name>
      <uniprot_id>P33433</uniprot_id>
      <gene_name>HRG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01637</protein_accession>
      <name>Solute carrier family 7 (Cationic amino acid transporter, y+ system), member 3</name>
      <uniprot_id>A0JNF2</uniprot_id>
      <gene_name>SLC7A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:20:38 UTC</creation_date>
  <update_date>2020-04-16 20:40:46 UTC</update_date>
  <accession>BMDB0000186</accession>
  <secondary_accessions>
    <accession>BMDB00186</accession>
  </secondary_accessions>
  <name>Alpha-Lactose</name>
  <description>Alpha-Lactose, also known as anhydrous lactose or tablettose, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Alpha-Lactose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Alpha-Lactose exists in all living organisms, ranging from bacteria to humans. Alpha-Lactose participates in a number of enzymatic reactions, within cattle. In particular, Alpha-Lactose can be converted into melibiose and D-galactose through the action of the enzyme Alpha-galactosidase a. In addition, Alpha-Lactose can be converted into D-galactose through the action of the enzyme Beta-galactosidase. In cattle, Alpha-lactose is involved in the metabolic pathway called the galactose metabolism pathway. Alpha-Lactose is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-beta-D-Galactopyranosyl-4-alpha-D-glucopyranose</synonym>
    <synonym>4-O-beta-D-Galactopyranosyl-alpha-D-glucopyranose</synonym>
    <synonym>Anhydrous lactose</synonym>
    <synonym>beta-D-Galp-(1-&gt;4)-alpha-D-GLCP</synonym>
    <synonym>Lactose</synonym>
    <synonym>Milk sugar</synonym>
    <synonym>1-b-D-Galactopyranosyl-4-a-D-glucopyranose</synonym>
    <synonym>1-Β-D-galactopyranosyl-4-α-D-glucopyranose</synonym>
    <synonym>4-O-b-D-Galactopyranosyl-a-D-glucopyranose</synonym>
    <synonym>4-O-Β-D-galactopyranosyl-α-D-glucopyranose</synonym>
    <synonym>b-D-Galp-(1-&gt;4)-a-D-GLCP</synonym>
    <synonym>Β-D-galp-(1-&gt;4)-α-D-GLCP</synonym>
    <synonym>a-Lactose</synonym>
    <synonym>Α-lactose</synonym>
    <synonym>(+)-Lactose</synonym>
    <synonym>1-beta-delta-Galactopyranosyl-4-alpha-delta-glucopyranose</synonym>
    <synonym>4-O-Hexopyranosylhexose</synonym>
    <synonym>Aletobiose</synonym>
    <synonym>Dilactose</synonym>
    <synonym>Fast-flo lactose</synonym>
    <synonym>Flowlac 100</synonym>
    <synonym>Galactinum</synonym>
    <synonym>GLC-(4-1)Gal</synonym>
    <synonym>Granulac 140m</synonym>
    <synonym>Lactin</synonym>
    <synonym>Lactin (carbohydrate)</synonym>
    <synonym>Lactobiose</synonym>
    <synonym>Lactohale 300</synonym>
    <synonym>Lactose anhydride</synonym>
    <synonym>Lactose fast-flo</synonym>
    <synonym>Osmolactan</synonym>
    <synonym>Pharmatosa DCL 21</synonym>
    <synonym>Pharmatose 21</synonym>
    <synonym>Pharmatose 325m</synonym>
    <synonym>Pharmatose DCL 15</synonym>
    <synonym>Prismalac</synonym>
    <synonym>Respitose ML 003</synonym>
    <synonym>Respitose SV 003</synonym>
    <synonym>Saccharum lactin</synonym>
    <synonym>Sachelac</synonym>
    <synonym>Sorbalac 400</synonym>
    <synonym>Sorbolac 400</synonym>
    <synonym>Spherolac</synonym>
    <synonym>Super-tab</synonym>
    <synonym>Tablettose</synonym>
    <synonym>Tablettose 70</synonym>
    <synonym>Tablettose 80</synonym>
    <synonym>Zeparox ep</synonym>
    <synonym>Lactose, anhydrous</synonym>
  </synonyms>
  <chemical_formula>C12H22O11</chemical_formula>
  <average_molecular_weight>342.2965</average_molecular_weight>
  <monisotopic_moleculate_weight>342.116211546</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>α-lactose</traditional_iupac>
  <cas_registry_number>63-42-3</cas_registry_number>
  <smiles>OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5+,6+,7-,8-,9-,10-,11+,12+/m1/s1</inchi>
  <inchikey>GUBGYTABKSRVRQ-XLOQQCSPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>O-glycosyl compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Disaccharides</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>lactose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>201 - 202 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>195 mg/mL at 20 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>342.2965</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>342.116211546</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H22O11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5+,6+,7-,8-,9-,10-,11+,12+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GUBGYTABKSRVRQ-XLOQQCSPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>189.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>30.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Degradation</name>
      <smpdb_id>SMP0087253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1192</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value>116857.753-146072.192</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gopal PK, Gill HS: Oligosaccharides and glycoconjugates in bovine milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S69-74.</reference_text>
          <pubmed_id>11242449</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value>78878.984-134386.416</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gopal PK, Gill HS: Oligosaccharides and glycoconjugates in bovine milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S69-74.</reference_text>
          <pubmed_id>11242449</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from Danish Holstein-Friesian (n = 456) and Jersey cows (n = 436)</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
          <pubmed_id>23182357</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>109682.11 +/- 4835.98</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>131172.828</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18.989</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>134386.416</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gopal PK, Gill HS: Oligosaccharides and glycoconjugates in bovine milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S69-74.</reference_text>
          <pubmed_id>11242449</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>135554.994</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>124736 - 153216</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>138768.582</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>45792 - 61243</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>139645.0154</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>140521.449</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>142858.604</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>143150.748</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>143735.0367</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>144027.181</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>144319.325</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>145780.0474</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>134970.705 +/- 1168.578</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>137600.00467 +/- 2045.0107</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>138768.582 +/- 1168.578</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>139645.0154 +/- 876.433</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>124636 - 150268</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>116857.583 - 146071.978</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>International Dairy Journal 16 (2006) 1334-1340</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>134970.508 +/- 6719.311</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Carbohydrate Polymers 37 (1998) 225-229</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>109179.54 +/- 4189.15</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>145195.759 +/- 3213.588</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>No milk type was specified in the literature. Assume it was raw milk.</comment>
      <references>
        <reference>
          <reference_text>RAJAN SHARMA YUDHISHTHIR S RAJPUT POONAM GAURAV DOGRA SUDHIR K TOMAR.  Estimation of sugars in milk by HPLC and its application in detection of adulteration of milk with soymilk. International Journal of Dairy Technology, 2009, 62(4):514-519</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>119779.197 +/- 2921.444</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Tommaso R.I. Cataldi, Massimiliano Angelotti, Giuliana Bianco. Determination of mono- and disaccharides in milk and milk products by high-performance anion-exchange chromatography with pulsed amperometric detection. Analytica Chimica Acta 485 (2003) 43–49</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>137892.149</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>137892.149</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>117931 +/- 5096</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>120445 +/- 4407</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>139060.727</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>113883 +/- 3432</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>138768.582</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>122036 +/- 8571</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>139060.727</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>134678.561</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>103625.15 +/- 5267.57</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>134970.705</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>134970.705</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00243</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB021789</foodb_id>
  <chemspider_id>76293</chemspider_id>
  <pubchem_compound_id>84571</pubchem_compound_id>
  <chebi_id>36219</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>LACTOSE</meta_cyc_id>
  <knapsack_id>C00001136</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34366</bigg_id>
  <wikipedia_id/>
  <metlin_id>267</metlin_id>
  <synthesis_reference>Ruffing, Anne; Mao, Zichao; Ruizhen Chen, Rachel. Metabolic engineering of Agrobacterium sp. for UDP-galactose regeneration and oligosaccharide synthesis. Metabolic Engineering  (2006),  8(5),  465-473.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
      <pubmed_id>23040012</pubmed_id>
    </reference>
    <reference>
      <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
      <pubmed_id>9718493</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
      <pubmed_id>23182357</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gopal PK, Gill HS: Oligosaccharides and glycoconjugates in bovine milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S69-74.</reference_text>
      <pubmed_id>11242449</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Carbohydrate Polymers 37 (1998) 225-229</reference_text>
    </reference>
    <reference>
      <reference_text>International Dairy Journal 16 (2006) 1334-1340</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00604</protein_accession>
      <name>Beta-1,4-galactosyltransferase 1</name>
      <uniprot_id>P08037</uniprot_id>
      <gene_name>B4GALT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01617</protein_accession>
      <name>Collectin-43</name>
      <uniprot_id>P42916</uniprot_id>
      <gene_name>CL43</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01889</protein_accession>
      <name>Galectin-4</name>
      <uniprot_id>Q3T0D6</uniprot_id>
      <gene_name>LGALS4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:27 UTC</creation_date>
  <update_date>2020-04-16 20:39:02 UTC</update_date>
  <accession>BMDB0000187</accession>
  <secondary_accessions>
    <accession>BMDB00187</accession>
  </secondary_accessions>
  <name>L-Serine</name>
  <description>L-Serine, also known as (S)-serine or L-ser, belongs to the class of organic compounds known as serine and derivatives. Serine and derivatives are compounds containing serine or a derivative thereof resulting from reaction of serine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Serine is a drug which is used as a natural moisturizing agent in some cosmetics and skin care products. L-Serine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Serine exists in all living species, ranging from bacteria to humans. L-Serine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2S)-2-Amino-3-hydroxypropanoic acid</synonym>
    <synonym>(S)-(-)-Serine</synonym>
    <synonym>(S)-2-Amino-3-hydroxypropanoic acid</synonym>
    <synonym>(S)-alpha-Amino-beta-hydroxypropionic acid</synonym>
    <synonym>(S)-Serine</synonym>
    <synonym>beta-Hydroxy-L-alanine</synonym>
    <synonym>beta-Hydroxyalanine</synonym>
    <synonym>L-(-)-Serine</synonym>
    <synonym>L-2-Amino-3-hydroxypropionic acid</synonym>
    <synonym>L-3-Hydroxy-2-aminopropionic acid</synonym>
    <synonym>L-3-Hydroxy-alanine</synonym>
    <synonym>L-Ser</synonym>
    <synonym>L-Serin</synonym>
    <synonym>S</synonym>
    <synonym>Ser</synonym>
    <synonym>SERINE</synonym>
    <synonym>(2S)-2-Amino-3-hydroxypropanoate</synonym>
    <synonym>(S)-2-Amino-3-hydroxypropanoate</synonym>
    <synonym>(S)-a-Amino-b-hydroxypropionate</synonym>
    <synonym>(S)-a-Amino-b-hydroxypropionic acid</synonym>
    <synonym>(S)-alpha-Amino-beta-hydroxypropionate</synonym>
    <synonym>(S)-Α-amino-β-hydroxypropionate</synonym>
    <synonym>(S)-Α-amino-β-hydroxypropionic acid</synonym>
    <synonym>b-Hydroxy-L-alanine</synonym>
    <synonym>Β-hydroxy-L-alanine</synonym>
    <synonym>b-Hydroxyalanine</synonym>
    <synonym>Β-hydroxyalanine</synonym>
    <synonym>L-2-Amino-3-hydroxypropionate</synonym>
    <synonym>L-3-Hydroxy-2-aminopropionate</synonym>
    <synonym>(-)-Serine</synonym>
    <synonym>(S)-2-Amino-3-hydroxy-propanoate</synonym>
    <synonym>(S)-2-Amino-3-hydroxy-propanoic acid</synonym>
    <synonym>(S)-b-Amino-3-hydroxypropionate</synonym>
    <synonym>(S)-b-Amino-3-hydroxypropionic acid</synonym>
    <synonym>(S)-beta-Amino-3-hydroxypropionate</synonym>
    <synonym>(S)-beta-Amino-3-hydroxypropionic acid</synonym>
    <synonym>2-Amino-3-hydroxypropanoate</synonym>
    <synonym>2-Amino-3-hydroxypropanoic acid</synonym>
    <synonym>3-Hydroxy-L-alanine</synonym>
    <synonym>L Serine</synonym>
    <synonym>(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-BETA,BETA-carotene-3,3'-diol</synonym>
    <synonym>Bo-xan</synonym>
    <synonym>e 161b</synonym>
    <synonym>Xanthophyll</synonym>
    <synonym>(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diol</synonym>
    <synonym>(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diol</synonym>
  </synonyms>
  <chemical_formula>C3H7NO3</chemical_formula>
  <average_molecular_weight>105.0926</average_molecular_weight>
  <monisotopic_moleculate_weight>105.042593095</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-hydroxypropanoic acid</iupac_name>
  <traditional_iupac>L-serine</traditional_iupac>
  <cas_registry_number>56-45-1</cas_registry_number>
  <smiles>N[C@@H](CO)C(O)=O</smiles>
  <inchi>InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1</inchi>
  <inchikey>MTCFGRXMJLQNBG-REOHCLBHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as serine and derivatives. Serine and derivatives are compounds containing serine or a derivative thereof resulting from reaction of serine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Serine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Serine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
      <external_descriptor>serine</external_descriptor>
      <external_descriptor>serine family amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>228 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>425.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.07</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-hydroxypropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>105.0926</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>105.042593095</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CO)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MTCFGRXMJLQNBG-REOHCLBHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>83.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>22.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Homocysteine Degradation</name>
      <smpdb_id>SMP0087201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis</name>
      <smpdb_id>SMP0072048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:0)</name>
      <smpdb_id>SMP0082233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0082234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/15:0)</name>
      <smpdb_id>SMP0082235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:0)</name>
      <smpdb_id>SMP0082236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0082237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:0)</name>
      <smpdb_id>SMP0082238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0082239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0082240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:0)</name>
      <smpdb_id>SMP0082245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0082246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:0)</name>
      <smpdb_id>SMP0082253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0082254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:0)</name>
      <smpdb_id>SMP0082260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0082261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0082262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0082263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0082264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/15:0)</name>
      <smpdb_id>SMP0082290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:0)</name>
      <smpdb_id>SMP0082291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0082292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:0)</name>
      <smpdb_id>SMP0082293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0082294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0082295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:0)</name>
      <smpdb_id>SMP0082300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0082301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:0)</name>
      <smpdb_id>SMP0082308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0082309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:0)</name>
      <smpdb_id>SMP0082315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0082316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:0)</name>
      <smpdb_id>SMP0082317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0082318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:0)</name>
      <smpdb_id>SMP0082319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0082320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0082321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:0)</name>
      <smpdb_id>SMP0082326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0082327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:0)</name>
      <smpdb_id>SMP0082334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0082335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:0)</name>
      <smpdb_id>SMP0082341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0082342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:0)</name>
      <smpdb_id>SMP0082368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0082369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0082370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:0)</name>
      <smpdb_id>SMP0082375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0082376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:0)</name>
      <smpdb_id>SMP0082383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0082384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:0)</name>
      <smpdb_id>SMP0082390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0082391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0082398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:0)</name>
      <smpdb_id>SMP0082520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0082521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:0)</name>
      <smpdb_id>SMP0082528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0082529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:0)</name>
      <smpdb_id>SMP0082535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0082536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0082574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0082581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:0)</name>
      <smpdb_id>SMP0082629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0082630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:0)</name>
      <smpdb_id>SMP0082636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0082637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0082644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:0)</name>
      <smpdb_id>SMP0082671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0082672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Serine</name>
      <smpdb_id>SMP0119409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Selenoamino Acid Metabolism</name>
      <smpdb_id>SMP0087161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3457</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>58.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>71-84</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>80.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>57-84</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>86-89</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>85+/-14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>422+/-114</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>165+/-36</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15.7 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19030.836</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19030.836</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19030.836</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19030.836</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18079.294</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18079.294</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18079.294</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>273-830</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>50 +/- 14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>85 +/- 29</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>123 +/- 57</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>49 +/- 25</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>49 +/- 25</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by GC-MS and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>45.29 +/- 23.71</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>547+/-187</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>161+/-31</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>630-830</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By paper chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Brown-Woodman PD, White IG: Amino acid composition of semen and the secretions of the male reproductive tract. Aust J Biol Sci. 1974 Aug;27(4):415-22. doi: 10.1071/bi9740415.</reference_text>
          <pubmed_id>4429492</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>230</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Sexton TJ, Amann RP, Flipse RJ: Free amino acids and protein in rete testis fluid, vas deferens plasma, accessory sex gland fluid, and seminal plasma of the conscious bull. J Dairy Sci. 1971 Mar;54(3):412-6. doi: 10.3168/jds.s0022-0302(71)85854-x.</reference_text>
          <pubmed_id>5096119</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>272+/-58</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00065</kegg_id>
  <drugbank_id>DB00133</drugbank_id>
  <foodb_id>FDB012739</foodb_id>
  <chemspider_id>5736</chemspider_id>
  <pubchem_compound_id>5951</pubchem_compound_id>
  <chebi_id>17115</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>SER</meta_cyc_id>
  <knapsack_id>C00001393</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33717</bigg_id>
  <wikipedia_id>L-serine</wikipedia_id>
  <metlin_id>5203</metlin_id>
  <synthesis_reference>Qin, Wei-min; Cao, Fei; Zhou, Hua; Li, Zhen-jiang; Wei, Ping. Asymmetric synthesis of D- and L-serine with "Glycine equivalent" method. Huaxue Shiji (2005), 27(11), 643-644, 670.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00082</protein_accession>
      <name>Serine racemase</name>
      <uniprot_id>A0JNI4</uniprot_id>
      <gene_name>SRR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00083</protein_accession>
      <name>Serine hydroxymethyltransferase, mitochondrial</name>
      <uniprot_id>Q3SZ20</uniprot_id>
      <gene_name>SHMT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00084</protein_accession>
      <name>Seryl-tRNA synthetase, mitochondrial</name>
      <uniprot_id>Q9N0F3</uniprot_id>
      <gene_name>SARS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00085</protein_accession>
      <name>Serine palmitoyltransferase 1</name>
      <uniprot_id>Q3MHG1</uniprot_id>
      <gene_name>SPTLC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00086</protein_accession>
      <name>Seryl-tRNA synthetase, cytoplasmic</name>
      <uniprot_id>Q9GMB8</uniprot_id>
      <gene_name>SARS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00087</protein_accession>
      <name>Serine hydroxymethyltransferase, cytosolic</name>
      <uniprot_id>Q5E9P9</uniprot_id>
      <gene_name>SHMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00088</protein_accession>
      <name>L-serine dehydratase</name>
      <uniprot_id>Q0VCW4</uniprot_id>
      <gene_name>SDS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:28 UTC</creation_date>
  <update_date>2020-04-15 21:57:54 UTC</update_date>
  <accession>BMDB0000189</accession>
  <secondary_accessions>
    <accession>BMDB00189</accession>
  </secondary_accessions>
  <name>Inosine triphosphate</name>
  <description/>
  <synonyms>
    <synonym>2'-Inosine-5'-triphosphate</synonym>
    <synonym>Inosine 5'-triphosphate</synonym>
    <synonym>Inosine tripolyphosphate</synonym>
    <synonym>O(5')-(Tetrahydroxytriphosphoryl)inosine</synonym>
    <synonym>2'-Inosine-5'-triphosphoric acid</synonym>
    <synonym>Inosine 5'-triphosphoric acid</synonym>
    <synonym>Inosine tripolyphosphoric acid</synonym>
    <synonym>Inosine triphosphoric acid</synonym>
    <synonym>5'-ITP</synonym>
    <synonym>5-ITP</synonym>
    <synonym>Inosine 5</synonym>
    <synonym>Inosine 5'-(tetrahydrogen triphosphate)</synonym>
    <synonym>Inosine 5(tetrahydrogen triphosphate)</synonym>
    <synonym>Inosine 5-triphopshate</synonym>
    <synonym>ITP</synonym>
    <synonym>ITT</synonym>
    <synonym>Triphosphate, inosine</synonym>
    <synonym>Inosine triphosphate</synonym>
  </synonyms>
  <chemical_formula>C10H15N4O14P3</chemical_formula>
  <average_molecular_weight>508.1658</average_molecular_weight>
  <monisotopic_moleculate_weight>507.979760744</monisotopic_moleculate_weight>
  <iupac_name>({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-9H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</iupac_name>
  <traditional_iupac>({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxypurin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>132-06-9</cas_registry_number>
  <smiles>O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN=C2O</smiles>
  <inchi>InChI=1S/C10H15N4O14P3/c15-6-4(1-25-30(21,22)28-31(23,24)27-29(18,19)20)26-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,21,22)(H,23,24)(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>HAEJPQIATWHALX-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group  linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside triphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside triphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>inosine phosphate</external_descriptor>
      <external_descriptor>purine ribonucleoside 5'-triphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>903.5 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-9H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>508.1658</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>507.979760744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN=C2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H15N4O14P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H15N4O14P3/c15-6-4(1-25-30(21,22)28-31(23,24)27-29(18,19)20)26-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,21,22)(H,23,24)(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HAEJPQIATWHALX-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>273.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>93.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>988</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182471</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00081</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB021902</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>8583</pubchem_compound_id>
  <chebi_id>16039</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>ITP</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Inosine triphosphate</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Nakayama, Kiyoshi; Tanaka, Haruo.  Fermentative preparation of inosine di- and triphosphate.    Jpn. Tokkyo Koho  (1972),     2 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00432</protein_accession>
      <name>GMP reductase 2</name>
      <uniprot_id>Q32L93</uniprot_id>
      <gene_name>GMPR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00999</protein_accession>
      <name>GMP reductase</name>
      <uniprot_id>Q08DA2</uniprot_id>
      <gene_name>GMPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01002</protein_accession>
      <name>Inosine-5'-monophosphate dehydrogenase 2</name>
      <uniprot_id>Q3SWY3</uniprot_id>
      <gene_name>IMPDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01003</protein_accession>
      <name>Inosine-5'-monophosphate dehydrogenase</name>
      <uniprot_id>A0JNA3</uniprot_id>
      <gene_name>IMPDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:29 UTC</creation_date>
  <update_date>2020-04-16 20:39:02 UTC</update_date>
  <accession>BMDB0000190</accession>
  <secondary_accessions>
    <accession>BMDB00190</accession>
  </secondary_accessions>
  <name>L-Lactic acid</name>
  <description>L-Lactic acid, also known as D-lactate or D-milchsaeure, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. L-Lactic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. L-Lactic acid exists in all living species, ranging from bacteria to humans. L-Lactic acid participates in a number of enzymatic reactions, within cattle. In particular, L-Lactic acid can be converted into pyruvic acid; which is catalyzed by the enzyme L-lactate dehydrogenase. In addition, L-Lactic acid can be converted into L-lactic acid through the action of the enzyme monocarboxylate transporter. In cattle, L-lactic acid is involved in the metabolic pathway called cancer (via the Warburg effect). L-Lactic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(+)-Lactic acid</synonym>
    <synonym>(S)-(+)-Lactic acid</synonym>
    <synonym>(S)-2-Hydroxypropanoic acid</synonym>
    <synonym>(S)-2-Hydroxypropionic acid</synonym>
    <synonym>L-(+)-alpha-Hydroxypropionic acid</synonym>
    <synonym>L-(+)-Lactic acid</synonym>
    <synonym>L-Milchsaeure</synonym>
    <synonym>L-Lactate</synonym>
    <synonym>(+)-Lactate</synonym>
    <synonym>(S)-(+)-Lactate</synonym>
    <synonym>(S)-2-Hydroxypropanoate</synonym>
    <synonym>(S)-2-Hydroxypropionate</synonym>
    <synonym>L-(+)-a-Hydroxypropionate</synonym>
    <synonym>L-(+)-a-Hydroxypropionic acid</synonym>
    <synonym>L-(+)-alpha-Hydroxypropionate</synonym>
    <synonym>L-(+)-Α-hydroxypropionate</synonym>
    <synonym>L-(+)-Α-hydroxypropionic acid</synonym>
    <synonym>L-(+)-Lactate</synonym>
    <synonym>(alpha)-Lactate</synonym>
    <synonym>(alpha)-Lactic acid</synonym>
    <synonym>(S)-(+)-2-Hydroxypropanoate</synonym>
    <synonym>(S)-(+)-2-Hydroxypropanoic acid</synonym>
    <synonym>(S)-2-Hydroxy-propanoate</synonym>
    <synonym>(S)-2-Hydroxy-propanoic acid</synonym>
    <synonym>(S)-Lactate</synonym>
    <synonym>(S)-Lactic acid</synonym>
    <synonym>1-Hydroxyethane 1-carboxylate</synonym>
    <synonym>1-Hydroxyethane 1-carboxylic acid</synonym>
    <synonym>1-Hydroxyethanecarboxylate</synonym>
    <synonym>1-Hydroxyethanecarboxylic acid</synonym>
    <synonym>2-Hydroxypropanoate</synonym>
    <synonym>2-Hydroxypropanoic acid</synonym>
    <synonym>2-Hydroxypropionate</synonym>
    <synonym>a-Hydroxypropanoate</synonym>
    <synonym>a-Hydroxypropanoic acid</synonym>
    <synonym>a-Hydroxypropionate</synonym>
    <synonym>a-Hydroxypropionic acid</synonym>
    <synonym>alpha-Hydroxypropanoate</synonym>
    <synonym>alpha-Hydroxypropanoic acid</synonym>
    <synonym>alpha-Hydroxypropionate</synonym>
    <synonym>alpha-Hydroxypropionic acid</synonym>
    <synonym>L-(+)- Lactic acid</synonym>
    <synonym>L-2-Hydroxypropanoate</synonym>
    <synonym>L-2-Hydroxypropanoic acid</synonym>
    <synonym>Lactate</synonym>
    <synonym>Lactic acid</synonym>
    <synonym>Milk acid</synonym>
    <synonym>Sarcolactic acid</synonym>
    <synonym>2-Hydroxypropionic acid</synonym>
    <synonym>D-Lactic acid</synonym>
    <synonym>D Lactic acid</synonym>
    <synonym>Lactate, ammonium</synonym>
    <synonym>2 Hydroxypropanoic acid</synonym>
    <synonym>2 Hydroxypropionic acid</synonym>
    <synonym>Ammonium lactate</synonym>
    <synonym>L Lactic acid</synonym>
    <synonym>D-Lactate</synonym>
    <synonym>L-Lactic acid</synonym>
  </synonyms>
  <chemical_formula>C3H6O3</chemical_formula>
  <average_molecular_weight>90.0779</average_molecular_weight>
  <monisotopic_moleculate_weight>90.031694058</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-hydroxypropanoic acid</iupac_name>
  <traditional_iupac>(α)-lactate</traditional_iupac>
  <cas_registry_number>79-33-4</cas_registry_number>
  <smiles>C[C@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1</inchi>
  <inchikey>JVTAAEKCZFNVCJ-REOHCLBHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Alpha hydroxy acids and derivatives</sub_class>
    <direct_parent>Alpha hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxypropanoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>16.8 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-hydroxypropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>90.0779</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>90.031694058</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H6O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JVTAAEKCZFNVCJ-REOHCLBHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>18.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438030</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 24 male 17-22-month-old Charolais beef cattles.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>500 +/- 90</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Spectrometry (Autoanalyzer/BT3000 Plus)</comment>
      <references>
        <reference>
          <reference_text>Abdullah BASOGLU, Nuri BASPINAR, Alparslan COSKUN. NMR-based metabolomic evaluation in dairy cows with displaced abomasum. Turk J Vet Anim Sci (2014) 38(3):325-330</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>658-1600</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Cobas mira chemistry analyzer</comment>
      <references>
        <reference>
          <reference_text>Kenny DA, Humpherson PG, Leese HJ, Morris DG, Tomos AD, Diskin MG, Sreenan JM: Effect of elevated systemic concentrations of ammonia and urea on the metabolite and ionic composition of oviductal fluid in cattle. Biol Reprod. 2002 Jun;66(6):1797-804. doi: 10.1095/biolreprod66.6.1797.</reference_text>
          <pubmed_id>12021065</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>320-550</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Membrane-immobilized enzyme with YSI 7100 MBS select biochemistry analyzer</comment>
      <references>
        <reference>
          <reference_text>Raun BM, Kristensen NB: Metabolic effects of feeding ethanol or propanol to postpartum transition Holstein cows. J Dairy Sci. 2011 May;94(5):2566-80. doi: 10.3168/jds.2010-3999.</reference_text>
          <pubmed_id>21524548</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>4850+/-2017</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>12311+/-1719</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>31131+/-8268</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from Danish Holstein-Friesian (n = 456) and Jersey cows (n = 436)</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
          <pubmed_id>23182357</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>73.34 +/- 93.23</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>138</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
          <pubmed_id>2760296</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2 - 3538</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32 - 136</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>45 - 95</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>75</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>97</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>102</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>47.31 +/- 26.19</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>61.4 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>57 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>55 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>59 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>33.43 +/- 9.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>37175-131553</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>14817.25 +/- 555.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>16764.97 +/- 482.13</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>17300.81 +/- 1145.11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>21406.66 +/- 443.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>14262-21850</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>7.10+/-1.14</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>392.24+/-63.98</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>367.58+/-50.52</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>383.14+/-51.35</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>53000</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>2230-3170</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>173.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>282</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>180.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>156.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>360 +/- 130</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Ewaschuk JB, Naylor JM, Barabash WA, Zello GA: High-performance liquid chromatographic assay of lactic, pyruvic and acetic acids and lactic acid stereoisomers in calf feces, rumen fluid and urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Jun 15;805(2):347-51. doi: 10.1016/j.jchromb.2004.03.004.</reference_text>
          <pubmed_id>15135111</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>224-1560</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>159 +/- 22</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>252 +/- 61</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>180 +/- 118</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>134 +/- 17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>134 +/- 17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR and GC-MS</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>10-73</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>700-1830</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS</comment>
      <references>
        <reference>
          <reference_text>Raun BM, Kristensen NB: Metabolic effects of feeding ethanol or propanol to postpartum transition Holstein cows. J Dairy Sci. 2011 May;94(5):2566-80. doi: 10.3168/jds.2010-3999.</reference_text>
          <pubmed_id>21524548</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hanne Christine Bertram, Niels Bastian Kristensen, Mogens Vestergaard, SÃ¸ren Krogh Jensen, Jakob Sehested, Niels Christian Nielsen, Anders Malmendal. Metabolic characterization of rumen epithelial tissue from dairy calves fed different starter diets using 1H NMR spectroscopy. Livestock Science (2008) 120:127-134   doi: 10.1016/j.livsci.2008.05.001</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>122</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>228</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>133</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>124</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>156.94 +/- 13.25</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2029+/-1165</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>37879+/-10580</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>7702+/-1649</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00186</kegg_id>
  <foodb_id>FDB003294</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>107689</pubchem_compound_id>
  <chemspider_id>96860</chemspider_id>
  <pdbe_id/>
  <chebi_id>422</chebi_id>
  <knapsack_id>C00001191</knapsack_id>
  <meta_cyc_id>L-LACTATE</meta_cyc_id>
  <wikipedia_id>Lactic_Acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34179</bigg_id>
  <metlin_id>5205</metlin_id>
  <synthesis_reference>Lao, Hanzhang; Sun, Jianrong; Wang, Jian; Qian, Zhiliang.  Process for preparation of high-purity L-lactic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu  (2007),     9pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
      <pubmed_id>2760296</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
      <pubmed_id>11132867</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
      <pubmed_id>23182357</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00573</protein_accession>
      <name>L-lactate dehydrogenase A-like 6B</name>
      <uniprot_id>Q3T056</uniprot_id>
      <gene_name>LDHAL6B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00574</protein_accession>
      <name>L-lactate dehydrogenase B chain</name>
      <uniprot_id>Q5E9B1</uniprot_id>
      <gene_name>LDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00575</protein_accession>
      <name>L-lactate dehydrogenase A chain</name>
      <uniprot_id>P19858</uniprot_id>
      <gene_name>LDHA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00576</protein_accession>
      <name>L-lactate dehydrogenase</name>
      <uniprot_id>B0JYN3</uniprot_id>
      <gene_name>LDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00577</protein_accession>
      <name>L-lactate dehydrogenase</name>
      <uniprot_id>Q2KJG0</uniprot_id>
      <gene_name>LDHC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:31 UTC</creation_date>
  <update_date>2020-04-16 20:39:03 UTC</update_date>
  <accession>BMDB0000191</accession>
  <secondary_accessions>
    <accession>BMDB00191</accession>
  </secondary_accessions>
  <name>L-Aspartic acid</name>
  <description>L-Aspartic acid, also known as Asp or D, belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Aspartic acid exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Aspartic acid exists in all living species, ranging from bacteria to humans. L-Aspartic acid has been found to be associated with several diseases known as frontotemporal dementia, pancreatic cancer, cirrhosis, and perillyl alcohol administration for cancer treatment; also l-aspartic acid has been linked to the inborn metabolic disorders including growth hormone deficiency.</description>
  <synonyms>
    <synonym>(S)-2-Aminobutanedioic acid</synonym>
    <synonym>(S)-2-Aminosuccinic acid</synonym>
    <synonym>2-Aminosuccinic acid</synonym>
    <synonym>Asp</synonym>
    <synonym>ASPARTIC ACID</synonym>
    <synonym>D</synonym>
    <synonym>L-Asparaginsaeure</synonym>
    <synonym>L-Asp</synonym>
    <synonym>(S)-2-Aminobutanedioate</synonym>
    <synonym>(S)-2-Aminosuccinate</synonym>
    <synonym>2-Aminosuccinate</synonym>
    <synonym>ASPARTate</synonym>
    <synonym>L-Aspartate</synonym>
    <synonym>(+)-Aspartate</synonym>
    <synonym>(+)-Aspartic acid</synonym>
    <synonym>(2S)-Aspartate</synonym>
    <synonym>(2S)-Aspartic acid</synonym>
    <synonym>(L)-Aspartate</synonym>
    <synonym>(L)-Aspartic acid</synonym>
    <synonym>(R)-2-Aminosuccinate</synonym>
    <synonym>(S)-(+)-Aspartate</synonym>
    <synonym>(S)-(+)-Aspartic acid</synonym>
    <synonym>(S)-Amino-butanedioate</synonym>
    <synonym>(S)-Amino-butanedioic acid</synonym>
    <synonym>(S)-Aminobutanedioate</synonym>
    <synonym>(S)-Aminobutanedioic acid</synonym>
    <synonym>(S)-Aspartate</synonym>
    <synonym>(S)-Aspartic acid</synonym>
    <synonym>2-Amino-3-methylsuccinate</synonym>
    <synonym>2-Amino-3-methylsuccinic acid</synonym>
    <synonym>alpha-Aminosuccinate</synonym>
    <synonym>alpha-Aminosuccinic acid</synonym>
    <synonym>Aminosuccinate</synonym>
    <synonym>Asparagate</synonym>
    <synonym>Asparagic acid</synonym>
    <synonym>Asparaginate</synonym>
    <synonym>Asparaginic acid</synonym>
    <synonym>Asparatate</synonym>
    <synonym>H-Asp-OH</synonym>
    <synonym>L-(+)-Aspartate</synonym>
    <synonym>L-(+)-Aspartic acid</synonym>
    <synonym>L-Aminosuccinate</synonym>
    <synonym>L-Aminosuccinic acid</synonym>
    <synonym>L-Asparagate</synonym>
    <synonym>L-Asparagic acid</synonym>
    <synonym>L-Asparaginate</synonym>
    <synonym>L-Asparaginic acid</synonym>
    <synonym>(+-)-Aspartic acid</synonym>
    <synonym>(R,S)-Aspartic acid</synonym>
    <synonym>Aspartate, disodium</synonym>
    <synonym>Aspartate, magnesium</synonym>
    <synonym>Aspartate, monopotassium</synonym>
    <synonym>Aspartic acid, dipotassium salt</synonym>
    <synonym>Aspartic acid, hydrobromide</synonym>
    <synonym>Aspartic acid, monopotassium salt</synonym>
    <synonym>Aspartic acid, monosodium salt</synonym>
    <synonym>Aspartic acid, potassium salt</synonym>
    <synonym>L Aspartate</synonym>
    <synonym>MG5Longoral</synonym>
    <synonym>Potassium aspartate</synonym>
    <synonym>Polysuccinimide</synonym>
    <synonym>Ammonium aspartate</synonym>
    <synonym>Aspartate, ammonium</synonym>
    <synonym>Aspartate, calcium</synonym>
    <synonym>Aspartate, monosodium</synonym>
    <synonym>Aspartic acid, calcium salt</synonym>
    <synonym>Aspartic acid, disodium salt</synonym>
    <synonym>Aspartic acid, magnesium (1:1) salt, hydrochloride, trihydrate</synonym>
    <synonym>Dipotassium aspartate</synonym>
    <synonym>Disodium aspartate</synonym>
    <synonym>Hydrochloride, aspartate magnesium</synonym>
    <synonym>Monopotassium aspartate</synonym>
    <synonym>Sodium aspartate</synonym>
    <synonym>Aspartate, dipotassium</synonym>
    <synonym>Aspartic acid, magnesium (2:1) salt</synonym>
    <synonym>Aspartic acid, sodium salt</synonym>
    <synonym>Hydrobromide aspartic acid</synonym>
    <synonym>Magnesium aspartate</synonym>
    <synonym>MG 5 Longoral</synonym>
    <synonym>Monosodium aspartate</synonym>
    <synonym>Aspartate magnesium hydrochloride</synonym>
    <synonym>Aspartate, potassium</synonym>
    <synonym>Aspartate, sodium</synonym>
    <synonym>Aspartic acid, ammonium salt</synonym>
    <synonym>Aspartic acid, hydrochloride</synonym>
    <synonym>Aspartic acid, magnesium-potassium (2:1:2) salt</synonym>
    <synonym>Calcium aspartate</synonym>
    <synonym>Hydrochloride aspartic acid</synonym>
    <synonym>L Aspartic acid</synonym>
    <synonym>Magnesiocard</synonym>
    <synonym>MG-5-Longoral</synonym>
    <synonym>Poly-DL-succinimide</synonym>
  </synonyms>
  <chemical_formula>C4H7NO4</chemical_formula>
  <average_molecular_weight>133.1027</average_molecular_weight>
  <monisotopic_moleculate_weight>133.037507717</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-aminobutanedioic acid</iupac_name>
  <traditional_iupac>L-aspartic acid</traditional_iupac>
  <cas_registry_number>56-84-8</cas_registry_number>
  <smiles>N[C@@H](CC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1</inchi>
  <inchikey>CKLJMWTZIZZHCS-REOHCLBHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Aspartic acid and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Aspartic acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Amino acids</external_descriptor>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>aspartate family amino acid</external_descriptor>
      <external_descriptor>aspartic acid</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>270 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>5.39 mg/mL</value>
      <source>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.89</value>
      <source>CHMELIK,J ET AL. (1991)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-aminobutanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>133.1027</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>133.037507717</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H7NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CKLJMWTZIZZHCS-REOHCLBHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>100.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>26.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Malate-Aspartate Shuttle</name>
      <smpdb_id>SMP0087204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Aspartic Acid</name>
      <smpdb_id>SMP0119386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3494</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>14.5-16</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>31.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>31-36</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>4.2-4.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>24+/-11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>384+/-165</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>70+/-28</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21787.687</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21787.687</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21787.687</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21787.687</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28.86 +/- 11.37</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21036.388</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21036.388</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21036.388</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10 - 77</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28.63 +/- 13.11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20.35 +/- 7.08</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>26.56+/-2.48</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>26.53+/-2.60</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>24.23+/-2.80</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>25.93+/-2.20</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>14-54</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>153-925</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>122 +/- 35</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>185 +/- 50</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>180 +/- 69</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>115 +/- 47</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>115 +/- 47</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR, GC-MS and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>68-228</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>164</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>201</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>123</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>157</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>132.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>196.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>179.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>126</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>124.71 +/- 40.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>566+/-204</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>57+/-28</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>310-550</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By paper chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Brown-Woodman PD, White IG: Amino acid composition of semen and the secretions of the male reproductive tract. Aust J Biol Sci. 1974 Aug;27(4):415-22. doi: 10.1071/bi9740415.</reference_text>
          <pubmed_id>4429492</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>597+/-215</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00049</kegg_id>
  <foodb_id>FDB012567</foodb_id>
  <drugbank_id>DB00128</drugbank_id>
  <pubchem_compound_id>5960</pubchem_compound_id>
  <chemspider_id>5745</chemspider_id>
  <pdbe_id/>
  <chebi_id>17053</chebi_id>
  <knapsack_id>C00001342</knapsack_id>
  <meta_cyc_id>L-ASPARTATE</meta_cyc_id>
  <wikipedia_id>Aspartic acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33663</bigg_id>
  <metlin_id>5206</metlin_id>
  <synthesis_reference>Pamfil, Maria; Lupescu, Irina; Savoiu, Valeria Gabriela.  L-aspartic acid production from fumarate using Escherichia coli whole cells.    Rom.  (2005),     3pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00237</protein_accession>
      <name>Argininosuccinate synthase</name>
      <uniprot_id>P14568</uniprot_id>
      <gene_name>ASS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00495</protein_accession>
      <name>Adenylosuccinate synthetase isozyme 1</name>
      <uniprot_id>A5PJR4</uniprot_id>
      <gene_name>ADSSL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00525</protein_accession>
      <name>Adenylosuccinate synthetase isozyme 2</name>
      <uniprot_id>A7MBG0</uniprot_id>
      <gene_name>ADSS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00562</protein_accession>
      <name>Aspartoacylase</name>
      <uniprot_id>P46446</uniprot_id>
      <gene_name>ASPA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00563</protein_accession>
      <name>Asparagine synthetase [glutamine-hydrolyzing]</name>
      <uniprot_id>Q1LZA3</uniprot_id>
      <gene_name>ASNS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00564</protein_accession>
      <name>Aspartyl-tRNA synthetase, cytoplasmic</name>
      <uniprot_id>Q3SYZ4</uniprot_id>
      <gene_name>DARS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00565</protein_accession>
      <name>L-asparaginase</name>
      <uniprot_id>Q32LE5</uniprot_id>
      <gene_name>ASRGL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00566</protein_accession>
      <name>Aspartyl aminopeptidase</name>
      <uniprot_id>Q2HJH1</uniprot_id>
      <gene_name>DNPEP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00567</protein_accession>
      <name>Aspartate aminotransferase, cytoplasmic</name>
      <uniprot_id>P33097</uniprot_id>
      <gene_name>GOT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00568</protein_accession>
      <name>Aspartyl/asparaginyl beta-hydroxylase</name>
      <uniprot_id>Q28056</uniprot_id>
      <gene_name>ASPH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00569</protein_accession>
      <name>Aspartate aminotransferase, mitochondrial</name>
      <uniprot_id>P12344</uniprot_id>
      <gene_name>GOT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00570</protein_accession>
      <name>Aspartyl-tRNA synthetase, mitochondrial</name>
      <uniprot_id>A6QPU5</uniprot_id>
      <gene_name>DARS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00571</protein_accession>
      <name>Putative aspartate aminotransferase, cytoplasmic 2</name>
      <uniprot_id>Q2T9S8</uniprot_id>
      <gene_name>GOT1L1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00572</protein_accession>
      <name>Glutamyl aminopeptidase</name>
      <uniprot_id>Q32LQ0</uniprot_id>
      <gene_name>ENPEP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01814</protein_accession>
      <name>Mitochondrial 2-oxoglutarate/malate carrier protein</name>
      <uniprot_id>P22292</uniprot_id>
      <gene_name>SLC25A11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:32 UTC</creation_date>
  <update_date>2020-04-15 20:47:58 UTC</update_date>
  <accession>BMDB0000192</accession>
  <secondary_accessions>
    <accession>BMDB00192</accession>
  </secondary_accessions>
  <name>L-Cystine</name>
  <description>Cystine, also known as L-dicysteine or E921, belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated. Cystine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Cystine exists in all living species, ranging from bacteria to humans. Cystine has been found to be associated with several diseases known as molybdenum cofactor deficiency, schizophrenia, parkinson's disease, and colorectal cancer; also cystine has been linked to the inborn metabolic disorders including fumarase deficiency.</description>
  <synonyms>
    <synonym>(R,R)-3,3'-Dithiobis(2-aminopropanoic acid)</synonym>
    <synonym>(R-(R*,r*))-3,3'-dithiobis(2-aminopropanoic acid)</synonym>
    <synonym>3,3'-Dithiobis-L-alanine</synonym>
    <synonym>beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulfide</synonym>
    <synonym>beta,Beta'-dithiodialanine</synonym>
    <synonym>Bis(beta-amino-beta-carboxyethyl) disulfide</synonym>
    <synonym>e921</synonym>
    <synonym>L-alpha-Diamino-beta-dithiolactic acid</synonym>
    <synonym>L-Dicysteine</synonym>
    <synonym>Oxidized L-cysteine</synonym>
    <synonym>(R,R)-3,3'-Dithiobis(2-aminopropanoate)</synonym>
    <synonym>(R-(R*,r*))-3,3'-dithiobis(2-aminopropanoate)</synonym>
    <synonym>b,Beta'-diamino-b,beta'-dicarboxydiethyl disulfide</synonym>
    <synonym>b,Beta'-diamino-b,beta'-dicarboxydiethyl disulphide</synonym>
    <synonym>beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulphide</synonym>
    <synonym>Β,beta'-diamino-β,beta'-dicarboxydiethyl disulfide</synonym>
    <synonym>Β,beta'-diamino-β,beta'-dicarboxydiethyl disulphide</synonym>
    <synonym>b,Beta'-dithiodialanine</synonym>
    <synonym>Β,beta'-dithiodialanine</synonym>
    <synonym>Bis(b-amino-b-carboxyethyl) disulfide</synonym>
    <synonym>Bis(b-amino-b-carboxyethyl) disulphide</synonym>
    <synonym>Bis(beta-amino-beta-carboxyethyl) disulphide</synonym>
    <synonym>Bis(β-amino-β-carboxyethyl) disulfide</synonym>
    <synonym>Bis(β-amino-β-carboxyethyl) disulphide</synonym>
    <synonym>L-a-Diamino-b-dithiolactate</synonym>
    <synonym>L-a-Diamino-b-dithiolactic acid</synonym>
    <synonym>L-alpha-Diamino-beta-dithiolactate</synonym>
    <synonym>L-Α-diamino-β-dithiolactate</synonym>
    <synonym>L-Α-diamino-β-dithiolactic acid</synonym>
    <synonym>(-)-Cystine</synonym>
    <synonym>(R-(R*,r*))-3,3'-dithiobis</synonym>
    <synonym>2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoate</synonym>
    <synonym>2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acid</synonym>
    <synonym>2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoate</synonym>
    <synonym>2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acid</synonym>
    <synonym>3,3'-Dithiobis</synonym>
    <synonym>3,3'-Dithiobis[2-amino-[R-(r*,r*)]-propanoate</synonym>
    <synonym>3,3'-Dithiobis[2-amino-[R-(r*,r*)]-propanoic acid</synonym>
    <synonym>3,3'-Dithiodialanine</synonym>
    <synonym>b,B'-diamino-b,b'-dicarboxydiethyl disulfide</synonym>
    <synonym>b,B'-dithiodialanine</synonym>
    <synonym>beta,Beta'-dithiobisalanine</synonym>
    <synonym>Bis(b-amino-beta-carboxyethyl) disulfide</synonym>
    <synonym>Cysteine disulfide</synonym>
    <synonym>Cystin</synonym>
    <synonym>Cystine</synonym>
    <synonym>Cystine acid</synonym>
    <synonym>D(+)-3,3'-Dithiobis(2-aminopropanoate</synonym>
    <synonym>D(+)-3,3'-Dithiobis(2-aminopropanoic acid</synonym>
    <synonym>Dicysteine</synonym>
    <synonym>Gelucystine</synonym>
    <synonym>L-(-)-Cystine</synonym>
    <synonym>L-Cysteine disulfide</synonym>
    <synonym>L-Cystin</synonym>
    <synonym>[R-(R*,r*)]-3,3'-dithiobis</synonym>
    <synonym>L Cystine</synonym>
    <synonym>Copper cystinate</synonym>
    <synonym>L-Cystine</synonym>
  </synonyms>
  <chemical_formula>C6H12N2O4S2</chemical_formula>
  <average_molecular_weight>240.3</average_molecular_weight>
  <monisotopic_moleculate_weight>240.023848262</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid</iupac_name>
  <traditional_iupac>L-cystine</traditional_iupac>
  <cas_registry_number>56-89-3</cas_registry_number>
  <smiles>N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1</inchi>
  <inchikey>LEVWYRKDKASIDU-IMJSIDKUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-cysteine-S-conjugates</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkyldisulfides</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dialkyldisulfide</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>L-cysteine-s-conjugate</substituent>
      <substituent>Organic disulfide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Sulfenyl compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-cysteine derivative</external_descriptor>
      <external_descriptor>cystine</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>260.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.19 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.08</value>
      <source>CHMELIK,J ET AL. (1991)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-amino-3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>240.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>240.023848262</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CSSC[C@H](N)C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12N2O4S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LEVWYRKDKASIDU-IMJSIDKUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>126.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4988</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179796</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182132</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1123.596</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1123.596</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1123.596</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1123.596</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1081.981</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1081.981</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1081.981</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00491</kegg_id>
  <foodb_id>FDB012672</foodb_id>
  <drugbank_id>DB00138</drugbank_id>
  <pubchem_compound_id>67678</pubchem_compound_id>
  <chemspider_id>60997</chemspider_id>
  <pdbe_id/>
  <chebi_id>16283</chebi_id>
  <knapsack_id>C00001352</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Cystine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35134</bigg_id>
  <metlin_id>5207</metlin_id>
  <synthesis_reference>Grossi, Loris; Montevecchi, Pier Carlo. S-Nitrosocysteine and Cystine from Reaction of Cysteine with Nitrous Acid. A Kinetic Investigation. Journal of Organic Chemistry  (2002),  67(24),  8625-8630.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:33 UTC</creation_date>
  <update_date>2020-04-15 20:46:15 UTC</update_date>
  <accession>BMDB0000193</accession>
  <secondary_accessions>
    <accession>BMDB00193</accession>
  </secondary_accessions>
  <name>Isocitric acid</name>
  <description>Isocitric acid, also known as isocitrate or i-cit, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Isocitric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Isocitric acid exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>1-Hydroxypropane-1,2,3-tricarboxylic acid</synonym>
    <synonym>1-Hydroxytricarballylic acid</synonym>
    <synonym>1-Hydroxypropane-1,2,3-tricarboxylate</synonym>
    <synonym>1-Hydroxytricarballylate</synonym>
    <synonym>Isocitrate</synonym>
    <synonym>1-Hydroxy-1,2,3-propanetricarboxylate</synonym>
    <synonym>1-Hydroxy-1,2,3-propanetricarboxylic acid</synonym>
    <synonym>3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylate</synonym>
    <synonym>3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid</synonym>
    <synonym>3-Carboxy-2,3-dideoxy-pentarate</synonym>
    <synonym>3-Carboxy-2,3-dideoxy-pentaric acid</synonym>
    <synonym>D-Isocitrate</synonym>
    <synonym>I-cit</synonym>
    <synonym>Threo-D(S)-iso-citrate</synonym>
    <synonym>Threo-DS-isocitrate</synonym>
    <synonym>Isocitric acid, sodium salt</synonym>
    <synonym>Isocitric acid, trisodium salt</synonym>
    <synonym>Isocitric acid, disodium salt</synonym>
    <synonym>Isocitric acid, (11)C-labeled</synonym>
    <synonym>Isocitric acid, calcium salt</synonym>
    <synonym>Isocitric acid, potassium salt</synonym>
  </synonyms>
  <chemical_formula>C6H8O7</chemical_formula>
  <average_molecular_weight>192.1235</average_molecular_weight>
  <monisotopic_moleculate_weight>192.02700261</monisotopic_moleculate_weight>
  <iupac_name>1-hydroxypropane-1,2,3-tricarboxylic acid</iupac_name>
  <traditional_iupac>isocitric acid</traditional_iupac>
  <cas_registry_number>320-77-4</cas_registry_number>
  <smiles>OC(C(CC(O)=O)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)</inchi>
  <inchikey>ODBLHEXUDAPZAU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Tricarboxylic acids and derivatives</sub_class>
    <direct_parent>Tricarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>tricarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>162 - 165 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>466 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-hydroxypropane-1,2,3-tricarboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>192.1235</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>192.02700261</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(C(CC(O)=O)C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H8O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ODBLHEXUDAPZAU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>132.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437927</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>108.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
          <pubmed_id>2760296</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>243</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Rulquin H, Verite R: Effects of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 1. Diets based on corn silage. J Dairy Sci. 1998 Dec;81(12):3239-47. doi: 10.3168/jds.S0022-0302(98)75888-6.</reference_text>
          <pubmed_id>9891269</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>191</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>219</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00311</kegg_id>
  <chemspider_id>1161</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB003281</foodb_id>
  <pubchem_compound_id>1198</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30887</chebi_id>
  <meta_cyc_id>Isocitrate</meta_cyc_id>
  <knapsack_id>C00001188</knapsack_id>
  <wikipedia_id>Isocitric_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34579</bigg_id>
  <metlin_id>3328</metlin_id>
  <synthesis_reference>Finogenova, T. V.; Kamzolova, S. V.; Dedyukhina, E. G.; Shishkanova, N. V.; Il'chenko, A. P.; Morgunov, I. G.; Chernyavskaya, O. G.; Sokolov, A. P.  Biosynthesis of citric and isocitric acids from ethanol by mutant Yarrowia lipolytica N 1 under continuous cultivation.    Applied Microbiology and Biotechnology  (2002),  59(4-5),  493-500.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
      <pubmed_id>2760296</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hurtaud C, Rulquin H, Verite R: Effects of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 1. Diets based on corn silage. J Dairy Sci. 1998 Dec;81(12):3239-47. doi: 10.3168/jds.S0022-0302(98)75888-6.</reference_text>
      <pubmed_id>9891269</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
      <pubmed_id>11132867</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00448</protein_accession>
      <name>Isocitrate dehydrogenase [NADP], mitochondrial</name>
      <uniprot_id>Q04467</uniprot_id>
      <gene_name>IDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00454</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit gamma, mitochondrial</name>
      <uniprot_id>Q58CP0</uniprot_id>
      <gene_name>IDH3G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00471</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial</name>
      <uniprot_id>O77784</uniprot_id>
      <gene_name>IDH3B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00516</protein_accession>
      <name>Isocitrate dehydrogenase [NADP] cytoplasmic</name>
      <uniprot_id>Q9XSG3</uniprot_id>
      <gene_name>IDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00521</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit alpha, mitochondrial</name>
      <uniprot_id>P41563</uniprot_id>
      <gene_name>IDH3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00681</protein_accession>
      <name>Cytoplasmic aconitate hydratase</name>
      <uniprot_id>Q0VCU1</uniprot_id>
      <gene_name>ACO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00687</protein_accession>
      <name>Aconitate hydratase, mitochondrial</name>
      <uniprot_id>P20004</uniprot_id>
      <gene_name>ACO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01814</protein_accession>
      <name>Mitochondrial 2-oxoglutarate/malate carrier protein</name>
      <uniprot_id>P22292</uniprot_id>
      <gene_name>SLC25A11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:34 UTC</creation_date>
  <update_date>2020-04-16 17:51:06 UTC</update_date>
  <accession>BMDB0000194</accession>
  <secondary_accessions>
    <accession>BMDB00194</accession>
  </secondary_accessions>
  <name>Anserine</name>
  <description/>
  <synonyms>
    <synonym>beta-Alanyl-3-methyl-L-histidine</synonym>
    <synonym>beta-Alanyl-N(pai)-methyl-L-histidine</synonym>
    <synonym>b-Alanyl-3-methyl-L-histidine</synonym>
    <synonym>Β-alanyl-3-methyl-L-histidine</synonym>
    <synonym>b-Alanyl-N(pai)-methyl-L-histidine</synonym>
    <synonym>Β-alanyl-N(pai)-methyl-L-histidine</synonym>
    <synonym>L-Anserine</synonym>
    <synonym>L-N-b-Alanyl-3-methyl-histidine</synonym>
    <synonym>L-N-beta-Alanyl-3-methyl-histidine</synonym>
    <synonym>N-b-Alanyl-3-methyl-L-histidine</synonym>
    <synonym>N-beta-Alanyl-3-methyl-L-histidine</synonym>
    <synonym>Balanine</synonym>
    <synonym>Beta Alanyl 3 methylhistidine</synonym>
    <synonym>Beta-Alanyl-3-methylhistidine</synonym>
    <synonym>Ophidine</synonym>
  </synonyms>
  <chemical_formula>C10H16N4O3</chemical_formula>
  <average_molecular_weight>240.259</average_molecular_weight>
  <monisotopic_moleculate_weight>240.122240398</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-(3-aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid</iupac_name>
  <traditional_iupac>anserine</traditional_iupac>
  <cas_registry_number>584-85-0</cas_registry_number>
  <smiles>CN1C=NC=C1C[C@H](NC(=O)CCN)C(O)=O</smiles>
  <inchi>InChI=1S/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1</inchi>
  <inchikey>MYYIAHXIVFADCU-QMMMGPOBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Peptidomimetics</class>
    <sub_class>Hybrid peptides</sub_class>
    <direct_parent>Hybrid peptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Histidine and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolyl carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Histidine or derivatives</substituent>
      <substituent>Hybrid peptide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazolyl carboxylic acid derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>beta-alanine derivative</external_descriptor>
      <external_descriptor>dipeptide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>226 - 228 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-(3-aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>240.259</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>240.122240398</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C=NC=C1C[C@H](NC(=O)CCN)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H16N4O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MYYIAHXIVFADCU-QMMMGPOBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>110.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181330</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>214.93 +/- 49.55</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>411.01 +/- 66.53</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>556.86 +/- 67.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>719.11 +/- 50.49</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01262</kegg_id>
  <foodb_id>FDB021903</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>112072</pubchem_compound_id>
  <chemspider_id>100482</chemspider_id>
  <pdbe_id/>
  <chebi_id>18323</chebi_id>
  <knapsack_id/>
  <meta_cyc_id>CPD-401</meta_cyc_id>
  <wikipedia_id>Anserine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5209</metlin_id>
  <synthesis_reference>Yudaev, N. A.  Biosynthesis of anserine.    Doklady Akademii Nauk SSSR  (1952),  82  615-17.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:35 UTC</creation_date>
  <update_date>2020-04-16 17:52:12 UTC</update_date>
  <accession>BMDB0000195</accession>
  <secondary_accessions>
    <accession>BMDB00195</accession>
  </secondary_accessions>
  <name>Inosine</name>
  <description>Inosine, also known as hypoxanthosine or panholic-L, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Inosine exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Inosine exists in all living species, ranging from bacteria to humans. Inosine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>9-beta-D-Ribofuranosyl-9H-purin-6-ol</synonym>
    <synonym>9-beta-D-Ribofuranosylhypoxanthine</synonym>
    <synonym>Hypoxanthine D-riboside</synonym>
    <synonym>Hypoxanthosine</synonym>
    <synonym>i</synonym>
    <synonym>Inosin</synonym>
    <synonym>Inosina</synonym>
    <synonym>Inosinum</synonym>
    <synonym>Inotin</synonym>
    <synonym>9-b-D-Ribofuranosyl-9H-purin-6-ol</synonym>
    <synonym>9-Β-D-ribofuranosyl-9H-purin-6-ol</synonym>
    <synonym>9-b-D-Ribofuranosylhypoxanthine</synonym>
    <synonym>9-Β-D-ribofuranosylhypoxanthine</synonym>
    <synonym>(-)-Inosine</synonym>
    <synonym>1,9-Dihydro-9-b-D-ribofuranosyl-6H-purin-6-one</synonym>
    <synonym>1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one</synonym>
    <synonym>1,9-Dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one</synonym>
    <synonym>9-b-D-Ribofuranosyl-hypoxanthine</synonym>
    <synonym>9-beta-D-Ribofuranosyl-hypoxanthine</synonym>
    <synonym>9-beta-delta-Ribofuranosyl-hypoxanthine</synonym>
    <synonym>9-beta-delta-Ribofuranosylhypoxanthine</synonym>
    <synonym>9beta-D-Ribofuranosylhypoxanthine</synonym>
    <synonym>9beta-delta-Ribofuranosylhypoxanthine</synonym>
    <synonym>Atorel</synonym>
    <synonym>beta-D-Ribofuranoside hypoxanthine-9</synonym>
    <synonym>beta-delta-Ribofuranoside hypoxanthine-9</synonym>
    <synonym>beta-Inosine</synonym>
    <synonym>HXR</synonym>
    <synonym>Hypoxanthine 9-beta-D-ribofuranoside</synonym>
    <synonym>Hypoxanthine 9-beta-delta-ribofuranoside</synonym>
    <synonym>Hypoxanthine nucleoside</synonym>
    <synonym>Hypoxanthine ribonucleoside</synonym>
    <synonym>Hypoxanthine riboside</synonym>
    <synonym>Hypoxanthine-9 beta-D-ribofuranoside</synonym>
    <synonym>Hypoxanthine-9 beta-delta-ribofuranoside</synonym>
    <synonym>Hypoxanthine-9-beta-D-ribofuranoside</synonym>
    <synonym>Hypoxanthine-9-beta-delta-ribofuranoside</synonym>
    <synonym>Hypoxanthine-9-D-ribofuranoside</synonym>
    <synonym>Hypoxanthine-9-delta-ribofuranoside</synonym>
    <synonym>Hypoxanthine-ribose</synonym>
    <synonym>Indole-3-carboxaldehyde</synonym>
    <synonym>Ino</synonym>
    <synonym>Inosie</synonym>
    <synonym>Iso-prinosine</synonym>
    <synonym>Oxiamin</synonym>
    <synonym>Panholic-L</synonym>
    <synonym>Pantholic-L</synonym>
    <synonym>Ribonosine</synonym>
    <synonym>Selfer</synonym>
    <synonym>Trophicardyl</synonym>
  </synonyms>
  <chemical_formula>C10H12N4O5</chemical_formula>
  <average_molecular_weight>268.2261</average_molecular_weight>
  <monisotopic_moleculate_weight>268.080769514</monisotopic_moleculate_weight>
  <iupac_name>9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one</iupac_name>
  <traditional_iupac>inosine</traditional_iupac>
  <cas_registry_number>58-63-9</cas_registry_number>
  <smiles>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(O)N=CN=C12</smiles>
  <inchi>InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>UGQMRVRMYYASKQ-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleosides</class>
    <sub_class/>
    <direct_parent>Purine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleoside</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>inosines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>218 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>15.8 mg/mL</value>
      <source>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>6.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>268.2261</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>268.080769514</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(O)N=CN=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N4O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UGQMRVRMYYASKQ-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>129.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3566</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>833+/-140</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.970 +/- 0.420</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52.</reference_text>
          <pubmed_id>1897275</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68.</reference_text>
          <pubmed_id>11242448</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>301.14 +/- 26.11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in beef muscle (longissimus dorsi).</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>356.78 +/- 41.47</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>395.56 +/- 38.59</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>427.49 +/- 33.47</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>225+/-95</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00294</kegg_id>
  <foodb_id>FDB011802</foodb_id>
  <drugbank_id>DB04335</drugbank_id>
  <pubchem_compound_id>6021</pubchem_compound_id>
  <chemspider_id>5799</chemspider_id>
  <pdbe_id/>
  <chebi_id>17596</chebi_id>
  <knapsack_id>C00019692</knapsack_id>
  <meta_cyc_id>INOSINE</meta_cyc_id>
  <wikipedia_id>Inosine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34525</bigg_id>
  <metlin_id>84</metlin_id>
  <synthesis_reference>Shi, Qingshan; Qiu, Yutang; Li, Liangqiu; Lin, Xiaoping.  New inosine-producing bacterium and method for producing inosine.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2003),     6 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52.</reference_text>
      <pubmed_id>1897275</pubmed_id>
    </reference>
    <reference>
      <reference_text>Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68.</reference_text>
      <pubmed_id>11242448</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00839</protein_accession>
      <name>Adenosine deaminase</name>
      <uniprot_id>P56658</uniprot_id>
      <gene_name>ADA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:36 UTC</creation_date>
  <update_date>2020-04-16 20:40:39 UTC</update_date>
  <accession>BMDB0000197</accession>
  <secondary_accessions>
    <accession>BMDB00197</accession>
  </secondary_accessions>
  <name>Indoleacetic acid</name>
  <description/>
  <synonyms>
    <synonym>Indoleacetate</synonym>
    <synonym>INDOLE-2-acetate</synonym>
    <synonym>2-(1H-indol-2-yl)Acetate</synonym>
  </synonyms>
  <chemical_formula>C10H9NO2</chemical_formula>
  <average_molecular_weight>175.184</average_molecular_weight>
  <monisotopic_moleculate_weight>175.063328537</monisotopic_moleculate_weight>
  <iupac_name>2-(1H-indol-2-yl)acetic acid</iupac_name>
  <traditional_iupac>1H-indol-2-ylacetic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>OC(=O)CC1=CC2=CC=CC=C2N1</smiles>
  <inchi>InChI=1S/C10H9NO2/c12-10(13)6-8-5-7-3-1-2-4-9(7)11-8/h1-5,11H,6H2,(H,12,13)</inchi>
  <inchikey>QOPBEBWGSGFROG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Indolyl carboxylic acids and derivatives</sub_class>
    <direct_parent>Indolyl carboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Indoles</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indole</substituent>
      <substituent>Indolyl carboxylic acid derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(1H-indol-2-yl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>175.184</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>175.063328537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC1=CC2=CC=CC=C2N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H9NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H9NO2/c12-10(13)6-8-5-7-3-1-2-4-9(7)11-8/h1-5,11H,6H2,(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QOPBEBWGSGFROG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>53.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>48.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1314904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1314905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1314906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1429378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1429379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1429380</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id>4371752</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Indole-3-acetic acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference> Snyder, H. R.; Pilgrim, Frederick J. Preparation of 3-indoleacetic acid; new synthesis of tryptophol. Journal of the American Chemical Society (1948), 70 3770-1.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:38 UTC</creation_date>
  <update_date>2020-04-16 21:05:30 UTC</update_date>
  <accession>BMDB0000201</accession>
  <secondary_accessions>
    <accession>BMDB00201</accession>
  </secondary_accessions>
  <name>L-Acetylcarnitine</name>
  <description>L-Acetylcarnitine, also known as alcar or branigen, belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Thus, L-acetylcarnitine is considered to be a fatty ester lipid molecule. L-Acetylcarnitine exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. L-Acetylcarnitine exists in all living species, ranging from bacteria to humans. L-Acetylcarnitine participates in a number of enzymatic reactions, within cattle. In particular, L-Acetylcarnitine and coenzyme A can be biosynthesized from acetyl-CoA and L-carnitine through the action of the enzyme carnitine O-acetyltransferase. In addition, L-Acetylcarnitine and L-carnitine can be converted into acetyl-CoA and coenzyme A; which is catalyzed by the enzyme carnitine O-acetyltransferase. In cattle, L-acetylcarnitine is involved in the metabolic pathway called the Beta oxidation OF very long chain fatty acids pathway. L-Acetylcarnitine has been found to be associated with several diseases known as colorectal cancer, crohn's disease, and 3-hydroxyacyl-coa dehydrogenase deficiency; also l-acetylcarnitine has been linked to several inborn metabolic disorders including very long chain acyl-coa dehydrogenase deficiency and 3-methyl-crotonyl-glycinuria.</description>
  <synonyms>
    <synonym>(-)-Acetylcarnitine</synonym>
    <synonym>(R)-Acetylcarnitine</synonym>
    <synonym>Acetyl-L-(-)-carnitine</synonym>
    <synonym>Acetyl-L-carnitine</synonym>
    <synonym>L-Acetylcarnitine</synonym>
    <synonym>L-Carnitine acetyl ester</synonym>
    <synonym>L-O-Acetylcarnitine</synonym>
    <synonym>O-Acetyl-(R)-carnitine</synonym>
    <synonym>R-Acetylcarnitine</synonym>
    <synonym>Branigen</synonym>
    <synonym>Levocarnitine acetyl</synonym>
    <synonym>Acetyl carnitine</synonym>
    <synonym>Carnitine, acetyl</synonym>
    <synonym>Alcar</synonym>
    <synonym>Acetyl L carnitine</synonym>
    <synonym>Acetylcarnitine, (R)-isomer</synonym>
    <synonym>Medosan</synonym>
    <synonym>ALC</synonym>
    <synonym>3-(Acetyloxy)-4-(trimethylammonio)butanoate</synonym>
    <synonym>Acetyl-DL-carnitine</synonym>
    <synonym>Acetylcarnitine</synonym>
    <synonym>DL-O-Acetylcarnitine</synonym>
    <synonym>3-(Acetyloxy)-4-(trimethylammonio)butanoic acid</synonym>
    <synonym>(+-)-Acetylcarnitine</synonym>
    <synonym>Acetyl-carnitine</synonym>
    <synonym>ALCAR</synonym>
    <synonym>Nicetile</synonym>
    <synonym>O-Acetyl-L-carnitine</synonym>
    <synonym>O-Acetylcarnitine</synonym>
    <synonym>(3R)-3-Acetyloxy-4-(trimethylazaniumyl)butanoate</synonym>
    <synonym>C2 Carnitine</synonym>
  </synonyms>
  <chemical_formula>C9H17NO4</chemical_formula>
  <average_molecular_weight>203.238</average_molecular_weight>
  <monisotopic_moleculate_weight>203.115758031</monisotopic_moleculate_weight>
  <iupac_name>(3R)-3-(acetyloxy)-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>acetyl-L-carnitine</traditional_iupac>
  <cas_registry_number>3040-38-8</cas_registry_number>
  <smiles>[H][C@@](CC([O-])=O)(C[N+](C)(C)C)OC(C)=O</smiles>
  <inchi>InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3/t8-/m1/s1</inchi>
  <inchikey>RDHQFKQIGNGIED-MRVPVSSYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Acyl carnitines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl-carnitine</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>O-acetylcarnitine</external_descriptor>
      <external_descriptor>O-acyl-L-carnitine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R)-3-(acetyloxy)-4-(trimethylazaniumyl)butanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>203.238</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>203.115758031</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](CC([O-])=O)(C[N+](C)(C)C)OC(C)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H17NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H17NO4/c1-7(11)14-8(5-9(12)13)6-10(2,3)4/h8H,5-6H2,1-4H3/t8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RDHQFKQIGNGIED-MRVPVSSYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218100</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.96 +/- 0.36</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by ESI-MS/MS in male Charolais x Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Widmann P, Reverter A, Weikard R, Suhre K, Hammon HM, Albrecht E, Kuehn C: Systems biology analysis merging phenotype, metabolomic and genomic data identifies Non-SMC Condensin I Complex, Subunit G (NCAPG) and cellular maintenance processes as major contributors to genetic variability in bovine feed efficiency. PLoS One. 2015 Apr 15;10(4):e0124574. doi: 10.1371/journal.pone.0124574. eCollection 2015.</reference_text>
          <pubmed_id>25875852</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.65-1.09</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Sadri H, von Soosten D, Meyer U, Kluess J, Danicke S, Saremi B, Sauerwein H: Plasma amino acids and metabolic profiling of dairy cows in response to a bolus duodenal infusion of leucine. PLoS One. 2017 Apr 28;12(4):e0176647. doi: 10.1371/journal.pone.0176647. eCollection 2017.</reference_text>
          <pubmed_id>28453535</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>5+/-2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>854+/-153</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>1892+/-398</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from 20 healthy Holstein Friesian dairy cows </comment>
      <references>
        <reference>
          <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
          <pubmed_id>23738862</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>45.97 +/- 7.39</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>48 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>48 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>48 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>50 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>51.71 +/- 12.86</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>37 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>39 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>37 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>41 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>49.66 +/- 12.65</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.24+/-0.11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>871+/-150</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>1612+/-318</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>40+/-11</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02571</kegg_id>
  <foodb_id>FDB093666</foodb_id>
  <drugbank_id>DB08842</drugbank_id>
  <pubchem_compound_id>7045767</pubchem_compound_id>
  <chemspider_id>5406074</chemspider_id>
  <pdbe_id/>
  <chebi_id>57589</chebi_id>
  <knapsack_id/>
  <meta_cyc_id>O-ACETYLCARNITINE</meta_cyc_id>
  <wikipedia_id>Acetyl-L-carnitine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Gu, Heng-da; Shi, Shuang; Yang, Ying; Shi, Zhao-xin; Yu, Zhan-long. Synthesis of acetyl-L-carnitine by direct acylation method. Shenyang Huagong Xueyuan Xuebao  (2006),  20(2),  154-155, 160. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
      <pubmed_id>23738862</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:39 UTC</creation_date>
  <update_date>2020-04-15 22:13:16 UTC</update_date>
  <accession>BMDB0000202</accession>
  <secondary_accessions>
    <accession>BMDB00202</accession>
  </secondary_accessions>
  <name>Methylmalonic acid</name>
  <description>Methylmalonic acid, also known as 2-methylmalonate or methyl-propanedioate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Methylmalonic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Methylmalonic acid exists in all living species, ranging from bacteria to humans. In cattle, methylmalonic acid is involved in the metabolic pathway called the vitamin K metabolism pathway. Methylmalonic acid is a potentially toxic compound. Methylmalonic acid has been found to be associated with several diseases known as eosinophilic esophagitis, combined malonic and methylmalonic aciduria, alzheimer's disease, and methylmalonic aciduria mitochondrial encephelopathy leigh-like; also methylmalonic acid has been linked to the inborn metabolic disorders including vitamin B12 deficiency.</description>
  <synonyms>
    <synonym>1,1-Ethanedicarboxylic acid</synonym>
    <synonym>2-Methylmalonic acid</synonym>
    <synonym>alpha-Methylmalonic acid</synonym>
    <synonym>Isosuccinic acid</synonym>
    <synonym>1,1-Ethanedicarboxylate</synonym>
    <synonym>2-Methylmalonate</synonym>
    <synonym>a-Methylmalonate</synonym>
    <synonym>a-Methylmalonic acid</synonym>
    <synonym>alpha-Methylmalonate</synonym>
    <synonym>Α-methylmalonate</synonym>
    <synonym>Α-methylmalonic acid</synonym>
    <synonym>Isosuccinate</synonym>
    <synonym>Methylmalonate</synonym>
    <synonym>Methyl-malonate</synonym>
    <synonym>Methyl-malonic acid</synonym>
    <synonym>Methyl-propanedioate</synonym>
    <synonym>Methyl-propanedioic acid</synonym>
    <synonym>Methylpropanedioate</synonym>
    <synonym>Methylpropanedioic acid</synonym>
    <synonym>Acid, methylmalonic</synonym>
    <synonym>Methylmalonic acid</synonym>
  </synonyms>
  <chemical_formula>C4H6O4</chemical_formula>
  <average_molecular_weight>118.088</average_molecular_weight>
  <monisotopic_moleculate_weight>118.02660868</monisotopic_moleculate_weight>
  <iupac_name>2-methylpropanedioic acid</iupac_name>
  <traditional_iupac>methylmalonic acid</traditional_iupac>
  <cas_registry_number>516-05-2</cas_registry_number>
  <smiles>CC(C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8)</inchi>
  <inchikey>ZIYVHBGGAOATLY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Dicarboxylic acids and derivatives</sub_class>
    <direct_parent>Dicarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-dicarbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C4-dicarboxylic acid</external_descriptor>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>135 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>679.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-methylpropanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>118.088</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>118.02660868</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H6O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZIYVHBGGAOATLY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>23.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin K Metabolism</name>
      <smpdb_id>SMP0087227</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438079</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by NMR and GC-MS</comment>
      <references>
        <reference>
          <reference_text>Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26.</reference_text>
          <pubmed_id>27236769</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.593 +/- 0.043</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Girard CL, Matte JJ: Effects of intramuscular injections of vitamin B12 on lactation performance of dairy cows fed dietary supplements of folic acid and rumen-protected methionine. J Dairy Sci. 2005 Feb;88(2):671-6. doi: 10.3168/jds.S0022-0302(05)72731-4.</reference_text>
          <pubmed_id>15653534</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02170</kegg_id>
  <foodb_id>FDB021905</foodb_id>
  <drugbank_id>DB04183</drugbank_id>
  <phenol_explorer_compound_id/>
  <chemspider_id>473</chemspider_id>
  <pdbe_id/>
  <chebi_id>30860</chebi_id>
  <pubchem_compound_id>487</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id>CPD-546</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Methylmalonic_acid</wikipedia_id>
  <metlin_id>3712</metlin_id>
  <synthesis_reference>Edamura, Koji; Arai, Takeshi.  Malonic and methylmalonic acids from b-hydroxypropionic acids.    Jpn. Kokai Tokkyo Koho  (1979),     5 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
      <pubmed_id>29197344</pubmed_id>
    </reference>
    <reference>
      <reference_text>Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26.</reference_text>
      <pubmed_id>27236769</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:40 UTC</creation_date>
  <update_date>2020-03-13 16:19:25 UTC</update_date>
  <accession>BMDB0000205</accession>
  <secondary_accessions>
    <accession>BMDB00205</accession>
  </secondary_accessions>
  <name>Phenylpyruvic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Phenyl-2-oxopropanoate</synonym>
    <synonym>3-Phenyl-2-oxopropanoic acid</synonym>
    <synonym>3-PHENYLPYRUVIC ACID</synonym>
    <synonym>alpha-Ketohydrocinnamic acid</synonym>
    <synonym>alpha-oxo-Benzenepropanoic acid</synonym>
    <synonym>beta-Phenylpyruvic acid</synonym>
    <synonym>Keto-phenylpyruvate</synonym>
    <synonym>Phenylbrenztraubensaeure</synonym>
    <synonym>Phenylpyruvate</synonym>
    <synonym>2-oxo-3-Phenylpropanoate</synonym>
    <synonym>3-PHENYLPYRUVate</synonym>
    <synonym>a-Ketohydrocinnamate</synonym>
    <synonym>a-Ketohydrocinnamic acid</synonym>
    <synonym>alpha-Ketohydrocinnamate</synonym>
    <synonym>Α-ketohydrocinnamate</synonym>
    <synonym>Α-ketohydrocinnamic acid</synonym>
    <synonym>a-oxo-Benzenepropanoate</synonym>
    <synonym>a-oxo-Benzenepropanoic acid</synonym>
    <synonym>alpha-oxo-Benzenepropanoate</synonym>
    <synonym>Α-oxo-benzenepropanoate</synonym>
    <synonym>Α-oxo-benzenepropanoic acid</synonym>
    <synonym>b-Phenylpyruvate</synonym>
    <synonym>b-Phenylpyruvic acid</synonym>
    <synonym>beta-Phenylpyruvate</synonym>
    <synonym>Β-phenylpyruvate</synonym>
    <synonym>Β-phenylpyruvic acid</synonym>
    <synonym>Keto-phenylpyruvic acid</synonym>
    <synonym>2-oxo-3-Phenylpropanoic acid</synonym>
    <synonym>2-Hydroxy-3-phenyl-2-propenoic acid, 9ci</synonym>
    <synonym>2-oxo-3-Phenylpropanoic acid (mixture oxo and keto)</synonym>
    <synonym>a-Hydroxycinnamic acid</synonym>
    <synonym>a-Oxobenzenepropanoic acid, 9ci</synonym>
    <synonym>FEMA 3892</synonym>
    <synonym>Phenylpyroracemate</synonym>
    <synonym>Phenylpyroracemic acid</synonym>
    <synonym>Phenylpyruvic acid, calcium salt</synonym>
    <synonym>Phenylpyruvic acid, sodium salt</synonym>
    <synonym>Phenylpyruvic acid</synonym>
  </synonyms>
  <chemical_formula>C9H8O3</chemical_formula>
  <average_molecular_weight>164.158</average_molecular_weight>
  <monisotopic_moleculate_weight>164.047344122</monisotopic_moleculate_weight>
  <iupac_name>2-oxo-3-phenylpropanoic acid</iupac_name>
  <traditional_iupac>phenylpyruvic acid</traditional_iupac>
  <cas_registry_number>156-06-9</cas_registry_number>
  <smiles>OC(=O)C(=O)CC1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)</inchi>
  <inchikey>BTNMPGBKDVTSJY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Phenylpyruvic acid derivatives</sub_class>
    <direct_parent>Phenylpyruvic acid derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Keto acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenylpyruvate</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>154 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>112 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-oxo-3-phenylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>164.158</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>164.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C(=O)CC1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BTNMPGBKDVTSJY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37354</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>16.7 +/- 13.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Khan RI, Onodera R, Amin MR, Mohammed N: Production of tyrosine and other aromatic compounds from phenylalanine by rumen microorganisms. Amino Acids. 1999;17(4):335-46.</reference_text>
          <pubmed_id>10707763</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00166</kegg_id>
  <drugbank_id>DB03884</drugbank_id>
  <foodb_id>FDB008272</foodb_id>
  <chemspider_id>972</chemspider_id>
  <pubchem_compound_id>997</pubchem_compound_id>
  <chebi_id>30851</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00000751</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Phenylpyruvic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34111</bigg_id>
  <metlin_id>328</metlin_id>
  <synthesis_reference>Li, Hongbin; Luo, Yuzhong.  Preparation of phenyl-pyruvic acid by dicarbonylation of benzyl halide.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (1996),  5 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00123</protein_accession>
      <name>Macrophage migration inhibitory factor</name>
      <uniprot_id>P80177</uniprot_id>
      <gene_name>MIF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:41 UTC</creation_date>
  <update_date>2020-04-14 22:46:58 UTC</update_date>
  <accession>BMDB0000206</accession>
  <secondary_accessions>
    <accession>BMDB00206</accession>
  </secondary_accessions>
  <name>N6-Acetyl-L-lysine</name>
  <description>N6-Acetyl-L-lysine, also known as N(6)-acetyllysine or omega-acetyllsine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. N6-Acetyl-L-lysine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. N6-Acetyl-L-lysine exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>(2S)-6-(Acetylamino)-2-aminohexanoic acid</synonym>
    <synonym>N(6)-ACETYLLYSINE</synonym>
    <synonym>N(zeta)-Acetyllysine</synonym>
    <synonym>N-epsilon-Acetyl-L-lysine</synonym>
    <synonym>N-Epsilon-Acetyllysine</synonym>
    <synonym>N(epsilon)-Acetyl-L-lysine</synonym>
    <synonym>N(zeta)-Acetyl-L-lysine</synonym>
    <synonym>(2S)-6-(Acetylamino)-2-aminohexanoate</synonym>
    <synonym>N(Z)-Acetyllysine</synonym>
    <synonym>N(Ζ)-acetyllysine</synonym>
    <synonym>N(Z)-Acetyl-L-lysine</synonym>
    <synonym>N(Ζ)-acetyl-L-lysine</synonym>
    <synonym>e-Acetyl-L-lysine</synonym>
    <synonym>e-N-Acetyl-L-lysine</synonym>
    <synonym>e-N-Acetyllysine</synonym>
    <synonym>epsilon-Acetyl-L-lysine</synonym>
    <synonym>epsilon-N-Acetyl-L-lysine</synonym>
    <synonym>epsilon-N-Acetyllysine</synonym>
    <synonym>L-e-N-Acetyllysine</synonym>
    <synonym>L-epsilon-N-Acetyllysine</synonym>
    <synonym>N-e-Acetyl-L-lysine</synonym>
    <synonym>N-e-Acetyllysine</synonym>
    <synonym>N6-Acetyllysine</synonym>
    <synonym>Ne-acetyl-L-lysine</synonym>
    <synonym>Ne-acetyllysine</synonym>
    <synonym>Omega-N-acetyl-L-lysine</synonym>
    <synonym>W-N-Acetyl-L-lysine</synonym>
    <synonym>N(6)-Acetyllsine</synonym>
    <synonym>Omega-acetyllsine</synonym>
    <synonym>(2S)-6-Acetamido-2-aminohexanoic acid</synonym>
    <synonym>6-Acetamido-2-aminohexanoic acid</synonym>
    <synonym>L-Ε-N-acetyllysine</synonym>
    <synonym>Nepsilon-acetyl-L-lysine</synonym>
    <synonym>Nepsilon-acetyllysine</synonym>
    <synonym>Nε-acetyl-L-lysine</synonym>
    <synonym>Nε-acetyllysine</synonym>
    <synonym>Ε-acetyl-L-lysine</synonym>
    <synonym>Ε-N-acetyl-L-lysine</synonym>
    <synonym>Ε-N-acetyllysine</synonym>
    <synonym>Ω-N-acetyl-L-lysine</synonym>
    <synonym>N6-Acetyl-L-lysine</synonym>
  </synonyms>
  <chemical_formula>C8H16N2O3</chemical_formula>
  <average_molecular_weight>188.2242</average_molecular_weight>
  <monisotopic_moleculate_weight>188.116092388</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-6-acetamidohexanoic acid</iupac_name>
  <traditional_iupac>N6-acetyllysine</traditional_iupac>
  <cas_registry_number>692-04-6</cas_registry_number>
  <smiles>CC(=O)NCCCC[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C8H16N2O3/c1-6(11)10-5-3-2-4-7(9)8(12)13/h7H,2-5,9H2,1H3,(H,10,11)(H,12,13)/t7-/m0/s1</inchi>
  <inchikey>DTERQYGMUDWYAZ-ZETCQYMHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N(6)-acyl-L-lysine</external_descriptor>
      <external_descriptor>acetyl-L-lysine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>250 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-6-acetamidohexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>188.2242</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>188.116092388</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)NCCCC[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16N2O3/c1-6(11)10-5-3-2-4-7(9)8(12)13/h7H,2-5,9H2,1H3,(H,10,11)(H,12,13)/t7-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DTERQYGMUDWYAZ-ZETCQYMHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445741</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fermented milk, by capillary electrophoresis-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
          <pubmed_id>26686724</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02727</kegg_id>
  <foodb_id>FDB000476</foodb_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <chemspider_id>83801</chemspider_id>
  <pdbe_id/>
  <chebi_id>17752</chebi_id>
  <pubchem_compound_id>92832</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id>CPD-567</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Acetyllysine</wikipedia_id>
  <metlin_id>5216</metlin_id>
  <synthesis_reference>Benoiton, Leo; Leclerc, Jean.  An improved synthesis of e-N-acetyl-L-lysine and similar compounds.  Canadian Journal of Chemistry  (1965),  43(4),  991-3.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
      <pubmed_id>26686724</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:42 UTC</creation_date>
  <update_date>2020-04-16 20:38:22 UTC</update_date>
  <accession>BMDB0000207</accession>
  <secondary_accessions>
    <accession>BMDB00207</accession>
  </secondary_accessions>
  <name>Oleic acid</name>
  <description>Oleic acid, also known as pamolyn or oleate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Oleic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Oleic acid exists in all living species, ranging from bacteria to humans. Oleic acid is a potentially toxic compound. Oleic acid has been found to be associated with several diseases known as colorectal cancer, schizophrenia, gestational diabetes, and lung cancer; also oleic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.</description>
  <synonyms>
    <synonym>(9Z)-Octadecenoic acid</synonym>
    <synonym>(Z)-Octadec-9-enoic acid</synonym>
    <synonym>18:1 N-9</synonym>
    <synonym>18:1DElta9cis</synonym>
    <synonym>C18:1 N-9</synonym>
    <synonym>cis-9-Octadecenoic acid</synonym>
    <synonym>cis-Delta(9)-Octadecenoic acid</synonym>
    <synonym>cis-Oleic acid</synonym>
    <synonym>FA 18:1</synonym>
    <synonym>Octadec-9-enoic acid</synonym>
    <synonym>Oelsaeure</synonym>
    <synonym>Oleate</synonym>
    <synonym>(9Z)-Octadecenoate</synonym>
    <synonym>(Z)-Octadec-9-enoate</synonym>
    <synonym>cis-9-Octadecenoate</synonym>
    <synonym>cis-delta(9)-Octadecenoate</synonym>
    <synonym>cis-Δ(9)-octadecenoate</synonym>
    <synonym>cis-Δ(9)-octadecenoic acid</synonym>
    <synonym>cis-Oleate</synonym>
    <synonym>Octadec-9-enoate</synonym>
    <synonym>(9Z)-9-Octadecenoate</synonym>
    <synonym>(9Z)-9-Octadecenoic acid</synonym>
    <synonym>(Z)-9-Octadecanoate</synonym>
    <synonym>(Z)-9-Octadecanoic acid</synonym>
    <synonym>9,10-Octadecenoate</synonym>
    <synonym>9,10-Octadecenoic acid</synonym>
    <synonym>9-(Z)-Octadecenoate</synonym>
    <synonym>9-(Z)-Octadecenoic acid</synonym>
    <synonym>9-Octadecenoate</synonym>
    <synonym>9-Octadecenoic acid</synonym>
    <synonym>Century CD fatty acid</synonym>
    <synonym>cis-Octadec-9-enoate</synonym>
    <synonym>cis-Octadec-9-enoic acid</synonym>
    <synonym>Distoline</synonym>
    <synonym>Emersol 210</synonym>
    <synonym>Emersol 211</synonym>
    <synonym>Emersol 213</synonym>
    <synonym>Emersol 220 white oleate</synonym>
    <synonym>Emersol 220 white oleic acid</synonym>
    <synonym>Emersol 221 low titer white oleate</synonym>
    <synonym>Emersol 221 low titer white oleic acid</synonym>
    <synonym>Emersol 233LL</synonym>
    <synonym>Emersol 6321</synonym>
    <synonym>Emersol 6333 NF</synonym>
    <synonym>Emersol 7021</synonym>
    <synonym>Glycon ro</synonym>
    <synonym>Glycon wo</synonym>
    <synonym>Groco 2</synonym>
    <synonym>Groco 4</synonym>
    <synonym>Groco 5l</synonym>
    <synonym>Groco 6</synonym>
    <synonym>Industrene 104</synonym>
    <synonym>Industrene 105</synonym>
    <synonym>Industrene 205</synonym>
    <synonym>Industrene 206</synonym>
    <synonym>L'acide oleique</synonym>
    <synonym>Metaupon</synonym>
    <synonym>Oelsauere</synonym>
    <synonym>Oleic acid extra pure</synonym>
    <synonym>Oleinate</synonym>
    <synonym>Oleinic acid</synonym>
    <synonym>Pamolyn</synonym>
    <synonym>Pamolyn 100</synonym>
    <synonym>Pamolyn 100 FG</synonym>
    <synonym>Pamolyn 100 FGK</synonym>
    <synonym>Pamolyn 125</synonym>
    <synonym>Priolene 6900</synonym>
    <synonym>Red oil</synonym>
    <synonym>Tego-oleic 130</synonym>
    <synonym>Vopcolene 27</synonym>
    <synonym>Wecoline oo</synonym>
    <synonym>Z-9-Octadecenoate</synonym>
    <synonym>Z-9-Octadecenoic acid</synonym>
    <synonym>Acid, 9-octadecenoic</synonym>
    <synonym>Acid, oleic</synonym>
    <synonym>9 Octadecenoic acid</synonym>
    <synonym>Acid, cis-9-octadecenoic</synonym>
    <synonym>cis 9 Octadecenoic acid</synonym>
    <synonym>FA(18:1(9Z))</synonym>
    <synonym>FA(18:1n9)</synonym>
  </synonyms>
  <chemical_formula>C18H34O2</chemical_formula>
  <average_molecular_weight>282.4614</average_molecular_weight>
  <monisotopic_moleculate_weight>282.255880332</monisotopic_moleculate_weight>
  <iupac_name>(9Z)-octadec-9-enoic acid</iupac_name>
  <traditional_iupac>oleic acid</traditional_iupac>
  <cas_registry_number>112-80-1</cas_registry_number>
  <smiles>CCCCCCCC\C=C/CCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-</inchi>
  <inchikey>ZQPPMHVWECSIRJ-KTKRTIGZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Monounsaturated fatty acids</external_descriptor>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>octadec-9-enoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>13.4 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(9Z)-octadec-9-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>282.4614</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>282.255880332</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCC\C=C/CCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H34O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZQPPMHVWECSIRJ-KTKRTIGZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>87.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440469</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>74191.38</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>72947.31</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>710540.98</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>804930.87</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>1047306.99</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>1070050.28</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>1242647.67</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Calf-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>1239461.39</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. With growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>1289804.55</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Without growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>1300531.68</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Yearling-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed barley silage diet for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed barley silage diet with flaxseed for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed hay for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed hay with flaxseed for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11.1 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21.1 +/- 0.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>24 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>79.64 +/- 7.47</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk from a Danish Holstein herd by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>87.11 +/- 9.30</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised whole milk (3.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>34.06 +/- 1.048</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised semi skimmed milk (1.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.76 +/- 0.52</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised skimmed milk (0.1% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>71.97 +/- 0.60</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25384.0353 +/- 7080.624</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23790.895 +/- 6584.980</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples have been collected from Heifer cows.</comment>
      <references>
        <reference>
          <reference_text>Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub  2013 Jun 5.</reference_text>
          <pubmed_id>23871026</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Oocyte</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by CP9010 autosampler onto a capillary column within a CP9001 gas chromatograph in slaughtered cow ovaries.</comment>
      <references>
        <reference>
          <reference_text>McEvoy TG, Coull GD, Broadbent PJ, Hutchinson JS, Speake BK: Fatty acid composition of lipids in immature cattle, pig and sheep oocytes with intact zona pellucida. J Reprod Fertil. 2000 Jan;118(1):163-70.</reference_text>
          <pubmed_id>10793638</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1.1 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by FAMEs/GC–MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1.1 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00712</kegg_id>
  <foodb_id>FDB012858</foodb_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <chemspider_id>393217</chemspider_id>
  <pdbe_id/>
  <chebi_id>16196</chebi_id>
  <pubchem_compound_id>445639</pubchem_compound_id>
  <knapsack_id>C00001232</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Oleic_acid</wikipedia_id>
  <metlin_id>190</metlin_id>
  <synthesis_reference>Hu, Sheng; Yuan, Ji-rong; Zhu, Jin; Yin, Ying-sui.  Preparation of high-purity oleic acid by selective reaction. Yingyong Huagong  (2005),  34(12),  748-750, 753.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.</reference_text>
      <pubmed_id>20855010</pubmed_id>
    </reference>
    <reference>
      <reference_text>van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.</reference_text>
      <pubmed_id>28219465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
    </reference>
    <reference>
      <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:43 UTC</creation_date>
  <update_date>2020-04-14 22:46:59 UTC</update_date>
  <accession>BMDB0000208</accession>
  <secondary_accessions>
    <accession>BMDB00208</accession>
  </secondary_accessions>
  <name>Oxoglutaric acid</name>
  <description>Oxoglutaric acid, also known as oxoglutarate or alpha-ketoglutarate, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Oxoglutaric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Oxoglutaric acid exists in all living species, ranging from bacteria to humans. Oxoglutaric acid is a potentially toxic compound. Oxoglutaric acid has been found to be associated with several diseases known as schizophrenia, eosinophilic esophagitis, amish lethal microcephaly, and anoxia; also oxoglutaric acid has been linked to the inborn metabolic disorders including d-2-hydroxyglutaric aciduria.</description>
  <synonyms>
    <synonym>2-Ketoglutaric acid</synonym>
    <synonym>alpha-Ketoglutaric acid</synonym>
    <synonym>2-Ketoglutarate</synonym>
    <synonym>a-Ketoglutarate</synonym>
    <synonym>a-Ketoglutaric acid</synonym>
    <synonym>alpha-Ketoglutarate</synonym>
    <synonym>Α-ketoglutarate</synonym>
    <synonym>Α-ketoglutaric acid</synonym>
    <synonym>Oxoglutarate</synonym>
    <synonym>2-oxo-1,5-Pentanedioate</synonym>
    <synonym>2-oxo-1,5-Pentanedioic acid</synonym>
    <synonym>2-Oxoglutarate</synonym>
    <synonym>2-Oxoglutaric acid</synonym>
    <synonym>2-Oxopentanedioate</synonym>
    <synonym>2-Oxopentanedioic acid</synonym>
    <synonym>alpha-Oxoglutarate</synonym>
    <synonym>Oxogluric acid</synonym>
    <synonym>2 Oxoglutaric acid</synonym>
    <synonym>Ketoglutaric acid</synonym>
    <synonym>alpha Ketoglutaric acid</synonym>
    <synonym>2 Ketoglutaric acid</synonym>
    <synonym>alpha Ketoglutarate</synonym>
    <synonym>alpha Oxoglutarate</synonym>
    <synonym>2 Ketoglutarate</synonym>
    <synonym>2 Oxoglutarate</synonym>
    <synonym>alpha-Oxoglutaric acid</synonym>
    <synonym>alpha-Oxopentanedioic acid</synonym>
    <synonym>alpha-Keto-glutaric acid</synonym>
    <synonym>Α-oxoglutaric acid</synonym>
    <synonym>Α-oxopentanedioic acid</synonym>
    <synonym>Α-keto-glutaric acid</synonym>
  </synonyms>
  <chemical_formula>C5H6O5</chemical_formula>
  <average_molecular_weight>146.0981</average_molecular_weight>
  <monisotopic_moleculate_weight>146.021523302</monisotopic_moleculate_weight>
  <iupac_name>2-oxopentanedioic acid</iupac_name>
  <traditional_iupac>oxoglutarate</traditional_iupac>
  <cas_registry_number>328-50-7</cas_registry_number>
  <smiles>OC(=O)CCC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)</inchi>
  <inchikey>KPGXRSRHYNQIFN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Gamma-keto acids and derivatives</sub_class>
    <direct_parent>Gamma-keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Short-chain keto acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Gamma-keto acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain keto acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>oxo dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>115.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>541.5 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-oxopentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>146.0981</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>146.021523302</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H6O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KPGXRSRHYNQIFN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>91.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glucose-Alanine Cycle</name>
      <smpdb_id>SMP0087221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Malate-Aspartate Shuttle</name>
      <smpdb_id>SMP0087204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Succinate Signalling</name>
      <smpdb_id>SMP0120941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21905</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>117.93 +/- 17.22</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>104 +/- 7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>277.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
          <pubmed_id>2760296</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>112 +/- 7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>103 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>109 +/- 6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>37 - 156</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>70 - 156</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>240</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Rulquin H, Verite R: Effects of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 1. Diets based on corn silage. J Dairy Sci. 1998 Dec;81(12):3239-47. doi: 10.3168/jds.S0022-0302(98)75888-6.</reference_text>
          <pubmed_id>9891269</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>90</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>102</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>116.48 +/- 18.59</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>111.39 +/- 15.62</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>40+/-24</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00026</kegg_id>
  <foodb_id>FDB003361</foodb_id>
  <drugbank_id>DB08845</drugbank_id>
  <phenol_explorer_compound_id/>
  <chemspider_id>50</chemspider_id>
  <pdbe_id/>
  <chebi_id>30915</chebi_id>
  <pubchem_compound_id>51</pubchem_compound_id>
  <knapsack_id>C00000769</knapsack_id>
  <meta_cyc_id>2-KETOGLUTARATE</meta_cyc_id>
  <bigg_id>33565</bigg_id>
  <wikipedia_id>Alpha-Ketoglutaric_acid</wikipedia_id>
  <metlin_id>5218</metlin_id>
  <synthesis_reference>Tanaka, Katsunobu; kimura, Kazu; Yamaguchi, Ken.  Fermentative production of a-oxoglutaric acid.    U.S.  (1973), 4 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
      <pubmed_id>2760296</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hurtaud C, Rulquin H, Verite R: Effects of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 1. Diets based on corn silage. J Dairy Sci. 1998 Dec;81(12):3239-47. doi: 10.3168/jds.S0022-0302(98)75888-6.</reference_text>
      <pubmed_id>9891269</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
      <pubmed_id>11132867</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26.</reference_text>
      <pubmed_id>27236769</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00226</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>A4IFQ7</uniprot_id>
      <gene_name>BCAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00227</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase, mitochondrial</name>
      <uniprot_id>Q5EA40</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00228</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>Q0V8J6</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00229</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>Q5E9U7</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00239</protein_accession>
      <name>Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial</name>
      <uniprot_id>Q5E9N4</uniprot_id>
      <gene_name>AADAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00357</protein_accession>
      <name>L-2-hydroxyglutarate dehydrogenase, mitochondrial</name>
      <uniprot_id>A7MBI3</uniprot_id>
      <gene_name>L2HGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00448</protein_accession>
      <name>Isocitrate dehydrogenase [NADP], mitochondrial</name>
      <uniprot_id>Q04467</uniprot_id>
      <gene_name>IDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00454</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit gamma, mitochondrial</name>
      <uniprot_id>Q58CP0</uniprot_id>
      <gene_name>IDH3G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00471</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial</name>
      <uniprot_id>O77784</uniprot_id>
      <gene_name>IDH3B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00516</protein_accession>
      <name>Isocitrate dehydrogenase [NADP] cytoplasmic</name>
      <uniprot_id>Q9XSG3</uniprot_id>
      <gene_name>IDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00521</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit alpha, mitochondrial</name>
      <uniprot_id>P41563</uniprot_id>
      <gene_name>IDH3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00567</protein_accession>
      <name>Aspartate aminotransferase, cytoplasmic</name>
      <uniprot_id>P33097</uniprot_id>
      <gene_name>GOT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00568</protein_accession>
      <name>Aspartyl/asparaginyl beta-hydroxylase</name>
      <uniprot_id>Q28056</uniprot_id>
      <gene_name>ASPH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00569</protein_accession>
      <name>Aspartate aminotransferase, mitochondrial</name>
      <uniprot_id>P12344</uniprot_id>
      <gene_name>GOT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00571</protein_accession>
      <name>Putative aspartate aminotransferase, cytoplasmic 2</name>
      <uniprot_id>Q2T9S8</uniprot_id>
      <gene_name>GOT1L1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00595</protein_accession>
      <name>Hydroxyacid-oxoacid transhydrogenase, mitochondrial</name>
      <uniprot_id>A6QP15</uniprot_id>
      <gene_name>ADHFE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00596</protein_accession>
      <name>4-aminobutyrate aminotransferase, mitochondrial</name>
      <uniprot_id>Q9BGI0</uniprot_id>
      <gene_name>ABAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00622</protein_accession>
      <name>Trimethyllysine dioxygenase, mitochondrial</name>
      <uniprot_id>Q0VC74</uniprot_id>
      <gene_name>TMLHE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00631</protein_accession>
      <name>Alpha-aminoadipic semialdehyde synthase, mitochondrial</name>
      <uniprot_id>A8E657</uniprot_id>
      <gene_name>AASS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00668</protein_accession>
      <name>Prolyl 4-hydroxylase subunit alpha-1</name>
      <uniprot_id>Q1RMU3</uniprot_id>
      <gene_name>P4HA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00682</protein_accession>
      <name>Procollagen-lysine,2-oxoglutarate 5-dioxygenase 1</name>
      <uniprot_id>O77588</uniprot_id>
      <gene_name>PLOD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00688</protein_accession>
      <name>Phytanoyl-CoA dioxygenase, peroxisomal</name>
      <uniprot_id>O18778</uniprot_id>
      <gene_name>PHYH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00691</protein_accession>
      <name>Prolyl 4-hydroxylase subunit alpha-3</name>
      <uniprot_id>Q75UG4</uniprot_id>
      <gene_name>P4HA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00800</protein_accession>
      <name>D-2-hydroxyglutarate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q1JPD3</uniprot_id>
      <gene_name>D2HGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00855</protein_accession>
      <name>Phosphoserine aminotransferase</name>
      <uniprot_id>A6QR28</uniprot_id>
      <gene_name>PSAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00856</protein_accession>
      <name>Glutamate dehydrogenase 1, mitochondrial</name>
      <uniprot_id>P00366</uniprot_id>
      <gene_name>GLUD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00858</protein_accession>
      <name>Alanine aminotransferase 1</name>
      <uniprot_id>A4IFH5</uniprot_id>
      <gene_name>GPT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00859</protein_accession>
      <name>Tyrosine aminotransferase</name>
      <uniprot_id>Q58CZ9</uniprot_id>
      <gene_name>TAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00861</protein_accession>
      <name>Kynurenine--oxoglutarate transaminase 3</name>
      <uniprot_id>Q0P5G4</uniprot_id>
      <gene_name>CCBL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01072</protein_accession>
      <name>D-3-phosphoglycerate dehydrogenase</name>
      <uniprot_id>Q5EAD2</uniprot_id>
      <gene_name>PHGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01073</protein_accession>
      <name>2-oxoglutarate dehydrogenase E1 component, mitochondrial</name>
      <uniprot_id>Q148N0</uniprot_id>
      <gene_name>OGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01814</protein_accession>
      <name>Mitochondrial 2-oxoglutarate/malate carrier protein</name>
      <uniprot_id>P22292</uniprot_id>
      <gene_name>SLC25A11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02540</protein_accession>
      <name>Solute carrier family 25 (Mitochondrial carrier</name>
      <uniprot_id>A5D954</uniprot_id>
      <gene_name>SLC25A11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:44 UTC</creation_date>
  <update_date>2020-03-13 16:19:27 UTC</update_date>
  <accession>BMDB0000209</accession>
  <secondary_accessions>
    <accession>BMDB00209</accession>
  </secondary_accessions>
  <name>Phenylacetic acid</name>
  <description>Phenylacetic acid, also known as phenylacetate or alpha-toluic acid, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Phenylacetic acid is a drug which is used for use as adjunctive therapy for the treatment of acute hyperammonemia and associated encephalopathy in patients with deficiencies in enzymes of the urea cycle. Phenylacetic acid exists as a solid, possibly soluble (in water), and a weakly acidic compound (based on its pKa) molecule. Phenylacetic acid exists in all living species, ranging from bacteria to humans. In cattle, phenylacetic acid is involved in the metabolic pathway called the phenylacetate metabolism pathway. Phenylacetic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2-PHENYLACETIC ACID</synonym>
    <synonym>2-Phenylethanoic acid</synonym>
    <synonym>alpha-Toluic acid</synonym>
    <synonym>Benzeneacetic acid</synonym>
    <synonym>Benzylformic acid</synonym>
    <synonym>Omega-phenylacetic acid</synonym>
    <synonym>PA</synonym>
    <synonym>Phenylacetate</synonym>
    <synonym>2-PHENYLACETate</synonym>
    <synonym>2-Phenylethanoate</synonym>
    <synonym>a-Toluate</synonym>
    <synonym>a-Toluic acid</synonym>
    <synonym>alpha-Toluate</synonym>
    <synonym>Α-toluate</synonym>
    <synonym>Α-toluic acid</synonym>
    <synonym>Benzeneacetate</synonym>
    <synonym>Benzylformate</synonym>
    <synonym>Omega-phenylacetate</synonym>
    <synonym>Phenylethanoate</synonym>
    <synonym>Phenylethanoic acid</synonym>
    <synonym>W-Phenylacetate</synonym>
    <synonym>W-Phenylacetic acid</synonym>
    <synonym>Phenylacetic acid, potassium salt</synonym>
    <synonym>Sodium phenylacetate</synonym>
    <synonym>Phenylacetic acid, lithium salt</synonym>
    <synonym>Phenylacetic acid, sodium salt</synonym>
    <synonym>Phenylacetic acid, ammonium salt</synonym>
    <synonym>Phenylacetic acid, calcium salt</synonym>
    <synonym>Phenylacetic acid, cesium salt</synonym>
    <synonym>Phenylacetic acid, mercury salt</synonym>
    <synonym>Phenylacetic acid, rubidium salt</synonym>
    <synonym>Phenylacetic acid, sodium salt , carboxy-(11)C-labeled CPD</synonym>
  </synonyms>
  <chemical_formula>C8H8O2</chemical_formula>
  <average_molecular_weight>136.1479</average_molecular_weight>
  <monisotopic_moleculate_weight>136.0524295</monisotopic_moleculate_weight>
  <iupac_name>2-phenylacetic acid</iupac_name>
  <traditional_iupac>ω-phenylacetic acid</traditional_iupac>
  <cas_registry_number>103-82-2</cas_registry_number>
  <smiles>OC(=O)CC1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)</inchi>
  <inchikey>WLJVXDMOQOGPHL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class/>
    <direct_parent>Benzene and substituted derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>benzenes</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>76.7 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>16.6 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.41</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-phenylacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>136.1479</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>136.0524295</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H8O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WLJVXDMOQOGPHL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Phenylacetate Metabolism</name>
      <smpdb_id>SMP0087208</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4994</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>189+/-57</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>480.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>582.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>640.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>347.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>212-785</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>462 +/- 121</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>541 +/- 118</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>143-572</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>640 +/- 101</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>317 +/- 62</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>317 +/- 62</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR and GC-MS</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>363</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>371</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>443</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>241</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>347.49 +/- 57.93</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C07086</kegg_id>
  <foodb_id>FDB031100</foodb_id>
  <drugbank_id>DB09269</drugbank_id>
  <phenol_explorer_compound_id/>
  <chemspider_id>10181341</chemspider_id>
  <pdbe_id/>
  <chebi_id>30745</chebi_id>
  <pubchem_compound_id>999</pubchem_compound_id>
  <knapsack_id>C00000750</knapsack_id>
  <meta_cyc_id>PHENYLACETATE</meta_cyc_id>
  <bigg_id>1486426</bigg_id>
  <wikipedia_id>Phenylacetic_acid</wikipedia_id>
  <metlin_id>129</metlin_id>
  <synthesis_reference>Zhou, Shu-jing; Li, Jin-lian; Luan, Fang.  New synthetic method for benzeneacetic acid.    Huaxue Yu Shengwu Gongcheng  (2005),  22(2),  43-44.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:45 UTC</creation_date>
  <update_date>2020-04-16 20:37:23 UTC</update_date>
  <accession>BMDB0000210</accession>
  <secondary_accessions>
    <accession>BMDB00210</accession>
  </secondary_accessions>
  <name>Pantothenic acid</name>
  <description>(R)-Pantothenic acid, also known as vitamin B5 or (R)-pantothenate, belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl) (R)-Pantothenic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule (R)-Pantothenic acid exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>(+)-Pantothenic acid</synonym>
    <synonym>(R)-N-(2,4-Dihydroxy-3,3-dimethyl-1-oxobutyl)-beta-alanine</synonym>
    <synonym>Chick antidermatitis factor</synonym>
    <synonym>D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-beta-alanine</synonym>
    <synonym>D-(+)-Pantothenic acid</synonym>
    <synonym>D-Pantothenic acid</synonym>
    <synonym>N-[(2R)-2,4-Dihydroxy-3,3-dimethylbutanoyl]-beta-alanine</synonym>
    <synonym>PANTOTHENOIC ACID</synonym>
    <synonym>Vitamin b5</synonym>
    <synonym>(R)-Pantothenate</synonym>
    <synonym>Pantothen pharmaselect</synonym>
    <synonym>(+)-Pantothenate</synonym>
    <synonym>(R)-N-(2,4-Dihydroxy-3,3-dimethyl-1-oxobutyl)-b-alanine</synonym>
    <synonym>(R)-N-(2,4-Dihydroxy-3,3-dimethyl-1-oxobutyl)-β-alanine</synonym>
    <synonym>D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-b-alanine</synonym>
    <synonym>D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-β-alanine</synonym>
    <synonym>D-(+)-Pantothenate</synonym>
    <synonym>D-Pantothenate</synonym>
    <synonym>N-[(2R)-2,4-Dihydroxy-3,3-dimethylbutanoyl]-b-alanine</synonym>
    <synonym>N-[(2R)-2,4-Dihydroxy-3,3-dimethylbutanoyl]-β-alanine</synonym>
    <synonym>PANTOTHENOate</synonym>
    <synonym>(R)-Pantothenic acid</synonym>
    <synonym>Pantothenate</synonym>
    <synonym>b5, Vitamin</synonym>
    <synonym>Pantothenate, zinc</synonym>
    <synonym>b 5, Vitamin</synonym>
    <synonym>Calcium pantothenate</synonym>
    <synonym>Pantothenate, calcium</synonym>
    <synonym>Vitamin b 5</synonym>
    <synonym>Dexol</synonym>
    <synonym>Zinc pantothenate</synonym>
    <synonym>Pantothenic acid</synonym>
  </synonyms>
  <chemical_formula>C9H17NO5</chemical_formula>
  <average_molecular_weight>219.235</average_molecular_weight>
  <monisotopic_moleculate_weight>219.110672659</monisotopic_moleculate_weight>
  <iupac_name>3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanoic acid</iupac_name>
  <traditional_iupac>(+)-pantothenic acid</traditional_iupac>
  <cas_registry_number>79-83-4</cas_registry_number>
  <smiles>CC(C)(CO)[C@@H](O)C(=O)NCCC(O)=O</smiles>
  <inchi>InChI=1S/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13)/t7-/m0/s1</inchi>
  <inchikey>GHOKWGTUZJEAQD-ZETCQYMHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Secondary alcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Water-soluble vitamins</external_descriptor>
      <external_descriptor>pantothenic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>219.235</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>219.110672659</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)(CO)[C@@H](O)C(=O)NCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H17NO5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13)/t7-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GHOKWGTUZJEAQD-ZETCQYMHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>106.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>49026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448179</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14.596</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15.508</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15.508</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16.421</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16.284</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16.421</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15.508</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15.508</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15.508</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20.3 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20.3 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11.2 +/- 0.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00864</kegg_id>
  <foodb_id>FDB030151</foodb_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <chemspider_id>6361</chemspider_id>
  <pdbe_id/>
  <chebi_id>46905</chebi_id>
  <pubchem_compound_id>6613</pubchem_compound_id>
  <knapsack_id>C00001550</knapsack_id>
  <meta_cyc_id>PANTOTHENATE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Pantothenic_Acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Kataoka, Michihiko; Shimizu, Sakayu; Doi, Yukiko; Yamada, Hideaki. Stereospecific reduction of ethyl 2'-ketopantothenate to ethyl D-(+)-pantothenate with microbial cells as a catalyst. Applied and Environmental Microbiology (1990), 56(11), 3595-7.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:46 UTC</creation_date>
  <update_date>2020-04-16 20:39:55 UTC</update_date>
  <accession>BMDB0000211</accession>
  <secondary_accessions>
    <accession>BMDB00211</accession>
  </secondary_accessions>
  <name>Myoinositol</name>
  <description>Myoinositol, also known as inosite or MI, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. Myoinositol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Myoinositol exists in all living species, ranging from bacteria to humans. In cattle, myoinositol is involved in the metabolic pathway called the inositol phosphate metabolism pathway. Myoinositol has been found to be associated with several diseases known as cachexia, eosinophilic esophagitis, colorectal cancer, and schizophrenia; also myoinositol has been linked to the inborn metabolic disorders including ribose-5-phosphate isomerase deficiency.</description>
  <synonyms>
    <synonym>(1R,2R,3S,4S,5R,6S)-Cyclohexane-1,2,3,4,5,6-hexol</synonym>
    <synonym>1,2,3,4,5,6-HEXAHYDROXY-cyclohexane</synonym>
    <synonym>1,2,3,5/4,6-cyclohexanehexol</synonym>
    <synonym>1D-Myo-inositol</synonym>
    <synonym>1l-Myo-inositol</synonym>
    <synonym>Bios I</synonym>
    <synonym>cis-1,2,3,5-trans-4,6-Cyclohexanehexol</synonym>
    <synonym>Cyclohexitol</synonym>
    <synonym>D-Myo-inositol</synonym>
    <synonym>Dambose</synonym>
    <synonym>I-inositol</synonym>
    <synonym>Inosite</synonym>
    <synonym>Inositol</synonym>
    <synonym>Ins</synonym>
    <synonym>L-Myo-inositol</synonym>
    <synonym>Meat sugar</synonym>
    <synonym>Meso-inositol</synonym>
    <synonym>Myoinositol</synonym>
    <synonym>Inosital</synonym>
    <synonym>Iso-inositol</synonym>
    <synonym>MI</synonym>
    <synonym>Myoinosite</synonym>
    <synonym>Phaseomannite</synonym>
    <synonym>Rat antispectacled eye factor</synonym>
    <synonym>Myo inositol</synonym>
    <synonym>Vitamin b8</synonym>
    <synonym>Myo-inositol</synonym>
  </synonyms>
  <chemical_formula>C6H12O6</chemical_formula>
  <average_molecular_weight>180.1559</average_molecular_weight>
  <monisotopic_moleculate_weight>180.063388116</monisotopic_moleculate_weight>
  <iupac_name>(1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol</iupac_name>
  <traditional_iupac>L-inositol</traditional_iupac>
  <cas_registry_number>87-89-8</cas_registry_number>
  <smiles>O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6-</inchi>
  <inchikey>CDAISMWEOUEBRE-GPIVLXJGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Cyclohexanols</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclitols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Sugar alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclitol or derivatives</substituent>
      <substituent>Cyclohexanol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Polyol</substituent>
      <substituent>Sugar alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>inositol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1R,2R,3r,4S,5S,6s)-cyclohexane-1,2,3,4,5,6-hexol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>180.1559</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>180.063388116</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CDAISMWEOUEBRE-GPIVLXJGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>121.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylinositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087258</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37360</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>45+/-11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>1177+/-221</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>504+/-133</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>588.379 +/- 55.507</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Colostrum</comment>
      <references>
        <reference>
          <reference_text>Ogasa K, Kuboyama M, Kiyosawa I, Suzuki T, Itoh M: The content of free and bound inositol in human and cow's milk. J Nutr Sci Vitaminol (Tokyo). 1975;21(2):129-35.</reference_text>
          <pubmed_id>1151503</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>227.581 +/- 55.507</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Mature milk</comment>
      <references>
        <reference>
          <reference_text>Ogasa K, Kuboyama M, Kiyosawa I, Suzuki T, Itoh M: The content of free and bound inositol in human and cow's milk. J Nutr Sci Vitaminol (Tokyo). 1975;21(2):129-35.</reference_text>
          <pubmed_id>1151503</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>222.0299</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Byun SM, Jenness R: Estimation of free myo-inositol in milks of various species and its source in milk of rats (Rattus norvegicus). J Dairy Sci. 1982 Apr;65(4):531-6. doi: 10.3168/jds.S0022-0302(82)82230-3.</reference_text>
          <pubmed_id>7096723</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>116.566 +/- 15.542</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Indyk HE, Woollard DC: Determination of free myo-inositol in milk and infant formula by high-performance liquid chromatography. Analyst. 1994 Mar;119(3):397-402.</reference_text>
          <pubmed_id>8192226</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>183.175 (122.116-205.378)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized whole milk</comment>
      <references>
        <reference>
          <reference_text>Esperanza Troyano, Mar Villamiel, Agustin Olano, Jesus Sanz, and Isabel Martinez-Castro. Monosaccharides and myo-Inositol in Commercial Milks. J. Agric. Food Chem., 1996, 44 (3), pp 815–817</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>593+/-126</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>7193+/-1232</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00137</kegg_id>
  <foodb_id>FDB010547</foodb_id>
  <drugbank_id>DB13178</drugbank_id>
  <phenol_explorer_compound_id/>
  <chemspider_id>10239179</chemspider_id>
  <pdbe_id/>
  <chebi_id>17268</chebi_id>
  <pubchem_compound_id/>
  <knapsack_id>C00001164</knapsack_id>
  <meta_cyc_id>MYO-INOSITOL</meta_cyc_id>
  <bigg_id>33990</bigg_id>
  <wikipedia_id>Inositol</wikipedia_id>
  <metlin_id>5221</metlin_id>
  <synthesis_reference>Iselin, Beat M. Synthesis of inositol-5-monophosphoric acid and scyllitol monophosphoric acid. Journal of the American Chemical Society (1949), 71 3822-5.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00426</protein_accession>
      <name>Inositol oxygenase</name>
      <uniprot_id>A7MBE4</uniprot_id>
      <gene_name>MIOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00445</protein_accession>
      <name>Diphosphoinositol polyphosphate phosphohydrolase 3-beta</name>
      <uniprot_id>Q58CW0</uniprot_id>
      <gene_name>NUDT11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00456</protein_accession>
      <name>Inositol monophosphatase</name>
      <uniprot_id>P20456</uniprot_id>
      <gene_name>IMPA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00487</protein_accession>
      <name>Inositol monophosphatase 3</name>
      <uniprot_id>Q2KJ53</uniprot_id>
      <gene_name>IMPAD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00496</protein_accession>
      <name>Glycerophosphodiester phosphodiesterase 1</name>
      <uniprot_id>Q3T0T0</uniprot_id>
      <gene_name>GDE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00500</protein_accession>
      <name>Diphosphoinositol polyphosphate phosphohydrolase 1</name>
      <uniprot_id>A2VE79</uniprot_id>
      <gene_name>NUDT3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01874</protein_accession>
      <name>Sodium/myo-inositol cotransporter 2</name>
      <uniprot_id>Q3ZC26</uniprot_id>
      <gene_name>SLC5A11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01875</protein_accession>
      <name>Na+/myo-inositol cotransporter</name>
      <uniprot_id>O19135</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:48 UTC</creation_date>
  <update_date>2020-04-16 20:39:55 UTC</update_date>
  <accession>BMDB0000212</accession>
  <secondary_accessions>
    <accession>BMDB00212</accession>
  </secondary_accessions>
  <name>N-Acetylgalactosamine</name>
  <description>N-Acetylgalactosamine, also known as Tn or alpha-galnac, belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group. N-Acetylgalactosamine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule.</description>
  <synonyms>
    <synonym>2-(Acetylamino)-2-deoxy-alpha-D-galactopyranose</synonym>
    <synonym>alpha-GalNAc</synonym>
    <synonym>alpha-GalpNAc</synonym>
    <synonym>GalNAc-alpha</synonym>
    <synonym>Tn</synonym>
    <synonym>TN Antigen saccharide</synonym>
    <synonym>TN Antigen saccharide component</synonym>
    <synonym>TN Saccharide</synonym>
    <synonym>TN Saccharide component</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-a-D-galactopyranose</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-α-D-galactopyranose</synonym>
    <synonym>a-GalNAc</synonym>
    <synonym>Α-galnac</synonym>
    <synonym>a-GalpNAc</synonym>
    <synonym>Α-galpnac</synonym>
    <synonym>GalNAc-a</synonym>
    <synonym>GalNAc-α</synonym>
    <synonym>2-Acetamido-2-deoxy-a-D-allopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-a-D-glucopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-alpha-D-allopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-alpha-D-glucopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-alpha-delta-allopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-alpha-delta-glucopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-b-D-glucopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-beta-D-glucopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-beta-delta-glucopyranose</synonym>
    <synonym>2-Acetamido-2-desoxy-b-D-talofuranose</synonym>
    <synonym>2-Acetamido-2-desoxy-beta-D-talofuranose</synonym>
    <synonym>2-Acetamido-2-desoxy-beta-delta-talofuranose</synonym>
    <synonym>2-Acetamino-2-deoxy-a-D-glucose</synonym>
    <synonym>2-Acetamino-2-deoxy-alpha-D-glucose</synonym>
    <synonym>2-Acetamino-2-deoxy-alpha-delta-glucose</synonym>
    <synonym>2-Acetamino-2-desoxy-a-D-glucopyranose</synonym>
    <synonym>2-Acetamino-2-desoxy-alpha-D-glucopyranose</synonym>
    <synonym>2-Acetamino-2-desoxy-alpha-delta-glucopyranose</synonym>
    <synonym>2-Acetamino-2-desoxy-D-galaktose</synonym>
    <synonym>2-Acetamino-2-desoxy-D-glucose</synonym>
    <synonym>2-Acetamino-2-desoxy-delta-galaktose</synonym>
    <synonym>2-Acetamino-2-desoxy-delta-glucose</synonym>
    <synonym>2-Acetylamino-2-deoxy-a-D-galactopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-a-D-glucopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-a-D-mannopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-alpha-D-galactopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-alpha-D-glucopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-alpha-D-mannopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-alpha-delta-galactopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-alpha-delta-glucopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-alpha-delta-mannopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-b-D-allopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-b-D-altropyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-b-D-galactopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-b-D-glucopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-b-D-mannopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-beta-D-allopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-beta-D-altropyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-beta-D-galactopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-beta-D-glucopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-beta-D-mannopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-beta-delta-allopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-beta-delta-altropyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-beta-delta-galactopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-beta-delta-glucopyranose</synonym>
    <synonym>2-Acetylamino-2-deoxy-beta-delta-mannopyranose</synonym>
    <synonym>2-Acetylamino-2-desoxy-a-D-galaktose</synonym>
    <synonym>2-Acetylamino-2-desoxy-a-D-mannose</synonym>
    <synonym>2-Acetylamino-2-desoxy-alpha-D-galaktose</synonym>
    <synonym>2-Acetylamino-2-desoxy-alpha-D-mannose</synonym>
    <synonym>2-Acetylamino-2-desoxy-alpha-delta-galaktose</synonym>
    <synonym>2-Acetylamino-2-desoxy-alpha-delta-mannose</synonym>
    <synonym>2-Acetylamino-2-desoxy-b-D-galaktose</synonym>
    <synonym>2-Acetylamino-2-desoxy-b-D-mannose</synonym>
    <synonym>2-Acetylamino-2-desoxy-beta-D-galaktose</synonym>
    <synonym>2-Acetylamino-2-desoxy-beta-D-mannose</synonym>
    <synonym>2-Acetylamino-2-desoxy-beta-delta-galaktose</synonym>
    <synonym>2-Acetylamino-2-desoxy-beta-delta-mannose</synonym>
    <synonym>2-Acetylamino-2-desoxy-D-mannose</synonym>
    <synonym>2-Acetylamino-2-desoxy-delta-mannose</synonym>
    <synonym>2-Acetylamino-2-desoxy-DL-glucopyranose</synonym>
    <synonym>2-Acetylamino-a-D-2-deoxy-galactopyranose</synonym>
    <synonym>2-Acetylamino-a-D-2-deoxy-glucopyranose</synonym>
    <synonym>2-Acetylamino-a-D-2-deoxy-glucose</synonym>
    <synonym>2-Acetylamino-a-D-2-deoxy-mannopyranose</synonym>
    <synonym>2-Acetylamino-alpha-D-2-deoxy-galactopyranose</synonym>
    <synonym>2-Acetylamino-alpha-D-2-deoxy-glucopyranose</synonym>
    <synonym>2-Acetylamino-alpha-D-2-deoxy-glucose</synonym>
    <synonym>2-Acetylamino-alpha-D-2-deoxy-mannopyranose</synonym>
    <synonym>2-Acetylamino-alpha-delta-2-deoxy-galactopyranose</synonym>
    <synonym>2-Acetylamino-alpha-delta-2-deoxy-glucopyranose</synonym>
    <synonym>2-Acetylamino-alpha-delta-2-deoxy-glucose</synonym>
    <synonym>2-Acetylamino-alpha-delta-2-deoxy-mannopyranose</synonym>
    <synonym>2-Acetylamino-b-D-2-deoxy-galactopyranose</synonym>
    <synonym>2-Acetylamino-b-D-2-deoxy-glucopyranose</synonym>
    <synonym>2-Acetylamino-b-D-2-deoxy-mannopyranose</synonym>
    <synonym>2-Acetylamino-beta-D-2-deoxy-galactopyranose</synonym>
    <synonym>2-Acetylamino-beta-D-2-deoxy-glucopyranose</synonym>
    <synonym>2-Acetylamino-beta-D-2-deoxy-mannopyranose</synonym>
    <synonym>2-Acetylamino-beta-delta-2-deoxy-galactopyranose</synonym>
    <synonym>2-Acetylamino-beta-delta-2-deoxy-glucopyranose</synonym>
    <synonym>2-Acetylamino-beta-delta-2-deoxy-mannopyranose</synonym>
    <synonym>2-Acetylamino-D-2-deoxy-galactose</synonym>
    <synonym>2-Acetylamino-D-2-deoxy-glucose</synonym>
    <synonym>2-Acetylamino-D-2-deoxy-gulose</synonym>
    <synonym>2-Acetylamino-D-2-deoxy-idose</synonym>
    <synonym>2-Acetylamino-D-2-deoxy-mannose</synonym>
    <synonym>2-Acetylamino-D-2-deoxy-talose</synonym>
    <synonym>2-Acetylamino-delta-2-deoxy-galactose</synonym>
    <synonym>2-Acetylamino-delta-2-deoxy-glucose</synonym>
    <synonym>2-Acetylamino-delta-2-deoxy-gulose</synonym>
    <synonym>2-Acetylamino-delta-2-deoxy-idose</synonym>
    <synonym>2-Acetylamino-delta-2-deoxy-mannose</synonym>
    <synonym>2-Acetylamino-delta-2-deoxy-talose</synonym>
    <synonym>2-Acetylamino-L-2-deoxy-galactose</synonym>
    <synonym>2-Acetylamino-L-2-deoxy-mannose</synonym>
    <synonym>a-2-Acetamido-2-deoxy-D-galactose</synonym>
    <synonym>alpha-2-Acetamido-2-deoxy-D-galactose</synonym>
    <synonym>alpha-2-Acetamido-2-deoxy-delta-galactose</synonym>
    <synonym>GalNAc</synonym>
    <synonym>N-(2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide</synonym>
    <synonym>N-Acetyl-a-D-glucosamine</synonym>
    <synonym>N-Acetyl-alpha-D-glucosamine</synonym>
    <synonym>N-Acetyl-alpha-delta-glucosamine</synonym>
    <synonym>N-Acetyl-D-allosamine</synonym>
    <synonym>N-Acetyl-D-galactosamine</synonym>
    <synonym>N-Acetyl-delta-allosamine</synonym>
    <synonym>N-Acetyl-delta-galactosamine</synonym>
    <synonym>N-Acetylgalactosamin</synonym>
    <synonym>N-Acetylglucosamin</synonym>
    <synonym>N-Acetylgluosamin</synonym>
    <synonym>N-Acetylmannosamin</synonym>
    <synonym>2 Acetamido 2 deoxy D galactose</synonym>
    <synonym>2-Acetamido-2-D-galactopyranose</synonym>
    <synonym>Acetylgalactosamine</synonym>
    <synonym>2-Acetamido-2-deoxygalactose</synonym>
    <synonym>N Acetyl D galactosamine</synonym>
    <synonym>2 Acetamido 2 D galactopyranose</synonym>
    <synonym>2 Acetamido 2 deoxygalactose</synonym>
    <synonym>2-Acetamido-2-deoxy-D-galactose</synonym>
    <synonym>N-Acetyl-a-D-galactosamine</synonym>
    <synonym>N-Acetyl-α-D-galactosamine</synonym>
    <synonym>a-N-Acetyl-D-galactosamine</synonym>
    <synonym>Α-N-acetyl-D-galactosamine</synonym>
  </synonyms>
  <chemical_formula>C8H15NO6</chemical_formula>
  <average_molecular_weight>221.2078</average_molecular_weight>
  <monisotopic_moleculate_weight>221.089937217</monisotopic_moleculate_weight>
  <iupac_name>N-[(2S,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide</iupac_name>
  <traditional_iupac>α-GalNAc</traditional_iupac>
  <cas_registry_number>1811-31-0</cas_registry_number>
  <smiles>CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8+/m1/s1</inchi>
  <inchikey>OVRNDRQMDRJTHS-CBQIKETKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>N-acyl-alpha-hexosamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acetyl-D-galactosamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>172 - 173 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[(2S,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>221.2078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>221.089937217</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15NO6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OVRNDRQMDRJTHS-CBQIKETKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>119.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>263838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>263839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>263840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>283767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>283768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>283769</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>158.222 (126.578-370.692)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized whole milk</comment>
      <references>
        <reference>
          <reference_text>Esperanza Troyano, Mar Villamiel, Agustin Olano, Jesus Sanz, and Isabel Martinez-Castro. Monosaccharides and myo-Inositol in Commercial Milks. J. Agric. Food Chem., 1996, 44 (3), pp 815–817</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01074</kegg_id>
  <chemspider_id>76020</chemspider_id>
  <drugbank_id>DB03567</drugbank_id>
  <pdbe_id/>
  <chebi_id>40356</chebi_id>
  <pubchem_compound_id>84265</pubchem_compound_id>
  <foodb_id>FDB031022</foodb_id>
  <meta_cyc_id>CPD-3604</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>N-Acetylgalactosamine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>36880</bigg_id>
  <metlin_id>5222</metlin_id>
  <synthesis_reference>Cardini, C. E.; Leloir, Luis F.  Enzymic formation of acetylgalactosamine.    Journal of Biological Chemistry  (1957),  225  317-24.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00381</protein_accession>
      <name>Polypeptide N-acetylgalactosaminyltransferase 6</name>
      <uniprot_id>Q5EA41</uniprot_id>
      <gene_name>GALNT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00481</protein_accession>
      <name>Glycoprotein-N-acetylgalactosamine 3-beta-galactosyltransferase 1</name>
      <uniprot_id>Q0VC84</uniprot_id>
      <gene_name>C1GALT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01616</protein_accession>
      <name>Collectin-12</name>
      <uniprot_id>A6QP79</uniprot_id>
      <gene_name>COLEC12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01617</protein_accession>
      <name>Collectin-43</name>
      <uniprot_id>P42916</uniprot_id>
      <gene_name>CL43</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:49 UTC</creation_date>
  <update_date>2020-04-14 22:47:02 UTC</update_date>
  <accession>BMDB0000213</accession>
  <secondary_accessions>
    <accession>BMDB00213</accession>
  </secondary_accessions>
  <name>Myo-inositol 1-phosphate</name>
  <description>1D-Myo-inositol 1-phosphate, also known as inositol 3-phosphoric acid, belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety. 1D-Myo-inositol 1-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 1D-Myo-inositol 1-phosphate exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>1D-Myo-inositol 3-monophosphate</synonym>
    <synonym>1l-Myo-inositol 1-phosphate</synonym>
    <synonym>D-Myo-inositol 3-monophosphate</synonym>
    <synonym>Inositol 3-phosphate</synonym>
    <synonym>L-Myo-inositol 1-phosphate</synonym>
    <synonym>Myoinositol 3-phosphate</synonym>
    <synonym>Myo-inositol 3-phosphate</synonym>
    <synonym>Myo-inositol 3-monophosphate</synonym>
    <synonym>Inositol 3-monophosphate</synonym>
    <synonym>1D-Myo-inositol 3-monophosphoric acid</synonym>
    <synonym>1l-Myo-inositol 1-phosphoric acid</synonym>
    <synonym>D-Myo-inositol 3-monophosphoric acid</synonym>
    <synonym>Inositol 3-phosphoric acid</synonym>
    <synonym>L-Myo-inositol 1-phosphoric acid</synonym>
    <synonym>Myoinositol 3-phosphoric acid</synonym>
    <synonym>Myo-inositol 3-phosphoric acid</synonym>
    <synonym>Myo-inositol 3-monophosphoric acid</synonym>
    <synonym>Inositol 3-monophosphoric acid</synonym>
    <synonym>D-Myo-inositol 3-phosphoric acid</synonym>
    <synonym>Myo-inositol 1-phosphoric acid</synonym>
    <synonym>1-(Dihydrogen phosphate) DL-myo-inositol</synonym>
    <synonym>1-(Dihydrogen phosphate) myo-inositol</synonym>
    <synonym>DL-Myo-inositol 1-phosphate</synonym>
    <synonym>Myo-inositol 1-monophosphate</synonym>
    <synonym>Myo-inositol-1-phosphate</synonym>
    <synonym>Myoinositol 1-phosphate</synonym>
    <synonym>1D-Myo-inositol 1-phosphoric acid</synonym>
    <synonym>D-myo-Inositol 3-phosphate</synonym>
  </synonyms>
  <chemical_formula>C6H13O9P</chemical_formula>
  <average_molecular_weight>260.1358</average_molecular_weight>
  <monisotopic_moleculate_weight>260.029718526</monisotopic_moleculate_weight>
  <iupac_name>{[(1R,2S,3R,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>myo-inositol 1-phosphate</traditional_iupac>
  <cas_registry_number>2831-74-5</cas_registry_number>
  <smiles>O[C@H]1[C@H](O)[C@H](O)[C@H](OP(O)(O)=O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H13O9P/c7-1-2(8)4(10)6(5(11)3(1)9)15-16(12,13)14/h1-11H,(H2,12,13,14)/t1-,2-,3+,4-,5-,6-/m0/s1</inchi>
  <inchikey>INAPMGSXUVUWAF-PTQMNWPWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Inositol phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclohexanols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Cyclohexanol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Inositol phosphate</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>myo-inositol monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>195 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>333.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(1R,2S,3R,4R,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>260.1358</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>260.029718526</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@H](O)[C@H](O)[C@H](OP(O)(O)=O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O9P/c7-1-2(8)4(10)6(5(11)3(1)9)15-16(12,13)14/h1-11H,(H2,12,13,14)/t1-,2-,3+,4-,5-,6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>INAPMGSXUVUWAF-PTQMNWPWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>167.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087256</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36166</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB021907</foodb_id>
  <chemspider_id>17215924</chemspider_id>
  <pubchem_compound_id>440194</pubchem_compound_id>
  <kegg_id>C04006</kegg_id>
  <chebi_id>18169</chebi_id>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Inositol phosphate</wikipedia_id>
  <metlin_id>5223</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Klyashchitskii, B. A.; Pimenova, V. V.; Shvets, V. I.; Sokolov, S. D.; Preobrazhenskii, N. A.  Total synthesis of sn-myoinositol 1-phosphate.    Zhurnal Obshchei Khimii  (1969),  39(10),  2373.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:50 UTC</creation_date>
  <update_date>2020-04-16 20:39:03 UTC</update_date>
  <accession>BMDB0000214</accession>
  <secondary_accessions>
    <accession>BMDB00214</accession>
  </secondary_accessions>
  <name>Ornithine</name>
  <description>Ornithine, also known as (S)-ornithine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Ornithine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. it has been claimed that ornithine improves athletic performance, has anabolic effects, has wound-healing effects, and is immuno-enhancing. Ornithine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Ornithine exists in all living species, ranging from bacteria to humans. Ornithine participates in a number of enzymatic reactions, within cattle. In particular, Carbamoyl phosphate and ornithine can be converted into citrulline; which is mediated by the enzyme ornithine carbamoyltransferase, mitochondrial. In addition, Ornithine and urea can be biosynthesized from L-arginine; which is mediated by the enzyme arginase-1. In cattle, ornithine is involved in the metabolic pathway called the urea cycle pathway. Ornithine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(S)-2,5-Diaminopentanoate</synonym>
    <synonym>(S)-2,5-Diaminopentanoic acid</synonym>
    <synonym>(S)-2,5-Diaminovaleric acid</synonym>
    <synonym>(S)-alpha,delta-Diaminovaleric acid</synonym>
    <synonym>(S)-Ornithine</synonym>
    <synonym>(S)-2,5-Diaminovalerate</synonym>
    <synonym>(S)-a,delta-Diaminovalerate</synonym>
    <synonym>(S)-a,delta-Diaminovaleric acid</synonym>
    <synonym>(S)-alpha,delta-Diaminovalerate</synonym>
    <synonym>(S)-Α,δ-diaminovalerate</synonym>
    <synonym>(S)-Α,δ-diaminovaleric acid</synonym>
    <synonym>(S)-a,Δ-diaminovalerate</synonym>
    <synonym>(S)-a,Δ-diaminovaleric acid</synonym>
    <synonym>(+)-S-Ornithine</synonym>
    <synonym>(S)-a,D-Diaminovalerate</synonym>
    <synonym>(S)-a,D-Diaminovaleric acid</synonym>
    <synonym>5-Amino-L-norvaline</synonym>
    <synonym>L-(-)-Ornithine</synonym>
    <synonym>L-Ornithine</synonym>
    <synonym>2,5-Diaminopentanoic acid</synonym>
    <synonym>Ornithine dihydrochloride, (L)-isomer</synonym>
    <synonym>Ornithine hydrochloride, (D)-isomer</synonym>
    <synonym>Ornithine, (D)-isomer</synonym>
    <synonym>Ornithine, (L)-isomer</synonym>
    <synonym>2,5 Diaminopentanoic acid</synonym>
    <synonym>Ornithine monoacetate, (L)-isomer</synonym>
    <synonym>Ornithine monohydrochloride, (D)-isomer</synonym>
    <synonym>Ornithine monohydrochloride, (DL)-isomer</synonym>
    <synonym>Ornithine phosphate (1:1), (L)-isomer</synonym>
    <synonym>Ornithine sulfate (1:1), (L)-isomer</synonym>
    <synonym>Ornithine hydrochloride, (DL)-isomer</synonym>
    <synonym>Ornithine hydrochloride, (L)-isomer</synonym>
    <synonym>Ornithine monohydrobromide, (L)-isomer</synonym>
    <synonym>Ornithine, (DL)-isomer</synonym>
  </synonyms>
  <chemical_formula>C5H12N2O2</chemical_formula>
  <average_molecular_weight>132.161</average_molecular_weight>
  <monisotopic_moleculate_weight>132.089877638</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2,5-diaminopentanoic acid</iupac_name>
  <traditional_iupac>ornithine</traditional_iupac>
  <cas_registry_number>3184-13-2</cas_registry_number>
  <smiles>NCCC[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1</inchi>
  <inchikey>AHLPHDHHMVZTML-BYPYZUCNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
      <external_descriptor>ornithine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>140 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>620 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.22</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2,5-diaminopentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.161</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.089877638</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCC[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H12N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AHLPHDHHMVZTML-BYPYZUCNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>89.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>33.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37363</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>61+/-13</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>80-98</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>55.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>62-135</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>31-41</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Sadri H, von Soosten D, Meyer U, Kluess J, Danicke S, Saremi B, Sauerwein H: Plasma amino acids and metabolic profiling of dairy cows in response to a bolus duodenal infusion of leucine. PLoS One. 2017 Apr 28;12(4):e0176647. doi: 10.1371/journal.pone.0176647. eCollection 2017.</reference_text>
          <pubmed_id>28453535</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>29-32</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>270+/-63</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>984-1184</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By HPLC with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Miles ED, McBride BW, Jia Y, Liao SF, Boling JA, Bridges PJ, Matthews JC: Glutamine synthetase and alanine transaminase expression are decreased in livers of aged vs. young beef cows and GS can be upregulated by 17beta-estradiol implants. J Anim Sci. 2015 Sep;93(9):4500-9. doi: 10.2527/jas.2015-9294.</reference_text>
          <pubmed_id>26440349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>35+/-12</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2 - 15</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>80-187</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>149+/-77</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>17 +/- 7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>25 +/- 12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>38 +/- 13</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>19 +/- 12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>19 +/- 12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>16.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>25.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>58.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>15.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>15.96 +/- 14.89</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>40+/-10</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>10+/-3</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00077</kegg_id>
  <chemspider_id>6026</chemspider_id>
  <drugbank_id>DB00129</drugbank_id>
  <pdbe_id/>
  <chebi_id>15729</chebi_id>
  <pubchem_compound_id>6262</pubchem_compound_id>
  <foodb_id>FDB030969</foodb_id>
  <meta_cyc_id>ORNITHINE</meta_cyc_id>
  <knapsack_id>C00001384</knapsack_id>
  <wikipedia_id>Ornithine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>37976</bigg_id>
  <metlin_id>27</metlin_id>
  <synthesis_reference>Zhang, Peng; Zhang, Shurong; Liu, Chunqiao; Yang, Yuhong.  Method for preparing L-ornithine by enzymatic conversion.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2007),     8pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00553</protein_accession>
      <name>Arginase-1</name>
      <uniprot_id>Q2KJ64</uniprot_id>
      <gene_name>ARG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00556</protein_accession>
      <name>Glycine amidinotransferase, mitochondrial</name>
      <uniprot_id>Q2HJ74</uniprot_id>
      <gene_name>GATM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00558</protein_accession>
      <name>Arginase-2, mitochondrial</name>
      <uniprot_id>Q58DL1</uniprot_id>
      <gene_name>ARG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00922</protein_accession>
      <name>Ornithine decarboxylase</name>
      <uniprot_id>P27117</uniprot_id>
      <gene_name>ODC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00923</protein_accession>
      <name>Ornithine decarboxylase</name>
      <uniprot_id>Q2TBX3</uniprot_id>
      <gene_name>ADC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00953</protein_accession>
      <name>Ornithine carbamoyltransferase, mitochondrial</name>
      <uniprot_id>Q9N1U7</uniprot_id>
      <gene_name>OTC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01140</protein_accession>
      <name>Ornithine decarboxylase antizyme</name>
      <uniprot_id>Q56K12</uniprot_id>
      <gene_name>OAZ1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01327</protein_accession>
      <name>Ornithine aminotransferase, mitochondrial</name>
      <uniprot_id>Q3ZCF5</uniprot_id>
      <gene_name>OAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02582</protein_accession>
      <name>Solute carrier family 25 (Mitochondrial carrier</name>
      <uniprot_id>Q2KHW4</uniprot_id>
      <gene_name>SLC25A15</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:51 UTC</creation_date>
  <update_date>2020-04-16 17:53:07 UTC</update_date>
  <accession>BMDB0000215</accession>
  <secondary_accessions>
    <accession>BMDB00215</accession>
  </secondary_accessions>
  <name>N-Acetyl-D-glucosamine</name>
  <description>N-Acetyl-D-glucosamine belongs to the class of chemical entities known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetyl-D-glucosamine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-D-glucosamine participates in a number of enzymatic reactions, within cattle. In particular, N-Acetyl-D-glucosamine can be biosynthesized from chitobiose; which is catalyzed by the enzyme Beta-hexosaminidase subunit alpha. In addition, N-Acetyl-D-glucosamine can be converted into N-acetyl-D-glucosamine 6-phosphate; which is mediated by the enzyme N-acetyl-D-glucosamine kinase. In cattle, N-acetyl-D-glucosamine is involved in the metabolic pathway called the amino sugar metabolism pathway.</description>
  <synonyms>
    <synonym>2-acetamido-2-Deoxyglucose</synonym>
    <synonym>N Acetyl D glucosamine</synonym>
    <synonym>2 acetamido 2 Deoxyglucose</synonym>
    <synonym>2-acetamido-2-Deoxy-D-glucose</synonym>
    <synonym>2 acetamido 2 Deoxy D glucose</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-a-L-glucopyranose</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-α-L-glucopyranose</synonym>
  </synonyms>
  <chemical_formula>C8H15NO6</chemical_formula>
  <average_molecular_weight>221.2078</average_molecular_weight>
  <monisotopic_moleculate_weight>221.089937217</monisotopic_moleculate_weight>
  <iupac_name>N-[(2R,3S,4S,5R,6S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide</iupac_name>
  <traditional_iupac>N-[(2R,3S,4S,5R,6S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H]OC([H])([H])[C@]1([H])O[C@@]([H])(O[H])[C@@]([H])(N([H])C(=O)C([H])([H])[H])[C@]([H])(O[H])[C@@]1([H])O[H]</smiles>
  <inchi>InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8+/m0/s1</inchi>
  <inchikey>OVRNDRQMDRJTHS-DMHSOCPYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Acylaminosugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Acylaminosugar</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[(2R,3S,4S,5R,6S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>221.2078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>221.089937217</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]OC([H])([H])[C@]1([H])O[C@@]([H])(O[H])[C@@]([H])(N([H])C(=O)C([H])([H])[H])[C@]([H])(O[H])[C@@]1([H])O[H]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15NO6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OVRNDRQMDRJTHS-DMHSOCPYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>119.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1255024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1255025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1255026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1370227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1370228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1370229</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>198.908 (126.578-370.692)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized whole milk</comment>
      <references>
        <reference>
          <reference_text>Esperanza Troyano, Mar Villamiel, Agustin Olano, Jesus Sanz, and Isabel Martinez-Castro. Monosaccharides and myo-Inositol in Commercial Milks. J. Agric. Food Chem., 1996, 44 (3), pp 815–817</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>506.311</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Johan E. Hoff. Determination of N-Acetylglucosamine-1-Phosphate and N-Acetylglucosamine in Milk. June 1963, Volume 46, Issue 6, Pages 573–574</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>230.10 +/- 2.26</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Tommaso R.I. Cataldi, Massimiliano Angelotti, Giuliana Bianco. Determination of mono- and disaccharides in milk and milk products by high-performance anion-exchange chromatography with pulsed amperometric detection. Analytica Chimica Acta 485 (2003) 43–49</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>238 +/- 90</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>302 +/- 76</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>278 +/- 94</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>351 +/- 34</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>16</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>N-acetyl-D-Glucosamine act as growth factor  in rumen of cows for methogenic bacteria</comment>
      <references>
        <reference>
          <reference_text>Prins RA: Presence of growth factors for Methanobacterium ruminantium in both gram-positive and gram-negative bacteria. Antonie Van Leeuwenhoek. 1974;40(4):585-9.</reference_text>
          <pubmed_id>4219266</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id/>
  <foodb_id/>
  <pubchem_compound_id>11861101</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id>NGZ</pdbe_id>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Zhang, He; Qi, Shanlong; Yang, Shenggui.  Production of N-acetyl-D-glucosamine from chitin.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2006),     6pp. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
      <pubmed_id>27999311</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00604</protein_accession>
      <name>Beta-1,4-galactosyltransferase 1</name>
      <uniprot_id>P08037</uniprot_id>
      <gene_name>B4GALT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00640</protein_accession>
      <name>Beta-1,4-galactosyltransferase 3</name>
      <uniprot_id>Q5EA87</uniprot_id>
      <gene_name>B4GALT3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00651</protein_accession>
      <name>Protein O-linked-mannose beta-1,2-N-acetylglucosaminyltransferase 1</name>
      <uniprot_id>Q5EAB6</uniprot_id>
      <gene_name>POMGNT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00699</protein_accession>
      <name>Lysozyme C, milk isozyme</name>
      <uniprot_id>Q6B411</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00700</protein_accession>
      <name>Lysozyme C-3</name>
      <uniprot_id>Q06284</uniprot_id>
      <gene_name>LYZ3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00701</protein_accession>
      <name>Lysozyme-like protein 6</name>
      <uniprot_id>Q29RT1</uniprot_id>
      <gene_name>LYZL6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00703</protein_accession>
      <name>N-acetyl-D-glucosamine kinase</name>
      <uniprot_id>Q3SZM9</uniprot_id>
      <gene_name>NAGK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00704</protein_accession>
      <name>Lysozyme C, non-stomach isozyme</name>
      <uniprot_id>P80189</uniprot_id>
      <gene_name>LYS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00705</protein_accession>
      <name>Lysozyme C, intestinal isozyme</name>
      <uniprot_id>Q6B410</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00706</protein_accession>
      <name>N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase</name>
      <uniprot_id>P68827</uniprot_id>
      <gene_name>NAGPA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00707</protein_accession>
      <name>Lysozyme C-1</name>
      <uniprot_id>Q06285</uniprot_id>
      <gene_name>LYZ1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00708</protein_accession>
      <name>Lysozyme C, tracheal isozyme</name>
      <uniprot_id>Q27996</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00709</protein_accession>
      <name>Lysozyme C</name>
      <uniprot_id>P04421</uniprot_id>
      <gene_name>LYZ1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00710</protein_accession>
      <name>Lysozyme-like protein 1</name>
      <uniprot_id>A0JNM6</uniprot_id>
      <gene_name>LYZL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00711</protein_accession>
      <name>Sperm acrosome-associated protein 5</name>
      <uniprot_id>Q32PD6</uniprot_id>
      <gene_name>SPACA5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00712</protein_accession>
      <name>Lysozyme C-2</name>
      <uniprot_id>Q06283</uniprot_id>
      <gene_name>LYZ2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01617</protein_accession>
      <name>Collectin-43</name>
      <uniprot_id>P42916</uniprot_id>
      <gene_name>CL43</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01908</protein_accession>
      <name>Conglutinin</name>
      <uniprot_id>P23805</uniprot_id>
      <gene_name>CGN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01910</protein_accession>
      <name>Mannose-binding protein C</name>
      <uniprot_id>O02659</uniprot_id>
      <gene_name>MBL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02058</protein_accession>
      <name>Ficolin-2</name>
      <uniprot_id>Q5I2E5</uniprot_id>
      <gene_name>FCN2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02541</protein_accession>
      <name>Sperm acrosome membrane-associated protein 3</name>
      <uniprot_id>A6QQ77</uniprot_id>
      <gene_name>SPACA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:52 UTC</creation_date>
  <update_date>2020-04-16 20:38:23 UTC</update_date>
  <accession>BMDB0000216</accession>
  <secondary_accessions>
    <accession>BMDB00216</accession>
  </secondary_accessions>
  <name>Norepinephrine</name>
  <description>Norepinephrine, also known as noradrenaline or arterenol, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Norepinephrine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Norepinephrine exists in all living organisms, ranging from bacteria to humans. Norepinephrine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(-)-Arterenol</synonym>
    <synonym>(-)-Noradrenaline</synonym>
    <synonym>(-)-Norepinephrine</synonym>
    <synonym>(R)-(-)-Norepinephrine</synonym>
    <synonym>(R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol</synonym>
    <synonym>(R)-Norepinephrine</synonym>
    <synonym>4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediol</synonym>
    <synonym>Arterenol</synonym>
    <synonym>L-Noradrenaline</synonym>
    <synonym>L-NOREPINEPHRINE</synonym>
    <synonym>Noradrenaline</synonym>
    <synonym>Norepinefrina</synonym>
    <synonym>Norepinephrinum</synonym>
    <synonym>Nor adrenalin</synonym>
    <synonym>(-)-(R)-Norepinephrine</synonym>
    <synonym>(-)-alpha-(Aminomethyl)protocatechuyl alcohol</synonym>
    <synonym>(R)-Noradrenaline</synonym>
    <synonym>4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol</synonym>
    <synonym>Adrenor</synonym>
    <synonym>Aktamin</synonym>
    <synonym>L-2-Amino-1-(3,4-dihydroxyphenyl)ethanol</synonym>
    <synonym>L-3,4-Dihydroxyphenylethanolamine</synonym>
    <synonym>L-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcohol</synonym>
    <synonym>L-Arterenol</synonym>
    <synonym>Levarterenol</synonym>
    <synonym>Levoarterenol</synonym>
    <synonym>Levonor</synonym>
    <synonym>Levonoradrenaline</synonym>
    <synonym>Levonorepinephrine</synonym>
    <synonym>Levophed</synonym>
    <synonym>Nor-epirenan</synonym>
    <synonym>Noradrenalin</synonym>
    <synonym>Norartrinal</synonym>
    <synonym>Norepirenamine</synonym>
    <synonym>Sympathin e</synonym>
    <synonym>Hydrochloride, norepinephrine</synonym>
    <synonym>Levophed bitartrate</synonym>
    <synonym>Noradrénaline tartrate renaudin</synonym>
    <synonym>Norepinephrine hydrochloride, (+)-isomer</synonym>
    <synonym>Norepinephrine hydrochloride, (+,-)-isomer</synonym>
    <synonym>Norepinephrine L-tartrate (1:1), monohydrate</synonym>
    <synonym>Norepinephrine, (+,-)-isomer</synonym>
    <synonym>Renaudin brand OF norepinephrine bitartrate</synonym>
    <synonym>Bitartrate, noradrenaline</synonym>
    <synonym>Noradrenaline bitartrate</synonym>
    <synonym>Norepinephrine L-tartrate (1:1)</synonym>
    <synonym>Norepinephrine L-tartrate (1:1), (+,-)-isomer</synonym>
    <synonym>Norepinephrine L-tartrate (1:1), monohydrate, (+)-isomer</synonym>
    <synonym>Abbott brand OF levophed bitartrate</synonym>
    <synonym>Aventis brand OF norepinephrine hydrochloride</synonym>
    <synonym>Bitartrate, norepinephrine</synonym>
    <synonym>Norepinephrin D-tartrate (1:1)</synonym>
    <synonym>Norepinephrine bitartrate</synonym>
    <synonym>Norepinephrine hydrochloride</synonym>
    <synonym>Norepinephrine D-tartrate (1:1)</synonym>
    <synonym>Norepinephrine L-tartrate, (+)-isomer</synonym>
    <synonym>Tartrate renaudin, noradrénaline</synonym>
    <synonym>Bitartrate, levophed</synonym>
    <synonym>Norepinephrine L-tartrate (1:2)</synonym>
    <synonym>Norepinephrine, (+)-isomer</synonym>
    <synonym>Renaudin, noradrénaline tartrate</synonym>
    <synonym>(2S)-2-{[(1S)-5-amino-1-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]-C-hydroxycarbonimidoyl}pentyl]amino}-4-phenylbutanoate</synonym>
    <synonym>(3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate</synonym>
    <synonym>(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoate</synonym>
    <synonym>Hexadecanoyl-L-carnitine</synonym>
    <synonym>Hexadecanoylcarnitine</synonym>
    <synonym>Hexadecenoyl carnitine</synonym>
    <synonym>L-Carnitine palmitoyl ester</synonym>
    <synonym>O-Hexadecanoyl-(R)-carnitine</synonym>
    <synonym>O-Hexadecanoyl-R-carnitine</synonym>
    <synonym>Palmitoyl-L-carnitine</synonym>
    <synonym>Palmitoylcarnitine</synonym>
    <synonym>(3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoic acid</synonym>
    <synonym>(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acid</synonym>
    <synonym>(+)-Palmitoylcarnitine</synonym>
    <synonym>(3S)-3-Hexadecanoyloxy-4-(trimethylammonio)butanoate</synonym>
    <synonym>(3S)-3-Hexadecanoyloxy-4-(trimethylammonio)butanoic acid</synonym>
    <synonym>(3S)-3-Palmitoyloxy-4-(trimethylammonio)butanoate</synonym>
    <synonym>(3S)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acid</synonym>
    <synonym>3-Carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-propanaminium</synonym>
    <synonym>D-Palmitylcarnitine</synonym>
    <synonym>L(-)-Palmitylcarnitine</synonym>
    <synonym>L-Palmitoyl-L-carnitine</synonym>
    <synonym>Palmitoyl D-carnitine</synonym>
    <synonym>Palmitoyl-(-)-carnitine</synonym>
    <synonym>Palmityl-L-carnitine</synonym>
    <synonym>Palmitylcarnitine</synonym>
    <synonym>2-Oxoadipate</synonym>
    <synonym>2-Oxoadipic acid</synonym>
    <synonym>Oxoadipate</synonym>
    <synonym>2-Keto-adipate</synonym>
    <synonym>2-Ketoadipate</synonym>
    <synonym>2-Ketoadipic acid</synonym>
    <synonym>2-oxo-Hexanedioate</synonym>
    <synonym>2-oxo-Hexanedioic acid</synonym>
    <synonym>2-Oxohexanedioate</synonym>
    <synonym>2-Oxohexanedioic acid</synonym>
    <synonym>2-Oxohexanedionic acid</synonym>
    <synonym>a-Ketoadipate</synonym>
    <synonym>a-Ketoadipic acid</synonym>
    <synonym>a-Oxoadipate</synonym>
    <synonym>a-Oxoadipic acid</synonym>
    <synonym>alpha-Ketoadipate</synonym>
    <synonym>alpha-Ketoadipic acid</synonym>
    <synonym>alpha-Oxoadipate</synonym>
    <synonym>alpha-Oxoadipic acid</synonym>
    <synonym>2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide</synonym>
    <synonym>2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide</synonym>
    <synonym>Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide</synonym>
    <synonym>Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide</synonym>
    <synonym>b-NADPH</synonym>
    <synonym>b-Nicotinamide-adenine-dinucleotide-phosphorate</synonym>
    <synonym>b-Nicotinamide-adenine-dinucleotide-phosphoric acid</synonym>
    <synonym>beta-NADPH</synonym>
    <synonym>beta-Nicotinamide-adenine-dinucleotide-phosphorate</synonym>
    <synonym>beta-Nicotinamide-adenine-dinucleotide-phosphoric acid</synonym>
    <synonym>Dihydrocodehydrogenase II</synonym>
    <synonym>Dihydronicotinamide adenine dinucleotide phosphate</synonym>
    <synonym>Dihydronicotinamide adenine dinucleotide-p</synonym>
    <synonym>Dihydrotriphosphopyridine nucleotide reduced</synonym>
    <synonym>NADP-reduced</synonym>
    <synonym>Nicotinamide adenine dinucleotide phosphate - reduced</synonym>
    <synonym>Nicotinamide-adenine-dinucleotide-phosphorate</synonym>
    <synonym>Nicotinamide-adenine-dinucleotide-phosphoric acid</synonym>
    <synonym>Reduced codehydrase II</synonym>
    <synonym>Reduced coenzyme II</synonym>
    <synonym>Reduced cozymase II</synonym>
    <synonym>Reduced triphosphopyridine nucleotide</synonym>
    <synonym>Triphosphopyridine nucleotide reduced</synonym>
  </synonyms>
  <chemical_formula>C8H11NO3</chemical_formula>
  <average_molecular_weight>169.1778</average_molecular_weight>
  <monisotopic_moleculate_weight>169.073893223</monisotopic_moleculate_weight>
  <iupac_name>4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol</iupac_name>
  <traditional_iupac>norepinephrine</traditional_iupac>
  <cas_registry_number>51-41-2</cas_registry_number>
  <smiles>NC[C@H](O)C1=CC(O)=C(O)C=C1</smiles>
  <inchi>InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1</inchi>
  <inchikey>SFLSHLFXELFNJZ-QMMMGPOBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Benzenediols</sub_class>
    <direct_parent>Catechols</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Catechol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Adrenalines</external_descriptor>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>noradrenaline</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>145.2 - 146.4 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>849 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.24</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>169.1778</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>169.073893223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC[C@H](O)C1=CC(O)=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H11NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SFLSHLFXELFNJZ-QMMMGPOBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>86.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>44.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>239968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>239969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>239970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446659</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by GC-TOF/MS</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
          <pubmed_id>29197344</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00547</kegg_id>
  <chemspider_id>388394</chemspider_id>
  <drugbank_id>DB00368</drugbank_id>
  <pdbe_id/>
  <chebi_id>18357</chebi_id>
  <pubchem_compound_id>439260</pubchem_compound_id>
  <foodb_id>FDB016812</foodb_id>
  <meta_cyc_id/>
  <knapsack_id>C00001424</knapsack_id>
  <wikipedia_id>Norepinephrine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35313</bigg_id>
  <metlin_id>5226</metlin_id>
  <synthesis_reference>Goodall, McC.; Kirshner, Norman.  Biosynthesis of adrenaline and norepinephrine by sympathetic nerves and ganglia.    Circulation  (1958),  17  366-71.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
      <pubmed_id>29197344</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00655</protein_accession>
      <name>Dopamine beta-hydroxylase</name>
      <uniprot_id>P15101</uniprot_id>
      <gene_name>DBH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01811</protein_accession>
      <name>Synaptic vesicular amine transporter</name>
      <uniprot_id>Q27963</uniprot_id>
      <gene_name>SLC18A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02577</protein_accession>
      <name>Sodium-dependent noradrenaline transporter</name>
      <uniprot_id>P51143</uniprot_id>
      <gene_name>SLC6A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02578</protein_accession>
      <name>Beta-2 adrenergic receptor</name>
      <uniprot_id>Q28044</uniprot_id>
      <gene_name>ADRB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02579</protein_accession>
      <name>Beta-1 adrenergic receptor</name>
      <uniprot_id>Q9TT96</uniprot_id>
      <gene_name>ADRB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:53 UTC</creation_date>
  <update_date>2020-04-15 20:47:58 UTC</update_date>
  <accession>BMDB0000217</accession>
  <secondary_accessions>
    <accession>BMDB00217</accession>
  </secondary_accessions>
  <name>NADP</name>
  <description/>
  <synonyms>
    <synonym>Codehydrase II</synonym>
    <synonym>Codehydrogenase II</synonym>
    <synonym>Coenzyme II</synonym>
    <synonym>NAD phosphate</synonym>
    <synonym>NADP nicotinamide-adenine-dinucleotide phosphATE</synonym>
    <synonym>TPN</synonym>
    <synonym>Triphosphopyridine nucleotide</synonym>
    <synonym>NAD phosphoric acid</synonym>
    <synonym>NADP nicotinamide-adenine-dinucleotide phosphoric acid</synonym>
    <synonym>Dinucleotide phosphate, nicotinamide-adenine</synonym>
    <synonym>NADPH</synonym>
    <synonym>Nicotinamide-adenine dinucleotide phosphate</synonym>
    <synonym>Nicotinamide adenine dinucleotide phosphate</synonym>
    <synonym>Nucleotide, triphosphopyridine</synonym>
    <synonym>Phosphate, nicotinamide-adenine dinucleotide</synonym>
    <synonym>Adenine-nicotinamide dinucleotide phosphate</synonym>
    <synonym>NADP+</synonym>
    <synonym>beta-NADP</synonym>
    <synonym>beta-Nicotinamide adenine dinucleotide phosphate</synonym>
    <synonym>beta-TPN</synonym>
    <synonym>Β-nadp</synonym>
    <synonym>Β-nicotinamide adenine dinucleotide phosphate</synonym>
    <synonym>Β-TPN</synonym>
    <synonym>NADP</synonym>
  </synonyms>
  <chemical_formula>C21H28N7O17P3</chemical_formula>
  <average_molecular_weight>743.405</average_molecular_weight>
  <monisotopic_moleculate_weight>743.075452041</monisotopic_moleculate_weight>
  <iupac_name>1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium</iupac_name>
  <traditional_iupac>1-[(2R,3R,4S,5R)-5-[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium</traditional_iupac>
  <cas_registry_number>53-59-8</cas_registry_number>
  <smiles>NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1</inchi>
  <inchikey>XJLXINKUBYWONI-NNYOXOHSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Benzenediols</sub_class>
    <direct_parent>Catechols</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Catechol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Adrenalines</external_descriptor>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>noradrenaline</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>743.405</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>743.075452041</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H28N7O17P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XJLXINKUBYWONI-NNYOXOHSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>367.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>151.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>62.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Androstenedione Metabolism</name>
      <smpdb_id>SMP0087271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Degradation of Superoxides</name>
      <smpdb_id>SMP0087191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ethanol Degradation</name>
      <smpdb_id>SMP0087192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Elongation in Mitochondria</name>
      <smpdb_id>SMP0087194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutathione Metabolism</name>
      <smpdb_id>SMP0087167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>LPS and Citrate Signaling and Inflammation</name>
      <smpdb_id>SMP0120946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pterine Biosynthesis</name>
      <smpdb_id>SMP0087250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Retinol Metabolism</name>
      <smpdb_id>SMP0087260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroidogenesis</name>
      <smpdb_id>SMP0087238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ubiquinone Biosynthesis</name>
      <smpdb_id>SMP0087215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin K Metabolism</name>
      <smpdb_id>SMP0087227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448528</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>16+/-8</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>12+/-3</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00006</kegg_id>
  <chemspider_id>5674</chemspider_id>
  <drugbank_id>DB03461</drugbank_id>
  <pdbe_id/>
  <chebi_id>44409</chebi_id>
  <pubchem_compound_id>5885</pubchem_compound_id>
  <foodb_id>FDB021908</foodb_id>
  <meta_cyc_id>NADP</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Nicotinamide adenine dinucleotide phosphate</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Simon, L. M.; Kotorman, M.; Szajani, B.  Coenzyme production using immobilized enzymes.  I.  Preparation, characterization, and laboratory-scale application of an immobilized NAD+ kinase.    Enzyme and Microbial Technology  (1992),  14(12),  997-1000.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00014</protein_accession>
      <name>Lanosterol 14-alpha demethylase</name>
      <uniprot_id>Q4PJW3</uniprot_id>
      <gene_name>CYP51A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00015</protein_accession>
      <name>Catalase</name>
      <uniprot_id>P00432</uniprot_id>
      <gene_name>CAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00022</protein_accession>
      <name>Nitric oxide synthase, endothelial</name>
      <uniprot_id>P29473</uniprot_id>
      <gene_name>NOS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00042</protein_accession>
      <name>Cytochrome P450 2U1</name>
      <uniprot_id>Q0IIF9</uniprot_id>
      <gene_name>CYP2U1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00047</protein_accession>
      <name>Cytochrome b-245 light chain</name>
      <uniprot_id>O46521</uniprot_id>
      <gene_name>CYBA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00062</protein_accession>
      <name>Cytochrome P450 2E1</name>
      <uniprot_id>O18963</uniprot_id>
      <gene_name>CYP2E1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00069</protein_accession>
      <name>Nitric oxide synthase, inducible</name>
      <uniprot_id>Q27995</uniprot_id>
      <gene_name>NOS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00071</protein_accession>
      <name>3-ketodihydrosphingosine reductase</name>
      <uniprot_id>Q2KIJ5</uniprot_id>
      <gene_name>KDSR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00116</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 4</name>
      <uniprot_id>Q8SPU8</uniprot_id>
      <gene_name>DHRS4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00119</protein_accession>
      <name>Dimethylaniline monooxygenase [N-oxide-forming] 3</name>
      <uniprot_id>Q8HYJ9</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00261</protein_accession>
      <name>Squalene synthetase</name>
      <uniprot_id>Q32KR6</uniprot_id>
      <gene_name>FDFT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00356</protein_accession>
      <name>6-phosphogluconate dehydrogenase, decarboxylating</name>
      <uniprot_id>Q3ZCI4</uniprot_id>
      <gene_name>PGD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00368</protein_accession>
      <name>Fatty acid synthase</name>
      <uniprot_id>Q71SP7</uniprot_id>
      <gene_name>FASN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00379</protein_accession>
      <name>Sepiapterin reductase</name>
      <uniprot_id>Q17QK8</uniprot_id>
      <gene_name>SPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00383</protein_accession>
      <name>Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase</name>
      <uniprot_id>Q148L6</uniprot_id>
      <gene_name>DHDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00432</protein_accession>
      <name>GMP reductase 2</name>
      <uniprot_id>Q32L93</uniprot_id>
      <gene_name>GMPR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00448</protein_accession>
      <name>Isocitrate dehydrogenase [NADP], mitochondrial</name>
      <uniprot_id>Q04467</uniprot_id>
      <gene_name>IDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00501</protein_accession>
      <name>Thioredoxin reductase 2, mitochondrial</name>
      <uniprot_id>Q9N2I8</uniprot_id>
      <gene_name>TXNRD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00512</protein_accession>
      <name>Peroxisomal NADH pyrophosphatase NUDT12</name>
      <uniprot_id>Q29RH3</uniprot_id>
      <gene_name>NUDT12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00516</protein_accession>
      <name>Isocitrate dehydrogenase [NADP] cytoplasmic</name>
      <uniprot_id>Q9XSG3</uniprot_id>
      <gene_name>IDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00540</protein_accession>
      <name>Thioredoxin reductase 1, cytoplasmic</name>
      <uniprot_id>O62768</uniprot_id>
      <gene_name>TXNRD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00585</protein_accession>
      <name>Flavin reductase</name>
      <uniprot_id>P52556</uniprot_id>
      <gene_name>BLVRB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00594</protein_accession>
      <name>L-xylulose reductase</name>
      <uniprot_id>Q1JP75</uniprot_id>
      <gene_name>DCXR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00597</protein_accession>
      <name>Dihydropteridine reductase</name>
      <uniprot_id>Q3T0Z7</uniprot_id>
      <gene_name>QDPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00602</protein_accession>
      <name>Carbonyl reductase [NADPH] 1</name>
      <uniprot_id>Q3SZD7</uniprot_id>
      <gene_name>CBR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00631</protein_accession>
      <name>Alpha-aminoadipic semialdehyde synthase, mitochondrial</name>
      <uniprot_id>A8E657</uniprot_id>
      <gene_name>AASS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00689</protein_accession>
      <name>Dihydropyrimidine dehydrogenase [NADP+]</name>
      <uniprot_id>Q28007</uniprot_id>
      <gene_name>DPYD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00713</protein_accession>
      <name>Retinol dehydrogenase 8</name>
      <uniprot_id>Q9N126</uniprot_id>
      <gene_name>RDH8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00716</protein_accession>
      <name>Retinol dehydrogenase 10</name>
      <uniprot_id>Q8HZT6</uniprot_id>
      <gene_name>RDH10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00798</protein_accession>
      <name>Aldose reductase</name>
      <uniprot_id>P16116</uniprot_id>
      <gene_name>AKR1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00821</protein_accession>
      <name>Dihydrofolate reductase</name>
      <uniprot_id>P00376</uniprot_id>
      <gene_name>DHFR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00830</protein_accession>
      <name>Ecto-ADP-ribosyltransferase 5</name>
      <uniprot_id>Q0VC22</uniprot_id>
      <gene_name>ART5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00856</protein_accession>
      <name>Glutamate dehydrogenase 1, mitochondrial</name>
      <uniprot_id>P00366</uniprot_id>
      <gene_name>GLUD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00878</protein_accession>
      <name>NADPH:adrenodoxin oxidoreductase, mitochondrial</name>
      <uniprot_id>P08165</uniprot_id>
      <gene_name>FDXR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00893</protein_accession>
      <name>NADPH--cytochrome P450 reductase</name>
      <uniprot_id>Q3SYT8</uniprot_id>
      <gene_name>POR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00901</protein_accession>
      <name>Pyridine nucleotide-disulfide oxidoreductase domain-containing protein 1</name>
      <uniprot_id>A7YVH9</uniprot_id>
      <gene_name>PYROXD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00906</protein_accession>
      <name>Methylenetetrahydrofolate reductase</name>
      <uniprot_id>Q5I598</uniprot_id>
      <gene_name>MTHFR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00909</protein_accession>
      <name>NADPH-dependent diflavin oxidoreductase 1</name>
      <uniprot_id>Q1JPJ0</uniprot_id>
      <gene_name>NDOR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00910</protein_accession>
      <name>7-dehydrocholesterol reductase</name>
      <uniprot_id>Q5E9J5</uniprot_id>
      <gene_name>DHCR7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00927</protein_accession>
      <name>Estradiol 17-beta-dehydrogenase 12</name>
      <uniprot_id>Q5E9H7</uniprot_id>
      <gene_name>HSD17B12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00986</protein_accession>
      <name>Aldehyde dehydrogenase, dimeric NADP-preferring</name>
      <uniprot_id>P30907</uniprot_id>
      <gene_name>ALDH3A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00987</protein_accession>
      <name>Alcohol dehydrogenase [NADP+]</name>
      <uniprot_id>Q3ZCJ2</uniprot_id>
      <gene_name>AKR1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00992</protein_accession>
      <name>Glucose-6-phosphate 1-dehydrogenase</name>
      <uniprot_id>Q0P587</uniprot_id>
      <gene_name>H6PD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00993</protein_accession>
      <name>Prostaglandin F synthase 1</name>
      <uniprot_id>P05980</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00994</protein_accession>
      <name>Fatty acyl-CoA reductase 2</name>
      <uniprot_id>Q0P5J1</uniprot_id>
      <gene_name>FAR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00995</protein_accession>
      <name>Prostaglandin F synthase 2</name>
      <uniprot_id>P52897</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00996</protein_accession>
      <name>Delta(14)-sterol reductase</name>
      <uniprot_id>Q8WMV1</uniprot_id>
      <gene_name>TM7SF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00997</protein_accession>
      <name>Glucose-6-phosphate 1-dehydrogenase</name>
      <uniprot_id>Q5EM56</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00999</protein_accession>
      <name>GMP reductase</name>
      <uniprot_id>Q08DA2</uniprot_id>
      <gene_name>GMPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01000</protein_accession>
      <name>Trans-2-enoyl-CoA reductase, mitochondrial</name>
      <uniprot_id>Q7YS70</uniprot_id>
      <gene_name>MECR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01001</protein_accession>
      <name>NAD(P) transhydrogenase, mitochondrial</name>
      <uniprot_id>P11024</uniprot_id>
      <gene_name>NNT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01007</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 7C</name>
      <uniprot_id>Q1RMJ5</uniprot_id>
      <gene_name>DHRS7C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01008</protein_accession>
      <name>Carbonyl reductase 4</name>
      <uniprot_id>A4IFA7</uniprot_id>
      <gene_name>CBR4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01011</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 7B</name>
      <uniprot_id>Q3T0R4</uniprot_id>
      <gene_name>DHRS7B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01012</protein_accession>
      <name>Hydroxysteroid dehydrogenase-like protein 2</name>
      <uniprot_id>A4FUZ6</uniprot_id>
      <gene_name>HSDL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01013</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 12</name>
      <uniprot_id>A6QP05</uniprot_id>
      <gene_name>DHRS12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01015</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 13</name>
      <uniprot_id>Q17QU7</uniprot_id>
      <gene_name>DHRS13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01016</protein_accession>
      <name>Pyrroline-5-carboxylate reductase 3</name>
      <uniprot_id>Q58D08</uniprot_id>
      <gene_name>PYCRL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01018</protein_accession>
      <name>Pyrroline-5-carboxylate reductase 2</name>
      <uniprot_id>Q17QJ7</uniprot_id>
      <gene_name>PYCR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01019</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 9</name>
      <uniprot_id>Q8HYR6</uniprot_id>
      <gene_name>DHRS9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01024</protein_accession>
      <name>Pyrroline-5-carboxylate reductase 1, mitochondrial</name>
      <uniprot_id>Q58DT4</uniprot_id>
      <gene_name>PYCR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01027</protein_accession>
      <name>Prostaglandin reductase 1</name>
      <uniprot_id>Q3SZJ4</uniprot_id>
      <gene_name>PTGR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01029</protein_accession>
      <name>Prostaglandin reductase 2</name>
      <uniprot_id>Q32L99</uniprot_id>
      <gene_name>PTGR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01282</protein_accession>
      <name>Short chain dehydrogenase/reductase family 9C member 7</name>
      <uniprot_id>A4IFM3</uniprot_id>
      <gene_name>SDR9C7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01283</protein_accession>
      <name>Short chain dehydrogenase/reductase family 16C member 6</name>
      <uniprot_id>A5PJJ7</uniprot_id>
      <gene_name>SDR16C6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01284</protein_accession>
      <name>Quinone oxidoreductase-like protein 1</name>
      <uniprot_id>Q59A28</uniprot_id>
      <gene_name>CRYZL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01285</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 11</name>
      <uniprot_id>Q3ZBV9</uniprot_id>
      <gene_name>DHRS11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01286</protein_accession>
      <name>Hydroxysteroid 11-beta-dehydrogenase 1-like protein</name>
      <uniprot_id>Q6Q7D1</uniprot_id>
      <gene_name>HSD11B1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01287</protein_accession>
      <name>Zinc-binding alcohol dehydrogenase domain-containing protein 2</name>
      <uniprot_id>Q24K16</uniprot_id>
      <gene_name>ZADH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01288</protein_accession>
      <name>Retinol dehydrogenase 12</name>
      <uniprot_id>P59837</uniprot_id>
      <gene_name>RDH12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01289</protein_accession>
      <name>Short-chain dehydrogenase/reductase 3</name>
      <uniprot_id>O77769</uniprot_id>
      <gene_name>DHRS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01290</protein_accession>
      <name>Dihydrodiol dehydrogenase 3</name>
      <uniprot_id>P52898</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01428</protein_accession>
      <name>Cytochrome b-245 heavy chain</name>
      <uniprot_id>O46522</uniprot_id>
      <gene_name>CYBB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02619</protein_accession>
      <name>Voltage-gated potassium channel subunit beta-2</name>
      <uniprot_id>Q27955</uniprot_id>
      <gene_name>KCNAB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02684</protein_accession>
      <name>Hydroxysteroid dehydrogenase-like protein 1</name>
      <uniprot_id>A5PJF6</uniprot_id>
      <gene_name>HSDL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:55 UTC</creation_date>
  <update_date>2020-04-14 22:47:04 UTC</update_date>
  <accession>BMDB0000218</accession>
  <secondary_accessions>
    <accession>BMDB00218</accession>
  </secondary_accessions>
  <name>Orotidylic acid</name>
  <description/>
  <synonyms>
    <synonym>6-Carboxy-5'-uridylic acid</synonym>
    <synonym>Orotidine 5'-(dihydrogen phosphate)</synonym>
    <synonym>6-Carboxy-5'-uridylate</synonym>
    <synonym>Orotidine 5'-(dihydrogen phosphoric acid)</synonym>
    <synonym>Orotidylate</synonym>
    <synonym>1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-phosphono-b-D-ribofuranosyl)-4-pyrimidinecarboxylate</synonym>
    <synonym>1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-phosphono-b-D-ribofuranosyl)-4-pyrimidinecarboxylic acid</synonym>
    <synonym>1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-phosphono-beta-delta-ribofuranosyl)-4-pyrimidinecarboxylate</synonym>
    <synonym>1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-phosphono-beta-delta-ribofuranosyl)-4-pyrimidinecarboxylic acid</synonym>
    <synonym>2,6-Dioxo-3-(5-O-phosphono-beta-D-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid</synonym>
    <synonym>2,6-Dioxo-3-(5-O-phosphono-beta-delta-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid</synonym>
    <synonym>5'-(Dihydrogen phosphate) 6-carboxy-uridine</synonym>
    <synonym>5'-(Dihydrogen phosphate) orotidine</synonym>
    <synonym>5'-OMP</synonym>
    <synonym>5'-Phosphate orotidine</synonym>
    <synonym>5-(Dihydrogen phosphate)orotidine</synonym>
    <synonym>Ometoprim</synonym>
    <synonym>OMP</synonym>
    <synonym>Omp (nucleotide)</synonym>
    <synonym>Orotidine 5'-monophosphate</synonym>
    <synonym>Orotidine 5'-phosphate</synonym>
    <synonym>Orotidine monophosphate</synonym>
    <synonym>Orotidine-5'-phosphate</synonym>
  </synonyms>
  <chemical_formula>C10H13N2O11P</chemical_formula>
  <average_molecular_weight>368.1908</average_molecular_weight>
  <monisotopic_moleculate_weight>368.02569578</monisotopic_moleculate_weight>
  <iupac_name>3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid</iupac_name>
  <traditional_iupac>6-carboxy-5'-uridylic acid</traditional_iupac>
  <cas_registry_number>2149-82-8</cas_registry_number>
  <smiles>O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C(=O)NC(=O)C=C1C(O)=O</smiles>
  <inchi>InChI=1S/C10H13N2O11P/c13-5-1-3(9(16)17)12(10(18)11-5)8-7(15)6(14)4(23-8)2-22-24(19,20)21/h1,4,6-8,14-15H,2H2,(H,16,17)(H,11,13,18)(H2,19,20,21)/t4-,6-,7-,8-/m1/s1</inchi>
  <inchikey>KYOBSHFOBAOFBF-XVFCMESISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group  linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine ribonucleotides</sub_class>
    <direct_parent>Pyrimidine ribonucleoside monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidine carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Pyrimidinecarboxylic acids</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydropyrimidine carboxylic acid derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine-6-carboxylic acid</substituent>
      <substituent>Pyrimidine-6-carboxylic acid or derivatives</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>pyrimidine ribonucleoside 5'-monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>368.1908</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>368.02569578</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C(=O)NC(=O)C=C1C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H13N2O11P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H13N2O11P/c13-5-1-3(9(16)17)12(10(18)11-5)8-7(15)6(14)4(23-8)2-22-24(19,20)21/h1,4,6-8,14-15H,2H2,(H,16,17)(H,11,13,18)(H2,19,20,21)/t4-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KYOBSHFOBAOFBF-XVFCMESISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>203.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>70.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33568</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB02957</drugbank_id>
  <foodb_id>FDB031073</foodb_id>
  <kegg_id>C01103</kegg_id>
  <chemspider_id>141140</chemspider_id>
  <pubchem_compound_id>160617</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15842</chebi_id>
  <meta_cyc_id/>
  <knapsack_id>C00007583</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>36813</bigg_id>
  <wikipedia_id>Orotidine 5'-monophosphate</wikipedia_id>
  <metlin_id>5228</metlin_id>
  <synthesis_reference>Ueda, Tohru; Yamamoto, Miyako; Yamane, Akira; Imazawa, Masaoki; Inoue, Hideo.  Nucleosides and nucleotides.  XXIII.  Conversion of uridine nucleotides to the 6-cyano derivatives:  synthesis of orotidylic acid.    Journal of Carbohydrates, Nucleosides, Nucleotides  (1978),  5(3),  261-71.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01004</protein_accession>
      <name>Uridine 5'-monophosphate synthase</name>
      <uniprot_id>P31754</uniprot_id>
      <gene_name>UMPS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:56 UTC</creation_date>
  <update_date>2020-04-16 20:39:14 UTC</update_date>
  <accession>BMDB0000220</accession>
  <secondary_accessions>
    <accession>BMDB00220</accession>
  </secondary_accessions>
  <name>Palmitic acid</name>
  <description>Palmitic acid, also known as C16 or palmitate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Palmitic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Palmitic acid exists in all living species, ranging from bacteria to humans. Palmitic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Hexyldecanoic acid</synonym>
    <synonym>1-Pentadecanecarboxylic acid</synonym>
    <synonym>16:00</synonym>
    <synonym>C16</synonym>
    <synonym>C16 Fatty acid</synonym>
    <synonym>C16:0</synonym>
    <synonym>Cetylic acid</synonym>
    <synonym>CH3-[CH2]14-COOH</synonym>
    <synonym>FA 16:0</synonym>
    <synonym>Hexadecanoate</synonym>
    <synonym>Hexadecoic acid</synonym>
    <synonym>Hexadecylic acid</synonym>
    <synonym>Hexaectylic acid</synonym>
    <synonym>N-Hexadecanoic acid</synonym>
    <synonym>N-Hexadecoic acid</synonym>
    <synonym>Palmitate</synonym>
    <synonym>Palmitinic acid</synonym>
    <synonym>Palmitinsaeure</synonym>
    <synonym>Pentadecanecarboxylic acid</synonym>
    <synonym>1-Hexyldecanoate</synonym>
    <synonym>1-Pentadecanecarboxylate</synonym>
    <synonym>Cetylate</synonym>
    <synonym>Hexadecanoic acid</synonym>
    <synonym>Hexadecoate</synonym>
    <synonym>Hexadecylate</synonym>
    <synonym>Hexaectylate</synonym>
    <synonym>N-Hexadecanoate</synonym>
    <synonym>N-Hexadecoate</synonym>
    <synonym>Palmitinate</synonym>
    <synonym>Pentadecanecarboxylate</synonym>
    <synonym>Edenor C16</synonym>
    <synonym>Emersol 140</synonym>
    <synonym>Emersol 143</synonym>
    <synonym>Glycon p-45</synonym>
    <synonym>Hexadecanoate (N-C16:0)</synonym>
    <synonym>Hexadecanoic acid palmitic acid</synonym>
    <synonym>Hydrofol</synonym>
    <synonym>Hydrofol acid 1690</synonym>
    <synonym>Hystrene 8016</synonym>
    <synonym>Hystrene 9016</synonym>
    <synonym>Industrene 4516</synonym>
    <synonym>Kortacid 1698</synonym>
    <synonym>Loxiol ep 278</synonym>
    <synonym>Lunac p 95</synonym>
    <synonym>Lunac p 95KC</synonym>
    <synonym>Lunac p 98</synonym>
    <synonym>Palmitoate</synonym>
    <synonym>Palmitoic acid</synonym>
    <synonym>PAM</synonym>
    <synonym>PLM</synonym>
    <synonym>Prifac 2960</synonym>
    <synonym>Prifrac 2960</synonym>
    <synonym>Pristerene 4934</synonym>
    <synonym>Univol u332</synonym>
    <synonym>Acid, hexadecanoic</synonym>
    <synonym>Acid, palmitic</synonym>
    <synonym>FA(16:0)</synonym>
  </synonyms>
  <chemical_formula>C16H32O2</chemical_formula>
  <average_molecular_weight>256.4241</average_molecular_weight>
  <monisotopic_moleculate_weight>256.240230268</monisotopic_moleculate_weight>
  <iupac_name>hexadecanoic acid</iupac_name>
  <traditional_iupac>palmitic acid</traditional_iupac>
  <cas_registry_number>57-10-3</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)</inchi>
  <inchikey>IPCSVZSSVZVIGE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Saturated fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>61.8 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>4e-05 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.17</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>hexadecanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>256.4241</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>256.240230268</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H32O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IPCSVZSSVZVIGE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>77.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Elongation in Mitochondria</name>
      <smpdb_id>SMP0087194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373613</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>52170.21</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>57060.16</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>701466.83</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>1011294.96</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>676992.53</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>856077.1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>965197.89</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Calf-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>944139.03</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. With growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>975883.31</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Without growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>968356.72</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Yearling-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed barley silage diet for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed barley silage diet with flaxseed for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed hay for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed hay with flaxseed for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by infra-red spectroscopy and silieic acid columns</comment>
      <references>
        <reference>
          <reference_text>Laura Evans, Stuart Patton, R.D. McCarthy. Fatty Acid Composition of the Lipid Fractions from Bovine Serum Lipoproteins. J. Dairy Science (1961) 44(3) 475-482   doi: 10.3168/jds.S0022-0302(61)89765-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>104 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>54.3 +/- 2.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>47.3 +/- 2.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16691.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15989.14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3470.813</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5303.71</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3470.813</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>40167.831</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>38997.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>36658.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>90.04 +/- 12.70</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk from a Danish Holstein herd by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>106.07 +/- 14.43</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised whole milk (3.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>50.79 +/- 2.60</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised semi skimmed milk (1.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13.85 +/- 2.31</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised skimmed milk (0.1% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
          <pubmed_id>1779072</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>78.82 +/- 1.33</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>45627.554 +/- 15209.185</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
          <pubmed_id>16899705</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>124.325 +/- 0.62</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Catrienus De Jong Herman T. Badings. Determination of free fatty acids in milk and cheese procedures for extraction, clean up, and capillary gas chromatographic analysis. Journal of High Resolution Chromatography Volume 13, Issue 2, 1990</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>220.8 +/- 41.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Fat content of plain milk wasn't specified in the reference. 3.25% is an estimate.</comment>
      <references>
        <reference>
          <reference_text>Lu CY, Wu HL, Chen SH, Kou HS, Wu SM: Simple and sensitive analysis of long-chain free fatty acids in milk by fluorogenic derivatization and high-performance liquid chromatography. J Agric Food Chem. 2002 Jan 2;50(1):71-3.</reference_text>
          <pubmed_id>11754544</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>131.1 +/- 22.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Fat content of low-fat milk wasn't specified in the reference. 1-2% is an estimate.</comment>
      <references>
        <reference>
          <reference_text>Lu CY, Wu HL, Chen SH, Kou HS, Wu SM: Simple and sensitive analysis of long-chain free fatty acids in milk by fluorogenic derivatization and high-performance liquid chromatography. J Agric Food Chem. 2002 Jan 2;50(1):71-3.</reference_text>
          <pubmed_id>11754544</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>48864.381 +/- 11699.373</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>49098.368 +/- 11270.396</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>396608.587</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>458615.239</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>479284.123</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>491373.471</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples have been collected from Heifer cows.</comment>
      <references>
        <reference>
          <reference_text>Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub  2013 Jun 5.</reference_text>
          <pubmed_id>23871026</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Oocyte</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by CP9010 autosampler onto a capillary column within a CP9001 gas chromatograph in slaughtered cow ovaries.</comment>
      <references>
        <reference>
          <reference_text>McEvoy TG, Coull GD, Broadbent PJ, Hutchinson JS, Speake BK: Fatty acid composition of lipids in immature cattle, pig and sheep oocytes with intact zona pellucida. J Reprod Fertil. 2000 Jan;118(1):163-70.</reference_text>
          <pubmed_id>10793638</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>243.0 +/- 35.0</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by FAMEs/GC–MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>243.1 +/- 35.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00249</kegg_id>
  <chemspider_id>960</chemspider_id>
  <drugbank_id>DB03796</drugbank_id>
  <pdbe_id/>
  <chebi_id>15756</chebi_id>
  <pubchem_compound_id>985</pubchem_compound_id>
  <foodb_id>FDB031084</foodb_id>
  <meta_cyc_id>PALMITATE</meta_cyc_id>
  <knapsack_id>C00030479</knapsack_id>
  <wikipedia_id>Palmitic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34386</bigg_id>
  <metlin_id>187</metlin_id>
  <synthesis_reference>Xu, Yan; Ling, Li.  A method for preparing conjugated linoleic acid and palmitic acid.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2005),     5 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
      <pubmed_id>16899705</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
      <pubmed_id>9718493</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
      <pubmed_id>1779072</pubmed_id>
    </reference>
    <reference>
      <reference_text>Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.</reference_text>
      <pubmed_id>20855010</pubmed_id>
    </reference>
    <reference>
      <reference_text>Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93.</reference_text>
      <pubmed_id>5409465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.</reference_text>
      <pubmed_id>19038946</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
    </reference>
    <reference>
      <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
    </reference>
    <reference>
      <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01137</protein_accession>
      <name>Acyl-protein thioesterase 1</name>
      <uniprot_id>Q3MHR0</uniprot_id>
      <gene_name>LYPLA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01138</protein_accession>
      <name>Palmitoyl-protein thioesterase 1</name>
      <uniprot_id>P45478</uniprot_id>
      <gene_name>PPT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01341</protein_accession>
      <name>Retinal pigment epithelium-specific 65 kDa protein</name>
      <uniprot_id>Q28175</uniprot_id>
      <gene_name>RPE65</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:57 UTC</creation_date>
  <update_date>2020-04-15 20:47:59 UTC</update_date>
  <accession>BMDB0000221</accession>
  <secondary_accessions>
    <accession>BMDB00221</accession>
  </secondary_accessions>
  <name>NADPH</name>
  <description/>
  <synonyms>
    <synonym>Dihydronicotinamide-adenine dinucleotide phosphate</synonym>
    <synonym>NADPH dihydro-nicotinamide-adenine-dinucleotide phosphATE</synonym>
    <synonym>Reduced nicotinamide adenine dinucleotide phosphate</synonym>
    <synonym>Reduced nicotinamide-adenine dinucleotide phosphate</synonym>
    <synonym>TPNH</synonym>
    <synonym>Dihydronicotinamide-adenine dinucleotide phosphoric acid</synonym>
    <synonym>NADPH dihydro-nicotinamide-adenine-dinucleotide phosphoric acid</synonym>
    <synonym>Reduced nicotinamide adenine dinucleotide phosphoric acid</synonym>
    <synonym>Reduced nicotinamide-adenine dinucleotide phosphoric acid</synonym>
    <synonym>Nadph dihydro-nicotinamide-adenine-dinucleotidephosphoric acid</synonym>
    <synonym>Coenzyme II</synonym>
    <synonym>Dinucleotide phosphate, nicotinamide-adenine</synonym>
    <synonym>NADP</synonym>
    <synonym>Nicotinamide adenine dinucleotide phosphate</synonym>
    <synonym>Nicotinamide-adenine dinucleotide phosphate</synonym>
    <synonym>Nucleotide, triphosphopyridine</synonym>
    <synonym>Phosphate, nicotinamide-adenine dinucleotide</synonym>
    <synonym>Triphosphopyridine nucleotide</synonym>
    <synonym>NADPH</synonym>
    <synonym>Nicotinamide-adenine dinucleotide phosphate, reduced</synonym>
    <synonym>Reduced triphosphopyridine nucleotide</synonym>
    <synonym>Triphosphopyridine nucleotide, reduced</synonym>
    <synonym>beta-NADPH</synonym>
    <synonym>beta-Nicotinamide-adenine-dinucleotide-phosphoric acid</synonym>
    <synonym>beta-TPNH</synonym>
    <synonym>β-NADPH</synonym>
    <synonym>β-Nicotinamide-adenine-dinucleotide-phosphoric acid</synonym>
    <synonym>β-TPNH</synonym>
  </synonyms>
  <chemical_formula>C21H30N7O17P3</chemical_formula>
  <average_molecular_weight>745.4209</average_molecular_weight>
  <monisotopic_moleculate_weight>745.091102105</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>nadph</traditional_iupac>
  <cas_registry_number>53-57-6</cas_registry_number>
  <smiles>NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1</inchi>
  <inchikey>ACFIXJIJDZMPPO-NNYOXOHSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Dihydropyridinecarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Enamines</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>N-substituted nicotinamides</alternative_parent>
      <alternative_parent>Nicotinamide nucleotides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside 2',5'-bisphosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Dihydropyridine</substituent>
      <substituent>Dihydropyridinecarboxylic acid derivative</substituent>
      <substituent>Enamine</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyridine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>N-substituted nicotinamide</substituent>
      <substituent>Nicotinamide-nucleotide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside 2',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>NAD(P)H</external_descriptor>
      <external_descriptor>NADP</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>745.4209</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>745.091102105</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H30N7O17P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ACFIXJIJDZMPPO-NNYOXOHSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>364.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>153.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>63.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Androstenedione Metabolism</name>
      <smpdb_id>SMP0087271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ethanol Degradation</name>
      <smpdb_id>SMP0087192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Elongation in Mitochondria</name>
      <smpdb_id>SMP0087194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutathione Metabolism</name>
      <smpdb_id>SMP0087167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>LPS and Citrate Signaling and Inflammation</name>
      <smpdb_id>SMP0120946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pterine Biosynthesis</name>
      <smpdb_id>SMP0087250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Retinol Metabolism</name>
      <smpdb_id>SMP0087260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroidogenesis</name>
      <smpdb_id>SMP0087238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ubiquinone Biosynthesis</name>
      <smpdb_id>SMP0087215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin K Metabolism</name>
      <smpdb_id>SMP0087227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448531</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00005</kegg_id>
  <chemspider_id>5673</chemspider_id>
  <drugbank_id>DB02338</drugbank_id>
  <pubchem_compound_id>5884</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16474</chebi_id>
  <meta_cyc_id>NADPH</meta_cyc_id>
  <wikipedia_id>Nicotinamide adenine dinucleotide phosphate</wikipedia_id>
  <knapsack_id>C00019545</knapsack_id>
  <foodb_id>FDB021909</foodb_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>3691</metlin_id>
  <synthesis_reference>Seelbach, Karsten; Riebel, Bettina; Hummel, Werner; Kula, Maria-Regina; Tishkov, Vladimir I.; Egorov, Alexey M.; Wandrey, Christian; Kragl, Udo.  A novel, efficient regenerating method of NADPH using a new formate dehydrogenase.    Tetrahedron Letters  (1996),  37(9),  1377-80.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00014</protein_accession>
      <name>Lanosterol 14-alpha demethylase</name>
      <uniprot_id>Q4PJW3</uniprot_id>
      <gene_name>CYP51A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00022</protein_accession>
      <name>Nitric oxide synthase, endothelial</name>
      <uniprot_id>P29473</uniprot_id>
      <gene_name>NOS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00062</protein_accession>
      <name>Cytochrome P450 2E1</name>
      <uniprot_id>O18963</uniprot_id>
      <gene_name>CYP2E1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00069</protein_accession>
      <name>Nitric oxide synthase, inducible</name>
      <uniprot_id>Q27995</uniprot_id>
      <gene_name>NOS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00071</protein_accession>
      <name>3-ketodihydrosphingosine reductase</name>
      <uniprot_id>Q2KIJ5</uniprot_id>
      <gene_name>KDSR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00116</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 4</name>
      <uniprot_id>Q8SPU8</uniprot_id>
      <gene_name>DHRS4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00119</protein_accession>
      <name>Dimethylaniline monooxygenase [N-oxide-forming] 3</name>
      <uniprot_id>Q8HYJ9</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00356</protein_accession>
      <name>6-phosphogluconate dehydrogenase, decarboxylating</name>
      <uniprot_id>Q3ZCI4</uniprot_id>
      <gene_name>PGD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00368</protein_accession>
      <name>Fatty acid synthase</name>
      <uniprot_id>Q71SP7</uniprot_id>
      <gene_name>FASN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00379</protein_accession>
      <name>Sepiapterin reductase</name>
      <uniprot_id>Q17QK8</uniprot_id>
      <gene_name>SPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00383</protein_accession>
      <name>Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase</name>
      <uniprot_id>Q148L6</uniprot_id>
      <gene_name>DHDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00432</protein_accession>
      <name>GMP reductase 2</name>
      <uniprot_id>Q32L93</uniprot_id>
      <gene_name>GMPR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00448</protein_accession>
      <name>Isocitrate dehydrogenase [NADP], mitochondrial</name>
      <uniprot_id>Q04467</uniprot_id>
      <gene_name>IDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00501</protein_accession>
      <name>Thioredoxin reductase 2, mitochondrial</name>
      <uniprot_id>Q9N2I8</uniprot_id>
      <gene_name>TXNRD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00516</protein_accession>
      <name>Isocitrate dehydrogenase [NADP] cytoplasmic</name>
      <uniprot_id>Q9XSG3</uniprot_id>
      <gene_name>IDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00540</protein_accession>
      <name>Thioredoxin reductase 1, cytoplasmic</name>
      <uniprot_id>O62768</uniprot_id>
      <gene_name>TXNRD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00585</protein_accession>
      <name>Flavin reductase</name>
      <uniprot_id>P52556</uniprot_id>
      <gene_name>BLVRB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00594</protein_accession>
      <name>L-xylulose reductase</name>
      <uniprot_id>Q1JP75</uniprot_id>
      <gene_name>DCXR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00602</protein_accession>
      <name>Carbonyl reductase [NADPH] 1</name>
      <uniprot_id>Q3SZD7</uniprot_id>
      <gene_name>CBR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00631</protein_accession>
      <name>Alpha-aminoadipic semialdehyde synthase, mitochondrial</name>
      <uniprot_id>A8E657</uniprot_id>
      <gene_name>AASS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00689</protein_accession>
      <name>Dihydropyrimidine dehydrogenase [NADP+]</name>
      <uniprot_id>Q28007</uniprot_id>
      <gene_name>DPYD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00713</protein_accession>
      <name>Retinol dehydrogenase 8</name>
      <uniprot_id>Q9N126</uniprot_id>
      <gene_name>RDH8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00716</protein_accession>
      <name>Retinol dehydrogenase 10</name>
      <uniprot_id>Q8HZT6</uniprot_id>
      <gene_name>RDH10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00821</protein_accession>
      <name>Dihydrofolate reductase</name>
      <uniprot_id>P00376</uniprot_id>
      <gene_name>DHFR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00868</protein_accession>
      <name>Flavin containing monooxygenase 2 (Non-functional)</name>
      <uniprot_id>Q0P566</uniprot_id>
      <gene_name>FMO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00869</protein_accession>
      <name>Truncated flavin-containing monooxygenase 3</name>
      <uniprot_id>Q8HYK2</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00878</protein_accession>
      <name>NADPH:adrenodoxin oxidoreductase, mitochondrial</name>
      <uniprot_id>P08165</uniprot_id>
      <gene_name>FDXR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00880</protein_accession>
      <name>Flavin-containing monooxygenase 3</name>
      <uniprot_id>Q8HYK1</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00882</protein_accession>
      <name>Flavin-containing monooxygenase 3</name>
      <uniprot_id>Q8HYK4</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00891</protein_accession>
      <name>Flavin-containing monooxygenase 3</name>
      <uniprot_id>Q8HYK3</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00893</protein_accession>
      <name>NADPH--cytochrome P450 reductase</name>
      <uniprot_id>Q3SYT8</uniprot_id>
      <gene_name>POR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00896</protein_accession>
      <name>Flavin-containing monooxygenase 3</name>
      <uniprot_id>Q8HYK0</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00898</protein_accession>
      <name>Thioredoxin reductase 3</name>
      <uniprot_id>Q9GKW9</uniprot_id>
      <gene_name>trxr3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00910</protein_accession>
      <name>7-dehydrocholesterol reductase</name>
      <uniprot_id>Q5E9J5</uniprot_id>
      <gene_name>DHCR7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00987</protein_accession>
      <name>Alcohol dehydrogenase [NADP+]</name>
      <uniprot_id>Q3ZCJ2</uniprot_id>
      <gene_name>AKR1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00992</protein_accession>
      <name>Glucose-6-phosphate 1-dehydrogenase</name>
      <uniprot_id>Q0P587</uniprot_id>
      <gene_name>H6PD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00993</protein_accession>
      <name>Prostaglandin F synthase 1</name>
      <uniprot_id>P05980</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00994</protein_accession>
      <name>Fatty acyl-CoA reductase 2</name>
      <uniprot_id>Q0P5J1</uniprot_id>
      <gene_name>FAR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00995</protein_accession>
      <name>Prostaglandin F synthase 2</name>
      <uniprot_id>P52897</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00996</protein_accession>
      <name>Delta(14)-sterol reductase</name>
      <uniprot_id>Q8WMV1</uniprot_id>
      <gene_name>TM7SF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00997</protein_accession>
      <name>Glucose-6-phosphate 1-dehydrogenase</name>
      <uniprot_id>Q5EM56</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00998</protein_accession>
      <name>Similar to 6-phosphogluconate dehydrogenase</name>
      <uniprot_id>Q862J6</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00999</protein_accession>
      <name>GMP reductase</name>
      <uniprot_id>Q08DA2</uniprot_id>
      <gene_name>GMPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01000</protein_accession>
      <name>Trans-2-enoyl-CoA reductase, mitochondrial</name>
      <uniprot_id>Q7YS70</uniprot_id>
      <gene_name>MECR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01001</protein_accession>
      <name>NAD(P) transhydrogenase, mitochondrial</name>
      <uniprot_id>P11024</uniprot_id>
      <gene_name>NNT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01029</protein_accession>
      <name>Prostaglandin reductase 2</name>
      <uniprot_id>Q32L99</uniprot_id>
      <gene_name>PTGR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02114</protein_accession>
      <name>FMO5 protein</name>
      <uniprot_id>A6QLN7</uniprot_id>
      <gene_name>FMO5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02119</protein_accession>
      <name>FMO3 protein</name>
      <uniprot_id>Q3SZW0</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02248</protein_accession>
      <name>Ras-related C3 botulinum toxin substrate 2</name>
      <uniprot_id>Q9TU25</uniprot_id>
      <gene_name>RAC2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02249</protein_accession>
      <name>HMGCR protein</name>
      <uniprot_id>A7Z064</uniprot_id>
      <gene_name>HMGCR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02250</protein_accession>
      <name>Zeta-crystallin</name>
      <uniprot_id>O97764</uniprot_id>
      <gene_name>CRYZ</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:58 UTC</creation_date>
  <update_date>2020-04-14 22:47:05 UTC</update_date>
  <accession>BMDB0000222</accession>
  <secondary_accessions>
    <accession>BMDB00222</accession>
  </secondary_accessions>
  <name>L-Palmitoylcarnitine</name>
  <description/>
  <synonyms>
    <synonym>(3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate</synonym>
    <synonym>(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoate</synonym>
    <synonym>Hexadecanoyl-L-carnitine</synonym>
    <synonym>Hexadecanoylcarnitine</synonym>
    <synonym>Hexadecenoyl carnitine</synonym>
    <synonym>L-Carnitine palmitoyl ester</synonym>
    <synonym>O-Hexadecanoyl-(R)-carnitine</synonym>
    <synonym>O-Hexadecanoyl-R-carnitine</synonym>
    <synonym>Palmitoyl-L-carnitine</synonym>
    <synonym>Palmitoylcarnitine</synonym>
    <synonym>(3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoic acid</synonym>
    <synonym>(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acid</synonym>
    <synonym>(+)-Palmitoylcarnitine</synonym>
    <synonym>3-Carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-propanaminium</synonym>
    <synonym>L(-)-Palmitylcarnitine</synonym>
    <synonym>L-Palmitoyl-L-carnitine</synonym>
    <synonym>Palmitoyl-(-)-carnitine</synonym>
    <synonym>Palmityl-L-carnitine</synonym>
    <synonym>Palmitylcarnitine</synonym>
    <synonym>(2R)-Palmitoylcarnitine</synonym>
    <synonym>C16 Carnitine</synonym>
    <synonym>L-Palmitoylcarnitine</synonym>
  </synonyms>
  <chemical_formula>C23H45NO4</chemical_formula>
  <average_molecular_weight>399.6077</average_molecular_weight>
  <monisotopic_moleculate_weight>399.334858933</monisotopic_moleculate_weight>
  <iupac_name>(3R)-3-(hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>palmitoylcarnitine</traditional_iupac>
  <cas_registry_number>2364-67-2</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C</smiles>
  <inchi>InChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h21H,5-20H2,1-4H3/t21-/m1/s1</inchi>
  <inchikey>XOMRRQXKHMYMOC-OAQYLSRUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Acyl carnitines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl-carnitine</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fatty acyl carnitines</external_descriptor>
      <external_descriptor>Fatty acyl carnitines</external_descriptor>
      <external_descriptor>O-acyl-L-carnitine</external_descriptor>
      <external_descriptor>O-palmitoylcarnitine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R)-3-(hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>399.6077</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>399.334858933</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C23H45NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h21H,5-20H2,1-4H3/t21-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XOMRRQXKHMYMOC-OAQYLSRUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>137.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>50.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449655</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.02+/-0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>0.012+/-0.004</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>0.02+/-0.01</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.016+/-0.004</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.03 +/- 0.011</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter).</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.03 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter).</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.04 +/- 0.015</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter).</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.02 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.03 +/- 0.004</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.028</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.027</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.036</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.029</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.02 +/- 0.012</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>0.009+/-0.004</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>0.02+/-0.01</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02990</kegg_id>
  <chemspider_id>10128117</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>17490</chebi_id>
  <pubchem_compound_id>11953816</pubchem_compound_id>
  <foodb_id>FDB021910</foodb_id>
  <meta_cyc_id>CPD-419</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Palmitoylcarnitine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>40966</bigg_id>
  <metlin_id>5231</metlin_id>
  <synthesis_reference>Norum, Kaare R.  Palmityl coenzyme A-carnitine palmityltransferase. Purification from calf-liver mitochondria and some properties of the enzyme.    Biochimica et Biophysica Acta, Specialized Section on Enzymological Subjects  (1964),  89(1),  95-108.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:26:59 UTC</creation_date>
  <update_date>2020-04-15 22:13:20 UTC</update_date>
  <accession>BMDB0000223</accession>
  <secondary_accessions>
    <accession>BMDB00223</accession>
  </secondary_accessions>
  <name>Oxalacetic acid</name>
  <description>Oxalacetic acid, also known as oxaloacetate or 2-oxosuccinate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. Oxalacetic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Oxalacetic acid exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>2-Oxobutanedioic acid</synonym>
    <synonym>2-Oxosuccinic acid</synonym>
    <synonym>3-Carboxy-3-oxopropanoic acid</synonym>
    <synonym>Keto-succinic acid</synonym>
    <synonym>Ketosuccinic acid</synonym>
    <synonym>OAA</synonym>
    <synonym>Oxobutanedioic acid</synonym>
    <synonym>Oxosuccinic acid</synonym>
    <synonym>Oxaloacetic acid</synonym>
    <synonym>Keto-oxaloacetate</synonym>
    <synonym>2-Oxobutanedioate</synonym>
    <synonym>2-Oxosuccinate</synonym>
    <synonym>3-Carboxy-3-oxopropanoate</synonym>
    <synonym>Keto-succinate</synonym>
    <synonym>Ketosuccinate</synonym>
    <synonym>Oxobutanedioate</synonym>
    <synonym>Oxosuccinate</synonym>
    <synonym>Oxaloacetate</synonym>
    <synonym>Keto-oxaloacetic acid</synonym>
    <synonym>Oxalacetate</synonym>
    <synonym>2-Ketosuccinate</synonym>
    <synonym>2-Ketosuccinic acid</synonym>
    <synonym>a-Ketosuccinate</synonym>
    <synonym>a-Ketosuccinic acid</synonym>
    <synonym>alpha-Ketosuccinate</synonym>
    <synonym>alpha-Ketosuccinic acid</synonym>
    <synonym>Oxaloethanoate</synonym>
    <synonym>Oxaloethanoic acid</synonym>
    <synonym>Acid, oxaloacetic</synonym>
    <synonym>Acid, oxalacetic</synonym>
    <synonym>2 Ketosuccinic acid</synonym>
    <synonym>2 oxo Butanedioic acid</synonym>
    <synonym>2-oxo-Butanedioic acid</synonym>
  </synonyms>
  <chemical_formula>C4H4O5</chemical_formula>
  <average_molecular_weight>132.0716</average_molecular_weight>
  <monisotopic_moleculate_weight>132.005873238</monisotopic_moleculate_weight>
  <iupac_name>2-oxobutanedioic acid</iupac_name>
  <traditional_iupac>oxalacetate</traditional_iupac>
  <cas_registry_number>328-42-7</cas_registry_number>
  <smiles>OC(=O)CC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)</inchi>
  <inchikey>KHPXUQMNIQBQEV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Short-chain keto acids and derivatives</sub_class>
    <direct_parent>Short-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-dicarbonyl compounds</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Beta-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Beta-keto acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain keto acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C4-dicarboxylic acid</external_descriptor>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>oxo dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>161 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>134 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.042</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-oxobutanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.0716</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.005873238</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H4O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KHPXUQMNIQBQEV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>91.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>24.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Malate-Aspartate Shuttle</name>
      <smpdb_id>SMP0087204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37368</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7 - 24</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00036</kegg_id>
  <chemspider_id>945</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>30744</chebi_id>
  <pubchem_compound_id>970</pubchem_compound_id>
  <foodb_id>FDB031075</foodb_id>
  <meta_cyc_id>OXALACETIC_ACID</meta_cyc_id>
  <knapsack_id>C00001197</knapsack_id>
  <wikipedia_id>Oxaloacetic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33604</bigg_id>
  <metlin_id>123</metlin_id>
  <synthesis_reference>Heidelberger, Charles; Hurlbert, Robert B. The synthesis of oxalacetic acid-I-C14 and orotic acid-6-C14. Journal of the American Chemical Society (1950), 72 4704-6.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26.</reference_text>
      <pubmed_id>27236769</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00175</protein_accession>
      <name>ATP-citrate synthase</name>
      <uniprot_id>Q32PF2</uniprot_id>
      <gene_name>ACLY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00362</protein_accession>
      <name>Citrate synthase, mitochondrial</name>
      <uniprot_id>Q29RK1</uniprot_id>
      <gene_name>CS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00567</protein_accession>
      <name>Aspartate aminotransferase, cytoplasmic</name>
      <uniprot_id>P33097</uniprot_id>
      <gene_name>GOT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00569</protein_accession>
      <name>Aspartate aminotransferase, mitochondrial</name>
      <uniprot_id>P12344</uniprot_id>
      <gene_name>GOT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00571</protein_accession>
      <name>Putative aspartate aminotransferase, cytoplasmic 2</name>
      <uniprot_id>Q2T9S8</uniprot_id>
      <gene_name>GOT1L1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00615</protein_accession>
      <name>Pyruvate carboxylase, mitochondrial</name>
      <uniprot_id>Q29RK2</uniprot_id>
      <gene_name>PC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00616</protein_accession>
      <name>Malate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q32LG3</uniprot_id>
      <gene_name>MDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00617</protein_accession>
      <name>Phosphoenolpyruvate carboxykinase, cytosolic [GTP]</name>
      <uniprot_id>Q8HYZ4</uniprot_id>
      <gene_name>PPCK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00618</protein_accession>
      <name>D-aspartate oxidase</name>
      <uniprot_id>P31228</uniprot_id>
      <gene_name>DDO</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00619</protein_accession>
      <name>Malate dehydrogenase</name>
      <uniprot_id>Q58DR9</uniprot_id>
      <gene_name>MDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00620</protein_accession>
      <name>Malate dehydrogenase, cytoplasmic</name>
      <uniprot_id>Q3T145</uniprot_id>
      <gene_name>MDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00621</protein_accession>
      <name>Malate dehydrogenase</name>
      <uniprot_id>Q0QF29</uniprot_id>
      <gene_name>MDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:00 UTC</creation_date>
  <update_date>2020-04-14 22:47:06 UTC</update_date>
  <accession>BMDB0000224</accession>
  <secondary_accessions>
    <accession>BMDB00224</accession>
  </secondary_accessions>
  <name>O-Phosphoethanolamine</name>
  <description>O-Phosphoethanolamine, also known as colamine phosphoric acid or ethanolamine phosphate, belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine. O-Phosphoethanolamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. O-Phosphoethanolamine exists in all living species, ranging from bacteria to humans. O-Phosphoethanolamine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2-Amino-ethanol dihydrogen phosphate</synonym>
    <synonym>2-Amino-ethanol phosphate</synonym>
    <synonym>Colamine phosphate</synonym>
    <synonym>Colamine phosphoric acid</synonym>
    <synonym>Colaminphosphoric acid</synonym>
    <synonym>EAP</synonym>
    <synonym>Ethanolamine acid phosphate</synonym>
    <synonym>Ethanolamine O-phosphate</synonym>
    <synonym>Ethanolamine phosphate</synonym>
    <synonym>mono(2-Aminoethyl) phosphate</synonym>
    <synonym>Monoaminoethyl phosphate</synonym>
    <synonym>O-Phosphocolamine</synonym>
    <synonym>O-Phosphorylethanolamine</synonym>
    <synonym>OPE</synonym>
    <synonym>PE</synonym>
    <synonym>PEA</synonym>
    <synonym>PETN</synonym>
    <synonym>Phosphoethanolamine</synonym>
    <synonym>Phosphoric acid 2-aminoethyl phenyl ester</synonym>
    <synonym>Phosphoryl-ethanolamine</synonym>
    <synonym>2-Amino-ethanol dihydrogen phosphoric acid</synonym>
    <synonym>2-Amino-ethanol phosphoric acid</synonym>
    <synonym>Colaminphosphate</synonym>
    <synonym>Ethanolamine acid phosphoric acid</synonym>
    <synonym>Ethanolamine O-phosphoric acid</synonym>
    <synonym>Ethanolamine phosphoric acid</synonym>
    <synonym>mono(2-Aminoethyl) phosphoric acid</synonym>
    <synonym>Monoaminoethyl phosphoric acid</synonym>
    <synonym>Phosphate 2-aminoethyl phenyl ester</synonym>
    <synonym>Phosphonoethanolamine</synonym>
    <synonym>2-Amino-ethanol dihydrogen phosphate (ester)</synonym>
    <synonym>2-Aminoethanol O-phosphate</synonym>
    <synonym>2-Aminoethyl dihydrogen phosphate</synonym>
    <synonym>2-Aminoethyl dihydrogen phosphate (acd/name 4.0)</synonym>
    <synonym>2-Aminoethyl phosphate</synonym>
    <synonym>Colamine acid phosphate</synonym>
    <synonym>Colaminephosphoric acid</synonym>
    <synonym>Ethamp</synonym>
    <synonym>O-Phosphonatoethanaminium</synonym>
    <synonym>Phosphoryethanolamine</synonym>
    <synonym>Phosphorylethanolamine</synonym>
    <synonym>Phosphorylethanolamine, 3H-labeled CPD</synonym>
    <synonym>Phosphorylethanolamine magnesium (1:1) salt</synonym>
    <synonym>Phosphorylethanolamine zinc salt</synonym>
    <synonym>Phosphorylethanolamine, cobalt (2+) (1:1) salt</synonym>
    <synonym>Calcium 2-aminoethanol phosphate</synonym>
    <synonym>Phosphorylethanolamine ca (1:1) salt</synonym>
  </synonyms>
  <chemical_formula>C2H8NO4P</chemical_formula>
  <average_molecular_weight>141.063</average_molecular_weight>
  <monisotopic_moleculate_weight>141.019094261</monisotopic_moleculate_weight>
  <iupac_name>(2-aminoethoxy)phosphonic acid</iupac_name>
  <traditional_iupac>phosphorylethanolamine</traditional_iupac>
  <cas_registry_number>1071-23-4</cas_registry_number>
  <smiles>NCCOP(O)(O)=O</smiles>
  <inchi>InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)</inchi>
  <inchikey>SUHOOTKUPISOBE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic phosphoric acids and derivatives</class>
    <sub_class>Phosphate esters</sub_class>
    <direct_parent>Phosphoethanolamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoethanolamine</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>phosphoethanolamine</external_descriptor>
      <external_descriptor>primary amino compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>241 - 243 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>72 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2-aminoethoxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>141.063</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>141.019094261</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCOP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H8NO4P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SUHOOTKUPISOBE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>27.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis</name>
      <smpdb_id>SMP0072037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:0)</name>
      <smpdb_id>SMP0080430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0080431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/15:0)</name>
      <smpdb_id>SMP0080432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:0)</name>
      <smpdb_id>SMP0080433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0080434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:0)</name>
      <smpdb_id>SMP0080435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0080436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0080437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:0)</name>
      <smpdb_id>SMP0080442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0080443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:0)</name>
      <smpdb_id>SMP0080450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0080451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:0)</name>
      <smpdb_id>SMP0080457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0080458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0080459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0080460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0080461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/15:0)</name>
      <smpdb_id>SMP0080487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:0)</name>
      <smpdb_id>SMP0080488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0080489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:0)</name>
      <smpdb_id>SMP0080490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0080491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0080492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:0)</name>
      <smpdb_id>SMP0080497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0080498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:0)</name>
      <smpdb_id>SMP0080505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0080506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:0)</name>
      <smpdb_id>SMP0080512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0080513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:0)</name>
      <smpdb_id>SMP0080514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0080515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:0)</name>
      <smpdb_id>SMP0080516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0080517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0080518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:0)</name>
      <smpdb_id>SMP0080523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0080524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:0)</name>
      <smpdb_id>SMP0080531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0080532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:0)</name>
      <smpdb_id>SMP0080538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0080539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:0)</name>
      <smpdb_id>SMP0080565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0080566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0080567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:0)</name>
      <smpdb_id>SMP0080572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0080573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:0)</name>
      <smpdb_id>SMP0080580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0080581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:0)</name>
      <smpdb_id>SMP0080587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0080588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0080595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:0)</name>
      <smpdb_id>SMP0080712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0080713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:0)</name>
      <smpdb_id>SMP0080720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0080721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:0)</name>
      <smpdb_id>SMP0080727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0080728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0080765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0080772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:0)</name>
      <smpdb_id>SMP0080820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0080821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:0)</name>
      <smpdb_id>SMP0080827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0080828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0080835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:0)</name>
      <smpdb_id>SMP0080864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0080865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis</name>
      <smpdb_id>SMP0072048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:0)</name>
      <smpdb_id>SMP0082233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0082234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/15:0)</name>
      <smpdb_id>SMP0082235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:0)</name>
      <smpdb_id>SMP0082236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0082237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:0)</name>
      <smpdb_id>SMP0082238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0082239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0082240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:0)</name>
      <smpdb_id>SMP0082245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0082246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:0)</name>
      <smpdb_id>SMP0082253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0082254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:0)</name>
      <smpdb_id>SMP0082260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0082261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0082262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0082263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0082264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/15:0)</name>
      <smpdb_id>SMP0082290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:0)</name>
      <smpdb_id>SMP0082291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0082292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:0)</name>
      <smpdb_id>SMP0082293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0082294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0082295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:0)</name>
      <smpdb_id>SMP0082300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0082301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:0)</name>
      <smpdb_id>SMP0082308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0082309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:0)</name>
      <smpdb_id>SMP0082315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0082316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:0)</name>
      <smpdb_id>SMP0082317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0082318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:0)</name>
      <smpdb_id>SMP0082319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0082320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0082321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:0)</name>
      <smpdb_id>SMP0082326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0082327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:0)</name>
      <smpdb_id>SMP0082334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0082335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:0)</name>
      <smpdb_id>SMP0082341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0082342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:0)</name>
      <smpdb_id>SMP0082368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0082369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0082370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:0)</name>
      <smpdb_id>SMP0082375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0082376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:0)</name>
      <smpdb_id>SMP0082383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0082384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:0)</name>
      <smpdb_id>SMP0082390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0082391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0082398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:0)</name>
      <smpdb_id>SMP0082520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0082521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:0)</name>
      <smpdb_id>SMP0082528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0082529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:0)</name>
      <smpdb_id>SMP0082535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0082536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0082574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0082581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:0)</name>
      <smpdb_id>SMP0082629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0082630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:0)</name>
      <smpdb_id>SMP0082636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0082637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0082644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:0)</name>
      <smpdb_id>SMP0082671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0082672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440091</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>6934+/-1186</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00346</kegg_id>
  <chemspider_id>990</chemspider_id>
  <drugbank_id>DB01738</drugbank_id>
  <foodb_id>FDB031115</foodb_id>
  <pubchem_compound_id>1015</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17553</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>PHOSPHORYL-ETHANOLAMINE</meta_cyc_id>
  <wikipedia_id>Phosphorylethanolamine</wikipedia_id>
  <bigg_id>1485304</bigg_id>
  <metlin_id>5233</metlin_id>
  <synthesis_reference>Muller K; Schulz J; Oemus R  Phosphoethanolamine--a substrate of alkaline phosphatase isolated from rat calvaria.    Biomedica biochimica acta  (1989),  48(8),  495-504.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00392</protein_accession>
      <name>Ethanolamine-phosphate cytidylyltransferase</name>
      <uniprot_id>Q5EA75</uniprot_id>
      <gene_name>PCYT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:02 UTC</creation_date>
  <update_date>2020-03-13 16:19:35 UTC</update_date>
  <accession>BMDB0000225</accession>
  <secondary_accessions>
    <accession>BMDB00225</accession>
  </secondary_accessions>
  <name>Oxoadipic acid</name>
  <description>Oxoadipic acid, also known as Oxoadipic acid or oxoadipic acid, belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. Oxoadipic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Oxoadipic acid exists in all living species, ranging from bacteria to humans. Oxoadipic acid participates in a number of enzymatic reactions, within cattle. In particular, Oxoadipic acid and L-glutamic acid can be biosynthesized from aminoadipic acid and oxoglutaric acid; which is catalyzed by the enzyme kynurenine/alpha-aminoadipate aminotransferase, mitochondrial. In addition, Oxoadipic acid can be converted into carbon dioxide through its interaction with the enzyme oxoglutarate dehydrogenase complex. In cattle, oxoadipic acid is involved in the metabolic pathway called the lysine degradation pathway. Oxoadipic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2-Oxoadipate</synonym>
    <synonym>2-Oxoadipic acid</synonym>
    <synonym>Oxoadipate</synonym>
    <synonym>2-Keto-adipate</synonym>
    <synonym>2-Ketoadipate</synonym>
    <synonym>2-Ketoadipic acid</synonym>
    <synonym>2-oxo-Hexanedioate</synonym>
    <synonym>2-oxo-Hexanedioic acid</synonym>
    <synonym>2-Oxohexanedioate</synonym>
    <synonym>2-Oxohexanedioic acid</synonym>
    <synonym>2-Oxohexanedionic acid</synonym>
    <synonym>a-Ketoadipate</synonym>
    <synonym>a-Ketoadipic acid</synonym>
    <synonym>a-Oxoadipate</synonym>
    <synonym>a-Oxoadipic acid</synonym>
    <synonym>alpha-Ketoadipate</synonym>
    <synonym>alpha-Ketoadipic acid</synonym>
    <synonym>alpha-Oxoadipate</synonym>
    <synonym>alpha-Oxoadipic acid</synonym>
    <synonym>α-Ketoadipic acid</synonym>
    <synonym>α-Oxoadipic acid</synonym>
  </synonyms>
  <chemical_formula>C6H8O5</chemical_formula>
  <average_molecular_weight>160.1247</average_molecular_weight>
  <monisotopic_moleculate_weight>160.037173366</monisotopic_moleculate_weight>
  <iupac_name>2-oxohexanedioic acid</iupac_name>
  <traditional_iupac>oxoadipate</traditional_iupac>
  <cas_registry_number>3184-35-8</cas_registry_number>
  <smiles>OC(=O)CCCC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H8O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3H2,(H,8,9)(H,10,11)</inchi>
  <inchikey>FGSBNBBHOZHUBO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12  carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Medium-chain keto acids and derivatives</sub_class>
    <direct_parent>Medium-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Medium-chain keto acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>oxo dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>127 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-oxohexanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>160.1247</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>160.037173366</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H8O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H8O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3H2,(H,8,9)(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FGSBNBBHOZHUBO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>91.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>33.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440164</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00322</kegg_id>
  <chemspider_id>70</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB003362</foodb_id>
  <pubchem_compound_id>71</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15753</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00000770</knapsack_id>
  <meta_cyc_id>2K-ADIPATE</meta_cyc_id>
  <wikipedia_id/>
  <bigg_id>1485244</bigg_id>
  <metlin_id>5234</metlin_id>
  <synthesis_reference>Nelson, Randall B.; Gribble, Gordon W.  Preparation of a-ketoadipic acid. Organic Preparations and Procedures International  (1973),  5(2),  55-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00239</protein_accession>
      <name>Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial</name>
      <uniprot_id>Q5E9N4</uniprot_id>
      <gene_name>AADAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:03 UTC</creation_date>
  <update_date>2020-04-15 22:24:15 UTC</update_date>
  <accession>BMDB0000226</accession>
  <secondary_accessions>
    <accession>BMDB00226</accession>
  </secondary_accessions>
  <name>Orotic acid</name>
  <description>Orotic acid, also known as orotate or orotsaeure, belongs to the class of organic compounds known as pyrimidinecarboxylic acids. These are pyrimidines with a structure containing a carboxyl group attached to the pyrimidine ring. Orotic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Orotic acid exists in all living species, ranging from bacteria to humans. Orotic acid is a potentially toxic compound. Orotic acid has been found to be associated with several diseases known as colorectal cancer, ulcerative colitis, canavan disease, and crohn's disease; also orotic acid has been linked to the inborn metabolic disorders including lysinuric protein intolerance.</description>
  <synonyms>
    <synonym>Orotsaeure</synonym>
    <synonym>Uracil-6-carboxylic acid</synonym>
    <synonym>Uracil-6-carboxylate</synonym>
    <synonym>Orotate</synonym>
    <synonym>1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidecarboxylic acid</synonym>
    <synonym>1,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid</synonym>
    <synonym>1,2,3,6-Tetrahydro-2,6-dioxopyrimidin-4-carbonsaeure</synonym>
    <synonym>2,6-Dihydroxy-4-pyrimidinecarboxylic acid</synonym>
    <synonym>2,6-Dihydroxypyrimidine-4-carboxylic acid</synonym>
    <synonym>2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid</synonym>
    <synonym>2,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid</synonym>
    <synonym>6-Carboxy-2,4-dihydroxypyrimidine</synonym>
    <synonym>6-Carboxyuracil</synonym>
    <synonym>6-Uracilcarboxylic acid</synonym>
    <synonym>Acide orotique</synonym>
    <synonym>Acido orotico</synonym>
    <synonym>Acidum oroticum</synonym>
    <synonym>Animal galactose factor</synonym>
    <synonym>Lactinium</synonym>
    <synonym>Molkensaeure</synonym>
    <synonym>ORO</synonym>
    <synonym>Orodin</synonym>
    <synonym>Oropur</synonym>
    <synonym>Orotonin</synonym>
    <synonym>Orotonsan</synonym>
    <synonym>Orotsaure</synonym>
    <synonym>Oroturic</synonym>
    <synonym>Orotyl</synonym>
    <synonym>Uracil-6-carbosaeure</synonym>
    <synonym>Vitamin b13</synonym>
    <synonym>Whey factor</synonym>
    <synonym>Zinc orotate</synonym>
    <synonym>Orotate, zinc</synonym>
    <synonym>Acid, orotic</synonym>
    <synonym>Orotate, potassium</synonym>
    <synonym>Potassium orotate</synonym>
    <synonym>Orotate, sodium</synonym>
    <synonym>Sodium orotate</synonym>
  </synonyms>
  <chemical_formula>C5H4N2O4</chemical_formula>
  <average_molecular_weight>156.0963</average_molecular_weight>
  <monisotopic_moleculate_weight>156.017106626</monisotopic_moleculate_weight>
  <iupac_name>2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid</iupac_name>
  <traditional_iupac>orotic acid</traditional_iupac>
  <cas_registry_number>65-86-1</cas_registry_number>
  <smiles>OC(=O)C1=CC(=O)NC(=O)N1</smiles>
  <inchi>InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)</inchi>
  <inchikey>PXQPEWDEAKTCGB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidinecarboxylic acids. These are pyrimidines with a structure containing a carboxyl group attached to the pyrimidine ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazines</class>
    <sub_class>Pyrimidines and pyrimidine derivatives</sub_class>
    <direct_parent>Pyrimidinecarboxylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidine carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydropyrimidine carboxylic acid derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrimidine-6-carboxylic acid</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>pyrimidinemonocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>345.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1.82 mg/mL at 18 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.83</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>156.0963</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>156.017106626</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1=CC(=O)NC(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H4N2O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PXQPEWDEAKTCGB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>95.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>33.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448052</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>542.52 +/- 165.89</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>783</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>commercial skim milk</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Krzeminski J, Podgurniak M, Witeszczak C, Zochowski P: Variability of orotic acid concentration in cow's milk. Endocr Regul. 1991 Jun;25(1-2):79-82.</reference_text>
          <pubmed_id>1958838</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>845</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Cows had leukemia</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Krzeminski J, Podgurniak M, Witeszczak C, Zochowski P: Variability of orotic acid concentration in cow's milk. Endocr Regul. 1991 Jun;25(1-2):79-82.</reference_text>
          <pubmed_id>1958838</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>124</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Mastitis infected cows</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Krzeminski J, Podgurniak M, Witeszczak C, Zochowski P: Variability of orotic acid concentration in cow's milk. Endocr Regul. 1991 Jun;25(1-2):79-82.</reference_text>
          <pubmed_id>1958838</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>618 +/- 233</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Krzeminski J, Podgurniak M, Witeszczak C, Zochowski P: Variability of orotic acid concentration in cow's milk. Endocr Regul. 1991 Jun;25(1-2):79-82.</reference_text>
          <pubmed_id>1958838</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>192.189 - 448.442</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Indyk HE, Woollard DC: Determination of orotic acid, uric acid, and creatinine in milk by liquid chromatography. J AOAC Int. 2004 Jan-Feb;87(1):116-22.</reference_text>
          <pubmed_id>15084094</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>208 - 1002</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>700 - 1200</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W, Leontowicz H: The orotic acid concentration in the blood, milk, and urine of dairy cows fed with urea supplemented diet. Arch Tierernahr. 1986 Jun;36(6):551-6.</reference_text>
          <pubmed_id>3755899</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 54 Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
          <pubmed_id>23394630</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from Danish Holstein-Friesian (n = 456) and Jersey cows (n = 436)</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
          <pubmed_id>23182357</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>578.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw whole milk</comment>
      <references>
        <reference>
          <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
          <pubmed_id>6539345</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>53.172</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Colostrum</comment>
      <references>
        <reference>
          <reference_text>Robinson JL, Dombrowski DB, Clark JH, Shanks RD: Orotate in milk and urine of dairy cows with a partial deficiency of uridine monophosphate synthase. J Dairy Sci. 1984 May;67(5):1024-9. doi: 10.3168/jds.S0022-0302(84)81401-0.</reference_text>
          <pubmed_id>6547459</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>515.0677</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Robinson JL, Dombrowski DB, Clark JH, Shanks RD: Orotate in milk and urine of dairy cows with a partial deficiency of uridine monophosphate synthase. J Dairy Sci. 1984 May;67(5):1024-9. doi: 10.3168/jds.S0022-0302(84)81401-0.</reference_text>
          <pubmed_id>6547459</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>49.200 - 419.400</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44.</reference_text>
          <pubmed_id>7196410</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>257.534 +/- 4.484</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Carbohydrate Polymers 37 (1998) 225-229</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>581.43 +/- 134.08</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>487.36 +/- 177.47</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>418.332</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. </comment>
      <references>
        <reference>
          <reference_text>Karatas F, Aydin S, Kaygusuzoglu E, Yildiz H, Erulas FA, Ozkan Y: Ghrelin and orotic acid increased in subclinical mastitis. Arch Physiol Biochem. 2008 Jul;114(3):178-82. doi: 10.1080/13813450802180940 .</reference_text>
          <pubmed_id>18629683</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>511 +/- 45</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>542 +/- 18</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>536 +/- 19</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>565 +/- 49</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00295</kegg_id>
  <chemspider_id>942</chemspider_id>
  <drugbank_id>DB02262</drugbank_id>
  <foodb_id>FDB031072</foodb_id>
  <pubchem_compound_id>967</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16742</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00019689</knapsack_id>
  <meta_cyc_id>OROTATE</meta_cyc_id>
  <wikipedia_id>Orotic_acid</wikipedia_id>
  <bigg_id>34527</bigg_id>
  <metlin_id>318</metlin_id>
  <synthesis_reference>Mitchell, Herschel K.; Nyc, Joseph F. Intermediates in the synthesis of orotic acid from oxalacetic ester and urea. Journal of the American Chemical Society (1947), 69 674-7.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Motyl T, Krzeminski J, Podgurniak M, Witeszczak C, Zochowski P: Variability of orotic acid concentration in cow's milk. Endocr Regul. 1991 Jun;25(1-2):79-82.</reference_text>
      <pubmed_id>1958838</pubmed_id>
    </reference>
    <reference>
      <reference_text>Motyl T, Barej W, Leontowicz H: The orotic acid concentration in the blood, milk, and urine of dairy cows fed with urea supplemented diet. Arch Tierernahr. 1986 Jun;36(6):551-6.</reference_text>
      <pubmed_id>3755899</pubmed_id>
    </reference>
    <reference>
      <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
      <pubmed_id>6539345</pubmed_id>
    </reference>
    <reference>
      <reference_text>Robinson JL, Dombrowski DB, Clark JH, Shanks RD: Orotate in milk and urine of dairy cows with a partial deficiency of uridine monophosphate synthase. J Dairy Sci. 1984 May;67(5):1024-9. doi: 10.3168/jds.S0022-0302(84)81401-0.</reference_text>
      <pubmed_id>6547459</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44.</reference_text>
      <pubmed_id>7196410</pubmed_id>
    </reference>
    <reference>
      <reference_text>Indyk HE, Woollard DC: Determination of orotic acid, uric acid, and creatinine in milk by liquid chromatography. J AOAC Int. 2004 Jan-Feb;87(1):116-22.</reference_text>
      <pubmed_id>15084094</pubmed_id>
    </reference>
    <reference>
      <reference_text>Karatas F, Aydin S, Kaygusuzoglu E, Yildiz H, Erulas FA, Ozkan Y: Ghrelin and orotic acid increased in subclinical mastitis. Arch Physiol Biochem. 2008 Jul;114(3):178-82. doi: 10.1080/13813450802180940 .</reference_text>
      <pubmed_id>18629683</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
      <pubmed_id>23182357</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
      <pubmed_id>23394630</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26.</reference_text>
      <pubmed_id>27236769</pubmed_id>
    </reference>
    <reference>
      <reference_text>Carbohydrate Polymers 37 (1998) 225-229</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00093</protein_accession>
      <name>Dihydroorotate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q5E9W3</uniprot_id>
      <gene_name>DHODH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01004</protein_accession>
      <name>Uridine 5'-monophosphate synthase</name>
      <uniprot_id>P31754</uniprot_id>
      <gene_name>UMPS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:04 UTC</creation_date>
  <update_date>2020-04-15 22:18:18 UTC</update_date>
  <accession>BMDB0000227</accession>
  <secondary_accessions>
    <accession>BMDB00227</accession>
  </secondary_accessions>
  <name>Mevalonic acid</name>
  <description>(R)-Mevalonic acid, also known as DL-mevalonate or MVA, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group (R)-Mevalonic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule (R)-Mevalonic acid exists in all living species, ranging from bacteria to humans (R)-Mevalonic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>DL-Mevalonic acid</synonym>
    <synonym>MVA</synonym>
    <synonym>RS-Mevalonic acid</synonym>
    <synonym>DL-Mevalonate</synonym>
    <synonym>RS-Mevalonate</synonym>
    <synonym>Mevalonate</synonym>
    <synonym>(3Rs)-Mevalonate</synonym>
    <synonym>(3Rs)-Mevalonic acid</synonym>
    <synonym>2,4-Dideoxy-3-C-methylpentonate</synonym>
    <synonym>2,4-Dideoxy-3-C-methylpentonic acid</synonym>
    <synonym>3,5-Dihydroxy-3-methyl-valerate</synonym>
    <synonym>3,5-Dihydroxy-3-methyl-valeric acid</synonym>
    <synonym>3,5-Dihydroxy-3-methylpentanoate</synonym>
    <synonym>3,5-Dihydroxy-3-methylpentanoic acid</synonym>
    <synonym>3,5-Dihydroxy-3-methylvalerate</synonym>
    <synonym>3,5-Dihydroxy-3-methylvaleric acid</synonym>
    <synonym>b,D-Dihydroxy-b-methylvalerate</synonym>
    <synonym>b,D-Dihydroxy-b-methylvaleric acid</synonym>
    <synonym>b,D-Dihydroxy-beta-methylvalerate</synonym>
    <synonym>b,D-Dihydroxy-beta-methylvaleric acid</synonym>
    <synonym>Hiochic acid</synonym>
    <synonym>MK 91</synonym>
    <synonym>MVS</synonym>
    <synonym>Acid, mevalonic</synonym>
    <synonym>(R)-Mevalonate</synonym>
    <synonym>Mevalonic acid</synonym>
  </synonyms>
  <chemical_formula>C6H12O4</chemical_formula>
  <average_molecular_weight>148.1571</average_molecular_weight>
  <monisotopic_moleculate_weight>148.073558872</monisotopic_moleculate_weight>
  <iupac_name>3,5-dihydroxy-3-methylpentanoic acid</iupac_name>
  <traditional_iupac>RS-mevalonic acid</traditional_iupac>
  <cas_registry_number>150-97-0</cas_registry_number>
  <smiles>CC(O)(CCO)CC(O)=O</smiles>
  <inchi>InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)</inchi>
  <inchikey>KJTLQQUUPVSXIM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dihydroxy monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>24 - 27 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3,5-dihydroxy-3-methylpentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>148.1571</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>148.073558872</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(O)(CCO)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KJTLQQUUPVSXIM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333468</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fermented milk, by capillary electrophoresis-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
          <pubmed_id>26686724</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id/>
  <pubchem_compound_id>449</pubchem_compound_id>
  <chemspider_id/>
  <pdbe_id/>
  <chebi_id>25351</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Mevalonic acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Takahara, Kenji; Nakamura, Yoshio; Ohashi, Takehisa; Watanabe, Kiyoshi.  Fermentative production of mevalonic acid.    Jpn. Kokai Tokkyo Koho  (1985),     4 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
      <pubmed_id>26686724</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:05 UTC</creation_date>
  <update_date>2020-04-15 22:25:34 UTC</update_date>
  <accession>BMDB0000229</accession>
  <secondary_accessions>
    <accession>BMDB00229</accession>
  </secondary_accessions>
  <name>Nicotinamide ribotide</name>
  <description>Nicotinamide ribotide, also known as NMN or beta-NMN, belongs to the class of organic compounds known as nicotinamide ribotides. These are pyridine nucleotides, in which the pyridine base is nicotinamide or a derivative thereof. Nicotinamide ribotide is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinamide ribotide exists in all eukaryotes, ranging from yeast to humans. Nicotinamide ribotide participates in a number of enzymatic reactions, within cattle. In particular, Nicotinamide ribotide can be biosynthesized from nicotinamide riboside through the action of the enzyme cytosolic purine 5'-nucleotidase. In addition, Nicotinamide ribotide can be biosynthesized from niacinamide and phosphoribosyl pyrophosphate; which is mediated by the enzyme nicotinamide phosphoribosyltransferase. In cattle, nicotinamide ribotide is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway.</description>
  <synonyms>
    <synonym>3-(Aminocarbonyl)-1-(5-O-phosphonato-beta-D-ribofuranosyl)pyridinium</synonym>
    <synonym>3-(Aminocarbonyl)-1-(5-O-phosphono-beta-D-ribofuranosyl)pyridinium, inner salt</synonym>
    <synonym>beta-Nicotinamide D-ribonucleotide</synonym>
    <synonym>beta-Nicotinamide mononucleotide</synonym>
    <synonym>beta-Nicotinamide ribonucleotide</synonym>
    <synonym>Nicotinamide D-ribonucleotide</synonym>
    <synonym>Nicotinamide mononucleotide</synonym>
    <synonym>Nicotinamide nucleotide</synonym>
    <synonym>Nicotinamide ribonucleotide</synonym>
    <synonym>NMN</synonym>
    <synonym>3-(Aminocarbonyl)-1-(5-O-phosphonato-b-D-ribofuranosyl)pyridinium</synonym>
    <synonym>3-(Aminocarbonyl)-1-(5-O-phosphonato-β-D-ribofuranosyl)pyridinium</synonym>
    <synonym>3-(Aminocarbonyl)-1-(5-O-phosphono-b-D-ribofuranosyl)pyridinium, inner salt</synonym>
    <synonym>3-(Aminocarbonyl)-1-(5-O-phosphono-β-D-ribofuranosyl)pyridinium, inner salt</synonym>
    <synonym>b-Nicotinamide D-ribonucleotide</synonym>
    <synonym>Β-nicotinamide D-ribonucleotide</synonym>
    <synonym>b-Nicotinamide mononucleotide</synonym>
    <synonym>Β-nicotinamide mononucleotide</synonym>
    <synonym>b-Nicotinamide ribonucleotide</synonym>
    <synonym>Β-nicotinamide ribonucleotide</synonym>
    <synonym>Mononucleotide, nicotinamide</synonym>
    <synonym>3-(Aminocarbonyl)-1-(5-O-phosphono-b-D-ribofuranosyl)-pyridinium hydroxide inner salt</synonym>
    <synonym>3-(Aminocarbonyl)-1-(5-O-phosphono-b-D-ribofuranosyl)-pyridinium inner salt</synonym>
    <synonym>3-(Aminocarbonyl)-1-(5-O-phosphono-beta-delta-ribofuranosyl)-pyridinium hydroxide inner salt</synonym>
    <synonym>3-(Aminocarbonyl)-1-(5-O-phosphono-beta-delta-ribofuranosyl)-pyridinium inner salt</synonym>
    <synonym>3-Carbamoyl-1-b-D-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt</synonym>
    <synonym>3-Carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt</synonym>
    <synonym>b-D-NMN</synonym>
    <synonym>b-NMN</synonym>
    <synonym>beta-delta-NMN</synonym>
    <synonym>beta-NMN</synonym>
    <synonym>Nicotinamide ribonucleoside 5'-phosphate</synonym>
    <synonym>Bibenzoyl</synonym>
    <synonym>Diphenylethanedione</synonym>
    <synonym>Diphenylglyoxal</synonym>
    <synonym>1,2-Diphenylethane-1,2-dione</synonym>
    <synonym>Diphenylethane-1,2-dione</synonym>
    <synonym>Diphenyl-alpha-beta-ketone</synonym>
    <synonym>Phosphatidylinositol 4,5-bisphosphoric acid</synonym>
    <synonym>Diadenosine triphosphoric acid</synonym>
    <synonym>Adenosine (5')triphospho(5')adenosine</synonym>
    <synonym>Adenosine 5'-triphosphate 5'-adenosine</synonym>
    <synonym>Adenosine(3)triphosphate adenosine</synonym>
    <synonym>Adenosine(5')triphospho(5')adenosine</synonym>
    <synonym>Bis(adenosine)-5'-triphosphate</synonym>
    <synonym>p(1),p(3)-Bis(5'-adenosyl) trihydrogen triphosphate</synonym>
    <synonym>p(1),p(3)-Bis(5'-adenosyl) triphosphate</synonym>
    <synonym>p(1)-p(3)-Bis(5'-adenosyl) triphosphate</synonym>
    <synonym>P1,P3-Bis(5'-adenosyl) triphosphate</synonym>
    <synonym>Ap3a</synonym>
    <synonym>5'Ap3a</synonym>
    <synonym>p(1),(P3)-Bis(5'-adenosyl)triphosphate</synonym>
    <synonym>ApppA</synonym>
    <synonym>Tetrahydrofolate</synonym>
    <synonym>(6S)-Tetrahydrofolate</synonym>
    <synonym>(6S)-Tetrahydrofolic acid</synonym>
    <synonym>5,6,7,8-Tetrahydrofolate</synonym>
    <synonym>5,6,7,8-Tetrahydrofolic acid</synonym>
    <synonym>Tetra-H-folate</synonym>
    <synonym>Tetrahydrafolate</synonym>
    <synonym>Tetrahydropteroyl mono-L-glutamate</synonym>
    <synonym>Tetrahydropteroylglutamate</synonym>
    <synonym>1,4-Butanediamine</synonym>
    <synonym>1,4-Butylenediamine</synonym>
    <synonym>1,4-DIAMINOBUTANE</synonym>
    <synonym>1,4-Tetramethylenediamine</synonym>
    <synonym>Butane-1,4-diamine</synonym>
    <synonym>Butylenediamine</synonym>
    <synonym>H2N(CH2)4nh2</synonym>
    <synonym>Putrescin</synonym>
    <synonym>Putrescina</synonym>
    <synonym>Putreszin</synonym>
    <synonym>Tetramethylendiamin</synonym>
    <synonym>Tetramethylenediamine</synonym>
    <synonym>1,4-Butanediammonium</synonym>
    <synonym>Tetramethyldiamine</synonym>
    <synonym>1,4 Diaminobutane</synonym>
    <synonym>1,4 Butanediamine</synonym>
  </synonyms>
  <chemical_formula>C11H15N2O8P</chemical_formula>
  <average_molecular_weight>334.2192</average_molecular_weight>
  <monisotopic_moleculate_weight>334.056601978</monisotopic_moleculate_weight>
  <iupac_name>3-carbamoyl-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1lambda5-pyridin-1-ylium</iupac_name>
  <traditional_iupac>3-carbamoyl-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1lambda5-pyridin-1-ylium</traditional_iupac>
  <cas_registry_number>1094-61-7</cas_registry_number>
  <smiles>NC(=O)C1=CC=C[N+](=C1)[C@@H]1O[C@H](COP(O)([O-])=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/t7-,8-,9-,11-/m1/s1</inchi>
  <inchikey>DAYLJWODMCOQEW-TURQNECASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as nicotinamide nucleotides. These are pyridine nucleotides, in which the pyridine base is nicotinamide or a derivative thereof.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyridine nucleotides</class>
    <sub_class>Nicotinamide nucleotides</sub_class>
    <direct_parent>Nicotinamide nucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Alkyl phosphates</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Nicotinamides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Pyridinium derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Nicotinamide</substituent>
      <substituent>Nicotinamide-nucleotide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridine carboxylic acid or derivatives</substituent>
      <substituent>Pyridinium</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>nicotinamide mononucleotide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-carbamoyl-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1lambda5-pyridin-1-ylium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>334.2192</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>334.056601978</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)C1=CC=C[N+](=C1)[C@@H]1O[C@H](COP(O)([O-])=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H15N2O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/t7-,8-,9-,11-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DAYLJWODMCOQEW-TURQNECASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>166.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>70.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448077</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00455</kegg_id>
  <chemspider_id/>
  <drugbank_id/>
  <foodb_id>FDB021912</foodb_id>
  <pubchem_compound_id>14180</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16171</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00019694</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Liu, Rihe; Visscher, Johannes. A novel preparation of nicotinamide mononucleotide. Nucleosides &amp; Nucleotides (1994), 13(5), 1215-16.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00105</protein_accession>
      <name>Nicotinamide mononucleotide adenylyltransferase 1</name>
      <uniprot_id>Q0VD50</uniprot_id>
      <gene_name>NMNAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00106</protein_accession>
      <name>Nicotinamide mononucleotide adenylyltransferase 2</name>
      <uniprot_id>Q0VC59</uniprot_id>
      <gene_name>NMNAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:07 UTC</creation_date>
  <update_date>2020-04-16 17:53:08 UTC</update_date>
  <accession>BMDB0000230</accession>
  <secondary_accessions>
    <accession>BMDB00230</accession>
  </secondary_accessions>
  <name>N-Acetylneuraminic acid</name>
  <description>N-Acetylneuraminic acid, also known as N-acetylneuraminate or sialic acid, belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. N-Acetylneuraminic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. N-Acetylneuraminic acid exists in all living organisms, ranging from bacteria to humans. N-Acetylneuraminic acid participates in a number of enzymatic reactions, within cattle. In particular, N-Acetylneuraminic acid can be biosynthesized from N-acetylmannosamine and phosphoenolpyruvic acid; which is catalyzed by the enzyme sialic acid synthase. In addition, N-Acetylneuraminic acid can be converted into N-acetylmannosamine and pyruvic acid; which is mediated by the enzyme N-acetylneuraminate lyase. In cattle, N-acetylneuraminic acid is involved in the metabolic pathway called the amino sugar metabolism pathway. N-Acetylneuraminic acid is a potentially toxic compound. N-Acetylneuraminic acid has been found to be associated with several diseases known as sialidosis, normosomatic type, irritable bowel syndrome, ulcerative colitis, and colorectal cancer; also n-acetylneuraminic acid has been linked to the inborn metabolic disorders including salla disease.</description>
  <synonyms>
    <synonym>5-N-ACETYL-BETA-D-neuraminIC ACID</synonym>
    <synonym>beta-Neu5ac</synonym>
    <synonym>5-N-ACETYL-b-D-neuraminate</synonym>
    <synonym>5-N-ACETYL-b-D-neuraminic acid</synonym>
    <synonym>5-N-ACETYL-beta-D-neuraminate</synonym>
    <synonym>5-N-ACETYL-β-D-neuraminate</synonym>
    <synonym>5-N-ACETYL-β-D-neuraminic acid</synonym>
    <synonym>b-Neu5ac</synonym>
    <synonym>Β-neu5ac</synonym>
    <synonym>N-Acetylneuraminate</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonate</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonic acid</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonate</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonate</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonic acid</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-delta-glycero-delta-galacto-2-nonulosonate</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-delta-glycero-delta-galacto-2-nonulosonic acid</synonym>
    <synonym>5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonate</synonym>
    <synonym>5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid</synonym>
    <synonym>5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulosonate</synonym>
    <synonym>5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulosonic acid</synonym>
    <synonym>5-N-Acetyl-beta-delta-neuraminic acid</synonym>
    <synonym>5-N-Acetyl-D-neuraminate</synonym>
    <synonym>5-N-Acetyl-D-neuraminic acid</synonym>
    <synonym>5-N-Acetyl-delta-neuraminate</synonym>
    <synonym>5-N-Acetyl-delta-neuraminic acid</synonym>
    <synonym>5-N-Acetylneuraminate</synonym>
    <synonym>5-N-Acetylneuraminic acid</synonym>
    <synonym>Aceneuramate</synonym>
    <synonym>Aceneuramic acid</synonym>
    <synonym>Acetylneuraminate</synonym>
    <synonym>Acetylneuraminic acid</synonym>
    <synonym>b-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulopyranosonate</synonym>
    <synonym>b-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulopyranosonic acid</synonym>
    <synonym>b-Sialic acid</synonym>
    <synonym>beta-5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulopyranosonate</synonym>
    <synonym>beta-5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulopyranosonic acid</synonym>
    <synonym>beta-Sialic acid</synonym>
    <synonym>Lactaminate</synonym>
    <synonym>Lactaminic acid</synonym>
    <synonym>N-Acetyl-b-D-neuraminate</synonym>
    <synonym>N-Acetyl-b-D-neuraminic acid</synonym>
    <synonym>N-Acetyl-b-neuraminate</synonym>
    <synonym>N-Acetyl-beta-delta-neuraminate</synonym>
    <synonym>N-Acetyl-beta-delta-neuraminic acid</synonym>
    <synonym>N-Acetyl-beta-neuraminate</synonym>
    <synonym>N-Acetyl-D-neuraminate</synonym>
    <synonym>N-Acetyl-D-neuraminic acid</synonym>
    <synonym>N-Acetyl-delta-neuraminate</synonym>
    <synonym>N-Acetyl-delta-neuraminic acid</synonym>
    <synonym>N-Acetyl-neuraminate</synonym>
    <synonym>N-Acetyl-neuraminic acid</synonym>
    <synonym>N-Acetylneuramate</synonym>
    <synonym>N-Acetylneuramic acid</synonym>
    <synonym>N-Acetylsialate</synonym>
    <synonym>N-Acetylsialic acid</synonym>
    <synonym>NAN</synonym>
    <synonym>NANA</synonym>
    <synonym>Neu5ac</synonym>
    <synonym>Sialic acid</synonym>
    <synonym>Acid, sialic</synonym>
    <synonym>Acid, N-acetylneuraminic</synonym>
    <synonym>N Acetylneuraminic acid</synonym>
    <synonym>N-Acetyl-beta-D-neuraminic acid</synonym>
    <synonym>N-Acetyl-beta-neuraminic acid</synonym>
    <synonym>N-Acetyl-β-D-neuraminic acid</synonym>
    <synonym>N-Acetyl-β-neuraminic acid</synonym>
    <synonym>N-Acetylneuraminic acid</synonym>
  </synonyms>
  <chemical_formula>C11H19NO9</chemical_formula>
  <average_molecular_weight>309.2699</average_molecular_weight>
  <monisotopic_moleculate_weight>309.105981211</monisotopic_moleculate_weight>
  <iupac_name>(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>β-neu5ac</traditional_iupac>
  <cas_registry_number>19342-33-7</cas_registry_number>
  <smiles>[H][C@]1(O[C@@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO</smiles>
  <inchi>InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11-/m0/s1</inchi>
  <inchikey>SQVRNKJHWKZAKO-PFQGKNLYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>N-acylneuraminic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>C-glucuronides</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Neuraminic acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>C-glucuronide</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acylneuraminic acid</substituent>
      <substituent>Neuraminic acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acetylneuraminic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>186 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>309.2699</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>309.105981211</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(O[C@@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H19NO9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SQVRNKJHWKZAKO-PFQGKNLYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>176.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>63.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>27.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281972</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>462.379</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw . mid lactation</comment>
      <references>
        <reference>
          <reference_text>The N-acetyl neuraminic-acid content of the milk of various species Journal of Dairy Research (1973), 40: 421-425 Cambridge University Press doi: 10.1017/S0022029900014795 (About doi) </reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32.334 - 42.0345</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Average over the milking season </comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C19910</kegg_id>
  <chemspider_id>392810</chemspider_id>
  <drugbank_id>DB04265</drugbank_id>
  <foodb_id/>
  <pubchem_compound_id>445063</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>45744</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>N-Acetylneuraminic acid</wikipedia_id>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Yamamoto, Toshihiro; Teshima, Tadashi; Inami, Kaoru; Shiba, Tetsuo. Synthesis of sialic acid through aldol condensation of glucose with oxalacetic acid. Tetrahedron Letters (1992), 33(3), 325-8.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>The N-acetyl neuraminic-acid content of the milk of various species Journal of Dairy Research (1973), 40: 421-425 Cambridge University Press doi: 10.1017/S0022029900014795 (About doi) </reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00109</protein_accession>
      <name>N-acetylneuraminate lyase</name>
      <uniprot_id>Q29RY9</uniprot_id>
      <gene_name>NPL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00951</protein_accession>
      <name>Sialidase-3</name>
      <uniprot_id>O97859</uniprot_id>
      <gene_name>NEU3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00952</protein_accession>
      <name>Sialidase-1</name>
      <uniprot_id>A6BMK7</uniprot_id>
      <gene_name>NEU1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02181</protein_accession>
      <name>Selectin P</name>
      <uniprot_id>A6QPF9</uniprot_id>
      <gene_name>SELP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02182</protein_accession>
      <name>C-C chemokine receptor type 5</name>
      <uniprot_id>Q2HJ17</uniprot_id>
      <gene_name>CCR5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:08 UTC</creation_date>
  <update_date>2020-04-16 20:36:50 UTC</update_date>
  <accession>BMDB0000232</accession>
  <secondary_accessions>
    <accession>BMDB00232</accession>
  </secondary_accessions>
  <name>Quinolinic acid</name>
  <description>Quinolinic acid, also known as quinolinic acid, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. Quinolinic acid exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Quinolinic acid exists in all living species, ranging from bacteria to humans. Quinolinic acid and phosphoribosyl pyrophosphate can be biosynthesized from nicotinic acid mononucleotide through the action of the enzyme nicotinate-nucleotide pyrophosphorylase [carboxylating]. In cattle, quinolinic acid is involved in a couple of metabolic pathways, which include the tryptophan metabolism pathway and the nicotinate and nicotinamide metabolism pathway.</description>
  <synonyms>
    <synonym>2,3-Pyridinedicarboxylic acid</synonym>
    <synonym>Pyridine-2,3-dicarboxylate</synonym>
    <synonym>2,3-Pyridinedicarboxylate</synonym>
    <synonym>Pyridine-2,3-dicarboxylic acid</synonym>
    <synonym>Quinolinate</synonym>
    <synonym>3,4-Pyridinedicarboxylic acid</synonym>
    <synonym>Pyridin-2,3-dicarbonsaeure</synonym>
    <synonym>Pyridine-2,3-carboxylate</synonym>
    <synonym>Pyridine-3,4-dicarboxylic acid</synonym>
    <synonym>Quinolinic acid, disodium salt</synonym>
    <synonym>Quinolinic acid, copper(2+) salt</synonym>
    <synonym>Quinolinic acid, strontium salt</synonym>
  </synonyms>
  <chemical_formula>C7H5NO4</chemical_formula>
  <average_molecular_weight>167.1189</average_molecular_weight>
  <monisotopic_moleculate_weight>167.021857653</monisotopic_moleculate_weight>
  <iupac_name>pyridine-2,3-dicarboxylic acid</iupac_name>
  <traditional_iupac>quinolinic acid</traditional_iupac>
  <cas_registry_number>89-00-9</cas_registry_number>
  <smiles>OC(=O)C1=CC=CN=C1C(O)=O</smiles>
  <inchi>InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)</inchi>
  <inchikey>GJAWHXHKYYXBSV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyridinecarboxylic acids and derivatives</sub_class>
    <direct_parent>Pyridinecarboxylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine carboxylic acid</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>pyridinedicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>190 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>11.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>pyridine-2,3-dicarboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>167.1189</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>167.021857653</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1=CC=CN=C1C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H5NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GJAWHXHKYYXBSV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>87.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438353</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03722</kegg_id>
  <chemspider_id>1037</chemspider_id>
  <drugbank_id>DB01796</drugbank_id>
  <foodb_id>FDB031142</foodb_id>
  <pubchem_compound_id>1066</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16675</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007381</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Quinolinic_acid</wikipedia_id>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Akhmerova, S. G.; Islamgulova, V. R.; Koksharov, V. G.; Sapozhnikov, Yu. E.; Manaeva, R. M.  Methods of preparation of quinolinic acid.    Bashkirskii Khimicheskii Zhurnal  (2001),  8(2),  9-14.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00636</protein_accession>
      <name>Nicotinate-nucleotide pyrophosphorylase [carboxylating]</name>
      <uniprot_id>Q3T063</uniprot_id>
      <gene_name>QPRT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:09 UTC</creation_date>
  <update_date>2020-04-16 21:05:26 UTC</update_date>
  <accession>BMDB0000234</accession>
  <secondary_accessions>
    <accession>BMDB00234</accession>
  </secondary_accessions>
  <name>Testosterone</name>
  <description>Testosterone belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, testosterone is considered to be a steroid lipid molecule. Testosterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Testosterone exists in all living organisms, ranging from bacteria to humans. Testosterone participates in a number of enzymatic reactions, within cattle. In particular, Testosterone can be converted into 19-hydroxytestosterone; which is catalyzed by the enzyme cytochrome P450 19A1. In addition, Testosterone can be converted into androstenedione; which is catalyzed by the enzyme testosterone 17-beta-dehydrogenase 3. In cattle, testosterone is involved in the metabolic pathway called the androgen and estrogen metabolism pathway. Testosterone is a potentially toxic compound.</description>
  <synonyms>
    <synonym>17beta-Hydroxy-4-androsten-3-one</synonym>
    <synonym>4-Androsten-17beta-ol-3-one</synonym>
    <synonym>Androderm</synonym>
    <synonym>Testosteron</synonym>
    <synonym>Testosterona</synonym>
    <synonym>Testosteronum</synonym>
    <synonym>Androgel</synonym>
    <synonym>Axiron</synonym>
    <synonym>Striant</synonym>
    <synonym>Testim</synonym>
    <synonym>17b-Hydroxy-4-androsten-3-one</synonym>
    <synonym>17Β-hydroxy-4-androsten-3-one</synonym>
    <synonym>4-Androsten-17b-ol-3-one</synonym>
    <synonym>4-Androsten-17β-ol-3-one</synonym>
    <synonym>(+)-Testosterone</synonym>
    <synonym>(+-)-8-Iso-testosterone</synonym>
    <synonym>(+-)-Retrotestosterone</synonym>
    <synonym>(+-)-Testosterone</synonym>
    <synonym>(17b)-17-Hydroxy-androst-4-en-3-one</synonym>
    <synonym>13-Iso-testosterone</synonym>
    <synonym>17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one</synonym>
    <synonym>17-Hydroxy-androst-4-en-3-one</synonym>
    <synonym>17-Hydroxy-D4-androsten-3-one</synonym>
    <synonym>17a-Hydroxy-(13a)-androst-4-en-3-one</synonym>
    <synonym>17a-Hydroxy-13a-androst-4-en-3-one</synonym>
    <synonym>17a-Hydroxy-14b-androst-4-en-3-one</synonym>
    <synonym>17a-Hydroxy-androst-4-en-3-one</synonym>
    <synonym>17b-Hydroxy-(10a)-androst-4-en-3-one</synonym>
    <synonym>17b-Hydroxy-(13a)-androst-4-en-3-one</synonym>
    <synonym>17b-Hydroxy-(8a)-androst-4-en-3-one</synonym>
    <synonym>17b-Hydroxy-(8a,10a)-androst-4-en-3-one</synonym>
    <synonym>17b-Hydroxy-(9b)-androst-4-en-3-one</synonym>
    <synonym>17b-Hydroxy-(9b,10a)-androst-4-en-3-one</synonym>
    <synonym>17b-Hydroxy-13a-androst-4-en-3-one</synonym>
    <synonym>17b-Hydroxy-8a-androst-4-en-3-one</synonym>
    <synonym>17b-Hydroxy-androst-4-en-3-ON</synonym>
    <synonym>17b-Hydroxy-androst-4-en-3-one</synonym>
    <synonym>17b-Hydroxy-D4-androsten-3-one</synonym>
    <synonym>17b-Hydroxyandrost-4-en-3-one</synonym>
    <synonym>17b-Hydroxyandrost-4-ene-3-one</synonym>
    <synonym>17b-Testosterone</synonym>
    <synonym>4-Androsten-3-one-17b-ol</synonym>
    <synonym>8-Iso-testosterone</synonym>
    <synonym>9b,10a-Testosterone</synonym>
    <synonym>9b-Testosterone</synonym>
    <synonym>Androlin</synonym>
    <synonym>Andronaq</synonym>
    <synonym>Andropatch</synonym>
    <synonym>Androst-4-en-17b-ol-3-one</synonym>
    <synonym>Androst-4-ene-17b-ol-3-one</synonym>
    <synonym>Andrusol</synonym>
    <synonym>Cristerona T</synonym>
    <synonym>D4-Androsten-17b-ol-3-one</synonym>
    <synonym>Epitestosteron</synonym>
    <synonym>Geno-cristaux gremy</synonym>
    <synonym>Homosteron</synonym>
    <synonym>Homosterone</synonym>
    <synonym>Lumitestosteron</synonym>
    <synonym>Mertestate</synonym>
    <synonym>Neotestis</synonym>
    <synonym>Oreton</synonym>
    <synonym>Orquisteron</synonym>
    <synonym>Perandren</synonym>
    <synonym>Percutacrine androgenique</synonym>
    <synonym>Primotest</synonym>
    <synonym>Primoteston</synonym>
    <synonym>rac-17b-Hydroxy-(13a)androst-4-en-3-one</synonym>
    <synonym>rac-17b-Hydroxy-(8a)-androst-4-en-3-one</synonym>
    <synonym>rac-17b-Hydroxy-(9b,10a)androst-4-en-3-one</synonym>
    <synonym>rac-17b-Hydroxy-androst-4-en-3-one</synonym>
    <synonym>Relibra</synonym>
    <synonym>Retrotestosterone</synonym>
    <synonym>Sustanon</synonym>
    <synonym>Sustanone</synonym>
    <synonym>Sustason 250</synonym>
    <synonym>Synandrol F</synonym>
    <synonym>Teslen</synonym>
    <synonym>Testandrone</synonym>
    <synonym>Testiculosterone</synonym>
    <synonym>Testobase</synonym>
    <synonym>Testoderm</synonym>
    <synonym>Testogel</synonym>
    <synonym>Testolent</synonym>
    <synonym>Testolin</synonym>
    <synonym>Testopropon</synonym>
    <synonym>Testosteroid</synonym>
    <synonym>Testoviron schering</synonym>
    <synonym>Testoviron T</synonym>
    <synonym>Testro aq</synonym>
    <synonym>Testrone</synonym>
    <synonym>Testryl</synonym>
    <synonym>Tostrelle</synonym>
    <synonym>Tostrex</synonym>
    <synonym>Viatrel</synonym>
    <synonym>Virormone</synonym>
    <synonym>Virosterone</synonym>
    <synonym>Androtop</synonym>
    <synonym>CEPA brand OF testosterone</synonym>
    <synonym>Histerone</synonym>
    <synonym>SmithKline beecham brand OF testosterone</synonym>
    <synonym>Solvay brand OF testosterone</synonym>
    <synonym>Sterotate</synonym>
    <synonym>17-beta-Hydroxy-8 alpha-4-androsten-3-one</synonym>
    <synonym>AstraZeneca brand OF testosterone</synonym>
    <synonym>Bartor brand OF testosterone</synonym>
    <synonym>Dr. kade brand OF testosterone</synonym>
    <synonym>Ferring brand OF testosterone</synonym>
    <synonym>Hauck brand OF testosterone</synonym>
    <synonym>Pasadena brand OF testosterone</synonym>
    <synonym>Testosterone sulfate</synonym>
    <synonym>Ulmer brand OF testosterone</synonym>
    <synonym>Unimed brand OF testosterone</synonym>
    <synonym>Watson brand OF testosterone</synonym>
    <synonym>17-beta-Hydroxy-4-androsten-3-one</synonym>
    <synonym>8 Isotestosterone</synonym>
    <synonym>8-Isotestosterone</synonym>
    <synonym>Auxilium pharmaceuticals inc. brand OF testosterone</synonym>
    <synonym>Faulding brand OF testosterone</synonym>
    <synonym>Paladin brand OF testosterone</synonym>
    <synonym>Schering brand OF testosterone</synonym>
    <synonym>17 beta Hydroxy 4 androsten 3 one</synonym>
    <synonym>17 beta Hydroxy 8 alpha 4 androsten 3 one</synonym>
    <synonym>GlaxoSmithKline brand OF testosterone</synonym>
    <synonym>Ortho brand OF testosterone</synonym>
    <synonym>Testopel</synonym>
  </synonyms>
  <chemical_formula>C19H28O2</chemical_formula>
  <average_molecular_weight>288.4244</average_molecular_weight>
  <monisotopic_moleculate_weight>288.20893014</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</traditional_iupac>
  <cas_registry_number>58-22-0</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1</inchi>
  <inchikey>MUMGGOZAMZWBJJ-DYKIIFRCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17beta-hydroxy steroid</external_descriptor>
      <external_descriptor>3-oxo steroid</external_descriptor>
      <external_descriptor>Androgens</external_descriptor>
      <external_descriptor>Androstane and derivatives</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>androstane</external_descriptor>
      <external_descriptor>androstanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>155 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0234 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.32</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>288.4244</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>288.20893014</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H28O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MUMGGOZAMZWBJJ-DYKIIFRCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452459</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.00167</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS in Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0000343</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Half-skim milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0000270</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0000312</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id/>
  <kegg_id>C00535</kegg_id>
  <chemspider_id>5791</chemspider_id>
  <drugbank_id>DB00624</drugbank_id>
  <pubchem_compound_id>6013</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17347</chebi_id>
  <knapsack_id>C00003675</knapsack_id>
  <wikipedia_id>Testosterone</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Ercoli, Alberto; De Ruggieri, Pietro. An improved method of preparing testosterone, dihydrotestosterone, and some of their esters. Journal of the American Chemical Society (1953), 75 650-3.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
      <pubmed_id>18412364</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00606</protein_accession>
      <name>Hydroxysteroid 17-beta dehydrogenase 6</name>
      <uniprot_id>Q3T001</uniprot_id>
      <gene_name>HSD17B6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:10 UTC</creation_date>
  <update_date>2020-04-16 20:38:24 UTC</update_date>
  <accession>BMDB0000235</accession>
  <secondary_accessions>
    <accession>BMDB00235</accession>
  </secondary_accessions>
  <name>Thiamine</name>
  <description>Thiamine, also known as vitamin B1 or aneurin, belongs to the class of organic compounds known as thiamines. Thiamines are compounds containing a thiamine moiety, which is structurally characterized by a 3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl backbone. Thiamine is a drug which is used for the treatment of thiamine and niacin deficiency states, korsakov's alcoholic psychosis, wernicke-korsakov syndrome, delirium, and peripheral neuritis. Thiamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Thiamine exists in all living species, ranging from bacteria to humans. In cattle, thiamine is involved in the metabolic pathway called the valine, leucine, and isoleucine degradation pathway. Thiamine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>3-(4-AMINO-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium</synonym>
    <synonym>Aneurin</synonym>
    <synonym>Antiberiberi factor</synonym>
    <synonym>Thiamin</synonym>
    <synonym>Thiamine(1+) ion</synonym>
    <synonym>Thiaminium</synonym>
    <synonym>Vitamin b1</synonym>
    <synonym>Apate drops</synonym>
    <synonym>Beatine</synonym>
    <synonym>Bedome</synonym>
    <synonym>Begiolan</synonym>
    <synonym>Benerva</synonym>
    <synonym>Bequin</synonym>
    <synonym>Berin</synonym>
    <synonym>Betalin S</synonym>
    <synonym>Betaxin</synonym>
    <synonym>Bethiazine</synonym>
    <synonym>Beuion</synonym>
    <synonym>Bevitex</synonym>
    <synonym>Bevitine</synonym>
    <synonym>Bewon</synonym>
    <synonym>Biamine</synonym>
    <synonym>Bithiamin</synonym>
    <synonym>Biuno</synonym>
    <synonym>Bivatin</synonym>
    <synonym>Bivita</synonym>
    <synonym>Cernevit-12</synonym>
    <synonym>Clotiamina</synonym>
    <synonym>Eskapen</synonym>
    <synonym>Eskaphen</synonym>
    <synonym>Hybee</synonym>
    <synonym>Lixa-beta</synonym>
    <synonym>Metabolin</synonym>
    <synonym>Slowten</synonym>
    <synonym>THD</synonym>
    <synonym>Thiadoxine</synonym>
    <synonym>Thiaminal</synonym>
    <synonym>Thiamol</synonym>
    <synonym>Thiavit</synonym>
    <synonym>Tiamidon</synonym>
    <synonym>Tiaminal</synonym>
    <synonym>Trophite</synonym>
    <synonym>Vetalin S</synonym>
    <synonym>VIB</synonym>
    <synonym>Vinothiam</synonym>
    <synonym>Vitaneuron</synonym>
    <synonym>Mononitrate, thiamine</synonym>
    <synonym>Thiamine mononitrate</synonym>
    <synonym>Vitamin b 1</synonym>
  </synonyms>
  <chemical_formula>C12H17N4OS</chemical_formula>
  <average_molecular_weight>265.355</average_molecular_weight>
  <monisotopic_moleculate_weight>265.112306876</monisotopic_moleculate_weight>
  <iupac_name>3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium</iupac_name>
  <traditional_iupac>thiamine</traditional_iupac>
  <cas_registry_number>59-43-8</cas_registry_number>
  <smiles>CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N</smiles>
  <inchi>InChI=1S/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1</inchi>
  <inchikey>JZRWCGZRTZMZEH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as thiamines. Thiamines are compounds containing a thiamine moiety, which is structurally characterized by a 3-[(4-Amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazines</class>
    <sub_class>Pyrimidines and pyrimidine derivatives</sub_class>
    <direct_parent>Thiamines</direct_parent>
    <alternative_parents>
      <alternative_parent>4,5-disubstituted thiazoles</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>4,5-disubstituted 1,3-thiazole</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Thiamine</substituent>
      <substituent>Thiazole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Water-soluble vitamins</external_descriptor>
      <external_descriptor>a vitamin</external_descriptor>
      <external_descriptor>thiamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>248 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>500.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>265.355</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>265.112306876</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H17N4OS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JZRWCGZRTZMZEH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>75.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>73.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Thiamine Metabolism</name>
      <smpdb_id>SMP0087212</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3704</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438547</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.696</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.131</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.131</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.754</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.357</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.754</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.696</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.507</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.754</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.696</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.545</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.696</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.696</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.432</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.696</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.507</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.696</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.47</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.47</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.734</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.734</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.668 - 51.629</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309.</reference_text>
          <pubmed_id>17558655</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.6 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.6 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.53 +/- 0.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.357 - 1.470</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Tafaj M, Schollenberger M, Feofilowa J, Zebeli Q, Steingass H, Drochner W: Relationship between thiamine concentration and fermentation patterns in the rumen fluid of dairy cows fed with graded concentrate levels. J Anim Physiol Anim Nutr (Berl). 2006 Aug;90(7-8):335-43. doi: 10.1111/j.1439-0396.2006.00608.x.</reference_text>
          <pubmed_id>16867079</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00378</kegg_id>
  <drugbank_id>DB00152</drugbank_id>
  <foodb_id>FDB008424</foodb_id>
  <pubchem_compound_id>1130</pubchem_compound_id>
  <chemspider_id/>
  <pdbe_id/>
  <chebi_id>18385</chebi_id>
  <meta_cyc_id/>
  <knapsack_id>C00000775</knapsack_id>
  <wikipedia_id>Thiamine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Sugimoto, Hirohiko; Ishiba, Teruyuki; Sato, Tomohiro; Nakai, Hiroshi; Hirai, Kentaro. Novel S-alkylation products from "isolated thiamin ylide" via thiaminium neothiaminthiolate ion pair. Journal of Organic Chemistry (1990), 55(2), 467-70.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309.</reference_text>
      <pubmed_id>17558655</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
      <pubmed_id>22081685</pubmed_id>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01985</protein_accession>
      <name>Mitochondrial thiamine pyrophosphate carrier</name>
      <uniprot_id>Q29RM1</uniprot_id>
      <gene_name>SLC25A19</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:11 UTC</creation_date>
  <update_date>2020-04-16 20:39:15 UTC</update_date>
  <accession>BMDB0000237</accession>
  <secondary_accessions>
    <accession>BMDB00237</accession>
  </secondary_accessions>
  <name>Propionic acid</name>
  <description>Propionic acid, also known as propionate or acide propanoique, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Propionic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Propionic acid exists in all living species, ranging from bacteria to humans. Propionic acid is a potentially toxic compound. Propionic acid has been found to be associated with several diseases known as rheumatoid arthritis, irritable bowel syndrome, colorectal cancer, and ulcerative colitis; also propionic acid has been linked to the inborn metabolic disorders including propionic acidemia.</description>
  <synonyms>
    <synonym>Acide propanoique</synonym>
    <synonym>Acide propionique</synonym>
    <synonym>Carboxyethane</synonym>
    <synonym>CH3-CH2-COOH</synonym>
    <synonym>Ethanecarboxylic acid</synonym>
    <synonym>Ethylformic acid</synonym>
    <synonym>Metacetonic acid</synonym>
    <synonym>Methylacetic acid</synonym>
    <synonym>PA</synonym>
    <synonym>Propanoic acid</synonym>
    <synonym>Propioic acid</synonym>
    <synonym>Propionsaeure</synonym>
    <synonym>Propoic acid</synonym>
    <synonym>Pseudoacetic acid</synonym>
    <synonym>Propionate</synonym>
    <synonym>Ethanecarboxylate</synonym>
    <synonym>Ethylformate</synonym>
    <synonym>Metacetonate</synonym>
    <synonym>Methylacetate</synonym>
    <synonym>Propanoate</synonym>
    <synonym>Propioate</synonym>
    <synonym>Propoate</synonym>
    <synonym>Pseudoacetate</synonym>
    <synonym>Adofeed</synonym>
    <synonym>Antischim b</synonym>
    <synonym>Luprosil</synonym>
    <synonym>MonoProp</synonym>
    <synonym>Propanate</synonym>
    <synonym>Propcorn</synonym>
    <synonym>Propkorn</synonym>
    <synonym>Prozoin</synonym>
    <synonym>Toxi-check</synonym>
    <synonym>Propionic acid, zinc salt</synonym>
    <synonym>Potassium propionate</synonym>
    <synonym>Chromium propionate</synonym>
    <synonym>Lithium propanoate</synonym>
    <synonym>Zinc propionate</synonym>
  </synonyms>
  <chemical_formula>C3H6O2</chemical_formula>
  <average_molecular_weight>74.0785</average_molecular_weight>
  <monisotopic_moleculate_weight>74.036779436</monisotopic_moleculate_weight>
  <iupac_name>propanoic acid</iupac_name>
  <traditional_iupac>propanoic acid</traditional_iupac>
  <cas_registry_number>79-09-4</cas_registry_number>
  <smiles>CCC(O)=O</smiles>
  <inchi>InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)</inchi>
  <inchikey>XBDQKXXYIPTUBI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Carboxylic acids</sub_class>
    <direct_parent>Carboxylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Saturated fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>saturated fatty acid</external_descriptor>
      <external_descriptor>short-chain fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-20.7 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.33</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>74.0785</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>74.036779436</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H6O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H6O2/c1-2-3(4)5/h2H2,1H3,(H,4,5)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XBDQKXXYIPTUBI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>17.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>7.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin K Metabolism</name>
      <smpdb_id>SMP0087227</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438248</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.9 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.3 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.71 +/- 7.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.94 +/- 0.12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.58 +/- 6.92</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.84 +/- 2.27</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.2 (0.1 - 0.6)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.2 (0.1 - 0.4)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.2 (0.1 - 0.5)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.5 (0.7 - 2.7)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>16103+/-4550</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1820</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2260</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>3180</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1680</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>14000-17000</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>13196-21732</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>18210 +/- 3210</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>22630 +/- 8030</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>31835 +/- 6795</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>16860 +/- 5180</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hanne Christine Bertram, Niels Bastian Kristensen, Mogens Vestergaard, SÃ¸ren Krogh Jensen, Jakob Sehested, Niels Christian Nielsen, Anders Malmendal. Metabolic characterization of rumen epithelial tissue from dairy calves fed different starter diets using 1H NMR spectroscopy. Livestock Science (2008) 120:127-134   doi: 10.1016/j.livsci.2008.05.001</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>17900</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>18000</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>27600</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>15000</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>21340  +/- 2970</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>O'Grady L, Doherty ML, Mulligan FJ: Subacute ruminal acidosis (SARA) in grazing Irish dairy cows. Vet J. 2008 Apr;176(1):44-9. doi: 10.1016/j.tvjl.2007.12.017. Epub 2008 Mar 6.</reference_text>
          <pubmed_id>18328751</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>16855.86 +/- 5180.48</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein.</comment>
      <references>
        <reference>
          <reference_text>Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17.</reference_text>
          <pubmed_id>22059599</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB031132</foodb_id>
  <kegg_id>C00163</kegg_id>
  <chemspider_id>1005</chemspider_id>
  <drugbank_id>DB03766</drugbank_id>
  <pubchem_compound_id>1032</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30768</chebi_id>
  <knapsack_id>C00044287</knapsack_id>
  <wikipedia_id>Propionic acid</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>34098</bigg_id>
  <metlin_id>3215</metlin_id>
  <synthesis_reference>Zhan, Jianghong; Meng, Wei; Gong, Tao; Huang, Fen-sheng.  Preparation of propionic acid by propionaldehyde oxidation.    Shihua Jishu Yu Yingyong  (2005),  23(6),  421-423.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
    <reference>
      <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:12 UTC</creation_date>
  <update_date>2020-03-13 16:19:40 UTC</update_date>
  <accession>BMDB0000238</accession>
  <secondary_accessions>
    <accession>BMDB00238</accession>
  </secondary_accessions>
  <name>Sepiapterin</name>
  <description/>
  <synonyms>
    <synonym>(S)-2-Amino-7,8-dihydro-6-(2-hydroxy-1-oxopropyl)-4(1H)-pteridinone</synonym>
    <synonym>1-(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)-2-hydroxy-1-propanone</synonym>
    <synonym>2-Amino-6-(S)-lactoyl-7,8-dihydro-4(3H)-pteridinone</synonym>
    <synonym>2-Amino-7,8-dihydro-6-[(2S)-2-hydroxy-1-oxopropyl]-4(1H)pteridinone</synonym>
    <synonym>L-Sepiapterin</synonym>
    <synonym>Lopac-S-154</synonym>
    <synonym>Sepiapterine</synonym>
    <synonym>Sepiapterin-C</synonym>
    <synonym>2-Amino-6-(S)-lactoyl-7,8-dihydro-4(3H)- pteridinone</synonym>
    <synonym>Sepia-pterin</synonym>
    <synonym>2-Amino-7,8-dihydro-6-((2S)-2-hydroxy-1-oxopropyl)-4(3H)-pteridinone acid</synonym>
  </synonyms>
  <chemical_formula>C9H11N5O3</chemical_formula>
  <average_molecular_weight>237.2153</average_molecular_weight>
  <monisotopic_moleculate_weight>237.086189243</monisotopic_moleculate_weight>
  <iupac_name>2-amino-6-[(2S)-2-hydroxypropanoyl]-1,4,7,8-tetrahydropteridin-4-one</iupac_name>
  <traditional_iupac>sepiapterin</traditional_iupac>
  <cas_registry_number>17094-01-8</cas_registry_number>
  <smiles>C[C@H](O)C(=O)C1=NC2=C(NC1)NC(N)=NC2=O</smiles>
  <inchi>InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,15H,2H2,1H3,(H4,10,11,13,14,17)/t3-/m0/s1</inchi>
  <inchikey>VPVOXUSPXFPWBN-VKHMYHEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Pterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Acyloins</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketimines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyloin</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Ketimine</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pterin</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-6-[(2S)-2-hydroxypropanoyl]-1,4,7,8-tetrahydropteridin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>237.2153</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>237.086189243</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](O)C(=O)C1=NC2=C(NC1)NC(N)=NC2=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11N5O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,15H,2H2,1H3,(H4,10,11,13,14,17)/t3-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VPVOXUSPXFPWBN-VKHMYHEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>129.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>67.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pterine Biosynthesis</name>
      <smpdb_id>SMP0087250</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>299917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>299918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>299919</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342060</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021914</foodb_id>
  <kegg_id>C00835</kegg_id>
  <chemspider_id>58746</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>65253</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>804632</chebi_id>
  <knapsack_id/>
  <wikipedia_id>Sepiapterin</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5244</metlin_id>
  <synthesis_reference>Pfleiderer, Wolfgang.  Synthesis and absolute configuration of sepiapterin.    Chem. Biol. Pteridines, Proc. Int. Symp., 5th  (1975),     941-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00379</protein_accession>
      <name>Sepiapterin reductase</name>
      <uniprot_id>Q17QK8</uniprot_id>
      <gene_name>SPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:13 UTC</creation_date>
  <update_date>2020-04-15 22:13:22 UTC</update_date>
  <accession>BMDB0000239</accession>
  <secondary_accessions>
    <accession>BMDB00239</accession>
  </secondary_accessions>
  <name>Pyridoxine</name>
  <description>Pyridoxine, also known as pyridoxol or vitamin B6, belongs to the class of organic compounds known as pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by a hydroxymethyl group. Pyridoxine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Pyridoxine exists in all living species, ranging from bacteria to humans. Pyridoxine participates in a number of enzymatic reactions, within cattle. In particular, Pyridoxine can be converted into pyridoxal; which is catalyzed by the enzyme pyridoxine-5'-phosphate oxidase. In addition, Pyridoxine can be converted into pyridoxine 5'-phosphate; which is catalyzed by the enzyme pyridoxal kinase. In cattle, pyridoxine is involved in the metabolic pathway called the vitamin B6 metabolism pathway. Pyridoxine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2-Methyl-3-hydroxy-4,5-dihydroxymethylpyridine</synonym>
    <synonym>3-Hydroxy-4,5-bis(hydroxymethyl)-2-methylpyridine</synonym>
    <synonym>3-Hydroxy-4,5-dimethylol-alpha-picoline</synonym>
    <synonym>5-Hydroxy-6-methyl-3,4-pyridinedimethanol</synonym>
    <synonym>Pyridoxol</synonym>
    <synonym>Vitamin b6</synonym>
    <synonym>3-Hydroxy-4,5-dimethylol-a-picoline</synonym>
    <synonym>3-Hydroxy-4,5-dimethylol-α-picoline</synonym>
    <synonym>2-Methyl-3-hydroxy-4,5-bis(hydroxymethyl)pyridine</synonym>
    <synonym>2-Methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridine</synonym>
    <synonym>2-Methyl-4,5-bis(hydroxymethyl)-3-hydroxypyridine</synonym>
    <synonym>3-Hydroxy-2-picoline-4,5-dimethanol</synonym>
    <synonym>Adermine</synonym>
    <synonym>Gravidox</synonym>
    <synonym>Hydoxin</synonym>
    <synonym>Piridossina</synonym>
    <synonym>Piridoxina</synonym>
    <synonym>Pyridoxin</synonym>
    <synonym>Pyridoxinum</synonym>
    <synonym>Pyridoxolum</synonym>
    <synonym>Pyridoxol hydrochloride</synonym>
    <synonym>Rodex</synonym>
    <synonym>Pyridoxine hydrochloride</synonym>
  </synonyms>
  <chemical_formula>C8H11NO3</chemical_formula>
  <average_molecular_weight>169.1778</average_molecular_weight>
  <monisotopic_moleculate_weight>169.073893223</monisotopic_moleculate_weight>
  <iupac_name>4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol</iupac_name>
  <traditional_iupac>pyridoxine</traditional_iupac>
  <cas_registry_number>65-23-6</cas_registry_number>
  <smiles>CC1=C(O)C(CO)=C(CO)C=N1</smiles>
  <inchi>InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3</inchi>
  <inchikey>LXNHXLLTXMVWPM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridoxines. These are pyridoxal derivatives in which the carbaldehyde group at position 2 of the pyridoxal moiety is replaced by a hydroxymethyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyridoxines</sub_class>
    <direct_parent>Pyridoxines</direct_parent>
    <alternative_parents>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyridines</alternative_parent>
      <alternative_parent>Methylpyridines</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyridine</substituent>
      <substituent>Methylpyridine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyridoxine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Water-soluble vitamins</external_descriptor>
      <external_descriptor>a vitamin B6</external_descriptor>
      <external_descriptor>hydroxymethylpyridine</external_descriptor>
      <external_descriptor>methylpyridines</external_descriptor>
      <external_descriptor>monohydroxypyridine</external_descriptor>
      <external_descriptor>vitamin B6</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>159 - 162 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>79 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.77</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>169.1778</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>169.073893223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(O)C(CO)=C(CO)C=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H11NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H11NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,10-12H,3-4H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LXNHXLLTXMVWPM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>73.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>44.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Vitamin B6 Metabolism</name>
      <smpdb_id>SMP0087240</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31882</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37380</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.483</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.364</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.364</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.187</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.364</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.00972</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.955</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.66</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.187</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.955</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.719</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.187</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.187</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.896</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.955</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.483</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.0146</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.66</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.719</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.246</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.246</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.955</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.896</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.955</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.128</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.128</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.778</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.719</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.955</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>41.377</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Enriched, sterilized, whole commercial milk</comment>
      <references>
        <reference>
          <reference_text>Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309.</reference_text>
          <pubmed_id>17558655</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB000574</foodb_id>
  <kegg_id>C00314</kegg_id>
  <chemspider_id>1025</chemspider_id>
  <drugbank_id>DB00165</drugbank_id>
  <pubchem_compound_id>1054</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16709</chebi_id>
  <knapsack_id>C00001551</knapsack_id>
  <wikipedia_id>Pyridoxine</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Itov, Z. I.; Stepanova, S. V.; El'yanov, B. S.; Gunar, V. I.  Synthesis of pyridoxine under high pressure.    Khimiko-Farmatsevticheskii Zhurnal  (1987),  21(7),  858-62.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309.</reference_text>
      <pubmed_id>17558655</pubmed_id>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:15 UTC</creation_date>
  <update_date>2020-04-15 22:23:52 UTC</update_date>
  <accession>BMDB0000240</accession>
  <secondary_accessions>
    <accession>BMDB00240</accession>
  </secondary_accessions>
  <name>Sulfite</name>
  <description/>
  <synonyms>
    <synonym>[SO(OH)2]</synonym>
    <synonym>Acide sulfureux</synonym>
    <synonym>Acido sulfuroso</synonym>
    <synonym>H2SO3</synonym>
    <synonym>S(O)(OH)2</synonym>
    <synonym>Schweflige saeure</synonym>
    <synonym>Sulphurous acid</synonym>
    <synonym>Sulfurous acid</synonym>
    <synonym>Acide sulphureux</synonym>
    <synonym>Acido sulphuroso</synonym>
    <synonym>Sulphite</synonym>
    <synonym>Sulfur dioxide solution</synonym>
    <synonym>Sulfuric(IV) acid (H2SO3)</synonym>
    <synonym>Hydrogen sulfite</synonym>
    <synonym>Sulfite</synonym>
  </synonyms>
  <chemical_formula>H2O3S</chemical_formula>
  <average_molecular_weight>82.079</average_molecular_weight>
  <monisotopic_moleculate_weight>81.97246462</monisotopic_moleculate_weight>
  <iupac_name>sulfurous acid</iupac_name>
  <traditional_iupac>sulfurous acid</traditional_iupac>
  <cas_registry_number>14265-45-3</cas_registry_number>
  <smiles>OS(O)=O</smiles>
  <inchi>InChI=1S/H2O3S/c1-4(2)3/h(H2,1,2,3)</inchi>
  <inchikey>LSNNMFCWUKXFEE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as non-metal sulfites. These are inorganic non-metallic compounds containing a sulfite as its largest oxoanion.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Non-metal oxoanionic compounds</class>
    <sub_class>Non-metal sulfites</sub_class>
    <direct_parent>Non-metal sulfites</direct_parent>
    <alternative_parents>
      <alternative_parent>Inorganic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Inorganic oxide</substituent>
      <substituent>Non-metal sulfite</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>sulfur oxoacid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>sulfurous acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>82.079</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>81.97246462</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OS(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>H2O3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/H2O3S/c1-4(2)3/h(H2,1,2,3)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LSNNMFCWUKXFEE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>12.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>5.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218076</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB013391</foodb_id>
  <kegg_id>C00094</kegg_id>
  <chemspider_id>1069</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>1100</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>48854</chebi_id>
  <knapsack_id>C00019662</knapsack_id>
  <wikipedia_id>Sulfite</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Dorain, P. B.; Von Raben, K. U.; Chang, R. K.; Laube, B. L.  Catalytic formation of sulfite and sulfate ions from sulfur dioxide on silver observed by surface-enhanced Raman scattering.    Chemical Physics Letters  (1981),  84(2),  405-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00114</protein_accession>
      <name>Thiosulfate sulfurtransferase</name>
      <uniprot_id>P00586</uniprot_id>
      <gene_name>TST</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:16 UTC</creation_date>
  <update_date>2020-04-16 20:40:32 UTC</update_date>
  <accession>BMDB0000241</accession>
  <secondary_accessions>
    <accession>BMDB00241</accession>
  </secondary_accessions>
  <name>Protoporphyrin IX</name>
  <description/>
  <synonyms>
    <synonym>3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid</synonym>
    <synonym>3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoic acid</synonym>
    <synonym>H2PpIX</synonym>
    <synonym>Kammerer's prophyrin</synonym>
    <synonym>Ooporphyrin</synonym>
    <synonym>Porphyrinogen IX</synonym>
    <synonym>3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionate</synonym>
    <synonym>3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoate</synonym>
    <synonym>3,3'-(3,7,12,17-Tetramethyl-8,13-divinylporphine-2,18-diyl)di</synonym>
    <synonym>PpIX</synonym>
    <synonym>Protoporphyrin</synonym>
    <synonym>Protoporphyrin-"ix"</synonym>
    <synonym>Protoporphyrin-IX</synonym>
  </synonyms>
  <chemical_formula>C34H34N4O4</chemical_formula>
  <average_molecular_weight>562.6582</average_molecular_weight>
  <monisotopic_moleculate_weight>562.258005596</monisotopic_moleculate_weight>
  <iupac_name>3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>protoporphyrin</traditional_iupac>
  <cas_registry_number>553-12-8</cas_registry_number>
  <smiles>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O</smiles>
  <inchi>InChI=1S/C34H34N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-</inchi>
  <inchikey>KSFOVUSSGSKXFI-UJJXFSCMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>300 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.169 mg/mL at 25 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>562.6582</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>562.258005596</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C34H34N4O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C34H34N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KSFOVUSSGSKXFI-UJJXFSCMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>131.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>163.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>65.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326991</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB004277</foodb_id>
  <kegg_id>C02191</kegg_id>
  <pubchem_compound_id/>
  <chemspider_id>10469486</chemspider_id>
  <drugbank_id>DB02285</drugbank_id>
  <pdbe_id/>
  <chebi_id>15430</chebi_id>
  <knapsack_id>C00007370</knapsack_id>
  <meta_cyc_id>PROTOPORPHYRIN_IX</meta_cyc_id>
  <wikipedia_id>Protoporphyrin_IX</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Games, David E.; Jackson, Anthony H.; Jackson, J. Richard; Belcher, Roderick V.; Smith, Sydney G.  Biosynthesis of protoporphyrin-IX from coproporphyrinogen-III.    Journal of the Chemical Society, Chemical Communications  (1976),   (6),  187-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00067</protein_accession>
      <name>Ferrochelatase, mitochondrial</name>
      <uniprot_id>P22600</uniprot_id>
      <gene_name>FECH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00527</protein_accession>
      <name>Protoporphyrinogen oxidase</name>
      <uniprot_id>P56602</uniprot_id>
      <gene_name>PPOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:17 UTC</creation_date>
  <update_date>2020-04-16 21:05:24 UTC</update_date>
  <accession>BMDB0000243</accession>
  <secondary_accessions>
    <accession>BMDB00243</accession>
  </secondary_accessions>
  <name>Pyruvic acid</name>
  <description>Pyruvic acid, also known as pyroracemic acid or 2-oxopropanoate, belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. Pyruvic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Pyruvic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Pyruvic acid exists in all living species, ranging from bacteria to humans. Pyruvic acid is a potentially toxic compound. Pyruvic acid has been found to be associated with several diseases known as leigh's syndrome, subacute necrotizing encephalopathy, sne, myopathy with lactic acidosis, hereditary, and 3-hydroxy-3-methylglutaryl-coa synthase deficiency; also pyruvic acid has been linked to several inborn metabolic disorders including 3-methylglutaconic aciduria type ii, x-linked and glucagon deficiency.</description>
  <synonyms>
    <synonym>2-Ketopropionic acid</synonym>
    <synonym>2-Oxopropanoic acid</synonym>
    <synonym>2-Oxopropansaeure</synonym>
    <synonym>2-Oxopropionsaeure</synonym>
    <synonym>Acetylformic acid</synonym>
    <synonym>Acide pyruvique</synonym>
    <synonym>alpha-Ketopropionic acid</synonym>
    <synonym>alpha-Oxopropionsaeure</synonym>
    <synonym>Brenztraubensaeure</synonym>
    <synonym>BTS</synonym>
    <synonym>CH3COCOOH</synonym>
    <synonym>Pyroracemic acid</synonym>
    <synonym>2-Oxopropanoate</synonym>
    <synonym>2-Ketopropionate</synonym>
    <synonym>Acetylformate</synonym>
    <synonym>a-Ketopropionate</synonym>
    <synonym>a-Ketopropionic acid</synonym>
    <synonym>alpha-Ketopropionate</synonym>
    <synonym>Α-ketopropionate</synonym>
    <synonym>Α-ketopropionic acid</synonym>
    <synonym>a-Oxopropionsaeure</synonym>
    <synonym>Α-oxopropionsaeure</synonym>
    <synonym>Pyroracemate</synonym>
    <synonym>Pyruvate</synonym>
    <synonym>2-Oxopropionate</synonym>
    <synonym>2-Oxopropionic acid</synonym>
    <synonym>Acid, pyruvic</synonym>
    <synonym>Pyruvic acid</synonym>
    <synonym>alpha-Ketopropanoic acid</synonym>
    <synonym>α-Ketopropanoic acid</synonym>
  </synonyms>
  <chemical_formula>C3H4O3</chemical_formula>
  <average_molecular_weight>88.0621</average_molecular_weight>
  <monisotopic_moleculate_weight>88.016043994</monisotopic_moleculate_weight>
  <iupac_name>2-oxopropanoic acid</iupac_name>
  <traditional_iupac>pyruvic acid</traditional_iupac>
  <cas_registry_number>127-17-3</cas_registry_number>
  <smiles>CC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)</inchi>
  <inchikey>LCTONWCANYUPML-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Alpha-keto acids and derivatives</sub_class>
    <direct_parent>Alpha-keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>Oxo fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>13.8 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.066</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-oxopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>88.0621</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>88.016043994</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H4O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LCTONWCANYUPML-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>17.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>7.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glucose-Alanine Cycle</name>
      <smpdb_id>SMP0087221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>LPS and Citrate Signaling and Inflammation</name>
      <smpdb_id>SMP0120946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvaldehyde Degradation</name>
      <smpdb_id>SMP0087210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37382</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>150+/-40</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in lactating Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>108+/-20</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>123+/-51</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>38.03 +/- 8.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2 - 188</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>57.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
          <pubmed_id>2760296</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>24.3 +/-  29.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from Simmental cows during late lactation</comment>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
          <pubmed_id>23931703</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>36.52 +/- 14.70</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31.75 +/- 8.44</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1-183</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>62+/-33</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>157+/-68</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>11+/-3</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB031141</foodb_id>
  <kegg_id>C00022</kegg_id>
  <chemspider_id/>
  <drugbank_id>DB00119</drugbank_id>
  <pubchem_compound_id>1060</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>32816</chebi_id>
  <knapsack_id>C00001200</knapsack_id>
  <wikipedia_id>Pyruvic_acid</wikipedia_id>
  <meta_cyc_id>PYRUVATE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Xiang, Wei; Okita, Motomu.  Preparation of pyruvic acid.    Jpn. Kokai Tokkyo Koho  (2003),     5 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
      <pubmed_id>2760296</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
      <pubmed_id>23931703</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00088</protein_accession>
      <name>L-serine dehydratase</name>
      <uniprot_id>Q0VCW4</uniprot_id>
      <gene_name>SDS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00109</protein_accession>
      <name>N-acetylneuraminate lyase</name>
      <uniprot_id>Q29RY9</uniprot_id>
      <gene_name>NPL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00449</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>B3IVN4</uniprot_id>
      <gene_name>PKM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00457</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>Q3ZC87</uniprot_id>
      <gene_name>PKM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00465</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>Q1JPG7</uniprot_id>
      <gene_name>PKLR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00497</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>A5D984</uniprot_id>
      <gene_name>PKM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00573</protein_accession>
      <name>L-lactate dehydrogenase A-like 6B</name>
      <uniprot_id>Q3T056</uniprot_id>
      <gene_name>LDHAL6B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00574</protein_accession>
      <name>L-lactate dehydrogenase B chain</name>
      <uniprot_id>Q5E9B1</uniprot_id>
      <gene_name>LDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00575</protein_accession>
      <name>L-lactate dehydrogenase A chain</name>
      <uniprot_id>P19858</uniprot_id>
      <gene_name>LDHA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00576</protein_accession>
      <name>L-lactate dehydrogenase</name>
      <uniprot_id>B0JYN3</uniprot_id>
      <gene_name>LDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00577</protein_accession>
      <name>L-lactate dehydrogenase</name>
      <uniprot_id>Q2KJG0</uniprot_id>
      <gene_name>LDHC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00615</protein_accession>
      <name>Pyruvate carboxylase, mitochondrial</name>
      <uniprot_id>Q29RK2</uniprot_id>
      <gene_name>PC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00793</protein_accession>
      <name>Alanine--glyoxylate aminotransferase 2, mitochondrial</name>
      <uniprot_id>Q17QF0</uniprot_id>
      <gene_name>AGXT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00858</protein_accession>
      <name>Alanine aminotransferase 1</name>
      <uniprot_id>A4IFH5</uniprot_id>
      <gene_name>GPT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00861</protein_accession>
      <name>Kynurenine--oxoglutarate transaminase 3</name>
      <uniprot_id>Q0P5G4</uniprot_id>
      <gene_name>CCBL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01074</protein_accession>
      <name>Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial</name>
      <uniprot_id>A7MB35</uniprot_id>
      <gene_name>PDHA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01076</protein_accession>
      <name>Pyruvate dehydrogenase E1 component subunit beta, mitochondrial</name>
      <uniprot_id>P11966</uniprot_id>
      <gene_name>PDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:18 UTC</creation_date>
  <update_date>2020-04-15 22:13:24 UTC</update_date>
  <accession>BMDB0000244</accession>
  <secondary_accessions>
    <accession>BMDB00244</accession>
  </secondary_accessions>
  <name>Riboflavin</name>
  <description>Riboflavin, also known as vitamin B2 or lactoflavin, belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring. Riboflavin is a drug which is used for the treatment of ariboflavinosis (vitamin b2 deficiency). Riboflavin exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Riboflavin exists in all living species, ranging from bacteria to humans. Riboflavin is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol</synonym>
    <synonym>6,7-Dimethyl-9-D-ribitylisoalloxazine</synonym>
    <synonym>7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione</synonym>
    <synonym>7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine</synonym>
    <synonym>7,8-Dimethyl-10-ribitylisoalloxazine</synonym>
    <synonym>e101</synonym>
    <synonym>Lactoflavin</synonym>
    <synonym>Riboflavina</synonym>
    <synonym>RIBOFLAVINE</synonym>
    <synonym>Riboflavinum</synonym>
    <synonym>Vitamin b2</synonym>
    <synonym>Vitamin g</synonym>
    <synonym>Bisulase</synonym>
    <synonym>(-)-Riboflavin</synonym>
    <synonym>1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol</synonym>
    <synonym>6,7-Dimethyl-9-ribitylisoalloxazine</synonym>
    <synonym>7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-benzo[g]pteridine-2,4(3H,10H)-dione</synonym>
    <synonym>Beflavin</synonym>
    <synonym>Beflavine</synonym>
    <synonym>Benzo[g]pteridine riboflavin deriv.</synonym>
    <synonym>e 101</synonym>
    <synonym>Flavaxin</synonym>
    <synonym>Flavin BB</synonym>
    <synonym>Flaxain</synonym>
    <synonym>FOOD Yellow 15</synonym>
    <synonym>Hyre</synonym>
    <synonym>Lactobene</synonym>
    <synonym>Lactoflavine</synonym>
    <synonym>Ribipca</synonym>
    <synonym>Ribocrisina</synonym>
    <synonym>Riboderm</synonym>
    <synonym>Ribosyn</synonym>
    <synonym>Ribotone</synonym>
    <synonym>Ribovel</synonym>
    <synonym>Russupteridine yellow III</synonym>
    <synonym>San yellow b</synonym>
    <synonym>Vitaflavine</synonym>
    <synonym>Vitasan b2</synonym>
    <synonym>Vitamin b 2</synonym>
  </synonyms>
  <chemical_formula>C17H20N4O6</chemical_formula>
  <average_molecular_weight>376.3639</average_molecular_weight>
  <monisotopic_moleculate_weight>376.138284392</monisotopic_moleculate_weight>
  <iupac_name>7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione</iupac_name>
  <traditional_iupac>riboflavin</traditional_iupac>
  <cas_registry_number>83-88-5</cas_registry_number>
  <smiles>CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1</smiles>
  <inchi>InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1</inchi>
  <inchikey>AUNGANRZJHBGPY-SCRDCRAPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Alloxazines and isoalloxazines</sub_class>
    <direct_parent>Flavins</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrazines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Quinoxalines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Diazanaphthalene</substituent>
      <substituent>Flavin</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrazine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Quinoxaline</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Water-soluble vitamins</external_descriptor>
      <external_descriptor>flavin</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>290 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0847 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.46</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>376.3639</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>376.138284392</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C17H20N4O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AUNGANRZJHBGPY-SCRDCRAPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>155.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>96.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Riboflavin Metabolism</name>
      <smpdb_id>SMP0087211</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449828</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.251</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.268</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.268</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.915</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.72</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.79</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.101</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.597</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.915</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.155</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.65</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.836</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.836</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.676</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.0483</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Enriched, sterilized, whole commercial milk</comment>
      <references>
        <reference>
          <reference_text>Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309.</reference_text>
          <pubmed_id>17558655</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.676</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.278</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.155</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.597</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.155</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.915</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.915</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.517</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.543</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.517</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18.599 - 63.237</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309.</reference_text>
          <pubmed_id>17558655</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.49</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.49</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.597</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.57</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.57</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.720 - 4.384</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.3 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB012160</foodb_id>
  <kegg_id>C00255</kegg_id>
  <pubchem_compound_id>493570</pubchem_compound_id>
  <chemspider_id>431981</chemspider_id>
  <drugbank_id>DB00140</drugbank_id>
  <pdbe_id/>
  <chebi_id>17015</chebi_id>
  <knapsack_id>C00001552</knapsack_id>
  <meta_cyc_id>RIBOFLAVIN</meta_cyc_id>
  <wikipedia_id>Riboflavin</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Tishler, Max; Pfister, Karl, III; Babson, R. D.; Ladenburg, Kurt; Fleming, Ann J. Reaction between o-aminoazo compounds and barbituric acid. A new synthesis of riboflavin. Journal of the American Chemical Society (1947), 69 1487-92.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309.</reference_text>
      <pubmed_id>17558655</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
      <pubmed_id>22081685</pubmed_id>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00387</protein_accession>
      <name>Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)</name>
      <uniprot_id>Q58DK4</uniprot_id>
      <gene_name>DAK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:19 UTC</creation_date>
  <update_date>2020-04-15 22:13:25 UTC</update_date>
  <accession>BMDB0000245</accession>
  <secondary_accessions>
    <accession>BMDB00245</accession>
  </secondary_accessions>
  <name>Porphobilinogen</name>
  <description>Porphobilinogen, also known as PBG, belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Porphobilinogen is possibly soluble (in water) and a very strong basic compound (based on its pKa). Porphobilinogen exists in all living species, ranging from bacteria to humans. Porphobilinogen can be biosynthesized from 5-aminolevulinic acid through its interaction with the enzyme Delta-aminolevulinic acid dehydratase. In cattle, porphobilinogen is involved in the metabolic pathway called the porphyrin metabolism pathway. Porphobilinogen is a potentially toxic compound.</description>
  <synonyms>
    <synonym>5-(Aminomethyl)-4-(carboxymethyl)-pyrrole-3-propionate</synonym>
    <synonym>5-(Aminomethyl)-4-(carboxymethyl)-pyrrole-3-propionic acid</synonym>
    <synonym>PBG</synonym>
    <synonym>Porphobilinogen</synonym>
  </synonyms>
  <chemical_formula>C10H14N2O4</chemical_formula>
  <average_molecular_weight>226.2292</average_molecular_weight>
  <monisotopic_moleculate_weight>226.095356946</monisotopic_moleculate_weight>
  <iupac_name>3-[5-(aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid</iupac_name>
  <traditional_iupac>porphobilinogen</traditional_iupac>
  <cas_registry_number>487-90-1</cas_registry_number>
  <smiles>NCC1=C(CC(O)=O)C(CCC(O)=O)=CN1</smiles>
  <inchi>InChI=1S/C10H14N2O4/c11-4-8-7(3-10(15)16)6(5-12-8)1-2-9(13)14/h5,12H,1-4,11H2,(H,13,14)(H,15,16)</inchi>
  <inchikey>QSHWIQZFGQKFMA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>Aralkylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aralkylamino compound</external_descriptor>
      <external_descriptor>dicarboxylic acid</external_descriptor>
      <external_descriptor>pyrroles</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[5-(aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>226.2292</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>226.095356946</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCC1=C(CC(O)=O)C(CCC(O)=O)=CN1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H14N2O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H14N2O4/c11-4-8-7(3-10(15)16)6(5-12-8)1-2-9(13)14/h5,12H,1-4,11H2,(H,13,14)(H,15,16)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QSHWIQZFGQKFMA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>116.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>56.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22696</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB02272</drugbank_id>
  <kegg_id>C00931</kegg_id>
  <chemspider_id>995</chemspider_id>
  <foodb_id>FDB021916</foodb_id>
  <pubchem_compound_id>1021</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17381</chebi_id>
  <knapsack_id>C00007339</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>PORPHOBILINOGEN</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Porphobilinogen</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Frydman, Benjamin; Despuy, Maria E.; Rapoport, Henry. Pyrroles from azaindoles. A synthesis of porphobilinogen. Journal of the American Chemical Society (1965), 87(15), 3530-1.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00110</protein_accession>
      <name>Porphobilinogen deaminase</name>
      <uniprot_id>Q2KIN5</uniprot_id>
      <gene_name>HMBS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00111</protein_accession>
      <name>Delta-aminolevulinic acid dehydratase</name>
      <uniprot_id>Q2KIL3</uniprot_id>
      <gene_name>ALAD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00112</protein_accession>
      <name>Delta-aminolevulinic acid dehydratase</name>
      <uniprot_id>Q58DK5</uniprot_id>
      <gene_name>ALAD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:20 UTC</creation_date>
  <update_date>2020-03-13 16:19:44 UTC</update_date>
  <accession>BMDB0000246</accession>
  <secondary_accessions>
    <accession>BMDB00246</accession>
  </secondary_accessions>
  <name>Tetrahydrofuran</name>
  <description>Tetrahydrofuran, also known as 1,4-epoxybutane or butylene oxide, belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Tetrahydrofuran exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule.</description>
  <synonyms>
    <synonym>1,4-Epoxybutane</synonym>
    <synonym>Butane alpha,delta-oxide</synonym>
    <synonym>Butylene oxide</synonym>
    <synonym>Furanidine</synonym>
    <synonym>Tetramethylene oxide</synonym>
    <synonym>THF</synonym>
    <synonym>Butane a,delta-oxide</synonym>
    <synonym>Butane α,δ-oxide</synonym>
    <synonym>Butane a,δ-oxide</synonym>
    <synonym>1,4-Epoxy-butane</synonym>
    <synonym>Butane a,D-oxide</synonym>
    <synonym>Cyclotetramethylene</synonym>
    <synonym>Cyclotetramethylene oxide</synonym>
    <synonym>Diethylene oxide</synonym>
    <synonym>Hydrofuran</synonym>
    <synonym>Oxacyclopentane</synonym>
    <synonym>Oxolane</synonym>
    <synonym>Polytetrahydrofuran</synonym>
    <synonym>Tetrahydrofuraan</synonym>
    <synonym>Tetrahydrofurane</synonym>
    <synonym>Tetrahydrofuranne</synonym>
    <synonym>Tetraidrofurano</synonym>
    <synonym>Tetrahydrofuran</synonym>
  </synonyms>
  <chemical_formula>C4H8O</chemical_formula>
  <average_molecular_weight>72.1057</average_molecular_weight>
  <monisotopic_moleculate_weight>72.057514878</monisotopic_moleculate_weight>
  <iupac_name>oxolane</iupac_name>
  <traditional_iupac>tetrahydrofuran</traditional_iupac>
  <cas_registry_number>109-99-9</cas_registry_number>
  <smiles>C1CCOC1</smiles>
  <inchi>InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2</inchi>
  <inchikey>WYURNTSHIVDZCO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrahydrofurans</class>
    <sub_class/>
    <direct_parent>Tetrahydrofurans</direct_parent>
    <alternative_parents>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>cyclic ether</external_descriptor>
      <external_descriptor>oxolanes</external_descriptor>
      <external_descriptor>saturated organic heteromonocyclic parent</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-108.3 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.46</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>oxolane</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>72.1057</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>72.057514878</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C1CCOC1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O/c1-2-4-5-3-1/h1-4H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WYURNTSHIVDZCO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>9.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>20.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366093</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by NMR and GC-MS</comment>
      <references>
        <reference>
          <reference_text>Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26.</reference_text>
          <pubmed_id>27236769</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>7737</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB021917</foodb_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id>26911</chebi_id>
  <pubchem_compound_id>8028</pubchem_compound_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>THF</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Li, Haixia; Yin, Hengbo; Jiang, Tingshun; Hu, Tongjie; Wu, Jing; Wada, Yuji. Cyclodehydration of 1,4-butanediol to tetrahydrofuran catalyzed by supported silicotungstic acid. Catalysis Communications  (2006),  7(10),  778-782.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26.</reference_text>
      <pubmed_id>27236769</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:21 UTC</creation_date>
  <update_date>2020-04-16 22:56:33 UTC</update_date>
  <accession>BMDB0000247</accession>
  <secondary_accessions>
    <accession>BMDB00247</accession>
  </secondary_accessions>
  <name>Sorbitol</name>
  <description>Sorbitolol, also known as sorbitolol or Sorbitolol, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. Sorbitolol is a drug which is used as a non-stimulant laxative via an oral suspension or enema. Sorbitolol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Sorbitolol exists in all living species, ranging from bacteria to humans. Sorbitolol participates in a number of enzymatic reactions, within cattle. In particular, D-Galactose and sorbitolol can be converted into melibiitol; which is mediated by the enzyme Alpha-galactosidase a. In addition, Sorbitolol can be converted into Alpha-D-glucose; which is catalyzed by the enzyme aldose reductase. In cattle, sorbitolol is involved in a couple of metabolic pathways, which include the galactose metabolism pathway and the fructose and mannose degradation pathway.</description>
  <synonyms>
    <synonym>(-)-Sorbitol</synonym>
    <synonym>(2R,3R,4R,5S)-Hexane-1,2,3,4,5,6-hexol</synonym>
    <synonym>D-(-)-Sorbitol</synonym>
    <synonym>D-Sorbit</synonym>
    <synonym>D-SORBITOL</synonym>
    <synonym>e 420</synonym>
    <synonym>e-420</synonym>
    <synonym>e420</synonym>
    <synonym>g-Ol</synonym>
    <synonym>GLC-Ol</synonym>
    <synonym>L-Gulitol</synonym>
    <synonym>D-Glucitol</synonym>
    <synonym>Sorbitol 3% in plastic container</synonym>
    <synonym>D-Sorbol</synonym>
    <synonym>Diakarmon</synonym>
    <synonym>Esasorb</synonym>
    <synonym>Foodol D 70</synonym>
    <synonym>Glucarine</synonym>
    <synonym>Glucitol</synonym>
    <synonym>Karion</synonym>
    <synonym>Karion instant</synonym>
    <synonym>Kyowa powder 50m</synonym>
    <synonym>Multitol</synonym>
    <synonym>Neosorb</synonym>
    <synonym>Neosorb 20/60dC</synonym>
    <synonym>Neosorb 70/02</synonym>
    <synonym>Neosorb 70/70</synonym>
    <synonym>Neosorb p 20/60</synonym>
    <synonym>Neosorb p 60</synonym>
    <synonym>Neosorb p 60W</synonym>
    <synonym>Nivitin</synonym>
    <synonym>Resulax</synonym>
    <synonym>Sionit</synonym>
    <synonym>Sionit K</synonym>
    <synonym>Sionite</synonym>
    <synonym>Sionon</synonym>
    <synonym>Siosan</synonym>
    <synonym>Sorbex m</synonym>
    <synonym>Sorbex R</synonym>
    <synonym>Sorbex RP</synonym>
    <synonym>Sorbex S</synonym>
    <synonym>Sorbex X</synonym>
    <synonym>Sorbilande</synonym>
    <synonym>Sorbilax</synonym>
    <synonym>Sorbit</synonym>
    <synonym>Sorbit D 70</synonym>
    <synonym>Sorbit D-powder</synonym>
    <synonym>Sorbit DP</synonym>
    <synonym>Sorbit DP 50</synonym>
    <synonym>Sorbit kyowa powder 50m</synonym>
    <synonym>Sorbit L 70</synonym>
    <synonym>Sorbit S</synonym>
    <synonym>Sorbit T 70</synonym>
    <synonym>Sorbit W 70</synonym>
    <synonym>Sorbit W-powder</synonym>
    <synonym>Sorbit W-powder 50</synonym>
    <synonym>Sorbit WP</synonym>
    <synonym>Sorbite</synonym>
    <synonym>Sorbitol F</synonym>
    <synonym>Sorbitol FK</synonym>
    <synonym>Sorbitol FP</synonym>
    <synonym>Sorbitol S</synonym>
    <synonym>Sorbitol syrup C</synonym>
    <synonym>Sorbitur</synonym>
    <synonym>Sorbo</synonym>
    <synonym>Sorbogem 712</synonym>
    <synonym>Sorbol</synonym>
    <synonym>Sorbostyl</synonym>
    <synonym>Medefield brand OF sorbitol</synonym>
    <synonym>Sorbitol pfizer brand</synonym>
    <synonym>Yal</synonym>
    <synonym>Klysma sorbit</synonym>
    <synonym>Medevac</synonym>
    <synonym>Trommsdorff brand OF sorbitol</synonym>
    <synonym>Baxter brand OF sorbitol</synonym>
    <synonym>Pfizer brand OF sorbitol</synonym>
  </synonyms>
  <chemical_formula>C6H14O6</chemical_formula>
  <average_molecular_weight>182.1718</average_molecular_weight>
  <monisotopic_moleculate_weight>182.07903818</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol</iupac_name>
  <traditional_iupac>D-sorbitol</traditional_iupac>
  <cas_registry_number>50-70-4</cas_registry_number>
  <smiles>OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO</smiles>
  <inchi>InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1</inchi>
  <inchikey>FBPFZTCFMRRESA-JGWLITMVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar alcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sugar alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>glucitol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>11 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>2750.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.2</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>182.1718</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>182.07903818</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H14O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FBPFZTCFMRRESA-JGWLITMVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>121.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449944</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449945</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>5576</chemspider_id>
  <drugbank_id>DB01638</drugbank_id>
  <foodb_id>FDB011676</foodb_id>
  <kegg_id>C00794</kegg_id>
  <pdbe_id/>
  <chebi_id>17924</chebi_id>
  <pubchem_compound_id>5780</pubchem_compound_id>
  <meta_cyc_id/>
  <knapsack_id>C00001173</knapsack_id>
  <wikipedia_id>Sorbitol</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Liu, Haichao; Luo, Chen.  Method for manufacturing sorbitol and mannitol with cellulose.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2007),     8pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:22 UTC</creation_date>
  <update_date>2020-04-16 20:39:55 UTC</update_date>
  <accession>BMDB0000248</accession>
  <secondary_accessions>
    <accession>BMDB00248</accession>
  </secondary_accessions>
  <name>Thyroxine</name>
  <description>Thyroxinee, also known as thyroxineee or Thyroxinee, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Thyroxinee is a drug which is used for use alone or in combination with antithyroid agents to treat hypothyroidism, goiter, chronic lymphocytic thyroiditis, myxedema coma, and stupor. Thyroxinee exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Thyroxinee exists in all living organisms, ranging from bacteria to humans. In cattle, thyroxinee is involved in the metabolic pathway called thyroid hormone synthesis pathway.</description>
  <synonyms>
    <synonym>3,3',5,5'-Tetraiodo-L-thyronine</synonym>
    <synonym>3,5,3',5'-TETRAIODO-L-thyronine</synonym>
    <synonym>4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanine</synonym>
    <synonym>L-T4</synonym>
    <synonym>Levothyroxin</synonym>
    <synonym>Levothyroxine</synonym>
    <synonym>LT4</synonym>
    <synonym>O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine</synonym>
    <synonym>T4</synonym>
    <synonym>L-Thyroxine</synonym>
    <synonym>O-(4-Hydroxy-3,5-diidophenyl)-3,5-diiodo-L-tyrosine</synonym>
    <synonym>3,5,3'5'-Tetraiodo-L-thyronine</synonym>
    <synonym>Forthyron</synonym>
    <synonym>(-)-Thyroxine</synonym>
    <synonym>3,3',5,5''-tetraiodo-L-Thyronine</synonym>
    <synonym>3,5,3',5'-Tetraiodothyronine</synonym>
    <synonym>D-Thyroxine</synonym>
    <synonym>DL-Thyroxin</synonym>
    <synonym>Henning</synonym>
    <synonym>L-3,5,3',5'-Tetraiodothyronine</synonym>
    <synonym>L-Thyroxin</synonym>
    <synonym>Laevothyroxinum</synonym>
    <synonym>Levothroid</synonym>
    <synonym>Levothyroxine sodium</synonym>
    <synonym>Levothyroxinum</synonym>
    <synonym>Levoxyl</synonym>
    <synonym>Prestwick_548</synonym>
    <synonym>Synthroid</synonym>
    <synonym>Tetraiodothyronine</synonym>
    <synonym>Tetramet</synonym>
    <synonym>THX</synonym>
    <synonym>Thyratabs</synonym>
    <synonym>Thyrax</synonym>
    <synonym>Thyreoideum</synonym>
    <synonym>Thyroxin</synonym>
    <synonym>Thyroxinal</synonym>
    <synonym>Thyroxine I 125</synonym>
    <synonym>Thyroxine iodine</synonym>
    <synonym>Allphar brand OF levothyroxine sodium</synonym>
    <synonym>Berlthyrox</synonym>
    <synonym>Delalande, levothyroxin</synonym>
    <synonym>Dexnon</synonym>
    <synonym>Eferox</synonym>
    <synonym>Eltroxin</synonym>
    <synonym>Kern brand OF levothyroxine sodium</synonym>
    <synonym>L-Thyrox</synonym>
    <synonym>L-Thyroxin henning</synonym>
    <synonym>L-Thyroxin beta</synonym>
    <synonym>L-Thyroxine roche</synonym>
    <synonym>Levothyroxin deladande</synonym>
    <synonym>Lévothyrox</synonym>
    <synonym>Merck lipha santé brand OF levothyroxine sodium</synonym>
    <synonym>Nourypharma brand OF levothyroxine sodium</synonym>
    <synonym>Oroxine</synonym>
    <synonym>Aventis brand OF levothyroxine sodium</synonym>
    <synonym>Euthyrox</synonym>
    <synonym>Eutirox</synonym>
    <synonym>Forest brand OF levothyroxine sodium</synonym>
    <synonym>Genpharm brand OF levothyroxine sodium</synonym>
    <synonym>GlaxoSmithKline brand OF levothyroxine sodium</synonym>
    <synonym>Goldshield brand OF levothyroxine sodium</synonym>
    <synonym>LThyroxin henning</synonym>
    <synonym>levo-T</synonym>
    <synonym>Sanofi synthelabo brand OF levothyroxine sodium</synonym>
    <synonym>Sigma brand OF levothyroxine sodium</synonym>
    <synonym>Synthrox</synonym>
    <synonym>Thevier</synonym>
    <synonym>Watson brand OF levothyroxine sodium</synonym>
    <synonym>Berlin chemie brand OF levothyroxine sodium</synonym>
    <synonym>Delalande brand OF levothyroxine sodium</synonym>
    <synonym>Eltroxine</synonym>
    <synonym>Hexal brand 2 OF levothyroxine sodium</synonym>
    <synonym>L Thyroxine roche</synonym>
    <synonym>Novothyral</synonym>
    <synonym>Tiroidine</synonym>
    <synonym>Vortex brand OF levothyroxine sodium</synonym>
    <synonym>Abbot brand OF levothyroxine sodium</synonym>
    <synonym>Berlin-chemie brand OF levothyroxine sodium</synonym>
    <synonym>Byk brand OF levothyroxine sodium</synonym>
    <synonym>Deladande, levothyroxin</synonym>
    <synonym>GlaxoWellcome brand OF levothyroxine sodium</synonym>
    <synonym>Henning berlin brand OF levothyroxine sodium</synonym>
    <synonym>Hexal brand 1 OF levothyroxine sodium</synonym>
    <synonym>L Thyrox</synonym>
    <synonym>L Thyroxin henning</synonym>
    <synonym>L Thyroxin beta</synonym>
    <synonym>L Thyroxine</synonym>
    <synonym>LThyroxin beta</synonym>
    <synonym>leo, Tiroxina</synonym>
    <synonym>levo T</synonym>
    <synonym>LevoT</synonym>
    <synonym>Levothyroid</synonym>
    <synonym>Levothyroxin delalande</synonym>
    <synonym>Levoxine</synonym>
    <synonym>Merck brand OF levothyroxine sodium</synonym>
    <synonym>Monarch brand OF levothyroxine sodium</synonym>
    <synonym>Mova brand OF levothyroxine sodium</synonym>
    <synonym>Novothyrox</synonym>
    <synonym>O-(4-Hydroxy-3,5-diiodophenyl) 3,5-diiodo-L-tyrosine</synonym>
    <synonym>O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodotyrosine</synonym>
    <synonym>Roche brand OF levothyroxine sodium</synonym>
    <synonym>Rudefsa brand OF levothyroxine sodium</synonym>
    <synonym>Sodium levothyroxine</synonym>
    <synonym>T4 Thyroid hormone</synonym>
    <synonym>Thyroid hormone, T4</synonym>
    <synonym>Tiroxina leo</synonym>
    <synonym>Unithroid</synonym>
    <synonym>Betapharm brand OF levothyroxine sodium</synonym>
  </synonyms>
  <chemical_formula>C15H11I4NO4</chemical_formula>
  <average_molecular_weight>776.87</average_molecular_weight>
  <monisotopic_moleculate_weight>776.686681525</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid</iupac_name>
  <traditional_iupac>levothyroxine</traditional_iupac>
  <cas_registry_number>51-48-9</cas_registry_number>
  <smiles>N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m0/s1</inchi>
  <inchikey>XUIIKFGFIJCVMT-LBPRGKRZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Phenylalanine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aryl iodides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Diarylethers</alternative_parent>
      <alternative_parent>Diphenylethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Iodobenzenes</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>O-iodophenols</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organoiodides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenol ethers</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-halophenol</substituent>
      <substituent>2-iodophenol</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Aryl iodide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Diaryl ether</substituent>
      <substituent>Diphenylether</substituent>
      <substituent>Ether</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Iodobenzene</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organoiodide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-halophenol</external_descriptor>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>L-phenylalanine derivative</external_descriptor>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>iodophenol</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
      <external_descriptor>thyroxine</external_descriptor>
      <external_descriptor>thyroxine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>235.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>776.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>776.686681525</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H11I4NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XUIIKFGFIJCVMT-LBPRGKRZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>126.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>49.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Thyroid Hormone Synthesis</name>
      <smpdb_id>SMP0087269</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>64449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450455</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <kegg_id>C01829</kegg_id>
  <chemspider_id>5614</chemspider_id>
  <pubchem_compound_id/>
  <drugbank_id>DB00451</drugbank_id>
  <pdbe_id/>
  <chebi_id>18332</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Levothyroxine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Martinovich, V. P.; Katok, Ya. M.; Fil'chenkov, N. A.; Sviridov, O. V. Conjugated synthesis of L-thyroxine and L-triiodothyronine. Vestsi Natsyyanal'nai Akademii Navuk Belarusi, Seryya Khimichnykh Navuk  (2004), (1),  85-92.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00546</protein_accession>
      <name>Type II iodothyronine deiodinase</name>
      <uniprot_id>Q5I3B2</uniprot_id>
      <gene_name>DIO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00548</protein_accession>
      <name>Type III iodothyronine deiodinase</name>
      <uniprot_id>Q5I3B1</uniprot_id>
      <gene_name>DIO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01916</protein_accession>
      <name>Solute carrier organic anion transporter family member 3A1</name>
      <uniprot_id>Q8HYW2</uniprot_id>
      <gene_name>SLCO3A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:24 UTC</creation_date>
  <update_date>2020-04-15 22:35:17 UTC</update_date>
  <accession>BMDB0000250</accession>
  <secondary_accessions>
    <accession>BMDB00250</accession>
  </secondary_accessions>
  <name>Pyrophosphate</name>
  <description/>
  <synonyms>
    <synonym>[(HO)2P(O)OP(O)(OH)2]</synonym>
    <synonym>Acide diphosphorique</synonym>
    <synonym>Diphosphorsaeure</synonym>
    <synonym>H4P2O7</synonym>
    <synonym>Pyrophosphoric acid</synonym>
    <synonym>Pyrophosphorsaeure</synonym>
    <synonym>Diphosphoric acid</synonym>
    <synonym>PPi</synonym>
    <synonym>Diphosphate</synonym>
    <synonym>PYROphosphATE</synonym>
    <synonym>Na4p2O7</synonym>
    <synonym>PPi CPD</synonym>
  </synonyms>
  <chemical_formula>H4O7P2</chemical_formula>
  <average_molecular_weight>177.9751</average_molecular_weight>
  <monisotopic_moleculate_weight>177.943225506</monisotopic_moleculate_weight>
  <iupac_name>(phosphonooxy)phosphonic acid</iupac_name>
  <traditional_iupac>pyrophosphoric acid</traditional_iupac>
  <cas_registry_number>2466-09-3</cas_registry_number>
  <smiles>OP(O)(=O)OP(O)(O)=O</smiles>
  <inchi>InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)</inchi>
  <inchikey>XPPKVPWEQAFLFU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as non-metal pyrophosphates. These are inorganic non-metallic compounds containing a pyrophosphate as its largest oxoanion.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Non-metal oxoanionic compounds</class>
    <sub_class>Non-metal pyrophosphates</sub_class>
    <direct_parent>Non-metal pyrophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Inorganic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Inorganic oxide</substituent>
      <substituent>Non-metal pyrophosphate</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>acyclic phosphorus acid anhydride</external_descriptor>
      <external_descriptor>phosphorus oxoacid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(phosphonooxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>177.9751</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>177.943225506</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OP(O)(=O)OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>H4O7P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XPPKVPWEQAFLFU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>124.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Activation of cAMP-dependent protein kinase, PKA</name>
      <smpdb_id>SMP0108201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Biotin Metabolism</name>
      <smpdb_id>SMP0087183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Butyrate Metabolism</name>
      <smpdb_id>SMP0087185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis</name>
      <smpdb_id>SMP0072032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:0)</name>
      <smpdb_id>SMP0077151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:0)</name>
      <smpdb_id>SMP0077153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:0)</name>
      <smpdb_id>SMP0077171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:0)</name>
      <smpdb_id>SMP0077173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077256</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077257</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077258</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077259</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077260</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077261</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077262</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077263</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077264</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077265</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077266</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077267</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077268</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077269</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077271</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077272</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077273</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077274</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077275</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077276</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077277</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077278</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077279</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077280</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077281</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077282</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077283</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077284</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077285</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077286</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077287</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077288</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077292</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077297</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077300</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077302</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077304</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077305</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077307</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077308</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077309</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077311</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077313</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077314</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077315</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077316</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077317</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077318</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077321</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077322</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077323</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077324</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077325</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077326</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077327</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077328</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077329</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077330</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077331</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077332</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077333</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077334</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077335</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077338</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077339</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077340</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077341</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077342</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077343</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077344</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077345</smpdb_id>
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    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077347</smpdb_id>
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    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077348</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077349</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077350</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077351</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077352</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077353</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077354</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077355</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077356</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077357</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077358</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077359</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077360</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077361</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077362</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077363</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077364</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077365</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077366</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077367</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077368</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077369</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077370</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077371</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077372</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077373</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077374</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077375</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077376</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077378</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077379</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077380</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077381</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077382</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077383</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077402</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077403</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077406</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077407</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077408</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077409</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077410</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077411</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077412</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077413</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077414</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077415</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077416</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077417</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077418</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077419</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077420</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077421</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077422</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077423</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077424</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077425</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077426</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077427</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077428</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077429</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077430</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077442</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077444</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077445</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077446</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077447</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077449</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077450</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077451</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077452</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077453</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077455</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077456</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077461</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077465</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077475</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077479</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077484</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077485</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077487</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077488</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077489</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077490</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077491</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077492</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077493</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077494</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077495</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077496</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077497</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077498</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077499</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077500</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077501</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077502</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077505</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077509</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077511</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077512</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077513</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077514</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077515</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077516</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077517</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077518</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077519</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077520</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077521</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077522</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077523</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077524</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077525</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077526</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077527</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077528</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077529</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077530</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077531</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077532</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077533</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077534</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077535</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077536</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077537</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077540</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077545</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077546</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077547</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077548</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077549</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077550</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077551</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077552</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077553</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077554</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077555</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077556</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077557</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077558</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077559</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077560</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077561</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077562</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077563</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077564</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077566</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077567</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077569</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077573</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077582</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077583</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077584</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077586</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077587</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077600</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077603</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077604</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077605</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077606</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077607</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077608</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077609</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077653</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077654</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077655</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077656</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077657</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077659</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077704</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077724</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077725</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077731</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077732</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077733</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077734</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077735</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077736</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077737</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077738</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077739</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077740</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077742</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077744</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077745</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077746</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077747</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077748</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077749</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077750</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077751</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077752</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077753</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077754</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077755</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077756</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077757</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077758</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077759</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077760</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077761</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077762</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077763</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077764</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077765</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077766</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077767</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077768</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077769</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077770</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077771</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077772</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077773</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077774</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077775</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077776</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077777</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077778</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077779</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077780</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077781</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077782</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077783</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077784</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077785</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077786</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077787</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077788</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077789</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077790</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077791</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077792</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077793</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077794</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077795</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077796</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077797</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077798</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077799</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077800</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077801</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077803</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077804</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077805</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077806</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077807</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077808</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077809</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077810</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077816</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077817</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077818</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077819</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077820</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077821</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077822</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077823</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077824</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077825</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077826</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077827</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077828</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077829</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077830</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077831</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077832</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077833</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077834</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077835</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077836</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077837</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077838</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077839</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077840</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077841</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077842</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077843</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077844</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077845</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077846</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077847</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077848</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077849</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077850</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077851</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077852</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077853</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077854</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077855</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077856</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077857</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077858</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077859</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077860</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077861</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077862</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077863</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077864</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077865</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077866</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077867</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077868</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077869</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077870</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077871</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077872</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077873</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077874</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077875</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077876</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077877</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077878</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077879</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077880</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077881</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077882</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077884</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077885</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077886</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077887</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077888</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077889</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077890</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077891</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077892</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077893</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077894</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077895</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077896</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077897</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077898</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077899</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077901</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077902</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077903</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077904</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077905</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077906</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077907</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077908</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077909</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077910</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077911</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077912</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077913</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077914</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077915</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077916</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077917</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077918</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077919</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077920</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077921</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077922</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077923</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077924</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077925</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077926</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077927</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077928</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077929</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077932</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077933</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077934</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077937</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077939</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077941</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077942</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077943</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077944</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077945</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077946</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077947</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077948</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077950</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077951</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077953</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077956</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077959</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077970</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077971</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077973</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077974</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078115</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078116</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078117</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078118</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078120</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078121</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078122</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078123</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078124</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078125</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078126</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/16:0)</name>
      <smpdb_id>SMP0078130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:0)</name>
      <smpdb_id>SMP0078132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078173</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078197</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078198</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078199</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078200</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078201</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078202</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078203</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078204</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078205</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078206</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078207</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078208</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078209</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078210</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078211</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078212</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078213</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078214</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078215</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078216</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078217</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078218</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:0)</name>
      <smpdb_id>SMP0078219</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078220</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078221</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078222</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078223</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078224</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078225</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078226</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078227</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078228</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078229</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078230</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078232</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078233</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078234</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078235</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078236</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078237</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078238</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078239</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078240</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078241</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078242</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078243</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078244</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078245</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078246</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078247</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078248</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078249</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078250</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078251</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078252</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078253</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078254</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078255</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078256</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078257</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078258</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078259</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078260</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078261</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078262</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078263</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078264</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078265</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078266</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078267</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078268</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078269</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078270</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078271</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078272</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078273</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078274</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078275</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078276</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078277</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078278</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078279</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078280</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078281</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078282</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078283</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078285</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078286</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078287</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078288</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078289</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078290</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078292</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078297</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078298</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078299</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078300</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078301</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078302</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078303</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078304</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078305</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078306</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078307</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078308</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078309</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078310</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078311</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078312</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078313</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078314</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078315</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078316</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078317</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078318</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078319</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078320</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078321</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078322</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078323</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078324</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078326</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078327</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078328</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078329</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078330</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078331</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078332</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078333</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078336</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078350</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078351</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078352</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078353</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078354</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078355</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078356</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078357</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078358</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078359</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078360</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078361</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078362</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078363</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078364</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078365</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078375</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078376</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078377</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078379</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078381</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078385</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078386</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078388</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078389</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078390</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078391</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078392</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078393</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078394</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078395</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078396</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078397</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078398</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078399</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078400</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078401</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078404</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078405</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078406</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078407</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078408</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078409</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078411</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078412</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078413</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078415</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078417</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078418</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078419</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078420</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078421</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078422</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078423</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078424</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078425</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078426</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078427</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078428</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078429</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078430</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078431</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078432</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078433</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078434</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078435</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078436</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078437</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078438</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078439</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078440</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078441</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078443</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078444</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078446</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078447</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078448</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078449</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078450</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078451</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078452</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078453</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078454</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078455</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078456</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078457</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078458</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078459</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078460</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078461</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078462</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078463</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078464</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078465</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078466</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078467</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078468</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078470</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078471</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078475</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078482</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078485</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078488</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078489</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078490</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078492</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078493</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078494</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078495</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078496</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078497</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078498</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078499</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078500</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078501</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078502</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078503</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078506</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078507</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078508</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078509</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078510</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078516</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078517</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078518</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078519</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078520</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078670</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078671</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078672</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078673</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078674</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078675</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078677</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078684</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078685</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078692</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078693</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078694</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078697</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078699</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078700</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078707</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078708</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078709</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078737</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078738</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078744</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078745</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078746</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078747</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078748</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078749</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078750</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078751</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078752</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078753</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078754</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078755</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078756</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078757</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078758</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078760</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078761</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078762</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078768</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078778</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078798</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078804</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078805</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078806</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078808</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078809</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078810</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078811</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078812</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078814</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078815</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078819</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078820</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078821</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078822</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078823</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078824</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078825</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078826</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078827</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078828</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078829</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079141</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079143</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079145</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079148</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079149</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0079152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079175</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079176</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079178</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079179</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079180</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079201</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079202</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079203</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079204</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079205</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079206</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079207</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079208</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079209</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079210</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079211</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079212</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079213</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079214</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079215</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079216</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079217</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079218</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079219</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079220</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079221</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079222</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079223</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079224</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079225</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079226</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079227</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079228</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079229</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079230</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079231</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079232</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079233</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079234</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079235</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079237</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079238</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079239</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079240</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079241</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079242</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079243</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079244</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079246</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079247</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079249</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079250</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079251</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079252</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079253</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079254</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079255</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079256</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079257</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079258</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079259</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079260</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079261</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079262</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079263</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079264</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079265</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079266</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079267</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079268</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079269</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079270</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079271</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079272</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079273</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079274</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079275</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079276</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079281</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079282</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079283</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079284</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079285</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079286</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079287</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079288</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079289</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079290</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079291</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079292</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079293</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079294</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079295</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079296</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079297</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079298</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079300</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079304</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079306</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079307</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079308</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079309</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079310</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079311</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079312</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079313</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079314</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079315</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079316</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079317</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079318</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079319</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079320</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079321</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079322</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079323</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079324</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079325</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079326</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079327</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079328</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079329</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079330</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079331</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079332</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079333</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079334</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079335</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079336</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079337</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079338</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079339</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079340</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079341</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079342</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079343</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079344</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079346</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079347</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079348</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079349</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079419</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079420</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079421</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079422</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079423</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079424</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079425</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079426</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079427</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079428</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079429</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079430</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079431</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079432</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079433</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079434</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079435</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079436</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079437</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079438</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079440</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079441</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079442</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079444</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079445</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079454</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079456</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079459</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079464</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079465</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079466</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079467</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079468</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079469</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079470</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079471</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079472</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079473</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079474</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079475</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079476</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079477</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079478</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079479</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079480</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079481</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079482</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079483</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079484</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079485</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079486</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079487</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079488</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079489</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079490</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079491</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079492</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079493</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079494</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079495</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079496</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079497</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079498</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079499</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079500</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079501</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079502</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079503</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079504</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079505</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079506</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079507</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079508</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079509</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079510</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079511</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079512</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079513</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079514</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079515</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079516</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079517</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079518</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079519</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079520</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079521</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079522</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079523</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079524</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079525</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079526</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079527</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079528</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079529</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079530</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079531</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079532</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079533</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079534</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079535</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079536</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079537</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079538</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079539</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079540</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079542</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079543</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079544</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079545</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079546</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079547</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079548</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079549</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079550</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079551</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079552</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079553</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079554</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079555</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079556</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079557</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079558</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079559</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079560</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079562</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079563</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079564</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079574</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079575</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079577</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079578</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079579</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079580</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079584</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0079603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0079604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079638</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079762</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079773</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079774</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079775</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079776</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079777</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079778</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079779</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079780</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079781</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079782</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079783</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079784</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079785</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079786</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079787</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079788</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079789</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079790</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079791</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079792</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079793</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079794</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079795</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079796</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079797</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079798</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079799</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079800</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079801</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079802</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079803</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079804</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079805</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079806</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079807</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079808</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079809</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079810</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079811</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079814</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079815</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079816</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079817</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079818</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079819</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079820</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079821</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079822</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079823</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079824</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079826</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079827</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079828</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079829</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079830</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079831</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079832</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079833</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079834</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079835</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079836</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079837</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079838</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079839</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079840</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079841</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079842</smpdb_id>
      <kegg_map_id/>
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    <pathway>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079973</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079975</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079976</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079977</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079978</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079999</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080000</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080001</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080004</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080008</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080009</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080010</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080011</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080012</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080013</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080014</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0080015</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080016</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080017</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0080018</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0080019</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080020</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0080021</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080022</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080023</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080024</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080025</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080026</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080028</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080029</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080030</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080031</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080032</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080033</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080034</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080035</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080036</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080228</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080229</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080230</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080231</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080232</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080233</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080235</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080236</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080237</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080238</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080239</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080240</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080241</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080242</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080243</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080244</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080245</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080246</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080247</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080248</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080250</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080251</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080252</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080253</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080258</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080262</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080263</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080264</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080265</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080266</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080271</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080274</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080275</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080276</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080277</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080282</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080283</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080287</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080288</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080293</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080356</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080360</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080371</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080373</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080374</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080375</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080393</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080394</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080395</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080396</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080398</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080399</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080400</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080401</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080402</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080408</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080409</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080410</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080411</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080412</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080413</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080414</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080418</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080419</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080420</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Corticotropin Activation of Cortisol Production</name>
      <smpdb_id>SMP0108167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dopamine Activation of Neurological Reward System</name>
      <smpdb_id>SMP0107994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ethanol Degradation</name>
      <smpdb_id>SMP0087192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 4 and Serotonin</name>
      <smpdb_id>SMP0108169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 6 and Serotonin</name>
      <smpdb_id>SMP0108172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 7 and Serotonin</name>
      <smpdb_id>SMP0108170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2a and Adenosine</name>
      <smpdb_id>SMP0108174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2b and Adenosine</name>
      <smpdb_id>SMP0108178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through FSH Receptor and Follicle Stimulating Hormone</name>
      <smpdb_id>SMP0108183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Histamine H2 Receptor and Histamine</name>
      <smpdb_id>SMP0107995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through LHCGR Receptor and Luteinizing Hormone/Choriogonadotropin</name>
      <smpdb_id>SMP0108184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through PGD2 receptor and Prostaglandin D2</name>
      <smpdb_id>SMP0107997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Prostacyclin Receptor and Prostacyclin</name>
      <smpdb_id>SMP0107998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ion Channels and Their Functional Role in Vascular Endothelium</name>
      <smpdb_id>SMP0108207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA1 Signalling</name>
      <smpdb_id>SMP0108191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA2 Signalling</name>
      <smpdb_id>SMP0108193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA3 Signalling</name>
      <smpdb_id>SMP0108194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA4 Signalling</name>
      <smpdb_id>SMP0108196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA5 Signalling</name>
      <smpdb_id>SMP0108198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA6 Signalling</name>
      <smpdb_id>SMP0108199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pantothenate and CoA Biosynthesis</name>
      <smpdb_id>SMP0087207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylacetate Metabolism</name>
      <smpdb_id>SMP0087208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis</name>
      <smpdb_id>SMP0072037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:0)</name>
      <smpdb_id>SMP0080430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0080431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/15:0)</name>
      <smpdb_id>SMP0080432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:0)</name>
      <smpdb_id>SMP0080433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0080434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:0)</name>
      <smpdb_id>SMP0080435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0080436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0080437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:0)</name>
      <smpdb_id>SMP0080442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0080443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:0)</name>
      <smpdb_id>SMP0080450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0080451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:0)</name>
      <smpdb_id>SMP0080457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0080458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0080459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0080460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0080461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/15:0)</name>
      <smpdb_id>SMP0080487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:0)</name>
      <smpdb_id>SMP0080488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0080489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:0)</name>
      <smpdb_id>SMP0080490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0080491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0080492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:0)</name>
      <smpdb_id>SMP0080497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0080498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:0)</name>
      <smpdb_id>SMP0080505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0080506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:0)</name>
      <smpdb_id>SMP0080512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0080513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:0)</name>
      <smpdb_id>SMP0080514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0080515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:0)</name>
      <smpdb_id>SMP0080516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0080517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0080518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:0)</name>
      <smpdb_id>SMP0080523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0080524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:0)</name>
      <smpdb_id>SMP0080531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0080532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:0)</name>
      <smpdb_id>SMP0080538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0080539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:0)</name>
      <smpdb_id>SMP0080565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0080566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0080567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:0)</name>
      <smpdb_id>SMP0080572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0080573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:0)</name>
      <smpdb_id>SMP0080580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0080581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:0)</name>
      <smpdb_id>SMP0080587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0080588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0080595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:0)</name>
      <smpdb_id>SMP0080712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0080713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:0)</name>
      <smpdb_id>SMP0080720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0080721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:0)</name>
      <smpdb_id>SMP0080727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0080728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0080765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0080772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:0)</name>
      <smpdb_id>SMP0080820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0080821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:0)</name>
      <smpdb_id>SMP0080827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0080828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0080835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:0)</name>
      <smpdb_id>SMP0080864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0080865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis</name>
      <smpdb_id>SMP0072048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:0)</name>
      <smpdb_id>SMP0082233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0082234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/15:0)</name>
      <smpdb_id>SMP0082235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:0)</name>
      <smpdb_id>SMP0082236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0082237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:0)</name>
      <smpdb_id>SMP0082238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0082239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0082240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:0)</name>
      <smpdb_id>SMP0082245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0082246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:0)</name>
      <smpdb_id>SMP0082253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0082254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:0)</name>
      <smpdb_id>SMP0082260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0082261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0082262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0082263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0082264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/15:0)</name>
      <smpdb_id>SMP0082290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:0)</name>
      <smpdb_id>SMP0082291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0082292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:0)</name>
      <smpdb_id>SMP0082293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0082294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0082295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:0)</name>
      <smpdb_id>SMP0082300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0082301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:0)</name>
      <smpdb_id>SMP0082308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0082309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:0)</name>
      <smpdb_id>SMP0082315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0082316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:0)</name>
      <smpdb_id>SMP0082317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0082318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:0)</name>
      <smpdb_id>SMP0082319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0082320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0082321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:0)</name>
      <smpdb_id>SMP0082326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0082327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:0)</name>
      <smpdb_id>SMP0082334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0082335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:0)</name>
      <smpdb_id>SMP0082341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0082342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:0)</name>
      <smpdb_id>SMP0082368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0082369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0082370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:0)</name>
      <smpdb_id>SMP0082375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0082376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:0)</name>
      <smpdb_id>SMP0082383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0082384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:0)</name>
      <smpdb_id>SMP0082390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0082391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0082398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:0)</name>
      <smpdb_id>SMP0082520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0082521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:0)</name>
      <smpdb_id>SMP0082528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0082529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:0)</name>
      <smpdb_id>SMP0082535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0082536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0082574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0082581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:0)</name>
      <smpdb_id>SMP0082629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0082630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:0)</name>
      <smpdb_id>SMP0082636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0082637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0082644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:0)</name>
      <smpdb_id>SMP0082671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0082672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Alanine</name>
      <smpdb_id>SMP0119369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Arginine</name>
      <smpdb_id>SMP0119383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Asparagine</name>
      <smpdb_id>SMP0119385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Aspartic Acid</name>
      <smpdb_id>SMP0119386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Cysteine</name>
      <smpdb_id>SMP0119388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Glutamic Acid</name>
      <smpdb_id>SMP0119390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Glutamine</name>
      <smpdb_id>SMP0119389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Glycine</name>
      <smpdb_id>SMP0119391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Histidine</name>
      <smpdb_id>SMP0119392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Isoleucine</name>
      <smpdb_id>SMP0119393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Leucine</name>
      <smpdb_id>SMP0119403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Lysine</name>
      <smpdb_id>SMP0119404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Methionine</name>
      <smpdb_id>SMP0119405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Phenylalanine</name>
      <smpdb_id>SMP0119406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Proline</name>
      <smpdb_id>SMP0119407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Serine</name>
      <smpdb_id>SMP0119409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Threonine</name>
      <smpdb_id>SMP0119410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Tryptophan</name>
      <smpdb_id>SMP0119414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Tyrosine</name>
      <smpdb_id>SMP0119416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Valine</name>
      <smpdb_id>SMP0119417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Riboflavin Metabolism</name>
      <smpdb_id>SMP0087211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Selenoamino Acid Metabolism</name>
      <smpdb_id>SMP0087161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sulfate/Sulfite Metabolism</name>
      <smpdb_id>SMP0087216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ubiquinone Biosynthesis</name>
      <smpdb_id>SMP0087215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vasopressin Regulation of Water Homeostasis</name>
      <smpdb_id>SMP0108181</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218084</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id/>
  <drugbank_id>DB04160</drugbank_id>
  <foodb_id/>
  <kegg_id>C00013</kegg_id>
  <pdbe_id/>
  <chebi_id>29888</chebi_id>
  <pubchem_compound_id>1023</pubchem_compound_id>
  <meta_cyc_id/>
  <knapsack_id>C00019561</knapsack_id>
  <wikipedia_id>Pyrophosphate</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Dittmer, Donald C.; Silverstein, V. Opshelor.  Production of pyrophosphate from S-n-butyl phosphorothioate.    Journal of Organic Chemistry  (1961),  26  4706-7. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00029</protein_accession>
      <name>Guanylate cyclase soluble subunit beta-1</name>
      <uniprot_id>P16068</uniprot_id>
      <gene_name>GUCY1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00079</protein_accession>
      <name>Phosphatidate cytidylyltransferase 2</name>
      <uniprot_id>A0JNC1</uniprot_id>
      <gene_name>CDS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00105</protein_accession>
      <name>Nicotinamide mononucleotide adenylyltransferase 1</name>
      <uniprot_id>Q0VD50</uniprot_id>
      <gene_name>NMNAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00106</protein_accession>
      <name>Nicotinamide mononucleotide adenylyltransferase 2</name>
      <uniprot_id>Q0VC59</uniprot_id>
      <gene_name>NMNAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00108</protein_accession>
      <name>Adenine phosphoribosyltransferase</name>
      <uniprot_id>Q56JW4</uniprot_id>
      <gene_name>APRT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00174</protein_accession>
      <name>S-adenosylmethionine synthetase</name>
      <uniprot_id>A7E3T7</uniprot_id>
      <gene_name>MAT2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00237</protein_accession>
      <name>Argininosuccinate synthase</name>
      <uniprot_id>P14568</uniprot_id>
      <gene_name>ASS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00367</protein_accession>
      <name>Acyl-CoA synthetase short-chain family member 3, mitochondrial</name>
      <uniprot_id>A7MB45</uniprot_id>
      <gene_name>ACSS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00392</protein_accession>
      <name>Ethanolamine-phosphate cytidylyltransferase</name>
      <uniprot_id>Q5EA75</uniprot_id>
      <gene_name>PCYT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00403</protein_accession>
      <name>S-adenosylmethionine synthetase isoform type-1</name>
      <uniprot_id>Q2KJC6</uniprot_id>
      <gene_name>MAT1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00436</protein_accession>
      <name>Atrial natriuretic peptide receptor B</name>
      <uniprot_id>P46197</uniprot_id>
      <gene_name>NPR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00440</protein_accession>
      <name>Hypoxanthine-guanine phosphoribosyltransferase</name>
      <uniprot_id>Q3SZ18</uniprot_id>
      <gene_name>HPRT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00442</protein_accession>
      <name>Adenylate cyclase type 1</name>
      <uniprot_id>P19754</uniprot_id>
      <gene_name>ADCY1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00466</protein_accession>
      <name>Adenylate cyclase type 7</name>
      <uniprot_id>Q29450</uniprot_id>
      <gene_name>ADCY7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00472</protein_accession>
      <name>DNA polymerase beta</name>
      <uniprot_id>Q27958</uniprot_id>
      <gene_name>POLB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00486</protein_accession>
      <name>Nucleoside diphosphate kinase 7</name>
      <uniprot_id>Q5E9Y9</uniprot_id>
      <gene_name>NME7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00490</protein_accession>
      <name>Inorganic pyrophosphatase</name>
      <uniprot_id>P37980</uniprot_id>
      <gene_name>PPA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00503</protein_accession>
      <name>Nucleoside diphosphate kinase A 1</name>
      <uniprot_id>P52174</uniprot_id>
      <gene_name>NME1-1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00507</protein_accession>
      <name>Nucleoside diphosphate kinase B</name>
      <uniprot_id>Q3T0Q4</uniprot_id>
      <gene_name>NME2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00508</protein_accession>
      <name>Inosine triphosphate pyrophosphatase</name>
      <uniprot_id>Q2KIC5</uniprot_id>
      <gene_name>ITPA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00509</protein_accession>
      <name>Acyl-coenzyme A synthetase ACSM1, mitochondrial</name>
      <uniprot_id>Q9BEA2</uniprot_id>
      <gene_name>ACSM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00518</protein_accession>
      <name>Nucleoside diphosphate kinase A 2</name>
      <uniprot_id>P52175</uniprot_id>
      <gene_name>NME1-2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00563</protein_accession>
      <name>Asparagine synthetase [glutamine-hydrolyzing]</name>
      <uniprot_id>Q1LZA3</uniprot_id>
      <gene_name>ASNS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00613</protein_accession>
      <name>dCTP pyrophosphatase 1</name>
      <uniprot_id>Q32KY6</uniprot_id>
      <gene_name>DCTPP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00635</protein_accession>
      <name>Nicotinate phosphoribosyltransferase</name>
      <uniprot_id>A5PK51</uniprot_id>
      <gene_name>NAPRT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00636</protein_accession>
      <name>Nicotinate-nucleotide pyrophosphorylase [carboxylating]</name>
      <uniprot_id>Q3T063</uniprot_id>
      <gene_name>QPRT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00652</protein_accession>
      <name>Protein prune homolog</name>
      <uniprot_id>Q5E9Y6</uniprot_id>
      <gene_name>PRUNE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00789</protein_accession>
      <name>N-acylneuraminate cytidylyltransferase</name>
      <uniprot_id>Q3SZM5</uniprot_id>
      <gene_name>CMAS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00852</protein_accession>
      <name>Glutamine-dependent NAD(+) synthetase</name>
      <uniprot_id>Q3ZBF0</uniprot_id>
      <gene_name>NADSYN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00980</protein_accession>
      <name>Lysyl-tRNA synthetase</name>
      <uniprot_id>Q3T0N2</uniprot_id>
      <gene_name>KARS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01004</protein_accession>
      <name>Uridine 5'-monophosphate synthase</name>
      <uniprot_id>P31754</uniprot_id>
      <gene_name>UMPS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01085</protein_accession>
      <name>DNA-directed RNA polymerase</name>
      <uniprot_id>A6QLS0</uniprot_id>
      <gene_name>POLR1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01086</protein_accession>
      <name>Ribonucleoside-diphosphate reductase</name>
      <uniprot_id>Q32LP1</uniprot_id>
      <gene_name>RRM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01087</protein_accession>
      <name>DNA-directed RNA polymerase</name>
      <uniprot_id>A5PJW8</uniprot_id>
      <gene_name>POLR2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01108</protein_accession>
      <name>DNA ligase</name>
      <uniprot_id>Q2T9Y5</uniprot_id>
      <gene_name>LIG3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01109</protein_accession>
      <name>Retinal guanylyl cyclase 2</name>
      <uniprot_id>O02740</uniprot_id>
      <gene_name>GUCY2F</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01110</protein_accession>
      <name>Poly(A) RNA polymerase GLD2</name>
      <uniprot_id>Q2HJ44</uniprot_id>
      <gene_name>PAPD4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01111</protein_accession>
      <name>DNA polymerase epsilon subunit 2</name>
      <uniprot_id>A7YWS7</uniprot_id>
      <gene_name>POLE2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01112</protein_accession>
      <name>DNA polymerase delta subunit 2</name>
      <uniprot_id>P49004</uniprot_id>
      <gene_name>POLD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01113</protein_accession>
      <name>DNA ligase</name>
      <uniprot_id>A4IFC8</uniprot_id>
      <gene_name>LIG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01114</protein_accession>
      <name>DNA polymerase epsilon subunit 4</name>
      <uniprot_id>A6QQ14</uniprot_id>
      <gene_name>POLE4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01115</protein_accession>
      <name>Poly(A) polymerase alpha</name>
      <uniprot_id>P25500</uniprot_id>
      <gene_name>PAPOLA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01116</protein_accession>
      <name>Nucleoside diphosphate kinase</name>
      <uniprot_id>A1A4N9</uniprot_id>
      <gene_name>NME1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01117</protein_accession>
      <name>Guanylate cyclase soluble subunit alpha-1</name>
      <uniprot_id>P19687</uniprot_id>
      <gene_name>GUCY1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01118</protein_accession>
      <name>DNA polymerase epsilon subunit 3</name>
      <uniprot_id>Q3SZN5</uniprot_id>
      <gene_name>POLE3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01119</protein_accession>
      <name>Mannose-1-phosphate guanyltransferase beta</name>
      <uniprot_id>Q2YDJ9</uniprot_id>
      <gene_name>GMPPB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01120</protein_accession>
      <name>Long-chain-fatty-acid--CoA ligase ACSBG1</name>
      <uniprot_id>Q2KHW5</uniprot_id>
      <gene_name>ACSBG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01121</protein_accession>
      <name>DNA polymerase subunit gamma-2, mitochondrial</name>
      <uniprot_id>Q0VC30</uniprot_id>
      <gene_name>POLG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01122</protein_accession>
      <name>Guanylate cyclase</name>
      <uniprot_id>O77690</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01123</protein_accession>
      <name>Nucleoside diphosphate kinase</name>
      <uniprot_id>Q56JV4</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01124</protein_accession>
      <name>Phospholysine phosphohistidine inorganic pyrophosphate phosphatase</name>
      <uniprot_id>Q0VD18</uniprot_id>
      <gene_name>LHPP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01125</protein_accession>
      <name>Retinal guanylyl cyclase 1</name>
      <uniprot_id>P55203</uniprot_id>
      <gene_name>GUCY2D</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01126</protein_accession>
      <name>DNA polymerase delta catalytic subunit</name>
      <uniprot_id>P28339</uniprot_id>
      <gene_name>POLD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01127</protein_accession>
      <name>Nucleoside diphosphate kinase</name>
      <uniprot_id>A5PK70</uniprot_id>
      <gene_name>NME3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01985</protein_accession>
      <name>Mitochondrial thiamine pyrophosphate carrier</name>
      <uniprot_id>Q29RM1</uniprot_id>
      <gene_name>SLC25A19</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02580</protein_accession>
      <name>Pleckstrin homology domain-containing family A member 2</name>
      <uniprot_id>Q3ZBA3</uniprot_id>
      <gene_name>PLEKHA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:25 UTC</creation_date>
  <update_date>2020-04-16 20:39:48 UTC</update_date>
  <accession>BMDB0000251</accession>
  <secondary_accessions>
    <accession>BMDB00251</accession>
  </secondary_accessions>
  <name>Taurine</name>
  <description>Taurine, also known as taufon or 2-sulfoethylamine, belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom). Taurine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Taurine exists in all living species, ranging from bacteria to humans. Taurine is a potentially toxic compound. Taurine has been found to be associated with several diseases known as perillyl alcohol administration for cancer treatment, schizophrenia, irritable bowel syndrome, and sulfite oxidase deficiency, isolated; also taurine has been linked to the inborn metabolic disorders including maple syrup urine disease.</description>
  <synonyms>
    <synonym>2-Aminoethanesulfonic acid</synonym>
    <synonym>2-Aminoethyl sulfonate</synonym>
    <synonym>Aminoethylsulfonic acid</synonym>
    <synonym>beta-Aminoethylsulfonic acid</synonym>
    <synonym>2-Aminoethanesulfonate</synonym>
    <synonym>2-Aminoethanesulphonate</synonym>
    <synonym>2-Aminoethanesulphonic acid</synonym>
    <synonym>2-Aminoethyl sulfonic acid</synonym>
    <synonym>2-Aminoethyl sulphonate</synonym>
    <synonym>2-Aminoethyl sulphonic acid</synonym>
    <synonym>Aminoethylsulfonate</synonym>
    <synonym>Aminoethylsulphonate</synonym>
    <synonym>Aminoethylsulphonic acid</synonym>
    <synonym>b-Aminoethylsulfonate</synonym>
    <synonym>b-Aminoethylsulfonic acid</synonym>
    <synonym>b-Aminoethylsulphonate</synonym>
    <synonym>b-Aminoethylsulphonic acid</synonym>
    <synonym>beta-Aminoethylsulfonate</synonym>
    <synonym>beta-Aminoethylsulphonate</synonym>
    <synonym>beta-Aminoethylsulphonic acid</synonym>
    <synonym>Β-aminoethylsulfonate</synonym>
    <synonym>Β-aminoethylsulfonic acid</synonym>
    <synonym>Β-aminoethylsulphonate</synonym>
    <synonym>Β-aminoethylsulphonic acid</synonym>
    <synonym>1-Aminoethane-2-sulfonate</synonym>
    <synonym>1-Aminoethane-2-sulfonic acid</synonym>
    <synonym>2-Aminoethylsulfonate</synonym>
    <synonym>2-Aminoethylsulfonic acid</synonym>
    <synonym>2-Sulfoethylamine</synonym>
    <synonym>Taurine hydrochloride</synonym>
    <synonym>Taurine zinc salt (2:1)</synonym>
    <synonym>Taurine, monopotassium salt</synonym>
    <synonym>Taufon</synonym>
    <synonym>Tauphon</synonym>
  </synonyms>
  <chemical_formula>C2H7NO3S</chemical_formula>
  <average_molecular_weight>125.147</average_molecular_weight>
  <monisotopic_moleculate_weight>125.014663785</monisotopic_moleculate_weight>
  <iupac_name>2-aminoethane-1-sulfonic acid</iupac_name>
  <traditional_iupac>taurine</traditional_iupac>
  <cas_registry_number>107-35-7</cas_registry_number>
  <smiles>NCCS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)</inchi>
  <inchikey>XOAAWQZATWQOTB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic sulfonic acids and derivatives</class>
    <sub_class>Organosulfonic acids and derivatives</sub_class>
    <direct_parent>Organosulfonic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkanesulfonic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Sulfonyls</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkanesulfonic acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Sulfonyl</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>amino sulfonic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>300 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>80.7 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-aminoethane-1-sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>125.147</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>125.014663785</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H7NO3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H7NO3S/c3-1-2-7(4,5)6/h1-3H2,(H,4,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XOAAWQZATWQOTB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>24.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Taurine and Hypotaurine Metabolism</name>
      <smpdb_id>SMP0087214</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3763</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>80+/-20</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>33-41</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>33-47</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>2243+/-1186</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>480+/-146</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10 - 30</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>NRC. 1989. Recommended Dietary Allowances.  10th ed. Natl. Acad. Press, Washington, DC.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>327 - 621</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>37 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>41 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>38 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>37 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>8+/-7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1.07 +/- 0.007</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>36.2 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>844+/-301</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>1510+/-296</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>1091</chemspider_id>
  <drugbank_id>DB01956</drugbank_id>
  <foodb_id>FDB003191</foodb_id>
  <kegg_id>C00245</kegg_id>
  <pdbe_id/>
  <chebi_id>15891</chebi_id>
  <pubchem_compound_id>1123</pubchem_compound_id>
  <meta_cyc_id>TAURINE</meta_cyc_id>
  <knapsack_id>C00048188</knapsack_id>
  <wikipedia_id>Taurine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34373</bigg_id>
  <metlin_id>31</metlin_id>
  <synthesis_reference>Hu, Libo; Zhu, Hui; Du, Da-Ming; Xu, Jiaxi. Efficient synthesis of taurine and structurally diverse substituted taurines from aziridines. Journal of Organic Chemistry  (2007),  72(12),  4543-4546.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>NRC. 1989. Recommended Dietary Allowances.  10th ed. Natl. Acad. Press, Washington, DC.</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01848</protein_accession>
      <name>Glycine receptor subunit alpha-1</name>
      <uniprot_id>P57695</uniprot_id>
      <gene_name>GLRA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02539</protein_accession>
      <name>Sodium- and chloride-dependent taurine transporter</name>
      <uniprot_id>Q9MZ34</uniprot_id>
      <gene_name>SLC6A6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:26 UTC</creation_date>
  <update_date>2020-04-16 20:39:16 UTC</update_date>
  <accession>BMDB0000252</accession>
  <secondary_accessions>
    <accession>BMDB00252</accession>
  </secondary_accessions>
  <name>Sphingosine</name>
  <description>Sphingosine, also known as (4e)-sphingenine, belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Sphingosine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Sphingosine exists in all eukaryotes, ranging from yeast to humans.</description>
  <synonyms>
    <synonym>(-)-D-Erythro-sphingosine</synonym>
    <synonym>(2S,3R)-Sphingosine</synonym>
    <synonym>(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol</synonym>
    <synonym>(4E)-Sphingenine</synonym>
    <synonym>4-Sphingenine</synonym>
    <synonym>4-trans-Sphingenine</synonym>
    <synonym>[R-[R*,s*-(e)]]-2-amino-4-octadecene-1,3-diol</synonym>
  </synonyms>
  <chemical_formula>C18H37NO2</chemical_formula>
  <average_molecular_weight>299.4919</average_molecular_weight>
  <monisotopic_moleculate_weight>299.282429433</monisotopic_moleculate_weight>
  <iupac_name>(4E)-2-aminooctadec-4-ene-1,3-diol</iupac_name>
  <traditional_iupac>sphingosine</traditional_iupac>
  <cas_registry_number>123-78-4</cas_registry_number>
  <smiles>CCCCCCCCCCCCC\C=C\C(O)C(N)CO</smiles>
  <inchi>InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+</inchi>
  <inchikey>WWUZIQQURGPMPG-CCEZHUSRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>1,2-aminoalcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>81 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4E)-2-aminooctadec-4-ene-1,3-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>299.4919</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>299.282429433</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCC\C=C\C(O)C(N)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H37NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WWUZIQQURGPMPG-CCEZHUSRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>91.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180593</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB021919</foodb_id>
  <kegg_id>C00319</kegg_id>
  <chemspider_id>4510275</chemspider_id>
  <pubchem_compound_id>5353955</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>16393</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Sphingosine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34606</bigg_id>
  <metlin_id>392</metlin_id>
  <synthesis_reference>Obayashi, Michio; Schlosser, Manfred. An efficient synthesis of (2S,3R)- and (2S,3S)-sphingosine. Chemistry Letters (1985), (11), 1715-18.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00129</protein_accession>
      <name>Acid ceramidase</name>
      <uniprot_id>Q17QB3</uniprot_id>
      <gene_name>ASAH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02171</protein_accession>
      <name>Sphingosine 1-phosphate receptor 1</name>
      <uniprot_id>Q5E9P3</uniprot_id>
      <gene_name>S1PR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:27 UTC</creation_date>
  <update_date>2020-04-16 20:39:56 UTC</update_date>
  <accession>BMDB0000253</accession>
  <secondary_accessions>
    <accession>BMDB00253</accession>
  </secondary_accessions>
  <name>Pregnenolone</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C21H32O2</chemical_formula>
  <average_molecular_weight>316.4776</average_molecular_weight>
  <monisotopic_moleculate_weight>316.240230268</monisotopic_moleculate_weight>
  <iupac_name>1-[(1S,2R,5R,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one</iupac_name>
  <traditional_iupac>pregnenolone</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O</smiles>
  <inchi>InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16+,17-,18+,19+,20+,21-/m1/s1</inchi>
  <inchikey>ORNBQBCIOKFOEO-QYYVTAPASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Pregnane steroids</sub_class>
    <direct_parent>Gluco/mineralocorticoids, progestogins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>20-oxosteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(1S,2R,5R,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>316.4776</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>316.240230268</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H32O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16+,17-,18+,19+,20+,21-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ORNBQBCIOKFOEO-QYYVTAPASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>93.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1308007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1308008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1308009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1422511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1422512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1422513</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.000345</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.00768</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS in Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id/>
  <kegg_id/>
  <chemspider_id/>
  <pubchem_compound_id>146469</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Pregnenolone</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Shingate, Bapurao B.; Hazra, Braja G.; Pore, Vandana S.; Gonnade, Rajesh G.; Bhadbhade, Mohan M. Stereoselective syntheses of 20-epi cholanic acid derivatives from 16-dehydropregnenolone acetate. Tetrahedron  (2007),  63(25),  5622-5635.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00053</protein_accession>
      <name>Cholesterol side-chain cleavage enzyme, mitochondrial</name>
      <uniprot_id>P00189</uniprot_id>
      <gene_name>CYP11A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:28 UTC</creation_date>
  <update_date>2020-04-16 20:38:26 UTC</update_date>
  <accession>BMDB0000254</accession>
  <secondary_accessions>
    <accession>BMDB00254</accession>
  </secondary_accessions>
  <name>Succinic acid</name>
  <description>Succinic acid, also known as butanedionic acid or succinate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Succinic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Succinic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Succinic acid exists in all living species, ranging from bacteria to humans. Succinic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1,2-Ethanedicarboxylic acid</synonym>
    <synonym>Acide butanedioique</synonym>
    <synonym>Acide succinique</synonym>
    <synonym>Acidum succinicum</synonym>
    <synonym>Amber acid</synonym>
    <synonym>Asuccin</synonym>
    <synonym>Bernsteinsaeure</synonym>
    <synonym>Butandisaeure</synonym>
    <synonym>Butanedionic acid</synonym>
    <synonym>Dihydrofumaric acid</synonym>
    <synonym>e363</synonym>
    <synonym>Ethylenesuccinic acid</synonym>
    <synonym>HOOC-CH2-CH2-COOH</synonym>
    <synonym>Spirit OF amber</synonym>
    <synonym>1,2-Ethanedicarboxylate</synonym>
    <synonym>Butanedionate</synonym>
    <synonym>Dihydrofumarate</synonym>
    <synonym>Ethylenesuccinate</synonym>
    <synonym>Succinate</synonym>
    <synonym>2-Acetamido-2-deoxy-D-glucose</synonym>
    <synonym>D-GlcNAc</synonym>
    <synonym>N-Acetyl-D-glucosamine</synonym>
    <synonym>N-Acetylchitosamine</synonym>
    <synonym>N Acetyl D glucosamine</synonym>
    <synonym>2 Acetamido 2 deoxy D glucose</synonym>
    <synonym>2 Acetamido 2 deoxyglucose</synonym>
    <synonym>2-Acetamido-2-deoxyglucose</synonym>
    <synonym>Acetylglucosamine</synonym>
    <synonym>1,4-Butanedioate</synonym>
    <synonym>1,4-Butanedioic acid</synonym>
    <synonym>Katasuccin</synonym>
    <synonym>Wormwood acid</synonym>
    <synonym>1,2 Ethanedicarboxylic acid</synonym>
    <synonym>1,4 Butanedioic acid</synonym>
    <synonym>Potassium succinate</synonym>
    <synonym>Succinate, ammonium</synonym>
    <synonym>Butanedioic acid</synonym>
    <synonym>Succinate, potassium</synonym>
    <synonym>Ammonium succinate</synonym>
  </synonyms>
  <chemical_formula>C4H6O4</chemical_formula>
  <average_molecular_weight>118.088</average_molecular_weight>
  <monisotopic_moleculate_weight>118.02660868</monisotopic_moleculate_weight>
  <iupac_name>butanedioic acid</iupac_name>
  <traditional_iupac>succinic acid</traditional_iupac>
  <cas_registry_number>110-15-6</cas_registry_number>
  <smiles>OC(=O)CCC(O)=O</smiles>
  <inchi>InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)</inchi>
  <inchikey>KDYFGRWQOYBRFD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Dicarboxylic acids and derivatives</sub_class>
    <direct_parent>Dicarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C4-dicarboxylic acid</external_descriptor>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>alpha,omega-dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>185 - 188 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>83.2 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.59</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>butanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>118.088</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>118.02660868</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H6O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KDYFGRWQOYBRFD-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>23.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Butyrate Metabolism</name>
      <smpdb_id>SMP0087185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ketone Body Metabolism</name>
      <smpdb_id>SMP0087202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Electron Transport Chain</name>
      <smpdb_id>SMP0087261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Succinate Signalling</name>
      <smpdb_id>SMP0120941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Succinate Signalling During Inflammation</name>
      <smpdb_id>SMP0120886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4850</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1717 +/- 365</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Abdullah BASOGLU, Nuri BASPINAR, Alparslan COSKUN. NMR-based metabolomic evaluation in dairy cows with displaced abomasum. Turk J Vet Anim Sci (2014) 38(3):325-330</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>1194+/-584</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>1133+/-308</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23.20 +/- 6.60</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16 - 106</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19.73 +/- 3.18</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23.06 +/- 3.75</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>891-2314</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>110.14 +/- 35.65</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>167.81 +/- 31.14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>172.53 +/- 22.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>74-492</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>453.8 +/- 37.98</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>590</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>125.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>158.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>117.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>597+/-344</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>40-289</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>112.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>23-250</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>147 +/- 35</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>178 +/- 65</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>118 +/- 52</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>124 +/- 21</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>124 +/- 21</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR and GC-MS</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>84.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>103.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>80.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>82</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>112.68 +/- 18.27</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>743+/-384</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>340+/-76</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>1078</chemspider_id>
  <drugbank_id>DB00139</drugbank_id>
  <foodb_id>FDB001931</foodb_id>
  <kegg_id>C00042</kegg_id>
  <pdbe_id/>
  <chebi_id>15741</chebi_id>
  <pubchem_compound_id>1738118</pubchem_compound_id>
  <meta_cyc_id>SUC</meta_cyc_id>
  <knapsack_id>C00001205</knapsack_id>
  <wikipedia_id>Succinic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Berglund, Kris Arvid; Andersson, Christian; Rova, Ulrika.  Process for the production of succinic acid.    PCT Int. Appl.  (2007),     30pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00297</protein_accession>
      <name>Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial</name>
      <uniprot_id>Q3T189</uniprot_id>
      <gene_name>SDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00339</protein_accession>
      <name>Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial</name>
      <uniprot_id>P31039</uniprot_id>
      <gene_name>SDHA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00568</protein_accession>
      <name>Aspartyl/asparaginyl beta-hydroxylase</name>
      <uniprot_id>Q28056</uniprot_id>
      <gene_name>ASPH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00622</protein_accession>
      <name>Trimethyllysine dioxygenase, mitochondrial</name>
      <uniprot_id>Q0VC74</uniprot_id>
      <gene_name>TMLHE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00625</protein_accession>
      <name>Succinyl-CoA ligase [ADP-forming] subunit beta, mitochondrial</name>
      <uniprot_id>Q148D5</uniprot_id>
      <gene_name>SUCLA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00626</protein_accession>
      <name>Succinyl-CoA ligase [GDP-forming] subunit alpha, mitochondrial</name>
      <uniprot_id>Q58DR8</uniprot_id>
      <gene_name>SUCLG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00627</protein_accession>
      <name>Succinyl-CoA ligase [GDP-forming] subunit beta, mitochondrial</name>
      <uniprot_id>Q3MHX5</uniprot_id>
      <gene_name>SUCLG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00668</protein_accession>
      <name>Prolyl 4-hydroxylase subunit alpha-1</name>
      <uniprot_id>Q1RMU3</uniprot_id>
      <gene_name>P4HA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00682</protein_accession>
      <name>Procollagen-lysine,2-oxoglutarate 5-dioxygenase 1</name>
      <uniprot_id>O77588</uniprot_id>
      <gene_name>PLOD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00688</protein_accession>
      <name>Phytanoyl-CoA dioxygenase, peroxisomal</name>
      <uniprot_id>O18778</uniprot_id>
      <gene_name>PHYH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00691</protein_accession>
      <name>Prolyl 4-hydroxylase subunit alpha-3</name>
      <uniprot_id>Q75UG4</uniprot_id>
      <gene_name>P4HA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:29 UTC</creation_date>
  <update_date>2020-04-16 20:37:47 UTC</update_date>
  <accession>BMDB0000256</accession>
  <secondary_accessions>
    <accession>BMDB00256</accession>
  </secondary_accessions>
  <name>Squalene</name>
  <description/>
  <synonyms>
    <synonym>(all-e)-2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene</synonym>
    <synonym>Spinacene</synonym>
    <synonym>Supraene</synonym>
    <synonym>(e,e,e,e)-Squalene</synonym>
    <synonym>all-trans-Squalene</synonym>
    <synonym>trans-Squalene</synonym>
    <synonym>Squalene</synonym>
  </synonyms>
  <chemical_formula>C30H50</chemical_formula>
  <average_molecular_weight>410.73</average_molecular_weight>
  <monisotopic_moleculate_weight>410.39125161</monisotopic_moleculate_weight>
  <iupac_name>(6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene</iupac_name>
  <traditional_iupac>squalene</traditional_iupac>
  <cas_registry_number>111-02-4</cas_registry_number>
  <smiles>CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C</smiles>
  <inchi>InChI=1S/C30H50/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23+,30-24+</inchi>
  <inchikey>YYGNTYWPHWGJRM-AAJYLUCBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Triterpenoids</sub_class>
    <direct_parent>Triterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Acyclic olefins</alternative_parent>
      <alternative_parent>Branched unsaturated hydrocarbons</alternative_parent>
      <alternative_parent>Unsaturated aliphatic hydrocarbons</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyclic olefin</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Branched unsaturated hydrocarbon</substituent>
      <substituent>Hydrocarbon</substituent>
      <substituent>Olefin</substituent>
      <substituent>Triterpenoid</substituent>
      <substituent>Unsaturated aliphatic hydrocarbon</substituent>
      <substituent>Unsaturated hydrocarbon</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Acyclic triterpenoids</external_descriptor>
      <external_descriptor>Acyclic triterpenoids</external_descriptor>
      <external_descriptor>Liner triterpenes</external_descriptor>
      <external_descriptor>triterpene</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-75 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>8.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>10.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>410.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>410.39125161</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C30H50</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C30H50/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23+,30-24+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YYGNTYWPHWGJRM-AAJYLUCBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>144.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>56.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448489</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00751</kegg_id>
  <drugbank_id>DB11460</drugbank_id>
  <foodb_id/>
  <chemspider_id>553635</chemspider_id>
  <pdbe_id/>
  <chebi_id>15440</chebi_id>
  <pubchem_compound_id>638072</pubchem_compound_id>
  <meta_cyc_id/>
  <knapsack_id>C00003755</knapsack_id>
  <wikipedia_id>Squalene</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Peng, Wanxi; Li, Kaifu.  Method of preparation of squalene.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2006), 9pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00261</protein_accession>
      <name>Squalene synthetase</name>
      <uniprot_id>Q32KR6</uniprot_id>
      <gene_name>FDFT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:31 UTC</creation_date>
  <update_date>2020-04-15 22:33:57 UTC</update_date>
  <accession>BMDB0000257</accession>
  <secondary_accessions>
    <accession>BMDB00257</accession>
  </secondary_accessions>
  <name>Thiosulfate</name>
  <description/>
  <synonyms>
    <synonym>[SO2(OH)(SH)]</synonym>
    <synonym>H2S2O3</synonym>
    <synonym>Thiosulfuric acid</synonym>
    <synonym>Thiosulphate</synonym>
    <synonym>Thiosulphuric acid</synonym>
    <synonym>Hydroxidodioxidosulfidosulfuric acid</synonym>
    <synonym>Hydroxidodioxidosulphidosulphate</synonym>
    <synonym>Hydroxidodioxidosulphidosulphuric acid</synonym>
    <synonym>Thiosulfate</synonym>
  </synonyms>
  <chemical_formula>H2O3S2</chemical_formula>
  <average_molecular_weight>114.144</average_molecular_weight>
  <monisotopic_moleculate_weight>113.94453531</monisotopic_moleculate_weight>
  <iupac_name>sulfanesulfonic acid</iupac_name>
  <traditional_iupac>sulfurothioic S-acid</traditional_iupac>
  <cas_registry_number>14383-50-7</cas_registry_number>
  <smiles>OS(S)(=O)=O</smiles>
  <inchi>InChI=1S/H2O3S2/c1-5(2,3)4/h(H2,1,2,3,4)</inchi>
  <inchikey>DHCDFWKWKRSZHF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as non-metal thiosulfates. These are inorganic non-metallic compounds containing a thiosulfate as its largest oxoanion.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Non-metal oxoanionic compounds</class>
    <sub_class>Non-metal thiosulfates</sub_class>
    <direct_parent>Non-metal thiosulfates</direct_parent>
    <alternative_parents>
      <alternative_parent>Inorganic oxides</alternative_parent>
      <alternative_parent>Inorganic sulfides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Inorganic oxide</substituent>
      <substituent>Inorganic sulfide</substituent>
      <substituent>Non-metal thiosulfate</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>thiosulfuric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.096</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>sulfanesulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>114.144</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>113.94453531</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OS(S)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>H2O3S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/H2O3S2/c1-5(2,3)4/h(H2,1,2,3,4)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DHCDFWKWKRSZHF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>17.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>33194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218081</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05529</kegg_id>
  <drugbank_id>DB09499</drugbank_id>
  <foodb_id>FDB034578</foodb_id>
  <chemspider_id/>
  <pdbe_id/>
  <chebi_id>5587</chebi_id>
  <pubchem_compound_id>1085</pubchem_compound_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Thiosulfate</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Serikova, E. A.; Racheva, I. V. Method for producing sodium thiosulfate.  U.S.S.R.  (1986), CODEN: URXXAF  SU  1279954  A1  19861230  Patent  written in Russian.  </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00114</protein_accession>
      <name>Thiosulfate sulfurtransferase</name>
      <uniprot_id>P00586</uniprot_id>
      <gene_name>TST</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:32 UTC</creation_date>
  <update_date>2020-04-16 20:39:56 UTC</update_date>
  <accession>BMDB0000258</accession>
  <secondary_accessions>
    <accession>BMDB00258</accession>
  </secondary_accessions>
  <name>Sucrose</name>
  <description>Sucrose, also known as cane sugar or saccharose, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Sucrose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Sucrose exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>1-alpha-D-Glucopyranosyl-2-beta-D-fructofuranoside</synonym>
    <synonym>beta-D-Fruf-(21)-alpha-D-GLCP</synonym>
    <synonym>Cane sugar</synonym>
    <synonym>Sacarosa</synonym>
    <synonym>Saccharose</synonym>
    <synonym>Sacharose</synonym>
    <synonym>Table sugar</synonym>
    <synonym>White sugar</synonym>
    <synonym>White soft sugar</synonym>
    <synonym>Sugar, compressible</synonym>
    <synonym>Sugar, confectioner's</synonym>
    <synonym>Sugar spheres</synonym>
    <synonym>Sucrose, purified</synonym>
    <synonym>1-a-D-Glucopyranosyl-2-b-D-fructofuranoside</synonym>
    <synonym>1-Α-D-glucopyranosyl-2-β-D-fructofuranoside</synonym>
    <synonym>b-D-Fruf-(21)-a-D-GLCP</synonym>
    <synonym>Β-D-fruf-(21)-α-D-GLCP</synonym>
    <synonym>(+)-Sucrose</synonym>
    <synonym>b -D-Fructofuranosyl a-D-glucopyranoside</synonym>
    <synonym>D-(+)-Saccharose</synonym>
    <synonym>D-(+)-Sucrose</synonym>
    <synonym>D-Sucrose</synonym>
    <synonym>Saccharum</synonym>
    <synonym>Sugar</synonym>
  </synonyms>
  <chemical_formula>C12H22O11</chemical_formula>
  <average_molecular_weight>342.2965</average_molecular_weight>
  <monisotopic_moleculate_weight>342.116211546</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>sucrose</traditional_iupac>
  <cas_registry_number>57-50-1</cas_registry_number>
  <smiles>OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C12H22O11/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11-,12+/m1/s1</inchi>
  <inchikey>CZMRCDWAGMRECN-UGDNZRGBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>O-glycosyl compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Disaccharides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketals</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketal</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Disaccharides</external_descriptor>
      <external_descriptor>glycosyl glycoside</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>185.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>2100.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>342.2965</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>342.116211546</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H22O11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H22O11/c13-1-4-6(16)8(18)9(19)11(21-4)23-12(3-15)10(20)7(17)5(2-14)22-12/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11-,12+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CZMRCDWAGMRECN-UGDNZRGBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>189.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439024</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00089</kegg_id>
  <drugbank_id>DB02772</drugbank_id>
  <foodb_id>FDB003715</foodb_id>
  <chemspider_id/>
  <pdbe_id/>
  <chebi_id>17992</chebi_id>
  <pubchem_compound_id>5988</pubchem_compound_id>
  <meta_cyc_id>SUCROSE</meta_cyc_id>
  <knapsack_id>C00001151</knapsack_id>
  <wikipedia_id>Sucrose</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Fitremann, Juliette; Queneau, Yves; Maitre, Jean-Paul; Bouchu, Alain. Co-melting of solid sucrose and multivalent cation soaps for solvent-free synthesis of sucrose esters.   Tetrahedron Letters  (2007),  48(23),  4111-4114.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00381</protein_accession>
      <name>Polypeptide N-acetylgalactosaminyltransferase 6</name>
      <uniprot_id>Q5EA41</uniprot_id>
      <gene_name>GALNT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00382</protein_accession>
      <name>Polypeptide N-acetylgalactosaminyltransferase 1</name>
      <uniprot_id>Q07537</uniprot_id>
      <gene_name>GALNT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00447</protein_accession>
      <name>DNA-(apurinic or apyrimidinic site) lyase</name>
      <uniprot_id>P23196</uniprot_id>
      <gene_name>APEX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00644</protein_accession>
      <name>UDP-N-acetyl-alpha-D-galactosamine:polypeptide N-acetylgalactosaminyltransferase 6 (GalNAc-T6)</name>
      <uniprot_id>A6H6Z5</uniprot_id>
      <gene_name>GALNT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00645</protein_accession>
      <name>UDP-N-acetyl-alpha-D-galactosamine:polypeptide N-acetylgalactosaminyltransferase 13 (GalNAc-T13)</name>
      <uniprot_id>Q08DM9</uniprot_id>
      <gene_name>GALNT13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00675</protein_accession>
      <name>Endonuclease III-like protein 1</name>
      <uniprot_id>Q2KID2</uniprot_id>
      <gene_name>NTHL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00823</protein_accession>
      <name>Mannan-binding lectin serine peptidase 1 (C4/C2 activating component of Ra-reactive factor)</name>
      <uniprot_id>Q08DW4</uniprot_id>
      <gene_name>MASP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00824</protein_accession>
      <name>Endonuclease VIII-like 2</name>
      <uniprot_id>Q6IE77</uniprot_id>
      <gene_name>NEIL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00825</protein_accession>
      <name>Aprataxin and PNK-like factor</name>
      <uniprot_id>A0JNH9</uniprot_id>
      <gene_name>APLF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00826</protein_accession>
      <name>Secretory phospholipase A2 receptor</name>
      <uniprot_id>P49259</uniprot_id>
      <gene_name>PLA2R1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00827</protein_accession>
      <name>Glucosamine--fructose-6-phosphate aminotransferase [isomerizing] 2</name>
      <uniprot_id>Q08DQ2</uniprot_id>
      <gene_name>GFPT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00828</protein_accession>
      <name>DNA-(apurinic or apyrimidinic site) lyase 2</name>
      <uniprot_id>Q5E9N9</uniprot_id>
      <gene_name>APEX2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01616</protein_accession>
      <name>Collectin-12</name>
      <uniprot_id>A6QP79</uniprot_id>
      <gene_name>COLEC12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01889</protein_accession>
      <name>Galectin-4</name>
      <uniprot_id>Q3T0D6</uniprot_id>
      <gene_name>LGALS4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01903</protein_accession>
      <name>Mannan-binding lectin A</name>
      <uniprot_id>Q5I2B0</uniprot_id>
      <gene_name>MBL-A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01918</protein_accession>
      <name>GALNTL1 protein</name>
      <uniprot_id>A6QLD9</uniprot_id>
      <gene_name>GALNTL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01920</protein_accession>
      <name>GALNT4 protein</name>
      <uniprot_id>A7YY74</uniprot_id>
      <gene_name>GALNT4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01921</protein_accession>
      <name>GALNT12 protein</name>
      <uniprot_id>A6QLX6</uniprot_id>
      <gene_name>GALNT12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01922</protein_accession>
      <name>UDP-N-acetyl-alpha-D-galactosamine:polypeptide N-acetylgalactosaminyltransferase-like 4</name>
      <uniprot_id>Q0IIK7</uniprot_id>
      <gene_name>GALNTL4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02010</protein_accession>
      <name>LGALS3 protein</name>
      <uniprot_id>A6QLZ0</uniprot_id>
      <gene_name>LGALS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02011</protein_accession>
      <name>Chitinase-3-like protein 1</name>
      <uniprot_id>P30922</uniprot_id>
      <gene_name>CHI3L1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02012</protein_accession>
      <name>Solute carrier family 35 (UDP-galactose transporter), member A2</name>
      <uniprot_id>Q8SPM1</uniprot_id>
      <gene_name>ugt</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02013</protein_accession>
      <name>P-selectin glycoprotein ligand 1</name>
      <uniprot_id>A7WPA6</uniprot_id>
      <gene_name>SELPLG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02014</protein_accession>
      <name>Latrophilin-3</name>
      <uniprot_id>O97827</uniprot_id>
      <gene_name>LPHN3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02015</protein_accession>
      <name>Pulmonary surfactant-associated protein A</name>
      <uniprot_id>Q6RXL1</uniprot_id>
      <gene_name>SFTPA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02016</protein_accession>
      <name>Dectin-2 alpha isoform</name>
      <uniprot_id>Q3LUH2</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02017</protein_accession>
      <name>Killer cell lectin-like receptor family J member 1</name>
      <uniprot_id>A6QPD3</uniprot_id>
      <gene_name>KLRJ1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02018</protein_accession>
      <name>Regenerating islet-derived family, member 4</name>
      <uniprot_id>Q3ZCG9</uniprot_id>
      <gene_name>REG4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02019</protein_accession>
      <name>Latrophilin 2 splice variant babae</name>
      <uniprot_id>O97806</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02020</protein_accession>
      <name>Calreticulin</name>
      <uniprot_id>P52193</uniprot_id>
      <gene_name>CALR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02021</protein_accession>
      <name>Killer cell lectin-like receptor family J member 1</name>
      <uniprot_id>Q863I0</uniprot_id>
      <gene_name>KLRJ1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02022</protein_accession>
      <name>Natural killer cell receptor group D variant 1</name>
      <uniprot_id>Q95JG6</uniprot_id>
      <gene_name>KLRC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02023</protein_accession>
      <name>Serum amyloid P-component</name>
      <uniprot_id>Q3T004</uniprot_id>
      <gene_name>APCS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02024</protein_accession>
      <name>Natural killer cells antigen CD94</name>
      <uniprot_id>Q863H3</uniprot_id>
      <gene_name>KLRD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02025</protein_accession>
      <name>Solute carrier family 2, facilitated glucose transporter member 4</name>
      <uniprot_id>Q27994</uniprot_id>
      <gene_name>SLC2A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02026</protein_accession>
      <name>E-selectin</name>
      <uniprot_id>P98107</uniprot_id>
      <gene_name>SELE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02027</protein_accession>
      <name>Pancreatic thread protein</name>
      <uniprot_id>Q56JW0</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02028</protein_accession>
      <name>Dectin-2 beta isoform</name>
      <uniprot_id>Q3LUH1</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02029</protein_accession>
      <name>C-type lectin domain family 12 member B</name>
      <uniprot_id>Q2NL33</uniprot_id>
      <gene_name>CLEC12B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02030</protein_accession>
      <name>Probable UDP-sugar transporter protein SLC35A5</name>
      <uniprot_id>A6QPI1</uniprot_id>
      <gene_name>SLC35A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02031</protein_accession>
      <name>Latrophilin 2 splice variant baabe</name>
      <uniprot_id>O97804</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02032</protein_accession>
      <name>Lectin, galactoside-binding, soluble, 8</name>
      <uniprot_id>Q2YDD7</uniprot_id>
      <gene_name>LGALS8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02033</protein_accession>
      <name>P-selectin glycoprotein ligand 1</name>
      <uniprot_id>Q32SI4</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02034</protein_accession>
      <name>Solute carrier family 2, facilitated glucose transporter member 1</name>
      <uniprot_id>P27674</uniprot_id>
      <gene_name>SLC2A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02035</protein_accession>
      <name>Oxidized low-density lipoprotein receptor 1</name>
      <uniprot_id>P79391</uniprot_id>
      <gene_name>OLR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02036</protein_accession>
      <name>Solute carrier family 2, facilitated glucose transporter member 8</name>
      <uniprot_id>P58354</uniprot_id>
      <gene_name>SLC2A8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02037</protein_accession>
      <name>Lectin, galactoside-binding, soluble, 3</name>
      <uniprot_id>Q0VBW6</uniprot_id>
      <gene_name>LGALS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02038</protein_accession>
      <name>Latrophilin-2</name>
      <uniprot_id>O97817</uniprot_id>
      <gene_name>LPHN2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02039</protein_accession>
      <name>Asialoglycoprotein receptor 1</name>
      <uniprot_id>Q32KM0</uniprot_id>
      <gene_name>ASGR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02040</protein_accession>
      <name>43kDa collectin</name>
      <uniprot_id>B7FEK7</uniprot_id>
      <gene_name>CL43</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02041</protein_accession>
      <name>Solute carrier family 35 member B1</name>
      <uniprot_id>Q8MII5</uniprot_id>
      <gene_name>SLC35B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02042</protein_accession>
      <name>Oxidised low density lipoprotein (Lectin-like) receptor 1</name>
      <uniprot_id>A1L4Z7</uniprot_id>
      <gene_name>OLR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02043</protein_accession>
      <name>Brevican core protein</name>
      <uniprot_id>Q28062</uniprot_id>
      <gene_name>BCAN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02044</protein_accession>
      <name>P2Y purinoceptor 14</name>
      <uniprot_id>Q3SX17</uniprot_id>
      <gene_name>P2RY14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02045</protein_accession>
      <name>Solute carrier family 35 (CMP-sialic acid transporter), member A1</name>
      <uniprot_id>Q3SZP1</uniprot_id>
      <gene_name>SLC35A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02046</protein_accession>
      <name>Calreticulin-3</name>
      <uniprot_id>Q2TBR8</uniprot_id>
      <gene_name>CALR3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02047</protein_accession>
      <name>UDP-galactose translocator</name>
      <uniprot_id>Q58DA6</uniprot_id>
      <gene_name>SLC35A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02048</protein_accession>
      <name>C-type lectin domain family 3 member A</name>
      <uniprot_id>Q28008</uniprot_id>
      <gene_name>CLEC3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02049</protein_accession>
      <name>Galectin 9 short isoform</name>
      <uniprot_id>Q5E9E0</uniprot_id>
      <gene_name>LGALS9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02050</protein_accession>
      <name>Latrophilin-1</name>
      <uniprot_id>O97831</uniprot_id>
      <gene_name>LPHN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02051</protein_accession>
      <name>Solute carrier family 2, facilitated glucose transporter member 12</name>
      <uniprot_id>Q5J316</uniprot_id>
      <gene_name>SLC2A12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02052</protein_accession>
      <name>Pulmonary surfactant-associated protein D</name>
      <uniprot_id>P35246</uniprot_id>
      <gene_name>SFTPD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02053</protein_accession>
      <name>Type I transmembrane C-type lectin receptor DCL-1</name>
      <uniprot_id>A8WH74</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02054</protein_accession>
      <name>GFPT1 protein</name>
      <uniprot_id>A8E645</uniprot_id>
      <gene_name>GFPT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02055</protein_accession>
      <name>Natural killer cell receptor group D variant 2</name>
      <uniprot_id>Q95JG5</uniprot_id>
      <gene_name>KLRC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02056</protein_accession>
      <name>Solute carrier family 2, facilitated glucose transporter member 3</name>
      <uniprot_id>P58352</uniprot_id>
      <gene_name>SLC2A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02057</protein_accession>
      <name>VIP36-like protein</name>
      <uniprot_id>Q2HJD1</uniprot_id>
      <gene_name>LMAN2L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02058</protein_accession>
      <name>Ficolin-2</name>
      <uniprot_id>Q5I2E5</uniprot_id>
      <gene_name>FCN2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02059</protein_accession>
      <name>Latrophilin 2 splice variant baaaf</name>
      <uniprot_id>O97803</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02060</protein_accession>
      <name>Aggrecan core protein</name>
      <uniprot_id>P13608</uniprot_id>
      <gene_name>ACAN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02061</protein_accession>
      <name>Tetranectin</name>
      <uniprot_id>Q2KIS7</uniprot_id>
      <gene_name>CLEC3B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02062</protein_accession>
      <name>Galectin-9</name>
      <uniprot_id>Q3MHZ8</uniprot_id>
      <gene_name>LGALS9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02063</protein_accession>
      <name>C-type lectin domain family 7 member A</name>
      <uniprot_id>Q49BZ4</uniprot_id>
      <gene_name>CLEC7A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02064</protein_accession>
      <name>NCAN protein</name>
      <uniprot_id>A8KC79</uniprot_id>
      <gene_name>NCAN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02065</protein_accession>
      <name>Putative immunoreceptor NKG2D</name>
      <uniprot_id>Q1XF12</uniprot_id>
      <gene_name>NKG2D</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02066</protein_accession>
      <name>L-selectin</name>
      <uniprot_id>P98131</uniprot_id>
      <gene_name>SELL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02067</protein_accession>
      <name>DC-SIGN-like protein</name>
      <uniprot_id>C0IP18</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02068</protein_accession>
      <name>C-type lectin domain family 14, member A</name>
      <uniprot_id>Q148M5</uniprot_id>
      <gene_name>CLEC14A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02069</protein_accession>
      <name>Latrophilin 2 splice variant baaae</name>
      <uniprot_id>O97802</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02070</protein_accession>
      <name>Solute carrier family 35 member A2</name>
      <uniprot_id>Q0V8N0</uniprot_id>
      <gene_name>SLC35A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02071</protein_accession>
      <name>Versican core protein</name>
      <uniprot_id>P81282</uniprot_id>
      <gene_name>VCAN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02072</protein_accession>
      <name>Asialoglycoprotein receptor 2</name>
      <uniprot_id>Q2KIU5</uniprot_id>
      <gene_name>ASGR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02073</protein_accession>
      <name>Aggrecan</name>
      <uniprot_id>Q6XL67</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02074</protein_accession>
      <name>Regenerating islet-derived 3 alpha</name>
      <uniprot_id>A4IFV8</uniprot_id>
      <gene_name>REG3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02075</protein_accession>
      <name>Solute carrier family 2, facilitated glucose transporter member 5</name>
      <uniprot_id>P58353</uniprot_id>
      <gene_name>SLC2A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02076</protein_accession>
      <name>Latrophilin 2 splice variant babbe</name>
      <uniprot_id>O97808</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02077</protein_accession>
      <name>C-type lectin domain family 1 member A</name>
      <uniprot_id>Q0VCS6</uniprot_id>
      <gene_name>CLEC1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02078</protein_accession>
      <name>Regenerating islet-derived 3 gamma</name>
      <uniprot_id>Q3ZCJ9</uniprot_id>
      <gene_name>REG3G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02079</protein_accession>
      <name>Lithostathine</name>
      <uniprot_id>P23132</uniprot_id>
      <gene_name>PTP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02080</protein_accession>
      <name>UDP-N-acetylglucosamine transporter</name>
      <uniprot_id>Q6YC49</uniprot_id>
      <gene_name>SLC35A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:33 UTC</creation_date>
  <update_date>2020-04-16 20:40:47 UTC</update_date>
  <accession>BMDB0000259</accession>
  <secondary_accessions>
    <accession>BMDB00259</accession>
  </secondary_accessions>
  <name>Serotonin</name>
  <description/>
  <synonyms>
    <synonym>3-(2-Aminoethyl)-1H-indol-5-ol</synonym>
    <synonym>5-HT</synonym>
    <synonym>5-Hydroxytryptamine</synonym>
    <synonym>Enteramine</synonym>
    <synonym>Serotonine</synonym>
    <synonym>Thrombocytin</synonym>
    <synonym>Thrombotonin</synonym>
    <synonym>Hippophaine</synonym>
    <synonym>Hydroxytryptamine</synonym>
    <synonym>5 Hydroxytryptamine</synonym>
    <synonym>3-(2-Aminoethyl)indol-5-ol</synonym>
    <synonym>3-(b-Aminoethyl)-5-hydroxyindole</synonym>
    <synonym>5-HTA</synonym>
    <synonym>5-Hydroxy-3-(b-aminoethyl)indole</synonym>
    <synonym>5-Hydroxy-tryptamine</synonym>
    <synonym>5-Hydroxyltryptamine</synonym>
    <synonym>5-Hydroxytriptamine</synonym>
    <synonym>Antemovis</synonym>
    <synonym>DS Substance</synonym>
    <synonym>Enteramin</synonym>
  </synonyms>
  <chemical_formula>C10H12N2O</chemical_formula>
  <average_molecular_weight>176.2151</average_molecular_weight>
  <monisotopic_moleculate_weight>176.094963016</monisotopic_moleculate_weight>
  <iupac_name>3-(2-aminoethyl)-1H-indol-5-ol</iupac_name>
  <traditional_iupac>serotonin</traditional_iupac>
  <cas_registry_number>50-67-9</cas_registry_number>
  <smiles>NCCC1=CNC2=C1C=C(O)C=C2</smiles>
  <inchi>InChI=1S/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2</inchi>
  <inchikey>QZAYGJVTTNCVMB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Tryptamines and derivatives</sub_class>
    <direct_parent>Serotonins</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>2-arylethylamines</alternative_parent>
      <alternative_parent>3-alkylindoles</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxyindoles</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>2-arylethylamine</substituent>
      <substituent>3-alkylindole</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyindole</substituent>
      <substituent>Indole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Serotonin</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>Indole alkaloids</external_descriptor>
      <external_descriptor>monoamine molecular messenger</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
      <external_descriptor>primary amino compound</external_descriptor>
      <external_descriptor>tryptamines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>25.5 mg/mL</value>
      <source>Human Metabolome Project</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.21</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(2-aminoethyl)-1H-indol-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>176.2151</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>176.094963016</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCC1=CNC2=C1C=C(O)C=C2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QZAYGJVTTNCVMB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>62.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>52.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 4 and Serotonin</name>
      <smpdb_id>SMP0108169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 6 and Serotonin</name>
      <smpdb_id>SMP0108172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 7 and Serotonin</name>
      <smpdb_id>SMP0108170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3792</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3796</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>241597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>241598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>241599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>243652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>243653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>243654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446968</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>9+/-3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>4-13</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ELISA</comment>
      <references>
        <reference>
          <reference_text>Hernandez-Castellano LE, Hernandez LL, Weaver S, Bruckmaier RM: Increased serum serotonin improves parturient calcium homeostasis in dairy cows. J Dairy Sci. 2017 Feb;100(2):1580-1587. doi: 10.3168/jds.2016-11638. Epub 2016 Dec 14.</reference_text>
          <pubmed_id>27988124</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>2+/-1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.1+/-0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1.02 +/- 0.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1.02 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00780</kegg_id>
  <drugbank_id>DB08839</drugbank_id>
  <foodb_id>FDB012158</foodb_id>
  <chemspider_id>5013</chemspider_id>
  <pdbe_id/>
  <chebi_id>28790</chebi_id>
  <pubchem_compound_id>5202</pubchem_compound_id>
  <meta_cyc_id>SEROTONIN</meta_cyc_id>
  <knapsack_id>C00001429</knapsack_id>
  <wikipedia_id>Serotonin</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Harley-Mason, John; Jackson, A. H. Hydroxytryptamines. I. Bufotenine, 6-hydroxybufotenine, and serotonin. Journal of the Chemical Society (1954), 1165-71.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00936</protein_accession>
      <name>Aromatic-L-amino-acid decarboxylase</name>
      <uniprot_id>P27718</uniprot_id>
      <gene_name>DDC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01811</protein_accession>
      <name>Synaptic vesicular amine transporter</name>
      <uniprot_id>Q27963</uniprot_id>
      <gene_name>SLC18A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02209</protein_accession>
      <name>5-hydroxytryptamine 2A receptor</name>
      <uniprot_id>Q8MI10</uniprot_id>
      <gene_name>5htr2a</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02210</protein_accession>
      <name>5-hydroxytryptamine 4 receptor</name>
      <uniprot_id>Q8MI07</uniprot_id>
      <gene_name>5htr4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02211</protein_accession>
      <name>5-hydroxytryptamine 1A receptor</name>
      <uniprot_id>Q8MI15</uniprot_id>
      <gene_name>5htr1a</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02212</protein_accession>
      <name>5-hydroxytryptamine 1E receptor</name>
      <uniprot_id>Q8MI12</uniprot_id>
      <gene_name>5htr1e</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02213</protein_accession>
      <name>5-hydroxytryptamine serotonin receptor 1B</name>
      <uniprot_id>A1Y9Q2</uniprot_id>
      <gene_name>HTR1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02214</protein_accession>
      <name>5-hydroxytryptamine 1F receptor</name>
      <uniprot_id>Q8MI11</uniprot_id>
      <gene_name>5htr1f</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02215</protein_accession>
      <name>5-hydroxytryptamine 2B receptor</name>
      <uniprot_id>Q8MI09</uniprot_id>
      <gene_name>5htr2b</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02216</protein_accession>
      <name>5-hydroxytryptamine serotonin receptor 1B</name>
      <uniprot_id>A1Y9Q0</uniprot_id>
      <gene_name>HTR1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02217</protein_accession>
      <name>5-hydroxytryptamine (Serotonin) receptor 4 isoform b</name>
      <uniprot_id>Q5E9Q5</uniprot_id>
      <gene_name>HTR4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02218</protein_accession>
      <name>Sodium-dependent serotonin transporter</name>
      <uniprot_id>Q9XT49</uniprot_id>
      <gene_name>SLC6A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02219</protein_accession>
      <name>5-hydroxytryptamine serotonin receptor 1B</name>
      <uniprot_id>A1Y9Q3</uniprot_id>
      <gene_name>HTR1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02220</protein_accession>
      <name>5-hydroxytryptamine 1B receptor</name>
      <uniprot_id>Q8MI14</uniprot_id>
      <gene_name>5htr1b</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02221</protein_accession>
      <name>5-hydroxytryptamine serotonin receptor 1B</name>
      <uniprot_id>A1Y9P9</uniprot_id>
      <gene_name>HTR1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02222</protein_accession>
      <name>5-hydroxytryptamine 1D receptor</name>
      <uniprot_id>Q8MI13</uniprot_id>
      <gene_name>5htr1d</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02223</protein_accession>
      <name>5-hydroxytryptamine receptor 2A</name>
      <uniprot_id>Q75Z89</uniprot_id>
      <gene_name>HTR2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02224</protein_accession>
      <name>5-hydroxytryptamine 2C receptor</name>
      <uniprot_id>Q8MI08</uniprot_id>
      <gene_name>5htr2c</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02225</protein_accession>
      <name>5-hydroxytryptamine serotonin receptor 1B</name>
      <uniprot_id>A1Y9Q1</uniprot_id>
      <gene_name>HTR1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:34 UTC</creation_date>
  <update_date>2020-04-16 20:37:47 UTC</update_date>
  <accession>BMDB0000262</accession>
  <secondary_accessions>
    <accession>BMDB00262</accession>
  </secondary_accessions>
  <name>Thymine</name>
  <description>Thymine, also known as 5-methyluracil, belongs to the class of organic compounds known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Thymine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Thymine exists in all living species, ranging from bacteria to humans. Thymine is a potentially toxic compound. Thymine has been found to be associated with several diseases known as colorectal cancer, thymidine treatment, and temporomandibular joint disorder; also thymine has been linked to the inborn metabolic disorders including dihydropyrimidine dehydrogenase deficiency.</description>
  <synonyms>
    <synonym>2,4-Dihydroxy-5-methylpyrimidine</synonym>
    <synonym>5-Methyl-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>5-Methylpyrimidine-2,4(1H,3H)-dione</synonym>
    <synonym>5-Methyluracil</synonym>
    <synonym>T</synonym>
    <synonym>Thy</synonym>
    <synonym>Thymin</synonym>
    <synonym>4-Hydroxy-5-methylpyrimidin-2(1H)-one</synonym>
    <synonym>5-Methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione</synonym>
    <synonym>5-Methyl-2,4-dihydroxypyrimidine</synonym>
    <synonym>5-Methylpyrimidine-2,4-dione</synonym>
    <synonym>5 Methyluracil</synonym>
  </synonyms>
  <chemical_formula>C5H6N2O2</chemical_formula>
  <average_molecular_weight>126.1133</average_molecular_weight>
  <monisotopic_moleculate_weight>126.042927446</monisotopic_moleculate_weight>
  <iupac_name>5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione</iupac_name>
  <traditional_iupac>thymine</traditional_iupac>
  <cas_registry_number>65-71-4</cas_registry_number>
  <smiles>CC1=CNC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C5H6N2O2/c1-3-2-6-5(9)7-4(3)8/h2H,1H3,(H2,6,7,8,9)</inchi>
  <inchikey>RWQNBRDOKXIBIV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazines</class>
    <sub_class>Pyrimidines and pyrimidine derivatives</sub_class>
    <direct_parent>Hydroxypyrimidines</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a pyrimidine base</external_descriptor>
      <external_descriptor>a pyrimidine-related compound</external_descriptor>
      <external_descriptor>pyrimidine nucleobase</external_descriptor>
      <external_descriptor>pyrimidines</external_descriptor>
      <external_descriptor>pyrimidone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>320 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>3.82 mg/mL</value>
      <source>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.62</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>126.1133</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>126.042927446</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CNC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H6N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H6N2O2/c1-3-2-6-5(9)7-4(3)8/h2H,1H3,(H2,6,7,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RWQNBRDOKXIBIV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>58.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438501</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>188+/-45</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>26.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>30.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>30.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>39.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>27 +/- 12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>30 +/- 14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>35 +/- 30</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>40 +/- 23</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>40 +/- 23</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>39.78 +/- 46.65</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00178</kegg_id>
  <chemspider_id>1103</chemspider_id>
  <pubchem_compound_id>1135</pubchem_compound_id>
  <drugbank_id>DB03462</drugbank_id>
  <foodb_id>FDB021922</foodb_id>
  <pdbe_id/>
  <chebi_id>17821</chebi_id>
  <meta_cyc_id/>
  <knapsack_id>C00001511</knapsack_id>
  <wikipedia_id>Thymine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34151</bigg_id>
  <metlin_id>290</metlin_id>
  <synthesis_reference>Zhang, Shi-Ying; Wu, Da-Jun; Zhang, Yan-Ping.  Synthesis of thymine.    Zhongguo Yiyao Gongye Zazhi  (1999),  30(7),  325.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:35 UTC</creation_date>
  <update_date>2020-04-14 22:47:13 UTC</update_date>
  <accession>BMDB0000263</accession>
  <secondary_accessions>
    <accession>BMDB00263</accession>
  </secondary_accessions>
  <name>Phosphoenolpyruvic acid</name>
  <description>Phosphoenolpyruvic acid, also known as PEP or 2-phosphonooxyprop-2-enoate, belongs to the class of organic compounds known as phosphate esters. These are organic compounds containing phosphoric acid ester functional group, with the general structure R1P(=O)(R2)OR3. R1,R2 = O,N, or halogen atom; R3 = organyl group. Phosphoenolpyruvic acid is possibly soluble (in water) and an extremely strong acidic compound (based on its pKa). Phosphoenolpyruvic acid exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>2-(Phosphonooxy)-2-propenoic acid</synonym>
    <synonym>2-PHOSPHOENOLPYRUVIC ACID</synonym>
    <synonym>PEP</synonym>
    <synonym>PHOSPHOENOLPYRUVATE</synonym>
    <synonym>2-(Phosphonooxy)-2-propenoate</synonym>
    <synonym>2-PHOSPHOENOLPYRUVate</synonym>
    <synonym>2-Hydroxy-acrylic acid dihydrogen phosphate</synonym>
    <synonym>2-Phosphonooxyprop-2-enoate</synonym>
    <synonym>2-Phosphonooxyprop-2-enoic acid</synonym>
    <synonym>p-enol-Pyruvate</synonym>
  </synonyms>
  <chemical_formula>C3H5O6P</chemical_formula>
  <average_molecular_weight>168.042</average_molecular_weight>
  <monisotopic_moleculate_weight>167.982374404</monisotopic_moleculate_weight>
  <iupac_name>2-(phosphonooxy)prop-2-enoic acid</iupac_name>
  <traditional_iupac>phosphoenolpyruvic acid</traditional_iupac>
  <cas_registry_number>138-08-9</cas_registry_number>
  <smiles>OC(=O)C(=C)OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)</inchi>
  <inchikey>DTBNBXWJWCWCIK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phosphate esters. These are organic compounds containing phosphoric acid ester functional group, with the general structure R1P(=O)(R2)OR3. R1,R2 = O,N,  or halogen atom; R3 = organyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic phosphoric acids and derivatives</class>
    <sub_class>Phosphate esters</sub_class>
    <direct_parent>Phosphate esters</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>carboxyalkyl phosphate</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(phosphonooxy)prop-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>168.042</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>167.982374404</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C(=C)OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H5O6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DTBNBXWJWCWCIK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>104.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3843</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00074</kegg_id>
  <drugbank_id>DB01819</drugbank_id>
  <foodb_id>FDB031112</foodb_id>
  <chemspider_id/>
  <pdbe_id/>
  <chebi_id>44897</chebi_id>
  <pubchem_compound_id>1005</pubchem_compound_id>
  <meta_cyc_id/>
  <knapsack_id>C00000798</knapsack_id>
  <wikipedia_id>Phosphoenolpyruvic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Simon, Ethan S.; Grabowski, Sven; Whitesides, George M.  Preparation of phosphoenolpyruvate from D-(-)-3-phosphoglyceric acid for use in regeneration of ATP.    Journal of the American Chemical Society  (1989),  111(24),  8920-1.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00449</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>B3IVN4</uniprot_id>
      <gene_name>PKM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00455</protein_accession>
      <name>Beta-enolase</name>
      <uniprot_id>Q3ZC09</uniprot_id>
      <gene_name>ENO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00457</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>Q3ZC87</uniprot_id>
      <gene_name>PKM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00464</protein_accession>
      <name>Alpha-enolase</name>
      <uniprot_id>Q9XSJ4</uniprot_id>
      <gene_name>ENO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00465</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>Q1JPG7</uniprot_id>
      <gene_name>PKLR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00491</protein_accession>
      <name>Enolase</name>
      <uniprot_id>A6QR19</uniprot_id>
      <gene_name>ENO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00497</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>A5D984</uniprot_id>
      <gene_name>PKM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00617</protein_accession>
      <name>Phosphoenolpyruvate carboxykinase, cytosolic [GTP]</name>
      <uniprot_id>Q8HYZ4</uniprot_id>
      <gene_name>PPCK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:36 UTC</creation_date>
  <update_date>2020-04-15 23:55:33 UTC</update_date>
  <accession>BMDB0000265</accession>
  <secondary_accessions>
    <accession>BMDB00265</accession>
  </secondary_accessions>
  <name>Liothyronine</name>
  <description>Liothyronine, also known as T3 or liotironina, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Liothyronine is a drug which is used as replacement or supplemental therapy in patients with hypothyroidism of any etiology, except transient hypothyrodism during the recovery phase of subacute thyroiditis. Liothyronine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Liothyronine exists in all living organisms, ranging from bacteria to humans. In cattle, liothyronine is involved in the metabolic pathway called thyroid hormone synthesis pathway. Liothyronine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>3,5,3'-Triiodo-L-thyronine</synonym>
    <synonym>3,5,3'-Triiodothyronine</synonym>
    <synonym>3,5,3'TRIIODOTHYRONINE</synonym>
    <synonym>4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanine</synonym>
    <synonym>L-3,5,3'-Triiodothyronine</synonym>
    <synonym>L-T3</synonym>
    <synonym>Liothyroninum</synonym>
    <synonym>Liotironina</synonym>
    <synonym>O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine</synonym>
    <synonym>T3</synonym>
    <synonym>Tertroxin</synonym>
    <synonym>Tresitope</synonym>
    <synonym>Triiodothyronine</synonym>
    <synonym>3,3',5-Triiodo-L-thyronine</synonym>
    <synonym>Thyrolar</synonym>
    <synonym>3,3',5-Triiodothyronine</synonym>
    <synonym>Cytomel</synonym>
    <synonym>T3 Thyroid hormone</synonym>
    <synonym>Thyroid hormone, T3</synonym>
    <synonym>Liothyronine sodium</synonym>
    <synonym>3,3',5'-Triiodo-L-thyronine</synonym>
    <synonym>3,3',5'-Triiodothyronine</synonym>
    <synonym>4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenylalanine</synonym>
    <synonym>Cyronine</synonym>
    <synonym>L-3,3',5-Triiodo-thyronine</synonym>
    <synonym>L-3,3',5-Triiodothyronine</synonym>
    <synonym>L-3-[4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-alanine</synonym>
    <synonym>L-Liothyronine</synonym>
    <synonym>L-Triiodothyronine</synonym>
    <synonym>Liothyronin</synonym>
    <synonym>Triiodo-L-thyronine</synonym>
  </synonyms>
  <chemical_formula>C15H12I3NO4</chemical_formula>
  <average_molecular_weight>650.9735</average_molecular_weight>
  <monisotopic_moleculate_weight>650.790038137</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid</iupac_name>
  <traditional_iupac>liothyronine</traditional_iupac>
  <cas_registry_number>6893-02-3</cas_registry_number>
  <smiles>N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1</inchi>
  <inchikey>AUYYCJSJGJYCDS-LBPRGKRZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Phenylalanine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aryl iodides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Diarylethers</alternative_parent>
      <alternative_parent>Diphenylethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Iodobenzenes</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>O-iodophenols</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organoiodides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenol ethers</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>2-halophenol</substituent>
      <substituent>2-iodophenol</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Aryl iodide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Diaryl ether</substituent>
      <substituent>Diphenylether</substituent>
      <substituent>Ether</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Iodobenzene</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organoiodide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-halophenol</external_descriptor>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>iodophenol</external_descriptor>
      <external_descriptor>iodothyronine</external_descriptor>
      <external_descriptor>thyroxine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>650.9735</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>650.790038137</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H12I3NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AUYYCJSJGJYCDS-LBPRGKRZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>113.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>43.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Thyroid Hormone Synthesis</name>
      <smpdb_id>SMP0087269</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3847</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447095</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>500</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Slebodzinski AB, Nowak J, Gawecka H, Sechman A: Thyroid hormones and insulin in milk; a comparative study. Endocrinol Exp. 1986 Aug;20(2-3):247-55.</reference_text>
          <pubmed_id>3530717</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02465</kegg_id>
  <drugbank_id>DB00279</drugbank_id>
  <foodb_id/>
  <chemspider_id/>
  <pdbe_id/>
  <chebi_id>18258</chebi_id>
  <pubchem_compound_id>5920</pubchem_compound_id>
  <meta_cyc_id>CPD-10813</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Triiodothyronine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Salamonczyk, Grzegorz M.; Oza, Vibha B.; Sih, Charles J. A concise synthesis of thyroxine (T4) and 3,5,3'-triiodo-L-thyronine (T3). Tetrahedron Letters (1997), 38(40), 6965-69</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Slebodzinski AB, Nowak J, Gawecka H, Sechman A: Thyroid hormones and insulin in milk; a comparative study. Endocrinol Exp. 1986 Aug;20(2-3):247-55.</reference_text>
      <pubmed_id>3530717</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00548</protein_accession>
      <name>Type III iodothyronine deiodinase</name>
      <uniprot_id>Q5I3B1</uniprot_id>
      <gene_name>DIO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:37 UTC</creation_date>
  <update_date>2020-04-16 17:53:56 UTC</update_date>
  <accession>BMDB0000267</accession>
  <secondary_accessions>
    <accession>BMDB00267</accession>
  </secondary_accessions>
  <name>Pyroglutamic acid</name>
  <description>Pyroglutamic acid, also known as pyroglutamate or pidolate, magnesium, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Pyroglutamic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Pyroglutamic acid exists in all living species, ranging from bacteria to humans. Pyroglutamic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(-)-2-Pyrrolidone-5-carboxylic acid</synonym>
    <synonym>(S)-(-)-2-Pyrrolidone-5-carboxylic acid</synonym>
    <synonym>(S)-Pyroglutamic acid</synonym>
    <synonym>5-Pyrrolidone-2-carboxylic acid</synonym>
    <synonym>L-5-Pyrrolidone-2-carboxylic acid</synonym>
    <synonym>L-Pyroglutamic acid</synonym>
    <synonym>Pidolic acid</synonym>
    <synonym>Pyroglutamate</synonym>
    <synonym>5-oxo-L-Proline</synonym>
    <synonym>(-)-2-Pyrrolidone-5-carboxylate</synonym>
    <synonym>(S)-(-)-2-Pyrrolidone-5-carboxylate</synonym>
    <synonym>(S)-Pyroglutamate</synonym>
    <synonym>5-Pyrrolidone-2-carboxylate</synonym>
    <synonym>L-5-Pyrrolidone-2-carboxylate</synonym>
    <synonym>L-Pyroglutamate</synonym>
    <synonym>Pidolate</synonym>
    <synonym>(-)-Pyroglutamate</synonym>
    <synonym>(-)-Pyroglutamic acid</synonym>
    <synonym>(5S)-2-Oxopyrrolidine-5-carboxylate</synonym>
    <synonym>(5S)-2-Oxopyrrolidine-5-carboxylic acid</synonym>
    <synonym>(S)-(-)-g-Butyrolactam-g-carboxylate</synonym>
    <synonym>(S)-(-)-g-Butyrolactam-g-carboxylic acid</synonym>
    <synonym>(S)-(-)-gamma-Butyrolactam-gamma-carboxylate</synonym>
    <synonym>(S)-(-)-gamma-Butyrolactam-gamma-carboxylic acid</synonym>
    <synonym>(S)-2-Pyrrolidone-5-carboxylate</synonym>
    <synonym>(S)-2-Pyrrolidone-5-carboxylic acid</synonym>
    <synonym>(S)-5-oxo-2-Pyrrolidinecarboxylate</synonym>
    <synonym>(S)-5-oxo-2-Pyrrolidinecarboxylic acid</synonym>
    <synonym>2-L-Pyrrolidone-5-carboxylate</synonym>
    <synonym>2-L-Pyrrolidone-5-carboxylic acid</synonym>
    <synonym>2-Oxopyrrolidine-5(S)-carboxylate</synonym>
    <synonym>2-Oxopyrrolidine-5(S)-carboxylic acid</synonym>
    <synonym>2-Pyrrolidinone-5-carboxylate</synonym>
    <synonym>2-Pyrrolidinone-5-carboxylic acid</synonym>
    <synonym>5-Carboxy-2-pyrrolidinone</synonym>
    <synonym>5-L-Oxoproline</synonym>
    <synonym>5-Oxoproline</synonym>
    <synonym>5-Pyrrolidinone-2-carboxylate</synonym>
    <synonym>5-Pyrrolidinone-2-carboxylic acid</synonym>
    <synonym>Ajidew a 100</synonym>
    <synonym>Glutimate</synonym>
    <synonym>Glutimic acid</synonym>
    <synonym>Glutiminate</synonym>
    <synonym>Glutiminic acid</synonym>
    <synonym>L-2-Pyrrolidone-5-carboxylate</synonym>
    <synonym>L-2-Pyrrolidone-5-carboxylic acid</synonym>
    <synonym>L-5-Carboxy-2-pyrrolidinone</synonym>
    <synonym>L-5-oxo-2-Pyrrolidinecarboxylate</synonym>
    <synonym>L-5-oxo-2-Pyrrolidinecarboxylic acid</synonym>
    <synonym>L-5-Oxoproline</synonym>
    <synonym>L-Glutamic acid g-lactam</synonym>
    <synonym>L-Glutimate</synonym>
    <synonym>L-Glutimic acid</synonym>
    <synonym>L-Glutiminate</synonym>
    <synonym>L-Glutiminic acid</synonym>
    <synonym>L-Pyrrolidinonecarboxylate</synonym>
    <synonym>L-Pyrrolidinonecarboxylic acid</synonym>
    <synonym>L-Pyrrolidonecarboxylate</synonym>
    <synonym>L-Pyrrolidonecarboxylic acid</synonym>
    <synonym>Oxoproline</synonym>
    <synonym>Oxopyrrolidinecarboxylate</synonym>
    <synonym>Oxopyrrolidinecarboxylic acid</synonym>
    <synonym>Pidolidone</synonym>
    <synonym>Pyrrolidinonecarboxylate</synonym>
    <synonym>Pyrrolidinonecarboxylic acid</synonym>
    <synonym>Pyrrolidone-5-carboxylate</synonym>
    <synonym>Pyrrolidone-5-carboxylic acid</synonym>
    <synonym>Pyrrolidonecarboxylic acid</synonym>
    <synonym>5-Ketoproline</synonym>
    <synonym>Pidolate, magnesium</synonym>
    <synonym>5-Oxopyrrolidine-2-carboxylic acid</synonym>
    <synonym>Magnesium pidolate</synonym>
    <synonym>2-Pyrrolidone-5-carboxylic acid</synonym>
    <synonym>5-Oxoprolinate</synonym>
    <synonym>PCA</synonym>
  </synonyms>
  <chemical_formula>C5H7NO3</chemical_formula>
  <average_molecular_weight>129.114</average_molecular_weight>
  <monisotopic_moleculate_weight>129.042593095</monisotopic_moleculate_weight>
  <iupac_name>(2S)-5-oxopyrrolidine-2-carboxylic acid</iupac_name>
  <traditional_iupac>pyroglutamic acid</traditional_iupac>
  <cas_registry_number>98-79-3</cas_registry_number>
  <smiles>OC(=O)[C@@H]1CCC(=O)N1</smiles>
  <inchi>InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1</inchi>
  <inchikey>ODHCTXKNWHHXJC-VKHMYHEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic carboximidic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactims</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrroline carboxylic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Cyclic carboximidic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactim</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyrroline</substituent>
      <substituent>Pyrroline carboxylic acid</substituent>
      <substituent>Pyrroline carboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>5-oxoproline</external_descriptor>
      <external_descriptor>L-proline derivative</external_descriptor>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>476.0 mg/mL at 13 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-5-oxopyrrolidine-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>129.114</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>129.042593095</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)[C@@H]1CCC(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H7NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ODHCTXKNWHHXJC-VKHMYHEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glutathione Metabolism</name>
      <smpdb_id>SMP0087167</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>2004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3858</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3871</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3878</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>233+/-64</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>384.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>486.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>524.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>355.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>384 +/- 59</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>486 +/- 94</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>525 +/- 120</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>356 +/- 45</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>356 +/- 45</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>355.94 +/- 44.73</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01879</kegg_id>
  <drugbank_id>DB03088</drugbank_id>
  <foodb_id>FDB014506</foodb_id>
  <chemspider_id/>
  <pdbe_id/>
  <chebi_id>18183</chebi_id>
  <pubchem_compound_id>7405</pubchem_compound_id>
  <meta_cyc_id>5-OXOPROLINE</meta_cyc_id>
  <knapsack_id>C00007403</knapsack_id>
  <wikipedia_id>Pyroglutamic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Pumpor, Ksenia; Boettcher, Christoph; Fehn, Susanna; Burger, Klaus. Hexafluoroacetone as protecting and activating reagent: an efficient strategy for activation of pyroglutamic acid and homologs.Heterocycles  (2003),  61  259-269.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
      <pubmed_id>29197344</pubmed_id>
    </reference>
    <reference>
      <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
      <pubmed_id>27999311</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00857</protein_accession>
      <name>5-oxoprolinase</name>
      <uniprot_id>Q75WB5</uniprot_id>
      <gene_name>OPLAH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01242</protein_accession>
      <name>Gamma-glutamylcyclotransferase</name>
      <uniprot_id>Q32LE4</uniprot_id>
      <gene_name>GGCT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:38 UTC</creation_date>
  <update_date>2020-03-13 16:19:52 UTC</update_date>
  <accession>BMDB0000268</accession>
  <secondary_accessions>
    <accession>BMDB00268</accession>
  </secondary_accessions>
  <name>Tetrahydrocorticosterone</name>
  <description/>
  <synonyms>
    <synonym>(3alpha,5beta,11beta)-3,11,21-Trihydroxypregnan-20-one</synonym>
    <synonym>(3α,5β,11β)-3,11,21-Trihydroxypregnan-20-one</synonym>
    <synonym>3alpha,11beta,21-Trihydroxy-5beta-pregnan-20-one</synonym>
    <synonym>3alpha,5beta-Tetrahydrocorticosterone</synonym>
    <synonym>3α,11β,21-Trihydroxy-5β-pregnan-20-one</synonym>
    <synonym>3α,5β-Tetrahydrocorticosterone</synonym>
    <synonym>5beta-Pregnane-3alpha,11beta,21-triol-20-one</synonym>
    <synonym>5β-Pregnane-3α,11β,21-triol-20-one</synonym>
    <synonym>THB</synonym>
    <synonym>Tetrahydrocorticosterone</synonym>
  </synonyms>
  <chemical_formula>C21H34O4</chemical_formula>
  <average_molecular_weight>350.4923</average_molecular_weight>
  <monisotopic_moleculate_weight>350.245709576</monisotopic_moleculate_weight>
  <iupac_name>1-[(1S,2S,5R,7R,10S,11S,14S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-hydroxyethan-1-one</iupac_name>
  <traditional_iupac>1-[(1S,2S,5R,7R,10S,11S,14S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-hydroxyethanone</traditional_iupac>
  <cas_registry_number>68-42-8</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H34O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-17,19,22-24H,3-11H2,1-2H3/t12-,13-,14+,15+,16-,17+,19-,20+,21+/m1/s1</inchi>
  <inchikey>RHQQHZQUAMFINJ-DTDWNVJFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>11-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>11-beta-hydroxysteroid</substituent>
      <substituent>11-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>21-hydroxy steroid</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(1S,2S,5R,7R,10S,11S,14S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-hydroxyethan-1-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>350.4923</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>350.245709576</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H34O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H34O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-17,19,22-24H,3-11H2,1-2H3/t12-,13-,14+,15+,16-,17+,19-,20+,21+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RHQQHZQUAMFINJ-DTDWNVJFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>96.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1244908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1244909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1244910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1360267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1360268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1360269</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05476</kegg_id>
  <chemspider_id>58996</chemspider_id>
  <pubchem_compound_id/>
  <drugbank_id/>
  <foodb_id/>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Tetrahydrocorticosterone</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Higashi, Tatsuya; Yokoi, Hiroyuki; Maekubo, Hitoe; Honda, Ayako; Shimada, Kazutake.  Studies on neurosteroids. XXIII. Analysis of tetrahydrocorticosterone isomers in the brain of rats exposed to immobilization using LC-MS.    Steroids  (2007),  72(13),  865-874.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:40 UTC</creation_date>
  <update_date>2020-04-15 22:36:47 UTC</update_date>
  <accession>BMDB0000269</accession>
  <secondary_accessions>
    <accession>BMDB00269</accession>
  </secondary_accessions>
  <name>Sphinganine</name>
  <description/>
  <synonyms>
    <synonym>(2S,3R)-2-Amino-1,3-octadecanediol</synonym>
    <synonym>(2S,3R)-2-Aminooctadecane-1,3-diol</synonym>
    <synonym>(R-(R*,s*))-2-aminooctadecane-1,3-diol</synonym>
    <synonym>2-Amino-1,3-dihydroxyoctadecane</synonym>
    <synonym>C18-Dihydrosphingosine</synonym>
    <synonym>C18-Sphinganine</synonym>
    <synonym>D-Erythro-1,3-dihydroxy-2-aminooctadecane</synonym>
    <synonym>D-Erythro-2-amino-1,3-octadecanediol</synonym>
    <synonym>D-Erythro-C18-dihydrosphingosine</synonym>
    <synonym>D18:0</synonym>
    <synonym>Dihydrosphingosine</synonym>
    <synonym>Octadecasphinganine</synonym>
    <synonym>Safingol</synonym>
    <synonym>Erythro-D-sphinganine</synonym>
    <synonym>2-Aminooctadecane-1,3-diol</synonym>
    <synonym>Threo-dihydrosphingosine</synonym>
    <synonym>2-Amino-D-erythro-1,3-octadecanediol</synonym>
    <synonym>C18-Dihydro-sphingosine</synonym>
    <synonym>D-Erythro-sphinganine</synonym>
    <synonym>Dihydro-C18-sphingosine</synonym>
    <synonym>Erythro-sphinganine</synonym>
    <synonym>[R-(R*,s*)]-2-amino-1,3-octadecanediol</synonym>
    <synonym>(2S,3R)-Sphinganine</synonym>
    <synonym>D-Erythro-dihydrosphingosine</synonym>
    <synonym>SP(D18:0)</synonym>
    <synonym>Sphinganine</synonym>
  </synonyms>
  <chemical_formula>C18H39NO2</chemical_formula>
  <average_molecular_weight>301.5078</average_molecular_weight>
  <monisotopic_moleculate_weight>301.298079497</monisotopic_moleculate_weight>
  <iupac_name>(2S,3R)-2-aminooctadecane-1,3-diol</iupac_name>
  <traditional_iupac>sphinganine</traditional_iupac>
  <cas_registry_number>764-22-7</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO</smiles>
  <inchi>InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/m0/s1</inchi>
  <inchikey>OTKJDMGTUTTYMP-ZWKOTPCHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>1,2-aminoalcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-aminooctadecane-1,3-diol</external_descriptor>
      <external_descriptor>Sphinganines</external_descriptor>
      <external_descriptor>Sphinganines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3R)-2-aminooctadecane-1,3-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>301.5078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>301.298079497</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H39NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OTKJDMGTUTTYMP-ZWKOTPCHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>90.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3881</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3882</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181847</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451802</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00836</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB030824</foodb_id>
  <chemspider_id>82609</chemspider_id>
  <pubchem_compound_id>91486</pubchem_compound_id>
  <chebi_id>16566</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00007540</knapsack_id>
  <meta_cyc_id>CPD-13612</meta_cyc_id>
  <wikipedia_id>Safingol</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Roush, William R.; Adam, Michael A. Directed openings of 2,3-epoxy alcohols via reactions with isocyanates: synthesis of (+)-erythro-dihydrosphingosine. Journal of Organic Chemistry (1985), 50(20), 3752-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00071</protein_accession>
      <name>3-ketodihydrosphingosine reductase</name>
      <uniprot_id>Q2KIJ5</uniprot_id>
      <gene_name>KDSR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:41 UTC</creation_date>
  <update_date>2020-04-16 20:38:26 UTC</update_date>
  <accession>BMDB0000271</accession>
  <secondary_accessions>
    <accession>BMDB00271</accession>
  </secondary_accessions>
  <name>Sarcosine</name>
  <description>Sarcosine, also known as N-methylglycine or megly, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Sarcosine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Sarcosine exists in all living organisms, ranging from bacteria to humans. Sarcosine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(Methylamino)acetic acid</synonym>
    <synonym>(Methylamino)ethanoic acid</synonym>
    <synonym>L-Sarcosine</synonym>
    <synonym>MeGly</synonym>
    <synonym>Methylaminoacetic acid</synonym>
    <synonym>N-Methylaminoacetic acid</synonym>
    <synonym>N-Methylglycine</synonym>
    <synonym>Sar</synonym>
    <synonym>Sarcosinic acid</synonym>
    <synonym>(Methylamino)acetate</synonym>
    <synonym>(Methylamino)ethanoate</synonym>
    <synonym>Methylaminoacetate</synonym>
    <synonym>N-Methylaminoacetate</synonym>
    <synonym>Sarcosinate</synonym>
    <synonym>(Methylamino)-acetate</synonym>
    <synonym>(Methylamino)-acetic acid</synonym>
    <synonym>Methylglycine</synonym>
    <synonym>N-Methyl-glycine</synonym>
    <synonym>Sarcosin</synonym>
    <synonym>Sodium sarcosinate</synonym>
    <synonym>Magnesium sarcosylate</synonym>
    <synonym>Sarcosinate, sodium</synonym>
    <synonym>Sarcosine hydrochloride</synonym>
    <synonym>Sarcosylate, magnesium</synonym>
    <synonym>N Methylglycine</synonym>
    <synonym>Sarcosine monosodium salt</synonym>
  </synonyms>
  <chemical_formula>C3H7NO2</chemical_formula>
  <average_molecular_weight>89.0932</average_molecular_weight>
  <monisotopic_moleculate_weight>89.047678473</monisotopic_moleculate_weight>
  <iupac_name>2-(methylamino)acetic acid</iupac_name>
  <traditional_iupac>sarcosine</traditional_iupac>
  <cas_registry_number>107-97-1</cas_registry_number>
  <smiles>CNCC(O)=O</smiles>
  <inchi>InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)</inchi>
  <inchikey>FSYKKLYZXJSNPZ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-alkylglycine</external_descriptor>
      <external_descriptor>N-methyl-amino acid</external_descriptor>
      <external_descriptor>N-methylglycines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>208 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>300.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.78</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(methylamino)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>89.0932</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>89.047678473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CNCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7NO2/c1-4-2-3(5)6/h4H,2H2,1H3,(H,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FSYKKLYZXJSNPZ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>49.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>20.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446944</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446945</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>10-12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>23+/-10</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>12+/-5</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>36.9 +/- 30.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>6.9 +/- 30.53</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>10+/-4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>5+/-2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00213</kegg_id>
  <drugbank_id>DB12519</drugbank_id>
  <foodb_id>FDB004048</foodb_id>
  <chemspider_id>1057</chemspider_id>
  <pubchem_compound_id>1088</pubchem_compound_id>
  <chebi_id>15611</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id>SARCOSINE</meta_cyc_id>
  <wikipedia_id>Sarcosine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34275</bigg_id>
  <metlin_id>51</metlin_id>
  <synthesis_reference>Cipens, G.; Slavinska, V.; Sile, D.; Kreile, D.; Strautina, A.; Krikis, A.; Gutmanis, A.  Synthesis of sarcosine and its use.    Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija  (1986),   (5),  515-24.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00895</protein_accession>
      <name>Peroxisomal sarcosine oxidase</name>
      <uniprot_id>Q29RU9</uniprot_id>
      <gene_name>PIPOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:42 UTC</creation_date>
  <update_date>2020-04-14 22:47:16 UTC</update_date>
  <accession>BMDB0000272</accession>
  <secondary_accessions>
    <accession>BMDB00272</accession>
  </secondary_accessions>
  <name>Phosphoserine</name>
  <description/>
  <synonyms>
    <synonym>(+)-L-Serine dihydrogen phosphate (ester)</synonym>
    <synonym>(2S)-2-Amino-3-(phosphonooxy)propanoic acid</synonym>
    <synonym>(S)-2-Amino-3-hydroxypropanoic acid 3-phosphate</synonym>
    <synonym>3-Phosphoserine</synonym>
    <synonym>Dexfosfoserine</synonym>
    <synonym>L-O-Phosphoserine</synonym>
    <synonym>O-Phosphoserine</synonym>
    <synonym>3-Phospho-L-serine</synonym>
    <synonym>(+)-L-Serine dihydrogen phosphoric acid (ester)</synonym>
    <synonym>(2S)-2-Amino-3-(phosphonooxy)propanoate</synonym>
    <synonym>(S)-2-Amino-3-hydroxypropanoate 3-phosphate</synonym>
    <synonym>(S)-2-Amino-3-hydroxypropanoic acid 3-phosphoric acid</synonym>
    <synonym>3-O-Phosphoserine</synonym>
    <synonym>Fosforina</synonym>
    <synonym>L-3-Phosphoserine</synonym>
    <synonym>L-O-Serine phosphate</synonym>
    <synonym>L-Phosphoserine</synonym>
    <synonym>L-Serine dihydrogen phosphate (ester)</synonym>
    <synonym>L-Serine phosphate</synonym>
    <synonym>L-Serinephosphorate</synonym>
    <synonym>L-Serinephosphoric acid</synonym>
    <synonym>L-Seryl phosphate</synonym>
    <synonym>Plasmenylserine</synonym>
  </synonyms>
  <chemical_formula>C3H8NO6P</chemical_formula>
  <average_molecular_weight>185.0725</average_molecular_weight>
  <monisotopic_moleculate_weight>185.008923505</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-(phosphonooxy)propanoic acid</iupac_name>
  <traditional_iupac>phosphoserine</traditional_iupac>
  <cas_registry_number>407-41-0</cas_registry_number>
  <smiles>N[C@@H](COP(O)(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1</inchi>
  <inchikey>BZQFBWGGLXLEPQ-REOHCLBHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phosphoethanolamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoethanolamine</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>O-phosphoserine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>170 - 171 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>71 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-(phosphonooxy)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>185.0725</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>185.008923505</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](COP(O)(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H8NO6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BZQFBWGGLXLEPQ-REOHCLBHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>130.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446801</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01005</kegg_id>
  <drugbank_id>DB04522</drugbank_id>
  <foodb_id>FDB021926</foodb_id>
  <chemspider_id>62074</chemspider_id>
  <pubchem_compound_id>68841</pubchem_compound_id>
  <chebi_id>15811</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00007287</knapsack_id>
  <meta_cyc_id>3-P-SERINE</meta_cyc_id>
  <wikipedia_id>3-phosphoserine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5270</metlin_id>
  <synthesis_reference>Barruel, Elena Mery.  Biosynthesis of phosphoserine in vitro.    Anales Fac. Quim. y Farm.  (1960),  12  228-33.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00240</protein_accession>
      <name>14-3-3 protein zeta/delta</name>
      <uniprot_id>P63103</uniprot_id>
      <gene_name>YWHAZ</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00241</protein_accession>
      <name>14-3-3 protein eta</name>
      <uniprot_id>P68509</uniprot_id>
      <gene_name>YWHAH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00242</protein_accession>
      <name>14-3-3 protein gamma</name>
      <uniprot_id>P68252</uniprot_id>
      <gene_name>YWHAG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00243</protein_accession>
      <name>14-3-3 protein beta/alpha</name>
      <uniprot_id>P68250</uniprot_id>
      <gene_name>YWHAB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01419</protein_accession>
      <name>14-3-3 protein theta</name>
      <uniprot_id>Q3SZI4</uniprot_id>
      <gene_name>YWHAQ</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01420</protein_accession>
      <name>14-3-3 protein epsilon</name>
      <uniprot_id>P62261</uniprot_id>
      <gene_name>YWHAE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01421</protein_accession>
      <name>14-3-3 protein sigma</name>
      <uniprot_id>Q0VC36</uniprot_id>
      <gene_name>SFN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:43 UTC</creation_date>
  <update_date>2020-04-16 20:39:17 UTC</update_date>
  <accession>BMDB0000273</accession>
  <secondary_accessions>
    <accession>BMDB00273</accession>
  </secondary_accessions>
  <name>Thymidine</name>
  <description>Thymidine, also known as deoxythymidine or DTHD, belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Thymidine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Thymidine exists in all living species, ranging from bacteria to humans. Thymidine participates in a number of enzymatic reactions, within cattle. In particular, Thymidine can be biosynthesized from 5-thymidylic acid through its interaction with the enzyme cytosolic purine 5'-nucleotidase. In addition, Thymidine can be converted into 5-thymidylic acid; which is catalyzed by the enzyme thymidine kinase, cytosolic. In cattle, thymidine is involved in the metabolic pathway called the pyrimidine metabolism pathway. Thymidine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-(2-Deoxy-beta-D-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione</synonym>
    <synonym>2'-Deoxy-5-methyluridine</synonym>
    <synonym>2'-Deoxythymidine</synonym>
    <synonym>2'-Thymidine</synonym>
    <synonym>5-Methyl-2'-deoxyuridine</synonym>
    <synonym>Deoxythymidine</synonym>
    <synonym>DTHD</synonym>
    <synonym>T</synonym>
    <synonym>Thymine 2'-deoxyriboside</synonym>
    <synonym>1-(2-Deoxy-b-D-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione</synonym>
    <synonym>1-(2-Deoxy-β-D-erythro-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione</synonym>
    <synonym>1-(2-Deoxy-b-D-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>1-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>1-[4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione</synonym>
    <synonym>2'-Deoxy-5-methyl-uridine</synonym>
    <synonym>5-Methyldeoxyuridine</synonym>
    <synonym>Deoxyribothymidine</synonym>
    <synonym>DT</synonym>
    <synonym>DThyd</synonym>
    <synonym>Thymidin</synonym>
    <synonym>Thymine 2-desoxyriboside</synonym>
    <synonym>Thymine deoxyriboside</synonym>
    <synonym>Thymine-1 2-deoxy-b-D-ribofuranoside</synonym>
    <synonym>Thymine-1 2-deoxy-beta-delta-ribofuranoside</synonym>
    <synonym>2' Deoxythymidine</synonym>
  </synonyms>
  <chemical_formula>C10H14N2O5</chemical_formula>
  <average_molecular_weight>242.2286</average_molecular_weight>
  <monisotopic_moleculate_weight>242.090271568</monisotopic_moleculate_weight>
  <iupac_name>1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione</iupac_name>
  <traditional_iupac>thymidine</traditional_iupac>
  <cas_registry_number>50-89-5</cas_registry_number>
  <smiles>CC1=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)NC1=O</smiles>
  <inchi>InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m0/s1</inchi>
  <inchikey>IQFYYKKMVGJFEH-XLPZGREQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleosides</class>
    <sub_class>Pyrimidine 2'-deoxyribonucleosides</sub_class>
    <direct_parent>Pyrimidine 2'-deoxyribonucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxyribonucleosides</external_descriptor>
      <external_descriptor>pyrimidine 2'-deoxyribonucleoside</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>73.5 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.93</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>242.2286</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>242.090271568</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H14N2O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)/t6-,7+,8+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IQFYYKKMVGJFEH-XLPZGREQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>99.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>55.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438496</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00214</kegg_id>
  <foodb_id>FDB031201</foodb_id>
  <chemspider_id>5585</chemspider_id>
  <drugbank_id>DB04485</drugbank_id>
  <pubchem_compound_id>5789</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17748</chebi_id>
  <knapsack_id>C00019698</knapsack_id>
  <meta_cyc_id>THYMIDINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>50348</bigg_id>
  <wikipedia_id>Thymidine</wikipedia_id>
  <metlin_id>3375</metlin_id>
  <synthesis_reference>Herdewijn, P.; Kerremans, L.; Wigerinck, P.; Vandendriessche, F.; Van Aerschot, A.  Synthesis of thymidine from 5-iodo-2'-deoxyuridine.    Tetrahedron Letters  (1991),  32(34),  4397-400.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:44 UTC</creation_date>
  <update_date>2020-04-15 22:27:40 UTC</update_date>
  <accession>BMDB0000277</accession>
  <secondary_accessions>
    <accession>BMDB00277</accession>
  </secondary_accessions>
  <name>Sphingosine 1-phosphate</name>
  <description/>
  <synonyms>
    <synonym>(2-Amino-3-hydroxy-octadec-4-enoxy)phosphonic acid</synonym>
    <synonym>(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-(dihydrogen phosphate)</synonym>
    <synonym>C18-Sphingosine 1-phosphate</synonym>
    <synonym>D-Erythro-sphingosine 1-phosphate</synonym>
    <synonym>S1P</synonym>
    <synonym>Sphing-4-enine 1-phosphate</synonym>
    <synonym>Sphingosine 1-phosphic acid</synonym>
    <synonym>Sphingosine-1-phosphate</synonym>
    <synonym>(2-Amino-3-hydroxy-octadec-4-enoxy)phosphonate</synonym>
    <synonym>(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-(dihydrogen phosphoric acid)</synonym>
    <synonym>C18-Sphingosine 1-phosphoric acid</synonym>
    <synonym>D-Erythro-sphingosine 1-phosphoric acid</synonym>
    <synonym>Sphing-4-enine 1-phosphoric acid</synonym>
    <synonym>Sphingosine 1-phosphoric acid</synonym>
    <synonym>Sphingosine-1-phosphoric acid</synonym>
    <synonym>Sphingosine 1-phosphate</synonym>
    <synonym>S1p Compound</synonym>
  </synonyms>
  <chemical_formula>C18H38NO5P</chemical_formula>
  <average_molecular_weight>379.4718</average_molecular_weight>
  <monisotopic_moleculate_weight>379.248759843</monisotopic_moleculate_weight>
  <iupac_name>{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>sphingosine 1-phosphate</traditional_iupac>
  <cas_registry_number>26993-30-6</cas_registry_number>
  <smiles>CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C18H38NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+/t17-,18+/m0/s1</inchi>
  <inchikey>DUYSYHSSBDVJSM-KRWOKUGFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Sphingolipids</class>
    <sub_class>Phosphosphingolipids</sub_class>
    <direct_parent>Phosphosphingolipids</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phosphoethanolamines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoethanolamine</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sphingoid-1-phosphate or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Sphingoid base 1-phosphates</external_descriptor>
      <external_descriptor>Sphingoid base 1-phosphates</external_descriptor>
      <external_descriptor>sphingoid 1-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2S,3R,4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>379.4718</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>379.248759843</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H38NO5P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H38NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+/t17-,18+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DUYSYHSSBDVJSM-KRWOKUGFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>102.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>43.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>48952</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C06124</kegg_id>
  <foodb_id/>
  <chemspider_id/>
  <drugbank_id/>
  <pubchem_compound_id>5283560</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>37550</chebi_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Sphingosine-1-phosphate</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Morigaki, Eiji; Miura, Yoshie; Takahata, Kyoya; Tada, Mikiro; Nakajima, Shuhei; Baba, Naomichi.  Enzymic preparation of sphingosine 1-phosphate.    Journal of Chemical Research, Synopses  (1998),   (12),  774-775.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP02171</protein_accession>
      <name>Sphingosine 1-phosphate receptor 1</name>
      <uniprot_id>Q5E9P3</uniprot_id>
      <gene_name>S1PR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:45 UTC</creation_date>
  <update_date>2020-04-14 22:47:16 UTC</update_date>
  <accession>BMDB0000279</accession>
  <secondary_accessions>
    <accession>BMDB00279</accession>
  </secondary_accessions>
  <name>Saccharopine</name>
  <description>Saccharopinee belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Saccharopinee exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Saccharopinee exists in all living species, ranging from bacteria to humans. Saccharopinee participates in a number of enzymatic reactions, within cattle. In particular, Saccharopinee can be biosynthesized from L-lysine and oxoglutaric acid; which is catalyzed by the enzyme Alpha-aminoadipic semialdehyde synthase, mitochondrial. In addition, Saccharopinee can be converted into allysine and L-glutamic acid through the action of the enzyme Alpha-aminoadipic semialdehyde synthase, mitochondrial. In cattle, saccharopinee is involved in the metabolic pathway called the lysine degradation pathway. Saccharopinee is a potentially toxic compound.</description>
  <synonyms>
    <synonym>epsilon-N-(L-Glutar-2-yl)-L-lysine</synonym>
    <synonym>N-[(S)-5-Amino-5-carboxypentyl]-L-glutamic acid</synonym>
    <synonym>N6-(L-1,3-Dicarboxypropyl)-L-lysine</synonym>
    <synonym>L-Saccharopine</synonym>
    <synonym>N-[(S)-5-Amino-5-carboxypentyl]-L-glutamate</synonym>
    <synonym>(S)-N-(5-Amino-5-carboxypentyl)-L-glutamic acid</synonym>
    <synonym>L-N-(5-Amino-5-carboxypentyl)-glutamic acid</synonym>
    <synonym>L-Saccharopin</synonym>
    <synonym>N(6)-(L-1,3-Dicarboxypropyl)-L-lysine</synonym>
    <synonym>N-(5-Amino-5-carboxypentyl)-glutamic acid</synonym>
    <synonym>N-(5-Amino-5-carboxypentyl)-L-glutamic acid</synonym>
    <synonym>N-[(5S)-5-Amino-5-carboxypentyl]-L-glutamic acid</synonym>
    <synonym>Saccharopin</synonym>
  </synonyms>
  <chemical_formula>C11H20N2O6</chemical_formula>
  <average_molecular_weight>276.2863</average_molecular_weight>
  <monisotopic_moleculate_weight>276.132136382</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-{[(5S)-5-amino-5-carboxypentyl]amino}pentanedioic acid</iupac_name>
  <traditional_iupac>saccharopine</traditional_iupac>
  <cas_registry_number>997-68-2</cas_registry_number>
  <smiles>N[C@@H](CCCCN[C@@H](CCC(O)=O)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1</inchi>
  <inchikey>ZDGJAHTZVHVLOT-YUMQZZPRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Glutamic acid and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-lysine derivative</external_descriptor>
      <external_descriptor>amino acid opine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>247 - 250 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-{[(5S)-5-amino-5-carboxypentyl]amino}pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>276.2863</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>276.132136382</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCCCN[C@@H](CCC(O)=O)C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H20N2O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZDGJAHTZVHVLOT-YUMQZZPRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>149.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>63.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448117</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00449</kegg_id>
  <drugbank_id>DB04207</drugbank_id>
  <foodb_id>FDB000461</foodb_id>
  <chemspider_id>141086</chemspider_id>
  <pubchem_compound_id>160556</pubchem_compound_id>
  <chebi_id>16927</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00007227</knapsack_id>
  <meta_cyc_id>SACCHAROPINE</meta_cyc_id>
  <wikipedia_id>Saccharopine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>1484994</bigg_id>
  <metlin_id>383</metlin_id>
  <synthesis_reference>Burkard, Ulrike; Walther, Ingrid; Effenberger, Franz. Amino acids. 6. Investigations on the synthesis of L-saccharopin. Liebigs Annalen der Chemie (1986), (6), 1030-43.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00631</protein_accession>
      <name>Alpha-aminoadipic semialdehyde synthase, mitochondrial</name>
      <uniprot_id>A8E657</uniprot_id>
      <gene_name>AASS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00632</protein_accession>
      <name>Probable saccharopine dehydrogenase</name>
      <uniprot_id>Q3T067</uniprot_id>
      <gene_name>SCCPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:46 UTC</creation_date>
  <update_date>2020-04-15 21:59:24 UTC</update_date>
  <accession>BMDB0000280</accession>
  <secondary_accessions>
    <accession>BMDB00280</accession>
  </secondary_accessions>
  <name>Phosphoribosyl pyrophosphate</name>
  <description/>
  <synonyms>
    <synonym>5-Phospho-alpha-D-ribose 1-diphosphate</synonym>
    <synonym>5-Phosphoribosyl 1-pyrophosphate</synonym>
    <synonym>5-Phosphoribosyl diphosphate</synonym>
    <synonym>alpha-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)</synonym>
    <synonym>alpha-Phosphoribosylpyrophosphoric acid</synonym>
    <synonym>Phosphoribosylpyrophosphate</synonym>
    <synonym>PRib-PP</synonym>
    <synonym>PRPP</synonym>
    <synonym>5-Phospho-a-D-ribose 1-diphosphate</synonym>
    <synonym>5-Phospho-a-D-ribose 1-diphosphoric acid</synonym>
    <synonym>5-Phospho-alpha-D-ribose 1-diphosphoric acid</synonym>
    <synonym>5-Phospho-α-D-ribose 1-diphosphate</synonym>
    <synonym>5-Phospho-α-D-ribose 1-diphosphoric acid</synonym>
    <synonym>Phosphoribosyl pyrophosphoric acid</synonym>
    <synonym>5-Phosphoribosyl 1-pyrophosphoric acid</synonym>
    <synonym>5-Phosphoribosyl diphosphoric acid</synonym>
    <synonym>a-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)</synonym>
    <synonym>a-D-Ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)</synonym>
    <synonym>alpha-D-Ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)</synonym>
    <synonym>α-D-Ribofuranose 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)</synonym>
    <synonym>α-D-Ribofuranose 5-(dihydrogen phosphoric acid) 1-(trihydrogen diphosphoric acid)</synonym>
    <synonym>a-Phosphoribosylpyrophosphate</synonym>
    <synonym>a-Phosphoribosylpyrophosphoric acid</synonym>
    <synonym>alpha-Phosphoribosylpyrophosphate</synonym>
    <synonym>α-Phosphoribosylpyrophosphate</synonym>
    <synonym>α-Phosphoribosylpyrophosphoric acid</synonym>
    <synonym>Phosphoribosylpyrophosphoric acid</synonym>
    <synonym>5-Phospho-a-D-ribose-1-diphosphate</synonym>
    <synonym>5-Phospho-a-D-ribosyl pyrophosphate</synonym>
    <synonym>5-Phospho-alpha-D-ribose-1-diphosphate</synonym>
    <synonym>5-Phospho-alpha-D-ribosyl pyrophosphate</synonym>
    <synonym>5-Phosphoribose 1-pyrophosphate</synonym>
    <synonym>5-Phosphoribosyl 1-diphosphate</synonym>
    <synonym>5-Phosphoribosyl a-1-pyrophosphate</synonym>
    <synonym>5-Phosphoribosyl-1-pyrophosphate</synonym>
    <synonym>5-Phosphorylribose 1-a-diphosphate</synonym>
    <synonym>5-Phosphorylribose 1-alpha-diphosphate</synonym>
    <synonym>5-Phosphorylribose 1-pyrophosphate</synonym>
    <synonym>5-Phosphorylribosyl 1-pyrophosphate</synonym>
    <synonym>a-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose</synonym>
    <synonym>a-D-5-Phosphoribosyl 1-pyrophosphate</synonym>
    <synonym>a-D-Ribofuranose 5-phosphate 1-pyrophosphate</synonym>
    <synonym>a-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)</synonym>
    <synonym>alpha-D-5-(Dihydrogen phosphate) 1-(trihydrogen pyrophosphate) ribofuranose</synonym>
    <synonym>alpha-D-5-Phosphoribosyl 1-pyrophosphate</synonym>
    <synonym>alpha-D-Ribofuranose 5-phosphate 1-pyrophosphate</synonym>
    <synonym>alpha-D-Ribofuranose, 5-(dihydrogen phosphate) 1-(trihydrogen diphosphate)</synonym>
    <synonym>Phosphoribosyl-1-pyrophosphate</synonym>
    <synonym>Phosphoribosyl-pyrophosphate</synonym>
    <synonym>Phosphoribosylpyrophosphorate</synonym>
    <synonym>PP-Ribose-P</synonym>
    <synonym>Pyrophosphate, phosphoribosyl</synonym>
    <synonym>5-Phospho-α-D-ribose-1-diphosphate</synonym>
    <synonym>5-Phospho-α-D-ribosyl pyrophosphate</synonym>
    <synonym>5-Phosphoribosyl alpha-1-pyrophosphate</synonym>
    <synonym>5-Phosphoribosyl pyrophosphate</synonym>
    <synonym>5-Phosphoribosyl α-1-pyrophosphate</synonym>
    <synonym>5-Phosphorylribose 1-α-diphosphate</synonym>
    <synonym>Phosphoribosyl pyrophosphate</synonym>
    <synonym>α-D-5-Phosphoribosyl 1-pyrophosphate</synonym>
  </synonyms>
  <chemical_formula>C5H13O14P3</chemical_formula>
  <average_molecular_weight>390.0696</average_molecular_weight>
  <monisotopic_moleculate_weight>389.95181466</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>phosphoribosylpyrophosphate</traditional_iupac>
  <cas_registry_number>7540-64-9</cas_registry_number>
  <smiles>O[C@H]1[C@@H](O)[C@@H](OP(O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C5H13O14P3/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1</inchi>
  <inchikey>PQGCEDQWHSBAJP-TXICZTDVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>5-O-phosphono-D-ribofuranosyl diphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>390.0696</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>389.95181466</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@@H](O)[C@@H](OP(O)(=O)OP(O)(O)=O)O[C@@H]1COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H13O14P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H13O14P3/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PQGCEDQWHSBAJP-TXICZTDVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>229.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>62.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>27.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32077</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB01632</drugbank_id>
  <chemspider_id>7062</chemspider_id>
  <foodb_id>FDB021928</foodb_id>
  <pdbe_id/>
  <chebi_id>17111</chebi_id>
  <pubchem_compound_id>7339</pubchem_compound_id>
  <kegg_id>C00119</kegg_id>
  <meta_cyc_id>PRPP</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007296</knapsack_id>
  <bigg_id>33926</bigg_id>
  <wikipedia_id>Phosphoribosyl pyrophosphate</wikipedia_id>
  <metlin_id>5274</metlin_id>
  <synthesis_reference>Gross, Akiva; Abril, Obsidiana; Lewis, Jerome M.; Geresh, Shimona; Whitesides, George M. Practical synthesis of 5-phospho-D-ribosyl a-1-pyrophosphate (PRPP):  enzymatic routes from ribose 5-phosphate or ribose.  Journal of the American Chemical Society  (1983),  105(25),  7428-35.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00482</protein_accession>
      <name>Ribose-phosphate pyrophosphokinase 1</name>
      <uniprot_id>Q2HJ58</uniprot_id>
      <gene_name>PRPS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00635</protein_accession>
      <name>Nicotinate phosphoribosyltransferase</name>
      <uniprot_id>A5PK51</uniprot_id>
      <gene_name>NAPRT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01004</protein_accession>
      <name>Uridine 5'-monophosphate synthase</name>
      <uniprot_id>P31754</uniprot_id>
      <gene_name>UMPS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:47 UTC</creation_date>
  <update_date>2020-04-15 22:35:21 UTC</update_date>
  <accession>BMDB0000283</accession>
  <secondary_accessions>
    <accession>BMDB00283</accession>
  </secondary_accessions>
  <name>D-Ribose</name>
  <description>D-Ribose, also known as D-ribofuranoside or ribose, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. D-Ribose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Ribose exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>(3R,4S,5R)-5-(Hydroxymethyl)tetrahydrofuran-2,3,4-triol</synonym>
    <synonym>Ribose</synonym>
    <synonym>D-Ribofuranoside</synonym>
    <synonym>D-​Ribofuranose</synonym>
    <synonym>Ribofuranoside</synonym>
    <synonym>Ribofuranose</synonym>
  </synonyms>
  <chemical_formula>C5H10O5</chemical_formula>
  <average_molecular_weight>150.1299</average_molecular_weight>
  <monisotopic_moleculate_weight>150.05282343</monisotopic_moleculate_weight>
  <iupac_name>(3R,4S,5R)-5-(hydroxymethyl)oxolane-2,3,4-triol</iupac_name>
  <traditional_iupac>D-ribofuranoside</traditional_iupac>
  <cas_registry_number>50-69-1</cas_registry_number>
  <smiles>OC[C@H]1OC(O)[C@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4-,5?/m1/s1</inchi>
  <inchikey>HMFHBZSHGGEWLO-SOOFDHNKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Aldoses</external_descriptor>
      <external_descriptor>D-ribose</external_descriptor>
      <external_descriptor>ribofuranose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>95 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.32</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4S,5R)-5-(hydroxymethyl)oxolane-2,3,4-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>150.1299</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>150.05282343</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1OC(O)[C@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4-,5?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HMFHBZSHGGEWLO-SOOFDHNKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>90.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>29.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37401</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By GC-MS and LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Characterization of the biochemical variability of bovine milk using metabolomics</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>322.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>406.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>254.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>311.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>886+/-201</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>323 +/- 70</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). Metabolite measured by NMR.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>406 +/- 95</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). Metabolite measured by NMR.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>255 +/- 78</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). Metabolite measured by NMR.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>312 +/- 40</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>238</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>298</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>219</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>237</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>311.38 +/- 39.97</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00121</kegg_id>
  <foodb_id>FDB031292</foodb_id>
  <chemspider_id>5575</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>5779</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>47013</chebi_id>
  <knapsack_id>C00034198</knapsack_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>33936</bigg_id>
  <wikipedia_id>Ribose</wikipedia_id>
  <metlin_id>313</metlin_id>
  <synthesis_reference>Park, Yong-Cheol; Choi, Jin-Ho; Bennett, George N.; Seo, Jin-Ho. Characterization of D-ribose biosynthesis in Bacillus subtilis JY200 deficient in transketolase gene. Journal of Biotechnology  (2006),  121(4),  508-516.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
    <reference>
      <reference_text>Characterization of the biochemical variability of bovine milk using metabolomics</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00132</protein_accession>
      <name>Poly(ADP-ribose) glycohydrolase ARH3</name>
      <uniprot_id>Q3SYV9</uniprot_id>
      <gene_name>ADPRHL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00135</protein_accession>
      <name>Poly(ADP-ribose) glycohydrolase</name>
      <uniprot_id>O02776</uniprot_id>
      <gene_name>PARG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:49 UTC</creation_date>
  <update_date>2020-03-13 16:19:57 UTC</update_date>
  <accession>BMDB0000285</accession>
  <secondary_accessions>
    <accession>BMDB00285</accession>
  </secondary_accessions>
  <name>Uridine triphosphate</name>
  <description/>
  <synonyms>
    <synonym>5'-UTP</synonym>
    <synonym>H4UTP</synonym>
    <synonym>Uridine 5'-triphosphate</synonym>
    <synonym>Uridine 5'-triphosphoric acid</synonym>
    <synonym>Uridine triphosphoric acid</synonym>
    <synonym>Uridine mono(tetrahydrogen triphosphate)</synonym>
    <synonym>Uteplex</synonym>
    <synonym>UTP</synonym>
    <synonym>MG UTP</synonym>
    <synonym>Magnesium UTP</synonym>
    <synonym>Magnesium uridine triphosphate</synonym>
    <synonym>Triphosphate, uridine</synonym>
    <synonym>MG-UTP</synonym>
    <synonym>Triphosphate, magnesium uridine</synonym>
    <synonym>UTP, Magnesium</synonym>
  </synonyms>
  <chemical_formula>C9H15N2O15P3</chemical_formula>
  <average_molecular_weight>484.1411</average_molecular_weight>
  <monisotopic_moleculate_weight>483.968527356</monisotopic_moleculate_weight>
  <iupac_name>({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</iupac_name>
  <traditional_iupac>uridine 5'-triphosphoric acid</traditional_iupac>
  <cas_registry_number>63-39-8</cas_registry_number>
  <smiles>O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C9H15N2O15P3/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1</inchi>
  <inchikey>PGAVKCOVUIYSFO-XVFCMESISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine ribonucleoside triphosphates. These are pyrimidine ribobucleotides with triphosphate group  linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine ribonucleotides</sub_class>
    <direct_parent>Pyrimidine ribonucleoside triphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine ribonucleoside triphosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ribonucleotides</external_descriptor>
      <external_descriptor>pyrimidine ribonucleoside 5'-triphosphate</external_descriptor>
      <external_descriptor>uridine 5'-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>484.1411</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>483.968527356</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H15N2O15P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H15N2O15P3/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PGAVKCOVUIYSFO-XVFCMESISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>258.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>85.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35518</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00075</kegg_id>
  <drugbank_id>DB04005</drugbank_id>
  <foodb_id>FDB031251</foodb_id>
  <chemspider_id>5903</chemspider_id>
  <pubchem_compound_id>6133</pubchem_compound_id>
  <chebi_id>15713</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Uridine triphosphate</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33760</bigg_id>
  <metlin_id>5277</metlin_id>
  <synthesis_reference>Kenner, G. W.; Todd, A. R.; Webb, R. F.; Weymouth, F. J.  Nucleotides. XXVIII. Synthesis of uridine 5'-triphosphate.    Journal of the Chemical Society  (1954),  46-52  2288-93.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:50 UTC</creation_date>
  <update_date>2020-04-15 22:30:53 UTC</update_date>
  <accession>BMDB0000286</accession>
  <secondary_accessions>
    <accession>BMDB00286</accession>
  </secondary_accessions>
  <name>Uridine diphosphate glucose</name>
  <description/>
  <synonyms>
    <synonym>GLUCOSE-uridine-C1,5'-diphosphATE</synonym>
    <synonym>UDP-D-Glucose</synonym>
    <synonym>UDPglucose</synonym>
    <synonym>URIDINE-5'-diphosphATE-glucose</synonym>
    <synonym>UDP-alpha-D-Glucose</synonym>
    <synonym>GLUCOSE-uridine-C1,5'-diphosphoric acid</synonym>
    <synonym>URIDINE-5'-diphosphoric acid-glucose</synonym>
    <synonym>UDP-a-D-Glucose</synonym>
    <synonym>UDP-Α-D-glucose</synonym>
    <synonym>Uridine diphosphoric acid glucose</synonym>
    <synonym>Diphosphate glucose, uridine</synonym>
    <synonym>Diphosphoglucose, uridine</synonym>
    <synonym>Glucose, UDP</synonym>
    <synonym>Glucose, uridine diphosphate</synonym>
    <synonym>UDP Glucose</synonym>
    <synonym>UDPG</synonym>
    <synonym>Uridine diphosphoglucose</synonym>
    <synonym>UDP-GLC</synonym>
    <synonym>UDP-Glucose</synonym>
    <synonym>Uridine 5'-(alpha-D-glucopyranosyl pyrophosphate)</synonym>
    <synonym>Uridine 5'-(α-D-glucopyranosyl pyrophosphate)</synonym>
    <synonym>Uridine 5'-diphosphate glucose</synonym>
    <synonym>Uridine 5'-diphospho-alpha-D-glucose</synonym>
    <synonym>Uridine 5'-diphospho-α-D-glucose</synonym>
    <synonym>Uridine 5'-diphosphoglucose</synonym>
    <synonym>Uridine 5’-(α-D-glucopyranosyl pyrophosphate)</synonym>
    <synonym>Uridine 5’-diphosphate glucose</synonym>
    <synonym>Uridine 5’-diphospho-α-D-glucose</synonym>
    <synonym>Uridine 5’-diphosphoglucose</synonym>
    <synonym>Uridine diphospho-D-glucose</synonym>
    <synonym>Uridine pyrophosphate-glucose</synonym>
    <synonym>Uridine diphosphate glucose</synonym>
  </synonyms>
  <chemical_formula>C15H24N2O17P2</chemical_formula>
  <average_molecular_weight>566.3018</average_molecular_weight>
  <monisotopic_moleculate_weight>566.055020376</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>udp-α-D-glucose</traditional_iupac>
  <cas_registry_number>133-89-1</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1</inchi>
  <inchikey>HSCJRCZFDFQWRP-JZMIEXBBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine nucleotide sugars</sub_class>
    <direct_parent>Pyrimidine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine nucleotide sugar</substituent>
      <substituent>Pyrimidine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>UDP-D-glucose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>566.3018</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>566.055020376</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H24N2O17P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HSCJRCZFDFQWRP-JZMIEXBBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>291.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>106.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>45.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>36799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>48056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448448</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>126+/-32</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00029</kegg_id>
  <drugbank_id>DB01861</drugbank_id>
  <foodb_id>FDB005660</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>8629</pubchem_compound_id>
  <chebi_id>46229</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00001514</knapsack_id>
  <meta_cyc_id>CPD-12575</meta_cyc_id>
  <wikipedia_id>Uridine_diphosphate_glucose</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Burma, D. P.; Mortimer, D. C.  Biosynthesis of uridine diphosphate glucose and sucrose in sugar-beet leaf.    Archives of Biochemistry and Biophysics  (1956),  62  16-28.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00848</protein_accession>
      <name>UDP-glucose 6-dehydrogenase</name>
      <uniprot_id>P12378</uniprot_id>
      <gene_name>UGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00957</protein_accession>
      <name>Galactose-1-phosphate uridylyltransferase</name>
      <uniprot_id>Q0V7N7</uniprot_id>
      <gene_name>GALT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00958</protein_accession>
      <name>Glycogen [starch] synthase, muscle</name>
      <uniprot_id>A7MB78</uniprot_id>
      <gene_name>GYS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00959</protein_accession>
      <name>Galactose-1-phosphate uridylyltransferase</name>
      <uniprot_id>Q58CX1</uniprot_id>
      <gene_name>GALT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00960</protein_accession>
      <name>UTP--glucose-1-phosphate uridylyltransferase</name>
      <uniprot_id>Q07130</uniprot_id>
      <gene_name>UGP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02044</protein_accession>
      <name>P2Y purinoceptor 14</name>
      <uniprot_id>Q3SX17</uniprot_id>
      <gene_name>P2RY14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:51 UTC</creation_date>
  <update_date>2020-04-14 22:47:17 UTC</update_date>
  <accession>BMDB0000288</accession>
  <secondary_accessions>
    <accession>BMDB00288</accession>
  </secondary_accessions>
  <name>Uridine 5'-monophosphate</name>
  <description>Uridine 5'-monophosphate, also known as uridylic acid or UMP, belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. Uridine 5'-monophosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine 5'-monophosphate exists in all living species, ranging from bacteria to humans. Uridine 5'-monophosphate participates in a number of enzymatic reactions, within cattle. In particular, Uridine 5'-monophosphate can be converted into uridine 5'-diphosphate; which is mediated by the enzyme UMP-CMP kinase. In addition, Uridine 5'-monophosphate can be biosynthesized from uridine 5'-diphosphate; which is catalyzed by the enzyme soluble calcium-activated nucleotidase 1. In cattle, uridine 5'-monophosphate is involved in the metabolic pathway called lactose synthesis pathway.</description>
  <synonyms>
    <synonym>5'-UMP</synonym>
    <synonym>5'Uridylic acid</synonym>
    <synonym>pU</synonym>
    <synonym>UMP</synonym>
    <synonym>Uridine 5'-(dihydrogen phosphate)</synonym>
    <synonym>Uridine 5'-phosphate</synonym>
    <synonym>Uridine 5'-phosphoric acid</synonym>
    <synonym>Uridine monophosphate</synonym>
    <synonym>URIDINE-5'-monophosphATE</synonym>
    <synonym>Uridylate</synonym>
    <synonym>Uridylic acid</synonym>
    <synonym>5'Uridylate</synonym>
    <synonym>Uridine 5'-(dihydrogen phosphoric acid)</synonym>
    <synonym>Uridine monophosphoric acid</synonym>
    <synonym>URIDINE-5'-monophosphoric acid</synonym>
    <synonym>Uridine 5'-monophosphoric acid</synonym>
    <synonym>Uridine 5'-phosphorate</synonym>
    <synonym>Uridine mono(dihydrogen phosphate)</synonym>
    <synonym>Uridine phosphate</synonym>
    <synonym>Acids, uridylic</synonym>
    <synonym>monoPhosphate, uridine</synonym>
    <synonym>5'-monoPhosphate, uridine</synonym>
    <synonym>Uridylic acids</synonym>
    <synonym>Acid, uridylic</synonym>
    <synonym>Uridine 5' monophosphate</synonym>
  </synonyms>
  <chemical_formula>C9H13N2O9P</chemical_formula>
  <average_molecular_weight>324.1813</average_molecular_weight>
  <monisotopic_moleculate_weight>324.035866536</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>uridine monophosphate</traditional_iupac>
  <cas_registry_number>58-97-9</cas_registry_number>
  <smiles>O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1</inchi>
  <inchikey>DJJCXFVJDGTHFX-XVFCMESISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group  linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine ribonucleotides</sub_class>
    <direct_parent>Pyrimidine ribonucleoside monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ribonucleotides</external_descriptor>
      <external_descriptor>pyrimidine ribonucleoside 5'-monophosphate</external_descriptor>
      <external_descriptor>uridine 5'-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>324.1813</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>324.035866536</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13N2O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DJJCXFVJDGTHFX-XVFCMESISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>165.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>63.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439120</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>58+/-31</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0 - 28.700</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44.</reference_text>
          <pubmed_id>7196410</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>56+/-11</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00105</kegg_id>
  <drugbank_id>DB03685</drugbank_id>
  <foodb_id>FDB031248</foodb_id>
  <chemspider_id>5808</chemspider_id>
  <pubchem_compound_id>6030</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16695</chebi_id>
  <knapsack_id>C00007311</knapsack_id>
  <meta_cyc_id>UMP</meta_cyc_id>
  <wikipedia_id>Uridine_monophosphate</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33873</bigg_id>
  <metlin_id/>
  <synthesis_reference>Wang Xing; Wang Xiuwen; Yin Mengxin; Xiao Zijun; Ma Cuiqing; Lin Zhixin; Wang Peng George; Xu Ping  Production of uridine 5'-monophosphate by Corynebacterium ammoniagenes ATCC 6872 using a statistically improved biocatalytic process.    Applied microbiology and biotechnology  (2007),  76(2),  321-8.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44.</reference_text>
      <pubmed_id>7196410</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:52 UTC</creation_date>
  <update_date>2020-04-16 17:51:14 UTC</update_date>
  <accession>BMDB0000289</accession>
  <secondary_accessions>
    <accession>BMDB00289</accession>
  </secondary_accessions>
  <name>Uric acid</name>
  <description>Uric acid, also known as urate or acid, uric, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Uric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Uric acid exists in all living species, ranging from bacteria to humans. Uric acid is a potentially toxic compound. Uric acid has been found to be associated with several diseases known as fanconi syndrome, impaired glucose tolerance, and d-lactic acidosis; also uric acid has been linked to several inborn metabolic disorders including atic deficiency and lesch-nyhan syndrome.</description>
  <synonyms>
    <synonym>2,6,8-Trioxopurine</synonym>
    <synonym>2,6,8-Trioxypurine</synonym>
    <synonym>Purine-2,6,8(1H,3H,9H)-trione</synonym>
    <synonym>Urate</synonym>
    <synonym>1H-Purine-2,6,8-triol</synonym>
    <synonym>2,6,8-Trihydroxypurine</synonym>
    <synonym>Lithate</synonym>
    <synonym>Lithic acid</synonym>
    <synonym>Acid urate, ammonium</synonym>
    <synonym>Ammonium acid urate</synonym>
    <synonym>Monohydrate, sodium urate</synonym>
    <synonym>Urate, ammonium acid</synonym>
    <synonym>Urate, monosodium</synonym>
    <synonym>Acid, uric</synonym>
    <synonym>Monosodium urate monohydrate</synonym>
    <synonym>Sodium acid urate</synonym>
    <synonym>Sodium urate</synonym>
    <synonym>Trioxopurine</synonym>
    <synonym>Urate, sodium acid</synonym>
    <synonym>Monohydrate, monosodium urate</synonym>
    <synonym>Monosodium urate</synonym>
    <synonym>Potassium urate</synonym>
    <synonym>Sodium acid urate monohydrate</synonym>
    <synonym>Urate monohydrate, sodium</synonym>
    <synonym>Acid urate, sodium</synonym>
    <synonym>Sodium urate monohydrate</synonym>
    <synonym>Urate monohydrate, monosodium</synonym>
    <synonym>Urate, potassium</synonym>
    <synonym>Urate, sodium</synonym>
  </synonyms>
  <chemical_formula>C5H4N4O3</chemical_formula>
  <average_molecular_weight>168.1103</average_molecular_weight>
  <monisotopic_moleculate_weight>168.028340014</monisotopic_moleculate_weight>
  <iupac_name>2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione</iupac_name>
  <traditional_iupac>uric acid</traditional_iupac>
  <cas_registry_number>69-93-2</cas_registry_number>
  <smiles>O=C1NC2=C(N1)C(=O)NC(=O)N2</smiles>
  <inchi>InChI=1S/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h(H4,6,7,8,9,10,11,12)</inchi>
  <inchikey>LEHOTFFKMJEONL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Xanthines</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
      <substituent>Xanthine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>uric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>&gt; 300 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.06 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.17</value>
      <source>NAHUM,A &amp; HORVATH,C (1980)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>168.1103</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>168.028340014</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O=C1NC2=C(N1)C(=O)NC(=O)N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H4N4O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h(H4,6,7,8,9,10,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LEHOTFFKMJEONL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>99.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31919</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>91.0117-191.541</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by procedure of Folin and Wu (1919)</comment>
      <references>
        <reference>
          <reference_text>Arthur K. Anderson, Howard E. Gayley, Avery D. Pratt. Studies on the Chemical Composition of Bovine Blood. J. Dairy Science (1930) 13(4):336-348   doi: 10.3168/jds.S0022-0302(30)93530-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>53.536 - 142.764</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Indyk HE, Woollard DC: Determination of orotic acid, uric acid, and creatinine in milk by liquid chromatography. J AOAC Int. 2004 Jan-Feb;87(1):116-22.</reference_text>
          <pubmed_id>15084094</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>199.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw whole milk</comment>
      <references>
        <reference>
          <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
          <pubmed_id>6539345</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>56.200 +/- 12.300</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Giesecke D, Ehrentreich L, Stangassinger M, Ahrens F: Mammary and renal excretion of purine metabolites in relation to energy intake and milk yield in dairy cows. J Dairy Sci. 1994 Aug;77(8):2376-81. doi: 10.3168/jds.S0022-0302(94)77180-0.</reference_text>
          <pubmed_id>7962859</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>122.539 +/- 0.595</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Carbohydrate Polymers 37 (1998) 225-229</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00366</kegg_id>
  <drugbank_id>DB08844</drugbank_id>
  <foodb_id>FDB015350</foodb_id>
  <chemspider_id>1142</chemspider_id>
  <pubchem_compound_id>1175</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17775</chebi_id>
  <knapsack_id>C00007301</knapsack_id>
  <meta_cyc_id>URATE</meta_cyc_id>
  <wikipedia_id>Uric_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34768</bigg_id>
  <metlin_id>88</metlin_id>
  <synthesis_reference>Brenner-Holzach, O.; Leuthardt, F.  Uric acid formation from glucose carbon in Drosophila melanogaster. Preliminary report.    Helvetica Chimica Acta  (1963),  46(4),  1426-8.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
      <pubmed_id>6539345</pubmed_id>
    </reference>
    <reference>
      <reference_text>Giesecke D, Ehrentreich L, Stangassinger M, Ahrens F: Mammary and renal excretion of purine metabolites in relation to energy intake and milk yield in dairy cows. J Dairy Sci. 1994 Aug;77(8):2376-81. doi: 10.3168/jds.S0022-0302(94)77180-0.</reference_text>
      <pubmed_id>7962859</pubmed_id>
    </reference>
    <reference>
      <reference_text>Indyk HE, Woollard DC: Determination of orotic acid, uric acid, and creatinine in milk by liquid chromatography. J AOAC Int. 2004 Jan-Feb;87(1):116-22.</reference_text>
      <pubmed_id>15084094</pubmed_id>
    </reference>
    <reference>
      <reference_text>Carbohydrate Polymers 37 (1998) 225-229</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00603</protein_accession>
      <name>Xanthine dehydrogenase/oxidase</name>
      <uniprot_id>P80457</uniprot_id>
      <gene_name>XDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01253</protein_accession>
      <name>Uricase</name>
      <uniprot_id>Q3MHG7</uniprot_id>
      <gene_name>UOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:53 UTC</creation_date>
  <update_date>2020-04-16 17:51:14 UTC</update_date>
  <accession>BMDB0000290</accession>
  <secondary_accessions>
    <accession>BMDB00290</accession>
  </secondary_accessions>
  <name>Uridine diphosphate-N-acetylglucosamine</name>
  <description/>
  <synonyms>
    <synonym>(2R,3R,4R,5S,6R)-3-(Acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphate (non-preferred name)</synonym>
    <synonym>UDP-GlcNAc</synonym>
    <synonym>UDP-N-Acetyl-D-glucosamine</synonym>
    <synonym>UDP-N-Acetylglucosamine</synonym>
    <synonym>URIDINE-diphosphATE-N-acetylglucosamine</synonym>
    <synonym>(2R,3R,4R,5S,6R)-3-(Acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphoric acid (non-preferred name)</synonym>
    <synonym>URIDINE-diphosphoric acid-N-acetylglucosamine</synonym>
    <synonym>Uridine diphosphoric acid-N-acetylglucosamine</synonym>
    <synonym>N-[2-[[[5-[(2,4-Dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide</synonym>
    <synonym>UDP-a-D-N-Acetylglucosamine</synonym>
    <synonym>UDP-Acetyl-D-glucosamine</synonym>
    <synonym>UDP-Acetyl-delta-glucosamine</synonym>
    <synonym>UDP-Acetylglucosamine</synonym>
    <synonym>UDP-alpha-D-N-Acetylglucosamine</synonym>
    <synonym>UDP-alpha-delta-N-Acetylglucosamine</synonym>
    <synonym>UDP-N-Acetyl-delta-glucosamine</synonym>
    <synonym>UDP-N-Acetyl-glucosamine</synonym>
    <synonym>UPPAG</synonym>
    <synonym>Uridine 5'-diphospho-N-acetlyglucosamine</synonym>
    <synonym>Uridine 5'-diphospho-N-acetylglucosamine</synonym>
    <synonym>Uridine diphosphate N-acetyl-D-glucosamine</synonym>
    <synonym>Uridine diphosphate N-acetyl-delta-glucosamine</synonym>
    <synonym>Uridine diphosphate N-acetylglucosamine</synonym>
    <synonym>Uridine diphospho-2-acetamido-2-deoxy-D-glucose</synonym>
    <synonym>Uridine diphospho-2-acetamido-2-deoxy-delta-glucose</synonym>
    <synonym>Uridine diphospho-N-acetyl-D-glucosamine</synonym>
    <synonym>Uridine diphospho-N-acetyl-delta-glucosamine</synonym>
    <synonym>Uridine diphospho-N-acetylglucosamine</synonym>
    <synonym>Uridine diphosphoacetylglucosamine</synonym>
    <synonym>Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-glucopyranosyl ester</synonym>
    <synonym>Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl ester</synonym>
    <synonym>Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl ester</synonym>
    <synonym>Uridine pyrophosphoacetylglucosamine</synonym>
    <synonym>[[3-Acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinate</synonym>
    <synonym>[[3-Acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinic acid</synonym>
    <synonym>Acetylglucosamine, UDP</synonym>
    <synonym>Diphosphate N-acetylglucosamine, uridine</synonym>
    <synonym>Diphospho-N-acetylglucosamine, uridine</synonym>
    <synonym>N-Acetylglucosamine, uridine diphosphate</synonym>
    <synonym>Pyrophosphoacetylglucosamine, uridine</synonym>
    <synonym>UDP Acetylglucosamine</synonym>
    <synonym>UDPGNAc</synonym>
    <synonym>Uridine diphosphate N acetylglucosamine</synonym>
    <synonym>Uridine diphospho N acetylglucosamine</synonym>
  </synonyms>
  <chemical_formula>C17H27N3O17P2</chemical_formula>
  <average_molecular_weight>607.3537</average_molecular_weight>
  <monisotopic_moleculate_weight>607.081569477</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>udp-N-acetyl-α-D-glucosamine</traditional_iupac>
  <cas_registry_number>528-04-1</cas_registry_number>
  <smiles>CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1</inchi>
  <inchikey>LFTYTUAZOPRMMI-CFRASDGPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine nucleotide sugars</sub_class>
    <direct_parent>Pyrimidine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine nucleotide sugar</substituent>
      <substituent>Pyrimidine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>UDP-amino sugar</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>607.3537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>607.081569477</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C17H27N3O17P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LFTYTUAZOPRMMI-CFRASDGPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>300.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>117.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>50.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439119</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>268+/-40</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00043</kegg_id>
  <drugbank_id>DB03397</drugbank_id>
  <foodb_id>FDB021930</foodb_id>
  <chemspider_id>393240</chemspider_id>
  <pubchem_compound_id>445675</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16264</chebi_id>
  <knapsack_id>C00019358</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>33638</bigg_id>
  <metlin_id>5281</metlin_id>
  <synthesis_reference>Takenouchi, Kenji; Ishige, Kazuya; Midorikawa, Yuichiro; Okuyama, Kiyoshi; Hamamoto, Tomoki; Noguchi, Toshitada.  Process for producing uridine diphosphate-N-acetylglucosamine.    PCT Int. Appl.  (1999),     38 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00651</protein_accession>
      <name>Protein O-linked-mannose beta-1,2-N-acetylglucosaminyltransferase 1</name>
      <uniprot_id>Q5EAB6</uniprot_id>
      <gene_name>POMGNT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00805</protein_accession>
      <name>UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase</name>
      <uniprot_id>Q5EA65</uniprot_id>
      <gene_name>DPAGT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00845</protein_accession>
      <name>Exostosin-2</name>
      <uniprot_id>O77783</uniprot_id>
      <gene_name>EXT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00847</protein_accession>
      <name>Exostosin-1</name>
      <uniprot_id>A5D7I4</uniprot_id>
      <gene_name>EXT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00914</protein_accession>
      <name>Alpha-1,3-mannosyl-glycoprotein 4-beta-N-acetylglucosaminyltransferase A</name>
      <uniprot_id>O77836</uniprot_id>
      <gene_name>MGAT4A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01294</protein_accession>
      <name>Phosphatidylinositol N-acetylglucosaminyltransferase subunit H</name>
      <uniprot_id>Q32L89</uniprot_id>
      <gene_name>PIGH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01295</protein_accession>
      <name>Phosphatidylinositol N-acetylglucosaminyltransferase subunit C</name>
      <uniprot_id>Q3ZBX1</uniprot_id>
      <gene_name>PIGC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01296</protein_accession>
      <name>Beta-1,3-galactosyl-O-glycosyl-glycoprotein beta-1,6-N-acetylglucosaminyltransferase</name>
      <uniprot_id>Q92180</uniprot_id>
      <gene_name>GCNT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01297</protein_accession>
      <name>Beta-1,3-galactosyl-O-glycosyl-glycoprotein beta-1,6-N-acetylglucosaminyltransferase 3</name>
      <uniprot_id>Q7YQE1</uniprot_id>
      <gene_name>GCNT3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01298</protein_accession>
      <name>N-acetyllactosaminide beta-1,3-N-acetylglucosaminyltransferase</name>
      <uniprot_id>Q5EA01</uniprot_id>
      <gene_name>B3GNT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02080</protein_accession>
      <name>UDP-N-acetylglucosamine transporter</name>
      <uniprot_id>Q6YC49</uniprot_id>
      <gene_name>SLC35A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:55 UTC</creation_date>
  <update_date>2020-04-15 22:36:48 UTC</update_date>
  <accession>BMDB0000291</accession>
  <secondary_accessions>
    <accession>BMDB00291</accession>
  </secondary_accessions>
  <name>Vanillylmandelic acid</name>
  <description>Vanillylmandelic acid, also known as vanillylmandelic acid or vanillylmandelic acid CPD, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Vanillylmandelic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Vanillylmandelic acid exists in all living organisms, ranging from bacteria to humans. Vanillylmandelic acid participates in a number of enzymatic reactions, within cattle. In particular, Vanillylmandelic acid can be biosynthesized from 3-methoxy-4-hydroxyphenylglycolaldehyde through the action of the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In addition, Vanillylmandelic acid and pyrocatechol can be biosynthesized from 3,4-dihydroxymandelic acid and guaiacol; which is catalyzed by the enzyme catechol O-methyltransferase. In cattle, vanillylmandelic acid is involved in the metabolic pathway called the tyrosine metabolism pathway.</description>
  <synonyms>
    <synonym>Vanillylmandelate</synonym>
    <synonym>(4-Hydroxy-3-methoxyphenyl)glycolate</synonym>
    <synonym>(4-Hydroxy-3-methoxyphenyl)glycolic acid</synonym>
    <synonym>3-Methoxy-4-hydroxy-mandelic acid</synonym>
    <synonym>3-Methoxy-4-hydroxymandelate</synonym>
    <synonym>3-Methoxy-4-hydroxymandelic acid</synonym>
    <synonym>3-Methoxy-4-hydroxyphenylhydroxyacetate</synonym>
    <synonym>3-Methoxy-4-hydroxyphenylhydroxyacetic acid</synonym>
    <synonym>4'-Hydroxy-3'-methoxymandelate</synonym>
    <synonym>4'-Hydroxy-3'-methoxymandelic acid</synonym>
    <synonym>4-Hydroxy 3-methoxymandelic acid</synonym>
    <synonym>4-Hydroxy-3-methoxy-DL-mandelate</synonym>
    <synonym>4-Hydroxy-3-methoxy-DL-mandelic acid</synonym>
    <synonym>4-Hydroxy-3-methoxy-mandelate</synonym>
    <synonym>4-Hydroxy-3-methoxy-mandelic acid</synonym>
    <synonym>4-Hydroxy-3-methoxymandelate</synonym>
    <synonym>4-Hydroxy-3-methoxymandelic acid</synonym>
    <synonym>DL-3-Methoxy-4-hydroxymandelate</synonym>
    <synonym>DL-3-Methoxy-4-hydroxymandelic acid</synonym>
    <synonym>DL-4-Hydroxy-3-methoxymandelate</synonym>
    <synonym>DL-4-Hydroxy-3-methoxymandelic acid</synonym>
    <synonym>DL-Vanillomandelate</synonym>
    <synonym>DL-Vanillomandelic acid</synonym>
    <synonym>DL-Vanillylmandelate</synonym>
    <synonym>DL-Vanillylmandelic acid</synonym>
    <synonym>HMMA</synonym>
    <synonym>Hydroxymethoxymandelic acid</synonym>
    <synonym>Lopac-H-0131</synonym>
    <synonym>Vainillylmandelic acid</synonym>
    <synonym>Vanillinmandelate</synonym>
    <synonym>Vanillinmandelic acid</synonym>
    <synonym>Vanillomandelate</synonym>
    <synonym>Vanillomandelic acid</synonym>
    <synonym>Vanillyl-mandelic acid</synonym>
    <synonym>Vanillylmandellic acid</synonym>
    <synonym>Vanillymandelic acid</synonym>
    <synonym>Vanilmandelate</synonym>
    <synonym>Vanilmandelic acid</synonym>
    <synonym>Vanilylmandelic acid</synonym>
    <synonym>Vanyl-mandelic acid</synonym>
    <synonym>Vanylmandelic acid</synonym>
    <synonym>VMA</synonym>
    <synonym>2-Phenyllactic acid</synonym>
    <synonym>VMA CPD</synonym>
    <synonym>Atrolactic acid</synonym>
    <synonym>Atrolactic acid monosodium salt, (S)-isomer</synonym>
    <synonym>Atrolactic acid, (+-)-isomer</synonym>
    <synonym>Hydroxymethylmandelic acid</synonym>
  </synonyms>
  <chemical_formula>C9H10O5</chemical_formula>
  <average_molecular_weight>198.1727</average_molecular_weight>
  <monisotopic_moleculate_weight>198.05282343</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid</iupac_name>
  <traditional_iupac>(S)-hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid</traditional_iupac>
  <cas_registry_number>55-10-7</cas_registry_number>
  <smiles>COC1=C(O)C=CC(=C1)[C@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)/t8-/m0/s1</inchi>
  <inchikey>CGQCWMIAEPEHNQ-QMMMGPOBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Methoxyphenols</sub_class>
    <direct_parent>Methoxyphenols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>132 - 134 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>198.1727</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>198.05282343</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=C(O)C=CC(=C1)[C@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)/t8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CGQCWMIAEPEHNQ-QMMMGPOBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>86.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1258</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05584</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB021931</foodb_id>
  <chemspider_id>643307</chemspider_id>
  <pubchem_compound_id>736172</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>1127735</chebi_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Vanillylmandelic acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>46071</bigg_id>
  <metlin_id>697</metlin_id>
  <synthesis_reference>Recondo, E. F.; Rinderknecht, H. Preparation of epinephrine and norepinephrine metabolites, 3-methoxy-4-hydroxymandelic acid and 3,4-dihydroxymandelic acid. Journal of Organic Chemistry (1960), 25 2248-50.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:56 UTC</creation_date>
  <update_date>2020-04-16 20:39:04 UTC</update_date>
  <accession>BMDB0000292</accession>
  <secondary_accessions>
    <accession>BMDB00292</accession>
  </secondary_accessions>
  <name>Xanthine</name>
  <description>Xanthine, also known as Xan or 2,6-dioxopurine, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Xanthine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Xanthine exists in all living species, ranging from bacteria to humans. Xanthine is a potentially toxic compound. Xanthine has been found to be associated with several diseases known as crohn's disease, colorectal cancer, degenerative disc disease, and cystic fibrosis; also xanthine has been linked to the inborn metabolic disorders including lesch-nyhan syndrome.</description>
  <synonyms>
    <synonym>2,6-Dihydroxypurine</synonym>
    <synonym>2,6-Dioxo-1,2,3,6-tetrahydropurine</synonym>
    <synonym>9H-Purine-2,6-(1H,3H)-dione</synonym>
    <synonym>Purine-2(3H),6(1H)-dione</synonym>
    <synonym>Xan</synonym>
    <synonym>1H-Purine-2,6-diol</synonym>
    <synonym>2,6(1,3)-Purinedion</synonym>
    <synonym>2,6-Dioxopurine</synonym>
    <synonym>3,7-Dihydro-1H-purine-2,6-dione</synonym>
    <synonym>3,7-Dihydropurine-2,6-dione</synonym>
    <synonym>9H-Purine-2,6(1H,3H)-dione</synonym>
    <synonym>9H-Purine-2,6-diol</synonym>
    <synonym>Dioxopurine</synonym>
    <synonym>Isoxanthine</synonym>
    <synonym>Pseudoxanthine</synonym>
    <synonym>Purine-2,6(1H,3H)-dione</synonym>
    <synonym>Purine-2,6-diol</synonym>
    <synonym>Xanthic oxide</synonym>
    <synonym>Xanthin</synonym>
  </synonyms>
  <chemical_formula>C5H4N4O2</chemical_formula>
  <average_molecular_weight>152.1109</average_molecular_weight>
  <monisotopic_moleculate_weight>152.033425392</monisotopic_moleculate_weight>
  <iupac_name>2,3,6,7-tetrahydro-1H-purine-2,6-dione</iupac_name>
  <traditional_iupac>xanthine</traditional_iupac>
  <cas_registry_number>69-89-6</cas_registry_number>
  <smiles>O=C1NC2=C(NC=N2)C(=O)N1</smiles>
  <inchi>InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)</inchi>
  <inchikey>LRFVTYWOQMYALW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Xanthines</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
      <substituent>Xanthine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Purine alkaloids</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>xanthine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>&gt; 300 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.069 mg/mL at 16 °C; 9.5 mg/mL (sodium salt)</value>
      <source>MERCK INDEX (1996); Human Metabolome Project (salt)</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.73</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,3,6,7-tetrahydro-1H-purine-2,6-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>152.1109</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>152.033425392</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O=C1NC2=C(NC=N2)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H4N4O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LRFVTYWOQMYALW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>86.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>36.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447350</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw whole milk</comment>
      <references>
        <reference>
          <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
          <pubmed_id>6539345</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.38+/-0.02</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.45+/-0.03</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.26+/-0.02</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.29+/-0.02</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00385</kegg_id>
  <drugbank_id>DB02134</drugbank_id>
  <foodb_id>FDB001977</foodb_id>
  <chemspider_id>1151</chemspider_id>
  <pubchem_compound_id>1188</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17712</chebi_id>
  <knapsack_id>C00019660</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Xanthine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34825</bigg_id>
  <metlin_id>82</metlin_id>
  <synthesis_reference>Procedure for the production of xanthine and xanthine-like materials.    Fr.  (1967),     4 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
      <pubmed_id>6539345</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00603</protein_accession>
      <name>Xanthine dehydrogenase/oxidase</name>
      <uniprot_id>P80457</uniprot_id>
      <gene_name>XDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:57 UTC</creation_date>
  <update_date>2020-04-14 22:47:18 UTC</update_date>
  <accession>BMDB0000293</accession>
  <secondary_accessions>
    <accession>BMDB00293</accession>
  </secondary_accessions>
  <name>Xanthosine 5-triphosphate</name>
  <description/>
  <synonyms>
    <synonym>O(5')-(Tetrahydroxytriphosphoryl)xanthosine</synonym>
    <synonym>Triphopsphoric acid 1-xanthosin-5'-yl ester</synonym>
    <synonym>Xanthosine 5'-triphosphate</synonym>
    <synonym>Xanthosine triphosphate</synonym>
    <synonym>Triphopsphate 1-xanthosin-5'-yl ester</synonym>
    <synonym>Triphopsphic acid 1-xanthosin-5'-yl ester</synonym>
    <synonym>Xanthosine 5'-triphosphoric acid</synonym>
    <synonym>Xanthosine triphosphoric acid</synonym>
    <synonym>Xanthosine 5-triphosphoric acid</synonym>
    <synonym>5'-XTP</synonym>
    <synonym>Xanthosine mono(tetrahydrogen triphosphate)</synonym>
    <synonym>XTP</synonym>
    <synonym>Xanthosine 5'-triphosphate 2Sodium salt</synonym>
  </synonyms>
  <chemical_formula>C10H15N4O15P3</chemical_formula>
  <average_molecular_weight>524.1652</average_molecular_weight>
  <monisotopic_moleculate_weight>523.974675366</monisotopic_moleculate_weight>
  <iupac_name>({[({[(2R,3S,4R,5R)-5-(2,6-dihydroxy-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</iupac_name>
  <traditional_iupac>xanthosine 5-triphosphate</traditional_iupac>
  <cas_registry_number>6253-56-1</cas_registry_number>
  <smiles>O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=C(O)N=C2O</smiles>
  <inchi>InChI=1S/C10H15N4O15P3/c15-5-3(1-26-31(22,23)29-32(24,25)28-30(19,20)21)27-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1</inchi>
  <inchikey>CAEFEWVYEZABLA-UUOKFMHZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group  linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside triphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Xanthines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside triphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Xanthine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>purine ribonucleoside 5'-triphosphate</external_descriptor>
      <external_descriptor>xanthosine 5'-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.016</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>({[({[(2R,3S,4R,5R)-5-(2,6-dihydroxy-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>524.1652</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>523.974675366</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=C(O)N=C2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H15N4O15P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H15N4O15P3/c15-5-3(1-26-31(22,23)29-32(24,25)28-30(19,20)21)27-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CAEFEWVYEZABLA-UUOKFMHZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>293.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>95.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27921</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27922</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34480</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00700</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB021932</foodb_id>
  <chemspider_id>388429</chemspider_id>
  <pdbe_id/>
  <chebi_id>10049</chebi_id>
  <pubchem_compound_id>439296</pubchem_compound_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>35735</bigg_id>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>anachkov I; Pan J Y; Wessling-Resnick M; Wright G E  Synthesis and effect of nonhydrolyzable xanthosine triphosphate derivatives on prenylation of Rab5D136N.    Molecular pharmacology  (1997),  51(1),  47-51.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:58 UTC</creation_date>
  <update_date>2020-04-16 20:37:48 UTC</update_date>
  <accession>BMDB0000294</accession>
  <secondary_accessions>
    <accession>BMDB00294</accession>
  </secondary_accessions>
  <name>Urea</name>
  <description>Urea, also known as ur or carbamide, belongs to the class of organic compounds known as ureas. Ureas are compounds containing two amine groups joined by a carbonyl (C=O) functional group. Urea exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Urea exists in all living species, ranging from bacteria to humans. Urea is a potentially toxic compound. Urea has been found to be associated with several diseases known as cirrhosis, tuberculous meningitis, perillyl alcohol administration for cancer treatment, and bartter syndrome, type 2, antenatal; also urea has been linked to the inborn metabolic disorders including cholesteryl ester storage disease.</description>
  <synonyms>
    <synonym>1728</synonym>
    <synonym>Carbamide</synonym>
    <synonym>Carbonyldiamide</synonym>
    <synonym>e927b</synonym>
    <synonym>H2NC(O)NH2</synonym>
    <synonym>Harnstoff</synonym>
    <synonym>Karbamid</synonym>
    <synonym>ur</synonym>
    <synonym>Uree</synonym>
    <synonym>Pastaron</synonym>
    <synonym>Alphadrate</synonym>
    <synonym>ARF</synonym>
    <synonym>b-I-K</synonym>
    <synonym>beta-I-K</synonym>
    <synonym>Bromisovalum</synonym>
    <synonym>Bubber shet</synonym>
    <synonym>Calmurid</synonym>
    <synonym>Calmurid HC</synonym>
    <synonym>Carbaderm</synonym>
    <synonym>Carbamide resin</synonym>
    <synonym>Carbonyl diamide</synonym>
    <synonym>Carbonyl diamine</synonym>
    <synonym>Carbonyldiamine</synonym>
    <synonym>Carmol</synonym>
    <synonym>Helicosol</synonym>
    <synonym>Hyanit</synonym>
    <synonym>Isourea</synonym>
    <synonym>Keratinamin</synonym>
    <synonym>Keratinamin kowa</synonym>
    <synonym>Mocovina</synonym>
    <synonym>Onychomal</synonym>
    <synonym>Panafil</synonym>
    <synonym>URE</synonym>
    <synonym>Ureaphil</synonym>
    <synonym>Ureophil</synonym>
    <synonym>Basodexan</synonym>
  </synonyms>
  <chemical_formula>CH4N2O</chemical_formula>
  <average_molecular_weight>60.0553</average_molecular_weight>
  <monisotopic_moleculate_weight>60.03236276</monisotopic_moleculate_weight>
  <iupac_name>urea</iupac_name>
  <traditional_iupac>urea</traditional_iupac>
  <cas_registry_number>57-13-6</cas_registry_number>
  <smiles>NC(N)=O</smiles>
  <inchi>InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)</inchi>
  <inchikey>XSQUKJJJFZCRTK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as ureas. Ureas are compounds containing two amine groups joined by a carbonyl (C=O) functional group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic carbonic acids and derivatives</class>
    <sub_class>Ureas</sub_class>
    <direct_parent>Ureas</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Urea</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>isourea</external_descriptor>
      <external_descriptor>one-carbon compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>132 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>545.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.11</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>urea</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>60.0553</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>60.03236276</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(N)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>CH4N2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XSQUKJJJFZCRTK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>69.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>13.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>5.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>D-Arginine and D-Ornithine Metabolism</name>
      <smpdb_id>SMP0087190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Kidney Function</name>
      <smpdb_id>SMP0119376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447325</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1321+/-282</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>6510</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Dacos Chemistry Analyzer in Hereford cows</comment>
      <references>
        <reference>
          <reference_text>Early RJ, McBride BW, Ball RO: Growth and metabolism in somatotropin-treated steers: I. Growth, serum chemistry and carcass weights. J Anim Sci. 1990 Dec;68(12):4134-43. doi: 10.2527/1990.68124134x.</reference_text>
          <pubmed_id>2286555</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2430-2890</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Cobas c311/501 chemistry analyzer</comment>
      <references>
        <reference>
          <reference_text>Consolo NRB, Munro JC, Bourgon SL, Karrow NA, Fredeen AH, Martell JE, Montanholi YR: Associations of Blood Analysis with Feed Efficiency and Developmental Stage in Grass-Fed Beef Heifers. Animals (Basel). 2018 Aug 2;8(8). pii: ani8080133. doi: 10.3390/ani8080133.</reference_text>
          <pubmed_id>30072590</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>732.658-3603.346</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by procedure of Folin and Wu (1919)</comment>
      <references>
        <reference>
          <reference_text>Arthur K. Anderson, Howard E. Gayley, Avery D. Pratt. Studies on the Chemical Composition of Bovine Blood. J. Dairy Science (1930) 13(4):336-348   doi: 10.3168/jds.S0022-0302(30)93530-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1145.611 +/- 449.586</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Marsh, Fingerhut &amp; Miller (1965) method. Samples have been collected from White Shorthorn x Galloway (Blue-grey).</comment>
      <references>
        <reference>
          <reference_text>C. R. E. Cogginsa and A. C. Field. Diurnal variation in the chemical composition of plasma from lactating beef cows on three dietary energy intakes. J. agric. Sri., Camb. (1976), 86, 595-602</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3840-4110</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Cobas c311/501 chemistry analyzer</comment>
      <references>
        <reference>
          <reference_text>Macdonald AGC, Bourgon SL, Palme R, Miller SP, Montanholi YR: Evaluation of blood metabolites reflects presence or absence of liver abscesses in beef cattle. Vet Rec Open. 2017 Apr 1;4(1):e000170. doi: 10.1136/vetreco-2016-000170. eCollection 2017.</reference_text>
          <pubmed_id>28890789</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>4121-4443</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1950-4080</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Urea OSR 6234 kit with Beckman-Olympus AU 600 chemistry analyzer</comment>
      <references>
        <reference>
          <reference_text>Liker B.,  L. Bačar-Huskić,  M. Knežević,  V. Rupić,  N. Vranešić,  Ž. Romić,  D. Grbeša,  D. Mačešić,  J. Leto,  Z. Antunović,  Ž. Krnić. 2005. Blood metabolites and haematological indices of pregnant beef cows fed rumen-protected methionine. J. Anim. Feed Sci. 14(4):625–638</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2331.196 - 2381.151</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Diet: Grass silage</comment>
      <references>
        <reference>
          <reference_text>Vanhatalo A, Kuoppala K, Ahvenjarvi S, Rinne M: Effects of feeding grass or red clover silage cut at two maturity stages in dairy cows. 1. Nitrogen metabolism and supply of amino acids. J Dairy Sci. 2009 Nov;92(11):5620-33. doi: 10.3168/jds.2009-2249.</reference_text>
          <pubmed_id>19841222</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5944.551 - 6144.368</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Diet: Red clover silage</comment>
      <references>
        <reference>
          <reference_text>Vanhatalo A, Kuoppala K, Ahvenjarvi S, Rinne M: Effects of feeding grass or red clover silage cut at two maturity stages in dairy cows. 1. Nitrogen metabolism and supply of amino acids. J Dairy Sci. 2009 Nov;92(11):5620-33. doi: 10.3168/jds.2009-2249.</reference_text>
          <pubmed_id>19841222</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>282.72 +/- 45.21</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1117 +/- 175</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1174 +/- 115</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1115 +/- 30</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1104 +/- 136</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4110</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4570</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5150</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6130</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6450</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6490</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6570</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6850</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6890</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7160</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7310</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7480</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2250 +/- 140</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2250 +/- 300</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2460 +/- 170</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2700 +/- 120</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2930 +/- 110</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4329.365</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Korhonen M, Vanhatalo A, Huhtanen P: Evaluation of isoleucine, leucine, and valine as a second-limiting amino acid for milk production in dairy cows fed grass silage diet. J Dairy Sci. 2002 Jun;85(6):1533-45. doi: 10.3168/jds.S0022-0302(02)74223-9.</reference_text>
          <pubmed_id>12146486</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>221.68 +/- 102.60</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>389.71 +/- 57.62</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1870</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2920</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2570</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>890</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1872 +/- 1191</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2928 +/- 1634</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1977 +/- 792</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>898 +/- 84</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>898.83 +/- 984.41</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein.</comment>
      <references>
        <reference>
          <reference_text>Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17.</reference_text>
          <pubmed_id>22059599</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00086</kegg_id>
  <drugbank_id>DB03904</drugbank_id>
  <foodb_id>FDB012174</foodb_id>
  <chemspider_id>1143</chemspider_id>
  <pubchem_compound_id>1176</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16199</chebi_id>
  <knapsack_id>C00007314</knapsack_id>
  <meta_cyc_id>UREA</meta_cyc_id>
  <wikipedia_id>Urea</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33799</bigg_id>
  <metlin_id>6</metlin_id>
  <synthesis_reference>Leuthardt, F.; Glasson, B.  Biological synthesis of urea.    Verhandl. Ver. schweiz. Physiol.  (1942),  21  25-7.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Korhonen M, Vanhatalo A, Huhtanen P: Evaluation of isoleucine, leucine, and valine as a second-limiting amino acid for milk production in dairy cows fed grass silage diet. J Dairy Sci. 2002 Jun;85(6):1533-45. doi: 10.3168/jds.S0022-0302(02)74223-9.</reference_text>
      <pubmed_id>12146486</pubmed_id>
    </reference>
    <reference>
      <reference_text>Vanhatalo A, Kuoppala K, Ahvenjarvi S, Rinne M: Effects of feeding grass or red clover silage cut at two maturity stages in dairy cows. 1. Nitrogen metabolism and supply of amino acids. J Dairy Sci. 2009 Nov;92(11):5620-33. doi: 10.3168/jds.2009-2249.</reference_text>
      <pubmed_id>19841222</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
      <pubmed_id>23040012</pubmed_id>
    </reference>
    <reference>
      <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
      <pubmed_id>9718493</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00553</protein_accession>
      <name>Arginase-1</name>
      <uniprot_id>Q2KJ64</uniprot_id>
      <gene_name>ARG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00558</protein_accession>
      <name>Arginase-2, mitochondrial</name>
      <uniprot_id>Q58DL1</uniprot_id>
      <gene_name>ARG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00801</protein_accession>
      <name>Probable allantoicase</name>
      <uniprot_id>Q2KIG4</uniprot_id>
      <gene_name>ALLC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02166</protein_accession>
      <name>Solute carrier family 14 (Urea transporter), member 1 (Kidd blood group)</name>
      <uniprot_id>Q2KJI0</uniprot_id>
      <gene_name>SLC14A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02167</protein_accession>
      <name>Urea transporter</name>
      <uniprot_id>Q5QF96</uniprot_id>
      <gene_name>SLC14A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02168</protein_accession>
      <name>Urea transporter splice variant</name>
      <uniprot_id>Q2TM53</uniprot_id>
      <gene_name>SLC14A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:27:59 UTC</creation_date>
  <update_date>2020-04-15 22:36:49 UTC</update_date>
  <accession>BMDB0000295</accession>
  <secondary_accessions>
    <accession>BMDB00295</accession>
  </secondary_accessions>
  <name>Uridine 5'-diphosphate</name>
  <description/>
  <synonyms>
    <synonym>Uridine diphosphate</synonym>
    <synonym>Uridine diphosphoric acid</synonym>
    <synonym>Uridine 5'-diphosphoric acid</synonym>
    <synonym>5'-UDP</synonym>
    <synonym>UDP</synonym>
    <synonym>Uridine 5'-pyrophosphate</synonym>
    <synonym>Uridine 5'-pyrophosphorate</synonym>
    <synonym>Uridine 5'-pyrophosphoric acid</synonym>
    <synonym>Uridine pyrophosphate</synonym>
    <synonym>Pyrophosphate, uridine</synonym>
    <synonym>Diphosphate, uridine</synonym>
  </synonyms>
  <chemical_formula>C9H14N2O12P2</chemical_formula>
  <average_molecular_weight>404.1612</average_molecular_weight>
  <monisotopic_moleculate_weight>404.002196946</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>UDP</traditional_iupac>
  <cas_registry_number>58-98-0</cas_registry_number>
  <smiles>O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C9H14N2O12P2/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1</inchi>
  <inchikey>XCCTYIAWTASOJW-XVFCMESISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group  linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine ribonucleotides</sub_class>
    <direct_parent>Pyrimidine ribonucleoside diphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ribonucleotides</external_descriptor>
      <external_descriptor>pyrimidine ribonucleoside 5'-diphosphate</external_descriptor>
      <external_descriptor>uridine 5'-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>404.1612</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>404.002196946</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H14N2O12P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H14N2O12P2/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XCCTYIAWTASOJW-XVFCMESISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>212.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>74.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>30.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Androstenedione Metabolism</name>
      <smpdb_id>SMP0087271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439115</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00015</kegg_id>
  <chemspider_id>5809</chemspider_id>
  <drugbank_id>DB03435</drugbank_id>
  <foodb_id>FDB031236</foodb_id>
  <pubchem_compound_id>6031</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17659</chebi_id>
  <knapsack_id>C00007313</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33518</bigg_id>
  <wikipedia_id>Uridine_Diphosphate</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Zeng, Bin; Rao, Linfan; Li, Gaowo.  Method for manufacturing uridine diphosphate.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2007),     14pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:00 UTC</creation_date>
  <update_date>2020-04-16 17:52:13 UTC</update_date>
  <accession>BMDB0000296</accession>
  <secondary_accessions>
    <accession>BMDB00296</accession>
  </secondary_accessions>
  <name>Uridine</name>
  <description>Uridine, also known as beta-uridine or allo uridine, belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. Uridine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Uridine exists in all living species, ranging from bacteria to humans. In cattle, uridine is involved in the metabolic pathway called lactose synthesis pathway. Uridine has been found to be associated with several diseases known as degenerative disc disease, canavan disease, and ulcerative colitis; also uridine has been linked to several inborn metabolic disorders including argininemia and lesch-nyhan syndrome.</description>
  <synonyms>
    <synonym>1-beta-D-Ribofuranosylpyrimidine-2,4(1H,3H)-dione</synonym>
    <synonym>1-beta-D-Ribofuranosyluracil</synonym>
    <synonym>beta-Uridine</synonym>
    <synonym>u</synonym>
    <synonym>Urd</synonym>
    <synonym>Uridin</synonym>
    <synonym>1-b-D-Ribofuranosylpyrimidine-2,4(1H,3H)-dione</synonym>
    <synonym>1-Β-D-ribofuranosylpyrimidine-2,4(1H,3H)-dione</synonym>
    <synonym>1-b-D-Ribofuranosyluracil</synonym>
    <synonym>1-Β-D-ribofuranosyluracil</synonym>
    <synonym>b-Uridine</synonym>
    <synonym>Β-uridine</synonym>
    <synonym>1-b-D-Ribofuranosyl-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>1-beta-delta-Ribofuranosyl-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>1-beta-delta-Ribofuranosyluracil</synonym>
    <synonym>b-D-Ribofuranoside 2,4(1H,3H)-pyrimidinedione-1</synonym>
    <synonym>beta-delta-Ribofuranoside 2,4(1H,3H)-pyrimidinedione-1</synonym>
    <synonym>Allo uridine</synonym>
    <synonym>Allo-uridine</synonym>
    <synonym>Allouridine</synonym>
  </synonyms>
  <chemical_formula>C9H12N2O6</chemical_formula>
  <average_molecular_weight>244.2014</average_molecular_weight>
  <monisotopic_moleculate_weight>244.069536126</monisotopic_moleculate_weight>
  <iupac_name>1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione</iupac_name>
  <traditional_iupac>uridine</traditional_iupac>
  <cas_registry_number>58-96-8</cas_registry_number>
  <smiles>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1</inchi>
  <inchikey>DRTQHJPVMGBUCF-XVFCMESISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleosides</class>
    <sub_class/>
    <direct_parent>Pyrimidine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine nucleoside</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ribonucleosides</external_descriptor>
      <external_descriptor>uridines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>163 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.98</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>244.2014</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>244.069536126</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H12N2O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DRTQHJPVMGBUCF-XVFCMESISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>119.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>52.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3944</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3936</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>344+/-86</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16.07 +/- 4.91</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14.690 +/- 4.730</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52.</reference_text>
          <pubmed_id>1897275</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>73.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw whole milk</comment>
      <references>
        <reference>
          <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
          <pubmed_id>6539345</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68.</reference_text>
          <pubmed_id>11242448</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11.76 +/- 1.81</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11.78 +/- 2.37</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>18+/-10</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2-17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>156+/-36</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein.</comment>
      <references>
        <reference>
          <reference_text>Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17.</reference_text>
          <pubmed_id>22059599</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00299</kegg_id>
  <chemspider_id>5807</chemspider_id>
  <drugbank_id>DB02745</drugbank_id>
  <foodb_id>FDB007411</foodb_id>
  <pubchem_compound_id>6029</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16704</chebi_id>
  <knapsack_id>C00019674</knapsack_id>
  <meta_cyc_id>URIDINE</meta_cyc_id>
  <wikipedia_id>Uridine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34541</bigg_id>
  <metlin_id>90</metlin_id>
  <synthesis_reference>Doi, Muneharu; Asahi, Satoru; Izawa, Motoo.  Fermentative production of uridine and cytidine.    Baiosaiensu to Indasutori  (1993),  51(12),  972-6.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52.</reference_text>
      <pubmed_id>1897275</pubmed_id>
    </reference>
    <reference>
      <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
      <pubmed_id>6539345</pubmed_id>
    </reference>
    <reference>
      <reference_text>Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68.</reference_text>
      <pubmed_id>11242448</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00579</protein_accession>
      <name>Pseudouridylate synthase</name>
      <uniprot_id>A6QP68</uniprot_id>
      <gene_name>PUSL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00580</protein_accession>
      <name>Activation-induced cytidine deaminase</name>
      <uniprot_id>Q2PT36</uniprot_id>
      <gene_name>AICDA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00581</protein_accession>
      <name>Pseudouridylate synthase 7 homolog</name>
      <uniprot_id>Q08DI8</uniprot_id>
      <gene_name>PUS7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00582</protein_accession>
      <name>tRNA pseudouridine synthase 3</name>
      <uniprot_id>Q3SX07</uniprot_id>
      <gene_name>PUS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00583</protein_accession>
      <name>Uridine-cytidine kinase 1</name>
      <uniprot_id>Q0P5A4</uniprot_id>
      <gene_name>UCK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:01 UTC</creation_date>
  <update_date>2020-04-14 22:47:21 UTC</update_date>
  <accession>BMDB0000299</accession>
  <secondary_accessions>
    <accession>BMDB00299</accession>
  </secondary_accessions>
  <name>Xanthosine</name>
  <description/>
  <synonyms>
    <synonym>9-beta-D-Ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione</synonym>
    <synonym>9-beta-D-Ribofuranosylxanthine</synonym>
    <synonym>Xanthine 9-beta-D-ribofuranoside</synonym>
    <synonym>Xanthine riboside</synonym>
    <synonym>9-b-D-Ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione</synonym>
    <synonym>9-Β-D-ribofuranosyl-3,9-dihydro-1H-purine-2,6-dione</synonym>
    <synonym>9-b-D-Ribofuranosylxanthine</synonym>
    <synonym>9-Β-D-ribofuranosylxanthine</synonym>
    <synonym>Xanthine 9-b-D-ribofuranoside</synonym>
    <synonym>Xanthine 9-β-D-ribofuranoside</synonym>
    <synonym>3,9-Dihydro-9-b-D-ribofuranosyl-1H-purine-2,6-dione</synonym>
    <synonym>3,9-Dihydro-9-beta-delta-ribofuranosyl-1H-purine-2,6-dione</synonym>
    <synonym>3,9-Dihydro-9-D-ribofuranosyl-1H-purine-2,6-dione</synonym>
    <synonym>3,9-Dihydro-9-delta-ribofuranosyl-1H-purine-2,6-dione</synonym>
    <synonym>9-beta-delta-Ribofuranosylxanthine</synonym>
    <synonym>9-D-Ribofuranosylxanthine</synonym>
    <synonym>9-delta-Ribofuranosylxanthine</synonym>
    <synonym>9 beta-D-Ribofuranosylxanthine</synonym>
  </synonyms>
  <chemical_formula>C10H12N4O6</chemical_formula>
  <average_molecular_weight>284.2255</average_molecular_weight>
  <monisotopic_moleculate_weight>284.075684136</monisotopic_moleculate_weight>
  <iupac_name>9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diol</iupac_name>
  <traditional_iupac>9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purine-2,6-diol</traditional_iupac>
  <cas_registry_number>146-80-5</cas_registry_number>
  <smiles>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O</smiles>
  <inchi>InChI=1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)/t3-,5-,6-,9-/m1/s1</inchi>
  <inchikey>UBORTCNDUKBEOP-UUOKFMHZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleosides</class>
    <sub_class/>
    <direct_parent>Purine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
      <alternative_parent>Xanthines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleoside</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
      <substituent>Xanthine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Purine alkaloids</external_descriptor>
      <external_descriptor>xanthosines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purine-2,6-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>284.2255</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>284.075684136</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=C(O)N=C2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N4O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)/t3-,5-,6-,9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UBORTCNDUKBEOP-UUOKFMHZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>153.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>62.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439238</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01762</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB001604</foodb_id>
  <chemspider_id>58484</chemspider_id>
  <pubchem_compound_id>64959</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18107</chebi_id>
  <knapsack_id>C00007222</knapsack_id>
  <wikipedia_id>Xanthosine</wikipedia_id>
  <meta_cyc_id>XANTHOSINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>38352</bigg_id>
  <metlin_id>3408</metlin_id>
  <synthesis_reference>Enei, Hitoshi; Sato, Katsuaki; Hirose, Yoshio.  Xanthosine production by fermentation.    Jpn. Kokai Tokkyo Koho  (1975),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:03 UTC</creation_date>
  <update_date>2020-04-15 20:48:00 UTC</update_date>
  <accession>BMDB0000300</accession>
  <secondary_accessions>
    <accession>BMDB00300</accession>
  </secondary_accessions>
  <name>Uracil</name>
  <description>Uracil, also known as U or hybar X, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Uracil exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Uracil exists in all living species, ranging from bacteria to humans. Uracil is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2,4(1H,3H)-Pyrimidinedione</synonym>
    <synonym>2,4-Dioxopyrimidine</synonym>
    <synonym>2,4-Pyrimidinedione</synonym>
    <synonym>U</synonym>
    <synonym>Ura</synonym>
    <synonym>Urazil</synonym>
    <synonym>2,4-Dihydroxypyrimidine</synonym>
    <synonym>2,4-Pyrimidinediol</synonym>
    <synonym>Hybar X</synonym>
    <synonym>Pirod</synonym>
    <synonym>Pyrod</synonym>
  </synonyms>
  <chemical_formula>C4H4N2O2</chemical_formula>
  <average_molecular_weight>112.0868</average_molecular_weight>
  <monisotopic_moleculate_weight>112.027277382</monisotopic_moleculate_weight>
  <iupac_name>1,2,3,4-tetrahydropyrimidine-2,4-dione</iupac_name>
  <traditional_iupac>uracil</traditional_iupac>
  <cas_registry_number>66-22-8</cas_registry_number>
  <smiles>O=C1NC=CC(=O)N1</smiles>
  <inchi>InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)</inchi>
  <inchikey>ISAKRJDGNUQOIC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazines</class>
    <sub_class>Pyrimidines and pyrimidine derivatives</sub_class>
    <direct_parent>Pyrimidones</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a pyrimidine base</external_descriptor>
      <external_descriptor>a pyrimidine-related compound</external_descriptor>
      <external_descriptor>pyrimidine nucleobase</external_descriptor>
      <external_descriptor>pyrimidines</external_descriptor>
      <external_descriptor>pyrimidone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>330 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>3.6 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.07</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-5.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1,2,3,4-tetrahydropyrimidine-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>112.0868</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>112.027277382</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O=C1NC=CC(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H4N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ISAKRJDGNUQOIC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>58.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440041</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>76+/-30</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>113.18 +/- 24.69</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>142.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>234.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>270.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>113.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1007+/-230</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>109-405</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>122 +/- 127</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>199 +/- 91</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>246 +/- 48</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>104 +/- 25</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>104 +/- 25</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR and GC-MS</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>149</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>193</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>224</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>92.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00106</kegg_id>
  <drugbank_id>DB03419</drugbank_id>
  <foodb_id>FDB006426</foodb_id>
  <chemspider_id>1141</chemspider_id>
  <pubchem_compound_id>1174</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17568</chebi_id>
  <knapsack_id>C00001513</knapsack_id>
  <wikipedia_id>Uracil</wikipedia_id>
  <meta_cyc_id>URACIL</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33879</bigg_id>
  <metlin_id>258</metlin_id>
  <synthesis_reference>Burckhalter, J. H.; Scarborough, Homer C. The synthesis of uracils as anticonvulsants. Journal of the American Pharmaceutical Association (1912-1977) (1955), 44 545-50.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00689</protein_accession>
      <name>Dihydropyrimidine dehydrogenase [NADP+]</name>
      <uniprot_id>Q28007</uniprot_id>
      <gene_name>DPYD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01107</protein_accession>
      <name>Uracil phosphoribosyltransferase</name>
      <uniprot_id>Q32LA4</uniprot_id>
      <gene_name>UPRT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:04 UTC</creation_date>
  <update_date>2020-04-16 17:53:57 UTC</update_date>
  <accession>BMDB0000301</accession>
  <secondary_accessions>
    <accession>BMDB00301</accession>
  </secondary_accessions>
  <name>Urocanic acid</name>
  <description>Urocanic acid, also known as urocanic acid or urocanic acid, belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. Urocanic acid exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Urocanic acid exists in all living organisms, ranging from bacteria to humans. Urocanic acid can be biosynthesized from L-histidine; which is mediated by the enzyme histidine ammonia-lyase. In cattle, urocanic acid is involved in the metabolic pathway called the ammonia recycling pathway.</description>
  <synonyms>
    <synonym>(2E)-3-(1H-Imidazol-4-yl)acrylic acid</synonym>
    <synonym>(e)-3-(1H-Imidazol-4-yl)-2-propenoic acid</synonym>
    <synonym>(2E)-3-(1H-Imidazol-4-yl)acrylate</synonym>
    <synonym>(e)-3-(1H-Imidazol-4-yl)-2-propenoate</synonym>
    <synonym>Urocanate</synonym>
    <synonym>3-(1H-Imidazol-4-yl)-2-propenoate</synonym>
    <synonym>3-(1H-Imidazol-4-yl)-2-propenoic acid</synonym>
    <synonym>3-(1H-Imidazol-4-yl)acrylate</synonym>
    <synonym>3-(1H-Imidazol-4-yl)acrylic acid</synonym>
    <synonym>3-(4-Imidazolyl)acrylate</synonym>
    <synonym>3-(4-Imidazolyl)acrylic acid</synonym>
    <synonym>5-Imidazoleacrylate</synonym>
    <synonym>5-Imidazoleacrylic acid</synonym>
    <synonym>Imidazole-4-acrylate</synonym>
    <synonym>Imidazole-4-acrylic acid</synonym>
    <synonym>Imidazoleacrylic acid</synonym>
    <synonym>Acid, glyoxalinylacrylic</synonym>
    <synonym>Acid, urocanic</synonym>
    <synonym>Glyoxalinylacrylic acid</synonym>
    <synonym>(2E)-3-(1H-Imidazol-5-yl)-2-propenoic acid</synonym>
    <synonym>(e)-3-(4-Imidazolyl)acrylic acid</synonym>
    <synonym>(e)-3-(Imidazol-4-yl)-2-propenoic acid</synonym>
    <synonym>(e)-Urocanic acid</synonym>
    <synonym>trans-Urocanic acid</synonym>
  </synonyms>
  <chemical_formula>C6H6N2O2</chemical_formula>
  <average_molecular_weight>138.124</average_molecular_weight>
  <monisotopic_moleculate_weight>138.042927446</monisotopic_moleculate_weight>
  <iupac_name>(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid</iupac_name>
  <traditional_iupac>trans-urocanic acid</traditional_iupac>
  <cas_registry_number>3465-72-3</cas_registry_number>
  <smiles>OC(=O)\C=C\C1=CNC=N1</smiles>
  <inchi>InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+</inchi>
  <inchikey>LOIYMIARKYCTBW-OWOJBTEDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Azoles</class>
    <sub_class>Imidazoles</sub_class>
    <direct_parent>Imidazolyl carboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazolyl carboxylic acid derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>urocanic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>225 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1.5 mg/mL at 17 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>138.124</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>138.042927446</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)\C=C\C1=CNC=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H6N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)/b2-1+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LOIYMIARKYCTBW-OWOJBTEDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>65.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30921</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448111</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00785</kegg_id>
  <drugbank_id>DB01971</drugbank_id>
  <foodb_id>FDB007506</foodb_id>
  <chemspider_id>643824</chemspider_id>
  <pubchem_compound_id>736715</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30817</chebi_id>
  <knapsack_id/>
  <wikipedia_id>Urocanic_acid</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>35990</bigg_id>
  <metlin_id>298</metlin_id>
  <synthesis_reference>Yamamoto, Kozo; Sato, Tadashi; Tosa, Tetsuya; Chibata, Ichiro. Continuous production of urocanic acid by immobilized Achromobacter liquidum cells. Biotechnology and Bioengineering (1974), 16(12), 1601-10.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01131</protein_accession>
      <name>Histidine ammonia-lyase</name>
      <uniprot_id>A7YWP4</uniprot_id>
      <gene_name>HAL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:05 UTC</creation_date>
  <update_date>2020-04-16 20:37:23 UTC</update_date>
  <accession>BMDB0000302</accession>
  <secondary_accessions>
    <accession>BMDB00302</accession>
  </secondary_accessions>
  <name>Uridine diphosphategalactose</name>
  <description>Uridine diphosphategalactose, also known as UDP-D-galactopyranose or UDP galactose, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Uridine diphosphategalactose is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine diphosphategalactose exists in all living organisms, ranging from bacteria to humans. Uridine diphosphategalactose participates in a number of enzymatic reactions, within cattle. In particular, Uridine diphosphategalactose and glucose 1-phosphate can be converted into uridine diphosphate glucose and galactose 1-phosphate; which is catalyzed by the enzyme galactose-1-phosphate uridylyltransferase. In addition, D-Glucose and uridine diphosphategalactose can be converted into uridine 5'-diphosphate and Alpha-lactose; which is catalyzed by the enzyme lactose synthase. In cattle, uridine diphosphategalactose is involved in the metabolic pathway called lactose synthesis pathway.</description>
  <synonyms>
    <synonym>UDP Galactose</synonym>
    <synonym>UDP-alpha-D-Galactopyranose</synonym>
    <synonym>UDP-D-Galactopyranose</synonym>
    <synonym>UDP-Galactose</synonym>
    <synonym>Uridine diphosphate galactose</synonym>
    <synonym>Uridine diphosphogalactose</synonym>
    <synonym>Uridine pyrophosphogalactose</synonym>
    <synonym>Uridinediphosphogalactose</synonym>
    <synonym>UDP-a-D-Galactopyranose</synonym>
    <synonym>UDP-Α-D-galactopyranose</synonym>
    <synonym>Uridine diphosphoric acid galactose</synonym>
    <synonym>GDU</synonym>
    <synonym>UDP-a-D-Galactose</synonym>
    <synonym>UDP-alpha-D-Galactose</synonym>
    <synonym>UDP-alpha-delta-Galactose</synonym>
    <synonym>UDP-D-Galactose</synonym>
    <synonym>UDP-delta-Galactopyranose</synonym>
    <synonym>UDP-delta-Galactose</synonym>
    <synonym>UDP-Gal</synonym>
    <synonym>UDP-Galactopyranose</synonym>
    <synonym>Udpgal</synonym>
    <synonym>UDPgalactose</synonym>
    <synonym>UPG</synonym>
    <synonym>Uridine 5'-(alpha-D-galactopyranosyl pyrophosphate)</synonym>
    <synonym>Uridine 5'-(alpha-delta-galactopyranosyl pyrophosphate)</synonym>
    <synonym>Uridine 5'-diphosphate galactose</synonym>
    <synonym>Uridine 5'-diphosphogalactose</synonym>
    <synonym>Uridine 5'-pyrophosphate a-D-galactopyranosyl ester</synonym>
    <synonym>Uridine 5'-pyrophosphate a-D-galactosyl ester</synonym>
    <synonym>Uridine 5'-pyrophosphate a-delta-galactopyranosyl ester</synonym>
    <synonym>Uridine 5'-pyrophosphate a-delta-galactosyl ester</synonym>
    <synonym>Uridine 5'-pyrophosphate alpha-D-galactosyl ester</synonym>
    <synonym>Uridine 5'-pyrophosphate alpha-delta-galactosyl ester</synonym>
    <synonym>Uridine 5'-pyrophosphate D-galactosyl ester</synonym>
    <synonym>Uridine 5'-[3-(D-galactopyranosyl) dihydrogen diphosphate]</synonym>
    <synonym>Uridine diphosphate-D-galactose</synonym>
    <synonym>Uridine diphosphate-delta-galactose</synonym>
    <synonym>Uridine diphosphate-galactose</synonym>
    <synonym>Uridine pyrophosphate a-D-galactopyranosyl ester</synonym>
    <synonym>Uridine pyrophosphate a-delta-galactopyranosyl ester</synonym>
    <synonym>Uridine pyrophosphate alpha-D-galactopyranosyl ester</synonym>
    <synonym>Uridine pyrophosphate alpha-delta-galactopyranosyl ester</synonym>
    <synonym>Uridinediphosphate galactose</synonym>
    <synonym>Diphosphate galactose, uridine</synonym>
    <synonym>Diphosphogalactose, uridine</synonym>
    <synonym>Galactose, UDP</synonym>
    <synonym>Galactose, uridine diphosphate</synonym>
    <synonym>Pyrophosphogalactose, uridine</synonym>
  </synonyms>
  <chemical_formula>C15H24N2O17P2</chemical_formula>
  <average_molecular_weight>566.3018</average_molecular_weight>
  <monisotopic_moleculate_weight>566.055020376</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>{[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid</traditional_iupac>
  <cas_registry_number>2956-16-3</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](O[P@@](O)(=O)O[P@@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@H](O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8+,9-,10+,11-,12-,13-,14-/m1/s1</inchi>
  <inchikey>HSCJRCZFDFQWRP-ABVWGUQPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine nucleotide sugars</sub_class>
    <direct_parent>Pyrimidine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine nucleotide sugar</substituent>
      <substituent>Pyrimidine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>UDP-D-galactose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>566.3018</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>566.055020376</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](O[P@@](O)(=O)O[P@@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@H](O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H24N2O17P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8+,9-,10+,11-,12-,13-,14-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HSCJRCZFDFQWRP-ABVWGUQPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>291.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>106.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>45.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279176</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>53+/-10</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00052</kegg_id>
  <drugbank_id>DB03501</drugbank_id>
  <foodb_id>FDB021811</foodb_id>
  <chemspider_id>17069</chemspider_id>
  <pubchem_compound_id>18068</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>67119</chebi_id>
  <knapsack_id>C00007390</knapsack_id>
  <wikipedia_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>33675</bigg_id>
  <metlin_id>5291</metlin_id>
  <synthesis_reference>Takeda, Satoshi; Noguchi, Toshitada.  Enzymic manufacture of 5'-uridine diphosphate galactose (UDP-Gal) from UMP.    Jpn. Kokai Tokkyo Koho  (2001),     9 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00381</protein_accession>
      <name>Polypeptide N-acetylgalactosaminyltransferase 6</name>
      <uniprot_id>Q5EA41</uniprot_id>
      <gene_name>GALNT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00382</protein_accession>
      <name>Polypeptide N-acetylgalactosaminyltransferase 1</name>
      <uniprot_id>Q07537</uniprot_id>
      <gene_name>GALNT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00481</protein_accession>
      <name>Glycoprotein-N-acetylgalactosamine 3-beta-galactosyltransferase 1</name>
      <uniprot_id>Q0VC84</uniprot_id>
      <gene_name>C1GALT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00604</protein_accession>
      <name>Beta-1,4-galactosyltransferase 1</name>
      <uniprot_id>P08037</uniprot_id>
      <gene_name>B4GALT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00640</protein_accession>
      <name>Beta-1,4-galactosyltransferase 3</name>
      <uniprot_id>Q5EA87</uniprot_id>
      <gene_name>B4GALT3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00653</protein_accession>
      <name>N-acetyllactosaminide alpha-1,3-galactosyltransferase</name>
      <uniprot_id>P14769</uniprot_id>
      <gene_name>GGTA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00957</protein_accession>
      <name>Galactose-1-phosphate uridylyltransferase</name>
      <uniprot_id>Q0V7N7</uniprot_id>
      <gene_name>GALT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00959</protein_accession>
      <name>Galactose-1-phosphate uridylyltransferase</name>
      <uniprot_id>Q58CX1</uniprot_id>
      <gene_name>GALT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02047</protein_accession>
      <name>UDP-galactose translocator</name>
      <uniprot_id>Q58DA6</uniprot_id>
      <gene_name>SLC35A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:06 UTC</creation_date>
  <update_date>2020-04-15 23:55:34 UTC</update_date>
  <accession>BMDB0000303</accession>
  <secondary_accessions>
    <accession>BMDB00303</accession>
  </secondary_accessions>
  <name>Tryptamine</name>
  <description>Tryptaminee belongs to the class of organic compounds known as tryptaminees and derivatives. Tryptaminees and derivatives are compounds containing the tryptaminee backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine. Tryptaminee exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Tryptaminee exists in all living organisms, ranging from bacteria to humans. Tryptaminee participates in a number of enzymatic reactions, within cattle. In particular, Tryptaminee can be biosynthesized from L-tryptophan; which is mediated by the enzyme aromatic-L-amino-acid decarboxylase. In addition, Tryptaminee can be converted into indoleacetaldehyde through the action of the enzyme kynurenine 3-monooxygenase. In cattle, tryptaminee is involved in the metabolic pathway called the tryptophan metabolism pathway.</description>
  <synonyms>
    <synonym>1H-Indole-3-ethanamine</synonym>
    <synonym>2-(1H-indol-3-yl)ETHANAMINE</synonym>
    <synonym>2-(3-Indolyl)ethylamine</synonym>
    <synonym>3-(2-Aminoethyl)indole</synonym>
    <synonym>(3-Indolyl)ethylamine</synonym>
    <synonym>2-(1H-indol-3-yl)Ethylamine</synonym>
    <synonym>2-indol-3-yl-Aethylamin</synonym>
    <synonym>2-indol-3-yl-Ethylamine</synonym>
    <synonym>3-(2-Aminoethyl)-1H-indole</synonym>
    <synonym>3-Indoleethanamine</synonym>
    <synonym>3-Indoleethylamine</synonym>
    <synonym>Tryptamin</synonym>
    <synonym>2-(1H-indol-3-yl)Ethan-1-amine</synonym>
    <synonym>beta-(3-Indolyl)ethylamine</synonym>
    <synonym>Β-(3-indolyl)ethylamine</synonym>
    <synonym>TRPN</synonym>
    <synonym>Tryptamine</synonym>
  </synonyms>
  <chemical_formula>C10H12N2</chemical_formula>
  <average_molecular_weight>160.2157</average_molecular_weight>
  <monisotopic_moleculate_weight>160.100048394</monisotopic_moleculate_weight>
  <iupac_name>2-(1H-indol-3-yl)ethan-1-amine</iupac_name>
  <traditional_iupac>tryptamine</traditional_iupac>
  <cas_registry_number>61-54-1</cas_registry_number>
  <smiles>NCCC1=CNC2=C1C=CC=C2</smiles>
  <inchi>InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2</inchi>
  <inchikey>APJYDQYYACXCRM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Tryptamines and derivatives</sub_class>
    <direct_parent>Tryptamines and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>2-arylethylamines</alternative_parent>
      <alternative_parent>3-alkylindoles</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-arylethylamine</substituent>
      <substituent>3-alkylindole</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
      <substituent>Tryptamine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Indole alkaloids</external_descriptor>
      <external_descriptor>aminoalkylindole</external_descriptor>
      <external_descriptor>aralkylamino compound</external_descriptor>
      <external_descriptor>indole alkaloid</external_descriptor>
      <external_descriptor>tryptamines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>114 - 119 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.55</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>17.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(1H-indol-3-yl)ethan-1-amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>160.2157</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>160.100048394</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCC1=CNC2=C1C=CC=C2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>APJYDQYYACXCRM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>41.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3988</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451969</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00398</kegg_id>
  <drugbank_id>DB08653</drugbank_id>
  <foodb_id>FDB000917</foodb_id>
  <chemspider_id>1118</chemspider_id>
  <pubchem_compound_id>1150</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16765</chebi_id>
  <knapsack_id>C00001434</knapsack_id>
  <wikipedia_id>Tryptamine</wikipedia_id>
  <meta_cyc_id>TRYPTAMINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Abramovitch, R. A.; Shapiro, D. Tryptamines, carbolines, and related compounds. II. A convenient synthesis of tryptamines and b-carbolines. Journal of the Chemical Society (1956), 4589-92.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:07 UTC</creation_date>
  <update_date>2020-04-16 17:51:15 UTC</update_date>
  <accession>BMDB0000304</accession>
  <secondary_accessions>
    <accession>BMDB00304</accession>
  </secondary_accessions>
  <name>Uridine diphosphate-N-acetylgalactosamine</name>
  <description/>
  <synonyms>
    <synonym>Uridine diphosphoric acid-N-acetylgalactosamine</synonym>
    <synonym>UDP-N-Acetyl-D-galactosamine</synonym>
    <synonym>UDP-N-Acetyl-delta-galactosamine</synonym>
    <synonym>UDP-N-Acetylgalactosamine</synonym>
    <synonym>Uridine 5'-diphospho-N-acetylgalactosamine</synonym>
    <synonym>Uridine diphosphate-N-acetyl-D-galactosamine</synonym>
    <synonym>Uridine diphosphate-N-acetyl-delta-galactosamine</synonym>
    <synonym>Uridine diphospho-2-acetamido-2-deoxy-D-galactose</synonym>
    <synonym>Uridine diphospho-2-acetamido-2-deoxy-delta-galactose</synonym>
    <synonym>Uridine diphospho-N-acetylgalactosamine</synonym>
    <synonym>Uridine diphosphoacetylgalactosamine</synonym>
    <synonym>Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-galactopyranosyl ester</synonym>
    <synonym>Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-galactopyranosyl ester</synonym>
    <synonym>Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-galactopyranosyl ester</synonym>
    <synonym>Uridine pyrophosphate N-acetyl-a-D-chondrosamine ester</synonym>
    <synonym>Uridine pyrophosphate N-acetyl-alpha-D-chondrosamine ester</synonym>
    <synonym>Uridine pyrophosphate N-acetyl-alpha-delta-chondrosamine ester</synonym>
    <synonym>Uridine pyrophosphoacetylgalactosamine</synonym>
    <synonym>Pyrophosphoacetylglucosamine, uridine</synonym>
    <synonym>UDP Acetylglucosamine</synonym>
    <synonym>Uridine diphospho-N-acetylglucosamine</synonym>
    <synonym>Acetylgalactosamine, UDP</synonym>
    <synonym>diphospho-N-Acetylglucosamine, uridine</synonym>
    <synonym>Uridine diphosphate N acetylgalactosamine</synonym>
    <synonym>Uridine diphosphate N acetylglucosamine</synonym>
    <synonym>Uridine diphosphate N-acetylglucosamine</synonym>
    <synonym>Diphosphate N-acetylglucosamine, uridine</synonym>
    <synonym>UDPGNAc</synonym>
    <synonym>Uridine diphosphate N-acetylgalactosamine</synonym>
    <synonym>Acetylglucosamine, UDP</synonym>
    <synonym>N-Acetylgalactosamine, uridine diphosphate</synonym>
    <synonym>UDP Acetylgalactosamine</synonym>
    <synonym>Uridine pyrophosphoacetylglucosamine</synonym>
    <synonym>Uridine diphospho N acetylglucosamine</synonym>
    <synonym>Diphosphate N-acetylgalactosamine, uridine</synonym>
    <synonym>N-Acetylglucosamine, uridine diphosphate</synonym>
    <synonym>N-[2-({[({[3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidate</synonym>
  </synonyms>
  <chemical_formula>C17H27N3O17P2</chemical_formula>
  <average_molecular_weight>607.3537</average_molecular_weight>
  <monisotopic_moleculate_weight>607.081569477</monisotopic_moleculate_weight>
  <iupac_name>[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>{[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(O)=NC1C(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=CC(O)=NC2=O)OC(CO)C(O)C1O</smiles>
  <inchi>InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)</inchi>
  <inchikey>LFTYTUAZOPRMMI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine nucleotide sugars</sub_class>
    <direct_parent>Pyrimidine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine nucleotide sugar</substituent>
      <substituent>Pyrimidine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>607.3537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>607.081569477</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(O)=NC1C(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=CC(O)=NC2=O)OC(CO)C(O)C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C17H27N3O17P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LFTYTUAZOPRMMI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>300.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>117.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451926</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB021933</foodb_id>
  <drugbank_id/>
  <chemspider_id/>
  <pubchem_compound_id>1167</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Yamamoto, Kenji; Kawai, Hiroyasu; Tochikura, Tatsurokurou. Preparation of uridine diphosphate-N-acetylgalactosamine from uridine diphosphate-N-acetylglucosamine by using microbial enzymes. Applied and Environmental Microbiology (1981), 41(2), 392-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00381</protein_accession>
      <name>Polypeptide N-acetylgalactosaminyltransferase 6</name>
      <uniprot_id>Q5EA41</uniprot_id>
      <gene_name>GALNT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00382</protein_accession>
      <name>Polypeptide N-acetylgalactosaminyltransferase 1</name>
      <uniprot_id>Q07537</uniprot_id>
      <gene_name>GALNT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:08 UTC</creation_date>
  <update_date>2020-04-16 20:39:17 UTC</update_date>
  <accession>BMDB0000305</accession>
  <secondary_accessions>
    <accession>BMDB00305</accession>
  </secondary_accessions>
  <name>Vitamin A</name>
  <description>Vitamin a, also known as (13cis)-retinol, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Thus, vitamin a is considered to be an isoprenoid lipid molecule. Vitamin a is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Vitamin a exists in all living organisms, ranging from bacteria to humans. Vitamin a participates in a number of enzymatic reactions, within cattle. In particular, Vitamin a and acetyl-CoA can be converted into retinyl ester through the action of the enzyme diacylglycerol O-acyltransferase 1. In addition, Vitamin a and acetyl-CoA can be converted into retinyl ester through the action of the enzyme acyl-CoA wax alcohol acyltransferase 1. In cattle, vitamin a is involved in the metabolic pathway called the retinol metabolism pathway. Vitamin a is a potentially toxic compound. Vitamin a has been found to be associated with several diseases known as pregnancy, hemodialysis, and thyroid cancer; also vitamin a has been linked to the inborn metabolic disorders including abetalipoproteinemia.</description>
  <synonyms>
    <synonym>(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol</synonym>
    <synonym>all-trans-Retinyl alcohol</synonym>
    <synonym>all-trans-Vitamin a alcohol</synonym>
    <synonym>Alphalin</synonym>
    <synonym>Chocola a</synonym>
    <synonym>Retinol</synonym>
    <synonym>Vitamin a1</synonym>
    <synonym>Aquasol a</synonym>
    <synonym>(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol</synonym>
    <synonym>all-trans-Retinol</synonym>
    <synonym>b-Retinol</synonym>
    <synonym>beta-Retinol</synonym>
    <synonym>trans-Retinol</synonym>
    <synonym>3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-e)-isomer</synonym>
    <synonym>all trans Retinol</synonym>
    <synonym>11-cis-Retinol</synonym>
    <synonym>Vitamin a</synonym>
  </synonyms>
  <chemical_formula>C20H30O</chemical_formula>
  <average_molecular_weight>286.4516</average_molecular_weight>
  <monisotopic_moleculate_weight>286.229665582</monisotopic_moleculate_weight>
  <iupac_name>(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol</iupac_name>
  <traditional_iupac>α-sol</traditional_iupac>
  <cas_registry_number>68-26-8</cas_registry_number>
  <smiles>C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C</smiles>
  <inchi>InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+</inchi>
  <inchikey>FPIPGXGPPPQFEQ-OVSJKPMPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Retinoids</sub_class>
    <direct_parent>Retinoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Diterpenoids</alternative_parent>
      <alternative_parent>Fatty alcohols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Diterpenoid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Retinoid skeleton</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fat-soluble vitamins</external_descriptor>
      <external_descriptor>Retinoids</external_descriptor>
      <external_descriptor>Retinoids</external_descriptor>
      <external_descriptor>retinol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>61 - 63 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.68</value>
      <source>BIOBYTE (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>16.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>286.4516</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>286.229665582</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H30O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FPIPGXGPPPQFEQ-OVSJKPMPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>97.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Retinol Metabolism</name>
      <smpdb_id>SMP0087260</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280670</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.052 - 4.797</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.653 - 2.308</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial milk</comment>
      <references>
        <reference>
          <reference_text>Delgado Zamarreno MM, Sanchez Perez A, Gomez Perez C, Hernandez Mendez J: High-performance liquid chromatography with electrochemical detection for the simultaneous determination of vitamin A, D3 and E in milk. J Chromatogr. 1992 Oct 9;623(1):69-74.</reference_text>
          <pubmed_id>1333471</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.566</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Diet: Low hay diet</comment>
      <references>
        <reference>
          <reference_text>Noziere P, Grolier P, Durand D, Ferlay A, Pradel P, Martin B: Variations in carotenoids, fat-soluble micronutrients, and color in cows' plasma and milk following changes in forage and feeding level. J Dairy Sci. 2006 Jul;89(7):2634-48. doi: 10.3168/jds.S0022-0302(06)72340-2.</reference_text>
          <pubmed_id>16772583</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>126</concentration_value>
      <concentration_units>IU/100 g</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0524</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.470 +/- 0.0400</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Spanish commercial milk; low-fat 1.5%</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.120 +/- 0.280</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Spanish commercial milk; low-fat 3.6%</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0800 +/- 0.0400</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Spanish commercial milk; skim 0.3% fat</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0733</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0733</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.797</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.126</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.0527</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.126</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.241</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.136</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.99</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.65 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.70 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.55 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.265 +/- 0.004</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.586 - 58.596</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Chotyakul N, Pateiro-Moure M, Saraiva JA, Torres JA, Pérez-Lamela C. 2014. Simultaneous HPLC–DAD quantification of vitamins A and E content in raw, pasteurized, and UHT cow’s milk and their changes during storage. European Food Research and Technology. 238(4):535–547 </reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.349 - 3.491</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Oste R, Jagerstad M, Anderson I: Vitamins in milk and milk products. In Fox PF (ed):‘‘Advanced Dairy Chemistry: Lactose, Water, Salts and Vitamins,’’vol 3, 2nd ed. London: Chapman &amp; Hall, pp 347–402, 1997</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.3195</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.492</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0997</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.136</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.157</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.471</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.663</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.445</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.136</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.785</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0682</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.105</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.147</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.105</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.697</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.697</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0822</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0613</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.187</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C17276</kegg_id>
  <drugbank_id>DB00162</drugbank_id>
  <foodb_id>FDB023841</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>445354</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17336</chebi_id>
  <knapsack_id>C00031437</knapsack_id>
  <wikipedia_id>Vitamin_A</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Isler, O.; Ronco, A.; Guex, W.; Hindley, N. C.; Huber, W.; Dialer, K.; Kofler, M. Esters and ethers of synthetic vitamin A. Helvetica Chimica Acta  (1949),  32  489-505.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Delgado Zamarreno MM, Sanchez Perez A, Gomez Perez C, Hernandez Mendez J: High-performance liquid chromatography with electrochemical detection for the simultaneous determination of vitamin A, D3 and E in milk. J Chromatogr. 1992 Oct 9;623(1):69-74.</reference_text>
      <pubmed_id>1333471</pubmed_id>
    </reference>
    <reference>
      <reference_text>Noziere P, Grolier P, Durand D, Ferlay A, Pradel P, Martin B: Variations in carotenoids, fat-soluble micronutrients, and color in cows' plasma and milk following changes in forage and feeding level. J Dairy Sci. 2006 Jul;89(7):2634-48. doi: 10.3168/jds.S0022-0302(06)72340-2.</reference_text>
      <pubmed_id>16772583</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
      <pubmed_id>28342601</pubmed_id>
    </reference>
    <reference>
      <reference_text>International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Chotyakul N, Pateiro-Moure M, Saraiva JA, Torres JA, Pérez-Lamela C. 2014. Simultaneous HPLC–DAD quantification of vitamins A and E content in raw, pasteurized, and UHT cow’s milk and their changes during storage. European Food Research and Technology. 238(4):535–547 </reference_text>
    </reference>
    <reference>
      <reference_text>Oste R, Jagerstad M, Anderson I: Vitamins in milk and milk products. In Fox PF (ed):‘‘Advanced Dairy Chemistry: Lactose, Water, Salts and Vitamins,’’vol 3, 2nd ed. London: Chapman &amp; Hall, pp 347–402, 1997</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00601</protein_accession>
      <name>Retinal dehydrogenase 1</name>
      <uniprot_id>P48644</uniprot_id>
      <gene_name>ALDH1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00606</protein_accession>
      <name>Hydroxysteroid 17-beta dehydrogenase 6</name>
      <uniprot_id>Q3T001</uniprot_id>
      <gene_name>HSD17B6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00713</protein_accession>
      <name>Retinol dehydrogenase 8</name>
      <uniprot_id>Q9N126</uniprot_id>
      <gene_name>RDH8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00714</protein_accession>
      <name>Lecithin retinol acyltransferase</name>
      <uniprot_id>Q9BGL2</uniprot_id>
      <gene_name>LRAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00715</protein_accession>
      <name>11-cis retinol dehydrogenase</name>
      <uniprot_id>Q27979</uniprot_id>
      <gene_name>RDH5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00716</protein_accession>
      <name>Retinol dehydrogenase 10</name>
      <uniprot_id>Q8HZT6</uniprot_id>
      <gene_name>RDH10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01341</protein_accession>
      <name>Retinal pigment epithelium-specific 65 kDa protein</name>
      <uniprot_id>Q28175</uniprot_id>
      <gene_name>RPE65</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01885</protein_accession>
      <name>Cellular retinoic acid-binding protein 1</name>
      <uniprot_id>P62964</uniprot_id>
      <gene_name>CRABP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01888</protein_accession>
      <name>Cellular retinoic acid-binding protein 2</name>
      <uniprot_id>Q5PXY7</uniprot_id>
      <gene_name>CRABP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01961</protein_accession>
      <name>Beta-lactoglobulin</name>
      <uniprot_id>P02754</uniprot_id>
      <gene_name>LGB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01962</protein_accession>
      <name>Interstitial retinol binding protein (IRBP)</name>
      <uniprot_id>Q28129</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01963</protein_accession>
      <name>Retinaldehyde-binding protein 1</name>
      <uniprot_id>P10123</uniprot_id>
      <gene_name>RLBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01964</protein_accession>
      <name>Retinol-binding protein 5</name>
      <uniprot_id>P82708</uniprot_id>
      <gene_name>RBP5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01965</protein_accession>
      <name>Retinol-binding protein 1</name>
      <uniprot_id>P02694</uniprot_id>
      <gene_name>RBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01966</protein_accession>
      <name>Retinol-binding protein 3</name>
      <uniprot_id>P12661</uniprot_id>
      <gene_name>RBP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01967</protein_accession>
      <name>Stimulated by retinoic acid gene 6 protein homolog</name>
      <uniprot_id>Q0V8E7</uniprot_id>
      <gene_name>STRA6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01968</protein_accession>
      <name>Retinol-binding protein 4</name>
      <uniprot_id>P18902</uniprot_id>
      <gene_name>RBP4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01969</protein_accession>
      <name>Retinol binding protein 1, cellular</name>
      <uniprot_id>Q58DG0</uniprot_id>
      <gene_name>RBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:09 UTC</creation_date>
  <update_date>2020-04-16 17:52:14 UTC</update_date>
  <accession>BMDB0000306</accession>
  <secondary_accessions>
    <accession>BMDB00306</accession>
  </secondary_accessions>
  <name>Tyramine</name>
  <description>Tyramine, also known as para-tyramine or systogene, belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. Tyramine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Tyramine exists in all living species, ranging from bacteria to humans. Tyramine participates in a number of enzymatic reactions, within cattle. In particular, Tyramine can be biosynthesized from L-tyrosine; which is catalyzed by the enzyme aromatic-L-amino-acid decarboxylase. In addition, Tyramine can be converted into dopamine; which is mediated by the enzyme tyrosinase. In cattle, tyramine is involved in the metabolic pathway called the tyrosine metabolism pathway. Tyramine is a potentially toxic compound. Tyramine has been found to be associated with several diseases known as brunner syndrome, ulcerative colitis, crohn's disease, and eosinophilic esophagitis; also tyramine has been linked to the inborn metabolic disorders including celiac disease.</description>
  <synonyms>
    <synonym>2-(p-Hydroxyphenyl)ethylamine</synonym>
    <synonym>4-Hydroxy-beta-phenylethylamine</synonym>
    <synonym>4-Hydroxyphenethylamine</synonym>
    <synonym>4-Hydroxyphenylethylamine</synonym>
    <synonym>beta-(4-Hydroxyphenyl)ethylamine</synonym>
    <synonym>p-(2-Aminoethyl)phenol</synonym>
    <synonym>p-Hydroxyphenethylamine</synonym>
    <synonym>p-Hydroxyphenylethylamine</synonym>
    <synonym>p-Tyramine</synonym>
    <synonym>Tyramin</synonym>
    <synonym>4-Hydroxy-b-phenylethylamine</synonym>
    <synonym>4-Hydroxy-β-phenylethylamine</synonym>
    <synonym>b-(4-Hydroxyphenyl)ethylamine</synonym>
    <synonym>Β-(4-hydroxyphenyl)ethylamine</synonym>
    <synonym>2-(4'-Hydroxyphenyl)ethylamine</synonym>
    <synonym>2-(4-Hydroxyphenyl)ethylamine</synonym>
    <synonym>4-(2-Aminoethyl)-phenol</synonym>
    <synonym>4-(2-Aminoethyl)-phenol(thyramin)</synonym>
    <synonym>4-(2-Aminoethyl)phenol</synonym>
    <synonym>4-Hydroxy-benzeneethanamine</synonym>
    <synonym>a-(4-Hydroxyphenyl)-b-aminoethane</synonym>
    <synonym>alpha-(4-Hydroxyphenyl)-beta-aminoethane</synonym>
    <synonym>p-(2-Aminoethyl)-phenol</synonym>
    <synonym>p-beta-Aminoethylphenol</synonym>
    <synonym>p-Hydroxy-b-phenethylamine</synonym>
    <synonym>p-Hydroxy-b-phenylethylamine</synonym>
    <synonym>p-Hydroxy-beta-phenethylamine</synonym>
    <synonym>p-Hydroxy-beta-phenylethylamine</synonym>
    <synonym>Systogene</synonym>
    <synonym>Tenosin-wirkstoff</synonym>
    <synonym>Tocosine</synonym>
    <synonym>Tyramine base</synonym>
    <synonym>Tyrosamine</synonym>
    <synonym>Uteramine</synonym>
    <synonym>Para-tyramine</synonym>
    <synonym>4 Hydroxyphenethylamine</synonym>
    <synonym>2-(4-Hydroxyphenyl)ethanamine</synonym>
    <synonym>2-(4’-hydroxyphenyl)ethylamine</synonym>
    <synonym>p-Hydroxy-β-phenylethylamine</synonym>
    <synonym>p-Β-aminoethylphenol</synonym>
    <synonym>Α-(4-hydroxyphenyl)-β-aminoethane</synonym>
  </synonyms>
  <chemical_formula>C8H11NO</chemical_formula>
  <average_molecular_weight>137.179</average_molecular_weight>
  <monisotopic_moleculate_weight>137.084063979</monisotopic_moleculate_weight>
  <iupac_name>4-(2-aminoethyl)phenol</iupac_name>
  <traditional_iupac>tyramine</traditional_iupac>
  <cas_registry_number>51-67-2</cas_registry_number>
  <smiles>NCCC1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2</inchi>
  <inchikey>DZGWFCGJZKJUFP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Phenethylamines</sub_class>
    <direct_parent>Phenethylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>2-arylethylamines</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>2-arylethylamine</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenethylamine</substituent>
      <substituent>Phenol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>Tyramine derivatives</external_descriptor>
      <external_descriptor>monoamine molecular messenger</external_descriptor>
      <external_descriptor>primary amino compound</external_descriptor>
      <external_descriptor>tyramines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>164 - 165 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>10.4 mg/mL at 15 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-(2-aminoethyl)phenol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>137.179</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>137.084063979</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCC1=CC=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H11NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DZGWFCGJZKJUFP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>46.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440131</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00483</kegg_id>
  <drugbank_id>DB08841</drugbank_id>
  <foodb_id>FDB000433</foodb_id>
  <chemspider_id>5408</chemspider_id>
  <pubchem_compound_id>5610</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15760</chebi_id>
  <knapsack_id>C00001435</knapsack_id>
  <wikipedia_id>Tyramine</wikipedia_id>
  <meta_cyc_id>TYRAMINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35110</bigg_id>
  <metlin_id>60</metlin_id>
  <synthesis_reference>Wang, Yalou; Xie, Dongmei.  Improved synthesis method of tyramine.    Zhongguo Yaowu Huaxue Zazhi  (1994),  4(2),  128-9.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:11 UTC</creation_date>
  <update_date>2020-04-15 22:06:10 UTC</update_date>
  <accession>BMDB0000307</accession>
  <secondary_accessions>
    <accession>BMDB00307</accession>
  </secondary_accessions>
  <name>1b-Hydroxycholic acid</name>
  <description>1b-Hydroxycholic acid, also known as 1b-hydroxycholate, belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. 1b-Hydroxycholic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 1b-Hydroxycholic acid exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>1b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-oate</synonym>
    <synonym>1b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-oic acid</synonym>
    <synonym>1b,3a,7a,12a-Tetrahydroxy-5b-cholanoate</synonym>
    <synonym>1b,3a,7a,12a-Tetrahydroxy-5b-cholanoic acid</synonym>
    <synonym>1b-Hydroxycholate</synonym>
    <synonym>(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R,16S)-3,5,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
    <synonym>(1beta,3alpha,5beta,7alpha,12alpha)-1,3,7,12-Tetrahydroxycholan-24-oic acid</synonym>
    <synonym>(1β,3α,5β,7α,12α)-1,3,7,12-Tetrahydroxycholan-24-oic acid</synonym>
    <synonym>1beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholan-24-oic acid</synonym>
    <synonym>1beta,3alpha,7alpha,12alpha-Tetrahydroxy-5beta-cholanoic acid</synonym>
    <synonym>1beta-Hydroxycholic acid</synonym>
    <synonym>1β,3α,7α,12α-Tetrahydroxy-5β-cholan-24-oic acid</synonym>
    <synonym>1β,3α,7α,12α-Tetrahydroxy-5β-cholanoic acid</synonym>
    <synonym>1β-Hydroxycholic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O6</chemical_formula>
  <average_molecular_weight>424.5708</average_molecular_weight>
  <monisotopic_moleculate_weight>424.282489012</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R,16S)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R,16S)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>80875-94-1</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)C[C@@H](O)[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O</smiles>
  <inchi>InChI=1S/C24H40O6/c1-12(4-7-21(29)30)15-5-6-16-22-17(11-20(28)24(15,16)3)23(2)13(9-18(22)26)8-14(25)10-19(23)27/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)/t12-,13+,14+,15-,16+,17+,18-,19-,20+,22+,23+,24-/m1/s1</inchi>
  <inchikey>UYVVLXVBEQAATF-WAIVXGPNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Tetrahydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxysteroids</alternative_parent>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxysteroid</substituent>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R,16S)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>424.5708</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>424.282489012</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)C[C@@H](O)[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O6/c1-12(4-7-21(29)30)15-5-6-16-22-17(11-20(28)24(15,16)3)23(2)13(9-18(22)26)8-14(25)10-19(23)27/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)/t12-,13+,14+,15-,16+,17+,18-,19-,20+,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UYVVLXVBEQAATF-WAIVXGPNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>112.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366531</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By GC-TOFMS and UPLC-QTOFMS</comment>
      <references>
        <reference>
          <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
          <pubmed_id>27999311</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB021934</foodb_id>
  <chemspider_id>4446981</chemspider_id>
  <pdbe_id/>
  <kegg_id/>
  <chebi_id/>
  <pubchem_compound_id>5283893</pubchem_compound_id>
  <knapsack_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5296</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Tohma, Masahiko; Mahara, Reijiro; Takeshita, Hiromi; Kurosawa, Takao; Ikegawa, Shigeo; Nittono, Hiroshi. Synthesis of the 1b-hydroxylated bile acids and identification of 1b,3a,7a-trihydroxy- and 1b,3a,7a,12a-tetrahydroxy-5b-cholan-24-oic acids in human meconium. Chem Pharm Bull (Tokyo). 1985 Jul;33(7):3071-3. Pubmed: 4085062</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
      <pubmed_id>27999311</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:13 UTC</creation_date>
  <update_date>2020-03-13 16:20:08 UTC</update_date>
  <accession>BMDB0000308</accession>
  <secondary_accessions>
    <accession>BMDB00308</accession>
  </secondary_accessions>
  <name>3b-Hydroxy-5-cholenoic acid</name>
  <description/>
  <synonyms>
    <synonym>3b-Hydroxy-5-cholenoate</synonym>
    <synonym>3b-Hydroxy-chol-5-en-24-Oate</synonym>
    <synonym>3b-Hydroxy-chol-5-en-24-Oic acid</synonym>
    <synonym>3b-Hydroxychol-5-en-24-ate</synonym>
    <synonym>3b-Hydroxychol-5-en-24-ic acid</synonym>
    <synonym>3b-Hydroxychol-5-en-24-Oate</synonym>
    <synonym>3b-Hydroxychol-5-en-24-Oic acid</synonym>
    <synonym>3b-Hydroxychol-5-enoate</synonym>
    <synonym>3b-Hydroxychol-5-enoic acid</synonym>
    <synonym>3b-Hydroxycholenoate</synonym>
    <synonym>3b-Hydroxycholenoic acid</synonym>
    <synonym>3beta-Hydroxy-5-cholenic acid</synonym>
    <synonym>3beta-Hydroxy-5-cholenoate</synonym>
    <synonym>3beta-Hydroxy-5-cholenoic acid</synonym>
    <synonym>3beta-Hydroxy-chol-5-en-24-Oate</synonym>
    <synonym>3beta-Hydroxy-chol-5-en-24-Oic acid</synonym>
    <synonym>3beta-Hydroxy-delta5-cholenic acid</synonym>
    <synonym>3beta-Hydroxychol-5-en-24-Oate</synonym>
    <synonym>3beta-Hydroxychol-5-en-24-Oic acid</synonym>
    <synonym>Cholenate</synonym>
    <synonym>Cholenic acid</synonym>
    <synonym>D5-Cholenate</synonym>
    <synonym>D5-Cholenic acid</synonym>
    <synonym>3 beta-Hydroxy-5-cholenic acid</synonym>
    <synonym>3 beta-Hydroxy-delta 5-cholenic acid, sodium salt</synonym>
    <synonym>3 beta-Hydroxy-delta 5-cholenic acid</synonym>
    <synonym>3 beta-Hydroxy-5-cholenoic acid</synonym>
    <synonym>(4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-Hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H38O3</chemical_formula>
  <average_molecular_weight>374.5567</average_molecular_weight>
  <monisotopic_moleculate_weight>374.282095082</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>5255-17-4</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H38O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h5,15,17-21,25H,4,6-14H2,1-3H3,(H,26,27)/t15-,17+,18+,19-,20+,21+,23+,24-/m1/s1</inchi>
  <inchikey>HIAJCGFYHIANNA-QIZZZRFXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Monohydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monohydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>374.5567</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>374.282095082</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H38O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H38O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h5,15,17-21,25H,4,6-14H2,1-3H3,(H,26,27)/t15-,17+,18+,19-,20+,21+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HIAJCGFYHIANNA-QIZZZRFXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>108.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>45.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373203</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB021935</foodb_id>
  <chemspider_id>83950</chemspider_id>
  <pubchem_compound_id>92997</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>384794</chebi_id>
  <knapsack_id/>
  <wikipedia_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5297</metlin_id>
  <synthesis_reference>Burton, Gerardo; Gros, Eduardo G.  Synthesis of 3b-hydroxy-5-cholenic acid from 3b-hydroxy-5-pregnen-20-one aimed at the preparation of labeled steroid compounds.    Journal of Steroid Biochemistry  (1977),  8(1),  69-72.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:14 UTC</creation_date>
  <update_date>2020-03-13 16:20:09 UTC</update_date>
  <accession>BMDB0000309</accession>
  <secondary_accessions>
    <accession>BMDB00309</accession>
  </secondary_accessions>
  <name>3a,16b-Dihydroxyandrostenone</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C19H28O3</chemical_formula>
  <average_molecular_weight>304.4238</average_molecular_weight>
  <monisotopic_moleculate_weight>304.203844762</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,10S,11S,13S,15R)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one</iupac_name>
  <traditional_iupac>3a,16b-dihydroxyandrostenone</traditional_iupac>
  <cas_registry_number>60828-06-0</cas_registry_number>
  <smiles>[H][C@@]12C[C@H](O)C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C</smiles>
  <inchi>InChI=1S/C19H28O3/c1-18-6-5-15-14(16(18)8-13(21)10-18)4-3-11-7-12(20)9-17(22)19(11,15)2/h9,11,13-16,20-21H,3-8,10H2,1-2H3/t11?,13-,14+,15-,16-,18+,19-/m0/s1</inchi>
  <inchikey>CUPQSMZELNNSIR-AATVIRSZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>16-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Enols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxosteroids</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-oxosteroid</substituent>
      <substituent>16-beta-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Enol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,10S,11S,13S,15R)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>304.4238</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>304.203844762</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@H](O)C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H28O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O3/c1-18-6-5-15-14(16(18)8-13(21)10-18)4-3-11-7-12(20)9-17(22)19(11,15)2/h9,11,13-16,20-21H,3-8,10H2,1-2H3/t11?,13-,14+,15-,16-,18+,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CUPQSMZELNNSIR-AATVIRSZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353154</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB021936</foodb_id>
  <drugbank_id/>
  <chemspider_id>13628053</chemspider_id>
  <pubchem_compound_id/>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5298</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:15 UTC</creation_date>
  <update_date>2020-03-13 16:20:09 UTC</update_date>
  <accession>BMDB0000310</accession>
  <secondary_accessions>
    <accession>BMDB00310</accession>
  </secondary_accessions>
  <name>Methylacetoacetic acid</name>
  <description/>
  <synonyms>
    <synonym>Methylacetoacetate</synonym>
    <synonym>1-Methoxybutane-1,3-dione</synonym>
    <synonym>3-oxo-Butanoate</synonym>
    <synonym>3-oxo-Butanoic acid</synonym>
    <synonym>3-oxo-Butanoic acid methyl ester</synonym>
    <synonym>3-Oxobutanoate</synonym>
    <synonym>3-Oxobutanoic acid</synonym>
    <synonym>3-Oxobutanoic acid methyl ester</synonym>
    <synonym>3-Oxobutyric acid methyl ester</synonym>
    <synonym>Acetoacetate methyl ester</synonym>
    <synonym>Acetoacetic acid methyl ester</synonym>
    <synonym>Acetoacetic methyl ester</synonym>
    <synonym>Methyl 3-oxobutanoate</synonym>
    <synonym>Methyl 3-oxobutanoic acid</synonym>
    <synonym>Methyl 3-oxobutyrate</synonym>
    <synonym>Methyl acetoacetate</synonym>
    <synonym>Methyl acetylacetate</synonym>
    <synonym>Methyl acetylacetonate</synonym>
  </synonyms>
  <chemical_formula>C5H8O3</chemical_formula>
  <average_molecular_weight>116.1152</average_molecular_weight>
  <monisotopic_moleculate_weight>116.047344122</monisotopic_moleculate_weight>
  <iupac_name>methyl 3-oxobutanoate</iupac_name>
  <traditional_iupac>methyl acetoacetate</traditional_iupac>
  <cas_registry_number>105-45-3</cas_registry_number>
  <smiles>COC(=O)CC(C)=O</smiles>
  <inchi>InChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3</inchi>
  <inchikey>WRQNANDWMGAFTP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Beta-keto acids and derivatives</sub_class>
    <direct_parent>Beta-keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-dicarbonyl compounds</alternative_parent>
      <alternative_parent>Fatty acid methyl esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Methyl esters</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-keto acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acid methyl ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Methyl ester</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-80 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>500.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>methyl 3-oxobutanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>116.1152</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>116.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC(=O)CC(C)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O3/c1-4(6)3-5(7)8-2/h3H2,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WRQNANDWMGAFTP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>43.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>27.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360477</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021937</foodb_id>
  <chemspider_id>13874867</chemspider_id>
  <pubchem_compound_id>7757</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5299</metlin_id>
  <synthesis_reference>Chan, Tak-Hang; Brownbridge, Peter. Reaction of electrophiles with 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene, a dianion equivalent of methyl acetoacetate. Journal of the Chemical Society, Chemical Communications (1979), (13), 578-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:21 UTC</creation_date>
  <update_date>2020-04-15 22:06:10 UTC</update_date>
  <accession>BMDB0000311</accession>
  <secondary_accessions>
    <accession>BMDB00311</accession>
  </secondary_accessions>
  <name>3b,4b,7a,12a-Tetrahydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3b,4b,7a,12a-Tetrahydroxy-5b-cholanoate</synonym>
    <synonym>(4R)-4-[(1S,2R,5S,6R,7S,9R,10R,11S,14R,15R,16S)-5,6,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O6</chemical_formula>
  <average_molecular_weight>424.5708</average_molecular_weight>
  <monisotopic_moleculate_weight>424.282489012</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5S,6R,7S,9R,10R,11S,14R,15R,16S)-5,6,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5S,6R,7S,9R,10R,11S,14R,15R,16S)-5,6,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>129099-70-3</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])[C@@H](O)[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O6/c1-12(4-7-20(28)29)13-5-6-14-21-15(11-19(27)24(13,14)3)23(2)9-8-17(25)22(30)16(23)10-18(21)26/h12-19,21-22,25-27,30H,4-11H2,1-3H3,(H,28,29)/t12-,13-,14+,15+,16-,17+,18-,19+,21+,22-,23-,24-/m1/s1</inchi>
  <inchikey>WGGZRKVUOFMQHM-VCELIZGUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Tetrahydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>4-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5S,6R,7S,9R,10R,11S,14R,15R,16S)-5,6,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>424.5708</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>424.282489012</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])[C@@H](O)[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O6/c1-12(4-7-20(28)29)13-5-6-14-21-15(11-19(27)24(13,14)3)23(2)9-8-17(25)22(30)16(23)10-18(21)26/h12-19,21-22,25-27,30H,4-11H2,1-3H3,(H,28,29)/t12-,13-,14+,15+,16-,17+,18-,19+,21+,22-,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WGGZRKVUOFMQHM-VCELIZGUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>112.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363948</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021938</foodb_id>
  <pubchem_compound_id>5283896</pubchem_compound_id>
  <chemspider_id>4446984</chemspider_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5300</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Iida, Takashi; Momose, Toshiaki; Chang, Frederic C.; Goto, Junichi; Nambara, Toshio.  Potential bile acid metabolites.  XV.  Synthesis of 4b-hydroxylated bile acids; unique bile acids in human fetal bile.    Chemical &amp; Pharmaceutical Bulletin  (1989),  37(12),  3323-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:22 UTC</creation_date>
  <update_date>2020-04-15 22:06:11 UTC</update_date>
  <accession>BMDB0000312</accession>
  <secondary_accessions>
    <accession>BMDB00312</accession>
  </secondary_accessions>
  <name>3a,7a,12b-Trihydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3alpha,7alpha,12beta-Trihydroxy-5beta-cholanate</synonym>
    <synonym>Lagocholic acid</synonym>
    <synonym>3a,7a,12b-Trihydroxy-5b-cholanate</synonym>
    <synonym>3a,7a,12b-Trihydroxy-5b-cholanic acid</synonym>
    <synonym>3alpha,7alpha,12beta-Trihydroxy-5beta-cholanic acid</synonym>
    <synonym>3α,7α,12β-trihydroxy-5β-cholanate</synonym>
    <synonym>3α,7α,12β-trihydroxy-5β-cholanic acid</synonym>
    <synonym>3a,7a,12b-Trihydroxy-5b-cholanoate</synonym>
    <synonym>Lagocholate</synonym>
    <synonym>12b-Hydroxyisocholate</synonym>
    <synonym>12b-Hydroxyisocholic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16R)-5,9,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
    <synonym>(3alpha,5beta,7alpha,12beta)-3,7,12-Trihydroxycholan-24-oic acid</synonym>
    <synonym>(3α,5β,7α,12β)-3,7,12-Trihydroxycholan-24-oic acid</synonym>
    <synonym>12beta-Hydroxyisocholic acid</synonym>
    <synonym>12β-Hydroxyisocholic acid</synonym>
    <synonym>3alpha,7alpha,12beta-Trihydroxy-5beta-cholanoic acid</synonym>
    <synonym>3α,7α,12β-Trihydroxy-5β-cholanoic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>71883-64-2</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@@H](O)[C@]12C)[C@H](C)CCC(O)=O</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20-,22+,23+,24-/m1/s1</inchi>
  <inchikey>BHQCQFFYRZLCQQ-KRHHAYMPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>trihydroxy-5beta-cholanic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@@H](O)[C@]12C)[C@H](C)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20-,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHQCQFFYRZLCQQ-KRHHAYMPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329127</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021939</foodb_id>
  <chemspider_id>4446957</chemspider_id>
  <pubchem_compound_id>5283869</pubchem_compound_id>
  <kegg_id/>
  <chebi_id>36240</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5301</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Batta, Ashok K.; Aggarwal, Suresht K.; Salen, Gerald; Shefer, Sarah.  Selective reduction of oxo bile acids:  synthesis of 3b-, 7b-, and 12b-hydroxy bile acids.  Journal of Lipid Research  (1991),  32(6),  977-83.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:23 UTC</creation_date>
  <update_date>2020-03-13 16:20:11 UTC</update_date>
  <accession>BMDB0000313</accession>
  <secondary_accessions>
    <accession>BMDB00313</accession>
  </secondary_accessions>
  <name>16b-Hydroxyestrone</name>
  <description/>
  <synonyms>
    <synonym>(16beta)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-one</synonym>
    <synonym>16-Hydroxyestrone</synonym>
    <synonym>3,16-Dihydroxyestra-1,3,5(10)-trien-17-one</synonym>
    <synonym>3,16beta-Dihydroxy-estra-1,3,5(10)-trien-17-one</synonym>
    <synonym>(16b)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-one</synonym>
    <synonym>(16Β)-3,16-dihydroxyestra-1,3,5(10)-trien-17-one</synonym>
    <synonym>3,16b-Dihydroxy-estra-1,3,5(10)-trien-17-one</synonym>
    <synonym>3,16Β-dihydroxy-estra-1,3,5(10)-trien-17-one</synonym>
    <synonym>16alpha-Hydroxyestrone</synonym>
    <synonym>16beta-Hydroxyestrone</synonym>
    <synonym>3,16-Dihydroxy-estra-1,3,5(10)-trien-17-one</synonym>
    <synonym>16 alpha-Hydroxyestrone</synonym>
    <synonym>16 beta-Hydroxyestrone</synonym>
    <synonym>16-alpha-Hydroxyestrone</synonym>
  </synonyms>
  <chemical_formula>C18H22O3</chemical_formula>
  <average_molecular_weight>286.3655</average_molecular_weight>
  <monisotopic_moleculate_weight>286.15689457</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,13S,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one</iupac_name>
  <traditional_iupac>16 α-hydroxyestrone</traditional_iupac>
  <cas_registry_number>966-06-3</cas_registry_number>
  <smiles>[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</smiles>
  <inchi>InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,18+/m1/s1</inchi>
  <inchikey>WPOCIZJTELRQMF-LFRCEIEQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>16-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>16-beta-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>16beta-hydroxy steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>organic molecular entity</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,13S,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>286.3655</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>286.15689457</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H22O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,18+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WPOCIZJTELRQMF-LFRCEIEQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>80.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348897</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021940</foodb_id>
  <chemspider_id>17215934</chemspider_id>
  <pubchem_compound_id>22833517</pubchem_compound_id>
  <chebi_id>87628</chebi_id>
  <drugbank_id/>
  <kegg_id>C05300</kegg_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5302</metlin_id>
  <synthesis_reference>Biggerstaff, W. R.; Gallagher, T. F.  3,16b-Dihydroxy-1,3,5-estratrien-17-one and related compounds.    Journal of Organic Chemistry  (1957),  22  1220-2.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:25 UTC</creation_date>
  <update_date>2020-03-13 16:20:11 UTC</update_date>
  <accession>BMDB0000314</accession>
  <secondary_accessions>
    <accession>BMDB00314</accession>
  </secondary_accessions>
  <name>3b-Allotetrahydrocortisol</name>
  <description/>
  <synonyms>
    <synonym>3b,5a-Tetrahydrocortisol</synonym>
    <synonym>Allo-3-beta-tetrahydrocortisol</synonym>
    <synonym>Reichstein'S substance V</synonym>
  </synonyms>
  <chemical_formula>C21H34O5</chemical_formula>
  <average_molecular_weight>366.4917</average_molecular_weight>
  <monisotopic_moleculate_weight>366.240624198</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-1-[(1S,2S,5S,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one</iupac_name>
  <traditional_iupac>reichstein substance V</traditional_iupac>
  <cas_registry_number>651-43-4</cas_registry_number>
  <smiles>[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,18+,19-,20-,21-/m0/s1</inchi>
  <inchikey>AODPIQQILQLWGS-VSJLKEFSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>11-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>11-beta-hydroxysteroid</substituent>
      <substituent>11-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Polyol</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>215 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-1-[(1S,2S,5S,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>366.4917</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>366.240624198</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H34O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,18+,19-,20-,21-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AODPIQQILQLWGS-VSJLKEFSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>97.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>41.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36061</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021941</foodb_id>
  <chemspider_id>13628056</chemspider_id>
  <pubchem_compound_id>12444612</pubchem_compound_id>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <kegg_id/>
  <drugbank_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5303</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Fukushima, David K.; Daum, Sol.  Synthesis of Reichstein's substance C and related compounds.  Journal of Organic Chemistry  (1961),  26  520-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:27 UTC</creation_date>
  <update_date>2020-04-15 22:37:12 UTC</update_date>
  <accession>BMDB0000315</accession>
  <secondary_accessions>
    <accession>BMDB00315</accession>
  </secondary_accessions>
  <name>16-a-Hydroxypregnenolone</name>
  <description/>
  <synonyms>
    <synonym>(3beta,16alpha)-3,16-Dihydroxypregn-5-en-20-one</synonym>
    <synonym>16-alpha-Hydroxypregnenolone</synonym>
    <synonym>(3b,16a)-3,16-Dihydroxypregn-5-en-20-one</synonym>
    <synonym>(3Β,16α)-3,16-dihydroxypregn-5-en-20-one</synonym>
    <synonym>16-Α-hydroxypregnenolone</synonym>
    <synonym>16 alpha-Hydroxypregnenolone</synonym>
    <synonym>16-a-Hydroxy-pregnenolone</synonym>
    <synonym>16-alpha-Hydroxy-pregnenolone</synonym>
    <synonym>16alpha-Hydroxypregnenolone</synonym>
    <synonym>3b,16a-Dihydroxypreg-5-en-20-one</synonym>
    <synonym>3b,16a-Dihydroxypregn-5-en-20-one</synonym>
    <synonym>3b,16a-Dihydroxypregnen-5-en-20-one</synonym>
    <synonym>5-Pregnene-3b,16a-diol-20-one</synonym>
    <synonym>Pregn-5-en-3b,16a-diol-20-one</synonym>
    <synonym>3 alpha,16 alpha-Dihydroxypregn-5-en-20-one</synonym>
    <synonym>3 beta,16 alpha-Dihydroxypregn-5-en-20-one</synonym>
    <synonym>3 beta,16 beta-Dihydroxypregn-5-en-20-one</synonym>
    <synonym>16a-Hydroxypregnenolone</synonym>
    <synonym>16Α-hydroxypregnenolone</synonym>
    <synonym>16-a-Hydroxypregnenolone</synonym>
  </synonyms>
  <chemical_formula>C21H32O3</chemical_formula>
  <average_molecular_weight>332.477</average_molecular_weight>
  <monisotopic_moleculate_weight>332.23514489</monisotopic_moleculate_weight>
  <iupac_name>1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one</iupac_name>
  <traditional_iupac>1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone</traditional_iupac>
  <cas_registry_number>520-88-7</cas_registry_number>
  <smiles>[H][C@@]12C[C@@H](O)[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H32O3/c1-12(22)19-18(24)11-17-15-5-4-13-10-14(23)6-8-20(13,2)16(15)7-9-21(17,19)3/h4,14-19,23-24H,5-11H2,1-3H3/t14-,15+,16-,17-,18+,19-,20-,21-/m0/s1</inchi>
  <inchikey>ZAKJZPQDUPCXSD-YRWKUUEZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Pregnane steroids</sub_class>
    <direct_parent>Gluco/mineralocorticoids, progestogins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>16-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>16-alpha-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>16alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>3beta-hydroxy steroid</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
      <external_descriptor>hydroxypregnenolone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>332.477</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>332.23514489</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@@H](O)[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H32O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H32O3/c1-12(22)19-18(24)11-17-15-5-4-13-10-14(23)6-8-20(13,2)16(15)7-9-21(17,19)3/h4,14-19,23-24H,5-11H2,1-3H3/t14-,15+,16-,17-,18+,19-,20-,21-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZAKJZPQDUPCXSD-YRWKUUEZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>95.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1271</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021942</foodb_id>
  <chemspider_id>4955002</chemspider_id>
  <pubchem_compound_id>6452574</pubchem_compound_id>
  <kegg_id>C06390  </kegg_id>
  <chebi_id>771</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5304</metlin_id>
  <synthesis_reference>Pierrepoint, C. G.; Griffiths, Keith; Grant, James K.  In vitro studies of feminizing tumors of the testis of man and dog.    Proc. Int. Congr. Horm. Steroids, 2nd  (1967),  Meeting Date 1966,     761-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:28 UTC</creation_date>
  <update_date>2020-04-15 22:06:12 UTC</update_date>
  <accession>BMDB0000316</accession>
  <secondary_accessions>
    <accession>BMDB00316</accession>
  </secondary_accessions>
  <name>2b,3a,7a,12a-Tetrahydroxy-5b-cholanoic acid</name>
  <description>2b,3a,7a,12a-Tetrahydroxy-5b-cholanoic acid, also known as 2b-hydroxycholate, belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. 2b,3a,7a,12a-Tetrahydroxy-5b-cholanoic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 2b,3a,7a,12a-Tetrahydroxy-5b-cholanoic acid exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>2b,3a,7a,12a-Tetrahydroxy-5b-cholanoate</synonym>
    <synonym>2b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-Oate</synonym>
    <synonym>2b,3a,7a,12a-Tetrahydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>2b,3a,7a,12a-Tetrahydroxy-5b-cholanoic</synonym>
    <synonym>2b-Hydroxycholate</synonym>
    <synonym>2b-Hydroxycholic acid</synonym>
    <synonym>(4S)-4-[(2S,4S,5S,7R,9R,15R,16S)-4,5,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O6</chemical_formula>
  <average_molecular_weight>424.5708</average_molecular_weight>
  <monisotopic_moleculate_weight>424.282489012</monisotopic_moleculate_weight>
  <iupac_name>(4S)-4-[(2S,4S,5S,7R,9R,15R,16S)-4,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>2b-hydroxycholate</traditional_iupac>
  <cas_registry_number>60696-60-8</cas_registry_number>
  <smiles>[H][C@@]12C[C@H](O)[C@@H](O)C[C@]1(C)C1C[C@H](O)[C@]3(C)C(CCC3C1[C@H](O)C2)[C@@H](C)CCC(O)=O</smiles>
  <inchi>InChI=1S/C24H40O6/c1-12(4-7-21(29)30)14-5-6-15-22-16(10-20(28)24(14,15)3)23(2)11-19(27)17(25)8-13(23)9-18(22)26/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)/t12-,13-,14?,15?,16?,17-,18+,19-,20-,22?,23-,24+/m0/s1</inchi>
  <inchikey>IMMADCCLTPCOKH-DLPNMVJGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Tetrahydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>2-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4S)-4-[(2S,4S,5S,7R,9R,15R,16S)-4,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>424.5708</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>424.282489012</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@H](O)[C@@H](O)C[C@]1(C)C1C[C@H](O)[C@]3(C)C(CCC3C1[C@H](O)C2)[C@@H](C)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O6/c1-12(4-7-21(29)30)14-5-6-15-22-16(10-20(28)24(14,15)3)23(2)11-19(27)17(25)8-13(23)9-18(22)26/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)/t12-,13-,14?,15?,16?,17-,18+,19-,20-,22?,23-,24+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IMMADCCLTPCOKH-DLPNMVJGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>112.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>48.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32485</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By GC-TOFMS and UPLC-QTOFMS</comment>
      <references>
        <reference>
          <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
          <pubmed_id>27999311</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB021943</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477680</pubchem_compound_id>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <kegg_id/>
  <drugbank_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5305</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Iida, Takashi; Komatsubara, Ichiro; Chang, Frederic C.; Goto, Junichi; Nambara, Toshio.  Potential bile acid metabolites.  17.  Synthesis of 2b-hydroxylated bile acids.    Steroids  (1991),  56(3),  114-22.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
      <pubmed_id>27999311</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:29 UTC</creation_date>
  <update_date>2020-03-13 16:20:13 UTC</update_date>
  <accession>BMDB0000317</accession>
  <secondary_accessions>
    <accession>BMDB00317</accession>
  </secondary_accessions>
  <name>2-Hydroxy-3-methylpentanoic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Hydroxy-3-methylpentanoate</synonym>
    <synonym>(2R,3R)-2-Hydroxy-3-methyl-pentanoate</synonym>
    <synonym>(2R,3R)-2-Hydroxy-3-methyl-pentanoic acid</synonym>
    <synonym>(2R,3R)-2-Hydroxy-3-methylpentanoate</synonym>
    <synonym>(2R,3R)-2-Hydroxy-3-methylpentanoic acid</synonym>
    <synonym>2-Hydroxy-3-methyl-pentanoate</synonym>
    <synonym>2-Hydroxy-3-methyl-pentanoic acid</synonym>
    <synonym>2-Hydroxy-3-methyl-valerate</synonym>
    <synonym>2-Hydroxy-3-methyl-valeric acid</synonym>
    <synonym>2-Hydroxy-3-methylvalerate</synonym>
    <synonym>2-Hydroxy-3-methylvaleric acid</synonym>
    <synonym>a-Hydroxy-b-methylvalerate</synonym>
    <synonym>a-Hydroxy-b-methylvaleric acid</synonym>
    <synonym>alpha-Hydroxy-beta-methylvalerate</synonym>
    <synonym>alpha-Hydroxy-beta-methylvaleric acid</synonym>
    <synonym>HMVA</synonym>
  </synonyms>
  <chemical_formula>C6H12O3</chemical_formula>
  <average_molecular_weight>132.1577</average_molecular_weight>
  <monisotopic_moleculate_weight>132.07864425</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R)-2-hydroxy-3-methylpentanoic acid</iupac_name>
  <traditional_iupac>2-hydroxy-3-methyl-valerate</traditional_iupac>
  <cas_registry_number>488-15-3</cas_registry_number>
  <smiles>CC[C@@H](C)[C@@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H12O3/c1-3-4(2)5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t4-,5-/m1/s1</inchi>
  <inchikey>RILPIWOPNGRASR-RFZPGFLSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R)-2-hydroxy-3-methylpentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.1577</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.07864425</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC[C@@H](C)[C@@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O3/c1-3-4(2)5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t4-,5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RILPIWOPNGRASR-RFZPGFLSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35401</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021944</foodb_id>
  <chemspider_id>8972081</chemspider_id>
  <pubchem_compound_id>10796774</pubchem_compound_id>
  <chebi_id>89228</chebi_id>
  <phenol_explorer_compound_id/>
  <kegg_id/>
  <drugbank_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5306</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Mamer, O.A. &amp; Reimer, M.L.J. "On the Mechanisms of the Formation of L-Alloisoleucine and the 2-Hydroxy-3-methylvaleric Acid.." J. Biol. Chem. 267: 22141-22147 (1992).</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:30 UTC</creation_date>
  <update_date>2020-04-15 22:20:27 UTC</update_date>
  <accession>BMDB0000318</accession>
  <secondary_accessions>
    <accession>BMDB00318</accession>
  </secondary_accessions>
  <name>3,4-Dihydroxyphenylglycol</name>
  <description>3,4-Dihydroxyphenylglycol, also known as DHPG or 3,4-dihydroxyphenylglycol, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-Dihydroxyphenylglycol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 3,4-Dihydroxyphenylglycol exists in all living organisms, ranging from bacteria to humans. 3,4-Dihydroxyphenylglycol participates in a number of enzymatic reactions, within cattle. In particular, 3,4-Dihydroxyphenylglycol can be biosynthesized from 3,4-dihydroxymandelaldehyde through its interaction with the enzyme alcohol dehydrogenase 1A. In addition, 3,4-Dihydroxyphenylglycol and guaiacol can be converted into vanylglycol and pyrocatechol; which is mediated by the enzyme catechol O-methyltransferase. In cattle, 3,4-dihydroxyphenylglycol is involved in the metabolic pathway called the tyrosine metabolism pathway.</description>
  <synonyms>
    <synonym>(3,4-Dihydroxyphenyl)ethylene glycol</synonym>
    <synonym>1-(3,4-Dihydroxyphenyl)-1,2-ethanediol</synonym>
    <synonym>2-Hydroxy-2-(3,4-dihydroxy)phenylethanol</synonym>
    <synonym>3,4-Dihydroxyphenethyl glycol</synonym>
    <synonym>3,4-Dihydroxyphenylethyl glycol</synonym>
    <synonym>beta,3,4-Trihydroxy phenethyl alcohol</synonym>
    <synonym>DHPG</synonym>
    <synonym>Dihydroxyphenylethylene glycol</synonym>
    <synonym>DOPEG</synonym>
    <synonym>b,3,4-Trihydroxy phenethyl alcohol</synonym>
    <synonym>Β,3,4-trihydroxy phenethyl alcohol</synonym>
    <synonym>3,4-Dihydroxyphenylethyleneglycol</synonym>
    <synonym>4-(1,2-Dihydroxyethyl)-1,2-benzenediol</synonym>
    <synonym>DL-3,4-Dihydroxyphenylglycol</synonym>
    <synonym>Dihydroxyphenylethylene glycol, (+-)-isomer</synonym>
    <synonym>Dihydroxyphenylethylene glycol, (S)-isomer</synonym>
    <synonym>Dihydroxyphenylglycine</synonym>
  </synonyms>
  <chemical_formula>C8H10O4</chemical_formula>
  <average_molecular_weight>170.1626</average_molecular_weight>
  <monisotopic_moleculate_weight>170.057908808</monisotopic_moleculate_weight>
  <iupac_name>4-(1,2-dihydroxyethyl)benzene-1,2-diol</iupac_name>
  <traditional_iupac>3,4-dihydroxyphenylglycol</traditional_iupac>
  <cas_registry_number>28822-73-3</cas_registry_number>
  <smiles>OCC(O)C1=CC(O)=C(O)C=C1</smiles>
  <inchi>InChI=1S/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2</inchi>
  <inchikey>MTVWFVDWRVYDOR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Benzenediols</sub_class>
    <direct_parent>Catechols</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Catechol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a catechol</external_descriptor>
      <external_descriptor>catechols</external_descriptor>
      <external_descriptor>tetrol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>130 - 132 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.01</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.032</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-(1,2-dihydroxyethyl)benzene-1,2-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>170.1626</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>170.057908808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(O)C1=CC(O)=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H10O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MTVWFVDWRVYDOR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440123</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB020084</foodb_id>
  <chemspider_id>82648</chemspider_id>
  <pubchem_compound_id>91528</pubchem_compound_id>
  <kegg_id>C05576</kegg_id>
  <chebi_id>1387</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id>661</phenol_explorer_compound_id>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-11878</meta_cyc_id>
  <bigg_id>46054</bigg_id>
  <wikipedia_id/>
  <metlin_id>5307</metlin_id>
  <synthesis_reference>Hunter L W; Rorie D K; Yaksh T L; Tyce G M  Concurrent separation of catecholamines, dihydroxyphenylglycol, vasoactive intestinal peptide, and neuropeptide Y in superfusate and tissue extract.    Analytical biochemistry  (1988),  173(2),  340-52.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:31 UTC</creation_date>
  <update_date>2020-04-15 20:46:22 UTC</update_date>
  <accession>BMDB0000319</accession>
  <secondary_accessions>
    <accession>BMDB00319</accession>
  </secondary_accessions>
  <name>18-Hydroxycorticosterone</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C21H30O5</chemical_formula>
  <average_molecular_weight>362.466</average_molecular_weight>
  <monisotopic_moleculate_weight>362.209324066</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10S,11S,14S,15R)-17-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10S,11S,14S,15R)-17-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])C([H])(O)C[C@]12CO)C(=O)CO</smiles>
  <inchi>InChI=1S/C21H30O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,14-17,19,22-23,25H,2-7,9-11H2,1H3/t14-,15-,16+,17?,19+,20-,21+/m0/s1</inchi>
  <inchikey>HFSXHZZDNDGLQN-SNGWAEAYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>11-hydroxysteroids</alternative_parent>
      <alternative_parent>18-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>11-hydroxysteroid</substituent>
      <substituent>18-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10S,11S,14S,15R)-17-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>362.466</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>362.209324066</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])C([H])(O)C[C@]12CO)C(=O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H30O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H30O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,14-17,19,22-23,25H,2-7,9-11H2,1H3/t14-,15-,16+,17?,19+,20-,21+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HFSXHZZDNDGLQN-SNGWAEAYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>97.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1240090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1240091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1240092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1355515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1355516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1355517</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id>57105429</pubchem_compound_id>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <kegg_id/>
  <drugbank_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>18-Hydroxycorticosterone</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Boudi, Ahmed; Lemoine, Pascale; Viossat, Bernard; Tomas, Alain; Fiet, Jean; Galons, Herve.  A convenient synthesis of 18-hydroxycorticosterone and 18-hydroxy-11-desoxycorticosterone via stereospecific hypoiodination of 20-hydroxysteroids.    Tetrahedron  (1999),  55(16),  5171-5176. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:33 UTC</creation_date>
  <update_date>2020-04-15 22:06:12 UTC</update_date>
  <accession>BMDB0000320</accession>
  <secondary_accessions>
    <accession>BMDB00320</accession>
  </secondary_accessions>
  <name>3a,4b,7a-Trihydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3a,4b,7a-Trihydroxy-5b-cholanoate</synonym>
    <synonym>3,4,7-Trihydroxycholanoate</synonym>
    <synonym>3,4,7-Trihydroxycholanoic acid</synonym>
    <synonym>3a,4b,7a-Trihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,4b,7a-Trihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3alpha,4beta,7alpha-Trihydroxy-5beta-cholan-24-Oate</synonym>
    <synonym>3alpha,4beta,7alpha-Trihydroxy-5beta-cholan-24-Oic acid</synonym>
    <synonym>3alpha,4beta,7alpha-Trihydroxy-5beta-cholanoate</synonym>
    <synonym>3alpha,4beta,7alpha-Trihydroxy-5beta-cholanoic acid</synonym>
    <synonym>3 alpha,4 beta,7 alpha-Trihydroxy-5 beta-cholanoic acid</synonym>
    <synonym>3,4,7-TCOA</synonym>
    <synonym>(4S)-4-[(1S,2R,5R,6R,7S,9R,10S,11S,15R)-5,6,9-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4S)-4-[(1S,2R,5R,6R,7S,9R,10S,11S,15R)-5,6,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>3,4,7-trihydroxycholanoic acid</traditional_iupac>
  <cas_registry_number>117590-81-5</cas_registry_number>
  <smiles>[H][C@@]12CCC([C@@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])[C@@H](O)[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-20(27)28)14-5-6-15-21-16(8-10-23(14,15)2)24(3)11-9-18(25)22(29)17(24)12-19(21)26/h13-19,21-22,25-26,29H,4-12H2,1-3H3,(H,27,28)/t13-,14?,15-,16-,17+,18+,19+,21-,22+,23+,24+/m0/s1</inchi>
  <inchikey>AIHWGPJJINPTRP-VSASKLEVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>4-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4S)-4-[(1S,2R,5R,6R,7S,9R,10S,11S,15R)-5,6,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC([C@@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])[C@@H](O)[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-20(27)28)14-5-6-15-21-16(8-10-23(14,15)2)24(3)11-9-18(25)22(29)17(24)12-19(21)26/h13-19,21-22,25-26,29H,4-12H2,1-3H3,(H,27,28)/t13-,14?,15-,16-,17+,18+,19+,21-,22+,23+,24+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AIHWGPJJINPTRP-VSASKLEVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30715</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021946</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477681</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5309</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Dumaswala R; Setchell K D; Zimmer-Nechemias L; Iida T; Goto J; Nambara T  Identification of 3 alpha,4 beta,7 alpha-trihydroxy-5 beta-cholanoic acid in human bile: reflection of a new pathway in bile acid metabolism in humans.    Journal of lipid research  (1989),  30(6),  847-56.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:34 UTC</creation_date>
  <update_date>2020-04-14 22:47:23 UTC</update_date>
  <accession>BMDB0000321</accession>
  <secondary_accessions>
    <accession>BMDB00321</accession>
  </secondary_accessions>
  <name>2-Hydroxyadipic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Hydroxyadipate</synonym>
    <synonym>2-Hydroxyhexanedioic acid</synonym>
    <synonym>2-Hydroxyhexanedioate</synonym>
    <synonym>2,3,4-Trideoxyhexarate</synonym>
    <synonym>2,3,4-Trideoxyhexaric acid</synonym>
    <synonym>2-Hydroxy-adipate</synonym>
    <synonym>2-Hydroxy-adipic acid</synonym>
    <synonym>2-Hydroxy-hexanedioate</synonym>
    <synonym>2-Hydroxy-hexanedioic acid</synonym>
    <synonym>a-Hydroxyadipate</synonym>
    <synonym>a-Hydroxyadipic acid</synonym>
    <synonym>alpha-Hydroxyadipate</synonym>
    <synonym>alpha-Hydroxyadipic acid</synonym>
    <synonym>DL-2-Hydroxyadipate</synonym>
    <synonym>DL-2-Hydroxyadipic acid</synonym>
  </synonyms>
  <chemical_formula>C6H10O5</chemical_formula>
  <average_molecular_weight>162.1406</average_molecular_weight>
  <monisotopic_moleculate_weight>162.05282343</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxyhexanedioic acid</iupac_name>
  <traditional_iupac>α-hydroxyadipic acid</traditional_iupac>
  <cas_registry_number>18294-85-4</cas_registry_number>
  <smiles>OC(CCCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)</inchi>
  <inchikey>OTTXIFWBPRRYOG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxydicarboxylic acid</external_descriptor>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxyhexanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>162.1406</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>162.05282343</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(CCCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OTTXIFWBPRRYOG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368145</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021947</foodb_id>
  <chemspider_id>167943</chemspider_id>
  <pubchem_compound_id>193530</pubchem_compound_id>
  <kegg_id>C02360</kegg_id>
  <chebi_id>17023</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5310</metlin_id>
  <synthesis_reference>Griot, Rudolf. a-Hydroxyadipic acid.  Helvetica Chimica Acta  (1958),  41  2236-41.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:35 UTC</creation_date>
  <update_date>2020-04-15 20:46:23 UTC</update_date>
  <accession>BMDB0000322</accession>
  <secondary_accessions>
    <accession>BMDB00322</accession>
  </secondary_accessions>
  <name>16-Oxoandrostenediol</name>
  <description/>
  <synonyms>
    <synonym>(3b,17b)-3b,17b-Dihydroxyandrost-5-en-16-one</synonym>
    <synonym>3b,17b-Dihydroxy-androst-5-en-16-one</synonym>
    <synonym>3b,17b-Dihydroxyandrost-5-en-16-one</synonym>
    <synonym>3beta,17beta-Dihydroxy-androst-5-en-16-one</synonym>
    <synonym>5-Androsten-3b,17b-diol-16-one</synonym>
    <synonym>Androst-5-ene-3b,17b-diol-16-one</synonym>
  </synonyms>
  <chemical_formula>C19H28O3</chemical_formula>
  <average_molecular_weight>304.4238</average_molecular_weight>
  <monisotopic_moleculate_weight>304.203844762</monisotopic_moleculate_weight>
  <iupac_name>(2R,5S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-one</iupac_name>
  <traditional_iupac>5-androsten-3b,17b-diol-16-one</traditional_iupac>
  <cas_registry_number>1159-66-6</cas_registry_number>
  <smiles>C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O</smiles>
  <inchi>InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-15,17,20,22H,4-10H2,1-2H3/t12-,13?,14?,15?,17-,18-,19-/m0/s1</inchi>
  <inchikey>AKRBLZKRYPEVIK-IACDPKRHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>16-oxosteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>16-oxosteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>203 - 205 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,5S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>304.4238</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>304.203844762</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H28O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-15,17,20,22H,4-10H2,1-2H3/t12-,13?,14?,15?,17-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AKRBLZKRYPEVIK-IACDPKRHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>85.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31801</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021948</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477682</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5311</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Aoki, Terumi; Yamamura, Hiroko; Takei, Kyoko; Mori, Hiromu.  Synthesis of 16-oxygenated androst-5-en-3b-ol derivatives.    Chemical &amp; Pharmaceutical Bulletin  (1964),  12(7),  808-12.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:36 UTC</creation_date>
  <update_date>2020-03-13 16:20:16 UTC</update_date>
  <accession>BMDB0000323</accession>
  <secondary_accessions>
    <accession>BMDB00323</accession>
  </secondary_accessions>
  <name>3-Amino-2-piperidone</name>
  <description/>
  <synonyms>
    <synonym>Cyclo-ornithine</synonym>
    <synonym>(+)-3-Aminopiperidin-2-one</synonym>
    <synonym>(R)-(+)-3-Amino-2-piperidinon</synonym>
    <synonym>(S)-(-)-3-Amino-2-piperidinon</synonym>
    <synonym>(S)-3-Amino-2-piperidinon</synonym>
    <synonym>3-Amino-2-piperidinone</synonym>
    <synonym>Ornithine N5-lactam</synonym>
    <synonym>3-Aminopiperidine-2-one</synonym>
    <synonym>3-Amino-2-piperidone</synonym>
  </synonyms>
  <chemical_formula>C5H10N2O</chemical_formula>
  <average_molecular_weight>114.1457</average_molecular_weight>
  <monisotopic_moleculate_weight>114.079312952</monisotopic_moleculate_weight>
  <iupac_name>3-aminopiperidin-2-one</iupac_name>
  <traditional_iupac>3-amino-2-piperidone</traditional_iupac>
  <cas_registry_number>1892-22-4</cas_registry_number>
  <smiles>NC1CCCNC1=O</smiles>
  <inchi>InChI=1S/C5H10N2O/c6-4-2-1-3-7-5(4)8/h4H,1-3,6H2,(H,7,8)</inchi>
  <inchikey>YCCMTCQQDULIFE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acid amides</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopiperidines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Delta lactams</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Piperidinones</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-aminopiperidine</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Amine</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Delta-lactam</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Piperidine</substituent>
      <substituent>Piperidinone</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>delta-lactam</external_descriptor>
      <external_descriptor>piperidones</external_descriptor>
      <external_descriptor>primary amino compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-aminopiperidin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>114.1457</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>114.079312952</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1CCCNC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10N2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10N2O/c6-4-2-1-3-7-5(4)8/h4H,1-3,6H2,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YCCMTCQQDULIFE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>55.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33013</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021949</foodb_id>
  <chemspider_id>4371576</chemspider_id>
  <pubchem_compound_id>5200225</pubchem_compound_id>
  <kegg_id/>
  <chebi_id>76341</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5312</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Moon, Byong Hoon; Martin, Charles Franklin.  3-Aminopiperidones.  V.  2-Ethoxy and 2-carbethoxy derivatives of 2-p-methoxyphenylglutarimide.    Journal of Pharmaceutical Sciences  (1971),  60(4),  618-20.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:38 UTC</creation_date>
  <update_date>2020-03-13 16:20:17 UTC</update_date>
  <accession>BMDB0000324</accession>
  <secondary_accessions>
    <accession>BMDB00324</accession>
  </secondary_accessions>
  <name>3a,16a-Dihydroxyandrostenone</name>
  <description/>
  <synonyms>
    <synonym>3a,16a-Dihydroxyandrost-5-en-17-one</synonym>
  </synonyms>
  <chemical_formula>C19H28O3</chemical_formula>
  <average_molecular_weight>304.4238</average_molecular_weight>
  <monisotopic_moleculate_weight>304.203844762</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,10S,11S,13R,15R)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one</iupac_name>
  <traditional_iupac>3a,16a-dihydroxyandrostenone</traditional_iupac>
  <cas_registry_number>14167-51-2</cas_registry_number>
  <smiles>[H][C@@]12C[C@@H](O)C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C</smiles>
  <inchi>InChI=1S/C19H28O3/c1-18-6-5-15-14(16(18)8-13(21)10-18)4-3-11-7-12(20)9-17(22)19(11,15)2/h9,11,13-16,20-21H,3-8,10H2,1-2H3/t11?,13-,14-,15+,16+,18-,19+/m1/s1</inchi>
  <inchikey>CUPQSMZELNNSIR-LZRZFMTJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>16-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Enols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxosteroids</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-oxosteroid</substituent>
      <substituent>16-alpha-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Enol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,10S,11S,13R,15R)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>304.4238</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>304.203844762</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@@H](O)C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H28O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O3/c1-18-6-5-15-14(16(18)8-13(21)10-18)4-3-11-7-12(20)9-17(22)19(11,15)2/h9,11,13-16,20-21H,3-8,10H2,1-2H3/t11?,13-,14-,15+,16+,18-,19+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CUPQSMZELNNSIR-LZRZFMTJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365850</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021950</foodb_id>
  <chemspider_id>13628060</chemspider_id>
  <pubchem_compound_id/>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5313</metlin_id>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:39 UTC</creation_date>
  <update_date>2020-03-13 16:20:17 UTC</update_date>
  <accession>BMDB0000325</accession>
  <secondary_accessions>
    <accession>BMDB00325</accession>
  </secondary_accessions>
  <name>3-Hydroxysuberic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Hydroxysuberate</synonym>
    <synonym>3-Hydroxyoctanedioate</synonym>
    <synonym>3-Hydroxyoctanedioic acid</synonym>
    <synonym>3-Hydroxy-suberate</synonym>
  </synonyms>
  <chemical_formula>C8H14O5</chemical_formula>
  <average_molecular_weight>190.1938</average_molecular_weight>
  <monisotopic_moleculate_weight>190.084123558</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxyoctanedioic acid</iupac_name>
  <traditional_iupac>3-hydroxysuberic acid</traditional_iupac>
  <cas_registry_number>73141-47-6</cas_registry_number>
  <smiles>OC(CCCCC(O)=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C8H14O5/c9-6(5-8(12)13)3-1-2-4-7(10)11/h6,9H,1-5H2,(H,10,11)(H,12,13)</inchi>
  <inchikey>ARJZZFJXSNJKGR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Medium-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Medium-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hydroxy carboxylic acid</external_descriptor>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxyoctanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>190.1938</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>190.084123558</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(CCCCC(O)=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H14O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H14O5/c9-6(5-8(12)13)3-1-2-4-7(10)11/h6,9H,1-5H2,(H,10,11)(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ARJZZFJXSNJKGR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356493</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021951</foodb_id>
  <chemspider_id>13498677</chemspider_id>
  <pubchem_compound_id>22328017</pubchem_compound_id>
  <kegg_id/>
  <chebi_id>70766</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5314</metlin_id>
  <synthesis_reference>Chiruta, Chandramouli; Jachak, Santosh; Clive, Derrick L. J.  A convenient general method for the synthesis of hydroxy diacids.    Tetrahedron Letters  (2007),  48(18),  3141-3143.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:40 UTC</creation_date>
  <update_date>2020-04-15 22:06:13 UTC</update_date>
  <accession>BMDB0000326</accession>
  <secondary_accessions>
    <accession>BMDB00326</accession>
  </secondary_accessions>
  <name>1b,3a,12a-Trihydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>1b,3a,12a-Trihydroxy-5b-cholanoate</synonym>
    <synonym>1,3,12-Trihydroxy-(5b)-cholan-24-Oate</synonym>
    <synonym>1,3,12-Trihydroxy-(5b)-cholan-24-Oic acid</synonym>
    <synonym>1b,3a,12a-Trihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>1b,3a,12a-Trihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>(4R)-4-[(2S,3R,5S,15R,16S)-3,5,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(2S,3R,5S,15R,16S)-3,5,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(2S,3R,5S,15R,16S)-3,5,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>80434-32-8</cas_registry_number>
  <smiles>C[C@H](CCC(O)=O)C1CCC2C3CCC4C[C@H](O)C[C@@H](O)[C@]4(C)C3C[C@H](O)[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-9-22(28)29)17-7-8-18-16-6-5-14-10-15(25)11-20(26)23(14,2)19(16)12-21(27)24(17,18)3/h13-21,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14?,15+,16?,17?,18?,19?,20-,21+,23+,24-/m1/s1</inchi>
  <inchikey>DAKYVYUAVGJDRK-LFMRMFNLSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxysteroids</alternative_parent>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxysteroid</substituent>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(2S,3R,5S,15R,16S)-3,5,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](CCC(O)=O)C1CCC2C3CCC4C[C@H](O)C[C@@H](O)[C@]4(C)C3C[C@H](O)[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-9-22(28)29)17-7-8-18-16-6-5-14-10-15(25)11-20(26)23(14,2)19(16)12-21(27)24(17,18)3/h13-21,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14?,15+,16?,17?,18?,19?,20-,21+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DAKYVYUAVGJDRK-LFMRMFNLSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156059</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021952</foodb_id>
  <pubchem_compound_id>53477683</pubchem_compound_id>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>89219</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5315</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>ohma, Masahiko; Mahara, Reijiro; Takeshita, Hiromi; Kurosawa, Takao; Ikegawa, Shigeo; Nittono, Hiroshi.  Synthesis of the 1b-hydroxylated bile acids and identification of 1b,3a,7a-trihydroxy- and 1b,3a,7a,12a-tetrahydroxy-5b-cholan-24-oic acids in human meconium.    Chemical &amp; Pharmaceutical Bulletin  (1985),  33(7),  3071-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:41 UTC</creation_date>
  <update_date>2020-03-13 16:20:18 UTC</update_date>
  <accession>BMDB0000328</accession>
  <secondary_accessions>
    <accession>BMDB00328</accession>
  </secondary_accessions>
  <name>12-Ketodeoxycholic acid</name>
  <description/>
  <synonyms>
    <synonym>12-Ketodeoxycholate</synonym>
    <synonym>(3a,5b)-3-Hydroxy-12-oxo-cholan-24-Oate</synonym>
    <synonym>(3a,5b)-3-Hydroxy-12-oxo-cholan-24-Oic acid</synonym>
    <synonym>(3alpha,5beta)-3-Hydroxy-12-oxo-cholan-24-Oate</synonym>
    <synonym>(3alpha,5beta)-3-Hydroxy-12-oxo-cholan-24-Oic acid</synonym>
    <synonym>12-Dehydrodeoxycholate</synonym>
    <synonym>12-Dehydrodeoxycholic acid</synonym>
    <synonym>12-Ketolithocholate</synonym>
    <synonym>12-Ketolithocholic acid</synonym>
    <synonym>12-oxo-3a-Hydroxy-5b-cholanate</synonym>
    <synonym>12-oxo-3a-Hydroxy-5b-cholanic acid</synonym>
    <synonym>12-Oxolithocholate</synonym>
    <synonym>12-Oxolithocholic acid</synonym>
    <synonym>3a-Hydroxy-12-oxo-5b-cholan-24-Oate</synonym>
    <synonym>3a-Hydroxy-12-oxo-5b-cholan-24-Oic acid</synonym>
    <synonym>3a-Hydroxy-12-oxo-5b-cholanate</synonym>
    <synonym>3a-Hydroxy-12-oxo-5b-cholanic acid</synonym>
    <synonym>3a-Hydroxy-12-oxo-5b-cholanoate</synonym>
    <synonym>3a-Hydroxy-12-oxo-5b-cholanoic acid</synonym>
    <synonym>3-Hydroxy-12-ketocholanoic acid</synonym>
    <synonym>12-Ketolithocholic acid, (3beta,5beta)-isomer</synonym>
    <synonym>3 alpha-Hydroxy-12-keto-5 beta-cholanoic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-Hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H38O4</chemical_formula>
  <average_molecular_weight>390.5561</average_molecular_weight>
  <monisotopic_moleculate_weight>390.277009704</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>12-ketolithocholic acid</traditional_iupac>
  <cas_registry_number>5130-29-0</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC(=O)[C@]12C)[C@H](C)CCC(O)=O</smiles>
  <inchi>InChI=1S/C24H38O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1</inchi>
  <inchikey>CVNYHSDFZXHMMJ-VPUMZWJWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Monohydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxosteroids</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-oxosteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monohydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>390.5561</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>390.277009704</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC(=O)[C@]12C)[C@H](C)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H38O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H38O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-20,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CVNYHSDFZXHMMJ-VPUMZWJWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>108.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>45.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35149</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021953</foodb_id>
  <chemspider_id>2338365</chemspider_id>
  <pubchem_compound_id>3080612</pubchem_compound_id>
  <kegg_id/>
  <chebi_id>803536</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5317</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Suzuki, Yoshinori; Okamura, Akio; Shimomura, Kazuo; Suzuki, Tadayuki.  Purification of bile acids.    Jpn. Kokai Tokkyo Koho  (1985),     6 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:42 UTC</creation_date>
  <update_date>2020-03-13 16:20:19 UTC</update_date>
  <accession>BMDB0000329</accession>
  <secondary_accessions>
    <accession>BMDB00329</accession>
  </secondary_accessions>
  <name>2-Phenylbutyric acid</name>
  <description/>
  <synonyms>
    <synonym>alpha-Ethyl-alpha-toluic acid</synonym>
    <synonym>alpha-Phenylbutyric acid</synonym>
    <synonym>a-Ethyl-a-toluate</synonym>
    <synonym>a-Ethyl-a-toluic acid</synonym>
    <synonym>alpha-Ethyl-alpha-toluate</synonym>
    <synonym>Α-ethyl-α-toluate</synonym>
    <synonym>Α-ethyl-α-toluic acid</synonym>
    <synonym>a-Phenylbutyrate</synonym>
    <synonym>a-Phenylbutyric acid</synonym>
    <synonym>alpha-Phenylbutyrate</synonym>
    <synonym>Α-phenylbutyrate</synonym>
    <synonym>Α-phenylbutyric acid</synonym>
    <synonym>2-Phenylbutyrate</synonym>
    <synonym>(RS)-2-Phenylbutanoate</synonym>
    <synonym>(RS)-2-Phenylbutanoic acid</synonym>
    <synonym>2-Phenylbutanoate</synonym>
    <synonym>2-Phenylbutanoic acid</synonym>
    <synonym>a-Ethylbenzeneacetate</synonym>
    <synonym>a-Ethylbenzeneacetic acid</synonym>
    <synonym>a-Ethylphenylacetate</synonym>
    <synonym>a-Ethylphenylacetic acid</synonym>
    <synonym>alpha-Ethylbenzeneacetate</synonym>
    <synonym>alpha-Ethylbenzeneacetic acid</synonym>
    <synonym>alpha-Ethylphenylacetate</synonym>
    <synonym>alpha-Ethylphenylacetic acid</synonym>
  </synonyms>
  <chemical_formula>C10H12O2</chemical_formula>
  <average_molecular_weight>164.2011</average_molecular_weight>
  <monisotopic_moleculate_weight>164.083729628</monisotopic_moleculate_weight>
  <iupac_name>2-phenylbutanoic acid</iupac_name>
  <traditional_iupac>α-phenylbutyric acid</traditional_iupac>
  <cas_registry_number>90-27-7</cas_registry_number>
  <smiles>CCC(C(O)=O)C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C10H12O2/c1-2-9(10(11)12)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,11,12)</inchi>
  <inchikey>OFJWFSNDPCAWDK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Phenylpropanes</sub_class>
    <direct_parent>Phenylpropanes</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenylpropane</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>benzenes</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>47.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>417 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-phenylbutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>164.2011</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>164.083729628</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(C(O)=O)C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12O2/c1-2-9(10(11)12)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OFJWFSNDPCAWDK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344253</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021954</foodb_id>
  <chemspider_id>6745</chemspider_id>
  <pubchem_compound_id>7012</pubchem_compound_id>
  <kegg_id/>
  <chebi_id>86545</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Sodium phenylbutyrate</wikipedia_id>
  <metlin_id>5318</metlin_id>
  <synthesis_reference>Aratake, Yuichiro; Hazama, Motoo.  Preparation of 2-phenylbutyric acids.    Jpn. Kokai Tokkyo Koho  (1998),     4 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:43 UTC</creation_date>
  <update_date>2020-04-15 22:08:54 UTC</update_date>
  <accession>BMDB0000330</accession>
  <secondary_accessions>
    <accession>BMDB00330</accession>
  </secondary_accessions>
  <name>3a,4b,12a-Trihydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>12-Ketodeoxycholate</synonym>
    <synonym>(3a,5b)-3-Hydroxy-12-oxo-cholan-24-Oate</synonym>
    <synonym>(3a,5b)-3-Hydroxy-12-oxo-cholan-24-Oic acid</synonym>
    <synonym>(3alpha,5beta)-3-Hydroxy-12-oxo-cholan-24-Oate</synonym>
    <synonym>(3alpha,5beta)-3-Hydroxy-12-oxo-cholan-24-Oic acid</synonym>
    <synonym>12-Dehydrodeoxycholate</synonym>
    <synonym>12-Dehydrodeoxycholic acid</synonym>
    <synonym>12-Ketolithocholate</synonym>
    <synonym>12-Ketolithocholic acid</synonym>
    <synonym>12-oxo-3a-Hydroxy-5b-cholanate</synonym>
    <synonym>12-oxo-3a-Hydroxy-5b-cholanic acid</synonym>
    <synonym>12-Oxolithocholate</synonym>
    <synonym>12-Oxolithocholic acid</synonym>
    <synonym>3a-Hydroxy-12-oxo-5b-cholan-24-Oate</synonym>
    <synonym>3a-Hydroxy-12-oxo-5b-cholan-24-Oic acid</synonym>
    <synonym>3a-Hydroxy-12-oxo-5b-cholanate</synonym>
    <synonym>3a-Hydroxy-12-oxo-5b-cholanic acid</synonym>
    <synonym>3a-Hydroxy-12-oxo-5b-cholanoate</synonym>
    <synonym>3a-Hydroxy-12-oxo-5b-cholanoic acid</synonym>
    <synonym>3-Hydroxy-12-ketocholanoic acid</synonym>
    <synonym>12-Ketolithocholic acid, (3beta,5beta)-isomer</synonym>
    <synonym>3 alpha-Hydroxy-12-keto-5 beta-cholanoic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-Hydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
    <synonym>3a,4b,12a-Trihydroxy-5b-cholanoate</synonym>
    <synonym>(4S)-4-[(2R,5R,6R,15R,16S)-5,6,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4S)-4-[(2R,5R,6R,15R,16S)-5,6,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4S)-4-[(2R,5R,6R,15R,16S)-5,6,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>5130-29-0</cas_registry_number>
  <smiles>C[C@@H](CCC(O)=O)C1CCC2C3CCC4[C@@H](O)[C@H](O)CC[C@]4(C)C3C[C@H](O)[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-9-21(27)28)15-7-8-16-14-5-6-17-22(29)19(25)10-11-23(17,2)18(14)12-20(26)24(15,16)3/h13-20,22,25-26,29H,4-12H2,1-3H3,(H,27,28)/t13-,14?,15?,16?,17?,18?,19+,20-,22+,23-,24+/m0/s1</inchi>
  <inchikey>FRYVQXCDSBCDAU-IQXKVUNVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Monohydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxosteroids</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-oxosteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monohydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4S)-4-[(2R,5R,6R,15R,16S)-5,6,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](CCC(O)=O)C1CCC2C3CCC4[C@@H](O)[C@H](O)CC[C@]4(C)C3C[C@H](O)[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-9-21(27)28)15-7-8-16-14-5-6-17-22(29)19(25)10-11-23(17,2)18(14)12-20(26)24(15,16)3/h13-20,22,25-26,29H,4-12H2,1-3H3,(H,27,28)/t13-,14?,15?,16?,17?,18?,19+,20-,22+,23-,24+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FRYVQXCDSBCDAU-IQXKVUNVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353496</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021953</foodb_id>
  <kegg_id/>
  <chemspider_id>2338365</chemspider_id>
  <pubchem_compound_id>3080612</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>803536</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5317</metlin_id>
  <synthesis_reference>Iida, Takashi; Momose, Toshiaki; Chang, Frederic C.; Goto, Junichi; Nambara, Toshio. Potential bile acid metabolites. XV. Synthesis of 4b-hydroxylated bile acids; unique bile acids in human fetal bile. Chemical &amp; Pharmaceutical Bulletin (1989), 37(12), 33</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:45 UTC</creation_date>
  <update_date>2020-04-15 22:13:34 UTC</update_date>
  <accession>BMDB0000331</accession>
  <secondary_accessions>
    <accession>BMDB00331</accession>
  </secondary_accessions>
  <name>3a,7b,12a-Trihydroxyoxocholanyl-Glycine</name>
  <description/>
  <synonyms>
    <synonym>2-{[(4R)-1-hydroxy-4-[(1S,2S,5R,7S,9S,10R,11S,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentylidene]amino}acetate</synonym>
    <synonym>2-{[(4R)-1-hydroxy-4-[(1S,2S,5R,7S,9S,10R,11S,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]pentylidene]amino}acetate</synonym>
  </synonyms>
  <chemical_formula>C26H43NO6</chemical_formula>
  <average_molecular_weight>465.631</average_molecular_weight>
  <monisotopic_moleculate_weight>465.309038109</monisotopic_moleculate_weight>
  <iupac_name>2-{[(4R)-1-hydroxy-4-[(1S,2S,5R,7S,9S,10R,11S,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentylidene]amino}acetic acid</iupac_name>
  <traditional_iupac>{[(4R)-1-hydroxy-4-[(1S,2S,5R,7S,9S,10R,11S,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentylidene]amino}acetic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@](C)(CCC(O)=NCC(O)=O)C1([H])CC[C@@]2([H])[C@]3([H])[C@@]([H])(O)C[C@]4([H])C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])C[C@]([H])(O)[C@]12C</smiles>
  <inchi>InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16-,17?,18+,19+,20+,21+,24+,25+,26-/m1/s1</inchi>
  <inchikey>RFDAIACWWDREDC-FSQFRIRYSA-N</inchikey>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-{[(4R)-1-hydroxy-4-[(1S,2S,5R,7S,9S,10R,11S,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentylidene]amino}acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>465.631</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>465.309038109</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](C)(CCC(O)=NCC(O)=O)C1([H])CC[C@@]2([H])[C@]3([H])[C@@]([H])(O)C[C@]4([H])C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])C[C@]([H])(O)[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H43NO6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16-,17?,18+,19+,20+,21+,24+,25+,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RFDAIACWWDREDC-FSQFRIRYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>130.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>124.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1248241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1248242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1248243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1363558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1363559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1363560</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pdbe_id/>
  <pubchem_compound_id/>
  <chebi_id/>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Dayal, B.; Rapole, K. R.; Salen, G.; Shefer, S.; Tint, G. S.; Wilson, S. R.  Microwave-induced rapid synthesis of bile acid conjugates. Synlett  (1995),   (8),  861-2. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:46 UTC</creation_date>
  <update_date>2020-04-15 20:45:46 UTC</update_date>
  <accession>BMDB0000332</accession>
  <secondary_accessions>
    <accession>BMDB00332</accession>
  </secondary_accessions>
  <name>18-Oxocortisol</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C21H28O6</chemical_formula>
  <average_molecular_weight>376.449</average_molecular_weight>
  <monisotopic_moleculate_weight>376.188588622</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10S,11S,14S,15R)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-15-carbaldehyde</iupac_name>
  <traditional_iupac>(1S,2R,10S,11S,14S,15R)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-15-carbaldehyde</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@]12CC[C@@](O)(C(=O)CO)[C@]1(CC([H])(O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C)C=O</smiles>
  <inchi>InChI=1S/C21H28O6/c1-19-6-4-13(24)8-12(19)2-3-14-15-5-7-21(27,17(26)10-22)20(15,11-23)9-16(25)18(14)19/h8,11,14-16,18,22,25,27H,2-7,9-10H2,1H3/t14-,15-,16?,18+,19-,20+,21+/m0/s1</inchi>
  <inchikey>XUQWWIFROYJHCU-MWBGJKHOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>11-hydroxysteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Aldehydes</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>11-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>18-oxosteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10S,11S,14S,15R)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-15-carbaldehyde</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>376.449</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>376.188588622</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@@](O)(C(=O)CO)[C@]1(CC([H])(O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C)C=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H28O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H28O6/c1-19-6-4-13(24)8-12(19)2-3-14-15-5-7-21(27,17(26)10-22)20(15,11-23)9-16(25)18(14)19/h8,11,14-16,18,22,25,27H,2-7,9-10H2,1H3/t14-,15-,16?,18+,19-,20+,21+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XUQWWIFROYJHCU-MWBGJKHOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>111.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>98.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>86137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1030244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1030245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1030246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1153652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1153653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1153654</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pdbe_id/>
  <pubchem_compound_id/>
  <chebi_id/>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Ulick S; Chu M D; Land M  Biosynthesis of 18-oxocortisol by aldosterone-producing adrenal tissue.    The Journal of biological chemistry  (1983),  258(9),  5498-502.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:48 UTC</creation_date>
  <update_date>2020-03-13 16:20:21 UTC</update_date>
  <accession>BMDB0000333</accession>
  <secondary_accessions>
    <accession>BMDB00333</accession>
  </secondary_accessions>
  <name>Isohomovanillic acid</name>
  <description/>
  <synonyms>
    <synonym>Homoisovanillic acid</synonym>
    <synonym>Homoisovanillate</synonym>
    <synonym>Isohomovanillate</synonym>
    <synonym>3-Hydroxy-4-methoxyphenylacetate</synonym>
    <synonym>3-Hydroxy-4-methoxyphenylacetic acid</synonym>
    <synonym>4-Methoxy-3-hydroxyphenylacetate</synonym>
    <synonym>4-Methoxy-3-hydroxyphenylacetic acid</synonym>
    <synonym>Homo-iso-vanillic acid</synonym>
  </synonyms>
  <chemical_formula>C9H10O4</chemical_formula>
  <average_molecular_weight>182.1733</average_molecular_weight>
  <monisotopic_moleculate_weight>182.057908808</monisotopic_moleculate_weight>
  <iupac_name>2-(3-hydroxy-4-methoxyphenyl)acetic acid</iupac_name>
  <traditional_iupac>isohomovanillic acid</traditional_iupac>
  <cas_registry_number>1131-94-8</cas_registry_number>
  <smiles>COC1=CC=C(CC(O)=O)C=C1O</smiles>
  <inchi>InChI=1S/C9H10O4/c1-13-8-3-2-6(4-7(8)10)5-9(11)12/h2-4,10H,5H2,1H3,(H,11,12)</inchi>
  <inchikey>BWXLCOBSWMQCGP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Methoxyphenols</sub_class>
    <direct_parent>Methoxyphenols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aromatic ether</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(3-hydroxy-4-methoxyphenyl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>182.1733</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>182.057908808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC=C(CC(O)=O)C=C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10O4/c1-13-8-3-2-6(4-7(8)10)5-9(11)12/h2-4,10H,5H2,1H3,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BWXLCOBSWMQCGP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364083</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021958</foodb_id>
  <chemspider_id>141092</chemspider_id>
  <pdbe_id/>
  <pubchem_compound_id>160562</pubchem_compound_id>
  <chebi_id>70818</chebi_id>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5322</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Harlay, Victor.  Synthesis of homoisovanillic acid. New method for the preparation of homoveratric acid.    Compt. rend.  (1946),  223  675-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:49 UTC</creation_date>
  <update_date>2020-03-13 16:20:22 UTC</update_date>
  <accession>BMDB0000335</accession>
  <secondary_accessions>
    <accession>BMDB00335</accession>
  </secondary_accessions>
  <name>16a-Hydroxyestrone</name>
  <description>16a-Hydroxyestrone, also known as 16a-hydroxyestrone or 16a-hydroxyestrone, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 16a-hydroxyestrone is considered to be a steroid lipid molecule. 16a-Hydroxyestrone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 16a-Hydroxyestrone participates in a number of enzymatic reactions, within cattle. In particular, 16a-Hydroxyestrone can be biosynthesized from estrone; which is catalyzed by the enzyme cytochrome P450 3A5. In addition, 16a-Hydroxyestrone can be converted into estriol through its interaction with the enzyme estradiol 17-beta-dehydrogenase 1. In cattle, 16a-hydroxyestrone is involved in the metabolic pathway called the estrone metabolism pathway.</description>
  <synonyms>
    <synonym>16 alpha OHE</synonym>
    <synonym>3,16alpha-Dihydroxy-1,3,5(10)-estratrien-17-one</synonym>
    <synonym>3,16alpha-Dihydroxyestra-1,3,5(10)-trien-17-one</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,16alpha-diol-17-one</synonym>
    <synonym>16 a OHE</synonym>
    <synonym>16 Α ohe</synonym>
    <synonym>3,16a-Dihydroxy-1,3,5(10)-estratrien-17-one</synonym>
    <synonym>3,16Α-dihydroxy-1,3,5(10)-estratrien-17-one</synonym>
    <synonym>3,16a-Dihydroxyestra-1,3,5(10)-trien-17-one</synonym>
    <synonym>3,16Α-dihydroxyestra-1,3,5(10)-trien-17-one</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,16a-diol-17-one</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,16α-diol-17-one</synonym>
    <synonym>16 alpha-Hydroxyestrone</synonym>
    <synonym>3,16a-Dihydroxy-estra-1,3,5(10)-trien-17-one</synonym>
    <synonym>16 beta-Hydroxyestrone</synonym>
    <synonym>16-alpha-Hydroxyestrone</synonym>
    <synonym>16-Hydroxyestrone</synonym>
  </synonyms>
  <chemical_formula>C18H22O3</chemical_formula>
  <average_molecular_weight>286.3655</average_molecular_weight>
  <monisotopic_moleculate_weight>286.15689457</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one</iupac_name>
  <traditional_iupac>(1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one</traditional_iupac>
  <cas_registry_number>566-76-7</cas_registry_number>
  <smiles>[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</smiles>
  <inchi>InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1</inchi>
  <inchikey>WPOCIZJTELRQMF-QFXBJFAPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>16-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>16-alpha-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>16alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>286.3655</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>286.15689457</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H22O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WPOCIZJTELRQMF-QFXBJFAPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>80.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1276</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.00151</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS in Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB021959</foodb_id>
  <chemspider_id>103012</chemspider_id>
  <pubchem_compound_id>115116</pubchem_compound_id>
  <kegg_id>C05300</kegg_id>
  <chebi_id>776</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>2580</metlin_id>
  <synthesis_reference>Knuppen, R.; Breuer, H.  Biogenesis of 11b-hydroxyestrone and 16a-hydroxyestrone by adrenal tissue.    Biochimica et Biophysica Acta  (1962),  58  147-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:50 UTC</creation_date>
  <update_date>2020-04-14 22:47:23 UTC</update_date>
  <accession>BMDB0000336</accession>
  <secondary_accessions>
    <accession>BMDB00336</accession>
  </secondary_accessions>
  <name>(R)-3-Hydroxyisobutyric acid</name>
  <description/>
  <synonyms>
    <synonym>(R)-3-Hydroxyisobutyrate</synonym>
    <synonym>(R)-3-Hydroxy-2-methylpropionate</synonym>
    <synonym>(R)-3-Hydroxy-2-methylpropionic acid</synonym>
    <synonym>2-Methyl-(R)-hydracrylate</synonym>
    <synonym>2-Methyl-(R)-hydracrylic acid</synonym>
    <synonym>3-Hydroxy-2-methylpropionate</synonym>
    <synonym>D-(-)-3-Hydroxyisobutyrate</synonym>
    <synonym>D-(-)-3-Hydroxyisobutyric acid</synonym>
    <synonym>D-b-Hydroxyisobutyrate</synonym>
    <synonym>D-b-Hydroxyisobutyric acid</synonym>
    <synonym>delta-(-)-3-Hydroxyisobutyrate</synonym>
    <synonym>delta-(-)-3-Hydroxyisobutyric acid</synonym>
    <synonym>delta-beta-Hydroxyisobutyrate</synonym>
    <synonym>delta-beta-Hydroxyisobutyric acid</synonym>
    <synonym>R-b-Hydroxyisobutyrate</synonym>
    <synonym>R-b-Hydroxyisobutyric acid</synonym>
    <synonym>R-beta-Hydroxyisobutyrate</synonym>
    <synonym>R-beta-Hydroxyisobutyric acid</synonym>
    <synonym>3R-Hydroxy-isobutyrate</synonym>
    <synonym>(2R)-3-Hydroxy-2-methylpropanoic acid</synonym>
    <synonym>(2R)-3-Hydroxy-2-methylpropionic acid</synonym>
    <synonym>(R)-3-Hydroxy-2-methyl-propanoic acid</synonym>
    <synonym>(R)-3-Hydroxy-2-methyl-propionic acid</synonym>
    <synonym>(R)-3-Hydroxy-2-methylpropanoic acid</synonym>
    <synonym>(±)-3-hydroxy-2-methylpropanoic acid</synonym>
    <synonym>(±)-3-hydroxy-2-methylpropionic acid</synonym>
    <synonym>2-(Hydroxymethyl)propanoic acid</synonym>
    <synonym>2-(Hydroxymethyl)propionic acid</synonym>
    <synonym>2-Methyl-3-hydroxypropanoic acid</synonym>
    <synonym>2-Methyl-3-hydroxypropionic acid</synonym>
    <synonym>3-HIBA</synonym>
    <synonym>3-Hydroxy-2-methylpropanoic acid</synonym>
    <synonym>3-Hydroxy-2-methylpropionic acid</synonym>
    <synonym>3-Hydroxyisobutyric acid</synonym>
    <synonym>D-beta-Hydroxyisobutyric acid</synonym>
    <synonym>D-Β-hydroxyisobutyric acid</synonym>
    <synonym>DL-3-Hydroxyisobutyric acid</synonym>
    <synonym>R-3-Hydroxyisobutyric acid</synonym>
    <synonym>R-Β-hydroxyisobutyric acid</synonym>
    <synonym>beta-Hydroxyisobutyric acid</synonym>
    <synonym>Β-hydroxyisobutyric acid</synonym>
    <synonym>3-Hydroxy-2-isobutyrate</synonym>
    <synonym>3-Hydroxy-2-isobutyric acid</synonym>
    <synonym>(R)-3-Hydroxyisobutyric acid</synonym>
  </synonyms>
  <chemical_formula>C4H8O3</chemical_formula>
  <average_molecular_weight>104.1045</average_molecular_weight>
  <monisotopic_moleculate_weight>104.047344122</monisotopic_moleculate_weight>
  <iupac_name>(2R)-3-hydroxy-2-methylpropanoic acid</iupac_name>
  <traditional_iupac>(R)-3-hydroxyisobutyric acid</traditional_iupac>
  <cas_registry_number>1910-47-0</cas_registry_number>
  <smiles>C[C@H](CO)C(O)=O</smiles>
  <inchi>InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1</inchi>
  <inchikey>DBXBTMSZEOQQDU-GSVOUGTGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Beta hydroxy acids and derivatives</sub_class>
    <direct_parent>Beta hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-3-hydroxy-2-methylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>104.1045</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>104.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](CO)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DBXBTMSZEOQQDU-GSVOUGTGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>23.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157634</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021960</foodb_id>
  <chemspider_id>9392288</chemspider_id>
  <pubchem_compound_id>11217234</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Sprecher, M.; Sprinson, David B.  Preparation of (R)-b-hydroxyisobutyric acid from threo-3-methyl-L-aspartate.    Journal of Biological Chemistry  (1966),  241(4),  868-71.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:51 UTC</creation_date>
  <update_date>2020-03-13 16:20:23 UTC</update_date>
  <accession>BMDB0000337</accession>
  <secondary_accessions>
    <accession>BMDB00337</accession>
  </secondary_accessions>
  <name>(S)-3,4-Dihydroxybutyric acid</name>
  <description/>
  <synonyms>
    <synonym>(S)-3,4-Dihydroxybutyrate</synonym>
    <synonym>(S)-3,4-Dihydroxy-butyric acid</synonym>
    <synonym>(S)-3,4-Dihydroxybutanoate</synonym>
    <synonym>(S)-3,4-Dihydroxybutanoic acid</synonym>
    <synonym>2-Deoxytetronate</synonym>
    <synonym>2-Deoxytetronic acid</synonym>
    <synonym>3,4-Dihydroxybutanoate</synonym>
    <synonym>3,4-Dihydroxybutanoic acid</synonym>
    <synonym>3,4-Dihydroxybutanoic acid, (S)-isomer</synonym>
    <synonym>3,4-Dihydroxybutanoic acid, monosodium salt</synonym>
  </synonyms>
  <chemical_formula>C4H8O4</chemical_formula>
  <average_molecular_weight>120.1039</average_molecular_weight>
  <monisotopic_moleculate_weight>120.042258744</monisotopic_moleculate_weight>
  <iupac_name>3,4-dihydroxybutanoic acid</iupac_name>
  <traditional_iupac>3,4-dihydroxybutanoic acid</traditional_iupac>
  <cas_registry_number>1518-61-2</cas_registry_number>
  <smiles>OCC(O)CC(O)=O</smiles>
  <inchi>InChI=1S/C4H8O4/c5-2-3(6)1-4(7)8/h3,5-6H,1-2H2,(H,7,8)</inchi>
  <inchikey>DZAIOXUZHHTJKN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Beta hydroxy acids and derivatives</sub_class>
    <direct_parent>Beta hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>omega-hydroxy fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3,4-dihydroxybutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>120.1039</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>120.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O4/c5-2-3(6)1-4(7)8/h3,5-6H,1-2H2,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DZAIOXUZHHTJKN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99565</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021961</foodb_id>
  <chemspider_id>133026</chemspider_id>
  <pdbe_id/>
  <pubchem_compound_id>150929</pubchem_compound_id>
  <chebi_id>86371</chebi_id>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Cho, Yik-haeng; Chun, Jongpil; Park, Youngmi; Roh, Kyoungrok; Yu, Hosung; Hwang, Daeil.  Process for preparing optically pure (S)-3,4-dihydroxybutyric acid derivatives.    PCT Int. Appl.  (2000),     29 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:52 UTC</creation_date>
  <update_date>2020-03-13 16:20:23 UTC</update_date>
  <accession>BMDB0000338</accession>
  <secondary_accessions>
    <accession>BMDB00338</accession>
  </secondary_accessions>
  <name>2-Hydroxyestradiol</name>
  <description/>
  <synonyms>
    <synonym>(17beta)-Estra-1,3,5(10)-triene-2,3,17-triol</synonym>
    <synonym>2-Hydroxyestradiol-17beta</synonym>
    <synonym>2-OH-e2</synonym>
    <synonym>2-OH-Estradiol</synonym>
    <synonym>(17b)-Estra-1,3,5(10)-triene-2,3,17-triol</synonym>
    <synonym>(17Β)-estra-1,3,5(10)-triene-2,3,17-triol</synonym>
    <synonym>2-Hydroxyestradiol-17b</synonym>
    <synonym>2-Hydroxyestradiol-17β</synonym>
    <synonym>(17b)-Estra-1,3, 5(10)-triene-2,3,17-triol</synonym>
    <synonym>(17beta)- Estra-1,3, 5 (10)-triene-2,3,17-triol</synonym>
    <synonym>1,3,5(10)-Estratriene-2,3,17Beta-triol</synonym>
    <synonym>17beta-2-Hydroxyestradiol</synonym>
    <synonym>2,3,17b-Trihydroxyestra-1,3,5(10)-triene</synonym>
    <synonym>2-Hydroxy-17beta-estradiol</synonym>
    <synonym>2-Hydroxy-estradiol</synonym>
    <synonym>ECS</synonym>
    <synonym>Estra-1,3,5 (10)-triene-2,3,17.beta.-triol</synonym>
    <synonym>Estra-1,3,5(10)-triene-2,3,17-beta-triol</synonym>
    <synonym>Estra-1,3,5(10)-triene-2,3,17-triol (acd/name 4.0)</synonym>
    <synonym>Estra-1,3,5(10)-triene-2,3,17b-triol</synonym>
    <synonym>Estra-1,3,5(10)-triene-2,3,17beta-triol</synonym>
    <synonym>2-Hydroxyestradiol-17 alpha</synonym>
    <synonym>2-Hydroxyestradiol-17 beta</synonym>
    <synonym>2-Hydroxyestradiol, (17alpha)-isomer</synonym>
    <synonym>2-Hydroxyestradiol, 4-(14)C-labeled</synonym>
  </synonyms>
  <chemical_formula>C18H24O3</chemical_formula>
  <average_molecular_weight>288.3814</average_molecular_weight>
  <monisotopic_moleculate_weight>288.172544634</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-4,5,14-triol</iupac_name>
  <traditional_iupac>(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-4,5,14-triol</traditional_iupac>
  <cas_registry_number>362-05-0</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3</smiles>
  <inchi>InChI=1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1</inchi>
  <inchikey>DILDHNKDVHLEQB-XSSYPUMDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>2-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17beta-hydroxy steroid</external_descriptor>
      <external_descriptor>2-hydroxy steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>Estrane and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>190 - 191 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-4,5,14-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>288.3814</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>288.172544634</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H24O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DILDHNKDVHLEQB-XSSYPUMDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>81.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1278</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021962</foodb_id>
  <chemspider_id>216475</chemspider_id>
  <drugbank_id>DB07706</drugbank_id>
  <chebi_id>28744</chebi_id>
  <pubchem_compound_id>247304</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id>C05301</kegg_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>2-Hydroxyestradiol</wikipedia_id>
  <metlin_id>5327</metlin_id>
  <synthesis_reference>Kiuru, Paula S.; Wahala, Kristiina.  Short synthesis of 2-methoxyestradiol and 2-hydroxyestradiol.    Steroids  (2003),  68(4),  373-375.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:53 UTC</creation_date>
  <update_date>2020-03-13 16:20:24 UTC</update_date>
  <accession>BMDB0000339</accession>
  <secondary_accessions>
    <accession>BMDB00339</accession>
  </secondary_accessions>
  <name>2-Methylbutyrylglycine</name>
  <description/>
  <synonyms>
    <synonym>alpha-Methylbutyrylglycine</synonym>
    <synonym>a-Methylbutyrylglycine</synonym>
    <synonym>Α-methylbutyrylglycine</synonym>
    <synonym>(2-Methyl-butyrylamino)-acetate</synonym>
    <synonym>(2-Methyl-butyrylamino)-acetic acid</synonym>
    <synonym>2-MBG</synonym>
    <synonym>2-Methylbutyryl glycine</synonym>
    <synonym>N-(2-Methylbutyryl)glycine</synonym>
    <synonym>N-Sec-valerylglycine</synonym>
    <synonym>2-Methylbutyrylglycine</synonym>
  </synonyms>
  <chemical_formula>C7H13NO3</chemical_formula>
  <average_molecular_weight>159.183</average_molecular_weight>
  <monisotopic_moleculate_weight>159.089543287</monisotopic_moleculate_weight>
  <iupac_name>2-(2-methylbutanamido)acetic acid</iupac_name>
  <traditional_iupac>2-methylbutyrylglycine</traditional_iupac>
  <cas_registry_number>52320-67-9</cas_registry_number>
  <smiles>CCC(C)C(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C7H13NO3/c1-3-5(2)7(11)8-4-6(9)10/h5H,3-4H2,1-2H3,(H,8,11)(H,9,10)</inchi>
  <inchikey>HOACIBQKYRHBOW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylglycine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(2-methylbutanamido)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>159.183</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>159.089543287</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(C)C(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H13NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H13NO3/c1-3-5(2)7(11)8-4-6(9)10/h5H,3-4H2,1-2H3,(H,8,11)(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HOACIBQKYRHBOW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352858</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352860</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021963</foodb_id>
  <chemspider_id>168243</chemspider_id>
  <drugbank_id/>
  <chebi_id>86366</chebi_id>
  <pubchem_compound_id>193872</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5328</metlin_id>
  <synthesis_reference>Korman, Stanley H.; Andresen, Brage S.; Zeharia, Avraham; Gutman, Alisa; Boneh, Avihu; Pitt, James J.  2-Ethylhydracrylic aciduria in short/branched-chain acyl-CoA dehydrogenase deficiency: application to diagnosis and implications for the R-pathway of isoleucine oxidation.    Clinical Chemistry (Washington, DC, United States)  (2005),  51(3),  610-617.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:55 UTC</creation_date>
  <update_date>2020-04-15 22:06:15 UTC</update_date>
  <accession>BMDB0000340</accession>
  <secondary_accessions>
    <accession>BMDB00340</accession>
  </secondary_accessions>
  <name>3a,7a,12a,19-Tetrahydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3a,7a,12a,19-Tetrahydroxy-5b-cholanoate</synonym>
    <synonym>3a,7a,12a,19-Tetrahydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,7a,12a,19-Tetrahydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3,7,12,19-THCA</synonym>
    <synonym>3,7,12,19-Tetrahydroxycholanoic acid</synonym>
    <synonym>(4R)-4-[(1S,2R,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-Trihydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
    <synonym>3alpha,7alpha,12alpha,19-Tetrahydroxy-5beta-cholan-24-Oic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O6</chemical_formula>
  <average_molecular_weight>424.5708</average_molecular_weight>
  <monisotopic_moleculate_weight>424.282489012</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>171524-64-4</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12CO</smiles>
  <inchi>InChI=1S/C24H40O6/c1-13(3-6-21(29)30)16-4-5-17-22-18(11-20(28)23(16,17)2)24(12-25)8-7-15(26)9-14(24)10-19(22)27/h13-20,22,25-28H,3-12H2,1-2H3,(H,29,30)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23-,24-/m1/s1</inchi>
  <inchikey>RFSKRKUKTCLIAV-OWXKUJNZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Tetrahydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>19-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.093</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>424.5708</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>424.282489012</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O6/c1-13(3-6-21(29)30)16-4-5-17-22-18(11-20(28)23(16,17)2)24(12-25)8-7-15(26)9-14(24)10-19(22)27/h13-20,22,25-28H,3-12H2,1-2H3,(H,29,30)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RFSKRKUKTCLIAV-OWXKUJNZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>112.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354960</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>4446993</chemspider_id>
  <pubchem_compound_id>5283905</pubchem_compound_id>
  <foodb_id>FDB021964</foodb_id>
  <chebi_id/>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5329</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Kurosawa, Takao; Nomura, Yukihiro; Mahara, Reijiro; Yoshimura, Teruki; Kimura, Akihiko; Ikegawa, Shigeo; Tohma, Masahiko. Synthesis of 19-hydroxylated bile acids and identification of 3a,7a,12a,19-tetrahydroxy-5b-cholan-24-oic acid in human neonatal urine. Chem Pharm Bull (Tokyo). 1995 Sep;43(9):1551-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:56 UTC</creation_date>
  <update_date>2020-03-13 16:20:25 UTC</update_date>
  <accession>BMDB0000341</accession>
  <secondary_accessions>
    <accession>BMDB00341</accession>
  </secondary_accessions>
  <name>2-Octenedioic acid</name>
  <description>2-Octenedioic acid, also known as 2-octenedioate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 2-Octenedioic acid is possibly soluble (in water) and a weakly acidic compound (based on its pKa). 2-Octenedioic acid has been linked to the inborn metabolic disorders including medium chain acyl-coa dehydrogenase deficiency.</description>
  <synonyms>
    <synonym>2-Octenedioate</synonym>
    <synonym>1-Hexene-1,6-dicarboxylate</synonym>
    <synonym>1-Hexene-1,6-dicarboxylic acid</synonym>
    <synonym>(2E)-Oct-2-enedioate</synonym>
  </synonyms>
  <chemical_formula>C8H12O4</chemical_formula>
  <average_molecular_weight>172.1785</average_molecular_weight>
  <monisotopic_moleculate_weight>172.073558872</monisotopic_moleculate_weight>
  <iupac_name>(2E)-oct-2-enedioic acid</iupac_name>
  <traditional_iupac>(E)-oct-2-enedioic acid</traditional_iupac>
  <cas_registry_number>5698-50-0</cas_registry_number>
  <smiles>OC(=O)CCCC\C=C\C(O)=O</smiles>
  <inchi>InChI=1S/C8H12O4/c9-7(10)5-3-1-2-4-6-8(11)12/h3,5H,1-2,4,6H2,(H,9,10)(H,11,12)/b5-3+</inchi>
  <inchikey>BNTPVRGYUHJFHN-HWKANZROSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-oct-2-enedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>172.1785</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>172.073558872</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCC\C=C\C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H12O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H12O4/c9-7(10)5-3-1-2-4-6-8(11)12/h3,5H,1-2,4,6H2,(H,9,10)(H,11,12)/b5-3+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BNTPVRGYUHJFHN-HWKANZROSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334919</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334920</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by UPLC-Q-TOF MS E</comment>
      <references>
        <reference>
          <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
          <pubmed_id>28342601</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB021965</foodb_id>
  <chemspider_id>4800646</chemspider_id>
  <drugbank_id/>
  <chebi_id>89192</chebi_id>
  <pubchem_compound_id>6079438</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5330</metlin_id>
  <synthesis_reference>Takada, Kenichi; Ouchi, Shiro; Mineshita, Tetsuo; Hirose, Katsumi.  Diuretic action of aliphatic unsaturated dicarboxylic acids.    Ann. Repts. Shionogi Research Lab.  (1955),  No. 5  17-24.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
      <pubmed_id>28342601</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:57 UTC</creation_date>
  <update_date>2020-03-13 16:20:25 UTC</update_date>
  <accession>BMDB0000343</accession>
  <secondary_accessions>
    <accession>BMDB00343</accession>
  </secondary_accessions>
  <name>2-Hydroxyestrone</name>
  <description>2-Hydroxyestrone belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 2-hydroxyestrone is considered to be a steroid lipid molecule. 2-Hydroxyestrone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Hydroxyestrone participates in a number of enzymatic reactions, within cattle. In particular, 2-Hydroxyestrone can be biosynthesized from estrone; which is catalyzed by the enzyme cytochrome P450 1A1. In addition, S-Adenosylmethionine and 2-hydroxyestrone can be converted into 2-methoxyestrone and S-adenosylhomocysteine through its interaction with the enzyme catechol O-methyltransferase. In cattle, 2-hydroxyestrone is involved in the metabolic pathway called the estrone metabolism pathway.</description>
  <synonyms>
    <synonym>2,3-Dihydroxyestra-1,3,5(10)-trien-17-one</synonym>
    <synonym>2-OHE1</synonym>
    <synonym>Catecholestrone</synonym>
    <synonym>2-Hydroxyestrone, 4-(14)C-labeled</synonym>
  </synonyms>
  <chemical_formula>C18H22O3</chemical_formula>
  <average_molecular_weight>286.3655</average_molecular_weight>
  <monisotopic_moleculate_weight>286.15689457</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one</iupac_name>
  <traditional_iupac>(1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one</traditional_iupac>
  <cas_registry_number>362-06-1</cas_registry_number>
  <smiles>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3</smiles>
  <inchi>InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1</inchi>
  <inchikey>SWINWPBPEKHUOD-JPVZDGGYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>17-oxosteroid</substituent>
      <substituent>2-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxy steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,15S)-4,5-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>286.3655</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>286.15689457</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H22O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SWINWPBPEKHUOD-JPVZDGGYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>81.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356481</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.000243</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.0138</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS in Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id/>
  <drugbank_id/>
  <foodb_id>FDB021966</foodb_id>
  <pubchem_compound_id/>
  <chebi_id>1156</chebi_id>
  <kegg_id>C05298</kegg_id>
  <pdbe_id/>
  <knapsack_id/>
  <wikipedia_id>2-Hydroxyestrone</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Kovacs, Katalin; Rakonczay, Z.; Matkovics, B.  Steroids.  XXIII.  Synthesis of 2- and 4-hydroxy and 2,4-dihydroxy derivatives of estrone and estradiol.  Acta Physica et Chemica  (1973),  19(3),  287-90.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:58 UTC</creation_date>
  <update_date>2020-03-13 16:20:26 UTC</update_date>
  <accession>BMDB0000344</accession>
  <secondary_accessions>
    <accession>BMDB00344</accession>
  </secondary_accessions>
  <name>2-Methoxyestradiol-3-methylether</name>
  <description/>
  <synonyms>
    <synonym>2-Octenedioate</synonym>
    <synonym>1-Hexene-1,6-dicarboxylate</synonym>
    <synonym>1-Hexene-1,6-dicarboxylic acid</synonym>
    <synonym>(2E)-Oct-2-enedioate</synonym>
    <synonym>(17b)-2,3-Dimethoxy-estra-1,3,5(10)-trien-17-ol</synonym>
    <synonym>2,3-Dimethoxy-estra-1,3,5(10)-trien-17b-ol</synonym>
    <synonym>2-Hydroxy-17b-estradiol 2,3-dimethyl ether</synonym>
    <synonym>2-Hydroxyestradiol 2,3-dimethyl ether</synonym>
    <synonym>2-Methoxy-17b-estradiol 3-methyl ether</synonym>
    <synonym>2-Methoxyestradiol-3-O-methyl ether</synonym>
  </synonyms>
  <chemical_formula>C20H28O3</chemical_formula>
  <average_molecular_weight>316.4345</average_molecular_weight>
  <monisotopic_moleculate_weight>316.203844762</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,14S,15S)-4,5-dimethoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-ol</iupac_name>
  <traditional_iupac>(1S,10R,11S,14S,15S)-4,5-dimethoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-ol</traditional_iupac>
  <cas_registry_number>5698-50-0</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(OC)=C3</smiles>
  <inchi>InChI=1S/C20H28O3/c1-20-9-8-13-14(16(20)6-7-19(20)21)5-4-12-10-17(22-2)18(23-3)11-15(12)13/h10-11,13-14,16,19,21H,4-9H2,1-3H3/t13-,14+,16-,19-,20-/m0/s1</inchi>
  <inchikey>AVCFXYYRWRZONV-BKRJIHRRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,14S,15S)-4,5-dimethoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>316.4345</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>316.203844762</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(OC)=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H28O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H28O3/c1-20-9-8-13-14(16(20)6-7-19(20)21)5-4-12-10-17(22-2)18(23-3)11-15(12)13/h10-11,13-14,16,19,21H,4-9H2,1-3H3/t13-,14+,16-,19-,20-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AVCFXYYRWRZONV-BKRJIHRRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>38.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>90.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364161</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021965</foodb_id>
  <chemspider_id>4800646</chemspider_id>
  <pubchem_compound_id>6079438</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>89192</chebi_id>
  <pdbe_id/>
  <kegg_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5330</metlin_id>
  <synthesis_reference>Rao, P. Narashimha; Axelrod, Leonard R.  2-Hydroxyestrogens. II. Synthesis of 2,3-dihydroxyestra-1,3,5(10)-trien-17-one and estra-1,3,5(10)-triene-2,3,16a,17b-tetraol.    Journal of the Chemical Society  (1961),     4769-73.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:28:59 UTC</creation_date>
  <update_date>2020-03-13 16:20:27 UTC</update_date>
  <accession>BMDB0000345</accession>
  <secondary_accessions>
    <accession>BMDB00345</accession>
  </secondary_accessions>
  <name>3-Hydroxyadipic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Hydroxyadipate</synonym>
    <synonym>(3S)-3-Hydroxyadipate</synonym>
    <synonym>(3S)-3-Hydroxyadipic acid</synonym>
    <synonym>3-Hydroxyhexanedioate</synonym>
    <synonym>3-Hydroxyhexanedioic acid</synonym>
    <synonym>3-Hydroxy-adipate</synonym>
    <synonym>3-Hydroxyadipic acid</synonym>
  </synonyms>
  <chemical_formula>C6H10O5</chemical_formula>
  <average_molecular_weight>162.1406</average_molecular_weight>
  <monisotopic_moleculate_weight>162.05282343</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxyhexanedioic acid</iupac_name>
  <traditional_iupac>3-hydroxyadipic acid</traditional_iupac>
  <cas_registry_number>14292-29-6</cas_registry_number>
  <smiles>OC(CCC(O)=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C6H10O5/c7-4(3-6(10)11)1-2-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)</inchi>
  <inchikey>YVOMYDHIQVMMTA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Medium-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Medium-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxyhexanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>162.1406</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>162.05282343</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(CCC(O)=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O5/c7-4(3-6(10)11)1-2-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YVOMYDHIQVMMTA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329880</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>133894</chemspider_id>
  <foodb_id>FDB021968</foodb_id>
  <pubchem_compound_id>151913</pubchem_compound_id>
  <drugbank_id/>
  <kegg_id/>
  <chebi_id>89205</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5334</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Chiruta, Chandramouli; Jachak, Santosh; Clive, Derrick L. J.  A convenient general method for the synthesis of hydroxy diacids.    Tetrahedron Letters  (2007),  48(18),  3141-3143.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:00 UTC</creation_date>
  <update_date>2020-03-13 16:20:27 UTC</update_date>
  <accession>BMDB0000346</accession>
  <secondary_accessions>
    <accession>BMDB00346</accession>
  </secondary_accessions>
  <name>3-Deoxyarabinohexonic acid</name>
  <description/>
  <synonyms>
    <synonym>(2S,4S,5R)-2,4,5,6-Tetrahydroxyhexanoic acid</synonym>
    <synonym>3-Deoxy-arabino-hexonic acid</synonym>
    <synonym>3-Deoxyarabino-hexonic acid</synonym>
    <synonym>(2S,4S,5R)-2,4,5,6-Tetrahydroxyhexanoate</synonym>
    <synonym>3-Deoxy-arabino-hexonate</synonym>
    <synonym>3-Deoxyarabino-hexonate</synonym>
    <synonym>3-Deoxyarabinohexonate</synonym>
    <synonym>3-Deoxy-D-arabino-hexonic acid</synonym>
    <synonym>Arabino-3-deoxyhexonate</synonym>
    <synonym>Arabino-3-deoxyhexonic acid</synonym>
    <synonym>D-2-Keto-3-deoxygluconate</synonym>
    <synonym>3-Deoxy-arabino-hexonic acid, monosodium salt, (D)-isomer</synonym>
    <synonym>3-Deoxy-arabino-hexonic acid, (D)-isomer</synonym>
    <synonym>3-Deoxy-D-arabino-hexonate</synonym>
  </synonyms>
  <chemical_formula>C6H12O6</chemical_formula>
  <average_molecular_weight>180.1559</average_molecular_weight>
  <monisotopic_moleculate_weight>180.063388116</monisotopic_moleculate_weight>
  <iupac_name>(2S,4S,5R)-2,4,5,6-tetrahydroxyhexanoic acid</iupac_name>
  <traditional_iupac>3-deoxy-arabinohexonic acid</traditional_iupac>
  <cas_registry_number>29625-79-4</cas_registry_number>
  <smiles>OC[C@@H](O)[C@@H](O)C[C@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H12O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3-5,7-10H,1-2H2,(H,11,12)/t3-,4-,5+/m0/s1</inchi>
  <inchikey>YGMNHEPVTNXLLS-VAYJURFESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Medium-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Medium-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,4S,5R)-2,4,5,6-tetrahydroxyhexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>180.1559</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>180.063388116</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)[C@@H](O)C[C@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3-5,7-10H,1-2H2,(H,11,12)/t3-,4-,5+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YGMNHEPVTNXLLS-VAYJURFESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1339</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021969</foodb_id>
  <chemspider_id>134838</chemspider_id>
  <drugbank_id>DB03303</drugbank_id>
  <chebi_id>45626</chebi_id>
  <pubchem_compound_id>152990</pubchem_compound_id>
  <pdbe_id>SSH</pdbe_id>
  <kegg_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5335</metlin_id>
  <synthesis_reference>Hanninen, Kari; Niemela, Klaus.  Alkaline degradation of peat humic acids.  Part II.  Identification of hydrophilic products.  Acta Chemica Scandinavica  (1992),  46(5),  459-63.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:02 UTC</creation_date>
  <update_date>2020-03-13 16:20:28 UTC</update_date>
  <accession>BMDB0000347</accession>
  <secondary_accessions>
    <accession>BMDB00347</accession>
  </secondary_accessions>
  <name>16b-Hydroxyestradiol</name>
  <description/>
  <synonyms>
    <synonym>16-Epiestriol</synonym>
    <synonym>16beta,17beta-Estriol</synonym>
    <synonym>Actriol</synonym>
    <synonym>Epiestriol</synonym>
    <synonym>Epiestriolum</synonym>
    <synonym>Epioestriolum</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,16beta,17-triol</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,16beta,17beta-triol</synonym>
    <synonym>16b,17b-Estriol</synonym>
    <synonym>16Β,17β-estriol</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,16b,17-triol</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,16β,17-triol</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,16b,17b-triol</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,16β,17β-triol</synonym>
    <synonym>16beta-Hydroxy-17beta-estradiol</synonym>
    <synonym>16b-Hydroxy-17b-estradiol</synonym>
    <synonym>16Β-hydroxy-17β-estradiol</synonym>
    <synonym>16-Epi-estriol</synonym>
    <synonym>16-Epiestratriol</synonym>
    <synonym>(16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol</synonym>
    <synonym>(16beta,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol</synonym>
    <synonym>16 alpha Hydroxy estradiol</synonym>
    <synonym>16-alpha-Hydroxy-estradiol</synonym>
    <synonym>16alpha,17beta Estriol</synonym>
    <synonym>16alpha,17beta-Estriol</synonym>
    <synonym>16beta Hydroxy estradiol</synonym>
    <synonym>16beta-Hydroxy-estradiol</synonym>
    <synonym>Estriol</synonym>
    <synonym>Ovestin</synonym>
    <synonym>16Β-hydroxyestradiol</synonym>
    <synonym>16b-Hydroxyestradiol</synonym>
  </synonyms>
  <chemical_formula>C18H24O3</chemical_formula>
  <average_molecular_weight>288.3814</average_molecular_weight>
  <monisotopic_moleculate_weight>288.172544634</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,13S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol</iupac_name>
  <traditional_iupac>(1S,10R,11S,13S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol</traditional_iupac>
  <cas_registry_number>547-81-9</cas_registry_number>
  <smiles>[H][C@@]12C[C@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</smiles>
  <inchi>InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17+,18+/m1/s1</inchi>
  <inchikey>PROQIPRRNZUXQM-ZMSHIADSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>16-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>16-beta-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>16beta-hydroxy steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>organic molecular entity</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,13S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>288.3814</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>288.172544634</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H24O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17+,18+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PROQIPRRNZUXQM-ZMSHIADSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>81.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364521</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021970</foodb_id>
  <chemspider_id>62155</chemspider_id>
  <drugbank_id/>
  <chebi_id>87620</chebi_id>
  <pubchem_compound_id>68929</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5336</metlin_id>
  <synthesis_reference>Ling, Yangzhi; Xu, Chunfang; Fang, Guofu; Liu, Weiqin.  Improved synthesis of estriol via hydroboration.    Yiyao Gongye  (1988),  19(12),  533-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:03 UTC</creation_date>
  <update_date>2020-04-15 22:13:35 UTC</update_date>
  <accession>BMDB0000348</accession>
  <secondary_accessions>
    <accession>BMDB00348</accession>
  </secondary_accessions>
  <name>3b,12a-Dihydroxy-5a-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3b,12a-Dihydroxy-5a-cholanoate</synonym>
    <synonym>3-Epi-deoxycholate</synonym>
    <synonym>3-Epi-deoxycholic acid</synonym>
    <synonym>3b,12a-Dihydroxy-(5a)-cholan-24-Oate</synonym>
    <synonym>3b,12a-Dihydroxy-(5a)-cholan-24-Oic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,5S,7S,10R,11S,14R,15R,16S)-5,16-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O4</chemical_formula>
  <average_molecular_weight>392.572</average_molecular_weight>
  <monisotopic_moleculate_weight>392.292659768</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5S,7S,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>3-epi-deoxycholate</traditional_iupac>
  <cas_registry_number>2569-04-2</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17+,18-,19+,20+,21+,23+,24-/m1/s1</inchi>
  <inchikey>KXGVEGMKQFWNSR-UPSXFCICSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5S,7S,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>392.572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.292659768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17+,18-,19+,20+,21+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KXGVEGMKQFWNSR-UPSXFCICSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369795</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021971</foodb_id>
  <chemspider_id>4446923</chemspider_id>
  <chebi_id/>
  <pubchem_compound_id>5283835</pubchem_compound_id>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5337</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Iqbal, Mohammed N.; Elliott, William H.  Bile acids.  LXXIX.  Synthesis and reduction of 1,4-dien-3-ones of various bile acids.    Steroids  (1989),  53(3-5),  413-25.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:04 UTC</creation_date>
  <update_date>2020-03-13 16:20:29 UTC</update_date>
  <accession>BMDB0000349</accession>
  <secondary_accessions>
    <accession>BMDB00349</accession>
  </secondary_accessions>
  <name>Erythrono-1,4-lactone</name>
  <description/>
  <synonyms>
    <synonym>D-Erythronolactone</synonym>
    <synonym>Erythronic acid gamma-lactone</synonym>
    <synonym>Erythronate g-lactone</synonym>
    <synonym>Erythronate gamma-lactone</synonym>
    <synonym>Erythronate γ-lactone</synonym>
    <synonym>Erythronic acid g-lactone</synonym>
    <synonym>Erythronic acid γ-lactone</synonym>
    <synonym>(3R,4R)-Dihydro-3,4-dihydroxy-threono-1,4-lactone 2(3H)-furanone</synonym>
    <synonym>(3R,4R)-Rel-dihydro-3,4-dihydroxy-2(3H)-furanone</synonym>
    <synonym>3,4-Dihydroxydihydro-2(3H)-furanone</synonym>
    <synonym>D-Erythronic acid gamma-lactone</synonym>
    <synonym>delta-Erythronic acid gamma-lactone</synonym>
    <synonym>Dihydro-3,4-dihydroxy-cis-2(3H)-furanone</synonym>
  </synonyms>
  <chemical_formula>C4H6O4</chemical_formula>
  <average_molecular_weight>118.088</average_molecular_weight>
  <monisotopic_moleculate_weight>118.02660868</monisotopic_moleculate_weight>
  <iupac_name>(3R,4R)-3,4-dihydroxyoxolan-2-one</iupac_name>
  <traditional_iupac>erythrono-1,4-lactone</traditional_iupac>
  <cas_registry_number>17675-99-9</cas_registry_number>
  <smiles>O[C@@H]1COC(=O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3-/m1/s1</inchi>
  <inchikey>SGMJBNSHAZVGMC-PWNYCUMCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Lactones</class>
    <sub_class>Gamma butyrolactones</sub_class>
    <direct_parent>Gamma butyrolactones</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Gamma butyrolactone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4R)-3,4-dihydroxyoxolan-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>118.088</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>118.02660868</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]1COC(=O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H6O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SGMJBNSHAZVGMC-PWNYCUMCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>22.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340239</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021972</foodb_id>
  <chemspider_id>4483398</chemspider_id>
  <chebi_id>87625</chebi_id>
  <pubchem_compound_id>5325915</pubchem_compound_id>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5338</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Isaac, I.; Aizel, G.; Stasik, I.; Wadouachi, A.; Beaupere, D.  A new efficient access to glycono 1,4-lactones by oxidation of unprotected itols by catalytic hydrogen transfer with RhH(PPh3)4-benzalacetone system.    Synlett  (1998),   (5),  475-476.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:05 UTC</creation_date>
  <update_date>2020-03-13 16:20:29 UTC</update_date>
  <accession>BMDB0000350</accession>
  <secondary_accessions>
    <accession>BMDB00350</accession>
  </secondary_accessions>
  <name>3-Hydroxysebacic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Hydroxy-decanedioic acid</synonym>
    <synonym>3-Hydroxy-sebacic acid</synonym>
    <synonym>3-Hydroxy-decanedioate</synonym>
    <synonym>3-Hydroxy-sebacate</synonym>
    <synonym>3-Hydroxysebacate</synonym>
    <synonym>3-Hydroxydecanedioate</synonym>
    <synonym>3-Hydroxydecanedioic acid</synonym>
  </synonyms>
  <chemical_formula>C10H18O5</chemical_formula>
  <average_molecular_weight>218.2469</average_molecular_weight>
  <monisotopic_moleculate_weight>218.115423686</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxydecanedioic acid</iupac_name>
  <traditional_iupac>3-hydroxysebacic acid</traditional_iupac>
  <cas_registry_number>68812-93-1</cas_registry_number>
  <smiles>OC(CCCCCCC(O)=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C10H18O5/c11-8(7-10(14)15)5-3-1-2-4-6-9(12)13/h8,11H,1-7H2,(H,12,13)(H,14,15)</inchi>
  <inchikey>OQYZCCKCJQWHIE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Medium-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Medium-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxydecanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>218.2469</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>218.115423686</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(CCCCCCC(O)=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H18O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H18O5/c11-8(7-10(14)15)5-3-1-2-4-6-9(12)13/h8,11H,1-7H2,(H,12,13)(H,14,15)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OQYZCCKCJQWHIE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>52.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343167</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021973</foodb_id>
  <chemspider_id>2285525</chemspider_id>
  <chebi_id>89182</chebi_id>
  <pubchem_compound_id>3017884</pubchem_compound_id>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5339</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Hill, Frank Friedrich.  Manufacture of 3-hydroxydicarboxylic acids. Ger. Offen.  (1986),  14 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:06 UTC</creation_date>
  <update_date>2020-03-13 16:20:30 UTC</update_date>
  <accession>BMDB0000351</accession>
  <secondary_accessions>
    <accession>BMDB00351</accession>
  </secondary_accessions>
  <name>3-Hydroxy-2-methyl-[R-(R,S)]-butanoic acid</name>
  <description/>
  <synonyms>
    <synonym>(2S,3R)-3-Hydroxy-2-methylbutanoate</synonym>
    <synonym>3-Hydroxy-2-methyl-[R-(R,S)]-butanoate</synonym>
    <synonym>3-Hydroxy-2-methyl-[R-(r*,s*)]-butanoate</synonym>
    <synonym>3-Hydroxy-2-methyl-[R-(r*,s*)]-butanoic acid</synonym>
    <synonym>(2S,3R)-3-Hydroxy-2-methylbutyric acid</synonym>
    <synonym>(2S,3R)-Nilic acid</synonym>
    <synonym>3-Hydroxy-2-methyl-[R-(R,S)]-butanoic acid</synonym>
    <synonym>HMBA</synonym>
    <synonym>(2S,3R)-3-Hydroxy-2-methylbutanoic acid</synonym>
  </synonyms>
  <chemical_formula>C5H10O3</chemical_formula>
  <average_molecular_weight>118.1311</average_molecular_weight>
  <monisotopic_moleculate_weight>118.062994186</monisotopic_moleculate_weight>
  <iupac_name>(2S,3R)-3-hydroxy-2-methylbutanoic acid</iupac_name>
  <traditional_iupac>(2S,3R)-3-hydroxy-2-methylbutanoic acid</traditional_iupac>
  <cas_registry_number>71526-30-2</cas_registry_number>
  <smiles>C[C@@H](O)[C@H](C)C(O)=O</smiles>
  <inchi>InChI=1S/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t3-,4+/m0/s1</inchi>
  <inchikey>VEXDRERIMPLZLU-IUYQGCFVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3R)-3-hydroxy-2-methylbutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>118.1311</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>118.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](O)[C@H](C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t3-,4+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VEXDRERIMPLZLU-IUYQGCFVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331329</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB021974</foodb_id>
  <drugbank_id/>
  <chemspider_id>13628066</chemspider_id>
  <pdbe_id/>
  <chebi_id/>
  <pubchem_compound_id>12313370</pubchem_compound_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5340</metlin_id>
  <synthesis_reference>Neri, Claudia; Williams, Jonathan M. J.  Racemic auxiliaries: applications to asymmetric synthesis.    Tetrahedron Letters  (2002),  43(23),  4257-4260.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:08 UTC</creation_date>
  <update_date>2020-03-13 16:20:30 UTC</update_date>
  <accession>BMDB0000352</accession>
  <secondary_accessions>
    <accession>BMDB00352</accession>
  </secondary_accessions>
  <name>16a-Hydroxydehydroisoandrosterone</name>
  <description/>
  <synonyms>
    <synonym>16alpha-Hydroxydehydroisoandrosterone</synonym>
    <synonym>3beta,16alpha-Dihydroxy-androst-5-en-17-one</synonym>
    <synonym>5-Androstene-3beta,16alpha-diol-17-one</synonym>
    <synonym>16Α-hydroxydehydroisoandrosterone</synonym>
    <synonym>3b,16a-Dihydroxy-androst-5-en-17-one</synonym>
    <synonym>3Β,16α-dihydroxy-androst-5-en-17-one</synonym>
    <synonym>5-Androstene-3b,16a-diol-17-one</synonym>
    <synonym>5-Androstene-3β,16α-diol-17-one</synonym>
    <synonym>16 alpha-Hydroxy-dehydroepiandrosterone</synonym>
    <synonym>16-Hydroxydehydroandrosterone</synonym>
    <synonym>16-Hydroxydehydroepiandrosterone</synonym>
    <synonym>16a-Hydroxy-dhea</synonym>
    <synonym>16a-Hydroxydehydroandrosterone</synonym>
    <synonym>16a-Hydroxydehydroepiandrosterone</synonym>
    <synonym>3b,16a-Dihydroxyandrost-5-en-17-one</synonym>
    <synonym>Androst-5-ene-3b-16a-diol-17-one</synonym>
    <synonym>16alpha-Hydroxy-dehydroepiandrosterone</synonym>
    <synonym>3beta,16alpha-Dihydroxyandrost-5-en-17-one</synonym>
    <synonym>16 alpha-Hydroxydehydroisoandrosterone</synonym>
    <synonym>3,16-Dihydroxyandrost-5-en-17-one</synonym>
    <synonym>3 beta,16 beta-Dihydroxyandrost-5-en-17-one</synonym>
    <synonym>16 beta-Hydroxydehydroepiandrosterone</synonym>
    <synonym>3 beta,16 alpha-Dihydroxyandrost-5-en-17-one</synonym>
    <synonym>16-Hydroxydehydroepiandrosterone, (16beta)-isomer</synonym>
    <synonym>16-Hydroxydehydroepiandrosterone, (3alpha,16alpha)-isomer</synonym>
    <synonym>16Α-hydroxydehydroepiandrosterone</synonym>
    <synonym>16a-Hydroxydehydroisoandrosterone</synonym>
  </synonyms>
  <chemical_formula>C19H28O3</chemical_formula>
  <average_molecular_weight>304.4238</average_molecular_weight>
  <monisotopic_moleculate_weight>304.203844762</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,10R,11S,13R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one</iupac_name>
  <traditional_iupac>16a-Hydroxy-DHEA</traditional_iupac>
  <cas_registry_number>1232-73-1</cas_registry_number>
  <smiles>[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,18-,19-/m0/s1</inchi>
  <inchikey>QQIVKFZWLZJXJT-DNKQKWOHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>16-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>16-alpha-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>16alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>17-oxo steroid</external_descriptor>
      <external_descriptor>3beta-hydroxy steroid</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>androstanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,10R,11S,13R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>304.4238</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>304.203844762</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H28O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QQIVKFZWLZJXJT-DNKQKWOHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>94671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>94672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>94673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158744</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021975</foodb_id>
  <chemspider_id>92168</chemspider_id>
  <chebi_id>27771</chebi_id>
  <pubchem_compound_id>102030</pubchem_compound_id>
  <kegg_id>C05139</kegg_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5341</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Siiter, Pentti K.; MacDonald, Paul C.  Placental estrogen biosynthesis during human pregnancy.    Journal of Clinical Endocrinology and Metabolism  (1966),  26(7),  751-61.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:09 UTC</creation_date>
  <update_date>2020-03-13 16:20:31 UTC</update_date>
  <accession>BMDB0000353</accession>
  <secondary_accessions>
    <accession>BMDB00353</accession>
  </secondary_accessions>
  <name>3b,15b,17a-Trihydroxy-pregnenone</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C21H32O4</chemical_formula>
  <average_molecular_weight>348.483</average_molecular_weight>
  <monisotopic_moleculate_weight>348.23005951</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,10R,11S,14R,15S)-14-ethyl-5,12,14-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-4-en-3-one</iupac_name>
  <traditional_iupac>(1S,2S,10R,11S,14R,15S)-14-ethyl-5,12,14-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-4-en-3-one</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H]C1(O)C[C@](O)(CC)[C@@]2(C)CC[C@@]3([H])[C@@]([H])(CCC4([H])CC(O)=CC(=O)[C@]34C)[C@]12[H]</smiles>
  <inchi>InChI=1S/C21H32O4/c1-4-21(25)11-16(23)18-14-6-5-12-9-13(22)10-17(24)20(12,3)15(14)7-8-19(18,21)2/h10,12,14-16,18,22-23,25H,4-9,11H2,1-3H3/t12?,14-,15+,16?,18-,19+,20+,21-/m1/s1</inchi>
  <inchikey>YXMCPINQJVUPGV-YLXYXXLNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Pregnane steroids</sub_class>
    <direct_parent>Gluco/mineralocorticoids, progestogins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Enols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxosteroids</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-oxosteroid</substituent>
      <substituent>15-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Enol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Polyol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>6.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,10R,11S,14R,15S)-14-ethyl-5,12,14-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-4-en-3-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>348.483</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>348.23005951</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]C1(O)C[C@](O)(CC)[C@@]2(C)CC[C@@]3([H])[C@@]([H])(CCC4([H])CC(O)=CC(=O)[C@]34C)[C@]12[H]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H32O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H32O4/c1-4-21(25)11-16(23)18-14-6-5-12-9-13(22)10-17(24)20(12,3)15(14)7-8-19(18,21)2/h10,12,14-16,18,22-23,25H,4-9,11H2,1-3H3/t12?,14-,15+,16?,18-,19+,20+,21-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YXMCPINQJVUPGV-YLXYXXLNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>97.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1270615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1270616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1270617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1385626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1385627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1385628</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <chebi_id/>
  <pubchem_compound_id/>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Joannou, George E.; Reeder, Anthony Y. 15b-Hydroxysteroids. (Part V). Steroids of the human perinatal period: the synthesis of 3b,15b,17a-trihydroxy-5-pregnen-20-one from 15b,17a-dihydroxy-4-pregnen-3,20-dione. Steroids (1996), 61(1), 18-21.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:10 UTC</creation_date>
  <update_date>2020-03-13 16:20:31 UTC</update_date>
  <accession>BMDB0000354</accession>
  <secondary_accessions>
    <accession>BMDB00354</accession>
  </secondary_accessions>
  <name>2-Methyl-3-hydroxybutyric acid</name>
  <description/>
  <synonyms>
    <synonym>2-Methyl-3-hydroxybutanoic acid</synonym>
    <synonym>3-Hydroxy-2-methylbutyric acid</synonym>
    <synonym>2-Methyl-3-hydroxybutanoate</synonym>
    <synonym>3-Hydroxy-2-methylbutyrate</synonym>
    <synonym>2-Methyl-3-hydroxybutyrate</synonym>
    <synonym>3-Hydroxy-2-methyl-butyrate</synonym>
    <synonym>3-Hydroxy-2-methyl-butyric acid</synonym>
    <synonym>3-Hydroxy-2-methylbutanoate</synonym>
    <synonym>3-Hydroxy-2-methylbutanoic acid</synonym>
    <synonym>a-Methyl-b-hydroxybutyrate</synonym>
    <synonym>a-Methyl-b-hydroxybutyric acid</synonym>
    <synonym>alpha-Methyl-beta-hydroxybutyrate</synonym>
    <synonym>alpha-Methyl-beta-hydroxybutyric acid</synonym>
    <synonym>Nilate</synonym>
    <synonym>Nilic acid</synonym>
    <synonym>2-Methyl-3-hydroxybutyric acid, (R-(r*,s*))-isomer</synonym>
  </synonyms>
  <chemical_formula>C5H10O3</chemical_formula>
  <average_molecular_weight>118.1311</average_molecular_weight>
  <monisotopic_moleculate_weight>118.062994186</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxy-2-methylbutanoic acid</iupac_name>
  <traditional_iupac>nilic acid</traditional_iupac>
  <cas_registry_number>473-86-9</cas_registry_number>
  <smiles>CC(O)C(C)C(O)=O</smiles>
  <inchi>InChI=1S/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)</inchi>
  <inchikey>VEXDRERIMPLZLU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxy-2-methylbutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>118.1311</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>118.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(O)C(C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VEXDRERIMPLZLU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14734</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021977</foodb_id>
  <chemspider_id>141015</chemspider_id>
  <chebi_id>37051</chebi_id>
  <pubchem_compound_id>160471</pubchem_compound_id>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>3786</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Inoue, Yoshio; Sano, Fumitaka; Nakamura, Kazuhiro; Yoshie, Naoko; Saito, Yuji; Satoh, Hiroyasu; Mino, Takashi; Matsuo, Tomonori; Doi, Yoshiharu.  Microstructure of copoly(3-hydroxyalkanoates) produced in the anaerobic-aerobic activated sludge process.  Polymer International  (1996),  39(3),  183-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:11 UTC</creation_date>
  <update_date>2020-04-14 22:47:24 UTC</update_date>
  <accession>BMDB0000355</accession>
  <secondary_accessions>
    <accession>BMDB00355</accession>
  </secondary_accessions>
  <name>3-Hydroxymethylglutaric acid</name>
  <description/>
  <synonyms>
    <synonym>3-Hydroxymethylglutarate</synonym>
    <synonym>3-Hydroxymethyl-glutarate</synonym>
  </synonyms>
  <chemical_formula>C6H10O5</chemical_formula>
  <average_molecular_weight>162.141</average_molecular_weight>
  <monisotopic_moleculate_weight>162.052823422</monisotopic_moleculate_weight>
  <iupac_name>3-(hydroxymethyl)pentanedioic acid</iupac_name>
  <traditional_iupac>3-hydroxymethylglutaric acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>OCC(CC(O)=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C6H10O5/c7-3-4(1-5(8)9)2-6(10)11/h4,7H,1-3H2,(H,8,9)(H,10,11)</inchi>
  <inchikey>IEPDKRIDROAXQP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Branched fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(hydroxymethyl)pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>162.141</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>162.052823422</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(CC(O)=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O5/c7-3-4(1-5(8)9)2-6(10)11/h4,7H,1-3H2,(H,8,9)(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IEPDKRIDROAXQP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1234597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1234598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1234599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1350082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1350083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1350084</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id>10329583</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Klosterman, Harold J.; Smith, F. The isolation of b-hydroxy-b-methylglutaric acid from the seed of flax (Linum usitatissimum). Journal of the American Chemical Society (1954), 76 1229-30.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:12 UTC</creation_date>
  <update_date>2020-03-13 16:20:33 UTC</update_date>
  <accession>BMDB0000356</accession>
  <secondary_accessions>
    <accession>BMDB00356</accession>
  </secondary_accessions>
  <name>17-Epiestriol</name>
  <description/>
  <synonyms>
    <synonym>16a,17a-Estriol</synonym>
    <synonym>16a-Hydroxy-17a-estradiol</synonym>
    <synonym>17-Epi-estriol</synonym>
    <synonym>17a-Estriol</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,16a,17a-triol</synonym>
  </synonyms>
  <chemical_formula>C18H24O3</chemical_formula>
  <average_molecular_weight>288.3814</average_molecular_weight>
  <monisotopic_moleculate_weight>288.172544634</monisotopic_moleculate_weight>
  <iupac_name>(13R,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol</iupac_name>
  <traditional_iupac>(13R,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol</traditional_iupac>
  <cas_registry_number>1228-72-4</cas_registry_number>
  <smiles>C[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1C[C@@H](O)[C@H]2O</smiles>
  <inchi>InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13?,14?,15?,16-,17-,18+/m1/s1</inchi>
  <inchikey>PROQIPRRNZUXQM-MAHASAQBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>16-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>16-alpha-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(13R,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>288.3814</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>288.172544634</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1C[C@@H](O)[C@H]2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H24O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13?,14?,15?,16-,17-,18+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PROQIPRRNZUXQM-MAHASAQBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>81.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350076</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021978</foodb_id>
  <chemspider_id>23214132</chemspider_id>
  <pubchem_compound_id>44358113</pubchem_compound_id>
  <chebi_id/>
  <kegg_id/>
  <drugbank_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>17α-Epiestriol</wikipedia_id>
  <metlin_id>5345</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Breuer, Heinz.  Isolation of 17-epiestriol from the urine of pregnant women.    Nature (London, United Kingdom)  (1960),  185  613-14.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:14 UTC</creation_date>
  <update_date>2020-04-16 20:39:05 UTC</update_date>
  <accession>BMDB0000357</accession>
  <secondary_accessions>
    <accession>BMDB00357</accession>
  </secondary_accessions>
  <name>3-Hydroxybutyric acid</name>
  <description>3-Hydroxybutyric acid, also known as 3-hydroxybutyrate or 3-hydroxybuttersaeure, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. 3-Hydroxybutyric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 3-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. 3-Hydroxybutyric acid is a potentially toxic compound. 3-Hydroxybutyric acid has been found to be associated with several diseases known as pyruvate dehydrogenase phosphatase deficiency, schizophrenia, adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency, and colorectal cancer; also 3-hydroxybutyric acid has been linked to the inborn metabolic disorders including medium chain acyl-coa dehydrogenase deficiency.</description>
  <synonyms>
    <synonym>(1)-3-Hydroxybutyric acid</synonym>
    <synonym>3 HBA</synonym>
    <synonym>3-Hydroxybuttersaeure</synonym>
    <synonym>3-OH-Butyric acid</synonym>
    <synonym>beta-Hydroxy-N-butyric acid</synonym>
    <synonym>beta-Hydroxybutanoic acid</synonym>
    <synonym>beta-Hydroxybuttersaeure</synonym>
    <synonym>beta-Hydroxybutyric acid</synonym>
    <synonym>BHBA</synonym>
    <synonym>DL-beta-Hydroxybutyric acid</synonym>
    <synonym>(1)-3-Hydroxybutyrate</synonym>
    <synonym>3-OH-Butyrate</synonym>
    <synonym>b-Hydroxy-N-butyrate</synonym>
    <synonym>b-Hydroxy-N-butyric acid</synonym>
    <synonym>beta-Hydroxy-N-butyrate</synonym>
    <synonym>Β-hydroxy-N-butyrate</synonym>
    <synonym>Β-hydroxy-N-butyric acid</synonym>
    <synonym>b-Hydroxybutanoate</synonym>
    <synonym>b-Hydroxybutanoic acid</synonym>
    <synonym>beta-Hydroxybutanoate</synonym>
    <synonym>Β-hydroxybutanoate</synonym>
    <synonym>Β-hydroxybutanoic acid</synonym>
    <synonym>b-Hydroxybuttersaeure</synonym>
    <synonym>Β-hydroxybuttersaeure</synonym>
    <synonym>b-Hydroxybutyrate</synonym>
    <synonym>b-Hydroxybutyric acid</synonym>
    <synonym>beta-Hydroxybutyrate</synonym>
    <synonym>Β-hydroxybutyrate</synonym>
    <synonym>Β-hydroxybutyric acid</synonym>
    <synonym>DL-b-Hydroxybutyrate</synonym>
    <synonym>DL-b-Hydroxybutyric acid</synonym>
    <synonym>DL-beta-Hydroxybutyrate</synonym>
    <synonym>DL-Β-hydroxybutyrate</synonym>
    <synonym>DL-Β-hydroxybutyric acid</synonym>
    <synonym>3-Hydroxybutyrate</synonym>
    <synonym>3-Hydroxy-butanoate</synonym>
    <synonym>3-Hydroxy-butanoic acid</synonym>
    <synonym>3-Hydroxy-butyrate</synonym>
    <synonym>3-Hydroxy-butyric acid</synonym>
    <synonym>3-Hydroxybutanoate</synonym>
    <synonym>3-Hydroxybutanoic acid</synonym>
    <synonym>Biopol</synonym>
    <synonym>DL-3-Hydroxybutyrate</synonym>
    <synonym>DL-3-Hydroxybutyric acid</synonym>
    <synonym>beta Hydroxybutyric acid</synonym>
    <synonym>3 Hydroxybutyric acid</synonym>
    <synonym>beta Hydroxybutyrate</synonym>
    <synonym>(+ -)-3-Hydroxybutyric acid</synonym>
    <synonym>3 Hydroxybutyrate</synonym>
  </synonyms>
  <chemical_formula>C4H8O3</chemical_formula>
  <average_molecular_weight>104.1045</average_molecular_weight>
  <monisotopic_moleculate_weight>104.047344122</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxybutanoic acid</iupac_name>
  <traditional_iupac>3 hydroxybutyrate</traditional_iupac>
  <cas_registry_number>300-85-6</cas_registry_number>
  <smiles>CC(O)CC(O)=O</smiles>
  <inchi>InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)</inchi>
  <inchikey>WHBMMWSBFZVSSR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Beta hydroxy acids and derivatives</sub_class>
    <direct_parent>Beta hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>(omega-1)-hydroxy fatty acid</external_descriptor>
      <external_descriptor>3-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
      <external_descriptor>hydroxybutyric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>46 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>444 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxybutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>104.1045</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>104.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WHBMMWSBFZVSSR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>23.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447333</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Charolais cows.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>500 +/- 30</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by ELISA</comment>
      <references>
        <reference>
          <reference_text>Abdullah BASOGLU, Nuri BASPINAR, Alparslan COSKUN. NMR-based metabolomic evaluation in dairy cows with displaced abomasum. Turk J Vet Anim Sci (2014) 38(3):325-330</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>4547 +/- 1058</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Abdullah BASOGLU, Nuri BASPINAR, Alparslan COSKUN. NMR-based metabolomic evaluation in dairy cows with displaced abomasum. Turk J Vet Anim Sci (2014) 38(3):325-330</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in lactating Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>340+/-145</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>660-950</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Cobas mira chemistry analyzer</comment>
      <references>
        <reference>
          <reference_text>Raun BM, Kristensen NB: Metabolic effects of feeding ethanol or propanol to postpartum transition Holstein cows. J Dairy Sci. 2011 May;94(5):2566-80. doi: 10.3168/jds.2010-3999.</reference_text>
          <pubmed_id>21524548</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>600-740</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Boehringer Mannheim F-kit for D-3-hydroxybutyric acid</comment>
      <references>
        <reference>
          <reference_text>Sato H, Matsumoto M, Hanasaka S: Relations between plasma acetate, 3-hydroxybutyrate, FFA, glucose levels and energy nutrition in lactating dairy cows. J Vet Med Sci. 1999 May;61(5):447-51. doi: 10.1292/jvms.61.447.</reference_text>
          <pubmed_id>10379932</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>250-2110</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Boehringer Mannheim F-kit for D-3-hydroxybutyric acid</comment>
      <references>
        <reference>
          <reference_text>Sato H: Increased blood concentration of isopropanol in ketotic dairy cows and isopropanol production from acetone in the rumen. Anim Sci J. 2009 Aug;80(4):381-6. doi: 10.1111/j.1740-0929.2009.00649.x.</reference_text>
          <pubmed_id>20163597</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>355+/-89</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>97+/-27</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>34.06 +/- 10.63</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>110 +/- 20</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Diet was fed ad libitum</comment>
      <references>
        <reference>
          <reference_text>Nielsen NI, Ingvartsen KL, Larsen T: Diurnal variation and the effect of feed restriction on plasma and milk metabolites in TMR-fed dairy cows. J Vet Med A Physiol Pathol Clin Med. 2003 Mar;50(2):88-97.</reference_text>
          <pubmed_id>12667199</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10 - 631</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Larsen T, Nielsen NI: Fluorometric determination of beta-hydroxybutyrate in milk and blood plasma. J Dairy Sci. 2005 Jun;88(6):2004-9. doi: 10.3168/jds.S0022-0302(05)72876-9.</reference_text>
          <pubmed_id>15905430</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>26 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>26 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10 - 531</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12 - 121</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from 20 healthy Holstein Friesian dairy cows </comment>
      <references>
        <reference>
          <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
          <pubmed_id>23738862</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from Danish Holstein-Friesian (n = 456) and Jersey cows (n = 436)</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
          <pubmed_id>23182357</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>69 +/- 7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Enjalbert F, Nicot MC, Bayourthe C, Moncoulon R: Ketone bodies in milk and blood of dairy cows: relationship between concentrations and utilization for detection of subclinical ketosis. J Dairy Sci. 2001 Mar;84(3):583-9. doi: 10.3168/jds.S0022-0302(01)74511-0.</reference_text>
          <pubmed_id>11286410</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28.18 +/- 2.92</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>24.63 +/- 4.75</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>114-242</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1.26+/-0.42</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1.47+/-0.39</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.86+/-0.18</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.94+/-0.26</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>88+/-33</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>101+/-23</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB021797</foodb_id>
  <chemspider_id>428</chemspider_id>
  <pubchem_compound_id>441</pubchem_compound_id>
  <chebi_id>20067</chebi_id>
  <kegg_id>C01089</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>3-hydroxybutyrate</wikipedia_id>
  <metlin_id>125</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Yang, Wenling; Ma, Peisheng; Wang, Jianing; Wang, Chunfang; Li, Haixia.  Study on the process of chemical synthesis of 3-hydroxybutyric acid.    Huaxue Gongcheng (Xi'an, China)  (2002),  30(5),  74-78.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Enjalbert F, Nicot MC, Bayourthe C, Moncoulon R: Ketone bodies in milk and blood of dairy cows: relationship between concentrations and utilization for detection of subclinical ketosis. J Dairy Sci. 2001 Mar;84(3):583-9. doi: 10.3168/jds.S0022-0302(01)74511-0.</reference_text>
      <pubmed_id>11286410</pubmed_id>
    </reference>
    <reference>
      <reference_text>Nielsen NI, Ingvartsen KL, Larsen T: Diurnal variation and the effect of feed restriction on plasma and milk metabolites in TMR-fed dairy cows. J Vet Med A Physiol Pathol Clin Med. 2003 Mar;50(2):88-97.</reference_text>
      <pubmed_id>12667199</pubmed_id>
    </reference>
    <reference>
      <reference_text>Larsen T, Nielsen NI: Fluorometric determination of beta-hydroxybutyrate in milk and blood plasma. J Dairy Sci. 2005 Jun;88(6):2004-9. doi: 10.3168/jds.S0022-0302(05)72876-9.</reference_text>
      <pubmed_id>15905430</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
      <pubmed_id>23182357</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
      <pubmed_id>23738862</pubmed_id>
    </reference>
    <reference>
      <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
      <pubmed_id>27999311</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:15 UTC</creation_date>
  <update_date>2020-03-13 16:20:34 UTC</update_date>
  <accession>BMDB0000359</accession>
  <secondary_accessions>
    <accession>BMDB00359</accession>
  </secondary_accessions>
  <name>3a,7a-Dihydroxycoprostanic acid</name>
  <description/>
  <synonyms>
    <synonym>3alpha,7alpha-Dihydroxy-5beta-cholestanate</synonym>
    <synonym>3alpha,7alpha-Dihydroxy-5beta-cholestanic acid</synonym>
    <synonym>3alpha,7alpha-Dihydroxy-5beta-cholestanoate</synonym>
    <synonym>3alpha,7alpha-Dihydroxy-5beta-cholestanoic acid</synonym>
    <synonym>3a,7a-Dihydroxy-5b-cholestanate</synonym>
    <synonym>3a,7a-Dihydroxy-5b-cholestanic acid</synonym>
    <synonym>3Α,7α-dihydroxy-5β-cholestanate</synonym>
    <synonym>3Α,7α-dihydroxy-5β-cholestanic acid</synonym>
    <synonym>3a,7a-Dihydroxy-5b-cholestanoate</synonym>
    <synonym>3a,7a-Dihydroxy-5b-cholestanoic acid</synonym>
    <synonym>3Α,7α-dihydroxy-5β-cholestanoate</synonym>
    <synonym>3Α,7α-dihydroxy-5β-cholestanoic acid</synonym>
    <synonym>3a,7a-Dihydroxycoprostanate</synonym>
    <synonym>3a,7a-Dihydroxycoprostanic acid</synonym>
    <synonym>3alpha,7alpha-Dihydroxycoprostanate</synonym>
    <synonym>3Α,7α-dihydroxycoprostanate</synonym>
    <synonym>3Α,7α-dihydroxycoprostanic acid</synonym>
    <synonym>3a,7a-Dihydroxy-5b-cholestan-26-Oate</synonym>
    <synonym>3a,7a-Dihydroxy-5b-cholestan-26-Oic acid</synonym>
    <synonym>3alpha,7alpha-Dihydroxy-5beta-cholestan-26-Oate</synonym>
    <synonym>3Α,7α-dihydroxy-5β-cholestan-26-Oate</synonym>
    <synonym>3Α,7α-dihydroxy-5β-cholestan-26-Oic acid</synonym>
    <synonym>(3Α,5β,7α)-3,7-dihydroxycholestan-26-Oic acid</synonym>
    <synonym>(3a,5b,7a)-3,7-Dihydroxycholestan-26-Oic acid</synonym>
    <synonym>(3alpha,5beta,7alpha)-3,7-Dihydroxycholestan-26-Oic acid</synonym>
    <synonym>3Α,7α-hydroxy-5β-cholestan-26-Oic acid</synonym>
    <synonym>3a,7a-Hydroxy-5β-cholestan-26-Oic acid</synonym>
    <synonym>3alpha,7alpha-Hydroxy-5β-cholestan-26-Oic acid</synonym>
    <synonym>3a,7a-Hydroxy-5b-cholestan-26-Oate</synonym>
    <synonym>3a,7a-Hydroxy-5b-cholestan-26-Oic acid</synonym>
    <synonym>3alpha,7alpha-Dihydroxy-5beta-cholestan-26-Oic acid</synonym>
    <synonym>3alpha,7alpha-Dihydroxycoprostanic acid</synonym>
  </synonyms>
  <chemical_formula>C27H46O4</chemical_formula>
  <average_molecular_weight>434.661</average_molecular_weight>
  <monisotopic_moleculate_weight>434.339609961</monisotopic_moleculate_weight>
  <iupac_name>(6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid</iupac_name>
  <traditional_iupac>(6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid</traditional_iupac>
  <cas_registry_number>17974-66-2</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O</smiles>
  <inchi>InChI=1S/C27H46O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h16-24,28-29H,5-15H2,1-4H3,(H,30,31)/t16-,17?,18+,19-,20-,21+,22+,23-,24+,26+,27-/m1/s1</inchi>
  <inchikey>ITZYGDKGRKKBSN-HKFUITGCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Steroid acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Steroid acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>7alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>C27 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>cholestanoid</external_descriptor>
      <external_descriptor>dihydroxy monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(6R)-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>434.661</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>434.339609961</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H46O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H46O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h16-24,28-29H,5-15H2,1-4H3,(H,30,31)/t16-,17?,18+,19-,20-,21+,22+,23-,24+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ITZYGDKGRKKBSN-HKFUITGCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>123.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>52.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1230220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1230221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1230222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1345762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1345763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1345764</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021979</foodb_id>
  <chemspider_id>4447327</chemspider_id>
  <pubchem_compound_id>5284239</pubchem_compound_id>
  <chebi_id>16577</chebi_id>
  <pdbe_id/>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5348</metlin_id>
  <synthesis_reference>Hanson, Russell Floyd.  Isolation, identification, formation, and metabolism of 3a, 7a-hydroxy-5b-cholestan-26-oic acid in man.    (1972),     73 pp.  CAN 78:27152  AN 1973:27152  </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:16 UTC</creation_date>
  <update_date>2020-03-13 16:20:34 UTC</update_date>
  <accession>BMDB0000360</accession>
  <secondary_accessions>
    <accession>BMDB00360</accession>
  </secondary_accessions>
  <name>2,4-Dihydroxybutanoic acid</name>
  <description/>
  <synonyms>
    <synonym>2,4-Dihydroxybutyric acid</synonym>
    <synonym>2,4-Dihydroxybutyrate</synonym>
    <synonym>2,4-Dihydroxybutanoate</synonym>
    <synonym>2,4-Dihydroxy-butyrate</synonym>
    <synonym>2,4-Dihydroxy-butyric acid</synonym>
    <synonym>3-Deoxytetronate</synonym>
    <synonym>3-Deoxytetronic acid</synonym>
    <synonym>2,4-Dihydroxy-butanoate</synonym>
  </synonyms>
  <chemical_formula>C4H8O4</chemical_formula>
  <average_molecular_weight>120.1039</average_molecular_weight>
  <monisotopic_moleculate_weight>120.042258744</monisotopic_moleculate_weight>
  <iupac_name>2,4-dihydroxybutanoic acid</iupac_name>
  <traditional_iupac>2,4-dihydroxybutyric acid</traditional_iupac>
  <cas_registry_number>1518-62-3</cas_registry_number>
  <smiles>OCCC(O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H8O4/c5-2-1-3(6)4(7)8/h3,5-6H,1-2H2,(H,7,8)</inchi>
  <inchikey>UFYGCFHQAXXBCF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Short-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Short-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
      <external_descriptor>hydroxybutyric acid</external_descriptor>
      <external_descriptor>omega-hydroxy fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,4-dihydroxybutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>120.1039</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>120.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCCC(O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O4/c5-2-1-3(6)4(7)8/h3,5-6H,1-2H2,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UFYGCFHQAXXBCF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>81405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>81406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>81407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142505</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021980</foodb_id>
  <chemspider_id>167259</chemspider_id>
  <pubchem_compound_id>192742</pubchem_compound_id>
  <chebi_id>86348</chebi_id>
  <pdbe_id/>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5349</metlin_id>
  <synthesis_reference>Radej, Z.; Kristofova, Z.  Hydroxy acid and lactone fraction of black liquor.    Papir a Celuloza  (1964),  19(6),  152-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:18 UTC</creation_date>
  <update_date>2020-04-15 22:13:36 UTC</update_date>
  <accession>BMDB0000361</accession>
  <secondary_accessions>
    <accession>BMDB00361</accession>
  </secondary_accessions>
  <name>3b,7a-Dihydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>(3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-Oic acid</synonym>
    <synonym>3-Epi-chenodeoxycholic acid</synonym>
    <synonym>3-Epichenodeoxycholic acid</synonym>
    <synonym>3beta,7alpha-Dihydroxy-5beta-cholanic acid</synonym>
    <synonym>3beta-Chenodeoxycholic acid</synonym>
    <synonym>Isochenodeoxycholic acid</synonym>
    <synonym>(3b,5b,7a)-3,7-Dihydroxycholan-24-Oate</synonym>
    <synonym>(3b,5b,7a)-3,7-Dihydroxycholan-24-Oic acid</synonym>
    <synonym>(3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-Oate</synonym>
    <synonym>(3Β,5β,7α)-3,7-dihydroxycholan-24-Oate</synonym>
    <synonym>(3Β,5β,7α)-3,7-dihydroxycholan-24-Oic acid</synonym>
    <synonym>3-Epi-chenodeoxycholate</synonym>
    <synonym>3-Epichenodeoxycholate</synonym>
    <synonym>3b,7a-Dihydroxy-5b-cholanate</synonym>
    <synonym>3b,7a-Dihydroxy-5b-cholanic acid</synonym>
    <synonym>3beta,7alpha-Dihydroxy-5beta-cholanate</synonym>
    <synonym>3Β,7α-dihydroxy-5β-cholanate</synonym>
    <synonym>3Β,7α-dihydroxy-5β-cholanic acid</synonym>
    <synonym>3b-Chenodeoxycholate</synonym>
    <synonym>3b-Chenodeoxycholic acid</synonym>
    <synonym>3beta-Chenodeoxycholate</synonym>
    <synonym>3Β-chenodeoxycholate</synonym>
    <synonym>3Β-chenodeoxycholic acid</synonym>
    <synonym>Isochenodeoxycholate</synonym>
    <synonym>3b,7a-Dihydroxy-5b-cholanoate</synonym>
    <synonym>3b,7a-Dihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3b,7a-Dihydroxy-5b-cholan-24-Oic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O4</chemical_formula>
  <average_molecular_weight>392.572</average_molecular_weight>
  <monisotopic_moleculate_weight>392.292659768</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5S,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5S,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>566-24-5</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17-,18+,19+,20-,22+,23+,24-/m1/s1</inchi>
  <inchikey>RUDATBOHQWOJDD-JGFDLHJZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>cholanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5S,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>392.572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.292659768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17-,18+,19+,20-,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RUDATBOHQWOJDD-JGFDLHJZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327585</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021981</foodb_id>
  <chemspider_id>144359</chemspider_id>
  <pubchem_compound_id>164673</pubchem_compound_id>
  <kegg_id>C17660</kegg_id>
  <chebi_id>88102</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5350</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Danielsson, Henry; Eneroth, Peter; Hellstrom, Kjell; Sjovall, Jan.  Bile acids and steroids. CXXIII. Synthesis of some 3b-hydroxylated bile acids and the isolation of 3b,12a-dihydroxy-5b-cholanic acid from feces.    Journal of Biological Chemistry  (1962),  237  3657-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:19 UTC</creation_date>
  <update_date>2020-03-13 16:20:35 UTC</update_date>
  <accession>BMDB0000362</accession>
  <secondary_accessions>
    <accession>BMDB00362</accession>
  </secondary_accessions>
  <name>2-Phosphoglyceric acid</name>
  <description>2-Phosphoglyceric acid, also known as 2-p-D-glycerate or glycerate 2-phosphate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. 2-Phosphoglyceric acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Phosphoglyceric acid exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>3-Hydroxy-2-(phosphonooxy)propanoic acid</synonym>
    <synonym>3-Hydroxy-2-(phosphonooxy)propanoate</synonym>
    <synonym>2-Phosphoglycerate</synonym>
    <synonym>2-(Dihydrogen phosphate)glycerate</synonym>
    <synonym>2-(Dihydrogen phosphate)glyceric acid</synonym>
    <synonym>2-P-D-Glycerate</synonym>
    <synonym>2-P-D-Glyceric acid</synonym>
    <synonym>2-P-Glycerate</synonym>
    <synonym>2-P-Glyceric acid</synonym>
    <synonym>2-phospho-D-Glycerate</synonym>
    <synonym>2-phospho-DL-Glyceric acid</synonym>
    <synonym>3-Hydroxy-2-phosphonooxypropanoate</synonym>
    <synonym>3-Hydroxy-2-phosphonooxypropanoic acid</synonym>
    <synonym>DL-2-Phosphoglycerate</synonym>
    <synonym>Glycerate 2-phosphate</synonym>
    <synonym>Glyceric acid 2-phosphate</synonym>
    <synonym>Phosphoglycerate</synonym>
    <synonym>2-Phosphoglycerate, (+-)-isomer</synonym>
    <synonym>2-Phosphoglycerate, (R)-isomer</synonym>
    <synonym>2-Phosphoglycerate, (S)-isomer</synonym>
    <synonym>2-Phosphoglycerate, monosodium salt</synonym>
    <synonym>2-Phospho-DL-glyceric acid</synonym>
    <synonym>2-Phosphoglyceric acid</synonym>
  </synonyms>
  <chemical_formula>C3H7O7P</chemical_formula>
  <average_molecular_weight>186.0572</average_molecular_weight>
  <monisotopic_moleculate_weight>185.99293909</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxy-2-(phosphonooxy)propanoic acid</iupac_name>
  <traditional_iupac>2-phosphoglyceric acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>OCC(OP(O)(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)</inchi>
  <inchikey>GXIURPTVHJPJLF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glyceric_acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>monophosphoglyceric acid</external_descriptor>
      <external_descriptor>tetronic acid derivative</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxy-2-(phosphonooxy)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>186.0572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>185.99293909</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(OP(O)(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GXIURPTVHJPJLF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>124.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16702</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB023161</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>59</pubchem_compound_id>
  <chebi_id>24344</chebi_id>
  <pdbe_id/>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>2-Phosphoglyceric_acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Wold, Finn.  L-Glyceric acid monophosphates.    Journal of Organic Chemistry  (1961),  26  197-9.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00455</protein_accession>
      <name>Beta-enolase</name>
      <uniprot_id>Q3ZC09</uniprot_id>
      <gene_name>ENO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00464</protein_accession>
      <name>Alpha-enolase</name>
      <uniprot_id>Q9XSJ4</uniprot_id>
      <gene_name>ENO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00491</protein_accession>
      <name>Enolase</name>
      <uniprot_id>A6QR19</uniprot_id>
      <gene_name>ENO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00919</protein_accession>
      <name>Phosphoglycerate mutase 2</name>
      <uniprot_id>Q32KV0</uniprot_id>
      <gene_name>PGAM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00920</protein_accession>
      <name>Bisphosphoglycerate mutase</name>
      <uniprot_id>Q3T014</uniprot_id>
      <gene_name>BPGM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00921</protein_accession>
      <name>Phosphoglycerate mutase 1</name>
      <uniprot_id>Q3SZ62</uniprot_id>
      <gene_name>PGAM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:20 UTC</creation_date>
  <update_date>2020-04-15 22:35:23 UTC</update_date>
  <accession>BMDB0000363</accession>
  <secondary_accessions>
    <accession>BMDB00363</accession>
  </secondary_accessions>
  <name>17a-Hydroxypregnenolone</name>
  <description>17a-17a-17a-hydroxypregnenolone belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Thus, 17a-17a-hydroxypregnenolone is considered to be a steroid lipid molecule. 17a-17a-17a-hydroxypregnenolone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 17a-17a-17a-hydroxypregnenolone participates in a number of enzymatic reactions, within cattle. In particular, 17a-17a-17a-hydroxypregnenolone can be converted into 17-hydroxyprogesterone; which is mediated by the enzyme 3-beta-HSD 1. In addition, 17a-17a-17a-hydroxypregnenolone can be biosynthesized from pregnenolone through the action of the enzyme steroid 17-alpha-hydroxylase/17,20 lyase. In cattle, 17a-17a-hydroxypregnenolone is involved in the metabolic pathway called the steroidogenesis pathway. 17a-17a-17a-hydroxypregnenolone is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(3beta)-3,17-Dihydroxypregn-5-en-20-one</synonym>
    <synonym>17-Hydroxypregnenolone</synonym>
    <synonym>5-Pregnen-3beta,17alpha-diol-20-one</synonym>
    <synonym>(3b)-3,17-Dihydroxypregn-5-en-20-one</synonym>
    <synonym>(3Β)-3,17-dihydroxypregn-5-en-20-one</synonym>
    <synonym>5-Pregnen-3b,17a-diol-20-one</synonym>
    <synonym>5-Pregnen-3β,17α-diol-20-one</synonym>
    <synonym>17-Hydroxy-D5-pregnenolone</synonym>
    <synonym>17-OH-Pregnenolone</synonym>
    <synonym>17a-Hydroxypregnolone</synonym>
    <synonym>17alpha-Hydroxypregnanolone</synonym>
    <synonym>17alpha-Hydroxypregnenolone</synonym>
    <synonym>3b,17-Dihydroxy-5-pregnen-20-one</synonym>
    <synonym>3b,17-Dihydroxy-pregn-5-en-20-one</synonym>
    <synonym>3b,17a-Dihydroxypregn-5-en-20-one</synonym>
    <synonym>17alpha Hydroxypregnenolone</synonym>
    <synonym>Hydroxypregnenolone</synonym>
    <synonym>17 Hydroxypregnenolone</synonym>
    <synonym>17 alpha Hydroxypregnenolone</synonym>
    <synonym>17-Hydroxypregnenolone, (3alpha)-isomer</synonym>
    <synonym>17-Hydroxypregnenolone, (3beta,13alpha)-isomer</synonym>
    <synonym>17-alpha-Hydroxypregnenolone</synonym>
    <synonym>17 alpha-Hydroxypregnenolone</synonym>
    <synonym>17-Hydroxypregnenolone, (3beta,13alpha,17alpha)-isomer</synonym>
    <synonym>17-Hydroxypregnenolone, (3beta,17alpha)-isomer</synonym>
  </synonyms>
  <chemical_formula>C21H32O3</chemical_formula>
  <average_molecular_weight>332.477</average_molecular_weight>
  <monisotopic_moleculate_weight>332.23514489</monisotopic_moleculate_weight>
  <iupac_name>1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one</iupac_name>
  <traditional_iupac>1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone</traditional_iupac>
  <cas_registry_number>387-79-1</cas_registry_number>
  <smiles>[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1</inchi>
  <inchikey>JERGUCIJOXJXHF-TVWVXWENSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Pregnane steroids</sub_class>
    <direct_parent>Gluco/mineralocorticoids, progestogins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>3beta-hydroxy steroid</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
      <external_descriptor>hydroxypregnenolone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>266 - 271 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>332.477</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>332.23514489</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H32O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JERGUCIJOXJXHF-TVWVXWENSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>95.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroidogenesis</name>
      <smpdb_id>SMP0087238</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370053</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.00022</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.00204</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS in Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB030278</foodb_id>
  <chemspider_id>82579</chemspider_id>
  <pubchem_compound_id>91451</pubchem_compound_id>
  <chebi_id>28750</chebi_id>
  <kegg_id>C05138</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>45199</bigg_id>
  <wikipedia_id>17-Hydroxypregnenolone</wikipedia_id>
  <metlin_id>5352</metlin_id>
  <meta_cyc_id>CPD66-23</meta_cyc_id>
  <synthesis_reference>Kaspar, Emanuel; Hiersemann, Wolfgang; Schenck, Martin.  Preparation from their esters of steroid alcohols that are sensitive to acids and alkali.    (1958),     DE  1028572  19580424  CAN 54:74845  AN 1960:74845    CAPLUS</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:21 UTC</creation_date>
  <update_date>2020-04-15 22:13:36 UTC</update_date>
  <accession>BMDB0000364</accession>
  <secondary_accessions>
    <accession>BMDB00364</accession>
  </secondary_accessions>
  <name>3a,6a,7b-Trihydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>(3alpha,5beta,6alpha,7beta)-3,6,7-Trihydroxycholan-24-Oic acid</synonym>
    <synonym>Omega-mca</synonym>
    <synonym>Omega-muricholic acid</synonym>
    <synonym>(3a,5b,6a,7b)-3,6,7-Trihydroxycholan-24-Oate</synonym>
    <synonym>(3a,5b,6a,7b)-3,6,7-Trihydroxycholan-24-Oic acid</synonym>
    <synonym>(3alpha,5beta,6alpha,7beta)-3,6,7-Trihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5β,6α,7β)-3,6,7-trihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5β,6α,7β)-3,6,7-trihydroxycholan-24-Oic acid</synonym>
    <synonym>Omega-muricholate</synonym>
    <synonym>3a,6a,7b-Trihydroxy-5b-cholanoate</synonym>
    <synonym>3a,6a,7b-Trihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,6a,7b-Trihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>W-Muricholate</synonym>
    <synonym>W-Muricholic acid</synonym>
    <synonym>Muricholic acid, (3alpha,5alpha,6alpha,7alpha)-isomer</synonym>
    <synonym>Muricholic acid, (3alpha,5beta,6alpha,7alpha)-isomer</synonym>
    <synonym>Trihydroxy-5 alpha-cholanoic acid</synonym>
    <synonym>3 alpha,6 alpha,7 beta-Trihydroxy-5 beta-cholanoic acid</synonym>
    <synonym>alpha-Muricholic acid</synonym>
    <synonym>Muricholic acid, (3alpha,5beta,6beta,7beta)-isomer</synonym>
    <synonym>3,6,7-Trihydroxy-5-cholanoic acid</synonym>
    <synonym>Muricholic acid, sodium salt</synonym>
    <synonym>beta-Muricholic acid</synonym>
    <synonym>Hyocholic acid</synonym>
    <synonym>Muricholic acid</synonym>
    <synonym>Muricholic acid, (3alpha,5beta,6alpha,7beta)-isomer</synonym>
    <synonym>Muricholic acid, (3alpha,5beta,6beta,7alpha)-isomer</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5R,7R,8R,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5R,7R,8R,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>6830-03-1</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)[C@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21-,22-,23-,24-/m1/s1</inchi>
  <inchikey>DKPMWHFRUGMUKF-NTPBNISXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>6-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>6-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>bile acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5R,7R,8R,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)[C@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21-,22-,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DKPMWHFRUGMUKF-NTPBNISXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365499</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021983</foodb_id>
  <chemspider_id>4446939</chemspider_id>
  <pubchem_compound_id>5283851</pubchem_compound_id>
  <chebi_id>81299</chebi_id>
  <kegg_id>C17727</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5353</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Iida, Takashi; Momose, Toshiaki; Tamura, Toshitake; Matsumoto, Taro; Chang, Frederic C.; Goto, Junichi; Nambara, Toshio. Potential bile acid metabolites. 14. Hyocholic and muricholic acid stereoisomers. Journal of Lipid Research (1989), 30(8), 1267-79.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:23 UTC</creation_date>
  <update_date>2020-04-15 20:46:24 UTC</update_date>
  <accession>BMDB0000365</accession>
  <secondary_accessions>
    <accession>BMDB00365</accession>
  </secondary_accessions>
  <name>Epiandrosterone</name>
  <description/>
  <synonyms>
    <synonym>3-Epiandrosterone</synonym>
    <synonym>3b-Androsterone</synonym>
    <synonym>3b-Hydroxy-17-oxo-5a-androstane</synonym>
    <synonym>3b-Hydroxy-5a-androstan-17-one</synonym>
    <synonym>3b-Hydroxy-5a-androstane-17-one</synonym>
    <synonym>3b-Hydroxyandrostan-17-one</synonym>
    <synonym>3b-Hydroxyetioallocholan-17-one</synonym>
    <synonym>3b-OH-5a-Androstane-17-one</synonym>
    <synonym>5a-Androstan-3b-ol-17-one</synonym>
    <synonym>5a-Androstane-3b-ol-17-one</synonym>
    <synonym>D-Epiandrosterone</synonym>
    <synonym>Epi-andosterone</synonym>
    <synonym>Epi-androsterone</synonym>
    <synonym>Iso-androsterone</synonym>
    <synonym>Isoandrosterone</synonym>
    <synonym>trans-Androsterone</synonym>
    <synonym>(3Β,5α)-3-hydroxyandrostan-17-one</synonym>
    <synonym>3Β-androsterone</synonym>
    <synonym>3Β-hydroxy-17-oxo-5α-androstane</synonym>
    <synonym>3Β-hydroxy-5α-androstan-17-one</synonym>
    <synonym>3Β-hydroxy-5α-androstane-17-one</synonym>
    <synonym>3Β-hydroxyandrostan-17-one</synonym>
    <synonym>3Β-hydroxyetioallocholan-17-one</synonym>
    <synonym>3Β-OH-5α-androstane-17-one</synonym>
    <synonym>5Α-androstan-17-one-3β-ol</synonym>
    <synonym>5Α-androstan-3β-ol-17-one</synonym>
    <synonym>5Α-androstane-3β-ol-17-one</synonym>
    <synonym>(3beta,5alpha)-3-Hydroxyandrostan-17-one</synonym>
    <synonym>3beta-Androsterone</synonym>
    <synonym>3beta-Hydroxy-17-oxo-5alpha-androstane</synonym>
    <synonym>3beta-Hydroxy-5alpha-androstan-17-one</synonym>
    <synonym>3beta-Hydroxy-5alpha-androstane-17-one</synonym>
    <synonym>3beta-Hydroxyandrostan-17-one</synonym>
    <synonym>3beta-Hydroxyetioallocholan-17-one</synonym>
    <synonym>3beta-OH-5alpha-Androstane-17-one</synonym>
    <synonym>5alpha-Androstan-17-one-3beta-ol</synonym>
    <synonym>5alpha-Androstan-3beta-ol-17-one</synonym>
    <synonym>5alpha-Androstane-3beta-ol-17-one</synonym>
  </synonyms>
  <chemical_formula>C19H30O2</chemical_formula>
  <average_molecular_weight>290.4403</average_molecular_weight>
  <monisotopic_moleculate_weight>290.224580204</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</iupac_name>
  <traditional_iupac>(1S,2S,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</traditional_iupac>
  <cas_registry_number>481-29-8</cas_registry_number>
  <smiles>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12?,13-,14-,15-,16-,18-,19-/m0/s1</inchi>
  <inchikey>QGXBDMJGAMFCBF-QRIARFFBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>178 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0202 mg/mL at 23 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>290.4403</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>290.224580204</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H30O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12?,13-,14-,15-,16-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QGXBDMJGAMFCBF-QRIARFFBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>83.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344850</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021984</foodb_id>
  <chemspider_id>9230560</chemspider_id>
  <pubchem_compound_id>11055399</pubchem_compound_id>
  <chebi_id/>
  <kegg_id>C07635</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>45201</bigg_id>
  <wikipedia_id>Epiandrosterone</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Johnson, Wm. S.; Bannister, Brian; Pappo, Raphael. Steroid total synthesis-hydrochrysene approach. VII. Metal-in-ammonia reduction of the aromatic nucleus. dl-Epiandrosterone and the lumi epimer. Journal of the American Chemical Society (1956), 78 6331-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:24 UTC</creation_date>
  <update_date>2020-03-13 16:20:37 UTC</update_date>
  <accession>BMDB0000366</accession>
  <secondary_accessions>
    <accession>BMDB00366</accession>
  </secondary_accessions>
  <name>2-Deoxyribonic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Deoxyribonate</synonym>
    <synonym>2-Deoxy-D-ribonate</synonym>
    <synonym>2-Deoxy-D-ribonic acid</synonym>
  </synonyms>
  <chemical_formula>C5H10O5</chemical_formula>
  <average_molecular_weight>150.1299</average_molecular_weight>
  <monisotopic_moleculate_weight>150.05282343</monisotopic_moleculate_weight>
  <iupac_name>(3S,4R)-3,4,5-trihydroxypentanoic acid</iupac_name>
  <traditional_iupac>(3S,4R)-3,4,5-trihydroxypentanoic acid</traditional_iupac>
  <cas_registry_number>29625-75-0</cas_registry_number>
  <smiles>OC[C@@H](O)[C@@H](O)CC(O)=O</smiles>
  <inchi>InChI=1S/C5H10O5/c6-2-4(8)3(7)1-5(9)10/h3-4,6-8H,1-2H2,(H,9,10)/t3-,4+/m0/s1</inchi>
  <inchikey>VBUWJOHKCBQXNU-IUYQGCFVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Beta hydroxy acids and derivatives</sub_class>
    <direct_parent>Beta hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>pentonic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3S,4R)-3,4,5-trihydroxypentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>150.1299</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>150.05282343</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)[C@@H](O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O5/c6-2-4(8)3(7)1-5(9)10/h3-4,6-8H,1-2H2,(H,9,10)/t3-,4+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VBUWJOHKCBQXNU-IUYQGCFVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333342</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021985</foodb_id>
  <pubchem_compound_id>11528367</pubchem_compound_id>
  <chemspider_id>9703151</chemspider_id>
  <chebi_id>86350</chebi_id>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5355</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Yang, Byung Yun; Montgomery, Rex.  Alkaline degradation of fructofuranosides.    Carbohydrate Research  (1996),  280(1),  47-57.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:25 UTC</creation_date>
  <update_date>2020-04-15 22:13:37 UTC</update_date>
  <accession>BMDB0000367</accession>
  <secondary_accessions>
    <accession>BMDB00367</accession>
  </secondary_accessions>
  <name>3a,6b,7b,12a-Tetrahydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3a,6b,7b,12a-Tetrahydroxy-5b-cholanic acid</synonym>
    <synonym>3a,6b,7b,12a-Tetrahydroxy-5b-cholanoate</synonym>
    <synonym>(4R)-4-[(1S,2R,5R,7R,8S,9R,10R,11S,14R,15R,16S)-5,8,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O6</chemical_formula>
  <average_molecular_weight>424.5708</average_molecular_weight>
  <monisotopic_moleculate_weight>424.282489012</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5R,7R,8S,9R,10R,11S,14R,15R,16S)-5,8,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5R,7R,8S,9R,10R,11S,14R,15R,16S)-5,8,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O6/c1-12(4-7-19(27)28)14-5-6-15-20-16(11-18(26)24(14,15)3)23(2)9-8-13(25)10-17(23)21(29)22(20)30/h12-18,20-22,25-26,29-30H,4-11H2,1-3H3,(H,27,28)/t12-,13-,14-,15+,16+,17+,18+,20+,21+,22-,23-,24-/m1/s1</inchi>
  <inchikey>COCMFMBNEAMQMA-KREOYVNCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gangliosides. These are lipid molecules composed of a glycosphingolipid (ceramide and saccharide) with one or more sialic acids linked on the sugar chain. They are usually oligoglycosylceramides derived from lactosylceramide and containing a sialic acid residue such as N-acetylneuraminic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Sphingolipids</class>
    <sub_class>Glycosphingolipids</sub_class>
    <direct_parent>Gangliosides</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alkyl glycosides</alternative_parent>
      <alternative_parent>C-glucuronides</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Glycosyl-N-acylsphingosines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketals</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acylneuraminic acids</alternative_parent>
      <alternative_parent>Neuraminic acids</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Oligosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl glycoside</substituent>
      <substituent>C-glucuronide</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty acyl glycoside</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Glycosyl-n-acylsphingosine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketal</substituent>
      <substituent>Ketone</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-acylneuraminic acid</substituent>
      <substituent>N-acylneuraminic acid or derivatives</substituent>
      <substituent>Neuaca2-3galb1-4glcb-cer_backbone</substituent>
      <substituent>Neuraminic acid</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Oligosaccharide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>240 - 242 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5R,7R,8S,9R,10R,11S,14R,15R,16S)-5,8,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>424.5708</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>424.282489012</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O6/c1-12(4-7-19(27)28)14-5-6-15-20-16(11-18(26)24(14,15)3)23(2)9-8-13(25)10-17(23)21(29)22(20)30/h12-18,20-22,25-26,29-30H,4-11H2,1-3H3,(H,27,28)/t12-,13-,14-,15+,16+,17+,18+,20+,21+,22-,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>COCMFMBNEAMQMA-KREOYVNCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>112.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347070</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB028655</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53481262</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Kagan, Henri B.; Jacques, Jean.  Bile acids containing hydroxyls in position 6 and 7.    Bull soc. chim. France  (1960),     871-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:26 UTC</creation_date>
  <update_date>2020-03-13 16:20:38 UTC</update_date>
  <accession>BMDB0000368</accession>
  <secondary_accessions>
    <accession>BMDB00368</accession>
  </secondary_accessions>
  <name>2(R)-Hydroxyadipic acid</name>
  <description/>
  <synonyms>
    <synonym>2(R)-Hydroxyadipate</synonym>
    <synonym>(2R)-2-Hydroxyadipate</synonym>
    <synonym>(2R)-2-Hydroxyadipic acid</synonym>
    <synonym>2-Hydroxy-(R)-hexanedioate</synonym>
    <synonym>2-Hydroxy-(R)-hexanedioic acid</synonym>
    <synonym>(R)-2-Hydroxyadipate</synonym>
  </synonyms>
  <chemical_formula>C6H10O5</chemical_formula>
  <average_molecular_weight>162.1406</average_molecular_weight>
  <monisotopic_moleculate_weight>162.05282343</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-hydroxyhexanedioic acid</iupac_name>
  <traditional_iupac>(R)-2-hydroxyadipic acid</traditional_iupac>
  <cas_registry_number>77252-44-9</cas_registry_number>
  <smiles>O[C@H](CCCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)/t4-/m1/s1</inchi>
  <inchikey>OTTXIFWBPRRYOG-SCSAIBSYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxyadipic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-hydroxyhexanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>162.1406</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>162.05282343</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H](CCCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)/t4-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OTTXIFWBPRRYOG-SCSAIBSYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354363</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021987</foodb_id>
  <pubchem_compound_id>9855559</pubchem_compound_id>
  <chemspider_id>8031259</chemspider_id>
  <chebi_id>55541</chebi_id>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5357</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Senkpeil, Richard F.; Pantaleone, David P.; Taylor, Paul P.  Production of a-hydroxy-carboxylic acids using a coupled enzyme system.    PCT Int. Appl.  (2002),     32 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:27 UTC</creation_date>
  <update_date>2020-03-13 16:20:39 UTC</update_date>
  <accession>BMDB0000369</accession>
  <secondary_accessions>
    <accession>BMDB00369</accession>
  </secondary_accessions>
  <name>3b,17b-Dihydroxyetiocholane</name>
  <description/>
  <synonyms>
    <synonym>5b-Androstan-3b,17b-diol</synonym>
    <synonym>5b-Androstane-3b,17b-diol</synonym>
  </synonyms>
  <chemical_formula>C19H32O2</chemical_formula>
  <average_molecular_weight>292.4562</average_molecular_weight>
  <monisotopic_moleculate_weight>292.240230268</monisotopic_moleculate_weight>
  <iupac_name>(2S,5S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol</iupac_name>
  <traditional_iupac>(2S,5S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol</traditional_iupac>
  <cas_registry_number>6038-31-9</cas_registry_number>
  <smiles>C[C@]12CCC3C(CCC4C[C@@H](O)CC[C@]34C)C1CC[C@@H]2O</smiles>
  <inchi>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12?,13-,14?,15?,16?,17-,18-,19-/m0/s1</inchi>
  <inchikey>CBMYJHIOYJEBSB-WTVXNACZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,5S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>292.4562</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>292.240230268</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@]12CCC3C(CCC4C[C@@H](O)CC[C@]34C)C1CC[C@@H]2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H32O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12?,13-,14?,15?,16?,17-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CBMYJHIOYJEBSB-WTVXNACZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37472</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id/>
  <foodb_id>FDB021988</foodb_id>
  <pubchem_compound_id>53477687</pubchem_compound_id>
  <kegg_id/>
  <chebi_id>36715</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5358</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Hanson, James R.; Liman, Mansur D.; Uyanik, Cavit.  The Stereochemistry of an Elimination Reaction accompanying the Hydroboration of a Steroidal Allylic Alcohol.    Journal of Chemical Research, Synopses  (1998),   (3),  126-127.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:28 UTC</creation_date>
  <update_date>2020-04-15 22:34:01 UTC</update_date>
  <accession>BMDB0000370</accession>
  <secondary_accessions>
    <accession>BMDB00370</accession>
  </secondary_accessions>
  <name>2-Amino-3-phosphonopropionic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Amino-3-phosphono-propanoic acid</synonym>
    <synonym>2-Amino-3-phosphono-propionic acid</synonym>
    <synonym>2-Amino-3-phosphopropionic acid</synonym>
    <synonym>2-Amino-3-phosprop</synonym>
    <synonym>2-AP3</synonym>
    <synonym>2-Azanyl-3-phosphono-propanoic acid</synonym>
    <synonym>Phosphonoalanine</synonym>
    <synonym>2-Amino-3-phosphono-propanoate</synonym>
    <synonym>2-Amino-3-phosphono-propionate</synonym>
    <synonym>2-Amino-3-phosphopropionate</synonym>
    <synonym>2-Azanyl-3-phosphono-propanoate</synonym>
    <synonym>2-Amino-3-phosphonopropionate</synonym>
    <synonym>1-Amino-3-(phosphohydroxy)propan-2-one</synonym>
    <synonym>1-Amino-propan-2-one-3-phosphate</synonym>
    <synonym>2-Amino-3-phosphonopropanoate</synonym>
    <synonym>2-Amino-3-phosphonopropanoic acid</synonym>
    <synonym>3-Amino-2-oxopropyl phosphate</synonym>
    <synonym>D-Alanyl-phosphate</synonym>
    <synonym>Glyphosate</synonym>
    <synonym>2-Amino-3-phosphonopropionic acid, sodium salt</synonym>
    <synonym>2-Amino-3-phosphonopropionic acid, (DL)-isomer</synonym>
    <synonym>L-AP3</synonym>
  </synonyms>
  <chemical_formula>C3H8NO5P</chemical_formula>
  <average_molecular_weight>169.0731</average_molecular_weight>
  <monisotopic_moleculate_weight>169.014008883</monisotopic_moleculate_weight>
  <iupac_name>2-amino-3-phosphonopropanoic acid</iupac_name>
  <traditional_iupac>phosphonoalanine</traditional_iupac>
  <cas_registry_number>5652-28-8</cas_registry_number>
  <smiles>NC(CP(O)(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H8NO5P/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)</inchi>
  <inchikey>LBTABPSJONFLPO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic phosphonic acids</alternative_parent>
      <alternative_parent>Organophosphorus compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organophosphonic acid</substituent>
      <substituent>Organophosphonic acid derivative</substituent>
      <substituent>Organophosphorus compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>alanine derivative</external_descriptor>
      <external_descriptor>non-proteinogenic alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-3-phosphonopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>169.0731</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>169.014008883</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CP(O)(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H8NO5P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H8NO5P/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LBTABPSJONFLPO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>120.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445701</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021989</foodb_id>
  <chemspider_id>3723</chemspider_id>
  <pubchem_compound_id>3857</pubchem_compound_id>
  <chebi_id>28388</chebi_id>
  <kegg_id>C05672</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5359</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Smith, Edward C. R.; McQuaid, Loretta A.; Paschal, Jonathan W.; DeHoniesto, Juel.  An enantioselective synthesis of D-(-)- and L-(+)-2-amino-3-phosphonopropanoic acid. Journal of Organic Chemistry  (1990),  55(14),  4472-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:30 UTC</creation_date>
  <update_date>2020-04-15 22:13:38 UTC</update_date>
  <accession>BMDB0000371</accession>
  <secondary_accessions>
    <accession>BMDB00371</accession>
  </secondary_accessions>
  <name>1,3,12-Trihydroxycholan-24-oic acid</name>
  <description/>
  <synonyms>
    <synonym>1,3,12-Trihydroxy-5b-cholanoate</synonym>
    <synonym>1,3,12-Trihydroxy-5b-cholanoic acid</synonym>
    <synonym>1,3,12-Trihydroxy-cholan-24-Oate</synonym>
    <synonym>1,3,12-Trihydroxy-cholan-24-Oic acid</synonym>
    <synonym>1,3,12-Trihydroxycholan-24-Oate</synonym>
    <synonym>1 beta,3 alpha,12 alpha-Trihydroxy-5 beta-cholanoic acid</synonym>
    <synonym>1,3,12-Trihydroxycholanoic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,10S,11S,14R,15R)-3,5,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,10S,11S,14R,15R)-3,5,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,10S,11S,14R,15R)-3,5,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)C(O)C[C@@]1([H])[C@@]2([H])CCC2CC(O)CC(O)[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-9-22(28)29)17-7-8-18-16-6-5-14-10-15(25)11-20(26)23(14,2)19(16)12-21(27)24(17,18)3/h13-21,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14?,15?,16+,17-,18+,19+,20?,21?,23+,24-/m1/s1</inchi>
  <inchikey>DAKYVYUAVGJDRK-JZBKOBKOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerophospholipids</class>
    <sub_class>Glycerophosphoglycerols</sub_class>
    <direct_parent>Phosphatidylglycerols</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Dialkyl phosphates</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diacylglycerophosphoglycerol</substituent>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dialkyl phosphate</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,10S,11S,14R,15R)-3,5,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)C(O)C[C@@]1([H])[C@@]2([H])CCC2CC(O)CC(O)[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-9-22(28)29)17-7-8-18-16-6-5-14-10-15(25)11-20(26)23(14,2)19(16)12-21(27)24(17,18)3/h13-21,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14?,15?,16+,17-,18+,19+,20?,21?,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DAKYVYUAVGJDRK-JZBKOBKOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>325906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>325907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>325908</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB027759</foodb_id>
  <kegg_id/>
  <chemspider_id/>
  <pubchem_compound_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:31 UTC</creation_date>
  <update_date>2020-04-15 22:25:44 UTC</update_date>
  <accession>BMDB0000372</accession>
  <secondary_accessions>
    <accession>BMDB00372</accession>
  </secondary_accessions>
  <name>16-Oxoestrone</name>
  <description/>
  <synonyms>
    <synonym>16-Ketoestrone</synonym>
    <synonym>3-Hydroxy-1,3,5(10)-estratriene-16,17-dione</synonym>
  </synonyms>
  <chemical_formula>C18H20O3</chemical_formula>
  <average_molecular_weight>284.3496</average_molecular_weight>
  <monisotopic_moleculate_weight>284.141244506</monisotopic_moleculate_weight>
  <iupac_name>(15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-13,14-dione</iupac_name>
  <traditional_iupac>(15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-13,14-dione</traditional_iupac>
  <cas_registry_number>1228-73-5</cas_registry_number>
  <smiles>C[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(=O)C2=O</smiles>
  <inchi>InChI=1S/C18H20O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-15,19H,2,4,6-7,9H2,1H3/t13?,14?,15?,18-/m0/s1</inchi>
  <inchikey>ANPHVANSJXDRTP-VLVBFLKRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>16-oxosteroids</alternative_parent>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>16-oxosteroid</substituent>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>231 - 235 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-5.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-13,14-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>284.3496</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>284.141244506</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@]12CCC3C(CCC4=C3C=CC(O)=C4)C1CC(=O)C2=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H20O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H20O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-15,19H,2,4,6-7,9H2,1H3/t13?,14?,15?,18-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ANPHVANSJXDRTP-VLVBFLKRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360792</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021991</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477688</pubchem_compound_id>
  <chebi_id/>
  <kegg_id>C14441</kegg_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5361</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>uffman, Max N.  16-Keto estrogens.    (1950),     US  2522178  19500912  CAN 45:6349  AN 1951:6349</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:32 UTC</creation_date>
  <update_date>2020-04-15 22:35:24 UTC</update_date>
  <accession>BMDB0000374</accession>
  <secondary_accessions>
    <accession>BMDB00374</accession>
  </secondary_accessions>
  <name>17-Hydroxyprogesterone</name>
  <description>17-17-17-hydroxyprogesterone, also known as 17-hydroxyprogesterone or 17-17-hydroxyprogesterone, belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Thus, 17-17-hydroxyprogesterone is considered to be a steroid lipid molecule. 17-17-17-hydroxyprogesterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 17-17-17-hydroxyprogesterone exists in all living organisms, ranging from bacteria to humans. 17-17-17-hydroxyprogesterone participates in a number of enzymatic reactions, within cattle. In particular, 17-17-17-hydroxyprogesterone can be converted into 21-deoxycortisol through the action of the enzyme cytochrome P450 11B1. In addition, 17-17-17-hydroxyprogesterone can be biosynthesized from progesterone through its interaction with the enzyme steroid 17-alpha-hydroxylase/17,20 lyase. In cattle, 17-17-hydroxyprogesterone is involved in the metabolic pathway called the steroidogenesis pathway. 17-17-17-hydroxyprogesterone is a potentially toxic compound.</description>
  <synonyms>
    <synonym>17-Hydroxypregn-4-en-3,20-dione</synonym>
    <synonym>17alpha-Hydroxy-4-pregnene-3,20-dione</synonym>
    <synonym>17alpha-Hydroxy-progesterone</synonym>
    <synonym>delta(4)-Pregnene-17alpha-ol-3,20-dione</synonym>
    <synonym>Hidroxiprogesterona</synonym>
    <synonym>Hydroxyprogesterone</synonym>
    <synonym>Hydroxyprogesteronum</synonym>
    <synonym>Pregn-4-ene-3,20-dione-17-ol</synonym>
    <synonym>17a-Hydroxy-4-pregnene-3,20-dione</synonym>
    <synonym>17Α-hydroxy-4-pregnene-3,20-dione</synonym>
    <synonym>17a-Hydroxy-progesterone</synonym>
    <synonym>17Α-hydroxy-progesterone</synonym>
    <synonym>delta(4)-Pregnene-17a-ol-3,20-dione</synonym>
    <synonym>Δ(4)-pregnene-17α-ol-3,20-dione</synonym>
    <synonym>Δ(4)-pregnene-17a-ol-3,20-dione</synonym>
    <synonym>17-alpha-Hydroxyprogesterone</synonym>
    <synonym>17-Hydroxypregn-4-ene-3,20-dione</synonym>
    <synonym>17-OH Progesterone</synonym>
    <synonym>17-OHP</synonym>
    <synonym>17a-Hydroxypregn-4-ene-3,20-dione</synonym>
    <synonym>17a-Hydroxyprogesterone</synonym>
    <synonym>17alpha-Hydroxyprogesterone</synonym>
    <synonym>D4-Pregnen-17a-ol-3,20-dione</synonym>
    <synonym>Gestageno</synonym>
    <synonym>Gestageno gador</synonym>
    <synonym>Pregn-4-en-17a-ol-3,20-dione</synonym>
    <synonym>Prodix</synonym>
    <synonym>Prodox</synonym>
    <synonym>17 Hydroxyprogesterone</synonym>
    <synonym>17-Hydroxyprogesterone, (17 alpha)-isomer</synonym>
    <synonym>17 alpha Hydroxyprogesterone</synonym>
    <synonym>17 alpha-Hydroxyprogesterone</synonym>
    <synonym>17-Hydroxyprogesterone, (9 beta, 10 alpha)-isomer</synonym>
  </synonyms>
  <chemical_formula>C21H30O3</chemical_formula>
  <average_molecular_weight>330.4611</average_molecular_weight>
  <monisotopic_moleculate_weight>330.219494826</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</traditional_iupac>
  <cas_registry_number>68-96-2</cas_registry_number>
  <smiles>[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1</inchi>
  <inchikey>DBPWSSGDRRHUNT-CEGNMAFCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Pregnane steroids</sub_class>
    <direct_parent>Gluco/mineralocorticoids, progestogins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
      <external_descriptor>Progestagens</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>219 - 220 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.00648 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.17</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>330.4611</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>330.219494826</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H30O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DBPWSSGDRRHUNT-CEGNMAFCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>94.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroidogenesis</name>
      <smpdb_id>SMP0087238</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451602</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>&lt;0.000675</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS in Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.000395</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB021992</foodb_id>
  <chemspider_id>6002</chemspider_id>
  <pubchem_compound_id>6238</pubchem_compound_id>
  <chebi_id>17252</chebi_id>
  <kegg_id>C01176</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>36989</bigg_id>
  <wikipedia_id>Hydroxyprogesterone</wikipedia_id>
  <metlin_id>5363</metlin_id>
  <meta_cyc_id>17-ALPHA-HYDROXYPROGESTERONE</meta_cyc_id>
  <synthesis_reference>Schneider, Carlos; Silva, Mario; Zunza, Hilda; Becerra, Jose.  Synthesis of 17.alpha.-hydroxyprogesterone from androstenedione.    Boletin de la Sociedad Chilena de Quimica  (1999),  44(2),  167-172.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00798</protein_accession>
      <name>Aldose reductase</name>
      <uniprot_id>P16116</uniprot_id>
      <gene_name>AKR1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:33 UTC</creation_date>
  <update_date>2020-03-13 16:20:42 UTC</update_date>
  <accession>BMDB0000375</accession>
  <secondary_accessions>
    <accession>BMDB00375</accession>
  </secondary_accessions>
  <name>3-(3-Hydroxyphenyl)propanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3-(3-Hydroxy-phenyl)-propanoic acid</synonym>
    <synonym>3-(3-Hydroxyphenyl)propionic acid</synonym>
    <synonym>3-(m-Hydroxyphenyl)propionic acid</synonym>
    <synonym>beta-(m-Hydroxyphenyl)propionic acid</synonym>
    <synonym>Dihydro-3-coumaric acid</synonym>
    <synonym>3-Hydroxyphenylpropanoate</synonym>
    <synonym>3-(3-Hydroxyphenyl)propanoate</synonym>
    <synonym>3-(3-Hydroxy-phenyl)-propanoate</synonym>
    <synonym>3-(3-Hydroxyphenyl)propionate</synonym>
    <synonym>3-(m-Hydroxyphenyl)propionate</synonym>
    <synonym>b-(m-Hydroxyphenyl)propionate</synonym>
    <synonym>b-(m-Hydroxyphenyl)propionic acid</synonym>
    <synonym>beta-(m-Hydroxyphenyl)propionate</synonym>
    <synonym>Β-(m-hydroxyphenyl)propionate</synonym>
    <synonym>Β-(m-hydroxyphenyl)propionic acid</synonym>
    <synonym>Dihydro-3-coumarate</synonym>
    <synonym>3-Hydroxyphenylpropanoic acid</synonym>
    <synonym>3-(3-Hydroxy-phenyl)-propionic acid</synonym>
    <synonym>3-Hydroxybenzenepropanoate</synonym>
    <synonym>3-Hydroxybenzenepropanoic acid</synonym>
    <synonym>3-Hydroxydihydrocinnamate</synonym>
    <synonym>3-Hydroxydihydrocinnamic acid</synonym>
    <synonym>3-Hydroxyhydrocinnamic acid</synonym>
    <synonym>3-Hydroxyphenylpropionate</synonym>
    <synonym>3-Hydroxyphenylpropionic acid</synonym>
    <synonym>b-(3-Hydroxyphenyl)propionate</synonym>
    <synonym>b-(3-Hydroxyphenyl)propionic acid</synonym>
    <synonym>beta-(3-Hydroxyphenyl)propionate</synonym>
    <synonym>beta-(3-Hydroxyphenyl)propionic acid</synonym>
    <synonym>Dihydro-m-coumarate</synonym>
    <synonym>Dihydro-m-coumaric acid</synonym>
    <synonym>m-Hydrocoumaric acid</synonym>
    <synonym>m-Hydroxy-hydrocinnamate</synonym>
    <synonym>m-Hydroxy-hydrocinnamic acid</synonym>
    <synonym>m-Hydroxyphenylpropionate</synonym>
    <synonym>m-Hydroxyphenylpropionic acid</synonym>
    <synonym>Dihydro-3-coumaric acid, monosodium salt</synonym>
  </synonyms>
  <chemical_formula>C9H10O3</chemical_formula>
  <average_molecular_weight>166.1739</average_molecular_weight>
  <monisotopic_moleculate_weight>166.062994186</monisotopic_moleculate_weight>
  <iupac_name>3-(3-hydroxyphenyl)propanoic acid</iupac_name>
  <traditional_iupac>3-hydroxyphenylpropionic acid</traditional_iupac>
  <cas_registry_number>621-54-5</cas_registry_number>
  <smiles>OC(=O)CCC1=CC(O)=CC=C1</smiles>
  <inchi>InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)</inchi>
  <inchikey>QVWAEZJXDYOKEH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Phenylpropanoic acids</class>
    <sub_class/>
    <direct_parent>Phenylpropanoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(3-hydroxyphenyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>166.1739</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>166.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC1=CC(O)=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QVWAEZJXDYOKEH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33250</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>89</chemspider_id>
  <foodb_id>FDB021993</foodb_id>
  <pubchem_compound_id>91</pubchem_compound_id>
  <chebi_id>1427</chebi_id>
  <phenol_explorer_compound_id/>
  <kegg_id>C11457</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id>3-HYDROXYPHENYL-PROPIONATE</meta_cyc_id>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>M-Coumaric acid</wikipedia_id>
  <metlin_id>5364</metlin_id>
  <synthesis_reference>Dombrow, M.; Linnell, W. H.  Preparation of m-hydroxyphenylpropionic acid.    Journal of Pharmacy and Pharmacology  (1952),  4  118-19.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:34 UTC</creation_date>
  <update_date>2020-04-15 22:13:40 UTC</update_date>
  <accession>BMDB0000376</accession>
  <secondary_accessions>
    <accession>BMDB00376</accession>
  </secondary_accessions>
  <name>3b,7a,12a-Trihydroxy-5a-Cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3b,7a,12a-Trihydroxy-5a-cholanoate</synonym>
    <synonym>3b,7a,12a-Trihydroxy-5a-cholan-24-Oate</synonym>
    <synonym>3b,7a,12a-Trihydroxy-5a-cholan-24-Oic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,5S,7R,9R,10R,11S,14R,15R,16S)-5,9,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5S,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5S,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>15073-87-7</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1</inchi>
  <inchikey>BHQCQFFYRZLCQQ-OJGXVJBCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5S,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHQCQFFYRZLCQQ-OJGXVJBCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358557</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>4446963</chemspider_id>
  <foodb_id>FDB021994</foodb_id>
  <pubchem_compound_id>5283875</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5365</metlin_id>
  <synthesis_reference>Iida, Takashi; Shinohara, Toshiyuki; Momose, Toshiaki; Tamura, Toshitake; Matsumoto, Taro; Nambara, Toshio; Chang, Frederic C.  Potential bile acid metabolites; 12.  Synthesis of stereoisomeric 3,7,12-trihydroxy-5a-cholanic acids and related compounds. Synthesis  (1986),   (12),  998-1004.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:36 UTC</creation_date>
  <update_date>2020-04-15 22:13:41 UTC</update_date>
  <accession>BMDB0000377</accession>
  <secondary_accessions>
    <accession>BMDB00377</accession>
  </secondary_accessions>
  <name>3a,6b,7b,12b-Tetrahydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3a,6b,7b,12b-Tetrahydroxy-5b-cholanoate</synonym>
    <synonym>(4R)-4-[(1S,2R,5R,7R,8S,9R,10R,11S,14R,15R,16R)-5,8,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O6</chemical_formula>
  <average_molecular_weight>424.5708</average_molecular_weight>
  <monisotopic_moleculate_weight>424.282489012</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5R,7R,8S,9R,10R,11S,14R,15R,16R)-5,8,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5R,7R,8S,9R,10R,11S,14R,15R,16R)-5,8,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>140852-41-1</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O6/c1-12(4-7-19(27)28)14-5-6-15-20-16(11-18(26)24(14,15)3)23(2)9-8-13(25)10-17(23)21(29)22(20)30/h12-18,20-22,25-26,29-30H,4-11H2,1-3H3,(H,27,28)/t12-,13-,14-,15+,16+,17+,18-,20+,21+,22-,23-,24-/m1/s1</inchi>
  <inchikey>COCMFMBNEAMQMA-XEGXWRQYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Tetrahydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>6-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>6-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5R,7R,8S,9R,10R,11S,14R,15R,16R)-5,8,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>424.5708</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>424.282489012</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O6/c1-12(4-7-19(27)28)14-5-6-15-20-16(11-18(26)24(14,15)3)23(2)9-8-13(25)10-17(23)21(29)22(20)30/h12-18,20-22,25-26,29-30H,4-11H2,1-3H3,(H,27,28)/t12-,13-,14-,15+,16+,17+,18-,20+,21+,22-,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>COCMFMBNEAMQMA-XEGXWRQYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>112.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351351</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021995</foodb_id>
  <chemspider_id>4446990</chemspider_id>
  <pubchem_compound_id>5283902</pubchem_compound_id>
  <chebi_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5366</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Aggarwal, Suresht K.; Batta, Ashok K.; Salen, Gerald; Shefer, Sarah. Synthesis of 3a,6b,7a,12b- and 3a,6b,7b,12b-tetrahydroxy-5b-cholanoic acids. Steroids  (1992),  57(3),  107-11.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:37 UTC</creation_date>
  <update_date>2020-04-14 22:47:24 UTC</update_date>
  <accession>BMDB0000378</accession>
  <secondary_accessions>
    <accession>BMDB00378</accession>
  </secondary_accessions>
  <name>2-Methylbutyroylcarnitine</name>
  <description>2-Methylbutyroylcarnitine belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Thus, 2-methylbutyroylcarnitine is considered to be a fatty ester lipid molecule. 2-Methylbutyroylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.</description>
  <synonyms>
    <synonym>3-[(2-Methylbutanoyl)oxy]-4-(trimethylammonio)butanoate</synonym>
    <synonym>3-[(2-Methylbutanoyl)oxy]-4-(trimethylammonio)butanoic acid</synonym>
    <synonym>(2-Methylbutyryl)carnitine</synonym>
    <synonym>L-2-Methylbutyrate (3-carboxy-2-hydroxypropyl)trimethyl-hydroxide ammonium inner salt</synonym>
    <synonym>Methylbutyroyl-carnitine</synonym>
  </synonyms>
  <chemical_formula>C12H23NO4</chemical_formula>
  <average_molecular_weight>245.3153</average_molecular_weight>
  <monisotopic_moleculate_weight>245.162708229</monisotopic_moleculate_weight>
  <iupac_name>3-[(2-methylbutanoyl)oxy]-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>2-methylbutyroylcarnitine</traditional_iupac>
  <cas_registry_number>31023-25-3</cas_registry_number>
  <smiles>CCC(C)C(=O)OC(CC([O-])=O)C[N+](C)(C)C</smiles>
  <inchi>InChI=1S/C12H23NO4/c1-6-9(2)12(16)17-10(7-11(14)15)8-13(3,4)5/h9-10H,6-8H2,1-5H3</inchi>
  <inchikey>IHCPDBBYTYJYIL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Acyl carnitines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Branched fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl-carnitine</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C5-acylcarnitine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(2-methylbutanoyl)oxy]-4-(trimethylazaniumyl)butanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>245.3153</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>245.162708229</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(C)C(=O)OC(CC([O-])=O)C[N+](C)(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H23NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H23NO4/c1-6-9(2)12(16)17-10(7-11(14)15)8-13(3,4)5/h9-10H,6-8H2,1-5H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IHCPDBBYTYJYIL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1350</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.1 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.5 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB021996</foodb_id>
  <chemspider_id>4932320</chemspider_id>
  <pubchem_compound_id>6426901</pubchem_compound_id>
  <chebi_id>73026</chebi_id>
  <kegg_id/>
  <drugbank_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5367</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Nakanishi, Toyofumi; Shimizu, Akira; Arimoto, Masao; Kanai, Michiko.  Synthesis of acylcarnitines for differential diagnosis of metabolic disorders.    Nippon Iyo Masu Supekutoru Gakkai Koenshu  (1993),  18  129-32.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
      <pubmed_id>28342601</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:38 UTC</creation_date>
  <update_date>2020-04-14 22:47:25 UTC</update_date>
  <accession>BMDB0000379</accession>
  <secondary_accessions>
    <accession>BMDB00379</accession>
  </secondary_accessions>
  <name>2-Methylcitric acid</name>
  <description>2-Methylcitric acid, also known as 2-methylcitrate, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 2-Methylcitric acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Methylcitric acid exists in all living organisms, ranging from bacteria to humans. 2-Methylcitric acid is a potentially toxic compound. 2-Methylcitric acid has been found to be associated with several diseases known as iron deficiency and crohn's disease; also 2-methylcitric acid has been linked to several inborn metabolic disorders including vitamin B12 deficiency, isovaleric acidemia, and propionic acidemia.</description>
  <synonyms>
    <synonym>2-Hydroxy-1,2,3-butanetricarboxylic acid</synonym>
    <synonym>2-Hydroxy-1,2,3-butanetricarboxylate</synonym>
    <synonym>2-Methylcitrate</synonym>
    <synonym>(2S,3S)-2-Methylcitrate</synonym>
    <synonym>2-Hydroxybutane-1,2,3-tricarboxylate</synonym>
    <synonym>2-Hydroxybutane-1,2,3-tricarboxylic acid</synonym>
    <synonym>2-Methylcitric acid, 3H-labeled</synonym>
    <synonym>3-Carboxy-3-hydroxy-2-methylpentanedioic acid</synonym>
    <synonym>Methylcitric acid</synonym>
  </synonyms>
  <chemical_formula>C7H10O7</chemical_formula>
  <average_molecular_weight>206.1501</average_molecular_weight>
  <monisotopic_moleculate_weight>206.042652674</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid</iupac_name>
  <traditional_iupac>methylcitric acid</traditional_iupac>
  <cas_registry_number>6061-96-7</cas_registry_number>
  <smiles>CC(C(O)=O)C(O)(CC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)</inchi>
  <inchikey>YNOXCRMFGMSKIJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Tricarboxylic acids and derivatives</sub_class>
    <direct_parent>Tricarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>tricarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>206.1501</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>206.042652674</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C(O)=O)C(O)(CC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H10O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YNOXCRMFGMSKIJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>132.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32938</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>500</chemspider_id>
  <foodb_id>FDB021997</foodb_id>
  <pubchem_compound_id>515</pubchem_compound_id>
  <chebi_id>30835</chebi_id>
  <phenol_explorer_compound_id/>
  <kegg_id/>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id>39369</bigg_id>
  <wikipedia_id/>
  <metlin_id>5368</metlin_id>
  <synthesis_reference>Ewering, Christian; Braemer, Christian Oliver; Steinbuechel, Alexander.  Production of 2-methylcitric acid by a recombinant Ralstonia eutropha strain.    PCT Int. Appl.  (2007),     30pp.  CODEN: PIXXD2  WO  2007101866  A2  20070913  CAN 147:363646  AN 2007:1033111</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:39 UTC</creation_date>
  <update_date>2020-03-13 16:20:44 UTC</update_date>
  <accession>BMDB0000380</accession>
  <secondary_accessions>
    <accession>BMDB00380</accession>
  </secondary_accessions>
  <name>2-Hydroxyestradiol-3-methyl ether</name>
  <description/>
  <synonyms>
    <synonym>2-Hydroxy-1,2,3-butanetricarboxylic acid</synonym>
    <synonym>2-Hydroxy-1,2,3-butanetricarboxylate</synonym>
    <synonym>2-Methylcitrate</synonym>
    <synonym>(2S,3S)-2-Methylcitrate</synonym>
    <synonym>2-Hydroxybutane-1,2,3-tricarboxylate</synonym>
    <synonym>2-Hydroxybutane-1,2,3-tricarboxylic acid</synonym>
    <synonym>2-Methylcitric acid, 3H-labeled</synonym>
    <synonym>3-Carboxy-3-hydroxy-2-methylpentanedioic acid</synonym>
    <synonym>Methylcitric acid</synonym>
    <synonym>(17b)-3-Methoxy-estra-1,3,5(10)-triene-2,17-diol</synonym>
    <synonym>2,3,17beta-Trihydroxy-1,3,5[10]-estratriene 2-methyl ether</synonym>
    <synonym>2-Hydroxy-17b-estradiol 3-methyl ether</synonym>
    <synonym>2-Hydroxy-3-methoxyestradiol</synonym>
    <synonym>2-Hydroxyestradiol 3-methyl ether</synonym>
    <synonym>2-Hydroxyestradiol-3-methylether2-hydroxy-3-methoxy-17beta-estradiol</synonym>
    <synonym>2H3MeOE2</synonym>
    <synonym>3,17beta-Dihydroxy-2-methoxy-1,3,5[10]-estratriene</synonym>
    <synonym>3-Methoxy-1,3,5[10]-estratriene-2,17beta-diol</synonym>
    <synonym>3-Methoxy-estra-1,3,5(10)-triene-2,17b-diol</synonym>
    <synonym>3-O-Methyl-2-hydroxyestradiol</synonym>
    <synonym>(17beta)-3-Methoxyestra-1(10),2,4-triene-2,17-diol</synonym>
    <synonym>2-Hydroxy-3-methoxy-17beta-estradiol</synonym>
    <synonym>(17b)-3-Methoxyestra-1(10),2,4-triene-2,17-diol</synonym>
    <synonym>(17Β)-3-methoxyestra-1(10),2,4-triene-2,17-diol</synonym>
    <synonym>2,3,17b-Trihydroxy-1,3,5[10]-estratriene 2-methyl ether</synonym>
    <synonym>2,3,17Β-trihydroxy-1,3,5[10]-estratriene 2-methyl ether</synonym>
    <synonym>2-Hydroxy-3-methoxy-17b-estradiol</synonym>
    <synonym>2-Hydroxy-3-methoxy-17β-estradiol</synonym>
    <synonym>3,17b-Dihydroxy-2-methoxy-1,3,5[10]-estratriene</synonym>
    <synonym>3,17Β-dihydroxy-2-methoxy-1,3,5[10]-estratriene</synonym>
    <synonym>3-Methoxy-1,3,5[10]-estratriene-2,17b-diol</synonym>
    <synonym>3-Methoxy-1,3,5[10]-estratriene-2,17β-diol</synonym>
    <synonym>2-OH-3-MeOE2</synonym>
  </synonyms>
  <chemical_formula>C19H26O3</chemical_formula>
  <average_molecular_weight>302.4079</average_molecular_weight>
  <monisotopic_moleculate_weight>302.188194698</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,14S,15S)-5-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-4,14-diol</iupac_name>
  <traditional_iupac>(1S,10R,11S,14S,15S)-5-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-4,14-diol</traditional_iupac>
  <cas_registry_number>6061-96-7</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(O)=C3</smiles>
  <inchi>InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-17(22-2)16(20)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1</inchi>
  <inchikey>MMKYSUOJWFKECQ-SSTWWWIQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Tricarboxylic acids and derivatives</sub_class>
    <direct_parent>Tricarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>tricarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,14S,15S)-5-methoxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-4,14-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>302.4079</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>302.188194698</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OC)C(O)=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H26O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-17(22-2)16(20)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MMKYSUOJWFKECQ-SSTWWWIQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>49.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>42789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>42790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>42791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>131190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>131191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>131192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37481</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021997</foodb_id>
  <chemspider_id>500</chemspider_id>
  <pubchem_compound_id>515</pubchem_compound_id>
  <chebi_id>30835</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id>39369</bigg_id>
  <wikipedia_id/>
  <metlin_id>5368</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Gill, Julie C.; Marples, Brian A.; Traynor, John R.  Regioselective 2-hydroxylation of 3-methoxyestra-1,3,5(10)-trienes via chromium carbonyl complexes.    Tetrahedron Letters  (1987),  28(23),  2643-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:40 UTC</creation_date>
  <update_date>2020-04-15 22:13:41 UTC</update_date>
  <accession>BMDB0000381</accession>
  <secondary_accessions>
    <accession>BMDB00381</accession>
  </secondary_accessions>
  <name>Allolithocholic acid</name>
  <description/>
  <synonyms>
    <synonym>Allolithocholate</synonym>
    <synonym>3a-Hydroxy-5a-cholan-24-Oate</synonym>
    <synonym>3a-Hydroxy-5a-cholan-24-Oic acid</synonym>
    <synonym>3a-Hydroxy-5a-cholanoate</synonym>
    <synonym>3a-Hydroxy-5a-cholanoic acid</synonym>
    <synonym>(4S)-4-[(2S,5R,15R)-5-Hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O3</chemical_formula>
  <average_molecular_weight>376.5726</average_molecular_weight>
  <monisotopic_moleculate_weight>376.297745146</monisotopic_moleculate_weight>
  <iupac_name>(4S)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>allolithocholic acid</traditional_iupac>
  <cas_registry_number>2276-94-0</cas_registry_number>
  <smiles>C[C@@H](CCC(O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16?,17+,18?,19?,20?,21?,23-,24+/m0/s1</inchi>
  <inchikey>SMEROWZSTRWXGI-IBUNROKMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Monohydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monohydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4S)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>376.5726</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>376.297745146</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](CCC(O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16?,17+,18?,19?,20?,21?,23-,24+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SMEROWZSTRWXGI-IBUNROKMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>107.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>45.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357567</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021999</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477689</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5370</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Goto, Tadashi.  Synthesis of stero-bile acids. XVIII. On the synthesis of bile acid hydroxylated at C-6 and of alloursodeoxycholic acid.    Proc. Japan Acad.  (1955),  31  466-70.  CAN 50:60337  AN 1956:60337</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:41 UTC</creation_date>
  <update_date>2020-03-13 16:20:45 UTC</update_date>
  <accession>BMDB0000382</accession>
  <secondary_accessions>
    <accession>BMDB00382</accession>
  </secondary_accessions>
  <name>3b,17a,21-Trihydroxypregnenone</name>
  <description/>
  <synonyms>
    <synonym>17,21-Dihydroxypregnenolone</synonym>
    <synonym>17a,21-Dihydroxypregnenolone</synonym>
    <synonym>3b,17a,21-Trihydroxypregn-5-en-20-one</synonym>
  </synonyms>
  <chemical_formula>C21H32O4</chemical_formula>
  <average_molecular_weight>348.4764</average_molecular_weight>
  <monisotopic_moleculate_weight>348.230059512</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,10S,11S,14S,15S)-5,14-dihydroxy-14-(2-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one</iupac_name>
  <traditional_iupac>(1S,2S,10S,11S,14S,15S)-5,14-dihydroxy-14-(2-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@]12CC[C@](O)(CCO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C</smiles>
  <inchi>InChI=1S/C21H32O4/c1-19-7-5-17-15(16(19)6-8-21(19,25)9-10-22)4-3-13-11-14(23)12-18(24)20(13,17)2/h12-13,15-17,22-23,25H,3-11H2,1-2H3/t13?,15-,16-,17-,19-,20-,21-/m0/s1</inchi>
  <inchikey>RJKJQHWLCLYSHD-DGFNXGTDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Enols</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxosteroids</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-oxosteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Enol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,10S,11S,14S,15S)-5,14-dihydroxy-14-(2-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>348.4764</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>348.230059512</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@](O)(CCO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H32O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H32O4/c1-19-7-5-17-15(16(19)6-8-21(19,25)9-10-22)4-3-13-11-14(23)12-18(24)20(13,17)2/h12-13,15-17,22-23,25H,3-11H2,1-2H3/t13?,15-,16-,17-,19-,20-,21-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RJKJQHWLCLYSHD-DGFNXGTDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>97.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344064</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022000</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id/>
  <chebi_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference>Heer, J.; Miescher, K.  Steroids. CIV. The synthesis of the dihydroxyacetone side chain in the steroid series.    Helvetica Chimica Acta  (1951),  34  359-72.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:43 UTC</creation_date>
  <update_date>2020-03-13 16:20:46 UTC</update_date>
  <accession>BMDB0000383</accession>
  <secondary_accessions>
    <accession>BMDB00383</accession>
  </secondary_accessions>
  <name>3a,17a-Dihydroxy-5b-androstane</name>
  <description/>
  <synonyms>
    <synonym>3 alpha,5 beta,7 alpha-3,7-Dihydroxyandrostan-17-one</synonym>
    <synonym>5b-Androstane-3a,17a-diol</synonym>
    <synonym>3,7-DHARN-17-one</synonym>
    <synonym>3,7-Dihydroxyandrostan-17-one, (3beta,5beta,7beta)-isomer</synonym>
    <synonym>3,7-Dihydroxyandrostan-17-one, (3beta,5alpha,7alpha)-isomer</synonym>
    <synonym>3,7-Dihydroxyandrostan-17-one</synonym>
    <synonym>3,7-Dihydroxyandrostan-17-one, (3beta,5alpha,7beta)-isomer</synonym>
    <synonym>3 alpha,7 alpha-5 beta-3,7-Dihydroxyandrostan-17-one</synonym>
  </synonyms>
  <chemical_formula>C19H32O2</chemical_formula>
  <average_molecular_weight>292.4562</average_molecular_weight>
  <monisotopic_moleculate_weight>292.240230268</monisotopic_moleculate_weight>
  <iupac_name>(2S,5R,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol</iupac_name>
  <traditional_iupac>(2S,5R,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol</traditional_iupac>
  <cas_registry_number>5856-10-0</cas_registry_number>
  <smiles>C[C@]12CCC3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@H]2O</smiles>
  <inchi>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12?,13-,14?,15?,16?,17-,18+,19+/m1/s1</inchi>
  <inchikey>CBMYJHIOYJEBSB-CRQQDORFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,5R,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>292.4562</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>292.240230268</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@]12CCC3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@H]2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H32O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12?,13-,14?,15?,16?,17-,18+,19+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CBMYJHIOYJEBSB-CRQQDORFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328815</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022001</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477690</pubchem_compound_id>
  <chebi_id>27727</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id>C07632</kegg_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5372</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Miller, A. M.; Dorfman, Ralph I.  Metabolism of the steroid hormones: Isolation of etiocholane-3(a),17(a)-diol from human urine.    Endocrinology  (1948),  42  174-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:44 UTC</creation_date>
  <update_date>2020-04-15 22:13:42 UTC</update_date>
  <accession>BMDB0000384</accession>
  <secondary_accessions>
    <accession>BMDB00384</accession>
  </secondary_accessions>
  <name>3a,7a-Dihydroxycholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3a,7a-Dihydroxycholanoate</synonym>
    <synonym>(3a,7a)-3,7-Dihydroxy-cholan-24-Oate</synonym>
    <synonym>(3a,7a)-3,7-Dihydroxy-cholan-24-Oic acid</synonym>
    <synonym>3a,7a-Dihydroxy-cholanoate</synonym>
    <synonym>3a,7a-Dihydroxy-cholanoic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O4</chemical_formula>
  <average_molecular_weight>392.572</average_molecular_weight>
  <monisotopic_moleculate_weight>392.292659768</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>3a,7a-dihydroxycholanoate</traditional_iupac>
  <cas_registry_number>30634-99-2</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15?,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1</inchi>
  <inchikey>RUDATBOHQWOJDD-BYRKYSOESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>392.572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.292659768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15?,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RUDATBOHQWOJDD-BYRKYSOESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358635</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022002</foodb_id>
  <chemspider_id>13628074</chemspider_id>
  <pubchem_compound_id>21252245</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5373</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Berner, E.; Lardon, A.; Reichstein, T.  Bile acids and related compounds. XLV. 3(a),12(a)-Dihydroxy-7-cholenic acid.    Helvetica Chimica Acta  (1947),  30  1542-53.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:45 UTC</creation_date>
  <update_date>2020-04-15 22:13:43 UTC</update_date>
  <accession>BMDB0000385</accession>
  <secondary_accessions>
    <accession>BMDB00385</accession>
  </secondary_accessions>
  <name>12a-Hydroxy-3-oxocholadienic acid</name>
  <description/>
  <synonyms>
    <synonym>12a-Hydroxy-3-oxocholadienate</synonym>
    <synonym>12a-Hydroxy-3-oxo-4,6-choladien-24-Oate</synonym>
    <synonym>12a-Hydroxy-3-oxo-4,6-choladien-24-Oic acid</synonym>
    <synonym>12a-Hydroxy-3-oxo-chola-4,6-dienate</synonym>
    <synonym>12a-Hydroxy-3-oxo-chola-4,6-dienic acid</synonym>
    <synonym>12a-Hydroxy-3-oxochola-4,6-dienate</synonym>
    <synonym>12a-Hydroxy-3-oxochola-4,6-dienic acid</synonym>
    <synonym>(4R)-4-[(2R,15R,16S)-16-Hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl]pentanoate</synonym>
    <synonym>12a-Hydroxy-3-oxocholadienic acid</synonym>
    <synonym>12alpha-Hydroxy-3-oxocholadienate</synonym>
    <synonym>12Α-hydroxy-3-oxocholadienate</synonym>
    <synonym>12Α-hydroxy-3-oxocholadienic acid</synonym>
  </synonyms>
  <chemical_formula>C24H34O4</chemical_formula>
  <average_molecular_weight>386.5244</average_molecular_weight>
  <monisotopic_moleculate_weight>386.245709576</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(2R,15R,16S)-16-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>12a-hydroxy-3-oxocholadienate</traditional_iupac>
  <cas_registry_number>13535-96-1</cas_registry_number>
  <smiles>C[C@H](CCC(O)=O)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O)[C@]12C</smiles>
  <inchi>InChI=1S/C24H34O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h5-6,12,14,17-21,26H,4,7-11,13H2,1-3H3,(H,27,28)/t14-,17?,18?,19?,20?,21+,23+,24-/m1/s1</inchi>
  <inchikey>DJVAMCYXFUWMLS-RVOJYKBWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Monohydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-oxosteroids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monohydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(2R,15R,16S)-16-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>386.5244</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>386.245709576</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](CCC(O)=O)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O)[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H34O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H34O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h5-6,12,14,17-21,26H,4,7-11,13H2,1-3H3,(H,27,28)/t14-,17?,18?,19?,20?,21+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DJVAMCYXFUWMLS-RVOJYKBWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>43.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335781</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022003</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477691</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5374</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Hayakawa, Shohei; Saburi, Yasuo; Fujii, Takao; Sonoda, Yoshiya.  Microbiological degradation of bile acids. VII. Partial synthesis of 3,12-dioxo-D4,6-choladienic acid and its derivatives from cholic acid.    Journal of Biochemistry (Tokyo, Japan)  (1956),  43  731-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:46 UTC</creation_date>
  <update_date>2020-04-14 22:47:26 UTC</update_date>
  <accession>BMDB0000386</accession>
  <secondary_accessions>
    <accession>BMDB00386</accession>
  </secondary_accessions>
  <name>3b,16a-Dihydroxyandrostenone sulfate</name>
  <description/>
  <synonyms>
    <synonym>3b,16a-Dihydroxyandrostenone sulfuric acid</synonym>
    <synonym>3b,16a-Dihydroxyandrostenone sulphate</synonym>
    <synonym>3b,16a-Dihydroxyandrostenone sulphuric acid</synonym>
    <synonym>16a-Hydroxydehydroepiandrosterone 3-sulfate</synonym>
    <synonym>16a-Hydroxydehydroepiandrosterone 3-sulphate</synonym>
    <synonym>16a-Hydroxydehydroisoandrosterone sulfate</synonym>
    <synonym>16a-Hydroxydehydroisoandrosterone sulphate</synonym>
    <synonym>3b,16a-Dihydroxy-5-androsten-17-one 3-sulfate</synonym>
    <synonym>3b,16a-Dihydroxy-5-androsten-17-one 3-sulphate</synonym>
    <synonym>3b,16a-Dihydroxy-androstenone sulfate</synonym>
    <synonym>3b,16a-Dihydroxy-androstenone sulphate</synonym>
    <synonym>[(1S,2S,10S,11S,13R,15R)-5-Hydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-13-yl]oxidanesulfonate</synonym>
    <synonym>[(1S,2S,10S,11S,13R,15R)-5-Hydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-13-yl]oxidanesulphonate</synonym>
    <synonym>[(1S,2S,10S,11S,13R,15R)-5-Hydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-13-yl]oxidanesulphonic acid</synonym>
  </synonyms>
  <chemical_formula>C19H28O6S</chemical_formula>
  <average_molecular_weight>384.487</average_molecular_weight>
  <monisotopic_moleculate_weight>384.160659318</monisotopic_moleculate_weight>
  <iupac_name>[(1S,2S,10S,11S,13R,15R)-5-hydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-13-yl]oxidanesulfonic acid</iupac_name>
  <traditional_iupac>[(1S,2S,10S,11S,13R,15R)-5-hydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-13-yl]oxidanesulfonic acid</traditional_iupac>
  <cas_registry_number>4873-65-8</cas_registry_number>
  <smiles>[H][C@@]12C[C@H](C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C)OS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C19H28O6S/c1-18-6-5-15-14(16(18)9-13(10-18)25-26(22,23)24)4-3-11-7-12(20)8-17(21)19(11,15)2/h8,11,13-16,20H,3-7,9-10H2,1-2H3,(H,22,23,24)/t11?,13-,14-,15+,16+,18-,19+/m1/s1</inchi>
  <inchikey>AWUIWQRSWWITFQ-LZRZFMTJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Sulfated steroids</sub_class>
    <direct_parent>Sulfated steroids</direct_parent>
    <alternative_parents>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Androgens and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Enols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxosteroids</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-oxosteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Androstane-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Enol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfated steroid skeleton</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-5.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(1S,2S,10S,11S,13R,15R)-5-hydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-13-yl]oxidanesulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>384.487</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>384.160659318</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@H](C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C)OS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H28O6S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O6S/c1-18-6-5-15-14(16(18)9-13(10-18)25-26(22,23)24)4-3-11-7-12(20)8-17(21)19(11,15)2/h8,11,13-16,20H,3-7,9-10H2,1-2H3,(H,22,23,24)/t11?,13-,14-,15+,16+,18-,19+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AWUIWQRSWWITFQ-LZRZFMTJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>100.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>96.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>371428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>371429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>371430</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022004</foodb_id>
  <chemspider_id>17215945</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id/>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5375</metlin_id>
  <synthesis_reference>Easterling, William E., Jr.; Simmer, Hans H.; Dignam, William J.; Frankland, Marjorie V.; Naftolin, Frederick.  Neutral C19 steroids and steroid sulfates in human pregnancy. II. Dehydroepiandrosterone sulfate, 16a-hydroxydehydroepiandrosterone, and 16a-hydroxydehydroepiandrosterone sulfate in maternal and fetal blood of pregnancies with anencephalic and normal fetuses.    Steroids  (1966),  8(2),  157-78.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:47 UTC</creation_date>
  <update_date>2020-04-14 22:47:26 UTC</update_date>
  <accession>BMDB0000387</accession>
  <secondary_accessions>
    <accession>BMDB00387</accession>
  </secondary_accessions>
  <name>3-Hydroxydodecanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Hydroxy-dodecanoic acid</synonym>
    <synonym>3-OH Dodecanoic acid</synonym>
    <synonym>3-OH Lauric acid</synonym>
    <synonym>beta-Hydroxydodecanoic acid</synonym>
    <synonym>beta-Hydroxylauric acid</synonym>
    <synonym>beta-OH Dodecanoic acid</synonym>
    <synonym>beta-OH Lauric acid</synonym>
    <synonym>3-Hydroxy-dodecanoate</synonym>
    <synonym>3-OH Dodecanoate</synonym>
    <synonym>3-OH Laate</synonym>
    <synonym>3-OH Laic acid</synonym>
    <synonym>b-Hydroxydodecanoate</synonym>
    <synonym>b-Hydroxydodecanoic acid</synonym>
    <synonym>beta-Hydroxydodecanoate</synonym>
    <synonym>Β-hydroxydodecanoate</synonym>
    <synonym>Β-hydroxydodecanoic acid</synonym>
    <synonym>b-Hydroxylaate</synonym>
    <synonym>b-Hydroxylaic acid</synonym>
    <synonym>beta-Hydroxylaate</synonym>
    <synonym>beta-Hydroxylaic acid</synonym>
    <synonym>Β-hydroxylaate</synonym>
    <synonym>Β-hydroxylaic acid</synonym>
    <synonym>b-OH Dodecanoate</synonym>
    <synonym>b-OH Dodecanoic acid</synonym>
    <synonym>beta-OH Dodecanoate</synonym>
    <synonym>Β-OH dodecanoate</synonym>
    <synonym>Β-OH dodecanoic acid</synonym>
    <synonym>b-OH Laate</synonym>
    <synonym>b-OH Laic acid</synonym>
    <synonym>beta-OH Laate</synonym>
    <synonym>beta-OH Laic acid</synonym>
    <synonym>Β-OH laate</synonym>
    <synonym>Β-OH laic acid</synonym>
    <synonym>3-Hydroxydodecanoate</synonym>
    <synonym>(RS)-3-Hydroxylaurate</synonym>
    <synonym>(RS)-3-Hydroxylauric acid</synonym>
    <synonym>11:0(3-OH)</synonym>
    <synonym>3-Hydroxylaurate</synonym>
    <synonym>3-Hydroxylauric acid</synonym>
    <synonym>b-Hydroxylaurate</synonym>
    <synonym>b-Hydroxylauric acid</synonym>
    <synonym>beta-Hydroxylaurate</synonym>
    <synonym>DL-b-Hydroxydodecanoate</synonym>
    <synonym>DL-b-Hydroxydodecanoic acid</synonym>
    <synonym>DL-beta-Hydroxydodecanoate</synonym>
    <synonym>DL-beta-Hydroxydodecanoic acid</synonym>
    <synonym>3-Hydroxydodecanoic acid, (S)-isomer</synonym>
    <synonym>3-Hydroxydodecanoic acid, (R)-isomer</synonym>
    <synonym>3-Hydroxydodecanoic acid, ion (1-)</synonym>
    <synonym>3-Hydroxydodecanoic acid, monosilver (1+) salt, (R)-isomer</synonym>
    <synonym>3-Hydroxydodecanoic acid, (+-)-isomer</synonym>
    <synonym>3-Hydroxydodecanoic acid, ion (1-), (+-)-isomer</synonym>
    <synonym>3-Hydroxydodecanoic acid</synonym>
  </synonyms>
  <chemical_formula>C12H24O3</chemical_formula>
  <average_molecular_weight>216.3172</average_molecular_weight>
  <monisotopic_moleculate_weight>216.172544634</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxydodecanoic acid</iupac_name>
  <traditional_iupac>3-hydroxydodecanoic acid</traditional_iupac>
  <cas_registry_number>1883-13-2</cas_registry_number>
  <smiles>CCCCCCCCCC(O)CC(O)=O</smiles>
  <inchi>InChI=1S/C12H24O3/c1-2-3-4-5-6-7-8-9-11(13)10-12(14)15/h11,13H,2-10H2,1H3,(H,14,15)</inchi>
  <inchikey>MUCMKTPAZLSKTL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Medium-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Medium-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hydroxy fatty acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
      <external_descriptor>medium-chain fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxydodecanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>216.3172</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>216.172544634</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCC(O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H24O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H24O3/c1-2-3-4-5-6-7-8-9-11(13)10-12(14)15/h11,13H,2-10H2,1H3,(H,14,15)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MUCMKTPAZLSKTL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18316</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022005</foodb_id>
  <chemspider_id>85026</chemspider_id>
  <pubchem_compound_id>94216</pubchem_compound_id>
  <chebi_id>36206</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5376</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Iwata, Tsutomu; Iwamoto, Osamu; Sugiyama, Haruhiko.  Process for preparing b-hydroxy fatty acid.    Eur. Pat. Appl.  (1990),   6 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:48 UTC</creation_date>
  <update_date>2020-03-13 16:20:48 UTC</update_date>
  <accession>BMDB0000388</accession>
  <secondary_accessions>
    <accession>BMDB00388</accession>
  </secondary_accessions>
  <name>3a,16-Dihydroxyandrostenone</name>
  <description/>
  <synonyms>
    <synonym>(3a)-3,16-Dihydroxy-androst-5-en-17-one</synonym>
    <synonym>3a,16-Dihydroxy-androstenone</synonym>
  </synonyms>
  <chemical_formula>C19H28O3</chemical_formula>
  <average_molecular_weight>304.4238</average_molecular_weight>
  <monisotopic_moleculate_weight>304.203844762</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,10S,11S,15R)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one</iupac_name>
  <traditional_iupac>3a,16-dihydroxy-androstenone</traditional_iupac>
  <cas_registry_number>64162-68-1</cas_registry_number>
  <smiles>[H][C@@]12CC(O)C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C</smiles>
  <inchi>InChI=1S/C19H28O3/c1-18-6-5-15-14(16(18)8-13(21)10-18)4-3-11-7-12(20)9-17(22)19(11,15)2/h9,11,13-16,20-21H,3-8,10H2,1-2H3/t11?,13?,14-,15+,16+,18-,19+/m1/s1</inchi>
  <inchikey>CUPQSMZELNNSIR-FBYGVVJCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>16-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Enols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxosteroids</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-oxosteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Enol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,10S,11S,15R)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>304.4238</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>304.203844762</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC(O)C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H28O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O3/c1-18-6-5-15-14(16(18)8-13(21)10-18)4-3-11-7-12(20)9-17(22)19(11,15)2/h9,11,13-16,20-21H,3-8,10H2,1-2H3/t11?,13?,14-,15+,16+,18-,19+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CUPQSMZELNNSIR-FBYGVVJCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37489</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022006</foodb_id>
  <chemspider_id>13628075</chemspider_id>
  <pubchem_compound_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5377</metlin_id>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:49 UTC</creation_date>
  <update_date>2020-03-13 16:20:49 UTC</update_date>
  <accession>BMDB0000389</accession>
  <secondary_accessions>
    <accession>BMDB00389</accession>
  </secondary_accessions>
  <name>2'-Deoxysepiapterin</name>
  <description/>
  <synonyms>
    <synonym>2-Amino-7,8-dihydro-6-(1-oxopropyl)-4(1H)-pteridin</synonym>
    <synonym>2-Amino-7,8-dihydro-6-propionyl-4(3H)-pteridinone</synonym>
    <synonym>Deoxysepiapterin</synonym>
    <synonym>Isosepiapterin</synonym>
  </synonyms>
  <chemical_formula>C9H11N5O2</chemical_formula>
  <average_molecular_weight>221.2159</average_molecular_weight>
  <monisotopic_moleculate_weight>221.091274621</monisotopic_moleculate_weight>
  <iupac_name>2-amino-6-propanoyl-1,4,7,8-tetrahydropteridin-4-one</iupac_name>
  <traditional_iupac>2-amino-6-propanoyl-7,8-dihydro-1H-pteridin-4-one</traditional_iupac>
  <cas_registry_number>1797-87-1</cas_registry_number>
  <smiles>CCC(=O)C1=NC2=C(NC1)NC(N)=NC2=O</smiles>
  <inchi>InChI=1S/C9H11N5O2/c1-2-5(15)4-3-11-7-6(12-4)8(16)14-9(10)13-7/h2-3H2,1H3,(H4,10,11,13,14,16)</inchi>
  <inchikey>MXQYRFPIGKAGPW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Pterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketimines</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Ketimine</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pterin</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-6-propanoyl-1,4,7,8-tetrahydropteridin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>221.2159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>221.091274621</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(=O)C1=NC2=C(NC1)NC(N)=NC2=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11N5O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11N5O2/c1-2-5(15)4-3-11-7-6(12-4)8(16)14-9(10)13-7/h2-3H2,1H3,(H4,10,11,13,14,16)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MXQYRFPIGKAGPW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>108.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>65.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15976</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022007</foodb_id>
  <chemspider_id>13628076</chemspider_id>
  <pubchem_compound_id>14055971</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference>Baur, Ralph; Sugimoto, Takashi; Pfleiderer, Wolfgang. Pteridines. LXXXV. Chemical synthesis of deoxysepiapterin and 6-acylpteridines by acyl radical substitution reactions. Helvetica Chimica Acta (1988), 71(3), 531-43.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:51 UTC</creation_date>
  <update_date>2020-04-15 22:13:43 UTC</update_date>
  <accession>BMDB0000390</accession>
  <secondary_accessions>
    <accession>BMDB00390</accession>
  </secondary_accessions>
  <name>3a,7b,12b-Trihydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3a,7b,12b-Trihydroxy-5b-cholanoate</synonym>
    <synonym>3a,7b,12b-Trihydroxy-5b-cholanate</synonym>
    <synonym>3a,7b,12b-Trihydroxy-5b-cholanic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R,16R)-5,9,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>81938-67-2</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19+,20-,22+,23+,24-/m1/s1</inchi>
  <inchikey>BHQCQFFYRZLCQQ-BJOVICNYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R,16R)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19+,20-,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHQCQFFYRZLCQQ-BJOVICNYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337281</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022008</foodb_id>
  <chemspider_id>4446960</chemspider_id>
  <pubchem_compound_id>5283872</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5379</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Goto, Junichi; Teraya, Yukari; Nambara, Toshio; Iida, Takashi.  Studies on steroids.  CCLIII.  Capillary gas chromatographic behavior of diethylhydrogensilyl-diethylsilylene derivatives of stereoisomeric bile acids.    Journal of Chromatography  (1991),  585(2),  281-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:52 UTC</creation_date>
  <update_date>2020-04-15 22:13:44 UTC</update_date>
  <accession>BMDB0000391</accession>
  <secondary_accessions>
    <accession>BMDB00391</accession>
  </secondary_accessions>
  <name>7-Ketodeoxycholic acid</name>
  <description/>
  <synonyms>
    <synonym>(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-Oic acid</synonym>
    <synonym>3alpha,12alpha-Dihydroxy-7-keto-5beta-cholanoic acid</synonym>
    <synonym>3alpha,12alpha-Dihydroxy-7-oxo-5beta-cholanate</synonym>
    <synonym>3alpha,12alpha-Diol-7-one-5beta-cholanoic acid</synonym>
    <synonym>7-Oxodeoxycholic acid</synonym>
    <synonym>(3a,5b,12a)-3,12-Dihydroxy-7-oxocholan-24-Oate</synonym>
    <synonym>(3a,5b,12a)-3,12-Dihydroxy-7-oxocholan-24-Oic acid</synonym>
    <synonym>(3alpha,5beta,12alpha)-3,12-Dihydroxy-7-oxocholan-24-Oate</synonym>
    <synonym>(3Α,5β,12α)-3,12-dihydroxy-7-oxocholan-24-Oate</synonym>
    <synonym>(3Α,5β,12α)-3,12-dihydroxy-7-oxocholan-24-Oic acid</synonym>
    <synonym>3a,12a-Dihydroxy-7-keto-5b-cholanoate</synonym>
    <synonym>3a,12a-Dihydroxy-7-keto-5b-cholanoic acid</synonym>
    <synonym>3alpha,12alpha-Dihydroxy-7-keto-5beta-cholanoate</synonym>
    <synonym>3Α,12α-dihydroxy-7-keto-5β-cholanoate</synonym>
    <synonym>3Α,12α-dihydroxy-7-keto-5β-cholanoic acid</synonym>
    <synonym>3a,12a-Dihydroxy-7-oxo-5b-cholanate</synonym>
    <synonym>3a,12a-Dihydroxy-7-oxo-5b-cholanic acid</synonym>
    <synonym>3alpha,12alpha-Dihydroxy-7-oxo-5beta-cholanic acid</synonym>
    <synonym>3Α,12α-dihydroxy-7-oxo-5β-cholanate</synonym>
    <synonym>3Α,12α-dihydroxy-7-oxo-5β-cholanic acid</synonym>
    <synonym>3a,12a-Diol-7-one-5b-cholanoate</synonym>
    <synonym>3a,12a-Diol-7-one-5b-cholanoic acid</synonym>
    <synonym>3alpha,12alpha-Diol-7-one-5beta-cholanoate</synonym>
    <synonym>3Α,12α-diol-7-one-5β-cholanoate</synonym>
    <synonym>3Α,12α-diol-7-one-5β-cholanoic acid</synonym>
    <synonym>7-Oxodeoxycholate</synonym>
    <synonym>7-Ketodeoxycholate</synonym>
    <synonym>(3a,5b,12a)-3,12-Dihydroxy-7-oxo-cholan-24-Oate</synonym>
    <synonym>(3a,5b,12a)-3,12-Dihydroxy-7-oxo-cholan-24-Oic acid</synonym>
    <synonym>3 alpha,12 alpha-Diol-7-one-5 beta-cholanoate</synonym>
    <synonym>3 alpha,12 alpha-Diol-7-one-5 beta-cholanoic acid</synonym>
    <synonym>3 alpha,7 alpha-Dihydroxy-7-keto-5 beta-cholanoate</synonym>
    <synonym>3 alpha,7 alpha-Dihydroxy-7-keto-5 beta-cholanoic acid</synonym>
    <synonym>3a,12a-Dihydroxy-7-oxo-5b-cholan-24-Oate</synonym>
    <synonym>3a,12a-Dihydroxy-7-oxo-5b-cholan-24-Oic acid</synonym>
    <synonym>7-Ketodeoxycholic acid, (3alpha,12alpha)-isomer</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,16-Dihydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
    <synonym>7-Ketodeoxycholic acid</synonym>
  </synonyms>
  <chemical_formula>C24H38O5</chemical_formula>
  <average_molecular_weight>406.5555</average_molecular_weight>
  <monisotopic_moleculate_weight>406.271924326</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>7-ketodeoxycholic acid</traditional_iupac>
  <cas_registry_number>911-40-0</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])C(=O)C[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-18,20,22,25,27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,20+,22+,23+,24-/m1/s1</inchi>
  <inchikey>RHCPKKNRWFXMAT-RRWYKFPJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-oxosteroids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>7-oxo steroid</external_descriptor>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>oxo-5beta-cholanic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>406.5555</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>406.271924326</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])C(=O)C[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H38O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-18,20,22,25,27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,20+,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RHCPKKNRWFXMAT-RRWYKFPJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355086</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022009</foodb_id>
  <chemspider_id>163659</chemspider_id>
  <pubchem_compound_id>188292</pubchem_compound_id>
  <chebi_id>16390</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5380</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Bortolini, Olga; Cova, Umberto; Fantin, Giancarlo; Medici, Alessandro.  A new non-enzymic route to chenodeoxycholic acid.    Chemistry Letters  (1996),   (5),  335-336</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:53 UTC</creation_date>
  <update_date>2020-04-15 22:13:45 UTC</update_date>
  <accession>BMDB0000392</accession>
  <secondary_accessions>
    <accession>BMDB00392</accession>
  </secondary_accessions>
  <name>2-Octenoic acid</name>
  <description>trans-2-Octenoic acid, also known as trans-2-octenoic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. trans-2-Octenoic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. trans-2-Octenoic acid exists in all eukaryotes, ranging from yeast to humans. trans-2-Octenoic acid participates in a number of enzymatic reactions, within cattle. In particular, trans-2-Octenoic acid can be biosynthesized from (R)-3-hydroxyoctanoic acid; which is mediated by the enzyme fatty acid synthase. dyhydrase domain. In addition, trans-2-Octenoic acid can be converted into caprylic acid through its interaction with the enzyme fatty acid synthase. enoyl reductase domain. In cattle, trans-2-octenoic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway.</description>
  <synonyms>
    <synonym>2-Octenoate</synonym>
    <synonym>cis-2-Octenoic acid</synonym>
    <synonym>(Z)-2-Octenoic acid</synonym>
    <synonym>2-Octenic acid</synonym>
    <synonym>2Z-Octenoate</synonym>
    <synonym>2Z-Octenoic acid</synonym>
    <synonym>Oct-2-enoate</synonym>
    <synonym>Oct-2-enoic acid</synonym>
    <synonym>trans-2-Octenoate</synonym>
    <synonym>2-Octenoic acid</synonym>
  </synonyms>
  <chemical_formula>C8H14O2</chemical_formula>
  <average_molecular_weight>142.1956</average_molecular_weight>
  <monisotopic_moleculate_weight>142.099379692</monisotopic_moleculate_weight>
  <iupac_name>(2Z)-oct-2-enoic acid</iupac_name>
  <traditional_iupac>cis-2-octenoic acid</traditional_iupac>
  <cas_registry_number>1577-96-4</cas_registry_number>
  <smiles>CCCCC\C=C/C(O)=O</smiles>
  <inchi>InChI=1S/C8H14O2/c1-2-3-4-5-6-7-8(9)10/h6-7H,2-5H2,1H3,(H,9,10)/b7-6-</inchi>
  <inchikey>CWMPPVPFLSZGCY-SREVYHEPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>5 - 6 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2Z)-oct-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>142.1956</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>142.099379692</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC\C=C/C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H14O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H14O2/c1-2-3-4-5-6-7-8(9)10/h6-7H,2-5H2,1H3,(H,9,10)/b7-6-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CWMPPVPFLSZGCY-SREVYHEPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339768</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022010</foodb_id>
  <chemspider_id>4445840</chemspider_id>
  <pubchem_compound_id>5282713</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>4146</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Dupont, Georges; Dulou, Raymond; Pigerol, Charles.  Kharasch reactions with 1-heptene. Synthesis of octanoic and 2-octenoic acid.    Compt. rend.  (1955),  240  628-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:54 UTC</creation_date>
  <update_date>2020-03-13 16:20:51 UTC</update_date>
  <accession>BMDB0000393</accession>
  <secondary_accessions>
    <accession>BMDB00393</accession>
  </secondary_accessions>
  <name>3-Hexenedioic acid</name>
  <description/>
  <synonyms>
    <synonym>(e)-3-Hexenedioic acid</synonym>
    <synonym>(e)-Hex-3-enedioic acid</synonym>
    <synonym>(e)-3-Hexenedioate</synonym>
    <synonym>(e)-Hex-3-enedioate</synonym>
    <synonym>3-Hexenedioate</synonym>
    <synonym>trans-2-Butene-1,4-dicarboxylate</synonym>
    <synonym>trans-2-Butene-1,4-dicarboxylic acid</synonym>
    <synonym>trans-3-Hexenedioate</synonym>
    <synonym>trans-3-Hexenedioic acid</synonym>
    <synonym>trans-b-Hydromuconate</synonym>
    <synonym>trans-b-Hydromuconic acid</synonym>
    <synonym>trans-beta-Hydromuconate</synonym>
    <synonym>trans-beta-Hydromuconic acid</synonym>
    <synonym>cis,cis-Muconate</synonym>
    <synonym>Muconic acid</synonym>
    <synonym>trans,trans-Muconic acid</synonym>
    <synonym>Muconic acid, (e,e)-isomer</synonym>
  </synonyms>
  <chemical_formula>C6H8O4</chemical_formula>
  <average_molecular_weight>144.1253</average_molecular_weight>
  <monisotopic_moleculate_weight>144.042258744</monisotopic_moleculate_weight>
  <iupac_name>(3E)-hex-3-enedioic acid</iupac_name>
  <traditional_iupac>3-hexenedioic acid</traditional_iupac>
  <cas_registry_number>29311-53-3</cas_registry_number>
  <smiles>OC(=O)C\C=C\CC(O)=O</smiles>
  <inchi>InChI=1S/C6H8O4/c7-5(8)3-1-2-4-6(9)10/h1-2H,3-4H2,(H,7,8)(H,9,10)/b2-1+</inchi>
  <inchikey>YHGNXQAFNHCBTK-OWOJBTEDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hexenedioic acid</external_descriptor>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>17 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3E)-hex-3-enedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>144.1253</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>144.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C\C=C\CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H8O4/c7-5(8)3-1-2-4-6(9)10/h1-2H,3-4H2,(H,7,8)(H,9,10)/b2-1+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YHGNXQAFNHCBTK-OWOJBTEDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>33.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348129</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>4508880</chemspider_id>
  <foodb_id>FDB022011</foodb_id>
  <kegg_id/>
  <pubchem_compound_id>5351896</pubchem_compound_id>
  <chebi_id>86952</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5382</metlin_id>
  <synthesis_reference>Stille, J. K.  Carbonylation of diolefins.    Belg.  (1979),     19 pp.  CODEN: BEXXAL  BE  877770  19791116  CAN 92:214907  AN 1980:214907</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:55 UTC</creation_date>
  <update_date>2020-03-13 16:20:52 UTC</update_date>
  <accession>BMDB0000394</accession>
  <secondary_accessions>
    <accession>BMDB00394</accession>
  </secondary_accessions>
  <name>3-Hydroxytetradecanedioic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Hydroxytetradecanedioate</synonym>
    <synonym>3-Hydroxy-tetradecanedioate</synonym>
  </synonyms>
  <chemical_formula>C14H26O5</chemical_formula>
  <average_molecular_weight>274.3532</average_molecular_weight>
  <monisotopic_moleculate_weight>274.178023942</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxytetradecanedioic acid</iupac_name>
  <traditional_iupac>3-hydroxytetradecanedioic acid</traditional_iupac>
  <cas_registry_number>73179-89-2</cas_registry_number>
  <smiles>OC(CCCCCCCCCCC(O)=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C14H26O5/c15-12(11-14(18)19)9-7-5-3-1-2-4-6-8-10-13(16)17/h12,15H,1-11H2,(H,16,17)(H,18,19)</inchi>
  <inchikey>CEDZIURHISELSQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxytetradecanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>274.3532</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>274.178023942</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(CCCCCCCCCCC(O)=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H26O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H26O5/c15-12(11-14(18)19)9-7-5-3-1-2-4-6-8-10-13(16)17/h12,15H,1-11H2,(H,16,17)(H,18,19)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CEDZIURHISELSQ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>71.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>97617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>97618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>97619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>162375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>162376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>162377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1354</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>13628077</chemspider_id>
  <foodb_id>FDB022012</foodb_id>
  <kegg_id/>
  <pubchem_compound_id>20848956</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5383</metlin_id>
  <synthesis_reference>Hill, Frank Friedrich.  Manufacture of 3-hydroxydicarboxylic acids.  Ger. Offen.  (1986), 14 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:56 UTC</creation_date>
  <update_date>2020-04-15 22:13:45 UTC</update_date>
  <accession>BMDB0000395</accession>
  <secondary_accessions>
    <accession>BMDB00395</accession>
  </secondary_accessions>
  <name>3b,7b,12a-Trihydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3b,7b,12a-Trihydroxy-5b-cholanoate</synonym>
    <synonym>3b,7b,12a-Trihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3b,7b,12a-Trihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3b,7b,12a-Trihydroxy-5b-cholanate</synonym>
    <synonym>3b,7b,12a-Trihydroxy-5b-cholanic acid</synonym>
    <synonym>Isoursodeoxycholate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5S,7S,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5S,7S,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>10322-18-6</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15+,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1</inchi>
  <inchikey>BHQCQFFYRZLCQQ-NSYKHXCCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5S,7S,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15+,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHQCQFFYRZLCQQ-NSYKHXCCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363267</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022013</foodb_id>
  <chemspider_id>4446961</chemspider_id>
  <pubchem_compound_id>5283873</pubchem_compound_id>
  <drugbank_id/>
  <kegg_id/>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5384</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Iida, Takashi; Chang, Frederic C.  Potential bile acid metabolites.  7.  3,7,12-Trihydroxy-5b-cholanic acids and related compounds.    Journal of Organic Chemistry  (1982),  47(15),  2972-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:58 UTC</creation_date>
  <update_date>2020-04-14 22:47:26 UTC</update_date>
  <accession>BMDB0000396</accession>
  <secondary_accessions>
    <accession>BMDB00396</accession>
  </secondary_accessions>
  <name>2-Ethylhydracrylic acid</name>
  <description/>
  <synonyms>
    <synonym>2-(Hydroxymethyl)-butyric acid</synonym>
    <synonym>3-Hydroxy-2-ethylpropanoic acid</synonym>
    <synonym>beta-Hydroxy-alpha-ethylpropionic acid</synonym>
    <synonym>2-(Hydroxymethyl)-butyrate</synonym>
    <synonym>3-Hydroxy-2-ethylpropanoate</synonym>
    <synonym>b-Hydroxy-a-ethylpropionate</synonym>
    <synonym>b-Hydroxy-a-ethylpropionic acid</synonym>
    <synonym>beta-Hydroxy-alpha-ethylpropionate</synonym>
    <synonym>Β-hydroxy-α-ethylpropionate</synonym>
    <synonym>Β-hydroxy-α-ethylpropionic acid</synonym>
    <synonym>2-Ethylhydracrylate</synonym>
    <synonym>2-(Hydroxymethyl)butyrate</synonym>
    <synonym>2-(Hydroxymethyl)butyric acid</synonym>
    <synonym>2-Ethyl-3-hydroxypropionate</synonym>
    <synonym>2-Ethyl-3-hydroxypropionic acid</synonym>
    <synonym>3-Hydroxy-2-ethylpropionate</synonym>
    <synonym>3-Hydroxy-2-ethylpropionic acid</synonym>
    <synonym>3-Hydroxy-propionic acid ethyl ester</synonym>
    <synonym>2-Ethyl-hydracrylate</synonym>
    <synonym>2-Ethylhydracrylic acid</synonym>
  </synonyms>
  <chemical_formula>C5H10O3</chemical_formula>
  <average_molecular_weight>118.1311</average_molecular_weight>
  <monisotopic_moleculate_weight>118.062994186</monisotopic_moleculate_weight>
  <iupac_name>2-(hydroxymethyl)butanoic acid</iupac_name>
  <traditional_iupac>2-ethylhydracrylic acid</traditional_iupac>
  <cas_registry_number>4374-62-3</cas_registry_number>
  <smiles>CCC(CO)C(O)=O</smiles>
  <inchi>InChI=1S/C5H10O3/c1-2-4(3-6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)</inchi>
  <inchikey>ZMZQVAUJTDKQGE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Branched fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
      <external_descriptor>branched-chain saturated fatty acid</external_descriptor>
      <external_descriptor>hydroxy fatty acid</external_descriptor>
      <external_descriptor>short-chain fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(hydroxymethyl)butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>118.1311</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>118.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(CO)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O3/c1-2-4(3-6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZMZQVAUJTDKQGE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>44892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>44893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>44894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136424</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022014</foodb_id>
  <chemspider_id>164207</chemspider_id>
  <pubchem_compound_id>188979</pubchem_compound_id>
  <chebi_id>82956</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>3785</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Price, Charles C.; Cypher, George A.; Krishnamurti, I. V.  Thermal reaction of formaldehyde with allyl cyanide.    Journal of the American Chemical Society  (1952),  74  2987-91.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:59 UTC</creation_date>
  <update_date>2020-03-13 16:20:53 UTC</update_date>
  <accession>BMDB0000397</accession>
  <secondary_accessions>
    <accession>BMDB00397</accession>
  </secondary_accessions>
  <name>2-Pyrocatechuic acid</name>
  <description>2-Pyrocatechuic acid, also known as 2,3-dihydroxybenzoate or O-pyrocatechuate, belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. 2-Pyrocatechuic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Pyrocatechuic acid exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>2,3 DHB</synonym>
    <synonym>2,3-DIHYDROXY-benzoIC ACID</synonym>
    <synonym>3-Hydroxysalicylic acid</synonym>
    <synonym>Catechol-3-carboxylic acid</synonym>
    <synonym>DOBK</synonym>
    <synonym>O-Pyrocatechuic acid</synonym>
    <synonym>Pyrocatechuic acid</synonym>
    <synonym>2,3-Dihydroxybenzoic acid</synonym>
    <synonym>2,3-DIHYDROXY-benzoate</synonym>
    <synonym>3-Hydroxysalicylate</synonym>
    <synonym>Catechol-3-carboxylate</synonym>
    <synonym>O-Pyrocatechuate</synonym>
    <synonym>Pyrocatechuate</synonym>
    <synonym>2,3-Dihydroxybenzoate</synonym>
    <synonym>2-Pyrocatechuate</synonym>
    <synonym>Catecholcarboxylate</synonym>
    <synonym>Catecholcarboxylic acid</synonym>
    <synonym>DHBA</synonym>
    <synonym>2,3-Dihydroxy benzoic acid</synonym>
    <synonym>2-Pyrocatechuic acid, sodium salt</synonym>
    <synonym>Ferri-2,3-dihydroxybenzoic acid</synonym>
  </synonyms>
  <chemical_formula>C7H6O4</chemical_formula>
  <average_molecular_weight>154.121</average_molecular_weight>
  <monisotopic_moleculate_weight>154.026608673</monisotopic_moleculate_weight>
  <iupac_name>2,3-dihydroxybenzoic acid</iupac_name>
  <traditional_iupac>2,3-dihydroxy-benzoic acid</traditional_iupac>
  <cas_registry_number>303-38-8</cas_registry_number>
  <smiles>OC(=O)C1=C(O)C(O)=CC=C1</smiles>
  <inchi>InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)</inchi>
  <inchikey>GLDQAMYCGOIJDV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>Salicylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Catechols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Catechol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Salicylic acid</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dihydroxybenzoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>logp</kind>
      <value>1.2</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,3-dihydroxybenzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>154.121</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>154.026608673</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1=C(O)C(O)=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H6O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GLDQAMYCGOIJDV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449822</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>18</chemspider_id>
  <foodb_id>FDB012200</foodb_id>
  <kegg_id>C00196</kegg_id>
  <pubchem_compound_id>19</pubchem_compound_id>
  <chebi_id>18026</chebi_id>
  <pdbe_id/>
  <drugbank_id>DB01672</drugbank_id>
  <phenol_explorer_compound_id>430</phenol_explorer_compound_id>
  <knapsack_id>C00002669</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>2,3-Dihydroxybenzoic_acid</wikipedia_id>
  <metlin_id>5386</metlin_id>
  <synthesis_reference>Mega, Izumi; Ozawa, Shuji.  Manufacture of 2,3-dihydroxybenzoic acid.    Jpn. Kokai Tokkyo Koho  (2001),     3 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:00 UTC</creation_date>
  <update_date>2020-03-13 16:20:54 UTC</update_date>
  <accession>BMDB0000398</accession>
  <secondary_accessions>
    <accession>BMDB00398</accession>
  </secondary_accessions>
  <name>3-Oxoadipic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Keto-adipate</synonym>
    <synonym>beta-Ketoadipic acid</synonym>
    <synonym>beta-Oxoadipic acid</synonym>
    <synonym>3-Keto-adipic acid</synonym>
    <synonym>b-Ketoadipate</synonym>
    <synonym>b-Ketoadipic acid</synonym>
    <synonym>beta-Ketoadipate</synonym>
    <synonym>Β-ketoadipate</synonym>
    <synonym>Β-ketoadipic acid</synonym>
    <synonym>b-Oxoadipate</synonym>
    <synonym>b-Oxoadipic acid</synonym>
    <synonym>beta-Oxoadipate</synonym>
    <synonym>Β-oxoadipate</synonym>
    <synonym>Β-oxoadipic acid</synonym>
    <synonym>3-Oxoadipate</synonym>
    <synonym>3-Ketoadipate</synonym>
    <synonym>3-Ketoadipic acid</synonym>
    <synonym>3-Oxohexanedioate</synonym>
    <synonym>3-Oxohexanedioic acid</synonym>
    <synonym>3-Oxoadipic acid, disodium salt</synonym>
    <synonym>3-Ketoadipic</synonym>
    <synonym>3-oxo-Adipate</synonym>
    <synonym>3-Oxoadipic acid</synonym>
  </synonyms>
  <chemical_formula>C6H8O5</chemical_formula>
  <average_molecular_weight>160.1247</average_molecular_weight>
  <monisotopic_moleculate_weight>160.037173366</monisotopic_moleculate_weight>
  <iupac_name>3-oxohexanedioic acid</iupac_name>
  <traditional_iupac>3-oxoadipic acid</traditional_iupac>
  <cas_registry_number>689-31-6</cas_registry_number>
  <smiles>OC(=O)CCC(=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C6H8O5/c7-4(3-6(10)11)1-2-5(8)9/h1-3H2,(H,8,9)(H,10,11)</inchi>
  <inchikey>RTGHRDFWYQHVFW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12  carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Medium-chain keto acids and derivatives</sub_class>
    <direct_parent>Medium-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-dicarbonyl compounds</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Beta-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Gamma-keto acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Beta-keto acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Gamma-keto acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Medium-chain keto acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>oxo dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>124 - 126 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-oxohexanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>160.1247</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>160.037173366</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC(=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H8O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H8O5/c7-4(3-6(10)11)1-2-5(8)9/h1-3H2,(H,8,9)(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RTGHRDFWYQHVFW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>91.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>33.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351219</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>91</chemspider_id>
  <foodb_id>FDB022015</foodb_id>
  <kegg_id>C00846</kegg_id>
  <pubchem_compound_id>93</pubchem_compound_id>
  <chebi_id>37440</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5387</metlin_id>
  <synthesis_reference>Darrah, Josephine A.; Cain, Ronald B.  Convenient biological method for preparing beta-ketoadipic acid.    Laboratory Practice  (1967),  16(8),  989-90.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:01 UTC</creation_date>
  <update_date>2020-04-15 22:13:46 UTC</update_date>
  <accession>BMDB0000399</accession>
  <secondary_accessions>
    <accession>BMDB00399</accession>
  </secondary_accessions>
  <name>3a,6b,7a,12a-Tetrahydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>beta-D-Fructose 1-phosphate</synonym>
    <synonym>b-D-Fructose 1-phosphate</synonym>
    <synonym>b-D-Fructose 1-phosphoric acid</synonym>
    <synonym>beta-D-Fructose 1-phosphoric acid</synonym>
    <synonym>Β-D-fructose 1-phosphate</synonym>
    <synonym>Β-D-fructose 1-phosphoric acid</synonym>
    <synonym>Fructose 1-phosphoric acid</synonym>
    <synonym>D-Fructose 1-phosphate</synonym>
    <synonym>D-Fructose-1-p</synonym>
    <synonym>D-Fructose-1-phosphate</synonym>
    <synonym>Fructose-1-p</synonym>
    <synonym>Fructose-1-phosphate</synonym>
    <synonym>3a,6b,7a,12a-Tetrahydroxy-5b-cholanoate</synonym>
    <synonym>(4R)-4-[(1S,2R,5R,7R,8S,9S,10R,11S,14R,15R,16S)-5,8,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O6</chemical_formula>
  <average_molecular_weight>424.5708</average_molecular_weight>
  <monisotopic_moleculate_weight>424.282489012</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5R,7R,8S,9S,10R,11S,14R,15R,16S)-5,8,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5R,7R,8S,9S,10R,11S,14R,15R,16S)-5,8,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>15978-08-2</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O6/c1-12(4-7-19(27)28)14-5-6-15-20-16(11-18(26)24(14,15)3)23(2)9-8-13(25)10-17(23)21(29)22(20)30/h12-18,20-22,25-26,29-30H,4-11H2,1-3H3,(H,27,28)/t12-,13-,14-,15+,16+,17+,18+,20+,21+,22+,23-,24-/m1/s1</inchi>
  <inchikey>COCMFMBNEAMQMA-VGKGADPCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>165 - 167 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5R,7R,8S,9S,10R,11S,14R,15R,16S)-5,8,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>424.5708</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>424.282489012</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O6/c1-12(4-7-19(27)28)14-5-6-15-20-16(11-18(26)24(14,15)3)23(2)9-8-13(25)10-17(23)21(29)22(20)30/h12-18,20-22,25-26,29-30H,4-11H2,1-3H3,(H,27,28)/t12-,13-,14-,15+,16+,17+,18+,20+,21+,22+,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>COCMFMBNEAMQMA-VGKGADPCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>112.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348762</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022410</foodb_id>
  <chemspider_id>8575807</chemspider_id>
  <pubchem_compound_id>10400369</pubchem_compound_id>
  <kegg_id>C01094</kegg_id>
  <chebi_id>139419</chebi_id>
  <meta_cyc_id>FRU1P</meta_cyc_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>40936</bigg_id>
  <wikipedia_id>Fructose 1-phosphate</wikipedia_id>
  <metlin_id>378</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Kurosawa, Takao; Mahara, Reijiro; Nittono, Hiroshi; Tohma, Masahiko.  Synthesis of 6-hydroxylated bile acids and identification of 3a,6a,7a,12a-tetrahydroxy-5b-cholan-24-oic acid in human meconium and neonatal urine.    Chemical &amp; Pharmaceutical Bulletin  (1989),  37(2),  557-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:02 UTC</creation_date>
  <update_date>2020-04-15 22:13:47 UTC</update_date>
  <accession>BMDB0000400</accession>
  <secondary_accessions>
    <accession>BMDB00400</accession>
  </secondary_accessions>
  <name>3,7-Dihydroxy-12-oxocholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>(3alpha,5beta,7alpha)-3,7-Dihydroxy-12-oxocholan-24-Oic acid</synonym>
    <synonym>3alpha,7alpha-Dihydroxy-12-oxo-5beta-cholanate</synonym>
    <synonym>(3a,5b,7a)-3,7-Dihydroxy-12-oxocholan-24-Oate</synonym>
    <synonym>(3a,5b,7a)-3,7-Dihydroxy-12-oxocholan-24-Oic acid</synonym>
    <synonym>(3alpha,5beta,7alpha)-3,7-Dihydroxy-12-oxocholan-24-Oate</synonym>
    <synonym>(3Α,5β,7α)-3,7-dihydroxy-12-oxocholan-24-Oate</synonym>
    <synonym>(3Α,5β,7α)-3,7-dihydroxy-12-oxocholan-24-Oic acid</synonym>
    <synonym>3a,7a-Dihydroxy-12-oxo-5b-cholanate</synonym>
    <synonym>3a,7a-Dihydroxy-12-oxo-5b-cholanic acid</synonym>
    <synonym>3alpha,7alpha-Dihydroxy-12-oxo-5beta-cholanic acid</synonym>
    <synonym>3Α,7α-dihydroxy-12-oxo-5β-cholanate</synonym>
    <synonym>3Α,7α-dihydroxy-12-oxo-5β-cholanic acid</synonym>
    <synonym>3,7-Dihydroxy-12-oxocholanoate</synonym>
    <synonym>(3a,5b,7a)-3,7-Dihydroxy-12-oxo-cholan-24-Oate</synonym>
    <synonym>(3a,5b,7a)-3,7-Dihydroxy-12-oxo-cholan-24-Oic acid</synonym>
    <synonym>12-Keto-3a,7a-dihydroxy-5b-cholanate</synonym>
    <synonym>12-Keto-3a,7a-dihydroxy-5b-cholanic acid</synonym>
    <synonym>12-Keto-chenodeoxycholate</synonym>
    <synonym>12-Keto-chenodeoxycholic acid</synonym>
    <synonym>12-Ketochenodeoxycholate</synonym>
    <synonym>12-Ketochenodeoxycholic acid</synonym>
    <synonym>12-oxo-3a,7a-Dihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>12-oxo-3a,7a-Dihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>12-Oxochenodeoxycholate</synonym>
    <synonym>12-Oxochenodeoxycholic acid</synonym>
    <synonym>3a,7a-Dihydroxy-12-keto-5b-cholanate</synonym>
    <synonym>3a,7a-Dihydroxy-12-keto-5b-cholanic acid</synonym>
    <synonym>3a,7a-Dihydroxy-12-ketocholanate</synonym>
    <synonym>3a,7a-Dihydroxy-12-ketocholanic acid</synonym>
    <synonym>3a,7a-Dihydroxy-12-ketocholate</synonym>
    <synonym>3a,7a-Dihydroxy-12-ketocholic acid</synonym>
    <synonym>3a,7a-Dihydroxy-12-oxo-5b-cholan-24-Oate</synonym>
    <synonym>3a,7a-Dihydroxy-12-oxo-5b-cholan-24-Oic acid</synonym>
    <synonym>3a,7a-Dihydroxy-12-oxo-5b-cholanoate</synonym>
    <synonym>3a,7a-Dihydroxy-12-oxo-5b-cholanoic acid</synonym>
    <synonym>3a,7a-Dihydroxy-12-oxocholate</synonym>
    <synonym>3a,7a-Dihydroxy-12-oxocholic acid</synonym>
    <synonym>5b-Cholanic acid-3a,7a-diol-12-one</synonym>
    <synonym>12-Monoketocholate</synonym>
    <synonym>12-Monoketocholic acid</synonym>
    <synonym>12-oxo-3,7-Dihydroxycholanoic acid</synonym>
    <synonym>3 alpha, 7 alpha-Dihydroxy-12-one-5 beta-cholanoic acid</synonym>
    <synonym>3 alpha,7 alpha-Dihydroxy-12-keto-5 beta-cholanoic acid</synonym>
    <synonym>3alpha,7alpha-Dihydroxy-12-keto-5beta-cholanoic acid</synonym>
    <synonym>Sodium monoketocholate</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
    <synonym>3,7-Dihydroxy-12-oxocholanoic acid</synonym>
  </synonyms>
  <chemical_formula>C24H38O5</chemical_formula>
  <average_molecular_weight>406.5555</average_molecular_weight>
  <monisotopic_moleculate_weight>406.271924326</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>12-ketochenodeoxycholic acid</traditional_iupac>
  <cas_registry_number>2458-08-4</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)C(=O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-19,22,25-26H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,22+,23+,24-/m1/s1</inchi>
  <inchikey>MIHNUBCEFJLAGN-DMMBONCOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxosteroids</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-oxosteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>oxo-5beta-cholanic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl-16-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>406.5555</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>406.271924326</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)C(=O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H38O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-19,22,25-26H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MIHNUBCEFJLAGN-DMMBONCOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356238</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022017</foodb_id>
  <kegg_id/>
  <chemspider_id>85044</chemspider_id>
  <pubchem_compound_id>94235</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>16312</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5389</metlin_id>
  <synthesis_reference>Fossati Elena; Polentini Fausto; Carrea Giacomo; Riva Sergio  Exploitation of the alcohol dehydrogenase-acetone NADP-regeneration system for the enzymatic preparative-scale production of 12-ketochenodeoxycholic acid.    Biotechnology and bioengineering  (2006),  93(6),  1216-20.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:03 UTC</creation_date>
  <update_date>2020-03-13 16:20:55 UTC</update_date>
  <accession>BMDB0000401</accession>
  <secondary_accessions>
    <accession>BMDB00401</accession>
  </secondary_accessions>
  <name>2,8-Dihydroxyadenine</name>
  <description/>
  <synonyms>
    <synonym>(6R)-2,6-2,8-Dihydroxyadenine</synonym>
    <synonym>2,8-Dioxyadenine</synonym>
    <synonym>6-Amino-1H-purine-2,8(3H,7H)-dione</synonym>
    <synonym>6-Amino-2,8-dihydroxypurine</synonym>
    <synonym>6-Amino-7H-purine-2,8-diol</synonym>
    <synonym>6-Amino-purine-2,8-diol</synonym>
    <synonym>Dimethyloctanoate</synonym>
    <synonym>Dimethyloctanoic acid</synonym>
    <synonym>2,8-Dihydroxyadenine</synonym>
  </synonyms>
  <chemical_formula>C5H5N5O2</chemical_formula>
  <average_molecular_weight>167.1255</average_molecular_weight>
  <monisotopic_moleculate_weight>167.044324429</monisotopic_moleculate_weight>
  <iupac_name>6-amino-7H-purine-2,8-diol</iupac_name>
  <traditional_iupac>6-amino-2,8-dihydroxypurine</traditional_iupac>
  <cas_registry_number>30377-37-8</cas_registry_number>
  <smiles>NC1=NC(O)=NC2=C1NC(O)=N2</smiles>
  <inchi>InChI=1S/C5H5N5O2/c6-2-1-3(9-4(11)7-1)10-5(12)8-2/h(H5,6,7,8,9,10,11,12)</inchi>
  <inchikey>XFBOJHLYDJZYSP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purinones. These are purines in which the purine moiety bears a C=O group. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Purinones</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>0.002 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6-amino-7H-purine-2,8-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>167.1255</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>167.044324429</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(O)=NC2=C1NC(O)=N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H5N5O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H5N5O2/c6-2-1-3(9-4(11)7-1)10-5(12)8-2/h(H5,6,7,8,9,10,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XFBOJHLYDJZYSP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>120.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364140</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022018</foodb_id>
  <kegg_id/>
  <chemspider_id>83302</chemspider_id>
  <pubchem_compound_id>92268</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>2,8-Dihydroxyadenine</wikipedia_id>
  <metlin_id>5390</metlin_id>
  <synthesis_reference>Stevens, Marcus A.; Smith, Herman W.; Brown, George Bosworth.  Purine N-oxides. VII. Reaction of aminopurine 1-N-oxides with acetic anhydride.    Journal of the American Chemical Society  (1960),  82  1148-52.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:05 UTC</creation_date>
  <update_date>2020-03-13 16:20:56 UTC</update_date>
  <accession>BMDB0000402</accession>
  <secondary_accessions>
    <accession>BMDB00402</accession>
  </secondary_accessions>
  <name>2-Isopropylmalic acid</name>
  <description/>
  <synonyms>
    <synonym>(2S)-2-Hydroxy-2-isopropylsuccinic acid</synonym>
    <synonym>(2S)-2-Isopropylmalate</synonym>
    <synonym>(3S)-3-Carboxy-3-hydroxy-4-methylpentanoic acid</synonym>
    <synonym>(3S)-3-Carboxy-3-hydroxyisocaproic acid</synonym>
    <synonym>(S)-2-Hydroxy-2-(isopropyl)succinic acid</synonym>
    <synonym>3-Carboxy-3-hydroxy-4-methylpentanoate</synonym>
    <synonym>3-Carboxy-3-hydroxyisocaproate</synonym>
    <synonym>(2S)-2-Hydroxy-2-isopropylsuccinate</synonym>
    <synonym>(2S)-2-Isopropylmalic acid</synonym>
    <synonym>(3S)-3-Carboxy-3-hydroxy-4-methylpentanoate</synonym>
    <synonym>(3S)-3-Carboxy-3-hydroxyisocaproate</synonym>
    <synonym>(S)-2-Hydroxy-2-(isopropyl)succinate</synonym>
    <synonym>3-Carboxy-3-hydroxy-4-methylpentanoic acid</synonym>
    <synonym>3-Carboxy-3-hydroxyisocaproic acid</synonym>
    <synonym>2-Isopropylmalate</synonym>
    <synonym>2-Hydroxy-2-isopropylsuccinate</synonym>
    <synonym>2-Hydroxy-2-isopropylsuccinic acid</synonym>
    <synonym>2-Isopropyl-2-hydroxybutanedioate</synonym>
    <synonym>2-Isopropyl-2-hydroxybutanedioic acid</synonym>
    <synonym>2-Isopropyl-malic acid</synonym>
    <synonym>a-Isopropylmalate</synonym>
    <synonym>a-Isopropylmalic acid</synonym>
    <synonym>alpha-Isopropylmalate</synonym>
    <synonym>alpha-Isopropylmalic acid</synonym>
    <synonym>(2S)-2-Hydroxy-2-(1-methylethyl)butanedioic acid</synonym>
    <synonym>(2S)-2-Hydroxy-2-(propan-2-yl)butanedioic acid</synonym>
    <synonym>(S)-(+)-2-Isopropylmalic acid</synonym>
    <synonym>2-Hydroxy-2-(1-methylethyl)butanedioic acid</synonym>
    <synonym>Α-isopropylmalate</synonym>
    <synonym>Α-isopropylmalic acid</synonym>
    <synonym>2-Isopropylmalic acid</synonym>
  </synonyms>
  <chemical_formula>C7H12O5</chemical_formula>
  <average_molecular_weight>176.1672</average_molecular_weight>
  <monisotopic_moleculate_weight>176.068473494</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-hydroxy-2-(propan-2-yl)butanedioic acid</iupac_name>
  <traditional_iupac>2-isopropyl-malic acid</traditional_iupac>
  <cas_registry_number>49601-06-1</cas_registry_number>
  <smiles>CC(C)[C@@](O)(CC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/t7-/m0/s1</inchi>
  <inchikey>BITYXLXUCSKTJS-ZETCQYMHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-isopropylmalic acid</external_descriptor>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>144 - 146 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-hydroxy-2-(propan-2-yl)butanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>176.1672</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>176.068473494</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)[C@@](O)(CC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H12O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)/t7-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BITYXLXUCSKTJS-ZETCQYMHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181412</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>4444155</chemspider_id>
  <foodb_id>FDB030115</foodb_id>
  <kegg_id>C02504</kegg_id>
  <pubchem_compound_id>5280523</pubchem_compound_id>
  <chebi_id>35128</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00019690</knapsack_id>
  <meta_cyc_id>3-CARBOXY-3-HYDROXY-ISOCAPROATE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Isopropylmalic acid</wikipedia_id>
  <metlin_id>339</metlin_id>
  <synthesis_reference>Schloss J V; Magolda R; Emptage M  Synthesis of alpha-isopropylmalate, beta-isopropylmalate, and dimethylcitraconate.    Methods in enzymology  (1988),  166 92-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:06 UTC</creation_date>
  <update_date>2020-03-13 16:20:56 UTC</update_date>
  <accession>BMDB0000403</accession>
  <secondary_accessions>
    <accession>BMDB00403</accession>
  </secondary_accessions>
  <name>2-Hydroxyadenine</name>
  <description/>
  <synonyms>
    <synonym>2-Oxoadenine</synonym>
    <synonym>6-Amino-1,3-dihydro-2H-purin-2-one</synonym>
    <synonym>6-Amino-3,7-dihydro-purin-2-one</synonym>
    <synonym>6-Amino-3,9-dihydro-2H-purin-2-one</synonym>
    <synonym>6-Amino-7H-purin-2-ol</synonym>
    <synonym>6-Amino-9H-purin-2-ol</synonym>
    <synonym>2-Hydroxy-6-aminopurine</synonym>
    <synonym>2-Oxyadenine</synonym>
    <synonym>6-Amino-2-hydroxypurine</synonym>
    <synonym>6-Amino-3,7(9)-dihydro-purin-2-one</synonym>
    <synonym>Isoguanine</synonym>
    <synonym>2-OH-Ade</synonym>
    <synonym>Crotonoside</synonym>
    <synonym>2-Hydroxyadenine</synonym>
  </synonyms>
  <chemical_formula>C5H5N5O</chemical_formula>
  <average_molecular_weight>151.1261</average_molecular_weight>
  <monisotopic_moleculate_weight>151.049409807</monisotopic_moleculate_weight>
  <iupac_name>6-amino-7H-purin-2-ol</iupac_name>
  <traditional_iupac>2-hydroxy-6-aminopurine</traditional_iupac>
  <cas_registry_number>3373-53-3</cas_registry_number>
  <smiles>NC1=NC(O)=NC2=C1NC=N2</smiles>
  <inchi>InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11)</inchi>
  <inchikey>DRAVOWXCEBXPTN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>6-aminopurines</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>oxopurine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>&gt; 360 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0625 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6-amino-7H-purin-2-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>151.1261</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>151.049409807</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(O)=NC2=C1NC=N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H5N5O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DRAVOWXCEBXPTN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>100.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326397</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022019</foodb_id>
  <kegg_id/>
  <chemspider_id>69351</chemspider_id>
  <pubchem_compound_id>76900</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>62462</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Isoguanine</wikipedia_id>
  <metlin_id>5392</metlin_id>
  <synthesis_reference>Hayashi, Taketo; Tamato, Toyomochi.  Preparation of isoguanine.    Jpn. Kokai Tokkyo Koho  (1994),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:07 UTC</creation_date>
  <update_date>2020-04-15 22:13:47 UTC</update_date>
  <accession>BMDB0000404</accession>
  <secondary_accessions>
    <accession>BMDB00404</accession>
  </secondary_accessions>
  <name>2b,3a,7a-Trihydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>2b,3a,7a-Trihydroxy-5b-cholanoate</synonym>
    <synonym>2b,3a,7a-Trihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>2b,3a,7a-Trihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,4S,5S,7R,9R,10R,11S,14R,15R)-4,5,9-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,4S,5S,7R,9R,10R,11S,14R,15R)-4,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,4S,5S,7R,9R,10R,11S,14R,15R)-4,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>133565-87-4</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)[C@@H](O)C[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)15-5-6-16-22-17(8-9-23(15,16)2)24(3)12-20(27)18(25)10-14(24)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16+,17+,18+,19-,20+,22+,23-,24+/m1/s1</inchi>
  <inchikey>NVTDAUYTNRUBQY-QCICEKRZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,4S,5S,7R,9R,10R,11S,14R,15R)-4,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)[C@@H](O)C[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)15-5-6-16-22-17(8-9-23(15,16)2)24(3)12-20(27)18(25)10-14(24)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16+,17+,18+,19-,20+,22+,23-,24+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NVTDAUYTNRUBQY-QCICEKRZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37504</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022020</foodb_id>
  <chemspider_id>4446935</chemspider_id>
  <pubchem_compound_id>5283847</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5393</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Iida, Takashi; Komatsubara, Ichiro; Chang, Frederic C.; Goto, Junichi; Nambara, Toshio.  Potential bile acid metabolites.  17.  Synthesis of 2b-hydroxylated bile acids.    Steroids  (1991),  56(3),  114-22.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:08 UTC</creation_date>
  <update_date>2020-04-15 22:29:40 UTC</update_date>
  <accession>BMDB0000405</accession>
  <secondary_accessions>
    <accession>BMDB00405</accession>
  </secondary_accessions>
  <name>2-Methoxyestradiol</name>
  <description/>
  <synonyms>
    <synonym>1,3,5(10)-ESTRATRIEN-2,3,17-BETA-triol 2-methyl ether</synonym>
    <synonym>2-Hydroxyestradol 2-methyl ether</synonym>
    <synonym>2-Methoxyestradiol-17beta</synonym>
    <synonym>Panzem</synonym>
    <synonym>1,3,5(10)-ESTRATRIEN-2,3,17-b-triol 2-methyl ether</synonym>
    <synonym>1,3,5(10)-ESTRATRIEN-2,3,17-β-triol 2-methyl ether</synonym>
    <synonym>2-Methoxyestradiol-17b</synonym>
    <synonym>2-Methoxyestradiol-17β</synonym>
    <synonym>2-(Methyl-11C)methoxyestradiol</synonym>
    <synonym>2-Methoxyestradiol, (17alpha)-isomer</synonym>
    <synonym>2-Methoxyoestradiol</synonym>
    <synonym>2-Methoxyestradiol-17 beta</synonym>
    <synonym>2ME2</synonym>
    <synonym>(17Β)-2-methoxyestra-1,3,5(10)-triene-3,17-diol</synonym>
    <synonym>(17beta)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol</synonym>
    <synonym>2-Hydroxyestradiol 2-methyl ether</synonym>
    <synonym>2-Methoxy-e2</synonym>
    <synonym>2-Methoxyestra-1,3,5(10)-triene-3,17β-diol</synonym>
    <synonym>2-Methoxyestra-1,3,5(10)-triene-3,17beta-diol</synonym>
    <synonym>2 Methoxyoestradiol</synonym>
    <synonym>(17 beta)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol</synonym>
    <synonym>2 Methoxyestradiol 17 beta</synonym>
    <synonym>2 Methoxyestradiol</synonym>
    <synonym>2-Methoxyestradiol</synonym>
  </synonyms>
  <chemical_formula>C19H26O3</chemical_formula>
  <average_molecular_weight>302.4079</average_molecular_weight>
  <monisotopic_moleculate_weight>302.188194698</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,14S,15S)-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol</iupac_name>
  <traditional_iupac>(1S,10R,11S,14S,15S)-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol</traditional_iupac>
  <cas_registry_number>362-07-2</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3</smiles>
  <inchi>InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1</inchi>
  <inchikey>CQOQDQWUFQDJMK-SSTWWWIQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17beta-hydroxy steroid</external_descriptor>
      <external_descriptor>3-hydroxy steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>Estrane and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>189 - 190 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,14S,15S)-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>302.4079</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>302.188194698</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(OC)=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H26O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CQOQDQWUFQDJMK-SSTWWWIQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>49.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369045</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>59788</chemspider_id>
  <foodb_id>FDB022021</foodb_id>
  <kegg_id>C05302</kegg_id>
  <pubchem_compound_id>66414</pubchem_compound_id>
  <chebi_id>28955</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>2-Methoxyestradiol</wikipedia_id>
  <metlin_id>5394</metlin_id>
  <synthesis_reference>Zhang, Beina; Wang, Hongbo; Zhang, Qian; Chen, Ying; Xia, Peng.  An improved process for synthesis of 2-methoxyestradiol.    Fudan Xuebao, Yixueban  (2003),  30(5),  494-495.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:10 UTC</creation_date>
  <update_date>2020-03-13 16:20:58 UTC</update_date>
  <accession>BMDB0000406</accession>
  <secondary_accessions>
    <accession>BMDB00406</accession>
  </secondary_accessions>
  <name>16-Ketoestradiol</name>
  <description/>
  <synonyms>
    <synonym>16-oxo-17beta-Estradiol</synonym>
    <synonym>16-oxo-17b-Estradiol</synonym>
    <synonym>16-oxo-17Β-estradiol</synonym>
    <synonym>1,3,5(10)-Estratriene-3,17b-diol-16-one</synonym>
    <synonym>16-Keto-17b-estradiol</synonym>
    <synonym>16-Oxoestradiol</synonym>
    <synonym>16-Oxoestradiol-17b</synonym>
    <synonym>3,17b-Dihydroxyestra-1,3,5(10)-trien-16-one</synonym>
    <synonym>16-Ketoestradiol, (17beta)-isomer, 4-(14)C-labeled</synonym>
    <synonym>16-Ketoestradiol, (17alpha)-isomer</synonym>
    <synonym>(17beta)-3,17-Dihydroxyestra-1,3,5(10)-trien-16-one</synonym>
  </synonyms>
  <chemical_formula>C18H22O3</chemical_formula>
  <average_molecular_weight>286.3655</average_molecular_weight>
  <monisotopic_moleculate_weight>286.15689457</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,14R,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-13-one</iupac_name>
  <traditional_iupac>16-ketoestradiol</traditional_iupac>
  <cas_registry_number>566-75-6</cas_registry_number>
  <smiles>[H][C@@]12CC(=O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</smiles>
  <inchi>InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-15,17,19,21H,2,4,6-7,9H2,1H3/t13-,14-,15+,17+,18+/m1/s1</inchi>
  <inchikey>KJDGFQJCHFJTRH-YONAWACDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>16-oxosteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>16-oxosteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>16-oxo steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,14R,15S)-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-13-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>286.3655</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>286.15689457</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC(=O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H22O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-15,17,19,21H,2,4,6-7,9H2,1H3/t13-,14-,15+,17+,18+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KJDGFQJCHFJTRH-YONAWACDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>80.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343596</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022022</foodb_id>
  <chemspider_id>59791</chemspider_id>
  <pubchem_compound_id>66417</pubchem_compound_id>
  <kegg_id>C14383</kegg_id>
  <chebi_id>1150238</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5395</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Tong, Zhengshou; Gan, Guizhi; Li, Lu.  Syntheses of 16-substituted estradiol derivatives.    Yiyao Gongye  (1984),   (8),  14-17.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:11 UTC</creation_date>
  <update_date>2020-04-14 22:47:27 UTC</update_date>
  <accession>BMDB0000407</accession>
  <secondary_accessions>
    <accession>BMDB00407</accession>
  </secondary_accessions>
  <name>2-Hydroxy-3-methylbutyric acid</name>
  <description/>
  <synonyms>
    <synonym>(S)-(+)-2-Hydroxy-3-methylbutanoic acid</synonym>
    <synonym>(S)-(+)-2-Hydroxy-3-methylbutyric acid</synonym>
    <synonym>2-Hydroxy-3-methyl-(S)-(+)-butyric acid</synonym>
    <synonym>2-Hydroxyisovalerate</synonym>
    <synonym>2-Oxyisovalerate</synonym>
    <synonym>a-Hydroxyisovaleric acid</synonym>
    <synonym>L-(+)-2-Hydroxyisovaleric acid</synonym>
    <synonym>L-(+)-alpha-Hydroxyisovaleric acid</synonym>
    <synonym>(S)-(+)-2-Hydroxy-3-methylbutanoate</synonym>
    <synonym>(S)-(+)-2-Hydroxy-3-methylbutyrate</synonym>
    <synonym>2-Hydroxy-3-methyl-(S)-(+)-butyrate</synonym>
    <synonym>2-Hydroxyisovaleric acid</synonym>
    <synonym>2-Oxyisovaleric acid</synonym>
    <synonym>a-Hydroxyisovalerate</synonym>
    <synonym>L-(+)-2-Hydroxyisovalerate</synonym>
    <synonym>L-(+)-a-Hydroxyisovalerate</synonym>
    <synonym>L-(+)-a-Hydroxyisovaleric acid</synonym>
    <synonym>L-(+)-alpha-Hydroxyisovalerate</synonym>
    <synonym>L-(+)-Α-hydroxyisovalerate</synonym>
    <synonym>L-(+)-Α-hydroxyisovaleric acid</synonym>
    <synonym>2-Hydroxy-3-methylbutyrate</synonym>
    <synonym>(S)-2-Hydroxy-3-methylbutyrate</synonym>
  </synonyms>
  <chemical_formula>C5H10O3</chemical_formula>
  <average_molecular_weight>118.132</average_molecular_weight>
  <monisotopic_moleculate_weight>118.062994182</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-hydroxy-3-methylbutanoic acid</iupac_name>
  <traditional_iupac>α-hydroxyisovaleric acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@](O)(C(C)C)C(O)=O</smiles>
  <inchi>InChI=1S/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t4-/m0/s1</inchi>
  <inchikey>NGEWQZIDQIYUNV-BYPYZUCNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>(2S)-2-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-hydroxy-3-methylbutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>118.132</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>118.062994182</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@](O)(C(C)C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O3/c1-3(2)4(6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t4-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NGEWQZIDQIYUNV-BYPYZUCNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>27.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>34086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>48971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>890053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>890054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>890055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>932257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>932258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>932259</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id>853180</pubchem_compound_id>
  <kegg_id/>
  <chebi_id>60631</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Perekalin, V. V.; Petryaeva, A. K.; Zobacheva, M. M.; Metelkina, E. L.  A new method of synthesis of a-hydroxy and a-oxo acids.    Doklady Akademii Nauk SSSR  (1966),  166(5),  1129-31. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:12 UTC</creation_date>
  <update_date>2020-03-13 16:20:59 UTC</update_date>
  <accession>BMDB0000408</accession>
  <secondary_accessions>
    <accession>BMDB00408</accession>
  </secondary_accessions>
  <name>2-Methyl-3-ketovaleric acid</name>
  <description/>
  <synonyms>
    <synonym>2-Methyl-3-oxo-pentanoic acid</synonym>
    <synonym>2-Methyl-3-oxovaleric acid</synonym>
    <synonym>beta-Ketoisocaproic acid</synonym>
    <synonym>2-Methyl-3-oxo-pentanoate</synonym>
    <synonym>2-Methyl-3-oxovalerate</synonym>
    <synonym>b-Ketoisocaproate</synonym>
    <synonym>b-Ketoisocaproic acid</synonym>
    <synonym>beta-Ketoisocaproate</synonym>
    <synonym>Β-ketoisocaproate</synonym>
    <synonym>Β-ketoisocaproic acid</synonym>
    <synonym>2-Methyl-3-ketovalerate</synonym>
  </synonyms>
  <chemical_formula>C6H10O3</chemical_formula>
  <average_molecular_weight>130.1418</average_molecular_weight>
  <monisotopic_moleculate_weight>130.062994186</monisotopic_moleculate_weight>
  <iupac_name>2-methyl-3-oxopentanoic acid</iupac_name>
  <traditional_iupac>2-methyl-3-oxovaleric acid</traditional_iupac>
  <cas_registry_number>14925-93-0</cas_registry_number>
  <smiles>CCC(=O)C(C)C(O)=O</smiles>
  <inchi>InChI=1S/C6H10O3/c1-3-5(7)4(2)6(8)9/h4H,3H2,1-2H3,(H,8,9)</inchi>
  <inchikey>QTLYPQZWYOHATR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Short-chain keto acids and derivatives</sub_class>
    <direct_parent>Short-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-dicarbonyl compounds</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Beta-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Beta-keto acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain keto acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-oxo monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>30 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-methyl-3-oxopentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>130.1418</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>130.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(=O)C(C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O3/c1-3-5(7)4(2)6(8)9/h4H,3H2,1-2H3,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QTLYPQZWYOHATR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328527</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022024</foodb_id>
  <pubchem_compound_id>189028</pubchem_compound_id>
  <chemspider_id>164251</chemspider_id>
  <kegg_id/>
  <chebi_id>86365</chebi_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5397</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Hirai, Yasuhiro; Aida, Takuzo; Inoue, Shohei.   Artificial photosynthesis of b-ketocarboxylic acids from carbon dioxide and ketones via enolate complexes of aluminum porphyrin. ,    Journal of the American Chemical Society  (1989),  111(8),  3062-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:13 UTC</creation_date>
  <update_date>2020-03-13 16:21:00 UTC</update_date>
  <accession>BMDB0000409</accession>
  <secondary_accessions>
    <accession>BMDB00409</accession>
  </secondary_accessions>
  <name>(5R)-5-Hydroxyhexanoic acid</name>
  <description/>
  <synonyms>
    <synonym>(-)-5-Hydroxycaproic acid</synonym>
    <synonym>(-)-5-Hydroxyhexanoic acid</synonym>
    <synonym>(5R)-5-Hydroxycaproic acid</synonym>
    <synonym>(R)-(-)-5-Hydroxyhexanoic acid</synonym>
    <synonym>(-)-5-Hydroxycaproate</synonym>
    <synonym>(-)-5-Hydroxyhexanoate</synonym>
    <synonym>(5R)-5-Hydroxycaproate</synonym>
    <synonym>(R)-(-)-5-Hydroxyhexanoate</synonym>
    <synonym>(5R)-5-Hydroxyhexanoate</synonym>
    <synonym>(5R)-5-Hydroxy-hexanoate</synonym>
    <synonym>(5R)-5-Hydroxy-hexanoic acid</synonym>
    <synonym>HMBA</synonym>
    <synonym>5R-Hydroxy-hexanoate</synonym>
  </synonyms>
  <chemical_formula>C6H12O3</chemical_formula>
  <average_molecular_weight>132.1577</average_molecular_weight>
  <monisotopic_moleculate_weight>132.07864425</monisotopic_moleculate_weight>
  <iupac_name>(5R)-5-hydroxyhexanoic acid</iupac_name>
  <traditional_iupac>HMBA</traditional_iupac>
  <cas_registry_number>83972-61-6</cas_registry_number>
  <smiles>C[C@@H](O)CCCC(O)=O</smiles>
  <inchi>InChI=1S/C6H12O3/c1-5(7)3-2-4-6(8)9/h5,7H,2-4H2,1H3,(H,8,9)/t5-/m1/s1</inchi>
  <inchikey>YDCRNMJQROAWFT-RXMQYKEDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>(omega-1)-hydroxy fatty acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
      <external_descriptor>medium-chain fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5R)-5-hydroxyhexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.1577</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.07864425</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](O)CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O3/c1-5(7)3-2-4-6(8)9/h5,7H,2-4H2,1H3,(H,8,9)/t5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YDCRNMJQROAWFT-RXMQYKEDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369759</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022025</foodb_id>
  <chemspider_id>5474600</chemspider_id>
  <pubchem_compound_id>7131043</pubchem_compound_id>
  <kegg_id/>
  <chebi_id>78842</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5398</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Fazio, Fabio; Schneider, Manfred P.  FA-catalyzed trimerization of R-(+)-6-methyltetrahydro-2-pyranone.   FB 9-Bergische Universitat-GH-Wuppertal,  Wuppertal,  Germany.    Tetrahedron Letters  (2002),  43(5),  811-814.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:14 UTC</creation_date>
  <update_date>2020-03-13 16:21:00 UTC</update_date>
  <accession>BMDB0000410</accession>
  <secondary_accessions>
    <accession>BMDB00410</accession>
  </secondary_accessions>
  <name>3-Hydroxy-2-methyl-[S-(R,R)]-butanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Hydroxy-2-methyl-[S-(R,R)]-butanoate</synonym>
    <synonym>3-Hydroxy-2-methyl-[S-(r*,r*)]-butanoate</synonym>
    <synonym>3-Hydroxy-2-methyl-[S-(r*,r*)]-butanoic acid</synonym>
    <synonym>[S-(R,R)]-3-Hydroxy-2-methyl-butanoate</synonym>
    <synonym>[S-(R,R)]-3-Hydroxy-2-methyl-butanoic acid</synonym>
  </synonyms>
  <chemical_formula>C5H10O3</chemical_formula>
  <average_molecular_weight>118.1311</average_molecular_weight>
  <monisotopic_moleculate_weight>118.062994186</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R)-3-hydroxy-2-methylbutanoic acid</iupac_name>
  <traditional_iupac>(2R,3R)-3-hydroxy-2-methylbutanoic acid</traditional_iupac>
  <cas_registry_number>84567-98-6</cas_registry_number>
  <smiles>C[C@@H](O)[C@@H](C)C(O)=O</smiles>
  <inchi>InChI=1S/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t3-,4-/m1/s1</inchi>
  <inchikey>VEXDRERIMPLZLU-QWWZWVQMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R)-3-hydroxy-2-methylbutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>118.1311</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>118.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](O)[C@@H](C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t3-,4-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VEXDRERIMPLZLU-QWWZWVQMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328047</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022026</foodb_id>
  <chemspider_id>13628080</chemspider_id>
  <pubchem_compound_id>12313369</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5399</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Kikukawa, Tadashi; Imaida, Motomasa; Tai, Akira.  Synthesis of the sex-attractant of pine sawflies (diprion species); (2S,3R,7R)- and (2S,3R,7S)-3,7-dimethylpentadecan-2-ol.    Chemistry Letters  (1982),   (11),  1799-802.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:16 UTC</creation_date>
  <update_date>2020-04-15 22:13:48 UTC</update_date>
  <accession>BMDB0000411</accession>
  <secondary_accessions>
    <accession>BMDB00411</accession>
  </secondary_accessions>
  <name>3a,12b-Dihydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>12-Epideoxycholate</synonym>
    <synonym>12-Epideoxycholic acid</synonym>
    <synonym>3a,12b-Dihydroxy-5b-cholanoate</synonym>
    <synonym>12-Epi-deoxy-cholate</synonym>
    <synonym>12-Epi-deoxy-cholic acid</synonym>
    <synonym>12-Epi-deoxycholate</synonym>
    <synonym>12-Epi-deoxycholic acid</synonym>
    <synonym>3a,12b-Dihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,12b-Dihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3a,12b-Dihydroxy-5b-cholanate</synonym>
    <synonym>3a,12b-Dihydroxy-5b-cholanic acid</synonym>
    <synonym>3a,12b-Dihydroxycholanoate</synonym>
    <synonym>3a,12b-Dihydroxycholanoic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O4</chemical_formula>
  <average_molecular_weight>392.572</average_molecular_weight>
  <monisotopic_moleculate_weight>392.292659768</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16R)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>12-epideoxycholate</traditional_iupac>
  <cas_registry_number>570-62-7</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21-,23+,24-/m1/s1</inchi>
  <inchikey>KXGVEGMKQFWNSR-MFSKYVBHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>cholanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16R)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>392.572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.292659768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21-,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KXGVEGMKQFWNSR-MFSKYVBHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329280</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022027</foodb_id>
  <chemspider_id>4446919</chemspider_id>
  <pubchem_compound_id>5283831</pubchem_compound_id>
  <kegg_id>C17646</kegg_id>
  <chebi_id>542045</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5400</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>hang, Frederic C.; Wood, Neville F.; Holton, William G.  3b,12b-Dihydroxycholanic acid.    Journal of Organic Chemistry  (1965),  30(6),  1718-23.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:17 UTC</creation_date>
  <update_date>2020-03-13 16:21:01 UTC</update_date>
  <accession>BMDB0000412</accession>
  <secondary_accessions>
    <accession>BMDB00412</accession>
  </secondary_accessions>
  <name>3b,17a-Dihydroxy-5a-androstane</name>
  <description/>
  <synonyms>
    <synonym>(3b,5a,17a)-Androstane-3,17-diol</synonym>
    <synonym>5a-Androstane-3b,17a-diol</synonym>
  </synonyms>
  <chemical_formula>C19H32O2</chemical_formula>
  <average_molecular_weight>292.4562</average_molecular_weight>
  <monisotopic_moleculate_weight>292.240230268</monisotopic_moleculate_weight>
  <iupac_name>(2S,5S,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol</iupac_name>
  <traditional_iupac>5a-androstane-3b,17a-diol</traditional_iupac>
  <cas_registry_number>5856-11-1</cas_registry_number>
  <smiles>C[C@]12CCC3C(CCC4C[C@@H](O)CC[C@]34C)C1CC[C@H]2O</smiles>
  <inchi>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12?,13-,14?,15?,16?,17+,18-,19-/m0/s1</inchi>
  <inchikey>CBMYJHIOYJEBSB-ILNNWSBUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,5S,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>292.4562</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>292.240230268</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@]12CCC3C(CCC4C[C@@H](O)CC[C@]34C)C1CC[C@H]2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H32O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12?,13-,14?,15?,16?,17+,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CBMYJHIOYJEBSB-ILNNWSBUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330003</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022028</foodb_id>
  <chemspider_id>8011440</chemspider_id>
  <pubchem_compound_id>9835719</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5401</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Han, Guang-Dian; Lin, Zi-Yun; Yan, Chong-Ping.  Synthesis of musk androgen 5a-androstane-3b,17a-diol.    Zhongguo Yiyao Gongye Zazhi  (1994),  25(11),  490-1.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:18 UTC</creation_date>
  <update_date>2020-03-13 16:21:02 UTC</update_date>
  <accession>BMDB0000413</accession>
  <secondary_accessions>
    <accession>BMDB00413</accession>
  </secondary_accessions>
  <name>3-Hydroxydodecanedioic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Hydroxydodecanedioate</synonym>
    <synonym>3-Hydroxy-dodecanedioate</synonym>
  </synonyms>
  <chemical_formula>C12H22O5</chemical_formula>
  <average_molecular_weight>246.3001</average_molecular_weight>
  <monisotopic_moleculate_weight>246.146723814</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxydodecanedioic acid</iupac_name>
  <traditional_iupac>3-hydroxydodecanedioic acid</traditional_iupac>
  <cas_registry_number>34574-69-1</cas_registry_number>
  <smiles>OC(CCCCCCCCC(O)=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C12H22O5/c13-10(9-12(16)17)7-5-3-1-2-4-6-8-11(14)15/h10,13H,1-9H2,(H,14,15)(H,16,17)</inchi>
  <inchikey>FYVQCLGZFXHEGL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Medium-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Medium-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxydodecanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>246.3001</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>246.146723814</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(CCCCCCCCC(O)=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H22O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H22O5/c13-10(9-12(16)17)7-5-3-1-2-4-6-8-11(14)15/h10,13H,1-9H2,(H,14,15)(H,16,17)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FYVQCLGZFXHEGL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>61.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>27.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351696</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022029</foodb_id>
  <pubchem_compound_id>16663321</pubchem_compound_id>
  <chemspider_id>13628081</chemspider_id>
  <kegg_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5402</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Schreurs, P. H. M.; Montijn, P. P.; Hoff, S.  New synthesis of trans-2-dodecene-1,12-dioic acid (traumatic acid).    Recueil des Travaux Chimiques des Pays-Bas  (1971),  90(12),  1331-2.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:19 UTC</creation_date>
  <update_date>2020-04-15 22:13:49 UTC</update_date>
  <accession>BMDB0000414</accession>
  <secondary_accessions>
    <accession>BMDB00414</accession>
  </secondary_accessions>
  <name>1b,3a,7a-Trihydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>1b,3a,7a-Trihydroxy-5b-cholanoate</synonym>
    <synonym>1 beta,3a,7a-Trihydroxy-5b-cholanoate</synonym>
    <synonym>1 beta,3a,7a-Trihydroxy-5b-cholanoic acid</synonym>
    <synonym>1b,3 alpha,7a-Trihydroxy-5b-cholanoate</synonym>
    <synonym>1b,3 alpha,7a-Trihydroxy-5b-cholanoic acid</synonym>
    <synonym>1b,3a,7 alpha-Trihydroxy-5b-cholanoate</synonym>
    <synonym>1b,3a,7 alpha-Trihydroxy-5b-cholanoic acid</synonym>
    <synonym>1b,3a,7a-Trihydroxy-5 beta-cholanoate</synonym>
    <synonym>1b,3a,7a-Trihydroxy-5 beta-cholanoic acid</synonym>
    <synonym>1b,3a,7a-Trihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>1b,3a,7a-Trihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>1b-Hydroxychenodeoxycholate</synonym>
    <synonym>1b-Hydroxychenodeoxycholic acid</synonym>
    <synonym>3-a,7-a,12-a-Trihydroxy-5-a-cholanoate</synonym>
    <synonym>3-a,7-a,12-a-Trihydroxy-5-a-cholanoic acid</synonym>
    <synonym>3-a,7-a,12-alpha-Trihydroxy-5-alpha-cholanoate</synonym>
    <synonym>3-a,7-a,12-alpha-Trihydroxy-5-alpha-cholanoic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R)-3,5,9-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>99598-04-6</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)C[C@@H](O)[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(8-9-23(16,17)2)24(3)14(11-19(22)26)10-15(25)12-20(24)27/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15+,16-,17+,18+,19-,20-,22+,23-,24+/m1/s1</inchi>
  <inchikey>GYUVAHWOVINGNE-RWXZXXAWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>238 - 240 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)C[C@@H](O)[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(8-9-23(16,17)2)24(3)14(11-19(22)26)10-15(25)12-20(24)27/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15+,16-,17+,18+,19-,20-,22+,23-,24+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GYUVAHWOVINGNE-RWXZXXAWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353241</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022030</foodb_id>
  <pubchem_compound_id>5283846</pubchem_compound_id>
  <kegg_id/>
  <chemspider_id>4446934</chemspider_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5403</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Tohma, Masahiko; Mahara, Reijiro; Takeshita, Hiromi; Kurosawa, Takao; Ikegawa, Shigeo; Nittono, Hiroshi.  Synthesis of the 1b-hydroxylated bile acids and identification of 1b,3a,7a-trihydroxy- and 1b,3a,7a,12a-tetrahydroxy-5b-cholan-24-oic acids in human meconium.    Chemical &amp; Pharmaceutical Bulletin  (1985),  33(7),  3071-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:20 UTC</creation_date>
  <update_date>2020-04-15 22:13:49 UTC</update_date>
  <accession>BMDB0000415</accession>
  <secondary_accessions>
    <accession>BMDB00415</accession>
  </secondary_accessions>
  <name>3a,6b,7b-Trihydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>(3alpha,5beta,6beta,7beta)-3,6,7-Trihydroxycholan-24-Oic acid</synonym>
    <synonym>3,6,7-Trihydroxy-5beta-cholan-24-Oic acid</synonym>
    <synonym>5beta-Cholanic acid-3alpha,6beta,7beta-triol</synonym>
    <synonym>beta-MCA</synonym>
    <synonym>beta-Muricholic acid</synonym>
    <synonym>3alpha,6beta,7beta-Trihydroxy-5beta-cholan-24-Oic acid</synonym>
    <synonym>(3a,5b,6b,7b)-3,6,7-Trihydroxycholan-24-Oate</synonym>
    <synonym>(3a,5b,6b,7b)-3,6,7-Trihydroxycholan-24-Oic acid</synonym>
    <synonym>(3alpha,5beta,6beta,7beta)-3,6,7-Trihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5β,6β,7β)-3,6,7-trihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5β,6β,7β)-3,6,7-trihydroxycholan-24-Oic acid</synonym>
    <synonym>3,6,7-Trihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3,6,7-Trihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3,6,7-Trihydroxy-5beta-cholan-24-Oate</synonym>
    <synonym>3,6,7-Trihydroxy-5β-cholan-24-Oate</synonym>
    <synonym>3,6,7-Trihydroxy-5β-cholan-24-Oic acid</synonym>
    <synonym>5b-Cholanate-3a,6b,7b-triol</synonym>
    <synonym>5b-Cholanic acid-3a,6b,7b-triol</synonym>
    <synonym>5beta-Cholanate-3alpha,6beta,7beta-triol</synonym>
    <synonym>5Β-cholanate-3α,6β,7β-triol</synonym>
    <synonym>5Β-cholanic acid-3α,6β,7β-triol</synonym>
    <synonym>b-MCA</synonym>
    <synonym>Β-mca</synonym>
    <synonym>b-Muricholate</synonym>
    <synonym>b-Muricholic acid</synonym>
    <synonym>beta-Muricholate</synonym>
    <synonym>Β-muricholate</synonym>
    <synonym>Β-muricholic acid</synonym>
    <synonym>3a,6b,7b-Trihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,6b,7b-Trihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3alpha,6beta,7beta-Trihydroxy-5beta-cholan-24-Oate</synonym>
    <synonym>3Α,6β,7β-trihydroxy-5β-cholan-24-Oate</synonym>
    <synonym>3Α,6β,7β-trihydroxy-5β-cholan-24-Oic acid</synonym>
    <synonym>3a,6b,7b-Trihydroxy-5b-cholanoate</synonym>
    <synonym>3a,6b,7b-Trihydroxy-5b-cholanate</synonym>
    <synonym>3a,6b,7b-Trihydroxy-5b-cholanic acid</synonym>
    <synonym>3 alpha,6 alpha,7 beta-Trihydroxy-5 beta-cholanoic acid</synonym>
    <synonym>3,6,7-Trihydroxy-5-cholanoic acid</synonym>
    <synonym>alpha-Muricholic acid</synonym>
    <synonym>Hyocholic acid</synonym>
    <synonym>Muricholic acid</synonym>
    <synonym>Muricholic acid, (3alpha,5alpha,6alpha,7alpha)-isomer</synonym>
    <synonym>Muricholic acid, (3alpha,5beta,6alpha,7alpha)-isomer</synonym>
    <synonym>Muricholic acid, (3alpha,5beta,6alpha,7beta)-isomer</synonym>
    <synonym>Muricholic acid, (3alpha,5beta,6beta,7alpha)-isomer</synonym>
    <synonym>Muricholic acid, (3alpha,5beta,6beta,7beta)-isomer</synonym>
    <synonym>Muricholic acid, sodium salt</synonym>
    <synonym>Omega-muricholic acid</synonym>
    <synonym>Trihydroxy-5 alpha-cholanoic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>2393-59-1</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21+,22-,23-,24-/m1/s1</inchi>
  <inchikey>DKPMWHFRUGMUKF-CRKPLTDNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>6-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>6-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>bile acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21+,22-,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DKPMWHFRUGMUKF-CRKPLTDNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340500</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022031</foodb_id>
  <pubchem_compound_id>5283853</pubchem_compound_id>
  <chemspider_id>4446941</chemspider_id>
  <kegg_id>C17726</kegg_id>
  <chebi_id>81298</chebi_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-16583</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5404</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Hsia, S. L.; Matschiner, John T.; Mahowald, Theodore A.; Elliott, Wm. H.; Doisy, E. A., Jr.; Thayer, Sidney A.; Doisy, Edward A.  Bile acids. VII. Structure of acid I.    Journal of Biological Chemistry  (1958),  230  573-80.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:22 UTC</creation_date>
  <update_date>2020-04-15 20:45:48 UTC</update_date>
  <accession>BMDB0000416</accession>
  <secondary_accessions>
    <accession>BMDB00416</accession>
  </secondary_accessions>
  <name>17-Hydroxypregnenolone sulfate</name>
  <description/>
  <synonyms>
    <synonym>17-Hydroxypregnenolone sulfuric acid</synonym>
    <synonym>17-Hydroxypregnenolone sulphate</synonym>
    <synonym>17-Hydroxypregnenolone sulphuric acid</synonym>
    <synonym>17-Hydroxy-pregnenolone sulfate</synonym>
    <synonym>17-Hydroxy-pregnenolone sulphate</synonym>
    <synonym>17-Hydroxypregnenolone 3-sulfate</synonym>
    <synonym>17-Hydroxypregnenolone 3-sulphate</synonym>
    <synonym>17alpha-Hydroxypregnenolone sulfate</synonym>
    <synonym>17alpha-Hydroxypregnenolone sulphate</synonym>
    <synonym>17b-Hydroxypregnenolone 3-sulfate</synonym>
    <synonym>17b-Hydroxypregnenolone 3-sulphate</synonym>
    <synonym>17 alpha-Hydroxypregnenolone sulfate</synonym>
  </synonyms>
  <chemical_formula>C21H32O6S</chemical_formula>
  <average_molecular_weight>412.54</average_molecular_weight>
  <monisotopic_moleculate_weight>412.191959446</monisotopic_moleculate_weight>
  <iupac_name>[(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulfonic acid</iupac_name>
  <traditional_iupac>17-hydroxypregnenolone sulfate</traditional_iupac>
  <cas_registry_number>2477-77-2</cas_registry_number>
  <smiles>[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(CC[C@]12C)OS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C21H32O6S/c1-13(22)21(23)11-8-18-16-5-4-14-12-15(27-28(24,25)26)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23H,5-12H2,1-3H3,(H,24,25,26)/t15?,16-,17+,18+,19+,20+,21+/m1/s1</inchi>
  <inchikey>OMOKWYAQVYBHMG-QUPIPBJSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Sulfated steroids</sub_class>
    <direct_parent>Sulfated steroids</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Pregnane steroids</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfated steroid skeleton</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Sulfates</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>412.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>412.191959446</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(CC[C@]12C)OS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H32O6S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H32O6S/c1-13(22)21(23)11-8-18-16-5-4-14-12-15(27-28(24,25)26)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23H,5-12H2,1-3H3,(H,24,25,26)/t15?,16-,17+,18+,19+,20+,21+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OMOKWYAQVYBHMG-QUPIPBJSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>100.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>105.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>44.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175247</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022032</foodb_id>
  <chemspider_id>134824</chemspider_id>
  <pubchem_compound_id>152971</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5405</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Gasparini, Francis J.; Hochberg, Richard B.; Lieberman, Seymour.  Biosynthesis of steroid sulfates by the boar testes.    Biochemistry  (1976),  15(18),  3969-75.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:23 UTC</creation_date>
  <update_date>2020-03-13 16:21:04 UTC</update_date>
  <accession>BMDB0000417</accession>
  <secondary_accessions>
    <accession>BMDB00417</accession>
  </secondary_accessions>
  <name>3D,7D,11D-Phytanic acid</name>
  <description/>
  <synonyms>
    <synonym>3D,7D,11D-Phytanate</synonym>
    <synonym>((3R,7R,11R)-)3,7,11,15-Tetramethylhexadecanoate</synonym>
    <synonym>((3R,7R,11R)-)3,7,11,15-Tetramethylhexadecanoic acid</synonym>
    <synonym>3,7,11,15-Tetramethyl-D,D,D-hexadecanoate</synonym>
    <synonym>3,7,11,15-Tetramethyl-D,D,D-hexadecanoic acid</synonym>
    <synonym>3,7,11,15-Tetramethyl-[3R-(3R*,7R*,11R*)]-hexadecanoate</synonym>
    <synonym>3,7,11,15-Tetramethyl-[3R-(3R*,7R*,11R*)]-hexadecanoic acid</synonym>
    <synonym>D,D,D-Phytanate</synonym>
    <synonym>D,D,D-Phytanic acid</synonym>
    <synonym>(3R,7R,11R)-1-Phytanoate</synonym>
  </synonyms>
  <chemical_formula>C20H40O2</chemical_formula>
  <average_molecular_weight>312.5304</average_molecular_weight>
  <monisotopic_moleculate_weight>312.302830524</monisotopic_moleculate_weight>
  <iupac_name>(3R,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid</iupac_name>
  <traditional_iupac>phytanoic acid</traditional_iupac>
  <cas_registry_number>18654-64-3</cas_registry_number>
  <smiles>CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@H](C)CC(O)=O</smiles>
  <inchi>InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)/t17-,18-,19-/m1/s1</inchi>
  <inchikey>RLCKHJSFHOZMDR-GUDVDZBRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Diterpenoids</sub_class>
    <direct_parent>Acyclic diterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyclic diterpenoid</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>312.5304</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>312.302830524</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@H](C)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H40O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)/t17-,18-,19-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RLCKHJSFHOZMDR-GUDVDZBRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>95.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128801</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB013514</foodb_id>
  <chemspider_id>8556273</chemspider_id>
  <pubchem_compound_id>10380830</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5406</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Sita, Lawrence R.  Convenient highly stereoselective syntheses of (3R,7R,11R)- and (3S,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid (phytanic acid) and the corresponding 3,7,11,15-tetramethylhexadecan-1-ols.  Journal of Organic Chemistry  (1993),  58(19),  5285-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:24 UTC</creation_date>
  <update_date>2020-04-15 22:32:23 UTC</update_date>
  <accession>BMDB0000418</accession>
  <secondary_accessions>
    <accession>BMDB00418</accession>
  </secondary_accessions>
  <name>18-Hydroxycortisol</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C21H30O6</chemical_formula>
  <average_molecular_weight>378.465</average_molecular_weight>
  <monisotopic_moleculate_weight>378.204238686</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10S,11S,14S,15S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10S,11S,14S,15S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@]12CC[C@@](O)(C(=O)CO)[C@@]1(CO)CC([H])(O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H30O6/c1-19-6-4-13(24)8-12(19)2-3-14-15-5-7-21(27,17(26)10-22)20(15,11-23)9-16(25)18(14)19/h8,14-16,18,22-23,25,27H,2-7,9-11H2,1H3/t14-,15-,16?,18+,19-,20+,21+/m0/s1</inchi>
  <inchikey>HESFZGWRDUVOMS-MWBGJKHOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>11-hydroxysteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>18-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>11-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>18-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.0056</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10S,11S,14S,15S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>378.465</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>378.204238686</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@@](O)(C(=O)CO)[C@@]1(CO)CC([H])(O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H30O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H30O6/c1-19-6-4-13(24)8-12(19)2-3-14-15-5-7-21(27,17(26)10-22)20(15,11-23)9-16(25)18(14)19/h8,14-16,18,22-23,25,27H,2-7,9-11H2,1H3/t14-,15-,16?,18+,19-,20+,21+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HESFZGWRDUVOMS-MWBGJKHOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>115.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>99.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>80410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1002104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1002105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1002106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1126085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1126086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1126087</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id/>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Gomez-Sanchez, Celso E.; Kirk, David N.; Farrant, R. Duncan; Milewich, Leon.  18-Substituted steroids:  synthesis of 18-hydroxycortisol (11b,17a,18,21-tetrahydroxy-4-pregnene-3,20-dione) and 18-hydroxycortisone (17a,18,21-trihydroxy-4-pregnene-3,11,20-trione).    Journal of Steroid Biochemistry  (1985),  22(1),  141-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:25 UTC</creation_date>
  <update_date>2020-04-15 22:13:50 UTC</update_date>
  <accession>BMDB0000419</accession>
  <secondary_accessions>
    <accession>BMDB00419</accession>
  </secondary_accessions>
  <name>3b,7a,12a-Trihydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>(3beta,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oic acid</synonym>
    <synonym>3-Epi-cholic acid</synonym>
    <synonym>3-Epicholic acid</synonym>
    <synonym>3beta-Cholic acid</synonym>
    <synonym>Isocholic acid</synonym>
    <synonym>(3b,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oate</synonym>
    <synonym>(3b,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acid</synonym>
    <synonym>(3beta,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oate</synonym>
    <synonym>(3β,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oate</synonym>
    <synonym>(3β,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oic acid</synonym>
    <synonym>3b,7a,12a-Trihydroxy-5b-cholanoate</synonym>
    <synonym>3-Epi-cholate</synonym>
    <synonym>3-Epicholate</synonym>
    <synonym>3b-Cholate</synonym>
    <synonym>3b-Cholic acid</synonym>
    <synonym>3beta-Cholate</synonym>
    <synonym>3β-cholate</synonym>
    <synonym>3β-cholic acid</synonym>
    <synonym>Isocholate</synonym>
    <synonym>3b,7a,12a-Trihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3b,7a,12a-Trihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3b,7a,12a-Trihydroxy-5b-cholanate</synonym>
    <synonym>3b,7a,12a-Trihydroxy-5b-cholanic acid</synonym>
    <synonym>3beta,7alpha,12alpha-Trihydroxy-5beta-cholan-24-Oate</synonym>
    <synonym>3Β,7α,12α-trihydroxy-5β-cholan-24-Oate</synonym>
    <synonym>3Β,7α,12α-trihydroxy-5β-cholan-24-Oic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,5S,7S,9R,10R,11S,14R,15R,16S)-5,9,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5S,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5S,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1</inchi>
  <inchikey>BHQCQFFYRZLCQQ-UXWVVXDJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerolipids</class>
    <sub_class>Diradylglycerols</sub_class>
    <direct_parent>1,2-diacylglycerols</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-acyl-sn-glycerol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5S,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHQCQFFYRZLCQQ-UXWVVXDJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353709</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB024394</foodb_id>
  <chemspider_id/>
  <drugbank_id/>
  <pubchem_compound_id/>
  <kegg_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference>Hasegawa, Kyohei.  The synthesis of steroid bile acids. XXXIV. Reduction of oxo bile acids with NaBH4.    Hiroshima Journal of Medical Sciences  (1959),  8  271-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:27 UTC</creation_date>
  <update_date>2020-03-13 16:21:06 UTC</update_date>
  <accession>BMDB0000421</accession>
  <secondary_accessions>
    <accession>BMDB00421</accession>
  </secondary_accessions>
  <name>2,3-Dihydroxyvaleric acid</name>
  <description/>
  <synonyms>
    <synonym>2,3-Dihydroxyvalerate</synonym>
    <synonym>2,3-Dihydroxy-valerate</synonym>
    <synonym>2,3-Dihydroxy-valeric acid</synonym>
  </synonyms>
  <chemical_formula>C5H10O4</chemical_formula>
  <average_molecular_weight>134.1305</average_molecular_weight>
  <monisotopic_moleculate_weight>134.057908808</monisotopic_moleculate_weight>
  <iupac_name>2,3-dihydroxypentanoic acid</iupac_name>
  <traditional_iupac>2,3-dihydroxyvaleric acid</traditional_iupac>
  <cas_registry_number>26386-47-0</cas_registry_number>
  <smiles>CCC(O)C(O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H10O4/c1-2-3(6)4(7)5(8)9/h3-4,6-7H,2H2,1H3,(H,8,9)</inchi>
  <inchikey>CJXCLBPFKGZXJP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,3-dihydroxypentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>134.1305</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>134.057908808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(O)C(O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O4/c1-2-3(6)4(7)5(8)9/h3-4,6-7H,2H2,1H3,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CJXCLBPFKGZXJP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>29.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328224</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022035</foodb_id>
  <pubchem_compound_id>20848966</pubchem_compound_id>
  <chemspider_id>13451358</chemspider_id>
  <kegg_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5410</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Kogl, Fritz; Duisberg, Herwarth; Erxleben, Hanni.  Fungus poisons. I. Muscarine. I.    Ann.  (1931),  489  156-92.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:28 UTC</creation_date>
  <update_date>2020-03-13 16:21:06 UTC</update_date>
  <accession>BMDB0000422</accession>
  <secondary_accessions>
    <accession>BMDB00422</accession>
  </secondary_accessions>
  <name>2-Methylglutaric acid</name>
  <description/>
  <synonyms>
    <synonym>alpha-Methylglutaric acid</synonym>
    <synonym>a-Methylglutarate</synonym>
    <synonym>a-Methylglutaric acid</synonym>
    <synonym>alpha-Methylglutarate</synonym>
    <synonym>Α-methylglutarate</synonym>
    <synonym>Α-methylglutaric acid</synonym>
    <synonym>2-Methylglutarate</synonym>
    <synonym>(+-)-2-Methylglutaric acid</synonym>
    <synonym>2-Methylpentanedioate</synonym>
    <synonym>2-Methylpentanedioic acid</synonym>
    <synonym>2-Methyleneglutaric acid</synonym>
    <synonym>2-Methyleneglutarate</synonym>
    <synonym>alpha-Methylene glutarate</synonym>
    <synonym>alpha-Methylene glutarate, ion(2-)</synonym>
    <synonym>2-Methylene glutarate</synonym>
    <synonym>2-Methyl-glutarate</synonym>
  </synonyms>
  <chemical_formula>C6H10O4</chemical_formula>
  <average_molecular_weight>146.1412</average_molecular_weight>
  <monisotopic_moleculate_weight>146.057908808</monisotopic_moleculate_weight>
  <iupac_name>2-methylpentanedioic acid</iupac_name>
  <traditional_iupac>α-methylglutaric acid</traditional_iupac>
  <cas_registry_number>617-62-9</cas_registry_number>
  <smiles>CC(CCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H10O4/c1-4(6(9)10)2-3-5(7)8/h4H,2-3H2,1H3,(H,7,8)(H,9,10)</inchi>
  <inchikey>AQYCMVICBNBXNA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Methyl-branched fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>alpha,omega-dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>908 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-methylpentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>146.1412</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>146.057908808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(CCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O4/c1-4(6(9)10)2-3-5(7)8/h4H,2-3H2,1H3,(H,7,8)(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AQYCMVICBNBXNA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439236</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022036</foodb_id>
  <pubchem_compound_id>12046</pubchem_compound_id>
  <chemspider_id>11549</chemspider_id>
  <kegg_id/>
  <chebi_id>68567</chebi_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5411</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Ignaczak, M.; Deka, M.  Synthesis of 2-methylglutaric acid by oxidation of 3-methyl-1,2-cyclopentanedione by anode-generated Ce(IV).    Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya  (1994),  37(7-9),  63-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:29 UTC</creation_date>
  <update_date>2020-03-13 16:21:07 UTC</update_date>
  <accession>BMDB0000423</accession>
  <secondary_accessions>
    <accession>BMDB00423</accession>
  </secondary_accessions>
  <name>3,4-Dihydroxyhydrocinnamic acid</name>
  <description/>
  <synonyms>
    <synonym>3,4-Dihydroxy-beta-phenylpropionic acid</synonym>
    <synonym>3,4-Dihydroxybenzenepropanoic acid</synonym>
    <synonym>3,4-Dihydroxybenzenepropionic acid</synonym>
    <synonym>3,4-Dihydroxydihydrocinnamic acid</synonym>
    <synonym>3,4-Dihydroxyphenylpropionic acid</synonym>
    <synonym>3-(3,4-Dihydroxyphenyl)propionic acid</synonym>
    <synonym>Dihydrocaffeic acid</synonym>
    <synonym>Hydrocaffeic acid</synonym>
    <synonym>3-(3,4-Dihydroxyphenyl)propanoate</synonym>
    <synonym>3,4-Dihydroxy-b-phenylpropionate</synonym>
    <synonym>3,4-Dihydroxy-b-phenylpropionic acid</synonym>
    <synonym>3,4-Dihydroxy-beta-phenylpropionate</synonym>
    <synonym>3,4-Dihydroxy-β-phenylpropionate</synonym>
    <synonym>3,4-Dihydroxy-β-phenylpropionic acid</synonym>
    <synonym>3,4-Dihydroxybenzenepropanoate</synonym>
    <synonym>3,4-Dihydroxybenzenepropionate</synonym>
    <synonym>3,4-Dihydroxydihydrocinnamate</synonym>
    <synonym>3,4-Dihydroxyphenylpropionate</synonym>
    <synonym>3-(3,4-Dihydroxyphenyl)propionate</synonym>
    <synonym>Dihydrocaffeate</synonym>
    <synonym>Hydrocaffeate</synonym>
    <synonym>3-(3,4-Dihydroxyphenyl)propanoic acid</synonym>
    <synonym>3,4-Dihydroxyhydrocinnamate</synonym>
    <synonym>3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamate</synonym>
    <synonym>3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamic acid</synonym>
    <synonym>3,4-Dihydroxyphenylpropionic acid, potassium salt</synonym>
    <synonym>DHC</synonym>
    <synonym>3,4-Dihydroxyhydrocinnamic acid</synonym>
  </synonyms>
  <chemical_formula>C9H10O4</chemical_formula>
  <average_molecular_weight>182.1733</average_molecular_weight>
  <monisotopic_moleculate_weight>182.057908808</monisotopic_moleculate_weight>
  <iupac_name>3-(3,4-dihydroxyphenyl)propanoic acid</iupac_name>
  <traditional_iupac>dihydrocaffeic acid</traditional_iupac>
  <cas_registry_number>1078-61-1</cas_registry_number>
  <smiles>OC(=O)CCC1=CC(O)=C(O)C=C1</smiles>
  <inchi>InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)</inchi>
  <inchikey>DZAUWHJDUNRCTF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Phenylpropanoic acids</class>
    <sub_class/>
    <direct_parent>Phenylpropanoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Catechols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Catechol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>catechols</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>136 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>428 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(3,4-dihydroxyphenyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>182.1733</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>182.057908808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC1=CC(O)=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DZAUWHJDUNRCTF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437538</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB008857</foodb_id>
  <pubchem_compound_id>348154</pubchem_compound_id>
  <chemspider_id>308986</chemspider_id>
  <kegg_id>C10447</kegg_id>
  <chebi_id>48400</chebi_id>
  <phenol_explorer_compound_id>579</phenol_explorer_compound_id>
  <drugbank_id/>
  <knapsack_id>C00002735</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5412</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Sabally Kebba; Karboune Salwa; St-Louis Richard; Kermasha Selim  Lipase-catalyzed transesterification of dihydrocaffeic acid with flaxseed oil for the synthesis of phenolic lipids.  Journal of biotechnology  (2006),  127(1),  167-76.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:30 UTC</creation_date>
  <update_date>2020-03-13 16:21:07 UTC</update_date>
  <accession>BMDB0000424</accession>
  <secondary_accessions>
    <accession>BMDB00424</accession>
  </secondary_accessions>
  <name>2-Hydroxydecanedioic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Hydroxydecanedioate</synonym>
    <synonym>2-Hydroxy-decandioate</synonym>
    <synonym>2-Hydroxy-decandioic acid</synonym>
    <synonym>2-Hydroxysebacate</synonym>
    <synonym>2-Hydroxysebacic acid</synonym>
    <synonym>a-Hydroxysebasate</synonym>
    <synonym>a-Hydroxysebasic acid</synonym>
    <synonym>alpha-Hydroxysebasate</synonym>
    <synonym>alpha-Hydroxysebasic acid</synonym>
    <synonym>2-Hydroxy-decanedioate</synonym>
  </synonyms>
  <chemical_formula>C10H18O5</chemical_formula>
  <average_molecular_weight>218.2469</average_molecular_weight>
  <monisotopic_moleculate_weight>218.115423686</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxydecanedioic acid</iupac_name>
  <traditional_iupac>2-hydroxysebacic acid</traditional_iupac>
  <cas_registry_number>103963-71-9</cas_registry_number>
  <smiles>OC(CCCCCCCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C10H18O5/c11-8(10(14)15)6-4-2-1-3-5-7-9(12)13/h8,11H,1-7H2,(H,12,13)(H,14,15)</inchi>
  <inchikey>LPIOYESQKJFWPQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Medium-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Medium-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>118 - 121 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxydecanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>218.2469</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>218.115423686</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(CCCCCCCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H18O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H18O5/c11-8(10(14)15)6-4-2-1-3-5-7-9(12)13/h8,11H,1-7H2,(H,12,13)(H,14,15)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LPIOYESQKJFWPQ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>52.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>58665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>58666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>58667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>114651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>114652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>114653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1364</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022037</foodb_id>
  <pubchem_compound_id>128458</pubchem_compound_id>
  <chemspider_id>113866</chemspider_id>
  <kegg_id/>
  <chebi_id>89312</chebi_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5413</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Chiruta, Chandramouli; Jachak, Santosh; Clive, Derrick L. J.  A convenient general method for the synthesis of hydroxy diacids.    Tetrahedron Letters  (2007),  48(18),  3141-3143.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:32 UTC</creation_date>
  <update_date>2020-03-13 16:21:08 UTC</update_date>
  <accession>BMDB0000425</accession>
  <secondary_accessions>
    <accession>BMDB00425</accession>
  </secondary_accessions>
  <name>3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Deoxy-D-glycero-D-galacto-2-nonulosonate</synonym>
    <synonym>2-KDN</synonym>
    <synonym>2-Keto-3-deoxy-D-glycero-D-galacto-NONONate</synonym>
    <synonym>2-Keto-3-deoxy-D-glycero-D-galacto-NONONic acid</synonym>
    <synonym>2-oxo-3-Deoxy-D-glycero-galactononulosonate</synonym>
    <synonym>2-oxo-3-Deoxy-D-glycero-galactononulosonic acid</synonym>
    <synonym>3-Deoxy-D-glycero-D-galacto-nonulosonate</synonym>
    <synonym>3-Deoxy-D-glycero-D-galacto-nonulosonic acid</synonym>
    <synonym>3-Deoxyglycero-galacto-nonulosonate</synonym>
    <synonym>3-Deoxyglycero-galacto-nonulosonic acid</synonym>
    <synonym>3-Deoxyglycerogalacto-2-nonulopyranosonate</synonym>
    <synonym>3-Deoxyglycerogalacto-2-nonulopyranosonic acid</synonym>
    <synonym>Deoxy-KDN</synonym>
    <synonym>KDN</synonym>
    <synonym>Sialosonate</synonym>
    <synonym>Sialosonic acid</synonym>
    <synonym>SiaX</synonym>
    <synonym>(4S,5R,6R,7R,8S)-4,5,6,7,8,9-Hexahydroxy-2-oxononanoate</synonym>
    <synonym>3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid</synonym>
  </synonyms>
  <chemical_formula>C9H16O9</chemical_formula>
  <average_molecular_weight>268.2179</average_molecular_weight>
  <monisotopic_moleculate_weight>268.07943211</monisotopic_moleculate_weight>
  <iupac_name>(4S,5R,6R,7R,8S)-4,5,6,7,8,9-hexahydroxy-2-oxononanoic acid</iupac_name>
  <traditional_iupac>siaX</traditional_iupac>
  <cas_registry_number>22594-61-2</cas_registry_number>
  <smiles>OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)CC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C9H16O9/c10-2-5(13)7(15)8(16)6(14)3(11)1-4(12)9(17)18/h3,5-8,10-11,13-16H,1-2H2,(H,17,18)/t3-,5-,6+,7+,8+/m0/s1</inchi>
  <inchikey>FQHUAUMYHAJTDH-IMSDGWMTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain keto acids and derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Nonoses</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Keto acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Medium-chain keto acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Nonose monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sugar acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4S,5R,6R,7R,8S)-4,5,6,7,8,9-hexahydroxy-2-oxononanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>268.2179</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>268.07943211</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)CC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H16O9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H16O9/c10-2-5(13)7(15)8(16)6(14)3(11)1-4(12)9(17)18/h3,5-8,10-11,13-16H,1-2H2,(H,17,18)/t3-,5-,6+,7+,8+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FQHUAUMYHAJTDH-IMSDGWMTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>175.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347736</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022038</foodb_id>
  <kegg_id/>
  <chemspider_id>17215951</chemspider_id>
  <pubchem_compound_id>22833524</pubchem_compound_id>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5414</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Nakamura, Mitsunobu; Fujita, Shuji; Furuhata, Kimio; Ogura, Haruo.  Synthesis of the nucleoside analogs of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN).    Nucleic Acids Symposium Series  (1991),  25(Symp. Nucleic Acids Chem., 18th, 1991),  137-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:33 UTC</creation_date>
  <update_date>2020-03-13 16:21:08 UTC</update_date>
  <accession>BMDB0000426</accession>
  <secondary_accessions>
    <accession>BMDB00426</accession>
  </secondary_accessions>
  <name>Citramalic acid</name>
  <description/>
  <synonyms>
    <synonym>(+-)-2-Hydroxy-2-methylsuccinic acid</synonym>
    <synonym>2-Hydroxy-2-methylbutanedioic acid</synonym>
    <synonym>2-Hydroxy-2-methylsuccinic acid</synonym>
    <synonym>2-Methylmalic acid</synonym>
    <synonym>alpha-Hydroxypyrotartaric acid</synonym>
    <synonym>Citramalic acids</synonym>
    <synonym>(+-)-2-Hydroxy-2-methylsuccinate</synonym>
    <synonym>2-Hydroxy-2-methylbutanedioate</synonym>
    <synonym>2-Hydroxy-2-methylsuccinate</synonym>
    <synonym>2-Methylmalate</synonym>
    <synonym>a-Hydroxypyrotartarate</synonym>
    <synonym>a-Hydroxypyrotartaric acid</synonym>
    <synonym>alpha-Hydroxypyrotartarate</synonym>
    <synonym>Α-hydroxypyrotartarate</synonym>
    <synonym>Α-hydroxypyrotartaric acid</synonym>
    <synonym>Citramalate</synonym>
    <synonym>(b)-2-Methylmalate</synonym>
    <synonym>(b)-2-Methylmalic acid</synonym>
    <synonym>(b)-Citramalate</synonym>
    <synonym>(b)-Citramalic acid</synonym>
    <synonym>(R,S)-(b)-Citramalate</synonym>
    <synonym>(R,S)-(b)-Citramalic acid</synonym>
    <synonym>(R,S)-b-Methylmalate</synonym>
    <synonym>(R,S)-b-Methylmalic acid</synonym>
    <synonym>(R,S)-beta-Methylmalate</synonym>
    <synonym>(R,S)-beta-Methylmalic acid</synonym>
    <synonym>2-Deoxy-3-C-methyltetrarate</synonym>
    <synonym>2-Deoxy-3-C-methyltetraric acid</synonym>
    <synonym>2-Hydroxy-2-methyl-(b)-butanedioate</synonym>
    <synonym>2-Hydroxy-2-methyl-(b)-butanedioic acid</synonym>
    <synonym>2-Hydroxy-2-methyl-butanedioate</synonym>
    <synonym>2-Hydroxy-2-methyl-butanedioic acid</synonym>
    <synonym>2-Methyl-(b)-malate</synonym>
    <synonym>2-Methyl-(b)-malic acid</synonym>
    <synonym>DL-Citramalate</synonym>
    <synonym>DL-Citramalic acid</synonym>
    <synonym>Citramalate, (+-)-isomer</synonym>
    <synonym>Citramalate, (R)-isomer</synonym>
    <synonym>Citramalate, (S)-isomer</synonym>
    <synonym>alpha-Methylmalate</synonym>
    <synonym>(R)-2-Hydroxy-2-methylbutanedioate</synonym>
    <synonym>Citramalic acid</synonym>
  </synonyms>
  <chemical_formula>C5H8O5</chemical_formula>
  <average_molecular_weight>148.114</average_molecular_weight>
  <monisotopic_moleculate_weight>148.037173366</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-2-methylbutanedioic acid</iupac_name>
  <traditional_iupac>citramalate, (+-)-</traditional_iupac>
  <cas_registry_number>597-44-4</cas_registry_number>
  <smiles>CC(O)(CC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)</inchi>
  <inchikey>XFTRTWQBIOMVPK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxydicarboxylic acid</external_descriptor>
      <external_descriptor>3-hydroxy carboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>107 - 111 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-2-methylbutanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>148.114</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>148.037173366</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(O)(CC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XFTRTWQBIOMVPK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>29.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440122</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB002815</foodb_id>
  <chemspider_id>1051</chemspider_id>
  <kegg_id>C00815</kegg_id>
  <pubchem_compound_id>1081</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15584</chebi_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id>C00001181</knapsack_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5415</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Barker, H. A.  Chemical synthesis and resolution of (±)-citramalic acid.    Biochemical Preparations  (1962),  9  25-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:34 UTC</creation_date>
  <update_date>2020-04-15 22:13:51 UTC</update_date>
  <accession>BMDB0000427</accession>
  <secondary_accessions>
    <accession>BMDB00427</accession>
  </secondary_accessions>
  <name>3b,7b,12a-Trihydroxy-5a-Cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3b,7b,12a-Trihydroxy-5a-cholanoate</synonym>
    <synonym>(4R)-4-[(1S,2S,5S,7R,9S,10R,11S,14R,15R,16S)-5,9,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5S,7R,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5S,7R,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>63324-20-9</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15+,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1</inchi>
  <inchikey>BHQCQFFYRZLCQQ-UEXPSFCYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5S,7R,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15+,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHQCQFFYRZLCQQ-UEXPSFCYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347037</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>4446967</chemspider_id>
  <foodb_id>FDB022039</foodb_id>
  <pubchem_compound_id>5283879</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5416</metlin_id>
  <synthesis_reference>Iida, Takashi; Shinohara, Toshiyuki; Momose, Toshiaki; Tamura, Toshitake; Matsumoto, Taro; Nambara, Toshio; Chang, Frederic C.  Potential bile acid metabolites; 12.  Synthesis of stereoisomeric 3,7,12-trihydroxy-5a-cholanic acids and related compounds.    Synthesis  (1986),   (12),  998-1004.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:35 UTC</creation_date>
  <update_date>2020-04-15 22:22:47 UTC</update_date>
  <accession>BMDB0000428</accession>
  <secondary_accessions>
    <accession>BMDB00428</accession>
  </secondary_accessions>
  <name>3-Hydroxyglutaric acid</name>
  <description/>
  <synonyms>
    <synonym>3-Hydroxyglutarate</synonym>
    <synonym>3-Hydroxy-glutarate</synonym>
    <synonym>3-Hydroxy-glutaric acid</synonym>
    <synonym>3-Hydroxypentanedioic acid</synonym>
    <synonym>2,4-Dideoxypentaric acid</synonym>
    <synonym>Β-hydroxyglutaric acid</synonym>
    <synonym>beta-Hydroxyglutaric acid</synonym>
    <synonym>3-Hydroxypentanedioate</synonym>
    <synonym>3-Hydroxyglutaric acid</synonym>
  </synonyms>
  <chemical_formula>C5H8O5</chemical_formula>
  <average_molecular_weight>148.114</average_molecular_weight>
  <monisotopic_moleculate_weight>148.037173366</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxypentanedioic acid</iupac_name>
  <traditional_iupac>3-hydroxyglutaric acid</traditional_iupac>
  <cas_registry_number>638-18-6</cas_registry_number>
  <smiles>OC(CC(O)=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C5H8O5/c6-3(1-4(7)8)2-5(9)10/h3,6H,1-2H2,(H,7,8)(H,9,10)</inchi>
  <inchikey>ZQHYXNSQOIDNTL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Beta hydroxy acids and derivatives</sub_class>
    <direct_parent>Beta hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxypentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>148.114</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>148.037173366</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(CC(O)=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O5/c6-3(1-4(7)8)2-5(9)10/h3,6H,1-2H2,(H,7,8)(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZQHYXNSQOIDNTL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>29.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>77385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>77386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>77387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>137493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>137494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>137495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1310</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022040</foodb_id>
  <chemspider_id>158277</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>181976</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <drugbank_id>DB04594</drugbank_id>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Alpha-Hydroxyglutaric acid</wikipedia_id>
  <metlin_id>5417</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Arnaud, Nathalie; Picard, Claude; Cazaux, Louis; Tisnes, Pierre.  Synthesis of macrocyclic polyhydroxy tetralactams derived from L-tartaric acid and b-hydroxyglutaric acid.    Tetrahedron  (1997),  53(40),  13757-13768.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:36 UTC</creation_date>
  <update_date>2020-03-13 16:21:10 UTC</update_date>
  <accession>BMDB0000429</accession>
  <secondary_accessions>
    <accession>BMDB00429</accession>
  </secondary_accessions>
  <name>17a-Estradiol</name>
  <description>17a-Estradiol, also known as alpha-estradiol or estradiol-17alpha, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 17a-estradiol is considered to be a steroid lipid molecule. 17a-Estradiol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 17a-Estradiol is a potentially toxic compound. 17a-Estradiol has been linked to the inborn metabolic disorders including glutaryl-coa dehydrogenase deficiency (gdhd).</description>
  <synonyms>
    <synonym>Alfatradiol</synonym>
    <synonym>alpha-Estradiol</synonym>
    <synonym>Estra-1,3,5(10)trien-3,17alpha-diol</synonym>
    <synonym>Estradiol-17alpha</synonym>
    <synonym>17alpha-Estradiol</synonym>
    <synonym>a-Estradiol</synonym>
    <synonym>Α-estradiol</synonym>
    <synonym>Estra-1,3,5(10)trien-3,17a-diol</synonym>
    <synonym>Estra-1,3,5(10)trien-3,17α-diol</synonym>
    <synonym>Estradiol-17a</synonym>
    <synonym>Estradiol-17α</synonym>
    <synonym>17Α-estradiol</synonym>
    <synonym>1,3,5-Estratriene-3,17a-diol</synonym>
    <synonym>13b-Methyl-1,3,5(10)-gonatriene-3,17a-diol</synonym>
    <synonym>17-Epiestradiol</synonym>
    <synonym>17a-Oestradiol</synonym>
    <synonym>3,17-Dihydroxyestratriene</synonym>
    <synonym>3,17a-Dihydroxyestra-1,3,5(10)-triene</synonym>
    <synonym>3,17a-Dihydroxyoestra-1,3,5(10)-triene</synonym>
    <synonym>Epiestradiol</synonym>
    <synonym>Epiestrol</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,17a-diol</synonym>
    <synonym>Oestra-1,3,5(10)-triene-3,17a-diol</synonym>
    <synonym>17a-Estradiol</synonym>
  </synonyms>
  <chemical_formula>C18H24O2</chemical_formula>
  <average_molecular_weight>272.382</average_molecular_weight>
  <monisotopic_moleculate_weight>272.177630012</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol</iupac_name>
  <traditional_iupac>(1S,10R,11S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol</traditional_iupac>
  <cas_registry_number>57-91-0</cas_registry_number>
  <smiles>[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</smiles>
  <inchi>InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1</inchi>
  <inchikey>VOXZDWNPVJITMN-SFFUCWETSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>3-hydroxy steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>Estrane and derivatives</external_descriptor>
      <external_descriptor>estradiol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>216 - 219 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0039 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,14R,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>272.382</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>272.177630012</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H24O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VOXZDWNPVJITMN-SFFUCWETSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344724</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000145 +/- 0.00003928</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk (commercial)</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637.</reference_text>
          <pubmed_id>17852390</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000111</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Half skim milk</comment>
      <references>
        <reference>
          <reference_text>Colazo MG, Ambrose DJ, Kastelic JP, Small JA: Comparison of 2 enzyme immunoassays and a radioimmunoassay for measurement of progesterone concentrations in bovine plasma, skim milk, and whole milk. Can J Vet Res. 2008 Jan;72(1):32-6.</reference_text>
          <pubmed_id>18214159</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000116</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB011524</foodb_id>
  <chemspider_id>61840</chemspider_id>
  <kegg_id>C02537</kegg_id>
  <pubchem_compound_id>68570</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17160</chebi_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5418</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Gardi, Rinaldo; Pedrali, Cesare; Ercoli, Alberto.  3-Cyclopentyl ethers of 16,17-oxygenated estrogens. New synthesis of 17a-estradiol.    Gazzetta Chimica Italiana  (1963),  93(8-9),  1028-43.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637.</reference_text>
      <pubmed_id>17852390</pubmed_id>
    </reference>
    <reference>
      <reference_text>Colazo MG, Ambrose DJ, Kastelic JP, Small JA: Comparison of 2 enzyme immunoassays and a radioimmunoassay for measurement of progesterone concentrations in bovine plasma, skim milk, and whole milk. Can J Vet Res. 2008 Jan;72(1):32-6.</reference_text>
      <pubmed_id>18214159</pubmed_id>
    </reference>
    <reference>
      <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
      <pubmed_id>18412364</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:37 UTC</creation_date>
  <update_date>2020-03-13 16:21:10 UTC</update_date>
  <accession>BMDB0000430</accession>
  <secondary_accessions>
    <accession>BMDB00430</accession>
  </secondary_accessions>
  <name>24,25-Dihydroxyvitamin D</name>
  <description>24,25-Dihydroxyvitamin D, also known as vitamin D or 24-hydroxycalcidiol, belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. 24,25-Dihydroxyvitamin D is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).</description>
  <synonyms>
    <synonym>(3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,24,25-triol</synonym>
    <synonym>24,25-Dihydroxycholecalciferol</synonym>
    <synonym>24,25-Dihydroxyvitamin</synonym>
    <synonym>24,25-Dihydroxyvitamin D3</synonym>
    <synonym>24-Hydroxycalcidiol</synonym>
    <synonym>Vitamin D</synonym>
    <synonym>24,25 Dihydroxyvitamin D3</synonym>
    <synonym>(24R)-24,25-Dihydroxyvitamin D3</synonym>
    <synonym>24,25-Dihydroxyvitamin D 3, (3beta,5Z,7E,24R)-isomer</synonym>
    <synonym>24,25 Dihydroxycholecalciferol</synonym>
    <synonym>Dihydroxyvitamin D3, 24,25</synonym>
    <synonym>24R,25-Dihydroxycholecalciferol</synonym>
    <synonym>24,25 Dihydroxyvitamin D 3</synonym>
    <synonym>24,25-Dihydroxyvitamin D 3</synonym>
    <synonym>24,25-Dihydroxy-vitamin D</synonym>
  </synonyms>
  <chemical_formula>C27H44O3</chemical_formula>
  <average_molecular_weight>416.6365</average_molecular_weight>
  <monisotopic_moleculate_weight>416.329045274</monisotopic_moleculate_weight>
  <iupac_name>(6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(1Z,5R)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol</iupac_name>
  <traditional_iupac>24,25-dihydroxyvitamin</traditional_iupac>
  <cas_registry_number>40013-87-4</cas_registry_number>
  <smiles>C[C@H](CCC(O)C(C)(C)O)[C@H]1CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@H](O)CCC1=C</smiles>
  <inchi>InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22-,23-,24+,25?,27-/m1/s1</inchi>
  <inchikey>FCKJYANJHNLEEP-OIMXRAFZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Vitamin D and derivatives</sub_class>
    <direct_parent>Vitamin D and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Triterpenoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(1Z,5R)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>416.6365</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>416.329045274</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](CCC(O)C(C)(C)O)[C@H]1CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@H](O)CCC1=C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H44O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22-,23-,24+,25?,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FCKJYANJHNLEEP-OIMXRAFZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>126.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300922</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300924</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37529</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2</concentration_value>
      <concentration_units>IU/100 g</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000065</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Reeve LE, Jorgensen NA, DeLuca HF: Vitamin D compounds in cows' milk. J Nutr. 1982 Apr;112(4):667-72. doi: 10.1093/jn/112.4.667.</reference_text>
          <pubmed_id>6279806</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0001 +/- 0.00001</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Received 4,000 iu/day supplement of cholecalciferol</comment>
      <references>
        <reference>
          <reference_text>Hollis BW, Roos BA, Draper HH, Lambert PW: Vitamin D and its metabolites in human and bovine milk. J Nutr. 1981 Jul;111(7):1240-8. doi: 10.1093/jn/111.7.1240.</reference_text>
          <pubmed_id>6788913</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00009 +/- 0.00002</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Hollis BW, Roos BA, Draper HH, Lambert PW: Vitamin D and its metabolites in human and bovine milk. J Nutr. 1981 Jul;111(7):1240-8. doi: 10.1093/jn/111.7.1240.</reference_text>
          <pubmed_id>6788913</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB021793</foodb_id>
  <chemspider_id>17215953</chemspider_id>
  <pubchem_compound_id>12895043</pubchem_compound_id>
  <chebi_id>89324</chebi_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5419</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Reeve LE, Jorgensen NA, DeLuca HF: Vitamin D compounds in cows' milk. J Nutr. 1982 Apr;112(4):667-72. doi: 10.1093/jn/112.4.667.</reference_text>
      <pubmed_id>6279806</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hollis BW, Roos BA, Draper HH, Lambert PW: Vitamin D and its metabolites in human and bovine milk. J Nutr. 1981 Jul;111(7):1240-8. doi: 10.1093/jn/111.7.1240.</reference_text>
      <pubmed_id>6788913</pubmed_id>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP02570</protein_accession>
      <name>Vitamin D-binding protein</name>
      <uniprot_id>Q3MHN5</uniprot_id>
      <gene_name>GC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02571</protein_accession>
      <name>Chromatin assembly factor 1 subunit A</name>
      <uniprot_id>A6QLA6</uniprot_id>
      <gene_name>CHAF1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02572</protein_accession>
      <name>TOB2 protein</name>
      <uniprot_id>A4FUY5</uniprot_id>
      <gene_name>TOB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02573</protein_accession>
      <name>Calbindin</name>
      <uniprot_id>P04467</uniprot_id>
      <gene_name>CALB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02574</protein_accession>
      <name>SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily B member 1</name>
      <uniprot_id>Q5BIN2</uniprot_id>
      <gene_name>SMARCB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02575</protein_accession>
      <name>SWI/SNF-related matrix-associated actin-dependent regulator of chromatin subfamily D member 1</name>
      <uniprot_id>Q2TBN1</uniprot_id>
      <gene_name>SMARCD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02576</protein_accession>
      <name>Protein S100-G</name>
      <uniprot_id>P02633</uniprot_id>
      <gene_name>S100G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:39 UTC</creation_date>
  <update_date>2020-03-13 16:21:11 UTC</update_date>
  <accession>BMDB0000431</accession>
  <secondary_accessions>
    <accession>BMDB00431</accession>
  </secondary_accessions>
  <name>16,17-Epiestriol</name>
  <description/>
  <synonyms>
    <synonym>1617-Epiestriol</synonym>
    <synonym>16,17-Epi-estriol</synonym>
    <synonym>16b,17a-Estriol</synonym>
    <synonym>16b-Hydroxy-17a-estradiol</synonym>
    <synonym>Estra-1,3,5(10)-triene-3,16b,17a-triol</synonym>
    <synonym>trans-Estriol</synonym>
  </synonyms>
  <chemical_formula>C18H24O3</chemical_formula>
  <average_molecular_weight>288.3814</average_molecular_weight>
  <monisotopic_moleculate_weight>288.172544634</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,13S,14S,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,13,14-triol</iupac_name>
  <traditional_iupac>16,17-epiestriol</traditional_iupac>
  <cas_registry_number>793-89-5</cas_registry_number>
  <smiles>[H][C@@]12C[C@H](O)[C@@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</smiles>
  <inchi>InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17-,18+/m1/s1</inchi>
  <inchikey>PROQIPRRNZUXQM-LMMHAMTPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>16-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>16-beta-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,13S,14S,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,13,14-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>288.3814</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>288.172544634</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@H](O)[C@@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H24O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17-,18+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PROQIPRRNZUXQM-LMMHAMTPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>81.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362520</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022041</foodb_id>
  <chemspider_id>13628086</chemspider_id>
  <pubchem_compound_id>21252247</pubchem_compound_id>
  <chebi_id>1150237</chebi_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id>16β,17α-Epiestriol</wikipedia_id>
  <metlin_id>5420</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Breuer, H.; Pangels, Gerta.  Isolation of 17-epiestriol and 16,17-epiestriol from the urine of pregnant women.    Z. physiol. Chem.  (1960),  322  177-83.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:40 UTC</creation_date>
  <update_date>2020-04-15 22:13:51 UTC</update_date>
  <accession>BMDB0000432</accession>
  <secondary_accessions>
    <accession>BMDB00432</accession>
  </secondary_accessions>
  <name>3a,7b,12a-Trihydroxy-5a-Cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>4-Methyl valeraldehyde</synonym>
    <synonym>Isocaproaldehyde</synonym>
    <synonym>Isohexanal</synonym>
    <synonym>4-Methyl-valeraldehyde</synonym>
    <synonym>4-Methylvaleraldehyde</synonym>
    <synonym>Isocaproaldehyde: 4-methyl-pentanal</synonym>
    <synonym>Isohexana</synonym>
    <synonym>3a,7b,12a-Trihydroxy-5a-cholanoate</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,7R,9S,10R,11S,14R,15R,16S)-5,9,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7R,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,7R,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>1119-16-0</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15-,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1</inchi>
  <inchikey>BHQCQFFYRZLCQQ-PWNRUWOFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Alpha-hydrogen aldehydes</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydrogen aldehyde</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>alpha-CH2-containing aldehyde</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7R,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15-,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHQCQFFYRZLCQQ-PWNRUWOFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342663</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>126</chemspider_id>
  <foodb_id>FDB022551</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>129</pubchem_compound_id>
  <kegg_id>C02373</kegg_id>
  <pdbe_id/>
  <chebi_id>17998</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>39716</bigg_id>
  <wikipedia_id/>
  <metlin_id>6155</metlin_id>
  <synthesis_reference>Iida, Takashi; Shinohara, Toshiyuki; Momose, Toshiaki; Tamura, Toshitake; Matsumoto, Taro; Nambara, Toshio; Chang, Frederic C.  Potential bile acid metabolites; 12.  Synthesis of stereoisomeric 3,7,12-trihydroxy-5a-cholanic acids and related compounds.    Synthesis  (1986),   (12),  998-1004.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:41 UTC</creation_date>
  <update_date>2020-04-15 22:13:52 UTC</update_date>
  <accession>BMDB0000433</accession>
  <secondary_accessions>
    <accession>BMDB00433</accession>
  </secondary_accessions>
  <name>1,3,7,12-Tetrahydroxycholan-24-oic acid</name>
  <description/>
  <synonyms>
    <synonym>1,3,7,12-Tetrahydroxycholan-24-Oate</synonym>
    <synonym>(4R)-4-[(1S,2S,9S,10S,11S,14R,15R)-3,5,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
    <synonym>(4R)-4-[(1S,2S,9S,10S,11S,14R,15R)-3,5,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O6</chemical_formula>
  <average_molecular_weight>424.578</average_molecular_weight>
  <monisotopic_moleculate_weight>424.282489008</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,9S,10S,11S,14R,15R)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,9S,10S,11S,14R,15R)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@](C)(CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@@]([H])(O)CC4([H])CC([H])(O)CC([H])(O)[C@]4(C)[C@@]3([H])CC([H])(O)[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O6/c1-12(4-7-21(29)30)15-5-6-16-22-17(11-20(28)24(15,16)3)23(2)13(9-18(22)26)8-14(25)10-19(23)27/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)/t12-,13?,14?,15-,16+,17+,18+,19?,20?,22+,23+,24-/m1/s1</inchi>
  <inchikey>UYVVLXVBEQAATF-QUHLNWFUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Tetrahydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxysteroids</alternative_parent>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxysteroid</substituent>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,9S,10S,11S,14R,15R)-3,5,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>424.578</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>424.282489008</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](C)(CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@@]([H])(O)CC4([H])CC([H])(O)CC([H])(O)[C@]4(C)[C@@]3([H])CC([H])(O)[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O6/c1-12(4-7-21(29)30)15-5-6-16-22-17(11-20(28)24(15,16)3)23(2)13(9-18(22)26)8-14(25)10-19(23)27/h12-20,22,25-28H,4-11H2,1-3H3,(H,29,30)/t12-,13?,14?,15-,16+,17+,18+,19?,20?,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UYVVLXVBEQAATF-QUHLNWFUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>112.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>48.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1257364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1257365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1257366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1372528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1372529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1372530</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:42 UTC</creation_date>
  <update_date>2020-03-13 16:21:13 UTC</update_date>
  <accession>BMDB0000434</accession>
  <secondary_accessions>
    <accession>BMDB00434</accession>
  </secondary_accessions>
  <name>Homoveratric acid</name>
  <description/>
  <synonyms>
    <synonym>2-(3,4-Dimethoxyphenyl)acetic acid</synonym>
    <synonym>2-(3,4-Dimethoxyphenyl)ethanoic acid</synonym>
    <synonym>3,4-Dimethoxybenzeneacetic acid</synonym>
    <synonym>3,4-Dimethoxyphenylacetic acid</synonym>
    <synonym>Homoveratrumic acid</synonym>
    <synonym>2-(3,4-Dimethoxyphenyl)acetate</synonym>
    <synonym>2-(3,4-Dimethoxyphenyl)ethanoate</synonym>
    <synonym>3,4-Dimethoxybenzeneacetate</synonym>
    <synonym>3,4-Dimethoxyphenylacetate</synonym>
    <synonym>Homoveratrumate</synonym>
    <synonym>Homoveratrate</synonym>
    <synonym>(3,4-Dimethoxyphenyl)acetate</synonym>
    <synonym>(3,4-Dimethoxyphenyl)acetic acid</synonym>
  </synonyms>
  <chemical_formula>C10H12O4</chemical_formula>
  <average_molecular_weight>196.1999</average_molecular_weight>
  <monisotopic_moleculate_weight>196.073558872</monisotopic_moleculate_weight>
  <iupac_name>2-(3,4-dimethoxyphenyl)acetic acid</iupac_name>
  <traditional_iupac>3,4-dimethoxyphenylacetic acid</traditional_iupac>
  <cas_registry_number>93-40-3</cas_registry_number>
  <smiles>COC1=CC=C(CC(O)=O)C=C1OC</smiles>
  <inchi>InChI=1S/C10H12O4/c1-13-8-4-3-7(6-10(11)12)5-9(8)14-2/h3-5H,6H2,1-2H3,(H,11,12)</inchi>
  <inchikey>WUAXWQRULBZETB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Methoxybenzenes</sub_class>
    <direct_parent>Dimethoxybenzenes</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dimethoxybenzene</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>O-dimethoxybenzene</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>96 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(3,4-dimethoxyphenyl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>196.1999</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>196.073558872</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC=C(CC(O)=O)C=C1OC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12O4/c1-13-8-4-3-7(6-10(11)12)5-9(8)14-2/h3-5H,6H2,1-2H3,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WUAXWQRULBZETB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>55.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1368</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242907</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB000317</foodb_id>
  <chemspider_id>6872</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>7139</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>86655</chebi_id>
  <phenol_explorer_compound_id>575</phenol_explorer_compound_id>
  <drugbank_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5423</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Aboulezz, A. F.; Quelet, R.  Derivatives of veratrole. Synthesis of homoveratric acid and some substituted diphenylmethane and fluorenone derivatives.    Journal of Chemistry of the United Arab Republic  (1962),  5(2),  137-46.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:44 UTC</creation_date>
  <update_date>2020-04-15 22:13:53 UTC</update_date>
  <accession>BMDB0000437</accession>
  <secondary_accessions>
    <accession>BMDB00437</accession>
  </secondary_accessions>
  <name>3a,4b,7a,12a-Tetrahydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3a,4b,7a,12a-Tetrahydroxy-5b-cholanoate</synonym>
    <synonym>3a,4b,7a,12a-Tetrahydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,4b,7a,12a-Tetrahydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>(4R)-4-[(1S,2R,5R,6R,7S,9R,10R,11S,14R,15R,16S)-5,6,9,16-Tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O6</chemical_formula>
  <average_molecular_weight>424.5708</average_molecular_weight>
  <monisotopic_moleculate_weight>424.282489012</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5R,6R,7S,9R,10R,11S,14R,15R,16S)-5,6,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5R,6R,7S,9R,10R,11S,14R,15R,16S)-5,6,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>122742-19-2</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])[C@@H](O)[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O6/c1-12(4-7-20(28)29)13-5-6-14-21-15(11-19(27)24(13,14)3)23(2)9-8-17(25)22(30)16(23)10-18(21)26/h12-19,21-22,25-27,30H,4-11H2,1-3H3,(H,28,29)/t12-,13-,14+,15+,16-,17-,18-,19+,21+,22-,23-,24-/m1/s1</inchi>
  <inchikey>WGGZRKVUOFMQHM-HPJHAEAHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Tetrahydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>4-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5R,6R,7S,9R,10R,11S,14R,15R,16S)-5,6,9,16-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>424.5708</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>424.282489012</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])[C@@H](O)[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O6/c1-12(4-7-20(28)29)13-5-6-14-21-15(11-19(27)24(13,14)3)23(2)9-8-17(25)22(30)16(23)10-18(21)26/h12-19,21-22,25-27,30H,4-11H2,1-3H3,(H,28,29)/t12-,13-,14+,15+,16-,17-,18-,19+,21+,22-,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WGGZRKVUOFMQHM-HPJHAEAHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>112.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>325252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>325253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>325254</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022044</foodb_id>
  <chemspider_id>4446983</chemspider_id>
  <pubchem_compound_id>5283895</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5426</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Iida, Takashi; Momose, Toshiaki; Chang, Frederic C.; Goto, Junichi; Nambara, Toshio.  Potential bile acid metabolites.  XV.  Synthesis of 4b-hydroxylated bile acids; unique bile acids in human fetal bile.    Chemical &amp; Pharmaceutical Bulletin  (1989),  37(12),  3323-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:45 UTC</creation_date>
  <update_date>2020-04-15 22:13:54 UTC</update_date>
  <accession>BMDB0000438</accession>
  <secondary_accessions>
    <accession>BMDB00438</accession>
  </secondary_accessions>
  <name>3b,12a-Dihydroxy-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>(3beta,5beta,12alpha)-3,12-Dihydroxycholan-24-Oic acid</synonym>
    <synonym>3-Epideoxycholic acid</synonym>
    <synonym>3beta-Deoxycholic acid</synonym>
    <synonym>Isodeoxycholic acid</synonym>
    <synonym>(3b,5b,12a)-3,12-Dihydroxycholan-24-Oate</synonym>
    <synonym>(3b,5b,12a)-3,12-Dihydroxycholan-24-Oic acid</synonym>
    <synonym>(3beta,5beta,12alpha)-3,12-Dihydroxycholan-24-Oate</synonym>
    <synonym>(3Β,5β,12α)-3,12-dihydroxycholan-24-Oate</synonym>
    <synonym>(3Β,5β,12α)-3,12-dihydroxycholan-24-Oic acid</synonym>
    <synonym>3-Epideoxycholate</synonym>
    <synonym>3b-Deoxycholate</synonym>
    <synonym>3b-Deoxycholic acid</synonym>
    <synonym>3beta-Deoxycholate</synonym>
    <synonym>3Β-deoxycholate</synonym>
    <synonym>3Β-deoxycholic acid</synonym>
    <synonym>Isodeoxycholate</synonym>
    <synonym>3b,12a-Dihydroxy-5b-cholanoate</synonym>
    <synonym>3b,12a-Dihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3b,12a-Dihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3b,12a-Dihydroxy-5b-cholanate</synonym>
    <synonym>3b,12a-Dihydroxy-5b-cholanic acid</synonym>
    <synonym>3b,12a-Dihydroxycholanoate</synonym>
    <synonym>3b,12a-Dihydroxycholanoic acid</synonym>
    <synonym>5b-Cholanic acid-3b,12a-diol</synonym>
  </synonyms>
  <chemical_formula>C24H40O4</chemical_formula>
  <average_molecular_weight>392.572</average_molecular_weight>
  <monisotopic_moleculate_weight>392.292659768</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5S,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>3-epideoxycholic acid</traditional_iupac>
  <cas_registry_number>570-63-8</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17+,18-,19+,20+,21+,23+,24-/m1/s1</inchi>
  <inchikey>KXGVEGMKQFWNSR-OFYXWCICSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5S,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>392.572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.292659768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17+,18-,19+,20+,21+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KXGVEGMKQFWNSR-OFYXWCICSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345216</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022045</foodb_id>
  <chemspider_id>141062</chemspider_id>
  <pubchem_compound_id>160530</pubchem_compound_id>
  <chebi_id>88098</chebi_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5427</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Danielsson, Henry; Eneroth, Peter; Hellstrom, Kjell; Sjovall, Jan.  Bile acids and steroids. CXXIII. Synthesis of some 3b-hydroxylated bile acids and the isolation of 3b,12a-dihydroxy-5b-cholanic acid from feces.    Journal of Biological Chemistry  (1962),  237  3657-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:46 UTC</creation_date>
  <update_date>2020-03-13 16:21:14 UTC</update_date>
  <accession>BMDB0000439</accession>
  <secondary_accessions>
    <accession>BMDB00439</accession>
  </secondary_accessions>
  <name>2-Furoylglycine</name>
  <description/>
  <synonyms>
    <synonym>N-(2-Furoyl)glycine</synonym>
    <synonym>Furfuroylglycine</synonym>
    <synonym>Furoylglycine</synonym>
    <synonym>N-(2-Furanylcarbonyl)glycine</synonym>
    <synonym>N-(Carboxymethyl)-2-furancarboxamide</synonym>
    <synonym>N-2-Furoyl-glycine</synonym>
    <synonym>Pyromucurate</synonym>
    <synonym>Pyromucuric acid</synonym>
    <synonym>[[(Furan-2-yl)carbonyl]amino]acetate</synonym>
    <synonym>[[(Furan-2-yl)carbonyl]amino]acetic acid</synonym>
  </synonyms>
  <chemical_formula>C7H7NO4</chemical_formula>
  <average_molecular_weight>169.1348</average_molecular_weight>
  <monisotopic_moleculate_weight>169.037507717</monisotopic_moleculate_weight>
  <iupac_name>2-[(furan-2-yl)formamido]acetic acid</iupac_name>
  <traditional_iupac>furoylglycine</traditional_iupac>
  <cas_registry_number>5657-19-2</cas_registry_number>
  <smiles>OC(=O)CNC(=O)C1=CC=CO1</smiles>
  <inchi>InChI=1S/C7H7NO4/c9-6(10)4-8-7(11)5-2-1-3-12-5/h1-3H,4H2,(H,8,11)(H,9,10)</inchi>
  <inchikey>KSPQDMRTZZYQLM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>2-heteroaryl carboxamides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Furoic acid and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-heteroaryl carboxamide</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Furan</substituent>
      <substituent>Furoic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylglycine</external_descriptor>
      <external_descriptor>furans</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>163 - 165 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>31.7 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(furan-2-yl)formamido]acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>169.1348</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>169.037507717</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CNC(=O)C1=CC=CO1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H7NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H7NO4/c9-6(10)4-8-7(11)5-2-1-3-12-5/h1-3H,4H2,(H,8,11)(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KSPQDMRTZZYQLM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>79.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450244</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022046</foodb_id>
  <chemspider_id>20549</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>21863</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>82912</chebi_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5428</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Laham, Souheil; Potvin, Marc.  Metabolism of furfural in the Sprague-Dawley rat.    Toxicological and Environmental Chemistry  (1989),  24(1-2),  35-47.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:47 UTC</creation_date>
  <update_date>2020-03-13 16:21:15 UTC</update_date>
  <accession>BMDB0000440</accession>
  <secondary_accessions>
    <accession>BMDB00440</accession>
  </secondary_accessions>
  <name>3-Hydroxyphenylacetic acid</name>
  <description>3-Hydroxyphenylacetic acid, also known as (m-hydroxyphenyl)acetate or 3-hydroxybenzeneacetate, belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. 3-Hydroxyphenylacetic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 3-Hydroxyphenylacetic acid exists in all living organisms, ranging from bacteria to humans. 3-Hydroxyphenylacetic acid has been found to be associated with several diseases known as colorectal cancer and eosinophilic esophagitis; also 3-hydroxyphenylacetic acid has been linked to the inborn metabolic disorders including phenylketonuria.</description>
  <synonyms>
    <synonym>(m-Hydroxyphenyl)acetic acid</synonym>
    <synonym>3-Hydroxybenzeneacetic acid</synonym>
    <synonym>m-Hydroxyphenylacetic acid</synonym>
    <synonym>(m-Hydroxyphenyl)acetate</synonym>
    <synonym>3-Hydroxybenzeneacetate</synonym>
    <synonym>m-Hydroxyphenylacetate</synonym>
    <synonym>3-Hydroxyphenylacetate</synonym>
    <synonym>(3-Hydroxy-phenyl)-acetate</synonym>
    <synonym>(3-Hydroxy-phenyl)-acetic acid</synonym>
    <synonym>3-Hydroxy-benzeneacetate</synonym>
    <synonym>3-Hydroxy-benzeneacetic acid</synonym>
    <synonym>Meta-hydroxyphenylacetic acid</synonym>
    <synonym>3-Hydroxyphenylacetic acid</synonym>
  </synonyms>
  <chemical_formula>C8H8O3</chemical_formula>
  <average_molecular_weight>152.1473</average_molecular_weight>
  <monisotopic_moleculate_weight>152.047344122</monisotopic_moleculate_weight>
  <iupac_name>2-(3-hydroxyphenyl)acetic acid</iupac_name>
  <traditional_iupac>3-hydroxyphenylacetic acid</traditional_iupac>
  <cas_registry_number>621-37-4</cas_registry_number>
  <smiles>OC(=O)CC1=CC(O)=CC=C1</smiles>
  <inchi>InChI=1S/C8H8O3/c9-7-3-1-2-6(4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)</inchi>
  <inchikey>FVMDYYGIDFPZAX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>1-hydroxy-4-unsubstituted benzenoids</sub_class>
    <direct_parent>1-hydroxy-4-unsubstituted benzenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>monocarboxylic acid</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(3-hydroxyphenyl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>152.1473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>152.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC1=CC(O)=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H8O3/c9-7-3-1-2-6(4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FVMDYYGIDFPZAX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440172</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022047</foodb_id>
  <chemspider_id>11624</chemspider_id>
  <kegg_id>C05593</kegg_id>
  <pubchem_compound_id>12122</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17445</chebi_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>4-Hydroxyphenylacetic acid</wikipedia_id>
  <metlin_id>5429</metlin_id>
  <meta_cyc_id>3-HYDROXYPHENYLACETATE</meta_cyc_id>
  <synthesis_reference>Staudenmaier, Horst Ralf; Hauer, Bernhard; Ladner, Wolfgang; Mueller, Ursula; Pressler, Uwe; Meyer, Joachim.  Fermentative manufacture of 3-hydroxyphenylacetic acid.    Ger. Offen.  (1993),     6 pp. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:48 UTC</creation_date>
  <update_date>2020-04-16 20:38:27 UTC</update_date>
  <accession>BMDB0000442</accession>
  <secondary_accessions>
    <accession>BMDB00442</accession>
  </secondary_accessions>
  <name>(S)-3-Hydroxybutyric acid</name>
  <description/>
  <synonyms>
    <synonym>(+)-3-Hydroxybutyric acid</synonym>
    <synonym>(3S)-3-Hydroxybutyric acid</synonym>
    <synonym>(S)-3-Hydroxybutanoic acid</synonym>
    <synonym>(S)-3Hb</synonym>
    <synonym>(S)-beta-Hydroxybutyric acid</synonym>
    <synonym>L-(+)-3-Hydroxybutyric acid</synonym>
    <synonym>L-3-Hydroxybutyric acid</synonym>
    <synonym>(+)-3-Hydroxybutyrate</synonym>
    <synonym>(3S)-3-Hydroxybutyrate</synonym>
    <synonym>(S)-3-Hydroxybutanoate</synonym>
    <synonym>(S)-b-Hydroxybutyrate</synonym>
    <synonym>(S)-b-Hydroxybutyric acid</synonym>
    <synonym>(S)-beta-Hydroxybutyrate</synonym>
    <synonym>(S)-Β-hydroxybutyrate</synonym>
    <synonym>(S)-Β-hydroxybutyric acid</synonym>
    <synonym>L-(+)-3-Hydroxybutyrate</synonym>
    <synonym>L-3-Hydroxybutyrate</synonym>
    <synonym>(S)-3-Hydroxybutyrate</synonym>
    <synonym>(+)-3-Hydroxy-N-butyric acid</synonym>
    <synonym>(3S)-3-Hydroxy-butanoate</synonym>
    <synonym>(3S)-3-Hydroxy-butanoic acid</synonym>
    <synonym>(S)-3-Hydroxy-2-methyl-propanoate</synonym>
    <synonym>(S)-3-Hydroxy-2-methyl-propanoic acid</synonym>
    <synonym>(S)-3-Hydroxy-butanoate</synonym>
    <synonym>(S)-3-Hydroxy-butanoic acid</synonym>
    <synonym>(S)-b-Hydroxyisobutyrate</synonym>
    <synonym>(S)-b-Hydroxyisobutyric acid</synonym>
    <synonym>(S)-beta-Hydroxyisobutyrate</synonym>
    <synonym>(S)-beta-Hydroxyisobutyric acid</synonym>
    <synonym>L-(+)-2-Methyl-hydracrylate</synonym>
    <synonym>L-(+)-2-Methyl-hydracrylic acid</synonym>
    <synonym>L-(+)-b-Hydroxyisobutyrate</synonym>
    <synonym>L-(+)-b-Hydroxyisobutyric acid</synonym>
    <synonym>L-(+)-beta-Hydroxyisobutyrate</synonym>
    <synonym>L-(+)-beta-Hydroxyisobutyric acid</synonym>
    <synonym>L-beta-Hydroxybutyrate</synonym>
    <synonym>(3S)-3-Hydroxybutanoic acid</synonym>
    <synonym>(S)-(+)-beta-Hydroxybutyric acid</synonym>
    <synonym>(S)-(+)-β-Hydroxybutyric acid</synonym>
    <synonym>(S)-3-Hydroxybutyric acid</synonym>
    <synonym>(S)-beta-Hydroxybutanoic acid</synonym>
    <synonym>(S)-β-Hydroxybutanoic acid</synonym>
    <synonym>3-Hydroxy-n-butyric acid</synonym>
    <synonym>3-Hydroxybutanoic acid</synonym>
    <synonym>3-Hydroxybutyric acid</synonym>
    <synonym>L-beta-Hydroxybutyric acid</synonym>
    <synonym>L-β-Hydroxybutyric acid</synonym>
    <synonym>beta-Hydroxy-n-butyric acid</synonym>
    <synonym>beta-Hydroxybutanoic acid</synonym>
    <synonym>beta-Hydroxybutyric acid</synonym>
    <synonym>β-Hydroxy-n-butyric acid</synonym>
    <synonym>β-Hydroxybutanoic acid</synonym>
    <synonym>β-Hydroxybutyric acid</synonym>
  </synonyms>
  <chemical_formula>C4H8O3</chemical_formula>
  <average_molecular_weight>104.1045</average_molecular_weight>
  <monisotopic_moleculate_weight>104.047344122</monisotopic_moleculate_weight>
  <iupac_name>(3S)-3-hydroxybutanoic acid</iupac_name>
  <traditional_iupac>β-hydroxybutyrate,l</traditional_iupac>
  <cas_registry_number>6168-83-8</cas_registry_number>
  <smiles>C[C@H](O)CC(O)=O</smiles>
  <inchi>InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1</inchi>
  <inchikey>WHBMMWSBFZVSSR-VKHMYHEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Beta hydroxy acids and derivatives</sub_class>
    <direct_parent>Beta hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hydroxybutyric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>45 - 48 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3S)-3-hydroxybutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>104.1045</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>104.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WHBMMWSBFZVSSR-VKHMYHEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>23.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348738</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022048</foodb_id>
  <chemspider_id>85121</chemspider_id>
  <kegg_id>C03197</kegg_id>
  <pubchem_compound_id>94318</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17290</chebi_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Beta-Hydroxybutyric_acid</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id>CPD-1843</meta_cyc_id>
  <synthesis_reference>Zhao, Jun.  Synthesis of (S)-b-hydroxybutanoic acid from L-lactic acid.    Hecheng Huaxue  (1998),  6(4),  442-444.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00595</protein_accession>
      <name>Hydroxyacid-oxoacid transhydrogenase, mitochondrial</name>
      <uniprot_id>A6QP15</uniprot_id>
      <gene_name>ADHFE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:49 UTC</creation_date>
  <update_date>2020-03-13 16:21:16 UTC</update_date>
  <accession>BMDB0000444</accession>
  <secondary_accessions>
    <accession>BMDB00444</accession>
  </secondary_accessions>
  <name>3-Furoic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Carboxyfuran</synonym>
    <synonym>3-Furancarboxylic acid</synonym>
    <synonym>3-Furancarboxylate</synonym>
    <synonym>3-Furoate</synonym>
    <synonym>3-Furanoate</synonym>
    <synonym>3-Furanoic acid</synonym>
  </synonyms>
  <chemical_formula>C5H4O3</chemical_formula>
  <average_molecular_weight>112.0835</average_molecular_weight>
  <monisotopic_moleculate_weight>112.016043994</monisotopic_moleculate_weight>
  <iupac_name>furan-3-carboxylic acid</iupac_name>
  <traditional_iupac>3-furoic acid</traditional_iupac>
  <cas_registry_number>488-93-7</cas_registry_number>
  <smiles>OC(=O)C1=COC=C1</smiles>
  <inchi>InChI=1S/C5H4O3/c6-5(7)4-1-2-8-3-4/h1-3H,(H,6,7)</inchi>
  <inchikey>IHCCAYCGZOLTEU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as furoic acids. These are organic compounds containing a furoic acid moiety, with a structure characterized by a furan ring bearing a carboxylic acid group at the C2 or C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Furans</class>
    <sub_class>Furoic acid and derivatives</sub_class>
    <direct_parent>Furoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Furan-3-carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Furan-3-carboxylic acid</substituent>
      <substituent>Furan-3-carboxylic acid or derivatives</substituent>
      <substituent>Furoic acid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>furoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>120 - 122 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>64 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.03</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>furan-3-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>112.0835</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>112.016043994</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1=COC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H4O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H4O3/c6-5(7)4-1-2-8-3-4/h1-3H,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IHCCAYCGZOLTEU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>50.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332241</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022049</foodb_id>
  <chemspider_id>9849</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>10268</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30846</chebi_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>2-Furoic acid</wikipedia_id>
  <metlin_id>5433</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Ghosh, A.; Raha, C. R. Synthesis of 3-furoic acid.  Indian Chem. Soc. (1954), 31 461-2.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:51 UTC</creation_date>
  <update_date>2020-03-13 16:21:16 UTC</update_date>
  <accession>BMDB0000445</accession>
  <secondary_accessions>
    <accession>BMDB00445</accession>
  </secondary_accessions>
  <name>Alpha-Tetrasaccharide</name>
  <description/>
  <synonyms>
    <synonym>a-Tetrasaccharide</synonym>
    <synonym>Α-tetrasaccharide</synonym>
    <synonym>a-D-GalNAc-(1-&gt;3)[a-L-fuc-(1-&gt;2)]-b-D-gal-(1-&gt;4)-D-GLC</synonym>
    <synonym>alpha-D-GalNAc-(1-&gt;3)[a-L-fuc-(1-&gt;2)]-beta-D-gal-(1-&gt;4)-D-GLC</synonym>
    <synonym>alpha-delta-GalNAc-(1-&gt;3)[a-L-fuc-(1-&gt;2)]-beta-delta-gal-(1-&gt;4)-delta-GLC</synonym>
    <synonym>O-2-(Acetylamino)-2-deoxy-a-D-galactopyranosyl-(1-&gt;3)-O-[6-deoxy-a-L-galactopyranosyl-(1-&gt;2)]-O-b-D-galactopyranosyl-(1-&gt;4)-D-glucose</synonym>
    <synonym>O-2-(Acetylamino)-2-deoxy-alpha-D-galactopyranosyl-(1-&gt;3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1-&gt;2)]-O-beta-D-galactopyranosyl-(1-&gt;4)-D-glucose</synonym>
    <synonym>O-2-(Acetylamino)-2-deoxy-alpha-delta-galactopyranosyl-(1-&gt;3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1-&gt;2)]-O-beta-delta-galactopyranosyl-(1-&gt;4)-delta-glucose</synonym>
    <synonym>GalNAc-1-3-(fuc-1-2)gal-1-4-GLC-pa</synonym>
    <synonym>N-Acetylgalactosaminyl-1-3-(fucopyranosyl-1-2)-galactopyranosyl-1-4-glucopyranosyl-pyridylamino</synonym>
    <synonym>N-[(2R,3R,4R,5R,6R)-4,5-Dihydroxy-2-{[(2R,3S,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]ethanimidate</synonym>
  </synonyms>
  <chemical_formula>C26H45NO20</chemical_formula>
  <average_molecular_weight>691.6302</average_molecular_weight>
  <monisotopic_moleculate_weight>691.253492885</monisotopic_moleculate_weight>
  <iupac_name>N-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-{[(2R,3S,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]acetamide</iupac_name>
  <traditional_iupac>N-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-{[(2R,3S,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]acetamide</traditional_iupac>
  <cas_registry_number>59957-92-5</cas_registry_number>
  <smiles>[H][C@@](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O[C@@]2([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]2NC(C)=O)[C@H]1O[C@]1([H])O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]1O)([C@H](O)CO)[C@H](O)[C@@H](O)C=O</smiles>
  <inchi>InChI=1S/C26H45NO20/c1-7-14(35)19(40)20(41)25(42-7)47-23-22(46-24-13(27-8(2)32)18(39)16(37)11(5-30)43-24)17(38)12(6-31)44-26(23)45-21(10(34)4-29)15(36)9(33)3-28/h3,7,9-26,29-31,33-41H,4-6H2,1-2H3,(H,27,32)/t7-,9-,10+,11+,12+,13+,14+,15+,16-,17-,18+,19+,20-,21+,22-,23+,24+,25-,26-/m0/s1</inchi>
  <inchikey>DLJLMAWPOOWMRF-BFJQYDNNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Oligosaccharides</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alkyl glycosides</alternative_parent>
      <alternative_parent>Alpha-hydroxyaldehydes</alternative_parent>
      <alternative_parent>Beta-hydroxy aldehydes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl glycoside</substituent>
      <substituent>Alpha-hydroxyaldehyde</substituent>
      <substituent>Beta-hydroxy aldehyde</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty acyl glycoside</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Oligosaccharide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-8.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-{[(2R,3S,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]acetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>691.6302</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>691.253492885</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O[C@@]2([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]2NC(C)=O)[C@H]1O[C@]1([H])O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]1O)([C@H](O)CO)[C@H](O)[C@@H](O)C=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H45NO20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H45NO20/c1-7-14(35)19(40)20(41)25(42-7)47-23-22(46-24-13(27-8(2)32)18(39)16(37)11(5-30)43-24)17(38)12(6-31)44-26(23)45-21(10(34)4-29)15(36)9(33)3-28/h3,7,9-26,29-31,33-41H,4-6H2,1-2H3,(H,27,32)/t7-,9-,10+,11+,12+,13+,14+,15+,16-,17-,18+,19+,20-,21+,22-,23+,24+,25-,26-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DLJLMAWPOOWMRF-BFJQYDNNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>344.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>144.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>64.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366993</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>13628089</chemspider_id>
  <foodb_id>FDB022050</foodb_id>
  <kegg_id>C06768</kegg_id>
  <phenol_explorer_compound_id/>
  <pubchem_compound_id>21252248</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5434</metlin_id>
  <synthesis_reference>Narimatsu, Hisashi; Kudo, Takashi; Sasaki, Katsutoshi.  Cloning of cDNA or gene for a1,3-Fucosyltransferase Fuc-TIX from mouse and human and use of the encoding sequences and protein products.    PCT Int. Appl.  (2000),     172 pp.  CODEN: PIXXD2  WO  2000006708  A1  20000210  CAN 132:148489  AN 2000:98730</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:52 UTC</creation_date>
  <update_date>2020-03-13 16:21:17 UTC</update_date>
  <accession>BMDB0000446</accession>
  <secondary_accessions>
    <accession>BMDB00446</accession>
  </secondary_accessions>
  <name>N-Alpha-ccetyllysine</name>
  <description>Acetyllysine belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Acetyllysine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Acetyllysine exists in all eukaryotes, ranging from yeast to humans.</description>
  <synonyms>
    <synonym>(2S)-2-(Acetylamino)-6-aminohexanoic acid</synonym>
    <synonym>N(alpha)-Acetyllysine</synonym>
    <synonym>N-Acetyl-L-lysine</synonym>
    <synonym>N2-Acetyl-L-lysine</synonym>
    <synonym>N(alpha)-Acetyl-L-lysine</synonym>
    <synonym>(2S)-2-(Acetylamino)-6-aminohexanoate</synonym>
    <synonym>N(a)-Acetyllysine</synonym>
    <synonym>N(Α)-acetyllysine</synonym>
    <synonym>N(a)-Acetyl-L-lysine</synonym>
    <synonym>N(Α)-acetyl-L-lysine</synonym>
    <synonym>N-a-Acetyl-L-lysine</synonym>
    <synonym>N-Α-acetyl-L-lysine</synonym>
    <synonym>6-Amino-L-2-acetamidohexanoic acid</synonym>
    <synonym>N2-Acetyllysine</synonym>
    <synonym>Nα-acetyl-L-lysine</synonym>
    <synonym>Nα-acetyllysine</synonym>
    <synonym>Nalpha-acetyl-L-lysine</synonym>
    <synonym>Nalpha-acetyllysine</synonym>
    <synonym>N-a-Acetyllysine</synonym>
    <synonym>N-Α-acetyllysine</synonym>
    <synonym>6-Amino-L-2-acetamidohexanoate</synonym>
    <synonym>N-Acetyl poly-L-lysine</synonym>
    <synonym>N-Acetyl polylysine</synonym>
    <synonym>Acetyllysine</synonym>
    <synonym>6-Amino-2-[(1-hydroxyethylidene)amino]hexanoate</synonym>
    <synonym>N(2)-Acetyllysine</synonym>
    <synonym>N(alpha)-Acetyllysine, (DL)-isomer</synonym>
    <synonym>N-alpha-Acetyllysine</synonym>
    <synonym>N-alpha-Acetyl-L-lysine</synonym>
  </synonyms>
  <chemical_formula>C8H16N2O3</chemical_formula>
  <average_molecular_weight>188.227</average_molecular_weight>
  <monisotopic_moleculate_weight>188.116092383</monisotopic_moleculate_weight>
  <iupac_name>(2S)-6-amino-2-acetamidohexanoic acid</iupac_name>
  <traditional_iupac>nα-acetyllysine</traditional_iupac>
  <cas_registry_number>1946-82-3</cas_registry_number>
  <smiles>CC(=O)N[C@@H](CCCCN)C(O)=O</smiles>
  <inchi>InChI=1S/C8H16N2O3/c1-6(11)10-7(8(12)13)4-2-3-5-9/h7H,2-5,9H2,1H3,(H,10,11)(H,12,13)/t7-/m0/s1</inchi>
  <inchikey>VEYYWZRYIYDQJM-ZETCQYMHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>acetyl-L-lysine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-6-amino-2-acetamidohexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>188.227</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>188.116092383</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H](CCCCN)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16N2O3/c1-6(11)10-7(8(12)13)4-2-3-5-9/h7H,2-5,9H2,1H3,(H,10,11)(H,12,13)/t7-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VEYYWZRYIYDQJM-ZETCQYMHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5200</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022051</foodb_id>
  <kegg_id>C12989</kegg_id>
  <chemspider_id>167134</chemspider_id>
  <drugbank_id/>
  <chebi_id>35704</chebi_id>
  <pubchem_compound_id>92907</pubchem_compound_id>
  <pdbe_id/>
  <meta_cyc_id>N-ACETYL-L-LYSINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Acetyllysine</wikipedia_id>
  <metlin_id>5435</metlin_id>
  <synthesis_reference>Akagi, Aru; Soejima, Yasuhiro; Izumiya, Nobuo.  Facile syntheses of e-acyl-L-lysines and abnormal optical rotations of a-acyl-L-lysines.    Kyushu Sangyo Daigaku Kogakubu Kenkyu Hokoku  (1992),  29  119-24.  </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:53 UTC</creation_date>
  <update_date>2020-03-13 16:21:17 UTC</update_date>
  <accession>BMDB0000447</accession>
  <secondary_accessions>
    <accession>BMDB00447</accession>
  </secondary_accessions>
  <name>7a,12a-Dihydroxy-3-oxo-4-cholenoic acid</name>
  <description/>
  <synonyms>
    <synonym>7alpha,12alpha-Dihydroxy-3-oxochol-4-enoate</synonym>
    <synonym>7alpha,12alpha-Dihydroxy-3-oxochol-4-enoic acid</synonym>
    <synonym>7a,12a-Dihydroxy-3-oxochol-4-enoate</synonym>
    <synonym>7a,12a-Dihydroxy-3-oxochol-4-enoic acid</synonym>
    <synonym>7Α,12α-dihydroxy-3-oxochol-4-enoate</synonym>
    <synonym>7Α,12α-dihydroxy-3-oxochol-4-enoic acid</synonym>
    <synonym>7a,12a-Dihydroxy-3-oxo-4-cholenoate</synonym>
    <synonym>7a,12a-Dihydroxy-3-oxo-chol-4-en-24-Oate</synonym>
    <synonym>7a,12a-Dihydroxy-3-oxo-chol-4-en-24-Oic acid</synonym>
    <synonym>(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-Dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H36O5</chemical_formula>
  <average_molecular_weight>404.5396</average_molecular_weight>
  <monisotopic_moleculate_weight>404.256274262</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>13587-11-6</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2=CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H36O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h10,13,16-20,22,26-27H,4-9,11-12H2,1-3H3,(H,28,29)/t13-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1</inchi>
  <inchikey>ZZUMXQCSMJCDDC-DFQOQHGMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>12alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>3-oxo Delta(4)-steroid</external_descriptor>
      <external_descriptor>7alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>404.5396</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>404.256274262</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2=CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H36O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H36O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h10,13,16-20,22,26-27H,4-9,11-12H2,1-3H3,(H,28,29)/t13-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZZUMXQCSMJCDDC-DFQOQHGMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>45.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332313</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022052</foodb_id>
  <chemspider_id>4447084</chemspider_id>
  <pubchem_compound_id>5283996</pubchem_compound_id>
  <kegg_id>C15568</kegg_id>
  <chebi_id>49269</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5436</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Kallner, Anders.  Bile acids and steroids. 182.  A method of synthesis of allochlanoic acids.    Acta Chemica Scandinavica (1947-1973)  (1967),  21(2),  322-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:54 UTC</creation_date>
  <update_date>2020-04-14 22:47:29 UTC</update_date>
  <accession>BMDB0000448</accession>
  <secondary_accessions>
    <accession>BMDB00448</accession>
  </secondary_accessions>
  <name>Adipic acid</name>
  <description/>
  <synonyms>
    <synonym>1,4-Butanedicarboxylic acid</synonym>
    <synonym>1,6-Hexanedioic acid</synonym>
    <synonym>Adipinic acid</synonym>
    <synonym>Adipinsaeure</synonym>
    <synonym>e 355</synonym>
    <synonym>e-355</synonym>
    <synonym>e355</synonym>
    <synonym>INS no. 355</synonym>
    <synonym>Hexanedioate</synonym>
    <synonym>Hexan-1,6-dicarboxylate</synonym>
    <synonym>1,4-Butanedicarboxylate</synonym>
    <synonym>1,6-Hexanedioate</synonym>
    <synonym>Adipinate</synonym>
    <synonym>Hexanedioic acid</synonym>
    <synonym>Hexan-1,6-dicarboxylic acid</synonym>
    <synonym>Adipate</synonym>
    <synonym>Acifloctin</synonym>
    <synonym>Acinetten</synonym>
    <synonym>Adi-pure</synonym>
    <synonym>Adilactetten</synonym>
    <synonym>Kyselina adipova</synonym>
    <synonym>Molten adipate</synonym>
    <synonym>Molten adipic acid</synonym>
    <synonym>Adipic acid, calcium salt</synonym>
    <synonym>Adipic acid, disodium salt</synonym>
    <synonym>Sodium adipate</synonym>
    <synonym>Adipic acid, cu(+2) salt</synonym>
    <synonym>Adipic acid, cu(+2) salt (1:1)</synonym>
    <synonym>Adipic acid, diammonium salt</synonym>
    <synonym>Adipic acid, sodium salt</synonym>
    <synonym>Adipic acid, cu salt</synonym>
    <synonym>Adipic acid, potassium salt</synonym>
    <synonym>Ammonium adipate</synonym>
    <synonym>Magnesium adipate</synonym>
    <synonym>Adipic acid, MG salt (1:1)</synonym>
    <synonym>Adipic acid, monoammonium salt</synonym>
    <synonym>Adipic acid, nickel salt</synonym>
    <synonym>Diammonium adipate</synonym>
    <synonym>Adipic acid</synonym>
  </synonyms>
  <chemical_formula>C6H10O4</chemical_formula>
  <average_molecular_weight>146.1412</average_molecular_weight>
  <monisotopic_moleculate_weight>146.057908808</monisotopic_moleculate_weight>
  <iupac_name>hexanedioic acid</iupac_name>
  <traditional_iupac>adipic acid</traditional_iupac>
  <cas_registry_number>124-04-9</cas_registry_number>
  <smiles>OC(=O)CCCCC(O)=O</smiles>
  <inchi>InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)</inchi>
  <inchikey>WNLRTRBMVRJNCN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>alpha,omega-dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>151 - 154 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>30.8 mg/mL at 34 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.08</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>hexanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>146.1412</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>146.057908808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WNLRTRBMVRJNCN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438621</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB008309</foodb_id>
  <kegg_id>C06104</kegg_id>
  <chemspider_id>191</chemspider_id>
  <drugbank_id/>
  <chebi_id>30832</chebi_id>
  <pubchem_compound_id>196</pubchem_compound_id>
  <pdbe_id/>
  <meta_cyc_id>ADIPATE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001178</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Adipic_acid</wikipedia_id>
  <metlin_id>115</metlin_id>
  <synthesis_reference>Saito, Kenji.  Recovery of adipic acid. Jpn. Kokai Tokkyo Koho  (1976),     5 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:55 UTC</creation_date>
  <update_date>2020-03-13 16:21:18 UTC</update_date>
  <accession>BMDB0000449</accession>
  <secondary_accessions>
    <accession>BMDB00449</accession>
  </secondary_accessions>
  <name>5a-Tetrahydrocorticosterone</name>
  <description/>
  <synonyms>
    <synonym>3a,11b,21-Trihydroxy-5a-pregnan-20-one</synonym>
    <synonym>3a,5a-Tetrahydrocorticosterone</synonym>
    <synonym>5a-Pregnane-3a,11b,21-triol-20-one</synonym>
    <synonym>Allotetrahydrocorticosterone</synonym>
    <synonym>5Α-tetrahydrocorticosterone</synonym>
    <synonym>Tetrahydrocorticosterone</synonym>
    <synonym>Tetrahydrocorticosterone, (3alpha,5beta,11alpha)-isomer</synonym>
    <synonym>Tetrahydrocorticosterone, (3beta,5alpha,11beta)-isomer</synonym>
    <synonym>Tetrahydrocorticosterone, (3beta,5beta)-isomer</synonym>
    <synonym>Tetrahydrocorticosterone, (5alpha)-isomer</synonym>
    <synonym>3 beta,11 beta,21-Trihydroxy-5 alpha-pregnan-20-one</synonym>
    <synonym>AlloTHB</synonym>
    <synonym>Allopregnane-3 beta,11 beta,21-triol-20-one</synonym>
    <synonym>Tetrahydrocorticosterone, (3alpha,5alpha)-isomer</synonym>
    <synonym>5a-Tetrahydrocorticosterone</synonym>
  </synonyms>
  <chemical_formula>C21H34O4</chemical_formula>
  <average_molecular_weight>350.4923</average_molecular_weight>
  <monisotopic_moleculate_weight>350.245709576</monisotopic_moleculate_weight>
  <iupac_name>1-[(1S,2S,5R,7S,10S,11S,14S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-hydroxyethan-1-one</iupac_name>
  <traditional_iupac>allotetrahydrocorticosterone</traditional_iupac>
  <cas_registry_number>600-63-5</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H34O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-17,19,22-24H,3-11H2,1-2H3/t12-,13+,14-,15-,16+,17-,19+,20-,21-/m0/s1</inchi>
  <inchikey>RHQQHZQUAMFINJ-NZTKVECHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>11-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>11-beta-hydroxysteroid</substituent>
      <substituent>11-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(1S,2S,5R,7S,10S,11S,14S,15S,17S)-5,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2-hydroxyethan-1-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>350.4923</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>350.245709576</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H34O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H34O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-17,19,22-24H,3-11H2,1-2H3/t12-,13+,14-,15-,16+,17-,19+,20-,21-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RHQQHZQUAMFINJ-NZTKVECHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>96.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>123666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>123667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>123668</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>91970</chemspider_id>
  <foodb_id>FDB022053</foodb_id>
  <kegg_id/>
  <phenol_explorer_compound_id/>
  <pubchem_compound_id>101790</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>89328</chebi_id>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5438</metlin_id>
  <synthesis_reference>Harnik, M.  Syntheses of steroid metabolites. III.    Steroids  (1963),  2(5),  485-98.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:56 UTC</creation_date>
  <update_date>2020-04-14 22:47:29 UTC</update_date>
  <accession>BMDB0000450</accession>
  <secondary_accessions>
    <accession>BMDB00450</accession>
  </secondary_accessions>
  <name>5-Hydroxylysine</name>
  <description>5-Hydroxylysine, also known as lysine, 5 hydroxy, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 5-Hydroxylysine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 5-Hydroxylysine exists in all eukaryotes, ranging from yeast to humans. In cattle, 5-hydroxylysine is involved in the metabolic pathway called the lysine degradation pathway.</description>
  <synonyms>
    <synonym>(2S,5R)-5-Hydroxylysine</synonym>
    <synonym>(5R)-5-Hydroxy-L-lysine</synonym>
    <synonym>alpha,epsilon-Diamino-delta-hydroxycaproic acid</synonym>
    <synonym>L-Erythro-5-hydroxylysine</synonym>
    <synonym>L-Normal-5-hydroxylysine</synonym>
    <synonym>5-Hydroxy-L-lysine</synonym>
    <synonym>a,epsilon-Diamino-delta-hydroxycaproate</synonym>
    <synonym>a,epsilon-Diamino-delta-hydroxycaproic acid</synonym>
    <synonym>alpha,epsilon-Diamino-delta-hydroxycaproate</synonym>
    <synonym>Α,epsilon-diamino-δ-hydroxycaproate</synonym>
    <synonym>Α,epsilon-diamino-δ-hydroxycaproic acid</synonym>
    <synonym>a,epsilon-Diamino-δ-hydroxycaproate</synonym>
    <synonym>a,epsilon-Diamino-δ-hydroxycaproic acid</synonym>
    <synonym>(2S,5R)-2,6-Diamino-5-hydroxyhexanoate</synonym>
    <synonym>(2S,5R)-2,6-Diamino-5-hydroxyhexanoic acid</synonym>
    <synonym>5-Hydroxy-lysine</synonym>
    <synonym>D-Hydroxy-L-lysine</synonym>
    <synonym>D-Hydroxylysine</synonym>
    <synonym>delta-DL-Hydroxylysine</synonym>
    <synonym>delta-Hydroxy-L-lysine</synonym>
    <synonym>delta-Hydroxylysine</synonym>
    <synonym>Erythro-5-hydroxy-L-lysine</synonym>
    <synonym>Hydroxy-lysine</synonym>
    <synonym>Hydroxylysine</synonym>
    <synonym>L-D-Hydroxylysine</synonym>
    <synonym>L-delta-Hydroxylysine</synonym>
    <synonym>Procollagen 5-hydroxy-L-lysine</synonym>
    <synonym>Procollagen L-erythro-5-hydroxy-L-lysine</synonym>
    <synonym>2,6-Diamino-5-hydroxyhexanoic acid</synonym>
    <synonym>2,6 Diamino 5 hydroxyhexanoic acid</synonym>
    <synonym>Lysine, 5 hydroxy</synonym>
    <synonym>5 Hydroxylysine</synonym>
    <synonym>5-HYDROXYLYSINE</synonym>
  </synonyms>
  <chemical_formula>C6H14N2O3</chemical_formula>
  <average_molecular_weight>162.187</average_molecular_weight>
  <monisotopic_moleculate_weight>162.100442324</monisotopic_moleculate_weight>
  <iupac_name>(2S,5R)-2,6-diamino-5-hydroxyhexanoic acid</iupac_name>
  <traditional_iupac>L-hydroxylysine</traditional_iupac>
  <cas_registry_number>1190-94-9</cas_registry_number>
  <smiles>NC[C@H](O)CC[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C6H14N2O3/c7-3-4(9)1-2-5(8)6(10)11/h4-5,9H,1-3,7-8H2,(H,10,11)/t4-,5+/m1/s1</inchi>
  <inchikey>YSMODUONRAFBET-UHNVWZDZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>5-hydroxylysine</external_descriptor>
      <external_descriptor>hydroxy-L-lysine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>23 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,5R)-2,6-diamino-5-hydroxyhexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>162.187</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>162.100442324</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC[C@H](O)CC[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H14N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H14N2O3/c7-3-4(9)1-2-5(8)6(10)11/h4-5,9H,1-3,7-8H2,(H,10,11)/t4-,5+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YSMODUONRAFBET-UHNVWZDZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>109.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182387</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB012682</foodb_id>
  <kegg_id>C16741</kegg_id>
  <chemspider_id>2297721</chemspider_id>
  <drugbank_id/>
  <chebi_id>18040</chebi_id>
  <pubchem_compound_id>3032849</pubchem_compound_id>
  <pdbe_id/>
  <meta_cyc_id>CPD-14226</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>53055</bigg_id>
  <wikipedia_id>Hydroxylysine</wikipedia_id>
  <metlin_id>5439</metlin_id>
  <synthesis_reference>Allevi, P.; Anastasia, M. Synthesis of all four possible stereoisomers of 5-hydroxylysine. Tetrahedron: Asymmetry (2000), 11(15), 3151-3160.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:58 UTC</creation_date>
  <update_date>2020-03-13 16:21:19 UTC</update_date>
  <accession>BMDB0000451</accession>
  <secondary_accessions>
    <accession>BMDB00451</accession>
  </secondary_accessions>
  <name>cis-4-Hydroxycyclohexylacetic acid</name>
  <description/>
  <synonyms>
    <synonym>cis-4-Hydroxycyclohexylacetate</synonym>
    <synonym>4-Hydroxy-cyclohexylessigsaeure</synonym>
    <synonym>4-Hydroxycyclohexylacetate</synonym>
    <synonym>4-Hydroxycyclohexylacetic acid</synonym>
    <synonym>2-(4-Hydroxycyclohexyl)acetate</synonym>
  </synonyms>
  <chemical_formula>C8H14O3</chemical_formula>
  <average_molecular_weight>158.195</average_molecular_weight>
  <monisotopic_moleculate_weight>158.094294314</monisotopic_moleculate_weight>
  <iupac_name>2-(4-hydroxycyclohexyl)acetic acid</iupac_name>
  <traditional_iupac>4-hydroxycyclohexylacetate</traditional_iupac>
  <cas_registry_number>68592-22-3</cas_registry_number>
  <smiles>OC1CCC(CC(O)=O)CC1</smiles>
  <inchi>InChI=1S/C8H14O3/c9-7-3-1-6(2-4-7)5-8(10)11/h6-7,9H,1-5H2,(H,10,11)</inchi>
  <inchikey>ALTAAUJNHYWOGS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Cyclohexanols</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclohexanol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(4-hydroxycyclohexyl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>158.195</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>158.094294314</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC1CCC(CC(O)=O)CC1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H14O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H14O3/c9-7-3-1-6(2-4-7)5-8(10)11/h6-7,9H,1-5H2,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ALTAAUJNHYWOGS-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>69999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128423</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022054</foodb_id>
  <chemspider_id>13628091</chemspider_id>
  <pubchem_compound_id>12702257</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id>89344</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Ungnade, Herbert E.; Morriss, Francis V.  Hydrogenation of phenolic acids.    Journal of the American Chemical Society  (1948),  70  1898-9.  CODEN: JACSAT  ISSN:0002-7863.  CAN 42:29753  AN 1948:29753</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:30:59 UTC</creation_date>
  <update_date>2020-04-14 22:47:30 UTC</update_date>
  <accession>BMDB0000452</accession>
  <secondary_accessions>
    <accession>BMDB00452</accession>
  </secondary_accessions>
  <name>L-Alpha-aminobutyric acid</name>
  <description>2-Aminobutyrate, also known as L-butyrine or L-homoalanine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 2-Aminobutyrate exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 2-Aminobutyrate exists in all eukaryotes, ranging from yeast to humans.</description>
  <synonyms>
    <synonym>(-)-2-Aminobutyric acid</synonym>
    <synonym>(2S)-2-Aminobutyric acid</synonym>
    <synonym>(S)-2-Aminobutanoate</synonym>
    <synonym>(S)-2-Aminobutanoic acid</synonym>
    <synonym>(S)-2-Aminobutyric acid</synonym>
    <synonym>L-(+)-2-Aminobutyric acid</synonym>
    <synonym>L-2-Aminobuttersaeure</synonym>
    <synonym>L-2-Aminobutyric acid</synonym>
    <synonym>L-alpha-Amino-N-butyric acid</synonym>
    <synonym>L-Butyrine</synonym>
    <synonym>S-Butyrine</synonym>
    <synonym>(-)-2-Aminobutyrate</synonym>
    <synonym>(2S)-2-Aminobutyrate</synonym>
    <synonym>(S)-2-Aminobutyrate</synonym>
    <synonym>L-(+)-2-Aminobutyrate</synonym>
    <synonym>L-2-Aminobutyrate</synonym>
    <synonym>L-a-Amino-N-butyrate</synonym>
    <synonym>L-a-Amino-N-butyric acid</synonym>
    <synonym>L-alpha-Amino-N-butyrate</synonym>
    <synonym>L-Α-amino-N-butyrate</synonym>
    <synonym>L-Α-amino-N-butyric acid</synonym>
    <synonym>L-a-Aminobutyrate</synonym>
    <synonym>L-a-Aminobutyric acid</synonym>
    <synonym>L-alpha-Aminobutyrate</synonym>
    <synonym>L-Α-aminobutyrate</synonym>
    <synonym>L-Α-aminobutyric acid</synonym>
    <synonym>(+)-2-Aminobutanoate</synonym>
    <synonym>(+)-2-Aminobutanoic acid</synonym>
    <synonym>(+)-2-Aminobutyric acid</synonym>
    <synonym>(+)-alpha-Aminobutyric acid</synonym>
    <synonym>(2S)-2-Aminobutanoate</synonym>
    <synonym>(2S)-2-Aminobutanoic acid</synonym>
    <synonym>(S)-(+)-alpha-Aminobutyric acid</synonym>
    <synonym>(S)-2-Amino-butanoate</synonym>
    <synonym>(S)-2-Amino-butanoic acid</synonym>
    <synonym>2-Aminobutanoate</synonym>
    <synonym>2-Aminobutanoic acid</synonym>
    <synonym>2-Aminobutyrate</synonym>
    <synonym>2S-Amino-butanoate</synonym>
    <synonym>2S-Amino-butanoic acid</synonym>
    <synonym>alpha-Aminobutyric acid</synonym>
    <synonym>L-2-Amino-N-butyric acid</synonym>
    <synonym>L-Ethylglycine</synonym>
    <synonym>Butyrine, (R)-isomer</synonym>
    <synonym>2-Aminobutyric acid</synonym>
    <synonym>alpha-Aminobutyric acid, (+-)-isomer</synonym>
    <synonym>Butyrine</synonym>
    <synonym>Butyrine, (S)-isomer</synonym>
    <synonym>L-Homoalanine</synonym>
    <synonym>alpha-Aminobutyric acid, (S)-isomer</synonym>
    <synonym>Homoalanine</synonym>
    <synonym>alpha-Aminobutyric acid, (R)-isomer</synonym>
    <synonym>Butyrine, (+-)-isomer</synonym>
    <synonym>L-2-Aminobutanoate</synonym>
  </synonyms>
  <chemical_formula>C4H9NO2</chemical_formula>
  <average_molecular_weight>103.1198</average_molecular_weight>
  <monisotopic_moleculate_weight>103.063328537</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-aminobutanoic acid</iupac_name>
  <traditional_iupac>(-)-2-aminobutyric acid</traditional_iupac>
  <cas_registry_number>1492-24-6</cas_registry_number>
  <smiles>CC[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1</inchi>
  <inchikey>QWCKQJZIFLGMSD-VKHMYHEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>alpha-aminobutyric acid</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>291 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.17</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-aminobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>103.1198</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>103.063328537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H9NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QWCKQJZIFLGMSD-VKHMYHEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439231</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1 - 10</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB012537</foodb_id>
  <kegg_id>C02356</kegg_id>
  <chemspider_id>72524</chemspider_id>
  <drugbank_id/>
  <chebi_id>35619</chebi_id>
  <pubchem_compound_id>80283</pubchem_compound_id>
  <pdbe_id/>
  <meta_cyc_id>CPD0-1942</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Alpha-Aminobutyric acid</wikipedia_id>
  <metlin_id>12</metlin_id>
  <synthesis_reference>Fotheringham, I. G.; Grinter, N.; Pantaleone, D. P.; Senkpeil, R. F.; Taylor, P. P.  Engineering of a novel biochemical pathway for the biosynthesis of l-2-aminobutyric acid in Escherichia coli K12.    Bioorganic &amp; Medicinal Chemistry  (1999),  7(10),  2209-2213.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:00 UTC</creation_date>
  <update_date>2020-03-13 16:21:21 UTC</update_date>
  <accession>BMDB0000453</accession>
  <secondary_accessions>
    <accession>BMDB00453</accession>
  </secondary_accessions>
  <name>Delta-Hexanolactone</name>
  <description/>
  <synonyms>
    <synonym>Δ-hexanolactone</synonym>
    <synonym>Epsilon-Caprolactone</synonym>
    <synonym>(RS)-delta-Hexalactone</synonym>
    <synonym>5-Hexanolide</synonym>
    <synonym>5-Hydroxy-hexanoate</synonym>
    <synonym>5-Hydroxy-hexanoic acid</synonym>
    <synonym>5-Hydroxy-hexanoic acid lactone</synonym>
    <synonym>5-Hydroxyhexanoate</synonym>
    <synonym>5-Hydroxyhexanoic acid</synonym>
    <synonym>5-Hydroxyhexanoic acid lactone</synonym>
    <synonym>6-Methyl-D-valerolactone</synonym>
    <synonym>6-Methylvalerolactone</synonym>
    <synonym>delta-Caprolactone</synonym>
    <synonym>delta-Hexalactone</synonym>
    <synonym>delta-Hexanolide</synonym>
    <synonym>delta-Methyl-delta-valerolactone</synonym>
    <synonym>Hexanolactone</synonym>
    <synonym>Tetrahydro-6-methyl-2H-pyran-2-one</synonym>
  </synonyms>
  <chemical_formula>C6H10O2</chemical_formula>
  <average_molecular_weight>114.1424</average_molecular_weight>
  <monisotopic_moleculate_weight>114.068079564</monisotopic_moleculate_weight>
  <iupac_name>6-methyloxan-2-one</iupac_name>
  <traditional_iupac>hexanolactone</traditional_iupac>
  <cas_registry_number>823-22-3</cas_registry_number>
  <smiles>CC1CCCC(=O)O1</smiles>
  <inchi>InChI=1S/C6H10O2/c1-5-3-2-4-6(7)8-5/h5H,2-4H2,1H3</inchi>
  <inchikey>RZTOWFMDBDPERY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Lactones</class>
    <sub_class>Delta valerolactones</sub_class>
    <direct_parent>Delta valerolactones</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Delta valerolactone</substituent>
      <substituent>Delta_valerolactone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6-methyloxan-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>114.1424</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>114.068079564</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1CCCC(=O)O1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O2/c1-5-3-2-4-6(7)8-5/h5H,2-4H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RZTOWFMDBDPERY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>26.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>29.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19570</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB008078</foodb_id>
  <kegg_id/>
  <chemspider_id>12649</chemspider_id>
  <drugbank_id/>
  <chebi_id>589927</chebi_id>
  <pubchem_compound_id>13204</pubchem_compound_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5442</metlin_id>
  <synthesis_reference>Mink, Daniel; Wolberg, Michael; Schuermann, Martin; Hilker, Iris.  Chemoenzymic preparation of d-lactones.  PCT Int. Appl.  (2007), 40pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:01 UTC</creation_date>
  <update_date>2020-03-13 16:21:21 UTC</update_date>
  <accession>BMDB0000455</accession>
  <secondary_accessions>
    <accession>BMDB00455</accession>
  </secondary_accessions>
  <name>Allocystathionine</name>
  <description>Allocystathionine belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Allocystathionine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule.</description>
  <synonyms>
    <synonym>a-Amino-g-(2-amino-2-carboxyethylmercapto)-butyric acid</synonym>
    <synonym>alpha-Amino-gamma-(2-amino-2-carboxyethylmercapto)-butyric acid</synonym>
    <synonym>DL-Allocystathionine</synonym>
    <synonym>DL-S-(2-Amino-2-carboxyethyl)-homocysteine</synonym>
    <synonym>(2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoate</synonym>
    <synonym>(2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulphanyl]butanoate</synonym>
    <synonym>(2S)-2-Amino-4-[(2-amino-2-carboxyethyl)sulphanyl]butanoic acid</synonym>
  </synonyms>
  <chemical_formula>C7H14N2O4S</chemical_formula>
  <average_molecular_weight>222.262</average_molecular_weight>
  <monisotopic_moleculate_weight>222.067427636</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid</iupac_name>
  <traditional_iupac>(2S)-2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid</traditional_iupac>
  <cas_registry_number>535-34-2</cas_registry_number>
  <smiles>N[C@@H](CCSCC(N)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5?/m0/s1</inchi>
  <inchikey>ILRYLPWNYFXEMH-ROLXFIACSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Cysteine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylthioethers</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Cysteine or derivatives</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thia fatty acid</substituent>
      <substituent>Thioether</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>281 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-4.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>222.262</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>222.067427636</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCSCC(N)C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H14N2O4S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ILRYLPWNYFXEMH-ROLXFIACSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>126.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349155</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022055</foodb_id>
  <kegg_id/>
  <chemspider_id>8280480</chemspider_id>
  <drugbank_id/>
  <chebi_id/>
  <pubchem_compound_id>10104953</pubchem_compound_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Mary L. Snow, Roy S. Dombro, and Charlotte Ressler. Synthesis of L-cystathionine and D-allocystathionine. J. Org. Chem., 1967, 32 (1), pp 246–248</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:02 UTC</creation_date>
  <update_date>2020-03-13 16:21:22 UTC</update_date>
  <accession>BMDB0000458</accession>
  <secondary_accessions>
    <accession>BMDB00458</accession>
  </secondary_accessions>
  <name>5a-Androstane-3a,17a-diol</name>
  <description/>
  <synonyms>
    <synonym>3a,17a-Dihydroxy-5a-androstane</synonym>
    <synonym>(3alpha,5alpha,17alpha)-Androstane-3,17-diol</synonym>
    <synonym>(3α,5α,17α)-Androstane-3,17-diol</synonym>
    <synonym>3alpha,17alpha-Dihydroxy-5alpha-androstane</synonym>
    <synonym>3α,17α-Dihydroxy-5α-androstane</synonym>
    <synonym>5alpha-Androstan-3alpha,17alpha-diol</synonym>
    <synonym>5alpha-Androstane-3alpha,17alpha-diol</synonym>
    <synonym>5α-Androstan-3α,17α-diol</synonym>
    <synonym>5α-Androstane-3α,17α-diol</synonym>
  </synonyms>
  <chemical_formula>C19H32O2</chemical_formula>
  <average_molecular_weight>292.4562</average_molecular_weight>
  <monisotopic_moleculate_weight>292.240230268</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7S,10R,11S,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol</iupac_name>
  <traditional_iupac>(1S,2S,5R,7S,10R,11S,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol</traditional_iupac>
  <cas_registry_number>6165-21-5</cas_registry_number>
  <smiles>[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17+,18-,19-/m0/s1</inchi>
  <inchikey>CBMYJHIOYJEBSB-CUZKMJQKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7S,10R,11S,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>292.4562</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>292.240230268</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H32O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17+,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CBMYJHIOYJEBSB-CUZKMJQKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368757</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022056</foodb_id>
  <chemspider_id>8032954</chemspider_id>
  <pubchem_compound_id>9857254</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>McDermott, Ian R.; Robinson, Cecil H.  Novel synthesis of 5a-androstane-3a,17a-diol.    Journal of the Chemical Society, Chemical Communications  (1979),   (1),  28-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:03 UTC</creation_date>
  <update_date>2020-04-15 21:59:28 UTC</update_date>
  <accession>BMDB0000459</accession>
  <secondary_accessions>
    <accession>BMDB00459</accession>
  </secondary_accessions>
  <name>3-Methylcrotonylglycine</name>
  <description/>
  <synonyms>
    <synonym>beta-Methylcrotonylglycine</synonym>
    <synonym>b-Methylcrotonylglycine</synonym>
    <synonym>Β-methylcrotonylglycine</synonym>
    <synonym>3-Methylcrotonyl glycine</synonym>
    <synonym>3-Methylcrotonyl-glycine</synonym>
    <synonym>3-Methylcrotonylglycin</synonym>
    <synonym>N-(3-Methyl-1-oxo-2-butenyl)-glycine</synonym>
    <synonym>3-Methylcrotonylglycine</synonym>
  </synonyms>
  <chemical_formula>C7H11NO3</chemical_formula>
  <average_molecular_weight>157.1671</average_molecular_weight>
  <monisotopic_moleculate_weight>157.073893223</monisotopic_moleculate_weight>
  <iupac_name>2-(3-methylbut-2-enamido)acetic acid</iupac_name>
  <traditional_iupac>(3-methylbut-2-enamido)acetic acid</traditional_iupac>
  <cas_registry_number>33008-07-0</cas_registry_number>
  <smiles>CC(C)=CC(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C7H11NO3/c1-5(2)3-6(9)8-4-7(10)11/h3H,4H2,1-2H3,(H,8,9)(H,10,11)</inchi>
  <inchikey>PFWQSHXPNKRLIV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylglycine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.058</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(3-methylbut-2-enamido)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>157.1671</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>157.073893223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)=CC(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H11NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H11NO3/c1-5(2)3-6(9)8-4-7(10)11/h3H,4H2,1-2H3,(H,8,9)(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PFWQSHXPNKRLIV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362619</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022057</foodb_id>
  <kegg_id/>
  <chemspider_id>148224</chemspider_id>
  <drugbank_id/>
  <chebi_id>68499</chebi_id>
  <pubchem_compound_id>169485</pubchem_compound_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5447</metlin_id>
  <synthesis_reference>Carter, S. M. Bonham; Watson, D. G.; Midgley, J. M.; Logan, R. W.  Synthesis and characterization of acyl glycines. Their measurement in single blood spots by gas chromatography-mass spectrometry to diagnose inborn errors of metabolism.    Journal of Chromatography, B: Biomedical Applications  (1996),  677(1),  29-35.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:04 UTC</creation_date>
  <update_date>2020-04-15 22:13:56 UTC</update_date>
  <accession>BMDB0000460</accession>
  <secondary_accessions>
    <accession>BMDB00460</accession>
  </secondary_accessions>
  <name>7-Hydroxy-3-oxocholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>7-Hydroxy-3-oxocholanoate</synonym>
    <synonym>(5a,7b)-7-Hydroxy-3-oxo-cholanoate</synonym>
    <synonym>(5a,7b)-7-Hydroxy-3-oxo-cholanoic acid</synonym>
    <synonym>7-Hydroxy-3-oxo-(5a,7b)-cholan-24-Oate</synonym>
    <synonym>7-Hydroxy-3-oxo-(5a,7b)-cholan-24-Oic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,7S,9S,10R,11S,15R)-9-Hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H38O4</chemical_formula>
  <average_molecular_weight>390.5561</average_molecular_weight>
  <monisotopic_moleculate_weight>390.277009704</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,7S,9S,10R,11S,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,7S,9S,10R,11S,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>77059-13-3</cas_registry_number>
  <smiles>[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@@]2([H])CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-15,17-20,22,26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,17?,18+,19+,20+,22+,23+,24-/m1/s1</inchi>
  <inchikey>KNVADAPHVNKTEP-MKYSPFRDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Monohydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-oxo-5-alpha-steroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-oxo-5-alpha-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monohydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,7S,9S,10R,11S,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>390.5561</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>390.277009704</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@@]2([H])CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H38O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-15,17-20,22,26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,17?,18+,19+,20+,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KNVADAPHVNKTEP-MKYSPFRDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>108.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>45.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354594</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022058</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477692</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5448</metlin_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:05 UTC</creation_date>
  <update_date>2020-04-14 22:47:31 UTC</update_date>
  <accession>BMDB0000462</accession>
  <secondary_accessions>
    <accession>BMDB00462</accession>
  </secondary_accessions>
  <name>Allantoin</name>
  <description>Allantoin, also known as glyoxyldiureide or 5-ureidohydantoin, belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms. Allantoin exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Allantoin exists in all living species, ranging from bacteria to humans. Allantoin is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2,5-Dioxo-4-imidazolidinyl)urea</synonym>
    <synonym>2,5-Dioxo-4-imidazolidinyl-urea</synonym>
    <synonym>4-Ureido-2,5-imidazolidinedione</synonym>
    <synonym>5-Ureido-2,4-imidazolidindione</synonym>
    <synonym>5-Ureidohydantoin</synonym>
    <synonym>Glyoxyldiureide</synonym>
    <synonym>N-(2,5-Dioxo-4-imidazolidinyl)urea</synonym>
    <synonym>(S)-Allantoin</synonym>
    <synonym>5-Ureido-hydantoin</synonym>
    <synonym>5-Ureidohydrantoin</synonym>
    <synonym>Alantan</synonym>
    <synonym>Allantol</synonym>
    <synonym>Alloxantin</synonym>
    <synonym>AVC/Dienestrolcream</synonym>
    <synonym>Cordianine</synonym>
    <synonym>D00121</synonym>
    <synonym>Fancol toin</synonym>
    <synonym>Glyoxyldiureid</synonym>
    <synonym>Glyoxylic diureide</synonym>
    <synonym>Psoralon</synonym>
    <synonym>Sebical</synonym>
    <synonym>Septalan</synonym>
    <synonym>Sween brand OF allantoin</synonym>
    <synonym>Herpecin-L</synonym>
    <synonym>HerpecinL</synonym>
    <synonym>Reed and carnrick brand OF allantoin</synonym>
    <synonym>Woun'dres</synonym>
    <synonym>Allantoin sween brand</synonym>
    <synonym>Campbell brand OF allantoin</synonym>
    <synonym>Allantoin campbell brand</synonym>
    <synonym>Herpecin L</synonym>
  </synonyms>
  <chemical_formula>C4H6N4O3</chemical_formula>
  <average_molecular_weight>158.1154</average_molecular_weight>
  <monisotopic_moleculate_weight>158.043990078</monisotopic_moleculate_weight>
  <iupac_name>(2,5-dioxoimidazolidin-4-yl)urea</iupac_name>
  <traditional_iupac>allantoin</traditional_iupac>
  <cas_registry_number>97-59-6</cas_registry_number>
  <smiles>NC(=O)NC1NC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)</inchi>
  <inchikey>POJWUDADGALRAB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Azoles</class>
    <sub_class>Imidazoles</sub_class>
    <direct_parent>Imidazoles</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Isoureas</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imine</substituent>
      <substituent>Isourea</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>imidazolidine-2,4-dione</external_descriptor>
      <external_descriptor>ureas</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>239 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>5.26 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2,5-dioxoimidazolidin-4-yl)urea</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>158.1154</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>158.043990078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)NC1NC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H6N4O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>POJWUDADGALRAB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4792</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22587</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>205</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw whole milk</comment>
      <references>
        <reference>
          <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
          <pubmed_id>6539345</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>198.100 +/- 39</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Giesecke D, Ehrentreich L, Stangassinger M, Ahrens F: Mammary and renal excretion of purine metabolites in relation to energy intake and milk yield in dairy cows. J Dairy Sci. 1994 Aug;77(8):2376-81. doi: 10.3168/jds.S0022-0302(94)77180-0.</reference_text>
          <pubmed_id>7962859</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein.</comment>
      <references>
        <reference>
          <reference_text>Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17.</reference_text>
          <pubmed_id>22059599</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB001613</foodb_id>
  <kegg_id>C01551</kegg_id>
  <chemspider_id>199</chemspider_id>
  <drugbank_id/>
  <chebi_id>15676</chebi_id>
  <pubchem_compound_id>204</pubchem_compound_id>
  <pdbe_id/>
  <meta_cyc_id>ALLANTOIN</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007468</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Allantoin</wikipedia_id>
  <metlin_id>89</metlin_id>
  <synthesis_reference>Du, Niansheng; Yang, Jianhua; Rena, Kasimu.  Method for isolation of allantoin from Cistanche deserticola.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2006),  5pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
      <pubmed_id>6539345</pubmed_id>
    </reference>
    <reference>
      <reference_text>Giesecke D, Ehrentreich L, Stangassinger M, Ahrens F: Mammary and renal excretion of purine metabolites in relation to energy intake and milk yield in dairy cows. J Dairy Sci. 1994 Aug;77(8):2376-81. doi: 10.3168/jds.S0022-0302(94)77180-0.</reference_text>
      <pubmed_id>7962859</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:07 UTC</creation_date>
  <update_date>2020-04-14 21:15:05 UTC</update_date>
  <accession>BMDB0000464</accession>
  <secondary_accessions>
    <accession>BMDB00464</accession>
  </secondary_accessions>
  <name>Calcium</name>
  <description>Calcium, also known as ca(2+) or calcium ion, belongs to the class of inorganic compounds known as homogeneous alkaline earth metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a alkaline earth metal atom. Calcium exists as a solid, possibly soluble (in water), and possibly neutral molecule. Calcium exists in all living species, ranging from bacteria to humans. Calcium is a potentially toxic compound. Calcium has been found to be associated with several diseases known as sucrase-isomaltase deficiency, bartter syndrome, type 3, mitochondrial trifunctional protein deficiency, and bartter syndrome, type 5, antenatal, transient; also calcium has been linked to the inborn metabolic disorders including primary hypomagnesemia.</description>
  <synonyms>
    <synonym>Ca(2+)</synonym>
    <synonym>Ca2+</synonym>
    <synonym>CALCIUM ion</synonym>
    <synonym>Calcium, doubly charged positive ion</synonym>
    <synonym>Calcium(2+)</synonym>
    <synonym>Ca</synonym>
    <synonym>Calcium element</synonym>
  </synonyms>
  <chemical_formula>Ca</chemical_formula>
  <average_molecular_weight>40.078</average_molecular_weight>
  <monisotopic_moleculate_weight>39.962591155</monisotopic_moleculate_weight>
  <iupac_name>calcium(2+) ion</iupac_name>
  <traditional_iupac>calcium(2+) ion</traditional_iupac>
  <cas_registry_number>14127-61-8</cas_registry_number>
  <smiles>[Ca++]</smiles>
  <inchi>InChI=1S/Ca/q+2</inchi>
  <inchikey>BHPQYMZQTOCNFJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous alkaline earth metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a alkaline earth metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous alkaline earth metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous alkaline earth metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous alkaline earth metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a cation</external_descriptor>
      <external_descriptor>calcium cation</external_descriptor>
      <external_descriptor>divalent metal cation</external_descriptor>
      <external_descriptor>monoatomic dication</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>850 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>calcium(2+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>40.078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>39.962591155</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Ca++]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Ca</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Ca/q+2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHPQYMZQTOCNFJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Activation of PKC Through G Protein-Coupled Receptor</name>
      <smpdb_id>SMP0108001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Alpha Linolenic Acid and Linoleic Acid Metabolism</name>
      <smpdb_id>SMP0087171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>BCR Signaling Pathway</name>
      <smpdb_id>SMP0120940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cadmium Induces DNA Synthesis and Proliferation in Macrophages </name>
      <smpdb_id>SMP0108212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Classical Complement Pathway</name>
      <smpdb_id>SMP0120932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Coagulation </name>
      <smpdb_id>SMP0119377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>CXCR4 Signaling Pathway</name>
      <smpdb_id>SMP0120933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>EGF Signalling Pathway</name>
      <smpdb_id>SMP0120924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>EPO Signaling Pathway</name>
      <smpdb_id>SMP0120938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fc Epsilon Receptor I Signaling in Mast Cells</name>
      <smpdb_id>SMP0108186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>GnRH Signaling Pathway</name>
      <smpdb_id>SMP0120925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Growth Hormone Signaling Pathway </name>
      <smpdb_id>SMP0120923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histamine H1 Receptor Activation</name>
      <smpdb_id>SMP0108002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Prostacyclin Receptor and Prostacyclin</name>
      <smpdb_id>SMP0107998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ion Channel and Phorbal Esters Signaling Pathway</name>
      <smpdb_id>SMP0120945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ion Channels and Their Functional Role in Vascular Endothelium</name>
      <smpdb_id>SMP0108207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lectin-Induced Complement Pathway </name>
      <smpdb_id>SMP0120930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA1 Signalling</name>
      <smpdb_id>SMP0108191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA2 Signalling</name>
      <smpdb_id>SMP0108193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA3 Signalling</name>
      <smpdb_id>SMP0108194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA4 Signalling</name>
      <smpdb_id>SMP0108196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA5 Signalling</name>
      <smpdb_id>SMP0108198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Malate-Aspartate Shuttle</name>
      <smpdb_id>SMP0087204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Muscle/Heart Contraction</name>
      <smpdb_id>SMP0119378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nitric Oxide Signaling Pathway</name>
      <smpdb_id>SMP0108206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pancreas Function</name>
      <smpdb_id>SMP0119380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pantothenate and CoA Biosynthesis</name>
      <smpdb_id>SMP0087207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylinositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipase C Signaling Pathway</name>
      <smpdb_id>SMP0100480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipase C Signaling Pathway </name>
      <smpdb_id>SMP0108209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Riboflavin Metabolism</name>
      <smpdb_id>SMP0087211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Succinate Signalling During Inflammation</name>
      <smpdb_id>SMP0120886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>T Cell Receptor Signaling Pathway </name>
      <smpdb_id>SMP0120935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Thyroid Hormone Synthesis</name>
      <smpdb_id>SMP0087269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30151</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>880 +/- 40</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Spectrometry (Autoanalyzer/BT3000 Plus)</comment>
      <references>
        <reference>
          <reference_text>Abdullah BASOGLU, Nuri BASPINAR, Alparslan COSKUN. NMR-based metabolomic evaluation in dairy cows with displaced abomasum. Turk J Vet Anim Sci (2014) 38(3):325-330</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2500</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Dacos Chemistry Analyzer in Hereford cows</comment>
      <references>
        <reference>
          <reference_text>Early RJ, McBride BW, Ball RO: Growth and metabolism in somatotropin-treated steers: I. Growth, serum chemistry and carcass weights. J Anim Sci. 1990 Dec;68(12):4134-43. doi: 10.2527/1990.68124134x.</reference_text>
          <pubmed_id>2286555</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3700 +/- 30</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>McAdam PA, O'Dell GD: Mineral profile of blood plasma of lactating dairy cows. J Dairy Sci. 1982 Jul;65(7):1219-26. doi: 10.3168/jds.S0022-0302(82)82333-3.</reference_text>
          <pubmed_id>7108016</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2228+/-221</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2485.154-4037.128</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Clark and Collip's modification of the Kramer and Tisdall method (1925)</comment>
      <references>
        <reference>
          <reference_text>Arthur K. Anderson, Howard E. Gayley, Avery D. Pratt. Studies on the Chemical Composition of Bovine Blood. J. Dairy Science (1930) 13(4):336-348   doi: 10.3168/jds.S0022-0302(30)93530-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by LC-MS and NMR in Angus-Hereford cows.</comment>
      <references>
        <reference>
          <reference_text>Aich P, Babiuk LA, Potter AA, Griebel P: Biomarkers for prediction of bovine respiratory disease outcome. OMICS. 2009 Jun;13(3):199-209. doi: 10.1089/omi.2009.0012.</reference_text>
          <pubmed_id>19275474</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2495.134 +/- 99.805</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Gitelman (1967) method. Samples have been collected from White Shorthorn x Galloway (Blue-grey).</comment>
      <references>
        <reference>
          <reference_text>C. R. E. Cogginsa and A. C. Field. Diurnal variation in the chemical composition of plasma from lactating beef cows on three dietary energy intakes. J. agric. Sri., Camb. (1976), 86, 595-602</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>17+/-8</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35680.423</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32187.235</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30440.641</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30440.641</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30440.641</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30440.641</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29692.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35680.423</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31937.721</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35680.423</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29941.614</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29941.614</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31724.14 +/- 544.19</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Total calcium in Holstein-Friesian cows milk with 4.43% fat</comment>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30939.668</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>40721.59 +/- 575.88</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Total calcium in Jersey cows milk with 6.05% fat</comment>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30939.668</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>26506.56 +/- 1132.54</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Total calcium in Holstein-Friesian cows milk with 3.51% fat</comment>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30939.668</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27949.50 +/- 653.98</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Total calcium in Holstein-Friesian cows milk with 3.69% fat</comment>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28195.0197</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>36377.065 +/- 598.58</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Total calcium in Jersey cows milk with 5.93% fat</comment>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28195.0197</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27945.506</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28943.56</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28943.56</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>26000 - 32000</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: The minerals of milk. Reprod Nutr Dev. 2005 Jul-Aug;45(4):473-83. doi: 10.1051/rnd:2005030.</reference_text>
          <pubmed_id>16045895</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30440.641</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>34430 +/- 3490</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw whole milk</comment>
      <references>
        <reference>
          <reference_text>Zhang P, Allen JC: A novel dialysis procedure measuring free Zn2+ in bovine milk and plasma. J Nutr. 1995 Jul;125(7):1904-10. doi: 10.1093/jn/125.7.1904.</reference_text>
          <pubmed_id>7616307</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28909 +/- 2255</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>26132 +/- 1964</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25529 +/- 803</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32909 +/- 2255</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29692.100 - 30939.668</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29941.614</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28300 - 54200</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk, range over first 90 day in lactation</comment>
      <references>
        <reference>
          <reference_text>Tsioulpas A, Grandison AS, Lewis MJ: Changes in physical properties of bovine milk from the colostrum period to early lactation. J Dairy Sci. 2007 Nov;90(11):5012-7. doi: 10.3168/jds.2007-0192.</reference_text>
          <pubmed_id>17954740</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31937.721</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31937.721</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31189.181</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>50900.744</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25200.858</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35430.91</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31937.721</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31189.181</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>371+/-722</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>931.0 +/- 27.0</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by ICP-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1000 - 4000</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>An increase in the acidity of the ruminal fluidalso increased the absorption of phosphate, as did an increase in the ruminal Ca2? concentration over the range (1-4)mmol per litre</comment>
      <references>
        <reference>
          <reference_text>Wadhwa DR, Care AD: The absorption of phosphate ions from the ovine reticulorumen. Vet J. 2002 Mar;163(2):182-6.</reference_text>
          <pubmed_id>12093193</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>13+/-4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00076</kegg_id>
  <foodb_id>FDB003513</foodb_id>
  <chemspider_id>266</chemspider_id>
  <pubchem_compound_id>271</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>29108</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>33764</bigg_id>
  <wikipedia_id>Calcium</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Zhang P, Allen JC: A novel dialysis procedure measuring free Zn2+ in bovine milk and plasma. J Nutr. 1995 Jul;125(7):1904-10. doi: 10.1093/jn/125.7.1904.</reference_text>
      <pubmed_id>7616307</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gaucheron F: The minerals of milk. Reprod Nutr Dev. 2005 Jul-Aug;45(4):473-83. doi: 10.1051/rnd:2005030.</reference_text>
      <pubmed_id>16045895</pubmed_id>
    </reference>
    <reference>
      <reference_text>Tsioulpas A, Grandison AS, Lewis MJ: Changes in physical properties of bovine milk from the colostrum period to early lactation. J Dairy Sci. 2007 Nov;90(11):5012-7. doi: 10.3168/jds.2007-0192.</reference_text>
      <pubmed_id>17954740</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
      <pubmed_id>23040012</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
      <pubmed_id>22081685</pubmed_id>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00081</protein_accession>
      <name>Arylsulfatase A</name>
      <uniprot_id>Q08DD1</uniprot_id>
      <gene_name>ARSA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00091</protein_accession>
      <name>Primary amine oxidase, liver isozyme</name>
      <uniprot_id>Q29437</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00092</protein_accession>
      <name>Glycerol-3-phosphate dehydrogenase, mitochondrial</name>
      <uniprot_id>A6QLU1</uniprot_id>
      <gene_name>GPD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00095</protein_accession>
      <name>Membrane primary amine oxidase</name>
      <uniprot_id>Q9TTK6</uniprot_id>
      <gene_name>AOC3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00096</protein_accession>
      <name>Primary amine oxidase, lung isozyme</name>
      <uniprot_id>O46406</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00115</protein_accession>
      <name>Heparanase</name>
      <uniprot_id>Q9MYY0</uniprot_id>
      <gene_name>HPSE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00153</protein_accession>
      <name>Calcium-transporting ATPase type 2C member 1</name>
      <uniprot_id>P57709</uniprot_id>
      <gene_name>ATP2C1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00156</protein_accession>
      <name>Ectonucleoside triphosphate diphosphohydrolase 8</name>
      <uniprot_id>A0JND9</uniprot_id>
      <gene_name>ENTPD8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00163</protein_accession>
      <name>Ectonucleoside triphosphate diphosphohydrolase 1</name>
      <uniprot_id>O18956</uniprot_id>
      <gene_name>ENTPD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00207</protein_accession>
      <name>Sarcoplasmic/endoplasmic reticulum calcium ATPase 1</name>
      <uniprot_id>Q0VCY0</uniprot_id>
      <gene_name>ATP2A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00231</protein_accession>
      <name>Platelet-activating factor acetylhydrolase IB subunit alpha</name>
      <uniprot_id>P43033</uniprot_id>
      <gene_name>PAFAH1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00380</protein_accession>
      <name>N-acetylglucosamine-6-sulfatase</name>
      <uniprot_id>Q1LZH9</uniprot_id>
      <gene_name>GNS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00381</protein_accession>
      <name>Polypeptide N-acetylgalactosaminyltransferase 6</name>
      <uniprot_id>Q5EA41</uniprot_id>
      <gene_name>GALNT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00382</protein_accession>
      <name>Polypeptide N-acetylgalactosaminyltransferase 1</name>
      <uniprot_id>Q07537</uniprot_id>
      <gene_name>GALNT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00427</protein_accession>
      <name>Fumarylacetoacetase</name>
      <uniprot_id>A5PKH3</uniprot_id>
      <gene_name>FAH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00477</protein_accession>
      <name>Bis(5'-adenosyl)-triphosphatase</name>
      <uniprot_id>Q1KZG4</uniprot_id>
      <gene_name>FHIT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00506</protein_accession>
      <name>Fumarylacetoacetate hydrolase domain-containing protein 2</name>
      <uniprot_id>Q2KIB0</uniprot_id>
      <gene_name>FAHD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00519</protein_accession>
      <name>Fumarylacetoacetate hydrolase domain-containing protein 1</name>
      <uniprot_id>Q2HJ98</uniprot_id>
      <gene_name>FAHD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00572</protein_accession>
      <name>Glutamyl aminopeptidase</name>
      <uniprot_id>Q32LQ0</uniprot_id>
      <gene_name>ENPEP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00644</protein_accession>
      <name>UDP-N-acetyl-alpha-D-galactosamine:polypeptide N-acetylgalactosaminyltransferase 6 (GalNAc-T6)</name>
      <uniprot_id>A6H6Z5</uniprot_id>
      <gene_name>GALNT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00854</protein_accession>
      <name>Coagulation factor XIII A chain</name>
      <uniprot_id>P12260</uniprot_id>
      <gene_name>F13A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01046</protein_accession>
      <name>Matrix metallopeptidase 2 (Gelatinase A, 72kDa gelatinase, 72kDa type IV collagenase)</name>
      <uniprot_id>A6QPN5</uniprot_id>
      <gene_name>MMP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01064</protein_accession>
      <name>Diacylglycerol kinase alpha</name>
      <uniprot_id>A0JN54</uniprot_id>
      <gene_name>DGKA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01161</protein_accession>
      <name>Protein kinase C beta type</name>
      <uniprot_id>P05126</uniprot_id>
      <gene_name>PRKCB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01203</protein_accession>
      <name>Protein kinase C gamma type</name>
      <uniprot_id>P05128</uniprot_id>
      <gene_name>PRKCG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01215</protein_accession>
      <name>Protein kinase C alpha type</name>
      <uniprot_id>P04409</uniprot_id>
      <gene_name>PRKCA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01299</protein_accession>
      <name>Guanylyl cyclase-activating protein 1</name>
      <uniprot_id>P46065</uniprot_id>
      <gene_name>GUCA1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01300</protein_accession>
      <name>Glucosidase 2 subunit beta</name>
      <uniprot_id>Q28034</uniprot_id>
      <gene_name>PRKCSH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01301</protein_accession>
      <name>Calpain small subunit 1</name>
      <uniprot_id>P13135</uniprot_id>
      <gene_name>CAPNS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01302</protein_accession>
      <name>Calcineurin subunit B type 2</name>
      <uniprot_id>Q2TBI5</uniprot_id>
      <gene_name>PPP3R2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01303</protein_accession>
      <name>Complement C1s subcomponent</name>
      <uniprot_id>Q0VCX1</uniprot_id>
      <gene_name>C1S</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01304</protein_accession>
      <name>Alpha-lactalbumin</name>
      <uniprot_id>P00711</uniprot_id>
      <gene_name>LALBA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01305</protein_accession>
      <name>Deoxyribonuclease-1</name>
      <uniprot_id>P00639</uniprot_id>
      <gene_name>DNASE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01306</protein_accession>
      <name>Coagulation factor VII</name>
      <uniprot_id>P22457</uniprot_id>
      <gene_name>F7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01307</protein_accession>
      <name>Arylsulfatase K</name>
      <uniprot_id>Q148F3</uniprot_id>
      <gene_name>ARSK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01308</protein_accession>
      <name>Calpain-3</name>
      <uniprot_id>P51186</uniprot_id>
      <gene_name>CAPN3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01309</protein_accession>
      <name>Furin</name>
      <uniprot_id>Q28193</uniprot_id>
      <gene_name>FURIN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01310</protein_accession>
      <name>Coagulation factor IX</name>
      <uniprot_id>P00741</uniprot_id>
      <gene_name>F9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01311</protein_accession>
      <name>Guanylyl cyclase-activating protein 2</name>
      <uniprot_id>P51177</uniprot_id>
      <gene_name>GUCA1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01312</protein_accession>
      <name>Coagulation factor X</name>
      <uniprot_id>P00743</uniprot_id>
      <gene_name>F10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01313</protein_accession>
      <name>FK506-binding protein 10</name>
      <uniprot_id>Q2HJ89</uniprot_id>
      <gene_name>FKBP10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01314</protein_accession>
      <name>Calcineurin subunit B type 1</name>
      <uniprot_id>P63099</uniprot_id>
      <gene_name>PPP3R1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01315</protein_accession>
      <name>Chymotrypsin-like elastase family member 1</name>
      <uniprot_id>Q28153</uniprot_id>
      <gene_name>CELA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01316</protein_accession>
      <name>Calpain-1 catalytic subunit</name>
      <uniprot_id>Q27970</uniprot_id>
      <gene_name>CAPN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01317</protein_accession>
      <name>FK506-binding protein 9</name>
      <uniprot_id>Q2KJC8</uniprot_id>
      <gene_name>FKBP9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01318</protein_accession>
      <name>Annexin A1</name>
      <uniprot_id>P46193</uniprot_id>
      <gene_name>ANXA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01319</protein_accession>
      <name>Hepatocyte growth factor-regulated tyrosine kinase substrate</name>
      <uniprot_id>Q0V8S0</uniprot_id>
      <gene_name>HGS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01320</protein_accession>
      <name>Calpain-2 catalytic subunit</name>
      <uniprot_id>Q27971</uniprot_id>
      <gene_name>CAPN2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01334</protein_accession>
      <name>Inositol 1,4,5-trisphosphate receptor type 2</name>
      <uniprot_id>Q8WN96</uniprot_id>
      <gene_name>ITPR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01337</protein_accession>
      <name>Inositol 1,4,5-trisphosphate receptor type 1</name>
      <uniprot_id>Q9TU34</uniprot_id>
      <gene_name>ITPR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01338</protein_accession>
      <name>Inositol 1,4,5-trisphosphate receptor type 3</name>
      <uniprot_id>Q8WN95</uniprot_id>
      <gene_name>ITPR3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01344</protein_accession>
      <name>Calcium-activated potassium channel subunit alpha-1</name>
      <uniprot_id>Q28204</uniprot_id>
      <gene_name>KCNMA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01345</protein_accession>
      <name>Cartilage oligomeric matrix protein</name>
      <uniprot_id>P35445</uniprot_id>
      <gene_name>COMP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01353</protein_accession>
      <name>CD97 antigen</name>
      <uniprot_id>Q8SQA4</uniprot_id>
      <gene_name>CD97</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01359</protein_accession>
      <name>Annexin A3</name>
      <uniprot_id>Q3SWX7</uniprot_id>
      <gene_name>ANXA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01391</protein_accession>
      <name>Heparin-binding growth factor 2</name>
      <uniprot_id>P03969</uniprot_id>
      <gene_name>FGF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01430</protein_accession>
      <name>Protein AMBP</name>
      <uniprot_id>P00978</uniprot_id>
      <gene_name>AMBP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01597</protein_accession>
      <name>Calcium-binding protein 1</name>
      <uniprot_id>Q9N1R0</uniprot_id>
      <gene_name>CABP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01602</protein_accession>
      <name>Integrin alpha-L</name>
      <uniprot_id>P61625</uniprot_id>
      <gene_name>ITGAL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01606</protein_accession>
      <name>Integrin alpha-2</name>
      <uniprot_id>P53710</uniprot_id>
      <gene_name>ITGA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01616</protein_accession>
      <name>Collectin-12</name>
      <uniprot_id>A6QP79</uniprot_id>
      <gene_name>COLEC12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01617</protein_accession>
      <name>Collectin-43</name>
      <uniprot_id>P42916</uniprot_id>
      <gene_name>CL43</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01846</protein_accession>
      <name>Epithelial chloride channel protein</name>
      <uniprot_id>P54281</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01900</protein_accession>
      <name>Collectin-11</name>
      <uniprot_id>Q17QH6</uniprot_id>
      <gene_name>COLEC11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01901</protein_accession>
      <name>Collectin-46</name>
      <uniprot_id>Q8MHZ9</uniprot_id>
      <gene_name>CL46</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01908</protein_accession>
      <name>Conglutinin</name>
      <uniprot_id>P23805</uniprot_id>
      <gene_name>CGN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01918</protein_accession>
      <name>GALNTL1 protein</name>
      <uniprot_id>A6QLD9</uniprot_id>
      <gene_name>GALNTL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01920</protein_accession>
      <name>GALNT4 protein</name>
      <uniprot_id>A7YY74</uniprot_id>
      <gene_name>GALNT4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01921</protein_accession>
      <name>GALNT12 protein</name>
      <uniprot_id>A6QLX6</uniprot_id>
      <gene_name>GALNT12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01932</protein_accession>
      <name>Coagulation factor V</name>
      <uniprot_id>Q28107</uniprot_id>
      <gene_name>F5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02020</protein_accession>
      <name>Calreticulin</name>
      <uniprot_id>P52193</uniprot_id>
      <gene_name>CALR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02040</protein_accession>
      <name>43kDa collectin</name>
      <uniprot_id>B7FEK7</uniprot_id>
      <gene_name>CL43</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02046</protein_accession>
      <name>Calreticulin-3</name>
      <uniprot_id>Q2TBR8</uniprot_id>
      <gene_name>CALR3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02071</protein_accession>
      <name>Versican core protein</name>
      <uniprot_id>P81282</uniprot_id>
      <gene_name>VCAN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02079</protein_accession>
      <name>Lithostathine</name>
      <uniprot_id>P23132</uniprot_id>
      <gene_name>PTP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02117</protein_accession>
      <name>Predicted NADPH oxidase-5</name>
      <uniprot_id>A7E3L4</uniprot_id>
      <gene_name>Nox5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02150</protein_accession>
      <name>Chromogranin-A</name>
      <uniprot_id>P05059</uniprot_id>
      <gene_name>CHGA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02182</protein_accession>
      <name>C-C chemokine receptor type 5</name>
      <uniprot_id>Q2HJ17</uniprot_id>
      <gene_name>CCR5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02251</protein_accession>
      <name>Type-1 angiotensin II receptor</name>
      <uniprot_id>P25104</uniprot_id>
      <gene_name>AGTR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02305</protein_accession>
      <name>MMP27 protein</name>
      <uniprot_id>A5PJJ3</uniprot_id>
      <gene_name>MMP27</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02573</protein_accession>
      <name>Calbindin</name>
      <uniprot_id>P04467</uniprot_id>
      <gene_name>CALB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02627</protein_accession>
      <name>Calsenilin</name>
      <uniprot_id>Q17QD9</uniprot_id>
      <gene_name>KCNIP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02656</protein_accession>
      <name>Kv channel-interacting protein 4</name>
      <uniprot_id>Q2KI69</uniprot_id>
      <gene_name>KCNIP4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02698</protein_accession>
      <name>Calcium channel, voltage-dependent, P/Q type, Cav2.1 alpha 1A subunit</name>
      <uniprot_id>A5ACB9</uniprot_id>
      <gene_name>CACNA1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02699</protein_accession>
      <name>Hippocalcin-like protein 4</name>
      <uniprot_id>P29104</uniprot_id>
      <gene_name>HPCAL4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02700</protein_accession>
      <name>EF-hand domain-containing protein D2</name>
      <uniprot_id>A5D7A0</uniprot_id>
      <gene_name>EFHD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02701</protein_accession>
      <name>High affinity interleukin-8 receptor B</name>
      <uniprot_id>Q28003</uniprot_id>
      <gene_name>IL8RB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02702</protein_accession>
      <name>Annexin A11</name>
      <uniprot_id>P27214</uniprot_id>
      <gene_name>ANXA11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02703</protein_accession>
      <name>CDH8 protein</name>
      <uniprot_id>A2VDQ2</uniprot_id>
      <gene_name>CDH8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02704</protein_accession>
      <name>Adseverin</name>
      <uniprot_id>Q28046</uniprot_id>
      <gene_name>SCIN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02705</protein_accession>
      <name>Calcium-binding protein 4</name>
      <uniprot_id>Q8HZJ4</uniprot_id>
      <gene_name>CABP4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02706</protein_accession>
      <name>Cysteine-rich with EGF-like domain protein 2</name>
      <uniprot_id>Q2KIT5</uniprot_id>
      <gene_name>CRELD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02707</protein_accession>
      <name>Annexin A7</name>
      <uniprot_id>P20072</uniprot_id>
      <gene_name>ANXA7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02708</protein_accession>
      <name>Cadherin 11, type 2, OB-cadherin (Osteoblast)</name>
      <uniprot_id>A2VDQ6</uniprot_id>
      <gene_name>CDH11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02709</protein_accession>
      <name>Transient receptor potential cation channel, subfamily C, member 1, short isoform</name>
      <uniprot_id>A7VJS3</uniprot_id>
      <gene_name>TRPC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02710</protein_accession>
      <name>Endoplasmin</name>
      <uniprot_id>Q95M18</uniprot_id>
      <gene_name>HSP90B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02711</protein_accession>
      <name>Desmocollin-1</name>
      <uniprot_id>Q01107</uniprot_id>
      <gene_name>DSC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02712</protein_accession>
      <name>Gelsolin</name>
      <uniprot_id>Q3SX14</uniprot_id>
      <gene_name>GSN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02713</protein_accession>
      <name>Desmocollin-3</name>
      <uniprot_id>Q28060</uniprot_id>
      <gene_name>DSC3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02714</protein_accession>
      <name>Cysteine-rich with EGF-like domain protein 1</name>
      <uniprot_id>Q5EA46</uniprot_id>
      <gene_name>CRELD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02715</protein_accession>
      <name>Voltage-dependent L-type calcium channel subunit beta-2</name>
      <uniprot_id>Q9MZL5</uniprot_id>
      <gene_name>CACNB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02716</protein_accession>
      <name>Centrin-1</name>
      <uniprot_id>Q32LE3</uniprot_id>
      <gene_name>CETN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02717</protein_accession>
      <name>MGC148871 protein</name>
      <uniprot_id>A5D7T2</uniprot_id>
      <gene_name>MGC148871</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02718</protein_accession>
      <name>Fibulin-5</name>
      <uniprot_id>Q5EA62</uniprot_id>
      <gene_name>FBLN5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02719</protein_accession>
      <name>Endoplasmic reticulum resident protein ERp44</name>
      <uniprot_id>Q3T0L2</uniprot_id>
      <gene_name>ERP44</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02720</protein_accession>
      <name>PCDHA13 protein</name>
      <uniprot_id>A6QNT5</uniprot_id>
      <gene_name>PCDHA13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02721</protein_accession>
      <name>MUPCDH protein</name>
      <uniprot_id>A7E2Z4</uniprot_id>
      <gene_name>MUPCDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02722</protein_accession>
      <name>MCFD2 protein</name>
      <uniprot_id>A6QQ22</uniprot_id>
      <gene_name>MCFD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02723</protein_accession>
      <name>Calcium and integrin-binding protein 1</name>
      <uniprot_id>Q17QE5</uniprot_id>
      <gene_name>CIB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02724</protein_accession>
      <name>PCDH12 protein</name>
      <uniprot_id>A5D7V2</uniprot_id>
      <gene_name>PCDH12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02725</protein_accession>
      <name>Alpha-actinin-4</name>
      <uniprot_id>A5D7D1</uniprot_id>
      <gene_name>ACTN4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02726</protein_accession>
      <name>RAGE-binding protein</name>
      <uniprot_id>B6VAP8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02727</protein_accession>
      <name>C-X-C chemokine receptor type 4</name>
      <uniprot_id>P25930</uniprot_id>
      <gene_name>CXCR4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02728</protein_accession>
      <name>CD97 molecule</name>
      <uniprot_id>A6QNW8</uniprot_id>
      <gene_name>CD97</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02729</protein_accession>
      <name>THBS3 protein</name>
      <uniprot_id>A6QQT1</uniprot_id>
      <gene_name>THBS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02730</protein_accession>
      <name>PCDH1 protein</name>
      <uniprot_id>A4IFK1</uniprot_id>
      <gene_name>PCDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02731</protein_accession>
      <name>Voltage-dependent calcium channel gamma-3 subunit</name>
      <uniprot_id>Q0VD05</uniprot_id>
      <gene_name>CACNG3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02732</protein_accession>
      <name>Endothelial differentiation-related factor 1</name>
      <uniprot_id>Q3T0V7</uniprot_id>
      <gene_name>EDF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02733</protein_accession>
      <name>Calcium binding and coiled-coil domain 2</name>
      <uniprot_id>B1H0X0</uniprot_id>
      <gene_name>CALCOCO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02734</protein_accession>
      <name>PEF1 protein</name>
      <uniprot_id>A5D7S6</uniprot_id>
      <gene_name>PEF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02735</protein_accession>
      <name>FK506 binding protein 9</name>
      <uniprot_id>A1L517</uniprot_id>
      <gene_name>FKBP9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02736</protein_accession>
      <name>Cadherin-1</name>
      <uniprot_id>Q6R8F2</uniprot_id>
      <gene_name>CDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02737</protein_accession>
      <name>Desmocollin-2</name>
      <uniprot_id>P33545</uniprot_id>
      <gene_name>DSC2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02738</protein_accession>
      <name>Hippocalcin-like protein 1</name>
      <uniprot_id>P29105</uniprot_id>
      <gene_name>HPCAL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02739</protein_accession>
      <name>Alpha-actinin-3</name>
      <uniprot_id>Q0III9</uniprot_id>
      <gene_name>ACTN3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02740</protein_accession>
      <name>Calcyphosin</name>
      <uniprot_id>Q0VCC0</uniprot_id>
      <gene_name>CAPS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02741</protein_accession>
      <name>FKBP7 protein</name>
      <uniprot_id>A6QPJ6</uniprot_id>
      <gene_name>FKBP7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02742</protein_accession>
      <name>Calcium channel, voltage-dependent, P/Q type, Cav2.1 alpha 1A subunit</name>
      <uniprot_id>A5ACB6</uniprot_id>
      <gene_name>CACNA1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02743</protein_accession>
      <name>Endothelin-1 receptor</name>
      <uniprot_id>P21450</uniprot_id>
      <gene_name>EDNRA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02744</protein_accession>
      <name>Clathrin light chain B</name>
      <uniprot_id>P04975</uniprot_id>
      <gene_name>CLTB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02745</protein_accession>
      <name>Cadherin-2</name>
      <uniprot_id>P19534</uniprot_id>
      <gene_name>CDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02746</protein_accession>
      <name>SLC25A12 protein</name>
      <uniprot_id>A6QNM9</uniprot_id>
      <gene_name>SLC25A12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02747</protein_accession>
      <name>Calpain 3, (P94)</name>
      <uniprot_id>A6QP82</uniprot_id>
      <gene_name>CAPN3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02748</protein_accession>
      <name>CDH17 protein</name>
      <uniprot_id>A6H7H6</uniprot_id>
      <gene_name>CDH17</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02749</protein_accession>
      <name>LETM1 and EF-hand domain-containing protein 1, mitochondrial</name>
      <uniprot_id>Q0VCA3</uniprot_id>
      <gene_name>LETM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02750</protein_accession>
      <name>Annexin A8</name>
      <uniprot_id>Q95L54</uniprot_id>
      <gene_name>ANXA8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02751</protein_accession>
      <name>Annexin A4</name>
      <uniprot_id>P13214</uniprot_id>
      <gene_name>ANXA4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02752</protein_accession>
      <name>NKD1 protein</name>
      <uniprot_id>A7Z042</uniprot_id>
      <gene_name>NKD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02753</protein_accession>
      <name>Cadherin-5</name>
      <uniprot_id>Q6URK6</uniprot_id>
      <gene_name>CDH5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02754</protein_accession>
      <name>Fibrous sheath CABYR-binding protein</name>
      <uniprot_id>Q2T9N0</uniprot_id>
      <gene_name>FSCB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02755</protein_accession>
      <name>Calretinin</name>
      <uniprot_id>Q3ZBY3</uniprot_id>
      <gene_name>CALB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02756</protein_accession>
      <name>Myosin regulatory light polypeptide 9</name>
      <uniprot_id>A1L5B0</uniprot_id>
      <gene_name>MYL9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02757</protein_accession>
      <name>CDH1 protein</name>
      <uniprot_id>A6QLC4</uniprot_id>
      <gene_name>CDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02758</protein_accession>
      <name>PPP2R3A protein</name>
      <uniprot_id>A6QNV9</uniprot_id>
      <gene_name>PPP2R3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02759</protein_accession>
      <name>Calcium channel, voltage-dependent, gamma subunit 2</name>
      <uniprot_id>A0JNG9</uniprot_id>
      <gene_name>CACNG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02760</protein_accession>
      <name>Desmoglein-1</name>
      <uniprot_id>Q03763</uniprot_id>
      <gene_name>DSG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02761</protein_accession>
      <name>Cav2.1 P/Q pore forming alpha 1A subunit</name>
      <uniprot_id>A8Y827</uniprot_id>
      <gene_name>CACNA1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02762</protein_accession>
      <name>Allograft inflammatory factor 1</name>
      <uniprot_id>Q9BDK2</uniprot_id>
      <gene_name>AIF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02763</protein_accession>
      <name>Calcium channel, voltage-dependent, P/Q type, Cav2.1 alpha 1A subunit</name>
      <uniprot_id>A5ACB7</uniprot_id>
      <gene_name>CACNA1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02764</protein_accession>
      <name>RCN1 protein</name>
      <uniprot_id>A4IF88</uniprot_id>
      <gene_name>RCN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02765</protein_accession>
      <name>Fibrillin-1</name>
      <uniprot_id>P98133</uniprot_id>
      <gene_name>FBN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02766</protein_accession>
      <name>FBLN1 protein</name>
      <uniprot_id>A5D7S8</uniprot_id>
      <gene_name>FBLN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02767</protein_accession>
      <name>Homer protein homolog 1</name>
      <uniprot_id>Q2KJ56</uniprot_id>
      <gene_name>HOMER1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02768</protein_accession>
      <name>CDH16 protein</name>
      <uniprot_id>A7E335</uniprot_id>
      <gene_name>CDH16</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02769</protein_accession>
      <name>Gastrin/cholecystokinin type B receptor</name>
      <uniprot_id>P79266</uniprot_id>
      <gene_name>CCKBR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02770</protein_accession>
      <name>EF-hand calcium-binding domain-containing protein 3</name>
      <uniprot_id>Q2T9P0</uniprot_id>
      <gene_name>EFCAB3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02771</protein_accession>
      <name>Cadherin-3</name>
      <uniprot_id>P19535</uniprot_id>
      <gene_name>CDH3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02772</protein_accession>
      <name>Annexin A6</name>
      <uniprot_id>P79134</uniprot_id>
      <gene_name>ANXA6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02773</protein_accession>
      <name>RASEF protein</name>
      <uniprot_id>A7Z031</uniprot_id>
      <gene_name>RASEF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02774</protein_accession>
      <name>Neuron-specific calcium-binding protein hippocalcin</name>
      <uniprot_id>Q4PL64</uniprot_id>
      <gene_name>HPCA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02775</protein_accession>
      <name>RAS guanyl-releasing protein 4</name>
      <uniprot_id>Q1LZ97</uniprot_id>
      <gene_name>RASGRP4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02776</protein_accession>
      <name>Calmodulin</name>
      <uniprot_id>P62157</uniprot_id>
      <gene_name>CALM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02777</protein_accession>
      <name>Cadherin-13</name>
      <uniprot_id>Q3B7N0</uniprot_id>
      <gene_name>CDH13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02778</protein_accession>
      <name>Gonadotropin-releasing hormone receptor</name>
      <uniprot_id>P32236</uniprot_id>
      <gene_name>GNRHR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02779</protein_accession>
      <name>Thrombospondin 3</name>
      <uniprot_id>A7E3P4</uniprot_id>
      <gene_name>THBS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02780</protein_accession>
      <name>Calcium-binding protein p22</name>
      <uniprot_id>Q3SYS6</uniprot_id>
      <gene_name>CHP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02781</protein_accession>
      <name>EF-hand calcium-binding domain-containing protein 1</name>
      <uniprot_id>Q32L26</uniprot_id>
      <gene_name>EFCAB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02782</protein_accession>
      <name>Annexin A5</name>
      <uniprot_id>P81287</uniprot_id>
      <gene_name>ANXA5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02783</protein_accession>
      <name>Alpha-actinin-2</name>
      <uniprot_id>Q3ZC55</uniprot_id>
      <gene_name>ACTN2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02784</protein_accession>
      <name>Calcineurin B</name>
      <uniprot_id>A9ZTJ9</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02785</protein_accession>
      <name>Calcium-binding protein 5</name>
      <uniprot_id>Q9N1Q8</uniprot_id>
      <gene_name>CABP5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02786</protein_accession>
      <name>DSC1 protein</name>
      <uniprot_id>A6QR67</uniprot_id>
      <gene_name>DSC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02787</protein_accession>
      <name>Alpha-actinin 1</name>
      <uniprot_id>A4ZZF8</uniprot_id>
      <gene_name>ACTN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02788</protein_accession>
      <name>Annexin A2</name>
      <uniprot_id>P04272</uniprot_id>
      <gene_name>ANXA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02789</protein_accession>
      <name>EH domain-containing protein 1</name>
      <uniprot_id>Q5E9R3</uniprot_id>
      <gene_name>EHD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02790</protein_accession>
      <name>Voltage-dependent L-type calcium channel subunit beta-3</name>
      <uniprot_id>Q9MZL3</uniprot_id>
      <gene_name>CACNB3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02791</protein_accession>
      <name>KCNIP2 protein</name>
      <uniprot_id>A6QPA9</uniprot_id>
      <gene_name>KCNIP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02792</protein_accession>
      <name>45 kDa calcium-binding protein</name>
      <uniprot_id>Q3ZBZ1</uniprot_id>
      <gene_name>SDF4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02793</protein_accession>
      <name>Integrin alpha-V</name>
      <uniprot_id>P80746</uniprot_id>
      <gene_name>ITGAV</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02794</protein_accession>
      <name>CDH15 protein</name>
      <uniprot_id>A6QP71</uniprot_id>
      <gene_name>CDH15</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02795</protein_accession>
      <name>Annexin 5</name>
      <uniprot_id>A1L5B6</uniprot_id>
      <gene_name>ANXA5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02796</protein_accession>
      <name>Cav2.1 P/Q pore forming alpha 1A subunit</name>
      <uniprot_id>A8Y829</uniprot_id>
      <gene_name>CACNA1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02797</protein_accession>
      <name>Endothelin B receptor</name>
      <uniprot_id>P28088</uniprot_id>
      <gene_name>EDNRB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02798</protein_accession>
      <name>SPARC related modular calcium binding 1</name>
      <uniprot_id>A0JNE0</uniprot_id>
      <gene_name>SMOC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02799</protein_accession>
      <name>Calsyntenin-3</name>
      <uniprot_id>Q0VCN6</uniprot_id>
      <gene_name>CLSTN3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02800</protein_accession>
      <name>Casein-like phosphoprotein</name>
      <uniprot_id>Q2TBJ9</uniprot_id>
      <gene_name>CLPH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02801</protein_accession>
      <name>EF-hand domain-containing protein D1</name>
      <uniprot_id>Q17QM6</uniprot_id>
      <gene_name>EFHD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02802</protein_accession>
      <name>Voltage-dependent calcium channel gamma-1 subunit</name>
      <uniprot_id>Q08DE1</uniprot_id>
      <gene_name>CACNG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02803</protein_accession>
      <name>Cadherin-18</name>
      <uniprot_id>Q08DJ5</uniprot_id>
      <gene_name>CDH18</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02804</protein_accession>
      <name>S-arrestin</name>
      <uniprot_id>P08168</uniprot_id>
      <gene_name>SAG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02805</protein_accession>
      <name>Centrin-2</name>
      <uniprot_id>Q2TBN3</uniprot_id>
      <gene_name>CETN2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02806</protein_accession>
      <name>CB1 cannabinoid receptor-interacting protein 1</name>
      <uniprot_id>Q17QM9</uniprot_id>
      <gene_name>CNRIP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02807</protein_accession>
      <name>ANXA13 protein</name>
      <uniprot_id>A3KN40</uniprot_id>
      <gene_name>ANXA13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02808</protein_accession>
      <name>Parvalbumin</name>
      <uniprot_id>C1KUF7</uniprot_id>
      <gene_name>pvalb1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02809</protein_accession>
      <name>CDH19 protein</name>
      <uniprot_id>A5PJM6</uniprot_id>
      <gene_name>CDH19</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02810</protein_accession>
      <name>Clathrin light chain A</name>
      <uniprot_id>P04973</uniprot_id>
      <gene_name>CLTA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02811</protein_accession>
      <name>Calcium-binding protein 2</name>
      <uniprot_id>Q9N1Q9</uniprot_id>
      <gene_name>CABP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02812</protein_accession>
      <name>NID2 protein</name>
      <uniprot_id>A7E306</uniprot_id>
      <gene_name>NID2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02813</protein_accession>
      <name>Calmegin</name>
      <uniprot_id>Q3SYT6</uniprot_id>
      <gene_name>CLGN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02814</protein_accession>
      <name>Calcium-binding atopy-related autoantigen 1</name>
      <uniprot_id>Q0IIL1</uniprot_id>
      <gene_name>CBARA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02815</protein_accession>
      <name>CAPSL protein</name>
      <uniprot_id>A6H790</uniprot_id>
      <gene_name>CAPSL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02816</protein_accession>
      <name>PCDHGC3 protein</name>
      <uniprot_id>A5D7F4</uniprot_id>
      <gene_name>PCDHGC3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02817</protein_accession>
      <name>Calcium channel, voltage-dependent, P/Q type, Cav2.1 alpha 1A subunit</name>
      <uniprot_id>A5ACB8</uniprot_id>
      <gene_name>CACNA1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02818</protein_accession>
      <name>RAS guanyl-releasing protein 2</name>
      <uniprot_id>A6N9I4</uniprot_id>
      <gene_name>RASGRP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02819</protein_accession>
      <name>Calumenin</name>
      <uniprot_id>Q3T0K1</uniprot_id>
      <gene_name>CALU</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02820</protein_accession>
      <name>Cadherin-6</name>
      <uniprot_id>Q3SWX5</uniprot_id>
      <gene_name>CDH6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02821</protein_accession>
      <name>PCDHGA8 protein</name>
      <uniprot_id>A5PKJ8</uniprot_id>
      <gene_name>PCDHGA8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02822</protein_accession>
      <name>Alpha-actinin-1</name>
      <uniprot_id>Q3B7N2</uniprot_id>
      <gene_name>ACTN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02823</protein_accession>
      <name>Annexin IV</name>
      <uniprot_id>A1L514</uniprot_id>
      <gene_name>ANXA4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02824</protein_accession>
      <name>Voltage-dependent L-type calcium channel subunit beta-1</name>
      <uniprot_id>Q9MZL7</uniprot_id>
      <gene_name>CACNB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02825</protein_accession>
      <name>PCDHGA2 protein</name>
      <uniprot_id>A5D7Q6</uniprot_id>
      <gene_name>PCDHGA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02826</protein_accession>
      <name>PCDHA13 protein</name>
      <uniprot_id>A7E317</uniprot_id>
      <gene_name>PCDHA13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02827</protein_accession>
      <name>Cav2.1 P/Q pore forming alpha 1A subunit</name>
      <uniprot_id>A8Y828</uniprot_id>
      <gene_name>CACNA1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02828</protein_accession>
      <name>CALML5 protein</name>
      <uniprot_id>A4IFQ6</uniprot_id>
      <gene_name>CALML5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02829</protein_accession>
      <name>PCDHGB4 protein</name>
      <uniprot_id>A6QNV3</uniprot_id>
      <gene_name>PCDHGB4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02830</protein_accession>
      <name>Fibrinogen gamma-B chain</name>
      <uniprot_id>P12799</uniprot_id>
      <gene_name>FGG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02831</protein_accession>
      <name>LOC515336 protein</name>
      <uniprot_id>A6QPE9</uniprot_id>
      <gene_name>LOC515336</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:08 UTC</creation_date>
  <update_date>2020-03-13 16:21:24 UTC</update_date>
  <accession>BMDB0000466</accession>
  <secondary_accessions>
    <accession>BMDB00466</accession>
  </secondary_accessions>
  <name>3-Methylindole</name>
  <description/>
  <synonyms>
    <synonym>3-Methyl-4,5-benzopyrrole</synonym>
    <synonym>beta-Methylindole</synonym>
    <synonym>Skatol</synonym>
    <synonym>b-Methylindole</synonym>
    <synonym>Β-methylindole</synonym>
    <synonym>3-Methyl-1H-indole</synonym>
    <synonym>3-MI</synonym>
    <synonym>Scatole</synonym>
    <synonym>Skatole</synonym>
    <synonym>3 Methylindole</synonym>
    <synonym>3-Methylindole</synonym>
  </synonyms>
  <chemical_formula>C9H9N</chemical_formula>
  <average_molecular_weight>131.1745</average_molecular_weight>
  <monisotopic_moleculate_weight>131.073499293</monisotopic_moleculate_weight>
  <iupac_name>3-methyl-1H-indole</iupac_name>
  <traditional_iupac>scatole</traditional_iupac>
  <cas_registry_number>83-34-1</cas_registry_number>
  <smiles>CC1=CNC2=C1C=CC=C2</smiles>
  <inchi>InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3</inchi>
  <inchikey>ZFRKQXVRDFCRJG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 3-methylindoles. These are aromatic heterocyclic compounds that contain an indole moiety substituted at the 3-position with a methyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Indoles</sub_class>
    <direct_parent>3-methylindoles</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-methylindole</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>methylindole</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>97.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.498 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.6</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>17.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-methyl-1H-indole</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>131.1745</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>131.073499293</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CNC2=C1C=CC=C2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H9N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZFRKQXVRDFCRJG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>15.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439754</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB004302</foodb_id>
  <kegg_id>C08313</kegg_id>
  <chemspider_id>6480</chemspider_id>
  <pubchem_compound_id>6736</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>9171</chebi_id>
  <drugbank_id/>
  <meta_cyc_id>SKATOLE</meta_cyc_id>
  <knapsack_id>C00001430</knapsack_id>
  <wikipedia_id>Skatole</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5453</metlin_id>
  <synthesis_reference>Xu, Jianguo; Xu, Lili; Shi, Hongxin.  Synthesis of 3-methylindole and its new purification method.    Huagong Shengchan Yu Jishu  (2005),  12(4),  12-14.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:09 UTC</creation_date>
  <update_date>2020-04-15 22:13:57 UTC</update_date>
  <accession>BMDB0000467</accession>
  <secondary_accessions>
    <accession>BMDB00467</accession>
  </secondary_accessions>
  <name>Nutriacholic acid</name>
  <description/>
  <synonyms>
    <synonym>Nutriacholate</synonym>
    <synonym>3a-Hydroxy-7-oxo-5b-cholanoate</synonym>
    <synonym>3a-Hydroxy-7-oxo-5b-cholanoic acid</synonym>
    <synonym>5b-Cholanic acid-3a-ol-7-one</synonym>
    <synonym>7-Ketochenodeoxycholate</synonym>
    <synonym>7-Ketochenodeoxycholic acid</synonym>
    <synonym>7-Ketolithocholate</synonym>
    <synonym>7-Ketolithocholic acid</synonym>
    <synonym>7-oxo-3a-Hydroxycholan-24-Oate</synonym>
    <synonym>7-oxo-3a-Hydroxycholan-24-Oic acid</synonym>
    <synonym>7-Oxolithocholate</synonym>
    <synonym>7-Oxolithocholic acid</synonym>
    <synonym>3 alpha-Hydroxy-7-keto-5 beta-cholanoate</synonym>
    <synonym>3 alpha-Ol-7-one-5 beta-cholanoic acid</synonym>
    <synonym>7-Ketolithocholic acid, (3beta,5alpha)-isomer</synonym>
    <synonym>(4S)-4-[(1S,2S,5R,7S,10R,11S,15R)-5-Hydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H38O4</chemical_formula>
  <average_molecular_weight>390.5561</average_molecular_weight>
  <monisotopic_moleculate_weight>390.277009704</monisotopic_moleculate_weight>
  <iupac_name>(4S)-4-[(1S,2S,5R,7S,10R,11S,15R)-5-hydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4S)-4-[(1S,2S,5R,7S,10R,11S,15R)-5-hydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>4651-67-6</cas_registry_number>
  <smiles>[H][C@@]12CCC([C@@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)C[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-19,22,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17?,18-,19-,22-,23-,24+/m0/s1</inchi>
  <inchikey>DXOCDBGWDZAYRQ-QPVZPPSOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Monohydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-oxosteroids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monohydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4S)-4-[(1S,2S,5R,7S,10R,11S,15R)-5-hydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>390.5561</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>390.277009704</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC([C@@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)C[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H38O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-19,22,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17?,18-,19-,22-,23-,24+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DXOCDBGWDZAYRQ-QPVZPPSOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>108.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>44.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357366</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022059</foodb_id>
  <kegg_id/>
  <chemspider_id/>
  <pubchem_compound_id>53477693</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5454</metlin_id>
  <synthesis_reference>Kimura, Noriyuki; Mikami, Kazutoshi; Iwase, Mitsuyoshi.  3a,7b-Dihydroxy-5b-cholanic acid.    Jpn. Kokai Tokkyo Koho  (1985),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:10 UTC</creation_date>
  <update_date>2020-04-15 22:13:57 UTC</update_date>
  <accession>BMDB0000468</accession>
  <secondary_accessions>
    <accession>BMDB00468</accession>
  </secondary_accessions>
  <name>Biopterin</name>
  <description/>
  <synonyms>
    <synonym>(-)-Biopterin</synonym>
    <synonym>(1'r,1's) Biopterin</synonym>
    <synonym>2-Amino-6-(L-erythro-1,2-dihydroxypropyl)-4(3H)-pteridinone</synonym>
    <synonym>6-Biopterin</synonym>
    <synonym>L-Biopterin</synonym>
    <synonym>L-Erythro-biopterin</synonym>
    <synonym>Pterin H b2</synonym>
    <synonym>[S-(R*,s*)]-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone</synonym>
    <synonym>Orinapterin</synonym>
    <synonym>Dictyopterin</synonym>
    <synonym>2-Amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone</synonym>
    <synonym>Biopterin</synonym>
  </synonyms>
  <chemical_formula>C9H11N5O3</chemical_formula>
  <average_molecular_weight>237.2153</average_molecular_weight>
  <monisotopic_moleculate_weight>237.086189243</monisotopic_moleculate_weight>
  <iupac_name>2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4,8-dihydropteridin-4-one</iupac_name>
  <traditional_iupac>2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-8H-pteridin-4-one</traditional_iupac>
  <cas_registry_number>22150-76-1</cas_registry_number>
  <smiles>C[C@H](O)[C@H](O)C1=CNC2=NC(N)=NC(=O)C2=N1</smiles>
  <inchi>InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1</inchi>
  <inchikey>LHQIJBMDNUYRAM-DZSWIPIPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Biopterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrazines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Biopterin</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrazine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>biopterin</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>0.7 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-4,8-dihydropteridin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>237.2153</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>237.086189243</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](O)[C@H](O)C1=CNC2=NC(N)=NC(=O)C2=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11N5O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LHQIJBMDNUYRAM-DZSWIPIPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>132.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>57.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361281</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022060</foodb_id>
  <kegg_id>C06313</kegg_id>
  <chemspider_id>392795</chemspider_id>
  <pubchem_compound_id>445040</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>63931</chebi_id>
  <drugbank_id/>
  <meta_cyc_id>CPD-10819</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Biopterin</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>247</metlin_id>
  <synthesis_reference>Mori, Kenji; Kikuchi, Haruhiko.  Synthesis of (-)-biopterin.    Liebigs Annalen der Chemie  (1989),   (10),  963-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:11 UTC</creation_date>
  <update_date>2020-03-13 16:21:26 UTC</update_date>
  <accession>BMDB0000469</accession>
  <secondary_accessions>
    <accession>BMDB00469</accession>
  </secondary_accessions>
  <name>5-Hydroxymethyluracil</name>
  <description>5-Hydroxymethyluracil, also known as A-hydroxythymine, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. 5-Hydroxymethyluracil is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Hydroxymethyluracil is a potentially toxic compound.</description>
  <synonyms>
    <synonym>5-(Hydroxymethyl)-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>5-(Hydroxymethyl)uracil</synonym>
    <synonym>5-HYDROXYMETHYL uracil</synonym>
    <synonym>5-(Hydroxymethyl)-1,3-dihydropyrimidine-2,4-dione</synonym>
    <synonym>a-Hydroxythymine</synonym>
    <synonym>alpha-Hydroxythymine</synonym>
    <synonym>Hydroxymethyluracil</synonym>
  </synonyms>
  <chemical_formula>C5H6N2O3</chemical_formula>
  <average_molecular_weight>142.1127</average_molecular_weight>
  <monisotopic_moleculate_weight>142.037842068</monisotopic_moleculate_weight>
  <iupac_name>5-(hydroxymethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione</iupac_name>
  <traditional_iupac>5-hydroxymethyluracil</traditional_iupac>
  <cas_registry_number>4433-40-3</cas_registry_number>
  <smiles>OCC1=CNC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C5H6N2O3/c8-2-3-1-6-5(10)7-4(3)9/h1,8H,2H2,(H2,6,7,9,10)</inchi>
  <inchikey>JDBGXEHEIRGOBU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazines</class>
    <sub_class>Pyrimidines and pyrimidine derivatives</sub_class>
    <direct_parent>Pyrimidones</direct_parent>
    <alternative_parents>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>primary alcohol</external_descriptor>
      <external_descriptor>pyrimidone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>44 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-(hydroxymethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>142.1127</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>142.037842068</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC1=CNC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H6N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H6N2O3/c8-2-3-1-6-5(10)7-4(3)9/h1,8H,2H2,(H2,6,7,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JDBGXEHEIRGOBU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>78.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440076</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022061</foodb_id>
  <kegg_id>C03088</kegg_id>
  <chemspider_id>70544</chemspider_id>
  <pubchem_compound_id>78168</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16964</chebi_id>
  <drugbank_id/>
  <meta_cyc_id>CPD-254</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5456</metlin_id>
  <synthesis_reference>Abbott, Mitchel Theodore.  The cell-free synthesis of 5-hydroxymethyluracil.  (1963), 140 pp</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:12 UTC</creation_date>
  <update_date>2020-04-14 22:47:31 UTC</update_date>
  <accession>BMDB0000472</accession>
  <secondary_accessions>
    <accession>BMDB00472</accession>
  </secondary_accessions>
  <name>5-Hydroxy-L-tryptophan</name>
  <description>5-Hydroxy-L-tryptophan, also known as 5-HTP or oxitriptan, belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5. 5-Hydroxy-L-tryptophan exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 5-Hydroxy-L-tryptophan participates in a number of enzymatic reactions, within cattle. In particular, 5-Hydroxy-L-tryptophan and 4a-hydroxytetrahydrobiopterin can be biosynthesized from L-tryptophan and tetrahydrobiopterin through its interaction with the enzyme tryptophan 5-hydroxylase 1. In addition, 5-Hydroxy-L-tryptophan can be converted into serotonin through its interaction with the enzyme aromatic-L-amino-acid decarboxylase. In cattle, 5-hydroxy-L-tryptophan is involved in the metabolic pathway called the tryptophan metabolism pathway. 5-Hydroxy-L-tryptophan is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(+-)-5-Hydroxytryptophan</synonym>
    <synonym>5-HTP</synonym>
    <synonym>5-Hydroxy-DL-tryptophan</synonym>
    <synonym>5-Hydroxytryptophan DL-form</synonym>
    <synonym>DL-5-HTP</synonym>
    <synonym>DL-5-Hydroxytryptophan</synonym>
    <synonym>(S)-5-Hydroxytryptophan</synonym>
    <synonym>5-Hydroxy-tryptophan</synonym>
    <synonym>5-Hydroxyl-L-tryptophan</synonym>
    <synonym>5-Hydroxytryptophan</synonym>
    <synonym>5-Hydroxytryptophan L form</synonym>
    <synonym>5-Hydroxytryptophan L-form</synonym>
    <synonym>Cincofarm</synonym>
    <synonym>Hydroxytryptophan</synonym>
    <synonym>L-5-Hydroxytryptophan</synonym>
    <synonym>Levothym</synonym>
    <synonym>Levotinine</synonym>
    <synonym>Oxitriptan</synonym>
    <synonym>Oxyfan</synonym>
    <synonym>Oxytryptophan</synonym>
    <synonym>Pretonine</synonym>
    <synonym>Quietim</synonym>
    <synonym>Serotonyl</synonym>
    <synonym>Telesol</synonym>
    <synonym>Triptene</synonym>
    <synonym>5 Hydroxytryptophan</synonym>
    <synonym>5-Hydroxy- tryptophan</synonym>
    <synonym>Tryptophan, 5 hydroxy</synonym>
  </synonyms>
  <chemical_formula>C11H12N2O3</chemical_formula>
  <average_molecular_weight>220.2246</average_molecular_weight>
  <monisotopic_moleculate_weight>220.08479226</monisotopic_moleculate_weight>
  <iupac_name>2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid</iupac_name>
  <traditional_iupac>DL-5-hydroxytryptophan</traditional_iupac>
  <cas_registry_number>56-69-9</cas_registry_number>
  <smiles>NC(CC1=CNC2=C1C=C(O)C=C2)C(O)=O</smiles>
  <inchi>InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)</inchi>
  <inchikey>LDCYZAJDBXYCGN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Tryptamines and derivatives</sub_class>
    <direct_parent>Serotonins</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>3-alkylindoles</alternative_parent>
      <alternative_parent>Alpha amino acids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxyindoles</alternative_parent>
      <alternative_parent>Indolyl carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-alkylindole</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyindole</substituent>
      <substituent>Indole</substituent>
      <substituent>Indolyl carboxylic acid derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Serotonin</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>hydroxytryptophan</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>220.2246</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>220.08479226</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CC1=CNC2=C1C=C(O)C=C2)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H12N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LDCYZAJDBXYCGN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>99.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>58.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451955</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by UPLC-Q-TOF MS E</comment>
      <references>
        <reference>
          <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
          <pubmed_id>28342601</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01017</kegg_id>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id>144</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>28171</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001371</knapsack_id>
  <bigg_id/>
  <wikipedia_id>5-Hydroxytryptophan</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Boroda, E.; Rakowska, S.; Kanski, R.; Kanska, M.  Enzymatic synthesis of L-tryptophan and 5'-hydroxy-L-tryptophan labeled with deuterium and tritium at the a-carbon position.    Journal of Labelled Compounds &amp; Radiopharmaceuticals  (2003),  46(8),  691-698.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
      <pubmed_id>28342601</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00936</protein_accession>
      <name>Aromatic-L-amino-acid decarboxylase</name>
      <uniprot_id>P27718</uniprot_id>
      <gene_name>DDC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:13 UTC</creation_date>
  <update_date>2020-03-13 16:21:27 UTC</update_date>
  <accession>BMDB0000473</accession>
  <secondary_accessions>
    <accession>BMDB00473</accession>
  </secondary_accessions>
  <name>6-Dimethylaminopurine</name>
  <description/>
  <synonyms>
    <synonym>6-(Dimethylamino)purine</synonym>
    <synonym>6-Dimethyladenine</synonym>
    <synonym>N,N-Dimethyl-1H-purin-6-amine</synonym>
    <synonym>N,N-Dimethyl-6-aminopurine</synonym>
    <synonym>N,N-Dimethyladenine</synonym>
    <synonym>N(6)-Dimethyladenine</synonym>
    <synonym>6,6-Dimethyladenine</synonym>
    <synonym>6-(Dimethylamino)-purine</synonym>
    <synonym>6-Dimethylamine purine</synonym>
    <synonym>Dimethyladenine</synonym>
    <synonym>DMAP</synonym>
    <synonym>N,N-Dimethyl-adenine</synonym>
    <synonym>N6,N6-Dimethyl-adenine</synonym>
    <synonym>N6,N6-Dimethyladenine</synonym>
    <synonym>6-DMAP</synonym>
    <synonym>Dimethylaminopurine</synonym>
    <synonym>N(6),N(6)-Dimethyladenine</synonym>
    <synonym>6-Dimethylaminopurine</synonym>
  </synonyms>
  <chemical_formula>C7H9N5</chemical_formula>
  <average_molecular_weight>163.1799</average_molecular_weight>
  <monisotopic_moleculate_weight>163.085795313</monisotopic_moleculate_weight>
  <iupac_name>N,N-dimethyl-7H-purin-6-amine</iupac_name>
  <traditional_iupac>6-(dimethylamino)-purine</traditional_iupac>
  <cas_registry_number>938-55-6</cas_registry_number>
  <smiles>CN(C)C1=NC=NC2=C1NC=N2</smiles>
  <inchi>InChI=1S/C7H9N5/c1-12(2)7-5-6(9-3-8-5)10-4-11-7/h3-4H,1-2H3,(H,8,9,10,11)</inchi>
  <inchikey>BVIAOQMSVZHOJM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 6-alkylaminopurines. 6-alkylaminopurines are compounds that contain an alkylamine group attached at the 6-position of a purine. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>6-alkylaminopurines</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Dialkylarylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-alkylaminopurine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Dialkylarylamine</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrimidine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>tertiary amine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N,N-dimethyl-7H-purin-6-amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>163.1799</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>163.085795313</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN(C)C1=NC=NC2=C1NC=N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H9N5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H9N5/c1-12(2)7-5-6(9-3-8-5)10-4-11-7/h3-4H,1-2H3,(H,8,9,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BVIAOQMSVZHOJM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14533</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022062</foodb_id>
  <kegg_id/>
  <chemspider_id>3022</chemspider_id>
  <pubchem_compound_id>3134</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>60281</chebi_id>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5460</metlin_id>
  <synthesis_reference>Baker, B. R.; Joseph, Joseph P.; Schaub, Robert E. Puromycin. Synthetic studies. I. Synthesis of 6-dimethylaminopurine, a hydrolytic fragment. Journal of Organic Chemistry (1954), 19 631-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:14 UTC</creation_date>
  <update_date>2020-04-16 17:52:15 UTC</update_date>
  <accession>BMDB0000474</accession>
  <secondary_accessions>
    <accession>BMDB00474</accession>
  </secondary_accessions>
  <name>Butanone</name>
  <description>Butanone, also known as aethylmethylketon or methyl acetone, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, butanone is considered to be an oxygenated hydrocarbon lipid molecule. Butanone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Butanone is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2-Butanon</synonym>
    <synonym>2-Butanone</synonym>
    <synonym>3-Butanone</synonym>
    <synonym>Aethylmethylketon</synonym>
    <synonym>Butanone 2</synonym>
    <synonym>C2H5COCH3</synonym>
    <synonym>Ethyl methyl cetone</synonym>
    <synonym>Ethyl methyl ketone</synonym>
    <synonym>Ethyl(methyl) ketone</synonym>
    <synonym>Ethylmethyl ketone</synonym>
    <synonym>Ethylmethylketon</synonym>
    <synonym>Meetco</synonym>
    <synonym>MEK</synonym>
    <synonym>Methyl acetone</synonym>
    <synonym>Methyl ethyl cetone</synonym>
    <synonym>Methyl ethyl ketone</synonym>
    <synonym>Methyl(ethyl) ketone</synonym>
    <synonym>Methylacetone</synonym>
    <synonym>Methylethyl ketone</synonym>
    <synonym>Methylethylketon</synonym>
    <synonym>Oxobutane</synonym>
    <synonym>Butan-2-one</synonym>
    <synonym>Butanone</synonym>
  </synonyms>
  <chemical_formula>C4H8O</chemical_formula>
  <average_molecular_weight>72.1057</average_molecular_weight>
  <monisotopic_moleculate_weight>72.057514878</monisotopic_moleculate_weight>
  <iupac_name>butan-2-one</iupac_name>
  <traditional_iupac>methyl(ethyl) ketone</traditional_iupac>
  <cas_registry_number>78-93-3</cas_registry_number>
  <smiles>CCC(C)=O</smiles>
  <inchi>InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3</inchi>
  <inchikey>ZWEHNKRNPOVVGH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as ketones. These are organic compounds  in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Ketones</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Oxygenated hydrocarbons</external_descriptor>
      <external_descriptor>a methyl-ethyl-ketone</external_descriptor>
      <external_descriptor>dialkyl ketone</external_descriptor>
      <external_descriptor>methyl ketone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-86.6 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>223.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.29</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>butan-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>72.1057</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>72.057514878</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(C)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZWEHNKRNPOVVGH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>20.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20704</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22255</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29.64 +/- 13.11</concentration_value>
      <concentration_units>mg/100g dry matter content</concentration_units>
      <comment>Italian raw milk</comment>
      <references>
        <reference>
          <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16.68 +/- 10.33</concentration_value>
      <concentration_units>mg/100g dry matter content</concentration_units>
      <comment>Slovenian raw milk</comment>
      <references>
        <reference>
          <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.272 +/- 0.0606</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>In raw milk samples for diets based on grass silage</comment>
      <references>
        <reference>
          <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
          <pubmed_id>12463694</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.226 +/- 0.197</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>In raw milk samples for diets based on maize silage</comment>
      <references>
        <reference>
          <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
          <pubmed_id>12463694</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0769 +/- 0.0464</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>In raw milk samples for diets based on hay</comment>
      <references>
        <reference>
          <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
          <pubmed_id>12463694</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB030703</foodb_id>
  <kegg_id>C02845</kegg_id>
  <chemspider_id>6321</chemspider_id>
  <pubchem_compound_id>6569</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28398</chebi_id>
  <drugbank_id/>
  <meta_cyc_id>MEK</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Butanone</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5461</metlin_id>
  <synthesis_reference>Vergnaud, Paul.  The manufacture of butanediol and butanone. (1950),</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
      <pubmed_id>12463694</pubmed_id>
    </reference>
    <reference>
      <reference_text>Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26.</reference_text>
      <pubmed_id>27236769</pubmed_id>
    </reference>
    <reference>
      <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:17 UTC</creation_date>
  <update_date>2020-04-15 22:13:58 UTC</update_date>
  <accession>BMDB0000476</accession>
  <secondary_accessions>
    <accession>BMDB00476</accession>
  </secondary_accessions>
  <name>3-Oxo-4,6-choladienoic acid</name>
  <description/>
  <synonyms>
    <synonym>3-oxo-4,6-Choladienoate</synonym>
    <synonym>3-oxo-4,6-Choladien-24-Oate</synonym>
    <synonym>3-oxo-4,6-Choladien-24-Oic acid</synonym>
    <synonym>3-Oxochola-4,6-dien-24-Oate</synonym>
    <synonym>(4R)-4-[(1S,2R,10S,11S,14R,15R)-2,15-Dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl]pentanoate</synonym>
    <synonym>3-oxo-4,6-Choladienoic acid</synonym>
  </synonyms>
  <chemical_formula>C24H34O3</chemical_formula>
  <average_molecular_weight>370.525</average_molecular_weight>
  <monisotopic_moleculate_weight>370.250794954</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>3-oxo-4,6-choladienoic acid</traditional_iupac>
  <cas_registry_number>88179-71-9</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H34O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h5-6,14-15,18-21H,4,7-13H2,1-3H3,(H,26,27)/t15-,18+,19-,20+,21+,23+,24-/m1/s1</inchi>
  <inchikey>CREVIXFSUWYGRJ-IHMUCKAYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-oxosteroids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-oxosteroid</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Bile acid, alcohol, or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>370.525</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>370.250794954</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H34O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H34O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h5-6,14-15,18-21H,4,7-13H2,1-3H3,(H,26,27)/t15-,18+,19-,20+,21+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CREVIXFSUWYGRJ-IHMUCKAYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>108.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>43.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320574</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022063</foodb_id>
  <drugbank_id/>
  <chemspider_id>4447080</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>5283992</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>88112</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5463</metlin_id>
  <synthesis_reference>Takehara, Jun; Fujiwara, Naoya; Endou, Kyouko; Kawai, Junya; Hosokawa, Akemi; Sumitani, Naoko.  Process for production of steroids.    PCT Int. Appl.  (2007),     138pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:18 UTC</creation_date>
  <update_date>2020-03-13 16:21:29 UTC</update_date>
  <accession>BMDB0000477</accession>
  <secondary_accessions>
    <accession>BMDB00477</accession>
  </secondary_accessions>
  <name>7Z,10Z-Hexadecadienoic acid</name>
  <description/>
  <synonyms>
    <synonym>(Z,Z)-7,10-Hexadecadienoic acid</synonym>
    <synonym>(Z,Z)-Hexadeca-7,10-dienoic acid</synonym>
    <synonym>7-cis,10-cis-Hexadecadienoic acid</synonym>
    <synonym>C16:2N-6,9</synonym>
    <synonym>(Z,Z)-7,10-Hexadecadienoate</synonym>
    <synonym>(Z,Z)-Hexadeca-7,10-dienoate</synonym>
    <synonym>7-cis,10-cis-Hexadecadienoate</synonym>
    <synonym>7Z,10Z-Hexadecadienoate</synonym>
    <synonym>7Z,10Z-Hexadecadienoic acid</synonym>
    <synonym>(7Z,10Z)-Hexadecadienoate</synonym>
  </synonyms>
  <chemical_formula>C16H28O2</chemical_formula>
  <average_molecular_weight>252.3923</average_molecular_weight>
  <monisotopic_moleculate_weight>252.20893014</monisotopic_moleculate_weight>
  <iupac_name>(7Z,10Z)-hexadeca-7,10-dienoic acid</iupac_name>
  <traditional_iupac>7Z,10Z-hexadecadienoic acid</traditional_iupac>
  <cas_registry_number>28290-73-5</cas_registry_number>
  <smiles>CCCCC\C=C/C\C=C/CCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C16H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h6-7,9-10H,2-5,8,11-15H2,1H3,(H,17,18)/b7-6-,10-9-</inchi>
  <inchikey>WPJGPAAPSBVXNU-HZJYTTRNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>hexadecadienoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(7Z,10Z)-hexadeca-7,10-dienoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>252.3923</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>252.20893014</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC\C=C/C\C=C/CCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H28O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h6-7,9-10H,2-5,8,11-15H2,1H3,(H,17,18)/b7-6-,10-9-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WPJGPAAPSBVXNU-HZJYTTRNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366204</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022066</foodb_id>
  <drugbank_id/>
  <chemspider_id>13628094</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>13932172</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>86147</chebi_id>
  <meta_cyc_id>CPD-17290</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5464</metlin_id>
  <synthesis_reference>Beaudoin, Adrien; Martin, Genevieve.  Method of extracting lipids from marine and aquatic animal tissues.    PCT Int. Appl.  (2000),     58 pp.  CODEN: PIXXD2  WO  2000023546  A1  20000427  CAN 132:305471  AN 2000:278070</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:19 UTC</creation_date>
  <update_date>2020-04-15 22:13:59 UTC</update_date>
  <accession>BMDB0000478</accession>
  <secondary_accessions>
    <accession>BMDB00478</accession>
  </secondary_accessions>
  <name>Allodeoxycholic acid</name>
  <description/>
  <synonyms>
    <synonym>Allodeoxycholate</synonym>
    <synonym>3a,12a-Dihydroxy-5a-cholan-24-Oate</synonym>
    <synonym>3a,12a-Dihydroxy-5a-cholan-24-Oic acid</synonym>
    <synonym>3a,12a-Dihydroxy-5a-cholanoate</synonym>
    <synonym>3a,12a-Dihydroxy-5a-cholanoic acid</synonym>
    <synonym>4-(3,12-Dihydroxy-10,13-dimethyl-tetradecahydro-20-oxa-cyclopropa[8,14]cyclopenta[a]phenanthren-17-yl)-pentanoate</synonym>
    <synonym>4-(3,12-Dihydroxy-10,13-dimethyl-tetradecahydro-20-oxa-cyclopropa[8,14]cyclopenta[a]phenanthren-17-yl)-pentanoic acid</synonym>
    <synonym>5a-Allodeoxycholate</synonym>
    <synonym>5a-Allodeoxycholic acid</synonym>
    <synonym>5a-Deoxycholate</synonym>
    <synonym>5a-Deoxycholic acid</synonym>
    <synonym>8,14-Epoxy-3a,12a-dihydroxy-5b,8X,14X-cholan-24-Oate</synonym>
    <synonym>8,14-Epoxy-3a,12a-dihydroxy-5b,8X,14X-cholan-24-Oic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,7S,10R,11S,15R,16S)-5,16-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O4</chemical_formula>
  <average_molecular_weight>392.572</average_molecular_weight>
  <monisotopic_moleculate_weight>392.292659768</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7S,10R,11S,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,7S,10R,11S,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>1912-55-6</cas_registry_number>
  <smiles>[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17+,18?,19+,20+,21+,23+,24-/m1/s1</inchi>
  <inchikey>KXGVEGMKQFWNSR-FBDAZGPESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7S,10R,11S,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>392.572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.292659768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17+,18?,19+,20+,21+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KXGVEGMKQFWNSR-FBDAZGPESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340311</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022065</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477694</pubchem_compound_id>
  <chebi_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5465</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Yukawa, Masashi.  Bile acids of the allo series. VIII. Synthesis of allodeoxycholic acid.    Hiroshima Journal of Medical Sciences  (1962),  11(4),  167-73.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:20 UTC</creation_date>
  <update_date>2020-04-16 20:38:27 UTC</update_date>
  <accession>BMDB0000479</accession>
  <secondary_accessions>
    <accession>BMDB00479</accession>
  </secondary_accessions>
  <name>3-Methylhistidine</name>
  <description>N(pros)-Methyl-L-histidine, also known as 3-methylhistidine, belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N(pros)-Methyl-L-histidine is possibly soluble (in water) and a very strong basic compound (based on its pKa). N(pros)-Methyl-L-histidine exists in all eukaryotes, ranging from yeast to humans.</description>
  <synonyms>
    <synonym>(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid</synonym>
    <synonym>3-Methyl-L-histidine</synonym>
    <synonym>N(Pai)-methyl-L-histidine</synonym>
    <synonym>N-pros-Methyl-L-histidine</synonym>
    <synonym>Tau-methylhistidine</synonym>
    <synonym>(2S)-2-Amino-3-(1-methyl-1H-imidazol-5-yl)propanoate</synonym>
    <synonym>3-N-Methyl-L-histidine</synonym>
    <synonym>L-3-Methylhistidine</synonym>
    <synonym>N(Pi)-methyl-L-histidine</synonym>
    <synonym>N(pros)-Methyl-L-histidine</synonym>
    <synonym>N3-Methyl-L-histidine</synonym>
    <synonym>Pi-methyl-L-histidine</synonym>
    <synonym>Tau-methyl-L-histidine</synonym>
    <synonym>3-Methylhistidine hydride</synonym>
    <synonym>N(Tau)-methylhistidine</synonym>
    <synonym>3-Methylhistidine dihydrochloride</synonym>
    <synonym>N Tau-methylhistidine</synonym>
    <synonym>3-Methylhistidine</synonym>
  </synonyms>
  <chemical_formula>C7H11N3O2</chemical_formula>
  <average_molecular_weight>169.1811</average_molecular_weight>
  <monisotopic_moleculate_weight>169.085126611</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid</iupac_name>
  <traditional_iupac>3,methylhistidine</traditional_iupac>
  <cas_registry_number>368-16-1</cas_registry_number>
  <smiles>[H][C@](N)(CC1=CN=CN1C)C(O)=O</smiles>
  <inchi>InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1</inchi>
  <inchikey>JDHILDINMRGULE-LURJTMIESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Histidine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolyl carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Histidine or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazolyl carboxylic acid derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-histidine derivative</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>200 mg/mL at 25 °C</value>
      <source>BEILSTEIN</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>169.1811</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>169.085126611</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@](N)(CC1=CN=CN1C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H11N3O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H11N3O2/c1-10-4-9-3-5(10)2-6(8)7(11)12/h3-4,6H,2,8H2,1H3,(H,11,12)/t6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JDHILDINMRGULE-LURJTMIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>81.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448170</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>14+/-2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>25+/-5</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>35+/-8</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>103 - 151</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>35+/-9</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>19+/-4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB093613</foodb_id>
  <kegg_id>C01152</kegg_id>
  <chemspider_id>58494</chemspider_id>
  <pubchem_compound_id>64969</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>27596</chebi_id>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>3-Methylhistidine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5466</metlin_id>
  <synthesis_reference>Ohba, Masashi; Mukaihira, Takafumi; Fujii, Tozo. Preparatory study for the synthesis of the starfish alkaloid imbricatine. Syntheses of 5-arylthio-3-methyl-L-histidines. Chemical &amp; Pharmaceutical Bulletin (1994), 42(9), 1784-90.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:22 UTC</creation_date>
  <update_date>2020-03-13 16:21:30 UTC</update_date>
  <accession>BMDB0000480</accession>
  <secondary_accessions>
    <accession>BMDB00480</accession>
  </secondary_accessions>
  <name>7,10-Hexadecadienoic acid</name>
  <description/>
  <synonyms>
    <synonym>7,10-Hexadecadienoate</synonym>
  </synonyms>
  <chemical_formula>C16H28O2</chemical_formula>
  <average_molecular_weight>252.398</average_molecular_weight>
  <monisotopic_moleculate_weight>252.208930142</monisotopic_moleculate_weight>
  <iupac_name>(7E,10E)-hexadeca-7,10-dienoic acid</iupac_name>
  <traditional_iupac>7,10-hexadecadienoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H]\C(CCCCC)=C(\[H])C\C([H])=C(/[H])CCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C16H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h6-7,9-10H,2-5,8,11-15H2,1H3,(H,17,18)/b7-6+,10-9+</inchi>
  <inchikey>WPJGPAAPSBVXNU-AVQMFFATSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(7E,10E)-hexadeca-7,10-dienoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>252.398</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>252.208930142</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]\C(CCCCC)=C(\[H])C\C([H])=C(/[H])CCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H28O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h6-7,9-10H,2-5,8,11-15H2,1H3,(H,17,18)/b7-6+,10-9+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WPJGPAAPSBVXNU-AVQMFFATSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1297693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1297694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1297695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1412314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1412315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1412316</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id/>
  <foodb_id/>
  <kegg_id/>
  <chebi_id/>
  <pubchem_compound_id>13932171</pubchem_compound_id>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <wikipedia_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference>Myagkova, G. I.; Novozhilov, A. V.; Bainova, M. S.; Bazilevskaya, G. I.; Yakimenko, S. M.; Preobrazhenskii, N. A.  Synthesis of aliphatic acids.  XXIII.  New process for synthesizing linoleic acid and substituted linoleic acids.    Biol. Aktiv. Soedin.  (1968),     3-6. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:23 UTC</creation_date>
  <update_date>2020-03-13 16:21:31 UTC</update_date>
  <accession>BMDB0000481</accession>
  <secondary_accessions>
    <accession>BMDB00481</accession>
  </secondary_accessions>
  <name>Allopurinol riboside</name>
  <description/>
  <synonyms>
    <synonym>4-Hydroxy[3,4-D]pyrazolopyrimidine riboside</synonym>
    <synonym>Allopurinol ribonucleoside</synonym>
    <synonym>Allopurinol-1-ribonucleoside</synonym>
  </synonyms>
  <chemical_formula>C10H12N4O5</chemical_formula>
  <average_molecular_weight>268.2261</average_molecular_weight>
  <monisotopic_moleculate_weight>268.080769514</monisotopic_moleculate_weight>
  <iupac_name>1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H,4H,7H-pyrazolo[3,4-d]pyrimidin-4-one</iupac_name>
  <traditional_iupac>1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-pyrazolo[3,4-d]pyrimidin-4-one</traditional_iupac>
  <cas_registry_number>16220-07-8</cas_registry_number>
  <smiles>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1N=CC2=C1NC=NC2=O</smiles>
  <inchi>InChI=1S/C10H12N4O5/c15-2-5-6(16)7(17)10(19-5)14-8-4(1-13-14)9(18)12-3-11-8/h1,3,5-7,10,15-17H,2H2,(H,11,12,18)/t5-,6-,7-,10-/m1/s1</inchi>
  <inchikey>KFQUAMTWOJHPEJ-DAGMQNCNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrazolo[3,4-d]pyrimidine glycosides. These are nucleosides or derivatives thereof that consist of a pyazolo[3,2-d]pyrimidine ring system that is N-glycosidically linked to a ribose or deoxyribose. They bear the sugar moiety on the pyrimidine part of the molecule.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrazolo[3,4-d]pyrimidine glycosides</class>
    <sub_class/>
    <direct_parent>Pyrazolo[3,4-d]pyrimidine glycosides</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrazoles</alternative_parent>
      <alternative_parent>Pyrazolo[3,4-d]pyrimidines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrazole</substituent>
      <substituent>Pyrazolo[3,4-d]pyrimidine</substituent>
      <substituent>Pyrazolo[3,4-d]pyrimidine glycoside</substituent>
      <substituent>Pyrazolopyrimidine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>nucleoside analogue</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H,4H,7H-pyrazolo[3,4-d]pyrimidin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>268.2261</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>268.080769514</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1N=CC2=C1NC=NC2=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N4O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N4O5/c15-2-5-6(16)7(17)10(19-5)14-8-4(1-13-14)9(18)12-3-11-8/h1,3,5-7,10,15-17H,2H2,(H,11,12,18)/t5-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KFQUAMTWOJHPEJ-DAGMQNCNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>129.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355686</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022067</foodb_id>
  <drugbank_id/>
  <chemspider_id>18512601</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>5273534</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>74074</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5468</metlin_id>
  <synthesis_reference>Korbukh, I. A.; Yakunina, N. G.; Preobrazhenskaya, M. N.  Synthesis and reactions of 4- and 4,6-substituted pyrazolo[3,4-d]pyrimidine nucleosides.    Bioorganicheskaya Khimiya  (1980),  6(11),  1632-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:24 UTC</creation_date>
  <update_date>2020-04-15 21:56:43 UTC</update_date>
  <accession>BMDB0000482</accession>
  <secondary_accessions>
    <accession>BMDB00482</accession>
  </secondary_accessions>
  <name>Caprylic acid</name>
  <description>Caprylic acid, also known as 8:0 or octylic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Caprylic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Caprylic acid exists in all living species, ranging from bacteria to humans. Caprylic acid participates in a number of enzymatic reactions, within cattle. In particular, Caprylic acid can be biosynthesized from trans-2-octenoic acid; which is mediated by the enzyme fatty acid synthase. enoyl reductase domain. In addition, Caprylic acid and malonic acid can be converted into 3-oxodecanoic acid through its interaction with the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In cattle, caprylic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway. Caprylic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Heptanecarboxylic acid</synonym>
    <synonym>8:0</synonym>
    <synonym>Acide octanoique</synonym>
    <synonym>Acido octanoico</synonym>
    <synonym>Acidum octanocium</synonym>
    <synonym>Acidum octanoicum</synonym>
    <synonym>C8:0</synonym>
    <synonym>CH3-[CH2]6-COOH</synonym>
    <synonym>Kaprylsaeure</synonym>
    <synonym>N-Caprylic acid</synonym>
    <synonym>N-Octanoic acid</synonym>
    <synonym>N-Octoic acid</synonym>
    <synonym>N-Octylic acid</synonym>
    <synonym>OCTANOIC ACID (caprylIC ACID)</synonym>
    <synonym>Octansaeure</synonym>
    <synonym>Octoic acid</synonym>
    <synonym>Octylic acid</synonym>
    <synonym>Octanoate</synonym>
    <synonym>1-Heptanecarboxylate</synonym>
    <synonym>N-Caprylate</synonym>
    <synonym>N-Octanoate</synonym>
    <synonym>N-Octoate</synonym>
    <synonym>N-Octylate</synonym>
    <synonym>OCTANOate (caprylate)</synonym>
    <synonym>Octoate</synonym>
    <synonym>Octylate</synonym>
    <synonym>Octanoic acid</synonym>
    <synonym>Caprylate</synonym>
    <synonym>Emery 657</synonym>
    <synonym>Kortacid 0899</synonym>
    <synonym>Lunac 8-95</synonym>
    <synonym>Lunac 8-98</synonym>
    <synonym>Neo-fat 8</synonym>
    <synonym>Neo-fat 8S</synonym>
    <synonym>Prifac 2901</synonym>
    <synonym>Caprylic acid, cadmium salt</synonym>
    <synonym>Caprylic acid, cesium salt</synonym>
    <synonym>Caprylic acid, manganese salt</synonym>
    <synonym>Caprylic acid, nickel(+2) salt</synonym>
    <synonym>Caprylic acid, zinc salt</synonym>
    <synonym>Caprylic acid, aluminum salt</synonym>
    <synonym>Caprylic acid, barium salt</synonym>
    <synonym>Caprylic acid, chromium(+2) salt</synonym>
    <synonym>Caprylic acid, lead(+2) salt</synonym>
    <synonym>Caprylic acid, potassium salt</synonym>
    <synonym>Caprylic acid, tin(+2) salt</synonym>
    <synonym>Sodium octanoate</synonym>
    <synonym>Caprylic acid, 14C-labeled</synonym>
    <synonym>Caprylic acid, lithium salt</synonym>
    <synonym>Caprylic acid, ruthenium(+3) salt</synonym>
    <synonym>Caprylic acid, sodium salt</synonym>
    <synonym>Caprylic acid, sodium salt, 11C-labeled</synonym>
    <synonym>Caprylic acid, tin salt</synonym>
    <synonym>Caprylic acid, zirconium salt</synonym>
    <synonym>Sodium caprylate</synonym>
    <synonym>Caprylic acid, ammonia salt</synonym>
    <synonym>Caprylic acid, calcium salt</synonym>
    <synonym>Caprylic acid, cobalt salt</synonym>
    <synonym>Caprylic acid, copper salt</synonym>
    <synonym>Caprylic acid, copper(+2) salt</synonym>
    <synonym>Caprylic acid, iridum(+3) salt</synonym>
    <synonym>Caprylic acid, iron(+3) salt</synonym>
    <synonym>Caprylic acid, lanthanum(+3) salt</synonym>
    <synonym>Caprylic acid, zirconium(+4) salt</synonym>
    <synonym>FA(8:0)</synonym>
    <synonym>Lithium octanoate</synonym>
  </synonyms>
  <chemical_formula>C8H16O2</chemical_formula>
  <average_molecular_weight>144.2114</average_molecular_weight>
  <monisotopic_moleculate_weight>144.115029756</monisotopic_moleculate_weight>
  <iupac_name>octanoic acid</iupac_name>
  <traditional_iupac>caprylic acid</traditional_iupac>
  <cas_registry_number>124-07-2</cas_registry_number>
  <smiles>CCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)</inchi>
  <inchikey>WWZKQHOCKIZLMA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Saturated fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>medium-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>16.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.789 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.05</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>octanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>144.2114</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>144.115029756</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WWZKQHOCKIZLMA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37560</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by infra-red spectroscopy and silieic acid columns</comment>
      <references>
        <reference>
          <reference_text>Laura Evans, Stuart Patton, R.D. McCarthy. Fatty Acid Composition of the Lipid Fractions from Bovine Serum Lipoproteins. J. Dairy Science (1961) 44(3) 475-482   doi: 10.3168/jds.S0022-0302(61)89765-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.5 +/- 0.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12.92 +/- 6.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13.4 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1594.88</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1386.85</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>277.371</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1317.51</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.2 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>277.371</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3397.79</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3328.45</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3120.42</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
          <pubmed_id>14168161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14.11 +/- 1.28</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk from a Danish Holstein herd by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12.83 +/- 2.57</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised whole milk (3.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.85 +/- 0.77</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised semi skimmed milk (1.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.11 +/- 1.026</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised skimmed milk (0.1% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12.9 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
          <pubmed_id>1779072</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4853.999 +/- 2080.285</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
          <pubmed_id>16899705</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17.682 +/- 0.42</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Catrienus De Jong Herman T. Badings. Determination of free fatty acids in milk and cheese procedures for extraction, clean up, and capillary gas chromatographic analysis. Journal of High Resolution Chromatography Volume 13, Issue 2, 1990</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23.01 +/- 8.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3536.485 +/- 832.114</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3397.799 +/- 693.428</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14.23 +/- 6.69</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.8 (0.6 - 1.6)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.8 (0.6 - 1.4)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.8 (0.6 - 1.7)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.6 (0.8 - 10.6)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C06423</kegg_id>
  <chemspider_id>370</chemspider_id>
  <foodb_id>FDB003336</foodb_id>
  <drugbank_id>DB04519</drugbank_id>
  <pubchem_compound_id>379</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28837</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001231</knapsack_id>
  <meta_cyc_id>CPD-195</meta_cyc_id>
  <bigg_id>48223</bigg_id>
  <wikipedia_id>Caprylic_acid</wikipedia_id>
  <metlin_id>5469</metlin_id>
  <synthesis_reference>Caprylic acid. Jpn. Kokai Tokkyo Koho  (1983),     4 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
      <pubmed_id>16899705</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
      <pubmed_id>1779072</pubmed_id>
    </reference>
    <reference>
      <reference_text>Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.</reference_text>
      <pubmed_id>20855010</pubmed_id>
    </reference>
    <reference>
      <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
      <pubmed_id>14168161</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.</reference_text>
      <pubmed_id>28219465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
    </reference>
    <reference>
      <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:25 UTC</creation_date>
  <update_date>2020-03-13 16:21:32 UTC</update_date>
  <accession>BMDB0000483</accession>
  <secondary_accessions>
    <accession>BMDB00483</accession>
  </secondary_accessions>
  <name>5b-Cholestane-3a,7a,12a,23S,25-pentol</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C27H48O5</chemical_formula>
  <average_molecular_weight>452.676</average_molecular_weight>
  <monisotopic_moleculate_weight>452.350174646</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7S,9R,10R,11S,15R,16S)-14-[(2S,4S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</iupac_name>
  <traditional_iupac>(1S,2S,5R,7S,9R,10R,11S,15R,16S)-14-[(2S,4S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@](O)(C[C@]([H])(C)C1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)C[C@]4([H])C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])C[C@]([H])(O)[C@]12C)CC(C)(C)O</smiles>
  <inchi>InChI=1S/C27H48O5/c1-15(10-18(29)14-25(2,3)32)19-6-7-20-24-21(13-23(31)27(19,20)5)26(4)9-8-17(28)11-16(26)12-22(24)30/h15-24,28-32H,6-14H2,1-5H3/t15-,16-,17+,18-,19?,20-,21-,22+,23-,24-,26-,27+/m0/s1</inchi>
  <inchikey>OXSBBBPDYVCAKC-UETGOZKZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Pentahydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Cholesterols and derivatives</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>23-hydroxysteroid</substituent>
      <substituent>25-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholestane-skeleton</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Pentahydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7S,9R,10R,11S,15R,16S)-14-[(2S,4S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>452.676</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>452.350174646</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@](O)(C[C@]([H])(C)C1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)C[C@]4([H])C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])C[C@]([H])(O)[C@]12C)CC(C)(C)O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H48O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H48O5/c1-15(10-18(29)14-25(2,3)32)19-6-7-20-24-21(13-23(31)27(19,20)5)26(4)9-8-17(28)11-16(26)12-22(24)30/h15-24,28-32H,6-14H2,1-5H3/t15-,16-,17+,18-,19?,20-,21-,22+,23-,24-,26-,27+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OXSBBBPDYVCAKC-UETGOZKZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>101.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>126.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>52.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1264885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1264886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1264887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1379959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1379960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1379961</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <drugbank_id/>
  <chemspider_id/>
  <kegg_id/>
  <pubchem_compound_id/>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Hoshita, Takahiko; Yasuhara, Misao; Kihira, Kenji; Kuramoto, Taiju.  Comparative biochemical studies of bile acids and bile alcohols.  V.  Identification of (23S)-5a-cholestane-3a,7a,12a,23,25-pentol in cerebrotendinous xanthomatosis.    Steroids  (1976),  27(5),  657-64. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:26 UTC</creation_date>
  <update_date>2020-03-13 16:21:32 UTC</update_date>
  <accession>BMDB0000486</accession>
  <secondary_accessions>
    <accession>BMDB00486</accession>
  </secondary_accessions>
  <name>7-Hydroxyoctanoic acid</name>
  <description/>
  <synonyms>
    <synonym>7-Hydroxyoctanoate</synonym>
    <synonym>7-Hydroxy-octanoate</synonym>
    <synonym>7-Hydroxy-octanoic acid</synonym>
    <synonym>7-Hydroxyoctanoic acid</synonym>
  </synonyms>
  <chemical_formula>C8H16O3</chemical_formula>
  <average_molecular_weight>160.2108</average_molecular_weight>
  <monisotopic_moleculate_weight>160.109944378</monisotopic_moleculate_weight>
  <iupac_name>7-hydroxyoctanoic acid</iupac_name>
  <traditional_iupac>7-hydroxyoctanoic acid</traditional_iupac>
  <cas_registry_number>17173-14-7</cas_registry_number>
  <smiles>CC(O)CCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C8H16O3/c1-7(9)5-3-2-4-6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)</inchi>
  <inchikey>OFCMTSZRXXFMBQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Medium-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Medium-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>7-hydroxyoctanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>160.2108</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>160.109944378</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(O)CCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16O3/c1-7(9)5-3-2-4-6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OFCMTSZRXXFMBQ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>704</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447340</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022069</foodb_id>
  <chemspider_id>146647</chemspider_id>
  <pubchem_compound_id>167627</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5473</metlin_id>
  <synthesis_reference>Sugiyama, Noboru; Gasha, Taketoshi; Kashima, Choji.  Macrocyclic dilactone.  I.  Synthesis of 7-hydroxyoctanoic acid dilactone.    Bulletin of the Chemical Society of Japan  (1967),  40(11),  02713-14.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:28 UTC</creation_date>
  <update_date>2020-03-13 16:21:33 UTC</update_date>
  <accession>BMDB0000488</accession>
  <secondary_accessions>
    <accession>BMDB00488</accession>
  </secondary_accessions>
  <name>4E,15Z-Bilirubin IXa</name>
  <description>Bilirubin belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. Bilirubin is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Bilirubin exists in all living species, ranging from bacteria to humans. In cattle, bilirubin is involved in the metabolic pathway called the porphyrin metabolism pathway. Bilirubin is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(4E)2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo--21H-biline-8,12-dipropanoic acid</synonym>
    <synonym>(4E)2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo--21H-biline-8,12-dipropanoate</synonym>
    <synonym>(4E,15Z)-Bilirubin ixa</synonym>
  </synonyms>
  <chemical_formula>C33H36N4O6</chemical_formula>
  <average_molecular_weight>584.6621</average_molecular_weight>
  <monisotopic_moleculate_weight>584.263484904</monisotopic_moleculate_weight>
  <iupac_name>3-(2-{[3-(2-carboxyethyl)-5-{[(2E)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid</iupac_name>
  <traditional_iupac>3-(2-{[3-(2-carboxyethyl)-5-{[(2E)-4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid</traditional_iupac>
  <cas_registry_number>69853-43-6</cas_registry_number>
  <smiles>CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2\NC(=O)C(C=C)=C2C)N1</smiles>
  <inchi>InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13+,27-14-</inchi>
  <inchikey>BPYKTIZUTYGOLE-KDUUSRDASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Bilirubins</sub_class>
    <direct_parent>Bilirubins</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrrolines</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Bilirubin skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Pyrroline</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>biladienes</external_descriptor>
      <external_descriptor>dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(2-{[3-(2-carboxyethyl)-5-{[(2E)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>584.6621</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>584.263484904</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2\NC(=O)C(C=C)=C2C)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C33H36N4O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13+,27-14-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BPYKTIZUTYGOLE-KDUUSRDASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>164.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>168.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>65.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1227070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1227071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1227072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1342666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1342667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1342668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5165</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id>13628097</chemspider_id>
  <foodb_id>FDB022070</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>21252250</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>72719</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Bilirubin</wikipedia_id>
  <metlin_id>5475</metlin_id>
  <synthesis_reference>McDonagh, Antony F.; Lightner, David A.; Wooldridge, Timothy A.  Geometric isomerization of bilirubin-IXa and its dimethyl ester.    Journal of the Chemical Society, Chemical Communications  (1979),   (3),  110-12. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:29 UTC</creation_date>
  <update_date>2020-04-15 22:32:23 UTC</update_date>
  <accession>BMDB0000489</accession>
  <secondary_accessions>
    <accession>BMDB00489</accession>
  </secondary_accessions>
  <name>Aspartylglycosamine</name>
  <description/>
  <synonyms>
    <synonym>1-beta-Aspartyl-N-acetyl-D-glucosaminylamine</synonym>
    <synonym>2-Acetamido-1-(beta-L-aspartamido)-1,2-dideoxy-beta-D-glucose</synonym>
    <synonym>2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-beta-D-glucopyranosylamine</synonym>
    <synonym>2-Acetamido-N-L-beta-aspartyl-2-deoxy-beta-D-glucopyranosylamine</synonym>
    <synonym>2-Acetamido-N(1)-L-beta-aspartyl-2-deoxy-beta-D-glucopyranosylamine</synonym>
    <synonym>AADG</synonym>
    <synonym>beta-N-Acetylglucosaminyl-L-asparagine</synonym>
    <synonym>N-Acetylglucosaminylasparagine</synonym>
    <synonym>N4-(Acetyl-beta-D-glucosaminyl)asparagine</synonym>
    <synonym>N4-(beta-N-Acetyl-D-glucosaminyl)-L-asparagine</synonym>
    <synonym>1-b-Aspartyl-N-acetyl-D-glucosaminylamine</synonym>
    <synonym>1-Β-aspartyl-N-acetyl-D-glucosaminylamine</synonym>
    <synonym>2-Acetamido-1-(b-L-aspartamido)-1,2-dideoxy-b-D-glucose</synonym>
    <synonym>2-Acetamido-1-(β-L-aspartamido)-1,2-dideoxy-β-D-glucose</synonym>
    <synonym>2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-b-D-glucopyranosylamine</synonym>
    <synonym>2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-β-D-glucopyranosylamine</synonym>
    <synonym>2-Acetamido-N-L-b-aspartyl-2-deoxy-b-D-glucopyranosylamine</synonym>
    <synonym>2-Acetamido-N-L-β-aspartyl-2-deoxy-β-D-glucopyranosylamine</synonym>
    <synonym>2-Acetamido-N(1)-L-b-aspartyl-2-deoxy-b-D-glucopyranosylamine</synonym>
    <synonym>2-Acetamido-N(1)-L-β-aspartyl-2-deoxy-β-D-glucopyranosylamine</synonym>
    <synonym>b-N-Acetylglucosaminyl-L-asparagine</synonym>
    <synonym>Β-N-acetylglucosaminyl-L-asparagine</synonym>
    <synonym>N4-(Acetyl-b-D-glucosaminyl)asparagine</synonym>
    <synonym>N4-(Acetyl-β-D-glucosaminyl)asparagine</synonym>
    <synonym>N4-(b-N-Acetyl-D-glucosaminyl)-L-asparagine</synonym>
    <synonym>N4-(Β-N-acetyl-D-glucosaminyl)-L-asparagine</synonym>
    <synonym>(N-g-(2-Acetamido-2-deoxy-b-D-gluco-pyranosyl)-L-asparagine</synonym>
    <synonym>(N-gamma-(2-Acetamido-2-deoxy-beta-D-gluco-pyranosyl)-L-asparagine</synonym>
    <synonym>(N-gamma-(2-Acetamido-2-deoxy-beta-delta-gluco-pyranosyl)-L-asparagine</synonym>
    <synonym>2-Acetamido-1-b-(L-aspartamido)-1,2-dideoxy-D-glucose</synonym>
    <synonym>2-Acetamido-1-beta-(L-aspartamido)-1,2-dideoxy-D-glucose</synonym>
    <synonym>2-Acetamido-1-beta-(L-aspartamido)-1,2-dideoxy-delta-glucose</synonym>
    <synonym>2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-beta-delta-glucopyranosylamine</synonym>
    <synonym>4-N-2-Acetamido-2-deoxy-beta-D-glucopyranosyl-L-asparagine</synonym>
    <synonym>4-N-2-Acetamido-2-deoxy-beta-delta-glucopyranosyl-L-asparagine</synonym>
    <synonym>Acetylglucosaminylasparagine</synonym>
    <synonym>Asparaginylglucosamine</synonym>
    <synonym>Aspartylglucosamine</synonym>
    <synonym>Aspartylglucosylamine</synonym>
    <synonym>b-D-GlcNAc-1-&gt;n-asn</synonym>
    <synonym>beta-D-GlcNAc-1-&gt;n-asn</synonym>
    <synonym>beta-delta-GlcNAc-1-&gt;n-asn</synonym>
    <synonym>H-Asn(glcnac-b-D)-OH</synonym>
    <synonym>H-Asn(glcnac-beta-D)-OH</synonym>
    <synonym>N(4)-(Acetyl-beta-D-glucosaminyl)asparagine</synonym>
    <synonym>N(4)-(beta-N-Acetyl-D-glucosaminyl)-L-asparagine</synonym>
    <synonym>N-(2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl)L-asparagine</synonym>
    <synonym>N-(2-(Acetylamino)-2-deoxy-beta-delta-glucopyranosyl)L-asparagine</synonym>
    <synonym>N-(2-Acetylamino)-2-deoxy-beta-D-glucopyranosyl-L-asparagine</synonym>
    <synonym>N-(2-Acetylamino)-2-deoxy-beta-delta-glucopyranosyl-L-asparagine</synonym>
    <synonym>N(4)-(2-Acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine</synonym>
    <synonym>N(4)-(2-Acetamido-2-deoxyglucopyranosyl)asparagine</synonym>
    <synonym>N-ADGP-asn</synonym>
    <synonym>N(4)-(b-N-Acetyl-D-glucosaminyl)-L-asparagine</synonym>
    <synonym>N(4)-(Β-N-acetyl-D-glucosaminyl)-L-asparagine</synonym>
    <synonym>Aspartylglycosamine</synonym>
  </synonyms>
  <chemical_formula>C12H21N3O8</chemical_formula>
  <average_molecular_weight>335.3104</average_molecular_weight>
  <monisotopic_moleculate_weight>335.132864663</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]carbamoyl}propanoic acid</iupac_name>
  <traditional_iupac>acetylglucosaminylasparagine</traditional_iupac>
  <cas_registry_number>2776-93-4</cas_registry_number>
  <smiles>CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1NC(=O)C[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C12H21N3O8/c1-4(17)14-8-10(20)9(19)6(3-16)23-11(8)15-7(18)2-5(13)12(21)22/h5-6,8-11,16,19-20H,2-3,13H2,1H3,(H,14,17)(H,15,18)(H,21,22)/t5-,6+,8+,9+,10+,11+/m0/s1</inchi>
  <inchikey>YTTRPBWEMMPYSW-HRRFRDKFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Glycosylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heterocyclic fatty acids</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Heterocyclic fatty acid</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N(4)-glycosyl-L-asparagine</external_descriptor>
      <external_descriptor>glucosaminylamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]carbamoyl}propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>335.3104</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>335.132864663</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1NC(=O)C[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H21N3O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H21N3O8/c1-4(17)14-8-10(20)9(19)6(3-16)23-11(8)15-7(18)2-5(13)12(21)22/h5-6,8-11,16,19-20H,2-3,13H2,1H3,(H,14,17)(H,15,18)(H,21,22)/t5-,6+,8+,9+,10+,11+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YTTRPBWEMMPYSW-HRRFRDKFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>191.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>74187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>74188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>74189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>133497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>133498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>133499</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04540</kegg_id>
  <foodb_id>FDB022071</foodb_id>
  <chemspider_id>110370</chemspider_id>
  <pubchem_compound_id>123826</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>17261</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5476</metlin_id>
  <synthesis_reference>Yamamoto, Akira; Miyashita, Chieko; Tsukamoto, Hisao.  Amino sugars. II. Preparation of 2-acetamido-1-N-[L-a(and b)-aspartyl]-2-deoxy-b-D-glucosylamine and 2-acetamido-2-deoxy-N-(L-g-glutamyl)-b-D-glucosylamine.    Chemical &amp; Pharmaceutical Bulletin  (1965),  13(9),  1041-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:30 UTC</creation_date>
  <update_date>2020-03-13 16:21:34 UTC</update_date>
  <accession>BMDB0000490</accession>
  <secondary_accessions>
    <accession>BMDB00490</accession>
  </secondary_accessions>
  <name>Etiocholanolone</name>
  <description>Etiocholanolone, also known as Etiocholanolone, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, etiocholanolone is considered to be a steroid lipid molecule. Etiocholanolone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Etiocholanolone exists in all living organisms, ranging from bacteria to humans. Etiocholanolone can be biosynthesized from etiocholanedione through the action of the enzyme aldo-keto reductase family 1 member C4. In cattle, etiocholanolone is involved in the metabolic pathway called the androstenedione metabolism pathway.</description>
  <synonyms>
    <synonym>(3alpha,5beta)-3-Hydroxyandrostan-17-one</synonym>
    <synonym>3alpha-Etiocholanolone</synonym>
    <synonym>3alpha-Hydroxyetiocholan-17-one</synonym>
    <synonym>5-Isoandrosterone</synonym>
    <synonym>5beta-Androstan-3alpha-ol-17-one</synonym>
    <synonym>5beta-Androsterone</synonym>
    <synonym>AETIOCHOLANOLONE</synonym>
    <synonym>Etiocholan-3alpha-ol-17-one</synonym>
    <synonym>3alpha-Hydroxy-5beta-androstan-17-one</synonym>
    <synonym>(3a,5b)-3-Hydroxyandrostan-17-one</synonym>
    <synonym>(3Α,5β)-3-hydroxyandrostan-17-one</synonym>
    <synonym>3a-Etiocholanolone</synonym>
    <synonym>3Α-etiocholanolone</synonym>
    <synonym>3a-Hydroxyetiocholan-17-one</synonym>
    <synonym>3Α-hydroxyetiocholan-17-one</synonym>
    <synonym>5b-Androstan-3a-ol-17-one</synonym>
    <synonym>5Β-androstan-3α-ol-17-one</synonym>
    <synonym>5b-Androsterone</synonym>
    <synonym>5Β-androsterone</synonym>
    <synonym>Etiocholan-3a-ol-17-one</synonym>
    <synonym>Etiocholan-3α-ol-17-one</synonym>
    <synonym>3a-Hydroxy-5b-androstan-17-one</synonym>
    <synonym>3Α-hydroxy-5β-androstan-17-one</synonym>
    <synonym>3a-Hydroxy-5b-androstane-17-one</synonym>
    <synonym>5 beta Androsterone</synonym>
    <synonym>5b-Androstane-3a-ol-17-one</synonym>
    <synonym>a-Etiocholanolone</synonym>
    <synonym>alpha-Etiocholanolone</synonym>
    <synonym>3-alpha-Hydroxy-5-beta-androstan-17-one</synonym>
    <synonym>5-beta-Androsterone</synonym>
    <synonym>3 alpha Hydroxy 5 beta androstan 17 one</synonym>
  </synonyms>
  <chemical_formula>C19H30O2</chemical_formula>
  <average_molecular_weight>290.4403</average_molecular_weight>
  <monisotopic_moleculate_weight>290.224580204</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</iupac_name>
  <traditional_iupac>(1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</traditional_iupac>
  <cas_registry_number>53-42-9</cas_registry_number>
  <smiles>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@]([H])(O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1</inchi>
  <inchikey>QGXBDMJGAMFCBF-BNSUEQOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17-oxo steroid</external_descriptor>
      <external_descriptor>3alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>Androstane and derivatives</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>androstanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>152 - 154 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>290.4403</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>290.224580204</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@]([H])(O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H30O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QGXBDMJGAMFCBF-BNSUEQOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>83.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androstenedione Metabolism</name>
      <smpdb_id>SMP0087271</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270473</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04373</kegg_id>
  <chemspider_id>5669</chemspider_id>
  <foodb_id>FDB022072</foodb_id>
  <drugbank_id>DB02854</drugbank_id>
  <pubchem_compound_id>5880</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28195</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id>43684</bigg_id>
  <wikipedia_id>Etiocholanolone</wikipedia_id>
  <metlin_id>5477</metlin_id>
  <synthesis_reference>Pelli, Beatrice; Traldi, Pietro; Gargano, Michele; Ravasio, Nicoletta; Rossi, Michele.  Easy determination of epimeric androsterones by collision spectroscopy: the molar ratio of 5b-androstan-3a-ol-17-one and 5b-androstan-3b-ol-17-one obtained by hydrogenation of 5b-androstane-3,17-dione on copper/alumina.    Organic Mass Spectrometry  (1987),  22(3),  183-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:31 UTC</creation_date>
  <update_date>2020-04-14 22:47:34 UTC</update_date>
  <accession>BMDB0000491</accession>
  <secondary_accessions>
    <accession>BMDB00491</accession>
  </secondary_accessions>
  <name>3-Methyl-2-oxovaleric acid</name>
  <description/>
  <synonyms>
    <synonym>2-oxo-3-Methyl-N-valeric acid</synonym>
    <synonym>2-oxo-3-Methylpentanoic acid</synonym>
    <synonym>2-oxo-3-Methylvalerate</synonym>
    <synonym>2-oxo-3-Methylvaleric acid</synonym>
    <synonym>2-Oxoisoleucine</synonym>
    <synonym>2-Oxokolavenic acid</synonym>
    <synonym>3-Ethyl-3-methylpyruvic acid</synonym>
    <synonym>3-Methyl-2-oxopentanoic acid</synonym>
    <synonym>alpha-Keto-beta-methyl-N-valeric acid</synonym>
    <synonym>alpha-Keto-beta-methylvaleric acid</synonym>
    <synonym>alpha-oxo-beta-Methyl-N-valeric acid</synonym>
    <synonym>alpha-oxo-beta-Methylvaleric acid</synonym>
    <synonym>Ketoisoleucine</synonym>
    <synonym>2-oxo-3-Methyl-N-valerate</synonym>
    <synonym>2-oxo-3-Methylpentanoate</synonym>
    <synonym>2-Oxokolavenate</synonym>
    <synonym>3-Ethyl-3-methylpyruvate</synonym>
    <synonym>3-Methyl-2-oxopentanoate</synonym>
    <synonym>a-Keto-b-methyl-N-valerate</synonym>
    <synonym>a-Keto-b-methyl-N-valeric acid</synonym>
    <synonym>alpha-Keto-beta-methyl-N-valerate</synonym>
    <synonym>Α-keto-β-methyl-N-valerate</synonym>
    <synonym>Α-keto-β-methyl-N-valeric acid</synonym>
    <synonym>a-Keto-b-methylvalerate</synonym>
    <synonym>a-Keto-b-methylvaleric acid</synonym>
    <synonym>alpha-Keto-beta-methylvalerate</synonym>
    <synonym>Α-keto-β-methylvalerate</synonym>
    <synonym>Α-keto-β-methylvaleric acid</synonym>
    <synonym>a-oxo-b-Methyl-N-valerate</synonym>
    <synonym>a-oxo-b-Methyl-N-valeric acid</synonym>
    <synonym>alpha-oxo-beta-Methyl-N-valerate</synonym>
    <synonym>Α-oxo-β-methyl-N-valerate</synonym>
    <synonym>Α-oxo-β-methyl-N-valeric acid</synonym>
    <synonym>a-oxo-b-Methylvalerate</synonym>
    <synonym>a-oxo-b-Methylvaleric acid</synonym>
    <synonym>alpha-oxo-beta-Methylvalerate</synonym>
    <synonym>Α-oxo-β-methylvalerate</synonym>
    <synonym>Α-oxo-β-methylvaleric acid</synonym>
    <synonym>3-Methyl-2-oxovalerate</synonym>
    <synonym>(3R)-3-Methyl-2-oxopentanoate</synonym>
    <synonym>(3R)-3-Methyl-2-oxopentanoic acid</synonym>
    <synonym>(R)-3-Methyl-2-oxopentanoate</synonym>
    <synonym>(R)-3-Methyl-2-oxopentanoic acid</synonym>
    <synonym>(S)-3-Methyl-2-oxopentanoate</synonym>
    <synonym>(S)-3-Methyl-2-oxopentanoic acid</synonym>
    <synonym>2-Keto-3-methylvalerate</synonym>
    <synonym>2-Keto-3-methylvaleric acid</synonym>
    <synonym>3-Methyl-2-oxo-pentanoate</synonym>
    <synonym>3-Methyl-2-oxo-pentanoic acid</synonym>
    <synonym>3-Methyl-2-oxo-valerate</synonym>
    <synonym>3-Methyl-2-oxo-valeric acid</synonym>
    <synonym>3-Methyl-2-oxovaleric</synonym>
    <synonym>2-Keto methylvalerate</synonym>
    <synonym>KMVA</synonym>
    <synonym>alpha-Keto-beta-methylvaleric acid, calcium salt, (S)-isomer</synonym>
    <synonym>alpha-Keto-beta-methylvaleric acid, monosodium salt, (S)-isomer</synonym>
    <synonym>alpha-Keto-beta-methylvaleric acid, (S)-isomer</synonym>
    <synonym>alpha-Keto-beta-methylvaleric acid, calcium salt</synonym>
    <synonym>alpha-Keto-beta-methylvaleric acid, sodium salt, (+-)-isomer</synonym>
    <synonym>alpha-Keto-beta-methylvaleric acid, (+-)-isomer</synonym>
    <synonym>alpha-Keto-beta-methylvaleric acid, sodium salt</synonym>
  </synonyms>
  <chemical_formula>C6H10O3</chemical_formula>
  <average_molecular_weight>130.1418</average_molecular_weight>
  <monisotopic_moleculate_weight>130.062994186</monisotopic_moleculate_weight>
  <iupac_name>3-methyl-2-oxopentanoic acid</iupac_name>
  <traditional_iupac>3-methyl-2-oxopentanoic acid</traditional_iupac>
  <cas_registry_number>1460-34-0</cas_registry_number>
  <smiles>CCC(C)C(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)</inchi>
  <inchikey>JVQYSWDUAOAHFM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Short-chain keto acids and derivatives</sub_class>
    <direct_parent>Short-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain keto acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>915.5 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-methyl-2-oxopentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>130.1418</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>130.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(C)C(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JVQYSWDUAOAHFM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438689</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03465</kegg_id>
  <chemspider_id>46</chemspider_id>
  <foodb_id>FDB021447</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>47</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>35932</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id>35662</bigg_id>
  <wikipedia_id/>
  <metlin_id>5478</metlin_id>
  <synthesis_reference>Kondo, Shigeo; Sudo, Tetsuji; Ogiwara, Mitsuo; Takeuchi, Hiroshi.  a-Oxo-b-methyl-n-valeric acid and its salts.  Jpn. Kokai Tokkyo Koho  (1979),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:32 UTC</creation_date>
  <update_date>2020-04-15 20:48:01 UTC</update_date>
  <accession>BMDB0000492</accession>
  <secondary_accessions>
    <accession>BMDB00492</accession>
  </secondary_accessions>
  <name>Chlorine</name>
  <description>Chloride ion, also known as chloride(1-) or Cl, belongs to the class of inorganic compounds known as homogeneous halogens. These are inorganic non-metallic compounds in which the largest atom is a nobel gas. Chloride ion exists as a solid, possibly soluble (in water), and an extremely strong acidic compound (based on its pKa) molecule. Chloride ion exists in all living species, ranging from bacteria to humans. In cattle, chloride ion is involved in the metabolic pathway called the kidney function pathway. Chloride ion is a potentially toxic compound.</description>
  <synonyms>
    <synonym>Chloride(1-)</synonym>
    <synonym>Chlorine anion</synonym>
    <synonym>CL(-)</synonym>
    <synonym>Chloride</synonym>
    <synonym>Bertholite</synonym>
    <synonym>Chloor</synonym>
    <synonym>Chlor</synonym>
    <synonym>Chlore</synonym>
    <synonym>Chlorine</synonym>
    <synonym>Chlorine gas</synonym>
    <synonym>Cl</synonym>
    <synonym>Cl2</synonym>
    <synonym>Diatomic chlorine</synonym>
    <synonym>Dichlorine</synonym>
    <synonym>Molecular chlorine</synonym>
    <synonym>Chloride ion level</synonym>
    <synonym>Ion level, chloride</synonym>
    <synonym>Chlorides</synonym>
    <synonym>Level, chloride ion</synonym>
    <synonym>MSR-1 Protein, nicotiana plumbaginifolia</synonym>
    <synonym>PLS216 Protein, nicotiana plumbaginifolia</synonym>
  </synonyms>
  <chemical_formula>Cl</chemical_formula>
  <average_molecular_weight>35.453</average_molecular_weight>
  <monisotopic_moleculate_weight>34.968852707</monisotopic_moleculate_weight>
  <iupac_name>chloride</iupac_name>
  <traditional_iupac>chloride</traditional_iupac>
  <cas_registry_number>16887-00-6</cas_registry_number>
  <smiles>[Cl-]</smiles>
  <inchi>InChI=1S/ClH/h1H/p-1</inchi>
  <inchikey>VEXZGXHMUGYJMC-UHFFFAOYSA-M</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous halogens. These are inorganic non-metallic compounds in which the largest atom is a nobel gas.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Homogeneous halogens</class>
    <sub_class/>
    <direct_parent>Homogeneous halogens</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous halogen</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>an anion</external_descriptor>
      <external_descriptor>halide anion</external_descriptor>
      <external_descriptor>monoatomic chlorine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Gas</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>chloride</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>35.453</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>34.968852707</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Cl-]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Cl</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/ClH/h1H/p-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VEXZGXHMUGYJMC-UHFFFAOYSA-M</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>5.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>2.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Angiotensin Metabolism</name>
      <smpdb_id>SMP0119379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gastric Acid Production</name>
      <smpdb_id>SMP0119381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Kidney Function</name>
      <smpdb_id>SMP0119376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36289</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>98400</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Dacos Chemistry Analyzer in Hereford cows</comment>
      <references>
        <reference>
          <reference_text>Early RJ, McBride BW, Ball RO: Growth and metabolism in somatotropin-treated steers: I. Growth, serum chemistry and carcass weights. J Anim Sci. 1990 Dec;68(12):4134-43. doi: 10.2527/1990.68124134x.</reference_text>
          <pubmed_id>2286555</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>107300 +/- 360</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>McAdam PA, O'Dell GD: Mineral profile of blood plasma of lactating dairy cows. J Dairy Sci. 1982 Jul;65(7):1219-26. doi: 10.3168/jds.S0022-0302(82)82333-3.</reference_text>
          <pubmed_id>7108016</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28206.358</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00698</kegg_id>
  <foodb_id>FDB006557</foodb_id>
  <chemspider_id>4514529</chemspider_id>
  <pubchem_compound_id>312</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>17996</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>50130</bigg_id>
  <wikipedia_id>Chloride</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Weber, Rainer; Bulan, Andreas; Haas, Michel; Warsitz, Rafael; Werner, Knud.  Production of chlorine from hydrogen chloride and oxygen.    PCT Int. Appl.  (2007),     30pp.  CODEN: PIXXD2  WO  2007134861  A1  20071129  CAN 148:35931  AN 2007:1361621   </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00138</protein_accession>
      <name>Cystic fibrosis transmembrane conductance regulator</name>
      <uniprot_id>P35071</uniprot_id>
      <gene_name>CFTR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01005</protein_accession>
      <name>Angiotensin-converting enzyme</name>
      <uniprot_id>P12820</uniprot_id>
      <gene_name>ACE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01039</protein_accession>
      <name>Angiotensin-converting enzyme 2</name>
      <uniprot_id>Q58DD0</uniprot_id>
      <gene_name>ACE2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01347</protein_accession>
      <name>Solute carrier family 26, member 6</name>
      <uniprot_id>Q08DQ8</uniprot_id>
      <gene_name>SLC26A6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01404</protein_accession>
      <name>Tenascin-X</name>
      <uniprot_id>O18977</uniprot_id>
      <gene_name>TN-X</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01835</protein_accession>
      <name>Dipeptidyl-peptidase 1</name>
      <uniprot_id>Q3ZCJ8</uniprot_id>
      <gene_name>CTSC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01836</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit beta-2</name>
      <uniprot_id>P0C2W5</uniprot_id>
      <gene_name>GABRB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01837</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit pi</name>
      <uniprot_id>Q5EA06</uniprot_id>
      <gene_name>GABRP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01838</protein_accession>
      <name>Chloride channel protein 5</name>
      <uniprot_id>Q68V31</uniprot_id>
      <gene_name>clcn5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01839</protein_accession>
      <name>Chloride channel protein 2</name>
      <uniprot_id>Q6A194</uniprot_id>
      <gene_name>clc2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01840</protein_accession>
      <name>Chloride intracellular channel protein 4</name>
      <uniprot_id>Q9XSA7</uniprot_id>
      <gene_name>CLIC4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01841</protein_accession>
      <name>Chloride channel accessory 4</name>
      <uniprot_id>Q3SYU0</uniprot_id>
      <gene_name>CLCA4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01842</protein_accession>
      <name>CLIC3 protein</name>
      <uniprot_id>A6QL90</uniprot_id>
      <gene_name>CLIC3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01843</protein_accession>
      <name>Chloride intracellular channel 2</name>
      <uniprot_id>A2VE46</uniprot_id>
      <gene_name>CLIC2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01844</protein_accession>
      <name>GABRG1 protein</name>
      <uniprot_id>A6QQP6</uniprot_id>
      <gene_name>GABRG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01845</protein_accession>
      <name>CLCN2 protein</name>
      <uniprot_id>A6QNR5</uniprot_id>
      <gene_name>CLCN2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01846</protein_accession>
      <name>Epithelial chloride channel protein</name>
      <uniprot_id>P54281</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01847</protein_accession>
      <name>Purinergic P2Y6 receptor</name>
      <uniprot_id>Q6QHU8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01848</protein_accession>
      <name>Glycine receptor subunit alpha-1</name>
      <uniprot_id>P57695</uniprot_id>
      <gene_name>GLRA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01849</protein_accession>
      <name>SLC12A5 protein</name>
      <uniprot_id>A8KC65</uniprot_id>
      <gene_name>SLC12A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01850</protein_accession>
      <name>Chloride channel 7</name>
      <uniprot_id>A6QQR2</uniprot_id>
      <gene_name>CLCN7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01851</protein_accession>
      <name>Chloride channel 4</name>
      <uniprot_id>Q4F894</uniprot_id>
      <gene_name>CLCN4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01852</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit alpha-5</name>
      <uniprot_id>Q08E50</uniprot_id>
      <gene_name>GABRA5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01853</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit beta-1</name>
      <uniprot_id>P08220</uniprot_id>
      <gene_name>GABRB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01854</protein_accession>
      <name>CLIC1</name>
      <uniprot_id>Q4QRP1</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01855</protein_accession>
      <name>Chloride channel protein 7</name>
      <uniprot_id>Q4PKH3</uniprot_id>
      <gene_name>CLCN7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01856</protein_accession>
      <name>Chloride intracellular channel protein 5</name>
      <uniprot_id>P35526</uniprot_id>
      <gene_name>CLIC5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01857</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit alpha-4</name>
      <uniprot_id>P20237</uniprot_id>
      <gene_name>GABRA4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01858</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit gamma-2</name>
      <uniprot_id>P22300</uniprot_id>
      <gene_name>GABRG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01859</protein_accession>
      <name>Putative uncharacterized protein</name>
      <uniprot_id>A0JN66</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01860</protein_accession>
      <name>GABRA3 protein</name>
      <uniprot_id>Q0II82</uniprot_id>
      <gene_name>GABRA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01861</protein_accession>
      <name>Chloride intracellular channel protein 1</name>
      <uniprot_id>Q5E9B7</uniprot_id>
      <gene_name>CLIC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01862</protein_accession>
      <name>Na-K-Cl cotransporter</name>
      <uniprot_id>O18978</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01863</protein_accession>
      <name>Sodium chloride cotransporter</name>
      <uniprot_id>O97740</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01864</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit alpha-3</name>
      <uniprot_id>P10064</uniprot_id>
      <gene_name>GABRA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01865</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit alpha-2</name>
      <uniprot_id>P10063</uniprot_id>
      <gene_name>GABRA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01866</protein_accession>
      <name>Chloride channel CLIC-like protein 1</name>
      <uniprot_id>Q1LZF8</uniprot_id>
      <gene_name>CLCC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01867</protein_accession>
      <name>Glycine receptor subunit beta</name>
      <uniprot_id>Q9GJS9</uniprot_id>
      <gene_name>GLRB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01868</protein_accession>
      <name>Protein tweety homolog 1</name>
      <uniprot_id>Q2KJ98</uniprot_id>
      <gene_name>TTYH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01869</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit rho-2</name>
      <uniprot_id>Q0II76</uniprot_id>
      <gene_name>GABRR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01870</protein_accession>
      <name>Anoctamin-4</name>
      <uniprot_id>A6QLE6</uniprot_id>
      <gene_name>ANO4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01871</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit alpha-1</name>
      <uniprot_id>P08219</uniprot_id>
      <gene_name>GABRA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01872</protein_accession>
      <name>Phospholemman</name>
      <uniprot_id>Q3SZX0</uniprot_id>
      <gene_name>FXYD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01873</protein_accession>
      <name>Chloride channel, nucleotide-sensitive, 1A</name>
      <uniprot_id>Q1LZ90</uniprot_id>
      <gene_name>CLNS1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:33 UTC</creation_date>
  <update_date>2020-03-13 16:21:35 UTC</update_date>
  <accession>BMDB0000493</accession>
  <secondary_accessions>
    <accession>BMDB00493</accession>
  </secondary_accessions>
  <name>5a-Androstane-3b,17b-diol</name>
  <description/>
  <synonyms>
    <synonym>(3beta,5alpha,17beta)-Androstane-3,17-diol</synonym>
    <synonym>3beta,17beta-Dihydroxy-5alpha-androstane</synonym>
    <synonym>5-ALPHA-ANDROSTANE-3-BETA,17BETA-diol</synonym>
    <synonym>5alpha-Androstan-3beta,17beta-diol</synonym>
    <synonym>(3b,5a,17b)-Androstane-3,17-diol</synonym>
    <synonym>(3Β,5α,17β)-androstane-3,17-diol</synonym>
    <synonym>3b,17b-Dihydroxy-5a-androstane</synonym>
    <synonym>3Β,17β-dihydroxy-5α-androstane</synonym>
    <synonym>5-a-ANDROSTANE-3-b,17b-diol</synonym>
    <synonym>5-Α-androstane-3-β,17β-diol</synonym>
    <synonym>5a-Androstan-3b,17b-diol</synonym>
    <synonym>5Α-androstan-3β,17β-diol</synonym>
    <synonym>5a-Androstane-3b,17b-diol</synonym>
    <synonym>5Α-androstane-3β,17β-diol</synonym>
    <synonym>3b,17b-Androstanediol</synonym>
    <synonym>3b-Androstanediol</synonym>
    <synonym>3Β-androstanediol</synonym>
    <synonym>5alpha-Androstane-3beta,17beta-diol</synonym>
  </synonyms>
  <chemical_formula>C19H32O2</chemical_formula>
  <average_molecular_weight>292.4562</average_molecular_weight>
  <monisotopic_moleculate_weight>292.240230268</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol</iupac_name>
  <traditional_iupac>(1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol</traditional_iupac>
  <cas_registry_number>571-20-0</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1</inchi>
  <inchikey>CBMYJHIOYJEBSB-YSZCXEEOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17beta-hydroxy steroid</external_descriptor>
      <external_descriptor>3beta-hydroxy steroid</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>androstane-3,17-diol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>3 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>292.4562</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>292.240230268</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H32O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CBMYJHIOYJEBSB-YSZCXEEOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268079</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C12525</kegg_id>
  <chemspider_id>211834</chemspider_id>
  <foodb_id>FDB022073</foodb_id>
  <drugbank_id>DB03882</drugbank_id>
  <pubchem_compound_id>242332</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18329</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>3β-Androstanediol</wikipedia_id>
  <metlin_id>5479</metlin_id>
  <synthesis_reference>Merlani, M. I.; Amiranashvili, L. Sh.; Men'shova, N. I.; Kemertelidze, E. P.  Synthesis of 5a-androstan-3b,17b-diol from tigogenin.    Chemistry of Natural Compounds  (2007),  43(1),  97-99.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:34 UTC</creation_date>
  <update_date>2020-04-15 22:30:56 UTC</update_date>
  <accession>BMDB0000494</accession>
  <secondary_accessions>
    <accession>BMDB00494</accession>
  </secondary_accessions>
  <name>Stigmastanol</name>
  <description/>
  <synonyms>
    <synonym>Methyl (20alpha)-16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylate</synonym>
    <synonym>Methyl (20a)-16,17-didehydro-19a-methyl-18-oxayohimban-16-carboxylate</synonym>
    <synonym>Methyl (20a)-16,17-didehydro-19a-methyl-18-oxayohimban-16-carboxylic acid</synonym>
    <synonym>Methyl (20alpha)-16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylic acid</synonym>
    <synonym>Methyl (20α)-16,17-didehydro-19α-methyl-18-oxayohimban-16-carboxylate</synonym>
    <synonym>Methyl (20α)-16,17-didehydro-19α-methyl-18-oxayohimban-16-carboxylic acid</synonym>
    <synonym>(3b)-Stigmastan-3-ol</synonym>
    <synonym>(3beta)-Stigmastan-3-ol</synonym>
    <synonym>(3beta,5alpha)-Stigmastan-3-ol</synonym>
    <synonym>24-alpha-Ethylcholestanol</synonym>
    <synonym>24a-Ethylcholestanol</synonym>
    <synonym>4a-Methyl-5a,14a-lumistan-3b-ol</synonym>
    <synonym>4a-Methylcampestanol</synonym>
    <synonym>5,6-dihydro-b-Sitosterol</synonym>
    <synonym>5,6-dihydro-beta-Sitosterol</synonym>
    <synonym>5a-Stigmastan-3b-ol</synonym>
    <synonym>5alpha-Stigmastan-3beta-ol</synonym>
    <synonym>b-Sitostanol</synonym>
    <synonym>beta-dihydro-Sitosterol</synonym>
    <synonym>beta-Sitostanol</synonym>
    <synonym>dihydro-b-Sitosterol</synonym>
    <synonym>dihydro-beta-Sitosterol</synonym>
    <synonym>Dihydrositosterin</synonym>
    <synonym>Dihydrositosterol</synonym>
    <synonym>Fucostanol</synonym>
    <synonym>Sitostanol</synonym>
    <synonym>Spinastanol</synonym>
    <synonym>Stigmastan-3-ol</synonym>
    <synonym>Stigmastane-3-beta-ol</synonym>
    <synonym>24 alpha-Ethyl-5 alpha-cholestan-3 beta-ol</synonym>
    <synonym>Stigmastanol, (3beta,5beta,24S)-isomer</synonym>
    <synonym>24 alpha-Ethyl-5 beta-cholestan-3 alpha-ol</synonym>
    <synonym>Stigmastanol</synonym>
  </synonyms>
  <chemical_formula>C29H52O</chemical_formula>
  <average_molecular_weight>416.734</average_molecular_weight>
  <monisotopic_moleculate_weight>416.401816294</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5S,10R,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol</iupac_name>
  <traditional_iupac>stigmastane-3-β-ol</traditional_iupac>
  <cas_registry_number>6474-90-4</cas_registry_number>
  <smiles>CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C</smiles>
  <inchi>InChI=1S/C29H52O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h19-27,30H,7-18H2,1-6H3/t20-,21-,22?,23+,24+,25-,26+,27+,28+,29-/m1/s1</inchi>
  <inchikey>LGJMUZUPVCAVPU-KZXGMYDKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Alkaloids and derivatives</super_class>
    <class>Yohimbine alkaloids</class>
    <sub_class/>
    <direct_parent>Yohimbine alkaloids</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alkylindoles</alternative_parent>
      <alternative_parent>Amino acids and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Beta carbolines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Corynanthean-type alkaloids</alternative_parent>
      <alternative_parent>Enoate esters</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl esters</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Piperidines</alternative_parent>
      <alternative_parent>Pyrroles</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
      <alternative_parent>Vinylogous esters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>18-oxayohimban</substituent>
      <substituent>3-alkylindole</substituent>
      <substituent>Ajmalicine-skeleton</substituent>
      <substituent>Alpha,beta-unsaturated carboxylic ester</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Beta-carboline</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Corynanthean skeleton</substituent>
      <substituent>Enoate ester</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indole</substituent>
      <substituent>Indole or derivatives</substituent>
      <substituent>Methyl ester</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Piperidine</substituent>
      <substituent>Pyridoindole</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
      <substituent>Vinylogous ester</substituent>
      <substituent>Yohimbine alkaloid</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Indole alkaloids</external_descriptor>
      <external_descriptor>yohimban alkaloid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>144 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>8.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5S,10R,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>416.734</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>416.401816294</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C29H52O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C29H52O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h19-27,30H,7-18H2,1-6H3/t20-,21-,22?,23+,24+,25-,26+,27+,28+,29-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LGJMUZUPVCAVPU-KZXGMYDKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>128.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>54.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37568</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C11682</kegg_id>
  <chemspider_id/>
  <pubchem_compound_id>72340</pubchem_compound_id>
  <drugbank_id/>
  <foodb_id/>
  <pdbe_id/>
  <chebi_id>9479</chebi_id>
  <knapsack_id>C00025214</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Bengtsson, B. E.  A comparison between sitostanol and stigmastanol.  Z. physiol. Chem.  (1935),  237  46-51.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:36 UTC</creation_date>
  <update_date>2020-04-15 22:35:24 UTC</update_date>
  <accession>BMDB0000495</accession>
  <secondary_accessions>
    <accession>BMDB00495</accession>
  </secondary_accessions>
  <name>Androstanediol</name>
  <description/>
  <synonyms>
    <synonym>Androstane-3,17-diol</synonym>
    <synonym>3-a-Androstanediol</synonym>
    <synonym>3-alpha-Androstanediol</synonym>
    <synonym>3alpha-Androstanediol</synonym>
    <synonym>5 a-Androstane-3 a, 17 b-diol</synonym>
    <synonym>5 alpha-Androstane-3 alpha, 17 beta-diol</synonym>
    <synonym>5-a-Androstane-3-a, 17-b-diol</synonym>
    <synonym>5-alpha-Androstan-3-alpha,17-beta-diol</synonym>
    <synonym>5-alpha-Androstane-3-a, 17-beta-diol</synonym>
    <synonym>5-alpha-Androstane-3-alpha-17-beta-diol</synonym>
    <synonym>5 Androstane 3,17 diol</synonym>
    <synonym>5 alpha Androstane 3 alpha,17 beta diol</synonym>
    <synonym>5 alpha Androstane 3 beta,17 alpha diol</synonym>
    <synonym>5 alpha Androstane 3 beta,17 beta diol</synonym>
    <synonym>5 alpha Androstane 3alpha,17 beta diol</synonym>
    <synonym>5 alpha-Androstane-3 alpha,17 beta-diol</synonym>
    <synonym>5 alpha-Androstane-3 beta,17 alpha-diol</synonym>
    <synonym>5 alpha-Androstane-3 beta,17 beta-diol</synonym>
    <synonym>5 alpha-Androstane-3alpha,17 beta-diol</synonym>
    <synonym>5 beta Androstane 3 alpha,17 beta diol</synonym>
    <synonym>5 beta-Androstane-3 alpha,17 beta-diol</synonym>
    <synonym>5-Androstane-3,17-diol</synonym>
    <synonym>5alpha Androstane 3beta,17alpha diol</synonym>
    <synonym>5alpha-Androstane-3beta,17alpha-diol</synonym>
    <synonym>Androstane 3,17 diol</synonym>
  </synonyms>
  <chemical_formula>C19H32O2</chemical_formula>
  <average_molecular_weight>292.4562</average_molecular_weight>
  <monisotopic_moleculate_weight>292.240230268</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol</iupac_name>
  <traditional_iupac>(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@]12CCC(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17?,18-,19-/m0/s1</inchi>
  <inchikey>CBMYJHIOYJEBSB-UNPXRYTGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerophospholipids</class>
    <sub_class>Glycerophosphocholines</sub_class>
    <direct_parent>Phosphatidylcholines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Dialkyl phosphates</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phosphocholines</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Diacylglycero-3-phosphocholine</substituent>
      <substituent>Dialkyl phosphate</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphocholine</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>292.4562</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>292.240230268</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H32O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17?,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CBMYJHIOYJEBSB-UNPXRYTGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>76934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>136901</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB025706</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id/>
  <kegg_id/>
  <chebi_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference>Vierhapper H  Formation of androstanediol from 13C-labeled testosterone in humans.  Steroids  (1990),  55(4),  177-80.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:37 UTC</creation_date>
  <update_date>2020-04-14 22:47:35 UTC</update_date>
  <accession>BMDB0000496</accession>
  <secondary_accessions>
    <accession>BMDB00496</accession>
  </secondary_accessions>
  <name>3-Methoxy-4-hydroxyphenylglycol glucuronide</name>
  <description/>
  <synonyms>
    <synonym>MHPG Glucuronide</synonym>
    <synonym>(2S,3S,4S,5R,6S)-6-[4-(1,2-Dihydroxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylate</synonym>
    <synonym>3-Methoxy-4-hydroxyphenylglycol glucuronide</synonym>
  </synonyms>
  <chemical_formula>C15H20O10</chemical_formula>
  <average_molecular_weight>360.3133</average_molecular_weight>
  <monisotopic_moleculate_weight>360.10564686</monisotopic_moleculate_weight>
  <iupac_name>(2S,3S,4S,5R,6S)-6-[4-(1,2-dihydroxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>mhpg glucuronide</traditional_iupac>
  <cas_registry_number>52002-41-2</cas_registry_number>
  <smiles>COC1=CC(=CC=C1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C(O)CO</smiles>
  <inchi>InChI=1S/C15H20O10/c1-23-9-4-6(7(17)5-16)2-3-8(9)24-15-12(20)10(18)11(19)13(25-15)14(21)22/h2-4,7,10-13,15-20H,5H2,1H3,(H,21,22)/t7?,10-,11-,12+,13-,15+/m0/s1</inchi>
  <inchikey>VMWCOZPKGQMCRO-UICVJNQZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Phenolic glycosides</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>O-glucuronides</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-o-glucuronide</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Glucuronic acid or derivatives</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>O-glucuronide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenolic glycoside</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3S,4S,5R,6S)-6-[4-(1,2-dihydroxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>360.3133</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>360.10564686</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC(=CC=C1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C(O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H20O10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H20O10/c1-23-9-4-6(7(17)5-16)2-3-8(9)24-15-12(20)10(18)11(19)13(25-15)14(21)22/h2-4,7,10-13,15-20H,5H2,1H3,(H,21,22)/t7?,10-,11-,12+,13-,15+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VMWCOZPKGQMCRO-UICVJNQZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>166.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>80247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>80248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>80249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>141066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>141067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>141068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37570</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022075</foodb_id>
  <chemspider_id>17215958</chemspider_id>
  <pubchem_compound_id>22833525</pubchem_compound_id>
  <drugbank_id/>
  <kegg_id>C03033</kegg_id>
  <chebi_id>89405</chebi_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>1593</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:39 UTC</creation_date>
  <update_date>2020-03-13 16:21:38 UTC</update_date>
  <accession>BMDB0000497</accession>
  <secondary_accessions>
    <accession>BMDB00497</accession>
  </secondary_accessions>
  <name>5,6-Dihydrouridine</name>
  <description/>
  <synonyms>
    <synonym>1-beta-D-Ribofuranosylhydrouracil</synonym>
    <synonym>3,4-Dihydrouridine</synonym>
    <synonym>D</synonym>
    <synonym>1-b-D-Ribofuranosylhydrouracil</synonym>
    <synonym>1-Β-D-ribofuranosylhydrouracil</synonym>
    <synonym>Dihydro-1-b-D-ribofuranosyl-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>Dihydro-1-beta-delta-ribofuranosyl-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>Dihydrouridine</synonym>
    <synonym>5,6-Dihydrouridine</synonym>
  </synonyms>
  <chemical_formula>C9H14N2O6</chemical_formula>
  <average_molecular_weight>246.2173</average_molecular_weight>
  <monisotopic_moleculate_weight>246.08518619</monisotopic_moleculate_weight>
  <iupac_name>1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-diazinane-2,4-dione</iupac_name>
  <traditional_iupac>dihydrouridine</traditional_iupac>
  <cas_registry_number>5627-05-4</cas_registry_number>
  <smiles>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1CCC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C9H14N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h4,6-8,12,14-15H,1-3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1</inchi>
  <inchikey>ZPTBLXKRQACLCR-XVFCMESISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Glycosylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Organic carbonic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2,5,6-tetrahydropyrimidine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonic acid derivative</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>uridines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-diazinane-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>246.2173</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>246.08518619</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1CCC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H14N2O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H14N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h4,6-8,12,14-15H,1-3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZPTBLXKRQACLCR-XVFCMESISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>119.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>52.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>79047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>79048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>79049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>139545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>139546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>139547</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022076</foodb_id>
  <chemspider_id>85115</chemspider_id>
  <pubchem_compound_id>94312</pubchem_compound_id>
  <drugbank_id/>
  <kegg_id/>
  <chebi_id>23774</chebi_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Dihydrouridine</wikipedia_id>
  <metlin_id>5483</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Cerutti, Peter; Kondo, Yoshikazu; Landis, W. R.; Witkop, Bernhard. Photoreduction of uridine and reduction of dihydrouridine with sodium borohydride. Journal of the American Chemical Society (1968), 90(3), 771-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:40 UTC</creation_date>
  <update_date>2020-03-13 16:21:38 UTC</update_date>
  <accession>BMDB0000498</accession>
  <secondary_accessions>
    <accession>BMDB00498</accession>
  </secondary_accessions>
  <name>4-Deoxyerythronic acid</name>
  <description/>
  <synonyms>
    <synonym>4-Deoxyerythronate</synonym>
    <synonym>(+/-)-erythro-2,3-dihydroxybutyric acid</synonym>
    <synonym>(R*,r*)-2,3-dihydroxy-butanoate</synonym>
    <synonym>(R*,r*)-2,3-dihydroxy-butanoic acid</synonym>
    <synonym>(R*,r*)-2,3-dihydroxybutanoate</synonym>
    <synonym>(R*,r*)-2,3-dihydroxybutanoic acid</synonym>
    <synonym>(R*,s*)-2,3-dihydroxybutanoate</synonym>
    <synonym>(R*,s*)-2,3-dihydroxybutanoic acid</synonym>
    <synonym>2,3-Dihydroxybutanoic acid</synonym>
    <synonym>2,3-Erythro-dihydroxybutyrate</synonym>
    <synonym>2,3-Erythro-dihydroxybutyric acid</synonym>
    <synonym>4-Deoxy-erythronate</synonym>
    <synonym>4-Deoxy-erythronic acid</synonym>
    <synonym>4-Deoxytetronic acid</synonym>
    <synonym>Erythro-2,3-dihydroxybutyric acid</synonym>
    <synonym>(2R,3R)-2,3-Dihydroxybutanoate</synonym>
  </synonyms>
  <chemical_formula>C4H8O4</chemical_formula>
  <average_molecular_weight>120.1039</average_molecular_weight>
  <monisotopic_moleculate_weight>120.042258744</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R)-2,3-dihydroxybutanoic acid</iupac_name>
  <traditional_iupac>4-deoxyerythronic acid</traditional_iupac>
  <cas_registry_number>759-06-8</cas_registry_number>
  <smiles>C[C@@H](O)[C@@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H8O4/c1-2(5)3(6)4(7)8/h2-3,5-6H,1H3,(H,7,8)/t2-,3-/m1/s1</inchi>
  <inchikey>LOUGYXZSURQALL-PWNYCUMCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
      <substituent>Sugar acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R)-2,3-dihydroxybutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>120.1039</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>120.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](O)[C@@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O4/c1-2(5)3(6)4(7)8/h2-3,5-6H,1H3,(H,7,8)/t2-,3-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LOUGYXZSURQALL-PWNYCUMCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>24.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33145</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022077</foodb_id>
  <chemspider_id>17215960</chemspider_id>
  <pubchem_compound_id>13120901</pubchem_compound_id>
  <drugbank_id/>
  <kegg_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5484</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Owen, L. N.  Oxygenation of crotonaldehyde.  Journal of the Chemical Society  (1943),     563-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:41 UTC</creation_date>
  <update_date>2020-03-19 20:35:41 UTC</update_date>
  <accession>BMDB0000499</accession>
  <secondary_accessions>
    <accession>BMDB00499</accession>
    <accession>BMDB0062586</accession>
    <accession>BMDB62586</accession>
  </secondary_accessions>
  <name>5-Tetradecenoic acid</name>
  <description>5-Tetradecenoic acid, also known as (Z)-5-tetradecenoate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 5-Tetradecenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-Tetradecenoic acid has been linked to the inborn metabolic disorders including very long chain acyl-coa dehydrogenase deficiency.</description>
  <synonyms>
    <synonym>5-Tetradecenoate</synonym>
    <synonym>Physeterate</synonym>
    <synonym>Physeteric acid</synonym>
    <synonym>Physoterate</synonym>
    <synonym>Physoteric acid</synonym>
    <synonym>(5E)-5-Tetradecenoic acid</synonym>
    <synonym>(e)-5-Tetradecenoic acid</synonym>
    <synonym>C14:1W9</synonym>
    <synonym>FA(14:1(5E))</synonym>
    <synonym>FA(14:1n9)</synonym>
    <synonym>trans-5-Tetradecenoic acid</synonym>
    <synonym>5-Tetradecenoic acid</synonym>
  </synonyms>
  <chemical_formula>C14H26O2</chemical_formula>
  <average_molecular_weight>226.355</average_molecular_weight>
  <monisotopic_moleculate_weight>226.193280076</monisotopic_moleculate_weight>
  <iupac_name>(5E)-tetradec-5-enoic acid</iupac_name>
  <traditional_iupac>physeteric acid</traditional_iupac>
  <cas_registry_number>5684-69-5</cas_registry_number>
  <smiles>CCCCCCCC\C=C\CCCC(O)=O</smiles>
  <inchi>InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h9-10H,2-8,11-13H2,1H3,(H,15,16)/b10-9+</inchi>
  <inchikey>AFGUVBVUFZMJMX-MDZDMXLPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5E)-tetradec-5-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>226.355</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>226.193280076</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCC\C=C\CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H26O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h9-10H,2-8,11-13H2,1H3,(H,15,16)/b10-9+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AFGUVBVUFZMJMX-MDZDMXLPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366243</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Two pasteurized milk brands from the Middle Eastern Region of Paraná State By Gas Chromatography (n = 15)</comment>
      <references>
        <reference>
          <reference_text>Julliana Isabelle Simionato, Juliana Carla Garcia, Geraldo Tadeu dos Santos, Cláudio Celestino Oliveira, Jesui Vergilio Visentainera and Nilson Evelázio de Souza. Validation of the Determination of Fatty Acids in Milk by Gas Chromatography. J. Braz. Chem. Soc., Vol. 21, No. 3, 520-524, 2010.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by UPLC-Q-TOF MS E</comment>
      <references>
        <reference>
          <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
          <pubmed_id>28342601</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id>4445867</chemspider_id>
  <foodb_id>FDB022089</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>5282740</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>89393</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5485</metlin_id>
  <synthesis_reference>Toyama, Yoshiyuki; Tsuchiya, Tomotaro.  The separation of physeteric acid from sardine and pilot-whale oils.    Kogyo Kagaku Zasshi  (1935),  38  Suppl. binding 680-4.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
      <pubmed_id>28342601</pubmed_id>
    </reference>
    <reference>
      <reference_text>Julliana Isabelle Simionato, Juliana Carla Garcia, Geraldo Tadeu dos Santos, Cláudio Celestino Oliveira, Jesui Vergilio Visentainera and Nilson Evelázio de Souza. Validation of the Determination of Fatty Acids in Milk by Gas Chromatography. J. Braz. Chem. Soc., Vol. 21, No. 3, 520-524, 2010.</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:42 UTC</creation_date>
  <update_date>2020-03-13 16:21:39 UTC</update_date>
  <accession>BMDB0000500</accession>
  <secondary_accessions>
    <accession>BMDB00500</accession>
  </secondary_accessions>
  <name>4-Hydroxybenzoic acid</name>
  <description>4-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-carboxyphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 4-Hydroxybenzoic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 4-Hydroxybenzoic acid exists in all living species, ranging from bacteria to humans. In cattle, 4-hydroxybenzoic acid is involved in the metabolic pathway called ubiquinone biosynthesis pathway.</description>
  <synonyms>
    <synonym>4-Carboxyphenol</synonym>
    <synonym>p-HYDROXYBENZOIC ACID</synonym>
    <synonym>p-Salicylic acid</synonym>
    <synonym>Hydroxybenzoic acid</synonym>
    <synonym>Hydroxybenzenecarboxylic acid</synonym>
    <synonym>p-HYDROXYBENZOate</synonym>
    <synonym>p-Salicylate</synonym>
    <synonym>Hydroxybenzoate</synonym>
    <synonym>Hydroxybenzenecarboxylate</synonym>
    <synonym>4-Hydroxybenzoate</synonym>
    <synonym>4-Hydroxy-benzoate</synonym>
    <synonym>4-Hydroxy-benzoesaeure</synonym>
    <synonym>4-Hydroxy-benzoic acid</synonym>
    <synonym>p-Carboxyphenol</synonym>
    <synonym>p-Hydroxy-benzoate</synonym>
    <synonym>p-Hydroxy-benzoic acid</synonym>
    <synonym>Paraben-acid</synonym>
    <synonym>4-Hydroxybenzoic acid, calcium salt</synonym>
    <synonym>4-Hydroxybenzoic acid, dilithium salt</synonym>
    <synonym>4-Hydroxybenzoic acid, disodium salt</synonym>
    <synonym>Para-hydroxybenzoic acid</synonym>
    <synonym>Sodium p-hydroxybenzoate tetrahydrate</synonym>
    <synonym>4-Hydroxybenzoic acid, copper(2+)(1:1) salt</synonym>
    <synonym>4-Hydroxybenzoic acid, dipotassium salt</synonym>
    <synonym>4-Hydroxybenzoic acid, monopotassium salt</synonym>
    <synonym>4-Hydroxybenzoic acid, monosodium salt</synonym>
    <synonym>4-Hydroxybenzoic acid, monosodium salt, 11C-labeled</synonym>
  </synonyms>
  <chemical_formula>C7H6O3</chemical_formula>
  <average_molecular_weight>138.122</average_molecular_weight>
  <monisotopic_moleculate_weight>138.031694053</monisotopic_moleculate_weight>
  <iupac_name>4-hydroxybenzoic acid</iupac_name>
  <traditional_iupac>P-hydroxybenzoic acid</traditional_iupac>
  <cas_registry_number>99-96-7</cas_registry_number>
  <smiles>OC(=O)C1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)</inchi>
  <inchikey>FJKROLUGYXJWQN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>Hydroxybenzoic acid derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxybenzoic acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>monohydroxybenzoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>5.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.58</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-hydroxybenzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>138.122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>138.031694053</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1=CC=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H6O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FJKROLUGYXJWQN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ubiquinone Biosynthesis</name>
      <smpdb_id>SMP0087215</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31881</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437774</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00156</kegg_id>
  <chemspider_id>132</chemspider_id>
  <foodb_id>FDB010508</foodb_id>
  <drugbank_id>DB04242</drugbank_id>
  <pubchem_compound_id>135</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30763</chebi_id>
  <phenol_explorer_compound_id>418</phenol_explorer_compound_id>
  <knapsack_id>C00000856</knapsack_id>
  <meta_cyc_id/>
  <bigg_id>34069</bigg_id>
  <wikipedia_id>4-Hydroxybenzoic_acid</wikipedia_id>
  <metlin_id>5486</metlin_id>
  <synthesis_reference>Ivanov, G. E.; Slavcheva, L.  Preparation, properties, and applications of p-hydroxy-benzoic acid.    Khimiya i Industriya (1922-1988)  (1966),  38(10),  458-63.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:45 UTC</creation_date>
  <update_date>2020-04-16 17:53:11 UTC</update_date>
  <accession>BMDB0000501</accession>
  <secondary_accessions>
    <accession>BMDB00501</accession>
  </secondary_accessions>
  <name>7-Ketocholesterol</name>
  <description/>
  <synonyms>
    <synonym>3b-Hydroxycholest-5-en-7-one</synonym>
    <synonym>7-Oxocholesterol</synonym>
    <synonym>Cholest-5-en-3b-ol-7-one</synonym>
    <synonym>Delta5-Cholesten-3b-ol-7-one</synonym>
    <synonym>3beta-Hydroxy-5-cholestene-7-one</synonym>
    <synonym>5-Cholesten-3 beta-ol-7-one</synonym>
  </synonyms>
  <chemical_formula>C27H44O2</chemical_formula>
  <average_molecular_weight>400.6371</average_molecular_weight>
  <monisotopic_moleculate_weight>400.334130652</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10S,11S,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one</iupac_name>
  <traditional_iupac>(1S,2R,10S,11S,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one</traditional_iupac>
  <cas_registry_number>566-28-9</cas_registry_number>
  <smiles>[H][C@@]12CCC([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)C=C2CC(O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20?,21?,22+,23+,25+,26+,27-/m1/s1</inchi>
  <inchikey>YIKKMWSQVKJCOP-QJFKPLHKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>7-oxosteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>168 - 170 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>17.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10S,11S,15R)-5-hydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>400.6371</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>400.334130652</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)C=C2CC(O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H44O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20?,21?,22+,23+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YIKKMWSQVKJCOP-QJFKPLHKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>121.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>50.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348552</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB022079</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477696</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5487</metlin_id>
  <synthesis_reference>Chicoye, Etzer; Powrie, William D.; Fennema, Owen R.  Synthesis, purification, and characterization of 7-ketocholesterol and epimeric 7-hydroxycholesterols.  Lipids  (1968),  3(6),  551-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:46 UTC</creation_date>
  <update_date>2020-04-15 22:13:59 UTC</update_date>
  <accession>BMDB0000502</accession>
  <secondary_accessions>
    <accession>BMDB00502</accession>
  </secondary_accessions>
  <name>3-Oxocholic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Oxocholate</synonym>
    <synonym>(4R)-4-[(1S,2S,7R,10R,11S,14S,15R,16R)-9,16-Dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
    <synonym>(4R)-4-[(1S,2S,7R,10R,11S,14S,15R,16R)-9,16-Dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H38O5</chemical_formula>
  <average_molecular_weight>406.5555</average_molecular_weight>
  <monisotopic_moleculate_weight>406.271924326</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,7R,10R,11S,14S,15R,16R)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>3-oxocholate</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@](C)(CCC(O)=O)[C@]1([H])CC[C@@]2([H])[C@]3([H])C([H])(O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])C[C@@]([H])(O)[C@]12C</smiles>
  <inchi>InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-20,22,26-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16+,17+,18+,19?,20-,22+,23+,24-/m1/s1</inchi>
  <inchikey>OEKUSRBIIZNLHZ-DAMPJUSJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-oxo-5-beta-steroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-oxo-5-beta-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,7R,10R,11S,14S,15R,16R)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>406.5555</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>406.271924326</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](C)(CCC(O)=O)[C@]1([H])CC[C@@]2([H])[C@]3([H])C([H])(O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])C[C@@]([H])(O)[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H38O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-20,22,26-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16+,17+,18+,19?,20-,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OEKUSRBIIZNLHZ-DAMPJUSJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1256548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1256549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1256550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1371715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1371716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1371717</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id/>
  <drugbank_id/>
  <kegg_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Production of 7a,12a-dihydroxy-3-keto-5b-cholanic acid.    Jpn. Kokai Tokkyo Koho  (1981),     12 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:47 UTC</creation_date>
  <update_date>2020-03-13 16:21:41 UTC</update_date>
  <accession>BMDB0000503</accession>
  <secondary_accessions>
    <accession>BMDB00503</accession>
  </secondary_accessions>
  <name>7a-Hydroxy-3-oxo-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>7a-Hydroxy-3-oxo-5b-cholanoate</synonym>
    <synonym>(4R)-4-[(1S,2S,7R,10R,11S,15R)-9-Hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
    <synonym>(4R)-4-[(1S,2S,7R,10R,11S,15R)-9-Hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H38O4</chemical_formula>
  <average_molecular_weight>390.5561</average_molecular_weight>
  <monisotopic_moleculate_weight>390.277009704</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,7R,10R,11S,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,7R,10R,11S,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@](C)(CCC(O)=O)C1([H])CC[C@@]2([H])[C@]3([H])C([H])(O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-15,17-20,22,26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,17?,18+,19+,20?,22+,23+,24-/m1/s1</inchi>
  <inchikey>KNVADAPHVNKTEP-VWEUZOFESA-N</inchikey>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,7R,10R,11S,15R)-9-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>390.5561</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>390.277009704</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](C)(CCC(O)=O)C1([H])CC[C@@]2([H])[C@]3([H])C([H])(O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H38O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-15,17-20,22,26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,17?,18+,19+,20?,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KNVADAPHVNKTEP-VWEUZOFESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>108.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>45.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1224187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1224188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1224189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1339804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1339805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1339806</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id/>
  <chemspider_id/>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id/>
  <pubchem_compound_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Riva, Sergio; Bovara, Roberto; Zetta, Lucia; Pasta, Piero; Ottolina, Gianluca; Carrea, Giacomo. Enzymic a/b inversion of C-3 hydroxyl of bile acids and study of the effects of organic solvents on reaction rates. Journal of Organic Chemistry  (1988),  53(1),  88-92.  </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:48 UTC</creation_date>
  <update_date>2020-04-15 22:14:00 UTC</update_date>
  <accession>BMDB0000505</accession>
  <secondary_accessions>
    <accession>BMDB00505</accession>
  </secondary_accessions>
  <name>Allocholic acid</name>
  <description/>
  <synonyms>
    <synonym>3alpha,7alpha,12alpha-Trihydroxy-5alpha-cholanoic acid</synonym>
    <synonym>5alpha-Cholic acid</synonym>
    <synonym>Allocholate</synonym>
    <synonym>(3a,5a,7a,12a)-3,7,12-Trihydroxycholan-24-Oate</synonym>
    <synonym>(3a,5a,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acid</synonym>
    <synonym>(3alpha,5alpha,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5α,7α,12α)-3,7,12-trihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5α,7α,12α)-3,7,12-trihydroxycholan-24-Oic acid</synonym>
    <synonym>3a,7a,12a-Trihydroxy-5a-cholanoate</synonym>
    <synonym>3a,7a,12a-Trihydroxy-5a-cholanoic acid</synonym>
    <synonym>3alpha,7alpha,12alpha-Trihydroxy-5alpha-cholanoate</synonym>
    <synonym>5a-Cholate</synonym>
    <synonym>5a-Cholic acid</synonym>
    <synonym>5alpha-Cholate</synonym>
    <synonym>(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oic acid</synonym>
    <synonym>(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oate</synonym>
    <synonym>(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acid</synonym>
    <synonym>(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5β,7α,12α)-3,7,12-trihydroxycholan-24-Oic acid</synonym>
    <synonym>3a,7a,12a-Trihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,7a,12a-Trihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3a,7a,12a-Trihydroxycholanate</synonym>
    <synonym>3a,7a,12a-Trihydroxycholanic acid</synonym>
    <synonym>5alpha-Allocholic acid</synonym>
    <synonym>5Α-allocholic acid</synonym>
    <synonym>Allocholic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.579</average_molecular_weight>
  <monisotopic_moleculate_weight>408.287574388</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>2464-18-8</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1</inchi>
  <inchikey>BHQCQFFYRZLCQQ-PGHAKIONSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>bile acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.579</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.287574388</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHQCQFFYRZLCQQ-PGHAKIONSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C17737</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB011602</foodb_id>
  <chemspider_id>141151</chemspider_id>
  <pubchem_compound_id>160636</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>81308</chebi_id>
  <knapsack_id/>
  <wikipedia_id/>
  <meta_cyc_id>CPD-16581</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5491</metlin_id>
  <synthesis_reference>Mitra, Manindra N.; Elliott, William Hueckel.  Bile acids.  XXIII.  New direct synthesis of allocholic acid and its 3b isomer.  Journal of Organic Chemistry  (1968),  33(1),  175-81. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:50 UTC</creation_date>
  <update_date>2020-04-15 22:14:01 UTC</update_date>
  <accession>BMDB0000506</accession>
  <secondary_accessions>
    <accession>BMDB00506</accession>
  </secondary_accessions>
  <name>Alpha-Muricholic acid</name>
  <description/>
  <synonyms>
    <synonym>a-Muricholate</synonym>
    <synonym>a-Muricholic acid</synonym>
    <synonym>alpha-Muricholate</synonym>
    <synonym>Α-muricholate</synonym>
    <synonym>Α-muricholic acid</synonym>
    <synonym>3a,6b,7a-Trihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,6b,7a-Trihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3a,6b,7a-Trihydroxy-5b-cholanate</synonym>
    <synonym>3a,6b,7a-Trihydroxy-5b-cholanic acid</synonym>
    <synonym>5b-Cholanic acid-3a,6b,7a-triol</synonym>
    <synonym>(4R)-4-[(1S,2R,5R,7R,8S,9S,10S,11S,15R)-5,8,9-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5R,7R,8S,9S,10S,11S,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5R,7R,8S,9S,10S,11S,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>2393-58-0</cas_registry_number>
  <smiles>[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15?,16+,17+,18+,20+,21+,22+,23-,24-/m1/s1</inchi>
  <inchikey>DKPMWHFRUGMUKF-LPMPYYIQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>6-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>6-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>199 - 200 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5R,7R,8S,9S,10S,11S,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15?,16+,17+,18+,20+,21+,22+,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DKPMWHFRUGMUKF-LPMPYYIQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352311</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022082</foodb_id>
  <pubchem_compound_id>53477700</pubchem_compound_id>
  <chemspider_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5492</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Hsia, S. L.; Elliott, Wm. H.; Matschiner, John T.; Doisy, E. A., Jr.; Thayer, Sidney A.; Doisy, Edward A.  Bile acids. XIII. Further contributions to the constitution of muricholic acids.   Journal of Biological Chemistry  (1960),  235  1963-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:51 UTC</creation_date>
  <update_date>2020-04-16 17:52:16 UTC</update_date>
  <accession>BMDB0000508</accession>
  <secondary_accessions>
    <accession>BMDB00508</accession>
  </secondary_accessions>
  <name>Ribitol</name>
  <description/>
  <synonyms>
    <synonym>(2R,3S,4S)-Pentane-1,2,3,4,5-pentol</synonym>
    <synonym>Adonitol</synonym>
    <synonym>D-Adonitol</synonym>
    <synonym>D-Ribitol</synonym>
    <synonym>L-Ribitol</synonym>
    <synonym>1,2,3,4,5-Pentanepentol</synonym>
    <synonym>Adonit</synonym>
    <synonym>Adonite</synonym>
    <synonym>Pentitol</synonym>
  </synonyms>
  <chemical_formula>C5H12O5</chemical_formula>
  <average_molecular_weight>152.1458</average_molecular_weight>
  <monisotopic_moleculate_weight>152.068473494</monisotopic_moleculate_weight>
  <iupac_name>(2R,3s,4S)-pentane-1,2,3,4,5-pentol</iupac_name>
  <traditional_iupac>ribitol</traditional_iupac>
  <cas_registry_number>488-81-3</cas_registry_number>
  <smiles>OC[C@H](O)[C@H](O)[C@H](O)CO</smiles>
  <inchi>InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-</inchi>
  <inchikey>HEBKCHPVOIAQTA-ZXFHETKHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar alcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sugar alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>ribitol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>102 - 105 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>936 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3s,4S)-pentane-1,2,3,4,5-pentol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>152.1458</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>152.068473494</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H](O)[C@H](O)[C@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H12O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HEBKCHPVOIAQTA-ZXFHETKHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>101.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447782</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00474</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022083</foodb_id>
  <chemspider_id>10254628</chemspider_id>
  <pubchem_compound_id/>
  <pdbe_id/>
  <chebi_id>15963</chebi_id>
  <knapsack_id>C00001171</knapsack_id>
  <wikipedia_id>Ribitol</wikipedia_id>
  <meta_cyc_id>RIBITOL</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35086</bigg_id>
  <metlin_id>316</metlin_id>
  <synthesis_reference>Yamazaki, Masayoshi; Yamazaki, Fumito; Muranaka, Chikako; Kozeki, Satomi; Tatsuno, Yoshiaki; Okamoto, Naoki.  Manufacture of ribitol with Trichosporonoides.    Jpn. Kokai Tokkyo Koho  (1999),     6 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:52 UTC</creation_date>
  <update_date>2020-03-13 16:21:43 UTC</update_date>
  <accession>BMDB0000509</accession>
  <secondary_accessions>
    <accession>BMDB00509</accession>
  </secondary_accessions>
  <name>Senecioic acid</name>
  <description/>
  <synonyms>
    <synonym>3,3-Dimethylacrylic acid</synonym>
    <synonym>3-Methyl-2-butenoic acid</synonym>
    <synonym>3-Methylcrotonic acid</synonym>
    <synonym>beta,beta-Dimethacrylic acid</synonym>
    <synonym>beta,beta-Dimethylacrylic acid</synonym>
    <synonym>beta-Methylcrotonic acid</synonym>
    <synonym>SENECIC ACID</synonym>
    <synonym>3,3-Dimethylacrylate</synonym>
    <synonym>3-Methyl-2-butenoate</synonym>
    <synonym>3-Methylcrotonate</synonym>
    <synonym>b,b-Dimethacrylate</synonym>
    <synonym>b,b-Dimethacrylic acid</synonym>
    <synonym>beta,beta-Dimethacrylate</synonym>
    <synonym>Β,β-dimethacrylate</synonym>
    <synonym>Β,β-dimethacrylic acid</synonym>
    <synonym>b,b-Dimethylacrylate</synonym>
    <synonym>b,b-Dimethylacrylic acid</synonym>
    <synonym>beta,beta-Dimethylacrylate</synonym>
    <synonym>Β,β-dimethylacrylate</synonym>
    <synonym>Β,β-dimethylacrylic acid</synonym>
    <synonym>b-Methylcrotonate</synonym>
    <synonym>b-Methylcrotonic acid</synonym>
    <synonym>beta-Methylcrotonate</synonym>
    <synonym>Β-methylcrotonate</synonym>
    <synonym>Β-methylcrotonic acid</synonym>
    <synonym>SENECate</synonym>
    <synonym>Senecioate</synonym>
    <synonym>3-Methyl-crotonate</synonym>
    <synonym>3-Methyl-crotonic acid</synonym>
    <synonym>3-Methylbut-2-enoate</synonym>
    <synonym>3-Methylbut-2-enoic acid</synonym>
    <synonym>b,b-Dimethyl acrylate</synonym>
    <synonym>b,b-Dimethyl acrylic acid</synonym>
    <synonym>beta,beta-Dimethyl acrylate</synonym>
    <synonym>Β,β-dimethyl acrylate</synonym>
    <synonym>Β,β-dimethyl acrylic acid</synonym>
    <synonym>Senecioic acid</synonym>
  </synonyms>
  <chemical_formula>C5H8O2</chemical_formula>
  <average_molecular_weight>100.1158</average_molecular_weight>
  <monisotopic_moleculate_weight>100.0524295</monisotopic_moleculate_weight>
  <iupac_name>3-methylbut-2-enoic acid</iupac_name>
  <traditional_iupac>β,β-dimethacrylate</traditional_iupac>
  <cas_registry_number>541-47-9</cas_registry_number>
  <smiles>CC(C)=CC(O)=O</smiles>
  <inchi>InChI=1S/C5H8O2/c1-4(2)3-5(6)7/h3H,1-2H3,(H,6,7)</inchi>
  <inchikey>YYPNJNDODFVZLE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Methyl-branched fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Branched fatty acids</external_descriptor>
      <external_descriptor>alpha,beta-unsaturated monocarboxylic acid</external_descriptor>
      <external_descriptor>methyl-branched fatty acid</external_descriptor>
      <external_descriptor>monounsaturated fatty acid</external_descriptor>
      <external_descriptor>short-chain fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>65 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>10 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-methylbut-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>100.1158</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>100.0524295</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)=CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O2/c1-4(2)3-5(6)7/h3H,1-2H3,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YYPNJNDODFVZLE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>27.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345066</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB000736</foodb_id>
  <chemspider_id>10468</chemspider_id>
  <pubchem_compound_id>10931</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>37127</chebi_id>
  <knapsack_id>C00010280</knapsack_id>
  <wikipedia_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5495</metlin_id>
  <synthesis_reference>Iordache, Florin; Badica, Sonia; Ionescu, Alina; Badea, Florin.  Synthesis of b,b-dimethylacrylic acid and its methyl and ethyl esters.    Revistade Chimie (Bucharest, Romania)  (1979),  30(7),  629-32.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:53 UTC</creation_date>
  <update_date>2020-04-14 22:47:37 UTC</update_date>
  <accession>BMDB0000510</accession>
  <secondary_accessions>
    <accession>BMDB00510</accession>
  </secondary_accessions>
  <name>Aminoadipic acid</name>
  <description>Aminoadipic acid, also known as aminoadipic acid or Aminoadipic acid, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Aminoadipic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Aminoadipic acid exists in all eukaryotes, ranging from yeast to humans. Aminoadipic acid participates in a number of enzymatic reactions, within cattle. In particular, Aminoadipic acid can be biosynthesized from allysine through the action of the enzyme Alpha-aminoadipic semialdehyde dehydrogenase. In addition, Aminoadipic acid and oxoglutaric acid can be converted into oxoadipic acid and L-glutamic acid through its interaction with the enzyme kynurenine/alphaminoadipic acid aminotransferase, mitochondrial. In cattle, aminoadipic acid is involved in the metabolic pathway called the lysine degradation pathway. Aminoadipic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(+/-)-2-aminoadipic acid</synonym>
    <synonym>Aad</synonym>
    <synonym>alpha-Aminoadipic acid</synonym>
    <synonym>DL-2-Aminoadipic acid</synonym>
    <synonym>DL-2-Aminohexanedioic acid</synonym>
    <synonym>DL-alpha-Aminoadipic acid</synonym>
    <synonym>(+/-)-2-aminoadipate</synonym>
    <synonym>a-Aminoadipate</synonym>
    <synonym>a-Aminoadipic acid</synonym>
    <synonym>alpha-Aminoadipate</synonym>
    <synonym>Α-aminoadipate</synonym>
    <synonym>Α-aminoadipic acid</synonym>
    <synonym>DL-2-Aminoadipate</synonym>
    <synonym>DL-2-Aminohexanedioate</synonym>
    <synonym>DL-a-Aminoadipate</synonym>
    <synonym>DL-a-Aminoadipic acid</synonym>
    <synonym>DL-alpha-Aminoadipate</synonym>
    <synonym>DL-Α-aminoadipate</synonym>
    <synonym>DL-Α-aminoadipic acid</synonym>
    <synonym>Aminoadipate</synonym>
    <synonym>2-Aminoadipate</synonym>
    <synonym>2-Aminoadipic acid</synonym>
    <synonym>alpha-Amino-adipic acid</synonym>
    <synonym>L-2-Aminoadipate</synonym>
    <synonym>L-2-Aminoadipic acid</synonym>
    <synonym>L-2-Aminohexanedioate</synonym>
    <synonym>L-2-Aminohexanedioic acid</synonym>
    <synonym>L-alpha-Aminoadipate</synonym>
    <synonym>L-alpha-Aminoadipic acid</synonym>
    <synonym>2 Aminoadipic acid</synonym>
    <synonym>Acid, 2-aminohexanedioic</synonym>
    <synonym>Acid, 2 aminoadipic</synonym>
    <synonym>alpha Aminoadipic acid</synonym>
    <synonym>2 Aminohexanedioic acid</synonym>
    <synonym>Aminoadipic acid, 2</synonym>
    <synonym>Acid, alpha-aminoadipic</synonym>
    <synonym>Acid, 2-aminoadipic</synonym>
    <synonym>2-Aminohexanedioic acid</synonym>
  </synonyms>
  <chemical_formula>C6H11NO4</chemical_formula>
  <average_molecular_weight>161.1558</average_molecular_weight>
  <monisotopic_moleculate_weight>161.068807845</monisotopic_moleculate_weight>
  <iupac_name>2-aminohexanedioic acid</iupac_name>
  <traditional_iupac>aminoadipic acid</traditional_iupac>
  <cas_registry_number>542-32-5</cas_registry_number>
  <smiles>NC(CCCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)</inchi>
  <inchikey>OYIFNHCXNCRBQI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>amino dicarboxylic acid</external_descriptor>
      <external_descriptor>non-proteinogenic alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>196 - 198 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>2.2 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-aminohexanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>161.1558</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>161.068807845</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CCCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H11NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OYIFNHCXNCRBQI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>100.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447303</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1.28+/-0.52</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>7.3-8.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>68+/-27</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>7+/-2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.3 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.1 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.4 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>195 - 427</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>10+/-4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>98+/-39</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00956</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB021812</foodb_id>
  <chemspider_id>456</chemspider_id>
  <pubchem_compound_id>469</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>37024</chebi_id>
  <knapsack_id/>
  <wikipedia_id>Alpha-Aminoadipic_acid</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>1485280</bigg_id>
  <metlin_id>5496</metlin_id>
  <synthesis_reference>Khan, Naseem H.; Ali, Mohd.; Panda, H.; Rakhshinda.  Synthesis of a-aminoadipic acid.    Journal of the Indian Chemical Society  (1982),  59(9),  1077-8.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:54 UTC</creation_date>
  <update_date>2020-04-15 22:34:02 UTC</update_date>
  <accession>BMDB0000511</accession>
  <secondary_accessions>
    <accession>BMDB00511</accession>
  </secondary_accessions>
  <name>Capric acid</name>
  <description>Capric acid, also known as decanoate or 10:0, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Capric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Capric acid exists in all living species, ranging from bacteria to humans. Capric acid participates in a number of enzymatic reactions, within cattle. In particular, Capric acid can be biosynthesized from trans-dec-2-enoic acid through its interaction with the enzyme fatty acid synthase. enoyl reductase domain. In addition, Capric acid and malonic acid can be converted into 3-oxododecanoic acid through the action of the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In cattle, capric acid is involved in the metabolic pathway called fatty acid biosynthesis pathway. Capric acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Nonanecarboxylic acid</synonym>
    <synonym>10:0</synonym>
    <synonym>C10:0</synonym>
    <synonym>Caprinic acid</synonym>
    <synonym>CH3-[CH2]8-COOH</synonym>
    <synonym>Decanoate</synonym>
    <synonym>Decoic acid</synonym>
    <synonym>Decylic acid</synonym>
    <synonym>Dekansaeure</synonym>
    <synonym>Kaprinsaeure</synonym>
    <synonym>N-Capric acid</synonym>
    <synonym>N-Decanoic acid</synonym>
    <synonym>N-Decoic acid</synonym>
    <synonym>N-Decylic acid</synonym>
    <synonym>1-Nonanecarboxylate</synonym>
    <synonym>Caprinate</synonym>
    <synonym>Decanoic acid</synonym>
    <synonym>Decoate</synonym>
    <synonym>Decylate</synonym>
    <synonym>N-Caprate</synonym>
    <synonym>N-Decanoate</synonym>
    <synonym>N-Decoate</synonym>
    <synonym>N-Decylate</synonym>
    <synonym>Caprate</synonym>
    <synonym>Caprynate</synonym>
    <synonym>Caprynic acid</synonym>
    <synonym>Emery 659</synonym>
    <synonym>Lunac 10-95</synonym>
    <synonym>Lunac 10-98</synonym>
    <synonym>Prifac 2906</synonym>
    <synonym>Prifac 296</synonym>
    <synonym>Decanoic acid, sodium salt</synonym>
    <synonym>Sodium caprate</synonym>
    <synonym>Sodium decanoate</synonym>
    <synonym>FA(10:0)</synonym>
  </synonyms>
  <chemical_formula>C10H20O2</chemical_formula>
  <average_molecular_weight>172.2646</average_molecular_weight>
  <monisotopic_moleculate_weight>172.146329884</monisotopic_moleculate_weight>
  <iupac_name>decanoic acid</iupac_name>
  <traditional_iupac>capric acid</traditional_iupac>
  <cas_registry_number>334-48-5</cas_registry_number>
  <smiles>CCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)</inchi>
  <inchikey>GHVNFZFCNZKVNT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Saturated fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>medium-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>31.9 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0618 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.09</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>decanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>172.2646</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>172.146329884</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H20O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GHVNFZFCNZKVNT-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>49.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451251</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by infra-red spectroscopy and silieic acid columns</comment>
      <references>
        <reference>
          <reference_text>Laura Evans, Stuart Patton, R.D. McCarthy. Fatty Acid Composition of the Lipid Fractions from Bovine Serum Lipoproteins. J. Dairy Science (1961) 44(3) 475-482   doi: 10.3168/jds.S0022-0302(61)89765-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.1 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20.66 +/- 5.75</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14.3 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12.7 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11.4 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2670.31</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2322.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>522.452</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1393.206</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>522.452</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6269.43</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5921.12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5514.77</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19 +/- 6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18.26 +/- 2.36</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk from a Danish Holstein herd by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19.76 +/- 2.58</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised whole milk (3.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.87 +/- 0.86</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised semi skimmed milk (1.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.16 +/- 0.86</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised skimmed milk (0.1% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17.01 +/- 0.05</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
          <pubmed_id>1779072</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8127.0136 +/- 3483.00583</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
          <pubmed_id>16899705</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21.885 +/- 0.18</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Catrienus De Jong Herman T. Badings. Determination of free fatty acids in milk and cheese procedures for extraction, clean up, and capillary gas chromatographic analysis. Journal of High Resolution Chromatography Volume 13, Issue 2, 1990</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23.59 +/- 7.41</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6791.861 +/- 2031.753</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6385.511 +/- 1741.503</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19.89 +/- 5.74</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31347.125</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>37152.148</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>38893.655</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>45279.181</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01571</kegg_id>
  <drugbank_id>DB03600</drugbank_id>
  <foodb_id>FDB012027</foodb_id>
  <chemspider_id>2863</chemspider_id>
  <pubchem_compound_id>2969</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30813</chebi_id>
  <knapsack_id>C00001213</knapsack_id>
  <wikipedia_id>Decanoic acid</wikipedia_id>
  <meta_cyc_id>CPD-3617</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>336</metlin_id>
  <synthesis_reference>Wang, Qin; Ni, Xindi; Shi, Jianying.  Manufacturing technology of capric acid and hydroxyalkyl amide from Litsea cubeba nucleolus oil.  Huaxue Shijie  (1993),  34(2),  84-7.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
      <pubmed_id>16899705</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
      <pubmed_id>1779072</pubmed_id>
    </reference>
    <reference>
      <reference_text>Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.</reference_text>
      <pubmed_id>20855010</pubmed_id>
    </reference>
    <reference>
      <reference_text>Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93.</reference_text>
      <pubmed_id>5409465</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.</reference_text>
      <pubmed_id>28219465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
    </reference>
    <reference>
      <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
    </reference>
    <reference>
      <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01876</protein_accession>
      <name>Probable G-protein coupled receptor 84</name>
      <uniprot_id>Q2KI97</uniprot_id>
      <gene_name>GPR84</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:55 UTC</creation_date>
  <update_date>2020-03-13 16:21:45 UTC</update_date>
  <accession>BMDB0000512</accession>
  <secondary_accessions>
    <accession>BMDB00512</accession>
  </secondary_accessions>
  <name>N-Acetyl-L-phenylalanine</name>
  <description/>
  <synonyms>
    <synonym>Acetyl-L-phenylalanine</synonym>
    <synonym>Acetylphenylalanine</synonym>
    <synonym>L-N-Acetylphenylalanine</synonym>
    <synonym>N-Acetylphenylalanine</synonym>
    <synonym>N-Acetyl-3-phenyl-L-alanine</synonym>
    <synonym>N-Acetyl-L-phenalanine</synonym>
    <synonym>N-Acetylphenylalanine, (D,L)-isomer, 3H-labeled</synonym>
    <synonym>N-Acetylphenylalanine, (L)-isomer</synonym>
    <synonym>N-Acetylphenylalanine, (L)-isomer, 3H-labeled</synonym>
    <synonym>N-Acetylphenylalanine, (D)-isomer</synonym>
  </synonyms>
  <chemical_formula>C11H13NO3</chemical_formula>
  <average_molecular_weight>207.2258</average_molecular_weight>
  <monisotopic_moleculate_weight>207.089543287</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-acetamido-3-phenylpropanoic acid</iupac_name>
  <traditional_iupac>acetyl-L-phenylalanine</traditional_iupac>
  <cas_registry_number>2018-61-3</cas_registry_number>
  <smiles>CC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m0/s1</inchi>
  <inchikey>CBQJSKKFNMDLON-JTQLQIEISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Phenylalanine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acetyl-L-amino acid</external_descriptor>
      <external_descriptor>N-acetylphenylalanine</external_descriptor>
      <external_descriptor>N-acyl-L-phenylalanine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>171 - 173 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.93</value>
      <source>GREEN,PG ET AL. (1991)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-acetamido-3-phenylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>207.2258</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>207.089543287</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H13NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CBQJSKKFNMDLON-JTQLQIEISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437189</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03519</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022084</foodb_id>
  <chemspider_id>67404</chemspider_id>
  <pubchem_compound_id>74839</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16259</chebi_id>
  <knapsack_id/>
  <wikipedia_id/>
  <meta_cyc_id>CPD-439</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5498</metlin_id>
  <synthesis_reference>Borovicka, Milos; Cervinka, Otakar; Gajewski, Karel; Lukac, Juraj.  Isolation of optically pure N-acetyl-L-phenylalanine after enantioselective hydrogenation of N-acetamidocinnamic acid.    Czech.  (1985),     2 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:57 UTC</creation_date>
  <update_date>2020-03-13 16:21:45 UTC</update_date>
  <accession>BMDB0000513</accession>
  <secondary_accessions>
    <accession>BMDB00513</accession>
  </secondary_accessions>
  <name>5b-Cholestane-3a,7a,12a,23R,25-pentol</name>
  <description/>
  <synonyms>
    <synonym>1-Nonanecarboxylic acid</synonym>
    <synonym>10:0</synonym>
    <synonym>C10:0</synonym>
    <synonym>Caprinic acid</synonym>
    <synonym>CH3-[CH2]8-COOH</synonym>
    <synonym>Decanoate</synonym>
    <synonym>Decoic acid</synonym>
    <synonym>Decylic acid</synonym>
    <synonym>Dekansaeure</synonym>
    <synonym>Kaprinsaeure</synonym>
    <synonym>N-Capric acid</synonym>
    <synonym>N-Decanoic acid</synonym>
    <synonym>N-Decoic acid</synonym>
    <synonym>N-Decylic acid</synonym>
    <synonym>1-Nonanecarboxylate</synonym>
    <synonym>Caprinate</synonym>
    <synonym>Decanoic acid</synonym>
    <synonym>Decoate</synonym>
    <synonym>Decylate</synonym>
    <synonym>N-Caprate</synonym>
    <synonym>N-Decanoate</synonym>
    <synonym>N-Decoate</synonym>
    <synonym>N-Decylate</synonym>
    <synonym>Caprate</synonym>
    <synonym>Caprynate</synonym>
    <synonym>Caprynic acid</synonym>
    <synonym>Emery 659</synonym>
    <synonym>Lunac 10-95</synonym>
    <synonym>Lunac 10-98</synonym>
    <synonym>Prifac 2906</synonym>
    <synonym>Prifac 296</synonym>
    <synonym>Decanoic acid, sodium salt</synonym>
    <synonym>Sodium caprate</synonym>
    <synonym>Sodium decanoate</synonym>
    <synonym>FA(10:0)</synonym>
    <synonym>17-(3,5-Dihydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,7,12-triol</synonym>
  </synonyms>
  <chemical_formula>C27H48O5</chemical_formula>
  <average_molecular_weight>452.667</average_molecular_weight>
  <monisotopic_moleculate_weight>452.350174646</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R,4R)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol</iupac_name>
  <traditional_iupac>(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R,4R)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol</traditional_iupac>
  <cas_registry_number>334-48-5</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)C[C@@H](O)CC(C)(C)O</smiles>
  <inchi>InChI=1S/C27H48O5/c1-15(10-18(29)14-25(2,3)32)19-6-7-20-24-21(13-23(31)27(19,20)5)26(4)9-8-17(28)11-16(26)12-22(24)30/h15-24,28-32H,6-14H2,1-5H3/t15-,16+,17-,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1</inchi>
  <inchikey>OXSBBBPDYVCAKC-DYGXNTOZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Saturated fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>medium-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R,4R)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>452.667</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>452.350174646</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)C[C@@H](O)CC(C)(C)O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H48O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H48O5/c1-15(10-18(29)14-25(2,3)32)19-6-7-20-24-21(13-23(31)27(19,20)5)26(4)9-8-17(28)11-16(26)12-22(24)30/h15-24,28-32H,6-14H2,1-5H3/t15-,16+,17-,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OXSBBBPDYVCAKC-DYGXNTOZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>101.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>126.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>53.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340734</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01571</kegg_id>
  <foodb_id>FDB012027</foodb_id>
  <chemspider_id>2863</chemspider_id>
  <drugbank_id>DB03600</drugbank_id>
  <pdbe_id/>
  <chebi_id>30813</chebi_id>
  <pubchem_compound_id>2969</pubchem_compound_id>
  <knapsack_id>C00001213</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD-3617</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Decanoic acid</wikipedia_id>
  <metlin_id>336</metlin_id>
  <synthesis_reference>Hoshita, Takahiko; Yasuhara, Misao; Kihira, Kenji; Kuramoto, Taiju.  Comparative biochemical studies of bile acids and bile alcohols.  V.  Identification of (23S)-5a-cholestane-3a,7a,12a,23,25-pentol in cerebrotendinous xanthomatosis.    Steroids  (1976),  27(5),  657-64.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:58 UTC</creation_date>
  <update_date>2020-04-15 22:14:01 UTC</update_date>
  <accession>BMDB0000514</accession>
  <secondary_accessions>
    <accession>BMDB00514</accession>
  </secondary_accessions>
  <name>Allochenodeoxycholic acid</name>
  <description/>
  <synonyms>
    <synonym>Allochenodeoxycholate</synonym>
    <synonym>3a,7a-Dihydroxy-(5a)-cholan-24-Oate</synonym>
    <synonym>3a,7a-Dihydroxy-(5a)-cholan-24-Oic acid</synonym>
    <synonym>3a,7a-Dihydroxy-5a-cholanate</synonym>
    <synonym>3a,7a-Dihydroxy-5a-cholanic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O4</chemical_formula>
  <average_molecular_weight>392.572</average_molecular_weight>
  <monisotopic_moleculate_weight>392.292659768</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>15357-34-3</cas_registry_number>
  <smiles>[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17?,18+,19+,20-,22+,23+,24-/m1/s1</inchi>
  <inchikey>RUDATBOHQWOJDD-FBMQJMKYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7R,9R,10R,11S,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>392.572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.292659768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17?,18+,19+,20-,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RUDATBOHQWOJDD-FBMQJMKYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357594</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022086</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477701</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5500</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Ziller, S. A., Jr.; Mitra, Manindra N.; Elliott, William Hueckel.  Two-step synthesis of allochenodeoxycholic acid.    Chemistry &amp; Industry (London, United Kingdom)  (1967),   (24),  999-1000.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:31:59 UTC</creation_date>
  <update_date>2020-04-16 17:52:16 UTC</update_date>
  <accession>BMDB0000516</accession>
  <secondary_accessions>
    <accession>BMDB00516</accession>
  </secondary_accessions>
  <name>Beta-D-Glucose</name>
  <description/>
  <synonyms>
    <synonym>Glucose</synonym>
    <synonym>b-D-Glucose</synonym>
    <synonym>β-D-glucose</synonym>
    <synonym>b-D-Glucopyranose</synonym>
    <synonym>b-Dextrose</synonym>
    <synonym>b-Glucose</synonym>
    <synonym>beta-D-Glucopyranose</synonym>
    <synonym>beta-Dextrose</synonym>
    <synonym>beta-Glucose</synonym>
    <synonym>D Glucose</synonym>
    <synonym>Glucose, (beta-D)-isomer</synonym>
    <synonym>Dextrose</synonym>
    <synonym>Glucose, (DL)-isomer</synonym>
    <synonym>D-Glucose</synonym>
    <synonym>D-Glucopyranose</synonym>
    <synonym>D-Glucopyranoside</synonym>
    <synonym>beta-D-Glucopyranoside</synonym>
    <synonym>beta-D-Glucose</synonym>
    <synonym>β-D-Glucopyranose</synonym>
    <synonym>β-D-Glucopyranoside</synonym>
    <synonym>β-D-Glucose</synonym>
    <synonym>β-Dextrose</synonym>
    <synonym>β-Glucose</synonym>
    <synonym>D-GLC</synonym>
    <synonym>D-GLCP</synonym>
    <synonym>GLC-OH</synonym>
  </synonyms>
  <chemical_formula>C6H12O6</chemical_formula>
  <average_molecular_weight>180.1559</average_molecular_weight>
  <monisotopic_moleculate_weight>180.063388116</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>glucoside</traditional_iupac>
  <cas_registry_number>492-61-5</cas_registry_number>
  <smiles>OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6-/m1/s1</inchi>
  <inchikey>WQZGKKKJIJFFOK-VFUOTHLCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D-glucopyranose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>logp</kind>
      <value>-3.24</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>180.1559</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>180.063388116</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WQZGKKKJIJFFOK-VFUOTHLCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>110.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Trehalose Degradation</name>
      <smpdb_id>SMP0087263</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448604</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>763.813 +/- 751.731</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB02379</drugbank_id>
  <kegg_id>C00221</kegg_id>
  <chemspider_id/>
  <pubchem_compound_id/>
  <foodb_id>FDB011824</foodb_id>
  <pdbe_id/>
  <chebi_id>15903</chebi_id>
  <meta_cyc_id>D-Glucose</meta_cyc_id>
  <knapsack_id>C00001122</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Glucose</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Wenck, Helmut; Kinedt, Claudia; Bader, Hans Joachim.  Production of b-D-glucose.    Praxis der Naturwissenschaften, Chemie  (1986),  35(4),  23.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00120</protein_accession>
      <name>Aldose 1-epimerase</name>
      <uniprot_id>Q5EA79</uniprot_id>
      <gene_name>GALM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:00 UTC</creation_date>
  <update_date>2020-04-16 20:39:57 UTC</update_date>
  <accession>BMDB0000517</accession>
  <secondary_accessions>
    <accession>BMDB00517</accession>
  </secondary_accessions>
  <name>L-Arginine</name>
  <description>L-Arginine, also known as Arg, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-Arginine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. L-Arginine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Arginine exists in all living species, ranging from bacteria to humans. L-Arginine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2S)-2-Amino-5-(carbamimidamido)pentanoic acid</synonym>
    <synonym>(2S)-2-Amino-5-guanidinopentanoic acid</synonym>
    <synonym>(S)-2-Amino-5-guanidinopentanoic acid</synonym>
    <synonym>(S)-2-Amino-5-guanidinovaleric acid</synonym>
    <synonym>Arg</synonym>
    <synonym>Arginine</synonym>
    <synonym>L-(+)-Arginine</synonym>
    <synonym>L-Arg</synonym>
    <synonym>L-Arginin</synonym>
    <synonym>R</synonym>
    <synonym>(2S)-2-Amino-5-(carbamimidamido)pentanoate</synonym>
    <synonym>(2S)-2-Amino-5-guanidinopentanoate</synonym>
    <synonym>(S)-2-Amino-5-guanidinopentanoate</synonym>
    <synonym>(S)-2-Amino-5-guanidinovalerate</synonym>
    <synonym>(S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoate</synonym>
    <synonym>(S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoic acid</synonym>
    <synonym>(S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoate</synonym>
    <synonym>(S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid</synonym>
    <synonym>2-Amino-5-guanidinovalerate</synonym>
    <synonym>2-Amino-5-guanidinovaleric acid</synonym>
    <synonym>5-[(Aminoiminomethyl)amino]-L-norvaline</synonym>
    <synonym>L-a-Amino-D-guanidinovalerate</synonym>
    <synonym>L-a-Amino-D-guanidinovaleric acid</synonym>
    <synonym>L-alpha-Amino-delta-guanidinovalerate</synonym>
    <synonym>L-alpha-Amino-delta-guanidinovaleric acid</synonym>
    <synonym>N5-(Aminoiminomethyl)-L-ornithine</synonym>
    <synonym>DL-Arginine acetate, monohydrate</synonym>
    <synonym>L-Isomer arginine</synonym>
    <synonym>Monohydrate DL-arginine acetate</synonym>
    <synonym>L Arginine</synonym>
    <synonym>Arginine, L isomer</synonym>
    <synonym>Arginine, L-isomer</synonym>
    <synonym>Hydrochloride, arginine</synonym>
    <synonym>Arginine hydrochloride</synonym>
    <synonym>DL Arginine acetate, monohydrate</synonym>
  </synonyms>
  <chemical_formula>C6H14N4O2</chemical_formula>
  <average_molecular_weight>174.201</average_molecular_weight>
  <monisotopic_moleculate_weight>174.111675712</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-5-carbamimidamidopentanoic acid</iupac_name>
  <traditional_iupac>L-arginine</traditional_iupac>
  <cas_registry_number>74-79-3</cas_registry_number>
  <smiles>N[C@@H](CCCNC(N)=N)C(O)=O</smiles>
  <inchi>InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m0/s1</inchi>
  <inchikey>ODKSFYDXXFIFQN-BYPYZUCNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Guanidines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>arginine</external_descriptor>
      <external_descriptor>glutamine family amino acid</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>222 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>182 mg/mL at 25 °C</value>
      <source>Human Metabolome Project</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.2</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>12.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-5-carbamimidamidopentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>174.201</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>174.111675712</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCCNC(N)=N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H14N4O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ODKSFYDXXFIFQN-BYPYZUCNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>125.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>53.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nitric Oxide Signaling Pathway</name>
      <smpdb_id>SMP0108206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Arginine</name>
      <smpdb_id>SMP0119383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4162</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>218+/-33</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>73-98</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>57.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>59</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Chan JR, Boger RH, Bode-Boger SM, Tangphao O, Tsao PS, Blaschke TF, Cooke JP: Asymmetric dimethylarginine increases mononuclear cell adhesiveness in hypercholesterolemic humans. Arterioscler Thromb Vasc Biol. 2000 Apr;20(4):1040-6. doi: 10.1161/01.atv.20.4.1040.</reference_text>
          <pubmed_id>10764670</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>135-182</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>54.7-60.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>93.3 +/- 21.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by ESI-MS/MS in male Charolais x Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Widmann P, Reverter A, Weikard R, Suhre K, Hammon HM, Albrecht E, Kuehn C: Systems biology analysis merging phenotype, metabolomic and genomic data identifies Non-SMC Condensin I Complex, Subunit G (NCAPG) and cellular maintenance processes as major contributors to genetic variability in bovine feed efficiency. PLoS One. 2015 Apr 15;10(4):e0124574. doi: 10.1371/journal.pone.0124574. eCollection 2015.</reference_text>
          <pubmed_id>25875852</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by ESI-MS/MS in male Charolais x Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Weikard R, Altmaier E, Suhre K, Weinberger KM, Hammon HM, Albrecht E, Setoguchi K, Takasuga A, Kuhn C: Metabolomic profiles indicate distinct physiological pathways affected by two loci with major divergent effect on Bos taurus growth and lipid deposition. Physiol Genomics. 2010 Oct;42A(2):79-88. doi: 10.1152/physiolgenomics.00120.2010. Epub 2010 Jul 20.</reference_text>
          <pubmed_id>20647382</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>9+/-5</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>61+/-14</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27.5 +/- 7.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27 +/- 12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31.4 +/- 10.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>299-686</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>18.84 +/- 14.13</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>17+/-11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>14.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>19.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>44.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>18.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>14 +/- 7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>20 +/- 10</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>44.5 +/- 35.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>19 +/- 14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>19 +/- 14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>70+/-16</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>200-460</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By paper chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Brown-Woodman PD, White IG: Amino acid composition of semen and the secretions of the male reproductive tract. Aust J Biol Sci. 1974 Aug;27(4):415-22. doi: 10.1071/bi9740415.</reference_text>
          <pubmed_id>4429492</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>51+/-12</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00062</kegg_id>
  <drugbank_id>DB00125</drugbank_id>
  <foodb_id>FDB002257</foodb_id>
  <chemspider_id>6082</chemspider_id>
  <pubchem_compound_id>6322</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16467</chebi_id>
  <knapsack_id>C00001340</knapsack_id>
  <wikipedia_id>L-arginine</wikipedia_id>
  <meta_cyc_id>ARG</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33707</bigg_id>
  <metlin_id>5502</metlin_id>
  <synthesis_reference>Meyer, Helmut E.; Swiderek, Kristine; Hoffmann-Posorske, Edeltraut; Korte, Horst; Heilmeyer, Ludwig M. G., Jr. Quantitative determination of phosphoserine by high-performance liquid chromatography as the phenylthiocarbamyl-S-ethylcysteine. Application to</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00022</protein_accession>
      <name>Nitric oxide synthase, endothelial</name>
      <uniprot_id>P29473</uniprot_id>
      <gene_name>NOS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00069</protein_accession>
      <name>Nitric oxide synthase, inducible</name>
      <uniprot_id>Q27995</uniprot_id>
      <gene_name>NOS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00076</protein_accession>
      <name>1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase gamma-1</name>
      <uniprot_id>P08487</uniprot_id>
      <gene_name>PLCG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00134</protein_accession>
      <name>[Protein ADP-ribosylarginine] hydrolase</name>
      <uniprot_id>Q32KR8</uniprot_id>
      <gene_name>ADPRH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00238</protein_accession>
      <name>Argininosuccinate lyase</name>
      <uniprot_id>Q3SZJ0</uniprot_id>
      <gene_name>ASL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00552</protein_accession>
      <name>Carboxypeptidase E</name>
      <uniprot_id>P04836</uniprot_id>
      <gene_name>CPE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00553</protein_accession>
      <name>Arginase-1</name>
      <uniprot_id>Q2KJ64</uniprot_id>
      <gene_name>ARG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00554</protein_accession>
      <name>Carboxypeptidase B</name>
      <uniprot_id>P00732</uniprot_id>
      <gene_name>CPB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00555</protein_accession>
      <name>Probable arginyl-tRNA synthetase, mitochondrial</name>
      <uniprot_id>Q0P5H7</uniprot_id>
      <gene_name>RARS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00556</protein_accession>
      <name>Glycine amidinotransferase, mitochondrial</name>
      <uniprot_id>Q2HJ74</uniprot_id>
      <gene_name>GATM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00557</protein_accession>
      <name>Inducible nitric oxid synthase</name>
      <uniprot_id>Q6ZXD5</uniprot_id>
      <gene_name>iNOS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00558</protein_accession>
      <name>Arginase-2, mitochondrial</name>
      <uniprot_id>Q58DL1</uniprot_id>
      <gene_name>ARG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01633</protein_accession>
      <name>Solute carrier family 7 member 1</name>
      <uniprot_id>Q27IK9</uniprot_id>
      <gene_name>SLC7A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01634</protein_accession>
      <name>Arginine vasopressin receptor 2</name>
      <uniprot_id>C5HF06</uniprot_id>
      <gene_name>AVPR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01635</protein_accession>
      <name>Arginine vasopressin receptor V3</name>
      <uniprot_id>Q95L48</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01636</protein_accession>
      <name>Vasopressin V2 receptor</name>
      <uniprot_id>P48044</uniprot_id>
      <gene_name>AVPR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01637</protein_accession>
      <name>Solute carrier family 7 (Cationic amino acid transporter, y+ system), member 3</name>
      <uniprot_id>A0JNF2</uniprot_id>
      <gene_name>SLC7A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:02 UTC</creation_date>
  <update_date>2020-04-15 22:14:02 UTC</update_date>
  <accession>BMDB0000518</accession>
  <secondary_accessions>
    <accession>BMDB00518</accession>
  </secondary_accessions>
  <name>Chenodeoxycholic acid</name>
  <description/>
  <synonyms>
    <synonym>3alpha,7alpha-Dihydroxy-5beta-cholanic acid</synonym>
    <synonym>7alpha-Hydroxylithocholic acid</synonym>
    <synonym>Anthropodeoxycholic acid</synonym>
    <synonym>Anthropodesoxycholic acid</synonym>
    <synonym>CDCA</synonym>
    <synonym>Chenic acid</synonym>
    <synonym>Chenix</synonym>
    <synonym>Chenodiol</synonym>
    <synonym>Gallodesoxycholic acid</synonym>
    <synonym>3a,7a-Dihydroxy-5b-cholanate</synonym>
    <synonym>3a,7a-Dihydroxy-5b-cholanic acid</synonym>
    <synonym>3alpha,7alpha-Dihydroxy-5beta-cholanate</synonym>
    <synonym>3Α,7α-dihydroxy-5β-cholanate</synonym>
    <synonym>3Α,7α-dihydroxy-5β-cholanic acid</synonym>
    <synonym>7a-Hydroxylithocholate</synonym>
    <synonym>7a-Hydroxylithocholic acid</synonym>
    <synonym>7alpha-Hydroxylithocholate</synonym>
    <synonym>7Α-hydroxylithocholate</synonym>
    <synonym>7Α-hydroxylithocholic acid</synonym>
    <synonym>Anthropodeoxycholate</synonym>
    <synonym>Anthropodesoxycholate</synonym>
    <synonym>Chenate</synonym>
    <synonym>Gallodesoxycholate</synonym>
    <synonym>Chenodeoxycholate</synonym>
    <synonym>(+)-Chenodeoxycholate</synonym>
    <synonym>(+)-Chenodeoxycholic acid</synonym>
    <synonym>(3a,5b,7a)-3,7-Dihydroxy-cholan-24-Oate</synonym>
    <synonym>(3a,5b,7a)-3,7-Dihydroxy-cholan-24-Oic acid</synonym>
    <synonym>3a,7a-Dihydroxy-5b,14a,17b-cholanate</synonym>
    <synonym>3a,7a-Dihydroxy-5b,14a,17b-cholanic acid</synonym>
    <synonym>3a,7a-Dihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,7a-Dihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>7a-Hydroxy-desoxycholsaeure</synonym>
    <synonym>Chenodesoxycholsaeure</synonym>
    <synonym>Acid, chenique</synonym>
    <synonym>Chenofalk</synonym>
    <synonym>Chenophalk</synonym>
    <synonym>Acid, chenodeoxycholic</synonym>
    <synonym>Chenodeoxycholate, sodium</synonym>
    <synonym>Quenocol</synonym>
    <synonym>Solvay brand OF chenodeoxycholic acid</synonym>
    <synonym>Antigen brand OF chenodeoxycholic acid</synonym>
    <synonym>Falk brand OF chenodeoxycholic acid</synonym>
    <synonym>Quenobilan</synonym>
    <synonym>Sodium chenodeoxycholate</synonym>
    <synonym>Tramedico brand OF chenodeoxycholic acid</synonym>
    <synonym>Zambon brand OF chenodeoxycholic acid</synonym>
    <synonym>Acid, chenic</synonym>
    <synonym>Acid, gallodesoxycholic</synonym>
    <synonym>Chenique acid</synonym>
    <synonym>Estedi brand OF chenodeoxycholic acid</synonym>
    <synonym>Henohol</synonym>
  </synonyms>
  <chemical_formula>C24H40O4</chemical_formula>
  <average_molecular_weight>392.572</average_molecular_weight>
  <monisotopic_moleculate_weight>392.292659768</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>474-25-9</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O</smiles>
  <inchi>InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1</inchi>
  <inchikey>RUDATBOHQWOJDD-BSWAIDMHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>Cholane and derivatives</external_descriptor>
      <external_descriptor>bile acid</external_descriptor>
      <external_descriptor>dihydroxy-5beta-cholanic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>165 - 167 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0899 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.15</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>392.572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.292659768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RUDATBOHQWOJDD-BSWAIDMHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>245607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>245608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>245609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>265554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>265555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>265556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438647</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB06777</drugbank_id>
  <foodb_id>FDB022087</foodb_id>
  <chemspider_id>9728</chemspider_id>
  <pdbe_id/>
  <chebi_id>16755</chebi_id>
  <pubchem_compound_id>10133</pubchem_compound_id>
  <kegg_id>C02528</kegg_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Chenodiol</wikipedia_id>
  <metlin_id>207</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Sato, Yoshio; Ikekawa, Nobuo.  Preparation of chenodeoxycholic acid.    Journal of Organic Chemistry  (1959),  24  1367-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01586</protein_accession>
      <name>Bile acid receptor</name>
      <uniprot_id>Q3SZL0</uniprot_id>
      <gene_name>NR1H4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:03 UTC</creation_date>
  <update_date>2020-03-13 16:21:48 UTC</update_date>
  <accession>BMDB0000520</accession>
  <secondary_accessions>
    <accession>BMDB00520</accession>
  </secondary_accessions>
  <name>5a-Cholestane-3a,7a,12a,25-tetrol</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C27H48O4</chemical_formula>
  <average_molecular_weight>436.6676</average_molecular_weight>
  <monisotopic_moleculate_weight>436.355260024</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7R,9R,10R,11S,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol</iupac_name>
  <traditional_iupac>(1S,2S,5R,7R,9R,10R,11S,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@]12CCC([C@H](C)CCCC(C)(C)O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17-,18-,19?,20+,21+,22-,23+,24+,26+,27-/m1/s1</inchi>
  <inchikey>NTIXPPFPXLYJCT-SUGKMTRFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerophospholipids</class>
    <sub_class>Glycerophosphoethanolamines</sub_class>
    <direct_parent>Phosphatidylethanolamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Dialkyl phosphates</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phosphoethanolamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Diacylglycero-3-phosphoethanolamine</substituent>
      <substituent>Dialkyl phosphate</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoethanolamine</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7R,9R,10R,11S,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>436.6676</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>436.355260024</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC([C@H](C)CCCC(C)(C)O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H48O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17-,18-,19?,20+,21+,22-,23+,24+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NTIXPPFPXLYJCT-SUGKMTRFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>124.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>53.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354699</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB026726</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id/>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <chebi_id/>
  <pdbe_id/>
  <synthesis_reference>Wang, Ming Yao; Elliott, William H.  Bile acids.  LXXVII.  Large-scale preparation of 5a-anhydrocyprinol from carp bile.    Preparative Biochemistry  (1985),  15(4),  191-209.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:04 UTC</creation_date>
  <update_date>2020-03-13 16:21:48 UTC</update_date>
  <accession>BMDB0000521</accession>
  <secondary_accessions>
    <accession>BMDB00521</accession>
  </secondary_accessions>
  <name>5Z-Tetradecenoic acid</name>
  <description>5-Tetradecenoic acid, also known as (Z)-5-tetradecenoate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 5-Tetradecenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-Tetradecenoic acid has been linked to the inborn metabolic disorders including very long chain acyl-coa dehydrogenase deficiency.</description>
  <synonyms>
    <synonym>(Z)-5-Tetradecenoic acid</synonym>
    <synonym>cis-5-Tetradecenoic acid</synonym>
    <synonym>(Z)-5-Tetradecenoate</synonym>
    <synonym>cis-5-Tetradecenoate</synonym>
    <synonym>5Z-Tetradecenoate</synonym>
    <synonym>5-Tetradecenoate</synonym>
    <synonym>(5Z)- 5-Tetradecenoate</synonym>
    <synonym>(5Z)- 5-Tetradecenoic acid</synonym>
    <synonym>cis-D5-Tetradecenoate</synonym>
    <synonym>cis-D5-Tetradecenoic acid</synonym>
    <synonym>Physeterate</synonym>
    <synonym>(5Z)-5-Tetradecenoic acid</synonym>
    <synonym>C14:1W9</synonym>
    <synonym>FA(14:1(5Z))</synonym>
    <synonym>FA(14:1n9)</synonym>
    <synonym>Physeteric acid</synonym>
    <synonym>Physoteric acid</synonym>
    <synonym>cis-Tetradec-5-enoate</synonym>
  </synonyms>
  <chemical_formula>C14H26O2</chemical_formula>
  <average_molecular_weight>226.355</average_molecular_weight>
  <monisotopic_moleculate_weight>226.193280076</monisotopic_moleculate_weight>
  <iupac_name>(5Z)-tetradec-5-enoic acid</iupac_name>
  <traditional_iupac>cis-5-tetradecenoic acid</traditional_iupac>
  <cas_registry_number>5684-70-8</cas_registry_number>
  <smiles>CCCCCCCC\C=C/CCCC(O)=O</smiles>
  <inchi>InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h9-10H,2-8,11-13H2,1H3,(H,15,16)/b10-9-</inchi>
  <inchikey>AFGUVBVUFZMJMX-KTKRTIGZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>monounsaturated fatty acid</external_descriptor>
      <external_descriptor>tetradecenoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5Z)-tetradec-5-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>226.355</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>226.193280076</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCC\C=C/CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H26O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h9-10H,2-8,11-13H2,1H3,(H,15,16)/b10-9-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AFGUVBVUFZMJMX-KTKRTIGZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332199</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022089</foodb_id>
  <kegg_id/>
  <chemspider_id>4471825</chemspider_id>
  <pubchem_compound_id>5312400</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>70716</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5506</metlin_id>
  <synthesis_reference>Jin, Shiow Jen; Tserng, Kou Yi.  Metabolic origins of urinary unsaturated dicarboxylic acids.    Biochemistry  (1990),  29(37),  8540-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:05 UTC</creation_date>
  <update_date>2020-04-14 22:47:45 UTC</update_date>
  <accession>BMDB0000522</accession>
  <secondary_accessions>
    <accession>BMDB00522</accession>
  </secondary_accessions>
  <name>3-Methylglutaconic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Methylglutaconate</synonym>
    <synonym>b-Methylglutaconate</synonym>
    <synonym>b-Methylglutaconic acid</synonym>
    <synonym>beta-Methylglutaconate</synonym>
    <synonym>beta-Methylglutaconic acid</synonym>
    <synonym>Β-methylglutaconic acid</synonym>
    <synonym>3-Methyl-2-pentenedioic acid</synonym>
    <synonym>3E-Methylglutaconate</synonym>
    <synonym>3-Methylglutaconic acid</synonym>
  </synonyms>
  <chemical_formula>C6H8O4</chemical_formula>
  <average_molecular_weight>144.1253</average_molecular_weight>
  <monisotopic_moleculate_weight>144.042258744</monisotopic_moleculate_weight>
  <iupac_name>(2E)-3-methylpent-2-enedioic acid</iupac_name>
  <traditional_iupac>β-methylglutaconic acid</traditional_iupac>
  <cas_registry_number>5746-90-7</cas_registry_number>
  <smiles>C\C(CC(O)=O)=C/C(O)=O</smiles>
  <inchi>InChI=1S/C6H8O4/c1-4(2-5(7)8)3-6(9)10/h2H,3H2,1H3,(H,7,8)(H,9,10)/b4-2+</inchi>
  <inchikey>WKRBKYFIJPGYQC-DUXPYHPUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Methyl-branched fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-3-methylpent-2-enedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>144.1253</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>144.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C\C(CC(O)=O)=C/C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H8O4/c1-4(2-5(7)8)3-6(9)10/h2H,3H2,1H3,(H,7,8)(H,9,10)/b4-2+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WKRBKYFIJPGYQC-DUXPYHPUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>33.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>89205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>89206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>89207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>152079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>152080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>152081</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022090</foodb_id>
  <kegg_id/>
  <chemspider_id>1267861</chemspider_id>
  <pubchem_compound_id>1551553</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>37245</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>3-Methylglutaconic acid</wikipedia_id>
  <metlin_id>5507</metlin_id>
  <synthesis_reference>Aoyama, Takayuki; Kato, Kazuo; Shimada, Nobuyoshi; Fujii, Akio; Takita, Tomohisa.  Production of 3-methylglutaconic acid.    Jpn. Kokai Tokkyo Koho  (1986),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:06 UTC</creation_date>
  <update_date>2020-03-13 16:21:49 UTC</update_date>
  <accession>BMDB0000523</accession>
  <secondary_accessions>
    <accession>BMDB00523</accession>
  </secondary_accessions>
  <name>5-Androstene-3b,16b,17a-triol</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C19H30O3</chemical_formula>
  <average_molecular_weight>306.4397</average_molecular_weight>
  <monisotopic_moleculate_weight>306.219494826</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,10R,11S,13S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,13,14-triol</iupac_name>
  <traditional_iupac>5-androstene-3b,16b,17a-triol</traditional_iupac>
  <cas_registry_number>25126-70-9</cas_registry_number>
  <smiles>[H][C@@]12C[C@H](O)[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-17,20-22H,4-10H2,1-2H3/t12-,13+,14-,15-,16-,17+,18-,19-/m0/s1</inchi>
  <inchikey>GUGSXATYPSGVAY-CUZKMJQKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>16-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>16-beta-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,10R,11S,13S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,13,14-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>306.4397</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>306.219494826</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@H](O)[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H30O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-17,20-22H,4-10H2,1-2H3/t12-,13+,14-,15-,16-,17+,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GUGSXATYPSGVAY-CUZKMJQKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362700</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>13628101</chemspider_id>
  <foodb_id>FDB022091</foodb_id>
  <pubchem_compound_id>21252251</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5508</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Huffman, Max N.; Lott, Mary Harriett.  Steric structure of estriol and related steroids.    Journal of the American Chemical Society  (1947),  69  1835.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:08 UTC</creation_date>
  <update_date>2020-03-13 16:21:50 UTC</update_date>
  <accession>BMDB0000524</accession>
  <secondary_accessions>
    <accession>BMDB00524</accession>
  </secondary_accessions>
  <name>5b-Cholestane-3a,7a,12a,25-tetrol</name>
  <description/>
  <synonyms>
    <synonym>5b-Cholestane-3a,7a,12a,25-tetrol</synonym>
    <synonym>5Β-cholestane-3α,7α,12α,25-tetrol</synonym>
    <synonym>5 beta Cholestane-3 alpha,7 alpha,12 alpha,25-tetrol</synonym>
    <synonym>5 beta-Cholestane-3 beta,7 alpha,12 alpha,25-tetrol</synonym>
    <synonym>Cholestane-3,7,12,25-tetrol</synonym>
    <synonym>(3Α,5β,7α,12α)-cholestane-3,7,12,25-tetrol</synonym>
    <synonym>3Α,7α,12α,25-tetrahydroxycoprostane</synonym>
    <synonym>(3alpha,5beta,7alpha,12alpha)-Cholestane-3,7,12,25-tetrol</synonym>
    <synonym>3alpha,7alpha,12alpha,25-Tetrahydroxycoprostane</synonym>
    <synonym>5b-Cholestan-3a,7a,12a,25-tetrol</synonym>
    <synonym>5beta-Cholestane-3alpha,7alpha,12alpha,25-tetrol</synonym>
  </synonyms>
  <chemical_formula>C27H48O4</chemical_formula>
  <average_molecular_weight>436.677</average_molecular_weight>
  <monisotopic_moleculate_weight>436.355260026</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</iupac_name>
  <traditional_iupac>(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</traditional_iupac>
  <cas_registry_number>18866-87-0</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)(C)O</smiles>
  <inchi>InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1</inchi>
  <inchikey>NTIXPPFPXLYJCT-RNUSRIHUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>25-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C27 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>436.677</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>436.355260026</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)(C)O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H48O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NTIXPPFPXLYJCT-RNUSRIHUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>124.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>53.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1249099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1249100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1249101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1364416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1364417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1364418</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022092</foodb_id>
  <chemspider_id>146751</chemspider_id>
  <pdbe_id/>
  <chebi_id/>
  <pubchem_compound_id>167758</pubchem_compound_id>
  <kegg_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5509</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Dayal B; Bagan E; Speck J; Salen G  A facile synthesis of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol.    Steroids  (1980),  35(4),  439-44. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:09 UTC</creation_date>
  <update_date>2020-03-13 16:21:51 UTC</update_date>
  <accession>BMDB0000525</accession>
  <secondary_accessions>
    <accession>BMDB00525</accession>
  </secondary_accessions>
  <name>5-Hydroxyhexanoic acid</name>
  <description/>
  <synonyms>
    <synonym>5-Hydroxy caproic acid</synonym>
    <synonym>5-Hydroxy-hexanoic acid</synonym>
    <synonym>5-Hydroxycaproic acid</synonym>
    <synonym>5-OH-Caproic acid</synonym>
    <synonym>5-Hydroxy caproate</synonym>
    <synonym>5-Hydroxy-hexanoate</synonym>
    <synonym>5-Hydroxycaproate</synonym>
    <synonym>5-OH-Caproate</synonym>
    <synonym>5-Hydroxyhexanoate</synonym>
    <synonym>5-Hydroxyhexanoic acid</synonym>
  </synonyms>
  <chemical_formula>C6H12O3</chemical_formula>
  <average_molecular_weight>132.1577</average_molecular_weight>
  <monisotopic_moleculate_weight>132.07864425</monisotopic_moleculate_weight>
  <iupac_name>5-hydroxyhexanoic acid</iupac_name>
  <traditional_iupac>5-hydroxyhexanoic acid</traditional_iupac>
  <cas_registry_number>44843-89-2</cas_registry_number>
  <smiles>CC(O)CCCC(O)=O</smiles>
  <inchi>InChI=1S/C6H12O3/c1-5(7)3-2-4-6(8)9/h5,7H,2-4H2,1H3,(H,8,9)</inchi>
  <inchikey>YDCRNMJQROAWFT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-hydroxyhexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.1577</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.07864425</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(O)CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O3/c1-5(7)3-2-4-6(8)9/h5,7H,2-4H2,1H3,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YDCRNMJQROAWFT-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144032</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>149280</chemspider_id>
  <foodb_id>FDB022093</foodb_id>
  <pubchem_compound_id>170748</pubchem_compound_id>
  <chebi_id>131434</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5510</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Valentin, H. E.; Schoenebaum, A.; Steinbuechel, A.  Identification of 5-hydroxyhexanoic acid, 4-hydroxyheptanoic acid and 4-hydroxyoctanoic acid as new constituents of bacterial polyhydroxyalkanoic acids.    Applied Microbiology and Biotechnology  (1996),  46(3),  261-267.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:11 UTC</creation_date>
  <update_date>2020-03-13 16:21:51 UTC</update_date>
  <accession>BMDB0000526</accession>
  <secondary_accessions>
    <accession>BMDB00526</accession>
  </secondary_accessions>
  <name>5a-Tetrahydrocortisol</name>
  <description/>
  <synonyms>
    <synonym>3,11,17,21-Tetrahydroxypregnan-20-one</synonym>
    <synonym>3a,11b,17,21-Tetrahydroxy-5a-pregnan-20-one</synonym>
    <synonym>3a,11b,17a,21-Tetrahydroxy-5a-pregnan-20-one</synonym>
    <synonym>3a,5a-Tetrahydrocortisol</synonym>
    <synonym>3a-Allotetrahydrocortisol</synonym>
    <synonym>3alpha, 5alpha-Tetrahydrocortisol</synonym>
    <synonym>3alpha,5alpha-Tetrahydrocortisol</synonym>
    <synonym>5a-Pregnane-3a,11b,17a,21-tetraol-20-one</synonym>
    <synonym>5a-Pregnane-3a,11b,17a,21-tetrol-20-one</synonym>
    <synonym>5alpha-Tetrahydrocortisol</synonym>
    <synonym>a-THF</synonym>
    <synonym>Allo-3a-tetrahydrocortisol</synonym>
    <synonym>Allo-3alpha-tetrahydrocortisol</synonym>
    <synonym>Allo-tetrahydrocortisol</synonym>
    <synonym>Allopregnane-3a,11b,17a,21-tetrol-20-one</synonym>
    <synonym>Allopregnane-3a,11b,21-tetrol-20-one</synonym>
    <synonym>Allopregnane-3alpha,11beta,17alpha,21-tetrol-20-one</synonym>
    <synonym>Allotetrahydro-compound F</synonym>
    <synonym>Allotetrahydro-cortisol</synonym>
    <synonym>Allotetrahydrocompound F</synonym>
    <synonym>Allotetrahydrocortisol</synonym>
    <synonym>alpha-THF</synonym>
    <synonym>ATHF</synonym>
    <synonym>Kendall'S compound c</synonym>
    <synonym>Reichstein'S substance C</synonym>
    <synonym>Tetrahydro-allocortisol</synonym>
    <synonym>Tetrahydroallocortisol</synonym>
    <synonym>Wintersteiner'S compound D</synonym>
    <synonym>Allotetrahydrocortisol, (3beta,5alpha,11beta)-isomer</synonym>
    <synonym>5AlphaTHF</synonym>
    <synonym>Allotetrahydrocortisol, (3alpha,5beta,11alpha)-isomer</synonym>
    <synonym>Allotetrahydrocortisol, (5alpha,11beta)-isomer</synonym>
    <synonym>Allotetrahydrocortisol, (3beta,5beta,11beta)-isomer</synonym>
    <synonym>(3alpha,5alpha,11beta)-3,11,17,21-Tetrahydroxypregnan-20-one</synonym>
    <synonym>(3α,5α,11β)-3,11,17,21-Tetrahydroxypregnan-20-one</synonym>
    <synonym>3alpha,11beta,17,21-Tetrahydroxy-5alpha-pregnan-20-one</synonym>
    <synonym>3alpha,11beta,17alpha,21-Tetrahydroxy-5alpha-pregnan-20-one</synonym>
    <synonym>3α,11β,17,21-Tetrahydroxy-5α-pregnan-20-one</synonym>
    <synonym>3α,11β,17α,21-Tetrahydroxy-5α-pregnan-20-one</synonym>
    <synonym>3α,5α-Tetrahydrocortisol</synonym>
    <synonym>5alpha-Pregnane-3alpha,11beta,17alpha,21-tetraol-20-one</synonym>
    <synonym>5alpha-Pregnane-3alpha,11beta,17alpha,21-tetrol-20-one</synonym>
    <synonym>5alpha-THF</synonym>
    <synonym>5α-Pregnane-3α,11β,17α,21-tetraol-20-one</synonym>
    <synonym>5α-Pregnane-3α,11β,17α,21-tetrol-20-one</synonym>
    <synonym>5α-THF</synonym>
    <synonym>5α-Tetrahydrocortisol</synonym>
    <synonym>Allopregnane-3α,11β,17α,21-tetrol-20-one</synonym>
    <synonym>allo-3α-Tetrahydrocortisol</synonym>
    <synonym>α-THF</synonym>
  </synonyms>
  <chemical_formula>C21H34O5</chemical_formula>
  <average_molecular_weight>366.4917</average_molecular_weight>
  <monisotopic_moleculate_weight>366.240624198</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-1-[(1S,2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one</iupac_name>
  <traditional_iupac>2-hydroxy-1-[(1S,2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone</traditional_iupac>
  <cas_registry_number>302-91-0</cas_registry_number>
  <smiles>[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18+,19-,20-,21-/m0/s1</inchi>
  <inchikey>AODPIQQILQLWGS-FDSHTENPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>11-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>11-beta-hydroxysteroid</substituent>
      <substituent>11-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Polyol</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>244.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-1-[(1S,2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>366.4917</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>366.240624198</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H34O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18+,19-,20-,21-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AODPIQQILQLWGS-FDSHTENPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>97.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>41.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>100689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>100690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>100691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>166110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>166111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>166112</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>83726</chemspider_id>
  <foodb_id>FDB022094</foodb_id>
  <pubchem_compound_id>92748</pubchem_compound_id>
  <chebi_id>89627</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5511</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Fukushima, David K.; Daum, Sol.  Synthesis of Reichstein's substance C and related compounds.    Journal of Organic Chemistry  (1961),  26  520-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:13 UTC</creation_date>
  <update_date>2020-04-15 22:14:03 UTC</update_date>
  <accession>BMDB0000527</accession>
  <secondary_accessions>
    <accession>BMDB00527</accession>
  </secondary_accessions>
  <name>6a,12a-Dihydroxylithocholic acid</name>
  <description/>
  <synonyms>
    <synonym>6a,12a-Dihydroxylithocholate</synonym>
    <synonym>3a,6a,12a-Trihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,6a,12a-Trihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3a,6a,12a-Trihydroxycholate</synonym>
    <synonym>3a,6a,12a-Trihydroxycholic acid</synonym>
    <synonym>(4R)-4-[(1S,2R,5R,8S,10R,11S,14R,15R,16S)-5,8,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
    <synonym>6a,12a-Dihydroxylithocholic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5R,8S,10R,11S,14R,15R,16S)-5,8,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>3a,6a,12a-trihydroxycholate</traditional_iupac>
  <cas_registry_number>21066-18-2</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-22(28)29)16-5-6-17-15-11-20(26)19-10-14(25)8-9-23(19,2)18(15)12-21(27)24(16,17)3/h13-21,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15+,16-,17+,18+,19?,20+,21+,23-,24-/m1/s1</inchi>
  <inchikey>GCAHOAMXTYBLNZ-YAZNBHORSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>6-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>6-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5R,8S,10R,11S,14R,15R,16S)-5,8,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-22(28)29)16-5-6-17-15-11-20(26)19-10-14(25)8-9-23(19,2)18(15)12-21(27)24(16,17)3/h13-21,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14-,15+,16-,17+,18+,19?,20+,21+,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GCAHOAMXTYBLNZ-YAZNBHORSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301053</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>17215966</chemspider_id>
  <foodb_id>FDB022095</foodb_id>
  <pubchem_compound_id>22833529</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5512</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Iida, Takashi; Tamaru, Tamaaki; Chang, Frederic C.; Goto, Junichi; Nambara, Toshio. Potential bile acid metabolites. XVIII. Synthesis of stereoisomeric 3,6,12a-trihydroxy-5b-cholanoic acids. Journal of Lipid Research (1991), 32(4), 649-58.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:14 UTC</creation_date>
  <update_date>2020-04-14 22:47:46 UTC</update_date>
  <accession>BMDB0000528</accession>
  <secondary_accessions>
    <accession>BMDB00528</accession>
  </secondary_accessions>
  <name>4,5-Dihydroorotic acid</name>
  <description>4,5-Dihydroorotic acid, also known as hydroorotate, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. 4,5-Dihydroorotic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 4,5-Dihydroorotic acid exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>5,6-Dihydro-orotic acid</synonym>
    <synonym>DL-Dihydroortotic acid</synonym>
    <synonym>Hydroorotic acid</synonym>
    <synonym>5,6-Dihydro-orotate</synonym>
    <synonym>DL-Dihydroortotate</synonym>
    <synonym>Hydroorotate</synonym>
    <synonym>4,5-Dihydroorotate</synonym>
    <synonym>(+)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylate</synonym>
    <synonym>(+)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylic acid</synonym>
    <synonym>(R)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylate</synonym>
    <synonym>(R)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylic acid</synonym>
    <synonym>(S)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylate</synonym>
    <synonym>(S)-2,6-Dioxo-hexahydro-pyrimidine-4-carboxylic acid</synonym>
    <synonym>2,6-Dioxo-hexahydro-pyrimidine-4-carboxylate</synonym>
    <synonym>2,6-Dioxo-hexahydro-pyrimidine-4-carboxylic acid</synonym>
    <synonym>5,6-Dihydroorotate</synonym>
    <synonym>L-Hydroorotate</synonym>
    <synonym>L-Hydroorotic acid</synonym>
    <synonym>R,S-Hydroorotate</synonym>
    <synonym>L-Dihydroorotate</synonym>
    <synonym>4,5-Dihydroorotic acid, (L)-isomer</synonym>
    <synonym>Dihydroorotate</synonym>
    <synonym>4,5-Dihydroorotic acid, (D)-isomer</synonym>
    <synonym>4,5-Dihydroorotic acid, (DL)-isomer</synonym>
  </synonyms>
  <chemical_formula>C5H6N2O4</chemical_formula>
  <average_molecular_weight>158.1121</average_molecular_weight>
  <monisotopic_moleculate_weight>158.03275669</monisotopic_moleculate_weight>
  <iupac_name>2,6-dioxo-1,3-diazinane-4-carboxylic acid</iupac_name>
  <traditional_iupac>dihydroorotic acid</traditional_iupac>
  <cas_registry_number>155-54-4</cas_registry_number>
  <smiles>OC(=O)C1CC(=O)NC(=O)N1</smiles>
  <inchi>InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)</inchi>
  <inchikey>UFIVEPVSAGBUSI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Diazinanes</alternative_parent>
      <alternative_parent>Dicarboximides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl ureas</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-diazinane</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonic acid derivative</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboximide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl urea</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
      <substituent>Ureide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylurea</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
      <external_descriptor>pyrimidinemonocarboxylic acid</external_descriptor>
      <external_descriptor>secondary amide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-8.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,6-dioxo-1,3-diazinane-4-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>158.1121</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>158.03275669</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1CC(=O)NC(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H6N2O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UFIVEPVSAGBUSI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>95.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183164</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fermented milk, by capillary electrophoresis-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
          <pubmed_id>26686724</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022096</foodb_id>
  <chemspider_id>628</chemspider_id>
  <pdbe_id/>
  <chebi_id>30865</chebi_id>
  <pubchem_compound_id>648</pubchem_compound_id>
  <kegg_id>C00337</kegg_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>4,5-Dihydroorotic_acid</wikipedia_id>
  <metlin_id>5513</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Burger, Klaus; Neuhauser, Horst; Rudolph, Martin.  A new, preparatively simple way to dihydroorotic acid, 1-methyl-4,5-dihydroorotic acid and their derivatives.    Chemiker-Zeitung  (1990),  114(7-8),  251-5.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
      <pubmed_id>26686724</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:15 UTC</creation_date>
  <update_date>2020-03-13 16:21:53 UTC</update_date>
  <accession>BMDB0000529</accession>
  <secondary_accessions>
    <accession>BMDB00529</accession>
  </secondary_accessions>
  <name>5-Dodecenoic acid</name>
  <description>5-Dodecenoic acid, also known as 5-dodecenoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 5-Dodecenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.</description>
  <synonyms>
    <synonym>5-Dodecenoate</synonym>
    <synonym>5-Dodecenoic acid</synonym>
    <synonym>5-Dodecenoic acid, (e)-isomer</synonym>
    <synonym>5E-Dodecenoate</synonym>
  </synonyms>
  <chemical_formula>C12H22O2</chemical_formula>
  <average_molecular_weight>198.306</average_molecular_weight>
  <monisotopic_moleculate_weight>198.161979948</monisotopic_moleculate_weight>
  <iupac_name>(5E)-dodec-5-enoic acid</iupac_name>
  <traditional_iupac>5-dodecenoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H]\C(CCCCCC)=C(\[H])CCCC(O)=O</smiles>
  <inchi>InChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h7-8H,2-6,9-11H2,1H3,(H,13,14)/b8-7+</inchi>
  <inchikey>IJBFSOLHRKELLR-BQYQJAHWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5E)-dodec-5-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>198.306</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>198.161979948</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]\C(CCCCCC)=C(\[H])CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H22O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h7-8H,2-6,9-11H2,1H3,(H,13,14)/b8-7+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IJBFSOLHRKELLR-BQYQJAHWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>59.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1260550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1260551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1260552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1375675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1375676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1375677</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id/>
  <foodb_id/>
  <pubchem_compound_id>5312377</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference>Rock, Charles O.; Garwin, Jeffrey L.; Cronan, John E., Jr.  Preparative enzymic synthesis of acyl-acyl carrier protein.    Methods in Enzymology  (1981),  72(Lipids, Part D),  397-403. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:16 UTC</creation_date>
  <update_date>2020-03-13 16:21:53 UTC</update_date>
  <accession>BMDB0000530</accession>
  <secondary_accessions>
    <accession>BMDB00530</accession>
  </secondary_accessions>
  <name>6-Ketoestriol</name>
  <description/>
  <synonyms>
    <synonym>(16a,17b)-3,16,17-Trihydroxy-estra-1,3,5(10)-trien-6-one</synonym>
    <synonym>6-oxo-16a,17b-Estriol</synonym>
    <synonym>6-Oxoestratriol</synonym>
    <synonym>6-Oxoestriol</synonym>
  </synonyms>
  <chemical_formula>C18H22O4</chemical_formula>
  <average_molecular_weight>302.3649</average_molecular_weight>
  <monisotopic_moleculate_weight>302.151809192</monisotopic_moleculate_weight>
  <iupac_name>(1S,10R,11S,13R,14R,15S)-5,13,14-trihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-8-one</iupac_name>
  <traditional_iupac>6-ketoestriol</traditional_iupac>
  <cas_registry_number>7323-86-6</cas_registry_number>
  <smiles>[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(C=C(O)C=C3)C(=O)C[C@@]21[H]</smiles>
  <inchi>InChI=1S/C18H22O4/c1-18-5-4-11-10-3-2-9(19)6-13(10)15(20)7-12(11)14(18)8-16(21)17(18)22/h2-3,6,11-12,14,16-17,19,21-22H,4-5,7-8H2,1H3/t11-,12-,14+,16-,17+,18+/m1/s1</inchi>
  <inchikey>PYFIDTBVOMQKDC-XCYHEEQWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Estrane steroids</sub_class>
    <direct_parent>Estrogens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>16-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>6-oxosteroids</alternative_parent>
      <alternative_parent>Aryl alkyl ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>16-alpha-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>6-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Aryl alkyl ketone</substituent>
      <substituent>Aryl ketone</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Estrogen-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,10R,11S,13R,14R,15S)-5,13,14-trihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-8-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>302.3649</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>302.151809192</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(C=C(O)C=C3)C(=O)C[C@@]21[H]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H22O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H22O4/c1-18-5-4-11-10-3-2-9(19)6-13(10)15(20)7-12(11)14(18)8-16(21)17(18)22/h2-3,6,11-12,14,16-17,19,21-22H,4-5,7-8H2,1H3/t11-,12-,14+,16-,17+,18+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PYFIDTBVOMQKDC-XCYHEEQWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>82.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337587</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>10051287</chemspider_id>
  <foodb_id>FDB022098</foodb_id>
  <pubchem_compound_id>11876959</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5515</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Marrian, G. F.; Sneddon, A.  Partial synthesis of 6-oxoestriol and 6a-hydroxyestriol.    Biochemical Journal  (1960),  74  430-2.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:17 UTC</creation_date>
  <update_date>2020-03-13 16:21:54 UTC</update_date>
  <accession>BMDB0000531</accession>
  <secondary_accessions>
    <accession>BMDB00531</accession>
  </secondary_accessions>
  <name>3-Hydroxyvaleric acid</name>
  <description/>
  <synonyms>
    <synonym>3-Hydroxy valeric acid</synonym>
    <synonym>3-Hydroxy-pentanoic acid</synonym>
    <synonym>3-Hydroxy-valeric acid</synonym>
    <synonym>beta-Hydroxypentanoic acid</synonym>
    <synonym>beta-Hydroxyvaleric acid</synonym>
    <synonym>3-Hydroxy valerate</synonym>
    <synonym>3-Hydroxy-pentanoate</synonym>
    <synonym>3-Hydroxy-valerate</synonym>
    <synonym>b-Hydroxypentanoate</synonym>
    <synonym>b-Hydroxypentanoic acid</synonym>
    <synonym>beta-Hydroxypentanoate</synonym>
    <synonym>Β-hydroxypentanoate</synonym>
    <synonym>Β-hydroxypentanoic acid</synonym>
    <synonym>b-Hydroxyvalerate</synonym>
    <synonym>b-Hydroxyvaleric acid</synonym>
    <synonym>beta-Hydroxyvalerate</synonym>
    <synonym>Β-hydroxyvalerate</synonym>
    <synonym>Β-hydroxyvaleric acid</synonym>
    <synonym>3-Hydroxyvalerate</synonym>
    <synonym>3-Hydroxy-N-valerate</synonym>
    <synonym>3-Hydroxy-N-valeric acid</synonym>
    <synonym>3-Hydroxypentanoate</synonym>
    <synonym>3-Hydroxypentanoic acid</synonym>
    <synonym>b-Hydroxy-N-valerate</synonym>
    <synonym>b-Hydroxy-N-valeric acid</synonym>
    <synonym>beta-Hydroxy-N-valerate</synonym>
    <synonym>beta-Hydroxy-N-valeric acid</synonym>
    <synonym>3-Hydroxyvaleric acid</synonym>
  </synonyms>
  <chemical_formula>C5H10O3</chemical_formula>
  <average_molecular_weight>118.1311</average_molecular_weight>
  <monisotopic_moleculate_weight>118.062994186</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxypentanoic acid</iupac_name>
  <traditional_iupac>β-hydroxyvaleric acid</traditional_iupac>
  <cas_registry_number>10237-77-1</cas_registry_number>
  <smiles>CCC(O)CC(O)=O</smiles>
  <inchi>InChI=1S/C5H10O3/c1-2-4(6)3-5(7)8/h4,6H,2-3H2,1H3,(H,7,8)</inchi>
  <inchikey>REKYPYSUBKSCAT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxypentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>118.1311</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>118.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O3/c1-2-4(6)3-5(7)8/h4,6H,2-3H2,1H3,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>REKYPYSUBKSCAT-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>27.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>174999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175001</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022099</foodb_id>
  <chemspider_id>96952</chemspider_id>
  <kegg_id/>
  <drugbank_id/>
  <chebi_id>139272</chebi_id>
  <pubchem_compound_id>107802</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>3-Hydroxypentanoic_acid</wikipedia_id>
  <metlin_id>5516</metlin_id>
  <synthesis_reference>Manufacture of b-hydroxyvaleric acid. Jpn. Kokai Tokkyo Koho  (1982), 3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:18 UTC</creation_date>
  <update_date>2020-04-14 22:47:46 UTC</update_date>
  <accession>BMDB0000532</accession>
  <secondary_accessions>
    <accession>BMDB00532</accession>
  </secondary_accessions>
  <name>Acetylglycine</name>
  <description/>
  <synonyms>
    <synonym>Ac-gly-OH</synonym>
    <synonym>Acetamidoacetic acid</synonym>
    <synonym>Aceturic acid</synonym>
    <synonym>Acetylamino-acetic acid</synonym>
    <synonym>Acetylaminoacetic acid</synonym>
    <synonym>Ethanoylaminoethanoic acid</synonym>
    <synonym>Acetamidoacetate</synonym>
    <synonym>Acetate</synonym>
    <synonym>Acetic acid</synonym>
    <synonym>Acetylamino-acetate</synonym>
    <synonym>Acetylaminoacetate</synonym>
    <synonym>Ethanoylaminoethanoate</synonym>
    <synonym>15N-Acetylglycine a-radical</synonym>
    <synonym>2-Acetamidoacetate</synonym>
    <synonym>2-Acetamidoacetic acid</synonym>
    <synonym>Ac gly</synonym>
    <synonym>Aceturate</synonym>
    <synonym>Acetylglycocoll</synonym>
    <synonym>N-Acetyl-glycine</synonym>
    <synonym>N-Acetylglycine</synonym>
    <synonym>N-Acetylglycine sodium salt</synonym>
    <synonym>Acetylglycinate</synonym>
    <synonym>Acetylglycine</synonym>
  </synonyms>
  <chemical_formula>C4H7NO3</chemical_formula>
  <average_molecular_weight>117.1033</average_molecular_weight>
  <monisotopic_moleculate_weight>117.042593095</monisotopic_moleculate_weight>
  <iupac_name>2-acetamidoacetic acid</iupac_name>
  <traditional_iupac>aceturate</traditional_iupac>
  <cas_registry_number>543-24-8</cas_registry_number>
  <smiles>CC(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C4H7NO3/c1-3(6)5-2-4(7)8/h2H2,1H3,(H,5,6)(H,7,8)</inchi>
  <inchikey>OKJIRPAQVSHGFK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acetyl-amino acid</external_descriptor>
      <external_descriptor>N-acylglycine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>207 - 209 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>26.3 mg/mL at 15 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-acetamidoacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>117.1033</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>117.042593095</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H7NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H7NO3/c1-3(6)5-2-4(7)8/h2H2,1H3,(H,5,6)(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OKJIRPAQVSHGFK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440084</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB02713</drugbank_id>
  <foodb_id>FDB022100</foodb_id>
  <chemspider_id>10507</chemspider_id>
  <pdbe_id/>
  <chebi_id>40410</chebi_id>
  <pubchem_compound_id>10972</pubchem_compound_id>
  <kegg_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Aceturic acid</wikipedia_id>
  <metlin_id>5517</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Lin, Jiang Jen; Knifton, John F.; Yeakey, Ernest L.  Preparation of N-acetylglycine.  U.S.  (1990),  5 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:19 UTC</creation_date>
  <update_date>2020-03-13 16:21:55 UTC</update_date>
  <accession>BMDB0000534</accession>
  <secondary_accessions>
    <accession>BMDB00534</accession>
  </secondary_accessions>
  <name>Campestanol</name>
  <description/>
  <synonyms>
    <synonym>(24R)-5a-Ergostan-3b-ol</synonym>
    <synonym>24b-Ethylcholestanol</synonym>
    <synonym>24b-Methylcholestanol</synonym>
    <synonym>5a-Dihydrocampesterol</synonym>
    <synonym>Chalinastanol</synonym>
    <synonym>Dihydro-neospongosterol</synonym>
    <synonym>Dihydrocampesterin</synonym>
  </synonyms>
  <chemical_formula>C28H50O</chemical_formula>
  <average_molecular_weight>402.696</average_molecular_weight>
  <monisotopic_moleculate_weight>402.386166222</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol</iupac_name>
  <traditional_iupac>(1S,2S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol</traditional_iupac>
  <cas_registry_number>474-60-2</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C28H50O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18-26,29H,7-17H2,1-6H3/t19-,20-,21?,22?,23+,24-,25+,26+,27+,28-/m1/s1</inchi>
  <inchikey>ARYTXMNEANMLMU-XKPVSPJHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a  derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Ergostane steroids</sub_class>
    <direct_parent>Ergosterols and derivatives</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="Aliphatic homopolycyclic compounds" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>402.696</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>402.386166222</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C28H50O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C28H50O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18-26,29H,7-17H2,1-6H3/t19-,20-,21?,22?,23+,24-,25+,26+,27+,28-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ARYTXMNEANMLMU-XKPVSPJHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>124.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>52.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358842</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB001925</foodb_id>
  <chemspider_id>17215967</chemspider_id>
  <pubchem_compound_id>22833530</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <knapsack_id>C00007516</knapsack_id>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Campestanol</wikipedia_id>
  <metlin_id>5519</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Kircher, Henry W.; Rosenstein, Fumiko U.  Purification of campesterol and preparation of 7-dehydrocampesterol, 7-campestenol, and campestanol.  Lipids  (1974),  9(5),  333-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:21 UTC</creation_date>
  <update_date>2020-04-14 22:47:47 UTC</update_date>
  <accession>BMDB0000535</accession>
  <secondary_accessions>
    <accession>BMDB00535</accession>
    <accession>BMDB0061883</accession>
    <accession>BMDB61883</accession>
  </secondary_accessions>
  <name>Caproic acid</name>
  <description>Caproic acid, also known as hexanoate or caproate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Caproic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Caproic acid exists in all living species, ranging from bacteria to humans. In cattle, caproic acid is involved in the metabolic pathway called the mitochondrial Beta-oxidation OF short chain saturated fatty acids pathway. Caproic acid is a potentially toxic compound. Caproic acid has been found to be associated with several diseases known as perillyl alcohol administration for cancer treatment, nonalcoholic fatty liver disease, ulcerative colitis, and crohn's disease; also caproic acid has been linked to the inborn metabolic disorders including medium chain acyl-coa dehydrogenase deficiency.</description>
  <synonyms>
    <synonym>1-Hexanoic acid</synonym>
    <synonym>1-Pentanecarboxylic acid</synonym>
    <synonym>6:0</synonym>
    <synonym>Butylacetic acid</synonym>
    <synonym>C6:0</synonym>
    <synonym>Capronic acid</synonym>
    <synonym>CH3-[CH2]4-COOH</synonym>
    <synonym>Hexanoate</synonym>
    <synonym>Hexoic acid</synonym>
    <synonym>Hexylic acid</synonym>
    <synonym>N-Caproic acid</synonym>
    <synonym>N-Hexanoic acid</synonym>
    <synonym>N-Hexoic acid</synonym>
    <synonym>N-Hexylic acid</synonym>
    <synonym>Pentanecarboxylic acid</synonym>
    <synonym>Pentiformic acid</synonym>
    <synonym>Pentylformic acid</synonym>
    <synonym>1-Hexanoate</synonym>
    <synonym>1-Pentanecarboxylate</synonym>
    <synonym>Butylacetate</synonym>
    <synonym>Capronate</synonym>
    <synonym>Hexanoic acid</synonym>
    <synonym>Hexoate</synonym>
    <synonym>Hexylate</synonym>
    <synonym>N-Caproate</synonym>
    <synonym>N-Hexanoate</synonym>
    <synonym>N-Hexoate</synonym>
    <synonym>N-Hexylate</synonym>
    <synonym>Pentanecarboxylate</synonym>
    <synonym>Pentiformate</synonym>
    <synonym>Pentylformate</synonym>
    <synonym>Caproate</synonym>
    <synonym>Hexanoic acid, calcium salt</synonym>
    <synonym>Hexanoic acid, sodium salt, 1-(11)C-labeled</synonym>
    <synonym>Hexanoic acid, nickel (2+) salt</synonym>
    <synonym>Hexanoic acid, sodium salt</synonym>
    <synonym>Bismuth(III)hexanoate</synonym>
    <synonym>Hexanoic acid, copper (2+) salt</synonym>
    <synonym>Hexanoic acid, manganese (2+) salt</synonym>
    <synonym>Bi(ohex)3</synonym>
    <synonym>Hexanoic acid, barium salt</synonym>
    <synonym>Hexanoic acid, potassium salt</synonym>
    <synonym>Hexanoic acid, rhodium (2+) salt</synonym>
    <synonym>FA(6:0)</synonym>
    <synonym>Calcium N-hexanoate</synonym>
    <synonym>Hexanoic acid, sodium salt (1:1)</synonym>
    <synonym>Sodium capronate</synonym>
    <synonym>Calcium hexanoate</synonym>
    <synonym>Caproic acid sodium salt</synonym>
    <synonym>Sodium caproate</synonym>
    <synonym>Sodium hexanoate</synonym>
  </synonyms>
  <chemical_formula>C6H12O2</chemical_formula>
  <average_molecular_weight>116.1583</average_molecular_weight>
  <monisotopic_moleculate_weight>116.083729628</monisotopic_moleculate_weight>
  <iupac_name>hexanoic acid</iupac_name>
  <traditional_iupac>hexanoic acid</traditional_iupac>
  <cas_registry_number>142-62-1</cas_registry_number>
  <smiles>CCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)</inchi>
  <inchikey>FUZZWVXGSFPDMH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Saturated fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>medium-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>10.3 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.92</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>hexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>116.1583</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>116.083729628</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FUZZWVXGSFPDMH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087265</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438697</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12.8 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14.3 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.5 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11.8 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20.39 +/- 1.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk from a Danish Holstein herd by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19.11 +/- 2.55</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised whole milk (3.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.65 +/- 1.91</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised semi skimmed milk (1.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.92 +/- 1.27</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised skimmed milk (0.1% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
          <pubmed_id>14168161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3615.76</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3443.58</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>602.626</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1893.967</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>602.626</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17.48 +/- 0.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6542.795</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7489.78</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6887.15</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
          <pubmed_id>1779072</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25.31 +/- 0.43</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Catrienus De Jong Herman T. Badings. Determination of free fatty acids in milk and cheese procedures for extraction, clean up, and capillary gas chromatographic analysis. Journal of High Resolution Chromatography Volume 13, Issue 2, 1990</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11191.653 +/- 5165.378</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
          <pubmed_id>16899705</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7661.978 +/- 1463.524</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7403.709 +/- 1291.345</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.7 (0.3 - 14)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.8 (0.3 - 15)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0 (0.4 - 18)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.0 (2.2 - 8.9)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB013897</foodb_id>
  <chemspider_id>8552</chemspider_id>
  <pdbe_id/>
  <chebi_id>30776</chebi_id>
  <pubchem_compound_id>8892</pubchem_compound_id>
  <kegg_id>C01585</kegg_id>
  <knapsack_id>C00001218</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Hexanoic_acid</wikipedia_id>
  <metlin_id>5520</metlin_id>
  <meta_cyc_id>HEXANOATE</meta_cyc_id>
  <synthesis_reference>Gao, Fei; Wu, Zongwei.  Process for preparation of hexanoic acid by oxidation of 2-octanol with nitric acid.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2005), 7pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
      <pubmed_id>16899705</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
      <pubmed_id>1779072</pubmed_id>
    </reference>
    <reference>
      <reference_text>Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.</reference_text>
      <pubmed_id>20855010</pubmed_id>
    </reference>
    <reference>
      <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
      <pubmed_id>14168161</pubmed_id>
    </reference>
    <reference>
      <reference_text>Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26.</reference_text>
      <pubmed_id>27236769</pubmed_id>
    </reference>
    <reference>
      <reference_text>van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.</reference_text>
      <pubmed_id>28219465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
    <reference>
      <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:22 UTC</creation_date>
  <update_date>2020-03-13 16:21:56 UTC</update_date>
  <accession>BMDB0000536</accession>
  <secondary_accessions>
    <accession>BMDB00536</accession>
  </secondary_accessions>
  <name>Adenylsuccinic acid</name>
  <description/>
  <synonyms>
    <synonym>Adenylosuccinate</synonym>
    <synonym>Adenylosuccinic acid</synonym>
    <synonym>Aspartyl adenylate</synonym>
    <synonym>N6-(1,2-Dicarboxyethyl)-AMP</synonym>
    <synonym>Aspartyl adenylic acid</synonym>
    <synonym>Adenylsuccinate</synonym>
    <synonym>6-Succino-5'-adenylate</synonym>
    <synonym>6-Succino-5'-adenylic acid</synonym>
    <synonym>Adenyl-succinic acid</synonym>
    <synonym>D-Ribofuranosyl)-9H-purin-6-yl]</synonym>
    <synonym>D-Ribofuranosyl-9H-purin-6-yl) mono(dihydrogen phosphate) (ester)</synonym>
    <synonym>N(6)-(1,2-Dicarboxyethyl)-AMP</synonym>
    <synonym>Succinyl AMP</synonym>
    <synonym>Succinyladenosine 5'-monophosphate</synonym>
    <synonym>Succinyladenosine monophosphorate</synonym>
    <synonym>Succinyladenosine monophosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C14H18N5O11P</chemical_formula>
  <average_molecular_weight>463.2934</average_molecular_weight>
  <monisotopic_moleculate_weight>463.074042955</monisotopic_moleculate_weight>
  <iupac_name>2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-9H-purin-6-yl}amino)butanedioic acid</iupac_name>
  <traditional_iupac>adenylosuccinate</traditional_iupac>
  <cas_registry_number>19046-78-7</cas_registry_number>
  <smiles>O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN=C2NC(CC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C14H18N5O11P/c20-7(21)1-5(14(24)25)18-11-8-12(16-3-15-11)19(4-17-8)13-10(23)9(22)6(30-13)2-29-31(26,27)28/h3-6,9-10,13,22-23H,1-2H2,(H,20,21)(H,24,25)(H,15,16,18)(H2,26,27,28)/t5?,6-,9-,10-,13-/m1/s1</inchi>
  <inchikey>OFBHPPMPBOJXRT-DPXQIYNJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-alkylaminopurines</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aspartic acid and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>6-alkylaminopurine</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Aspartic acid or derivatives</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>purine ribonucleoside 5'-monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-9H-purin-6-yl}amino)butanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>463.2934</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>463.074042955</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN=C2NC(CC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H18N5O11P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H18N5O11P/c20-7(21)1-5(14(24)25)18-11-8-12(16-3-15-11)19(4-17-8)13-10(23)9(22)6(30-13)2-29-31(26,27)28/h3-6,9-10,13,22-23H,1-2H2,(H,20,21)(H,24,25)(H,15,16,18)(H2,26,27,28)/t5?,6-,9-,10-,13-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OFBHPPMPBOJXRT-DPXQIYNJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>246.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>96.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182546</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022101</foodb_id>
  <chemspider_id>389122</chemspider_id>
  <pdbe_id/>
  <chebi_id>15919</chebi_id>
  <pubchem_compound_id>440122</pubchem_compound_id>
  <kegg_id>C03794</kegg_id>
  <knapsack_id>C00007229</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Adenylosuccinate</wikipedia_id>
  <metlin_id>5521</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Buck, Ildiko; Reese, Colin B.  An unambiguous synthesis of adenylosuccinic acid and its constituent nucleoside.    Journal of the Chemical Society, Perkin Transactions 1:  Organic and Bio-Organic Chemistry (1972-1999)  (1990),   (11),  2937-42.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00495</protein_accession>
      <name>Adenylosuccinate synthetase isozyme 1</name>
      <uniprot_id>A5PJR4</uniprot_id>
      <gene_name>ADSSL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00525</protein_accession>
      <name>Adenylosuccinate synthetase isozyme 2</name>
      <uniprot_id>A7MBG0</uniprot_id>
      <gene_name>ADSS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:23 UTC</creation_date>
  <update_date>2020-04-16 20:39:57 UTC</update_date>
  <accession>BMDB0000538</accession>
  <secondary_accessions>
    <accession>BMDB00538</accession>
  </secondary_accessions>
  <name>Adenosine triphosphate</name>
  <description>Adenosine triphosphate, also known as ATP or atriphos, belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety. Adenosine triphosphate is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Adenosine triphosphate is possibly soluble (in water) and a strong basic compound (based on its pKa). Adenosine triphosphate exists in all living species, ranging from bacteria to humans. Adenosine triphosphate is a potentially toxic compound.</description>
  <synonyms>
    <synonym>Adenosine 5'-triphosphate</synonym>
    <synonym>ADENOSINE-5'-triphosphATE</synonym>
    <synonym>Adephos</synonym>
    <synonym>Adetol</synonym>
    <synonym>Adynol</synonym>
    <synonym>Atipi</synonym>
    <synonym>Atriphos</synonym>
    <synonym>Cardenosine</synonym>
    <synonym>Fosfobion</synonym>
    <synonym>Glucobasin</synonym>
    <synonym>H4ATP</synonym>
    <synonym>Myotriphos</synonym>
    <synonym>Triadenyl</synonym>
    <synonym>Triphosphaden</synonym>
    <synonym>ATP</synonym>
    <synonym>Adenosine 5'-triphosphoric acid</synonym>
    <synonym>ADENOSINE-5'-triphosphoric acid</synonym>
    <synonym>Adenosine triphosphoric acid</synonym>
    <synonym>5'-(Tetrahydrogen triphosphate) adenosine</synonym>
    <synonym>5'-ATP</synonym>
    <synonym>Adenosine 5'-triphosphorate</synonym>
    <synonym>Adenylpyrophosphorate</synonym>
    <synonym>Adenylpyrophosphoric acid</synonym>
    <synonym>Phosphobion</synonym>
    <synonym>Striadyne</synonym>
    <synonym>Triphosphoric acid adenosine ester</synonym>
    <synonym>Adenosine triphosphate, chromium salt</synonym>
    <synonym>CrATP</synonym>
    <synonym>Manganese adenosine triphosphate</synonym>
    <synonym>MgATP</synonym>
    <synonym>MnATP</synonym>
    <synonym>ATP MGCL2</synonym>
    <synonym>ATP-MGCL2</synonym>
    <synonym>Adenosine triphosphate, magnesium salt</synonym>
    <synonym>Adenosine triphosphate, manganese salt</synonym>
    <synonym>Magnesium adenosine triphosphate</synonym>
    <synonym>Adenosine triphosphate, calcium salt</synonym>
    <synonym>Adenylpyrophosphate</synonym>
    <synonym>CaATP</synonym>
    <synonym>CR(H2O)4 ATP</synonym>
    <synonym>Adenosine triphosphate, chromium ammonium salt</synonym>
    <synonym>Adenosine triphosphate, magnesium chloride</synonym>
    <synonym>Chromium adenosine triphosphate</synonym>
  </synonyms>
  <chemical_formula>C10H16N5O13P3</chemical_formula>
  <average_molecular_weight>507.181</average_molecular_weight>
  <monisotopic_moleculate_weight>506.995745159</monisotopic_moleculate_weight>
  <iupac_name>({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</iupac_name>
  <traditional_iupac>adenosine triphosphate</traditional_iupac>
  <cas_registry_number>56-65-5</cas_registry_number>
  <smiles>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>ZKHQWZAMYRWXGA-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group  linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside triphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside triphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Coenzymes</external_descriptor>
      <external_descriptor>Ribonucleotides</external_descriptor>
      <external_descriptor>adenosine 5'-phosphate</external_descriptor>
      <external_descriptor>purine ribonucleoside 5'-triphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL; 862 mg/mL (magnesium salt)</value>
      <source>MERCK INDEX (1996); Human Metabolome Project (salt)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>507.181</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>506.995745159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H16N5O13P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZKHQWZAMYRWXGA-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>279.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>95.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Activation of cAMP-dependent protein kinase, PKA</name>
      <smpdb_id>SMP0108201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Beta Oxidation of Very Long Chain Fatty Acids</name>
      <smpdb_id>SMP0087259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Biotin Metabolism</name>
      <smpdb_id>SMP0087183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Butyrate Metabolism</name>
      <smpdb_id>SMP0087185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Corticotropin Activation of Cortisol Production</name>
      <smpdb_id>SMP0108167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dopamine Activation of Neurological Reward System</name>
      <smpdb_id>SMP0107994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ethanol Degradation</name>
      <smpdb_id>SMP0087192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 4 and Serotonin</name>
      <smpdb_id>SMP0108169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 6 and Serotonin</name>
      <smpdb_id>SMP0108172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 7 and Serotonin</name>
      <smpdb_id>SMP0108170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gastric Acid Production</name>
      <smpdb_id>SMP0119381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutathione Metabolism</name>
      <smpdb_id>SMP0087167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2a and Adenosine</name>
      <smpdb_id>SMP0108174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2b and Adenosine</name>
      <smpdb_id>SMP0108178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through FSH Receptor and Follicle Stimulating Hormone</name>
      <smpdb_id>SMP0108183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Histamine H2 Receptor and Histamine</name>
      <smpdb_id>SMP0107995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through LHCGR Receptor and Luteinizing Hormone/Choriogonadotropin</name>
      <smpdb_id>SMP0108184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through PGD2 receptor and Prostaglandin D2</name>
      <smpdb_id>SMP0107997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Prostacyclin Receptor and Prostacyclin</name>
      <smpdb_id>SMP0107998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ion Channels and Their Functional Role in Vascular Endothelium</name>
      <smpdb_id>SMP0108207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Degradation</name>
      <smpdb_id>SMP0087253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA1 Signalling</name>
      <smpdb_id>SMP0108191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA2 Signalling</name>
      <smpdb_id>SMP0108193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA3 Signalling</name>
      <smpdb_id>SMP0108194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA4 Signalling</name>
      <smpdb_id>SMP0108196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA5 Signalling</name>
      <smpdb_id>SMP0108198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA6 Signalling</name>
      <smpdb_id>SMP0108199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Electron Transport Chain</name>
      <smpdb_id>SMP0087261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Muscle/Heart Contraction</name>
      <smpdb_id>SMP0119378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pancreas Function</name>
      <smpdb_id>SMP0119380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pantothenate and CoA Biosynthesis</name>
      <smpdb_id>SMP0087207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylacetate Metabolism</name>
      <smpdb_id>SMP0087208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis</name>
      <smpdb_id>SMP0072037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:0)</name>
      <smpdb_id>SMP0080430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0080431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/15:0)</name>
      <smpdb_id>SMP0080432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:0)</name>
      <smpdb_id>SMP0080433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0080434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:0)</name>
      <smpdb_id>SMP0080435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0080436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0080437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:0)</name>
      <smpdb_id>SMP0080442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0080443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:0)</name>
      <smpdb_id>SMP0080450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0080451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:0)</name>
      <smpdb_id>SMP0080457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0080458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0080459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0080460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0080461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/15:0)</name>
      <smpdb_id>SMP0080487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:0)</name>
      <smpdb_id>SMP0080488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0080489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:0)</name>
      <smpdb_id>SMP0080490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0080491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0080492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:0)</name>
      <smpdb_id>SMP0080497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0080498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:0)</name>
      <smpdb_id>SMP0080505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0080506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:0)</name>
      <smpdb_id>SMP0080512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0080513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:0)</name>
      <smpdb_id>SMP0080514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0080515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:0)</name>
      <smpdb_id>SMP0080516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0080517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0080518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:0)</name>
      <smpdb_id>SMP0080523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0080524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:0)</name>
      <smpdb_id>SMP0080531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0080532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:0)</name>
      <smpdb_id>SMP0080538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0080539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:0)</name>
      <smpdb_id>SMP0080565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0080566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0080567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:0)</name>
      <smpdb_id>SMP0080572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0080573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:0)</name>
      <smpdb_id>SMP0080580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0080581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:0)</name>
      <smpdb_id>SMP0080587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0080588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0080595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:0)</name>
      <smpdb_id>SMP0080712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0080713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:0)</name>
      <smpdb_id>SMP0080720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0080721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:0)</name>
      <smpdb_id>SMP0080727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0080728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0080765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0080772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:0)</name>
      <smpdb_id>SMP0080820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0080821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:0)</name>
      <smpdb_id>SMP0080827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0080828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0080835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:0)</name>
      <smpdb_id>SMP0080864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0080865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis</name>
      <smpdb_id>SMP0072048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:0)</name>
      <smpdb_id>SMP0082233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0082234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/15:0)</name>
      <smpdb_id>SMP0082235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:0)</name>
      <smpdb_id>SMP0082236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0082237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:0)</name>
      <smpdb_id>SMP0082238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0082239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0082240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:0)</name>
      <smpdb_id>SMP0082245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0082246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:0)</name>
      <smpdb_id>SMP0082253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0082254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:0)</name>
      <smpdb_id>SMP0082260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0082261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0082262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0082263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0082264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/15:0)</name>
      <smpdb_id>SMP0082290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:0)</name>
      <smpdb_id>SMP0082291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0082292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:0)</name>
      <smpdb_id>SMP0082293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0082294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0082295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:0)</name>
      <smpdb_id>SMP0082300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0082301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:0)</name>
      <smpdb_id>SMP0082308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0082309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:0)</name>
      <smpdb_id>SMP0082315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0082316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:0)</name>
      <smpdb_id>SMP0082317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0082318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:0)</name>
      <smpdb_id>SMP0082319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0082320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0082321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:0)</name>
      <smpdb_id>SMP0082326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0082327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:0)</name>
      <smpdb_id>SMP0082334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0082335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:0)</name>
      <smpdb_id>SMP0082341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0082342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:0)</name>
      <smpdb_id>SMP0082368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0082369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0082370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:0)</name>
      <smpdb_id>SMP0082375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0082376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:0)</name>
      <smpdb_id>SMP0082383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0082384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:0)</name>
      <smpdb_id>SMP0082390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0082391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0082398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:0)</name>
      <smpdb_id>SMP0082520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0082521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:0)</name>
      <smpdb_id>SMP0082528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0082529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:0)</name>
      <smpdb_id>SMP0082535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0082536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0082574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0082581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:0)</name>
      <smpdb_id>SMP0082629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0082630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:0)</name>
      <smpdb_id>SMP0082636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0082637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0082644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:0)</name>
      <smpdb_id>SMP0082671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0082672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylinositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Alanine</name>
      <smpdb_id>SMP0119369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Arginine</name>
      <smpdb_id>SMP0119383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Asparagine</name>
      <smpdb_id>SMP0119385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Aspartic Acid</name>
      <smpdb_id>SMP0119386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Cysteine</name>
      <smpdb_id>SMP0119388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Glutamic Acid</name>
      <smpdb_id>SMP0119390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Glutamine</name>
      <smpdb_id>SMP0119389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Glycine</name>
      <smpdb_id>SMP0119391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Histidine</name>
      <smpdb_id>SMP0119392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Isoleucine</name>
      <smpdb_id>SMP0119393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Leucine</name>
      <smpdb_id>SMP0119403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Lysine</name>
      <smpdb_id>SMP0119404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Methionine</name>
      <smpdb_id>SMP0119405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Phenylalanine</name>
      <smpdb_id>SMP0119406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Proline</name>
      <smpdb_id>SMP0119407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Serine</name>
      <smpdb_id>SMP0119409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Threonine</name>
      <smpdb_id>SMP0119410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Tryptophan</name>
      <smpdb_id>SMP0119414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Tyrosine</name>
      <smpdb_id>SMP0119416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Valine</name>
      <smpdb_id>SMP0119417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Riboflavin Metabolism</name>
      <smpdb_id>SMP0087211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Selenoamino Acid Metabolism</name>
      <smpdb_id>SMP0087161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sulfate/Sulfite Metabolism</name>
      <smpdb_id>SMP0087216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Thiamine Metabolism</name>
      <smpdb_id>SMP0087212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Threonine and 2-Oxobutanoate Degradation</name>
      <smpdb_id>SMP0087262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Trehalose Degradation</name>
      <smpdb_id>SMP0087263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ubiquitin–Proteasome Pathway</name>
      <smpdb_id>SMP0120929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vasopressin Regulation of Water Homeostasis</name>
      <smpdb_id>SMP0108181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438914</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.210 - 0.240</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Aged skim milk</comment>
      <references>
        <reference>
          <reference_text>Richardson T, McGann TC, Kearney RD: Levels and location of adenosine 5'-triphosphate in bovine milk. J Dairy Res. 1980 Feb;47(1):91-6.</reference_text>
          <pubmed_id>7372888</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.210 - 0.240</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw fresh skim milk</comment>
      <references>
        <reference>
          <reference_text>Richardson T, McGann TC, Kearney RD: Levels and location of adenosine 5'-triphosphate in bovine milk. J Dairy Res. 1980 Feb;47(1):91-6.</reference_text>
          <pubmed_id>7372888</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.220 - 0.280</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw fresh whole milk</comment>
      <references>
        <reference>
          <reference_text>Richardson T, McGann TC, Kearney RD: Levels and location of adenosine 5'-triphosphate in bovine milk. J Dairy Res. 1980 Feb;47(1):91-6.</reference_text>
          <pubmed_id>7372888</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1.12+/-0.02</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.73+/-0.04</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>2.31+/-0.03</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1.83+/-0.02</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB00171</drugbank_id>
  <foodb_id>FDB030683</foodb_id>
  <chemspider_id>5742</chemspider_id>
  <pdbe_id/>
  <chebi_id>15422</chebi_id>
  <pubchem_compound_id>5957</pubchem_compound_id>
  <kegg_id>C00002</kegg_id>
  <knapsack_id>C00001491</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33477</bigg_id>
  <wikipedia_id>Adenosine_triphosphate</wikipedia_id>
  <metlin_id>5523</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Clark, V. M.; Kirby, G. W.; Todd, Alexander. Phosphorylation. XV. Use of phosphoramidic esters in acylation-new preparation of adenosine 5'-pyrophosphate and adenosine 5'-triphosphate. Journal of the Chemical Society (1957), 1497-1501.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Richardson T, McGann TC, Kearney RD: Levels and location of adenosine 5'-triphosphate in bovine milk. J Dairy Res. 1980 Feb;47(1):91-6.</reference_text>
      <pubmed_id>7372888</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:24 UTC</creation_date>
  <update_date>2020-04-14 22:47:47 UTC</update_date>
  <accession>BMDB0000539</accession>
  <secondary_accessions>
    <accession>BMDB00539</accession>
  </secondary_accessions>
  <name>Arabinonic acid</name>
  <description/>
  <synonyms>
    <synonym>D-Arabonic acid</synonym>
    <synonym>D-Arabinonic acid</synonym>
    <synonym>D-Arabonate</synonym>
    <synonym>D-Arabinonate</synonym>
    <synonym>Arabinonate</synonym>
    <synonym>Arabate</synonym>
    <synonym>Arabic acid, sodium salt</synonym>
    <synonym>Sodium arabate</synonym>
    <synonym>Arabic acid</synonym>
    <synonym>2,3,4,5-Tetrahydroxypentanoic acid</synonym>
    <synonym>Arabonate</synonym>
    <synonym>Arabonic acid</synonym>
  </synonyms>
  <chemical_formula>C5H10O6</chemical_formula>
  <average_molecular_weight>166.1293</average_molecular_weight>
  <monisotopic_moleculate_weight>166.047738052</monisotopic_moleculate_weight>
  <iupac_name>(2S,3R,4R)-2,3,4,5-tetrahydroxypentanoic acid</iupac_name>
  <traditional_iupac>arabinonate</traditional_iupac>
  <cas_registry_number>488-30-2</cas_registry_number>
  <smiles>OC[C@@H](O)[C@@H](O)[C@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H10O6/c6-1-2(7)3(8)4(9)5(10)11/h2-4,6-9H,1H2,(H,10,11)/t2-,3-,4+/m1/s1</inchi>
  <inchikey>QXKAIJAYHKCRRA-JJYYJPOSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
      <substituent>Sugar acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>arabinonic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3R,4R)-2,3,4,5-tetrahydroxypentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>166.1293</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>166.047738052</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)[C@@H](O)[C@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O6/c6-1-2(7)3(8)4(9)5(10)11/h2-4,6-9H,1H2,(H,10,11)/t2-,3-,4+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QXKAIJAYHKCRRA-JJYYJPOSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359400</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022102</foodb_id>
  <chemspider_id>108861</chemspider_id>
  <kegg_id>C00878</kegg_id>
  <drugbank_id/>
  <chebi_id>20912</chebi_id>
  <pubchem_compound_id>122045</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Dolnik, V.; Bocek, P.; Sistkova, L.; Korbl, J.  Analytical control of arabonic acid production by isotachophoresis.  Journal of Chromatography  (1982),  246(2),  343-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:25 UTC</creation_date>
  <update_date>2020-03-13 16:21:58 UTC</update_date>
  <accession>BMDB0000540</accession>
  <secondary_accessions>
    <accession>BMDB00540</accession>
  </secondary_accessions>
  <name>5-Androstene-3b,16a,17a-triol</name>
  <description/>
  <synonyms>
    <synonym>Androst-5-ene-3b,16a,17a-triol</synonym>
  </synonyms>
  <chemical_formula>C19H30O3</chemical_formula>
  <average_molecular_weight>306.4397</average_molecular_weight>
  <monisotopic_moleculate_weight>306.219494826</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,10R,11S,13R,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,13,14-triol</iupac_name>
  <traditional_iupac>5-androstene-3b,16a,17a-triol</traditional_iupac>
  <cas_registry_number>23409-40-7</cas_registry_number>
  <smiles>[H][C@@]12C[C@@H](O)[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-17,20-22H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,17+,18-,19-/m0/s1</inchi>
  <inchikey>GUGSXATYPSGVAY-LFJLJVMTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>16-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>16-alpha-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,10R,11S,13R,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,13,14-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>306.4397</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>306.219494826</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@@H](O)[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H30O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-17,20-22H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,17+,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GUGSXATYPSGVAY-LFJLJVMTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365139</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022103</foodb_id>
  <chemspider_id>13628104</chemspider_id>
  <kegg_id/>
  <drugbank_id/>
  <chebi_id/>
  <pubchem_compound_id>21252252</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5525</metlin_id>
  <synthesis_reference>Huffman, Max N.; Lott, Mary Harriett.  Steric structure of estriol and related steroids.    Journal of the American Chemical Society  (1947),  69  1835.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:27 UTC</creation_date>
  <update_date>2020-04-15 22:14:03 UTC</update_date>
  <accession>BMDB0000541</accession>
  <secondary_accessions>
    <accession>BMDB00541</accession>
  </secondary_accessions>
  <name>7b-Hydroxy-3-oxo-5b-cholanoic acid</name>
  <description/>
  <synonyms>
    <synonym>7b-Hydroxy-3-oxo-5b-cholanoate</synonym>
    <synonym>(5b,7b)-7-Hydroxy-3-oxo-cholan-24-Oate</synonym>
    <synonym>(5b,7b)-7-Hydroxy-3-oxo-cholan-24-Oic acid</synonym>
    <synonym>7b-Hydroxy-3-oxo-5b-cholan-24-Oate</synonym>
    <synonym>7b-Hydroxy-3-oxo-5b-cholan-24-Oic acid</synonym>
    <synonym>Methyl (4R)-4-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyl-5,9-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</synonym>
    <synonym>Methyl 3,7-dioxocholan-24-Oic acid</synonym>
  </synonyms>
  <chemical_formula>C25H38O4</chemical_formula>
  <average_molecular_weight>402.5668</average_molecular_weight>
  <monisotopic_moleculate_weight>402.277009704</monisotopic_moleculate_weight>
  <iupac_name>methyl (4R)-4-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyl-5,9-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</iupac_name>
  <traditional_iupac>7b-hydroxy-3-oxo-5b-cholanoate</traditional_iupac>
  <cas_registry_number>77060-26-5</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(=O)OC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)CC2CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C25H38O4/c1-15(5-8-22(28)29-4)18-6-7-19-23-20(10-12-25(18,19)3)24(2)11-9-17(26)13-16(24)14-21(23)27/h15-16,18-20,23H,5-14H2,1-4H3/t15-,16?,18-,19+,20+,23+,24+,25-/m1/s1</inchi>
  <inchikey>UZRRNRRCPZZPNY-ZECRIGHZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-oxosteroids</alternative_parent>
      <alternative_parent>7-oxosteroids</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Fatty acid methyl esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl esters</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-oxosteroid</substituent>
      <substituent>7-oxosteroid</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Bile acid, alcohol, or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acid methyl ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Methyl ester</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>171 - 173 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>methyl (4R)-4-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyl-5,9-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>402.5668</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>402.277009704</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(=O)OC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)CC2CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H38O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C25H38O4/c1-15(5-8-22(28)29-4)18-6-7-19-23-20(10-12-25(18,19)3)24(2)11-9-17(26)13-16(24)14-21(23)27/h15-16,18-20,23H,5-14H2,1-4H3/t15-,16?,18-,19+,20+,23+,24+,25-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UZRRNRRCPZZPNY-ZECRIGHZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>112.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327165</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022104</foodb_id>
  <drugbank_id/>
  <kegg_id/>
  <pubchem_compound_id>22833531</pubchem_compound_id>
  <chemspider_id>17215969</chemspider_id>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5526</metlin_id>
  <synthesis_reference>Bortolini, Olga; Fantin, Giancarlo; Fogagnolo, Marco; Forlani, Roberto; Maietti, Silvia; Pedrini, Paola.  Improved Enantioselectivity in the Epoxidation of Cinnamic Acid Derivatives with Dioxiranes from Keto Bile Acids.    Journal of Organic Chemistry  (2002),  67(16),  5802-5806.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:28 UTC</creation_date>
  <update_date>2020-03-13 16:21:59 UTC</update_date>
  <accession>BMDB0000542</accession>
  <secondary_accessions>
    <accession>BMDB00542</accession>
  </secondary_accessions>
  <name>8-Hydroxyadenine</name>
  <description/>
  <synonyms>
    <synonym>7,8-Dihydro-8-oxoadenine</synonym>
    <synonym>8-oxo-7,8-Dihydroadenine</synonym>
    <synonym>8-OxoA</synonym>
    <synonym>Oxyadenine</synonym>
    <synonym>6-Amino-1,7-dihydro-8H-purin-8-one</synonym>
    <synonym>6-Amino-8-hydroxypurine</synonym>
    <synonym>6-Amino-purin-8(9H)-one</synonym>
    <synonym>6-Amino-purin-8-ol</synonym>
    <synonym>8-Hydroxy-1H-purin-6-amine</synonym>
    <synonym>8-Oxoadenine</synonym>
    <synonym>Oksaden</synonym>
    <synonym>Oxaden</synonym>
    <synonym>7,8-DHOA</synonym>
  </synonyms>
  <chemical_formula>C5H5N5O</chemical_formula>
  <average_molecular_weight>151.1261</average_molecular_weight>
  <monisotopic_moleculate_weight>151.049409807</monisotopic_moleculate_weight>
  <iupac_name>6-amino-7H-purin-8-ol</iupac_name>
  <traditional_iupac>6-amino-8-hydroxypurine</traditional_iupac>
  <cas_registry_number>21149-26-8</cas_registry_number>
  <smiles>NC1=NC=NC2=C1NC(O)=N2</smiles>
  <inchi>InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-3)10-5(11)9-2/h1H,(H4,6,7,8,9,10,11)</inchi>
  <inchikey>RGKBRPAAQSHTED-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purinones. These are purines in which the purine moiety bears a C=O group. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Purinones</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Urea</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6-amino-7H-purin-8-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>151.1261</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>151.049409807</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC=NC2=C1NC(O)=N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H5N5O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-3)10-5(11)9-2/h1H,(H4,6,7,8,9,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RGKBRPAAQSHTED-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>100.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347187</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022105</foodb_id>
  <drugbank_id/>
  <kegg_id/>
  <pubchem_compound_id>95215</pubchem_compound_id>
  <chemspider_id>4511108</chemspider_id>
  <pdbe_id/>
  <chebi_id>134104</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00043227</knapsack_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5527</metlin_id>
  <synthesis_reference>Makarieva, Tatyana N.; Guzii, Alla G.; Dmitrenok, Andrei S.; Dmitrenok, Pavel S.; Krasokhin, Vladimir B.; Stonik, Valentin A.  8-Oxoadenine, 9-methyl-8-oxoadenine, and trihydroxylated sterols from a Far Eastern thorectidae sponge.    Natural Product Communications  (2006),  1(9),  711-714.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:29 UTC</creation_date>
  <update_date>2020-04-15 22:24:22 UTC</update_date>
  <accession>BMDB0000543</accession>
  <secondary_accessions>
    <accession>BMDB00543</accession>
  </secondary_accessions>
  <name>Benzenebutanoic acid</name>
  <description/>
  <synonyms>
    <synonym>4-PHENYL-butanoIC ACID</synonym>
    <synonym>4-Phenyl-N-butyric acid</synonym>
    <synonym>Benzenebutyric acid</synonym>
    <synonym>gamma-Phenyl-N-butyric acid</synonym>
    <synonym>gamma-Phenylbutyric acid</synonym>
    <synonym>Omega-phenylbutanoic acid</synonym>
    <synonym>Omega-phenylbutyric acid</synonym>
    <synonym>PBA</synonym>
    <synonym>4-PHENYL-butanoate</synonym>
    <synonym>4-Phenyl-N-butyrate</synonym>
    <synonym>Benzenebutyrate</synonym>
    <synonym>g-Phenyl-N-butyrate</synonym>
    <synonym>g-Phenyl-N-butyric acid</synonym>
    <synonym>gamma-Phenyl-N-butyrate</synonym>
    <synonym>Γ-phenyl-N-butyrate</synonym>
    <synonym>Γ-phenyl-N-butyric acid</synonym>
    <synonym>g-Phenylbutyrate</synonym>
    <synonym>g-Phenylbutyric acid</synonym>
    <synonym>gamma-Phenylbutyrate</synonym>
    <synonym>Γ-phenylbutyrate</synonym>
    <synonym>Γ-phenylbutyric acid</synonym>
    <synonym>Omega-phenylbutanoate</synonym>
    <synonym>Omega-phenylbutyrate</synonym>
    <synonym>Benzenebutanoate</synonym>
    <synonym>4-Phenyl-butyrate</synonym>
    <synonym>4-Phenyl-butyric acid</synonym>
    <synonym>4-Phenylbutanoate</synonym>
    <synonym>4-Phenylbutanoic acid</synonym>
    <synonym>4-Phenylbutyrate</synonym>
    <synonym>4-Phenylbutyric acid</synonym>
    <synonym>g-Phenyl-butyrate</synonym>
    <synonym>g-Phenyl-butyric acid</synonym>
    <synonym>g-Phenylbutanoate</synonym>
    <synonym>g-Phenylbutanoic acid</synonym>
    <synonym>gamma-Phenyl-butyrate</synonym>
    <synonym>gamma-Phenyl-butyric acid</synonym>
    <synonym>gamma-Phenylbutanoate</synonym>
    <synonym>gamma-Phenylbutanoic acid</synonym>
    <synonym>W-Phenylbutanoate</synonym>
    <synonym>W-Phenylbutanoic acid</synonym>
    <synonym>4-Phenylbutyric acid, calcium salt</synonym>
    <synonym>Buphenyl</synonym>
    <synonym>Sodium 4-phenylbutyrate</synonym>
    <synonym>Ammonaps</synonym>
    <synonym>Sodium 4-phenylbutanoate</synonym>
    <synonym>4-Phenylbutyric acid, sodium salt</synonym>
    <synonym>Sodium phenylbutyrate</synonym>
    <synonym>Phenylbutyrate</synonym>
  </synonyms>
  <chemical_formula>C10H12O2</chemical_formula>
  <average_molecular_weight>164.2011</average_molecular_weight>
  <monisotopic_moleculate_weight>164.083729628</monisotopic_moleculate_weight>
  <iupac_name>4-phenylbutanoic acid</iupac_name>
  <traditional_iupac>4-phenylbutyric acid</traditional_iupac>
  <cas_registry_number>1821-12-1</cas_registry_number>
  <smiles>OC(=O)CCCC1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C10H12O2/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,11,12)</inchi>
  <inchikey>OBKXEAXTFZPCHS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class/>
    <direct_parent>Benzene and substituted derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>47 - 49 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>18 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.42</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-phenylbutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>164.2011</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>164.083729628</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCC1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12O2/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OBKXEAXTFZPCHS-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>264018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>264019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>264020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>283947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>283948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>283949</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022106</foodb_id>
  <chemspider_id>4611</chemspider_id>
  <drugbank_id>DB06819</drugbank_id>
  <pubchem_compound_id>4775</pubchem_compound_id>
  <chebi_id>41500</chebi_id>
  <pdbe_id/>
  <kegg_id/>
  <meta_cyc_id>CPD-14367</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5528</metlin_id>
  <synthesis_reference>Galat, Alexander.  The reaction of phenylpyruvic acid and related compounds with ammonia.    Journal of the American Chemical Society  (1950),  72  4436-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:30 UTC</creation_date>
  <update_date>2020-03-13 16:22:00 UTC</update_date>
  <accession>BMDB0000544</accession>
  <secondary_accessions>
    <accession>BMDB00544</accession>
  </secondary_accessions>
  <name>5-Hydroxymethyl-4-methyluracil</name>
  <description/>
  <synonyms>
    <synonym>4-Methyl-5-hydroxymethyluracil</synonym>
    <synonym>5-Hydroxymethyl-6-methyluracil</synonym>
    <synonym>Pentoxil</synonym>
    <synonym>Pentoxyl</synonym>
  </synonyms>
  <chemical_formula>C6H8N2O3</chemical_formula>
  <average_molecular_weight>156.1393</average_molecular_weight>
  <monisotopic_moleculate_weight>156.053492132</monisotopic_moleculate_weight>
  <iupac_name>5-(hydroxymethyl)-6-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione</iupac_name>
  <traditional_iupac>5-hydroxymethyl-6-methyluracil</traditional_iupac>
  <cas_registry_number>147-61-5</cas_registry_number>
  <smiles>CC1=C(CO)C(=O)NC(=O)N1</smiles>
  <inchi>InChI=1S/C6H8N2O3/c1-3-4(2-9)5(10)8-6(11)7-3/h9H,2H2,1H3,(H2,7,8,10,11)</inchi>
  <inchikey>XBAVGYMDOXCWQU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazines</class>
    <sub_class>Pyrimidines and pyrimidine derivatives</sub_class>
    <direct_parent>Pyrimidones</direct_parent>
    <alternative_parents>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-(hydroxymethyl)-6-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>156.1393</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>156.053492132</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CO)C(=O)NC(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H8N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H8N2O3/c1-3-4(2-9)5(10)8-6(11)7-3/h9H,2H2,1H3,(H2,7,8,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XBAVGYMDOXCWQU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>78.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343332</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022107</foodb_id>
  <chemspider_id>8635</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>8983</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5529</metlin_id>
  <synthesis_reference>Cannon-Carlson S V; Gokhale H; Teebor G W  Purification and characterization of 5-hydroxymethyluracil-DNA glycosylase from calf thymus. Its possible role in the maintenance of methylated cytosine residues.    The Journal of biological chemistry  (1989),  264(22),  13306-12.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:31 UTC</creation_date>
  <update_date>2020-04-15 22:14:04 UTC</update_date>
  <accession>BMDB0000545</accession>
  <secondary_accessions>
    <accession>BMDB00545</accession>
  </secondary_accessions>
  <name>Chenodeoxycholic acid disulfate</name>
  <description/>
  <synonyms>
    <synonym>Chenodeoxycholate disulfate</synonym>
    <synonym>Chenodeoxycholate disulphate</synonym>
    <synonym>Chenodeoxycholic acid disulfuric acid</synonym>
    <synonym>Chenodeoxycholic acid disulphuric acid</synonym>
    <synonym>Chenodeoxycholic acid disulphate</synonym>
  </synonyms>
  <chemical_formula>C24H40O10S2</chemical_formula>
  <average_molecular_weight>552.698</average_molecular_weight>
  <monisotopic_moleculate_weight>552.20628888</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-2,15-dimethyl-5,9-bis(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-2,15-dimethyl-5,9-bis(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>60262-91-1</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](C[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)OS(O)(=O)=O)[C@H](C)CCC(O)=O</smiles>
  <inchi>InChI=1S/C24H40O10S2/c1-14(4-7-21(25)26)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(33-35(27,28)29)12-15(23)13-20(22)34-36(30,31)32/h14-20,22H,4-13H2,1-3H3,(H,25,26)(H,27,28,29)(H,30,31,32)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1</inchi>
  <inchikey>BWXSDJHAJWTEAD-BSWAIDMHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Sulfated steroids</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Bile acid, alcohol, or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfated steroid skeleton</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Sulfates</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-2,15-dimethyl-5,9-bis(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>552.698</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>552.20628888</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](C[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)OS(O)(=O)=O)[C@H](C)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O10S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O10S2/c1-14(4-7-21(25)26)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(33-35(27,28)29)12-15(23)13-20(22)34-36(30,31)32/h14-20,22H,4-13H2,1-3H3,(H,25,26)(H,27,28,29)(H,30,31,32)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BWXSDJHAJWTEAD-BSWAIDMHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>164.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>129.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>56.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358902</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <pubchem_compound_id>13990213</pubchem_compound_id>
  <chemspider_id>24850138</chemspider_id>
  <foodb_id>FDB022108</foodb_id>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5530</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Princen, Hans M. G.; Meijer, Piet; Kuipers, Folkert.  One-step solvolysis of 3-, 7- and 12-sulfated free and conjugated bile acids.    Clinica Chimica Acta  (1990),  192(1),  77-83.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:32 UTC</creation_date>
  <update_date>2020-04-15 22:09:20 UTC</update_date>
  <accession>BMDB0000546</accession>
  <secondary_accessions>
    <accession>BMDB00546</accession>
  </secondary_accessions>
  <name>Epietiocholanolone</name>
  <description/>
  <synonyms>
    <synonym>3b-Etiocholanolone</synonym>
    <synonym>3b-Hydroxy-17-oxo-5b-androstane</synonym>
    <synonym>3b-Hydroxy-5b-androstan-17-one</synonym>
    <synonym>3b-Hydroxy-5b-androstane-17-one</synonym>
    <synonym>3b-Hydroxyetiocholan-17-one</synonym>
    <synonym>5b-Androstan-3b-ol-17-one</synonym>
    <synonym>5b-Androstane-3b-ol-17-one</synonym>
    <synonym>5b-Epiandrosterone</synonym>
    <synonym>b-Etiocholanolone</synonym>
    <synonym>beta-Etiocholanolone</synonym>
    <synonym>Epi-5b-androsterone</synonym>
    <synonym>Epiaetiocholanolone</synonym>
    <synonym>Etiocholan-3b-ol-17-one</synonym>
    <synonym>M1A</synonym>
    <synonym>Methyl-1-alpha</synonym>
  </synonyms>
  <chemical_formula>C19H30O2</chemical_formula>
  <average_molecular_weight>290.4403</average_molecular_weight>
  <monisotopic_moleculate_weight>290.224580204</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5S,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</iupac_name>
  <traditional_iupac>(1S,2S,5S,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</traditional_iupac>
  <cas_registry_number>571-31-3</cas_registry_number>
  <smiles>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14+,15+,16+,18+,19+/m1/s1</inchi>
  <inchikey>QGXBDMJGAMFCBF-XRJZGPCZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>154 - 155 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5S,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>290.4403</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>290.224580204</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H30O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14+,15+,16+,18+,19+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QGXBDMJGAMFCBF-XRJZGPCZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>83.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451218</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022109</foodb_id>
  <chemspider_id>216866</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>247732</pubchem_compound_id>
  <chebi_id>542034</chebi_id>
  <pdbe_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Epietiocholanolone</wikipedia_id>
  <metlin_id>5531</metlin_id>
  <synthesis_reference>Fajkos, J.; Sanda, V.  Steroids. LXVI. 16-Bromo derivatives in the 5b-androstane series.    Collection of Czechoslovak Chemical Communications  (1962),  27  355-61.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:34 UTC</creation_date>
  <update_date>2020-04-16 20:38:29 UTC</update_date>
  <accession>BMDB0000547</accession>
  <secondary_accessions>
    <accession>BMDB00547</accession>
  </secondary_accessions>
  <name>Magnesium</name>
  <description>Magnesium, also known as magnesium ion or MG2+, belongs to the class of inorganic compounds known as homogeneous alkaline earth metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a alkaline earth metal atom. Magnesium exists as a solid, possibly soluble (in water), and possibly neutral molecule. Magnesium exists in all living species, ranging from bacteria to humans. Magnesium has been found to be associated with several diseases known as multiple sclerosis, alzheimer's disease, bartter syndrome, type 4a, neonatal, with sensorineural deafness, and bartter syndrome, type 3; also magnesium has been linked to the inborn metabolic disorders including primary hypomagnesemia.</description>
  <synonyms>
    <synonym>MAGNESIUM ion</synonym>
    <synonym>Magnesium, doubly charged positive ion</synonym>
    <synonym>Magnesium, ion (MG(2+))</synonym>
    <synonym>MG(2+)</synonym>
    <synonym>MG2+</synonym>
    <synonym>Magnesium(2+)</synonym>
    <synonym>Magnesium ions</synonym>
    <synonym>Neuropeptide y (1-27)</synonym>
  </synonyms>
  <chemical_formula>Mg</chemical_formula>
  <average_molecular_weight>24.305</average_molecular_weight>
  <monisotopic_moleculate_weight>23.985041898</monisotopic_moleculate_weight>
  <iupac_name>magnesium(2+) ion</iupac_name>
  <traditional_iupac>magnesium(2+) ion</traditional_iupac>
  <cas_registry_number>7439-95-4</cas_registry_number>
  <smiles>[Mg++]</smiles>
  <inchi>InChI=1S/Mg/q+2</inchi>
  <inchikey>JLVVSXFLKOJNIY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous alkaline earth metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a alkaline earth metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous alkaline earth metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous alkaline earth metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous alkaline earth metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a cation</external_descriptor>
      <external_descriptor>divalent metal cation</external_descriptor>
      <external_descriptor>magnesium cation</external_descriptor>
      <external_descriptor>monoatomic dication</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>651 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>magnesium(2+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>24.305</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>23.985041898</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Mg++]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Mg</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Mg/q+2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JLVVSXFLKOJNIY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Activation of cAMP-dependent protein kinase, PKA</name>
      <smpdb_id>SMP0108201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Alternative Complement Pathway</name>
      <smpdb_id>SMP0120928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Beta Oxidation of Very Long Chain Fatty Acids</name>
      <smpdb_id>SMP0087259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Butyrate Metabolism</name>
      <smpdb_id>SMP0087185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>CD40L Signalling Pathway</name>
      <smpdb_id>SMP0120942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Classical Complement Pathway</name>
      <smpdb_id>SMP0120932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Corticotropin Activation of Cortisol Production</name>
      <smpdb_id>SMP0108167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis</name>
      <smpdb_id>SMP0071338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/10:0)</name>
      <smpdb_id>SMP0108241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/12:0)</name>
      <smpdb_id>SMP0108483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/13:0)</name>
      <smpdb_id>SMP0108481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/14:0)</name>
      <smpdb_id>SMP0108477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/15:0)</name>
      <smpdb_id>SMP0108517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/16:0)</name>
      <smpdb_id>SMP0108480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/17:0)</name>
      <smpdb_id>SMP0108472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/18:0)</name>
      <smpdb_id>SMP0108485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/19:0)</name>
      <smpdb_id>SMP0108526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/8:0)</name>
      <smpdb_id>SMP0108478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-13:0)</name>
      <smpdb_id>SMP0108541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-15:0)</name>
      <smpdb_id>SMP0108542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-17:0)</name>
      <smpdb_id>SMP0108543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-21:0)</name>
      <smpdb_id>SMP0108544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-25:0)</name>
      <smpdb_id>SMP0108545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-12:0)</name>
      <smpdb_id>SMP0108546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-13:0)</name>
      <smpdb_id>SMP0108547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-14:0)</name>
      <smpdb_id>SMP0108548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-15:0)</name>
      <smpdb_id>SMP0108549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-16:0)</name>
      <smpdb_id>SMP0108550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-17:0)</name>
      <smpdb_id>SMP0108551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-18:0)</name>
      <smpdb_id>SMP0108552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-19:0)</name>
      <smpdb_id>SMP0108553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-20:0)</name>
      <smpdb_id>SMP0108554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-21:0)</name>
      <smpdb_id>SMP0108555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-22:0)</name>
      <smpdb_id>SMP0108556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-24:0)</name>
      <smpdb_id>SMP0108557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/12:0)</name>
      <smpdb_id>SMP0108470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/13:0)</name>
      <smpdb_id>SMP0108512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/14:0)</name>
      <smpdb_id>SMP0108445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/15:0)</name>
      <smpdb_id>SMP0108471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0108558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0108559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0108560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0108561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0108562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0108563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0108564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0108565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0108566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0108567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0108568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0108569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0108570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0108571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0108572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0108573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0108574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/13:0)</name>
      <smpdb_id>SMP0108460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/15:0)</name>
      <smpdb_id>SMP0108469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/16:0)</name>
      <smpdb_id>SMP0108463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/8:0)</name>
      <smpdb_id>SMP0108451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0108575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0108576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0108577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0108578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0108579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0108580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0108581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0108582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0108583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0108584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0108585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0108586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0108587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0108588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0108589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0108590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0108591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/13:0)</name>
      <smpdb_id>SMP0108534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/14:0)</name>
      <smpdb_id>SMP0108525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/15:0)</name>
      <smpdb_id>SMP0108522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/17:0)</name>
      <smpdb_id>SMP0108488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/18:0)</name>
      <smpdb_id>SMP0108489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/19:0)</name>
      <smpdb_id>SMP0108447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0108592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0108593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0108594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0108595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0108596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0108597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0108598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0108599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0108600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0108601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0108602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0108603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0108604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0108605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0108606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0108607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0108608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/15:0)</name>
      <smpdb_id>SMP0108476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/17:0)</name>
      <smpdb_id>SMP0108461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/18:0)</name>
      <smpdb_id>SMP0108523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/8:0)</name>
      <smpdb_id>SMP0108494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0108609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0108610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0108611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0108612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0108613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0108614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0108615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0108616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0108617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0108618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0108619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0108620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0108621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0108622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0108623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0108624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0108625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/12:0)</name>
      <smpdb_id>SMP0108479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/14:0)</name>
      <smpdb_id>SMP0108468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/15:0)</name>
      <smpdb_id>SMP0108507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/16:0)</name>
      <smpdb_id>SMP0108467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/17:0)</name>
      <smpdb_id>SMP0108458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/18:0)</name>
      <smpdb_id>SMP0108518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/8:0)</name>
      <smpdb_id>SMP0108504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0108626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0108627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0108628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0108629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0108630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0108631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0108632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0108633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0108634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0108635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0108636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0108637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0108638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0108639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0108640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0108641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0108642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/12:0)</name>
      <smpdb_id>SMP0108465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/13:0)</name>
      <smpdb_id>SMP0108456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/17:0)</name>
      <smpdb_id>SMP0108506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0108643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0108644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0108645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0108646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0108647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0108648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0108649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0108650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0108651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0108652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0108653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0108654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0108655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0108656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0108657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0108658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0108659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/12:0)</name>
      <smpdb_id>SMP0108495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/13:0)</name>
      <smpdb_id>SMP0108492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/17:0)</name>
      <smpdb_id>SMP0108452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/18:0)</name>
      <smpdb_id>SMP0108448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/19:0)</name>
      <smpdb_id>SMP0108503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/8:0)</name>
      <smpdb_id>SMP0108466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0108660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0108661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0108662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0108663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0108664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0108665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0108666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0108667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0108668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0108669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0108670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0108671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0108672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0108673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0108674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0108675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0108676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/12:0)</name>
      <smpdb_id>SMP0108511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/13:0)</name>
      <smpdb_id>SMP0108473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/15:0)</name>
      <smpdb_id>SMP0108533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/16:0)</name>
      <smpdb_id>SMP0108496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/17:0)</name>
      <smpdb_id>SMP0108521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/19:0)</name>
      <smpdb_id>SMP0108514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0108677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0108678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0108679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-21:0)</name>
      <smpdb_id>SMP0108680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-25:0)</name>
      <smpdb_id>SMP0108681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0108682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0108683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0108684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0108685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0108686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0108687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0108688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0108689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-20:0)</name>
      <smpdb_id>SMP0108690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-21:0)</name>
      <smpdb_id>SMP0108691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-22:0)</name>
      <smpdb_id>SMP0108692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-24:0)</name>
      <smpdb_id>SMP0108693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-13:0)</name>
      <smpdb_id>SMP0108694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-15:0)</name>
      <smpdb_id>SMP0108695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-17:0)</name>
      <smpdb_id>SMP0108696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0108697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0108698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-12:0)</name>
      <smpdb_id>SMP0108699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-13:0)</name>
      <smpdb_id>SMP0108700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-14:0)</name>
      <smpdb_id>SMP0108701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-15:0)</name>
      <smpdb_id>SMP0108702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-16:0)</name>
      <smpdb_id>SMP0108703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-17:0)</name>
      <smpdb_id>SMP0108704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-18:0)</name>
      <smpdb_id>SMP0108705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0108706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0108707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0108708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0108709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0108710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0108711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0108712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0108713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0108714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0108715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0108716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0108717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0108718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0108719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0108720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0108721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0108722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0108723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0108724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0108725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0108726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0108727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0108728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0108729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0108730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0108731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0108732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0108733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0108734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0108735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0108736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0108737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0108738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0108739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0108740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0108741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0108742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0108743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0108744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/17:0)</name>
      <smpdb_id>SMP0108457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/8:0)</name>
      <smpdb_id>SMP0108519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0108745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0108746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0108747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0108748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0108749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0108750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0108751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0108752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0108753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0108754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0108755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0108756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0108757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0108759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0111848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0108761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0108763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0108765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0108767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0108768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0108770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0108772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0108774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0108775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0108777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0108778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0108779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0108780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0108781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0108782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0108783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0108784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0108785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0108786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0108787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0108788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0108789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0108790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0108791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0108792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0108793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0108794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0108795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0108796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0108797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0108798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0108799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0108800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0108801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0108802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0108803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0108804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0108805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0108806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0108807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0108808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0108809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0108810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0108811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0108812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0108813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0108814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0108815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0108816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0108817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0108818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0108819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0108820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0108821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0108822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0108823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0108824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0108825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0108826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0108827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0108828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0108829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0108830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0108831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0108832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0108833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0108834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0108835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0108836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0108837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0108838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0108839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0108840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0108841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0108842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0108843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0108844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0108845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0108846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0108847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0108848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0108849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0108850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0108851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0108852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0108853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0108854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0108855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0108856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0108857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0108858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0108859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0108860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0108861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0108862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0108863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0108864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0108865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0108866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0108867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0108868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0108869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0108870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0108871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0108872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0108873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0108874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0108875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0108876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0108877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0108878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0108879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0108880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0108881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0108882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0108883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0108884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0108885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0108886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0108887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0108888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0108889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0108890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0108891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0108892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0108893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0108894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0108895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0108896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0108897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0108898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0108899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0108900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0108901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0108902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0108903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0108904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0108905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0108906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0108907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0108908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0108909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0108910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0108911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0108912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/a-25:0)</name>
      <smpdb_id>SMP0108913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0108914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0108915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0108916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/a-25:0)</name>
      <smpdb_id>SMP0108917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0108918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0108919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-24:0/a-25:0)</name>
      <smpdb_id>SMP0108920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0108921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(12:0/12:0/12:0)</name>
      <smpdb_id>SMP0108243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/20:0)</name>
      <smpdb_id>SMP0108262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/21:0)</name>
      <smpdb_id>SMP0108257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/22:0)</name>
      <smpdb_id>SMP0108278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/a-21:0)</name>
      <smpdb_id>SMP0108922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/a-25:0)</name>
      <smpdb_id>SMP0108923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-21:0)</name>
      <smpdb_id>SMP0108924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-22:0)</name>
      <smpdb_id>SMP0108925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-24:0)</name>
      <smpdb_id>SMP0108926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/21:0)</name>
      <smpdb_id>SMP0108277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/22:0)</name>
      <smpdb_id>SMP0108311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0108927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0108928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0108929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0108930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0108931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0108932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0108933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/10:0)</name>
      <smpdb_id>SMP0108328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/12:0)</name>
      <smpdb_id>SMP0108244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/13:0)</name>
      <smpdb_id>SMP0108317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/14:0)</name>
      <smpdb_id>SMP0108266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/15:0)</name>
      <smpdb_id>SMP0108275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/16:0)</name>
      <smpdb_id>SMP0108332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/17:0)</name>
      <smpdb_id>SMP0108292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/18:0)</name>
      <smpdb_id>SMP0108327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/21:0)</name>
      <smpdb_id>SMP0108305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/22:0)</name>
      <smpdb_id>SMP0108316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/8:0)</name>
      <smpdb_id>SMP0108301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0108934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0108935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0108936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0108937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0108938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0108939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0108940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0108941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0108942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0108943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0108944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0108945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0108946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0108947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0108948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0108949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0108950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/10:0)</name>
      <smpdb_id>SMP0108279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/12:0)</name>
      <smpdb_id>SMP0108261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/13:0)</name>
      <smpdb_id>SMP0108286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/14:0)</name>
      <smpdb_id>SMP0108255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/15:0)</name>
      <smpdb_id>SMP0108252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/16:0)</name>
      <smpdb_id>SMP0108299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/17:0)</name>
      <smpdb_id>SMP0108308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/18:0)</name>
      <smpdb_id>SMP0108282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/22:0)</name>
      <smpdb_id>SMP0108265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/8:0)</name>
      <smpdb_id>SMP0108319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0108951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0108952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0108953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0108954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0108955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0108956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0108957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0108958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0108959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0108960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0108961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0108962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0108963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0108964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0108965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0108966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0108967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0108968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/13:0)</name>
      <smpdb_id>SMP0108969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/14:0)</name>
      <smpdb_id>SMP0108970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/15:0)</name>
      <smpdb_id>SMP0108971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/16:0)</name>
      <smpdb_id>SMP0108972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/17:0)</name>
      <smpdb_id>SMP0108973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/18:0)</name>
      <smpdb_id>SMP0108974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/8:0)</name>
      <smpdb_id>SMP0108975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-13:0)</name>
      <smpdb_id>SMP0108976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-15:0)</name>
      <smpdb_id>SMP0108977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-17:0)</name>
      <smpdb_id>SMP0108978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0108979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0108980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0108981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0108982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0108983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0108984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0108985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0108986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0108987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0108988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0108989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0108990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0108991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0108992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/12:0)</name>
      <smpdb_id>SMP0108993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/13:0)</name>
      <smpdb_id>SMP0108994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/14:0)</name>
      <smpdb_id>SMP0108995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/15:0)</name>
      <smpdb_id>SMP0108996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/16:0)</name>
      <smpdb_id>SMP0108997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/17:0)</name>
      <smpdb_id>SMP0108998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/18:0)</name>
      <smpdb_id>SMP0108999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/8:0)</name>
      <smpdb_id>SMP0109000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-13:0)</name>
      <smpdb_id>SMP0109001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-15:0)</name>
      <smpdb_id>SMP0109002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-17:0)</name>
      <smpdb_id>SMP0109003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0109021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0109022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0109023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0109024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0109025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0109026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0109027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/8:0)</name>
      <smpdb_id>SMP0109028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0109029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0109030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0109031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0109032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0109033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0109034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0109035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0109036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0109037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0109038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-19:0)</name>
      <smpdb_id>SMP0109039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0109043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0109044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0109045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0109046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0109047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0109048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0109049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/8:0)</name>
      <smpdb_id>SMP0109050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0109051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0109052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0109053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0109054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0109055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0109056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0109057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0109058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0109059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0109060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-19:0)</name>
      <smpdb_id>SMP0109061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0109064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0109065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0109066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0109067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0109068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0109069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0109070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/8:0)</name>
      <smpdb_id>SMP0109071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0109072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0109073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0109074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0109075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0109076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0109078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0109079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0109080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0109081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0109082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-19:0)</name>
      <smpdb_id>SMP0109083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/10:0)</name>
      <smpdb_id>SMP0108330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/14:0)</name>
      <smpdb_id>SMP0108290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/17:0)</name>
      <smpdb_id>SMP0108312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/19:0)</name>
      <smpdb_id>SMP0108270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/21:0)</name>
      <smpdb_id>SMP0108300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/22:0)</name>
      <smpdb_id>SMP0108259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/10:0)</name>
      <smpdb_id>SMP0108320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/12:0)</name>
      <smpdb_id>SMP0108331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/13:0)</name>
      <smpdb_id>SMP0108318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/16:0)</name>
      <smpdb_id>SMP0108293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/17:0)</name>
      <smpdb_id>SMP0108304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/18:0)</name>
      <smpdb_id>SMP0108297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/19:0)</name>
      <smpdb_id>SMP0108288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/21:0)</name>
      <smpdb_id>SMP0108322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/22:0)</name>
      <smpdb_id>SMP0108314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/8:0)</name>
      <smpdb_id>SMP0108263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/10:0)</name>
      <smpdb_id>SMP0108256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/13:0)</name>
      <smpdb_id>SMP0108326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/15:0)</name>
      <smpdb_id>SMP0108250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/16:0)</name>
      <smpdb_id>SMP0108247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/21:0)</name>
      <smpdb_id>SMP0108313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/22:0)</name>
      <smpdb_id>SMP0108283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/8:0)</name>
      <smpdb_id>SMP0108276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/12:0)</name>
      <smpdb_id>SMP0108248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/13:0)</name>
      <smpdb_id>SMP0108295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/19:0)</name>
      <smpdb_id>SMP0108249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/21:0)</name>
      <smpdb_id>SMP0108271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/10:0)</name>
      <smpdb_id>SMP0108267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/12:0)</name>
      <smpdb_id>SMP0108324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/17:0)</name>
      <smpdb_id>SMP0108284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/21:0)</name>
      <smpdb_id>SMP0108306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/10:0)</name>
      <smpdb_id>SMP0108274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/19:0)</name>
      <smpdb_id>SMP0108269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/21:0)</name>
      <smpdb_id>SMP0108251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/13:0)</name>
      <smpdb_id>SMP0108289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/14:0)</name>
      <smpdb_id>SMP0108253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/16:0)</name>
      <smpdb_id>SMP0108302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/17:0)</name>
      <smpdb_id>SMP0108254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/19:0)</name>
      <smpdb_id>SMP0108264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/21:0)</name>
      <smpdb_id>SMP0108281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/22:0)</name>
      <smpdb_id>SMP0108294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/8:0)</name>
      <smpdb_id>SMP0108296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/10:0)</name>
      <smpdb_id>SMP0108315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/13:0)</name>
      <smpdb_id>SMP0108307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/17:0)</name>
      <smpdb_id>SMP0108273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/21:0)</name>
      <smpdb_id>SMP0108323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/8:0)</name>
      <smpdb_id>SMP0108287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/13:0)</name>
      <smpdb_id>SMP0108291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/15:0)</name>
      <smpdb_id>SMP0108272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/18:0)</name>
      <smpdb_id>SMP0108258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0109204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0109205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0109206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0109207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0109208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0109209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0109210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0109211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0109212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0109213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/10:0)</name>
      <smpdb_id>SMP0108309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/12:0)</name>
      <smpdb_id>SMP0108333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/13:0)</name>
      <smpdb_id>SMP0108329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/17:0)</name>
      <smpdb_id>SMP0108303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/19:0)</name>
      <smpdb_id>SMP0108321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/21:0)</name>
      <smpdb_id>SMP0108390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/8:0)</name>
      <smpdb_id>SMP0108268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-13:0)</name>
      <smpdb_id>SMP0109214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-15:0)</name>
      <smpdb_id>SMP0109215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-17:0)</name>
      <smpdb_id>SMP0109216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0109217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0109218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-12:0)</name>
      <smpdb_id>SMP0109219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-13:0)</name>
      <smpdb_id>SMP0109220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-14:0)</name>
      <smpdb_id>SMP0109221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-15:0)</name>
      <smpdb_id>SMP0109222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-16:0)</name>
      <smpdb_id>SMP0109223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-17:0)</name>
      <smpdb_id>SMP0109224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-18:0)</name>
      <smpdb_id>SMP0109225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0109226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0109227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0109228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0109229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0109230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/21:0)</name>
      <smpdb_id>SMP0108389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/22:0)</name>
      <smpdb_id>SMP0108370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0109231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0109232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0109233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0109234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0109235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0109236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0109237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0109238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0109239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0109240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0109241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0109242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0109243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0109244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0109245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0109246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0109247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/10:0)</name>
      <smpdb_id>SMP0108298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/14:0)</name>
      <smpdb_id>SMP0108246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/15:0)</name>
      <smpdb_id>SMP0108285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/16:0)</name>
      <smpdb_id>SMP0108280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/19:0)</name>
      <smpdb_id>SMP0108310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/21:0)</name>
      <smpdb_id>SMP0108245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/22:0)</name>
      <smpdb_id>SMP0108260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/8:0)</name>
      <smpdb_id>SMP0108325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0109330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0109370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0109371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0109372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0109373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0109374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0109375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0109376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0109377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0109378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0109379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0109380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0109381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0109382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0109383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0109384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0109385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0109386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0109387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0109388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0109389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0109390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0109391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0109392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0109393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0109394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0109395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0109396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0109397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0109398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0109400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0109401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0109402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0109403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0109404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0109405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0109406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0109407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0109408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0109409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0109410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0109411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0109412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0109413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0109414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0109415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0109416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0109417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0109418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0109419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0109420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0109421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0109422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0109423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0109424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0109425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0109426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/10:0)</name>
      <smpdb_id>SMP0108335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/12:0)</name>
      <smpdb_id>SMP0108363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/13:0)</name>
      <smpdb_id>SMP0108339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/17:0)</name>
      <smpdb_id>SMP0108349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/18:0)</name>
      <smpdb_id>SMP0108337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/22:0)</name>
      <smpdb_id>SMP0108367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/12:0)</name>
      <smpdb_id>SMP0108361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/13:0)</name>
      <smpdb_id>SMP0108351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/14:0)</name>
      <smpdb_id>SMP0108344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/15:0)</name>
      <smpdb_id>SMP0108371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/16:0)</name>
      <smpdb_id>SMP0108383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/18:0)</name>
      <smpdb_id>SMP0108387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/22:0)</name>
      <smpdb_id>SMP0108366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0109440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/13:0)</name>
      <smpdb_id>SMP0108368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/16:0)</name>
      <smpdb_id>SMP0108380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/17:0)</name>
      <smpdb_id>SMP0108345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/18:0)</name>
      <smpdb_id>SMP0108341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/22:0)</name>
      <smpdb_id>SMP0108388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/10:0)</name>
      <smpdb_id>SMP0108347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/13:0)</name>
      <smpdb_id>SMP0108342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/14:0)</name>
      <smpdb_id>SMP0108338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/16:0)</name>
      <smpdb_id>SMP0108346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/17:0)</name>
      <smpdb_id>SMP0108352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/18:0)</name>
      <smpdb_id>SMP0108386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/22:0)</name>
      <smpdb_id>SMP0108334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/8:0)</name>
      <smpdb_id>SMP0108365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/10:0)</name>
      <smpdb_id>SMP0108372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/13:0)</name>
      <smpdb_id>SMP0108358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/14:0)</name>
      <smpdb_id>SMP0108375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/15:0)</name>
      <smpdb_id>SMP0108348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/17:0)</name>
      <smpdb_id>SMP0108384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/18:0)</name>
      <smpdb_id>SMP0108369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/22:0)</name>
      <smpdb_id>SMP0108392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/8:0)</name>
      <smpdb_id>SMP0108354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/10:0)</name>
      <smpdb_id>SMP0108350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/15:0)</name>
      <smpdb_id>SMP0108355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/16:0)</name>
      <smpdb_id>SMP0108381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/17:0)</name>
      <smpdb_id>SMP0108364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/18:0)</name>
      <smpdb_id>SMP0108356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/22:0)</name>
      <smpdb_id>SMP0108385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/12:0)</name>
      <smpdb_id>SMP0108376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/17:0)</name>
      <smpdb_id>SMP0108393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/8:0)</name>
      <smpdb_id>SMP0108377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/17:0)</name>
      <smpdb_id>SMP0108396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/18:0)</name>
      <smpdb_id>SMP0108399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/10:0)</name>
      <smpdb_id>SMP0108340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/12:0)</name>
      <smpdb_id>SMP0108374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/13:0)</name>
      <smpdb_id>SMP0108336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/14:0)</name>
      <smpdb_id>SMP0108373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/15:0)</name>
      <smpdb_id>SMP0108382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/16:0)</name>
      <smpdb_id>SMP0108391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/17:0)</name>
      <smpdb_id>SMP0108397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/18:0)</name>
      <smpdb_id>SMP0108398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/22:0)</name>
      <smpdb_id>SMP0108400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/8:0)</name>
      <smpdb_id>SMP0108343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0109556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0109557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0109558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0109559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0109560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0109561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0109562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0109563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0109564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0109565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0109566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0109567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0109568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0109569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0109570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0109571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0109572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/17:0)</name>
      <smpdb_id>SMP0108395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/18:0)</name>
      <smpdb_id>SMP0108394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/22:0)</name>
      <smpdb_id>SMP0108401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/10:0)</name>
      <smpdb_id>SMP0108360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/12:0)</name>
      <smpdb_id>SMP0108357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/13:0)</name>
      <smpdb_id>SMP0108353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/16:0)</name>
      <smpdb_id>SMP0108359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/18:0)</name>
      <smpdb_id>SMP0108378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/22:0)</name>
      <smpdb_id>SMP0108362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/8:0)</name>
      <smpdb_id>SMP0108379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0109694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0109695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0109696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0109697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0109698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0109699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0109700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0109701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0109702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0109703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0109704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0109705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0109706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0109707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0109708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0109709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0109710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0109711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0109712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0109713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0109714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0109715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0109716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0109717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0109718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0109719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0109720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0109721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0109722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0109723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0109724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0109725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0109726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0109727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0109728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0109729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0109730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0109731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0109732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0109733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0109734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0109735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0109736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0109737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0109738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0109739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0109740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0109741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0109742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0109743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0109744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0109745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0109746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0109747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0109748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0109749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/10:0)</name>
      <smpdb_id>SMP0108437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/12:0)</name>
      <smpdb_id>SMP0108408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/13:0)</name>
      <smpdb_id>SMP0108423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/12:0)</name>
      <smpdb_id>SMP0108405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/13:0)</name>
      <smpdb_id>SMP0108403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/14:0)</name>
      <smpdb_id>SMP0108414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/15:0)</name>
      <smpdb_id>SMP0108426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/18:0)</name>
      <smpdb_id>SMP0108407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/8:0)</name>
      <smpdb_id>SMP0108420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0109763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/13:0)</name>
      <smpdb_id>SMP0108436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/15:0)</name>
      <smpdb_id>SMP0108428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/16:0)</name>
      <smpdb_id>SMP0108430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/17:0)</name>
      <smpdb_id>SMP0108419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/18:0)</name>
      <smpdb_id>SMP0108413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/8:0)</name>
      <smpdb_id>SMP0108411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/10:0)</name>
      <smpdb_id>SMP0108440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/13:0)</name>
      <smpdb_id>SMP0108422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/10:0)</name>
      <smpdb_id>SMP0108425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/8:0)</name>
      <smpdb_id>SMP0108410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/10:0)</name>
      <smpdb_id>SMP0108404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/12:0)</name>
      <smpdb_id>SMP0108406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/10:0)</name>
      <smpdb_id>SMP0108439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/12:0)</name>
      <smpdb_id>SMP0108402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/14:0)</name>
      <smpdb_id>SMP0108415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/15:0)</name>
      <smpdb_id>SMP0108434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/16:0)</name>
      <smpdb_id>SMP0108412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/17:0)</name>
      <smpdb_id>SMP0108431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/8:0)</name>
      <smpdb_id>SMP0108409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/10:0)</name>
      <smpdb_id>SMP0108421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/17:0)</name>
      <smpdb_id>SMP0108417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/8:0)</name>
      <smpdb_id>SMP0108432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/10:0)</name>
      <smpdb_id>SMP0108424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/12:0)</name>
      <smpdb_id>SMP0108435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/13:0)</name>
      <smpdb_id>SMP0108433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/17:0)</name>
      <smpdb_id>SMP0108438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/8:0)</name>
      <smpdb_id>SMP0108441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/10:0)</name>
      <smpdb_id>SMP0108416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/14:0)</name>
      <smpdb_id>SMP0108418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/16:0)</name>
      <smpdb_id>SMP0108427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/8:0)</name>
      <smpdb_id>SMP0108429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0108540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/10:0)</name>
      <smpdb_id>SMP0108443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/12:0)</name>
      <smpdb_id>SMP0108502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/16:0)</name>
      <smpdb_id>SMP0108450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/18:0)</name>
      <smpdb_id>SMP0108535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0110069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0110070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/12:0)</name>
      <smpdb_id>SMP0108459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/13:0)</name>
      <smpdb_id>SMP0108498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/14:0)</name>
      <smpdb_id>SMP0108462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/15:0)</name>
      <smpdb_id>SMP0108442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/17:0)</name>
      <smpdb_id>SMP0108464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/19:0)</name>
      <smpdb_id>SMP0108499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0110086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0110087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/10:0)</name>
      <smpdb_id>SMP0108455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/12:0)</name>
      <smpdb_id>SMP0108475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/14:0)</name>
      <smpdb_id>SMP0108532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/15:0)</name>
      <smpdb_id>SMP0108529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/17:0)</name>
      <smpdb_id>SMP0108491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/18:0)</name>
      <smpdb_id>SMP0108510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0110103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0110104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/12:0)</name>
      <smpdb_id>SMP0108486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/15:0)</name>
      <smpdb_id>SMP0108528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/17:0)</name>
      <smpdb_id>SMP0108505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0110120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0110121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/13:0)</name>
      <smpdb_id>SMP0108513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/14:0)</name>
      <smpdb_id>SMP0108449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/15:0)</name>
      <smpdb_id>SMP0108493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/16:0)</name>
      <smpdb_id>SMP0108500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/18:0)</name>
      <smpdb_id>SMP0108474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/19:0)</name>
      <smpdb_id>SMP0108446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0110137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0110138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/12:0)</name>
      <smpdb_id>SMP0108516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/16:0)</name>
      <smpdb_id>SMP0108530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/17:0)</name>
      <smpdb_id>SMP0108509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0110154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0110155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/13:0)</name>
      <smpdb_id>SMP0108524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/15:0)</name>
      <smpdb_id>SMP0108501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/17:0)</name>
      <smpdb_id>SMP0108453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/18:0)</name>
      <smpdb_id>SMP0108520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0110171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0110172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/10:0)</name>
      <smpdb_id>SMP0108482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/12:0)</name>
      <smpdb_id>SMP0108444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/14:0)</name>
      <smpdb_id>SMP0108497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/15:0)</name>
      <smpdb_id>SMP0108487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/17:0)</name>
      <smpdb_id>SMP0108484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/18:0)</name>
      <smpdb_id>SMP0108531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/19:0)</name>
      <smpdb_id>SMP0108538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0110185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0110186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0110187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0110188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0110189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0110190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0110191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0110192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0110193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0110194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0110195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-20:0)</name>
      <smpdb_id>SMP0110196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/12:0)</name>
      <smpdb_id>SMP0108508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/13:0)</name>
      <smpdb_id>SMP0108539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/14:0)</name>
      <smpdb_id>SMP0108515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/15:0)</name>
      <smpdb_id>SMP0108454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/16:0)</name>
      <smpdb_id>SMP0108490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/17:0)</name>
      <smpdb_id>SMP0108527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/18:0)</name>
      <smpdb_id>SMP0108537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/19:0)</name>
      <smpdb_id>SMP0108536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/8:0)</name>
      <smpdb_id>SMP0108242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0110197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0110198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0110199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0110200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0110201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0110202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0110203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0110204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0110205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0110206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0110207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0110208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0110209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0110210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0110211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0110212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0110213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0110217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0110218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0110223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0110233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0110234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0110248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0110249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0110262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0110263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0110264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0110265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0110266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0110267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0110268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0110269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0110270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0110271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0110272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0110273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0110274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0110275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/12:0)</name>
      <smpdb_id>SMP0110367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/13:0)</name>
      <smpdb_id>SMP0110368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/14:0)</name>
      <smpdb_id>SMP0110369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/15:0)</name>
      <smpdb_id>SMP0110370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/16:0)</name>
      <smpdb_id>SMP0110371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/17:0)</name>
      <smpdb_id>SMP0110372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/18:0)</name>
      <smpdb_id>SMP0110373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0110377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/13:0)</name>
      <smpdb_id>SMP0110390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/14:0)</name>
      <smpdb_id>SMP0110391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/15:0)</name>
      <smpdb_id>SMP0110392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/16:0)</name>
      <smpdb_id>SMP0110393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/17:0)</name>
      <smpdb_id>SMP0110394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/18:0)</name>
      <smpdb_id>SMP0110395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0110399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/14:0)</name>
      <smpdb_id>SMP0110412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/15:0)</name>
      <smpdb_id>SMP0110413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/16:0)</name>
      <smpdb_id>SMP0110414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/17:0)</name>
      <smpdb_id>SMP0110415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/18:0)</name>
      <smpdb_id>SMP0110416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0110420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/15:0)</name>
      <smpdb_id>SMP0110433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/16:0)</name>
      <smpdb_id>SMP0110434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/17:0)</name>
      <smpdb_id>SMP0110435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/18:0)</name>
      <smpdb_id>SMP0110436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0110440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/16:0)</name>
      <smpdb_id>SMP0110453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/17:0)</name>
      <smpdb_id>SMP0110454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/18:0)</name>
      <smpdb_id>SMP0110455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0110459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/17:0)</name>
      <smpdb_id>SMP0110472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/18:0)</name>
      <smpdb_id>SMP0110473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0110477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/18:0)</name>
      <smpdb_id>SMP0110490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0110494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0110510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0110524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0110538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0110551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/13:0)</name>
      <smpdb_id>SMP0110552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/14:0)</name>
      <smpdb_id>SMP0110553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/15:0)</name>
      <smpdb_id>SMP0110554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/16:0)</name>
      <smpdb_id>SMP0110555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/17:0)</name>
      <smpdb_id>SMP0110556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/18:0)</name>
      <smpdb_id>SMP0110557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-13:0)</name>
      <smpdb_id>SMP0110558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-15:0)</name>
      <smpdb_id>SMP0110559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-17:0)</name>
      <smpdb_id>SMP0110560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0110561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0110562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0110563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0110564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0110565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0110566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0110567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0110568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0110569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0110570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0110571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0110572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0110573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0110574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/a-13:0)</name>
      <smpdb_id>SMP0110630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/12:0)</name>
      <smpdb_id>SMP0110667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/13:0)</name>
      <smpdb_id>SMP0110668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/14:0)</name>
      <smpdb_id>SMP0110669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/15:0)</name>
      <smpdb_id>SMP0110670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/16:0)</name>
      <smpdb_id>SMP0110671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/17:0)</name>
      <smpdb_id>SMP0110672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/18:0)</name>
      <smpdb_id>SMP0110673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/13:0)</name>
      <smpdb_id>SMP0110689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/14:0)</name>
      <smpdb_id>SMP0110690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/15:0)</name>
      <smpdb_id>SMP0110691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/16:0)</name>
      <smpdb_id>SMP0110692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/17:0)</name>
      <smpdb_id>SMP0110693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/18:0)</name>
      <smpdb_id>SMP0110694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/14:0)</name>
      <smpdb_id>SMP0110710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/15:0)</name>
      <smpdb_id>SMP0110711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/16:0)</name>
      <smpdb_id>SMP0110712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/17:0)</name>
      <smpdb_id>SMP0110713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/18:0)</name>
      <smpdb_id>SMP0110714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/15:0)</name>
      <smpdb_id>SMP0110730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/16:0)</name>
      <smpdb_id>SMP0110731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/17:0)</name>
      <smpdb_id>SMP0110732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/18:0)</name>
      <smpdb_id>SMP0110733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/16:0)</name>
      <smpdb_id>SMP0110749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/17:0)</name>
      <smpdb_id>SMP0110750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/18:0)</name>
      <smpdb_id>SMP0110751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/17:0)</name>
      <smpdb_id>SMP0110767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/18:0)</name>
      <smpdb_id>SMP0110768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/18:0)</name>
      <smpdb_id>SMP0110784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0110807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/10:0)</name>
      <smpdb_id>SMP0110842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/12:0)</name>
      <smpdb_id>SMP0110843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/13:0)</name>
      <smpdb_id>SMP0110844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/14:0)</name>
      <smpdb_id>SMP0110845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/15:0)</name>
      <smpdb_id>SMP0110846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/16:0)</name>
      <smpdb_id>SMP0110847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/17:0)</name>
      <smpdb_id>SMP0110848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/18:0)</name>
      <smpdb_id>SMP0110849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-13:0)</name>
      <smpdb_id>SMP0110850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-15:0)</name>
      <smpdb_id>SMP0110851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-17:0)</name>
      <smpdb_id>SMP0110852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0110952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0110953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0110954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0110955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0110956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0110957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0110958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0110959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0110960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0110961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0110962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0110963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0110964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0110965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0110966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0110967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0110968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0110972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0110973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0110974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0110975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0110976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0110977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0110978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0110979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0110980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0110981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0110982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0110983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0110984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0110985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0110986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0110987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0110988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0110991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0110992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0110993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0110994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0110995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0110996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0110997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0110998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0110999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0111000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0111001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0111002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0111003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0111004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0111005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0111006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0111007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/12:0)</name>
      <smpdb_id>SMP0111009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/13:0)</name>
      <smpdb_id>SMP0111010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/14:0)</name>
      <smpdb_id>SMP0111011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/15:0)</name>
      <smpdb_id>SMP0111012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/16:0)</name>
      <smpdb_id>SMP0111013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/17:0)</name>
      <smpdb_id>SMP0111014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/18:0)</name>
      <smpdb_id>SMP0111015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/19:0)</name>
      <smpdb_id>SMP0111016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0111027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0111028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0111029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/13:0)</name>
      <smpdb_id>SMP0111031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/14:0)</name>
      <smpdb_id>SMP0111032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/15:0)</name>
      <smpdb_id>SMP0111033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/16:0)</name>
      <smpdb_id>SMP0111034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/17:0)</name>
      <smpdb_id>SMP0111035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/18:0)</name>
      <smpdb_id>SMP0111036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/19:0)</name>
      <smpdb_id>SMP0111037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0111048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0111049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0111050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/14:0)</name>
      <smpdb_id>SMP0111052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/15:0)</name>
      <smpdb_id>SMP0111053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/16:0)</name>
      <smpdb_id>SMP0111054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/17:0)</name>
      <smpdb_id>SMP0111055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/18:0)</name>
      <smpdb_id>SMP0111056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/19:0)</name>
      <smpdb_id>SMP0111057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0111068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0111069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0111070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/15:0)</name>
      <smpdb_id>SMP0111072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/16:0)</name>
      <smpdb_id>SMP0111073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/17:0)</name>
      <smpdb_id>SMP0111074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/18:0)</name>
      <smpdb_id>SMP0111075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/19:0)</name>
      <smpdb_id>SMP0111076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0111087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0111088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0111089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/16:0)</name>
      <smpdb_id>SMP0111091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/17:0)</name>
      <smpdb_id>SMP0111092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/18:0)</name>
      <smpdb_id>SMP0111093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/19:0)</name>
      <smpdb_id>SMP0111094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0111105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0111106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0111107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/17:0)</name>
      <smpdb_id>SMP0111109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/18:0)</name>
      <smpdb_id>SMP0111110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/19:0)</name>
      <smpdb_id>SMP0111111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0111122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0111123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0111124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/18:0)</name>
      <smpdb_id>SMP0111126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/19:0)</name>
      <smpdb_id>SMP0111127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0111138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0111139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0111140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/19:0)</name>
      <smpdb_id>SMP0111142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0111143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0111144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0111145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0111146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0111147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0111148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0111149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0111150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0111151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0111152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0111153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0111164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0111165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0111166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0111177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0111178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0111179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0111189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0111190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0111191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0111200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0111201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0111202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0111210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0111211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0111212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0111219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0111220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0111221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0111227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0111228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0111229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0111234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0111235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0111236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0111240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0111241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0111242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0111245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0111246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0111247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/12:0)</name>
      <smpdb_id>SMP0111249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/13:0)</name>
      <smpdb_id>SMP0111250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/14:0)</name>
      <smpdb_id>SMP0111251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/15:0)</name>
      <smpdb_id>SMP0111252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/16:0)</name>
      <smpdb_id>SMP0111253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/17:0)</name>
      <smpdb_id>SMP0111254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/18:0)</name>
      <smpdb_id>SMP0111255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-13:0)</name>
      <smpdb_id>SMP0111256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-15:0)</name>
      <smpdb_id>SMP0111257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-17:0)</name>
      <smpdb_id>SMP0111258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-12:0)</name>
      <smpdb_id>SMP0111259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-13:0)</name>
      <smpdb_id>SMP0111260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-14:0)</name>
      <smpdb_id>SMP0111261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-15:0)</name>
      <smpdb_id>SMP0111262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-16:0)</name>
      <smpdb_id>SMP0111263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-17:0)</name>
      <smpdb_id>SMP0111264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-18:0)</name>
      <smpdb_id>SMP0111265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0111266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0111267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0111268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0111269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0111270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0111271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0111272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/12:0)</name>
      <smpdb_id>SMP0111276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/13:0)</name>
      <smpdb_id>SMP0111277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/14:0)</name>
      <smpdb_id>SMP0111278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/15:0)</name>
      <smpdb_id>SMP0111279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/16:0)</name>
      <smpdb_id>SMP0111280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/17:0)</name>
      <smpdb_id>SMP0111281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/18:0)</name>
      <smpdb_id>SMP0111282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0111293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/13:0)</name>
      <smpdb_id>SMP0111295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/14:0)</name>
      <smpdb_id>SMP0111296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/15:0)</name>
      <smpdb_id>SMP0111297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/16:0)</name>
      <smpdb_id>SMP0111298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/17:0)</name>
      <smpdb_id>SMP0111299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/18:0)</name>
      <smpdb_id>SMP0111300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0111311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/14:0)</name>
      <smpdb_id>SMP0111313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/15:0)</name>
      <smpdb_id>SMP0111314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/16:0)</name>
      <smpdb_id>SMP0111315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/17:0)</name>
      <smpdb_id>SMP0111316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/18:0)</name>
      <smpdb_id>SMP0111317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0111328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/15:0)</name>
      <smpdb_id>SMP0111330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/16:0)</name>
      <smpdb_id>SMP0111331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/17:0)</name>
      <smpdb_id>SMP0111332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/18:0)</name>
      <smpdb_id>SMP0111333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0111344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/16:0)</name>
      <smpdb_id>SMP0111346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/17:0)</name>
      <smpdb_id>SMP0111347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/18:0)</name>
      <smpdb_id>SMP0111348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0111359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/17:0)</name>
      <smpdb_id>SMP0111361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/18:0)</name>
      <smpdb_id>SMP0111362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0111373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/18:0)</name>
      <smpdb_id>SMP0111375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0111386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0111398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0111409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0111419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0111428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0111436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0111443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0111449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0111454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0111458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0111461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0111463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0111464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0111465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0111466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0111467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0111468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0111469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0111470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0111471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0111472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0111473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0111474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0111475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0111476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0111477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0111478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0111479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0111480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0111481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0111482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/12:0)</name>
      <smpdb_id>SMP0111486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/13:0)</name>
      <smpdb_id>SMP0111487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/14:0)</name>
      <smpdb_id>SMP0111488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/15:0)</name>
      <smpdb_id>SMP0111489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/16:0)</name>
      <smpdb_id>SMP0111490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/17:0)</name>
      <smpdb_id>SMP0111491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/18:0)</name>
      <smpdb_id>SMP0111492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/13:0)</name>
      <smpdb_id>SMP0111504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/14:0)</name>
      <smpdb_id>SMP0111505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/15:0)</name>
      <smpdb_id>SMP0111506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/16:0)</name>
      <smpdb_id>SMP0111507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/17:0)</name>
      <smpdb_id>SMP0111508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/18:0)</name>
      <smpdb_id>SMP0111509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/14:0)</name>
      <smpdb_id>SMP0111521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/15:0)</name>
      <smpdb_id>SMP0111522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/16:0)</name>
      <smpdb_id>SMP0111523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/17:0)</name>
      <smpdb_id>SMP0111524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/18:0)</name>
      <smpdb_id>SMP0111525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/15:0)</name>
      <smpdb_id>SMP0111537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/16:0)</name>
      <smpdb_id>SMP0111538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/17:0)</name>
      <smpdb_id>SMP0111539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/18:0)</name>
      <smpdb_id>SMP0111540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/16:0)</name>
      <smpdb_id>SMP0111552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/17:0)</name>
      <smpdb_id>SMP0111553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/18:0)</name>
      <smpdb_id>SMP0111554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/17:0)</name>
      <smpdb_id>SMP0111566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/18:0)</name>
      <smpdb_id>SMP0111567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/18:0)</name>
      <smpdb_id>SMP0111579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0111656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0111657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0111658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0111659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0111660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0111661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0111662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0111663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0111664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0111665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0111666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0111667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0111668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0111669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0111670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0111671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0111672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/12:0)</name>
      <smpdb_id>SMP0111676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/13:0)</name>
      <smpdb_id>SMP0111677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/14:0)</name>
      <smpdb_id>SMP0111678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/15:0)</name>
      <smpdb_id>SMP0111679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/16:0)</name>
      <smpdb_id>SMP0111680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/17:0)</name>
      <smpdb_id>SMP0111681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/18:0)</name>
      <smpdb_id>SMP0111682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/13:0)</name>
      <smpdb_id>SMP0111693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/14:0)</name>
      <smpdb_id>SMP0111694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/15:0)</name>
      <smpdb_id>SMP0111695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/16:0)</name>
      <smpdb_id>SMP0111696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/17:0)</name>
      <smpdb_id>SMP0111697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/18:0)</name>
      <smpdb_id>SMP0111698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/14:0)</name>
      <smpdb_id>SMP0111709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/15:0)</name>
      <smpdb_id>SMP0111710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/16:0)</name>
      <smpdb_id>SMP0111711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/17:0)</name>
      <smpdb_id>SMP0111712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/18:0)</name>
      <smpdb_id>SMP0111713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/15:0)</name>
      <smpdb_id>SMP0111724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/16:0)</name>
      <smpdb_id>SMP0111725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/17:0)</name>
      <smpdb_id>SMP0111726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/18:0)</name>
      <smpdb_id>SMP0111727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/16:0)</name>
      <smpdb_id>SMP0111738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/17:0)</name>
      <smpdb_id>SMP0111739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/18:0)</name>
      <smpdb_id>SMP0111740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/17:0)</name>
      <smpdb_id>SMP0111751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/18:0)</name>
      <smpdb_id>SMP0111752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/18:0)</name>
      <smpdb_id>SMP0111763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0111829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0111830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0111831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0111832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0111833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0111834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0111835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0111836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0111837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0111838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0111839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0111840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0111841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0111842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0111843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0111844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0111845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dopamine Activation of Neurological Reward System</name>
      <smpdb_id>SMP0107994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>EPO Signaling Pathway</name>
      <smpdb_id>SMP0120938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 4 and Serotonin</name>
      <smpdb_id>SMP0108169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 6 and Serotonin</name>
      <smpdb_id>SMP0108172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 7 and Serotonin</name>
      <smpdb_id>SMP0108170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fc Epsilon Receptor I Signaling in Mast Cells</name>
      <smpdb_id>SMP0108186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Insulin Signalling</name>
      <smpdb_id>SMP0108189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2a and Adenosine</name>
      <smpdb_id>SMP0108174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2b and Adenosine</name>
      <smpdb_id>SMP0108178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through FSH Receptor and Follicle Stimulating Hormone</name>
      <smpdb_id>SMP0108183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Histamine H2 Receptor and Histamine</name>
      <smpdb_id>SMP0107995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through LHCGR Receptor and Luteinizing Hormone/Choriogonadotropin</name>
      <smpdb_id>SMP0108184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through PGD2 receptor and Prostaglandin D2</name>
      <smpdb_id>SMP0107997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Prostacyclin Receptor and Prostacyclin</name>
      <smpdb_id>SMP0107998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ion Channels and Their Functional Role in Vascular Endothelium</name>
      <smpdb_id>SMP0108207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lectin-Induced Complement Pathway </name>
      <smpdb_id>SMP0120930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA1 Signalling</name>
      <smpdb_id>SMP0108191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA2 Signalling</name>
      <smpdb_id>SMP0108193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA3 Signalling</name>
      <smpdb_id>SMP0108194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA4 Signalling</name>
      <smpdb_id>SMP0108196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA5 Signalling</name>
      <smpdb_id>SMP0108198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA6 Signalling</name>
      <smpdb_id>SMP0108199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Muscle/Heart Contraction</name>
      <smpdb_id>SMP0119378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylacetate Metabolism</name>
      <smpdb_id>SMP0087208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylinositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Plasmalogen Synthesis</name>
      <smpdb_id>SMP0087264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Riboflavin Metabolism</name>
      <smpdb_id>SMP0087211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Stat3 Signaling Pathway</name>
      <smpdb_id>SMP0120936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Succinate Signalling During Inflammation</name>
      <smpdb_id>SMP0120886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sulfate/Sulfite Metabolism</name>
      <smpdb_id>SMP0087216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vasopressin Regulation of Water Homeostasis</name>
      <smpdb_id>SMP0108181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin B6 Metabolism</name>
      <smpdb_id>SMP0087240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1980 +/- 10</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>McAdam PA, O'Dell GD: Mineral profile of blood plasma of lactating dairy cows. J Dairy Sci. 1982 Jul;65(7):1219-26. doi: 10.3168/jds.S0022-0302(82)82333-3.</reference_text>
          <pubmed_id>7108016</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>931+/-88</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>933.964 +/- 98.745</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Atomic Absorption Spectrophotometry. Samples have been collected from White Shorthorn x Galloway (Blue-grey).</comment>
      <references>
        <reference>
          <reference_text>C. R. E. Cogginsa and A. C. Field. Diurnal variation in the chemical composition of plasma from lactating beef cows on three dietary energy intakes. J. agric. Sri., Camb. (1976), 86, 595-602</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>10+/-7</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>279+/-84</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4000 - 6000</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: The minerals of milk. Reprod Nutr Dev. 2005 Jul-Aug;45(4):473-83. doi: 10.1051/rnd:2005030.</reference_text>
          <pubmed_id>16045895</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4937.256</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4340.671 +/- 113.968</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4570.664 +/- 95.0422</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5272.989 +/- 105.740</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5298.0868 +/- 102.0366</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>990.743 +/- 113.557</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1074.265 +/- 65.419</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1268.0518 +/- 54.310</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1495.988 +/- 66.242</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1588.562 +/- 63.773</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3058.218 +/- 157.581</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3266.406 +/- 90.928</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3302.613 +/- 75.705</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3709.525 +/- 93.396</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3777.000617 +/- 97.0994</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4048.961 +/- 197.490</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4139 +/- 712</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw whole milk</comment>
      <references>
        <reference>
          <reference_text>Zhang P, Allen JC: A novel dialysis procedure measuring free Zn2+ in bovine milk and plasma. J Nutr. 1995 Jul;125(7):1904-10. doi: 10.1093/jn/125.7.1904.</reference_text>
          <pubmed_id>7616307</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5348.694</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5348.694</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4525.818</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4525.818</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2057.19</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6583.00761</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5760.132</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4525.818</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6583.00761</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6171.57</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4525.818</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4525.818</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4854.968</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4854.968</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5348.694</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6583.00761</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5760.132</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6171.57</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4525.818</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4525.818</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5019.543</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4978.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5019.543</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4114.38</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4114.38</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4608.105</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3815 +/- 255</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4566.962</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3857 +/- 286</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4566.962</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4325 +/- 473</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4011 +/- 192</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4525.818 - 5348.694</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4400 - 12100</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk, range of  first 90 days in lactation</comment>
      <references>
        <reference>
          <reference_text>Tsioulpas A, Grandison AS, Lewis MJ: Changes in physical properties of bovine milk from the colostrum period to early lactation. J Dairy Sci. 2007 Nov;90(11):5012-7. doi: 10.3168/jds.2007-0192.</reference_text>
          <pubmed_id>17954740</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4937.256</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5727.628 - 37844.0650</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>7465+/-3511</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>102.0 +/- 6.0</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by ICP-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>286+/-105</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>70+/-23</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB01378</drugbank_id>
  <kegg_id>C00305</kegg_id>
  <chemspider_id>865</chemspider_id>
  <pubchem_compound_id>888</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18420</chebi_id>
  <foodb_id>FDB031004</foodb_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Magnesium</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Zhang P, Allen JC: A novel dialysis procedure measuring free Zn2+ in bovine milk and plasma. J Nutr. 1995 Jul;125(7):1904-10. doi: 10.1093/jn/125.7.1904.</reference_text>
      <pubmed_id>7616307</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gaucheron F: The minerals of milk. Reprod Nutr Dev. 2005 Jul-Aug;45(4):473-83. doi: 10.1051/rnd:2005030.</reference_text>
      <pubmed_id>16045895</pubmed_id>
    </reference>
    <reference>
      <reference_text>Tsioulpas A, Grandison AS, Lewis MJ: Changes in physical properties of bovine milk from the colostrum period to early lactation. J Dairy Sci. 2007 Nov;90(11):5012-7. doi: 10.3168/jds.2007-0192.</reference_text>
      <pubmed_id>17954740</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
      <pubmed_id>23040012</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
      <pubmed_id>22081685</pubmed_id>
    </reference>
    <reference>
      <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00082</protein_accession>
      <name>Serine racemase</name>
      <uniprot_id>A0JNI4</uniprot_id>
      <gene_name>SRR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00089</protein_accession>
      <name>Inositol-tetrakisphosphate 1-kinase</name>
      <uniprot_id>P0C0T1</uniprot_id>
      <gene_name>ITPK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00105</protein_accession>
      <name>Nicotinamide mononucleotide adenylyltransferase 1</name>
      <uniprot_id>Q0VD50</uniprot_id>
      <gene_name>NMNAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00106</protein_accession>
      <name>Nicotinamide mononucleotide adenylyltransferase 2</name>
      <uniprot_id>Q0VC59</uniprot_id>
      <gene_name>NMNAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00115</protein_accession>
      <name>Heparanase</name>
      <uniprot_id>Q9MYY0</uniprot_id>
      <gene_name>HPSE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00132</protein_accession>
      <name>Poly(ADP-ribose) glycohydrolase ARH3</name>
      <uniprot_id>Q3SYV9</uniprot_id>
      <gene_name>ADPRHL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00133</protein_accession>
      <name>Manganese-dependent ADP-ribose/CDP-alcohol diphosphatase</name>
      <uniprot_id>A7YY53</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00134</protein_accession>
      <name>[Protein ADP-ribosylarginine] hydrolase</name>
      <uniprot_id>Q32KR8</uniprot_id>
      <gene_name>ADPRH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00145</protein_accession>
      <name>Sodium/potassium-transporting ATPase subunit alpha-1</name>
      <uniprot_id>Q08DA1</uniprot_id>
      <gene_name>ATP1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00146</protein_accession>
      <name>Activin receptor type-2A</name>
      <uniprot_id>Q28043</uniprot_id>
      <gene_name>ACVR2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00149</protein_accession>
      <name>Cytosolic purine 5'-nucleotidase</name>
      <uniprot_id>O46411</uniprot_id>
      <gene_name>NT5C2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00150</protein_accession>
      <name>Fructose-1,6-bisphosphatase isozyme 2</name>
      <uniprot_id>Q2KJJ9</uniprot_id>
      <gene_name>FBP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00152</protein_accession>
      <name>Activin receptor type-2B</name>
      <uniprot_id>Q95126</uniprot_id>
      <gene_name>ACVR2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00153</protein_accession>
      <name>Calcium-transporting ATPase type 2C member 1</name>
      <uniprot_id>P57709</uniprot_id>
      <gene_name>ATP2C1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00157</protein_accession>
      <name>Probable phospholipid-transporting ATPase IIB</name>
      <uniprot_id>A1A4J6</uniprot_id>
      <gene_name>ATP9B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00158</protein_accession>
      <name>Sodium/potassium-transporting ATPase subunit alpha-2</name>
      <uniprot_id>A2VDL6</uniprot_id>
      <gene_name>ATP1A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00163</protein_accession>
      <name>Ectonucleoside triphosphate diphosphohydrolase 1</name>
      <uniprot_id>O18956</uniprot_id>
      <gene_name>ENTPD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00174</protein_accession>
      <name>S-adenosylmethionine synthetase</name>
      <uniprot_id>A7E3T7</uniprot_id>
      <gene_name>MAT2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00175</protein_accession>
      <name>ATP-citrate synthase</name>
      <uniprot_id>Q32PF2</uniprot_id>
      <gene_name>ACLY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00176</protein_accession>
      <name>Fructose-1,6-bisphosphatase 1</name>
      <uniprot_id>Q3SZB7</uniprot_id>
      <gene_name>FBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00185</protein_accession>
      <name>Activated CDC42 kinase 1</name>
      <uniprot_id>Q17R13</uniprot_id>
      <gene_name>TNK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00191</protein_accession>
      <name>ATP10D protein</name>
      <uniprot_id>A7Z029</uniprot_id>
      <gene_name>ATP10D</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00194</protein_accession>
      <name>Eyes absent homolog 2</name>
      <uniprot_id>Q58DB6</uniprot_id>
      <gene_name>EYA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00195</protein_accession>
      <name>3'(2'),5'-bisphosphate nucleotidase 1</name>
      <uniprot_id>Q3ZCK3</uniprot_id>
      <gene_name>BPNT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00196</protein_accession>
      <name>Probable phospholipid-transporting ATPase IA</name>
      <uniprot_id>Q29449</uniprot_id>
      <gene_name>ATP8A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00198</protein_accession>
      <name>Alkaline phosphatase</name>
      <uniprot_id>A6QQR9</uniprot_id>
      <gene_name>LOC100125266</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00205</protein_accession>
      <name>Activin receptor type-1</name>
      <uniprot_id>Q28041</uniprot_id>
      <gene_name>ACVR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00207</protein_accession>
      <name>Sarcoplasmic/endoplasmic reticulum calcium ATPase 1</name>
      <uniprot_id>Q0VCY0</uniprot_id>
      <gene_name>ATP2A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00210</protein_accession>
      <name>Enolase-phosphatase E1</name>
      <uniprot_id>Q0VD27</uniprot_id>
      <gene_name>ENOPH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00216</protein_accession>
      <name>Pyridoxal phosphate phosphatase</name>
      <uniprot_id>Q3ZBF9</uniprot_id>
      <gene_name>PDXP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00223</protein_accession>
      <name>Pyridoxal phosphate phosphatase PHOSPHO2</name>
      <uniprot_id>Q2KI06</uniprot_id>
      <gene_name>PHOSPHO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00261</protein_accession>
      <name>Squalene synthetase</name>
      <uniprot_id>Q32KR6</uniprot_id>
      <gene_name>FDFT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00374</protein_accession>
      <name>Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrial</name>
      <uniprot_id>Q0P5C2</uniprot_id>
      <gene_name>MTHFD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00387</protein_accession>
      <name>Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)</name>
      <uniprot_id>Q58DK4</uniprot_id>
      <gene_name>DAK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00390</protein_accession>
      <name>Cholinephosphotransferase 1</name>
      <uniprot_id>Q1LZE6</uniprot_id>
      <gene_name>CHPT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00391</protein_accession>
      <name>Ethanolaminephosphotransferase 1</name>
      <uniprot_id>Q17QM4</uniprot_id>
      <gene_name>SELI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00403</protein_accession>
      <name>S-adenosylmethionine synthetase isoform type-1</name>
      <uniprot_id>Q2KJC6</uniprot_id>
      <gene_name>MAT1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00421</protein_accession>
      <name>Catechol O-methyltransferase</name>
      <uniprot_id>A7MBI7</uniprot_id>
      <gene_name>COMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00427</protein_accession>
      <name>Fumarylacetoacetase</name>
      <uniprot_id>A5PKH3</uniprot_id>
      <gene_name>FAH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00434</protein_accession>
      <name>cGMP-specific 3',5'-cyclic phosphodiesterase</name>
      <uniprot_id>Q28156</uniprot_id>
      <gene_name>PDE5A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00440</protein_accession>
      <name>Hypoxanthine-guanine phosphoribosyltransferase</name>
      <uniprot_id>Q3SZ18</uniprot_id>
      <gene_name>HPRT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00441</protein_accession>
      <name>Galactose-3-O-sulfotransferase 3</name>
      <uniprot_id>Q0VCH4</uniprot_id>
      <gene_name>GAL3ST3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00442</protein_accession>
      <name>Adenylate cyclase type 1</name>
      <uniprot_id>P19754</uniprot_id>
      <gene_name>ADCY1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00443</protein_accession>
      <name>Poly(A)-specific ribonuclease PARN</name>
      <uniprot_id>P69341</uniprot_id>
      <gene_name>PARN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00444</protein_accession>
      <name>U8 snoRNA-decapping enzyme</name>
      <uniprot_id>A1A4Q9</uniprot_id>
      <gene_name>NUDT16</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00445</protein_accession>
      <name>Diphosphoinositol polyphosphate phosphohydrolase 3-beta</name>
      <uniprot_id>Q58CW0</uniprot_id>
      <gene_name>NUDT11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00446</protein_accession>
      <name>Phosphoglucomutase-1</name>
      <uniprot_id>Q08DP0</uniprot_id>
      <gene_name>PGM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00447</protein_accession>
      <name>DNA-(apurinic or apyrimidinic site) lyase</name>
      <uniprot_id>P23196</uniprot_id>
      <gene_name>APEX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00448</protein_accession>
      <name>Isocitrate dehydrogenase [NADP], mitochondrial</name>
      <uniprot_id>Q04467</uniprot_id>
      <gene_name>IDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00449</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>B3IVN4</uniprot_id>
      <gene_name>PKM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00450</protein_accession>
      <name>Endonuclease G, mitochondrial</name>
      <uniprot_id>P38447</uniprot_id>
      <gene_name>ENDOG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00451</protein_accession>
      <name>Isopentenyl-diphosphate Delta-isomerase 1</name>
      <uniprot_id>Q1LZ95</uniprot_id>
      <gene_name>IDI1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00452</protein_accession>
      <name>Flap endonuclease 1</name>
      <uniprot_id>Q58DH8</uniprot_id>
      <gene_name>FEN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00453</protein_accession>
      <name>Mitochondrial enolase superfamily member 1</name>
      <uniprot_id>Q2KIA9</uniprot_id>
      <gene_name>ENOSF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00454</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit gamma, mitochondrial</name>
      <uniprot_id>Q58CP0</uniprot_id>
      <gene_name>IDH3G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00455</protein_accession>
      <name>Beta-enolase</name>
      <uniprot_id>Q3ZC09</uniprot_id>
      <gene_name>ENO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00456</protein_accession>
      <name>Inositol monophosphatase</name>
      <uniprot_id>P20456</uniprot_id>
      <gene_name>IMPA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00457</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>Q3ZC87</uniprot_id>
      <gene_name>PKM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00458</protein_accession>
      <name>Interleukin-1 receptor-associated kinase 1</name>
      <uniprot_id>Q2LGB3</uniprot_id>
      <gene_name>IRAK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00459</protein_accession>
      <name>Myosin light chain kinase, smooth muscle</name>
      <uniprot_id>Q28824</uniprot_id>
      <gene_name>MYLK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00460</protein_accession>
      <name>Polyribonucleotide 5'-hydroxyl-kinase Clp1</name>
      <uniprot_id>A2VE01</uniprot_id>
      <gene_name>CLP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00461</protein_accession>
      <name>Inositol polyphosphate 1-phosphatase</name>
      <uniprot_id>P21327</uniprot_id>
      <gene_name>INPP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00462</protein_accession>
      <name>Testis-specific serine/threonine-protein kinase 1</name>
      <uniprot_id>Q3SZW1</uniprot_id>
      <gene_name>TSSK1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00463</protein_accession>
      <name>Alkaline phosphatase, tissue-nonspecific isozyme</name>
      <uniprot_id>P09487</uniprot_id>
      <gene_name>ALPL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00464</protein_accession>
      <name>Alpha-enolase</name>
      <uniprot_id>Q9XSJ4</uniprot_id>
      <gene_name>ENO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00465</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>Q1JPG7</uniprot_id>
      <gene_name>PKLR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00466</protein_accession>
      <name>Adenylate cyclase type 7</name>
      <uniprot_id>Q29450</uniprot_id>
      <gene_name>ADCY7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00467</protein_accession>
      <name>Intestinal alkaline phosphatase</name>
      <uniprot_id>P19111</uniprot_id>
      <gene_name>ALPI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00468</protein_accession>
      <name>Protein phosphatase 1B</name>
      <uniprot_id>O62830</uniprot_id>
      <gene_name>PPM1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00469</protein_accession>
      <name>Ribonuclease ZC3H12A</name>
      <uniprot_id>A6QQJ8</uniprot_id>
      <gene_name>ZC3H12A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00470</protein_accession>
      <name>Integrin-linked kinase-associated serine/threonine phosphatase 2C</name>
      <uniprot_id>Q0IIF0</uniprot_id>
      <gene_name>ILKAP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00471</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial</name>
      <uniprot_id>O77784</uniprot_id>
      <gene_name>IDH3B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00472</protein_accession>
      <name>DNA polymerase beta</name>
      <uniprot_id>Q27958</uniprot_id>
      <gene_name>POLB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00473</protein_accession>
      <name>Serine/threonine-protein kinase 4</name>
      <uniprot_id>Q5E9L6</uniprot_id>
      <gene_name>STK4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00474</protein_accession>
      <name>Mitogen-activated protein kinase kinase kinase 7</name>
      <uniprot_id>A2VDU3</uniprot_id>
      <gene_name>MAP3K7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00475</protein_accession>
      <name>Mitogen-activated protein kinase kinase kinase 13</name>
      <uniprot_id>A7MBB4</uniprot_id>
      <gene_name>MAP3K13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00476</protein_accession>
      <name>Alkaline phosphatase</name>
      <uniprot_id>O77578</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00477</protein_accession>
      <name>Bis(5'-adenosyl)-triphosphatase</name>
      <uniprot_id>Q1KZG4</uniprot_id>
      <gene_name>FHIT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00478</protein_accession>
      <name>Ribose-phosphate pyrophosphokinase</name>
      <uniprot_id>A6QQ58</uniprot_id>
      <gene_name>LOC504248</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00479</protein_accession>
      <name>6-phosphofructokinase, liver type</name>
      <uniprot_id>A1A4J1</uniprot_id>
      <gene_name>PFKL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00480</protein_accession>
      <name>5'-nucleotidase domain-containing protein 1</name>
      <uniprot_id>Q2TBU5</uniprot_id>
      <gene_name>NT5DC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00481</protein_accession>
      <name>Glycoprotein-N-acetylgalactosamine 3-beta-galactosyltransferase 1</name>
      <uniprot_id>Q0VC84</uniprot_id>
      <gene_name>C1GALT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00482</protein_accession>
      <name>Ribose-phosphate pyrophosphokinase 1</name>
      <uniprot_id>Q2HJ58</uniprot_id>
      <gene_name>PRPS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00483</protein_accession>
      <name>Interleukin-1 receptor-associated kinase 4</name>
      <uniprot_id>Q1RMT8</uniprot_id>
      <gene_name>IRAK4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00484</protein_accession>
      <name>Endoribonuclease Dicer</name>
      <uniprot_id>Q6TUI4</uniprot_id>
      <gene_name>DICER1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00485</protein_accession>
      <name>Phosphoserine phosphatase</name>
      <uniprot_id>Q2KHU0</uniprot_id>
      <gene_name>PSPH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00486</protein_accession>
      <name>Nucleoside diphosphate kinase 7</name>
      <uniprot_id>Q5E9Y9</uniprot_id>
      <gene_name>NME7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00487</protein_accession>
      <name>Inositol monophosphatase 3</name>
      <uniprot_id>Q2KJ53</uniprot_id>
      <gene_name>IMPAD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00488</protein_accession>
      <name>Acetolactate synthase-like protein</name>
      <uniprot_id>A6QQT9</uniprot_id>
      <gene_name>ILVBL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00489</protein_accession>
      <name>Nucleoside diphosphate-linked moiety X motif 17</name>
      <uniprot_id>A4FUG7</uniprot_id>
      <gene_name>NUDT17</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00490</protein_accession>
      <name>Inorganic pyrophosphatase</name>
      <uniprot_id>P37980</uniprot_id>
      <gene_name>PPA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00491</protein_accession>
      <name>Enolase</name>
      <uniprot_id>A6QR19</uniprot_id>
      <gene_name>ENO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00492</protein_accession>
      <name>TFIIH basal transcription factor complex helicase subunit</name>
      <uniprot_id>A6QLJ0</uniprot_id>
      <gene_name>ERCC2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00493</protein_accession>
      <name>Alkaline phosphatase</name>
      <uniprot_id>O77579</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00494</protein_accession>
      <name>Protein phosphatase 1K, mitochondrial</name>
      <uniprot_id>Q2PC20</uniprot_id>
      <gene_name>PPM1K</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00495</protein_accession>
      <name>Adenylosuccinate synthetase isozyme 1</name>
      <uniprot_id>A5PJR4</uniprot_id>
      <gene_name>ADSSL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00496</protein_accession>
      <name>Glycerophosphodiester phosphodiesterase 1</name>
      <uniprot_id>Q3T0T0</uniprot_id>
      <gene_name>GDE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00497</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>A5D984</uniprot_id>
      <gene_name>PKM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00498</protein_accession>
      <name>[Pyruvate dehydrogenase [acetyl-transferring]]-phosphatase 1, mitochondrial</name>
      <uniprot_id>P35816</uniprot_id>
      <gene_name>PDP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00499</protein_accession>
      <name>Cytosol aminopeptidase</name>
      <uniprot_id>P00727</uniprot_id>
      <gene_name>LAP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00500</protein_accession>
      <name>Diphosphoinositol polyphosphate phosphohydrolase 1</name>
      <uniprot_id>A2VE79</uniprot_id>
      <gene_name>NUDT3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00501</protein_accession>
      <name>Thioredoxin reductase 2, mitochondrial</name>
      <uniprot_id>Q9N2I8</uniprot_id>
      <gene_name>TXNRD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00502</protein_accession>
      <name>TGF-beta receptor type-1</name>
      <uniprot_id>O46680</uniprot_id>
      <gene_name>TGFBR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00503</protein_accession>
      <name>Nucleoside diphosphate kinase A 1</name>
      <uniprot_id>P52174</uniprot_id>
      <gene_name>NME1-1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00504</protein_accession>
      <name>Protein phosphatase 1G</name>
      <uniprot_id>P79126</uniprot_id>
      <gene_name>PPM1G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00505</protein_accession>
      <name>Tubulin--tyrosine ligase</name>
      <uniprot_id>P38584</uniprot_id>
      <gene_name>TTL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00506</protein_accession>
      <name>Fumarylacetoacetate hydrolase domain-containing protein 2</name>
      <uniprot_id>Q2KIB0</uniprot_id>
      <gene_name>FAHD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00507</protein_accession>
      <name>Nucleoside diphosphate kinase B</name>
      <uniprot_id>Q3T0Q4</uniprot_id>
      <gene_name>NME2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00508</protein_accession>
      <name>Inosine triphosphate pyrophosphatase</name>
      <uniprot_id>Q2KIC5</uniprot_id>
      <gene_name>ITPA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00509</protein_accession>
      <name>Acyl-coenzyme A synthetase ACSM1, mitochondrial</name>
      <uniprot_id>Q9BEA2</uniprot_id>
      <gene_name>ACSM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00510</protein_accession>
      <name>Serine/threonine-protein kinase 25</name>
      <uniprot_id>Q3SWY6</uniprot_id>
      <gene_name>STK25</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00511</protein_accession>
      <name>Protein phosphatase 1L</name>
      <uniprot_id>A5PJZ2</uniprot_id>
      <gene_name>PPM1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00512</protein_accession>
      <name>Peroxisomal NADH pyrophosphatase NUDT12</name>
      <uniprot_id>Q29RH3</uniprot_id>
      <gene_name>NUDT12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00513</protein_accession>
      <name>Serine/threonine-protein kinase 12</name>
      <uniprot_id>Q7YRC6</uniprot_id>
      <gene_name>AURKB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00514</protein_accession>
      <name>DNA-directed RNA polymerase III subunit RPC1</name>
      <uniprot_id>A4IF62</uniprot_id>
      <gene_name>POLR3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00515</protein_accession>
      <name>Serine/threonine-protein kinase 38</name>
      <uniprot_id>A2VDV2</uniprot_id>
      <gene_name>STK38</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00516</protein_accession>
      <name>Isocitrate dehydrogenase [NADP] cytoplasmic</name>
      <uniprot_id>Q9XSG3</uniprot_id>
      <gene_name>IDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00517</protein_accession>
      <name>Putative ATP-dependent Clp protease proteolytic subunit, mitochondrial</name>
      <uniprot_id>Q2KHU4</uniprot_id>
      <gene_name>CLPP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00518</protein_accession>
      <name>Nucleoside diphosphate kinase A 2</name>
      <uniprot_id>P52175</uniprot_id>
      <gene_name>NME1-2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00519</protein_accession>
      <name>Fumarylacetoacetate hydrolase domain-containing protein 1</name>
      <uniprot_id>Q2HJ98</uniprot_id>
      <gene_name>FAHD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00520</protein_accession>
      <name>Three prime repair exonuclease 1</name>
      <uniprot_id>Q9BG99</uniprot_id>
      <gene_name>TREX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00521</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit alpha, mitochondrial</name>
      <uniprot_id>P41563</uniprot_id>
      <gene_name>IDH3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00522</protein_accession>
      <name>ADP-dependent glucokinase</name>
      <uniprot_id>A2VE47</uniprot_id>
      <gene_name>ADPGK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00523</protein_accession>
      <name>6-phosphofructokinase, muscle type</name>
      <uniprot_id>Q0IIG5</uniprot_id>
      <gene_name>PFKM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00524</protein_accession>
      <name>Protein phosphatase 1A</name>
      <uniprot_id>O62829</uniprot_id>
      <gene_name>PPM1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00525</protein_accession>
      <name>Adenylosuccinate synthetase isozyme 2</name>
      <uniprot_id>A7MBG0</uniprot_id>
      <gene_name>ADSS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00526</protein_accession>
      <name>Uridine diphosphate glucose pyrophosphatase</name>
      <uniprot_id>Q05B60</uniprot_id>
      <gene_name>NUDT14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00846</protein_accession>
      <name>Hyaluronan synthase 2</name>
      <uniprot_id>O97711</uniprot_id>
      <gene_name>HAS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01142</protein_accession>
      <name>Serine/threonine-protein kinase PAK 1</name>
      <uniprot_id>Q08E52</uniprot_id>
      <gene_name>PAK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01143</protein_accession>
      <name>Mitogen-activated protein kinase 7</name>
      <uniprot_id>A5PKJ4</uniprot_id>
      <gene_name>MAPK7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01183</protein_accession>
      <name>MAP kinase-interacting serine/threonine-protein kinase 1</name>
      <uniprot_id>Q58D94</uniprot_id>
      <gene_name>MKNK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01191</protein_accession>
      <name>Mitogen-activated protein kinase 1</name>
      <uniprot_id>P46196</uniprot_id>
      <gene_name>MAPK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01200</protein_accession>
      <name>Pyridoxal kinase</name>
      <uniprot_id>Q0II59</uniprot_id>
      <gene_name>PDXK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01201</protein_accession>
      <name>Mitogen-activated protein kinase 13</name>
      <uniprot_id>Q3T0N5</uniprot_id>
      <gene_name>MAPK13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01305</protein_accession>
      <name>Deoxyribonuclease-1</name>
      <uniprot_id>P00639</uniprot_id>
      <gene_name>DNASE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01344</protein_accession>
      <name>Calcium-activated potassium channel subunit alpha-1</name>
      <uniprot_id>Q28204</uniprot_id>
      <gene_name>KCNMA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01589</protein_accession>
      <name>Cyclic AMP-responsive element-binding protein 1</name>
      <uniprot_id>P27925</uniprot_id>
      <gene_name>CREB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01590</protein_accession>
      <name>ADP-ribosylation factor-like protein 3</name>
      <uniprot_id>Q2TBW6</uniprot_id>
      <gene_name>ARL3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01591</protein_accession>
      <name>PGM2 protein</name>
      <uniprot_id>A6QQ11</uniprot_id>
      <gene_name>PGM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01592</protein_accession>
      <name>LYR motif-containing protein 4</name>
      <uniprot_id>Q0VCG0</uniprot_id>
      <gene_name>LYRM4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01593</protein_accession>
      <name>Ras GTPase-activating protein-binding protein 1</name>
      <uniprot_id>Q32LC7</uniprot_id>
      <gene_name>G3BP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01594</protein_accession>
      <name>GTP-binding protein SAR1b</name>
      <uniprot_id>Q3T0T7</uniprot_id>
      <gene_name>SAR1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01595</protein_accession>
      <name>Ribonuclease H2 subunit A</name>
      <uniprot_id>Q2TBT5</uniprot_id>
      <gene_name>RNASEH2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01596</protein_accession>
      <name>Rho-related GTP-binding protein RhoU</name>
      <uniprot_id>A5D7J5</uniprot_id>
      <gene_name>RHOU</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01597</protein_accession>
      <name>Calcium-binding protein 1</name>
      <uniprot_id>Q9N1R0</uniprot_id>
      <gene_name>CABP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01598</protein_accession>
      <name>GTP-binding protein Rheb</name>
      <uniprot_id>Q56JV3</uniprot_id>
      <gene_name>RHEB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01599</protein_accession>
      <name>Transforming protein RhoA</name>
      <uniprot_id>P61585</uniprot_id>
      <gene_name>RHOA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01600</protein_accession>
      <name>Rho-related GTP-binding protein RhoV</name>
      <uniprot_id>Q17QI8</uniprot_id>
      <gene_name>Rhov</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01601</protein_accession>
      <name>PGM1 protein</name>
      <uniprot_id>A6QPB5</uniprot_id>
      <gene_name>PGM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01602</protein_accession>
      <name>Integrin alpha-L</name>
      <uniprot_id>P61625</uniprot_id>
      <gene_name>ITGAL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01603</protein_accession>
      <name>Ubiquitin-like domain-containing CTD phosphatase 1</name>
      <uniprot_id>Q2KJD7</uniprot_id>
      <gene_name>UBLCP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01604</protein_accession>
      <name>Membrane magnesium transporter 1</name>
      <uniprot_id>Q32LC4</uniprot_id>
      <gene_name>MMGT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01605</protein_accession>
      <name>Claudin-16</name>
      <uniprot_id>Q9XT98</uniprot_id>
      <gene_name>CLDN16</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01606</protein_accession>
      <name>Integrin alpha-2</name>
      <uniprot_id>P53710</uniprot_id>
      <gene_name>ITGA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01607</protein_accession>
      <name>PGM5 protein</name>
      <uniprot_id>A6QNJ7</uniprot_id>
      <gene_name>PGM5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:35 UTC</creation_date>
  <update_date>2020-03-13 16:22:02 UTC</update_date>
  <accession>BMDB0000548</accession>
  <secondary_accessions>
    <accession>BMDB00548</accession>
  </secondary_accessions>
  <name>TG(10:0/10:0/10:0)[iso]</name>
  <description>TG(10:0/10:0/10:0), also known as caprin or glycerol tridecanoate, belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Thus, TG(10:0/10:0/10:0) is considered to be a triradylglycerol lipid molecule. TG(10:0/10:0/10:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. TG(10:0/10:0/10:0) exists in all eukaryotes, ranging from yeast to humans. TG(10:0/10:0/10:0) can be biosynthesized from DG(10:0/10:0/0:0) and decanoyl-CoA; which is catalyzed by the enzyme diacylglycerol O-acyltransferase. In cattle, TG(10:0/10:0/10:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(10:0/10:0/10:0) pathway.</description>
  <synonyms>
    <synonym>1,2,3-Propanol tridecanoate</synonym>
    <synonym>1,2,3-Tridecanoylglycerol</synonym>
    <synonym>Capric acid triglyceride</synonym>
    <synonym>Capric triglyceride</synonym>
    <synonym>Caprin</synonym>
    <synonym>Decanoic acid, 1,2,3-propanetriyl ester</synonym>
    <synonym>Glycerin tridecanoate</synonym>
    <synonym>Glycerol tricaprate</synonym>
    <synonym>Glycerol tridecanoate</synonym>
    <synonym>Glyceryl tricaprate</synonym>
    <synonym>Glyceryl tridecanoate</synonym>
    <synonym>TG 10:0/10:0/10:0</synonym>
    <synonym>Tri-N-caprin</synonym>
    <synonym>Tricapric glyceride</synonym>
    <synonym>Tridecanoin</synonym>
    <synonym>Tridecanoylglycerol</synonym>
    <synonym>1,2,3-Propanol tridecanoic acid</synonym>
    <synonym>Caprate triglyceride</synonym>
    <synonym>Decanoate, 1,2,3-propanetriyl ester</synonym>
    <synonym>Glycerin tridecanoic acid</synonym>
    <synonym>Glycerol tricapric acid</synonym>
    <synonym>Glycerol tridecanoic acid</synonym>
    <synonym>Glyceryl tricapric acid</synonym>
    <synonym>Glyceryl tridecanoic acid</synonym>
    <synonym>1-Animal fats-2-animal fats-3-animal fats-glycerol</synonym>
    <synonym>1-Decanoic acid-2-decanoic acid-3-decanoic acid-glycerol</synonym>
    <synonym>TAG(10:0/10:0/10:0)</synonym>
    <synonym>Triacylglycerol</synonym>
    <synonym>Tracylglycerol(30:0)</synonym>
    <synonym>Triglyceride</synonym>
    <synonym>Tracylglycerol(10:0/10:0/10:0)</synonym>
    <synonym>TAG(30:0)</synonym>
    <synonym>TG(30:0)</synonym>
    <synonym>1,2, 3-Propanetriyl-decanoate</synonym>
    <synonym>1,2, 3-Propanetriyl-decanoic acid</synonym>
    <synonym>2,3-Bis(decanoyloxy)propyl decanoate</synonym>
    <synonym>2,3-Bis(decanoyloxy)propyl decanoate (acd/name 4.0)</synonym>
    <synonym>2,3-Bis(decanoyloxy)propyl decanoic acid</synonym>
    <synonym>Glycerol tricaprin</synonym>
    <synonym>Tri-decanoin</synonym>
    <synonym>Tricaprin</synonym>
    <synonym>TG(10:0/10:0/10:0)</synonym>
  </synonyms>
  <chemical_formula>C33H62O6</chemical_formula>
  <average_molecular_weight>554.853</average_molecular_weight>
  <monisotopic_moleculate_weight>554.454639716</monisotopic_moleculate_weight>
  <iupac_name>1,3-bis(decanoyloxy)propan-2-yl decanoate</iupac_name>
  <traditional_iupac>tricaprin</traditional_iupac>
  <cas_registry_number>621-71-6</cas_registry_number>
  <smiles>[H]C(COC(=O)CCCCCCCCC)(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCC</smiles>
  <inchi>InChI=1S/C33H62O6/c1-4-7-10-13-16-19-22-25-31(34)37-28-30(39-33(36)27-24-21-18-15-12-9-6-3)29-38-32(35)26-23-20-17-14-11-8-5-2/h30H,4-29H2,1-3H3</inchi>
  <inchikey>LADGBHLMCUINGV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerolipids</class>
    <sub_class>Triradylcglycerols</sub_class>
    <direct_parent>Triacylglycerols</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Triacyl-sn-glycerol</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Triacylglycerols</external_descriptor>
      <external_descriptor>triglyceride</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>8.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>10.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1,3-bis(decanoyloxy)propan-2-yl decanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>554.853</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>554.454639716</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]C(COC(=O)CCCCCCCCC)(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C33H62O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C33H62O6/c1-4-7-10-13-16-19-22-25-31(34)37-28-30(39-33(36)27-24-21-18-15-12-9-6-3)29-38-32(35)26-23-20-17-14-11-8-5-2/h30H,4-29H2,1-3H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LADGBHLMCUINGV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>78.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>158.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>70.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/10:0)</name>
      <smpdb_id>SMP0108241</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>621385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>621386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>621387</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Mottram HR, Evershed RP: Elucidation of the composition of bovine milk fat triacylglycerols using high-performance liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry. J Chromatogr A. 2001 Aug 17;926(2):239-53.</reference_text>
          <pubmed_id>11556330</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB003134</foodb_id>
  <drugbank_id/>
  <kegg_id/>
  <pubchem_compound_id>69310</pubchem_compound_id>
  <chemspider_id>62521</chemspider_id>
  <pdbe_id/>
  <chebi_id>77388</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5532</metlin_id>
  <synthesis_reference>Selmi, B.; Gontier, E.; Ergan, F.; Thomas, D.  Effects of fatty acid chain length and unsaturation number on triglyceride synthesis catalyzed by immobilized lipase in solvent-free medium.    Enzyme and Microbial Technology  (1998),  23(3/4),  182-186.  </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mottram HR, Evershed RP: Elucidation of the composition of bovine milk fat triacylglycerols using high-performance liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry. J Chromatogr A. 2001 Aug 17;926(2):239-53.</reference_text>
      <pubmed_id>11556330</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:36 UTC</creation_date>
  <update_date>2020-04-15 22:22:49 UTC</update_date>
  <accession>BMDB0000549</accession>
  <secondary_accessions>
    <accession>BMDB00549</accession>
  </secondary_accessions>
  <name>Gamma-Butyrolactone</name>
  <description/>
  <synonyms>
    <synonym>1,2-Butanolide</synonym>
    <synonym>1,4-Butanolide</synonym>
    <synonym>1,4-Lactone</synonym>
    <synonym>4-Butyrolactone</synonym>
    <synonym>4-Deoxytetronic acid</synonym>
    <synonym>4-Hydroxybutyric acid lactone</synonym>
    <synonym>Butyrolactone</synonym>
    <synonym>Dihydro-2(3H)-furanone</synonym>
    <synonym>gamma-Butanolactone</synonym>
    <synonym>gamma-Hydroxybutyric acid lactone</synonym>
    <synonym>gamma-Hydroxybutyrolactone</synonym>
    <synonym>Tetrahydrofuran-2-one</synonym>
    <synonym>4-Deoxytetronate</synonym>
    <synonym>4-Hydroxybutyrate lactone</synonym>
    <synonym>g-Butanolactone</synonym>
    <synonym>Γ-butanolactone</synonym>
    <synonym>g-Hydroxybutyrate lactone</synonym>
    <synonym>g-Hydroxybutyric acid lactone</synonym>
    <synonym>gamma-Hydroxybutyrate lactone</synonym>
    <synonym>Γ-hydroxybutyrate lactone</synonym>
    <synonym>Γ-hydroxybutyric acid lactone</synonym>
    <synonym>g-Hydroxybutyrolactone</synonym>
    <synonym>Γ-hydroxybutyrolactone</synonym>
    <synonym>g-Butyrolactone</synonym>
    <synonym>Γ-butyrolactone</synonym>
    <synonym>1-Oxacyclopentan-2-one</synonym>
    <synonym>2,3,4,5-Tetrahydro-2-furanone</synonym>
    <synonym>2-Oxolanone</synonym>
    <synonym>2-Oxotetrahydrofuran</synonym>
    <synonym>4,5-Dihydro-2(3H)-furanone</synonym>
    <synonym>4-Butanolide</synonym>
    <synonym>4-Hydroxy-butanoate</synonym>
    <synonym>4-Hydroxy-butanoic acid</synonym>
    <synonym>4-Hydroxy-butanoic acid g-lactone</synonym>
    <synonym>4-Hydroxybutanoate</synonym>
    <synonym>4-Hydroxybutanoic acid</synonym>
    <synonym>4-Hydroxybutanoic acid lactone</synonym>
    <synonym>Butyric acid lactone</synonym>
    <synonym>g-Butalactone</synonym>
    <synonym>g-Butyryllactone</synonym>
    <synonym>gamma-Butalactone</synonym>
    <synonym>gamma-Butyryllactone</synonym>
    <synonym>GBL</synonym>
    <synonym>Paint clean g</synonym>
    <synonym>Tetrahydro-2-furanone</synonym>
    <synonym>4 Butyrolactone</synonym>
    <synonym>gamma Butyrolactone</synonym>
    <synonym>Furanone, tetrahydro 2</synonym>
    <synonym>1,4 Butanolide</synonym>
    <synonym>4 Hydroxybutyric acid lactone</synonym>
    <synonym>Lactone, 4-hydroxybutyric acid</synonym>
    <synonym>gamma-Butyrolactone</synonym>
  </synonyms>
  <chemical_formula>C4H6O2</chemical_formula>
  <average_molecular_weight>86.0892</average_molecular_weight>
  <monisotopic_moleculate_weight>86.036779436</monisotopic_moleculate_weight>
  <iupac_name>oxolan-2-one</iupac_name>
  <traditional_iupac>butyrolactone</traditional_iupac>
  <cas_registry_number>96-48-0</cas_registry_number>
  <smiles>O=C1CCCO1</smiles>
  <inchi>InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2</inchi>
  <inchikey>YEJRWHAVMIAJKC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Lactones</class>
    <sub_class>Gamma butyrolactones</sub_class>
    <direct_parent>Gamma butyrolactones</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Gamma butyrolactone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Lactones</external_descriptor>
      <external_descriptor>butan-4-olide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-45 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.64</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>oxolan-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>86.0892</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>86.036779436</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O=C1CCCO1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H6O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YEJRWHAVMIAJKC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>26.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>20.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181934</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB003392</foodb_id>
  <chemspider_id>7029</chemspider_id>
  <drugbank_id>DB04699</drugbank_id>
  <pubchem_compound_id>7302</pubchem_compound_id>
  <chebi_id>42639</chebi_id>
  <pdbe_id/>
  <kegg_id>C01770</kegg_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Gamma-Butyrolactone</wikipedia_id>
  <metlin_id>5533</metlin_id>
  <synthesis_reference>Zhu, Yulei; Li, Yongwang; Xiang, Hongwei; Su, Hualian; Wu, Jiaxiang.  Process for preparation of g-butyrolactone with high yield and selectivity.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2001), 13 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00595</protein_accession>
      <name>Hydroxyacid-oxoacid transhydrogenase, mitochondrial</name>
      <uniprot_id>A6QP15</uniprot_id>
      <gene_name>ADHFE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:37 UTC</creation_date>
  <update_date>2020-03-13 16:22:03 UTC</update_date>
  <accession>BMDB0000550</accession>
  <secondary_accessions>
    <accession>BMDB00550</accession>
  </secondary_accessions>
  <name>5-Androstenetriol</name>
  <description/>
  <synonyms>
    <synonym>5-Androstene-3 beta,16 alpha,17 beta-triol</synonym>
    <synonym>5-Androstene-3,16,17-triol</synonym>
  </synonyms>
  <chemical_formula>C19H30O3</chemical_formula>
  <average_molecular_weight>306.4397</average_molecular_weight>
  <monisotopic_moleculate_weight>306.219494826</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,10R,11S,13R,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,13,14-triol</iupac_name>
  <traditional_iupac>5-androstenetriol</traditional_iupac>
  <cas_registry_number>4150-30-5</cas_registry_number>
  <smiles>[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-17,20-22H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,17-,18-,19-/m0/s1</inchi>
  <inchikey>GUGSXATYPSGVAY-DHKQUUGRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>16-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>16-alpha-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,10R,11S,13R,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,13,14-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>306.4397</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>306.219494826</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@@H](O)[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H30O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-17,20-22H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,17-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GUGSXATYPSGVAY-DHKQUUGRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>159354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>159355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>159356</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022110</foodb_id>
  <chemspider_id>7993771</chemspider_id>
  <pubchem_compound_id>9818021</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id/>
  <kegg_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5534</metlin_id>
  <synthesis_reference>Huffman, Max N.  Steroid esters from steroid ethers.    (1952),     US  2585553  19520212  CAN 46:52034  AN 1952:52034</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:38 UTC</creation_date>
  <update_date>2020-03-13 16:22:03 UTC</update_date>
  <accession>BMDB0000551</accession>
  <secondary_accessions>
    <accession>BMDB00551</accession>
  </secondary_accessions>
  <name>Etiocholanediol</name>
  <description/>
  <synonyms>
    <synonym>(3alpha,5beta,17beta)-Androstane-3,17-diol</synonym>
    <synonym>3alpha,17beta-Dihydroxyetiocholane</synonym>
    <synonym>(3a,5b,17b)-Androstane-3,17-diol</synonym>
    <synonym>(3Α,5β,17β)-androstane-3,17-diol</synonym>
    <synonym>3a,17b-Dihydroxyetiocholane</synonym>
    <synonym>3Α,17β-dihydroxyetiocholane</synonym>
    <synonym>5b-Androstane-3a,17b-diol</synonym>
    <synonym>b-Androstane-3a,17b-diol</synonym>
    <synonym>beta-Androstane-3a,17b-diol</synonym>
    <synonym>5Β-androstane-3α,17β-diol</synonym>
  </synonyms>
  <chemical_formula>C19H32O2</chemical_formula>
  <average_molecular_weight>292.4562</average_molecular_weight>
  <monisotopic_moleculate_weight>292.240230268</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7R,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol</iupac_name>
  <traditional_iupac>(1S,2S,5R,7R,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol</traditional_iupac>
  <cas_registry_number>1851-23-6</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,17+,18+,19+/m1/s1</inchi>
  <inchikey>CBMYJHIOYJEBSB-GCXXXECGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>androstane-3alpha,17beta-diol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7R,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>292.4562</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>292.240230268</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H32O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,17+,18+,19+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CBMYJHIOYJEBSB-GCXXXECGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372600</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022111</foodb_id>
  <chemspider_id>118551</chemspider_id>
  <pubchem_compound_id>134494</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>36714</chebi_id>
  <kegg_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Etiocholanediol</wikipedia_id>
  <metlin_id>5535</metlin_id>
  <synthesis_reference>Baulieu, Etienne Emile; Robel, Paul.  Androst-5-ene-3b,17b-diol-17a-H3 to testosterone-17a-H3 and 5a- and 5b-androstane-3a,17b-diol-17a-H3 in vivo.    Steroids  (1963),  2(1),  111-18.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:39 UTC</creation_date>
  <update_date>2020-03-23 17:43:08 UTC</update_date>
  <accession>BMDB0000552</accession>
  <secondary_accessions>
    <accession>BMDB00552</accession>
  </secondary_accessions>
  <name>3-Methylglutarylcarnitine</name>
  <description/>
  <synonyms>
    <synonym>(3R)-3-{[(3R)-4-carboxy-3-methylbutanoyl]oxy}-4-(trimethylazaniumyl)butanoic acid</synonym>
    <synonym>3-Methylglutarylcarnitine</synonym>
    <synonym>Methylglutarylcarnitine</synonym>
    <synonym>O-3-Methylglutarylcarnitine</synonym>
  </synonyms>
  <chemical_formula>C13H23NO6</chemical_formula>
  <average_molecular_weight>289.328</average_molecular_weight>
  <monisotopic_moleculate_weight>289.152537465</monisotopic_moleculate_weight>
  <iupac_name>(3R)-3-{[(3R)-4-carboxy-3-methylbutanoyl]oxy}-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>(3R)-3-{[(3R)-4-carboxy-3-methylbutanoyl]oxy}-4-(trimethylammonio)butanoate</traditional_iupac>
  <cas_registry_number/>
  <smiles>C[C@H](CC(O)=O)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C</smiles>
  <inchi>InChI=1S/C13H23NO6/c1-9(5-11(15)16)6-13(19)20-10(7-12(17)18)8-14(2,3)4/h9-10H,5-8H2,1-4H3,(H-,15,16,17,18)/t9-,10-/m1/s1</inchi>
  <inchikey>HFCPFJNSBPQJDP-NXEZZACHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Acyl carnitines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl-carnitine</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R)-3-{[(3R)-4-carboxy-3-methylbutanoyl]oxy}-4-(trimethylazaniumyl)butanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>289.328</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>289.152537465</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](CC(O)=O)CC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H23NO6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H23NO6/c1-9(5-11(15)16)6-13(19)20-10(7-12(17)18)8-14(2,3)4/h9-10H,5-8H2,1-4H3,(H-,15,16,17,18)/t9-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HFCPFJNSBPQJDP-NXEZZACHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>103.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>92.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.187 +/- 0.013</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id/>
  <chebi_id/>
  <chemspider_id/>
  <pubchem_compound_id/>
  <foodb_id>FDB022112</foodb_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference>Jooste, S.; Erasmus, E.; Mienie, L. J.; de Wet, W. J.; Gibson, K. M.  The detection of 3-methylglutarylcarnitine and a new dicarboxylic conjugate, 3-methylglutaconylcarnitine, in 3-methylglutaconic aciduria.    Clinica Chimica Acta  (1994),  230(1),  1-8. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:41 UTC</creation_date>
  <update_date>2020-03-13 16:22:05 UTC</update_date>
  <accession>BMDB0000553</accession>
  <secondary_accessions>
    <accession>BMDB00553</accession>
  </secondary_accessions>
  <name>3L,7D,11D-Phytanic acid</name>
  <description/>
  <synonyms>
    <synonym>3l,7D,11D-Phytanate</synonym>
    <synonym>3,7,11,15-Tetramethyl-[3S-(3R*,7S*,11S*)]-hexadecanoate</synonym>
    <synonym>3,7,11,15-Tetramethyl-[3S-(3R*,7S*,11S*)]-hexadecanoic acid</synonym>
    <synonym>(3S,7R,11R)-3,7,11,15-Tetramethylhexadecanoate</synonym>
  </synonyms>
  <chemical_formula>C20H40O2</chemical_formula>
  <average_molecular_weight>312.5304</average_molecular_weight>
  <monisotopic_moleculate_weight>312.302830524</monisotopic_moleculate_weight>
  <iupac_name>(3S,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid</iupac_name>
  <traditional_iupac>3L,7D,11D-phytanate</traditional_iupac>
  <cas_registry_number>31653-05-1</cas_registry_number>
  <smiles>CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](C)CC(O)=O</smiles>
  <inchi>InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)/t17-,18-,19+/m1/s1</inchi>
  <inchikey>RLCKHJSFHOZMDR-QRVBRYPASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Diterpenoids</sub_class>
    <direct_parent>Acyclic diterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyclic diterpenoid</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Branched fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3S,7R,11R)-3,7,11,15-tetramethylhexadecanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>312.5304</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>312.302830524</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](C)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H40O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)/t17-,18-,19+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RLCKHJSFHOZMDR-QRVBRYPASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>95.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369888</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022113</foodb_id>
  <chemspider_id>8148435</chemspider_id>
  <pubchem_compound_id>9972843</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id/>
  <kegg_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5537</metlin_id>
  <synthesis_reference>Burns, Christopher J.; Field, Leslie D.; Hashimoto, Kikuko; Petteys, Brian J.; Ridley, Damon D.; Rose, Michael.  Synthesis of stereoisomerically pure monoether lipids.    Australian Journal of Chemistry  (1999),  52(5),  387-394.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:42 UTC</creation_date>
  <update_date>2020-04-16 17:53:58 UTC</update_date>
  <accession>BMDB0000554</accession>
  <secondary_accessions>
    <accession>BMDB00554</accession>
  </secondary_accessions>
  <name>Dihydroandrosterone</name>
  <description/>
  <synonyms>
    <synonym>(3alpha,5alpha,17beta)-Androstane-3,17-diol</synonym>
    <synonym>3alpha,17beta-Dihydroxy-5alpha-androstane</synonym>
    <synonym>Hombreol</synonym>
    <synonym>(3a,5a,17b)-Androstane-3,17-diol</synonym>
    <synonym>(3Α,5α,17β)-androstane-3,17-diol</synonym>
    <synonym>3a,17b-Dihydroxy-5a-androstane</synonym>
    <synonym>3Α,17β-dihydroxy-5α-androstane</synonym>
    <synonym>Adiol</synonym>
    <synonym>Etiocholane-3a,17b-diol</synonym>
    <synonym>3a,5a-Tetrahydrotestosterone</synonym>
    <synonym>5a-Androstane-3a,17b-diol</synonym>
    <synonym>5alpha-Androstane-3alpha,17beta-androstanediol</synonym>
    <synonym>5alpha-Androstane-3alpha,17beta-diol</synonym>
    <synonym>Androstane-3a,17b-diol</synonym>
    <synonym>Etiocholane-3alpha,17beta-diol</synonym>
    <synonym>3a-Androstanediol</synonym>
    <synonym>3Α-androstanediol</synonym>
    <synonym>5Α-androstane-3α,17β-diol</synonym>
  </synonyms>
  <chemical_formula>C19H32O2</chemical_formula>
  <average_molecular_weight>292.4562</average_molecular_weight>
  <monisotopic_moleculate_weight>292.240230268</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol</iupac_name>
  <traditional_iupac>(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol</traditional_iupac>
  <cas_registry_number>1852-53-5</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17-,18-,19-/m0/s1</inchi>
  <inchikey>CBMYJHIOYJEBSB-KHOSGYARSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>androstane-3alpha,17beta-diol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>219 - 221 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>292.4562</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>292.240230268</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H32O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CBMYJHIOYJEBSB-KHOSGYARSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>256248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>256249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>256250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>276189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>276190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>276191</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022114</foodb_id>
  <chemspider_id>15039</chemspider_id>
  <drugbank_id>DB01530</drugbank_id>
  <pubchem_compound_id>15818</pubchem_compound_id>
  <chebi_id>36713</chebi_id>
  <pdbe_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5538</metlin_id>
  <synthesis_reference>Kieslich, Klaus.  5a-Androstane-3a,17b-diol.    Ger. Offen.  (1980),     6 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:43 UTC</creation_date>
  <update_date>2020-03-13 16:22:06 UTC</update_date>
  <accession>BMDB0000555</accession>
  <secondary_accessions>
    <accession>BMDB00555</accession>
  </secondary_accessions>
  <name>3-Methyladipic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Methyladipate</synonym>
    <synonym>(+/-)-3-methyladipic acid</synonym>
    <synonym>3-Methyl-hexanedioate</synonym>
    <synonym>3-Methyl-hexanedioic acid</synonym>
    <synonym>3-Methylhexanedioate</synonym>
    <synonym>3-Methylhexanedioic acid</synonym>
    <synonym>b-Methyl-adipic acid</synonym>
    <synonym>b-Methyladipate</synonym>
    <synonym>b-Methyladipic acid</synonym>
    <synonym>beta-Methyl-adipic acid</synonym>
    <synonym>beta-Methyladipate</synonym>
    <synonym>beta-Methyladipic acid</synonym>
    <synonym>(3S)-3-Methylhexanedioate</synonym>
    <synonym>3-Methyladipic acid</synonym>
  </synonyms>
  <chemical_formula>C7H12O4</chemical_formula>
  <average_molecular_weight>160.1678</average_molecular_weight>
  <monisotopic_moleculate_weight>160.073558872</monisotopic_moleculate_weight>
  <iupac_name>(3S)-3-methylhexanedioic acid</iupac_name>
  <traditional_iupac>(3S)-3-methylhexanedioic acid</traditional_iupac>
  <cas_registry_number>3058-01-3</cas_registry_number>
  <smiles>C[C@@H](CCC(O)=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C7H12O4/c1-5(4-7(10)11)2-3-6(8)9/h5H,2-4H2,1H3,(H,8,9)(H,10,11)/t5-/m0/s1</inchi>
  <inchikey>SYEOWUNSTUDKGM-YFKPBYRVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>101 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>248 mg/mL at 26 °C</value>
      <source>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3S)-3-methylhexanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>160.1678</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>160.073558872</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](CCC(O)=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H12O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H12O4/c1-5(4-7(10)11)2-3-6(8)9/h5H,2-4H2,1H3,(H,8,9)(H,10,11)/t5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SYEOWUNSTUDKGM-YFKPBYRVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332958</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022115</foodb_id>
  <chemspider_id>5367267</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>6999745</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>3797</metlin_id>
  <synthesis_reference>Vogel, Arthur I. Syntheses of cyclic compounds. VIII. Conversion of b-methyladipic acid into 3-methylcyclopentanone and the preparation of 3-methylcyclopentane-1,1-diacetic acid. Journal of the Chemical Society (1931), 907-14.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:44 UTC</creation_date>
  <update_date>2020-03-13 16:22:06 UTC</update_date>
  <accession>BMDB0000556</accession>
  <secondary_accessions>
    <accession>BMDB00556</accession>
  </secondary_accessions>
  <name>5b-Cholestane-3a,7a,12a,24,25-pentol</name>
  <description/>
  <synonyms>
    <synonym>3a,7a,12a,24,25-Pentahydroxycoprostane</synonym>
    <synonym>3alpha,7alpha,12alpha,24R,25-Pentahydroxy-5beta-cholestane</synonym>
    <synonym>5beta-Cholestane-3alpha,7alpha,12alpha,24R,25-pentol</synonym>
    <synonym>5b-Cholestane-3a,7a,12a,24R,25-pentol</synonym>
    <synonym>5Β-cholestane-3α,7α,12α,24R,25-pentol</synonym>
  </synonyms>
  <chemical_formula>C27H48O5</chemical_formula>
  <average_molecular_weight>452.667</average_molecular_weight>
  <monisotopic_moleculate_weight>452.350174646</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,9R,10R,11S,14R,15R,16S)-14-[(2R)-5,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</iupac_name>
  <traditional_iupac>(1S,2S,5R,9R,10R,11S,14R,15R,16S)-14-[(2R)-5,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</traditional_iupac>
  <cas_registry_number>58469-95-7</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)C(C)(C)O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C27H48O5/c1-15(6-9-22(30)25(2,3)32)18-7-8-19-24-20(14-23(31)27(18,19)5)26(4)11-10-17(28)12-16(26)13-21(24)29/h15-24,28-32H,6-14H2,1-5H3/t15-,16?,17-,18-,19+,20+,21-,22?,23+,24+,26+,27-/m1/s1</inchi>
  <inchikey>NHPWQASMMFUHIZ-OOOZRTEJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Pentahydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>24-hydroxysteroid</substituent>
      <substituent>25-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Pentahydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,9R,10R,11S,14R,15R,16S)-14-[(2R)-5,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>452.667</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>452.350174646</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)C(C)(C)O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H48O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H48O5/c1-15(6-9-22(30)25(2,3)32)18-7-8-19-24-20(14-23(31)27(18,19)5)26(4)11-10-17(28)12-16(26)13-21(24)29/h15-24,28-32H,6-14H2,1-5H3/t15-,16?,17-,18-,19+,20+,21-,22?,23+,24+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NHPWQASMMFUHIZ-OOOZRTEJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>101.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>126.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>54.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369108</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022116</foodb_id>
  <chemspider_id>13628107</chemspider_id>
  <pubchem_compound_id>21252253</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id/>
  <kegg_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5540</metlin_id>
  <synthesis_reference>Hoshita, Takahiko.  Bile acids and sterols. XLVII. Synthesis of 3a,7a,12a,25x,26-and 3a,7a,12a,24x,25-pentahydroxycoprostanes.    Journal of Biochemistry (Tokyo, Japan)  (1962),  52  176-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:45 UTC</creation_date>
  <update_date>2020-03-13 16:22:07 UTC</update_date>
  <accession>BMDB0000557</accession>
  <secondary_accessions>
    <accession>BMDB00557</accession>
  </secondary_accessions>
  <name>L-Alloisoleucine</name>
  <description>L-Alloisoleucine, also known as threo-L-isoleucine or alle, belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Alloisoleucine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Alloisoleucine has been found to be associated with several diseases known as eosinophilic esophagitis, short/branched chain acyl-coa dehydrogenase deficiency, and colorectal cancer; also l-alloisoleucine has been linked to the inborn metabolic disorders including maple syrup urine disease.</description>
  <synonyms>
    <synonym>(2S,3R)-2-Amino-3-methylpentanoic acid</synonym>
    <synonym>Alle</synonym>
    <synonym>Allo-L-isoleucine</synonym>
    <synonym>L(+)-Alloisoleucine</synonym>
    <synonym>Threo-3-methyl-L-norvaline</synonym>
    <synonym>Threo-L-isoleucine</synonym>
    <synonym>(2S,3R)-2-Amino-3-methylpentanoate</synonym>
    <synonym>(3R)-LS-Isoleucine</synonym>
    <synonym>2-Amino-3-methyl-[S-(r*,s*)]-pentanoate</synonym>
    <synonym>2-Amino-3-methyl-[S-(r*,s*)]-pentanoic acid</synonym>
    <synonym>Allo-isoleucine</synonym>
    <synonym>L-Allo-isoleucine</synonym>
    <synonym>[S-(R*,s*)]-2-amino-3-methylpentanoate</synonym>
    <synonym>[S-(R*,s*)]-2-amino-3-methylpentanoic acid</synonym>
    <synonym>Alloisoleucine</synonym>
    <synonym>Isoleucine, L isomer</synonym>
    <synonym>Isoleucine, L-isomer</synonym>
    <synonym>L-Isomer isoleucine</synonym>
    <synonym>L-Isoleucine</synonym>
    <synonym>Isoleucine</synonym>
  </synonyms>
  <chemical_formula>C6H13NO2</chemical_formula>
  <average_molecular_weight>131.1729</average_molecular_weight>
  <monisotopic_moleculate_weight>131.094628665</monisotopic_moleculate_weight>
  <iupac_name>(2S,3R)-2-amino-3-methylpentanoic acid</iupac_name>
  <traditional_iupac>allo-isoleucine</traditional_iupac>
  <cas_registry_number>1509-34-8</cas_registry_number>
  <smiles>CC[C@@H](C)[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5+/m1/s1</inchi>
  <inchikey>AGPKZVBTJJNPAG-UHNVWZDZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Isoleucine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isoleucine or derivatives</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>alloisoleucine</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>60 - 64 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>34.4 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.7</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3R)-2-amino-3-methylpentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>131.1729</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>131.094628665</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC[C@@H](C)[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AGPKZVBTJJNPAG-UHNVWZDZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281795</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022117</foodb_id>
  <chemspider_id>89698</chemspider_id>
  <drugbank_id>DB01739</drugbank_id>
  <pubchem_compound_id>99288</pubchem_compound_id>
  <chebi_id>43433</chebi_id>
  <pdbe_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:47 UTC</creation_date>
  <update_date>2020-03-13 16:22:07 UTC</update_date>
  <accession>BMDB0000558</accession>
  <secondary_accessions>
    <accession>BMDB00558</accession>
  </secondary_accessions>
  <name>5a-Cholestane-3a,7a,12a,23,25-pentol</name>
  <description/>
  <synonyms>
    <synonym>(3a,5a,7a,12a,23S)-Cholestane-3,7,12,23,25-pentol</synonym>
  </synonyms>
  <chemical_formula>C27H48O5</chemical_formula>
  <average_molecular_weight>452.667</average_molecular_weight>
  <monisotopic_moleculate_weight>452.350174646</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-14-[(2S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</iupac_name>
  <traditional_iupac>(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-14-[(2S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</traditional_iupac>
  <cas_registry_number>137252-15-4</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@@H](C)CC(O)CC(C)(C)O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C27H48O5/c1-15(10-18(29)14-25(2,3)32)19-6-7-20-24-21(13-23(31)27(19,20)5)26(4)9-8-17(28)11-16(26)12-22(24)30/h15-24,28-32H,6-14H2,1-5H3/t15-,16+,17+,18?,19+,20-,21-,22+,23-,24-,26-,27+/m0/s1</inchi>
  <inchikey>OXSBBBPDYVCAKC-KHMINMIBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Pentahydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Cholesterols and derivatives</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>23-hydroxysteroid</substituent>
      <substituent>25-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholestane-skeleton</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Pentahydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-14-[(2S)-4,6-dihydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>452.667</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>452.350174646</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@@H](C)CC(O)CC(C)(C)O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H48O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H48O5/c1-15(10-18(29)14-25(2,3)32)19-6-7-20-24-21(13-23(31)27(19,20)5)26(4)9-8-17(28)11-16(26)12-22(24)30/h15-24,28-32H,6-14H2,1-5H3/t15-,16+,17+,18?,19+,20-,21-,22+,23-,24-,26-,27+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OXSBBBPDYVCAKC-KHMINMIBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>101.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>126.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>53.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347607</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022118</foodb_id>
  <chemspider_id>13628108</chemspider_id>
  <pubchem_compound_id>21252254</pubchem_compound_id>
  <drugbank_id/>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5542</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:48 UTC</creation_date>
  <update_date>2020-03-13 16:22:08 UTC</update_date>
  <accession>BMDB0000559</accession>
  <secondary_accessions>
    <accession>BMDB00559</accession>
  </secondary_accessions>
  <name>3-Methoxy-4-hydroxyphenylethyleneglycol sulfate</name>
  <description/>
  <synonyms>
    <synonym>3-Methoxy-4-hydroxyphenylethyleneglycol sulfuric acid</synonym>
    <synonym>3-Methoxy-4-hydroxyphenylethyleneglycol sulphate</synonym>
    <synonym>3-Methoxy-4-hydroxyphenylethyleneglycol sulphuric acid</synonym>
    <synonym>(3-Methoxy-4-hydroxyphenyl)ethylene glycol sulfate</synonym>
    <synonym>(3-Methoxy-4-hydroxyphenyl)ethylene glycol sulphate</synonym>
    <synonym>(3-Methoxy-4-hydroxyphenyl)glycol O-sulfate</synonym>
    <synonym>(3-Methoxy-4-hydroxyphenyl)glycol O-sulphate</synonym>
    <synonym>(3-Methoxy-4-hydroxyphenyl)glycol sulfate ester</synonym>
    <synonym>(3-Methoxy-4-hydroxyphenyl)glycol sulphate ester</synonym>
    <synonym>3-Methoxy-4-hydroxyphenylglycol 4-sulfate</synonym>
    <synonym>3-Methoxy-4-hydroxyphenylglycol 4-sulphate</synonym>
    <synonym>MOPEG sulfate</synonym>
    <synonym>MOPEG sulphate</synonym>
    <synonym>[4-(1,2-Dihydroxyethyl)-2-methoxyphenyl]oxidanesulfonate</synonym>
    <synonym>[4-(1,2-Dihydroxyethyl)-2-methoxyphenyl]oxidanesulphonate</synonym>
    <synonym>[4-(1,2-Dihydroxyethyl)-2-methoxyphenyl]oxidanesulphonic acid</synonym>
    <synonym>MOPEG sulfuric acid</synonym>
    <synonym>MOPEG sulphuric acid</synonym>
    <synonym>1-[3-Methoxy-4-(sulfooxy)phenyl]-1,2-ethanediol</synonym>
    <synonym>4-Hydroxy-3-methoxyphenylglycol sulfate</synonym>
    <synonym>HMPG Sulfate</synonym>
    <synonym>MHPG-SO4</synonym>
  </synonyms>
  <chemical_formula>C9H12O7S</chemical_formula>
  <average_molecular_weight>264.252</average_molecular_weight>
  <monisotopic_moleculate_weight>264.030373428</monisotopic_moleculate_weight>
  <iupac_name>[4-(1,2-dihydroxyethyl)-2-methoxyphenyl]oxidanesulfonic acid</iupac_name>
  <traditional_iupac>mopeg sulfate</traditional_iupac>
  <cas_registry_number>3415-67-6</cas_registry_number>
  <smiles>COC1=C(OS(O)(=O)=O)C=CC(=C1)C(O)CO</smiles>
  <inchi>InChI=1S/C9H12O7S/c1-15-9-4-6(7(11)5-10)2-3-8(9)16-17(12,13)14/h2-4,7,10-11H,5H2,1H3,(H,12,13,14)</inchi>
  <inchikey>WUFPNASKMLJSND-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic sulfuric acids and derivatives</class>
    <sub_class>Arylsulfates</sub_class>
    <direct_parent>Phenylsulfates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenylsulfate</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[4-(1,2-dihydroxyethyl)-2-methoxyphenyl]oxidanesulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>264.252</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>264.030373428</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=C(OS(O)(=O)=O)C=CC(=C1)C(O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H12O7S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H12O7S/c1-15-9-4-6(7(11)5-10)2-3-8(9)16-17(12,13)14/h2-4,7,10-11H,5H2,1H3,(H,12,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WUFPNASKMLJSND-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>57.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335280</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022119</foodb_id>
  <chemspider_id>4039</chemspider_id>
  <pubchem_compound_id>4183</pubchem_compound_id>
  <drugbank_id/>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id>137054</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5543</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:49 UTC</creation_date>
  <update_date>2020-03-13 16:22:08 UTC</update_date>
  <accession>BMDB0000560</accession>
  <secondary_accessions>
    <accession>BMDB00560</accession>
  </secondary_accessions>
  <name>5,8-Tetradecadienoic acid</name>
  <description/>
  <synonyms>
    <synonym>5,8-Tetradecadienoate</synonym>
  </synonyms>
  <chemical_formula>C14H24O2</chemical_formula>
  <average_molecular_weight>224.344</average_molecular_weight>
  <monisotopic_moleculate_weight>224.177630013</monisotopic_moleculate_weight>
  <iupac_name>(5E,8E)-tetradeca-5,8-dienoic acid</iupac_name>
  <traditional_iupac>5,8-tetradecadienoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H]\C(CCCCC)=C(\[H])C\C([H])=C(/[H])CCCC(O)=O</smiles>
  <inchi>InChI=1S/C14H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h6-7,9-10H,2-5,8,11-13H2,1H3,(H,15,16)/b7-6+,10-9+</inchi>
  <inchikey>HXHZGHRLVRFQDR-AVQMFFATSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5E,8E)-tetradeca-5,8-dienoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>224.344</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>224.177630013</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]\C(CCCCC)=C(\[H])C\C([H])=C(/[H])CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H24O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h6-7,9-10H,2-5,8,11-13H2,1H3,(H,15,16)/b7-6+,10-9+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HXHZGHRLVRFQDR-AVQMFFATSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>70.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>27.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1256371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1256372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1256373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1371544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1371545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1371546</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id>5312408</pubchem_compound_id>
  <drugbank_id/>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Guex, Waldemar; Rueegg, Rudolf; Schwieter, Ulrich.  Unsaturated alcohols and their esters.    (1960),     DE  1111615  19600129  CAN 56:31075  AN 1962:31075 </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:50 UTC</creation_date>
  <update_date>2020-04-16 20:39:18 UTC</update_date>
  <accession>BMDB0000561</accession>
  <secondary_accessions>
    <accession>BMDB00561</accession>
  </secondary_accessions>
  <name>B-Carotene</name>
  <description>Beta-Carotene, also known as B-carotene, belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Beta-Carotene is possibly soluble (in water) and possibly neutral. Beta-Carotene exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>1,1'-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl]bis(2,6,6-trimethylcyclohexene)</synonym>
    <synonym>all-trans-beta-Carotene</synonym>
    <synonym>beta-Karotin</synonym>
    <synonym>all-trans-b-Carotene</synonym>
    <synonym>all-trans-Β-carotene</synonym>
    <synonym>b-Karotin</synonym>
    <synonym>Β-karotin</synonym>
    <synonym>b-Carotene</synonym>
    <synonym>Β-carotene</synonym>
    <synonym>(all-e)-1,1'-(3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis</synonym>
    <synonym>(all-e)-1,1'-(3,7,12,16-Tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene-1,18-diyl)bis[2,6,6-trimethyl-cyclohexene</synonym>
    <synonym>all-e-b-Carotene</synonym>
    <synonym>all-epsilon-beta-Carotene</synonym>
    <synonym>Betacarotene</synonym>
    <synonym>BetaVit</synonym>
    <synonym>Carotaben</synonym>
    <synonym>Carotene base 80S</synonym>
    <synonym>FOOD Orange 5</synonym>
    <synonym>KPMK</synonym>
    <synonym>Lucaratin</synonym>
    <synonym>Lucarotin</synonym>
    <synonym>Lurotin</synonym>
    <synonym>Provatene</synonym>
    <synonym>Provatenol</synonym>
    <synonym>Rovimix b-carotene</synonym>
    <synonym>Serlabo</synonym>
    <synonym>Solatene</synonym>
    <synonym>Hermal brand OF betacarotene</synonym>
    <synonym>Max-caro</synonym>
    <synonym>Merck brand OF betacarotene</synonym>
    <synonym>Roche brand OF betacarotene</synonym>
    <synonym>BellaCarotin</synonym>
    <synonym>Betacarotene roche brand</synonym>
    <synonym>Betacarotene solgar brand</synonym>
    <synonym>Marlyn brand OF betacarotene</synonym>
    <synonym>Betacarotene hermal brand</synonym>
    <synonym>Max caro</synonym>
    <synonym>Solgar brand OF betacarotene</synonym>
    <synonym>3m Brand OF betacarotene</synonym>
    <synonym>Betacarotene 3m brand</synonym>
    <synonym>Betacarotene marlyn brand</synonym>
    <synonym>Betacarotene merck brand</synonym>
    <synonym>Carotene, beta</synonym>
    <synonym>MaxCaro</synonym>
    <synonym>Vetoron</synonym>
    <synonym>beta Carotene</synonym>
    <synonym>b Carotene</synonym>
    <synonym>Β carotene</synonym>
    <synonym>beta-Carotene</synonym>
  </synonyms>
  <chemical_formula>C40H56</chemical_formula>
  <average_molecular_weight>536.888</average_molecular_weight>
  <monisotopic_moleculate_weight>536.438201803</monisotopic_moleculate_weight>
  <iupac_name>1,3,3-trimethyl-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene</iupac_name>
  <traditional_iupac>β-carotene</traditional_iupac>
  <cas_registry_number>7235-40-7</cas_registry_number>
  <smiles>C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C</smiles>
  <inchi>InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+</inchi>
  <inchikey>OENHQHLEOONYIE-JLTXGRSLSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Tetraterpenoids</sub_class>
    <direct_parent>Carotenes</direct_parent>
    <alternative_parents>
      <alternative_parent>Branched unsaturated hydrocarbons</alternative_parent>
      <alternative_parent>Cycloalkenes</alternative_parent>
      <alternative_parent>Unsaturated aliphatic hydrocarbons</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Branched unsaturated hydrocarbon</substituent>
      <substituent>Carotene</substituent>
      <substituent>Cyclic olefin</substituent>
      <substituent>Cycloalkene</substituent>
      <substituent>Hydrocarbon</substituent>
      <substituent>Olefin</substituent>
      <substituent>Unsaturated aliphatic hydrocarbon</substituent>
      <substituent>Unsaturated hydrocarbon</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C40 isoprenoids (tetraterpenes)</external_descriptor>
      <external_descriptor>C40 isoprenoids (tetraterpenes)</external_descriptor>
      <external_descriptor>Carotenoids</external_descriptor>
      <external_descriptor>cyclic carotene</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>183 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.6 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>9.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>11.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1,3,3-trimethyl-2-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>536.888</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>536.438201803</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C40H56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OENHQHLEOONYIE-JLTXGRSLSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>191.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>72.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Retinol Metabolism</name>
      <smpdb_id>SMP0087260</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451859</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.127</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Diet: low hay diet</comment>
      <references>
        <reference>
          <reference_text>Noziere P, Grolier P, Durand D, Ferlay A, Pradel P, Martin B: Variations in carotenoids, fat-soluble micronutrients, and color in cows' plasma and milk following changes in forage and feeding level. J Dairy Sci. 2006 Jul;89(7):2634-48. doi: 10.3168/jds.S0022-0302(06)72340-2.</reference_text>
          <pubmed_id>16772583</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0713</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk collected 8-14 wks after parturition; 2nd lactation; paper also contains values for other lactations/seasons</comment>
      <references>
        <reference>
          <reference_text>Larson LL, Wallen SE, Owen FG, Lowry SR: Relation of age, season, production, and health indices to iodine and beta-carotene concentrations in cow's milk. J Dairy Sci. 1983 Dec;66(12):2557-62. doi: 10.3168/jds.S0022-0302(83)82126-2.</reference_text>
          <pubmed_id>6668379</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.415 +/- 0.0466</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Diet: corn silage with concentrates; Breed: Holstein</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.298 +/- 0.142</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw. Diet: grass silage with concentates; Breed: holstein</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0400 +/- 0.0200</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Spanish commercial milk; low-fat 1.5%</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.110 +/- 0.0400</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Spanish commercial milk; low-fat 3.6%</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0700 +/- 0.0100</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Spanish commercial milk; skim 0.3% fat</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.131</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.131</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0246</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0412</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0246</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.285</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.298</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.298</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0745 - 10.293</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Chotyakul N, Pateiro-Moure M, Saraiva JA, Torres JA, Pérez-Lamela C. 2014. Simultaneous HPLC–DAD quantification of vitamins A and E content in raw, pasteurized, and UHT cow’s milk and their changes during storage. European Food Research and Technology. 238(4):535–547 </reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples have been collected from Heifer cows.</comment>
      <references>
        <reference>
          <reference_text>Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub  2013 Jun 5.</reference_text>
          <pubmed_id>23871026</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02094</kegg_id>
  <pubchem_compound_id>5280489</pubchem_compound_id>
  <foodb_id>FDB014613</foodb_id>
  <chemspider_id/>
  <drugbank_id>DB06755</drugbank_id>
  <pdbe_id/>
  <chebi_id>17579</chebi_id>
  <meta_cyc_id>CPD1F-129</meta_cyc_id>
  <knapsack_id>C00000919</knapsack_id>
  <wikipedia_id>Beta_Carotene</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Larson LL, Wallen SE, Owen FG, Lowry SR: Relation of age, season, production, and health indices to iodine and beta-carotene concentrations in cow's milk. J Dairy Sci. 1983 Dec;66(12):2557-62. doi: 10.3168/jds.S0022-0302(83)82126-2.</reference_text>
      <pubmed_id>6668379</pubmed_id>
    </reference>
    <reference>
      <reference_text>Noziere P, Grolier P, Durand D, Ferlay A, Pradel P, Martin B: Variations in carotenoids, fat-soluble micronutrients, and color in cows' plasma and milk following changes in forage and feeding level. J Dairy Sci. 2006 Jul;89(7):2634-48. doi: 10.3168/jds.S0022-0302(06)72340-2.</reference_text>
      <pubmed_id>16772583</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570</reference_text>
    </reference>
    <reference>
      <reference_text>International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526</reference_text>
    </reference>
    <reference>
      <reference_text>Chotyakul N, Pateiro-Moure M, Saraiva JA, Torres JA, Pérez-Lamela C. 2014. Simultaneous HPLC–DAD quantification of vitamins A and E content in raw, pasteurized, and UHT cow’s milk and their changes during storage. European Food Research and Technology. 238(4):535–547 </reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:51 UTC</creation_date>
  <update_date>2020-04-16 20:38:29 UTC</update_date>
  <accession>BMDB0000562</accession>
  <secondary_accessions>
    <accession>BMDB00562</accession>
  </secondary_accessions>
  <name>Creatinine</name>
  <description>Creatinine, also known as krebiozen, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Creatinine exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Creatinine exists in all living organisms, ranging from bacteria to humans. Creatinine is a potentially toxic compound. Creatinine has been found to be associated with several diseases known as partial lipodystrophy, crohn's disease, long-chain fatty acids, defect in transport of, and chronic renal failure; also creatinine has been linked to the inborn metabolic disorders including hyperoxalemia.</description>
  <synonyms>
    <synonym>1-Methylglycocyamidine</synonym>
    <synonym>1-Methylhydantoin-2-imide</synonym>
    <synonym>2-Amino-1,5-dihydro-1-methyl-4H-imidazol-4-one</synonym>
    <synonym>2-Amino-1-methylimidazolin-4-one</synonym>
    <synonym>Creatine anhydride</synonym>
    <synonym>Creatinina</synonym>
    <synonym>Kreatinin</synonym>
    <synonym>2-Amino-1-methyl-1,5-dihydroimidazol-4-one</synonym>
    <synonym>Krebiozen</synonym>
    <synonym>Sulfate salt, creatinine</synonym>
    <synonym>Creatinine sulfate salt</synonym>
    <synonym>Salt, creatinine sulfate</synonym>
  </synonyms>
  <chemical_formula>C4H7N3O</chemical_formula>
  <average_molecular_weight>113.1179</average_molecular_weight>
  <monisotopic_moleculate_weight>113.058911861</monisotopic_moleculate_weight>
  <iupac_name>2-imino-1-methylimidazolidin-4-one</iupac_name>
  <traditional_iupac>creatinina</traditional_iupac>
  <cas_registry_number>60-27-5</cas_registry_number>
  <smiles>CN1CC(=O)NC1=N</smiles>
  <inchi>InChI=1S/C4H7N3O/c1-7-2-3(8)6-4(7)5/h2H2,1H3,(H2,5,6,8)</inchi>
  <inchikey>DDRJAANPRJIHGJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Guanidines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolinones</alternative_parent>
      <alternative_parent>N-acylimines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-imidazoline</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazolinone</substituent>
      <substituent>N-acylimine</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>imidazolidinone</external_descriptor>
      <external_descriptor>lactam</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>303 °C (decomposes)</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>80.1 mg/mL at 16 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.76</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-imino-1-methylimidazolidin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>113.1179</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>113.058911861</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1CC(=O)NC1=N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H7N3O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H7N3O/c1-7-2-3(8)6-4(7)5/h2H2,1H3,(H2,5,6,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DDRJAANPRJIHGJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>56.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437414</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>97.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Dacos Chemistry Analyzer in Hereford cows</comment>
      <references>
        <reference>
          <reference_text>Early RJ, McBride BW, Ball RO: Growth and metabolism in somatotropin-treated steers: I. Growth, serum chemistry and carcass weights. J Anim Sci. 1990 Dec;68(12):4134-43. doi: 10.2527/1990.68124134x.</reference_text>
          <pubmed_id>2286555</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in lactating Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>105.200-171.502</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by procedure of Folin and Wu (1919)</comment>
      <references>
        <reference>
          <reference_text>Arthur K. Anderson, Howard E. Gayley, Avery D. Pratt. Studies on the Chemical Composition of Bovine Blood. J. Dairy Science (1930) 13(4):336-348   doi: 10.3168/jds.S0022-0302(30)93530-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>109-140</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Cobas c311/501 chemistry analyzer</comment>
      <references>
        <reference>
          <reference_text>Consolo NRB, Munro JC, Bourgon SL, Karrow NA, Fredeen AH, Martell JE, Montanholi YR: Associations of Blood Analysis with Feed Efficiency and Developmental Stage in Grass-Fed Beef Heifers. Animals (Basel). 2018 Aug 2;8(8). pii: ani8080133. doi: 10.3390/ani8080133.</reference_text>
          <pubmed_id>30072590</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>113+/-17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>143-179</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Creatinine OSR6118 kit with Beckman-Olympus AU 600 chemistry analyzer</comment>
      <references>
        <reference>
          <reference_text>Liker B.,  L. Bačar-Huskić,  M. Knežević,  V. Rupić,  N. Vranešić,  Ž. Romić,  D. Grbeša,  D. Mačešić,  J. Leto,  Z. Antunović,  Ž. Krnić. 2005. Blood metabolites and haematological indices of pregnant beef cows fed rumen-protected methionine. J. Anim. Feed Sci. 14(4):625–638</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>58+/-12</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>313+/-48</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>50.69 +/- 7.42</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>53.0420 - 106.0839</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Indyk HE, Woollard DC: Determination of orotic acid, uric acid, and creatinine in milk by liquid chromatography. J AOAC Int. 2004 Jan-Feb;87(1):116-22.</reference_text>
          <pubmed_id>15084094</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>80 - 176</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>80 - 167</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>81 - 125</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>81 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>87 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>83 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>68 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>66 +/- 7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>70 +/- 6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>71 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>66 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>53.41 +/- 9.12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>45.12 +/- 8.40</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>138.25 +/- 10.52</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>189.32 +/- 12.46</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>242.65 +/- 27.29</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>128-429</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>413.08 +/- 15.73</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1200</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>469-1050</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>315+/-47</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>123+/-26</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein.</comment>
      <references>
        <reference>
          <reference_text>Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17.</reference_text>
          <pubmed_id>22059599</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00791</kegg_id>
  <pubchem_compound_id>588</pubchem_compound_id>
  <foodb_id>FDB021814</foodb_id>
  <chemspider_id>568</chemspider_id>
  <drugbank_id>DB11846</drugbank_id>
  <pdbe_id/>
  <chebi_id>16737</chebi_id>
  <meta_cyc_id>CREATININE</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Creatinine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>36009</bigg_id>
  <metlin_id>8</metlin_id>
  <synthesis_reference>Reddick, Rebecca E.; Kenyon, George L. Syntheses and NMR studies of specifically labeled [2-15N]phosphocreatine, [2-15N]creatinine, and related 15N-labeled compounds. Journal of the American Chemical Society (1987), 109(14), 4380-7.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Indyk HE, Woollard DC: Determination of orotic acid, uric acid, and creatinine in milk by liquid chromatography. J AOAC Int. 2004 Jan-Feb;87(1):116-22.</reference_text>
      <pubmed_id>15084094</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:52 UTC</creation_date>
  <update_date>2020-04-14 22:47:48 UTC</update_date>
  <accession>BMDB0000564</accession>
  <secondary_accessions>
    <accession>BMDB00564</accession>
  </secondary_accessions>
  <name>PC(16:0/16:0)</name>
  <description>PC(16:0/16:0), also known as DPPC or 16:0-16:0-PC, belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. Thus, PC(16:0/16:0) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/16:0) exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. PC(16:0/16:0) exists in all eukaryotes, ranging from yeast to humans. In cattle, PC(16:0/16:0) is involved in the metabolic pathway called phospholipid biosynthesis pathway.</description>
  <synonyms>
    <synonym>1,2-Bis(hexadecanoyl)-sn-glycero-3-phosphocholine</synonym>
    <synonym>1,2-Dipalmitoyl-L-lecithin</synonym>
    <synonym>1,2-Dipalmitoyl-sn-glycero-3-phosphatidylcholine</synonym>
    <synonym>1,2-Dipalmitoyl-sn-glycero-3-phosphocholine</synonym>
    <synonym>1,2-Dipalmitoylphosphatidylcholine</synonym>
    <synonym>1-16:0-2-16:0-Phosphatidylcholine</synonym>
    <synonym>16:0-16:0-PC</synonym>
    <synonym>Colfosceril palmitate</synonym>
    <synonym>Colfoscerili palmitas</synonym>
    <synonym>Dipalmitoyl phosphatidylcholine</synonym>
    <synonym>Dipalmitoyl-GPC</synonym>
    <synonym>Dipalmitoylphosphatidylcholine</synonym>
    <synonym>GPC(16:0/16:0)</synonym>
    <synonym>GPCho 16:0/16:0</synonym>
    <synonym>GPCho(16:0/16:0)</synonym>
    <synonym>Palmitate de colfosceril</synonym>
    <synonym>Palmitato de colfoscerilo</synonym>
    <synonym>PC 16:0/16:0</synonym>
    <synonym>PC(32:0)</synonym>
    <synonym>Phosphatidylcholine 16:0/16:0</synonym>
    <synonym>Phosphatidylcholine(16:0/16:0)</synonym>
    <synonym>Phosphatidylcholine(32:0)</synonym>
    <synonym>Colfosceril palmitic acid</synonym>
    <synonym>Palmitic acid de colfosceril</synonym>
    <synonym>1,2-Dipalmitoyl-rac-glycero-3-phosphocholine</synonym>
    <synonym>Lecithin</synonym>
    <synonym>1,2-Dihexadecanoyl-rac-glycero-3-phosphocholine</synonym>
    <synonym>GPCho(32:0)</synonym>
    <synonym>(R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide hydroxide inner salt</synonym>
    <synonym>(R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide inner salt</synonym>
    <synonym>1,2-Bis(palmitoyl)-sn-glycero-3-phosphocholine</synonym>
    <synonym>1,2-Dihexadecanoyl-sn-glycerol-3-phosphorylcholine</synonym>
    <synonym>1,2-Dipalmitoyl-3-sn-phosphatidylcholine</synonym>
    <synonym>1,2-Dipalmitoyl-L-3-phosphatidylcholine</synonym>
    <synonym>1,2-Dipalmitoyl-L-a-lecithin</synonym>
    <synonym>1,2-Dipalmitoyl-L-a-phosphatidylcholine</synonym>
    <synonym>1,2-Dipalmitoyl-L-alpha-lecithin</synonym>
    <synonym>1,2-Dipalmitoyl-L-alpha-phosphatidylcholine</synonym>
    <synonym>1,2-Dipalmitoyl-L-phosphatidylcholine</synonym>
    <synonym>1,2-Dipalmitoyl-sn-3-glycerophosphocholine</synonym>
    <synonym>1,2-Dipalmitoyl-sn-glycero-3-phosphorylcholine</synonym>
    <synonym>1,2-Dipalmitoyl-sn-glycerol-3-phosphocholine</synonym>
    <synonym>1,2-Dipalmitoyl-sn-glycerophosphocholine</synonym>
    <synonym>1,2-Dipalmitoyl-sn-glycerophosphorylcholine</synonym>
    <synonym>1,2-Dipalmitoyl-sn-glyceryl-3-phosphocholine</synonym>
    <synonym>1,2-Dipalmitoyl-sn-phosphatidylcholine</synonym>
    <synonym>1,2-Dipalmitoylglycero-3-phosphocholine</synonym>
    <synonym>1,2-L-a-Dipalmitoylphosphatidylcholine</synonym>
    <synonym>1,2-L-alpha-Dipalmitoylphosphatidylcholine</synonym>
    <synonym>b,g-Dipalmitoyl L-a-phosphatidylcholine</synonym>
    <synonym>b,g-Dipalmitoyl L-alpha-phosphatidylcholine</synonym>
    <synonym>b,g-Dipalmitoyl-L-(a)-lecithin</synonym>
    <synonym>b,g-Dipalmitoyl-L-phosphatidylcholine</synonym>
    <synonym>Dihexadecanoyl-sn-glycero-3-phosphocholine</synonym>
    <synonym>Dipalmitoyl L-a-phosphatidylcholine</synonym>
    <synonym>Dipalmitoyl L-alpha-phosphatidylcholine</synonym>
    <synonym>Dipalmitoyl-L-3-glycerylphosphorylcholine</synonym>
    <synonym>Dipalmitoyl-L-a-lecithin</synonym>
    <synonym>Dipalmitoyl-L-a-phosphatidylcholine</synonym>
    <synonym>Dipalmitoyl-L-alpha-lecithin</synonym>
    <synonym>Dipalmitoyl-L-alpha-phosphatidylcholine</synonym>
    <synonym>Dipalmitoyl-sn-3-phosphatidylcholine</synonym>
    <synonym>DPPC</synonym>
    <synonym>L-1,2-Dipalmitoyl-a-lecithin</synonym>
    <synonym>L-1,2-Dipalmitoyl-alpha-lecithin</synonym>
    <synonym>L-1,2-Dipalmitoylphosphatidylcholine</synonym>
    <synonym>L-a-1,2-Dipalmitoyl lecithin</synonym>
    <synonym>L-a-Dipalmitoylecithin</synonym>
    <synonym>L-a-Dipalmitoyllecithin</synonym>
    <synonym>L-a-Dipalmitoylphosphatidylcholine</synonym>
    <synonym>L-a-DPPC</synonym>
    <synonym>L-alpha-1,2-Dipalmitoyl lecithin</synonym>
    <synonym>L-alpha-Dipalmitoylecithin</synonym>
    <synonym>L-alpha-Dipalmitoyllecithin</synonym>
    <synonym>L-alpha-Dipalmitoylphosphatidylcholine</synonym>
    <synonym>L-alpha-DPPC</synonym>
    <synonym>L-b,g-Dipalmitoyl-a-lecithin</synonym>
    <synonym>L-b,g-Dipalmitoyl-a-phosphatidylcholine</synonym>
    <synonym>L-b,g-Dipalmitoyl-alpha-lecithin</synonym>
    <synonym>L-b,g-Dipalmitoyl-alpha-phosphatidylcholine</synonym>
    <synonym>L-b,g-Dipalmitoylphosphatidylcholine</synonym>
    <synonym>L-Dipalmitoyl lecithin</synonym>
    <synonym>L-DPPC</synonym>
    <synonym>PC Aa C32:0</synonym>
    <synonym>sn-3-Dipalmitoyllecithin</synonym>
    <synonym>1,2-Dipalmitoyl-GPC</synonym>
    <synonym>PC(16:0/16:0)</synonym>
  </synonyms>
  <chemical_formula>C40H80NO8P</chemical_formula>
  <average_molecular_weight>734.0389</average_molecular_weight>
  <monisotopic_moleculate_weight>733.562155053</monisotopic_moleculate_weight>
  <iupac_name>(2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium</iupac_name>
  <traditional_iupac>(2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium</traditional_iupac>
  <cas_registry_number>63-89-8</cas_registry_number>
  <smiles>[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC</smiles>
  <inchi>InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1</inchi>
  <inchikey>KILNVBDSWZSGLL-KXQOOQHDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerophospholipids</class>
    <sub_class>Glycerophosphocholines</sub_class>
    <direct_parent>Phosphatidylcholines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Dialkyl phosphates</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phosphocholines</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Diacylglycero-3-phosphocholine</substituent>
      <substituent>Dialkyl phosphate</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphocholine</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Diacylglycerophosphocholines</external_descriptor>
      <external_descriptor>phosphatidylcholine 32:0</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>8.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>734.0389</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>733.562155053</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C40H80NO8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KILNVBDSWZSGLL-KXQOOQHDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>111.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>215.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>40</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:0)</name>
      <smpdb_id>SMP0080514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:0)</name>
      <smpdb_id>SMP0082317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>666493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>666494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>666495</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.4 +/- 0.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12.5 +/- 0.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15.1 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.2 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.040 +/- 0.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00157</kegg_id>
  <pubchem_compound_id>452110</pubchem_compound_id>
  <foodb_id>FDB022121</foodb_id>
  <chemspider_id>398235</chemspider_id>
  <drugbank_id>DB09114</drugbank_id>
  <pdbe_id/>
  <chebi_id>72999</chebi_id>
  <meta_cyc_id>1-2-DIPALMITOYLPHOSPHATIDYLCHOLINE</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5548</metlin_id>
  <synthesis_reference>Bouirig, H.; Eloy, D.; Jardon, P.  Formation and reactivity of the singlet oxygen photosensitized by hypericin in the liposomes of dipalmitoylphosphatidylcholine.  Evidence of delayed oxidation.    Journal de Chimie Physique et de Physico-Chimie Biologique  (1992),  89(6),  1391-411. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:54 UTC</creation_date>
  <update_date>2020-04-15 22:30:29 UTC</update_date>
  <accession>BMDB0000565</accession>
  <secondary_accessions>
    <accession>BMDB00565</accession>
  </secondary_accessions>
  <name>Galactonic acid</name>
  <description/>
  <synonyms>
    <synonym>D-Galactonic acid</synonym>
    <synonym>D-Galactonate</synonym>
    <synonym>Galactonate</synonym>
    <synonym>Galactonic acid, (D)-isomer</synonym>
    <synonym>Galactonic acid, monopotassium salt</synonym>
    <synonym>Galactonic acid, (L)-isomer</synonym>
  </synonyms>
  <chemical_formula>C6H12O7</chemical_formula>
  <average_molecular_weight>196.1553</average_molecular_weight>
  <monisotopic_moleculate_weight>196.058302738</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanoic acid</iupac_name>
  <traditional_iupac>galactonic acid</traditional_iupac>
  <cas_registry_number>13382-27-9</cas_registry_number>
  <smiles>OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3+,4+,5-/m1/s1</inchi>
  <inchikey>RGHNJXZEOKUKBD-MGCNEYSASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Medium-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Medium-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>galactonic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>133 - 136 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>196.1553</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>196.058302738</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3+,4+,5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RGHNJXZEOKUKBD-MGCNEYSASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>138.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329229</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00880</kegg_id>
  <pubchem_compound_id>128869</pubchem_compound_id>
  <foodb_id>FDB022122</foodb_id>
  <chemspider_id>114198</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>16534</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>3336</metlin_id>
  <synthesis_reference>Levene, P. A.; Simms, H. S.  Lactone formation mono- and dicarboxylic sugar acids.    Journal of Biological Chemistry  (1925),  65  31-47.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:55 UTC</creation_date>
  <update_date>2020-04-15 22:14:06 UTC</update_date>
  <accession>BMDB0000567</accession>
  <secondary_accessions>
    <accession>BMDB00567</accession>
  </secondary_accessions>
  <name>Cinnamic acid</name>
  <description/>
  <synonyms>
    <synonym>(2Z)-3-Phenyl-2-propenoic acid</synonym>
    <synonym>(2Z)-3-Phenylacrylic acid</synonym>
    <synonym>(Z)-3-Phenyl-2-propenoic acid</synonym>
    <synonym>(Z)-Cinnamic acid</synonym>
    <synonym>cis-beta-Carboxystyrene</synonym>
    <synonym>cis-Zimtsaeure</synonym>
    <synonym>(2Z)-3-Phenyl-2-propenoate</synonym>
    <synonym>(2Z)-3-Phenylacrylate</synonym>
    <synonym>(Z)-3-Phenyl-2-propenoate</synonym>
    <synonym>(Z)-Cinnamate</synonym>
    <synonym>cis-b-Carboxystyrene</synonym>
    <synonym>cis-Β-carboxystyrene</synonym>
    <synonym>Cinnamate</synonym>
    <synonym>(e)-3-Phenyl-2-propenoate</synonym>
    <synonym>(e)-3-Phenyl-2-propenoic acid</synonym>
    <synonym>3-Phenyl-2-propenoate</synonym>
    <synonym>3-Phenyl-2-propenoic acid</synonym>
    <synonym>3-Phenyl-acrylate</synonym>
    <synonym>3-Phenyl-acrylic acid</synonym>
    <synonym>3-Phenylacrylate</synonym>
    <synonym>3-Phenylacrylic acid</synonym>
    <synonym>3-Phenylpropenoate</synonym>
    <synonym>3-Phenylpropenoic acid</synonym>
    <synonym>Benzenepropenoate</synonym>
    <synonym>Benzenepropenoic acid</synonym>
    <synonym>Benzylideneacetic acid</synonym>
    <synonym>beta-Phenylacrylic acid</synonym>
    <synonym>Cinnamylic acid</synonym>
    <synonym>Phenylacrylate</synonym>
    <synonym>Phenylacrylic acid</synonym>
    <synonym>cis-Cinnamate</synonym>
    <synonym>(Z)-3-Phenylacrylic acid</synonym>
    <synonym>Allocinnamic acid</synonym>
    <synonym>Isocinnamic acid</synonym>
    <synonym>cis-Cinnamic acid</synonym>
    <synonym>Β-phenylacrylic acid</synonym>
    <synonym>Cinnamic acid</synonym>
  </synonyms>
  <chemical_formula>C9H8O2</chemical_formula>
  <average_molecular_weight>148.1586</average_molecular_weight>
  <monisotopic_moleculate_weight>148.0524295</monisotopic_moleculate_weight>
  <iupac_name>(2Z)-3-phenylprop-2-enoic acid</iupac_name>
  <traditional_iupac>cis-cinnamic acid</traditional_iupac>
  <cas_registry_number>102-94-3</cas_registry_number>
  <smiles>OC(=O)\C=C/C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6-</inchi>
  <inchikey>WBYWAXJHAXSJNI-SREVYHEPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Cinnamic acids and derivatives</class>
    <sub_class>Cinnamic acids</sub_class>
    <direct_parent>Cinnamic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cinnamic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Styrene</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>cinnamic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>132 - 135 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.57 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.13</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2Z)-3-phenylprop-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>148.1586</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>148.0524295</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)\C=C/C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H8O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WBYWAXJHAXSJNI-SREVYHEPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1368</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>792</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352287</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB012698</foodb_id>
  <chemspider_id>10286933</chemspider_id>
  <pubchem_compound_id>5372954</pubchem_compound_id>
  <kegg_id>C10438</kegg_id>
  <pdbe_id/>
  <chebi_id>35699</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00029961</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Cinnamic acid</wikipedia_id>
  <metlin_id>310</metlin_id>
  <synthesis_reference>An, Hong; He, Xifeng; Fu, Jing.  Synthesis of cinnamic acid.    Huagong Shikan  (2005),  19(7),  32-33, 41.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:56 UTC</creation_date>
  <update_date>2020-04-14 22:47:48 UTC</update_date>
  <accession>BMDB0000568</accession>
  <secondary_accessions>
    <accession>BMDB00568</accession>
  </secondary_accessions>
  <name>D-Arabitol</name>
  <description>D-Arabitol, also known as D-lyxitol or D-arabinol, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. D-Arabitol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Arabitol exists in all living organisms, ranging from bacteria to humans. D-Arabitol is a potentially toxic compound. D-Arabitol has been found to be associated with several diseases known as colorectal cancer, invasive candidiasis, and eosinophilic esophagitis; also d-arabitol has been linked to the inborn metabolic disorders including ribose-5-phosphate isomerase deficiency.</description>
  <synonyms>
    <synonym>D-Arabinol</synonym>
    <synonym>D-Lyxitol</synonym>
    <synonym>D-Arabinitol</synonym>
    <synonym>Arabitol, (D)-isomer</synonym>
    <synonym>Arabitol</synonym>
    <synonym>D-(+)-Arabitol</synonym>
    <synonym>(+--)-Arabitol</synonym>
    <synonym>DL-Arabitol</synonym>
    <synonym>Arabino-pentitol</synonym>
    <synonym>Lyxitol</synonym>
    <synonym>D-Arabitol</synonym>
  </synonyms>
  <chemical_formula>C5H12O5</chemical_formula>
  <average_molecular_weight>152.1458</average_molecular_weight>
  <monisotopic_moleculate_weight>152.068473494</monisotopic_moleculate_weight>
  <iupac_name>(2R,4R)-pentane-1,2,3,4,5-pentol</iupac_name>
  <traditional_iupac>arabitol</traditional_iupac>
  <cas_registry_number>488-82-4</cas_registry_number>
  <smiles>OC[C@@H](O)C(O)[C@H](O)CO</smiles>
  <inchi>InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m1/s1</inchi>
  <inchikey>HEBKCHPVOIAQTA-QWWZWVQMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar alcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sugar alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>arabinitol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,4R)-pentane-1,2,3,4,5-pentol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>152.1458</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>152.068473494</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)C(O)[C@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H12O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HEBKCHPVOIAQTA-QWWZWVQMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>101.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>104844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>104845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>104846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218111</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01904</kegg_id>
  <pubchem_compound_id>94154</pubchem_compound_id>
  <foodb_id>FDB001475</foodb_id>
  <chemspider_id>84971</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>18333</chebi_id>
  <meta_cyc_id/>
  <knapsack_id>C00001156</knapsack_id>
  <wikipedia_id>D-arabinitol</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5551</metlin_id>
  <synthesis_reference>Delobeau, Didier; Moine, Didier.  Process for the preparation of d-arabitol from lactose.    Eur. Pat. Appl.  (1997),     9 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:57 UTC</creation_date>
  <update_date>2020-04-16 17:51:18 UTC</update_date>
  <accession>BMDB0000569</accession>
  <secondary_accessions>
    <accession>BMDB00569</accession>
  </secondary_accessions>
  <name>Deoxypyridinoline</name>
  <description/>
  <synonyms>
    <synonym>4-(2-Amino-2-carboxyethyl)-1-(5-amino-5-carboxypentyl)-3-(3-amino-3-carboxypropyl)-5-hydroxy-pyridinium  inner salt stereoisomer</synonym>
    <synonym>Deoxipyridinoline</synonym>
    <synonym>Deoxy-pyridinoline</synonym>
    <synonym>Deoxypiridinoline</synonym>
    <synonym>Deoxypirydynoline</synonym>
    <synonym>Deoxypyridinolone</synonym>
    <synonym>Deoxypyridoline</synonym>
    <synonym>Desoxypyridinoline</synonym>
    <synonym>Lysylpyridinoline</synonym>
    <synonym>N-(5-Amino-5-carboxypentyl)-3-hydroxy-4-(2-amino-2-carboxyethyl)-5-(3-amino-3-carboxypropyl)pyridine</synonym>
  </synonyms>
  <chemical_formula>C18H28N4O7</chemical_formula>
  <average_molecular_weight>412.4375</average_molecular_weight>
  <monisotopic_moleculate_weight>412.19579927</monisotopic_moleculate_weight>
  <iupac_name>4-[(2S)-2-amino-2-carboxyethyl]-3-[(3S)-3-amino-3-carboxypropyl]-1-[(5S)-5-amino-5-carboxypentyl]-5-hydroxypyridin-1-ium</iupac_name>
  <traditional_iupac>4-[(2S)-2-amino-2-carboxyethyl]-3-[(3S)-3-amino-3-carboxypropyl]-1-[(5S)-5-amino-5-carboxypentyl]-5-hydroxypyridin-1-ium</traditional_iupac>
  <cas_registry_number>83462-55-9</cas_registry_number>
  <smiles>N[C@@H](CCCC[N+]1=CC(CC[C@H](N)C([O-])=O)=C(C[C@H](N)C(O)=O)C(O)=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C18H28N4O7/c19-12(16(24)25)3-1-2-6-22-8-10(4-5-13(20)17(26)27)11(15(23)9-22)7-14(21)18(28)29/h8-9,12-14H,1-7,19-21H2,(H3-,23,24,25,26,27,28,29)/t12-,13-,14-/m0/s1</inchi>
  <inchikey>ZAHDXEIQWWLQQL-IHRRRGAJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridinium derivatives</alternative_parent>
      <alternative_parent>Pyridinolates</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridinium</substituent>
      <substituent>Pyridinolate</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-4.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-[(2S)-2-amino-2-carboxyethyl]-3-[(3S)-3-amino-3-carboxypropyl]-1-[(5S)-5-amino-5-carboxypentyl]-5-hydroxypyridin-1-ium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>412.4375</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>412.19579927</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCCC[N+]1=CC(CC[C@H](N)C([O-])=O)=C(C[C@H](N)C(O)=O)C(O)=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H28N4O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H28N4O7/c19-12(16(24)25)3-1-2-6-22-8-10(4-5-13(20)17(26)27)11(15(23)9-22)7-14(21)18(28)29/h8-9,12-14H,1-7,19-21H2,(H3-,23,24,25,26,27,28,29)/t12-,13-,14-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZAHDXEIQWWLQQL-IHRRRGAJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>216.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>113.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>42.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>81084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>81085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>81086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142118</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB013750</foodb_id>
  <chemspider_id>9479456</chemspider_id>
  <pubchem_compound_id>11304480</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id>89510</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Deoxypyridinoline</wikipedia_id>
  <metlin_id>5552</metlin_id>
  <synthesis_reference>Hatch, Robert P. Method for the synthesis of deoxypyridinoline. U.S. (1998), 7 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:58 UTC</creation_date>
  <update_date>2020-04-15 22:14:07 UTC</update_date>
  <accession>BMDB0000570</accession>
  <secondary_accessions>
    <accession>BMDB00570</accession>
  </secondary_accessions>
  <name>Coproporphyrin III</name>
  <description>Coproporphyrin III belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure. Coproporphyrin III is possibly soluble (in water) and a very strong basic compound (based on its pKa). Coproporphyrin III exists in all living species, ranging from bacteria to humans. In cattle, coproporphyrin iii is involved in the metabolic pathway called the porphyrin metabolism pathway. Coproporphyrin III is a potentially toxic compound.</description>
  <synonyms>
    <synonym>3,8,13,17-Tetramethylporphyrin-2,7,12,18-tetrapropanoic acid</synonym>
    <synonym>3,8,13,17-Tetramethylporphyrin-2,7,12,18-tetrapropanoate</synonym>
  </synonyms>
  <chemical_formula>C36H38N4O8</chemical_formula>
  <average_molecular_weight>654.7089</average_molecular_weight>
  <monisotopic_moleculate_weight>654.268964212</monisotopic_moleculate_weight>
  <iupac_name>3-[9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>14643-66-4</cas_registry_number>
  <smiles>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)/C(CCC(O)=O)=C3C</smiles>
  <inchi>InChI=1S/C36H38N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h13-16,37,40H,5-12H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-</inchi>
  <inchikey>JWFCYWSMNRLXLX-UJJXFSCMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>654.7089</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>654.268964212</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)/C(CCC(O)=O)=C3C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C36H38N4O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C36H38N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h13-16,37,40H,5-12H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JWFCYWSMNRLXLX-UJJXFSCMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>206.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>176.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>73.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13636</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB005557</foodb_id>
  <chemspider_id>16736509</chemspider_id>
  <pubchem_compound_id/>
  <kegg_id>C05770</kegg_id>
  <pdbe_id/>
  <chebi_id>27609</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>COPROPORPHYRIN_III</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5553</metlin_id>
  <synthesis_reference>Minoda, Taiji; Takada, Toshihiro; Horii, Shinichi.  Coproporphyrin III.    Jpn. Kokai Tokkyo Koho  (1979),  3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:32:59 UTC</creation_date>
  <update_date>2020-04-16 17:53:59 UTC</update_date>
  <accession>BMDB0000572</accession>
  <secondary_accessions>
    <accession>BMDB00572</accession>
  </secondary_accessions>
  <name>Desmosine</name>
  <description/>
  <synonyms>
    <synonym>4-(4-Amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)-3,5-bis(3-amino-3-carboxypropyl)pyridinium</synonym>
    <synonym>Desmosine</synonym>
  </synonyms>
  <chemical_formula>C24H40N5O8</chemical_formula>
  <average_molecular_weight>526.6031</average_molecular_weight>
  <monisotopic_moleculate_weight>526.287688281</monisotopic_moleculate_weight>
  <iupac_name>3,5-bis[(3S)-3-amino-3-carboxypropyl]-4-[(4S)-4-amino-4-carboxybutyl]-1-(5-amino-5-carboxypentyl)pyridin-1-ium</iupac_name>
  <traditional_iupac>3,5-bis[(3S)-3-amino-3-carboxypropyl]-4-[(4S)-4-amino-4-carboxybutyl]-1-(5-amino-5-carboxypentyl)pyridin-1-ium</traditional_iupac>
  <cas_registry_number>11003-57-9</cas_registry_number>
  <smiles>NC(CCCC[N+]1=CC(CC[C@H](N)C(O)=O)=C(CCC[C@H](N)C(O)=O)C(CC[C@H](N)C(O)=O)=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C24H39N5O8/c25-17(21(30)31)5-1-2-11-29-12-14(7-9-19(27)23(34)35)16(4-3-6-18(26)22(32)33)15(13-29)8-10-20(28)24(36)37/h12-13,17-20H,1-11,25-28H2,(H3-,30,31,32,33,34,35,36,37)/p+1/t17?,18-,19-,20-/m0/s1</inchi>
  <inchikey>VEVRNHHLCPGNDU-NIVVRJPPSA-O</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Tetracarboxylic acids and derivatives</sub_class>
    <direct_parent>Tetracarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridinium derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridinium</substituent>
      <substituent>Tetracarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-4.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3,5-bis[(3S)-3-amino-3-carboxypropyl]-4-[(4S)-4-amino-4-carboxybutyl]-1-(5-amino-5-carboxypentyl)pyridin-1-ium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>526.6031</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>526.287688281</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CCCC[N+]1=CC(CC[C@H](N)C(O)=O)=C(CCC[C@H](N)C(O)=O)C(CC[C@H](N)C(O)=O)=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40N5O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H39N5O8/c25-17(21(30)31)5-1-2-11-29-12-14(7-9-19(27)23(34)35)16(4-3-6-18(26)22(32)33)15(13-29)8-10-20(28)24(36)37/h12-13,17-20H,1-11,25-28H2,(H3-,30,31,32,33,34,35,36,37)/p+1/t17?,18-,19-,20-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VEVRNHHLCPGNDU-NIVVRJPPSA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>257.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>133.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>56.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156578</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB000516</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477704</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id>37628</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Desmosine</wikipedia_id>
  <metlin_id>5554</metlin_id>
  <synthesis_reference>Rencher, William Franklin, Jr.  Design and synthesis of desmosine-like peptidyl carbamates as novel inhibitors of human leukocyte elastase.    (1988),     164 pp.  CAN 111:233627  AN 1989:633627</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:00 UTC</creation_date>
  <update_date>2020-04-16 17:52:18 UTC</update_date>
  <accession>BMDB0000573</accession>
  <secondary_accessions>
    <accession>BMDB00573</accession>
    <accession>BMDB0063575</accession>
    <accession>BMDB63575</accession>
  </secondary_accessions>
  <name>Elaidic acid</name>
  <description>Elaidic acid, also known as (9E)-octadecenoic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Elaidic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Elaidic acid is the major trans fat found in hydrogenated vegetable oils and occurs in small amounts in caprine and bovine milk (very roughly 0.1 % of the fatty acids) and some meats. It is the trans isomer of oleic acid. The name of the elaidinization reaction comes from elaidic acid. Elaidic acid increases CETP activity, which in turn raises VLDL and lowers HDL cholesterol (Wikipedia).</description>
  <synonyms>
    <synonym>(9E)-Octadecenoic acid</synonym>
    <synonym>(E)-Oleic acid</synonym>
    <synonym>9-OCTADECENOIC ACID</synonym>
    <synonym>9-trans-Octadecenoic acid</synonym>
    <synonym>Acide elaidique</synonym>
    <synonym>D9-trans-Octadecenoic acid</synonym>
    <synonym>Elaidinsaure</synonym>
    <synonym>Elaidinsaeure</synonym>
    <synonym>trans-9-Octadecenoic acid</synonym>
    <synonym>trans-D9-Octadecenoic acid</synonym>
    <synonym>trans-delta(9)-Octadecenoic acid</synonym>
    <synonym>trans-Elaidic acid</synonym>
    <synonym>trans-Oleic acid</synonym>
    <synonym>(9E)-Octadecenoate</synonym>
    <synonym>Elaidate</synonym>
    <synonym>(E)-Oleate</synonym>
    <synonym>9-OCTADECENOate</synonym>
    <synonym>9-trans-Octadecenoate</synonym>
    <synonym>D9-trans-Octadecenoate</synonym>
    <synonym>trans-9-Octadecenoate</synonym>
    <synonym>trans-D9-Octadecenoate</synonym>
    <synonym>trans-delta(9)-Octadecenoate</synonym>
    <synonym>trans-Δ(9)-Octadecenoate</synonym>
    <synonym>trans-Δ(9)-Octadecenoic acid</synonym>
    <synonym>trans-Elaidate</synonym>
    <synonym>trans-Oleate</synonym>
    <synonym>FA(18:1(9E))</synonym>
    <synonym>Elaidic acid</synonym>
    <synonym>9-Elaidate</synonym>
    <synonym>18:1 N-9</synonym>
    <synonym>C18:1 N-9</synonym>
    <synonym>Octadec-9-enoic acid</synonym>
    <synonym>Octadec-9-enoate</synonym>
    <synonym>9,10-Octadecenoate</synonym>
    <synonym>9,10-Octadecenoic acid</synonym>
    <synonym>Acid, 9-octadecenoic</synonym>
    <synonym>9 Octadecenoic acid</synonym>
    <synonym>(9E)-9-Octadecenoic acid</synonym>
    <synonym>(E)-9-Octadecenoic acid</synonym>
    <synonym>9-trans-Oleic acid</synonym>
    <synonym>Elaidinic acid</synonym>
    <synonym>delta9-trans-Octadecenoic acid</synonym>
    <synonym>trans-delta9-Octadecenoic acid</synonym>
    <synonym>trans-Δ9-Octadecenoic acid</synonym>
    <synonym>Δ9-trans-Octadecenoic acid</synonym>
  </synonyms>
  <chemical_formula>C18H34O2</chemical_formula>
  <average_molecular_weight>282.4614</average_molecular_weight>
  <monisotopic_moleculate_weight>282.255880332</monisotopic_moleculate_weight>
  <iupac_name>(9E)-octadec-9-enoic acid</iupac_name>
  <traditional_iupac>elaidic acid</traditional_iupac>
  <cas_registry_number>112-79-8</cas_registry_number>
  <smiles>[H]\C(CCCCCCCC)=C(\[H])CCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+</inchi>
  <inchikey>ZQPPMHVWECSIRJ-MDZDMXLPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Monounsaturated fatty acids</external_descriptor>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>octadec-9-enoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>42 - 44 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.78</value>
      <source>Extrapolated</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(9E)-octadec-9-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>282.4614</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>282.255880332</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]\C(CCCCCCCC)=C(\[H])CCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H34O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZQPPMHVWECSIRJ-MDZDMXLPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>87.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1881</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1370</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>933.22</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>368.62</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>17763.52</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>6465.31</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>14110.42</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>5799.73</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>8602.95</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Calf-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>8921.57</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. With growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>8468.41</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Without growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>8889.71</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Yearling-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed barley silage diet for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed barley silage diet with flaxseed for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed hay for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed hay with flaxseed for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk from 6 Holstein and 6 Montbeliarde cows</comment>
      <references>
        <reference>
          <reference_text>Lopez C, Briard-Bion V, Menard O, Rousseau F, Pradel P, Besle JM: Phospholipid, sphingolipid, and fatty acid compositions of the milk fat globule membrane are modified by diet. J Agric Food Chem. 2008 Jul 9;56(13):5226-36. doi: 10.1021/jf7036104. Epub 2008 Jun 4.</reference_text>
          <pubmed_id>18522410</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>This is a duplicate concentration of concentration_id 4476, unpexported by An Chi on Aug 20, 2018</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10691.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10691.726</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2372.00552</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3681.919</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2372.00552</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27224.959</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>26198.27</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>26198.27</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples have been collected from Heifer cows.</comment>
      <references>
        <reference>
          <reference_text>Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub  2013 Jun 5.</reference_text>
          <pubmed_id>23871026</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01712</kegg_id>
  <pubchem_compound_id>637517</pubchem_compound_id>
  <foodb_id>FDB002951</foodb_id>
  <chemspider_id>553123</chemspider_id>
  <drugbank_id>DB04224</drugbank_id>
  <pdbe_id/>
  <chebi_id>27997</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Elaidic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>38213</bigg_id>
  <metlin_id>3406</metlin_id>
  <synthesis_reference>Vitagliano, Michele.  Formation of elaidic acid.    Oli, Grassi, Derivati  (1967),  111(12),  77-8.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.</reference_text>
      <pubmed_id>20855010</pubmed_id>
    </reference>
    <reference>
      <reference_text>Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026.</reference_text>
      <pubmed_id>29570652</pubmed_id>
    </reference>
    <reference>
      <reference_text>van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.</reference_text>
      <pubmed_id>28219465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lopez C, Briard-Bion V, Menard O, Rousseau F, Pradel P, Besle JM: Phospholipid, sphingolipid, and fatty acid compositions of the milk fat globule membrane are modified by diet. J Agric Food Chem. 2008 Jul 9;56(13):5226-36. doi: 10.1021/jf7036104. Epub 2008 Jun 4.</reference_text>
      <pubmed_id>18522410</pubmed_id>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:02 UTC</creation_date>
  <update_date>2020-04-16 20:39:58 UTC</update_date>
  <accession>BMDB0000574</accession>
  <secondary_accessions>
    <accession>BMDB00574</accession>
  </secondary_accessions>
  <name>L-Cysteine</name>
  <description>L-Cysteine, also known as C or e 920, belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Cysteine is a drug which is used for the prevention of liver damage and kidney damage associated with overdoses of acetaminophen. L-Cysteine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Cysteine exists in all living species, ranging from bacteria to humans. L-Cysteine participates in a number of enzymatic reactions, within cattle. In particular, L-Cysteine can be converted into 3-sulfinoalanine through its interaction with the enzyme cysteine dioxygenase type 1. In addition, L-Cysteine can be converted into hydrogen sulfide and pyruvic acid through its interaction with the enzyme cystathionine gamma-lyase. In cattle, L-cysteine is involved in the metabolic pathway called the cysteine metabolism pathway. L-Cysteine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2R)-2-Amino-3-mercaptopropanoic acid</synonym>
    <synonym>(2R)-2-Amino-3-sulfanylpropanoic acid</synonym>
    <synonym>(R)-2-Amino-3-mercaptopropanoic acid</synonym>
    <synonym>C</synonym>
    <synonym>Cys</synonym>
    <synonym>CYSTEINE</synonym>
    <synonym>e 920</synonym>
    <synonym>e-920</synonym>
    <synonym>e920</synonym>
    <synonym>FREE cysteine</synonym>
    <synonym>L-2-Amino-3-mercaptopropionic acid</synonym>
    <synonym>L-Cystein</synonym>
    <synonym>L-Zystein</synonym>
    <synonym>Ecolan</synonym>
    <synonym>(2R)-2-Amino-3-mercaptopropanoate</synonym>
    <synonym>(2R)-2-Amino-3-sulfanylpropanoate</synonym>
    <synonym>(2R)-2-Amino-3-sulphanylpropanoate</synonym>
    <synonym>(2R)-2-Amino-3-sulphanylpropanoic acid</synonym>
    <synonym>(R)-2-Amino-3-mercaptopropanoate</synonym>
    <synonym>L-2-Amino-3-mercaptopropionate</synonym>
    <synonym>(+)-2-Amino-3-mercaptopropionic acid</synonym>
    <synonym>(R)-(+)-Cysteine</synonym>
    <synonym>(R)-2-Amino-3-mercapto-propanoate</synonym>
    <synonym>(R)-2-Amino-3-mercapto-propanoic acid</synonym>
    <synonym>(R)-Cysteine</synonym>
    <synonym>2-Amino-3-mercaptopropanoate</synonym>
    <synonym>2-Amino-3-mercaptopropanoic acid</synonym>
    <synonym>2-Amino-3-mercaptopropionate</synonym>
    <synonym>2-Amino-3-mercaptopropionic acid</synonym>
    <synonym>3-Mercapto-L-alanine</synonym>
    <synonym>Acetylcysteine</synonym>
    <synonym>alpha-Amino-beta-thiolpropionic acid</synonym>
    <synonym>b-Mercaptoalanine</synonym>
    <synonym>beta-Mercaptoalanine</synonym>
    <synonym>Carbocysteine</synonym>
    <synonym>Cisteina</synonym>
    <synonym>Cisteinum</synonym>
    <synonym>Cystein</synonym>
    <synonym>Cysteinum</synonym>
    <synonym>Half-cystine</synonym>
    <synonym>L Cysteine</synonym>
    <synonym>L-(+)-Cysteine</synonym>
    <synonym>L-2-Amino-3-mercaptopropanoate</synonym>
    <synonym>L-2-Amino-3-mercaptopropanoic acid</synonym>
    <synonym>Polycysteine</synonym>
    <synonym>Thioserine</synonym>
    <synonym>Cysteine hydrochloride</synonym>
    <synonym>Zinc cysteinate</synonym>
    <synonym>Half cystine</synonym>
  </synonyms>
  <chemical_formula>C3H7NO2S</chemical_formula>
  <average_molecular_weight>121.158</average_molecular_weight>
  <monisotopic_moleculate_weight>121.019749163</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-amino-3-sulfanylpropanoic acid</iupac_name>
  <traditional_iupac>L-cysteine</traditional_iupac>
  <cas_registry_number>52-90-4</cas_registry_number>
  <smiles>N[C@@H](CS)C(O)=O</smiles>
  <inchi>InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1</inchi>
  <inchikey>XUJNEKJLAYXESH-REOHCLBHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Cysteine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Cysteine or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>cysteine</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
      <external_descriptor>serine family amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>220 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>277 mg/mL at 25 °C</value>
      <source>BEILSTEIN</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.49</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-amino-3-sulfanylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>121.158</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>121.019749163</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CS)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7NO2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XUJNEKJLAYXESH-REOHCLBHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutathione Metabolism</name>
      <smpdb_id>SMP0087167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Homocysteine Degradation</name>
      <smpdb_id>SMP0087201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Kidney Function</name>
      <smpdb_id>SMP0119376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pantothenate and CoA Biosynthesis</name>
      <smpdb_id>SMP0087207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Cysteine</name>
      <smpdb_id>SMP0119388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Taurine and Hypotaurine Metabolism</name>
      <smpdb_id>SMP0087214</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447738</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB012678</foodb_id>
  <kegg_id>C00097</kegg_id>
  <chemspider_id>5653</chemspider_id>
  <pubchem_compound_id>5862</pubchem_compound_id>
  <chebi_id>17561</chebi_id>
  <drugbank_id>DB00151</drugbank_id>
  <pdbe_id/>
  <meta_cyc_id>CYS</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001351</knapsack_id>
  <bigg_id>33843</bigg_id>
  <wikipedia_id>Cysteine</wikipedia_id>
  <metlin_id>5556</metlin_id>
  <synthesis_reference>Kumagai, Hidehiko; Tanaka, Hideyuki; Sejima, Shunsuke; Yamada, Hideaki. Elimination and replacement reactions of b-chloro-L-alanine by cysteine desulfhydrase from Aerobacter aerogenes. Agricultural and Biological Chemistry (1977), 41(10), 2071-5.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00233</protein_accession>
      <name>Disintegrin and metalloproteinase domain-containing protein 10</name>
      <uniprot_id>Q10741</uniprot_id>
      <gene_name>ADAM10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00683</protein_accession>
      <name>Cysteine dioxygenase type 1</name>
      <uniprot_id>Q3SZU4</uniprot_id>
      <gene_name>CDO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00811</protein_accession>
      <name>Interstitial collagenase</name>
      <uniprot_id>P28053</uniprot_id>
      <gene_name>MMP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00812</protein_accession>
      <name>Cysteinyl-tRNA synthetase, mitochondrial</name>
      <uniprot_id>Q2KIF8</uniprot_id>
      <gene_name>CARS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00813</protein_accession>
      <name>Matrix metalloproteinase-9</name>
      <uniprot_id>P52176</uniprot_id>
      <gene_name>MMP9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00814</protein_accession>
      <name>Matrix metalloproteinase-14</name>
      <uniprot_id>Q9GLE4</uniprot_id>
      <gene_name>MMP14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00815</protein_accession>
      <name>Collagenase 3</name>
      <uniprot_id>O77656</uniprot_id>
      <gene_name>MMP13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00816</protein_accession>
      <name>Matrix metalloproteinase-20</name>
      <uniprot_id>O18767</uniprot_id>
      <gene_name>MMP20</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00817</protein_accession>
      <name>Methylated-DNA--protein-cysteine methyltransferase</name>
      <uniprot_id>P29177</uniprot_id>
      <gene_name>MGMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00818</protein_accession>
      <name>Cystathionine gamma-lyase</name>
      <uniprot_id>Q58DW2</uniprot_id>
      <gene_name>CTH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00819</protein_accession>
      <name>72 kDa type IV collagenase</name>
      <uniprot_id>Q9GLE5</uniprot_id>
      <gene_name>MMP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00820</protein_accession>
      <name>A disintegrin and metalloproteinase with thrombospondin motifs 4</name>
      <uniprot_id>Q9TT93</uniprot_id>
      <gene_name>ADAMTS4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02004</protein_accession>
      <name>Calpastatin</name>
      <uniprot_id>P20811</uniprot_id>
      <gene_name>CAST</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:03 UTC</creation_date>
  <update_date>2020-03-13 16:22:15 UTC</update_date>
  <accession>BMDB0000575</accession>
  <secondary_accessions>
    <accession>BMDB00575</accession>
  </secondary_accessions>
  <name>DL-Homocystine</name>
  <description/>
  <synonyms>
    <synonym>4,4'-Dithiobis(2-aminobutyric acid)</synonym>
    <synonym>Homocystine</synonym>
    <synonym>4,4'-Dithiobis(2-aminobutyrate)</synonym>
    <synonym>4,4'-Dithiobis</synonym>
  </synonyms>
  <chemical_formula>C8H16N2O4S2</chemical_formula>
  <average_molecular_weight>268.354</average_molecular_weight>
  <monisotopic_moleculate_weight>268.05514839</monisotopic_moleculate_weight>
  <iupac_name>2-amino-4-[(3-amino-3-carboxypropyl)disulfanyl]butanoic acid</iupac_name>
  <traditional_iupac>homocystine</traditional_iupac>
  <cas_registry_number>870-93-9</cas_registry_number>
  <smiles>NC(CCSSCCC(N)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)</inchi>
  <inchikey>ZTVZLYBCZNMWCF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkyldisulfides</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dialkyldisulfide</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic disulfide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thia fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>homocystines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>263 - 265 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-4.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-4-[(3-amino-3-carboxypropyl)disulfanyl]butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>268.354</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>268.05514839</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CCSSCCC(N)C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16N2O4S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZTVZLYBCZNMWCF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>126.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>64.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440078</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022123</foodb_id>
  <kegg_id>C01817</kegg_id>
  <chemspider_id>9616</chemspider_id>
  <pubchem_compound_id>10010</pubchem_compound_id>
  <chebi_id>17485</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5557</metlin_id>
  <synthesis_reference>Lang, K.; Keller, C.  Effect of the cyclophorase system on sulfur-containing amino acids.  Biochemische Zeitschrift  (1955),  327  202-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:04 UTC</creation_date>
  <update_date>2020-03-13 16:22:15 UTC</update_date>
  <accession>BMDB0000576</accession>
  <secondary_accessions>
    <accession>BMDB00576</accession>
  </secondary_accessions>
  <name>Monoethyl malonic acid</name>
  <description/>
  <synonyms>
    <synonym>Monoethyl malonate</synonym>
    <synonym>(Ethoxycarbonyl)acetate</synonym>
    <synonym>(Ethoxycarbonyl)acetic acid</synonym>
    <synonym>3-Ethoxy-3-oxopropanoate</synonym>
    <synonym>3-Ethoxy-3-oxopropanoic acid</synonym>
    <synonym>Ethyl hydrogen malonate</synonym>
    <synonym>Ethyl malonate</synonym>
    <synonym>Malonic acid ethyl ester</synonym>
    <synonym>Malonic acid monoethyl ester</synonym>
    <synonym>Monoethyl hydrogen malonate</synonym>
    <synonym>Ethyl hydrogen malonic acid</synonym>
  </synonyms>
  <chemical_formula>C5H8O4</chemical_formula>
  <average_molecular_weight>132.1146</average_molecular_weight>
  <monisotopic_moleculate_weight>132.042258744</monisotopic_moleculate_weight>
  <iupac_name>3-ethoxy-3-oxopropanoic acid</iupac_name>
  <traditional_iupac>ethyl hydrogen malonate</traditional_iupac>
  <cas_registry_number>1071-46-1</cas_registry_number>
  <smiles>CCOC(=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C5H8O4/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3,(H,6,7)</inchi>
  <inchikey>HGINADPHJQTSKN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Dicarboxylic acids and derivatives</sub_class>
    <direct_parent>Dicarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-dicarbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aromatic carboxylic acid</external_descriptor>
      <external_descriptor>pyridinemonocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>47 - 50 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-ethoxy-3-oxopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.1146</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCOC(=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O4/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HGINADPHJQTSKN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1428</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022124</foodb_id>
  <kegg_id/>
  <chemspider_id>63783</chemspider_id>
  <pubchem_compound_id>70615</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5558</metlin_id>
  <synthesis_reference>Ozaki, Eiji; Endo, Ryuichi.  Manufacture of malonic acid monoesters from cyanoacetate esters with microbial nitrilase.    Jpn. Kokai Tokkyo Koho  (1998),     4 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:05 UTC</creation_date>
  <update_date>2020-04-15 22:06:44 UTC</update_date>
  <accession>BMDB0000577</accession>
  <secondary_accessions>
    <accession>BMDB00577</accession>
  </secondary_accessions>
  <name>5beta-Coprostanol</name>
  <description/>
  <synonyms>
    <synonym>(3beta,5beta)-Cholestan-3-ol</synonym>
    <synonym>5beta Coprostanol</synonym>
    <synonym>5beta-Cholestan-3beta-ol</synonym>
    <synonym>Coprosterol</synonym>
    <synonym>(3b,5b)-Cholestan-3-ol</synonym>
    <synonym>(3Β,5β)-cholestan-3-ol</synonym>
    <synonym>5b Coprostanol</synonym>
    <synonym>5Β coprostanol</synonym>
    <synonym>5b-Cholestan-3b-ol</synonym>
    <synonym>5Β-cholestan-3β-ol</synonym>
    <synonym>5b-Coprostanol</synonym>
    <synonym>5Β-coprostanol</synonym>
    <synonym>3b-Hydroxy-5b-cholestanol</synonym>
    <synonym>Stercorin</synonym>
    <synonym>5 beta-Cholestan-3 beta-ol</synonym>
    <synonym>5 alpha Cholestan 3 alpha ol</synonym>
    <synonym>Coprostanol</synonym>
    <synonym>5 beta-Cholestan-3 alpha-ol</synonym>
    <synonym>Cholestan 3 ol</synonym>
    <synonym>Cholestanol, (3alpha, 5beta)-isomer</synonym>
    <synonym>beta-Cholestanol</synonym>
    <synonym>beta-Cholestan-3 beta-ol, 5</synonym>
    <synonym>Cholestan-3-ol</synonym>
    <synonym>Cholestanol</synonym>
    <synonym>Dihydrocholesterol</synonym>
    <synonym>beta-Ol, 5 beta-cholestan-3</synonym>
    <synonym>5 alpha Cholestan 3 beta ol</synonym>
    <synonym>beta Cholestanol</synonym>
    <synonym>5 alpha-Cholestan-3 alpha-ol</synonym>
    <synonym>5 alpha-Cholestan-3 beta-ol</synonym>
    <synonym>5 beta Cholestan 3 beta ol</synonym>
  </synonyms>
  <chemical_formula>C27H48O</chemical_formula>
  <average_molecular_weight>388.6694</average_molecular_weight>
  <monisotopic_moleculate_weight>388.370516158</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5S,7R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol</iupac_name>
  <traditional_iupac>(1S,2S,5S,7R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol</traditional_iupac>
  <cas_registry_number>360-68-9</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</smiles>
  <inchi>InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>QYIXCDOBOSTCEI-NWKZBHTNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>102 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5S,7R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>388.6694</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>388.370516158</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H48O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QYIXCDOBOSTCEI-NWKZBHTNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>119.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>50.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1429</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022125</foodb_id>
  <kegg_id/>
  <chemspider_id>191826</chemspider_id>
  <pubchem_compound_id>221122</pubchem_compound_id>
  <chebi_id>89519</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Coprosterol</wikipedia_id>
  <metlin_id>5559</metlin_id>
  <synthesis_reference>Lieber, Iris Ilona.  Metabolism of cholesterol. New theory of the formation of coprosterol.    Prensa Medica Argentina  (1960),  47  3097-3100.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:06 UTC</creation_date>
  <update_date>2020-04-15 22:27:49 UTC</update_date>
  <accession>BMDB0000579</accession>
  <secondary_accessions>
    <accession>BMDB00579</accession>
  </secondary_accessions>
  <name>Deuteroporphyrin IX</name>
  <description/>
  <synonyms>
    <synonym>Deuteroporphyrin</synonym>
    <synonym>Deuteroporphyrin-IX</synonym>
    <synonym>3-[20-(2-Carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C30H30N4O4</chemical_formula>
  <average_molecular_weight>510.5836</average_molecular_weight>
  <monisotopic_moleculate_weight>510.226705468</monisotopic_moleculate_weight>
  <iupac_name>3-[20-(2-carboxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[20-(2-carboxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>448-65-7</cas_registry_number>
  <smiles>CC1=C/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(C=C4C)\C=C\1/N\2)/C(CCC(O)=O)=C3C</smiles>
  <inchi>InChI=1S/C30H30N4O4/c1-15-9-20-12-25-17(3)21(5-7-29(35)36)27(33-25)14-28-22(6-8-30(37)38)18(4)26(34-28)13-24-16(2)10-19(32-24)11-23(15)31-20/h9-14,31,34H,5-8H2,1-4H3,(H,35,36)(H,37,38)/b19-11-,20-12-,23-11-,24-13-,25-12-,26-13-,27-14-,28-14-</inchi>
  <inchikey>KWKUIRGQJJFUCG-LMKUSPAJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[20-(2-carboxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>510.5836</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>510.226705468</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(C=C4C)\C=C\1/N\2)/C(CCC(O)=O)=C3C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C30H30N4O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C30H30N4O4/c1-15-9-20-12-25-17(3)21(5-7-29(35)36)27(33-25)14-28-22(6-8-30(37)38)18(4)26(34-28)13-24-16(2)10-19(32-24)11-23(15)31-20/h9-14,31,34H,5-8H2,1-4H3,(H,35,36)(H,37,38)/b19-11-,20-12-,23-11-,24-13-,25-12-,26-13-,27-14-,28-14-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KWKUIRGQJJFUCG-LMKUSPAJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>131.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>144.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>58.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343452</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022126</foodb_id>
  <kegg_id/>
  <chemspider_id>16736707</chemspider_id>
  <pubchem_compound_id/>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5561</metlin_id>
  <synthesis_reference>Borovkov, V. V.; Filippovich, E. I.; Evstigneeva, R. P.  Synthesis and spectral investigation of deuteroporphyrin IX-based porphyrinquinone derivatives.    Khimiya Geterotsiklicheskikh Soedinenii  (1988),   (5),  608-16.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:07 UTC</creation_date>
  <update_date>2020-04-16 20:39:58 UTC</update_date>
  <accession>BMDB0000580</accession>
  <secondary_accessions>
    <accession>BMDB00580</accession>
  </secondary_accessions>
  <name>Chondroitin sulfate</name>
  <description/>
  <synonyms>
    <synonym>Chondroitin sulfuric acid</synonym>
    <synonym>Chondroitin sulphate</synonym>
    <synonym>Chondroitin sulphuric acid</synonym>
    <synonym>Chondritinsulfate</synonym>
    <synonym>Chondritinsulphate</synonym>
    <synonym>Chondroitin 6-sulfate</synonym>
    <synonym>Chondroitin 6-sulphate</synonym>
    <synonym>Chondroitin polysulfate</synonym>
    <synonym>Chondroitin polysulphate</synonym>
    <synonym>Chondroitin sodium sulfate ex shark</synonym>
    <synonym>Chondroitin sulfate C</synonym>
    <synonym>Chondroitin sulfate from swine</synonym>
    <synonym>Chondroitin sulphate C</synonym>
    <synonym>Chondroitin sulphate from swine</synonym>
    <synonym>Chondroitinsulfurate</synonym>
    <synonym>Chondroitinsulfuric acid</synonym>
    <synonym>Chondroitinsulfuric acids</synonym>
    <synonym>Blutal</synonym>
    <synonym>Chondroitin 4 sulfate, aluminum salt</synonym>
    <synonym>Chondroitin 4-sulfate, aluminum salt</synonym>
    <synonym>Chondroitin 6 sulfate, potassium salt</synonym>
    <synonym>Chondroitin 6 sulfate, sodium salt</synonym>
    <synonym>Chondroitin sulfate a</synonym>
    <synonym>Sulfate, sodium chondroitin</synonym>
    <synonym>Chondroitin 4-sulfate, potassium salt</synonym>
    <synonym>Chondroitin 6-sulfate, potassium salt</synonym>
    <synonym>Chondroitin sulfate 4 sulfate, sodium salt</synonym>
    <synonym>Chondroitin sulfate, calcium salt</synonym>
    <synonym>Chondroitin sulfate, iron (+3) salt</synonym>
    <synonym>Chondroitin sulfate, iron salt</synonym>
    <synonym>Chondroitin sulfate, potassium salt</synonym>
    <synonym>Sulfate, chondroitin</synonym>
    <synonym>Translagen</synonym>
    <synonym>Chondroitin 4-sulfate</synonym>
    <synonym>Chondroitin 6 sulfate</synonym>
    <synonym>Chondroitin sulfate, sodium</synonym>
    <synonym>Chondroitin sulfate, sodium salt</synonym>
    <synonym>Chonsurid</synonym>
    <synonym>Sulfates, chondroitin</synonym>
    <synonym>Chondroitin 4 sulfate</synonym>
    <synonym>Chondroitin 4 sulfate, potassium salt</synonym>
    <synonym>Chondroitin 6-sulfate, sodium salt</synonym>
    <synonym>Chondroitin sulfate 4-sulfate, sodium salt</synonym>
    <synonym>Chondroitin sulfate, zinc salt</synonym>
    <synonym>Chondroitin sulfates</synonym>
    <synonym>Sodium chondroitin sulfate</synonym>
    <synonym>(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate</synonym>
    <synonym>(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(sulphooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate</synonym>
    <synonym>(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(sulphooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid</synonym>
    <synonym>Chondroitin sulfate</synonym>
  </synonyms>
  <chemical_formula>C13H21NO15S</chemical_formula>
  <average_molecular_weight>463.369</average_molecular_weight>
  <monisotopic_moleculate_weight>463.063189697</monisotopic_moleculate_weight>
  <iupac_name>(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid</traditional_iupac>
  <cas_registry_number>9007-28-7</cas_registry_number>
  <smiles>CC(=O)N[C@H]1[C@H](O)O[C@H](OS(O)(=O)=O)[C@H](O)[C@@H]1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O</smiles>
  <inchi>InChI=1S/C13H21NO15S/c1-2(15)14-3-8(7(19)13(28-11(3)22)29-30(23,24)25)26-12-6(18)4(16)5(17)9(27-12)10(20)21/h3-9,11-13,16-19,22H,1H3,(H,14,15)(H,20,21)(H,23,24,25)/t3-,4+,5+,6-,7-,8-,9+,11-,12-,13-/m1/s1</inchi>
  <inchikey>KXKPYJOVDUMHGS-OSRGNVMNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>O-glucuronides</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Disaccharides</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-o-glucuronide</substituent>
      <substituent>Acetal</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>O-glucuronide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3S,4S,5R,6R)-6-{[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>463.369</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>463.063189697</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@H]1[C@H](O)O[C@H](OS(O)(=O)=O)[C@H](O)[C@@H]1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H21NO15S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H21NO15S/c1-2(15)14-3-8(7(19)13(28-11(3)22)29-30(23,24)25)26-12-6(18)4(16)5(17)9(27-12)10(20)21/h3-9,11-13,16-19,22H,1H3,(H,14,15)(H,20,21)(H,23,24,25)/t3-,4+,5+,6-,7-,8-,9+,11-,12-,13-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KXKPYJOVDUMHGS-OSRGNVMNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>258.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326430</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022127</foodb_id>
  <kegg_id>C00607</kegg_id>
  <chemspider_id>23152</chemspider_id>
  <pubchem_compound_id>24766</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>37397</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Chondroitin sulfate</wikipedia_id>
  <metlin_id>5562</metlin_id>
  <synthesis_reference>Zhang, Wanshan; Yang, Huaying; Zhang, Zhiwu; Qu, Wei; Zhu, Yuehua; Liu, Lanhua; Zeng, Ying; Wan, Cai; Li, Jugen.  Extracting chondroitin sulfate from cartilage.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2007),     6pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01345</protein_accession>
      <name>Cartilage oligomeric matrix protein</name>
      <uniprot_id>P35445</uniprot_id>
      <gene_name>COMP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01353</protein_accession>
      <name>CD97 antigen</name>
      <uniprot_id>Q8SQA4</uniprot_id>
      <gene_name>CD97</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01574</protein_accession>
      <name>Vitrin</name>
      <uniprot_id>Q95LI2</uniprot_id>
      <gene_name>VIT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02081</protein_accession>
      <name>Olfactomedin-like protein 2B</name>
      <uniprot_id>A6QLD2</uniprot_id>
      <gene_name>OLFML2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:09 UTC</creation_date>
  <update_date>2020-04-15 21:35:24 UTC</update_date>
  <accession>BMDB0000582</accession>
  <secondary_accessions>
    <accession>BMDB00582</accession>
  </secondary_accessions>
  <name>3,5-Diiodothyronine</name>
  <description/>
  <synonyms>
    <synonym>35-Diiodothyronine</synonym>
    <synonym>(3,5-Diiodo-4-(-p-hydroxyphenoxy)phenyl)-alanine</synonym>
    <synonym>3',5'-Diiodothyronine</synonym>
    <synonym>3,5-Diiodo-D-thyronine</synonym>
    <synonym>3,5-Diiodo-DL-thryronine</synonym>
    <synonym>3,5-Diiodo-DL-thyronine</synonym>
    <synonym>3,5-Diiodo-L-thyronine</synonym>
    <synonym>3,5-T2</synonym>
    <synonym>4-(4-Hydroxyphenoxy)-3,5-diiodophenylalanine</synonym>
    <synonym>D-O-(4-Hydroxyphenyl)-3,5-diiodo-tyrosine</synonym>
    <synonym>Diiodo-L-thyronine</synonym>
    <synonym>Diiodothyronine</synonym>
    <synonym>DL-3,5-Diiodothyronine</synonym>
    <synonym>DL-Diiodothyronine</synonym>
    <synonym>L-3,5-Diiodothyronine</synonym>
    <synonym>L-O-(4-Hydroxyphenyl)-3,5-diiodo-tyrosine</synonym>
    <synonym>O-(4-Hydroxyphenyl)-3,5-diiodo-tyrosine</synonym>
    <synonym>3,5-Diiodothyronine, (L)-isomer</synonym>
    <synonym>3,5-Diiodothyronine, (DL)-isomer</synonym>
    <synonym>2-Amino-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]propanoate</synonym>
    <synonym>3,5-Diiodothyronine</synonym>
  </synonyms>
  <chemical_formula>C15H13I2NO4</chemical_formula>
  <average_molecular_weight>525.077</average_molecular_weight>
  <monisotopic_moleculate_weight>524.893394749</monisotopic_moleculate_weight>
  <iupac_name>2-amino-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]propanoic acid</iupac_name>
  <traditional_iupac>3,5-diiodo-dl-thryronine</traditional_iupac>
  <cas_registry_number>534-51-0</cas_registry_number>
  <smiles>NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C15H13I2NO4/c16-11-5-8(7-13(18)15(20)21)6-12(17)14(11)22-10-3-1-9(19)2-4-10/h1-6,13,19H,7,18H2,(H,20,21)</inchi>
  <inchikey>ZHSOTLOTTDYIIK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Phenylalanine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alpha amino acids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aryl iodides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Diarylethers</alternative_parent>
      <alternative_parent>Diphenylethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Iodobenzenes</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organoiodides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenol ethers</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Aryl iodide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Diaryl ether</substituent>
      <substituent>Diphenylether</substituent>
      <substituent>Ether</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Iodobenzene</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organoiodide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-3-[4-(4-hydroxyphenoxy)-3,5-diiodophenyl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>525.077</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>524.893394749</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CC1=CC(I)=C(OC2=CC=C(O)C=C2)C(I)=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H13I2NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H13I2NO4/c16-11-5-8(7-13(18)15(20)21)6-12(17)14(11)22-10-3-1-9(19)2-4-10/h1-6,13,19H,7,18H2,(H,20,21)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZHSOTLOTTDYIIK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>100.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332484</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022128</foodb_id>
  <kegg_id/>
  <chemspider_id>110252</chemspider_id>
  <pubchem_compound_id>123675</pubchem_compound_id>
  <chebi_id>350682</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>3,5-Diiodothyronine</wikipedia_id>
  <metlin_id>5564</metlin_id>
  <synthesis_reference>Valashek, I. E.; Kochergin, P. M.; Vinogradova, E. M.; Budanova, L. I.  Synthesis of 3,5-diiodo-DL-thyronine.    Khimiko-Farmatsevticheskii Zhurnal  (1995),  29(6),  44.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:10 UTC</creation_date>
  <update_date>2020-03-13 16:22:18 UTC</update_date>
  <accession>BMDB0000583</accession>
  <secondary_accessions>
    <accession>BMDB00583</accession>
  </secondary_accessions>
  <name>Docosanamide</name>
  <description/>
  <synonyms>
    <synonym>Behenamide</synonym>
    <synonym>Behenic acid amide</synonym>
    <synonym>Behenic amide</synonym>
    <synonym>Behenylamide</synonym>
  </synonyms>
  <chemical_formula>C22H45NO</chemical_formula>
  <average_molecular_weight>339.5988</average_molecular_weight>
  <monisotopic_moleculate_weight>339.350115067</monisotopic_moleculate_weight>
  <iupac_name>docosanamide</iupac_name>
  <traditional_iupac>behenamide</traditional_iupac>
  <cas_registry_number>3061-75-4</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCCCCCCCC(N)=O</smiles>
  <inchi>InChI=1S/C22H45NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H2,23,24)</inchi>
  <inchikey>ORAWFNKFUWGRJG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty amides</sub_class>
    <direct_parent>Fatty amides</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>110 - 113 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>9.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>8.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>16.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>docosanamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>339.5988</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>339.350115067</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCCCCCCCC(N)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C22H45NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C22H45NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H2,23,24)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ORAWFNKFUWGRJG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>43.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>106.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>151089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>151090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>151091</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022129</foodb_id>
  <kegg_id/>
  <chemspider_id>68940</chemspider_id>
  <pubchem_compound_id>76468</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5565</metlin_id>
  <synthesis_reference>Long-chain aliphatic amides.    (1963),     3 pp.  GB  939378  19631016  CAN 60:30544  AN 1964:30544</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:11 UTC</creation_date>
  <update_date>2020-03-13 16:22:18 UTC</update_date>
  <accession>BMDB0000585</accession>
  <secondary_accessions>
    <accession>BMDB00585</accession>
  </secondary_accessions>
  <name>Glucosylgalactosyl hydroxylysine</name>
  <description/>
  <synonyms>
    <synonym>1,2alpha-Glucosylgalactosyl-O-hydroxylysine</synonym>
    <synonym>2-O-a-D-Glucopyranosyl-O-b-D-galactopyranosylhydroxylysine</synonym>
    <synonym>2-O-alpha-D-Glucopyranosyl-O-beta-D-galactopyranosylhydroxylysine</synonym>
    <synonym>2-O-alpha-delta-Glucopyranosyl-O-beta-delta-galactopyranosylhydroxylysine</synonym>
    <synonym>5-[O-a-D-Glucopyranosyl-(1-&gt;2)-b-D-galactopyranosyloxy]-L-lysine</synonym>
    <synonym>5-[O-alpha-D-Glucopyranosyl-(1-&gt;2)-beta-D-galactopyranosyloxy]-L-lysine</synonym>
    <synonym>5-[O-alpha-delta-Glucopyranosyl-(1-&gt;2)-beta-delta-galactopyranosyloxy]-L-lysine</synonym>
    <synonym>Glucopyranosylgalactopyranosylhydroxylysine</synonym>
    <synonym>Glucosido-galactosyl-hydroxylysine</synonym>
    <synonym>Glucosyl galactosyl-D-hydroxylysine</synonym>
    <synonym>Glucosyl galactosyl-delta-hydroxylysine</synonym>
    <synonym>Glucosylgalactosylhydroxylysine</synonym>
    <synonym>Hydroxylysine-galactose-glucose</synonym>
    <synonym>Hydroxylysine-glucose-galactose</synonym>
    <synonym>L-5-((2-O-alpha-D-Glucopyranosyl-beta-D-galactopyranosyl)oxy)-lysine</synonym>
    <synonym>L-5-((2-O-alpha-delta-Glucopyranosyl-beta-delta-galactopyranosyl)oxy)-lysine</synonym>
    <synonym>1,2 alpha-Glucosylgalactosyl-O-hydroxylysine</synonym>
    <synonym>(2S)-2,6-Diamino-5-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}hexanoate</synonym>
  </synonyms>
  <chemical_formula>C18H34N2O13</chemical_formula>
  <average_molecular_weight>486.4682</average_molecular_weight>
  <monisotopic_moleculate_weight>486.206089184</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2,6-diamino-5-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}hexanoic acid</iupac_name>
  <traditional_iupac>(2S)-2,6-diamino-5-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}hexanoic acid</traditional_iupac>
  <cas_registry_number>32448-35-4</cas_registry_number>
  <smiles>NCC(CC[C@H](N)C(O)=O)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)C(O)[C@H]1O</smiles>
  <inchi>InChI=1S/C18H34N2O13/c19-3-6(1-2-7(20)16(28)29)30-18-15(13(26)11(24)9(5-22)32-18)33-17-14(27)12(25)10(23)8(4-21)31-17/h6-15,17-18,21-27H,1-5,19-20H2,(H,28,29)/t6?,7-,8+,9+,10+,11-,12?,13-,14+,15+,17+,18+/m0/s1</inchi>
  <inchikey>UTIRJVJBKWSIOX-SRMFCGEKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous alkali metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a alkali metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous alkali metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous alkali metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous alkali metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a cation</external_descriptor>
      <external_descriptor>alkali metal cation</external_descriptor>
      <external_descriptor>elemental potassium</external_descriptor>
      <external_descriptor>monoatomic monocation</external_descriptor>
      <external_descriptor>monovalent inorganic cation</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2,6-diamino-5-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}hexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>486.4682</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>486.206089184</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCC(CC[C@H](N)C(O)=O)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)C(O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H34N2O13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H34N2O13/c19-3-6(1-2-7(20)16(28)29)30-18-15(13(26)11(24)9(5-22)32-18)33-17-14(27)12(25)10(23)8(4-21)31-17/h6-15,17-18,21-27H,1-5,19-20H2,(H,28,29)/t6?,7-,8+,9+,10+,11-,12?,13-,14+,15+,17+,18+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UTIRJVJBKWSIOX-SRMFCGEKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>267.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>104</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>111414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>111415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>111416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448412</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022130</foodb_id>
  <kegg_id/>
  <chemspider_id>109059</chemspider_id>
  <pubchem_compound_id>122304</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>89573</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5567</metlin_id>
  <synthesis_reference>Garza, Hector; Bennett, Nelson Jr.; Rodriguez, Gladys P.  Improved rapid method for the isolation, purification and identification of collagen glycosides.    Journal of Chromatography, A  (1996),  732(2),  385-389.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:12 UTC</creation_date>
  <update_date>2020-04-14 21:15:08 UTC</update_date>
  <accession>BMDB0000586</accession>
  <secondary_accessions>
    <accession>BMDB00586</accession>
  </secondary_accessions>
  <name>Potassium</name>
  <description>Potassium, also known as K+ or potassium ion, belongs to the class of inorganic compounds known as homogeneous alkali metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a alkali metal atom. Potassium exists as a solid, possibly soluble (in water), and possibly neutral molecule. Potassium exists in all living species, ranging from bacteria to humans. Potassium is a potentially toxic compound.</description>
  <synonyms>
    <synonym>K(+)</synonym>
    <synonym>K+</synonym>
    <synonym>POTASSIUM ion</synonym>
    <synonym>Potassium(1+)</synonym>
    <synonym>Nabumeton a</synonym>
    <synonym>Kalium</synonym>
    <synonym>Potassium (ion)</synonym>
    <synonym>Potassium (k+)</synonym>
    <synonym>Potassium cation</synonym>
    <synonym>Potassium ion (k+)</synonym>
    <synonym>Potassium ion (K1+)</synonym>
    <synonym>Potassium ion(+)</synonym>
    <synonym>Potassium ion(1+)</synonym>
    <synonym>Potassium monocation</synonym>
    <synonym>Potassium(+)</synonym>
    <synonym>Potassium(1+) ion</synonym>
    <synonym>Potassium(I) cation</synonym>
    <synonym>Liver regeneration factor 1</synonym>
    <synonym>LRF-1</synonym>
    <synonym>LRF1 Transcription factor</synonym>
  </synonyms>
  <chemical_formula>K</chemical_formula>
  <average_molecular_weight>39.0983</average_molecular_weight>
  <monisotopic_moleculate_weight>38.963706861</monisotopic_moleculate_weight>
  <iupac_name>potassium(1+) ion</iupac_name>
  <traditional_iupac>potassium(1+) ion</traditional_iupac>
  <cas_registry_number>24203-36-9</cas_registry_number>
  <smiles>[K+]</smiles>
  <inchi>InChI=1S/K/q+1</inchi>
  <inchikey>NPYPAHLBTDXSSS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous alkali metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a alkali metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous alkali metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous alkali metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous alkali metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a cation</external_descriptor>
      <external_descriptor>alkali metal cation</external_descriptor>
      <external_descriptor>elemental potassium</external_descriptor>
      <external_descriptor>monoatomic monocation</external_descriptor>
      <external_descriptor>monovalent inorganic cation</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>63.2 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>potassium(1+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>39.0983</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>38.963706861</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[K+]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>K</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/K/q+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NPYPAHLBTDXSSS-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gastric Acid Production</name>
      <smpdb_id>SMP0119381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Kidney Function</name>
      <smpdb_id>SMP0119376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Degradation</name>
      <smpdb_id>SMP0087253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Muscle/Heart Contraction</name>
      <smpdb_id>SMP0119378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pancreas Function</name>
      <smpdb_id>SMP0119380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Trehalose Degradation</name>
      <smpdb_id>SMP0087263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32296</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>4710</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Dacos Chemistry Analyzer in Hereford cows</comment>
      <references>
        <reference>
          <reference_text>Early RJ, McBride BW, Ball RO: Growth and metabolism in somatotropin-treated steers: I. Growth, serum chemistry and carcass weights. J Anim Sci. 1990 Dec;68(12):4134-43. doi: 10.2527/1990.68124134x.</reference_text>
          <pubmed_id>2286555</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3900 +/- 20</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>McAdam PA, O'Dell GD: Mineral profile of blood plasma of lactating dairy cows. J Dairy Sci. 1982 Jul;65(7):1219-26. doi: 10.3168/jds.S0022-0302(82)82333-3.</reference_text>
          <pubmed_id>7108016</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3810 +/- 80</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Spectrometry (Autoanalyzer/BT3000 Plus)</comment>
      <references>
        <reference>
          <reference_text>Abdullah BASOGLU, Nuri BASPINAR, Alparslan COSKUN. NMR-based metabolomic evaluation in dairy cows with displaced abomasum. Turk J Vet Anim Sci (2014) 38(3):325-330</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>4296+/-388</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>46154+/-8295</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>49300+/-7605</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>34912.272</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>NRC. 1989. Recommended Dietary Allowances.  10th ed. Natl. Acad. Press, Washington, DC.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>31000 - 43000</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: The minerals of milk. Reprod Nutr Dev. 2005 Jul-Aug;45(4):473-83. doi: 10.1051/rnd:2005030.</reference_text>
          <pubmed_id>16045895</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>38876.371</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35039.887</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>37853.308</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>38876.371</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>39387.902</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>40155.199</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>40666.73</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>41178.261</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27763 +/- 5593</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32800 +/- 2591</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35991 +/- 3736</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>33641 +/- 811</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35400 - 40600</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw. colostrum (1-5d)</comment>
      <references>
        <reference>
          <reference_text>Tsioulpas A, Grandison AS, Lewis MJ: Changes in physical properties of bovine milk from the colostrum period to early lactation. J Dairy Sci. 2007 Nov;90(11):5012-7. doi: 10.3168/jds.2007-0192.</reference_text>
          <pubmed_id>17954740</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35500 - 42400</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk, fresh whole milk (early lactation)</comment>
      <references>
        <reference>
          <reference_text>Tsioulpas A, Grandison AS, Lewis MJ: Changes in physical properties of bovine milk from the colostrum period to early lactation. J Dairy Sci. 2007 Nov;90(11):5012-7. doi: 10.3168/jds.2007-0192.</reference_text>
          <pubmed_id>17954740</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>38620.605 - 42457.0889</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35551.418</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35551.418</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>38364.839</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>42457.0889</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>64708.696</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>46037.807</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>41434.0265</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>38364.839</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>46549.338</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>43735.917</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>39899.433</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>39899.433</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>39132.136</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>39132.136</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>38620.605</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>46549.338</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>41434.0265</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>46549.338</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35807.183</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35807.183</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>40410.964</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>40155.199</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>40410.964</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>33761.0587</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>33761.0587</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>37853.308</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>36830.246</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>36830.246</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>39878+/-6579</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>18120 +/- 153</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by ICP-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>51519+/-7094</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>48919+/-8298</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB003521</foodb_id>
  <kegg_id>C00238</kegg_id>
  <chemspider_id/>
  <pubchem_compound_id>813</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>29103</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id>34349</bigg_id>
  <wikipedia_id>Potassium</wikipedia_id>
  <metlin_id>3197</metlin_id>
  <synthesis_reference>Alberti, Augusto.  Recovering potassium salts from the refuse liquor of the manufacture of tartaric acid.    (1910),     US  957295  19100510  CAN 4:13164  AN 1910:13164</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Gaucheron F: The minerals of milk. Reprod Nutr Dev. 2005 Jul-Aug;45(4):473-83. doi: 10.1051/rnd:2005030.</reference_text>
      <pubmed_id>16045895</pubmed_id>
    </reference>
    <reference>
      <reference_text>Tsioulpas A, Grandison AS, Lewis MJ: Changes in physical properties of bovine milk from the colostrum period to early lactation. J Dairy Sci. 2007 Nov;90(11):5012-7. doi: 10.3168/jds.2007-0192.</reference_text>
      <pubmed_id>17954740</pubmed_id>
    </reference>
    <reference>
      <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
      <pubmed_id>9718493</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
      <pubmed_id>22081685</pubmed_id>
    </reference>
    <reference>
      <reference_text>NRC. 1989. Recommended Dietary Allowances.  10th ed. Natl. Acad. Press, Washington, DC.</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00145</protein_accession>
      <name>Sodium/potassium-transporting ATPase subunit alpha-1</name>
      <uniprot_id>Q08DA1</uniprot_id>
      <gene_name>ATP1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00158</protein_accession>
      <name>Sodium/potassium-transporting ATPase subunit alpha-2</name>
      <uniprot_id>A2VDL6</uniprot_id>
      <gene_name>ATP1A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00174</protein_accession>
      <name>S-adenosylmethionine synthetase</name>
      <uniprot_id>A7E3T7</uniprot_id>
      <gene_name>MAT2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00371</protein_accession>
      <name>Acetyl-CoA acetyltransferase, mitochondrial</name>
      <uniprot_id>Q29RZ0</uniprot_id>
      <gene_name>ACAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00403</protein_accession>
      <name>S-adenosylmethionine synthetase isoform type-1</name>
      <uniprot_id>Q2KJC6</uniprot_id>
      <gene_name>MAT1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00432</protein_accession>
      <name>GMP reductase 2</name>
      <uniprot_id>Q32L93</uniprot_id>
      <gene_name>GMPR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00449</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>B3IVN4</uniprot_id>
      <gene_name>PKM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00457</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>Q3ZC87</uniprot_id>
      <gene_name>PKM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00465</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>Q1JPG7</uniprot_id>
      <gene_name>PKLR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00497</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>A5D984</uniprot_id>
      <gene_name>PKM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00505</protein_accession>
      <name>Tubulin--tyrosine ligase</name>
      <uniprot_id>P38584</uniprot_id>
      <gene_name>TTL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00637</protein_accession>
      <name>2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial</name>
      <uniprot_id>P11178</uniprot_id>
      <gene_name>BCKDHA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00999</protein_accession>
      <name>GMP reductase</name>
      <uniprot_id>Q08DA2</uniprot_id>
      <gene_name>GMPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01002</protein_accession>
      <name>Inosine-5'-monophosphate dehydrogenase 2</name>
      <uniprot_id>Q3SWY3</uniprot_id>
      <gene_name>IMPDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01003</protein_accession>
      <name>Inosine-5'-monophosphate dehydrogenase</name>
      <uniprot_id>A0JNA3</uniprot_id>
      <gene_name>IMPDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01031</protein_accession>
      <name>Sodium/potassium-transporting ATPase subunit beta-2</name>
      <uniprot_id>Q28030</uniprot_id>
      <gene_name>ATP1B2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01032</protein_accession>
      <name>Sodium/potassium-transporting ATPase subunit beta-3</name>
      <uniprot_id>Q3T0C6</uniprot_id>
      <gene_name>ATP1B3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01033</protein_accession>
      <name>Sodium/potassium-transporting ATPase gamma chain</name>
      <uniprot_id>Q04645</uniprot_id>
      <gene_name>FXYD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01205</protein_accession>
      <name>Cell division protein kinase 2</name>
      <uniprot_id>Q5E9Y0</uniprot_id>
      <gene_name>CDK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01244</protein_accession>
      <name>Caseinolytic peptidase B protein homolog</name>
      <uniprot_id>Q5E9N5</uniprot_id>
      <gene_name>CLPB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01344</protein_accession>
      <name>Calcium-activated potassium channel subunit alpha-1</name>
      <uniprot_id>Q28204</uniprot_id>
      <gene_name>KCNMA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01818</protein_accession>
      <name>Muscarinic acetylcholine receptor M2</name>
      <uniprot_id>P41985</uniprot_id>
      <gene_name>CHRM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01820</protein_accession>
      <name>Muscarinic acetylcholine receptor M3</name>
      <uniprot_id>P41984</uniprot_id>
      <gene_name>CHRM3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01825</protein_accession>
      <name>Muscarinic acetylcholine receptor M4</name>
      <uniprot_id>P41986</uniprot_id>
      <gene_name>CHRM4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02170</protein_accession>
      <name>Calcium-activated potassium channel subunit beta-1</name>
      <uniprot_id>Q28067</uniprot_id>
      <gene_name>KCNMB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02268</protein_accession>
      <name>ATPase, Na+/K+ transporting, beta 1 polypeptide</name>
      <uniprot_id>Q3ZCH8</uniprot_id>
      <gene_name>ATP1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02278</protein_accession>
      <name>Sodium/potassium/calcium exchanger 1</name>
      <uniprot_id>Q28139</uniprot_id>
      <gene_name>SLC24A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02279</protein_accession>
      <name>ATP1B4 protein</name>
      <uniprot_id>A7MB71</uniprot_id>
      <gene_name>ATP1B4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02283</protein_accession>
      <name>ATP1B2 protein</name>
      <uniprot_id>A6QLL5</uniprot_id>
      <gene_name>ATP1B2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02602</protein_accession>
      <name>Potassium intermediate/small conductance calcium-activated channel, subfamily N, member 4</name>
      <uniprot_id>Q08D94</uniprot_id>
      <gene_name>KCNN4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02603</protein_accession>
      <name>Potassium voltage-gated channel, shaker-related subfamily, beta member 3</name>
      <uniprot_id>A2VDT0</uniprot_id>
      <gene_name>KCNAB3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02604</protein_accession>
      <name>KCNK2 protein</name>
      <uniprot_id>Q0VCD1</uniprot_id>
      <gene_name>KCNK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02605</protein_accession>
      <name>Potassium inwardly-rectifying channel, subfamily J, member 12</name>
      <uniprot_id>A2VDS5</uniprot_id>
      <gene_name>KCNJ12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02606</protein_accession>
      <name>KCNA2 protein</name>
      <uniprot_id>A6H7J0</uniprot_id>
      <gene_name>KCNA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02607</protein_accession>
      <name>BTB/POZ domain-containing protein KCTD18</name>
      <uniprot_id>Q29RJ0</uniprot_id>
      <gene_name>KCTD18</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02608</protein_accession>
      <name>Large conductance calcium-activated potassium channel alpha subunit isoform A</name>
      <uniprot_id>Q5G273</uniprot_id>
      <gene_name>Kcnma1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02609</protein_accession>
      <name>Potassium voltage-gated channel subfamily E member</name>
      <uniprot_id>Q2KHV0</uniprot_id>
      <gene_name>KCNE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02610</protein_accession>
      <name>BTB/POZ domain-containing protein KCTD4</name>
      <uniprot_id>A6H6X4</uniprot_id>
      <gene_name>KCTD4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02611</protein_accession>
      <name>Potassium inwardly-rectifying channel, subfamily J, member 11</name>
      <uniprot_id>A2VDS4</uniprot_id>
      <gene_name>KCNJ11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02612</protein_accession>
      <name>KCNF1 protein</name>
      <uniprot_id>A4FV89</uniprot_id>
      <gene_name>KCNF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02613</protein_accession>
      <name>BTB/POZ domain-containing protein KCTD1</name>
      <uniprot_id>Q2HJ48</uniprot_id>
      <gene_name>KCTD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02614</protein_accession>
      <name>Large conductance calcium-activated potassium channel alpha subunit isoform B</name>
      <uniprot_id>Q5G272</uniprot_id>
      <gene_name>Kcnma1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02615</protein_accession>
      <name>KCNC1 protein</name>
      <uniprot_id>A7E3B1</uniprot_id>
      <gene_name>KCNC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02616</protein_accession>
      <name>CDKN1B protein</name>
      <uniprot_id>A6QLS3</uniprot_id>
      <gene_name>CDKN1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02617</protein_accession>
      <name>Small conductance potassium channel type2</name>
      <uniprot_id>Q766U8</uniprot_id>
      <gene_name>SK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02618</protein_accession>
      <name>Potassium inwardly-rectifying channel, subfamily J, member 16</name>
      <uniprot_id>Q0VD28</uniprot_id>
      <gene_name>KCNJ16</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02619</protein_accession>
      <name>Voltage-gated potassium channel subunit beta-2</name>
      <uniprot_id>Q27955</uniprot_id>
      <gene_name>KCNAB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02620</protein_accession>
      <name>KCTD9 protein</name>
      <uniprot_id>A6QQG5</uniprot_id>
      <gene_name>KCTD9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02621</protein_accession>
      <name>KCTD5 protein</name>
      <uniprot_id>A5PKG7</uniprot_id>
      <gene_name>KCTD5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02622</protein_accession>
      <name>BTB/POZ domain-containing protein KCTD15</name>
      <uniprot_id>Q0VD00</uniprot_id>
      <gene_name>KCTD15</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02623</protein_accession>
      <name>Protein S100-B</name>
      <uniprot_id>P02638</uniprot_id>
      <gene_name>S100B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02624</protein_accession>
      <name>Potassium voltage-gated channel subfamily A member 4</name>
      <uniprot_id>Q05037</uniprot_id>
      <gene_name>KCNA4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02625</protein_accession>
      <name>Potassium voltage-gated channel subfamily H member 1</name>
      <uniprot_id>O18965</uniprot_id>
      <gene_name>KCNH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02626</protein_accession>
      <name>Potassium channel subfamily U member 1</name>
      <uniprot_id>C6KH61</uniprot_id>
      <gene_name>KCNU1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02627</protein_accession>
      <name>Calsenilin</name>
      <uniprot_id>Q17QD9</uniprot_id>
      <gene_name>KCNIP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02628</protein_accession>
      <name>Inwardly rectifying potassium channel Kir6.1</name>
      <uniprot_id>Q8WMF2</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02629</protein_accession>
      <name>Potassium voltage-gated channel subfamily KQT member 3</name>
      <uniprot_id>P58126</uniprot_id>
      <gene_name>KCNQ3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02630</protein_accession>
      <name>KCNJ15 protein</name>
      <uniprot_id>A5PJL2</uniprot_id>
      <gene_name>KCNJ15</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02631</protein_accession>
      <name>Voltage-gated K+ channel Kv1.4</name>
      <uniprot_id>Q9GLF1</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02632</protein_accession>
      <name>Potassium voltage-gated channel subfamily E member</name>
      <uniprot_id>A2VDV8</uniprot_id>
      <gene_name>KCNE4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02633</protein_accession>
      <name>Potassium voltage-gated channel subfamily B member 2</name>
      <uniprot_id>Q4ZHA6</uniprot_id>
      <gene_name>KCNB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02634</protein_accession>
      <name>Small conductance potassium channel type2 variant2</name>
      <uniprot_id>Q766U7</uniprot_id>
      <gene_name>SK2 variant2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02635</protein_accession>
      <name>BTB/POZ domain-containing protein KCTD11</name>
      <uniprot_id>Q58DF7</uniprot_id>
      <gene_name>KCTD11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02636</protein_accession>
      <name>KCTD6 protein</name>
      <uniprot_id>A6QLT0</uniprot_id>
      <gene_name>KCTD6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02637</protein_accession>
      <name>Potassium channel subfamily K member 2</name>
      <uniprot_id>Q8HY88</uniprot_id>
      <gene_name>Kcnk2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02638</protein_accession>
      <name>Potassium voltage-gated channel shaker-related subfamily 5</name>
      <uniprot_id>Q56G64</uniprot_id>
      <gene_name>KCNA5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02639</protein_accession>
      <name>Inward rectifier potassium channel 2</name>
      <uniprot_id>O19182</uniprot_id>
      <gene_name>KCNJ2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02640</protein_accession>
      <name>Putative potassium channel regulatory protein</name>
      <uniprot_id>Q863D4</uniprot_id>
      <gene_name>KCNRG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02641</protein_accession>
      <name>SH3KBP1-binding protein 1</name>
      <uniprot_id>A3KMV1</uniprot_id>
      <gene_name>SHKBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02642</protein_accession>
      <name>KCNJ10 protein</name>
      <uniprot_id>A2VDQ4</uniprot_id>
      <gene_name>KCNJ10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02643</protein_accession>
      <name>Potassium large conductance calcium-activated channel, subfamily M beta member 3</name>
      <uniprot_id>Q1RMW7</uniprot_id>
      <gene_name>KCNMB3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02644</protein_accession>
      <name>KCNH8-like protein</name>
      <uniprot_id>Q5BLU6</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02645</protein_accession>
      <name>Potassium voltage-gated channel, shaker-related subfamily, beta member 2, transcript variant 2</name>
      <uniprot_id>Q58HC3</uniprot_id>
      <gene_name>KCNAB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02646</protein_accession>
      <name>G-protein-coupled inward rectifier potassium channel</name>
      <uniprot_id>P79109</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02647</protein_accession>
      <name>Trimeric intracellular cation channel type A</name>
      <uniprot_id>A4FV75</uniprot_id>
      <gene_name>TMEM38A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02648</protein_accession>
      <name>Potassium voltage-gated channel delayed rectifier subfamily S member 3</name>
      <uniprot_id>Q5BLW6</uniprot_id>
      <gene_name>KCNS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02649</protein_accession>
      <name>ATP-sensitive inward rectifier potassium channel 12</name>
      <uniprot_id>Q4TZY1</uniprot_id>
      <gene_name>KCNJ12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02650</protein_accession>
      <name>TSC1 protein</name>
      <uniprot_id>A6QQZ6</uniprot_id>
      <gene_name>TSC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02651</protein_accession>
      <name>Mu-type opioid receptor</name>
      <uniprot_id>P79350</uniprot_id>
      <gene_name>OPRM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02652</protein_accession>
      <name>Voltage-gated potassium channel KCNC1</name>
      <uniprot_id>Q5BN36</uniprot_id>
      <gene_name>KCNC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02653</protein_accession>
      <name>KCTD10 protein</name>
      <uniprot_id>A6QLV6</uniprot_id>
      <gene_name>KCTD10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02654</protein_accession>
      <name>Potassium channel (BGK5)</name>
      <uniprot_id>Q08635</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02655</protein_accession>
      <name>KCTD17 protein</name>
      <uniprot_id>A7YWL3</uniprot_id>
      <gene_name>KCTD17</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02656</protein_accession>
      <name>Kv channel-interacting protein 4</name>
      <uniprot_id>Q2KI69</uniprot_id>
      <gene_name>KCNIP4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02657</protein_accession>
      <name>Voltage-gated potassium channel subunit beta-1</name>
      <uniprot_id>Q4PJK1</uniprot_id>
      <gene_name>KCNAB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02658</protein_accession>
      <name>BTB/POZ domain-containing protein KCTD7</name>
      <uniprot_id>A4IFB4</uniprot_id>
      <gene_name>KCTD7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02659</protein_accession>
      <name>Potassium channel subfamily K member 1</name>
      <uniprot_id>Q0P5A0</uniprot_id>
      <gene_name>KCNK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02660</protein_accession>
      <name>KCNAB1 protein</name>
      <uniprot_id>A6QPP0</uniprot_id>
      <gene_name>KCNAB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02661</protein_accession>
      <name>Potassium inwardly-rectifying channel J8</name>
      <uniprot_id>Q2KHY6</uniprot_id>
      <gene_name>KCNJ8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02662</protein_accession>
      <name>BAK5=DELAYED rectifier potassium channel KV1.5 homolog</name>
      <uniprot_id>Q9TS07</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02663</protein_accession>
      <name>Potassium channel TASK-4</name>
      <uniprot_id>Q8HZT2</uniprot_id>
      <gene_name>KCNK17</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02664</protein_accession>
      <name>Trimeric intracellular cation channel type B</name>
      <uniprot_id>Q0VC58</uniprot_id>
      <gene_name>TMEM38B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02665</protein_accession>
      <name>BTB/POZ domain-containing protein KCTD19</name>
      <uniprot_id>A7YWH3</uniprot_id>
      <gene_name>KCTD19</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02666</protein_accession>
      <name>KCTD20 protein</name>
      <uniprot_id>A7MB65</uniprot_id>
      <gene_name>KCTD20</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02667</protein_accession>
      <name>BTB/POZ domain-containing protein KCTD13</name>
      <uniprot_id>Q2T9W0</uniprot_id>
      <gene_name>KCTD13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02668</protein_accession>
      <name>High conductance calcium-activated potassium channel, MAXI-K channel</name>
      <uniprot_id>Q9TS86</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02669</protein_accession>
      <name>Kappa-type opioid receptor</name>
      <uniprot_id>Q2KIP6</uniprot_id>
      <gene_name>OPRK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02670</protein_accession>
      <name>Protein S100-A1</name>
      <uniprot_id>P02639</uniprot_id>
      <gene_name>S100A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02671</protein_accession>
      <name>Potassium voltage-gated channel subfamily V member 1</name>
      <uniprot_id>Q0P583</uniprot_id>
      <gene_name>KCNV1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02672</protein_accession>
      <name>Potassium voltage-gated channel subfamily E member</name>
      <uniprot_id>Q2NKS7</uniprot_id>
      <gene_name>KCNE2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02673</protein_accession>
      <name>Potassium voltage-gated channel subfamily D member 1</name>
      <uniprot_id>Q52PG9</uniprot_id>
      <gene_name>KCND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02674</protein_accession>
      <name>KCNH2 protein</name>
      <uniprot_id>A5PKI1</uniprot_id>
      <gene_name>KCNH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:13 UTC</creation_date>
  <update_date>2020-04-15 22:09:25 UTC</update_date>
  <accession>BMDB0000588</accession>
  <secondary_accessions>
    <accession>BMDB00588</accession>
  </secondary_accessions>
  <name>Sodium</name>
  <description>Sodium, also known as Na+ or sodium ion, belongs to the class of inorganic compounds known as homogeneous alkali metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a alkali metal atom. Sodium exists as a solid, possibly soluble (in water), and possibly neutral molecule. Sodium exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>Na(+)</synonym>
    <synonym>Na+</synonym>
    <synonym>SODIUM ion</synonym>
    <synonym>Sodium(1+)</synonym>
  </synonyms>
  <chemical_formula>Na</chemical_formula>
  <average_molecular_weight>22.9898</average_molecular_weight>
  <monisotopic_moleculate_weight>22.989769675</monisotopic_moleculate_weight>
  <iupac_name>sodium(1+) ion</iupac_name>
  <traditional_iupac>sodium(1+) ion</traditional_iupac>
  <cas_registry_number>17341-25-2</cas_registry_number>
  <smiles>[Na+]</smiles>
  <inchi>InChI=1S/Na/q+1</inchi>
  <inchikey>FKNQFGJONOIPTF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous alkali metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a alkali metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous alkali metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous alkali metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous alkali metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a cation</external_descriptor>
      <external_descriptor>alkali metal cation</external_descriptor>
      <external_descriptor>elemental sodium</external_descriptor>
      <external_descriptor>monoatomic monocation</external_descriptor>
      <external_descriptor>monovalent inorganic cation</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>97.82 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>sodium(1+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>22.9898</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>22.989769675</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Na+]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Na</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Na/q+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FKNQFGJONOIPTF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Kidney Function</name>
      <smpdb_id>SMP0119376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Degradation</name>
      <smpdb_id>SMP0087253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Muscle/Heart Contraction</name>
      <smpdb_id>SMP0119378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Thyroid Hormone Synthesis</name>
      <smpdb_id>SMP0087269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Trehalose Degradation</name>
      <smpdb_id>SMP0087263</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31339</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>143000</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Dacos Chemistry Analyzer in Hereford cows</comment>
      <references>
        <reference>
          <reference_text>Early RJ, McBride BW, Ball RO: Growth and metabolism in somatotropin-treated steers: I. Growth, serum chemistry and carcass weights. J Anim Sci. 1990 Dec;68(12):4134-43. doi: 10.2527/1990.68124134x.</reference_text>
          <pubmed_id>2286555</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>144500 +/- 260</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>McAdam PA, O'Dell GD: Mineral profile of blood plasma of lactating dairy cows. J Dairy Sci. 1982 Jul;65(7):1219-26. doi: 10.3168/jds.S0022-0302(82)82333-3.</reference_text>
          <pubmed_id>7108016</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>142500 +/- 1110</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Spectrometry (Autoanalyzer/BT3000 Plus)</comment>
      <references>
        <reference>
          <reference_text>Abdullah BASOGLU, Nuri BASPINAR, Alparslan COSKUN. NMR-based metabolomic evaluation in dairy cows with displaced abomasum. Turk J Vet Anim Sci (2014) 38(3):325-330</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>133515+/-13658</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>25588+/-4753</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>10109+/-2109</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17000 - 28000</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: The minerals of milk. Reprod Nutr Dev. 2005 Jul-Aug;45(4):473-83. doi: 10.1051/rnd:2005030.</reference_text>
          <pubmed_id>16045895</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25228.58</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18703.947</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19573.898</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20008.874</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20878.825</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21313.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21748.776</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23053.702</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25228.58</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
          <pubmed_id>9718493</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16345 +/- 1257</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16560 +/- 1174.25</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16197 +/- 1765</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15926 +/- 1396</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21313.800 - 22183.751</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>24793.604</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>24793.604</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19138.922</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>22618.727</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1304.927</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25228.58</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>22618.727</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19138.922</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25663.555</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23053.702</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18268.971</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18268.971</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18877.937</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18877.937</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21313.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25663.555</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>22618.727</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25663.555</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20443.849</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20443.849</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19269.415</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19225.918</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19269.415</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18703.947</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18703.947</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18529.957</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19747.888</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19747.888</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>235634+/-19788</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>113362 +/- 3434</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by ICP-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>12037+/-2852</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>35578+/-6600</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>899</chemspider_id>
  <pubchem_compound_id>923</pubchem_compound_id>
  <foodb_id>FDB031052</foodb_id>
  <kegg_id>C01330</kegg_id>
  <chebi_id>29101</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>37376</bigg_id>
  <wikipedia_id>Sodium</wikipedia_id>
  <metlin_id>3192</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Gaucheron F: The minerals of milk. Reprod Nutr Dev. 2005 Jul-Aug;45(4):473-83. doi: 10.1051/rnd:2005030.</reference_text>
      <pubmed_id>16045895</pubmed_id>
    </reference>
    <reference>
      <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
      <pubmed_id>9718493</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
      <pubmed_id>22081685</pubmed_id>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00145</protein_accession>
      <name>Sodium/potassium-transporting ATPase subunit alpha-1</name>
      <uniprot_id>Q08DA1</uniprot_id>
      <gene_name>ATP1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00158</protein_accession>
      <name>Sodium/potassium-transporting ATPase subunit alpha-2</name>
      <uniprot_id>A2VDL6</uniprot_id>
      <gene_name>ATP1A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00472</protein_accession>
      <name>DNA polymerase beta</name>
      <uniprot_id>Q27958</uniprot_id>
      <gene_name>POLB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00966</protein_accession>
      <name>Ubiquitin-conjugating enzyme E2 E3</name>
      <uniprot_id>Q2T9X7</uniprot_id>
      <gene_name>UBE2E3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01006</protein_accession>
      <name>Protein tyrosine phosphatase type IVA 3</name>
      <uniprot_id>A2VDT1</uniprot_id>
      <gene_name>PTP4A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01031</protein_accession>
      <name>Sodium/potassium-transporting ATPase subunit beta-2</name>
      <uniprot_id>Q28030</uniprot_id>
      <gene_name>ATP1B2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01032</protein_accession>
      <name>Sodium/potassium-transporting ATPase subunit beta-3</name>
      <uniprot_id>Q3T0C6</uniprot_id>
      <gene_name>ATP1B3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01033</protein_accession>
      <name>Sodium/potassium-transporting ATPase gamma chain</name>
      <uniprot_id>Q04645</uniprot_id>
      <gene_name>FXYD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01610</protein_accession>
      <name>Prostaglandin E2 receptor EP3 subtype</name>
      <uniprot_id>P34979</uniprot_id>
      <gene_name>PTGER3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01643</protein_accession>
      <name>Solute carrier family 10 (Sodium/bile acid cotransporter family), member 4</name>
      <uniprot_id>A0JNQ1</uniprot_id>
      <gene_name>SLC10A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01849</protein_accession>
      <name>SLC12A5 protein</name>
      <uniprot_id>A8KC65</uniprot_id>
      <gene_name>SLC12A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01862</protein_accession>
      <name>Na-K-Cl cotransporter</name>
      <uniprot_id>O18978</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01863</protein_accession>
      <name>Sodium chloride cotransporter</name>
      <uniprot_id>O97740</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01874</protein_accession>
      <name>Sodium/myo-inositol cotransporter 2</name>
      <uniprot_id>Q3ZC26</uniprot_id>
      <gene_name>SLC5A11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01875</protein_accession>
      <name>Na+/myo-inositol cotransporter</name>
      <uniprot_id>O19135</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01896</protein_accession>
      <name>Sodium- and chloride-dependent creatine transporter 1</name>
      <uniprot_id>O18875</uniprot_id>
      <gene_name>SLC6A8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02002</protein_accession>
      <name>Sodium iodide symporter</name>
      <uniprot_id>B6ZBT4</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02003</protein_accession>
      <name>Truncated sodium iodide symporter</name>
      <uniprot_id>B2CSJ0</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02085</protein_accession>
      <name>Sodium-coupled neutral amino acid transporter 2</name>
      <uniprot_id>A2VE31</uniprot_id>
      <gene_name>SLC38A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02086</protein_accession>
      <name>Solute carrier family 5 (Choline transporter), member 7</name>
      <uniprot_id>Q2KI26</uniprot_id>
      <gene_name>SLC5A7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02092</protein_accession>
      <name>Sodium-coupled neutral amino acid transporter 5</name>
      <uniprot_id>Q5E9S9</uniprot_id>
      <gene_name>SLC38A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02141</protein_accession>
      <name>Solute carrier family 13 (Sodium-dependent dicarboxylate transporter), member 2</name>
      <uniprot_id>Q3SYV8</uniprot_id>
      <gene_name>SLC13A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02143</protein_accession>
      <name>Solute carrier family 13 (Sodium-dependent dicarboxylate transporter), member 3</name>
      <uniprot_id>A1A4I3</uniprot_id>
      <gene_name>SLC13A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02149</protein_accession>
      <name>Putative sodium-glucose cotransporter</name>
      <uniprot_id>Q9TTR6</uniprot_id>
      <gene_name>sglt1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02157</protein_accession>
      <name>Na+/glucose cotransporter</name>
      <uniprot_id>Q8MKB7</uniprot_id>
      <gene_name>SGLT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02158</protein_accession>
      <name>Sodium-dependent glucose transporter SGLT-I</name>
      <uniprot_id>Q95JG8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02173</protein_accession>
      <name>Amiloride-sensitive sodium channel subunit alpha</name>
      <uniprot_id>P55270</uniprot_id>
      <gene_name>SCNN1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02261</protein_accession>
      <name>SCNN1B protein</name>
      <uniprot_id>A5D7U4</uniprot_id>
      <gene_name>SCNN1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02262</protein_accession>
      <name>Sodium channel subunit beta-4</name>
      <uniprot_id>Q08E08</uniprot_id>
      <gene_name>SCN4B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02263</protein_accession>
      <name>Solute carrier family 10 (Sodium/bile acid cotransporter family), member 1</name>
      <uniprot_id>Q2KJ85</uniprot_id>
      <gene_name>SLC10A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02264</protein_accession>
      <name>Voltage-gated sodium channel alpha subunit</name>
      <uniprot_id>Q8WMP8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02265</protein_accession>
      <name>Sodium-driven chloride bicarbonate exchanger</name>
      <uniprot_id>Q32LP4</uniprot_id>
      <gene_name>SLC4A10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02266</protein_accession>
      <name>Sodium/calcium exchanger 1</name>
      <uniprot_id>P48765</uniprot_id>
      <gene_name>SLC8A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02267</protein_accession>
      <name>Vesicular glutamate transporter 1</name>
      <uniprot_id>A4FV52</uniprot_id>
      <gene_name>SLC17A7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02268</protein_accession>
      <name>ATPase, Na+/K+ transporting, beta 1 polypeptide</name>
      <uniprot_id>Q3ZCH8</uniprot_id>
      <gene_name>ATP1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02269</protein_accession>
      <name>Sodium/hydrogen exchanger 1</name>
      <uniprot_id>Q28036</uniprot_id>
      <gene_name>SLC9A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02270</protein_accession>
      <name>Sodium-dependent phosphate transporter 2</name>
      <uniprot_id>A1A4I1</uniprot_id>
      <gene_name>SLC20A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02271</protein_accession>
      <name>Electrogenic sodium bicarbonate cotransporter 1</name>
      <uniprot_id>Q9GL77</uniprot_id>
      <gene_name>SLC4A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02272</protein_accession>
      <name>Sodium/hydrogen exchanger</name>
      <uniprot_id>Q0VD46</uniprot_id>
      <gene_name>SLC9A9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02273</protein_accession>
      <name>Sodium proton exchanger</name>
      <uniprot_id>O97738</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02274</protein_accession>
      <name>Solute carrier family 13 (Sodium/sulfate symporters), member 4</name>
      <uniprot_id>Q08E60</uniprot_id>
      <gene_name>SLC13A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02275</protein_accession>
      <name>Sodium-coupled monocarboxylate transporter 2</name>
      <uniprot_id>A7MBD8</uniprot_id>
      <gene_name>SLC5A12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02276</protein_accession>
      <name>P3 protein</name>
      <uniprot_id>Q0V8N6</uniprot_id>
      <gene_name>SLC10A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02277</protein_accession>
      <name>Solute carrier family 5 (Sodium-dependent vitamin transporter), member 6</name>
      <uniprot_id>A1L530</uniprot_id>
      <gene_name>SLC5A6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02278</protein_accession>
      <name>Sodium/potassium/calcium exchanger 1</name>
      <uniprot_id>Q28139</uniprot_id>
      <gene_name>SLC24A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02279</protein_accession>
      <name>ATP1B4 protein</name>
      <uniprot_id>A7MB71</uniprot_id>
      <gene_name>ATP1B4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02280</protein_accession>
      <name>Putative sodium-coupled neutral amino acid transporter 11</name>
      <uniprot_id>Q5EA97</uniprot_id>
      <gene_name>SLC38A11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02281</protein_accession>
      <name>Putative sodium-coupled neutral amino acid transporter 7</name>
      <uniprot_id>A7E3U5</uniprot_id>
      <gene_name>SLC38A7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02282</protein_accession>
      <name>Na+/glucose cotransporter 2</name>
      <uniprot_id>Q6XUI1</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02283</protein_accession>
      <name>ATP1B2 protein</name>
      <uniprot_id>A6QLL5</uniprot_id>
      <gene_name>ATP1B2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02284</protein_accession>
      <name>Sodium channel subunit beta-3</name>
      <uniprot_id>Q2KI11</uniprot_id>
      <gene_name>SCN3B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02285</protein_accession>
      <name>Sodium/myo-inositol cotransporter</name>
      <uniprot_id>P53793</uniprot_id>
      <gene_name>SLC5A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02286</protein_accession>
      <name>Sodium channel subunit beta-1</name>
      <uniprot_id>Q17QN4</uniprot_id>
      <gene_name>SCN1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02287</protein_accession>
      <name>Vesicular glutamate transporter 2</name>
      <uniprot_id>A6QLI1</uniprot_id>
      <gene_name>SLC17A6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02288</protein_accession>
      <name>Sodium-dependent phosphate transport protein 3</name>
      <uniprot_id>Q32LF0</uniprot_id>
      <gene_name>SLC17A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02289</protein_accession>
      <name>Sodium/glucose cotransporter 5</name>
      <uniprot_id>Q6R4Q5</uniprot_id>
      <gene_name>SLC5A10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02290</protein_accession>
      <name>Sodium-dependent phosphate transport protein 2B</name>
      <uniprot_id>Q27960</uniprot_id>
      <gene_name>SLC34A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02291</protein_accession>
      <name>Sodium channel modifier 1</name>
      <uniprot_id>Q3ZBR0</uniprot_id>
      <gene_name>SCNM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02292</protein_accession>
      <name>Solute carrier family 10 member 6</name>
      <uniprot_id>A6QP84</uniprot_id>
      <gene_name>SLC10A6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02293</protein_accession>
      <name>Similar to solute carrier family 5 (Sodium/glucose cotransporter), member 1</name>
      <uniprot_id>Q2KJ00</uniprot_id>
      <gene_name>LOC531152</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02294</protein_accession>
      <name>Sodium/hydrogen exchanger</name>
      <uniprot_id>A7MB44</uniprot_id>
      <gene_name>SLC9A6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02295</protein_accession>
      <name>Sodium proton exchanger</name>
      <uniprot_id>O97739</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02296</protein_accession>
      <name>Amiloride-sensitive cation channel 1, neuronal</name>
      <uniprot_id>Q0VC38</uniprot_id>
      <gene_name>ACCN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02297</protein_accession>
      <name>Solute carrier family 4 sodium bicarbonate cotransporter member 4 variant NBCe1B</name>
      <uniprot_id>B2NIZ2</uniprot_id>
      <gene_name>SLC4A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:15 UTC</creation_date>
  <update_date>2020-03-13 16:22:20 UTC</update_date>
  <accession>BMDB0000590</accession>
  <secondary_accessions>
    <accession>BMDB00590</accession>
  </secondary_accessions>
  <name>Glutarylglycine</name>
  <description/>
  <synonyms>
    <synonym>5-[(Carboxymethyl)amino]-5-oxo-pentanoate</synonym>
    <synonym>5-[(Carboxymethyl)amino]-5-oxo-pentanoic acid</synonym>
    <synonym>N-(Carboxymethyl)-glutaramic acid</synonym>
    <synonym>4-[(Carboxymethyl)-C-hydroxycarbonimidoyl]butanoate</synonym>
  </synonyms>
  <chemical_formula>C7H11NO5</chemical_formula>
  <average_molecular_weight>189.1659</average_molecular_weight>
  <monisotopic_moleculate_weight>189.063722467</monisotopic_moleculate_weight>
  <iupac_name>4-[(carboxymethyl)carbamoyl]butanoic acid</iupac_name>
  <traditional_iupac>4-(carboxymethylcarbamoyl)butanoic acid</traditional_iupac>
  <cas_registry_number>17686-38-3</cas_registry_number>
  <smiles>OC(=O)CCCC(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C7H11NO5/c9-5(8-4-7(12)13)2-1-3-6(10)11/h1-4H2,(H,8,9)(H,10,11)(H,12,13)</inchi>
  <inchikey>NBLKTRLPZFCMJG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-[(carboxymethyl)carbamoyl]butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>189.1659</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>189.063722467</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCC(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H11NO5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H11NO5/c9-5(8-4-7(12)13)2-1-3-6(10)11/h1-4H2,(H,8,9)(H,10,11)(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NBLKTRLPZFCMJG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>103.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338961</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022131</foodb_id>
  <kegg_id/>
  <chemspider_id>19712034</chemspider_id>
  <pubchem_compound_id>23592950</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5569</metlin_id>
  <synthesis_reference>Paul, Lieselotte; Dittmar, Adelheid; Rusch, Christel.  Synthesis of maleoyl- and glutarylglycyl chlorides.    Chemische Berichte  (1967),  100(8),  2757-60.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:16 UTC</creation_date>
  <update_date>2020-03-13 16:22:21 UTC</update_date>
  <accession>BMDB0000592</accession>
  <secondary_accessions>
    <accession>BMDB00592</accession>
  </secondary_accessions>
  <name>Glucosamine 6-sulfate</name>
  <description/>
  <synonyms>
    <synonym>2-Amino-2-deoxy-beta-D-glucopyranose 6-sulfate</synonym>
    <synonym>2-Amino-2-deoxy-D-glucose 6-sulfate</synonym>
    <synonym>2-Amino-2-deoxy-D-glucose 6-sulphate</synonym>
    <synonym>6-O-SulfO-beta-D-glucosamine</synonym>
    <synonym>beta-D-Glucosamine 6-O-sulfate</synonym>
    <synonym>D-Glucosamine-6-sulfate</synonym>
    <synonym>D-Glucosamine-6-sulphate</synonym>
    <synonym>GLCN-6S</synonym>
    <synonym>Glucosamine 6-O-sulfate</synonym>
    <synonym>Glucosamine 6-O-sulphate</synonym>
    <synonym>Glucosamine 6-sulphate</synonym>
    <synonym>2-Amino-2-deoxy-b-D-glucopyranose 6-sulfate</synonym>
    <synonym>2-Amino-2-deoxy-b-D-glucopyranose 6-sulfuric acid</synonym>
    <synonym>2-Amino-2-deoxy-b-D-glucopyranose 6-sulphate</synonym>
    <synonym>2-Amino-2-deoxy-b-D-glucopyranose 6-sulphuric acid</synonym>
    <synonym>2-Amino-2-deoxy-beta-D-glucopyranose 6-sulfuric acid</synonym>
    <synonym>2-Amino-2-deoxy-beta-D-glucopyranose 6-sulphate</synonym>
    <synonym>2-Amino-2-deoxy-beta-D-glucopyranose 6-sulphuric acid</synonym>
    <synonym>2-Amino-2-deoxy-β-D-glucopyranose 6-sulfate</synonym>
    <synonym>2-Amino-2-deoxy-β-D-glucopyranose 6-sulfuric acid</synonym>
    <synonym>2-Amino-2-deoxy-β-D-glucopyranose 6-sulphate</synonym>
    <synonym>2-Amino-2-deoxy-β-D-glucopyranose 6-sulphuric acid</synonym>
    <synonym>2-Amino-2-deoxy-D-glucose 6-sulfuric acid</synonym>
    <synonym>2-Amino-2-deoxy-D-glucose 6-sulphuric acid</synonym>
    <synonym>6-O-SulfO-b-D-glucosamine</synonym>
    <synonym>6-O-SulfO-β-D-glucosamine</synonym>
    <synonym>6-O-SulphO-b-D-glucosamine</synonym>
    <synonym>6-O-SulphO-beta-D-glucosamine</synonym>
    <synonym>6-O-SulphO-β-D-glucosamine</synonym>
    <synonym>b-D-Glucosamine 6-O-sulfate</synonym>
    <synonym>b-D-Glucosamine 6-O-sulfuric acid</synonym>
    <synonym>b-D-Glucosamine 6-O-sulphate</synonym>
    <synonym>b-D-Glucosamine 6-O-sulphuric acid</synonym>
    <synonym>beta-D-Glucosamine 6-O-sulfuric acid</synonym>
    <synonym>beta-D-Glucosamine 6-O-sulphate</synonym>
    <synonym>beta-D-Glucosamine 6-O-sulphuric acid</synonym>
    <synonym>Β-D-glucosamine 6-O-sulfate</synonym>
    <synonym>Β-D-glucosamine 6-O-sulfuric acid</synonym>
    <synonym>Β-D-glucosamine 6-O-sulphate</synonym>
    <synonym>Β-D-glucosamine 6-O-sulphuric acid</synonym>
    <synonym>D-Glucosamine-6-sulfuric acid</synonym>
    <synonym>D-Glucosamine-6-sulphuric acid</synonym>
    <synonym>Glucosamine 6-O-sulfuric acid</synonym>
    <synonym>Glucosamine 6-O-sulphuric acid</synonym>
    <synonym>Glucosamine 6-sulfuric acid</synonym>
    <synonym>Glucosamine 6-sulphuric acid</synonym>
    <synonym>b-D-Glucosamine 6-sulfate</synonym>
    <synonym>b-D-Glucosamine 6-sulfuric acid</synonym>
    <synonym>b-D-Glucosamine 6-sulphate</synonym>
    <synonym>b-D-Glucosamine 6-sulphuric acid</synonym>
    <synonym>beta-D-Glucosamine 6-sulfuric acid</synonym>
    <synonym>beta-D-Glucosamine 6-sulphate</synonym>
    <synonym>beta-D-Glucosamine 6-sulphuric acid</synonym>
    <synonym>Β-D-glucosamine 6-sulfate</synonym>
    <synonym>Β-D-glucosamine 6-sulfuric acid</synonym>
    <synonym>Β-D-glucosamine 6-sulphate</synonym>
    <synonym>Β-D-glucosamine 6-sulphuric acid</synonym>
    <synonym>Glucosamine 6-sulfate</synonym>
  </synonyms>
  <chemical_formula>C6H13NO8S</chemical_formula>
  <average_molecular_weight>259.234</average_molecular_weight>
  <monisotopic_moleculate_weight>259.036187087</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R,6R)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}sulfonic acid</iupac_name>
  <traditional_iupac>glucosamine 6-sulfate</traditional_iupac>
  <cas_registry_number>91674-26-9</cas_registry_number>
  <smiles>N[C@H]1[C@H](O)O[C@H](COS(O)(=O)=O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H13NO8S/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H,11,12,13)/t2-,3-,4-,5-,6-/m1/s1</inchi>
  <inchikey>MTDHILKWIRSIHB-QZABAPFNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexoses</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Aminosaccharides</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monosaccharide sulfates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino saccharide</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide sulfate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R,6R)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>259.234</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>259.036187087</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@H]1[C@H](O)O[C@H](COS(O)(=O)=O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13NO8S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13NO8S/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H,11,12,13)/t2-,3-,4-,5-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MTDHILKWIRSIHB-QZABAPFNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>159.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>325018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>325019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>325020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451963</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022132</foodb_id>
  <kegg_id>C04132</kegg_id>
  <chemspider_id>65298</chemspider_id>
  <pubchem_compound_id>72361</pubchem_compound_id>
  <chebi_id>133343</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5571</metlin_id>
  <synthesis_reference>Saito, Tomoo; Noguchi, Junzo; Komatsu, Kiroku.  The esterification of carbohydrates in concentrated sul-furic acid. III.  The synthesis of 2-amino-2-deoxy-D-glucose O-sulfate, 2-acetamido-2-deoxy-D-glucose-6-sulfate and its calcium and barium salts.    Nippon Kagaku Zasshi  (1961),  82  472-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:17 UTC</creation_date>
  <update_date>2020-03-19 18:59:46 UTC</update_date>
  <accession>BMDB0000593</accession>
  <secondary_accessions>
    <accession>BMDB00593</accession>
  </secondary_accessions>
  <name>PC(18:1(9Z)/18:1(9Z))</name>
  <description>PC(18:1(9Z)/18:1(9Z)) , also known as dielaidinoyl lecithin or 1,2-DOCPC, belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. PC(18:1(9Z)/18:1(9Z)) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).</description>
  <synonyms>
    <synonym>(R-(Z,Z))-(7-Oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxide</synonym>
    <synonym>1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine</synonym>
    <synonym>1,2-Dioleoyl-L-alpha-lecithin</synonym>
    <synonym>1-(9Z)-Octadecenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine</synonym>
    <synonym>1-C18:1(Omega-9)-2-C18:1(omega-9)-phosphatidylcholine</synonym>
    <synonym>Dioleoyl lecithin</synonym>
    <synonym>Dioleoyl phosphatidylcholine</synonym>
    <synonym>PC 18:1</synonym>
    <synonym>PC(18:1(9Z)/18:1(9Z))</synonym>
    <synonym>PC(18:1/18:1)</synonym>
    <synonym>Phosphatidylcholine 18:1</synonym>
    <synonym>1,2-Dioleoyl-L-a-lecithin</synonym>
    <synonym>1,2-Dioleoyl-L-α-lecithin</synonym>
    <synonym>1,2-Di-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine</synonym>
    <synonym>1,2-Dioleoyl-sn-glycerol-3-ethylphosphocholine</synonym>
    <synonym>Dioleylphosphatidylcholine</synonym>
    <synonym>1,2-Oleoylphosphatidylcholine, (L-alpha)-(R-(Z,Z))-isomer</synonym>
    <synonym>Dielaidoylphosphatidylcholine</synonym>
    <synonym>Dioleoylphosphatidylcholine</synonym>
    <synonym>1,2-Dioleoylglycerophosphocholine</synonym>
    <synonym>1,2-Oleoyl-sn-glycero-3-phosphocholine</synonym>
    <synonym>DOPC</synonym>
    <synonym>Dielaidinoyl lecithin</synonym>
    <synonym>1,2-DOCPC</synonym>
    <synonym>1,2-Dioleoyl glycerophosphocholine</synonym>
    <synonym>1,2-Dioleoyl-sn-glycero-3-phosphocholine</synonym>
    <synonym>1,2-Oleoylphosphatidylcholine</synonym>
    <synonym>1,2-Dioleoyl-GPC</synonym>
    <synonym>1,2-Dioleoyl-sn-glycero-phosphatidylcholine</synonym>
    <synonym>GPC(18:1(9Z)/18:1(9Z))</synonym>
    <synonym>GPC(18:1/18:1)</synonym>
    <synonym>GPC(18:1n9/18:1n9)</synonym>
    <synonym>GPC(18:1w9/18:1w9)</synonym>
    <synonym>GPC(36:2)</synonym>
    <synonym>GPCho(18:1(9Z)/18:1(9Z))</synonym>
    <synonym>GPCho(18:1/18:1)</synonym>
    <synonym>GPCho(18:1n9/18:1n9)</synonym>
    <synonym>GPCho(18:1w9/18:1w9)</synonym>
    <synonym>GPCho(36:2)</synonym>
    <synonym>PC(18:1n9/18:1n9)</synonym>
    <synonym>PC(18:1w9/18:1w9)</synonym>
    <synonym>PC(36:2)</synonym>
    <synonym>Phosphatidylcholine(18:1(9Z)/18:1(9Z))</synonym>
    <synonym>Phosphatidylcholine(18:1/18:1)</synonym>
    <synonym>Phosphatidylcholine(18:1n9/18:1n9)</synonym>
    <synonym>Phosphatidylcholine(18:1w9/18:1w9)</synonym>
    <synonym>Phosphatidylcholine(36:2)</synonym>
    <synonym>1,2-Dioleoyl-3-sn-phosphatidylcholine</synonym>
    <synonym>1,2-Dioleoyl-sn-glycero-3-phosphochline</synonym>
    <synonym>1,2-Dioleoyl-sn-glycero-3-phosphorylcholine</synonym>
    <synonym>1,2-Dioleoyl-sn-phosphatidylcholine</synonym>
    <synonym>1,2-Dioleoylphosphatidylcholine</synonym>
    <synonym>1,2-Dioleyl-L-lecithin</synonym>
    <synonym>Dioleoyl L-alpha-lecithin</synonym>
    <synonym>Dioleoyl L-α-lecithin</synonym>
    <synonym>Dioleoyl-3-sn-phosphatidylcholine</synonym>
    <synonym>Dioleoyl-L-alpha-glycerophosphocholine</synonym>
    <synonym>Dioleoyl-L-alpha-glycerophosphorylcholine</synonym>
    <synonym>Dioleoyl-L-alpha-phosphatidylcholine</synonym>
    <synonym>Dioleoyl-L-α-glycerophosphocholine</synonym>
    <synonym>Dioleoyl-L-α-glycerophosphorylcholine</synonym>
    <synonym>Dioleoyl-L-α-phosphatidylcholine</synonym>
    <synonym>Dioleoyllecithin</synonym>
    <synonym>L-Dioleoyl lecithin</synonym>
    <synonym>L-Dioleoylphosphatidylcholine</synonym>
    <synonym>L-alpha-Di(cis-9-octadecanoyl) lecithin</synonym>
    <synonym>L-alpha-Dioleoyl phosphatidylcholine</synonym>
    <synonym>L-alpha-Dioleoyllecithin</synonym>
    <synonym>L-alpha-Dioleylphosphatidylcholine</synonym>
    <synonym>L-α-Di(cis-9-octadecanoyl) lecithin</synonym>
    <synonym>L-α-Dioleoyl phosphatidylcholine</synonym>
    <synonym>L-α-Dioleoyllecithin</synonym>
    <synonym>L-α-Dioleylphosphatidylcholine</synonym>
    <synonym>sn-3-Dioleoyllecithin</synonym>
    <synonym>1,2-Dioleoylglycerol-3-phosphorylcholine</synonym>
    <synonym>1,2-Dioleoylglyceryl-3-phosphorylcholine</synonym>
    <synonym>1,2-Dioleoyllecithin</synonym>
    <synonym>Dioleoylglycerophosphocholine</synonym>
    <synonym>Dioleoylglycerophosphorylcholine</synonym>
    <synonym>Dioleoylglycerylphosphorylcholine</synonym>
    <synonym>Dioleyl lecithin</synonym>
    <synonym>Dioleyl phosphatidylcholine</synonym>
  </synonyms>
  <chemical_formula>C44H84NO8P</chemical_formula>
  <average_molecular_weight>786.1134</average_molecular_weight>
  <monisotopic_moleculate_weight>785.593455181</monisotopic_moleculate_weight>
  <iupac_name>(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium</iupac_name>
  <traditional_iupac>(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium</traditional_iupac>
  <cas_registry_number>4235-95-4</cas_registry_number>
  <smiles>[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC</smiles>
  <inchi>InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-/t42-/m1/s1</inchi>
  <inchikey>SNKAWJBJQDLSFF-NVKMUCNASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerophospholipids</class>
    <sub_class>Glycerophosphocholines</sub_class>
    <direct_parent>Phosphatidylcholines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Dialkyl phosphates</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phosphocholines</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Diacylglycero-3-phosphocholine</substituent>
      <substituent>Dialkyl phosphate</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphocholine</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Diacylglycerophosphocholines</external_descriptor>
      <external_descriptor>phosphatidylcholine 36:2</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>9.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>786.1134</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>785.593455181</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C44H84NO8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-/t42-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SNKAWJBJQDLSFF-NVKMUCNASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>111.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>236.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>96.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>648751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>648752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>648753</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.82 +/- 0.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.0 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9.5 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.48 +/- 0.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.263</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.104</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.019</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.642</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.564 +/- 0.381</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.501 +/- 0.341</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.531 +/- 0.436</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.601 +/- 0.735</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>8525772</chemspider_id>
  <pubchem_compound_id>10350317</pubchem_compound_id>
  <foodb_id/>
  <kegg_id/>
  <chebi_id>74669</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id>CPD-2181</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Tokuyama, Satoru; Morisawa, Kazuya; Nakachi, Osamu; Nakano, Yoshiro; Miki, Tomoharu.  Preparation of phosphatidylcholines.    Jpn. Kokai Tokkyo Koho  (1989),     6 pp. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:18 UTC</creation_date>
  <update_date>2020-04-15 22:09:26 UTC</update_date>
  <accession>BMDB0000594</accession>
  <secondary_accessions>
    <accession>BMDB00594</accession>
  </secondary_accessions>
  <name>Glutamylphenylalanine</name>
  <description/>
  <synonyms>
    <synonym>γ-Glu-Phe</synonym>
    <synonym>γ-L-Glu-L-Phe</synonym>
    <synonym>γ-Glutamylphenylalanine</synonym>
    <synonym>γ-L-Glutamyl-L-phenylalanine</synonym>
    <synonym>L-γ-Glutamyl-L-phenylalanine</synonym>
    <synonym>N-γ-Glutamylphenylalanine</synonym>
    <synonym>N-L-γ-Glutamylphenylalanine</synonym>
    <synonym>N-L-γ-Glutamyl-L-phenylalanine</synonym>
    <synonym>gamma-Glu-Phe</synonym>
    <synonym>gamma-L-Glu-L-Phe</synonym>
    <synonym>gamma-L-Glutamyl-L-phenylalanine</synonym>
    <synonym>L-gamma-Glutamyl-L-phenylalanine</synonym>
    <synonym>N-gamma-Glutamylphenylalanine</synonym>
    <synonym>N-L-gamma-Glutamylphenylalanine</synonym>
    <synonym>N-L-gamma-Glutamyl-L-phenylalanine</synonym>
    <synonym>H-γ-Glu-Phe-OH</synonym>
    <synonym>H-gamma-Glu-Phe-OH</synonym>
    <synonym>gamma-Glutamylphenylalanine</synonym>
    <synonym>N-gamma-L-Glutamyl-L-phenylalanine</synonym>
    <synonym>N-(gamma-L-Glutamyl)phenylalanine</synonym>
    <synonym>N-L-gamma-Glutamyl-3-phenyl-L-alanine</synonym>
    <synonym>N-γ-L-Glutamyl-L-phenylalanine</synonym>
    <synonym>(2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid</synonym>
    <synonym>L-gamma-Glu-L-Phe</synonym>
    <synonym>(2S)-2-Amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoate</synonym>
    <synonym>g-Glutamylphenylalanine</synonym>
    <synonym>L-g-Glu-L-Phe</synonym>
    <synonym>L-γ-Glu-L-Phe</synonym>
    <synonym>L-g-Glutamyl-L-phenylalanine</synonym>
    <synonym>N-(g-L-Glutamyl)phenylalanine</synonym>
    <synonym>N-(γ-L-Glutamyl)phenylalanine</synonym>
    <synonym>N-L-g-Glutamyl-3-phenyl-L-alanine</synonym>
    <synonym>N-L-γ-Glutamyl-3-phenyl-L-alanine</synonym>
    <synonym>N-L-g-Glutamyl-L-phenylalanine</synonym>
    <synonym>g-Glu-Phe</synonym>
  </synonyms>
  <chemical_formula>C14H18N2O5</chemical_formula>
  <average_molecular_weight>294.3031</average_molecular_weight>
  <monisotopic_moleculate_weight>294.121571696</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid</iupac_name>
  <traditional_iupac>gamma-glutamylphenylalanine</traditional_iupac>
  <cas_registry_number>7432-24-8</cas_registry_number>
  <smiles>N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C14H18N2O5/c15-10(13(18)19)6-7-12(17)16-11(14(20)21)8-9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,17)(H,18,19)(H,20,21)/t10-,11-/m0/s1</inchi>
  <inchikey>XHHOHZPNYFQJKL-QWRGUYRKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Phenylalanine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>294.3031</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>294.121571696</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H18N2O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H18N2O5/c15-10(13(18)19)6-7-12(17)16-11(14(20)21)8-9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,17)(H,18,19)(H,20,21)/t10-,11-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XHHOHZPNYFQJKL-QWRGUYRKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>129.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>73.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447338</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id/>
  <pubchem_compound_id>111299</pubchem_compound_id>
  <foodb_id/>
  <kegg_id/>
  <chebi_id>89582</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Bodnaryk, Robert P.  Preparative-scale enzymic synthesis of g-L-glutamyl-L-phenylalanine.    Insect Biochemistry  (1972),  2(1),  49-52. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:19 UTC</creation_date>
  <update_date>2020-03-13 16:22:22 UTC</update_date>
  <accession>BMDB0000595</accession>
  <secondary_accessions>
    <accession>BMDB00595</accession>
  </secondary_accessions>
  <name>Hydrogen carbonate</name>
  <description/>
  <synonyms>
    <synonym>[CO(OH)2]</synonym>
    <synonym>Dihydrogen carbonate</synonym>
    <synonym>H2CO3</synonym>
    <synonym>Koehlensaeure</synonym>
    <synonym>Dihydrogen carbonic acid</synonym>
    <synonym>Hydrogen carbonic acid</synonym>
    <synonym>Carbonate</synonym>
    <synonym>Acid OF air</synonym>
    <synonym>Aerial acid</synonym>
    <synonym>Bisodium carbonate</synonym>
    <synonym>Calcined</synonym>
    <synonym>Carbonic acid sodium salt</synonym>
    <synonym>Consal</synonym>
    <synonym>Crystol carbonate</synonym>
    <synonym>Disodium carbonate</synonym>
    <synonym>Mild alkali</synonym>
    <synonym>Na-X</synonym>
    <synonym>Oxyper</synonym>
    <synonym>Sal soda</synonym>
    <synonym>Salt OF soda</synonym>
    <synonym>Scotch soda</synonym>
    <synonym>Soda</synonym>
    <synonym>Soda ash</synonym>
    <synonym>Sodium carbonate</synonym>
    <synonym>Sodium carbonate anhydrous</synonym>
    <synonym>Sodium carbonate hydrated</synonym>
    <synonym>Sodium carbonate peroxyhydrate</synonym>
    <synonym>Solvay soda</synonym>
    <synonym>Trona soda ash</synonym>
    <synonym>Tronalight light soda ash</synonym>
    <synonym>Acid, carbonic</synonym>
    <synonym>Carbonic acid</synonym>
    <synonym>Ions, bicarbonate</synonym>
    <synonym>Carbonate, hydrogen</synonym>
    <synonym>Carbonates, hydrogen</synonym>
    <synonym>Bicarbonate ion</synonym>
    <synonym>Hydrogen carbonates</synonym>
    <synonym>Bicarbonates</synonym>
    <synonym>Bicarbonate ions</synonym>
    <synonym>Carbonic acid ions</synonym>
    <synonym>Ions, carbonic acid</synonym>
  </synonyms>
  <chemical_formula>CH2O3</chemical_formula>
  <average_molecular_weight>62.0248</average_molecular_weight>
  <monisotopic_moleculate_weight>62.00039393</monisotopic_moleculate_weight>
  <iupac_name>carbonic acid</iupac_name>
  <traditional_iupac>carbonic acid</traditional_iupac>
  <cas_registry_number>71-52-3</cas_registry_number>
  <smiles>OC(O)=O</smiles>
  <inchi>InChI=1S/CH2O3/c2-1(3)4/h(H2,2,3,4)</inchi>
  <inchikey>BVKZGUZCCUSVTD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as organic carbonic acids. Organic carbonic acids are compounds comprising the carbonic acid functional group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic carbonic acids and derivatives</class>
    <sub_class>Organic carbonic acids</sub_class>
    <direct_parent>Organic carbonic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonic acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>carbon oxoacid</external_descriptor>
      <external_descriptor>chalcocarbonic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>6.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>carbonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>62.0248</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>62.00039393</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>CH2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/CH2O3/c2-1(3)4/h(H2,2,3,4)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BVKZGUZCCUSVTD-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>9.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>4.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gastric Acid Production</name>
      <smpdb_id>SMP0119381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Kidney Function</name>
      <smpdb_id>SMP0119376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Threonine and 2-Oxobutanoate Degradation</name>
      <smpdb_id>SMP0087262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30571</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>24400 +/- 260</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>McAdam PA, O'Dell GD: Mineral profile of blood plasma of lactating dairy cows. J Dairy Sci. 1982 Jul;65(7):1219-26. doi: 10.3168/jds.S0022-0302(82)82333-3.</reference_text>
          <pubmed_id>7108016</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB023191</foodb_id>
  <kegg_id>C01353</kegg_id>
  <chemspider_id>747</chemspider_id>
  <pubchem_compound_id>767</pubchem_compound_id>
  <chebi_id>28976</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>1436647</bigg_id>
  <wikipedia_id>Carbonic acid</wikipedia_id>
  <metlin_id>6944</metlin_id>
  <synthesis_reference>Nakajima, Fumiaki; Arima, Toshikazu; Kikuchi, Shintaro; Hirano, Hachiro.  Production of alkaline hydrogen carbonate.    Jpn. Kokai Tokkyo Koho  (2005),     15 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00138</protein_accession>
      <name>Cystic fibrosis transmembrane conductance regulator</name>
      <uniprot_id>P35071</uniprot_id>
      <gene_name>CFTR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01347</protein_accession>
      <name>Solute carrier family 26, member 6</name>
      <uniprot_id>Q08DQ8</uniprot_id>
      <gene_name>SLC26A6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01433</protein_accession>
      <name>Serotransferrin</name>
      <uniprot_id>Q29443</uniprot_id>
      <gene_name>TF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02079</protein_accession>
      <name>Lithostathine</name>
      <uniprot_id>P23132</uniprot_id>
      <gene_name>PTP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02297</protein_accession>
      <name>Solute carrier family 4 sodium bicarbonate cotransporter member 4 variant NBCe1B</name>
      <uniprot_id>B2NIZ2</uniprot_id>
      <gene_name>SLC4A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:20 UTC</creation_date>
  <update_date>2020-04-16 20:39:18 UTC</update_date>
  <accession>BMDB0000596</accession>
  <secondary_accessions>
    <accession>BMDB00596</accession>
  </secondary_accessions>
  <name>Glucosylsphingosine</name>
  <description/>
  <synonyms>
    <synonym>(R-(R*,s*-(e)))-beta-D-glucopyranoside 2-amino-3-hydroxy-4-octadecenyl</synonym>
    <synonym>(R-(R*,s*-(e)))-beta-delta-glucopyranoside 2-amino-3-hydroxy-4-octadecenyl</synonym>
    <synonym>D-Glucosyl-N-acylsphingosine</synonym>
    <synonym>delta-Glucosyl-N-acylsphingosine</synonym>
    <synonym>Glucopsychosine</synonym>
    <synonym>Glucosyl psychosine</synonym>
    <synonym>Glucosyl sphingosine</synonym>
    <synonym>Sphingosyl beta-glucoside</synonym>
    <synonym>GLCSPH</synonym>
    <synonym>Glucosylsphingosine</synonym>
  </synonyms>
  <chemical_formula>C24H47NO7</chemical_formula>
  <average_molecular_weight>461.6325</average_molecular_weight>
  <monisotopic_moleculate_weight>461.335252863</monisotopic_moleculate_weight>
  <iupac_name>(3R,4S,5S,6R)-2-{[(4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>glucopsychosine</traditional_iupac>
  <cas_registry_number>52050-17-6</cas_registry_number>
  <smiles>CCCCCCCCCCCCC\C=C\C(O)C(N)COC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/b15-14+/t18?,19?,20-,21-,22+,23-,24?/m1/s1</inchi>
  <inchikey>HHJTWTPUPVQKNA-KEVGHMQTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Sphingolipids</class>
    <sub_class>Glycosphingolipids</sub_class>
    <direct_parent>Glycosphingolipids</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Alkyl glycosides</alternative_parent>
      <alternative_parent>Fatty acyl glycosides of mono- and disaccharides</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl glycoside</substituent>
      <substituent>Amine</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty acyl glycoside</substituent>
      <substituent>Fatty acyl glycoside of mono- or disaccharide</substituent>
      <substituent>Glycosphingolipid</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4S,5S,6R)-2-{[(4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>461.6325</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>461.335252863</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCC\C=C\C(O)C(N)COC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H47NO7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/b15-14+/t18?,19?,20-,21-,22+,23-,24?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HHJTWTPUPVQKNA-KEVGHMQTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>145.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>124.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>55.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37643</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>17215974</chemspider_id>
  <pubchem_compound_id>22833534</pubchem_compound_id>
  <foodb_id>FDB022135</foodb_id>
  <kegg_id>C03108</kegg_id>
  <chebi_id/>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5574</metlin_id>
  <synthesis_reference>Yamaguchi Y; Sasagasako N; Goto I; Kobayashi T  The synthetic pathway for glucosylsphingosine in cultured fibroblasts.    Journal of biochemistry  (1994),  116(3),  704-10.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00131</protein_accession>
      <name>Glucosylceramidase</name>
      <uniprot_id>Q2KHZ8</uniprot_id>
      <gene_name>GBA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:21 UTC</creation_date>
  <update_date>2020-04-16 20:37:41 UTC</update_date>
  <accession>BMDB0000598</accession>
  <secondary_accessions>
    <accession>BMDB00598</accession>
  </secondary_accessions>
  <name>Sulfide</name>
  <description>Sulfide, also known as sulphide or S(2-), belongs to the class of inorganic compounds known as other non-metal sulfides. These are inorganic compounds containing a sulfur atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen belongs to the class of other non-metals. Sulfide exists as a solid, possibly soluble (in water), and possibly neutral molecule. Sulfide exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>S(2-)</synonym>
    <synonym>Sulphide</synonym>
    <synonym>Sulfanediide</synonym>
    <synonym>Sulfur</synonym>
    <synonym>Sulphide(2-)</synonym>
    <synonym>Sulfide</synonym>
  </synonyms>
  <chemical_formula>S</chemical_formula>
  <average_molecular_weight>32.065</average_molecular_weight>
  <monisotopic_moleculate_weight>31.97207069</monisotopic_moleculate_weight>
  <iupac_name>sulfanediide</iupac_name>
  <traditional_iupac>sulfanediide</traditional_iupac>
  <cas_registry_number>18496-25-8</cas_registry_number>
  <smiles>[S--]</smiles>
  <inchi>InChI=1S/S/q-2</inchi>
  <inchikey>UCKMPCXJQFINFW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as other non-metal sulfides. These are inorganic compounds containing a sulfur atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen belongs to the class of other non-metals.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Other non-metal organides</class>
    <sub_class>Other non-metal sulfides</sub_class>
    <direct_parent>Other non-metal sulfides</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Other non-metal sulfide</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>an anion</external_descriptor>
      <external_descriptor>divalent inorganic anion</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>112 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.038</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>sulfanediide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>32.065</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>31.97207069</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[S--]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/S/q-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UCKMPCXJQFINFW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>5.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>2.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>2006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>174948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>174949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>174950</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9979.729</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>27079</chemspider_id>
  <pubchem_compound_id>29109</pubchem_compound_id>
  <foodb_id>FDB022136</foodb_id>
  <kegg_id>C00087</kegg_id>
  <chebi_id>15138</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Sulfide</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Green, Martina; Verkoczy, Bela; Lown, Elizabeth M.; Strausz, Otto P. The reactions of sulfur atoms with propadiene and 1,2-butadiene. Canadian Journal of Chemistry (1985), 63(3), 667-75.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:23 UTC</creation_date>
  <update_date>2020-04-16 17:54:01 UTC</update_date>
  <accession>BMDB0000599</accession>
  <secondary_accessions>
    <accession>BMDB00599</accession>
  </secondary_accessions>
  <name>Chromium</name>
  <description>Chromium, also known as CR(3+) or chromic ion, belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Chromium exists as a solid, possibly soluble (in water), and possibly neutral molecule.</description>
  <synonyms>
    <synonym>Chromic ion</synonym>
    <synonym>Chromium (III) ion</synonym>
    <synonym>CHROMIUM ion</synonym>
    <synonym>Chromium(III)</synonym>
    <synonym>CR(3+)</synonym>
    <synonym>Chrome</synonym>
    <synonym>Chromium metal</synonym>
    <synonym>Cr</synonym>
  </synonyms>
  <chemical_formula>Cr</chemical_formula>
  <average_molecular_weight>51.9961</average_molecular_weight>
  <monisotopic_moleculate_weight>51.940511904</monisotopic_moleculate_weight>
  <iupac_name>chromium(3+) ion</iupac_name>
  <traditional_iupac>chromium(3+) ion</traditional_iupac>
  <cas_registry_number>16065-83-1</cas_registry_number>
  <smiles>[Cr+3]</smiles>
  <inchi>InChI=1S/Cr/q+3</inchi>
  <inchikey>BFGKITSFLPAWGI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous transition metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous transition metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous transition metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a cation</external_descriptor>
      <external_descriptor>chromium cation</external_descriptor>
      <external_descriptor>monoatomic trication</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>1900 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>chromium(3+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>51.9961</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>51.940511904</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Cr+3]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Cr</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Cr/q+3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BFGKITSFLPAWGI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>45102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>45103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>45104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144665</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.7 - 1.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.5 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.5 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.7 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.50 +/- 0.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0490 +/- 0.000962</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0981 +/- 0.0115</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0589 +/- 0.00115</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS.  Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.121 +/- 0.00962</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00392 +/- 0.000154</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0423 +/- 0.00962</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.769 - 3.462</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.442 - 1.692</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.34 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by ICP-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>25743</chemspider_id>
  <foodb_id>FDB003516</foodb_id>
  <kegg_id>C19368</kegg_id>
  <pubchem_compound_id>27668</pubchem_compound_id>
  <chebi_id>49544</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Chromium</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
    </reference>
    <reference>
      <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:24 UTC</creation_date>
  <update_date>2020-04-16 20:37:36 UTC</update_date>
  <accession>BMDB0000600</accession>
  <secondary_accessions>
    <accession>BMDB00600</accession>
  </secondary_accessions>
  <name>Galactosylhydroxylysine</name>
  <description/>
  <synonyms>
    <synonym>5-(beta-D-Galactopyranosyloxy)-L-lysine</synonym>
    <synonym>5-(beta-delta-Galactopyranosyloxy)-L-lysine</synonym>
    <synonym>5-O-beta-D-Galactopyranosylhydroxy-L-lysine</synonym>
    <synonym>5-O-beta-delta-Galactopyranosylhydroxy-L-lysine</synonym>
    <synonym>beta-1-Galactosyl-O-hydroxylysine</synonym>
    <synonym>Galactopyranosylhydroxy-L-lysine</synonym>
    <synonym>Galactosyl-delta-hydroxylysine</synonym>
    <synonym>Hydroxylysine-galactose</synonym>
    <synonym>L-5-(beta-D-Galactopyranosyloxy)-lysine</synonym>
    <synonym>L-5-(beta-delta-Galactopyranosyloxy)-lysine</synonym>
    <synonym>O-beta-D-Galactopyranosylhydroxy-L-lysine</synonym>
    <synonym>O-beta-delta-Galactopyranosylhydroxy-L-lysine</synonym>
    <synonym>Procollagen (5-galactosyloxy)-L-lysine</synonym>
    <synonym>(2S)-6-Amino-2-{n-hydroxy[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}hexanoate</synonym>
  </synonyms>
  <chemical_formula>C12H24N2O8</chemical_formula>
  <average_molecular_weight>324.3276</average_molecular_weight>
  <monisotopic_moleculate_weight>324.153265754</monisotopic_moleculate_weight>
  <iupac_name>(2S)-6-amino-2-{N-hydroxy[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}hexanoic acid</iupac_name>
  <traditional_iupac>galactosylhydroxylysine</traditional_iupac>
  <cas_registry_number>32448-36-5</cas_registry_number>
  <smiles>NCCCC[C@H](N(O)C1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)C(O)=O</smiles>
  <inchi>InChI=1S/C12H24N2O8/c13-4-2-1-3-6(12(19)20)14(21)11-10(18)9(17)8(16)7(5-15)22-11/h6-11,15-18,21H,1-5,13H2,(H,19,20)/t6-,7+,8-,9-,10+,11?/m0/s1</inchi>
  <inchikey>RCPOVANIIKXVTB-YPPRVYOWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Short-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Short-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxyglutaric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>257.0 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-6-amino-2-{N-hydroxy[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino}hexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>324.3276</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>324.153265754</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCC[C@H](N(O)C1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H24N2O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H24N2O8/c13-4-2-1-3-6(12(19)20)14(21)11-10(18)9(17)8(16)7(5-15)22-11/h6-11,15-18,21H,1-5,13H2,(H,19,20)/t6-,7+,8-,9-,10+,11?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RCPOVANIIKXVTB-YPPRVYOWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>176.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>102723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>102724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>102725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>168591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>168592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>168593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448410</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>17215976</chemspider_id>
  <foodb_id>FDB011652</foodb_id>
  <kegg_id>C05547</kegg_id>
  <pubchem_compound_id>22833535</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5576</metlin_id>
  <synthesis_reference>Adamczyk, Maciej; Reddy, Rajarathnam E.; Rege, Sushil D. Synthesis of galactosylhydroxylysine and its analogs. Synthetic Communications (2000), 30(18), 3281-3290.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:25 UTC</creation_date>
  <update_date>2020-04-15 22:14:10 UTC</update_date>
  <accession>BMDB0000601</accession>
  <secondary_accessions>
    <accession>BMDB00601</accession>
  </secondary_accessions>
  <name>Coprocholic acid</name>
  <description/>
  <synonyms>
    <synonym>(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestan-26-Oic acid</synonym>
    <synonym>3,7,12-Trihydroxycholestan-26-Oic acid</synonym>
    <synonym>(3a,5b,7a,12a)-3,7,12-Trihydroxycholestan-26-Oate</synonym>
    <synonym>(3a,5b,7a,12a)-3,7,12-Trihydroxycholestan-26-Oic acid</synonym>
    <synonym>(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestan-26-Oate</synonym>
    <synonym>(3Α,5β,7α,12α)-3,7,12-trihydroxycholestan-26-Oate</synonym>
    <synonym>(3Α,5β,7α,12α)-3,7,12-trihydroxycholestan-26-Oic acid</synonym>
    <synonym>3,7,12-Trihydroxycholestan-26-Oate</synonym>
    <synonym>Coprocholate</synonym>
    <synonym>3a,7a,12a-Trihydroxy-(6ci,7ci,8ci)5b-cholestan-26-Oate</synonym>
    <synonym>3a,7a,12a-Trihydroxy-(6ci,7ci,8ci)5b-cholestan-26-Oic acid</synonym>
    <synonym>3a,7a,12a-Trihydroxy-5b-cholestan-26-Oate</synonym>
    <synonym>3a,7a,12a-Trihydroxy-5b-cholestan-26-Oic acid</synonym>
    <synonym>3a,7a,12a-Trihydroxycoprostanate</synonym>
    <synonym>3a,7a,12a-Trihydroxycoprostanic acid</synonym>
    <synonym>5b-Cholestane-3a,7a,12a-triol-26-Oate</synonym>
    <synonym>5b-Cholestane-3a,7a,12a-triol-26-Oic acid</synonym>
    <synonym>3 alpha,7 alpha,12 alpha-Trihydroxy-5-beta-cholestan-26-Oic acid</synonym>
    <synonym>3,7,12-Trihydroxycholestan-26-Oic acid, (25R)-isomer</synonym>
    <synonym>3,7,12-Trihydroxycholestan-26-Oic acid, (25S)-isomer</synonym>
    <synonym>3Α,7α,12α-trihydroxy-5β-cholestan-26-Oic acid</synonym>
    <synonym>3Α,7α,12α-trihydroxycoprostanic acid</synonym>
    <synonym>5Β-cholestane-3α,7α,12α-triol-26-Oic acid</synonym>
    <synonym>3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-Oic acid</synonym>
    <synonym>3alpha,7alpha,12alpha-Trihydroxycoprostanic acid</synonym>
    <synonym>5beta-Cholestane-3alpha,7alpha,12alpha-triol-26-Oic acid</synonym>
    <synonym>Trihydroxycoprostanic acid</synonym>
    <synonym>Trihydroxycoprostanoic acid</synonym>
    <synonym>3a,7a,12a-Trihydroxy-5b-cholestanoic acid</synonym>
    <synonym>3a,7a,12a-Trihydroxy-5b-cholestanoate</synonym>
    <synonym>3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoate</synonym>
    <synonym>3Α,7α,12α-trihydroxy-5β-cholestanoate</synonym>
    <synonym>3Α,7α,12α-trihydroxy-5β-cholestanoic acid</synonym>
    <synonym>Coprocholic acid</synonym>
  </synonyms>
  <chemical_formula>C27H46O5</chemical_formula>
  <average_molecular_weight>450.6511</average_molecular_weight>
  <monisotopic_moleculate_weight>450.334524582</monisotopic_moleculate_weight>
  <iupac_name>(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid</iupac_name>
  <traditional_iupac>(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid</traditional_iupac>
  <cas_registry_number>547-98-8</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C(O)=O</smiles>
  <inchi>InChI=1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16?,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1</inchi>
  <inchikey>CNWPIIOQKZNXBB-VCVMUKOKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Steroid acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Steroid acid</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>12alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>3alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>7alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>C27 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>steroid acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>450.6511</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>450.334524582</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H46O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H46O5/c1-15(6-5-7-16(2)25(31)32)19-8-9-20-24-21(14-23(30)27(19,20)4)26(3)11-10-18(28)12-17(26)13-22(24)29/h15-24,28-30H,5-14H2,1-4H3,(H,31,32)/t15-,16?,17+,18-,19-,20+,21+,22-,23+,24+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CNWPIIOQKZNXBB-VCVMUKOKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>124.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>53.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37645</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>109066</chemspider_id>
  <foodb_id>FDB022137</foodb_id>
  <kegg_id/>
  <pubchem_compound_id>122312</pubchem_compound_id>
  <chebi_id>18402</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5577</metlin_id>
  <synthesis_reference>Batta A K; Mirchandani R; Salen G; Shefer S  Synthesis of 3 alpha, 7 alpha-dihydroxy-5 beta-cholestan-26-oic acid from 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestan-26-oic acid: configuration in the bile of Alligator mississippiensis.    Steroids  (1992),  57(4),  162-6. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:26 UTC</creation_date>
  <update_date>2020-03-13 16:22:25 UTC</update_date>
  <accession>BMDB0000603</accession>
  <secondary_accessions>
    <accession>BMDB00603</accession>
  </secondary_accessions>
  <name>Decenedioic acid</name>
  <description/>
  <synonyms>
    <synonym>Decenedioate</synonym>
    <synonym>2E-Decenedioate</synonym>
  </synonyms>
  <chemical_formula>C10H16O4</chemical_formula>
  <average_molecular_weight>200.234</average_molecular_weight>
  <monisotopic_moleculate_weight>200.104858995</monisotopic_moleculate_weight>
  <iupac_name>(2E)-dec-2-enedioic acid</iupac_name>
  <traditional_iupac>decenedioic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H]\C(CCCCCCC(O)=O)=C(\[H])C(O)=O</smiles>
  <inchi>InChI=1S/C10H16O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h5,7H,1-4,6,8H2,(H,11,12)(H,13,14)/b7-5+</inchi>
  <inchikey>XUNMWLWTZWWEIE-FNORWQNLSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-dec-2-enedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>200.234</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>200.104858995</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]\C(CCCCCCC(O)=O)=C(\[H])C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H16O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H16O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h5,7H,1-4,6,8H2,(H,11,12)(H,13,14)/b7-5+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XUNMWLWTZWWEIE-FNORWQNLSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>52.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1327315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1327316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1327317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1441654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1441655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1441656</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id/>
  <foodb_id/>
  <kegg_id/>
  <pubchem_compound_id>6442613</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Pourfarzam, Morteza; Bartlett, Kim.  Synthesis, characterization and high-performance liquid chromatography of C6-C16 dicarboxylyl-mono-coenzyme A and -mono-carnitine esters.    Journal of Chromatography  (1991),  570(2),  253-76. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:28 UTC</creation_date>
  <update_date>2020-04-14 22:47:50 UTC</update_date>
  <accession>BMDB0000606</accession>
  <secondary_accessions>
    <accession>BMDB00606</accession>
  </secondary_accessions>
  <name>D-2-Hydroxyglutaric acid</name>
  <description>D-2-Hydroxyglutaric acid, also known as (R)-hydroxyglutarate or (R)-2-hydroxy-pentanedioate, belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms. D-2-Hydroxyglutaric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-2-Hydroxyglutaric acid exists in all living organisms, ranging from bacteria to humans. D-2-Hydroxyglutaric acid is a potentially toxic compound. D-2-Hydroxyglutaric acid has been found to be associated with several diseases known as spondyloenchondrodysplasia and d, l-2-hydroxyglutaric aciduria; also d-2-hydroxyglutaric acid has been linked to the inborn metabolic disorders including d-2-hydroxyglutaric aciduria.</description>
  <synonyms>
    <synonym>(R)-2-Hydroxyglutarate</synonym>
    <synonym>(R)-Hydroxyglutarate</synonym>
    <synonym>(R)-2-Hydroxyglutaric acid</synonym>
    <synonym>(R)-Hydroxyglutaric acid</synonym>
    <synonym>D-2-Hydroxyglutarate</synonym>
    <synonym>(R)-2-Hydroxy-pentanedioate</synonym>
    <synonym>(R)-2-Hydroxy-pentanedioic acid</synonym>
    <synonym>(R)-a-Hydroxyglutarate</synonym>
    <synonym>(R)-a-Hydroxyglutaric acid</synonym>
    <synonym>(R)-alpha-Hydroxyglutarate</synonym>
    <synonym>(R)-alpha-Hydroxyglutaric acid</synonym>
    <synonym>2-Hydroxy-D-glutarate</synonym>
    <synonym>2-Hydroxy-D-glutaric acid</synonym>
    <synonym>2-Hydroxy-delta-glutarate</synonym>
    <synonym>2-Hydroxy-delta-glutaric acid</synonym>
    <synonym>D-a-Hydroxyglutarate</synonym>
    <synonym>D-a-Hydroxyglutaric acid</synonym>
    <synonym>delta-2-Hydroxyglutarate</synonym>
    <synonym>delta-2-Hydroxyglutaric acid</synonym>
    <synonym>delta-alpha-Hydroxyglutarate</synonym>
    <synonym>delta-alpha-Hydroxyglutaric acid</synonym>
    <synonym>2-Hydroxyglutarate</synonym>
    <synonym>alpha-Hydroxyglutarate, (D)-isomer</synonym>
    <synonym>alpha-Hydroxyglutarate, (DL)-isomer</synonym>
    <synonym>2-Hydroxyglutaric acid</synonym>
    <synonym>alpha-Hydroxyglutarate</synonym>
    <synonym>alpha-Hydroxyglutarate, (L)-isomer</synonym>
    <synonym>alpha-Hydroxyglutarate, disodium salt</synonym>
  </synonyms>
  <chemical_formula>C5H8O5</chemical_formula>
  <average_molecular_weight>148.114</average_molecular_weight>
  <monisotopic_moleculate_weight>148.037173366</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-hydroxypentanedioic acid</iupac_name>
  <traditional_iupac>D-2-hydroxyglutaric acid</traditional_iupac>
  <cas_registry_number>13095-47-1</cas_registry_number>
  <smiles>O[C@H](CCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/t3-/m1/s1</inchi>
  <inchikey>HWXBTNAVRSUOJR-GSVOUGTGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Short-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Short-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxyglutaric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>&gt; 300 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-hydroxypentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>148.114</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>148.037173366</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H](CCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/t3-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HWXBTNAVRSUOJR-GSVOUGTGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>29.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>47787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>47788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>47789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>123639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>123640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>123641</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>388508</chemspider_id>
  <foodb_id>FDB022139</foodb_id>
  <kegg_id>C01087</kegg_id>
  <pubchem_compound_id>439391</pubchem_compound_id>
  <chebi_id>32796</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id>R-2-HYDROXYGLUTARATE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Alpha-Hydroxyglutaric acid</wikipedia_id>
  <metlin_id>5581</metlin_id>
  <synthesis_reference>Kobayashi, Hidehiko; Yamaguchi, Koretaka; Yamashita, Takeshi.  a-Hydroxyglutaric acid from glutamic acid.    Jpn. Tokkyo Koho  (1968),     3 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00595</protein_accession>
      <name>Hydroxyacid-oxoacid transhydrogenase, mitochondrial</name>
      <uniprot_id>A6QP15</uniprot_id>
      <gene_name>ADHFE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00800</protein_accession>
      <name>D-2-hydroxyglutarate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q1JPD3</uniprot_id>
      <gene_name>D2HGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:30 UTC</creation_date>
  <update_date>2020-04-16 17:51:19 UTC</update_date>
  <accession>BMDB0000607</accession>
  <secondary_accessions>
    <accession>BMDB00607</accession>
  </secondary_accessions>
  <name>Cyanocobalamin</name>
  <description>Cyanocobalamin is possibly soluble (in water) and a moderately acidic compound (based on its pKa).</description>
  <synonyms>
  </synonyms>
  <chemical_formula>C63H88CoN14O14P</chemical_formula>
  <average_molecular_weight>1355.388</average_molecular_weight>
  <monisotopic_moleculate_weight>1354.5674</monisotopic_moleculate_weight>
  <iupac_name>lambda2-cobalt(2+) ion 1-[(2S,3R,4S,5R)-3-hydroxy-4-{[hydroxy({[(2R)-1-({1-hydroxy-3-[(1R,3R,8S,13S,14S,18S,19S)-8,13,18-tris[2-(C-hydroxycarbonimidoyl)ethyl]-3,14,19-tris[(C-hydroxycarbonimidoyl)methyl]-1,4,6,9,9,14,16,19-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1^{2,5}.1^{7,10}.1^{12,15}]tricosa-5(23),6,10(22),11,15(21),16-hexaen-4-yl]propylidene}amino)propan-2-yl]oxy})phosphoryl]oxy}-5-(hydroxymethyl)oxolan-2-yl]-5,6-dimethyl-3H-1lambda5,3-benzodiazol-1-ylium cyano</iupac_name>
  <traditional_iupac>lambda2-cobalt(2+) ion 1-[(2S,3R,4S,5R)-3-hydroxy-4-{[hydroxy([(2R)-1-({1-hydroxy-3-[(1R,3R,8S,13S,14S,18S,19S)-8,13,18-tris[2-(C-hydroxycarbonimidoyl)ethyl]-3,14,19-tris(C-hydroxycarbonimidoylmethyl)-1,4,6,9,9,14,16,19-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1^{2,5}.1^{7,10}.1^{12,15}]tricosa-5(23),6,10(22),11,15(21),16-hexaen-4-yl]propylidene}amino)propan-2-yl]oxy)phosphoryl]oxy}-5-(hydroxymethyl)oxolan-2-yl]-5,6-dimethyl-3H-1lambda5,3-benzodiazol-1-ylium cyano radical</traditional_iupac>
  <cas_registry_number/>
  <smiles>[Co++].[C]#N.[H][C@@](C)(CN=C(O)CCC1(C)C2=NC([H])([C@]1([H])CC(O)=N)[C@]1(C)NC(=C(C)C3=NC(=CC4=NC(=C2C)[C@@]([H])(CCC([O-])=N)C4(C)C)[C@@]([H])(CCC([O-])=N)[C@]3(C)CC(O)=N)[C@@]([H])(CCC([O-])=N)[C@]1(C)CC(O)=N)OP(O)(=O)O[C@]1([H])[C@@]([H])(CO)O[C@]([H])([N+]2=CNC3=C2C=C(C)C(C)=C3)[C@]1([H])O</smiles>
  <inchi>InChI=1S/C62H90N13O14P.CN.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-2;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);;/q;;+2/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56?,57+,59?,60+,61+,62+;;/m1../s1</inchi>
  <inchikey>RMRCNWBMXRMIRW-JHUHWLDHSA-L</inchikey>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>lambda2-cobalt(2+) ion 1-[(2S,3R,4S,5R)-3-hydroxy-4-{[hydroxy({[(2R)-1-({1-hydroxy-3-[(1R,3R,8S,13S,14S,18S,19S)-8,13,18-tris[2-(C-hydroxycarbonimidoyl)ethyl]-3,14,19-tris[(C-hydroxycarbonimidoyl)methyl]-1,4,6,9,9,14,16,19-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1^{2,5}.1^{7,10}.1^{12,15}]tricosa-5(23),6,10(22),11,15(21),16-hexaen-4-yl]propylidene}amino)propan-2-yl]oxy})phosphoryl]oxy}-5-(hydroxymethyl)oxolan-2-yl]-5,6-dimethyl-3H-1lambda5,3-benzodiazol-1-ylium cyano</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1355.388</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1354.5674</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Co++].[C]#N.[H][C@@](C)(CN=C(O)CCC1(C)C2=NC([H])([C@]1([H])CC(O)=N)[C@]1(C)NC(=C(C)C3=NC(=CC4=NC(=C2C)[C@@]([H])(CCC([O-])=N)C4(C)C)[C@@]([H])(CCC([O-])=N)[C@]3(C)CC(O)=N)[C@@]([H])(CCC([O-])=N)[C@]1(C)CC(O)=N)OP(O)(=O)O[C@]1([H])[C@@]([H])(CO)O[C@]([H])([N+]2=CNC3=C2C=C(C)C(C)=C3)[C@]1([H])O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C63H88CoN14O14P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C62H90N13O14P.CN.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-2;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);;/q;;+2/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56?,57+,59?,60+,61+,62+;;/m1../s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RMRCNWBMXRMIRW-JHUHWLDHSA-L</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>479.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>430.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>133.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00347</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0028</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00266</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00317</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0028</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00347</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00317</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00288</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00369</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00369</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00362</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00362</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00266</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00317</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0028</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00288</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00391</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00391</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00354</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00356</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00354</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00332</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00332</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00332</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00332</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00332</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00263</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00251</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00251</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id/>
  <foodb_id/>
  <kegg_id/>
  <pubchem_compound_id/>
  <chebi_id/>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Cyanocobalamin</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Gardner, N.; Champagne, C. P. Production of Propionibacterium shermanii biomass and vitamin B12 on spent media. Journal of Applied Microbiology (2005), 99(5), 1236-1245.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP02162</protein_accession>
      <name>Coagulation factor II (Thrombin) receptor-like 2</name>
      <uniprot_id>A4IFB7</uniprot_id>
      <gene_name>F2RL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:31 UTC</creation_date>
  <update_date>2020-04-16 17:54:02 UTC</update_date>
  <accession>BMDB0000608</accession>
  <secondary_accessions>
    <accession>BMDB00608</accession>
  </secondary_accessions>
  <name>Cobalt</name>
  <description>Cobalt, also known as co(ii) or cobalt(2+) ion, belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Cobalt exists as a solid, possibly soluble (in water), and possibly neutral molecule. Cobalt exists in all living organisms, ranging from bacteria to humans. Cobalt is a potentially toxic compound.</description>
  <synonyms>
    <synonym>Co(II)</synonym>
    <synonym>CO2+</synonym>
    <synonym>Co(2+)</synonym>
    <synonym>COBALT (II) ion</synonym>
    <synonym>Cobalt(2+) ion</synonym>
    <synonym>Cobalt(II) cation</synonym>
    <synonym>Cobaltous ion</synonym>
    <synonym>Cobalt(2+)</synonym>
    <synonym>Aquacat</synonym>
    <synonym>Co</synonym>
    <synonym>Cobalt-59</synonym>
    <synonym>Cobatope-57</synonym>
    <synonym>Kobalt</synonym>
    <synonym>Super cobalt</synonym>
  </synonyms>
  <chemical_formula>Co</chemical_formula>
  <average_molecular_weight>58.9332</average_molecular_weight>
  <monisotopic_moleculate_weight>58.933200194</monisotopic_moleculate_weight>
  <iupac_name>lambda2-cobalt(2+) ion</iupac_name>
  <traditional_iupac>lambda2-cobalt(2+) ion</traditional_iupac>
  <cas_registry_number>22541-53-3</cas_registry_number>
  <smiles>[Co++]</smiles>
  <inchi>InChI=1S/Co/q+2</inchi>
  <inchikey>XLJKHNWPARRRJB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous transition metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous transition metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous transition metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a cation</external_descriptor>
      <external_descriptor>cobalt cation</external_descriptor>
      <external_descriptor>divalent metal cation</external_descriptor>
      <external_descriptor>monoatomic dication</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>1495 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>lambda2-cobalt(2+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>58.9332</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>58.933200194</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Co++]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Co</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Co/q+2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XLJKHNWPARRRJB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>100968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>100969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>100970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>166446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>166447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>166448</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>0.8+/-0.2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>0.02+/-0.01</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.04 - 0.08</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Z. Dobrzañski et al. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Polish Journal of Environmental Studies Vol. 14, No 5 (2005), 685-689</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.02 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.02 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.03 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.03 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0197 +/- 0.000679</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0390 +/- 0.00170</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0210 +/- 0.000509</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS.  Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0373 +/- 0.00339</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0176 +/- 0.00136</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0209 +/- 0.000679</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0876 - 0.142</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1+/-0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>0.022+/-0.003</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>0.05+/-0.01</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>94546</chemspider_id>
  <foodb_id>FDB003581</foodb_id>
  <kegg_id>C00175</kegg_id>
  <pubchem_compound_id>104729</pubchem_compound_id>
  <chebi_id>48828</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Cobalt</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Z. Dobrzañski et al. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Polish Journal of Environmental Studies Vol. 14, No 5 (2005), 685-689</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
    </reference>
    <reference>
      <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00174</protein_accession>
      <name>S-adenosylmethionine synthetase</name>
      <uniprot_id>A7E3T7</uniprot_id>
      <gene_name>MAT2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00177</protein_accession>
      <name>Ectonucleotide pyrophosphatase/phosphodiesterase family member 2</name>
      <uniprot_id>A1A4K5</uniprot_id>
      <gene_name>ENPP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00387</protein_accession>
      <name>Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)</name>
      <uniprot_id>Q58DK4</uniprot_id>
      <gene_name>DAK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00403</protein_accession>
      <name>S-adenosylmethionine synthetase isoform type-1</name>
      <uniprot_id>Q2KJC6</uniprot_id>
      <gene_name>MAT1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00414</protein_accession>
      <name>Methionine synthase</name>
      <uniprot_id>Q4JIJ3</uniprot_id>
      <gene_name>MTR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00434</protein_accession>
      <name>cGMP-specific 3',5'-cyclic phosphodiesterase</name>
      <uniprot_id>Q28156</uniprot_id>
      <gene_name>PDE5A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00444</protein_accession>
      <name>U8 snoRNA-decapping enzyme</name>
      <uniprot_id>A1A4Q9</uniprot_id>
      <gene_name>NUDT16</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00477</protein_accession>
      <name>Bis(5'-adenosyl)-triphosphatase</name>
      <uniprot_id>Q1KZG4</uniprot_id>
      <gene_name>FHIT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00623</protein_accession>
      <name>Methylmalonyl-CoA mutase, mitochondrial</name>
      <uniprot_id>Q9GK13</uniprot_id>
      <gene_name>MUT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00794</protein_accession>
      <name>Methionine aminopeptidase</name>
      <uniprot_id>Q862K9</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00795</protein_accession>
      <name>Methionine aminopeptidase 1</name>
      <uniprot_id>A6QLA4</uniprot_id>
      <gene_name>METAP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00796</protein_accession>
      <name>Methionine aminopeptidase</name>
      <uniprot_id>Q2HJ25</uniprot_id>
      <gene_name>MAP1D</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00797</protein_accession>
      <name>Methionine aminopeptidase 2</name>
      <uniprot_id>Q3ZC89</uniprot_id>
      <gene_name>METAP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01592</protein_accession>
      <name>LYR motif-containing protein 4</name>
      <uniprot_id>Q0VCG0</uniprot_id>
      <gene_name>LYRM4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01982</protein_accession>
      <name>Transcobalamin-2</name>
      <uniprot_id>Q9XSC9</uniprot_id>
      <gene_name>TCN2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01983</protein_accession>
      <name>Methylmalonic aciduria and homocystinuria type C homolog</name>
      <uniprot_id>Q5E9C8</uniprot_id>
      <gene_name>MMACHC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01984</protein_accession>
      <name>Probable lysosomal cobalamin transporter</name>
      <uniprot_id>Q3SYY9</uniprot_id>
      <gene_name>LMBRD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:32 UTC</creation_date>
  <update_date>2020-03-13 16:22:27 UTC</update_date>
  <accession>BMDB0000609</accession>
  <secondary_accessions>
    <accession>BMDB00609</accession>
  </secondary_accessions>
  <name>DL-Dopa</name>
  <description/>
  <synonyms>
    <synonym>(+-)-3-(3,4-Dihydroxyphenyl)alanine</synonym>
    <synonym>(+-)-Dopa</synonym>
    <synonym>(R,S)-Dopa</synonym>
    <synonym>3',4'-Dihydroxyphenylalanine</synonym>
    <synonym>3-Hydroxy-DL-tyrosine</synonym>
    <synonym>3-Hydroxytyrosine</synonym>
    <synonym>beta-(3,4-Dihydroxyphenyl)-DL-alpha-alanine</synonym>
    <synonym>DL-3,4-Dopa</synonym>
    <synonym>DL-beta-(3,4-Dihydroxyphenyl)-alpha-alanine</synonym>
    <synonym>DL-beta-(3,4-Dihydroxyphenyl)alanine</synonym>
    <synonym>DL-Dihydroxyphenylalanine</synonym>
    <synonym>DL-Dioxyphenylalanine</synonym>
    <synonym>b-(3,4-Dihydroxyphenyl)-DL-a-alanine</synonym>
    <synonym>Β-(3,4-dihydroxyphenyl)-DL-α-alanine</synonym>
    <synonym>DL-b-(3,4-Dihydroxyphenyl)-a-alanine</synonym>
    <synonym>DL-Β-(3,4-dihydroxyphenyl)-α-alanine</synonym>
    <synonym>DL-b-(3,4-Dihydroxyphenyl)alanine</synonym>
    <synonym>DL-Β-(3,4-dihydroxyphenyl)alanine</synonym>
    <synonym>(+/-) 3-(3,4-dihydroxyphenyl)alanine</synonym>
    <synonym>2-Amino-3-(3,4-dihydroxyphenyl)propanoate</synonym>
    <synonym>2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid</synonym>
    <synonym>3,4-Dihydroxy-DL-phenylalanine</synonym>
    <synonym>3,4-Dihydroxyphenylalanine</synonym>
    <synonym>3-(3,4-Dihydroxyphenyl)-DL-alanine</synonym>
    <synonym>a-Amino-3,4-dihydroxy-benzenepropanoate</synonym>
    <synonym>a-Amino-3,4-dihydroxy-benzenepropanoic acid</synonym>
    <synonym>alpha-Amino-3,4-dihydroxy-benzenepropanoate</synonym>
    <synonym>alpha-Amino-3,4-dihydroxy-benzenepropanoic acid</synonym>
    <synonym>alpha-Amino-hydrocaffeic acid</synonym>
    <synonym>b-(3,4-Dihydroxyphenyl)-a-alanine</synonym>
    <synonym>beta-(3,4-Dihydroxyphenyl)-alpha-alanine</synonym>
    <synonym>DL-3',4'-Dihydroxyphenylalanine</synonym>
    <synonym>DL-3,4-Dihydroxyphenylalanine</synonym>
    <synonym>DL-3-Hydroxytyrosine</synonym>
    <synonym>DL-4,5-Dihydroxyphenylalanine</synonym>
    <synonym>Dopa</synonym>
    <synonym>3 Hydroxy DL tyrosine</synonym>
    <synonym>3,4 Dihydroxyphenylalanine</synonym>
    <synonym>beta-Hydroxytyrosine</synonym>
    <synonym>Dihydroxyphenylalanine hydrochloride, (2:1)</synonym>
    <synonym>beta Hydroxytyrosine</synonym>
    <synonym>Dihydroxyphenylalanine</synonym>
  </synonyms>
  <chemical_formula>C9H11NO4</chemical_formula>
  <average_molecular_weight>197.1879</average_molecular_weight>
  <monisotopic_moleculate_weight>197.068807845</monisotopic_moleculate_weight>
  <iupac_name>2-amino-3-(3,4-dihydroxyphenyl)propanoic acid</iupac_name>
  <traditional_iupac>3',4'-dihydroxyphenylalanine</traditional_iupac>
  <cas_registry_number>63-84-3</cas_registry_number>
  <smiles>NC(CC1=CC=C(O)C(O)=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)</inchi>
  <inchikey>WTDRDQBEARUVNC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Tyrosine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alpha amino acids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Catechols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalanine and derivatives</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Catechol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Tyrosine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>hydroxyphenylalanine</external_descriptor>
      <external_descriptor>non-proteinogenic alpha-amino acid</external_descriptor>
      <external_descriptor>tyrosine derivative</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>270 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>3.6 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-3-(3,4-dihydroxyphenyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>197.1879</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>197.068807845</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CC1=CC=C(O)C(O)=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WTDRDQBEARUVNC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>103.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>49.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451879</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00355</kegg_id>
  <foodb_id>FDB022140</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>836</pubchem_compound_id>
  <chemspider_id>813</chemspider_id>
  <pdbe_id/>
  <chebi_id>49168</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Dihydroxyphenylalanine</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:33 UTC</creation_date>
  <update_date>2020-03-19 22:01:57 UTC</update_date>
  <accession>BMDB0000610</accession>
  <secondary_accessions>
    <accession>BMDB00610</accession>
  </secondary_accessions>
  <name>CE(18:2(9Z,12Z))</name>
  <description>Cholesteryl linoleate, also known as 18:2 cholesteryl ester or ce(18:2(9Z,12Z)), belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety. Cholesteryl linoleate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.</description>
  <synonyms>
    <synonym>Cholesterol ester(18:2)</synonym>
    <synonym>Cholesteryl 1-linoleoic acid</synonym>
    <synonym>Cholesterol ester(18:2/0:0)</synonym>
    <synonym>Cholesterol 1-(9Z,12Z-octadecadienoate)</synonym>
    <synonym>Cholesteryl 1-(9Z,12Z-octadecadienoate)</synonym>
    <synonym>18:2(9Z,12Z) Cholesterol ester</synonym>
    <synonym>Cholesteryl 1-linoleoate</synonym>
    <synonym>1-Linoleoyl-cholesterol</synonym>
    <synonym>Cholesterol 1-(9Z,12Z-octadecadienoic acid)</synonym>
    <synonym>CE(18:2)</synonym>
    <synonym>CE(18:2/0:0)</synonym>
    <synonym>Cholesterol 1-linoleoate</synonym>
    <synonym>Cholesteryl 1-(9Z,12Z-octadecadienoic acid)</synonym>
    <synonym>1-(9Z,12Z-Octadecadienoyl)-cholesterol</synonym>
    <synonym>Cholesterol 1-linoleoic acid</synonym>
    <synonym>CE(18:2n6/0:0)</synonym>
    <synonym>CE(18:2W6/0:0)</synonym>
    <synonym>Cholest-5-en-3beta-yl (9Z,12Z-octadecadienoate</synonym>
    <synonym>Cholest-5-en-3beta-yl (9Z,12Z-octadecadienoate)</synonym>
    <synonym>Cholest-5-en-3beta-yl (9Z,12Z-octadecadienoic acid</synonym>
    <synonym>Cholesterol 1-(9Z,12Z-octadecadienoate</synonym>
    <synonym>Cholesterol 1-(9Z,12Z-octadecadienoic acid</synonym>
    <synonym>Cholesterol ester(18:2n6/0:0)</synonym>
    <synonym>Cholesterol ester(18:2W6/0:0)</synonym>
    <synonym>Cholesteryl 1-(9Z,12Z-octadecadienoate</synonym>
    <synonym>Cholesteryl 1-(9Z,12Z-octadecadienoic acid</synonym>
    <synonym>CE(18:2(9Z,12Z))</synonym>
  </synonyms>
  <chemical_formula>C45H76O2</chemical_formula>
  <average_molecular_weight>649.101</average_molecular_weight>
  <monisotopic_moleculate_weight>648.584531687</monisotopic_moleculate_weight>
  <iupac_name>(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z,12Z)-octadeca-9,12-dienoate</iupac_name>
  <traditional_iupac>(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z,12Z)-octadeca-9,12-dienoate</traditional_iupac>
  <cas_registry_number>604-33-1</cas_registry_number>
  <smiles>CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C</smiles>
  <inchi>InChI=1S/C45H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h11-12,14-15,26,35-36,38-42H,7-10,13,16-25,27-34H2,1-6H3/b12-11-,15-14-/t36-,38+,39?,40?,41?,42?,44+,45-/m1/s1</inchi>
  <inchikey>NAACPBBQTFFYQB-XHDSEGDBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Steroid esters</sub_class>
    <direct_parent>Cholesteryl esters</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Cholesterols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lineolic acids and derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cholestane-skeleton</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesteryl ester</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Octadecanoid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>10.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-8.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>14.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z,12Z)-octadeca-9,12-dienoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>649.101</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>648.584531687</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C45H76O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C45H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h11-12,14-15,26,35-36,38-42H,7-10,13,16-25,27-34H2,1-6H3/b12-11-,15-14-/t36-,38+,39?,40?,41?,42?,44+,45-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NAACPBBQTFFYQB-XHDSEGDBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>26.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>205.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>85.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>33158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>913015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>913016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>913017</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>15.1 +/- 7.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C15441</kegg_id>
  <pubchem_compound_id>131801653</pubchem_compound_id>
  <chemspider_id>4450205</chemspider_id>
  <foodb_id>FDB022141</foodb_id>
  <pdbe_id/>
  <chebi_id>41509</chebi_id>
  <drugbank_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5584</metlin_id>
  <synthesis_reference>Lundberg, Bo; Pellas, Lars.  Preparation and characterization of cholesteryl linoleate.    Acta Academiae Aboensis, Series B:  Mathematica et Physica  (1973),  33(4),  4 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:34 UTC</creation_date>
  <update_date>2020-04-15 22:14:11 UTC</update_date>
  <accession>BMDB0000611</accession>
  <secondary_accessions>
    <accession>BMDB00611</accession>
  </secondary_accessions>
  <name>Coproporphyrin II</name>
  <description/>
  <synonyms>
    <synonym>3-[10,14,20-Tris(2-carboxyethyl)-5,9,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C36H38N4O8</chemical_formula>
  <average_molecular_weight>654.7089</average_molecular_weight>
  <monisotopic_moleculate_weight>654.268964212</monisotopic_moleculate_weight>
  <iupac_name>3-[10,14,20-tris(2-carboxyethyl)-5,9,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[10,14,20-tris(2-carboxyethyl)-5,9,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>3082-03-9</cas_registry_number>
  <smiles>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)/C(C)=C3CCC(O)=O</smiles>
  <inchi>InChI=1S/C36H38N4O8/c1-17-21(5-9-33(41)42)29-15-30-23(7-11-35(45)46)19(3)27(39-30)14-28-20(4)24(8-12-36(47)48)32(40-28)16-31-22(6-10-34(43)44)18(2)26(38-31)13-25(17)37-29/h13-16,37,40H,5-12H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)/b25-13-,26-13-,27-14-,28-14-,29-15-,30-15-,31-16-,32-16-</inchi>
  <inchikey>WBRBPZMVKKDPIT-GDDAKTJHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[10,14,20-tris(2-carboxyethyl)-5,9,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>654.7089</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>654.268964212</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)/C(C)=C3CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C36H38N4O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C36H38N4O8/c1-17-21(5-9-33(41)42)29-15-30-23(7-11-35(45)46)19(3)27(39-30)14-28-20(4)24(8-12-36(47)48)32(40-28)16-31-22(6-10-34(43)44)18(2)26(38-31)13-25(17)37-29/h13-16,37,40H,5-12H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)/b25-13-,26-13-,27-14-,28-14-,29-15-,30-15-,31-16-,32-16-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WBRBPZMVKKDPIT-GDDAKTJHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>206.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>176.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>73.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365553</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022142</foodb_id>
  <chemspider_id>16736702</chemspider_id>
  <pubchem_compound_id/>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5585</metlin_id>
  <synthesis_reference>Jacob K; Egeler E; Hennel B; Luppa P  Coproporphyrin isomers II and IV are normal constituents of human urine.    Journal of clinical chemistry and clinical biochemistry. Zeitschrift fur klinische Chemie und klinische Biochemie  (1989),  27(9),  659-61.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:36 UTC</creation_date>
  <update_date>2020-04-14 22:47:50 UTC</update_date>
  <accession>BMDB0000613</accession>
  <secondary_accessions>
    <accession>BMDB00613</accession>
  </secondary_accessions>
  <name>Erythronic acid</name>
  <description/>
  <synonyms>
    <synonym>Erythro-2,3,4-trihydroxybutyric acid</synonym>
    <synonym>Erythro-2,3,4-trihydroxybutyrate</synonym>
    <synonym>Erythronate</synonym>
    <synonym>(R*,r*)-2,3,4-trihydroxy-butanoate</synonym>
    <synonym>(R*,r*)-2,3,4-trihydroxy-butanoic acid</synonym>
    <synonym>2,3,4-Trihydroxybutanoate</synonym>
    <synonym>2,3,4-Trihydroxybutanoic acid</synonym>
    <synonym>D-Erythronate</synonym>
    <synonym>Erythronic acid</synonym>
  </synonyms>
  <chemical_formula>C4H8O5</chemical_formula>
  <average_molecular_weight>136.1033</average_molecular_weight>
  <monisotopic_moleculate_weight>136.037173366</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R)-2,3,4-trihydroxybutanoic acid</iupac_name>
  <traditional_iupac>erythronic acid</traditional_iupac>
  <cas_registry_number>13752-84-6</cas_registry_number>
  <smiles>OC[C@@H](O)[C@@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3-/m1/s1</inchi>
  <inchikey>JPIJQSOTBSSVTP-PWNYCUMCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
      <substituent>Sugar acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>erythronic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>100 - 102 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R)-2,3,4-trihydroxybutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>136.1033</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>136.037173366</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)[C@@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JPIJQSOTBSSVTP-PWNYCUMCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>26.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>159279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>159280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>159281</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022143</foodb_id>
  <chemspider_id>2061231</chemspider_id>
  <pubchem_compound_id>2781043</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id>37655</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-19877</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5586</metlin_id>
  <synthesis_reference>Heikkila, Heikki; Alen, Raimo; Kauko, Siru; Lindroos, Mirja; Nurmi, Juha; Sarmala, Paivi; Tylli, Matti.  Method for producing xylitol and erythritol from arabinoxylan-containing materials.    Eur. Pat. Appl.  (2000),     9 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:37 UTC</creation_date>
  <update_date>2020-04-14 22:47:51 UTC</update_date>
  <accession>BMDB0000614</accession>
  <secondary_accessions>
    <accession>BMDB00614</accession>
  </secondary_accessions>
  <name>PS(16:0/16:0)</name>
  <description/>
  <synonyms>
    <synonym>1,2-Dipalmitoylglycerophosphorylserine</synonym>
    <synonym>1,2-Dipalmitoylphosphatidylserine</synonym>
    <synonym>Dipalmitoyl-DL-a-phosphatidyl-L-serine</synonym>
    <synonym>Dipalmitoyl-DL-alpha-phosphatidyl-L-serine</synonym>
    <synonym>Dipalmitoylglycerophosphoserine</synonym>
    <synonym>Dipalmitoylphosphatidylserine</synonym>
    <synonym>DL-a-Dipalmitoyl phosphatidyl-L-serine</synonym>
    <synonym>DL-alpha-Dipalmitoyl phosphatidyl-L-serine</synonym>
    <synonym>DPPS</synonym>
    <synonym>Phosphatidylserine (16:0/16:0)</synonym>
    <synonym>Phosphatidylserine (32:0)</synonym>
    <synonym>PS(32:0)</synonym>
    <synonym>pSer(16:0/16:0)</synonym>
    <synonym>pSer(32:0)</synonym>
    <synonym>(2S)-2-Amino-3-({[2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoate</synonym>
  </synonyms>
  <chemical_formula>C38H74NO10P</chemical_formula>
  <average_molecular_weight>735.9686</average_molecular_weight>
  <monisotopic_moleculate_weight>735.505034105</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-({[2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid</iupac_name>
  <traditional_iupac>(2S)-2-amino-3-{[2,3-bis(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCC</smiles>
  <inchi>InChI=1S/C38H74NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h34-35H,3-33,39H2,1-2H3,(H,42,43)(H,44,45)/t34?,35-/m0/s1</inchi>
  <inchikey>KLFKZIQAIPDJCW-HTIIIDOHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phosphatidylserines. These are glycerophosphoserines in which two fatty acids are bonded to the glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerophospholipids</class>
    <sub_class>Glycerophosphoserines</sub_class>
    <direct_parent>Phosphatidylserines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkyl phosphates</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phosphoethanolamines</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Diacyl-glycerol-3-phosphoserine</substituent>
      <substituent>Dialkyl phosphate</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoethanolamine</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>9.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-({[2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>735.9686</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>735.505034105</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C38H74NO10P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C38H74NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h34-35H,3-33,39H2,1-2H3,(H,42,43)(H,44,45)/t34?,35-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KLFKZIQAIPDJCW-HTIIIDOHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>171.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>196.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>89.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>40</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33637</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id>3081382</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Hermetter, A.; Paltauf, F.; Hauser, H.  Synthesis of diacyl and alkylacyl glycerophosphoserines.    Chemistry and Physics of Lipids  (1982),  30(1),  35-45.  </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:38 UTC</creation_date>
  <update_date>2020-03-13 16:22:30 UTC</update_date>
  <accession>BMDB0000617</accession>
  <secondary_accessions>
    <accession>BMDB00617</accession>
  </secondary_accessions>
  <name>2-Furoic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Carboxyfuran</synonym>
    <synonym>2-Furancarboxylic acid</synonym>
    <synonym>2-Furanoic acid</synonym>
    <synonym>Acide 2-furoique</synonym>
    <synonym>Acido 2-furoico</synonym>
    <synonym>alpha-Furancarboxylic acid</synonym>
    <synonym>alpha-Furoic acid</synonym>
    <synonym>Furan-2-carbonsaeure</synonym>
    <synonym>Pyromucic acid</synonym>
    <synonym>2-Furancarboxylate</synonym>
    <synonym>2-Furanoate</synonym>
    <synonym>a-Furancarboxylate</synonym>
    <synonym>a-Furancarboxylic acid</synonym>
    <synonym>alpha-Furancarboxylate</synonym>
    <synonym>Α-furancarboxylate</synonym>
    <synonym>Α-furancarboxylic acid</synonym>
    <synonym>a-Furoate</synonym>
    <synonym>a-Furoic acid</synonym>
    <synonym>alpha-Furoate</synonym>
    <synonym>Α-furoate</synonym>
    <synonym>Α-furoic acid</synonym>
    <synonym>Pyromucate</synonym>
    <synonym>2-Furoate</synonym>
    <synonym>b-Furancarboxylate</synonym>
    <synonym>b-Furancarboxylic acid</synonym>
    <synonym>b-Furoate</synonym>
    <synonym>b-Furoic acid</synonym>
    <synonym>beta-Furancarboxylate</synonym>
    <synonym>beta-Furancarboxylic acid</synonym>
    <synonym>beta-Furoate</synonym>
    <synonym>beta-Furoic acid</synonym>
    <synonym>Furancarboxylate</synonym>
    <synonym>Furancarboxylic acid</synonym>
    <synonym>Furoate</synonym>
    <synonym>Furoic acid</synonym>
    <synonym>Furan-3-carboxylic</synonym>
    <synonym>2-Furoic acid, sodium salt</synonym>
    <synonym>Furan-2-ylacetate</synonym>
    <synonym>Furan-2-carboxylate</synonym>
    <synonym>2-Furoic acid</synonym>
  </synonyms>
  <chemical_formula>C5H4O3</chemical_formula>
  <average_molecular_weight>112.0835</average_molecular_weight>
  <monisotopic_moleculate_weight>112.016043994</monisotopic_moleculate_weight>
  <iupac_name>furan-2-carboxylic acid</iupac_name>
  <traditional_iupac>furoic acid</traditional_iupac>
  <cas_registry_number>88-14-2</cas_registry_number>
  <smiles>OC(=O)C1=CC=CO1</smiles>
  <inchi>InChI=1S/C5H4O3/c6-5(7)4-2-1-3-8-4/h1-3H,(H,6,7)</inchi>
  <inchikey>SMNDYUVBFMFKNZ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as furoic acids. These are organic compounds containing a furoic acid moiety, with a structure characterized by a furan ring bearing a carboxylic acid group at the C2 or C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Furans</class>
    <sub_class>Furoic acid and derivatives</sub_class>
    <direct_parent>Furoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Furoic acid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>furoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>133.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>37.1 mg/mL at 15 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.64</value>
      <source>POMONA (1987)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-6.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>furan-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>112.0835</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>112.016043994</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1=CC=CO1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H4O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H4O3/c6-5(7)4-2-1-3-8-4/h1-3H,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SMNDYUVBFMFKNZ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>50.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437646</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01546</kegg_id>
  <foodb_id>FDB000951</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>6919</pubchem_compound_id>
  <chemspider_id>10251740</chemspider_id>
  <pdbe_id/>
  <chebi_id>30845</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00000151</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>2-Furoic_acid</wikipedia_id>
  <metlin_id>2266</metlin_id>
  <synthesis_reference>Hurd, Charles D.; Garrett, J. W.; Osborne, E. N. Furan reactions. IV. Furoic acid from furfural. Journal of the American Chemical Society (1933), 55 1082-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:39 UTC</creation_date>
  <update_date>2020-04-14 22:47:51 UTC</update_date>
  <accession>BMDB0000618</accession>
  <secondary_accessions>
    <accession>BMDB00618</accession>
  </secondary_accessions>
  <name>D-Ribulose 5-phosphate</name>
  <description>D-Ribulose 5-phosphate belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. D-Ribulose 5-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).</description>
  <synonyms>
    <synonym>D-Ribulose 5-phosphoric acid</synonym>
    <synonym>{[(2S,3R,4S)-3,4,5-trihydroxyoxolan-2-yl]methoxy}phosphonate</synonym>
  </synonyms>
  <chemical_formula>C5H11O8P</chemical_formula>
  <average_molecular_weight>230.1098</average_molecular_weight>
  <monisotopic_moleculate_weight>230.01915384</monisotopic_moleculate_weight>
  <iupac_name>{[(2S,3R,4S)-3,4,5-trihydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2S,3R,4S)-3,4,5-trihydroxyoxolan-2-yl]methoxyphosphonic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>OC1O[C@@H](COP(O)(O)=O)[C@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C5H11O8P/c6-3-2(1-12-14(9,10)11)13-5(8)4(3)7/h2-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5?/m0/s1</inchi>
  <inchikey>KTVPXOYAKDPRHY-OWMBCFKOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxolanes</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxolane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2S,3R,4S)-3,4,5-trihydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>230.1098</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>230.01915384</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC1O[C@@H](COP(O)(O)=O)[C@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H11O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H11O8P/c6-3-2(1-12-14(9,10)11)13-5(8)4(3)7/h2-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KTVPXOYAKDPRHY-OWMBCFKOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>136.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1263913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1263914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1263915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1378996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1378997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1378998</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by GC-TOF/MS</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id>53477706</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Wong, Chi-Huey; McCurry, Stephen D.; Whitesides, George M.  Practical enzymic syntheses of ribulose 1,5 bisphosphate and ribose 5-phosphate.    Journal of the American Chemical Society  (1980),  102(27),  7938-9. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
      <pubmed_id>25599412</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00355</protein_accession>
      <name>Ribose-5-phosphate isomerase</name>
      <uniprot_id>Q3T186</uniprot_id>
      <gene_name>RPIA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00356</protein_accession>
      <name>6-phosphogluconate dehydrogenase, decarboxylating</name>
      <uniprot_id>Q3ZCI4</uniprot_id>
      <gene_name>PGD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:41 UTC</creation_date>
  <update_date>2020-04-16 20:39:10 UTC</update_date>
  <accession>BMDB0000619</accession>
  <secondary_accessions>
    <accession>BMDB00619</accession>
  </secondary_accessions>
  <name>Cholic acid</name>
  <description>Cholic acid, also known as cholate, belongs to the class of chemical entities known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. Cholic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).</description>
  <synonyms>
    <synonym>Cholate</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,9,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@](C)(CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C([H])(O)C[C@]4([H])C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])C[C@]([H])(O)[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19?,20+,22+,23+,24-/m1/s1</inchi>
  <inchikey>BHQCQFFYRZLCQQ-IATNSQEUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](C)(CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C([H])(O)C[C@]4([H])C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])C[C@]([H])(O)[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19?,20+,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHQCQFFYRZLCQQ-IATNSQEUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1326262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1326263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1326264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1440607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1440608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1440609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1383</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id>13020205</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Cholic acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Calimente, Daniel.  Synthesis and characterization of new naphthalimide and cholic acid-containing complexing agents.  (1998),   104 pp. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:42 UTC</creation_date>
  <update_date>2020-03-13 16:22:32 UTC</update_date>
  <accession>BMDB0000620</accession>
  <secondary_accessions>
    <accession>BMDB00620</accession>
  </secondary_accessions>
  <name>Glutaconic acid</name>
  <description/>
  <synonyms>
    <synonym>(e)-Glutaconate</synonym>
    <synonym>trans-Glutaconate</synonym>
    <synonym>trans-Glutaconic acid</synonym>
    <synonym>(e)-Glutaconic acid</synonym>
    <synonym>Glutaconate</synonym>
    <synonym>(e)-2-Pentenedioate</synonym>
    <synonym>(e)-2-Pentenedioic acid</synonym>
    <synonym>1,3-Propenedicarboxylate</synonym>
    <synonym>1,3-Propenedicarboxylic acid</synonym>
    <synonym>1-Propene-1,3-dicarboxylate</synonym>
    <synonym>1-Propene-1,3-dicarboxylic acid</synonym>
    <synonym>Pentenedioate</synonym>
    <synonym>Pentenedioic acid</synonym>
    <synonym>Glutaconic acid, (e)-isomer</synonym>
    <synonym>2-Pentendioate</synonym>
    <synonym>2-Pentenedioic acid</synonym>
    <synonym>Glutaconic acid</synonym>
  </synonyms>
  <chemical_formula>C5H6O4</chemical_formula>
  <average_molecular_weight>130.0987</average_molecular_weight>
  <monisotopic_moleculate_weight>130.02660868</monisotopic_moleculate_weight>
  <iupac_name>(2E)-pent-2-enedioic acid</iupac_name>
  <traditional_iupac>glutaconic acid</traditional_iupac>
  <cas_registry_number>1724-02-3</cas_registry_number>
  <smiles>OC(=O)C\C=C\C(O)=O</smiles>
  <inchi>InChI=1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+</inchi>
  <inchikey>XVOUMQNXTGKGMA-OWOJBTEDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Dicarboxylic acids and derivatives</sub_class>
    <direct_parent>Dicarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>glutaconic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>133 - 135 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.044</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-pent-2-enedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>130.0987</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>130.02660868</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C\C=C\C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H6O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XVOUMQNXTGKGMA-OWOJBTEDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>29.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362445</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02214</kegg_id>
  <foodb_id>FDB022146</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>5280498</pubchem_compound_id>
  <chemspider_id>4444138</chemspider_id>
  <pdbe_id/>
  <chebi_id>15670</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>GLUTACONATE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Glutaconic_acid</wikipedia_id>
  <metlin_id>5593</metlin_id>
  <synthesis_reference>Schwarz, Siegfried; Bohn, Helmut; Schmidt, Dieter; Kulpa, Manfred; Spakowski, Horst; Becker, Manfred.  Glutaconic acid.    Ger. (East)  (1967),     2 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:43 UTC</creation_date>
  <update_date>2020-04-15 21:59:36 UTC</update_date>
  <accession>BMDB0000621</accession>
  <secondary_accessions>
    <accession>BMDB00621</accession>
  </secondary_accessions>
  <name>D-Ribulose</name>
  <description/>
  <synonyms>
    <synonym>D-Arabinoketose</synonym>
    <synonym>D-Arabinulose</synonym>
    <synonym>D-Erythro-2-pentulose</synonym>
    <synonym>D-Erythro-pent-2-ulose</synonym>
    <synonym>D-Riboketose</synonym>
    <synonym>D-Rul</synonym>
    <synonym>D(-)-Ribulose</synonym>
    <synonym>D-Adonose</synonym>
    <synonym>D-Araboketose</synonym>
    <synonym>D-erythro-2-Keptopentose</synonym>
    <synonym>D-erythro-Pentulose</synonym>
    <synonym>D-Erythropentulose</synonym>
    <synonym>D-Ribosone</synonym>
    <synonym>Ribulose, (erythro-L)-isomer</synonym>
    <synonym>DL-erythro-Pentulose</synonym>
    <synonym>Ribulose</synonym>
    <synonym>Ribulose, (erythro-D)-isomer</synonym>
  </synonyms>
  <chemical_formula>C5H10O5</chemical_formula>
  <average_molecular_weight>150.1299</average_molecular_weight>
  <monisotopic_moleculate_weight>150.05282343</monisotopic_moleculate_weight>
  <iupac_name>(3R,4R)-1,3,4,5-tetrahydroxypentan-2-one</iupac_name>
  <traditional_iupac>D-ribulose</traditional_iupac>
  <cas_registry_number>488-84-6</cas_registry_number>
  <smiles>OC[C@@H](O)[C@@H](O)C(=O)CO</smiles>
  <inchi>InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5-/m1/s1</inchi>
  <inchikey>ZAQJHHRNXZUBTE-NQXXGFSBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Acyloins</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyloin</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>ribulose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4R)-1,3,4,5-tetrahydroxypentan-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>150.1299</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>150.05282343</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)[C@@H](O)C(=O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZAQJHHRNXZUBTE-NQXXGFSBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363414</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <drugbank_id/>
  <kegg_id/>
  <chemspider_id/>
  <pubchem_compound_id>151261</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17173</chebi_id>
  <meta_cyc_id>D-RIBULOSE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001131</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Ribulose</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Drueckhammer, D.G.; Durrwachter, J.R.; Pederson, R.L.; Crans, D.C.; Wong, C.H.  Reversible and in situ formation of organic arsenates and vanadates as organic phosphate mimics in enzymatic-reactions - mechanistic investigation of aldol reactions and synthetic applications.  J.Org. Chem. 1989, 54, 70.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:44 UTC</creation_date>
  <update_date>2020-04-15 22:30:59 UTC</update_date>
  <accession>BMDB0000622</accession>
  <secondary_accessions>
    <accession>BMDB00622</accession>
  </secondary_accessions>
  <name>Ethylmalonic acid</name>
  <description/>
  <synonyms>
    <synonym>1,1-Propanedicarboxylic acid</synonym>
    <synonym>2-Ethylmalonic acid</synonym>
    <synonym>alpha-Carboxybutyric acid</synonym>
    <synonym>1,1-Propanedicarboxylate</synonym>
    <synonym>Ethylmalonate</synonym>
    <synonym>2-Ethylmalonate</synonym>
    <synonym>a-Carboxybutyrate</synonym>
    <synonym>a-Carboxybutyric acid</synonym>
    <synonym>alpha-Carboxybutyrate</synonym>
    <synonym>α-Carboxybutyrate</synonym>
    <synonym>α-Carboxybutyric acid</synonym>
    <synonym>Ethyl-malonic acid</synonym>
    <synonym>2-Ethylpropanedioic acid</synonym>
    <synonym>Ethylmalonic acid</synonym>
  </synonyms>
  <chemical_formula>C5H8O4</chemical_formula>
  <average_molecular_weight>132.1146</average_molecular_weight>
  <monisotopic_moleculate_weight>132.042258744</monisotopic_moleculate_weight>
  <iupac_name>2-ethylpropanedioic acid</iupac_name>
  <traditional_iupac>ethylmalonic acid</traditional_iupac>
  <cas_registry_number>601-75-2</cas_registry_number>
  <smiles>CCC(C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H8O4/c1-2-3(4(6)7)5(8)9/h3H,2H2,1H3,(H,6,7)(H,8,9)</inchi>
  <inchikey>UKFXDFUAPNAMPJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Branched fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-dicarbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>112 - 114 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>712.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-ethylpropanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.1146</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O4/c1-2-3(4(6)7)5(8)9/h3H,2H2,1H3,(H,6,7)(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UKFXDFUAPNAMPJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1385</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022147</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>11756</pubchem_compound_id>
  <chemspider_id>11263</chemspider_id>
  <pdbe_id/>
  <chebi_id>741548</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>4180</metlin_id>
  <synthesis_reference>Zakharova, T. V.; Ternovaya, T. V.; Pirkes, S. B.; Kostromina, N. A.  Study of complexing in the neodymium-ethylmalonic acid system by a spectrographic method.    Zhurnal Neorganicheskoi Khimii  (1979),  24(7),  1827-31.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:45 UTC</creation_date>
  <update_date>2020-03-13 16:22:33 UTC</update_date>
  <accession>BMDB0000623</accession>
  <secondary_accessions>
    <accession>BMDB00623</accession>
  </secondary_accessions>
  <name>Dodecanedioic acid</name>
  <description/>
  <synonyms>
    <synonym>1,10-Decanedicarboxylic acid</synonym>
    <synonym>1,10-Dicarboxydecane</synonym>
    <synonym>1,12-Dodecanedioic acid</synonym>
    <synonym>Decamethylenedicarboxylic acid</synonym>
    <synonym>1,10-Decanedicarboxylate</synonym>
    <synonym>1,12-Dodecanedioate</synonym>
    <synonym>Decamethylenedicarboxylate</synonym>
    <synonym>Dodecanedioate</synonym>
    <synonym>Corfree m 2</synonym>
    <synonym>N-Dodecane-a,W-dioate</synonym>
    <synonym>N-Dodecane-a,W-dioic acid</synonym>
    <synonym>N-Dodecanedioate</synonym>
    <synonym>N-Dodecanedioic acid</synonym>
    <synonym>SL-AH</synonym>
    <synonym>Dodecandioic acid</synonym>
    <synonym>Dodecanedioic acid, sodium salt</synonym>
  </synonyms>
  <chemical_formula>C12H22O4</chemical_formula>
  <average_molecular_weight>230.3007</average_molecular_weight>
  <monisotopic_moleculate_weight>230.151809192</monisotopic_moleculate_weight>
  <iupac_name>dodecanedioic acid</iupac_name>
  <traditional_iupac>dodecanedioic acid</traditional_iupac>
  <cas_registry_number>693-23-2</cas_registry_number>
  <smiles>OC(=O)CCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16)</inchi>
  <inchikey>TVIDDXQYHWJXFK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>alpha,omega-dicarboxylic acid</external_descriptor>
      <external_descriptor>an &amp;alpha; &amp;omega; dicarboxylate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>127 - 129 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.04 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>dodecanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>230.3007</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>230.151809192</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H22O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H22O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h1-10H2,(H,13,14)(H,15,16)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>TVIDDXQYHWJXFK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>847</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437543</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02678</kegg_id>
  <foodb_id>FDB022148</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>12736</pubchem_compound_id>
  <chemspider_id>12213</chemspider_id>
  <pdbe_id/>
  <chebi_id>4676</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-10670</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Dodecanedioic acid</wikipedia_id>
  <metlin_id>5596</metlin_id>
  <synthesis_reference>Zhang, Xuwen; Li, Yuwei; He, Jianhua; Wang, Chen.  Method for separating and purifying dodecanedioic acid.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2003),     9 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:47 UTC</creation_date>
  <update_date>2020-03-13 16:22:34 UTC</update_date>
  <accession>BMDB0000624</accession>
  <secondary_accessions>
    <accession>BMDB00624</accession>
  </secondary_accessions>
  <name>D-Leucic acid</name>
  <description/>
  <synonyms>
    <synonym>(R)-2-Hydroxy-4-methylvaleric acid</synonym>
    <synonym>(R)-2-Hydroxyisocaproic acid</synonym>
    <synonym>(R)-Leucic acid</synonym>
    <synonym>2-Hydroxy-4-methyl-D-valeric acid</synonym>
    <synonym>alpha-Hydroxyisocaproic acid</synonym>
    <synonym>D-2-Hydroxy-4-methylpentanoic acid</synonym>
    <synonym>D-2-Hydroxy-4-methylvaleric acid</synonym>
    <synonym>D-2-Hydroxyisocaproic acid</synonym>
    <synonym>delta-Leucic acid</synonym>
    <synonym>Leucic acid</synonym>
    <synonym>D-2-Hydroxyisocaproate</synonym>
    <synonym>(R)-2-Hydroxy-4-methylpentanoate</synonym>
    <synonym>D-Leucate</synonym>
    <synonym>(R)-2-Hydroxy-4-methylvalerate</synonym>
    <synonym>(R)-2-Hydroxyisocaproate</synonym>
    <synonym>(R)-Leucate</synonym>
    <synonym>2-Hydroxy-4-methyl-D-valerate</synonym>
    <synonym>a-Hydroxyisocaproate</synonym>
    <synonym>a-Hydroxyisocaproic acid</synonym>
    <synonym>alpha-Hydroxyisocaproate</synonym>
    <synonym>Α-hydroxyisocaproate</synonym>
    <synonym>Α-hydroxyisocaproic acid</synonym>
    <synonym>D-2-Hydroxy-4-methylpentanoate</synonym>
    <synonym>D-2-Hydroxy-4-methylvalerate</synonym>
    <synonym>delta-Leucate</synonym>
    <synonym>Δ-leucate</synonym>
    <synonym>Δ-leucic acid</synonym>
    <synonym>Leucate</synonym>
    <synonym>(R)-2-Hydroxy-4-methylpentanoic acid</synonym>
    <synonym>(-)-2-Hydroxyisocaproate</synonym>
    <synonym>(-)-2-Hydroxyisocaproic acid</synonym>
    <synonym>(-)-a-Hydroxyisocaproate</synonym>
    <synonym>(-)-a-Hydroxyisocaproic acid</synonym>
    <synonym>(-)-alpha-Hydroxyisocaproate</synonym>
    <synonym>(-)-alpha-Hydroxyisocaproic acid</synonym>
    <synonym>(R)-2-Hydroxy-4-methyl-pentanoate</synonym>
    <synonym>(R)-2-Hydroxy-4-methyl-pentanoic acid</synonym>
    <synonym>2-Hydroxy-4-methyl-delta-valerate</synonym>
    <synonym>2-Hydroxy-4-methyl-delta-valeric acid</synonym>
    <synonym>D-a-Hydroxyisocaproate</synonym>
    <synonym>D-a-Hydroxyisocaproic acid</synonym>
    <synonym>delta-2-Hydroxy-4-methylpentanoate</synonym>
    <synonym>delta-2-Hydroxy-4-methylpentanoic acid</synonym>
    <synonym>delta-2-Hydroxy-4-methylvalerate</synonym>
    <synonym>delta-2-Hydroxy-4-methylvaleric acid</synonym>
    <synonym>delta-2-Hydroxyisocaproate</synonym>
    <synonym>delta-2-Hydroxyisocaproic acid</synonym>
    <synonym>delta-alpha-Hydroxyisocaproate</synonym>
    <synonym>delta-alpha-Hydroxyisocaproic acid</synonym>
  </synonyms>
  <chemical_formula>C6H12O3</chemical_formula>
  <average_molecular_weight>132.1577</average_molecular_weight>
  <monisotopic_moleculate_weight>132.07864425</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-hydroxy-4-methylpentanoic acid</iupac_name>
  <traditional_iupac>(-)-α-hydroxyisocaproate</traditional_iupac>
  <cas_registry_number>20312-37-2</cas_registry_number>
  <smiles>CC(C)C[C@@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t5-/m1/s1</inchi>
  <inchikey>LVRFTAZAXQPQHI-RXMQYKEDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>(2R)-2-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>2-hydroxy-4-methylvaleric acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-hydroxy-4-methylpentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.1577</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.07864425</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)C[C@@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LVRFTAZAXQPQHI-RXMQYKEDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437904</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022149</foodb_id>
  <drugbank_id/>
  <kegg_id>C03264</kegg_id>
  <chemspider_id>388986</chemspider_id>
  <pubchem_compound_id>439960</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>55534</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>2-Hydroxyisocaproic acid</wikipedia_id>
  <metlin_id>5597</metlin_id>
  <synthesis_reference>Kallwass, Helmut K. W.  Potential of R-2-hydroxyisocaproate dehydrogenase from Lactobacillus casei for stereospecific reductions.    Enzyme and Microbial Technology  (1992),  14(1),  28-35.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:48 UTC</creation_date>
  <update_date>2020-04-14 22:47:53 UTC</update_date>
  <accession>BMDB0000625</accession>
  <secondary_accessions>
    <accession>BMDB00625</accession>
  </secondary_accessions>
  <name>Gluconic acid</name>
  <description>Gluconic acid, also known as D-gluconate or dextronic acid, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Gluconic acid is a drug which is used for use as part of electrolyte supplementation in total parenteral nutrition [fda label]. Gluconic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Gluconic acid exists in all living species, ranging from bacteria to humans. In cattle, gluconic acid is involved in the metabolic pathway called the pentose phosphate pathway.</description>
  <synonyms>
    <synonym>(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoic acid</synonym>
    <synonym>D-Gluco-hexonic acid</synonym>
    <synonym>D-Gluconsaeure</synonym>
    <synonym>D-Glukonsaeure</synonym>
    <synonym>Dextronic acid</synonym>
    <synonym>Glycogenic acid</synonym>
    <synonym>Hexonic acid</synonym>
    <synonym>Maltonic acid</synonym>
    <synonym>D-Gluconate</synonym>
    <synonym>(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoate</synonym>
    <synonym>D-Gluco-hexonate</synonym>
    <synonym>Dextronate</synonym>
    <synonym>Glycogenate</synonym>
    <synonym>Hexonate</synonym>
    <synonym>Maltonate</synonym>
    <synonym>D-Gluconic acid</synonym>
    <synonym>Gluconate</synonym>
    <synonym>2,3,4,5,6-Pentahydroxy-hexanoate</synonym>
    <synonym>2,3,4,5,6-Pentahydroxy-hexanoic acid</synonym>
    <synonym>2,3,4,5,6-Pentahydroxyhexanoate</synonym>
    <synonym>2,3,4,5,6-Pentahydroxyhexanoic acid</synonym>
    <synonym>GCO</synonym>
    <synonym>Glosanto</synonym>
    <synonym>Glyconate</synonym>
    <synonym>Glyconic acid</synonym>
    <synonym>Pentahydroxycaproate</synonym>
    <synonym>Pentahydroxycaproic acid</synonym>
    <synonym>Boron gluconate</synonym>
    <synonym>Gluconic acid, (113)indium-labeled</synonym>
    <synonym>Gluconic acid, calcium salt</synonym>
    <synonym>Gluconic acid, cesium(+3) salt</synonym>
    <synonym>Gluconic acid, lanthanum(+3) salt</synonym>
    <synonym>Gluconic acid, sodium salt</synonym>
    <synonym>Gluconic acid, strontium (2:1) salt</synonym>
    <synonym>Magnerot</synonym>
    <synonym>Manganese gluconate</synonym>
    <synonym>Sodium gluconate</synonym>
    <synonym>Zinc gluconate</synonym>
    <synonym>Gluconic acid, (159)dysprosium-labeled salt</synonym>
    <synonym>Gluconic acid, aluminum (3:1) salt</synonym>
    <synonym>Gluconic acid, ammonium salt</synonym>
    <synonym>Gluconic acid, magnesium (2:1) salt</synonym>
    <synonym>Gluconic acid, (14)C-labeled</synonym>
    <synonym>Gluconic acid, 1-(14)C-labeled</synonym>
    <synonym>Gluconic acid, 6-(14)C-labeled</synonym>
    <synonym>Gluconic acid, cobalt (2:1) salt</synonym>
    <synonym>Gluconic acid, copper salt</synonym>
    <synonym>Gluconic acid, manganese (2:1) salt</synonym>
    <synonym>Gluconic acid, potassium salt</synonym>
    <synonym>Gluconic acid, tin(+2) salt</synonym>
    <synonym>Gluconic acid, zinc salt</synonym>
    <synonym>Lithium gluconate</synonym>
    <synonym>Magnesium gluconate</synonym>
    <synonym>Gluconic acid, (99)technecium (5+) salt</synonym>
    <synonym>Gluconic acid, fe(+2) salt, dihydrate</synonym>
    <synonym>Gluconic acid, monolithium salt</synonym>
    <synonym>Gluconic acid, monopotassium salt</synonym>
    <synonym>Gluconic acid, monosodium salt</synonym>
  </synonyms>
  <chemical_formula>C6H12O7</chemical_formula>
  <average_molecular_weight>196.1553</average_molecular_weight>
  <monisotopic_moleculate_weight>196.058302738</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid</iupac_name>
  <traditional_iupac>gluconate</traditional_iupac>
  <cas_registry_number>526-95-4</cas_registry_number>
  <smiles>OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1</inchi>
  <inchikey>RGHNJXZEOKUKBD-SQOUGZDYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Medium-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Gluconic_acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Uronic acids</external_descriptor>
      <external_descriptor>gluconic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>113 - 118 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>316 mg/mL at 25 °C</value>
      <source>MERCK INDEX (1996)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>196.1553</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>196.058302738</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RGHNJXZEOKUKBD-SQOUGZDYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>138.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437715</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB001980</foodb_id>
  <drugbank_id>DB13180</drugbank_id>
  <kegg_id>C00257</kegg_id>
  <chemspider_id>10240</chemspider_id>
  <pubchem_compound_id>10690</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>33198</chebi_id>
  <meta_cyc_id>GLUCONATE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007303</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Gluconic_acid</wikipedia_id>
  <metlin_id>345</metlin_id>
  <synthesis_reference>Anastassiadis, Savas; Morgunov, Igor G.  Gluconic acid production.    Recent Patents on Biotechnology  (2007),  1(2),  167-180.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:49 UTC</creation_date>
  <update_date>2020-04-15 22:06:46 UTC</update_date>
  <accession>BMDB0000626</accession>
  <secondary_accessions>
    <accession>BMDB00626</accession>
  </secondary_accessions>
  <name>Deoxycholic acid</name>
  <description/>
  <synonyms>
    <synonym>(3ALPHA,5ALPHA,12ALPHA)-3,12-DIHYDROXYCHOLAN-24-OIC ACID</synonym>
    <synonym>(3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-Oic acid</synonym>
    <synonym>3alpha,12alpha-Dihydroxy-5beta-cholanic acid</synonym>
    <synonym>7alpha-Deoxycholic acid</synonym>
    <synonym>Desoxycholic acid</synonym>
    <synonym>Desoxycholsaeure</synonym>
    <synonym>Deoxycholate</synonym>
    <synonym>3alpha,12alpha-Dihydroxy-5beta-cholanate</synonym>
    <synonym>(3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-Oate</synonym>
    <synonym>(3a,5a,12a)-3,12-DIHYDROXYCHOLAN-24-Oic acid</synonym>
    <synonym>(3alpha,5alpha,12alpha)-3,12-DIHYDROXYCHOLAN-24-Oate</synonym>
    <synonym>(3Α,5α,12α)-3,12-dihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5α,12α)-3,12-dihydroxycholan-24-Oic acid</synonym>
    <synonym>(3a,5b,12a)-3,12-Dihydroxycholan-24-Oate</synonym>
    <synonym>(3a,5b,12a)-3,12-Dihydroxycholan-24-Oic acid</synonym>
    <synonym>(3alpha,5beta,12alpha)-3,12-Dihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5β,12α)-3,12-dihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5β,12α)-3,12-dihydroxycholan-24-Oic acid</synonym>
    <synonym>3a,12a-Dihydroxy-5b-cholanate</synonym>
    <synonym>3a,12a-Dihydroxy-5b-cholanic acid</synonym>
    <synonym>3Α,12α-dihydroxy-5β-cholanate</synonym>
    <synonym>3Α,12α-dihydroxy-5β-cholanic acid</synonym>
    <synonym>7a-Deoxycholate</synonym>
    <synonym>7a-Deoxycholic acid</synonym>
    <synonym>7alpha-Deoxycholate</synonym>
    <synonym>7Α-deoxycholate</synonym>
    <synonym>7Α-deoxycholic acid</synonym>
    <synonym>Desoxycholate</synonym>
    <synonym>5b-Cholanic acid-3a,12a-diol</synonym>
    <synonym>5b-Deoxycholate</synonym>
    <synonym>5b-Deoxycholic acid</synonym>
    <synonym>7-Deoxycholate</synonym>
    <synonym>7-Deoxycholic acid</synonym>
    <synonym>Cholerebic</synonym>
    <synonym>Cholorebic</synonym>
    <synonym>Degalol</synonym>
    <synonym>Deoxy-cholate</synonym>
    <synonym>Deoxy-cholic acid</synonym>
    <synonym>Deoxycholatate</synonym>
    <synonym>Deoxycholatic acid</synonym>
    <synonym>Acid, lagodeoxycholic</synonym>
    <synonym>Deoxycholic acid, 5alpha isomer</synonym>
    <synonym>Deoxycholic acid, sodium salt, 12beta-isomer</synonym>
    <synonym>Lagodeoxycholic acid</synonym>
    <synonym>Acid, choleic</synonym>
    <synonym>Deoxycholic acid, 12beta isomer</synonym>
    <synonym>Deoxycholic acid, 3beta-isomer</synonym>
    <synonym>Deoxycholic acid, monoammonium salt</synonym>
    <synonym>12beta-Isomer deoxycholic acid</synonym>
    <synonym>3beta-Isomer deoxycholic acid</synonym>
    <synonym>Acid, 5alpha-isomer deoxycholic</synonym>
    <synonym>Acid, deoxycholic</synonym>
    <synonym>Acid, desoxycholic</synonym>
    <synonym>Deoxycholate, sodium</synonym>
    <synonym>Deoxycholic acid, 12beta-isomer</synonym>
    <synonym>Deoxycholic acid, 5alpha-isomer</synonym>
    <synonym>Deoxycholic acid, monopotassium salt</synonym>
    <synonym>Deoxycholic acid, monosodium salt</synonym>
    <synonym>5alpha-Isomer deoxycholic acid</synonym>
    <synonym>Acid, dihydroxycholanoic</synonym>
    <synonym>Choleic acid</synonym>
    <synonym>Deoxycholic acid, 3beta isomer</synonym>
    <synonym>Deoxycholic acid, disodium salt</synonym>
    <synonym>Deoxycholic acid, magnesium (2:1) salt</synonym>
    <synonym>Dihydroxycholanoic acid</synonym>
    <synonym>Sodium deoxycholate</synonym>
  </synonyms>
  <chemical_formula>C24H40O4</chemical_formula>
  <average_molecular_weight>392.572</average_molecular_weight>
  <monisotopic_moleculate_weight>392.292659768</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>83-44-3</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O</smiles>
  <inchi>InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1</inchi>
  <inchikey>KXGVEGMKQFWNSR-LLQZFEROSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>Cholane and derivatives</external_descriptor>
      <external_descriptor>bile acid</external_descriptor>
      <external_descriptor>dihydroxy-5beta-cholanic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>392.572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.292659768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KXGVEGMKQFWNSR-LLQZFEROSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439281</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB03619</drugbank_id>
  <foodb_id>FDB012780</foodb_id>
  <chemspider_id>193196</chemspider_id>
  <pubchem_compound_id>222528</pubchem_compound_id>
  <kegg_id>C04483</kegg_id>
  <pdbe_id/>
  <chebi_id>28834</chebi_id>
  <knapsack_id>C00030117</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Deoxycholic acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>265</metlin_id>
  <synthesis_reference>He, Zhiquan.  in-situ generation of deoxycholic acid by poultry for Chinese medicine.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (1993),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01586</protein_accession>
      <name>Bile acid receptor</name>
      <uniprot_id>Q3SZL0</uniprot_id>
      <gene_name>NR1H4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:50 UTC</creation_date>
  <update_date>2020-04-15 23:56:26 UTC</update_date>
  <accession>BMDB0000628</accession>
  <secondary_accessions>
    <accession>BMDB00628</accession>
  </secondary_accessions>
  <name>Epitestosterone</name>
  <description>Testosterone belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, testosterone is considered to be a steroid lipid molecule. Testosterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Testosterone exists in all living organisms, ranging from bacteria to humans. Testosterone participates in a number of enzymatic reactions, within cattle. In particular, Testosterone can be converted into 19-hydroxytestosterone; which is catalyzed by the enzyme cytochrome P450 19A1. In addition, Testosterone can be converted into androstenedione; which is catalyzed by the enzyme testosterone 17-beta-dehydrogenase 3. In cattle, testosterone is involved in the metabolic pathway called the androgen and estrogen metabolism pathway. Testosterone is a potentially toxic compound.</description>
  <synonyms>
    <synonym>Epi-testosterone</synonym>
    <synonym>17-Epitestosterone</synonym>
    <synonym>17a-cis-Testosterone</synonym>
    <synonym>cis-Testosterone</synonym>
    <synonym>Isotestosterone</synonym>
    <synonym>17-alpha-Testosterone</synonym>
    <synonym>17 alpha Testosterone</synonym>
    <synonym>Epitestosterone</synonym>
  </synonyms>
  <chemical_formula>C19H28O2</chemical_formula>
  <average_molecular_weight>288.4244</average_molecular_weight>
  <monisotopic_moleculate_weight>288.20893014</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10R,11S,14R,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10R,11S,14R,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</traditional_iupac>
  <cas_registry_number>481-30-1</cas_registry_number>
  <smiles>[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17+,18-,19-/m0/s1</inchi>
  <inchikey>MUMGGOZAMZWBJJ-KZYORJDKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>3-oxo steroid</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>androstanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10R,11S,14R,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>288.4244</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>288.20893014</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H28O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17+,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MUMGGOZAMZWBJJ-KZYORJDKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Androstenedione Metabolism</name>
      <smpdb_id>SMP0087271</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>247947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>247948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>247949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>267888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>267889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>267890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102639</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000245</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Half skim milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000177</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000344</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
          <pubmed_id>18412364</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB07768</drugbank_id>
  <pdbe_id/>
  <chebi_id>42534</chebi_id>
  <pubchem_compound_id>10204</pubchem_compound_id>
  <foodb_id>FDB011544</foodb_id>
  <chemspider_id>9789</chemspider_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id>Epitestosterone</wikipedia_id>
  <metlin_id>5601</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Alvarez, Francisco.  Steroids. CCXLIX. A new synthesis of epitestosterone from pregnenolone acetate via nitrosation.  Steroids  (1963),  2(4),  393-8.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16.</reference_text>
      <pubmed_id>18412364</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:51 UTC</creation_date>
  <update_date>2020-04-15 22:35:28 UTC</update_date>
  <accession>BMDB0000629</accession>
  <secondary_accessions>
    <accession>BMDB00629</accession>
  </secondary_accessions>
  <name>Chondroitin</name>
  <description>Chondroitin belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Chondroitin is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Phosphoadenosine phosphosulfate and chondroitin can be converted into adenosine 3',5'-diphosphate and chondroitin 4-sulfate; which is catalyzed by the enzyme carbohydrate sulfotransferase 11. In cattle, chondroitin is involved in the metabolic pathway called the sulfate/sulfite metabolism pathway.</description>
  <synonyms>
    <synonym>(2R,3R,4S)-2-[(2R,3R,4R,5R,6R)-3-Acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid</synonym>
    <synonym>4-Deoxy-L-threo-hex-4-enopyranosyluronic acid-(1,3)-N-acetyl-D-galactosamine</synonym>
    <synonym>Chondroitin disaccharide</synonym>
    <synonym>Chondroitin-D-glucuronate</synonym>
    <synonym>Unsaturated chondroitin disaccharide</synonym>
  </synonyms>
  <chemical_formula>C14H21NO11</chemical_formula>
  <average_molecular_weight>379.3166</average_molecular_weight>
  <monisotopic_moleculate_weight>379.111460519</monisotopic_moleculate_weight>
  <iupac_name>(3R,4R)-2-{[(2R,3S,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid</iupac_name>
  <traditional_iupac>(4R,5R)-6-{[(2R,3S,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxy-5,6-dihydro-4H-pyran-2-carboxylic acid</traditional_iupac>
  <cas_registry_number>9007-27-6</cas_registry_number>
  <smiles>CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1OC1OC(=C[C@@H](O)[C@H]1O)C(O)=O</smiles>
  <inchi>InChI=1S/C14H21NO11/c1-4(17)15-8-11(10(20)7(3-16)24-13(8)23)26-14-9(19)5(18)2-6(25-14)12(21)22/h2,5,7-11,13-14,16,18-20,23H,3H2,1H3,(H,15,17)(H,21,22)/t5-,7-,8+,9-,10+,11-,13-,14?/m1/s1</inchi>
  <inchikey>DLGJWSVWTWEWBJ-HGGSSLSASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Acylaminosugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Disaccharides</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Acylaminosugar</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4R)-2-{[(2R,3S,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>379.3166</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>379.111460519</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1OC1OC(=C[C@@H](O)[C@H]1O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H21NO11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H21NO11/c1-4(17)15-8-11(10(20)7(3-16)24-13(8)23)26-14-9(19)5(18)2-6(25-14)12(21)22/h2,5,7-11,13-14,16,18-20,23H,3H2,1H3,(H,15,17)(H,21,22)/t5-,7-,8+,9-,10+,11-,13-,14?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DLGJWSVWTWEWBJ-HGGSSLSASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>195.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Sulfate/Sulfite Metabolism</name>
      <smpdb_id>SMP0087216</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345444</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022150</foodb_id>
  <drugbank_id/>
  <kegg_id>C00401</kegg_id>
  <chemspider_id/>
  <pubchem_compound_id>53477707</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16137</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Chondroitin</wikipedia_id>
  <metlin_id>5602</metlin_id>
  <synthesis_reference>Hallen, Anund; Nasir-Ud-Din; Jeanloz, Roger W. Chemical structure of shark cartilage chondroitin sulfate. Journal of the Chemical Society of Pakistan (1989), 11(2), 168-77.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00373</protein_accession>
      <name>Dermatan-sulfate epimerase</name>
      <uniprot_id>P0C2H4</uniprot_id>
      <gene_name>DSE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01345</protein_accession>
      <name>Cartilage oligomeric matrix protein</name>
      <uniprot_id>P35445</uniprot_id>
      <gene_name>COMP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01353</protein_accession>
      <name>CD97 antigen</name>
      <uniprot_id>Q8SQA4</uniprot_id>
      <gene_name>CD97</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01574</protein_accession>
      <name>Vitrin</name>
      <uniprot_id>Q95LI2</uniprot_id>
      <gene_name>VIT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01575</protein_accession>
      <name>Cysteine-rich secretory protein LCCL domain-containing 2</name>
      <uniprot_id>A6QLZ7</uniprot_id>
      <gene_name>CRISPLD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02081</protein_accession>
      <name>Olfactomedin-like protein 2B</name>
      <uniprot_id>A6QLD2</uniprot_id>
      <gene_name>OLFML2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:52 UTC</creation_date>
  <update_date>2020-04-16 20:38:30 UTC</update_date>
  <accession>BMDB0000630</accession>
  <secondary_accessions>
    <accession>BMDB00630</accession>
  </secondary_accessions>
  <name>Cytosine</name>
  <description>Cytosine, also known as C, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Cytosine exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Cytosine exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>4-Amino-2(1H)-pyrimidinone</synonym>
    <synonym>4-Amino-2-hydroxypyrimidine</synonym>
    <synonym>C</synonym>
    <synonym>Cyt</synonym>
    <synonym>Cytosin</synonym>
    <synonym>Zytosin</synonym>
    <synonym>4-Amino-2-oxo-1,2-dihydropyrimidine</synonym>
    <synonym>4-Aminouracil</synonym>
    <synonym>Cytosinimine</synonym>
  </synonyms>
  <chemical_formula>C4H5N3O</chemical_formula>
  <average_molecular_weight>111.102</average_molecular_weight>
  <monisotopic_moleculate_weight>111.043261797</monisotopic_moleculate_weight>
  <iupac_name>6-amino-1,2-dihydropyrimidin-2-one</iupac_name>
  <traditional_iupac>2(1H)-pyrimidinone, 6-amino-</traditional_iupac>
  <cas_registry_number>71-30-7</cas_registry_number>
  <smiles>NC1=CC=NC(=O)N1</smiles>
  <inchi>InChI=1S/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8)</inchi>
  <inchikey>OPTASPLRGRRNAP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazines</class>
    <sub_class>Pyrimidines and pyrimidine derivatives</sub_class>
    <direct_parent>Pyrimidones</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidone</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a pyrimidine base</external_descriptor>
      <external_descriptor>a pyrimidine-related compound</external_descriptor>
      <external_descriptor>aminopyrimidine</external_descriptor>
      <external_descriptor>pyrimidine nucleobase</external_descriptor>
      <external_descriptor>pyrimidines</external_descriptor>
      <external_descriptor>pyrimidone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>&gt; 300 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>8.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.73</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6-amino-1,2-dihydropyrimidin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>111.102</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>111.043261797</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=CC=NC(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H5N3O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OPTASPLRGRRNAP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>67.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>858</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437407</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022151</foodb_id>
  <chemspider_id>577</chemspider_id>
  <kegg_id>C00380</kegg_id>
  <drugbank_id/>
  <pubchem_compound_id>597</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16040</chebi_id>
  <knapsack_id>C00001498</knapsack_id>
  <meta_cyc_id>CYTOSINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34812</bigg_id>
  <wikipedia_id>Cytosine</wikipedia_id>
  <metlin_id>283</metlin_id>
  <synthesis_reference>Hitchings, George H.; Elion, Gertrude B.; Falco, Elvira A.; Russell, Peter B. New synthesis of cytosine and 5-methylcytosine. Journal of Biological Chemistry (1949), 177 357-60.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:53 UTC</creation_date>
  <update_date>2020-04-14 22:47:54 UTC</update_date>
  <accession>BMDB0000631</accession>
  <secondary_accessions>
    <accession>BMDB00631</accession>
  </secondary_accessions>
  <name>Deoxycholic acid glycine conjugate</name>
  <description/>
  <synonyms>
    <synonym>Deoxycholate glycine conjugate</synonym>
    <synonym>Deoxycholic acid glycine conjugic acid</synonym>
    <synonym>Deoxycholylglycine</synonym>
    <synonym>Deoxyglycocholate</synonym>
    <synonym>Deoxyglycocholic acid</synonym>
    <synonym>Glycodeoxycholate</synonym>
    <synonym>Glycodeoxycholic acid</synonym>
    <synonym>Glycodesoxycholate</synonym>
    <synonym>Glycodesoxycholic acid</synonym>
    <synonym>Glycyldeoxycholate</synonym>
    <synonym>Glycyldeoxycholic acid</synonym>
    <synonym>N-(3a,12a-Dihydroxy-5b-cholan-24-oyl)-glycine</synonym>
    <synonym>N-(Carboxymethyl)-3a,12a-dihydroxy-5b-cholan-24-amide</synonym>
    <synonym>Deoxycholate, glycine</synonym>
    <synonym>Acid, glycodeoxycholic</synonym>
    <synonym>Glycine deoxycholate</synonym>
  </synonyms>
  <chemical_formula>C26H43NO5</chemical_formula>
  <average_molecular_weight>449.6233</average_molecular_weight>
  <monisotopic_moleculate_weight>449.314123491</monisotopic_moleculate_weight>
  <iupac_name>2-[(4R)-4-[(2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid</iupac_name>
  <traditional_iupac>[(4R)-4-[(2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid</traditional_iupac>
  <cas_registry_number>360-65-6</cas_registry_number>
  <smiles>[H][C@]12CCC3C4CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]4(C)[C@@H](O)CC3[C@@]1(C)CC[C@@H](O)C2</smiles>
  <inchi>InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18?,19-,20?,21?,22+,25+,26-/m1/s1</inchi>
  <inchikey>WVULKSPCQVQLCU-ZMBDPXIHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Glycinated bile acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Dihydroxy bile acids, alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycinated bile acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>0.0027 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.25</value>
      <source>RODA,A ET AL. (1990)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4R)-4-[(2S,5R,7R,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>449.6233</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>449.314123491</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]12CCC3C4CC[C@H]([C@H](C)CCC(=O)NCC(O)=O)[C@@]4(C)[C@@H](O)CC3[C@@]1(C)CC[C@@H](O)C2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H43NO5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18?,19-,20?,21?,22+,25+,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WVULKSPCQVQLCU-ZMBDPXIHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>106.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>52.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357807</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022152</foodb_id>
  <chemspider_id>17215983</chemspider_id>
  <pubchem_compound_id>22833539</pubchem_compound_id>
  <kegg_id>C05464 </kegg_id>
  <pdbe_id/>
  <chebi_id>27471</chebi_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5604</metlin_id>
  <synthesis_reference>Parmentier G; Eyssen H  Synthesis and characteristics of the specific monosulfates of chenodeoxycholate, deoxycholate and their taurine or glycine conjugates.    Steroids  (1977),  30(5),  583-90.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:33:59 UTC</creation_date>
  <update_date>2020-04-16 20:39:59 UTC</update_date>
  <accession>BMDB0000632</accession>
  <secondary_accessions>
    <accession>BMDB00632</accession>
  </secondary_accessions>
  <name>Dermatan</name>
  <description/>
  <synonyms>
    <synonym>b-Heparin</synonym>
    <synonym>beta-Heparin</synonym>
    <synonym>Chondroitin sulfate b</synonym>
    <synonym>Chondroitin sulfate type b</synonym>
    <synonym>Chondroitin sulphate b</synonym>
    <synonym>Chondroitin sulphate type b</synonym>
    <synonym>Chondroitinsulfuric acid b</synonym>
    <synonym>Chondroitinsulfuric acid type b</synonym>
    <synonym>Dermatan 4-sulfate</synonym>
    <synonym>Dermatan 4-sulphate</synonym>
    <synonym>Dermatan hydrogen sulfate</synonym>
    <synonym>Dermatan hydrogen sulphate</synonym>
    <synonym>Dermatan sulfate</synonym>
    <synonym>Dermatan sulphate</synonym>
    <synonym>Desmin 370</synonym>
    <synonym>DS 435</synonym>
    <synonym>MF 701</synonym>
    <synonym>3-Ethyl-4,5-dihydroxy-6-[({3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-4-yl}oxy)methyl]oxane-2-carboxylate</synonym>
    <synonym>3-Ethyl-4,5-dihydroxy-6-[({3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-2-methoxy-5-(sulphooxy)oxan-4-yl}oxy)methyl]oxane-2-carboxylate</synonym>
    <synonym>3-Ethyl-4,5-dihydroxy-6-[({3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-2-methoxy-5-(sulphooxy)oxan-4-yl}oxy)methyl]oxane-2-carboxylic acid</synonym>
  </synonyms>
  <chemical_formula>C18H31NO14S</chemical_formula>
  <average_molecular_weight>517.5</average_molecular_weight>
  <monisotopic_moleculate_weight>517.146525856</monisotopic_moleculate_weight>
  <iupac_name>6-({[3-acetamido-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-4-yl]oxy}methyl)-3-ethyl-4,5-dihydroxyoxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>6-({[3-acetamido-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-4-yl]oxy}methyl)-3-ethyl-4,5-dihydroxyoxane-2-carboxylic acid</traditional_iupac>
  <cas_registry_number>24967-94-0</cas_registry_number>
  <smiles>CCC1C(O)C(O)C(COC2C(NC(C)=O)C(OC)OC(CO)C2OS(O)(=O)=O)OC1C(O)=O</smiles>
  <inchi>InChI=1S/C18H31NO14S/c1-4-8-12(22)13(23)10(31-14(8)17(24)25)6-30-16-11(19-7(2)21)18(29-3)32-9(5-20)15(16)33-34(26,27)28/h8-16,18,20,22-23H,4-6H2,1-3H3,(H,19,21)(H,24,25)(H,26,27,28)</inchi>
  <inchikey>DYTJJIPHSVVNGF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>N-acyl-alpha-hexosamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharide sulfates</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide sulfate</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6-({[3-acetamido-6-(hydroxymethyl)-2-methoxy-5-(sulfooxy)oxan-4-yl]oxy}methyl)-3-ethyl-4,5-dihydroxyoxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>517.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>517.146525856</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC1C(O)C(O)C(COC2C(NC(C)=O)C(OC)OC(CO)C2OS(O)(=O)=O)OC1C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H31NO14S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H31NO14S/c1-4-8-12(22)13(23)10(31-14(8)17(24)25)6-30-16-11(19-7(2)21)18(29-3)32-9(5-20)15(16)33-34(26,27)28/h8-16,18,20,22-23H,4-6H2,1-3H3,(H,19,21)(H,24,25)(H,26,27,28)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DYTJJIPHSVVNGF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>227.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>106.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>48.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1220713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1220714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1220715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1336390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1336391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1336392</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022153</foodb_id>
  <chemspider_id/>
  <kegg_id>C00426</kegg_id>
  <drugbank_id/>
  <pubchem_compound_id>72682693</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Dermatan sulfate</wikipedia_id>
  <metlin_id>5605</metlin_id>
  <synthesis_reference>Nagasawa, Kinzo; Inoue, Yuko.  Desulfation of glycosaminoglycuronan sulfates.    Methods in Carbohydrate Chemistry  (1980),  8  287-9. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00373</protein_accession>
      <name>Dermatan-sulfate epimerase</name>
      <uniprot_id>P0C2H4</uniprot_id>
      <gene_name>DSE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01574</protein_accession>
      <name>Vitrin</name>
      <uniprot_id>Q95LI2</uniprot_id>
      <gene_name>VIT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01575</protein_accession>
      <name>Cysteine-rich secretory protein LCCL domain-containing 2</name>
      <uniprot_id>A6QLZ7</uniprot_id>
      <gene_name>CRISPLD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:00 UTC</creation_date>
  <update_date>2020-03-13 16:22:38 UTC</update_date>
  <accession>BMDB0000633</accession>
  <secondary_accessions>
    <accession>BMDB00633</accession>
  </secondary_accessions>
  <name>D-Biopterin</name>
  <description/>
  <synonyms>
    <synonym>(S,R)-Biopterin</synonym>
    <synonym>Biopterin</synonym>
    <synonym>2-Amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone</synonym>
    <synonym>Dictyopterin</synonym>
    <synonym>Orinapterin</synonym>
  </synonyms>
  <chemical_formula>C9H11N5O3</chemical_formula>
  <average_molecular_weight>237.2153</average_molecular_weight>
  <monisotopic_moleculate_weight>237.086189243</monisotopic_moleculate_weight>
  <iupac_name>2-amino-6-[(1S,2R)-1,2-dihydroxypropyl]-4,8-dihydropteridin-4-one</iupac_name>
  <traditional_iupac>2-amino-6-[(1S,2R)-1,2-dihydroxypropyl]-8H-pteridin-4-one</traditional_iupac>
  <cas_registry_number>13039-62-8</cas_registry_number>
  <smiles>C[C@@H](O)[C@@H](O)C1=CNC2=NC(N)=NC(=O)C2=N1</smiles>
  <inchi>InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m1/s1</inchi>
  <inchikey>LHQIJBMDNUYRAM-AWFVSMACSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Biopterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrazines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Biopterin</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrazine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>biopterin</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-6-[(1S,2R)-1,2-dihydroxypropyl]-4,8-dihydropteridin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>237.2153</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>237.086189243</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](O)[C@@H](O)C1=CNC2=NC(N)=NC(=O)C2=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11N5O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LHQIJBMDNUYRAM-AWFVSMACSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>132.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>57.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>254604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>254605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>254606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>274545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>274546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>274547</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB03886</drugbank_id>
  <foodb_id>FDB022154</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>444475</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id>41183</chebi_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Biopterin</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Andrews, Kenneth J. M.; Barber, W. E.; Tong, B. P.  Synthesis of biopterin.    Journal of the Chemical Society [Section] C:  Organic  (1969),   (6),  928-30.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:01 UTC</creation_date>
  <update_date>2020-03-13 16:22:39 UTC</update_date>
  <accession>BMDB0000634</accession>
  <secondary_accessions>
    <accession>BMDB00634</accession>
  </secondary_accessions>
  <name>Citraconic acid</name>
  <description>Citraconic acid, also known as 2-methylmaleate or methylmaleic acid, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Citraconic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Citraconic acid exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>(Z)-2-Methyl-2-butenedioic acid</synonym>
    <synonym>2-Methyl-2-butenedioic acid</synonym>
    <synonym>2-Methylmaleic acid</synonym>
    <synonym>alpha-Methylmaleic acid</synonym>
    <synonym>cis-2-Methylbutenedioic acid</synonym>
    <synonym>cis-Methylbutenedioic acid</synonym>
    <synonym>Citraconsaeure</synonym>
    <synonym>Methyl-maleinsaeure</synonym>
    <synonym>Methylmaleic acid</synonym>
    <synonym>Citraconate</synonym>
    <synonym>(Z)-2-Methyl-2-butenedioate</synonym>
    <synonym>2-Methyl-2-butenedioate</synonym>
    <synonym>2-Methylmaleate</synonym>
    <synonym>a-Methylmaleate</synonym>
    <synonym>a-Methylmaleic acid</synonym>
    <synonym>alpha-Methylmaleate</synonym>
    <synonym>Α-methylmaleate</synonym>
    <synonym>Α-methylmaleic acid</synonym>
    <synonym>cis-2-Methylbutenedioate</synonym>
    <synonym>cis-Methylbutenedioate</synonym>
    <synonym>Methylmaleate</synonym>
    <synonym>Citraconic acid, ammonium salt</synonym>
    <synonym>Citraconic acid, calcium salt</synonym>
    <synonym>Citraconic acid, sodium salt</synonym>
    <synonym>Methylfumaric acid</synonym>
    <synonym>(e)-2-Methyl-2-butenedioic acid</synonym>
    <synonym>Citraconic acid, (e)-isomer</synonym>
    <synonym>Mesaconic acid</synonym>
    <synonym>Monomethylfumarate</synonym>
  </synonyms>
  <chemical_formula>C5H6O4</chemical_formula>
  <average_molecular_weight>130.0987</average_molecular_weight>
  <monisotopic_moleculate_weight>130.02660868</monisotopic_moleculate_weight>
  <iupac_name>(2Z)-2-methylbut-2-enedioic acid</iupac_name>
  <traditional_iupac>citraconic acid</traditional_iupac>
  <cas_registry_number>498-23-7</cas_registry_number>
  <smiles>C\C(=C\C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-</inchi>
  <inchikey>HNEGQIOMVPPMNR-IHWYPQMZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Methyl-branched fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>88 - 94 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>783.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2Z)-2-methylbut-2-enedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>130.0987</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>130.02660868</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C\C(=C\C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H6O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HNEGQIOMVPPMNR-IHWYPQMZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439199</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by GC-TOF/MS</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB04734</drugbank_id>
  <foodb_id>FDB022155</foodb_id>
  <chemspider_id>553689</chemspider_id>
  <pubchem_compound_id>643798</pubchem_compound_id>
  <kegg_id>C02226</kegg_id>
  <pdbe_id/>
  <chebi_id>17626</chebi_id>
  <knapsack_id/>
  <meta_cyc_id>2-METHYLMALEATE</meta_cyc_id>
  <wikipedia_id>Citraconic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5607</metlin_id>
  <synthesis_reference>Berg, Rudolph G.  Catalytic preparation of citraconic and itaconic acids. U.S.  (1972), 5 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
      <pubmed_id>25599412</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:02 UTC</creation_date>
  <update_date>2020-03-13 16:22:39 UTC</update_date>
  <accession>BMDB0000635</accession>
  <secondary_accessions>
    <accession>BMDB00635</accession>
  </secondary_accessions>
  <name>Succinylacetone</name>
  <description/>
  <synonyms>
    <synonym>4,6-Dioxoheptanoate</synonym>
    <synonym>4,6-Dioxoheptanoic acid</synonym>
    <synonym>Succinylacetone</synonym>
  </synonyms>
  <chemical_formula>C7H10O4</chemical_formula>
  <average_molecular_weight>158.1519</average_molecular_weight>
  <monisotopic_moleculate_weight>158.057908808</monisotopic_moleculate_weight>
  <iupac_name>4,6-dioxoheptanoic acid</iupac_name>
  <traditional_iupac>succinylacetone</traditional_iupac>
  <cas_registry_number>51568-18-4</cas_registry_number>
  <smiles>CC(=O)CC(=O)CCC(O)=O</smiles>
  <inchi>InChI=1S/C7H10O4/c1-5(8)4-6(9)2-3-7(10)11/h2-4H2,1H3,(H,10,11)</inchi>
  <inchikey>WYEPBHZLDUPIOD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12  carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Medium-chain keto acids and derivatives</sub_class>
    <direct_parent>Medium-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta-diketones</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Gamma-keto acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>1,3-diketone</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Gamma-keto acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Medium-chain keto acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>66 - 67 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4,6-dioxoheptanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>158.1519</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>158.057908808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)CC(=O)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H10O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H10O4/c1-5(8)4-6(9)2-3-7(10)11/h2-4H2,1H3,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WYEPBHZLDUPIOD-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>71.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>36.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10081</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022156</foodb_id>
  <chemspider_id>5121</chemspider_id>
  <pubchem_compound_id>5312</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id>87897</chebi_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Succinylacetone</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5608</metlin_id>
  <synthesis_reference>Levenson, Corey H. Process for the preparation of succinylacetone.    PCT Int. Appl.  (1991),     9 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:03 UTC</creation_date>
  <update_date>2020-04-14 22:47:55 UTC</update_date>
  <accession>BMDB0000637</accession>
  <secondary_accessions>
    <accession>BMDB00637</accession>
  </secondary_accessions>
  <name>Chenodeoxycholic acid glycine conjugate</name>
  <description/>
  <synonyms>
    <synonym>Chenodeoxycholate glycine conjugate</synonym>
    <synonym>Chenodeoxycholic acid glycine conjugic acid</synonym>
    <synonym>(23R)-Hydroxychenodeoxycholylglycine</synonym>
    <synonym>12-Deoxycholylglycine</synonym>
    <synonym>12-Desoxycholylglycine</synonym>
    <synonym>3a,7a-Dihydroxy-N-(carboxymethyl)-5b-cholan-24-amide</synonym>
    <synonym>Chenodeoxycholylglycine</synonym>
    <synonym>Glycine chenodeoxycholate</synonym>
    <synonym>Glycochenodeoxycholate</synonym>
    <synonym>Glycochenodeoxycholic acid</synonym>
    <synonym>Glycylchenodeoxycholate</synonym>
    <synonym>Glycylchenodeoxycholic acid</synonym>
    <synonym>N-(3a,7a-Dihydroxy-5b-cholan-24-oyl)-glycine</synonym>
    <synonym>N-(Carboxymethyl)-3a,7a-dihydroxy-5b-cholan-24-amide</synonym>
    <synonym>Acid, glycochenodeoxycholic</synonym>
    <synonym>Chenodeoxycholate, glycine</synonym>
    <synonym>3alpha,7alpha-Dihydroxy-N-(carboxymethyl)-5beta-cholan-24-amide</synonym>
    <synonym>3α,7α-Dihydroxy-N-(carboxymethyl)-5β-cholan-24-amide</synonym>
    <synonym>Chenodeoxycholic acid glycine conjugate</synonym>
    <synonym>Chenodeoxyglycocholic acid</synonym>
    <synonym>N-[(3alpha,5beta,7alpha)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine</synonym>
    <synonym>N-[(3α,5β,7α)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine</synonym>
  </synonyms>
  <chemical_formula>C26H43NO5</chemical_formula>
  <average_molecular_weight>449.6233</average_molecular_weight>
  <monisotopic_moleculate_weight>449.314123491</monisotopic_moleculate_weight>
  <iupac_name>2-[(4R)-4-[(2S,5R,7S,9R,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid</iupac_name>
  <traditional_iupac>[(4R)-4-[(2S,5R,7S,9R,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid</traditional_iupac>
  <cas_registry_number>640-79-9</cas_registry_number>
  <smiles>[H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[C@H](C)CCC(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19?,20?,21-,24?,25+,26-/m1/s1</inchi>
  <inchikey>GHCZAUBVMUEKKP-AHBZRTSYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Glycinated bile acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Dihydroxy bile acids, alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycinated bile acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>0.00315 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.12</value>
      <source>RODA,A ET AL. (1990)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4R)-4-[(2S,5R,7S,9R,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>449.6233</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>449.314123491</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[C@H](C)CCC(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H43NO5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19?,20?,21-,24?,25+,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GHCZAUBVMUEKKP-AHBZRTSYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>106.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>122.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>52.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>66087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>66088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>66089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>123558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>123559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>123560</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022157</foodb_id>
  <chemspider_id>17215984</chemspider_id>
  <kegg_id>C05466</kegg_id>
  <drugbank_id/>
  <pubchem_compound_id>22833540</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>45866</bigg_id>
  <wikipedia_id/>
  <metlin_id>5610</metlin_id>
  <synthesis_reference>Parmentier G; Eyssen H  Synthesis and characteristics of the specific monosulfates of chenodeoxycholate, deoxycholate and their taurine or glycine conjugates.  Steroids  (1977),  30(5),  583-90.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:04 UTC</creation_date>
  <update_date>2020-04-15 22:36:52 UTC</update_date>
  <accession>BMDB0000638</accession>
  <secondary_accessions>
    <accession>BMDB00638</accession>
  </secondary_accessions>
  <name>Dodecanoic acid</name>
  <description>Dodecanoic acid, also known as dodecanoate or potassium laurate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Dodecanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Dodecanoic acid exists in all living species, ranging from bacteria to humans. Dodecanoic acid participates in a number of enzymatic reactions, within cattle. In particular, Dodecanoic acid and coenzyme A can be converted into lauroyl-CoA and L-carnitine; which is catalyzed by the enzyme carnitine O-palmitoyltransferase 2, mitochondrial. In addition, Dodecanoic acid can be converted into dodecanoic acid; which is catalyzed by the enzyme peroxisomal membrane protein 11C. In cattle, dodecanoic acid is involved in the metabolic pathway called the Beta oxidation OF very long chain fatty acids pathway. Dodecanoic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Undecanecarboxylic acid</synonym>
    <synonym>ABL</synonym>
    <synonym>C12 Fatty acid</synonym>
    <synonym>C12:0</synonym>
    <synonym>CH3-[CH2]10-COOH</synonym>
    <synonym>Coconut oil fatty acids</synonym>
    <synonym>DAO</synonym>
    <synonym>Dodecoic acid</synonym>
    <synonym>Dodecylcarboxylate</synonym>
    <synonym>Dodecylic acid</synonym>
    <synonym>Duodecyclic acid</synonym>
    <synonym>Duodecylic acid</synonym>
    <synonym>Lauric acid</synonym>
    <synonym>Laurinsaeure</synonym>
    <synonym>Laurostearic acid</synonym>
    <synonym>N-Dodecanoic acid</synonym>
    <synonym>Undecane-1-carboxylic acid</synonym>
    <synonym>Vulvic acid</synonym>
    <synonym>Dodecanoate</synonym>
    <synonym>1-Undecanecarboxylate</synonym>
    <synonym>Dodecoate</synonym>
    <synonym>Dodecylcarboxylic acid</synonym>
    <synonym>Dodecylate</synonym>
    <synonym>Duodecyclate</synonym>
    <synonym>Duodecylate</synonym>
    <synonym>Laate</synonym>
    <synonym>Laic acid</synonym>
    <synonym>Laurostearate</synonym>
    <synonym>N-Dodecanoate</synonym>
    <synonym>Undecane-1-carboxylate</synonym>
    <synonym>Vulvate</synonym>
    <synonym>Aliphat no. 4</synonym>
    <synonym>Edenor C 1298-100</synonym>
    <synonym>Emery 651</synonym>
    <synonym>Hystrene 9512</synonym>
    <synonym>Kortacid 1299</synonym>
    <synonym>Laurate</synonym>
    <synonym>Lunac L 70</synonym>
    <synonym>Lunac L 98</synonym>
    <synonym>Neo-fat 12</synonym>
    <synonym>Neo-fat 12-43</synonym>
    <synonym>Nissan naa 122</synonym>
    <synonym>Philacid 1200</synonym>
    <synonym>Prifac 2920</synonym>
    <synonym>Univol u 314</synonym>
    <synonym>1-Dodecanoic acid</synonym>
    <synonym>FA(12:0)</synonym>
  </synonyms>
  <chemical_formula>C12H24O2</chemical_formula>
  <average_molecular_weight>200.3178</average_molecular_weight>
  <monisotopic_moleculate_weight>200.177630012</monisotopic_moleculate_weight>
  <iupac_name>dodecanoic acid</iupac_name>
  <traditional_iupac>lauric acid</traditional_iupac>
  <cas_registry_number>143-07-7</cas_registry_number>
  <smiles>CCCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)</inchi>
  <inchikey>POULHZVOKOAJMA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Saturated fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>medium-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>44 - 46 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.00481 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.6</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>dodecanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>200.3178</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>200.177630012</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H24O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>POULHZVOKOAJMA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>58.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Beta Oxidation of Very Long Chain Fatty Acids</name>
      <smpdb_id>SMP0087259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087266</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>871</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438033</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by infra-red spectroscopy and silieic acid columns</comment>
      <references>
        <reference>
          <reference_text>Laura Evans, Stuart Patton, R.D. McCarthy. Fatty Acid Composition of the Lipid Fractions from Bovine Serum Lipoproteins. J. Dairy Science (1961) 44(3) 475-482   doi: 10.3168/jds.S0022-0302(61)89765-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9.8 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9.4 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2446.11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2496.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>599.0481</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1297.938</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>599.0481</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6689.37</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.2 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6290.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5740.88</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19.97 +/- 2.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk from a Danish Holstein herd by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21.06 +/- 2.77</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised whole milk (3.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.13 +/- 0.19</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised semi skimmed milk (1.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.33 +/- 0.74</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised skimmed milk (0.1% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17.42 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
          <pubmed_id>1779072</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5990.475 +/- 1996.825</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
          <pubmed_id>16899705</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>26.0586 +/- 0.42</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Catrienus De Jong Herman T. Badings. Determination of free fatty acids in milk and cheese procedures for extraction, clean up, and capillary gas chromatographic analysis. Journal of High Resolution Chromatography Volume 13, Issue 2, 1990</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>48.5 +/- 23.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Fat content of plain milk wasn't specified in the reference. 3.25% is an estimate.</comment>
      <references>
        <reference>
          <reference_text>Lu CY, Wu HL, Chen SH, Kou HS, Wu SM: Simple and sensitive analysis of long-chain free fatty acids in milk by fluorogenic derivatization and high-performance liquid chromatography. J Agric Food Chem. 2002 Jan 2;50(1):71-3.</reference_text>
          <pubmed_id>11754544</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19.4 +/- 6.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Fat content of low-fat milk wasn't specified in the reference. 1-2% is an estimate.</comment>
      <references>
        <reference>
          <reference_text>Lu CY, Wu HL, Chen SH, Kou HS, Wu SM: Simple and sensitive analysis of long-chain free fatty acids in milk by fluorogenic derivatization and high-performance liquid chromatography. J Agric Food Chem. 2002 Jan 2;50(1):71-3.</reference_text>
          <pubmed_id>11754544</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6689.364 +/- 2146.587</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6190.158 +/- 1847.0632</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>33946.0597</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>41434.161</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>43430.988</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>53914.33</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Oocyte</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by CP9010 autosampler onto a capillary column within a CP9001 gas chromatograph in slaughtered cow ovaries.</comment>
      <references>
        <reference>
          <reference_text>McEvoy TG, Coull GD, Broadbent PJ, Hutchinson JS, Speake BK: Fatty acid composition of lipids in immature cattle, pig and sheep oocytes with intact zona pellucida. J Reprod Fertil. 2000 Jan;118(1):163-70.</reference_text>
          <pubmed_id>10793638</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02679</kegg_id>
  <chemspider_id>3756</chemspider_id>
  <drugbank_id>DB03017</drugbank_id>
  <foodb_id>FDB003010</foodb_id>
  <pubchem_compound_id>3893</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30805</chebi_id>
  <meta_cyc_id>DODECANOATE</meta_cyc_id>
  <knapsack_id>C00001221</knapsack_id>
  <wikipedia_id>Lauric_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>40351</bigg_id>
  <metlin_id>5611</metlin_id>
  <synthesis_reference>Stepanova, G. A.; Markevich, V. S.; Garanin, V. I.; Stychinskii, G. F.  Synthesis of lauric acid.    Khimicheskaya Promyshlennost (Moscow, Russian Federation)  (1974),   (12),  930.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
      <pubmed_id>16899705</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
      <pubmed_id>1779072</pubmed_id>
    </reference>
    <reference>
      <reference_text>Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.</reference_text>
      <pubmed_id>20855010</pubmed_id>
    </reference>
    <reference>
      <reference_text>Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93.</reference_text>
      <pubmed_id>5409465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026.</reference_text>
      <pubmed_id>29570652</pubmed_id>
    </reference>
    <reference>
      <reference_text>van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.</reference_text>
      <pubmed_id>28219465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
    </reference>
    <reference>
      <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
    </reference>
    <reference>
      <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01876</protein_accession>
      <name>Probable G-protein coupled receptor 84</name>
      <uniprot_id>Q2KI97</uniprot_id>
      <gene_name>GPR84</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:05 UTC</creation_date>
  <update_date>2020-03-13 16:22:41 UTC</update_date>
  <accession>BMDB0000639</accession>
  <secondary_accessions>
    <accession>BMDB00639</accession>
  </secondary_accessions>
  <name>Galactaric acid</name>
  <description/>
  <synonyms>
    <synonym>Acido galactarico</synonym>
    <synonym>Acido mucico</synonym>
    <synonym>Galactarsaeure</synonym>
    <synonym>Galactosaccharic acid</synonym>
    <synonym>Galaktarsaeure</synonym>
    <synonym>Mucic acid</synonym>
    <synonym>Mucinsaeure</synonym>
    <synonym>Saccharolactic acid</synonym>
    <synonym>Schleimsaeure</synonym>
    <synonym>D-Mucic acid</synonym>
    <synonym>D-Galactaric acid</synonym>
    <synonym>Galactarate</synonym>
    <synonym>Galactosaccharate</synonym>
    <synonym>Mucate</synonym>
    <synonym>Saccharolactate</synonym>
    <synonym>D-Mucate</synonym>
    <synonym>D-Galactarate</synonym>
    <synonym>(2R,3S,4R,5S)-2,3,4,5-Tetrahydroxyhexanedioate</synonym>
    <synonym>(2R,3S,4R,5S)-2,3,4,5-Tetrahydroxyhexanedioic acid</synonym>
    <synonym>Hexaric acid</synonym>
    <synonym>Meso-galactaric acid</synonym>
    <synonym>Schleimsaure</synonym>
    <synonym>Strontium galactarate mono-hydrate</synonym>
    <synonym>Galactaric acid, sodium salt</synonym>
  </synonyms>
  <chemical_formula>C6H10O8</chemical_formula>
  <average_molecular_weight>210.1388</average_molecular_weight>
  <monisotopic_moleculate_weight>210.037567296</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioic acid</iupac_name>
  <traditional_iupac>mucin</traditional_iupac>
  <cas_registry_number>526-99-8</cas_registry_number>
  <smiles>O[C@@H]([C@@H](O)[C@H](O)C(O)=O)[C@@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2+,3+,4-</inchi>
  <inchikey>DSLZVSRJTYRBFB-DUHBMQHGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Glucuronic acid derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Medium-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Glucuronic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>hexaric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>220 - 225 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>3.3 mg/mL at 14 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>210.1388</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>210.037567296</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]([C@@H](O)[C@H](O)C(O)=O)[C@@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2+,3+,4-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DSLZVSRJTYRBFB-DUHBMQHGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>155.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439259</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00879</kegg_id>
  <chemspider_id>2301286</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB001205</foodb_id>
  <pubchem_compound_id>3037582</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30852</chebi_id>
  <meta_cyc_id>D-GALACTARATE</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Galactaric_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5612</metlin_id>
  <synthesis_reference>Fauvarque, Jean-Francois; Guerin, Christophe; Petit, Serge; De Regis, Baynast.  Process and electrolytic cell for preparing galactaric acid.    Fr. Demande  (1994),     14 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:07 UTC</creation_date>
  <update_date>2020-03-13 16:22:41 UTC</update_date>
  <accession>BMDB0000640</accession>
  <secondary_accessions>
    <accession>BMDB00640</accession>
  </secondary_accessions>
  <name>Glucosan</name>
  <description/>
  <synonyms>
    <synonym>1,6-Anhydro-beta-D-glucose</synonym>
    <synonym>1,6-Anhydro-beta-glucopyranose</synonym>
    <synonym>1,6-Anhydroglucose</synonym>
    <synonym>Glucosan</synonym>
    <synonym>Leucoglucosan</synonym>
    <synonym>1,6-Anhydro-b-D-glucose</synonym>
    <synonym>1,6-Anhydro-β-D-glucose</synonym>
    <synonym>1,6-Anhydro-b-glucopyranose</synonym>
    <synonym>1,6-Anhydro-β-glucopyranose</synonym>
    <synonym>1,6-Anhydro-b-D-glucopyranose</synonym>
    <synonym>1,6-Anhydro-beta-D-glucopyranose</synonym>
    <synonym>1,6-Anhydro-beta-delta-glucopyranose</synonym>
    <synonym>1,6-Anhydro-beta-delta-glucose</synonym>
    <synonym>1,6-Anhydro-D-glucose</synonym>
    <synonym>1,6-Anhydro-delta-glucose</synonym>
    <synonym>6,8-Dioxabicyclo[3.2.1]octane b-D-glucopyranose deriv.</synonym>
    <synonym>6,8-Dioxabicyclo[3.2.1]octane b-delta-glucopyranose deriv.</synonym>
    <synonym>Anhydro-D-mannosan</synonym>
    <synonym>Anhydro-delta-mannosan</synonym>
    <synonym>L-Glucosan</synonym>
  </synonyms>
  <chemical_formula>C6H10O5</chemical_formula>
  <average_molecular_weight>162.1406</average_molecular_weight>
  <monisotopic_moleculate_weight>162.05282343</monisotopic_moleculate_weight>
  <iupac_name>(1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol</iupac_name>
  <traditional_iupac>levoglucosan</traditional_iupac>
  <cas_registry_number>498-07-7</cas_registry_number>
  <smiles>[H][C@@]12OC[C@@H](O1)[C@@H](O)[C@H](O)[C@H]2O</smiles>
  <inchi>InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2/t2-,3-,4+,5-,6-/m1/s1</inchi>
  <inchikey>TWNIBLMWSKIRAT-VFUOTHLCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Oxepanes</class>
    <sub_class/>
    <direct_parent>Oxepanes</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-dioxolanes</alternative_parent>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Meta-dioxolane</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Oxepane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>anhydrohexose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>162.1406</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>162.05282343</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12OC[C@@H](O1)[C@@H](O)[C@H](O)[C@H]2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2/t2-,3-,4+,5-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>TWNIBLMWSKIRAT-VFUOTHLCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>79.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448144</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id>9587432</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB005117</foodb_id>
  <pubchem_compound_id>2724705</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30997</chebi_id>
  <meta_cyc_id>CPD-12923</meta_cyc_id>
  <knapsack_id>C00007411</knapsack_id>
  <wikipedia_id>Levoglucosan</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5613</metlin_id>
  <synthesis_reference>Tanaka, Choji.  Anhydrosugars. I. Constitutions of anhydrosugars.    Memoirs of the College of Science, University of Kyoto, Series A  (1930),  13  239-53.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:08 UTC</creation_date>
  <update_date>2020-04-16 20:40:47 UTC</update_date>
  <accession>BMDB0000641</accession>
  <secondary_accessions>
    <accession>BMDB00641</accession>
  </secondary_accessions>
  <name>L-Glutamine</name>
  <description>L-Glutamine, also known as levoglutamide or Q, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-Glutamine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. It is used to reduce the acute complications of sickle cell disease in adult and pediatric patients 5 years of age and older [fda label]. L-Glutamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Glutamine exists in all living species, ranging from bacteria to humans. L-Glutamine can be converted into phenylacetylglutamine; which is mediated by the enzyme glycine N-acyltransferase. In cattle, L-glutamine is involved in the metabolic pathway called the phenylacetate metabolism pathway. L-Glutamine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2S)-2,5-Diamino-5-oxopentanoic acid</synonym>
    <synonym>(2S)-2-Amino-4-carbamoylbutanoic acid</synonym>
    <synonym>(S)-2,5-Diamino-5-oxopentanoic acid</synonym>
    <synonym>Glutamic acid 5-amide</synonym>
    <synonym>Glutamic acid amide</synonym>
    <synonym>GLUTAMINE</synonym>
    <synonym>L-(+)-Glutamine</synonym>
    <synonym>L-2-Aminoglutaramic acid</synonym>
    <synonym>L-Glutamic acid gamma-amide</synonym>
    <synonym>L-Glutamin</synonym>
    <synonym>L-Glutaminsaeure-5-amid</synonym>
    <synonym>Levoglutamide</synonym>
    <synonym>Q</synonym>
    <synonym>Endari</synonym>
    <synonym>Nutrestore</synonym>
    <synonym>(2S)-2,5-Diamino-5-oxopentanoate</synonym>
    <synonym>(2S)-2-Amino-4-carbamoylbutanoate</synonym>
    <synonym>(S)-2,5-Diamino-5-oxopentanoate</synonym>
    <synonym>Glutamate 5-amide</synonym>
    <synonym>Glutamate amide</synonym>
    <synonym>L-2-Aminoglutaramate</synonym>
    <synonym>L-Glutamate g-amide</synonym>
    <synonym>L-Glutamate gamma-amide</synonym>
    <synonym>L-Glutamate γ-amide</synonym>
    <synonym>L-Glutamic acid g-amide</synonym>
    <synonym>L-Glutamic acid γ-amide</synonym>
    <synonym>2-Aminoglutaramic acid</synonym>
    <synonym>Cebrogen</synonym>
    <synonym>gamma-Glutamine</synonym>
    <synonym>Glavamin</synonym>
    <synonym>Glumin</synonym>
    <synonym>L-2-Aminoglutaramidic acid</synonym>
    <synonym>L-Glutamic acid 5-amide</synonym>
    <synonym>L-Glutamid</synonym>
    <synonym>L-Glutamide</synonym>
    <synonym>Levoglutamid</synonym>
    <synonym>Levoglutamida</synonym>
    <synonym>Levoglutamidum</synonym>
    <synonym>Levoglutamina</synonym>
    <synonym>Polyglutamine</synonym>
    <synonym>Stimulina</synonym>
    <synonym>D-Glutamine</synonym>
    <synonym>D Glutamine</synonym>
    <synonym>L Glutamine</synonym>
  </synonyms>
  <chemical_formula>C5H10N2O3</chemical_formula>
  <average_molecular_weight>146.1445</average_molecular_weight>
  <monisotopic_moleculate_weight>146.069142196</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-carbamoylbutanoic acid</iupac_name>
  <traditional_iupac>L-glutamine</traditional_iupac>
  <cas_registry_number>56-85-9</cas_registry_number>
  <smiles>N[C@@H](CCC(N)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1</inchi>
  <inchikey>ZDXPYRJPNDTMRX-VKHMYHEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>glutamine</external_descriptor>
      <external_descriptor>glutamine family amino acid</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>185 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>41.3 mg/mL</value>
      <source>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.64</value>
      <source>CHMELIK,J ET AL. (1991)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-carbamoylbutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>146.1445</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>146.069142196</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCC(N)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZDXPYRJPNDTMRX-VKHMYHEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>106.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>33.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylacetate Metabolism</name>
      <smpdb_id>SMP0087208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Glutamine</name>
      <smpdb_id>SMP0119389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Succinate Signalling</name>
      <smpdb_id>SMP0120941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>881</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37669</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 24 male 17-22-month-old Charolais beef cattles.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>95-126</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in Holstein and Red-Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Imhasly S, Naegeli H, Baumann S, von Bergen M, Luch A, Jungnickel H, Potratz S, Gerspach C: Metabolomic biomarkers correlating with hepatic lipidosis in dairy cows. BMC Vet Res. 2014 Jun 2;10:122. doi: 10.1186/1746-6148-10-122.</reference_text>
          <pubmed_id>24888604</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>35.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>330+/-42</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>246-260</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>1433+/-231</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>1911-2576</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By HPLC with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Miles ED, McBride BW, Jia Y, Liao SF, Boling JA, Bridges PJ, Matthews JC: Glutamine synthetase and alanine transaminase expression are decreased in livers of aged vs. young beef cows and GS can be upregulated by 17beta-estradiol implants. J Anim Sci. 2015 Sep;93(9):4500-9. doi: 10.2527/jas.2015-9294.</reference_text>
          <pubmed_id>26440349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>2841+/-828</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.0 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1148.18 +/- 201.58</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1508.29 +/- 185.39</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1582.02 +/- 237.99</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>412-1820</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>9.33+/-0.96</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>6.47+/-1.36</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>6.06+/-0.68</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>6.18+/-0.65</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>476.93 +/- 64.67</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>910</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>277-443</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>3051-4834</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>830.5 +/- 251.38</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>945.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>993.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>907.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>830.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>946 +/- 239</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>994 +/- 358</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>907 +/- 255</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>831 +/- 252</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>831 +/- 251</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>2492+/-668</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>1517+/-338</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00064</kegg_id>
  <chemspider_id>5746</chemspider_id>
  <drugbank_id>DB00130</drugbank_id>
  <foodb_id>FDB030965</foodb_id>
  <pubchem_compound_id>5961</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18050</chebi_id>
  <meta_cyc_id>GLN</meta_cyc_id>
  <knapsack_id>C00001359</knapsack_id>
  <wikipedia_id>Glutamine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33714</bigg_id>
  <metlin_id>5614</metlin_id>
  <synthesis_reference>Jiao, Qingcai; Qian, Shaosong; Chen, Ran; Wu, Xiaoyan.  Synthesis of L-glutamine.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2005),  7 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00148</protein_accession>
      <name>Glutamine synthetase</name>
      <uniprot_id>P15103</uniprot_id>
      <gene_name>GLUL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00563</protein_accession>
      <name>Asparagine synthetase [glutamine-hydrolyzing]</name>
      <uniprot_id>Q1LZA3</uniprot_id>
      <gene_name>ASNS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00827</protein_accession>
      <name>Glucosamine--fructose-6-phosphate aminotransferase [isomerizing] 2</name>
      <uniprot_id>Q08DQ2</uniprot_id>
      <gene_name>GFPT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00850</protein_accession>
      <name>Glutamyl-tRNA(Gln) amidotransferase subunit A homolog</name>
      <uniprot_id>Q29RP9</uniprot_id>
      <gene_name>QRSL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00851</protein_accession>
      <name>Protein-glutamine gamma-glutamyltransferase 2</name>
      <uniprot_id>P51176</uniprot_id>
      <gene_name>TGM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00852</protein_accession>
      <name>Glutamine-dependent NAD(+) synthetase</name>
      <uniprot_id>Q3ZBF0</uniprot_id>
      <gene_name>NADSYN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00853</protein_accession>
      <name>Glutaminyl-tRNA synthetase</name>
      <uniprot_id>Q3MHH4</uniprot_id>
      <gene_name>QARS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00854</protein_accession>
      <name>Coagulation factor XIII A chain</name>
      <uniprot_id>P12260</uniprot_id>
      <gene_name>F13A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02092</protein_accession>
      <name>Sodium-coupled neutral amino acid transporter 5</name>
      <uniprot_id>Q5E9S9</uniprot_id>
      <gene_name>SLC38A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02093</protein_accession>
      <name>Solute carrier family 38 member 1</name>
      <uniprot_id>B0LSH3</uniprot_id>
      <gene_name>SLC38A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02094</protein_accession>
      <name>Na+ and H+ coupled amino acid transport system N1</name>
      <uniprot_id>Q866Q8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02095</protein_accession>
      <name>SLC38A3 protein</name>
      <uniprot_id>Q3MHG9</uniprot_id>
      <gene_name>SLC38A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02096</protein_accession>
      <name>Polyglutamine-binding protein 1</name>
      <uniprot_id>Q2HJC9</uniprot_id>
      <gene_name>PQBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02097</protein_accession>
      <name>Solute carrier family 38 member 3</name>
      <uniprot_id>B0LSH5</uniprot_id>
      <gene_name>SLC38A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02098</protein_accession>
      <name>Solute carrier family 38, member 3</name>
      <uniprot_id>Q5BIN7</uniprot_id>
      <gene_name>SLC38A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:09 UTC</creation_date>
  <update_date>2020-03-19 22:01:59 UTC</update_date>
  <accession>BMDB0000642</accession>
  <secondary_accessions>
    <accession>BMDB00642</accession>
  </secondary_accessions>
  <name>Erythronilic acid</name>
  <description/>
  <synonyms>
    <synonym>Erythronilate</synonym>
    <synonym>(-)-Erythro-nilic acid</synonym>
    <synonym>(2R,3S)-3-Hydroxy-2-methylbutanoic acid</synonym>
    <synonym>(2R,3S)-3-Hydroxy-2-methylbutyric acid</synonym>
    <synonym>HMBA</synonym>
    <synonym>Erythronilic acid</synonym>
  </synonyms>
  <chemical_formula>C5H10O3</chemical_formula>
  <average_molecular_weight>118.1311</average_molecular_weight>
  <monisotopic_moleculate_weight>118.062994186</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S)-3-hydroxy-2-methylbutanoic acid</iupac_name>
  <traditional_iupac>erythronilate</traditional_iupac>
  <cas_registry_number>66729-02-0</cas_registry_number>
  <smiles>C[C@H](O)[C@@H](C)C(O)=O</smiles>
  <inchi>InChI=1S/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t3-,4+/m1/s1</inchi>
  <inchikey>VEXDRERIMPLZLU-DMTCNVIQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S)-3-hydroxy-2-methylbutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>118.1311</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>118.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](O)[C@@H](C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O3/c1-3(4(2)6)5(7)8/h3-4,6H,1-2H3,(H,7,8)/t3-,4+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VEXDRERIMPLZLU-DMTCNVIQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB022158</foodb_id>
  <chemspider_id>9990501</chemspider_id>
  <pdbe_id/>
  <chebi_id/>
  <pubchem_compound_id>11815846</pubchem_compound_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Sugiyama, Yoshio; Miya, Hiroyuki; Kawada, Mitsuru.  Process for producing optically active 3-hydroxy-2-methylbutyrates.    PCT Int. Appl.  (1991),     31 pp. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:10 UTC</creation_date>
  <update_date>2020-04-15 22:14:13 UTC</update_date>
  <accession>BMDB0000643</accession>
  <secondary_accessions>
    <accession>BMDB00643</accession>
  </secondary_accessions>
  <name>Coproporphyrin I</name>
  <description>Coproporphyrin I belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure. Coproporphyrin I is possibly soluble (in water) and a very strong basic compound (based on its pKa). Coproporphyrin I exists in all eukaryotes, ranging from yeast to humans. In cattle, coproporphyrin i is involved in the metabolic pathway called the porphyrin metabolism pathway. Coproporphyrin I is a potentially toxic compound.</description>
  <synonyms>
    <synonym>3,8,13,17-Tetramethylporphyrin-2,7,12,18-tetrapropanoic acid</synonym>
    <synonym>3,8,13,17-Tetramethylporphyrin-2,7,12,18-tetrapropanoate</synonym>
    <synonym>3,8,13,18-Tetramethyl-2,7,12,17-porphinetetrapropionate</synonym>
    <synonym>3,8,13,18-Tetramethyl-2,7,12,17-porphinetetrapropionic acid</synonym>
    <synonym>3,8,13,18-Tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionate</synonym>
    <synonym>3,8,13,18-Tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionic acid</synonym>
  </synonyms>
  <chemical_formula>C36H38N4O8</chemical_formula>
  <average_molecular_weight>654.7089</average_molecular_weight>
  <monisotopic_moleculate_weight>654.268964212</monisotopic_moleculate_weight>
  <iupac_name>3-[9,14,19-tris(2-carboxyethyl)-5,10,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[9,14,19-tris(2-carboxyethyl)-5,10,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>531-14-6</cas_registry_number>
  <smiles>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4C)/C(CCC(O)=O)=C3C</smiles>
  <inchi>InChI=1S/C36H38N4O8/c1-17-21(5-9-33(41)42)29-14-26-19(3)23(7-11-35(45)46)31(39-26)16-28-20(4)24(8-12-36(47)48)32(40-28)15-27-18(2)22(6-10-34(43)44)30(38-27)13-25(17)37-29/h13-16,37,40H,5-12H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)/b25-13-,26-14-,27-15-,28-16-,29-14-,30-13-,31-16-,32-15-</inchi>
  <inchikey>VORBHEGMEBOMMB-JRHDEHKPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[9,14,19-tris(2-carboxyethyl)-5,10,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>654.7089</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>654.268964212</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4C)/C(CCC(O)=O)=C3C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C36H38N4O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C36H38N4O8/c1-17-21(5-9-33(41)42)29-14-26-19(3)23(7-11-35(45)46)31(39-26)16-28-20(4)24(8-12-36(47)48)32(40-28)15-27-18(2)22(6-10-34(43)44)30(38-27)13-25(17)37-29/h13-16,37,40H,5-12H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)/b25-13-,26-14-,27-15-,28-16-,29-14-,30-13-,31-16-,32-15-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VORBHEGMEBOMMB-JRHDEHKPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>206.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>176.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>74.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15739</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>16736701</chemspider_id>
  <drugbank_id>DB03727</drugbank_id>
  <kegg_id>C05769</kegg_id>
  <chebi_id>28421</chebi_id>
  <pubchem_compound_id/>
  <foodb_id>FDB022159</foodb_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5616</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Schonheyder, Fritz.  The formation of coproporphyrin I and hemoglobin during embryonic life.    Journal of Biological Chemistry  (1938),  123  491-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:11 UTC</creation_date>
  <update_date>2020-04-15 22:14:14 UTC</update_date>
  <accession>BMDB0000644</accession>
  <secondary_accessions>
    <accession>BMDB00644</accession>
  </secondary_accessions>
  <name>Coproporphyrin IV</name>
  <description/>
  <synonyms>
    <synonym>3,8,12,17-Tetramethyl-2,7,13,18-porphinetetrapropionate</synonym>
    <synonym>3,8,12,17-Tetramethyl-2,7,13,18-porphinetetrapropionic acid</synonym>
    <synonym>3-[10,15,19-Tris(2-carboxyethyl)-5,9,14,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C36H38N4O8</chemical_formula>
  <average_molecular_weight>654.7089</average_molecular_weight>
  <monisotopic_moleculate_weight>654.268964212</monisotopic_moleculate_weight>
  <iupac_name>3-[10,15,19-tris(2-carboxyethyl)-5,9,14,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[10,15,19-tris(2-carboxyethyl)-5,9,14,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>18372-11-7</cas_registry_number>
  <smiles>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)/C(CCC(O)=O)=C3C</smiles>
  <inchi>InChI=1S/C36H38N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)23(7-11-35(45)46)31(39-27)16-32-24(8-12-36(47)48)20(4)28(40-32)15-30-22(6-10-34(43)44)18(2)26(38-30)13-25(17)37-29/h13-16,37,40H,5-12H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-</inchi>
  <inchikey>WEUFSMQSXVJGBC-UJJXFSCMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[10,15,19-tris(2-carboxyethyl)-5,9,14,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>654.7089</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>654.268964212</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)/C(CCC(O)=O)=C3C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C36H38N4O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C36H38N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)23(7-11-35(45)46)31(39-27)16-32-24(8-12-36(47)48)20(4)28(40-32)15-30-22(6-10-34(43)44)18(2)26(38-30)13-25(17)37-29/h13-16,37,40H,5-12H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WEUFSMQSXVJGBC-UJJXFSCMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>206.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>176.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>73.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326301</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022160</foodb_id>
  <drugbank_id/>
  <chemspider_id>16736703</chemspider_id>
  <pdbe_id/>
  <chebi_id/>
  <pubchem_compound_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5617</metlin_id>
  <synthesis_reference>Jacob K; Egeler E; Hennel B; Luppa P  Coproporphyrin isomers II and IV are normal constituents of human urine.    Journal of clinical chemistry and clinical biochemistry. Zeitschrift fur klinische Chemie und klinische Biochemie  (1989),  27(9),  659-61.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:12 UTC</creation_date>
  <update_date>2020-04-16 22:56:33 UTC</update_date>
  <accession>BMDB0000645</accession>
  <secondary_accessions>
    <accession>BMDB00645</accession>
  </secondary_accessions>
  <name>Galactose 1-phosphate</name>
  <description>Galactose 1-phosphate, also known as delta-glucose 1-phosphate or cori ester, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Galactose 1-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Galactose 1-phosphate exists in all living species, ranging from bacteria to humans. Galactose 1-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Uridine diphosphate glucose and galactose 1-phosphate can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate through its interaction with the enzyme galactose-1-phosphate uridylyltransferase. Furthermore, Galactose 1-phosphate can be biosynthesized from D-galactose through the action of the enzyme galactokinase. Finally, Uridine diphosphate glucose and galactose 1-phosphate can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate; which is mediated by the enzyme galactose-1-phosphate uridylyltransferase. In cattle, galactose 1-phosphate is involved in a couple of metabolic pathways, which include the nucleotide sugars metabolism pathway and lactose synthesis pathway. Galactose 1-phosphate is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-O-Phosphono-alpha-D-galactopyranose</synonym>
    <synonym>alpha-D-Gal-1-p</synonym>
    <synonym>alpha-D-Galactopyranose 1-phosphate</synonym>
    <synonym>alpha-D-Galactopyranose, 1-(dihydrogen phosphate)</synonym>
    <synonym>alpha-D-Galactopyranosyl phosphate</synonym>
    <synonym>alpha-D-Galactosyl phosphate</synonym>
    <synonym>Galactose-1-phosphate</synonym>
    <synonym>1-O-Phosphono-a-D-galactopyranose</synonym>
    <synonym>1-O-Phosphono-α-D-galactopyranose</synonym>
    <synonym>a-D-Gal-1-p</synonym>
    <synonym>Α-D-gal-1-p</synonym>
    <synonym>a-D-Galactopyranose 1-phosphate</synonym>
    <synonym>a-D-Galactopyranose 1-phosphoric acid</synonym>
    <synonym>alpha-D-Galactopyranose 1-phosphoric acid</synonym>
    <synonym>Α-D-galactopyranose 1-phosphate</synonym>
    <synonym>Α-D-galactopyranose 1-phosphoric acid</synonym>
    <synonym>a-D-Galactopyranose, 1-(dihydrogen phosphate)</synonym>
    <synonym>a-D-Galactopyranose, 1-(dihydrogen phosphoric acid)</synonym>
    <synonym>alpha-D-Galactopyranose, 1-(dihydrogen phosphoric acid)</synonym>
    <synonym>Α-D-galactopyranose, 1-(dihydrogen phosphate)</synonym>
    <synonym>Α-D-galactopyranose, 1-(dihydrogen phosphoric acid)</synonym>
    <synonym>a-D-Galactopyranosyl phosphate</synonym>
    <synonym>a-D-Galactopyranosyl phosphoric acid</synonym>
    <synonym>alpha-D-Galactopyranosyl phosphoric acid</synonym>
    <synonym>Α-D-galactopyranosyl phosphate</synonym>
    <synonym>Α-D-galactopyranosyl phosphoric acid</synonym>
    <synonym>a-D-Galactosyl phosphate</synonym>
    <synonym>a-D-Galactosyl phosphoric acid</synonym>
    <synonym>alpha-D-Galactosyl phosphoric acid</synonym>
    <synonym>Α-D-galactosyl phosphate</synonym>
    <synonym>Α-D-galactosyl phosphoric acid</synonym>
    <synonym>Galactose-1-phosphoric acid</synonym>
    <synonym>Galactose 1-phosphoric acid</synonym>
    <synonym>a-D-Galactose-1-phosphate</synonym>
    <synonym>a-D-Galactose-1-phosphoric acid</synonym>
    <synonym>alpha-D-Galactose-1-phosphoric acid</synonym>
    <synonym>Α-D-galactose-1-phosphate</synonym>
    <synonym>Α-D-galactose-1-phosphoric acid</synonym>
    <synonym>Galactose-1-phosphate, (beta-L-gal)-isomer</synonym>
    <synonym>Galactose-1-phosphate, 14C-labeled</synonym>
    <synonym>Galactose-1-phosphate, disilver (+1) salt, (D-gal)-isomer</synonym>
    <synonym>Galactose-1-phosphate, sodium salt</synonym>
    <synonym>Galactose-1-phosphate, (beta-D-gal)-isomer</synonym>
    <synonym>1-(Dihydrogen phosphate) galactitol</synonym>
    <synonym>1-Phosphate a-D-galactopyranose</synonym>
    <synonym>a-D-1-(Dihydrogen phosphate) galactopyranose</synonym>
    <synonym>a-D-Galactose 1-phosphate</synonym>
    <synonym>alpha-D-1-(Dihydrogen phosphate) galactopyranose</synonym>
    <synonym>alpha-D-Galactose 1-phosphate</synonym>
    <synonym>D-Galactose 1-phosphate</synonym>
    <synonym>Galactopyranose 1-phosphate</synonym>
    <synonym>D-Galactopyranose 1-phosphate</synonym>
    <synonym>D-Galactopyranose 1-phosphoric acid</synonym>
    <synonym>D-Galactose 1-phosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C6H13O9P</chemical_formula>
  <average_molecular_weight>260.1358</average_molecular_weight>
  <monisotopic_moleculate_weight>260.029718526</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>galactose 1 phosphate</traditional_iupac>
  <cas_registry_number>2255-14-3</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3+,4+,5-,6-/m1/s1</inchi>
  <inchikey>HXXFSFRBOHSIMQ-FPRJBGLDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharide phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D-galactopyranose 1-phosphate</external_descriptor>
      <external_descriptor>alpha-D-hexose 1-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>260.1358</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>260.029718526</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3+,4+,5-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HXXFSFRBOHSIMQ-FPRJBGLDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>156.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440089</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>561 - 2070</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from 20 healthy Holstein Friesian dairy cows </comment>
      <references>
        <reference>
          <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
          <pubmed_id>23738862</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00446</kegg_id>
  <chemspider_id/>
  <drugbank_id>DB02317</drugbank_id>
  <foodb_id>FDB001159</foodb_id>
  <pubchem_compound_id>123912</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17973</chebi_id>
  <meta_cyc_id>GALACTOSE-1P</meta_cyc_id>
  <knapsack_id>C00007391</knapsack_id>
  <wikipedia_id>Galactose_1-phosphate</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Chen Jie; Yager Claire; Reynolds Robert; Palmieri Michael; Segal Stanton  Erythrocyte galactose 1-phosphate quantified by isotope-dilution gas chromatography-mass spectrometry.    Clinical chemistry  (2002),  48(4),  604-12.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
      <pubmed_id>23738862</pubmed_id>
    </reference>
    <reference>
      <reference_text>Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26.</reference_text>
      <pubmed_id>27236769</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00957</protein_accession>
      <name>Galactose-1-phosphate uridylyltransferase</name>
      <uniprot_id>Q0V7N7</uniprot_id>
      <gene_name>GALT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00959</protein_accession>
      <name>Galactose-1-phosphate uridylyltransferase</name>
      <uniprot_id>Q58CX1</uniprot_id>
      <gene_name>GALT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:14 UTC</creation_date>
  <update_date>2020-04-14 22:47:57 UTC</update_date>
  <accession>BMDB0000646</accession>
  <secondary_accessions>
    <accession>BMDB00646</accession>
  </secondary_accessions>
  <name>L-Arabinose</name>
  <description>L-Arabinose, also known as L-arabinopyranose, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. L-Arabinose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. L-Arabinose exists in all living species, ranging from bacteria to humans. L-Arabinose has been found to be associated with several diseases known as eosinophilic esophagitis and colorectal cancer; also l-arabinose has been linked to the inborn metabolic disorders including ribose-5-phosphate isomerase deficiency.</description>
  <synonyms>
    <synonym>L-Arabinopyranose</synonym>
    <synonym>Arabinose</synonym>
    <synonym>L-(+)-Arabinose</synonym>
    <synonym>L Arabinose</synonym>
  </synonyms>
  <chemical_formula>C5H10O5</chemical_formula>
  <average_molecular_weight>150.1299</average_molecular_weight>
  <monisotopic_moleculate_weight>150.05282343</monisotopic_moleculate_weight>
  <iupac_name>(3R,4S,5S)-oxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>L-arabinopyranose</traditional_iupac>
  <cas_registry_number>5328-37-0</cas_registry_number>
  <smiles>O[C@H]1COC(O)[C@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4+,5?/m0/s1</inchi>
  <inchikey>SRBFZHDQGSBBOR-HWQSCIPKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Aldoses</external_descriptor>
      <external_descriptor>L-arabinose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>158 - 160 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>500.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.02</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4S,5S)-oxane-2,3,4,5-tetrol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>150.1299</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>150.05282343</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1COC(O)[C@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4+,5?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SRBFZHDQGSBBOR-HWQSCIPKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>90.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>29.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1399</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By GC-TOFMS and UPLC-QTOFMS</comment>
      <references>
        <reference>
          <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
          <pubmed_id>27999311</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
          <pubmed_id>14168161</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00259</kegg_id>
  <chemspider_id>388335</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB012306</foodb_id>
  <pubchem_compound_id>439195</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17535</chebi_id>
  <meta_cyc_id/>
  <knapsack_id>C00041349</knapsack_id>
  <wikipedia_id>Arabinose</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34429</bigg_id>
  <metlin_id>5474</metlin_id>
  <synthesis_reference>Whistler, Roy L.; Schweiger, Richard. Preparation of D-arabinose from D-glucose with hypochlorite. Journal of the American Chemical Society (1959), 81 5190-2.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
      <pubmed_id>14168161</pubmed_id>
    </reference>
    <reference>
      <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
      <pubmed_id>27999311</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:15 UTC</creation_date>
  <update_date>2020-04-16 20:37:29 UTC</update_date>
  <accession>BMDB0000648</accession>
  <secondary_accessions>
    <accession>BMDB00648</accession>
  </secondary_accessions>
  <name>Galactosylsphingosine</name>
  <description/>
  <synonyms>
    <synonym>(2S,3R,4E)-2-Amino-1-(beta-D-galactopyranosyloxy)-3-hydroxyoctadec-4-ene</synonym>
    <synonym>1-beta-D-Galactosphingosine</synonym>
    <synonym>1-beta-D-Galactosylsphingosine</synonym>
    <synonym>1-O-beta-D-Galactopyranosylsphingosine</synonym>
    <synonym>1-O-beta-D-Galactosylsphingosine</synonym>
    <synonym>beta-Psychosine</synonym>
    <synonym>O-Galactosylsphingosine</synonym>
    <synonym>Sphingosine galactoside</synonym>
    <synonym>(2S,3R,4E)-2-Amino-1-(b-D-galactopyranosyloxy)-3-hydroxyoctadec-4-ene</synonym>
    <synonym>(2S,3R,4E)-2-Amino-1-(β-D-galactopyranosyloxy)-3-hydroxyoctadec-4-ene</synonym>
    <synonym>1-b-D-Galactosphingosine</synonym>
    <synonym>1-b-D-Galactosylsphingosine</synonym>
    <synonym>1-O-b-D-Galactopyranosylsphingosine</synonym>
    <synonym>1-O-b-D-Galactosylsphingosine</synonym>
    <synonym>b-Psychosine</synonym>
    <synonym>Galactoside, sphingosine</synonym>
    <synonym>Psychosine</synonym>
    <synonym>Erythro-psychosine</synonym>
    <synonym>Galactosylsphingosine</synonym>
  </synonyms>
  <chemical_formula>C24H47NO7</chemical_formula>
  <average_molecular_weight>461.64</average_molecular_weight>
  <monisotopic_moleculate_weight>461.335252857</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4S,5R,6R)-2-{[(4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>(2R,3R,4S,5R,6R)-2-{[(4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</traditional_iupac>
  <cas_registry_number>2238-90-6</cas_registry_number>
  <smiles>CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/b15-14+/t18-,19+,20+,21-,22-,23+,24+/m0/s1</inchi>
  <inchikey>HHJTWTPUPVQKNA-PIIMIWFASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Sphingolipids</class>
    <sub_class>Glycosphingolipids</sub_class>
    <direct_parent>Glycosphingolipids</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Alkyl glycosides</alternative_parent>
      <alternative_parent>Fatty acyl glycosides of mono- and disaccharides</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl glycoside</substituent>
      <substituent>Amine</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty acyl glycoside</substituent>
      <substituent>Fatty acyl glycoside of mono- or disaccharide</substituent>
      <substituent>Glycosphingolipid</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Basic glycosphingolipids</external_descriptor>
      <external_descriptor>Sphingoid base analogs</external_descriptor>
      <external_descriptor>glycosylsphingoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R,4S,5R,6R)-2-{[(4E)-2-amino-3-hydroxyoctadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>461.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>461.335252857</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H47NO7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/b15-14+/t18-,19+,20+,21-,22-,23+,24+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HHJTWTPUPVQKNA-PIIMIWFASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>145.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>124.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>54.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01747</kegg_id>
  <chemspider_id>4444111</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB022161</foodb_id>
  <pubchem_compound_id>5280458</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16874</chebi_id>
  <meta_cyc_id>PSYCHOSINE</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Psychosine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5620</metlin_id>
  <synthesis_reference>Shapiro, David; Rachaman, Eliezer S.; Sheradsky, Tuvia. Synthetic studies on sphingolipids. X. Synthesis of psychosine. Journal of the American Chemical Society (1964), 86(20), 4472-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:16 UTC</creation_date>
  <update_date>2020-03-13 16:22:46 UTC</update_date>
  <accession>BMDB0000649</accession>
  <secondary_accessions>
    <accession>BMDB00649</accession>
  </secondary_accessions>
  <name>Clionasterol</name>
  <description/>
  <synonyms>
    <synonym>(3beta,24S)-Stigmast-5-en-3-ol</synonym>
    <synonym>22,23-Dihydroporiferasterol</synonym>
    <synonym>24-Ethylcholest-5-en-3 beta-ol</synonym>
    <synonym>24beta-Ethyl-5-cholesten-3beta-ol</synonym>
    <synonym>24beta-Ethylcholesterol</synonym>
    <synonym>24S-Ethylcholest-5-en-3beta-ol</synonym>
    <synonym>beta-Dihydrofucosterol</synonym>
    <synonym>gamma-Sitosterol</synonym>
    <synonym>Poriferast-5-en-3beta-ol</synonym>
    <synonym>(3b,24S)-Stigmast-5-en-3-ol</synonym>
    <synonym>(3Β,24S)-stigmast-5-en-3-ol</synonym>
    <synonym>24-Ethylcholest-5-en-3 b-ol</synonym>
    <synonym>24-Ethylcholest-5-en-3 β-ol</synonym>
    <synonym>24b-Ethyl-5-cholesten-3b-ol</synonym>
    <synonym>24Β-ethyl-5-cholesten-3β-ol</synonym>
    <synonym>24b-Ethylcholesterol</synonym>
    <synonym>24Β-ethylcholesterol</synonym>
    <synonym>24S-Ethylcholest-5-en-3b-ol</synonym>
    <synonym>24S-Ethylcholest-5-en-3β-ol</synonym>
    <synonym>b-Dihydrofucosterol</synonym>
    <synonym>Β-dihydrofucosterol</synonym>
    <synonym>g-Sitosterol</synonym>
    <synonym>Γ-sitosterol</synonym>
    <synonym>Poriferast-5-en-3b-ol</synonym>
    <synonym>Poriferast-5-en-3β-ol</synonym>
    <synonym>24b-Ethylcholest-5-en-3b-ol</synonym>
    <synonym>24-Ethylcholesterol</synonym>
    <synonym>3beta-Stigmast-5-en-3-ol</synonym>
    <synonym>Sitosterol</synonym>
    <synonym>Sitosterol, (3beta,24xi)-isomer</synonym>
    <synonym>Sitosterol, 26-(14)C-labeled</synonym>
    <synonym>3beta-Sitosterol</synonym>
    <synonym>Harzol</synonym>
    <synonym>beta-Sitosterol</synonym>
    <synonym>Sitosterol, (3beta)-isomer</synonym>
  </synonyms>
  <chemical_formula>C29H50O</chemical_formula>
  <average_molecular_weight>414.7067</average_molecular_weight>
  <monisotopic_moleculate_weight>414.386166222</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol</iupac_name>
  <traditional_iupac>(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol</traditional_iupac>
  <cas_registry_number>83-47-6</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CC[C@H](CC)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21+,23+,24+,25-,26+,27+,28+,29-/m1/s1</inchi>
  <inchikey>KZJWDPNRJALLNS-FBZNIEFRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Stigmastanes and derivatives</sub_class>
    <direct_parent>Stigmastanes and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>C24-propyl sterols and derivatives</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Triterpenoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>C24-propyl-sterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Stigmastane-skeleton</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Stigmasterols and C24-ethyl derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>147 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>414.7067</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>414.386166222</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CC[C@H](CC)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C29H50O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21+,23+,24+,25-,26+,27+,28+,29-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KZJWDPNRJALLNS-FBZNIEFRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>129.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>54.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346545</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>402901</chemspider_id>
  <foodb_id>FDB012131</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>457801</pubchem_compound_id>
  <kegg_id>C19654</kegg_id>
  <pdbe_id/>
  <chebi_id>132823</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00023769</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5621</metlin_id>
  <synthesis_reference>Kind, C. Albert; Bergmann, Werner.  Marine products. X. Clionasterol.    Journal of Organic Chemistry  (1942),  7  341-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:17 UTC</creation_date>
  <update_date>2020-04-14 22:47:57 UTC</update_date>
  <accession>BMDB0000650</accession>
  <secondary_accessions>
    <accession>BMDB00650</accession>
  </secondary_accessions>
  <name>D-Alpha-aminobutyric acid</name>
  <description>D-alpha-Aminobutyric acid, also known as a-aminobutyrate or (R)-2-aminobutanoic acid, belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. D-alpha-Aminobutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.</description>
  <synonyms>
    <synonym>(2R)-2-Aminobutyric acid</synonym>
    <synonym>(R)-2-Aminobutanoic acid</synonym>
    <synonym>(R)-2-Aminobutyric acid</synonym>
    <synonym>alpha-Aminobutyric acid</synonym>
    <synonym>D-(-)-2-Aminobutyric acid</synonym>
    <synonym>D-2-Aminobutanoic acid</synonym>
    <synonym>D-2-Aminobuttersaeure</synonym>
    <synonym>D-2-Aminobutyrate</synonym>
    <synonym>D-2-Aminobutyric acid</synonym>
    <synonym>(2R)-2-Aminobutyrate</synonym>
    <synonym>(R)-2-Aminobutanoate</synonym>
    <synonym>(R)-2-Aminobutyrate</synonym>
    <synonym>a-Aminobutyrate</synonym>
    <synonym>a-Aminobutyric acid</synonym>
    <synonym>alpha-Aminobutyrate</synonym>
    <synonym>Α-aminobutyrate</synonym>
    <synonym>Α-aminobutyric acid</synonym>
    <synonym>D-(-)-2-Aminobutyrate</synonym>
    <synonym>D-2-Aminobutanoate</synonym>
    <synonym>D-a-Aminobutyrate</synonym>
    <synonym>D-a-Aminobutyric acid</synonym>
    <synonym>D-alpha-Aminobutyrate</synonym>
    <synonym>D-Α-aminobutyrate</synonym>
    <synonym>D-Α-aminobutyric acid</synonym>
    <synonym>(2R)-2-Aminobutanoate</synonym>
    <synonym>(2R)-2-Aminobutanoic acid</synonym>
    <synonym>(R)-2-Amino-butanoate</synonym>
    <synonym>(R)-2-Amino-butanoic acid</synonym>
    <synonym>delta-(-)-2-Aminobutyric acid</synonym>
    <synonym>delta-2-Aminobutanoate</synonym>
    <synonym>delta-2-Aminobutanoic acid</synonym>
    <synonym>delta-2-Aminobuttersaeure</synonym>
    <synonym>delta-2-Aminobutyrate</synonym>
    <synonym>delta-2-Aminobutyric acid</synonym>
    <synonym>delta-alpha-Aminobutyric acid</synonym>
    <synonym>2R-Amino-butanoate</synonym>
    <synonym>(2S)-2-Aminobutanoic acid</synonym>
    <synonym>alpha-Aminobutyric acid, (S)-isomer</synonym>
    <synonym>Butyrine, (S)-isomer</synonym>
    <synonym>L-2-Aminobutyric acid</synonym>
    <synonym>Homoalanine</synonym>
    <synonym>2-Aminobutyric acid</synonym>
    <synonym>2-Aminobutanoic acid</synonym>
    <synonym>alpha-Aminobutyric acid, (+-)-isomer</synonym>
    <synonym>Butyrine, (R)-isomer</synonym>
    <synonym>Butyrine</synonym>
    <synonym>Butyrine, (+-)-isomer</synonym>
    <synonym>L-Homoalanine</synonym>
    <synonym>alpha-Aminobutyric acid, (R)-isomer</synonym>
  </synonyms>
  <chemical_formula>C4H9NO2</chemical_formula>
  <average_molecular_weight>103.1198</average_molecular_weight>
  <monisotopic_moleculate_weight>103.063328537</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-aminobutanoic acid</iupac_name>
  <traditional_iupac>D-2-aminobutyric acid</traditional_iupac>
  <cas_registry_number>2623-91-8</cas_registry_number>
  <smiles>CC[C@@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m1/s1</inchi>
  <inchikey>QWCKQJZIFLGMSD-GSVOUGTGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>D-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>D-alpha-amino acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>D-alpha-amino acid</external_descriptor>
      <external_descriptor>alpha-aminobutyric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>278 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-aminobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>103.1198</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>103.063328537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC[C@@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H9NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QWCKQJZIFLGMSD-GSVOUGTGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268697</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02261</kegg_id>
  <chemspider_id>388757</chemspider_id>
  <drugbank_id>DB04454</drugbank_id>
  <foodb_id>FDB012680</foodb_id>
  <pubchem_compound_id>439691</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28797</chebi_id>
  <meta_cyc_id>CPD0-1952</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Alpha-Aminobutyric acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:18 UTC</creation_date>
  <update_date>2020-04-14 22:47:57 UTC</update_date>
  <accession>BMDB0000651</accession>
  <secondary_accessions>
    <accession>BMDB00651</accession>
  </secondary_accessions>
  <name>Decanoylcarnitine</name>
  <description/>
  <synonyms>
    <synonym>Decanoyl-L-carnitine</synonym>
    <synonym>Decanoylcarnitine, (+-)-isomer</synonym>
    <synonym>Decanoylcarnitine, (R)-isomer</synonym>
    <synonym>Decanoylcarnitine, (S)-isomer</synonym>
  </synonyms>
  <chemical_formula>C17H33NO4</chemical_formula>
  <average_molecular_weight>315.4482</average_molecular_weight>
  <monisotopic_moleculate_weight>315.240958549</monisotopic_moleculate_weight>
  <iupac_name>3-(decanoyloxy)-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>(+-)-decanoylcarnitine</traditional_iupac>
  <cas_registry_number>1492-27-9</cas_registry_number>
  <smiles>CCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C</smiles>
  <inchi>InChI=1S/C17H33NO4/c1-5-6-7-8-9-10-11-12-17(21)22-15(13-16(19)20)14-18(2,3)4/h15H,5-14H2,1-4H3</inchi>
  <inchikey>LZOSYCMHQXPBFU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Acyl carnitines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl-carnitine</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>O-acylcarnitine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(decanoyloxy)-4-(trimethylazaniumyl)butanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>315.4482</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>315.240958549</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C17H33NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C17H33NO4/c1-5-6-7-8-9-10-11-12-17(21)22-15(13-16(19)20)14-18(2,3)4/h15H,5-14H2,1-4H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LZOSYCMHQXPBFU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>890</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.18+/-0.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>0.16+/-0.03</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>0.2+/-0.2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.1+/-0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>0.2+/-0.2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>0.06+/-0.01</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022162</foodb_id>
  <drugbank_id/>
  <chemspider_id>8420677</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>10245190</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>68830</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5623</metlin_id>
  <synthesis_reference>Strack, Erich; Mueller, Detlef M.  Preparation of O-acylcarnitines.    Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie  (1970),  351(1),  95-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:20 UTC</creation_date>
  <update_date>2020-03-13 16:22:47 UTC</update_date>
  <accession>BMDB0000652</accession>
  <secondary_accessions>
    <accession>BMDB00652</accession>
  </secondary_accessions>
  <name>Chondroitin 4-sulfate</name>
  <description>Chondroitin 4-sulfate belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Chondroitin 4-sulfate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Adenosine 3',5'-diphosphate and chondroitin 4-sulfate can be biosynthesized from phosphoadenosine phosphosulfate and chondroitin through the action of the enzyme carbohydrate sulfotransferase 11. In cattle, chondroitin 4-sulfate is involved in the metabolic pathway called the sulfate/sulfite metabolism pathway.</description>
  <synonyms>
    <synonym>Chondroitin 4-sulfuric acid</synonym>
    <synonym>Chondroitin 4-sulphate</synonym>
    <synonym>Chondroitin 4-sulphuric acid</synonym>
    <synonym>Chondroitin 4'-sulfate</synonym>
    <synonym>Chondroitin 4'-sulphate</synonym>
    <synonym>Chondroitin sulfate a</synonym>
    <synonym>Chondroitin sulphate a</synonym>
  </synonyms>
  <chemical_formula>C14H23NO15S</chemical_formula>
  <average_molecular_weight>477.39</average_molecular_weight>
  <monisotopic_moleculate_weight>477.078840219</monisotopic_moleculate_weight>
  <iupac_name>6-{[3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>6-{[3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(=O)NC1C(O)OC(CO)C(OS(O)(=O)=O)C1OC1OC(C(O)C(O)C1O)C(O)=O</smiles>
  <inchi>InChI=1S/C14H23NO15S/c1-3(17)15-5-10(9(30-31(24,25)26)4(2-16)27-13(5)23)28-14-8(20)6(18)7(19)11(29-14)12(21)22/h4-11,13-14,16,18-20,23H,2H2,1H3,(H,15,17)(H,21,22)(H,24,25,26)</inchi>
  <inchikey>AVJBPWGFOQAPRH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Acylaminosugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Disaccharide sulfates</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>O-glucuronides</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-o-glucuronide</substituent>
      <substituent>Acetal</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Acylaminosugar</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Disaccharide sulfate</substituent>
      <substituent>Glucuronic acid or derivatives</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>O-glucuronide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6-{[3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>477.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>477.078840219</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)NC1C(O)OC(CO)C(OS(O)(=O)=O)C1OC1OC(C(O)C(O)C1O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H23NO15S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H23NO15S/c1-3(17)15-5-10(9(30-31(24,25)26)4(2-16)27-13(5)23)28-14-8(20)6(18)7(19)11(29-14)12(21)22/h4-11,13-14,16,18-20,23H,2H2,1H3,(H,15,17)(H,21,22)(H,24,25,26)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AVJBPWGFOQAPRH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>258.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>89.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>41.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1304041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1304042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1304043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1418596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1418597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1418598</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>3570966</chemspider_id>
  <foodb_id>FDB022163</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>4368136</pubchem_compound_id>
  <kegg_id>C00634</kegg_id>
  <pdbe_id/>
  <chebi_id>37397</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:21 UTC</creation_date>
  <update_date>2020-04-16 20:39:19 UTC</update_date>
  <accession>BMDB0000653</accession>
  <secondary_accessions>
    <accession>BMDB00653</accession>
  </secondary_accessions>
  <name>Cholesterol sulfate</name>
  <description/>
  <synonyms>
    <synonym>CHOLEST-5-en-3-yl hydrogen sulfATE</synonym>
    <synonym>Cholest-5-en-3beta-ol sulfate</synonym>
    <synonym>Cholesterol 3-sulfate</synonym>
    <synonym>Cholesterol 3-sulphate</synonym>
    <synonym>Cholesterol hydrogen sulfate</synonym>
    <synonym>Cholesterol hydrogen sulphate</synonym>
    <synonym>Cholesterol sulphate</synonym>
    <synonym>Cholesteryl sulfate</synonym>
    <synonym>Cholesteryl sulphate</synonym>
    <synonym>CHOLEST-5-en-3-yl hydrogen sulfuric acid</synonym>
    <synonym>CHOLEST-5-en-3-yl hydrogen sulphate</synonym>
    <synonym>CHOLEST-5-en-3-yl hydrogen sulphuric acid</synonym>
    <synonym>Cholest-5-en-3b-ol sulfate</synonym>
    <synonym>Cholest-5-en-3b-ol sulfuric acid</synonym>
    <synonym>Cholest-5-en-3b-ol sulphate</synonym>
    <synonym>Cholest-5-en-3b-ol sulphuric acid</synonym>
    <synonym>Cholest-5-en-3beta-ol sulfuric acid</synonym>
    <synonym>Cholest-5-en-3beta-ol sulphate</synonym>
    <synonym>Cholest-5-en-3beta-ol sulphuric acid</synonym>
    <synonym>Cholest-5-en-3β-ol sulfate</synonym>
    <synonym>Cholest-5-en-3β-ol sulfuric acid</synonym>
    <synonym>Cholest-5-en-3β-ol sulphate</synonym>
    <synonym>Cholest-5-en-3β-ol sulphuric acid</synonym>
    <synonym>Cholesterol 3-sulfuric acid</synonym>
    <synonym>Cholesterol 3-sulphuric acid</synonym>
    <synonym>Cholesterol hydrogen sulfuric acid</synonym>
    <synonym>Cholesterol hydrogen sulphuric acid</synonym>
    <synonym>Cholesterol sulfuric acid</synonym>
    <synonym>Cholesterol sulphuric acid</synonym>
    <synonym>Cholesteryl sulfuric acid</synonym>
    <synonym>Cholesteryl sulphuric acid</synonym>
    <synonym>5-Cholesten-3b-yl sulfate</synonym>
    <synonym>5-Cholesten-3b-yl sulphate</synonym>
    <synonym>Cholesteryl sulfate, sodium salt, (3beta)-isomer</synonym>
    <synonym>Cholesteryl sulfate, ammonium salt, (3beta)-isomer</synonym>
    <synonym>Cholesteryl sulfate, sodium salt, 26-(14)C-labeled</synonym>
    <synonym>Cholesteryl sulfate, 3H-labeled, (3beta)-isomer</synonym>
    <synonym>Cholesteryl sulfate, potassium salt, (3beta)-isomer</synonym>
  </synonyms>
  <chemical_formula>C27H46O4S</chemical_formula>
  <average_molecular_weight>466.717</average_molecular_weight>
  <monisotopic_moleculate_weight>466.31168065</monisotopic_moleculate_weight>
  <iupac_name>[(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid</iupac_name>
  <traditional_iupac>[(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid</traditional_iupac>
  <cas_registry_number>1256-86-6</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C27H46O4S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30)/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>BHYOQNUELFTYRT-DPAQBDIFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Sulfated steroids</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfated steroid skeleton</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Sulfates</external_descriptor>
      <external_descriptor>steroid sulfate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>466.717</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>466.31168065</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H46O4S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H46O4S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30)/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHYOQNUELFTYRT-DPAQBDIFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>130.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>56.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273740</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022164</foodb_id>
  <drugbank_id>DB01990</drugbank_id>
  <chemspider_id>58586</chemspider_id>
  <kegg_id>C18043</kegg_id>
  <pubchem_compound_id>65076</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>41321</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>2705326</bigg_id>
  <wikipedia_id>Cholesterol sulfate</wikipedia_id>
  <metlin_id>5625</metlin_id>
  <synthesis_reference>Drayer, N. M.; Lieberman, S.  Isolation of cholesterol sulfate from human blood and gallstones.    Biochemical and Biophysical Research Communications  (1965),  18(1),  126-30.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:22 UTC</creation_date>
  <update_date>2020-03-13 16:22:48 UTC</update_date>
  <accession>BMDB0000655</accession>
  <secondary_accessions>
    <accession>BMDB00655</accession>
  </secondary_accessions>
  <name>Cholestane-3,7,12,25-tetrol</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C27H48O4</chemical_formula>
  <average_molecular_weight>436.677</average_molecular_weight>
  <monisotopic_moleculate_weight>436.355260026</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,9S,10R,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</iupac_name>
  <traditional_iupac>(1S,2S,9S,10R,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@](C)(CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@@]([H])(O)CC4([H])CC([H])(O)CC[C@]4(C)[C@@]3([H])CC([H])(O)[C@]12C</smiles>
  <inchi>InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17?,18?,19-,20+,21+,22+,23?,24+,26+,27-/m1/s1</inchi>
  <inchikey>NTIXPPFPXLYJCT-SFWYEZDTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>25-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,9S,10R,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>436.677</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>436.355260026</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](C)(CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@@]([H])(O)CC4([H])CC([H])(O)CC[C@]4(C)[C@@]3([H])CC([H])(O)[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H48O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H48O4/c1-16(7-6-11-25(2,3)31)19-8-9-20-24-21(15-23(30)27(19,20)5)26(4)12-10-18(28)13-17(26)14-22(24)29/h16-24,28-31H,6-15H2,1-5H3/t16-,17?,18?,19-,20+,21+,22+,23?,24+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NTIXPPFPXLYJCT-SFWYEZDTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>124.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>53.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1304503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1304504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1304505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1419052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1419053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1419054</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id/>
  <foodb_id/>
  <drugbank_id/>
  <pubchem_compound_id/>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:23 UTC</creation_date>
  <update_date>2020-04-14 22:47:58 UTC</update_date>
  <accession>BMDB0000656</accession>
  <secondary_accessions>
    <accession>BMDB00656</accession>
  </secondary_accessions>
  <name>Cysteineglutathione disulfide</name>
  <description/>
  <synonyms>
    <synonym>Cysteineglutathione disulphide</synonym>
    <synonym>CYSSG</synonym>
    <synonym>Cysteine-glutathione disulfide</synonym>
    <synonym>Cysteine-glutathione mixed disulfide</synonym>
    <synonym>Nereithione</synonym>
    <synonym>(2S)-2-Amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulfanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoate</synonym>
    <synonym>(2S)-2-Amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulphanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoate</synonym>
    <synonym>(2S)-2-Amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulphanyl]-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid</synonym>
    <synonym>Cysteine glutathione disulphide</synonym>
  </synonyms>
  <chemical_formula>C13H22N4O8S2</chemical_formula>
  <average_molecular_weight>426.466</average_molecular_weight>
  <monisotopic_moleculate_weight>426.08790508</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid</iupac_name>
  <traditional_iupac>(2S)-2-amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulfanyl]-1-(carboxymethylcarbamoyl)ethyl]carbamoyl}butanoic acid</traditional_iupac>
  <cas_registry_number>13081-14-6</cas_registry_number>
  <smiles>N[C@@H](CCC(=O)N[C@@H](CSSCC(N)C(O)=O)C(=O)NCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C13H22N4O8S2/c14-6(12(22)23)1-2-9(18)17-8(11(21)16-3-10(19)20)5-27-26-4-7(15)13(24)25/h6-8H,1-5,14-15H2,(H,16,21)(H,17,18)(H,19,20)(H,22,23)(H,24,25)/t6-,7?,8-/m0/s1</inchi>
  <inchikey>BNRXZEPOHPEEAS-PPSBICQBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Oligopeptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cysteine and derivatives</alternative_parent>
      <alternative_parent>Dialkyldisulfides</alternative_parent>
      <alternative_parent>Gamma-glutamyl peptides</alternative_parent>
      <alternative_parent>Glutamine and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-oligopeptide</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Cysteine or derivatives</substituent>
      <substituent>Dialkyldisulfide</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Gamma-glutamyl alpha peptide</substituent>
      <substituent>Glutamine or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-substituted-alpha-amino acid</substituent>
      <substituent>Organic disulfide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>234 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-{[(1R)-2-[(2-amino-2-carboxyethyl)disulfanyl]-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>426.466</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>426.08790508</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCC(=O)N[C@@H](CSSCC(N)C(O)=O)C(=O)NCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H22N4O8S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H22N4O8S2/c14-6(12(22)23)1-2-9(18)17-8(11(21)16-3-10(19)20)5-27-26-4-7(15)13(24)25/h6-8H,1-5,14-15H2,(H,16,21)(H,17,18)(H,19,20)(H,22,23)(H,24,25)/t6-,7?,8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BNRXZEPOHPEEAS-PPSBICQBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>222.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>95.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334026</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022166</foodb_id>
  <drugbank_id/>
  <chemspider_id/>
  <kegg_id/>
  <pubchem_compound_id>53477713</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>143243</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5628</metlin_id>
  <synthesis_reference>Eriksson, Bengt; Eriksson, Stellan A.  Synthesis and characterization of the L-cysteine-glutathione mixed disulfide.    Acta Chemica Scandinavica (1947-1973)  (1967),  21(5),  1304-12.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:24 UTC</creation_date>
  <update_date>2020-04-15 22:09:30 UTC</update_date>
  <accession>BMDB0000657</accession>
  <secondary_accessions>
    <accession>BMDB00657</accession>
  </secondary_accessions>
  <name>Copper</name>
  <description>Copper, also known as cu(ii) or copper (ii) ion, belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Copper exists as a solid, possibly soluble (in water), and possibly neutral molecule. Copper exists in all living species, ranging from bacteria to humans. In cattle, copper is involved in the metabolic pathway called the tyrosine metabolism pathway. Copper is a potentially toxic compound. Copper has been found to be associated with several diseases known as aceruloplasminemia, mental retardation, enteropathy, deafness, peripheral neuropathy, ichthyosis, and keratoderma, and alzheimer's disease; also copper has been linked to several inborn metabolic disorders including hyperzincaemia and hypercalprotectinaemia and menkes disease.</description>
  <synonyms>
    <synonym>COPPER (II) ion</synonym>
    <synonym>Copper(II) cation</synonym>
    <synonym>Copper, ion (cu2+)</synonym>
    <synonym>Cu(II)</synonym>
    <synonym>Cu2+</synonym>
    <synonym>Cu(2+)</synonym>
    <synonym>Cupric ion</synonym>
    <synonym>Cu</synonym>
  </synonyms>
  <chemical_formula>Cu</chemical_formula>
  <average_molecular_weight>63.546</average_molecular_weight>
  <monisotopic_moleculate_weight>62.929601079</monisotopic_moleculate_weight>
  <iupac_name>copper(2+) ion</iupac_name>
  <traditional_iupac>copper(2+) ion</traditional_iupac>
  <cas_registry_number>15158-11-9</cas_registry_number>
  <smiles>[Cu++]</smiles>
  <inchi>InChI=1S/Cu/q+2</inchi>
  <inchikey>JPVYNHNXODAKFH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous transition metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous transition metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous transition metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a cation</external_descriptor>
      <external_descriptor>copper cation</external_descriptor>
      <external_descriptor>divalent metal cation</external_descriptor>
      <external_descriptor>monoatomic dication</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>1083 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>copper(2+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>63.546</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>62.929601079</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Cu++]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Cu</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Cu/q+2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JPVYNHNXODAKFH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Degradation of Superoxides</name>
      <smpdb_id>SMP0087191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Riboflavin Metabolism</name>
      <smpdb_id>SMP0087211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118586</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>14.950 +/- 3.462</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Summers (1960) method</comment>
      <references>
        <reference>
          <reference_text>C. R. E. Cogginsa and A. C. Field. Diurnal variation in the chemical composition of plasma from lactating beef cows on three dietary energy intakes. J. agric. Sri., Camb. (1976), 86, 595-602</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>9+/-2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>27+/-19</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>0.25+/-0.13</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.416</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>NRC. 1989. Recommended Dietary Allowances.  10th ed. Natl. Acad. Press, Washington, DC.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.58</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Z. Dobrzañski et al. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Polish Journal of Environmental Studies Vol. 14, No 5 (2005), 685-689</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9.442</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.574</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.574</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.574</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.574</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.574</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.574</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.574</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.574</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.57 +/- 0.23</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>A. PECHOVÁ et al. Contents of Zn, Cu, Mn and Se in Milk in Relation to their Concentrations in Blood, Milk Yield and Stage of Lactation in Dairy Cattle. Acta Vet. Brno 2008, 77: 523-531</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.1 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.4 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.3 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.0572 +/- 0.0944</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.401 +/- 0.0472</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.875 +/- 0.126</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS.  Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.212 +/- 0.0944</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.0772 +/- 0.346</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.567 +/- 0.0944</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.259 - 1.731</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.574</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.259 - 8.498</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.976 +/- 0.0787</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Campillo N, Vinas P, Lopez-Garcia I, Hernandez-Cordoba M: Direct determination of copper and zinc in cow milk, human milk and infant formula samples using electrothermal atomization atomic absorption spectrometry. Talanta. 1998 Aug;46(4):615-22.</reference_text>
          <pubmed_id>18967184</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0229 - 1.401</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2.59 +/- 0.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by ICP-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>5+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>0.2+/-0.1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>0.7+/-0.1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB030749</foodb_id>
  <kegg_id>C00070</kegg_id>
  <drugbank_id/>
  <chemspider_id>25221</chemspider_id>
  <pubchem_compound_id>27099</pubchem_compound_id>
  <chebi_id>29036</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Copper</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Campillo N, Vinas P, Lopez-Garcia I, Hernandez-Cordoba M: Direct determination of copper and zinc in cow milk, human milk and infant formula samples using electrothermal atomization atomic absorption spectrometry. Talanta. 1998 Aug;46(4):615-22.</reference_text>
      <pubmed_id>18967184</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
      <pubmed_id>22081685</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. PECHOVÁ et al. Contents of Zn, Cu, Mn and Se in Milk in Relation to their Concentrations in Blood, Milk Yield and Stage of Lactation in Dairy Cattle. Acta Vet. Brno 2008, 77: 523-531</reference_text>
    </reference>
    <reference>
      <reference_text>NRC. 1989. Recommended Dietary Allowances.  10th ed. Natl. Acad. Press, Washington, DC.</reference_text>
    </reference>
    <reference>
      <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
    </reference>
    <reference>
      <reference_text>Z. Dobrzañski et al. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Polish Journal of Environmental Studies Vol. 14, No 5 (2005), 685-689</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
    </reference>
    <reference>
      <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00003</protein_accession>
      <name>Cytochrome c oxidase subunit 2</name>
      <uniprot_id>P68530</uniprot_id>
      <gene_name>MT-CO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00004</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>P00396</uniprot_id>
      <gene_name>MT-CO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00011</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>Q45LD5</uniprot_id>
      <gene_name>COX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00013</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>Q862S6</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00020</protein_accession>
      <name>Cytochrome c oxidase subunit 2</name>
      <uniprot_id>B1P072</uniprot_id>
      <gene_name>COX2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00021</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>Q5BP91</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00027</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YMV6</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00030</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YMT7</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00032</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YMS5</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00033</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>Q6QTG9</uniprot_id>
      <gene_name>COX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00034</protein_accession>
      <name>Cytochrome c oxidase subunit 2</name>
      <uniprot_id>Q8M444</uniprot_id>
      <gene_name>COX2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00035</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YMS1</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00036</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>Q7JAT4</uniprot_id>
      <gene_name>COI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00037</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>Q45LE8</uniprot_id>
      <gene_name>COX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00038</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>C5IS82</uniprot_id>
      <gene_name>COI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00039</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YN12</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00043</protein_accession>
      <name>Cytochrome c oxidase subunit 2</name>
      <uniprot_id>A1XEF2</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00045</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>Q45LN9</uniprot_id>
      <gene_name>COX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00048</protein_accession>
      <name>Cytochrome c oxidase subunit 2</name>
      <uniprot_id>Q7JAT3</uniprot_id>
      <gene_name>COII</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00050</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>Q85E88</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00051</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>C5IS85</uniprot_id>
      <gene_name>COI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00052</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YN01</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00054</protein_accession>
      <name>Cytochrome c oxidase subunit 2</name>
      <uniprot_id>Q3L5W1</uniprot_id>
      <gene_name>COX2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00058</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YMR7</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00059</protein_accession>
      <name>Cytochrome c oxidase subunit 2</name>
      <uniprot_id>B2KPB9</uniprot_id>
      <gene_name>COII</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00061</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YMW7</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00063</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A1XP62</uniprot_id>
      <gene_name>COI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00065</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>B1NZU1</uniprot_id>
      <gene_name>COX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00091</protein_accession>
      <name>Primary amine oxidase, liver isozyme</name>
      <uniprot_id>Q29437</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00095</protein_accession>
      <name>Membrane primary amine oxidase</name>
      <uniprot_id>Q9TTK6</uniprot_id>
      <gene_name>AOC3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00096</protein_accession>
      <name>Primary amine oxidase, lung isozyme</name>
      <uniprot_id>O46406</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00098</protein_accession>
      <name>Copper amine oxidase</name>
      <uniprot_id>Q3MHQ1</uniprot_id>
      <gene_name>ABP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00587</protein_accession>
      <name>Superoxide dismutase [Cu-Zn]</name>
      <uniprot_id>A4URH1</uniprot_id>
      <gene_name>SOD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00589</protein_accession>
      <name>Superoxide dismutase [Cu-Zn]</name>
      <uniprot_id>A3KLR9</uniprot_id>
      <gene_name>ECSOD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00590</protein_accession>
      <name>Superoxide dismutase [Cu-Zn]</name>
      <uniprot_id>Q861T4</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00591</protein_accession>
      <name>Superoxide dismutase [Cu-Zn]</name>
      <uniprot_id>P00442</uniprot_id>
      <gene_name>SOD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00592</protein_accession>
      <name>Superoxide dismutase [Cu-Zn]</name>
      <uniprot_id>Q9TS96</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00655</protein_accession>
      <name>Dopamine beta-hydroxylase</name>
      <uniprot_id>P15101</uniprot_id>
      <gene_name>DBH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00656</protein_accession>
      <name>Cytochrome c oxidase subunit 2</name>
      <uniprot_id>A1XEF0</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00657</protein_accession>
      <name>Cytochrome c oxidase subunit 2</name>
      <uniprot_id>A1XEE6</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00658</protein_accession>
      <name>Lysyl oxidase homolog 1</name>
      <uniprot_id>Q95L39</uniprot_id>
      <gene_name>LOXL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00659</protein_accession>
      <name>Protein-lysine 6-oxidase</name>
      <uniprot_id>P33072</uniprot_id>
      <gene_name>LOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00660</protein_accession>
      <name>Lysyl oxidase homolog 4</name>
      <uniprot_id>Q8MJ24</uniprot_id>
      <gene_name>LOXL4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00661</protein_accession>
      <name>Cytochrome c oxidase assembly protein COX11, mitochondrial</name>
      <uniprot_id>A3KMZ6</uniprot_id>
      <gene_name>COX11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00662</protein_accession>
      <name>Tyrosinase</name>
      <uniprot_id>Q8MIU0</uniprot_id>
      <gene_name>TYR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00663</protein_accession>
      <name>Cytochrome c oxidase subunit 2</name>
      <uniprot_id>A1XEE9</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00664</protein_accession>
      <name>5,6-dihydroxyindole-2-carboxylic acid oxidase</name>
      <uniprot_id>Q8WN57</uniprot_id>
      <gene_name>TYRP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00665</protein_accession>
      <name>Peptidyl-glycine alpha-amidating monooxygenase</name>
      <uniprot_id>P10731</uniprot_id>
      <gene_name>PAM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01370</protein_accession>
      <name>Serum albumin</name>
      <uniprot_id>P02769</uniprot_id>
      <gene_name>ALB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01592</protein_accession>
      <name>LYR motif-containing protein 4</name>
      <uniprot_id>Q0VCG0</uniprot_id>
      <gene_name>LYRM4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01923</protein_accession>
      <name>Metallothionein-3</name>
      <uniprot_id>P37359</uniprot_id>
      <gene_name>MT3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01924</protein_accession>
      <name>COMM domain-containing protein 1</name>
      <uniprot_id>Q2M2T5</uniprot_id>
      <gene_name>COMMD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01925</protein_accession>
      <name>COX assembly mitochondrial protein homolog</name>
      <uniprot_id>Q3SZM6</uniprot_id>
      <gene_name>CMC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01926</protein_accession>
      <name>Protein SCO1 homolog, mitochondrial</name>
      <uniprot_id>A1A4J8</uniprot_id>
      <gene_name>SCO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01927</protein_accession>
      <name>Copper transport protein ATOX1</name>
      <uniprot_id>Q3T0E0</uniprot_id>
      <gene_name>ATOX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01928</protein_accession>
      <name>Protein SCO2 homolog, mitochondrial</name>
      <uniprot_id>A6H784</uniprot_id>
      <gene_name>SCO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01929</protein_accession>
      <name>Alpha-fetoprotein</name>
      <uniprot_id>Q3SZ57</uniprot_id>
      <gene_name>AFP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01930</protein_accession>
      <name>SPARC</name>
      <uniprot_id>P13213</uniprot_id>
      <gene_name>SPARC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01931</protein_accession>
      <name>Metallothionein-1</name>
      <uniprot_id>P58280</uniprot_id>
      <gene_name>MT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01932</protein_accession>
      <name>Coagulation factor V</name>
      <uniprot_id>Q28107</uniprot_id>
      <gene_name>F5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:26 UTC</creation_date>
  <update_date>2020-03-13 16:22:50 UTC</update_date>
  <accession>BMDB0000658</accession>
  <secondary_accessions>
    <accession>BMDB00658</accession>
  </secondary_accessions>
  <name>CE(16:1(9Z))</name>
  <description/>
  <synonyms>
    <synonym>(Z)-Cholesterol 9-hexadecenoate</synonym>
    <synonym>(Z)-Cholesterol 9-hexadecenoic acid</synonym>
    <synonym>1-Palmitoleoyl-cholesterol</synonym>
    <synonym>16:1(9Z) Cholesterol ester</synonym>
    <synonym>CE(16:1)</synonym>
    <synonym>CE(16:1/0:0)</synonym>
    <synonym>CE(16:1n7/0:0)</synonym>
    <synonym>CE(16:1W7/0:0)</synonym>
    <synonym>Cholest-5-en-3beta-yl (9Z hexadecenoate</synonym>
    <synonym>Cholest-5-en-3beta-yl (9Z hexadecenoate)</synonym>
    <synonym>Cholest-5-en-3beta-yl (9Z hexadecenoic acid</synonym>
    <synonym>Cholesterol 1-(9Z-hexadecenoate</synonym>
    <synonym>Cholesterol 1-(9Z-hexadecenoate)</synonym>
    <synonym>Cholesterol 1-(9Z-hexadecenoic acid</synonym>
    <synonym>Cholesterol 1-(9Z-hexadecenoic acid)</synonym>
    <synonym>Cholesterol 1-palmitoleoate</synonym>
    <synonym>Cholesterol 1-palmitoleoic acid</synonym>
    <synonym>Cholesterol ester(16:1)</synonym>
    <synonym>Cholesterol ester(16:1/0:0)</synonym>
    <synonym>Cholesterol ester(16:1n7/0:0)</synonym>
    <synonym>Cholesterol ester(16:1W7/0:0)</synonym>
    <synonym>Cholesterol palmitoleate</synonym>
    <synonym>Cholesteryl 1-(9Z-hexadecenoate</synonym>
    <synonym>Cholesteryl 1-(9Z-hexadecenoate)</synonym>
    <synonym>Cholesteryl 1-(9Z-hexadecenoic acid</synonym>
    <synonym>Cholesteryl 1-(9Z-hexadecenoic acid)</synonym>
    <synonym>Cholesteryl 1-palmitoleoate</synonym>
    <synonym>Cholesteryl 1-palmitoleoic acid</synonym>
    <synonym>Cholesteryl cis-hexadecenoate</synonym>
    <synonym>Cholesteryl cis-hexadecenoic acid</synonym>
    <synonym>Cholesteryl palmitoleat</synonym>
    <synonym>Cholesteryl palmitoleate</synonym>
    <synonym>Cholesteryl palmitoleic acid</synonym>
    <synonym>(2R,14R,15R)-2,15-Dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0,.0,]heptadec-7-en-5-yl (9Z)-hexadec-9-enoic acid</synonym>
  </synonyms>
  <chemical_formula>C43H74O2</chemical_formula>
  <average_molecular_weight>623.0465</average_molecular_weight>
  <monisotopic_moleculate_weight>622.568881612</monisotopic_moleculate_weight>
  <iupac_name>(2R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (9Z)-hexadec-9-enoate</iupac_name>
  <traditional_iupac>cholesteryl palmitoleate</traditional_iupac>
  <cas_registry_number/>
  <smiles>CCCCCC\C=C/CCCCCCCC(=O)OC1CC[C@@]2(C)C(=CCC3C4CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CCC23)C1</smiles>
  <inchi>InChI=1S/C43H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h12-13,24,33-34,36-40H,7-11,14-23,25-32H2,1-6H3/b13-12-/t34-,36?,37?,38-,39?,40?,42+,43-/m1/s1</inchi>
  <inchikey>HODJWNWCVNUPAQ-FSAOOAOSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Steroid esters</sub_class>
    <direct_parent>Cholesteryl esters</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Cholesterols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cholestane-skeleton</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesteryl ester</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>10.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-8.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>13.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (9Z)-hexadec-9-enoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>623.0465</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>622.568881612</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCC\C=C/CCCCCCCC(=O)OC1CC[C@@]2(C)C(=CCC3C4CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CCC23)C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C43H74O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C43H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h12-13,24,33-34,36-40H,7-11,14-23,25-32H2,1-6H3/b13-12-/t34-,36?,37?,38-,39?,40?,42+,43-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HODJWNWCVNUPAQ-FSAOOAOSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>26.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>195.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>82.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338433</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1.7 +/- 1.21</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1.7 +/- 1.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by FAMEs/GC–MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id/>
  <kegg_id/>
  <drugbank_id/>
  <chemspider_id/>
  <pubchem_compound_id>22833543</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Wang, Stephen T.; Peter, Frank.  Gas-liquid chromatographic determination of fatty acid composition of cholesteryl esters in human serum using silica Sep-Pak cartridges.    Journal of Chromatography  (1983),  276(2),  249-56.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:27 UTC</creation_date>
  <update_date>2020-03-13 16:22:50 UTC</update_date>
  <accession>BMDB0000659</accession>
  <secondary_accessions>
    <accession>BMDB00659</accession>
  </secondary_accessions>
  <name>Deoxycholic acid disulfate</name>
  <description/>
  <synonyms>
    <synonym>Deoxycholate disulfate</synonym>
    <synonym>Deoxycholate disulphate</synonym>
    <synonym>Deoxycholic acid disulfuric acid</synonym>
    <synonym>Deoxycholic acid disulphuric acid</synonym>
    <synonym>Deoxycholic acid disulphate</synonym>
  </synonyms>
  <chemical_formula>C24H40O10S2</chemical_formula>
  <average_molecular_weight>552.698</average_molecular_weight>
  <monisotopic_moleculate_weight>552.20628888</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-2,15-dimethyl-5,16-bis(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-2,15-dimethyl-5,16-bis(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>67030-51-7</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O)OS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C24H40O10S2/c1-14(4-9-22(25)26)18-7-8-19-17-6-5-15-12-16(33-35(27,28)29)10-11-23(15,2)20(17)13-21(24(18,19)3)34-36(30,31)32/h14-21H,4-13H2,1-3H3,(H,25,26)(H,27,28,29)(H,30,31,32)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1</inchi>
  <inchikey>BYHNMIVTBIJJFZ-LLQZFEROSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Sulfated steroids</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Bile acid, alcohol, or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfated steroid skeleton</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Sulfates</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-2,15-dimethyl-5,16-bis(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>552.698</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>552.20628888</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@H](C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)OS(O)(=O)=O)OS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O10S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O10S2/c1-14(4-9-22(25)26)18-7-8-19-17-6-5-15-12-16(33-35(27,28)29)10-11-23(15,2)20(17)13-21(24(18,19)3)34-36(30,31)32/h14-21H,4-13H2,1-3H3,(H,25,26)(H,27,28,29)(H,30,31,32)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BYHNMIVTBIJJFZ-LLQZFEROSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>164.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>129.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>57.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353856</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022168</foodb_id>
  <kegg_id/>
  <drugbank_id/>
  <chemspider_id>402421</chemspider_id>
  <pubchem_compound_id>457190</pubchem_compound_id>
  <chebi_id>491276</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5630</metlin_id>
  <synthesis_reference>Bureeva, Svetlana; Andia-Pravdivy, Julian; Symon, Andrey; Bichucher, Anna; Moskaleva, Vera; Popenko, Vladimir; Shpak, Alexey; Shvets, Vitaly; Kozlov, Leonid; Kaplun, Alexander.  Selective inhibition of the interaction of C1q with immunoglobulins and the classical pathway of complement activation by steroids and triterpenoids sulfates.    Bioorganic &amp; Medicinal Chemistry  (2007),  15(10),  3489-3498.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:28 UTC</creation_date>
  <update_date>2020-04-16 21:05:27 UTC</update_date>
  <accession>BMDB0000660</accession>
  <secondary_accessions>
    <accession>BMDB00660</accession>
  </secondary_accessions>
  <name>D-Fructose</name>
  <description>D-Fructose, also known as D-tagatose or D-lyxo-2-hexulose, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. D-Fructose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Fructose exists in all living species, ranging from bacteria to humans. D-Fructose participates in a number of enzymatic reactions, within cattle. In particular, D-Fructose can be biosynthesized from sorbitol through its interaction with the enzyme sorbitol dehydrogenase. In addition, D-Fructose can be biosynthesized from Beta-D-fructose 2-phosphate through the action of the enzyme 14 kda phosphohistidine phosphatase. In cattle, D-fructose is involved in the metabolic pathway called the fructose and mannose degradation pathway. D-Fructose is a potentially toxic compound.</description>
  <synonyms>
    <synonym>beta-D-Arabino-hexulose</synonym>
    <synonym>beta-D-Fructose</synonym>
    <synonym>beta-Fruit sugar</synonym>
    <synonym>beta-Levulose</synonym>
    <synonym>FRUCTOSE</synonym>
    <synonym>b-D-Arabino-hexulose</synonym>
    <synonym>Β-D-arabino-hexulose</synonym>
    <synonym>b-D-Fructose</synonym>
    <synonym>Β-D-fructose</synonym>
    <synonym>b-Fruit sugar</synonym>
    <synonym>Β-fruit sugar</synonym>
    <synonym>b-Levulose</synonym>
    <synonym>Β-levulose</synonym>
    <synonym>beta-D-Fructofuranose</synonym>
    <synonym>beta-delta-Arabino-hexulose</synonym>
    <synonym>beta-delta-Fructofuranose</synonym>
    <synonym>beta-delta-Fructose</synonym>
    <synonym>D-(-)-Fructose</synonym>
    <synonym>delta-(-)-Fructose</synonym>
    <synonym>delta-Fructose</synonym>
    <synonym>FRU</synonym>
    <synonym>Fructon</synonym>
    <synonym>Levulose</synonym>
    <synonym>Braun brand OF fructose</synonym>
    <synonym>Fleboplast levulosa</synonym>
    <synonym>Fresenius kabi brand OF fructose</synonym>
    <synonym>Instituto farmacologico brand OF fructose</synonym>
    <synonym>Levulosa</synonym>
    <synonym>Levulosa ife</synonym>
    <synonym>Grifols brand OF fructose</synonym>
    <synonym>Levulosa baxter</synonym>
    <synonym>Levulosado braun</synonym>
    <synonym>Ern brand OF fructose</synonym>
    <synonym>Levulosa grifols</synonym>
    <synonym>Levulosa mein</synonym>
    <synonym>Levulosado vitulia</synonym>
    <synonym>Apir levulosa</synonym>
    <synonym>Baxter brand OF fructose</synonym>
    <synonym>Bieffe brand OF fructose</synonym>
    <synonym>Levulosa braun</synonym>
    <synonym>Levulosa ibys</synonym>
    <synonym>Levulosa, apir</synonym>
    <synonym>Levulosa, fleboplast</synonym>
    <synonym>Levulosado bieffe medit</synonym>
    <synonym>Plast apyr levulosa mein</synonym>
  </synonyms>
  <chemical_formula>C6H12O6</chemical_formula>
  <average_molecular_weight>180.1559</average_molecular_weight>
  <monisotopic_moleculate_weight>180.063388116</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol</iupac_name>
  <traditional_iupac>fructose</traditional_iupac>
  <cas_registry_number>53188-23-1</cas_registry_number>
  <smiles>OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H12O6/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/m1/s1</inchi>
  <inchikey>RFSUNEUAIZKAJO-ARQDHWQXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>C-glycosyl compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D-fructofuranose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>119 - 122 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>778 mg/mL at 20 °C</value>
      <source>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>180.1559</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>180.063388116</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O6/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RFSUNEUAIZKAJO-ARQDHWQXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>110.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>36.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>371530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>371531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>371532</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>763.813 +/- 751.731</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB031286</foodb_id>
  <drugbank_id/>
  <chemspider_id>388775</chemspider_id>
  <kegg_id>C02336</kegg_id>
  <pubchem_compound_id>439709</pubchem_compound_id>
  <pdbe_id>FRU</pdbe_id>
  <chebi_id>28645</chebi_id>
  <meta_cyc_id>BETA-D-FRUCTOSE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001117</knapsack_id>
  <bigg_id>33835</bigg_id>
  <wikipedia_id>Fructose</wikipedia_id>
  <metlin_id>135</metlin_id>
  <synthesis_reference>Liu, Hong; Han, Dong; Meng, Xiang-bao; Li, Zhong-jun.  Improved synthesis of fructose-derived 1,3,4-oxadiazole as novel antitumor agents.    Journal of Chinese Pharmaceutical Sciences  (2005),  14(4),  209-212.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01874</protein_accession>
      <name>Sodium/myo-inositol cotransporter 2</name>
      <uniprot_id>Q3ZC26</uniprot_id>
      <gene_name>SLC5A11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02036</protein_accession>
      <name>Solute carrier family 2, facilitated glucose transporter member 8</name>
      <uniprot_id>P58354</uniprot_id>
      <gene_name>SLC2A8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02075</protein_accession>
      <name>Solute carrier family 2, facilitated glucose transporter member 5</name>
      <uniprot_id>P58353</uniprot_id>
      <gene_name>SLC2A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:29 UTC</creation_date>
  <update_date>2020-04-14 22:48:00 UTC</update_date>
  <accession>BMDB0000661</accession>
  <secondary_accessions>
    <accession>BMDB00661</accession>
  </secondary_accessions>
  <name>Glutaric acid</name>
  <description/>
  <synonyms>
    <synonym>1,3-Propanedicarboxylic acid</synonym>
    <synonym>1,5-Pentanedioic acid</synonym>
    <synonym>Glutarsaeure</synonym>
    <synonym>Pentanedioic acid</synonym>
    <synonym>1,3-Propanedicarboxylate</synonym>
    <synonym>1,5-Pentanedioate</synonym>
    <synonym>Pentanedioate</synonym>
    <synonym>Glutarate</synonym>
    <synonym>Pentandioate</synonym>
    <synonym>Pentandioic acid</synonym>
  </synonyms>
  <chemical_formula>C5H8O4</chemical_formula>
  <average_molecular_weight>132.1146</average_molecular_weight>
  <monisotopic_moleculate_weight>132.042258744</monisotopic_moleculate_weight>
  <iupac_name>pentanedioic acid</iupac_name>
  <traditional_iupac>glutaric acid</traditional_iupac>
  <cas_registry_number>110-94-1</cas_registry_number>
  <smiles>OC(=O)CCCC(O)=O</smiles>
  <inchi>InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9)</inchi>
  <inchikey>JFCQEDHGNNZCLN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Dicarboxylic acids and derivatives</sub_class>
    <direct_parent>Dicarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>alpha,omega-dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>95.8 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1600.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.29</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.046</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.1146</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O4/c6-4(7)2-1-3-5(8)9/h1-3H2,(H,6,7)(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JFCQEDHGNNZCLN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439067</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB001477</foodb_id>
  <drugbank_id>DB03553</drugbank_id>
  <chemspider_id>723</chemspider_id>
  <kegg_id>C00489</kegg_id>
  <pubchem_compound_id>743</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17859</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001184</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Glutaric_acid</wikipedia_id>
  <metlin_id>3254</metlin_id>
  <synthesis_reference>Petrova, E. G.; Kasumova, N. M.; Kagramanova, N. A.; Dadasheva, A. D.  Mechanism of glutaric acid synthesis.    Issledovaniya v Oblasti Kinetiki, Modelirovaniya i Optimizatsii Khimicheskikh Protsessov  (1974),  2  277-89.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:30 UTC</creation_date>
  <update_date>2020-04-16 20:37:39 UTC</update_date>
  <accession>BMDB0000662</accession>
  <secondary_accessions>
    <accession>BMDB00662</accession>
  </secondary_accessions>
  <name>Fluorine</name>
  <description>Fluorine, also known as fluoride ion, belongs to the class of inorganic compounds known as homogeneous halogens. These are inorganic non-metallic compounds in which the largest atom is a nobel gas. Fluorine exists as a solid, possibly soluble (in water), and a weakly acidic compound (based on its pKa) molecule. Fluorine exists in all eukaryotes, ranging from yeast to humans. Fluorine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>F(-)</synonym>
    <synonym>FLUORIDE ion</synonym>
    <synonym>Fluorine anion</synonym>
    <synonym>Fluorides</synonym>
  </synonyms>
  <chemical_formula>F</chemical_formula>
  <average_molecular_weight>18.9984</average_molecular_weight>
  <monisotopic_moleculate_weight>18.998403205</monisotopic_moleculate_weight>
  <iupac_name>fluoride</iupac_name>
  <traditional_iupac>fluoride</traditional_iupac>
  <cas_registry_number>16984-48-8</cas_registry_number>
  <smiles>[F-]</smiles>
  <inchi>InChI=1S/FH/h1H/p-1</inchi>
  <inchikey>KRHYYFGTRYWZRS-UHFFFAOYSA-M</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous halogens. These are inorganic non-metallic compounds in which the largest atom is a nobel gas.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Homogeneous halogens</class>
    <sub_class/>
    <direct_parent>Homogeneous halogens</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous halogen</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>an anion</external_descriptor>
      <external_descriptor>halide anion</external_descriptor>
      <external_descriptor>monoatomic fluorine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Gas</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>fluoride</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>18.9984</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>18.998403205</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[F-]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>F</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/FH/h1H/p-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KRHYYFGTRYWZRS-UHFFFAOYSA-M</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>0.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>68973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>68974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>68975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>127140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>127141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>127142</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>200 +/- 6</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>McAdam PA, O'Dell GD: Mineral profile of blood plasma of lactating dairy cows. J Dairy Sci. 1982 Jul;65(7):1219-26. doi: 10.3168/jds.S0022-0302(82)82333-3.</reference_text>
          <pubmed_id>7108016</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0527</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>NRC. 1989. Recommended Dietary Allowances.  10th ed. Natl. Acad. Press, Washington, DC.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB004485</foodb_id>
  <kegg_id>C00742</kegg_id>
  <drugbank_id>DB11257</drugbank_id>
  <chemspider_id>26214</chemspider_id>
  <pubchem_compound_id>28179</pubchem_compound_id>
  <chebi_id>17051</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Fluorine</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Li, Rong.  Electrolytic cell for manufacturing fluorine at intermediate temperature.    Shiyong Xinxing Zhuanli Shuomingshu  (2007),     13pp.  CODEN: CNXXAR  CN  2895439  Y  20070502  CAN 147:310009  AN 2007:902560</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>NRC. 1989. Recommended Dietary Allowances.  10th ed. Natl. Acad. Press, Washington, DC.</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00500</protein_accession>
      <name>Diphosphoinositol polyphosphate phosphohydrolase 1</name>
      <uniprot_id>A2VE79</uniprot_id>
      <gene_name>NUDT3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:31 UTC</creation_date>
  <update_date>2020-04-15 22:14:16 UTC</update_date>
  <accession>BMDB0000663</accession>
  <secondary_accessions>
    <accession>BMDB00663</accession>
  </secondary_accessions>
  <name>Glucaric acid</name>
  <description>Glucaric acid, also known as glucarate or D-saccharic acid, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Glucaric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Glucaric acid exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>D-(+)-Saccharic acid</synonym>
    <synonym>D-Glucosaccharic acid</synonym>
    <synonym>D-Saccharic acid</synonym>
    <synonym>L-Gularic acid</synonym>
    <synonym>Saccharic acid</synonym>
    <synonym>D-Glucaric acid</synonym>
    <synonym>Glucarate</synonym>
    <synonym>D-(+)-Saccharate</synonym>
    <synonym>D-Glucosaccharate</synonym>
    <synonym>D-Saccharate</synonym>
    <synonym>L-Gularate</synonym>
    <synonym>Saccharate</synonym>
    <synonym>D-Glucarate</synonym>
    <synonym>(2R,3S,4S,5S)-2,3,4,5-Tetrahydroxyhexanedioate</synonym>
    <synonym>(2R,3S,4S,5S)-2,3,4,5-Tetrahydroxyhexanedioic acid</synonym>
    <synonym>D-Tetrahydroxyadipate</synonym>
    <synonym>D-Tetrahydroxyadipic acid</synonym>
    <synonym>DL-Glucaric acid</synonym>
    <synonym>GKR</synonym>
    <synonym>Glucosaccharic acid</synonym>
    <synonym>Tetrahydroxyadipic acid</synonym>
    <synonym>Acid, saccharic</synonym>
    <synonym>Anhydrous calcium glucarate</synonym>
    <synonym>Anhydrous calcium saccharate</synonym>
    <synonym>Calcium saccharate</synonym>
    <synonym>Glucarate, calcium</synonym>
    <synonym>Levo gularic acid</synonym>
    <synonym>Levo-gularic acid</synonym>
    <synonym>Tetrahydrate, calcium saccharate</synonym>
    <synonym>Calcium glucarate</synonym>
    <synonym>Calcium glucarate, anhydrous</synonym>
    <synonym>Calcium saccharate anhydrous</synonym>
    <synonym>Calcium saccharate, anhydrous</synonym>
    <synonym>D Glucaric acid</synonym>
    <synonym>Saccharate tetrahydrate, calcium</synonym>
    <synonym>Saccharate, calcium</synonym>
    <synonym>Calcium saccharate tetrahydrate</synonym>
    <synonym>D Saccharic acid</synonym>
    <synonym>Glucarate, anhydrous calcium</synonym>
    <synonym>L Gularic acid</synonym>
    <synonym>Saccharate, anhydrous calcium</synonym>
  </synonyms>
  <chemical_formula>C6H10O8</chemical_formula>
  <average_molecular_weight>210.1388</average_molecular_weight>
  <monisotopic_moleculate_weight>210.037567296</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid</iupac_name>
  <traditional_iupac>saccharic acid</traditional_iupac>
  <cas_registry_number>87-73-0</cas_registry_number>
  <smiles>O[C@@H]([C@H](O)[C@@H](O)C(O)=O)[C@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2-,3-,4+/m0/s1</inchi>
  <inchikey>DSLZVSRJTYRBFB-LLEIAEIESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Glucuronic acid derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Medium-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Glucuronic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>glucaric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>912 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>210.1388</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>210.037567296</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]([C@H](O)[C@@H](O)C(O)=O)[C@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2-,3-,4+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DSLZVSRJTYRBFB-LLEIAEIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>155.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451950</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022169</foodb_id>
  <kegg_id>C00818</kegg_id>
  <drugbank_id>DB03603</drugbank_id>
  <chemspider_id>30577</chemspider_id>
  <pubchem_compound_id>33037</pubchem_compound_id>
  <chebi_id>16002</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>D-GLUCARATE</meta_cyc_id>
  <knapsack_id>C00034205</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35926</bigg_id>
  <wikipedia_id>Saccharic_acid</wikipedia_id>
  <metlin_id>5633</metlin_id>
  <synthesis_reference>Bamba, K.; Kokoh, K. B.; Servat, K.; Leger, J.-M.  Electrocatalytic oxidation of monosaccharides on platinum electrodes modified by thallium adatoms in carbonate buffered medium.    Journal of Applied Electrochemistry  (2006),  36(2),  233-238.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:32 UTC</creation_date>
  <update_date>2020-04-15 22:14:17 UTC</update_date>
  <accession>BMDB0000664</accession>
  <secondary_accessions>
    <accession>BMDB00664</accession>
  </secondary_accessions>
  <name>Isohyodeoxycholic acid</name>
  <description/>
  <synonyms>
    <synonym>Isohyodeoxycholate</synonym>
    <synonym>3b,6a-Dihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3b,6a-Dihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3b,6a-Dihydroxy-5b-cholanoate</synonym>
    <synonym>3b,6a-Dihydroxy-5b-cholanoic acid</synonym>
    <synonym>b-Hyodeoxycholate</synonym>
    <synonym>b-Hyodeoxycholic acid</synonym>
    <synonym>beta-Hyodeoxycholate</synonym>
    <synonym>beta-Hyodeoxycholic acid</synonym>
    <synonym>Isohydroxycholate</synonym>
  </synonyms>
  <chemical_formula>C24H40O4</chemical_formula>
  <average_molecular_weight>392.572</average_molecular_weight>
  <monisotopic_moleculate_weight>392.292659768</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5S,7R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5S,7R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>570-84-3</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)[C@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17-,18+,19+,20+,21+,23-,24-/m1/s1</inchi>
  <inchikey>DGABKXLVXPYZII-MMTMODRTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>6-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>6-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5S,7R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>392.572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.292659768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)[C@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17-,18+,19+,20+,21+,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DGABKXLVXPYZII-MMTMODRTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344508</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022170</foodb_id>
  <kegg_id/>
  <drugbank_id/>
  <chemspider_id>4446910</chemspider_id>
  <pubchem_compound_id>5283822</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5634</metlin_id>
  <synthesis_reference>Lida, Takashi; Momose, Toshiaki; Tamura, Toshitake; Matsumoto, Taro; Chang, Frederic C.; Goto, Junichi; Nambara, Toshio.  Potential bile acid metabolites.  13.  Improved routes to 3b,6b- and 3b,6a-dihydroxy-5b-cholanoic acids.  Journal of Lipid Research  (1988),  29(2),  165-71.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:34 UTC</creation_date>
  <update_date>2020-03-13 16:22:54 UTC</update_date>
  <accession>BMDB0000665</accession>
  <secondary_accessions>
    <accession>BMDB00665</accession>
  </secondary_accessions>
  <name>Leucinic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Hydroxyisocaproic acid</synonym>
    <synonym>2-Hydroxyisohexanoic acid</synonym>
    <synonym>alpha-Hydroxyisocaproic acid</synonym>
    <synonym>Leucic acid</synonym>
    <synonym>2-Hydroxyisocaproate</synonym>
    <synonym>2-Hydroxyisohexanoate</synonym>
    <synonym>a-Hydroxyisocaproate</synonym>
    <synonym>a-Hydroxyisocaproic acid</synonym>
    <synonym>alpha-Hydroxyisocaproate</synonym>
    <synonym>Α-hydroxyisocaproate</synonym>
    <synonym>Α-hydroxyisocaproic acid</synonym>
    <synonym>Leucate</synonym>
    <synonym>Leucinate</synonym>
    <synonym>2-Hydroxy-4-methyl-valerate</synonym>
    <synonym>2-Hydroxy-4-methyl-valeric acid</synonym>
    <synonym>2-Hydroxy-4-methylpentanoate</synonym>
    <synonym>2-Hydroxy-4-methylpentanoic acid</synonym>
    <synonym>2-Hydroxy-4-methylvalerate</synonym>
    <synonym>2-Hydroxy-4-methylvaleric acid</synonym>
    <synonym>a-Hydroxy-iso-caproate</synonym>
    <synonym>a-Hydroxy-iso-caproic acid</synonym>
    <synonym>alpha-Hydroxy-iso-caproate</synonym>
    <synonym>alpha-Hydroxy-iso-caproic acid</synonym>
    <synonym>DL-2-Hydroxy-4-methylpentanoate</synonym>
    <synonym>DL-2-Hydroxy-4-methylpentanoic acid</synonym>
    <synonym>DL-2-Hydroxyisocaproate</synonym>
    <synonym>DL-2-Hydroxyisocaproic acid</synonym>
    <synonym>DL-a-Hydroxyisocaproate</synonym>
    <synonym>DL-a-Hydroxyisocaproic acid</synonym>
    <synonym>DL-alpha-Hydroxyisocaproate</synonym>
    <synonym>DL-alpha-Hydroxyisocaproic acid</synonym>
    <synonym>DL-Leucate</synonym>
    <synonym>DL-Leucic acid</synonym>
    <synonym>alpha-Hydroxyisocaproic acid, monosodium salt</synonym>
    <synonym>alpha-Hydroxyisocaproic acid, (R)-isomer</synonym>
    <synonym>alpha-Hydroxyisocaproic acid, calcium (2:1) salt, (S)-isomer</synonym>
    <synonym>alpha-Hydroxyisocaproic acid, (S)-isomer</synonym>
    <synonym>Leucinic acid</synonym>
  </synonyms>
  <chemical_formula>C6H12O3</chemical_formula>
  <average_molecular_weight>132.1577</average_molecular_weight>
  <monisotopic_moleculate_weight>132.07864425</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-4-methylpentanoic acid</iupac_name>
  <traditional_iupac>leucate</traditional_iupac>
  <cas_registry_number>498-36-2</cas_registry_number>
  <smiles>CC(C)CC(O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)</inchi>
  <inchikey>LVRFTAZAXQPQHI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxy fatty acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
      <external_descriptor>branched-chain fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>886 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-4-methylpentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.1577</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.07864425</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CC(O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LVRFTAZAXQPQHI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439233</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022171</foodb_id>
  <drugbank_id/>
  <chemspider_id>83753</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>92779</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>59783</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5635</metlin_id>
  <synthesis_reference>Camien, Merill N.; Fowler, Audree V.; Dunn, Max S.  Production of a-hydroxy fatty acids by two strains of Lactobacillus casei.    Archives of Biochemistry and Biophysics  (1959),  83  408-18.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:35 UTC</creation_date>
  <update_date>2020-04-15 22:09:32 UTC</update_date>
  <accession>BMDB0000666</accession>
  <secondary_accessions>
    <accession>BMDB00666</accession>
  </secondary_accessions>
  <name>Heptanoic acid</name>
  <description>Heptanoic acid, also known as enanthic acid or heptylic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Heptanoic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Heptanoic acid exists in all eukaryotes, ranging from yeast to humans. Heptanoic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>CH3-[CH2]5-COOH</synonym>
    <synonym>Enanthic acid</synonym>
    <synonym>Enanthylic acid</synonym>
    <synonym>Heptansaeure</synonym>
    <synonym>Heptoic acid</synonym>
    <synonym>Heptylic acid</synonym>
    <synonym>N-Heptanoic acid</synonym>
    <synonym>N-Heptoic acid</synonym>
    <synonym>N-Heptylic acid</synonym>
    <synonym>Oenanthic acid</synonym>
    <synonym>Oenanthylic acid</synonym>
    <synonym>Oenanthsaeure</synonym>
    <synonym>Enanthate</synonym>
    <synonym>Enanthylate</synonym>
    <synonym>Heptoate</synonym>
    <synonym>Heptylate</synonym>
    <synonym>N-Heptanoate</synonym>
    <synonym>N-Heptoate</synonym>
    <synonym>N-Heptylate</synonym>
    <synonym>Oenanthate</synonym>
    <synonym>Oenanthylate</synonym>
    <synonym>Heptanoate</synonym>
    <synonym>1-Hexanecarboxylate</synonym>
    <synonym>1-Hexanecarboxylic acid</synonym>
  </synonyms>
  <chemical_formula>C7H14O2</chemical_formula>
  <average_molecular_weight>130.1849</average_molecular_weight>
  <monisotopic_moleculate_weight>130.099379692</monisotopic_moleculate_weight>
  <iupac_name>heptanoic acid</iupac_name>
  <traditional_iupac>heptanoic acid</traditional_iupac>
  <cas_registry_number>111-14-8</cas_registry_number>
  <smiles>CCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9)</inchi>
  <inchikey>MNWFXJYAOYHMED-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>medium-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-7.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>2.82 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.42</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>heptanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>130.1849</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>130.099379692</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H14O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H14O2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MNWFXJYAOYHMED-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>944</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438659</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.441 +/- 0.014</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.568 +/- 0.024</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.448 +/- 0.012</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.45 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB02938</drugbank_id>
  <foodb_id>FDB008051</foodb_id>
  <pubchem_compound_id>8094</pubchem_compound_id>
  <chemspider_id>7803</chemspider_id>
  <pdbe_id/>
  <kegg_id>C17714</kegg_id>
  <chebi_id>45571</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD-7619</meta_cyc_id>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Heptanoic_acid</wikipedia_id>
  <metlin_id>5636</metlin_id>
  <synthesis_reference>Jain, R. K.; Venkatesan, T. K.  Heptanoic acid from heptaldehyde.    Journal of the Oil Technologists' Association of India (Mumbai, India)  (1984),  16(4),  111-12.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026.</reference_text>
      <pubmed_id>29570652</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:36 UTC</creation_date>
  <update_date>2020-04-15 22:36:53 UTC</update_date>
  <accession>BMDB0000667</accession>
  <secondary_accessions>
    <accession>BMDB00667</accession>
  </secondary_accessions>
  <name>L-Thyronine</name>
  <description/>
  <synonyms>
    <synonym>4-(4-Hydroxyphenoxy)-L-phenylalanine</synonym>
    <synonym>O-(4-Hydroxyphenyl)-L-tyrosine</synonym>
    <synonym>b-(p-Hydroxyphenoxy)phenylalanine</synonym>
    <synonym>beta-(p-Hydroxyphenoxy)phenylalanine</synonym>
    <synonym>Desiodothyroxine</synonym>
    <synonym>O-(4-Hydroxyphenyl)tyrosine</synonym>
    <synonym>Thyronine</synonym>
    <synonym>Thyronines</synonym>
  </synonyms>
  <chemical_formula>C15H15NO4</chemical_formula>
  <average_molecular_weight>273.2839</average_molecular_weight>
  <monisotopic_moleculate_weight>273.100107973</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-[4-(4-hydroxyphenoxy)phenyl]propanoic acid</iupac_name>
  <traditional_iupac>thyronine</traditional_iupac>
  <cas_registry_number>1596-67-4</cas_registry_number>
  <smiles>N[C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C15H15NO4/c16-14(15(18)19)9-10-1-5-12(6-2-10)20-13-7-3-11(17)4-8-13/h1-8,14,17H,9,16H2,(H,18,19)/t14-/m0/s1</inchi>
  <inchikey>KKCIOUWDFWQUBT-AWEZNQCLSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Phenylalanine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Diarylethers</alternative_parent>
      <alternative_parent>Diphenylethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenol ethers</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Diaryl ether</substituent>
      <substituent>Diphenylether</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>thyronine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>255 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.012</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-[4-(4-hydroxyphenoxy)phenyl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>273.2839</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>273.100107973</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CC1=CC=C(OC2=CC=C(O)C=C2)C=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H15NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H15NO4/c16-14(15(18)19)9-10-1-5-12(6-2-10)20-13-7-3-11(17)4-8-13/h1-8,14,17H,9,16H2,(H,18,19)/t14-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KKCIOUWDFWQUBT-AWEZNQCLSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>73.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>27.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352788</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022172</foodb_id>
  <pubchem_compound_id>5461103</pubchem_compound_id>
  <chemspider_id>4574450</chemspider_id>
  <pdbe_id/>
  <kegg_id/>
  <chebi_id>30662</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Thyronine</wikipedia_id>
  <metlin_id>5637</metlin_id>
  <synthesis_reference>Harrington, C. R.; Rivers, Rosalind V. Pitt.  New synthesis of thyronine.    Journal of the Chemical Society  (1940),     1101-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:37 UTC</creation_date>
  <update_date>2020-04-15 22:32:31 UTC</update_date>
  <accession>BMDB0000668</accession>
  <secondary_accessions>
    <accession>BMDB00668</accession>
  </secondary_accessions>
  <name>Hematoporphyrin IX</name>
  <description/>
  <synonyms>
    <synonym>1,3,5,8-Tetramethyl-2,4-bis( -hydroxyethyl)porphine-6,7-dipropionate</synonym>
    <synonym>1,3,5,8-Tetramethyl-2,4-bis( -hydroxyethyl)porphine-6,7-dipropionic acid</synonym>
    <synonym>1,3,5,8-Tetramethyl-2,4-bis(a-hydroxyethyl)porphine-6,7-dipropionate</synonym>
    <synonym>1,3,5,8-Tetramethyl-2,4-bis(a-hydroxyethyl)porphine-6,7-dipropionic acid</synonym>
    <synonym>1,3,5,8-Tetramethyl-2,4-bis(alpha-hydroxyethyl)prophine-6,7-dipropionate</synonym>
    <synonym>1,3,5,8-Tetramethyl-2,4-bis(alpha-hydroxyethyl)prophine-6,7-dipropionic acid</synonym>
    <synonym>7,12-Bis(1-hydroxyethyl)-3,8,13,17-tetramethyl-2,18-porphinedipropionate</synonym>
    <synonym>7,12-Bis(1-hydroxyethyl)-3,8,13,17-tetramethyl-2,18-porphinedipropionic acid</synonym>
    <synonym>Haematoporphyrin</synonym>
    <synonym>Hematoporphyrin</synonym>
    <synonym>HP</synonym>
    <synonym>HpIX</synonym>
    <synonym>Photodyn</synonym>
    <synonym>3-[20-(2-Carboxyethyl)-10,15-bis(1-hydroxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C34H38N4O6</chemical_formula>
  <average_molecular_weight>598.6887</average_molecular_weight>
  <monisotopic_moleculate_weight>598.279134968</monisotopic_moleculate_weight>
  <iupac_name>3-[20-(2-carboxyethyl)-10,15-bis(1-hydroxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[20-(2-carboxyethyl)-10,15-bis(1-hydroxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>14459-29-1</cas_registry_number>
  <smiles>CC(O)C1=C2NC(\C=C3/N\C(=C/C4=N/C(=C\C5=N\C(=C/2)\C(C)=C5C(C)O)/C(C)=C4CCC(O)=O)C(CCC(O)=O)=C3C)=C1C</smiles>
  <inchi>InChI=1S/C34H38N4O6/c1-15-21(7-9-31(41)42)27-14-28-22(8-10-32(43)44)16(2)24(36-28)12-29-34(20(6)40)18(4)26(38-29)13-30-33(19(5)39)17(3)25(37-30)11-23(15)35-27/h11-14,19-20,35,37,39-40H,7-10H2,1-6H3,(H,41,42)(H,43,44)/b23-11-,24-12-,25-11-,26-13-,27-14-,28-14-,29-12-,30-13-</inchi>
  <inchikey>QXNKGOQXMZXHIB-AMPAVEGJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>172.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[20-(2-carboxyethyl)-10,15-bis(1-hydroxyethyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>598.6887</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>598.279134968</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(O)C1=C2NC(\C=C3/N\C(=C/C4=N/C(=C\C5=N\C(=C/2)\C(C)=C5C(C)O)/C(C)=C4CCC(O)=O)C(CCC(O)=O)=C3C)=C1C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C34H38N4O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C34H38N4O6/c1-15-21(7-9-31(41)42)27-14-28-22(8-10-32(43)44)16(2)24(36-28)12-29-34(20(6)40)18(4)26(38-29)13-30-33(19(5)39)17(3)25(37-30)11-23(15)35-27/h11-14,19-20,35,37,39-40H,7-10H2,1-6H3,(H,41,42)(H,43,44)/b23-11-,24-12-,25-11-,26-13-,27-14-,28-14-,29-12-,30-13-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QXNKGOQXMZXHIB-AMPAVEGJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>172.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>166.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>69.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327153</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022173</foodb_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <chemspider_id/>
  <pubchem_compound_id/>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Hematoporphyrin</wikipedia_id>
  <metlin_id>5638</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:38 UTC</creation_date>
  <update_date>2020-03-13 16:22:56 UTC</update_date>
  <accession>BMDB0000669</accession>
  <secondary_accessions>
    <accession>BMDB00669</accession>
  </secondary_accessions>
  <name>Ortho-Hydroxyphenylacetic acid</name>
  <description>Ortho-hydroxyphenylacetic acid, also known as (O-hydroxyphenyl)acetate or 2-hydroxybenzeneacetic acid, belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position. Ortho-hydroxyphenylacetic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Ortho-hydroxyphenylacetic acid exists in all living organisms, ranging from bacteria to humans. Ortho-hydroxyphenylacetic acid has been found to be associated with several diseases known as eosinophilic esophagitis and irritable bowel syndrome; also ortho-hydroxyphenylacetic acid has been linked to the inborn metabolic disorders including phenylketonuria.</description>
  <synonyms>
    <synonym>(O-Hydroxyphenyl)acetic acid</synonym>
    <synonym>2'-Hydroxyphenylacetic acid</synonym>
    <synonym>2-Hydroxybenzeneacetic acid</synonym>
    <synonym>2-Hydroxyphenylacetic acid</synonym>
    <synonym>O-Hydroxyphenylacetic acid</synonym>
    <synonym>(O-Hydroxyphenyl)acetate</synonym>
    <synonym>2'-Hydroxyphenylacetate</synonym>
    <synonym>2-Hydroxybenzeneacetate</synonym>
    <synonym>2-Hydroxyphenylacetate</synonym>
    <synonym>O-Hydroxyphenylacetate</synonym>
    <synonym>Ortho-hydroxyphenylacetate</synonym>
    <synonym>(2-Hydroxyphenyl)acetate</synonym>
    <synonym>(2-Hydroxyphenyl)acetic acid</synonym>
    <synonym>(O-Hydroxyphenyl)-acetate</synonym>
    <synonym>(O-Hydroxyphenyl)-acetic acid</synonym>
    <synonym>2-HPAA</synonym>
    <synonym>Hydroxyphenylacetate</synonym>
    <synonym>Hydroxyphenylacetic acid</synonym>
    <synonym>O-Hydroxyphenyl acetic acid</synonym>
    <synonym>Ortho-hydroxyphenylacetic acid</synonym>
  </synonyms>
  <chemical_formula>C8H8O3</chemical_formula>
  <average_molecular_weight>152.1473</average_molecular_weight>
  <monisotopic_moleculate_weight>152.047344122</monisotopic_moleculate_weight>
  <iupac_name>2-(2-hydroxyphenyl)acetic acid</iupac_name>
  <traditional_iupac>o-hydroxyphenylacetic acid</traditional_iupac>
  <cas_registry_number>614-75-5</cas_registry_number>
  <smiles>OC(=O)CC1=C(O)C=CC=C1</smiles>
  <inchi>InChI=1S/C8H8O3/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4,9H,5H2,(H,10,11)</inchi>
  <inchikey>CCVYRRGZDBSHFU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Phenylacetic acids</sub_class>
    <direct_parent>2(hydroxyphenyl)acetic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>2(hydroxyphenyl)acetic acid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>145 - 147 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>44 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.85</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(2-hydroxyphenyl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>152.1473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>152.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC1=C(O)C=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H8O3/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4,9H,5H2,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CCVYRRGZDBSHFU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>919</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439239</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB012331</foodb_id>
  <pubchem_compound_id>11970</pubchem_compound_id>
  <chemspider_id>11476</chemspider_id>
  <pdbe_id/>
  <kegg_id>C05852</kegg_id>
  <chebi_id>28478</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5639</metlin_id>
  <synthesis_reference>Levine, Joseph; Eble, T. E.; Fischbach, Henry. Preparation of o-hydroxyphenylacetic acid. Journal of the American Chemical Society (1948), 70 1930.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:39 UTC</creation_date>
  <update_date>2020-04-15 22:35:30 UTC</update_date>
  <accession>BMDB0000670</accession>
  <secondary_accessions>
    <accession>BMDB00670</accession>
  </secondary_accessions>
  <name>Homo-L-arginine</name>
  <description>Homo-L-arginine, also known as n6-amidino-lysine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Homo-L-arginine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Homo-L-arginine exists in all living organisms, ranging from bacteria to humans. Homo-L-arginine is a potentially toxic compound. Homo-L-arginine has been found to be associated with the diseases known as cirrhosis; also homo-l-arginine has been linked to the inborn metabolic disorders including hyperargininemia.</description>
  <synonyms>
    <synonym>Homoarginine</synonym>
    <synonym>L-N(6)-Amidinolysine</synonym>
    <synonym>N6-(Aminoiminomethyl)-L-lysine</synonym>
    <synonym>N6-Amidino-L-lysine</synonym>
    <synonym>N6-Amidino-lysine</synonym>
    <synonym>L-Homoarginine</synonym>
    <synonym>Homo-L-arginine</synonym>
  </synonyms>
  <chemical_formula>C7H16N4O2</chemical_formula>
  <average_molecular_weight>188.2275</average_molecular_weight>
  <monisotopic_moleculate_weight>188.127325776</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-6-carbamimidamidohexanoic acid</iupac_name>
  <traditional_iupac>L-homoarginine</traditional_iupac>
  <cas_registry_number>156-86-5</cas_registry_number>
  <smiles>N[C@@H](CCCCNC(N)=N)C(O)=O</smiles>
  <inchi>InChI=1S/C7H16N4O2/c8-5(6(12)13)3-1-2-4-11-7(9)10/h5H,1-4,8H2,(H,12,13)(H4,9,10,11)/t5-/m0/s1</inchi>
  <inchikey>QUOGESRFPZDMMT-YFKPBYRVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Guanidines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-lysine derivative</external_descriptor>
      <external_descriptor>homoarginine</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>213 - 215 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>12.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-6-carbamimidamidohexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>188.2275</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>188.127325776</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCCCNC(N)=N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H16N4O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H16N4O2/c8-5(6(12)13)3-1-2-4-11-7(9)10/h5H,1-4,8H2,(H,12,13)(H4,9,10,11)/t5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QUOGESRFPZDMMT-YFKPBYRVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>125.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>58.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>921</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>922</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>264618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>264619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>264620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>284547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>284548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>284549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446320</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB03974</drugbank_id>
  <foodb_id>FDB001490</foodb_id>
  <pubchem_compound_id>9085</pubchem_compound_id>
  <chemspider_id>8732</chemspider_id>
  <pdbe_id/>
  <kegg_id>C01924</kegg_id>
  <chebi_id>27747</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id>C00001364</knapsack_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5640</metlin_id>
  <synthesis_reference>Izumiya, Nobuo.  Synthesis of DL-homoarginine and Na-methyl-DL-homoarginine.    Nippon Kagaku Zasshi  (1951),  72  521-3.  CODEN: NPKZAZ  ISSN:0369-5387.  CAN 46:42183  AN 1952:42183</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:40 UTC</creation_date>
  <update_date>2020-04-14 22:48:02 UTC</update_date>
  <accession>BMDB0000671</accession>
  <secondary_accessions>
    <accession>BMDB00671</accession>
  </secondary_accessions>
  <name>Indolelactic acid</name>
  <description/>
  <synonyms>
    <synonym>Indolelactate</synonym>
    <synonym>3-(indol-3-yl) LACTic acid</synonym>
    <synonym>(2S)-2-Hydroxy-3-(1H-indol-3-yl)propanoic acid</synonym>
    <synonym>(2S)-2-Hydroxy-3-(1H-indol-3-yl)propionic acid</synonym>
    <synonym>(2S)-2-Hydroxy-3-indoylpropanoic acid</synonym>
    <synonym>(2S)-2-Hydroxy-3-indoylpropionic acid</synonym>
    <synonym>(S)-2-Hydroxy-3-(1H-indol-3-yl)propanoic acid</synonym>
    <synonym>(S)-2-Hydroxy-3-(1H-indol-3-yl)propionic acid</synonym>
    <synonym>(S)-Indole-3-lactic acid</synonym>
    <synonym>(AlphaS)-alpha-hydroxy-1H-indole-3-propanoic acid</synonym>
    <synonym>(AlphaS)-alpha-hydroxy-1H-indole-3-propionic acid</synonym>
    <synonym>(ΑS)-α-hydroxy-1H-indole-3-propanoic acid</synonym>
    <synonym>(ΑS)-α-hydroxy-1H-indole-3-propionic acid</synonym>
    <synonym>2-(1H-indol-3-yl)Acetaldehyde</synonym>
    <synonym>2-Hydroxy-3-(1H-indol-3-yl)propanoic acid</synonym>
    <synonym>2-Hydroxy-3-(1H-indol-3-yl)propionic acid</synonym>
    <synonym>2-Hydroxy-3-(3-indolyl)propanoic acid</synonym>
    <synonym>2-Hydroxy-3-(3-indolyl)propionic acid</synonym>
    <synonym>3-(3-Indolyl)-2-hydroxypropanoic acid</synonym>
    <synonym>3-(3-Indolyl)-2-hydroxypropionic acid</synonym>
    <synonym>3-(3-Indolyl)-DL-lactic acid</synonym>
    <synonym>3-Indolyllactic acid</synonym>
    <synonym>Indole-3-L-lactic acid</synonym>
    <synonym>Indole-3-lactic acid</synonym>
    <synonym>L-3-(3-Indolyl)lactic acid</synonym>
    <synonym>L-Indole-3-lactic acid</synonym>
    <synonym>alpha-Hydroxy-1H-indole-3-propanoic acid</synonym>
    <synonym>alpha-Hydroxy-1H-indole-3-propionic acid</synonym>
    <synonym>beta-(3-Indolyl)lactic acid</synonym>
    <synonym>beta-Indolyllactic acid</synonym>
    <synonym>Α-hydroxy-1H-indole-3-propanoic acid</synonym>
    <synonym>Α-hydroxy-1H-indole-3-propionic acid</synonym>
    <synonym>Β-(3-indolyl)lactic acid</synonym>
    <synonym>Β-indolyllactic acid</synonym>
    <synonym>Indolelactic acid</synonym>
  </synonyms>
  <chemical_formula>C11H11NO3</chemical_formula>
  <average_molecular_weight>205.2099</average_molecular_weight>
  <monisotopic_moleculate_weight>205.073893223</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid</iupac_name>
  <traditional_iupac>3-(indol-3-yl) lactate</traditional_iupac>
  <cas_registry_number>7417-65-4</cas_registry_number>
  <smiles>O[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O</smiles>
  <inchi>InChI=1S/C11H11NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,10,12-13H,5H2,(H,14,15)/t10-/m0/s1</inchi>
  <inchikey>XGILAAMKEQUXLS-JTQLQIEISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Indolyl carboxylic acids and derivatives</sub_class>
    <direct_parent>Indolyl carboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alkylindoles</alternative_parent>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alkylindole</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Indole</substituent>
      <substituent>Indolyl carboxylic acid derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>17 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>205.2099</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>205.073893223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H11NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H11NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,10,12-13H,5H2,(H,14,15)/t10-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XGILAAMKEQUXLS-JTQLQIEISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>73.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>254661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>254662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>254663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>274602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>274603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>274604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2066</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB07060</drugbank_id>
  <foodb_id>FDB022174</foodb_id>
  <pubchem_compound_id>676157</pubchem_compound_id>
  <chemspider_id>588900</chemspider_id>
  <pdbe_id/>
  <kegg_id>C02043</kegg_id>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>INDOLE_LACTATE</meta_cyc_id>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Narayanan, T. K.; Rao, G. Ramananda.  Beta-indoleethanol and beta-indolelactic acid production by Candida species:  Their antibacterial and autoantibiotic action.    Antimicrobial Agents and Chemotherapy  (1976),  9(3),  375-80.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:41 UTC</creation_date>
  <update_date>2020-03-13 16:22:57 UTC</update_date>
  <accession>BMDB0000672</accession>
  <secondary_accessions>
    <accession>BMDB00672</accession>
  </secondary_accessions>
  <name>Hexadecanedioic acid</name>
  <description/>
  <synonyms>
    <synonym>1,14-Tetradecanedicarboxylic acid</synonym>
    <synonym>1,16-Hexadecanedioic acid</synonym>
    <synonym>Thapsic acid</synonym>
    <synonym>1,14-Tetradecanedicarboxylate</synonym>
    <synonym>1,16-Hexadecanedioate</synonym>
    <synonym>Thapsate</synonym>
    <synonym>Hexadecanedioate</synonym>
    <synonym>Α,ω-tetrαdecαnedicαrboxylαte</synonym>
    <synonym>N-Tetradecane-ω,ω'-dicarboxylate</synonym>
    <synonym>N-Tetradecane-ω,ω'-dicarboxylic acid</synonym>
    <synonym>alpha,Omega-tetradecanedicarboxylic acid</synonym>
    <synonym>N-Tetradecane-omega,omega'-dicarboxylic acid</synonym>
    <synonym>N-Tetradecane-ω,ω’-dicarboxylic acid</synonym>
    <synonym>Α,ω-tetradecanedicarboxylic acid</synonym>
    <synonym>Hexadecanedioic acid</synonym>
  </synonyms>
  <chemical_formula>C16H30O4</chemical_formula>
  <average_molecular_weight>286.407</average_molecular_weight>
  <monisotopic_moleculate_weight>286.214409448</monisotopic_moleculate_weight>
  <iupac_name>hexadecanedioic acid</iupac_name>
  <traditional_iupac>hexadecanedioic acid</traditional_iupac>
  <cas_registry_number>505-54-4</cas_registry_number>
  <smiles>OC(=O)CCCCCCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C16H30O4/c17-15(18)13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(19)20/h1-14H2,(H,17,18)(H,19,20)</inchi>
  <inchikey>QQHJDPROMQRDLA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>alpha,omega-dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>120 - 123 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>hexadecanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>286.407</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>286.214409448</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCCCCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H30O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H30O4/c17-15(18)13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(19)20/h1-14H2,(H,17,18)(H,19,20)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QQHJDPROMQRDLA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>78.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347046</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB003049</foodb_id>
  <pubchem_compound_id>10459</pubchem_compound_id>
  <chemspider_id>10027</chemspider_id>
  <pdbe_id/>
  <kegg_id>C19615</kegg_id>
  <chebi_id>73722</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD-10511</meta_cyc_id>
  <knapsack_id>C00007429</knapsack_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5642</metlin_id>
  <synthesis_reference>Kreuchunas, Algird.  The synthesis of higher aliphatic a,w-dicarboxylic acids.    Journal of the American Chemical Society  (1953),  75  3339-44.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:43 UTC</creation_date>
  <update_date>2020-04-16 20:39:19 UTC</update_date>
  <accession>BMDB0000673</accession>
  <secondary_accessions>
    <accession>BMDB00673</accession>
  </secondary_accessions>
  <name>Linoleic acid</name>
  <description>Linoleic acid, also known as LA or linoleate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Linoleic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Linoleic acid exists in all living organisms, ranging from bacteria to humans. Linoleic acid is a potentially toxic compound. Linoleic acid has been found to be associated with several diseases known as hypertension, ulcerative colitis, essential hypertension, and thyroid cancer; also linoleic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.</description>
  <synonyms>
    <synonym>(9Z,12Z)-Octadecadienoic acid</synonym>
    <synonym>(Z,Z)-9,12-Octadecadienoic acid</synonym>
    <synonym>9-cis,12-cis-Octadecadienoic acid</synonym>
    <synonym>9Z,12Z-Octadecadienoic acid</synonym>
    <synonym>Acide cis-linoleique</synonym>
    <synonym>Acide linoleique</synonym>
    <synonym>Acido linoleico</synonym>
    <synonym>all-cis-9,12-Octadecadienoic acid</synonym>
    <synonym>C18:2 9C, 12C Omega6 todos cis-9,12-octadienoico</synonym>
    <synonym>C18:2, N-6,9 all-cis</synonym>
    <synonym>cis,cis-9,12-Octadecadienoic acid</synonym>
    <synonym>cis,cis-Linoleic acid</synonym>
    <synonym>cis-Delta(9,12)-Octadecadienoic acid</synonym>
    <synonym>LA</synonym>
    <synonym>Linolic acid</synonym>
    <synonym>9-cis,12-cis-Octadecadienoate</synonym>
    <synonym>(9Z,12Z)-Octadecadienoate</synonym>
    <synonym>(Z,Z)-9,12-Octadecadienoate</synonym>
    <synonym>9Z,12Z-Octadecadienoate</synonym>
    <synonym>all-cis-9,12-Octadecadienoate</synonym>
    <synonym>cis,cis-9,12-Octadecadienoate</synonym>
    <synonym>cis,cis-Linoleate</synonym>
    <synonym>cis-delta(9,12)-Octadecadienoate</synonym>
    <synonym>cis-Δ(9,12)-octadecadienoate</synonym>
    <synonym>cis-Δ(9,12)-octadecadienoic acid</synonym>
    <synonym>Linolate</synonym>
    <synonym>Linoleate</synonym>
    <synonym>(9Z,12Z)-9,12-Octadecadienoate</synonym>
    <synonym>(9Z,12Z)-9,12-Octadecadienoic acid</synonym>
    <synonym>9-cis,12-cis-Linoleate</synonym>
    <synonym>9-cis,12-cis-Linoleic acid</synonym>
    <synonym>9Z,12Z-Linoleate</synonym>
    <synonym>9Z,12Z-Linoleic acid</synonym>
    <synonym>cis-9,cis-12-Octadecadienoate</synonym>
    <synonym>cis-9,cis-12-Octadecadienoic acid</synonym>
    <synonym>cis-D9,12-Octadecadienoate</synonym>
    <synonym>cis-D9,12-Octadecadienoic acid</synonym>
    <synonym>Emersol 315</synonym>
    <synonym>Extra linoleic 90</synonym>
    <synonym>Polylin 515</synonym>
    <synonym>Unifac 6550</synonym>
    <synonym>Acid, 9,12-octadecadienoic</synonym>
    <synonym>Linoelaidic acid</synonym>
    <synonym>Linoleic acid, (e,e)-isomer</synonym>
    <synonym>Linoleic acid, (Z,Z)-isomer</synonym>
    <synonym>Linoleic acid, (Z,Z)-isomer, 14C-labeled</synonym>
    <synonym>Linoleic acid, ammonium salt, (Z,Z)-isomer</synonym>
    <synonym>Linoleic acid, potassium salt, (Z,Z)-isomer</synonym>
    <synonym>9 trans,12 trans Octadecadienoic acid</synonym>
    <synonym>9-trans,12-trans-Octadecadienoic acid</synonym>
    <synonym>Linoleic acid, sodium salt, (e,e)-isomer</synonym>
    <synonym>Linoleic acid, sodium salt, (Z,Z)-isomer</synonym>
    <synonym>trans,trans-9,12-Octadecadienoic acid</synonym>
    <synonym>9,12-Octadecadienoic acid</synonym>
    <synonym>Linoelaidic acid, (e,Z)-isomer</synonym>
    <synonym>Linoleic acid, calcium salt, (Z,Z)-isomer</synonym>
    <synonym>Linolelaidic acid</synonym>
    <synonym>9,12 Octadecadienoic acid</synonym>
    <synonym>Linoleic acid, (Z,e)-isomer</synonym>
    <synonym>FA(18:2(9Z,12Z))</synonym>
  </synonyms>
  <chemical_formula>C18H32O2</chemical_formula>
  <average_molecular_weight>280.4455</average_molecular_weight>
  <monisotopic_moleculate_weight>280.240230268</monisotopic_moleculate_weight>
  <iupac_name>(9Z,12Z)-octadeca-9,12-dienoic acid</iupac_name>
  <traditional_iupac>linoleic</traditional_iupac>
  <cas_registry_number>60-33-3</cas_registry_number>
  <smiles>CCCCC\C=C/C\C=C/CCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-</inchi>
  <inchikey>OYHQOLUKZRVURQ-HZJYTTRNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Lineolic acids and derivatives</sub_class>
    <direct_parent>Lineolic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Octadecanoid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Polyunsaturated fatty acids</external_descriptor>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>octadecadienoic acid</external_descriptor>
      <external_descriptor>omega-6 fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-8.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.05</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(9Z,12Z)-octadeca-9,12-dienoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>280.4455</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>280.240230268</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC\C=C/C\C=C/CCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H32O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OYHQOLUKZRVURQ-HZJYTTRNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>88.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alpha Linolenic Acid and Linoleic Acid Metabolism</name>
      <smpdb_id>SMP0087171</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4368</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373604</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.04 +/- 0.14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12.4 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.56 +/- 1.06</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk from a Danish Holstein herd by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.03 +/- 1.06</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised whole milk (3.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.17 +/- 0.53</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised semi skimmed milk (1.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>213.945</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
          <pubmed_id>1779072</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>178.288</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9.49 +/- 0.08</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>213.945</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2567.344</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3779.701</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3779.701</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3209.185 +/- 1069.728</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
          <pubmed_id>16899705</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1854.196 +/- 392.234</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2816.952 +/- 677.495</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1747.223 +/- 356.576</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2674.321 +/- 570.522</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21394.531</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>26386.588</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27456.315</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28882.617</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples have been collected from Heifer cows.</comment>
      <references>
        <reference>
          <reference_text>Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub  2013 Jun 5.</reference_text>
          <pubmed_id>23871026</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Oocyte</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by CP9010 autosampler onto a capillary column within a CP9001 gas chromatograph in slaughtered cow ovaries.</comment>
      <references>
        <reference>
          <reference_text>McEvoy TG, Coull GD, Broadbent PJ, Hutchinson JS, Speake BK: Fatty acid composition of lipids in immature cattle, pig and sheep oocytes with intact zona pellucida. J Reprod Fertil. 2000 Jan;118(1):163-70.</reference_text>
          <pubmed_id>10793638</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>3.5 +/- 2.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB006562</foodb_id>
  <pubchem_compound_id>5280450</pubchem_compound_id>
  <chemspider_id>4444105</chemspider_id>
  <pdbe_id/>
  <kegg_id>C01595</kegg_id>
  <chebi_id>17351</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>LINOLEIC_ACID</meta_cyc_id>
  <knapsack_id>C00001224</knapsack_id>
  <bigg_id>37956</bigg_id>
  <wikipedia_id>Linoleic_acid</wikipedia_id>
  <metlin_id>191</metlin_id>
  <synthesis_reference>Walborsky, Harry M.; Davis, Robert H.; Howton, David R. A total synthesis of linoleic acid. Journal of the American Chemical Society (1951), 73 2590-4.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
      <pubmed_id>16899705</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Auldist MJ, Walsh BJ, Thomson NA: Seasonal and lactational influences on bovine milk composition in New Zealand. J Dairy Res. 1998 Aug;65(3):401-11.</reference_text>
      <pubmed_id>9718493</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
      <pubmed_id>1779072</pubmed_id>
    </reference>
    <reference>
      <reference_text>Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.</reference_text>
      <pubmed_id>20855010</pubmed_id>
    </reference>
    <reference>
      <reference_text>Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93.</reference_text>
      <pubmed_id>5409465</pubmed_id>
    </reference>
    <reference>
      <reference_text>van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.</reference_text>
      <pubmed_id>28219465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
    </reference>
    <reference>
      <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
    </reference>
    <reference>
      <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:44 UTC</creation_date>
  <update_date>2020-03-13 16:22:58 UTC</update_date>
  <accession>BMDB0000674</accession>
  <secondary_accessions>
    <accession>BMDB00674</accession>
  </secondary_accessions>
  <name>PA(16:0/16:0)</name>
  <description/>
  <synonyms>
    <synonym>1,2-Dipalmitoyl-3-sn-phosphatidic acid</synonym>
    <synonym>1,2-Dipalmitoyl-sn-glycerol-3-phosphate</synonym>
    <synonym>1,2-Dipalmitoyl-sn-glycerol-3-phosphoric acid</synonym>
    <synonym>Dipalmitoyl phosphatidic acid</synonym>
    <synonym>PA(32:0)</synonym>
    <synonym>Phosphatidic acid(16:0/16:0)</synonym>
    <synonym>Phosphatidic acid(32:0)</synonym>
    <synonym>1,2-Dipalmitoyl-3-sn-phosphatidate</synonym>
    <synonym>Dipalmitoyl phosphatidate</synonym>
    <synonym>Phosphatidate(16:0/16:0)</synonym>
    <synonym>Phosphatidate(32:0)</synonym>
    <synonym>1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphorate</synonym>
    <synonym>1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphoric acid</synonym>
    <synonym>1,2-Dihexadecanoyl-rac-phosphatidic acid</synonym>
    <synonym>1,2-Dipalmitoyl-sn-glycerol 3-phosphate</synonym>
    <synonym>1,2-Dipalmitoyl-sn-glycerol-3-phosphorate</synonym>
    <synonym>Dipalmitoyl-L-a-phosphatidate</synonym>
    <synonym>Dipalmitoyl-L-a-phosphatidic acid</synonym>
    <synonym>Dipalmitoyl-L-alpha-phosphatidate</synonym>
    <synonym>Dipalmitoyl-L-alpha-phosphatidic acid</synonym>
    <synonym>Dipalmitoylphosphatidate</synonym>
    <synonym>Dipalmitoylphosphatidic acid</synonym>
    <synonym>L-a-Dipalmitoyl-phosphatidate</synonym>
    <synonym>L-a-Dipalmitoyl-phosphatidic acid</synonym>
    <synonym>L-a-Dipalmitoylphosphatidate</synonym>
    <synonym>L-a-Dipalmitoylphosphatidic acid</synonym>
    <synonym>L-alpha-Dipalmitoyl-phosphatidate</synonym>
    <synonym>L-alpha-Dipalmitoyl-phosphatidic acid</synonym>
    <synonym>L-alpha-Dipalmitoylphosphatidate</synonym>
    <synonym>L-alpha-Dipalmitoylphosphatidic acid</synonym>
    <synonym>Dipalmitoylphosphatidic acid, calcium salt</synonym>
    <synonym>Dipalmitoylphosphatidic acid, ammonium salt</synonym>
    <synonym>1,2-Dipalmitoyl-sn-glycero-3-phosphate</synonym>
    <synonym>Dipalmitoylphosphatidic acid, sodium salt</synonym>
    <synonym>Dipalmitoylphosphatidic acid, (+-)-isomer</synonym>
    <synonym>Dipalmitoylphosphatidic acid, (R)-isomer</synonym>
  </synonyms>
  <chemical_formula>C35H69O8P</chemical_formula>
  <average_molecular_weight>648.903</average_molecular_weight>
  <monisotopic_moleculate_weight>648.47300618</monisotopic_moleculate_weight>
  <iupac_name>[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphonic acid</iupac_name>
  <traditional_iupac>dipalmitoyl</traditional_iupac>
  <cas_registry_number>7091-44-3</cas_registry_number>
  <smiles>[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC</smiles>
  <inchi>InChI=1S/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40)/t33-/m1/s1</inchi>
  <inchikey>PORPENFLTBBHSG-MGBGTMOVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Glycerophospholipids</class>
    <sub_class>Glycerophosphates</sub_class>
    <direct_parent>1,2-diacylglycerol-3-phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diacylglycerol-3-phosphate</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>1-acyl-2-hexadecanoyl-sn-glycero-3-phosphate</external_descriptor>
      <external_descriptor>Diacylglycerophosphates</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>161 - 165 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>8.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>11.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>648.903</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>648.47300618</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C35H69O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40)/t33-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PORPENFLTBBHSG-MGBGTMOVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>119.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>178.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>80.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:0)</name>
      <smpdb_id>SMP0077151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:0)</name>
      <smpdb_id>SMP0077153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:0)</name>
      <smpdb_id>SMP0077171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:0)</name>
      <smpdb_id>SMP0077173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:0)</name>
      <smpdb_id>SMP0073871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:0)</name>
      <smpdb_id>SMP0073873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:0)</name>
      <smpdb_id>SMP0073880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:0)</name>
      <smpdb_id>SMP0073888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/24:0)</name>
      <smpdb_id>SMP0073895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332394</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022175</foodb_id>
  <pubchem_compound_id>446066</pubchem_compound_id>
  <chemspider_id>393518</chemspider_id>
  <pdbe_id/>
  <kegg_id>C00416</kegg_id>
  <chebi_id>73246</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD0-1422</meta_cyc_id>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5644</metlin_id>
  <synthesis_reference>Ando, Yoshihiro; Oda, Hiroshi; Matsuyoshi, Shigeru; Maekawa, Naoya.  Manufacture of phosphatidic acid alkali metal or ammonium salts using phospholipase D. Jpn. Kokai Tokkyo Koho  (2001),   8 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:45 UTC</creation_date>
  <update_date>2020-03-13 16:22:59 UTC</update_date>
  <accession>BMDB0000675</accession>
  <secondary_accessions>
    <accession>BMDB00675</accession>
  </secondary_accessions>
  <name>Iodine</name>
  <description>Iodine, also known as I2 or Jod, belongs to the class of inorganic compounds known as homogeneous halogens. These are inorganic non-metallic compounds in which the largest atom is a nobel gas. Iodine exists as a solid, possibly soluble (in water), and possibly neutral molecule. Iodine exists in all living organisms, ranging from bacteria to humans. In cattle, iodine is involved in the metabolic pathway called thyroid hormone synthesis pathway. Iodine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>I2</synonym>
    <synonym>Jod</synonym>
    <synonym>Molecular iodine</synonym>
    <synonym>Diiodine</synonym>
    <synonym>Cadex</synonym>
    <synonym>Iode</synonym>
    <synonym>Iodine-molecule</synonym>
    <synonym>Iodio</synonym>
    <synonym>Iodum</synonym>
    <synonym>Jood</synonym>
    <synonym>Tincture iodine</synonym>
    <synonym>Iodine 127</synonym>
    <synonym>Iodine-127</synonym>
    <synonym>Iodine</synonym>
  </synonyms>
  <chemical_formula>I2</chemical_formula>
  <average_molecular_weight>253.8089</average_molecular_weight>
  <monisotopic_moleculate_weight>253.80893684</monisotopic_moleculate_weight>
  <iupac_name>diiodine</iupac_name>
  <traditional_iupac>iodine</traditional_iupac>
  <cas_registry_number>7553-56-2</cas_registry_number>
  <smiles>II</smiles>
  <inchi>InChI=1S/I2/c1-2</inchi>
  <inchikey>PNDPGZBMCMUPRI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous halogens. These are inorganic non-metallic compounds in which the largest atom is a nobel gas.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Homogeneous halogens</class>
    <sub_class/>
    <direct_parent>Homogeneous halogens</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous halogen</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>an inorganic compound</external_descriptor>
      <external_descriptor>diatomic iodine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>113.6 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.33 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.49</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>diiodine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>253.8089</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>253.80893684</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>II</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>I2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/I2/c1-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PNDPGZBMCMUPRI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>26.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25645</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0867</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>From Niger</comment>
      <references>
        <reference>
          <reference_text>Aquaron R, Aquaron C, Daouda H, Madi N, Roux F, Bisset JP: [Study of two goitrous endemic areas in Niger: Belley-Koira and Tiguey-Tallawal]. Ann Endocrinol (Paris). 1990;51(5-6):231-40.</reference_text>
          <pubmed_id>1966663</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.827</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0236 - 0.130</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from Morrocco</comment>
      <references>
        <reference>
          <reference_text>Aquaron R, Zarrouck K, el Jarari M, Ababou R, Talibi A, Ardissone JP: Endemic goiter in Morocco (Skoura-Toundoute areas in the high atlas). J Endocrinol Invest. 1993 Jan;16(1):9-14.</reference_text>
          <pubmed_id>8445160</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.705</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.355</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.957</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.918</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.355</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.957</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.957</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.658</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB05382</drugbank_id>
  <foodb_id>FDB003635</foodb_id>
  <kegg_id>C01382</kegg_id>
  <pubchem_compound_id>807</pubchem_compound_id>
  <chemspider_id/>
  <pdbe_id/>
  <chebi_id>17606</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Iodine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Aquaron R, Aquaron C, Daouda H, Madi N, Roux F, Bisset JP: [Study of two goitrous endemic areas in Niger: Belley-Koira and Tiguey-Tallawal]. Ann Endocrinol (Paris). 1990;51(5-6):231-40.</reference_text>
      <pubmed_id>1966663</pubmed_id>
    </reference>
    <reference>
      <reference_text>Aquaron R, Zarrouck K, el Jarari M, Ababou R, Talibi A, Ardissone JP: Endemic goiter in Morocco (Skoura-Toundoute areas in the high atlas). J Endocrinol Invest. 1993 Jan;16(1):9-14.</reference_text>
      <pubmed_id>8445160</pubmed_id>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:46 UTC</creation_date>
  <update_date>2020-03-13 16:22:59 UTC</update_date>
  <accession>BMDB0000676</accession>
  <secondary_accessions>
    <accession>BMDB00676</accession>
  </secondary_accessions>
  <name>L-Homocystine</name>
  <description/>
  <synonyms>
    <synonym>4,4'-Dithiobis(2-aminobutyric acid)</synonym>
    <synonym>4,4'-Dithiobis-2-amino-L-butyrate</synonym>
    <synonym>4,4'-Dithiobis-2-amino-L-butyric acid</synonym>
    <synonym>[S-(R*,r*)]-4,4'-dithiobis-2-amino-butanoate</synonym>
    <synonym>[S-(R*,r*)]-4,4'-dithiobis-2-amino-butanoic acid</synonym>
    <synonym>2-Amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoate</synonym>
    <synonym>2-Amino-4-{[(3S)-3-amino-3-carboxypropyl]disulphanyl}butanoate</synonym>
    <synonym>2-Amino-4-{[(3S)-3-amino-3-carboxypropyl]disulphanyl}butanoic acid</synonym>
  </synonyms>
  <chemical_formula>C8H16N2O4S2</chemical_formula>
  <average_molecular_weight>268.354</average_molecular_weight>
  <monisotopic_moleculate_weight>268.05514839</monisotopic_moleculate_weight>
  <iupac_name>2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid</iupac_name>
  <traditional_iupac>2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid</traditional_iupac>
  <cas_registry_number>626-72-2</cas_registry_number>
  <smiles>NC(CCSSCC[C@H](N)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)/t5-,6?/m0/s1</inchi>
  <inchikey>ZTVZLYBCZNMWCF-ZBHICJROSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkyldisulfides</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dialkyldisulfide</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Organic disulfide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thia fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>300 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.2 mg/mL at 25 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-4.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>268.354</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>268.05514839</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CCSSCC[C@H](N)C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16N2O4S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)/t5-,6?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZTVZLYBCZNMWCF-ZBHICJROSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>126.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>64.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343002</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022176</foodb_id>
  <kegg_id>C01817</kegg_id>
  <chemspider_id>62590</chemspider_id>
  <pdbe_id/>
  <chebi_id>89698</chebi_id>
  <pubchem_compound_id>69382</pubchem_compound_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Homocystine</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:47 UTC</creation_date>
  <update_date>2020-03-13 16:23:00 UTC</update_date>
  <accession>BMDB0000678</accession>
  <secondary_accessions>
    <accession>BMDB00678</accession>
  </secondary_accessions>
  <name>Isovalerylglycine</name>
  <description/>
  <synonyms>
    <synonym>2-(3-Methylbutanoylamino)ethanoic acid</synonym>
    <synonym>Isopentanoylglycine</synonym>
    <synonym>N-Isopentanoylglycine</synonym>
    <synonym>N-Isovaleroylglycine</synonym>
    <synonym>2-(3-Methylbutanoylamino)ethanoate</synonym>
    <synonym>3-Methylbutyrylglycine</synonym>
    <synonym>N-Isovaleryl-glycine</synonym>
    <synonym>[(3-Methylbutanoyl)amino]acetate</synonym>
    <synonym>[(3-Methylbutanoyl)amino]acetic acid</synonym>
    <synonym>N-Isovalerylglycine</synonym>
    <synonym>Isovalerylglycine</synonym>
  </synonyms>
  <chemical_formula>C7H13NO3</chemical_formula>
  <average_molecular_weight>159.183</average_molecular_weight>
  <monisotopic_moleculate_weight>159.089543287</monisotopic_moleculate_weight>
  <iupac_name>2-(3-methylbutanamido)acetic acid</iupac_name>
  <traditional_iupac>isovalerylglycine</traditional_iupac>
  <cas_registry_number>16284-60-9</cas_registry_number>
  <smiles>CC(C)CC(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C7H13NO3/c1-5(2)3-6(9)8-4-7(10)11/h5H,3-4H2,1-2H3,(H,8,9)(H,10,11)</inchi>
  <inchikey>ZRQXMKMBBMNNQC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylglycine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>87 - 90 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(3-methylbutanamido)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>159.183</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>159.089543287</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CC(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H13NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H13NO3/c1-5(2)3-6(9)8-4-7(10)11/h5H,3-4H2,1-2H3,(H,8,9)(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZRQXMKMBBMNNQC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>371299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>371300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>371301</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022177</foodb_id>
  <kegg_id/>
  <chemspider_id>475516</chemspider_id>
  <pdbe_id/>
  <chebi_id>70984</chebi_id>
  <pubchem_compound_id>546304</pubchem_compound_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5647</metlin_id>
  <synthesis_reference>Bondi, S.; Eissler, F.  Lipoproteins and the Fatty Degeneration of Cells.    Biochemische Zeitschrift  (1910),  23  499-513.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:48 UTC</creation_date>
  <update_date>2020-04-14 22:48:03 UTC</update_date>
  <accession>BMDB0000679</accession>
  <secondary_accessions>
    <accession>BMDB00679</accession>
  </secondary_accessions>
  <name>Homocitrulline</name>
  <description/>
  <synonyms>
    <synonym>N(6)-(Aminocarbonyl)-L-lysine</synonym>
    <synonym>Homo-L-citrulline</synonym>
    <synonym>L-Homocitrulline</synonym>
    <synonym>N-e-Carbamyl-L-lysine</synonym>
    <synonym>N-epsilon-Carbamyl-L-lysine</synonym>
    <synonym>N6-Carbamoyl-L-lysine</synonym>
    <synonym>N6-Carbamoyl-lysine</synonym>
    <synonym>Ureidocaproic acid</synonym>
    <synonym>(S)-2-Amino-6-ureidohexanoic acid</synonym>
    <synonym>N-Ε-carbamyl-L-lysine</synonym>
    <synonym>N6-(Aminocarbonyl)-L-lysine</synonym>
    <synonym>Homocitrulline</synonym>
  </synonyms>
  <chemical_formula>C7H15N3O3</chemical_formula>
  <average_molecular_weight>189.2123</average_molecular_weight>
  <monisotopic_moleculate_weight>189.111341361</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-6-(carbamoylamino)hexanoic acid</iupac_name>
  <traditional_iupac>homocitrulline</traditional_iupac>
  <cas_registry_number>1190-49-4</cas_registry_number>
  <smiles>N[C@@H](CCCCNC(N)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C7H15N3O3/c8-5(6(11)12)3-1-2-4-10-7(9)13/h5H,1-4,8H2,(H,11,12)(H3,9,10,13)/t5-/m0/s1</inchi>
  <inchikey>XIGSAGMEBXLVJJ-YFKPBYRVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonic acid derivative</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Urea</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-lysine derivative</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
      <external_descriptor>ureas</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>211 - 212 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>600 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-6-(carbamoylamino)hexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>189.2123</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>189.111341361</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCCCNC(N)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H15N3O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H15N3O3/c8-5(6(11)12)3-1-2-4-10-7(9)13/h5H,1-4,8H2,(H,11,12)(H3,9,10,13)/t5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XIGSAGMEBXLVJJ-YFKPBYRVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>944</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361329</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022178</foodb_id>
  <kegg_id>C02427</kegg_id>
  <chemspider_id>58582</chemspider_id>
  <pdbe_id/>
  <chebi_id>17443</chebi_id>
  <pubchem_compound_id>65072</pubchem_compound_id>
  <meta_cyc_id>CPD-161</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Homocitrulline</wikipedia_id>
  <metlin_id>46</metlin_id>
  <synthesis_reference>Stark, George R.  Reactions of cyanate with functional groups of proteins. III. Reactions with amino and carboxyl groups.    Biochemistry  (1965),  4(6),  1030-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:49 UTC</creation_date>
  <update_date>2020-04-16 17:51:20 UTC</update_date>
  <accession>BMDB0000682</accession>
  <secondary_accessions>
    <accession>BMDB00682</accession>
  </secondary_accessions>
  <name>Indoxyl sulfate</name>
  <description/>
  <synonyms>
    <synonym>3-Indolyl hydrogen sulfate</synonym>
    <synonym>3-Indolyl sulfate</synonym>
    <synonym>3-Indoxyl sulfate</synonym>
    <synonym>3-Indoxylsulfuric acid</synonym>
    <synonym>Indican</synonym>
    <synonym>indol-3-yl Hydrogen sulfate</synonym>
    <synonym>indol-3-yl Sulfate</synonym>
    <synonym>indol-3-yl Sulphate</synonym>
    <synonym>Indoxyl sulfic acid</synonym>
    <synonym>Indoxyl sulphate</synonym>
    <synonym>Indoxyl-3-sulphate</synonym>
    <synonym>Indoxylsulfuric acid</synonym>
    <synonym>3-Indolyl hydrogen sulfuric acid</synonym>
    <synonym>3-Indolyl hydrogen sulphate</synonym>
    <synonym>3-Indolyl hydrogen sulphuric acid</synonym>
    <synonym>3-Indolyl sulfuric acid</synonym>
    <synonym>3-Indolyl sulphate</synonym>
    <synonym>3-Indolyl sulphuric acid</synonym>
    <synonym>3-Indoxyl sulfuric acid</synonym>
    <synonym>3-Indoxyl sulphate</synonym>
    <synonym>3-Indoxyl sulphuric acid</synonym>
    <synonym>3-Indoxylsulfate</synonym>
    <synonym>3-Indoxylsulphate</synonym>
    <synonym>3-Indoxylsulphuric acid</synonym>
    <synonym>indol-3-yl Hydrogen sulfuric acid</synonym>
    <synonym>indol-3-yl Hydrogen sulphate</synonym>
    <synonym>indol-3-yl Hydrogen sulphuric acid</synonym>
    <synonym>indol-3-yl Sulfuric acid</synonym>
    <synonym>indol-3-yl Sulphuric acid</synonym>
    <synonym>Indoxyl sulfuric acid</synonym>
    <synonym>Indoxyl sulphuric acid</synonym>
    <synonym>Indoxyl-3-sulfate</synonym>
    <synonym>Indoxyl-3-sulfuric acid</synonym>
    <synonym>Indoxyl-3-sulphuric acid</synonym>
    <synonym>Indoxylsulfate</synonym>
    <synonym>Indoxylsulphate</synonym>
    <synonym>Indoxylsulphuric acid</synonym>
    <synonym>1H-indol-3-yl Hydrogen sulfate</synonym>
    <synonym>1H-indol-3-yl Hydrogen sulphate</synonym>
    <synonym>indol-3-Ol</synonym>
    <synonym>Indican monosodium salt</synonym>
    <synonym>Monopotassium salt, indican</synonym>
    <synonym>Monosodium salt, indican</synonym>
    <synonym>Sulfate, indoxyl</synonym>
    <synonym>Indican monopotassium salt</synonym>
    <synonym>1H-indol-3-Ol hydrogen sulfate ester</synonym>
    <synonym>Indoxyl sulfate</synonym>
    <synonym>3-Sulphooxy-1H-indole</synonym>
  </synonyms>
  <chemical_formula>C8H7NO4S</chemical_formula>
  <average_molecular_weight>213.21</average_molecular_weight>
  <monisotopic_moleculate_weight>213.009578407</monisotopic_moleculate_weight>
  <iupac_name>(1H-indol-3-yl)oxidanesulfonic acid</iupac_name>
  <traditional_iupac>3-sulfooxy-1H-indole</traditional_iupac>
  <cas_registry_number>487-94-5</cas_registry_number>
  <smiles>OS(=O)(=O)OC1=CNC2=CC=CC=C12</smiles>
  <inchi>InChI=1S/C8H7NO4S/c10-14(11,12)13-8-5-9-7-4-2-1-3-6(7)8/h1-5,9H,(H,10,11,12)</inchi>
  <inchikey>BXFFHSIDQOFMLE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as arylsulfates. These are organic compounds containing a sulfate group that carries an aryl group through an ether group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic sulfuric acids and derivatives</class>
    <sub_class>Arylsulfates</sub_class>
    <direct_parent>Arylsulfates</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Indoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Arylsulfate</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indole</substituent>
      <substituent>Indole or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aryl sulfate</external_descriptor>
      <external_descriptor>indoles</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1H-indol-3-yl)oxidanesulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>213.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>213.009578407</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OS(=O)(=O)OC1=CNC2=CC=CC=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H7NO4S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H7NO4S/c10-14(11,12)13-8-5-9-7-4-2-1-3-6(7)8/h1-5,9H,(H,10,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BXFFHSIDQOFMLE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>79.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>49.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251480</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB07992</drugbank_id>
  <foodb_id>FDB022179</foodb_id>
  <kegg_id/>
  <chemspider_id>9840</chemspider_id>
  <pdbe_id/>
  <chebi_id>43355</chebi_id>
  <pubchem_compound_id>10258</pubchem_compound_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Indoxyl sulfate</wikipedia_id>
  <metlin_id>524</metlin_id>
  <synthesis_reference>Robertson, Alexander.  Synthesis of glucosides. I. Synthesis of indican.    Journal of the Chemical Society  (1927),     1937-43.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:51 UTC</creation_date>
  <update_date>2020-04-15 22:14:18 UTC</update_date>
  <accession>BMDB0000683</accession>
  <secondary_accessions>
    <accession>BMDB00683</accession>
  </secondary_accessions>
  <name>Harderoporphyrin</name>
  <description/>
  <synonyms>
    <synonym>3,8,13,17-Tetramethyl-12-vinyl-2,7,18-porphinetripropionate</synonym>
    <synonym>3,8,13,17-Tetramethyl-12-vinyl-2,7,18-porphinetripropionic acid</synonym>
    <synonym>4,6,7-Tris(2-carboxyethyl)-1,3,5,8-tetramethyl-2-vinylporphyrin</synonym>
    <synonym>3-[15,20-Bis(2-carboxyethyl)-10-ethenyl-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C35H36N4O6</chemical_formula>
  <average_molecular_weight>608.6835</average_molecular_weight>
  <monisotopic_moleculate_weight>608.263484904</monisotopic_moleculate_weight>
  <iupac_name>3-[15,19-bis(2-carboxyethyl)-9-ethenyl-5,10,14,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[15,19-bis(2-carboxyethyl)-9-ethenyl-5,10,14,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>30783-27-8</cas_registry_number>
  <smiles>CC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(CCC(O)=O)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O</smiles>
  <inchi>InChI=1S/C35H36N4O6/c1-6-21-17(2)25-13-26-18(3)23(8-11-34(42)43)31(37-26)16-32-24(9-12-35(44)45)20(5)28(39-32)15-30-22(7-10-33(40)41)19(4)27(38-30)14-29(21)36-25/h6,13-16,36,39H,1,7-12H2,2-5H3,(H,40,41)(H,42,43)(H,44,45)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-</inchi>
  <inchikey>KECOXFKVIHSIBO-UJJXFSCMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[15,19-bis(2-carboxyethyl)-9-ethenyl-5,10,14,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>608.6835</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>608.263484904</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(CCC(O)=O)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C35H36N4O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C35H36N4O6/c1-6-21-17(2)25-13-26-18(3)23(8-11-34(42)43)31(37-26)16-32-24(9-12-35(44)45)20(5)28(39-32)15-30-22(7-10-33(40)41)19(4)27(38-30)14-29(21)36-25/h6,13-16,36,39H,1,7-12H2,2-5H3,(H,40,41)(H,42,43)(H,44,45)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KECOXFKVIHSIBO-UJJXFSCMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>169.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>170.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>69.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370560</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022180</foodb_id>
  <drugbank_id/>
  <chemspider_id>2339065</chemspider_id>
  <pubchem_compound_id/>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5652</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:52 UTC</creation_date>
  <update_date>2020-04-16 20:36:51 UTC</update_date>
  <accession>BMDB0000684</accession>
  <secondary_accessions>
    <accession>BMDB00684</accession>
  </secondary_accessions>
  <name>L-Kynurenine</name>
  <description>L-Kynurenine, also known as quinurenine, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. L-Kynurenine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Kynurenine exists in all eukaryotes, ranging from yeast to humans. L-Kynurenine participates in a number of enzymatic reactions, within cattle. In particular, L-Kynurenine and formic acid can be biosynthesized from n'-formylkynurenine; which is mediated by the enzyme kynurenine formamidase. In addition, L-Kynurenine can be converted into 2-aminobenzoic acid and L-alanine through the action of the enzyme kynureninase. In cattle, L-kynurenine is involved in the metabolic pathway called the tryptophan metabolism pathway.</description>
  <synonyms>
    <synonym>(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid</synonym>
    <synonym>3-Anthraniloyl-L-alanine</synonym>
    <synonym>KYNURENINE</synonym>
    <synonym>(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoate</synonym>
    <synonym>(AlphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-benzenebutanoate</synonym>
    <synonym>(AlphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-benzenebutanoic acid</synonym>
    <synonym>(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoate</synonym>
    <synonym>(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoic acid</synonym>
    <synonym>3-(3-Hydroxyanthraniloyl)-L-alanine</synonym>
    <synonym>3-Anthraniloyl-alanine</synonym>
    <synonym>3-Anthraniloylalanine</synonym>
    <synonym>3-Hydroxy-L-kynurenine</synonym>
    <synonym>alpha,2-Diamino-gamma-oxo-benzenebutanoate</synonym>
    <synonym>alpha,2-Diamino-gamma-oxo-benzenebutanoic acid</synonym>
    <synonym>DL-Kynurenine</synonym>
    <synonym>DL-Kynureninefree base</synonym>
    <synonym>Kynurenin</synonym>
    <synonym>Quinurenine</synonym>
  </synonyms>
  <chemical_formula>C10H12N2O3</chemical_formula>
  <average_molecular_weight>208.2139</average_molecular_weight>
  <monisotopic_moleculate_weight>208.08479226</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid</iupac_name>
  <traditional_iupac>L-kynurenine</traditional_iupac>
  <cas_registry_number>2922-83-0</cas_registry_number>
  <smiles>N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O</smiles>
  <inchi>InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1</inchi>
  <inchikey>YGPSJZOEDVAXAB-QMMMGPOBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Alkyl-phenylketones</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Aryl alkyl ketones</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Beta-amino ketones</alternative_parent>
      <alternative_parent>Butyrophenones</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Gamma-keto acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkyl-phenylketone</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl alkyl ketone</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Beta-aminoketone</substituent>
      <substituent>Butyrophenone</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Gamma-keto acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Keto acid</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>kynurenine</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>191 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>208.2139</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>208.08479226</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YGPSJZOEDVAXAB-QMMMGPOBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>106.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>55.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4871</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439556</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.5-2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>HPLC with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Bochniarz M, Kocki T, Dabrowski R, Szczubial M, Wawron W, Turski WA: Tryptophan, kynurenine, kynurenic acid concentrations and indoleamine 2,3-dioxygenase activity in serum and milk of dairy cows with subclinical mastitis caused by coagulase-negative staphylococci. Reprod Domest Anim. 2018 Dec;53(6):1491-1497. doi: 10.1111/rda.13299. Epub 2018 Aug 28.</reference_text>
          <pubmed_id>30066969</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>7+/-2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>3.9-7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Sadri H, von Soosten D, Meyer U, Kluess J, Danicke S, Saremi B, Sauerwein H: Plasma amino acids and metabolic profiling of dairy cows in response to a bolus duodenal infusion of leucine. PLoS One. 2017 Apr 28;12(4):e0176647. doi: 10.1371/journal.pone.0176647. eCollection 2017.</reference_text>
          <pubmed_id>28453535</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>3+/-2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>0.6+/-0.2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>20.2 +/- 0.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>20.23 +/- 0.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>0.5+/-0.2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>0.9+/-0.4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB02070</drugbank_id>
  <foodb_id>FDB022181</foodb_id>
  <kegg_id>C00328</kegg_id>
  <chemspider_id>141580</chemspider_id>
  <pdbe_id/>
  <chebi_id>16946</chebi_id>
  <pubchem_compound_id>161166</pubchem_compound_id>
  <meta_cyc_id>CPD-14736</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007604</knapsack_id>
  <bigg_id>1445574</bigg_id>
  <wikipedia_id>Kynurenine</wikipedia_id>
  <metlin_id>72</metlin_id>
  <synthesis_reference>Hayaishi, Osamu. L-Kynurenine sulfate monohydrate. Biochemical Preparations (1953), 3 108-11.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00239</protein_accession>
      <name>Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial</name>
      <uniprot_id>Q5E9N4</uniprot_id>
      <gene_name>AADAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00861</protein_accession>
      <name>Kynurenine--oxoglutarate transaminase 3</name>
      <uniprot_id>Q0P5G4</uniprot_id>
      <gene_name>CCBL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:53 UTC</creation_date>
  <update_date>2020-04-15 22:14:19 UTC</update_date>
  <accession>BMDB0000686</accession>
  <secondary_accessions>
    <accession>BMDB00686</accession>
  </secondary_accessions>
  <name>Isoursodeoxycholic acid</name>
  <description/>
  <synonyms>
    <synonym>(3beta,5beta,7beta)-3,7-Dihydroxycholan-24-Oic acid</synonym>
    <synonym>3beta,7beta-Dihydroxy-5beta-cholan-24-Oic acid</synonym>
    <synonym>3beta,7beta-Dihydroxy-5beta-cholanoic acid</synonym>
    <synonym>ISO-ursodeoxycholIC ACID</synonym>
    <synonym>(3b,5b,7b)-3,7-Dihydroxycholan-24-Oate</synonym>
    <synonym>(3b,5b,7b)-3,7-Dihydroxycholan-24-Oic acid</synonym>
    <synonym>(3beta,5beta,7beta)-3,7-Dihydroxycholan-24-Oate</synonym>
    <synonym>(3Β,5β,7β)-3,7-dihydroxycholan-24-Oate</synonym>
    <synonym>(3Β,5β,7β)-3,7-dihydroxycholan-24-Oic acid</synonym>
    <synonym>3b,7b-Dihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3b,7b-Dihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3beta,7beta-Dihydroxy-5beta-cholan-24-Oate</synonym>
    <synonym>3Β,7β-dihydroxy-5β-cholan-24-Oate</synonym>
    <synonym>3Β,7β-dihydroxy-5β-cholan-24-Oic acid</synonym>
    <synonym>3b,7b-Dihydroxy-5b-cholanoate</synonym>
    <synonym>3b,7b-Dihydroxy-5b-cholanoic acid</synonym>
    <synonym>3beta,7beta-Dihydroxy-5beta-cholanoate</synonym>
    <synonym>3Β,7β-dihydroxy-5β-cholanoate</synonym>
    <synonym>3Β,7β-dihydroxy-5β-cholanoic acid</synonym>
    <synonym>ISO-ursodeoxycholate</synonym>
    <synonym>Isoursodeoxycholate</synonym>
    <synonym>3b,7b-Dihydroxy-5b-cholanate</synonym>
    <synonym>3b,7b-Dihydroxy-5b-cholanic acid</synonym>
    <synonym>3b-Ursodeoxycholate</synonym>
    <synonym>3b-Ursodeoxycholic acid</synonym>
    <synonym>3,7-Dihydroxycholan-24-Oic acid</synonym>
    <synonym>Sodium OF isoursodeoxycholic acid</synonym>
    <synonym>3beta,7beta-Dihydroxy-5beta-cholanic acid</synonym>
    <synonym>3beta-Ursodeoxycholic acid</synonym>
    <synonym>3β,7β-Dihydroxy-5β-cholanic acid</synonym>
    <synonym>3β-Ursodeoxycholic acid</synonym>
    <synonym>Isoursodeoxycholic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O4</chemical_formula>
  <average_molecular_weight>392.572</average_molecular_weight>
  <monisotopic_moleculate_weight>392.292659768</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5S,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5S,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>78919-26-3</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O</smiles>
  <inchi>InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17-,18+,19+,20+,22+,23+,24-/m1/s1</inchi>
  <inchikey>RUDATBOHQWOJDD-DNMBCGTGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>dihydroxy-5beta-cholanic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5S,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>392.572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.292659768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16+,17-,18+,19+,20+,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RUDATBOHQWOJDD-DNMBCGTGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142736</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022182</foodb_id>
  <kegg_id>C17662</kegg_id>
  <chemspider_id>113205</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>127601</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>43419</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5655</metlin_id>
  <synthesis_reference>Thomas, Hans Guenter. Procedure for the preparation of isoursodeoxychloic acid. Ger. Offen.  (1996),     8 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:54 UTC</creation_date>
  <update_date>2020-04-16 20:38:31 UTC</update_date>
  <accession>BMDB0000687</accession>
  <secondary_accessions>
    <accession>BMDB00687</accession>
  </secondary_accessions>
  <name>L-Leucine</name>
  <description>L-Leucine, also known as (S)-leucine or L-leucin, belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Leucine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Leucine exists in all living species, ranging from bacteria to humans. L-Leucine can be converted into L-leucine through its interaction with the enzyme large neutral amino acids transporter small subunit 1. In cattle, L-leucine is involved in the metabolic pathway called the leucine stimulation ON insulin signaling pathway. L-Leucine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2S)-2-Amino-4-methylpentanoic acid</synonym>
    <synonym>(2S)-alpha-2-Amino-4-methylvaleric acid</synonym>
    <synonym>(2S)-alpha-Leucine</synonym>
    <synonym>(S)-(+)-Leucine</synonym>
    <synonym>(S)-Leucine</synonym>
    <synonym>2-Amino-4-methylvaleric acid</synonym>
    <synonym>L</synonym>
    <synonym>L-Leucin</synonym>
    <synonym>L-Leuzin</synonym>
    <synonym>Leu</synonym>
    <synonym>LEUCINE</synonym>
    <synonym>(2S)-2-Amino-4-methylpentanoate</synonym>
    <synonym>(2S)-a-2-Amino-4-methylvalerate</synonym>
    <synonym>(2S)-a-2-Amino-4-methylvaleric acid</synonym>
    <synonym>(2S)-alpha-2-Amino-4-methylvalerate</synonym>
    <synonym>(2S)-Α-2-amino-4-methylvalerate</synonym>
    <synonym>(2S)-Α-2-amino-4-methylvaleric acid</synonym>
    <synonym>(2S)-a-Leucine</synonym>
    <synonym>(2S)-Α-leucine</synonym>
    <synonym>2-Amino-4-methylvalerate</synonym>
    <synonym>(S)-2-Amino-4-methylpentanoate</synonym>
    <synonym>(S)-2-Amino-4-methylpentanoic acid</synonym>
    <synonym>(S)-2-Amino-4-methylvalerate</synonym>
    <synonym>(S)-2-Amino-4-methylvaleric acid</synonym>
    <synonym>4-Methyl-L-norvaline</synonym>
    <synonym>L-(+)-Leucine</synonym>
    <synonym>L-a-Aminoisocaproate</synonym>
    <synonym>L-a-Aminoisocaproic acid</synonym>
    <synonym>L-alpha-Aminoisocaproate</synonym>
    <synonym>L-alpha-Aminoisocaproic acid</synonym>
    <synonym>Leucine, L-isomer</synonym>
    <synonym>L-Isomer leucine</synonym>
    <synonym>Leucine, L isomer</synonym>
  </synonyms>
  <chemical_formula>C6H13NO2</chemical_formula>
  <average_molecular_weight>131.1729</average_molecular_weight>
  <monisotopic_moleculate_weight>131.094628665</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-methylpentanoic acid</iupac_name>
  <traditional_iupac>L-leucine</traditional_iupac>
  <cas_registry_number>61-90-5</cas_registry_number>
  <smiles>CC(C)C[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1</inchi>
  <inchikey>ROHFNLRQFUQHCH-YFKPBYRVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Leucine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Leucine or derivatives</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>leucine</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
      <external_descriptor>pyruvate family amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>268 - 288 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>21.5 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.52</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-methylpentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>131.1729</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>131.094628665</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)C[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ROHFNLRQFUQHCH-YFKPBYRVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Leucine Stimulation on Insulin Signaling</name>
      <smpdb_id>SMP0108000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Leucine</name>
      <smpdb_id>SMP0119403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37697</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 24 male 17-22-month-old Charolais beef cattles.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>107.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>205-264</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>132.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>90-117</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>212+/-24</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>67-1877</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Sadri H, von Soosten D, Meyer U, Kluess J, Danicke S, Saremi B, Sauerwein H: Plasma amino acids and metabolic profiling of dairy cows in response to a bolus duodenal infusion of leucine. PLoS One. 2017 Apr 28;12(4):e0176647. doi: 10.1371/journal.pone.0176647. eCollection 2017.</reference_text>
          <pubmed_id>28453535</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>152-162</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>426+/-117</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>154+/-37</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.64 +/- 1.55</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2 - 22</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25919.988</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25919.988</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25919.988</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25919.988</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25157.635</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25157.635</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25157.635</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.80 +/- 1.31</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.8 +/- 0.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.9 +/- 0.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.5 +/- 0.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.3 +/- 1.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.81 +/- 0.83</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected after TiO2 phosphopeptide enrichment and nano-HPLC-MS/MS analysis in longissimus dorsi muscle.</comment>
      <references>
        <reference>
          <reference_text>D'Alessandro A, Rinalducci S, Marrocco C, Zolla V, Napolitano F, Zolla L: Love me tender: an Omics window on the bovine meat tenderness network. J Proteomics. 2012 Jul 19;75(14):4360-80. doi: 10.1016/j.jprot.2012.02.013. Epub  2012 Feb 21.</reference_text>
          <pubmed_id>22361340</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>138.21 +/- 19.52</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>150.85 +/- 24.51</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>80-424</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>390.39 +/- 33.32</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>770</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>7.10+/-1.14</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>8.63+/-1.80</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1.86+/-0.4</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>4.03+/-0.99</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>86.05 +/- 6.13</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>180-256</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>238-960</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>119.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>182.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>191.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>125.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>125.79 +/- 5.98</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>76-571</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>70-159</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hanne Christine Bertram, Niels Bastian Kristensen, Mogens Vestergaard, SÃ¸ren Krogh Jensen, Jakob Sehested, Niels Christian Nielsen, Anders Malmendal. Metabolic characterization of rumen epithelial tissue from dairy calves fed different starter diets using 1H NMR spectroscopy. Livestock Science (2008) 120:127-134   doi: 10.1016/j.livsci.2008.05.001</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>119 +/- 17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>183 +/- 76</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>191 +/- 44</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>146 +/- 46</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>145 +/- 46</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>603+/-119</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>99.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>164</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>155</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>109</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>158+/-33</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>40</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Sexton TJ, Amann RP, Flipse RJ: Free amino acids and protein in rete testis fluid, vas deferens plasma, accessory sex gland fluid, and seminal plasma of the conscious bull. J Dairy Sci. 1971 Mar;54(3):412-6. doi: 10.3168/jds.s0022-0302(71)85854-x.</reference_text>
          <pubmed_id>5096119</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>138+/-23</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB00149</drugbank_id>
  <foodb_id>FDB000899</foodb_id>
  <kegg_id>C00123</kegg_id>
  <chemspider_id>5880</chemspider_id>
  <pdbe_id/>
  <chebi_id>15603</chebi_id>
  <pubchem_compound_id>6106</pubchem_compound_id>
  <meta_cyc_id>LEU</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001377</knapsack_id>
  <bigg_id>33942</bigg_id>
  <wikipedia_id>Leucine</wikipedia_id>
  <metlin_id>24</metlin_id>
  <synthesis_reference>Leuchtenberger, Wolfgang; Karrenbauer, Michael; Ploecker, Ulf.  Scale-up of an enzyme membrane reactor process for the manufacture of L-enantiomeric compounds.    Annals of the New York Academy of Sciences  (1984),  434(Enzyme Eng.),  78-86.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00226</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>A4IFQ7</uniprot_id>
      <gene_name>BCAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00227</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase, mitochondrial</name>
      <uniprot_id>Q5EA40</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00228</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>Q0V8J6</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00229</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>Q5E9U7</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01993</protein_accession>
      <name>Cyclic AMP-dependent transcription factor ATF-4</name>
      <uniprot_id>Q3ZCH6</uniprot_id>
      <gene_name>ATF4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02160</protein_accession>
      <name>Blood-brain barrier large neutral amino acid transporter</name>
      <uniprot_id>Q9TU26</uniprot_id>
      <gene_name>LAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:55 UTC</creation_date>
  <update_date>2020-04-14 22:48:04 UTC</update_date>
  <accession>BMDB0000688</accession>
  <secondary_accessions>
    <accession>BMDB00688</accession>
  </secondary_accessions>
  <name>Isovalerylcarnitine</name>
  <description>Isovalerylcarnitine belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Thus, isovalerylcarnitine is considered to be a fatty ester lipid molecule. Isovalerylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Isovalerylcarnitine has been linked to several inborn metabolic disorders including very long chain acyl-coa dehydrogenase deficiency, isovaleric acidemia, and celiac disease.</description>
  <synonyms>
    <synonym>3-Methylbutyrylcarnitine</synonym>
    <synonym>Isovaleryl L-carnitine</synonym>
    <synonym>3-Methylbutyrylcarnitine, (+-)-isomer</synonym>
  </synonyms>
  <chemical_formula>C12H23NO4</chemical_formula>
  <average_molecular_weight>245.3153</average_molecular_weight>
  <monisotopic_moleculate_weight>245.162708229</monisotopic_moleculate_weight>
  <iupac_name>3-[(3-methylbutanoyl)oxy]-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>isovalerylcarnitine</traditional_iupac>
  <cas_registry_number>31023-24-2</cas_registry_number>
  <smiles>CC(C)CC(=O)OC(CC([O-])=O)C[N+](C)(C)C</smiles>
  <inchi>InChI=1S/C12H23NO4/c1-9(2)6-12(16)17-10(7-11(14)15)8-13(3,4)5/h9-10H,6-8H2,1-5H3</inchi>
  <inchikey>IGQBPDJNUXPEMT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Acyl carnitines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Branched fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl-carnitine</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C5-acylcarnitine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(3-methylbutanoyl)oxy]-4-(trimethylazaniumyl)butanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>245.3153</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>245.162708229</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CC(=O)OC(CC([O-])=O)C[N+](C)(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H23NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H23NO4/c1-9(2)6-12(16)17-10(7-11(14)15)8-13(3,4)5/h9-10H,6-8H2,1-5H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IGQBPDJNUXPEMT-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1424</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.1 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.5 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022183</foodb_id>
  <kegg_id/>
  <chemspider_id>4932271</chemspider_id>
  <pdbe_id/>
  <chebi_id>73025</chebi_id>
  <pubchem_compound_id>6426851</pubchem_compound_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5657</metlin_id>
  <synthesis_reference>Nakanishi, Toyofumi; Shimizu, Akira; Arimoto, Masao; Kanai, Michiko.  Synthesis of acylcarnitines for differential diagnosis of metabolic disorders.    Nippon Iyo Masu Supekutoru Gakkai Koenshu  (1993),  18  129-32.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:56 UTC</creation_date>
  <update_date>2020-03-13 16:23:05 UTC</update_date>
  <accession>BMDB0000689</accession>
  <secondary_accessions>
    <accession>BMDB00689</accession>
  </secondary_accessions>
  <name>Isocaproic acid</name>
  <description/>
  <synonyms>
    <synonym>4,4-Dimethylbutanoic acid</synonym>
    <synonym>4-Methyl-N-valeric acid</synonym>
    <synonym>4-Methyl-pentanoic acid</synonym>
    <synonym>4-Methyl-valeric acid</synonym>
    <synonym>4-Methylvaleric acid</synonym>
    <synonym>Isobutylacetic acid</synonym>
    <synonym>Isohexanoic acid</synonym>
    <synonym>Isohexoic acid</synonym>
    <synonym>4,4-Dimethylbutanoate</synonym>
    <synonym>4-Methyl-N-valerate</synonym>
    <synonym>4-Methyl-pentanoate</synonym>
    <synonym>4-Methyl-valerate</synonym>
    <synonym>4-Methylvalerate</synonym>
    <synonym>Isobutylacetate</synonym>
    <synonym>Isohexanoate</synonym>
    <synonym>Isohexoate</synonym>
    <synonym>Isocaproate</synonym>
    <synonym>4-Methylpentanoate</synonym>
    <synonym>4-Methylpentanoic acid</synonym>
    <synonym>Isocaproic acid, sodium salt</synonym>
    <synonym>4-Methyl valerate</synonym>
    <synonym>Isocaproic acid</synonym>
  </synonyms>
  <chemical_formula>C6H12O2</chemical_formula>
  <average_molecular_weight>116.1583</average_molecular_weight>
  <monisotopic_moleculate_weight>116.083729628</monisotopic_moleculate_weight>
  <iupac_name>4-methylpentanoic acid</iupac_name>
  <traditional_iupac>isocaproate</traditional_iupac>
  <cas_registry_number>646-07-1</cas_registry_number>
  <smiles>CC(C)CCC(O)=O</smiles>
  <inchi>InChI=1S/C6H12O2/c1-5(2)3-4-6(7)8/h5H,3-4H2,1-2H3,(H,7,8)</inchi>
  <inchikey>FGKJLKRYENPLQH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Methyl-branched fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Branched fatty acids</external_descriptor>
      <external_descriptor>branched-chain saturated fatty acid</external_descriptor>
      <external_descriptor>medium-chain fatty acid</external_descriptor>
      <external_descriptor>methyl-branched fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-33 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-methylpentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>116.1583</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>116.083729628</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O2/c1-5(2)3-4-6(7)8/h5H,3-4H2,1-2H3,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FGKJLKRYENPLQH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438130</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB03993</drugbank_id>
  <foodb_id>FDB008206</foodb_id>
  <kegg_id/>
  <chemspider_id>12067</chemspider_id>
  <pdbe_id/>
  <chebi_id>74903</chebi_id>
  <pubchem_compound_id>12587</pubchem_compound_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>4-Methylpentanoic acid</wikipedia_id>
  <metlin_id>4191</metlin_id>
  <synthesis_reference>Shimizu, K.; Dorfman, Ralph I.; Gut, Marcel.  Isocaproic acid, a metabolite of 20a-hydroxycholesterol.    Journal of Biological Chemistry  (1960),  235  PC25.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:57 UTC</creation_date>
  <update_date>2020-04-16 17:52:18 UTC</update_date>
  <accession>BMDB0000691</accession>
  <secondary_accessions>
    <accession>BMDB00691</accession>
  </secondary_accessions>
  <name>Malonic acid</name>
  <description>Malonate, also known as H2MALO or HOOC-CH2-COOH, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Malonate exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Malonate exists in all living species, ranging from bacteria to humans. In cattle, malonate is involved in the metabolic pathway called fatty acid biosynthesis pathway. Malonate has been found to be associated with several diseases known as combined malonic and methylmalonic aciduria, eosinophilic esophagitis, early preeclampsia, and colorectal cancer; also malonate has been linked to the inborn metabolic disorders including malonyl-coa decarboxylase deficiency.</description>
  <synonyms>
    <synonym>H2Malo</synonym>
    <synonym>HOOC-CH2-COOH</synonym>
    <synonym>Propanedioic acid</synonym>
    <synonym>Propanedioate</synonym>
    <synonym>Malonate</synonym>
    <synonym>alpha,Omega-dicarboxylic acid</synonym>
    <synonym>Carboxyacetic acid</synonym>
    <synonym>Dicarboxylate</synonym>
    <synonym>Dicarboxylic acid</synonym>
    <synonym>Dicarboxymethane</synonym>
    <synonym>Kyselina malonova</synonym>
    <synonym>Malonate dicarboxylic acid</synonym>
    <synonym>Metahnedicarboxylic acid</synonym>
    <synonym>Methanedicarbonic acid</synonym>
    <synonym>Methanedicarboxylic acid</synonym>
    <synonym>Propanedioic acid dithallium salt</synonym>
    <synonym>Propanediolic acid</synonym>
    <synonym>Thallium malonate</synonym>
    <synonym>Malonic acid, 2-(14)C-labeled</synonym>
    <synonym>Malonic acid, monocalcium salt</synonym>
    <synonym>Malonic acid, 1,3-(14)C2-labeled</synonym>
    <synonym>Malonic acid, diammonium salt</synonym>
    <synonym>Malonic acid, disodium salt</synonym>
    <synonym>Malonic acid, dithallium salt</synonym>
    <synonym>Malonic acid, dipotassium salt</synonym>
    <synonym>Malonic acid, disodium salt, 1-(14)C-labeled</synonym>
    <synonym>Malonic acid, monosodium salt</synonym>
    <synonym>Malonic acid, potassium salt</synonym>
    <synonym>Malonic acid, sodium salt</synonym>
    <synonym>Thallous malonate</synonym>
    <synonym>Dithallium malonate</synonym>
    <synonym>Monosodium malonate</synonym>
    <synonym>Malonic acid</synonym>
  </synonyms>
  <chemical_formula>C3H4O4</chemical_formula>
  <average_molecular_weight>104.0615</average_molecular_weight>
  <monisotopic_moleculate_weight>104.010958616</monisotopic_moleculate_weight>
  <iupac_name>propanedioic acid</iupac_name>
  <traditional_iupac>malonic acid</traditional_iupac>
  <cas_registry_number>141-82-2</cas_registry_number>
  <smiles>OC(=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)</inchi>
  <inchikey>OFOBLEOULBTSOW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Dicarboxylic acids and derivatives</sub_class>
    <direct_parent>Dicarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-dicarbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>alpha,omega-dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>135 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>763.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.81</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>propanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>104.0615</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>104.010958616</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H4O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OFOBLEOULBTSOW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>18.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451869</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C04025</kegg_id>
  <drugbank_id>DB02175</drugbank_id>
  <foodb_id>FDB008117</foodb_id>
  <chemspider_id>844</chemspider_id>
  <pdbe_id/>
  <chebi_id>30794</chebi_id>
  <pubchem_compound_id>867</pubchem_compound_id>
  <meta_cyc_id>MALONATE</meta_cyc_id>
  <knapsack_id>C00001193</knapsack_id>
  <wikipedia_id>Malonic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>3237</metlin_id>
  <synthesis_reference>Behr, Arno; Botulinski, Andreas; Carduck, Franz Josef; Schneider, Michael.  Process for preparation of malonic acid.    Ger. Offen.  (1992),     4 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26.</reference_text>
      <pubmed_id>27236769</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01668</protein_accession>
      <name>Solute carrier family 1 member 4</name>
      <uniprot_id>A5HSH2</uniprot_id>
      <gene_name>SLC1A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01748</protein_accession>
      <name>Solute carrier family 1 member 5</name>
      <uniprot_id>A5HSH3</uniprot_id>
      <gene_name>SLC1A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02100</protein_accession>
      <name>SLC1A6 protein</name>
      <uniprot_id>A6H774</uniprot_id>
      <gene_name>SLC1A6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02101</protein_accession>
      <name>Solute carrier family 1 member 2</name>
      <uniprot_id>A5HSH1</uniprot_id>
      <gene_name>SLC1A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02136</protein_accession>
      <name>Excitatory amino acid transporter 3</name>
      <uniprot_id>Q95135</uniprot_id>
      <gene_name>SLC1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02137</protein_accession>
      <name>Neutral amino acid transporter A</name>
      <uniprot_id>A2VDL4</uniprot_id>
      <gene_name>SLC1A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02138</protein_accession>
      <name>Neutral amino acid transporter B(0)</name>
      <uniprot_id>Q95JC7</uniprot_id>
      <gene_name>SLC1A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02139</protein_accession>
      <name>Excitatory amino acid transporter 1</name>
      <uniprot_id>P46411</uniprot_id>
      <gene_name>SLC1A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02140</protein_accession>
      <name>Solute carrier family 1 member 1</name>
      <uniprot_id>A5HSH0</uniprot_id>
      <gene_name>SLC1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02141</protein_accession>
      <name>Solute carrier family 13 (Sodium-dependent dicarboxylate transporter), member 2</name>
      <uniprot_id>Q3SYV8</uniprot_id>
      <gene_name>SLC13A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02142</protein_accession>
      <name>SLC1A1 protein</name>
      <uniprot_id>A7MB31</uniprot_id>
      <gene_name>SLC1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02143</protein_accession>
      <name>Solute carrier family 13 (Sodium-dependent dicarboxylate transporter), member 3</name>
      <uniprot_id>A1A4I3</uniprot_id>
      <gene_name>SLC13A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02144</protein_accession>
      <name>Sodium-dependent neutral amino acid transporter ASCT1</name>
      <uniprot_id>Q866Q9</uniprot_id>
      <gene_name>SLC1A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:34:59 UTC</creation_date>
  <update_date>2020-04-15 22:14:19 UTC</update_date>
  <accession>BMDB0000692</accession>
  <secondary_accessions>
    <accession>BMDB00692</accession>
  </secondary_accessions>
  <name>Iron</name>
  <description>Iron, also known as fe (ii) ion or fe(ii), belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Iron exists as a solid, possibly soluble (in water), and possibly neutral molecule. Iron exists in all living species, ranging from bacteria to humans. Iron is a potentially toxic compound.</description>
  <synonyms>
    <synonym>FE (II) ion</synonym>
    <synonym>Fe(II)</synonym>
    <synonym>Fe2+</synonym>
    <synonym>Fe(2+)</synonym>
    <synonym>Ferrous ion</synonym>
    <synonym>Iron ion(2+)</synonym>
    <synonym>Iron(2+)</synonym>
    <synonym>Armco iron</synonym>
    <synonym>Carbonyl iron</synonym>
    <synonym>FE</synonym>
    <synonym>Ferrovac e</synonym>
    <synonym>Hematite</synonym>
    <synonym>Infed</synonym>
    <synonym>Limonite</synonym>
    <synonym>LOHA</synonym>
    <synonym>Magnetite</synonym>
    <synonym>Malleable iron</synonym>
    <synonym>Metopirone</synonym>
    <synonym>Metyrapone</synonym>
    <synonym>PZH2m</synonym>
    <synonym>PZHO</synonym>
    <synonym>Remko</synonym>
    <synonym>Suy-b 2</synonym>
    <synonym>Taconite</synonym>
    <synonym>Venofer</synonym>
    <synonym>Wrought iron</synonym>
    <synonym>Iron hydroxide (fe(OH)3)</synonym>
    <synonym>Iron oxyhydroxide</synonym>
    <synonym>Ferric hydroxide</synonym>
    <synonym>Iron hydroxide (III)</synonym>
  </synonyms>
  <chemical_formula>Fe</chemical_formula>
  <average_molecular_weight>55.845</average_molecular_weight>
  <monisotopic_moleculate_weight>55.934942133</monisotopic_moleculate_weight>
  <iupac_name>lambda2-iron(2+) ion</iupac_name>
  <traditional_iupac>lambda2-iron(2+) ion</traditional_iupac>
  <cas_registry_number>15438-31-0</cas_registry_number>
  <smiles>[Fe++]</smiles>
  <inchi>InChI=1S/Fe/q+2</inchi>
  <inchikey>CWYNVVGOOAEACU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous transition metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous transition metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous transition metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a cation</external_descriptor>
      <external_descriptor>divalent metal cation</external_descriptor>
      <external_descriptor>iron cation</external_descriptor>
      <external_descriptor>monoatomic dication</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>lambda2-iron(2+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>55.845</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>55.934942133</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Fe++]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Fe</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Fe/q+2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CWYNVVGOOAEACU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Retinol Metabolism</name>
      <smpdb_id>SMP0087260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Taurine and Hypotaurine Metabolism</name>
      <smpdb_id>SMP0087214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118661</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>52+/-13</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>10+/-4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.372 - 12.535</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Š. ZAMBERLIN et al.: Mineral elements in milk and dairy products, Mljekarstvo 62 (2), 111-125</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0314 - 13.597</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Sola-Larrañaga C., Navarro-Blasco I. 2009. Chemometric analysis of minerals and trace elements in raw cow milk from the community of Navarra, Spain. Volume 112, Issue 1, Pages 189-196</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14.325</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4 +/- 0.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>39.395 +/- 1.791</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23.279 +/- 1.791</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>41.185 +/- 1.791</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS.  Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>33.127 +/- 1.433</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>44.767 +/- 89.534</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14.683 +/- 1.433</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.953</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.953</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.372</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.163</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.163 - 8.953</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.953</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.953</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.744</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.953</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.372</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.744</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.953</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.372</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.372</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.551</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.551</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.953</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.744</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.953</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.744</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.581</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.581</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.372</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.372</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.372</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.372</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.372</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.744</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.163</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.163</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14.325 - 389.113</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>26.4 +/- 5.0</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by ICP-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>40+/-8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>8+/-3</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB030855</foodb_id>
  <kegg_id>C14818</kegg_id>
  <chemspider_id>25394</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>27284</pubchem_compound_id>
  <pdbe_id>FE2</pdbe_id>
  <chebi_id>29033</chebi_id>
  <meta_cyc_id>Ferric-Hydroxamate-Complexes</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>33552</bigg_id>
  <wikipedia_id>Iron</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
      <pubmed_id>22081685</pubmed_id>
    </reference>
    <reference>
      <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
    </reference>
    <reference>
      <reference_text>Š. ZAMBERLIN et al.: Mineral elements in milk and dairy products, Mljekarstvo 62 (2), 111-125</reference_text>
    </reference>
    <reference>
      <reference_text>Sola-Larrañaga C., Navarro-Blasco I. 2009. Chemometric analysis of minerals and trace elements in raw cow milk from the community of Navarra, Spain. Volume 112, Issue 1, Pages 189-196</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00004</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>P00396</uniprot_id>
      <gene_name>MT-CO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00005</protein_accession>
      <name>Cytochrome P450 19A1</name>
      <uniprot_id>P46194</uniprot_id>
      <gene_name>CYP19A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00007</protein_accession>
      <name>Cytochrome c oxidase subunit 5A, mitochondrial</name>
      <uniprot_id>P00426</uniprot_id>
      <gene_name>COX5A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00008</protein_accession>
      <name>Ferric-chelate reductase 1</name>
      <uniprot_id>A2VE04</uniprot_id>
      <gene_name>FRRS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00010</protein_accession>
      <name>Cytochrome P450 11B1, mitochondrial</name>
      <uniprot_id>P15150</uniprot_id>
      <gene_name>CYP11B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00014</protein_accession>
      <name>Lanosterol 14-alpha demethylase</name>
      <uniprot_id>Q4PJW3</uniprot_id>
      <gene_name>CYP51A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00015</protein_accession>
      <name>Catalase</name>
      <uniprot_id>P00432</uniprot_id>
      <gene_name>CAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00016</protein_accession>
      <name>Cytochrome P450 3A28</name>
      <uniprot_id>P79102</uniprot_id>
      <gene_name>CYP3A28</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00017</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>P00157</uniprot_id>
      <gene_name>MT-CYB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00018</protein_accession>
      <name>Succinate dehydrogenase cytochrome b560 subunit, mitochondrial</name>
      <uniprot_id>P35720</uniprot_id>
      <gene_name>SDHC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00022</protein_accession>
      <name>Nitric oxide synthase, endothelial</name>
      <uniprot_id>P29473</uniprot_id>
      <gene_name>NOS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00023</protein_accession>
      <name>Cytochrome c1, heme protein, mitochondrial</name>
      <uniprot_id>P00125</uniprot_id>
      <gene_name>CYC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00024</protein_accession>
      <name>Prostacyclin synthase</name>
      <uniprot_id>Q29626</uniprot_id>
      <gene_name>PTGIS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00026</protein_accession>
      <name>Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial</name>
      <uniprot_id>Q95123</uniprot_id>
      <gene_name>SDHD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00027</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YMV6</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00028</protein_accession>
      <name>Cytochrome b ascorbate-dependent protein 3</name>
      <uniprot_id>A5D9A7</uniprot_id>
      <gene_name>CYBASC3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00029</protein_accession>
      <name>Guanylate cyclase soluble subunit beta-1</name>
      <uniprot_id>P16068</uniprot_id>
      <gene_name>GUCY1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00030</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YMT7</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00032</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YMS5</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00035</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YMS1</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00038</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>C5IS82</uniprot_id>
      <gene_name>COI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00039</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YN12</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00040</protein_accession>
      <name>Steroid 17-alpha-hydroxylase/17,20 lyase</name>
      <uniprot_id>P05185</uniprot_id>
      <gene_name>CYP17A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00041</protein_accession>
      <name>Cytochrome P450 2D14</name>
      <uniprot_id>Q01361</uniprot_id>
      <gene_name>CYP2D14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00042</protein_accession>
      <name>Cytochrome P450 2U1</name>
      <uniprot_id>Q0IIF9</uniprot_id>
      <gene_name>CYP2U1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00044</protein_accession>
      <name>Prostaglandin G/H synthase 2</name>
      <uniprot_id>O62698</uniprot_id>
      <gene_name>PTGS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00046</protein_accession>
      <name>Prostaglandin G/H synthase 1</name>
      <uniprot_id>O62664</uniprot_id>
      <gene_name>PTGS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00047</protein_accession>
      <name>Cytochrome b-245 light chain</name>
      <uniprot_id>O46521</uniprot_id>
      <gene_name>CYBA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00049</protein_accession>
      <name>Lactoperoxidase</name>
      <uniprot_id>P80025</uniprot_id>
      <gene_name>LPO</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00051</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>C5IS85</uniprot_id>
      <gene_name>COI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00052</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YN01</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00053</protein_accession>
      <name>Cholesterol side-chain cleavage enzyme, mitochondrial</name>
      <uniprot_id>P00189</uniprot_id>
      <gene_name>CYP11A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00056</protein_accession>
      <name>Cytochrome P450 20A1</name>
      <uniprot_id>Q5E980</uniprot_id>
      <gene_name>CYP20A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00057</protein_accession>
      <name>Cytochrome P450 2A</name>
      <uniprot_id>P22779</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00058</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YMR7</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00060</protein_accession>
      <name>Steroid 21-hydroxylase</name>
      <uniprot_id>P00191</uniprot_id>
      <gene_name>CYP21</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00061</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A5YMW7</uniprot_id>
      <gene_name>COXI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00062</protein_accession>
      <name>Cytochrome P450 2E1</name>
      <uniprot_id>O18963</uniprot_id>
      <gene_name>CYP2E1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00063</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>A1XP62</uniprot_id>
      <gene_name>COI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00065</protein_accession>
      <name>Cytochrome c oxidase subunit 1</name>
      <uniprot_id>B1NZU1</uniprot_id>
      <gene_name>COX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00066</protein_accession>
      <name>Cytochrome b5 reductase 4</name>
      <uniprot_id>Q32LH7</uniprot_id>
      <gene_name>CYB5R4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00067</protein_accession>
      <name>Ferrochelatase, mitochondrial</name>
      <uniprot_id>P22600</uniprot_id>
      <gene_name>FECH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00068</protein_accession>
      <name>Cytochrome c-type heme lyase</name>
      <uniprot_id>A5PJG7</uniprot_id>
      <gene_name>HCCS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00069</protein_accession>
      <name>Nitric oxide synthase, inducible</name>
      <uniprot_id>Q27995</uniprot_id>
      <gene_name>NOS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00070</protein_accession>
      <name>Heme oxygenase 1</name>
      <uniprot_id>Q5E9F2</uniprot_id>
      <gene_name>HMOX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00097</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial</name>
      <uniprot_id>P42026</uniprot_id>
      <gene_name>NDUFS7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00099</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial</name>
      <uniprot_id>P17694</uniprot_id>
      <gene_name>NDUFS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00184</protein_accession>
      <name>Serine/threonine protein phosphatase</name>
      <uniprot_id>A9ZTK8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00188</protein_accession>
      <name>Serine/threonine protein phosphatase</name>
      <uniprot_id>A5D7T5</uniprot_id>
      <gene_name>PPP3CC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00208</protein_accession>
      <name>Serine/threonine protein phosphatase</name>
      <uniprot_id>A6H703</uniprot_id>
      <gene_name>PPP3CB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00273</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] flavoprotein 2, mitochondrial</name>
      <uniprot_id>P04394</uniprot_id>
      <gene_name>NDUFV2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00297</protein_accession>
      <name>Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial</name>
      <uniprot_id>Q3T189</uniprot_id>
      <gene_name>SDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00305</protein_accession>
      <name>NADH-ubiquinone oxidoreductase 75 kDa subunit, mitochondrial</name>
      <uniprot_id>P15690</uniprot_id>
      <gene_name>NDUFS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00344</protein_accession>
      <name>Electron transfer flavoprotein-ubiquinone oxidoreductase, mitochondrial</name>
      <uniprot_id>Q2KIG0</uniprot_id>
      <gene_name>ETFDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00345</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 8, mitochondrial</name>
      <uniprot_id>P42028</uniprot_id>
      <gene_name>NDUFS8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00348</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial</name>
      <uniprot_id>P25708</uniprot_id>
      <gene_name>NDUFV1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00361</protein_accession>
      <name>Elongator complex protein 3</name>
      <uniprot_id>Q2KJ61</uniprot_id>
      <gene_name>ELP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00389</protein_accession>
      <name>Phenylalanine-4-hydroxylase</name>
      <uniprot_id>Q2KIH7</uniprot_id>
      <gene_name>PAH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00396</protein_accession>
      <name>Lipoyl synthase, mitochondrial</name>
      <uniprot_id>Q5BIP7</uniprot_id>
      <gene_name>LIAS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00426</protein_accession>
      <name>Inositol oxygenase</name>
      <uniprot_id>A7MBE4</uniprot_id>
      <gene_name>MIOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00492</protein_accession>
      <name>TFIIH basal transcription factor complex helicase subunit</name>
      <uniprot_id>A6QLJ0</uniprot_id>
      <gene_name>ERCC2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00568</protein_accession>
      <name>Aspartyl/asparaginyl beta-hydroxylase</name>
      <uniprot_id>Q28056</uniprot_id>
      <gene_name>ASPH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00578</protein_accession>
      <name>Probable imidazolonepropionase</name>
      <uniprot_id>A5PJV3</uniprot_id>
      <gene_name>AMDHD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00642</protein_accession>
      <name>Serine/threonine-protein phosphatase 2A catalytic subunit alpha isoform</name>
      <uniprot_id>P67774</uniprot_id>
      <gene_name>PPP2CA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00643</protein_accession>
      <name>Serine/threonine-protein phosphatase PP1-alpha catalytic subunit</name>
      <uniprot_id>Q3T0E7</uniprot_id>
      <gene_name>PPP1CA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00646</protein_accession>
      <name>Serine/threonine-protein phosphatase PP1-beta catalytic subunit</name>
      <uniprot_id>Q3SWW9</uniprot_id>
      <gene_name>PPP1CB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00647</protein_accession>
      <name>Serine/threonine-protein phosphatase 4 catalytic subunit</name>
      <uniprot_id>A6H772</uniprot_id>
      <gene_name>PPP4C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00649</protein_accession>
      <name>Serine/threonine-protein phosphatase PP1-gamma catalytic subunit</name>
      <uniprot_id>P61287</uniprot_id>
      <gene_name>PPP1CC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00654</protein_accession>
      <name>Serine/threonine-protein phosphatase 2A catalytic subunit beta isoform</name>
      <uniprot_id>Q0P594</uniprot_id>
      <gene_name>PPP2CB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00666</protein_accession>
      <name>3-hydroxyanthranilate 3,4-dioxygenase</name>
      <uniprot_id>Q0VCA8</uniprot_id>
      <gene_name>HAAO</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00667</protein_accession>
      <name>Serine/threonine protein phosphatase</name>
      <uniprot_id>Q0V8L5</uniprot_id>
      <gene_name>PPP5C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00668</protein_accession>
      <name>Prolyl 4-hydroxylase subunit alpha-1</name>
      <uniprot_id>Q1RMU3</uniprot_id>
      <gene_name>P4HA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00669</protein_accession>
      <name>Phytanoyl-CoA dioxygenase domain-containing protein 1</name>
      <uniprot_id>Q0IIB1</uniprot_id>
      <gene_name>PHYHD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00670</protein_accession>
      <name>Acyl-CoA desaturase</name>
      <uniprot_id>Q9TT94</uniprot_id>
      <gene_name>SCD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00671</protein_accession>
      <name>Ferritin heavy chain</name>
      <uniprot_id>O46414</uniprot_id>
      <gene_name>FTH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00672</protein_accession>
      <name>Deoxyhypusine hydroxylase</name>
      <uniprot_id>Q0VC53</uniprot_id>
      <gene_name>DOHH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00673</protein_accession>
      <name>2-oxoglutarate and iron-dependent oxygenase domain-containing protein 1</name>
      <uniprot_id>Q3MI03</uniprot_id>
      <gene_name>OGFOD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00674</protein_accession>
      <name>Ferritin, mitochondrial</name>
      <uniprot_id>Q2YDI9</uniprot_id>
      <gene_name>FTMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00675</protein_accession>
      <name>Endonuclease III-like protein 1</name>
      <uniprot_id>Q2KID2</uniprot_id>
      <gene_name>NTHL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00676</protein_accession>
      <name>Serine/threonine protein phosphatase</name>
      <uniprot_id>Q0V8M3</uniprot_id>
      <gene_name>PPP5C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00677</protein_accession>
      <name>Aldehyde oxidase</name>
      <uniprot_id>P48034</uniprot_id>
      <gene_name>AOX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00678</protein_accession>
      <name>Serine/threonine-protein phosphatase 2B catalytic subunit alpha isoform</name>
      <uniprot_id>P48452</uniprot_id>
      <gene_name>PPP3CA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00679</protein_accession>
      <name>Alpha-ketoglutarate-dependent dioxygenase alkB homolog 2</name>
      <uniprot_id>Q58DM4</uniprot_id>
      <gene_name>ALKBH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00680</protein_accession>
      <name>Alpha-ketoglutarate-dependent dioxygenase alkB homolog 3</name>
      <uniprot_id>Q32L00</uniprot_id>
      <gene_name>ALKBH3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00681</protein_accession>
      <name>Cytoplasmic aconitate hydratase</name>
      <uniprot_id>Q0VCU1</uniprot_id>
      <gene_name>ACO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00682</protein_accession>
      <name>Procollagen-lysine,2-oxoglutarate 5-dioxygenase 1</name>
      <uniprot_id>O77588</uniprot_id>
      <gene_name>PLOD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00683</protein_accession>
      <name>Cysteine dioxygenase type 1</name>
      <uniprot_id>Q3SZU4</uniprot_id>
      <gene_name>CDO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00684</protein_accession>
      <name>4-hydroxyphenylpyruvate dioxygenase</name>
      <uniprot_id>Q5EA20</uniprot_id>
      <gene_name>HPD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00685</protein_accession>
      <name>Arachidonate 12-lipoxygenase, 12S-type</name>
      <uniprot_id>P27479</uniprot_id>
      <gene_name>ALOX12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00686</protein_accession>
      <name>Bifunctional arginine demethylase and lysyl-hydroxylase JMJD6</name>
      <uniprot_id>Q58DS6</uniprot_id>
      <gene_name>JMJD6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00687</protein_accession>
      <name>Aconitate hydratase, mitochondrial</name>
      <uniprot_id>P20004</uniprot_id>
      <gene_name>ACO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00688</protein_accession>
      <name>Phytanoyl-CoA dioxygenase, peroxisomal</name>
      <uniprot_id>O18778</uniprot_id>
      <gene_name>PHYH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00689</protein_accession>
      <name>Dihydropyrimidine dehydrogenase [NADP+]</name>
      <uniprot_id>Q28007</uniprot_id>
      <gene_name>DPYD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00690</protein_accession>
      <name>Serine/threonine protein phosphatase</name>
      <uniprot_id>Q2KIC7</uniprot_id>
      <gene_name>PPP6C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00691</protein_accession>
      <name>Prolyl 4-hydroxylase subunit alpha-3</name>
      <uniprot_id>Q75UG4</uniprot_id>
      <gene_name>P4HA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00795</protein_accession>
      <name>Methionine aminopeptidase 1</name>
      <uniprot_id>A6QLA4</uniprot_id>
      <gene_name>METAP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00797</protein_accession>
      <name>Methionine aminopeptidase 2</name>
      <uniprot_id>Q3ZC89</uniprot_id>
      <gene_name>METAP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01339</protein_accession>
      <name>NDUFS7 protein</name>
      <uniprot_id>A8WFQ0</uniprot_id>
      <gene_name>NDUFS7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01424</protein_accession>
      <name>LOC517246 protein</name>
      <uniprot_id>A6QPX5</uniprot_id>
      <gene_name>LOC517246</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01428</protein_accession>
      <name>Cytochrome b-245 heavy chain</name>
      <uniprot_id>O46522</uniprot_id>
      <gene_name>CYBB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01431</protein_accession>
      <name>CYP39A1 protein</name>
      <uniprot_id>A6H722</uniprot_id>
      <gene_name>CYP39A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01438</protein_accession>
      <name>CYP4A22 protein</name>
      <uniprot_id>A5PK83</uniprot_id>
      <gene_name>CYP4A22</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01439</protein_accession>
      <name>Cytochrome P450, subfamily IIIA, polypeptide 4</name>
      <uniprot_id>A5D9D8</uniprot_id>
      <gene_name>CYP3A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01440</protein_accession>
      <name>CYP1A2 protein</name>
      <uniprot_id>A6H748</uniprot_id>
      <gene_name>CYP1A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01447</protein_accession>
      <name>Neuroglobin</name>
      <uniprot_id>Q6WZ19</uniprot_id>
      <gene_name>NGB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01448</protein_accession>
      <name>Cytochrome P450, family 4, subfamily B, polypeptide 1</name>
      <uniprot_id>Q148E6</uniprot_id>
      <gene_name>CYP4B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01449</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>Q1P9M0</uniprot_id>
      <gene_name>cytB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01450</protein_accession>
      <name>Putative uncharacterized protein MGC127055</name>
      <uniprot_id>Q2KJJ2</uniprot_id>
      <gene_name>MGC127055</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01452</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>B8XJX1</uniprot_id>
      <gene_name>cytb</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01454</protein_accession>
      <name>Cytochrome P450, family 8, subfamily B, polypeptide 1</name>
      <uniprot_id>Q2KIG6</uniprot_id>
      <gene_name>CYP8B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01455</protein_accession>
      <name>Cytochrome P450, family 2, subfamily J, polypeptide 2</name>
      <uniprot_id>Q2TBK1</uniprot_id>
      <gene_name>CYP2J2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01459</protein_accession>
      <name>Cytochrome c</name>
      <uniprot_id>P62894</uniprot_id>
      <gene_name>CYCS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01461</protein_accession>
      <name>Cytochrome P450, family 4, subfamily F, polypeptide 3</name>
      <uniprot_id>Q2HJB3</uniprot_id>
      <gene_name>CYP4F3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01462</protein_accession>
      <name>CYP2S1 protein</name>
      <uniprot_id>A6QLC0</uniprot_id>
      <gene_name>CYP2S1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01463</protein_accession>
      <name>Cytochrome P450 1B1</name>
      <uniprot_id>A9CSR6</uniprot_id>
      <gene_name>CYP1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01465</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>C5IXE3</uniprot_id>
      <gene_name>CYTB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01469</protein_accession>
      <name>CYP26A1 protein</name>
      <uniprot_id>A6QPJ8</uniprot_id>
      <gene_name>CYP26A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01470</protein_accession>
      <name>Transcription factor NF-E2 45 kDa subunit</name>
      <uniprot_id>Q5EAD3</uniprot_id>
      <gene_name>NFE2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01471</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>C1K0L5</uniprot_id>
      <gene_name>cytb</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01473</protein_accession>
      <name>Membrane-associated progesterone receptor component 1</name>
      <uniprot_id>Q17QC0</uniprot_id>
      <gene_name>PGRMC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01474</protein_accession>
      <name>CYP2C19 protein</name>
      <uniprot_id>A8E652</uniprot_id>
      <gene_name>CYP2C19</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01475</protein_accession>
      <name>Cytochrome P450, family 2, subfamily R, polypeptide 1</name>
      <uniprot_id>Q0P5I1</uniprot_id>
      <gene_name>CYP2R1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01476</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>B1NZM3</uniprot_id>
      <gene_name>CYTB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01478</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>C5IX39</uniprot_id>
      <gene_name>CYTB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01479</protein_accession>
      <name>Cytochrome P450, subfamily IIIA (Niphedipine oxidase), polypeptide 4</name>
      <uniprot_id>Q29RV2</uniprot_id>
      <gene_name>CYP3A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01486</protein_accession>
      <name>Neudesin</name>
      <uniprot_id>Q1JQA5</uniprot_id>
      <gene_name>NENF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01488</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>Q1P9Q2</uniprot_id>
      <gene_name>cytB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01489</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>Q1P9Q0</uniprot_id>
      <gene_name>cytB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01492</protein_accession>
      <name>Hemoglobin subunit beta</name>
      <uniprot_id>P02070</uniprot_id>
      <gene_name>HBB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01494</protein_accession>
      <name>Hemopexin</name>
      <uniprot_id>Q3SZV7</uniprot_id>
      <gene_name>HPX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01496</protein_accession>
      <name>Cytochrome b5</name>
      <uniprot_id>P00171</uniprot_id>
      <gene_name>CYB5A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01498</protein_accession>
      <name>Hemoglobin subunit mu</name>
      <uniprot_id>A1A4Q3</uniprot_id>
      <gene_name>HBM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01499</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>B1NZR2</uniprot_id>
      <gene_name>CYTB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01502</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>B1P081</uniprot_id>
      <gene_name>CYTB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01506</protein_accession>
      <name>Hemoglobin subunit epsilon-2</name>
      <uniprot_id>P06642</uniprot_id>
      <gene_name>HBE2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01509</protein_accession>
      <name>Cytochrome P450, family 46, subfamily A, polypeptide 1</name>
      <uniprot_id>Q08DD0</uniprot_id>
      <gene_name>CYP46A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01513</protein_accession>
      <name>Hemoglobin subunit epsilon-4</name>
      <uniprot_id>P06643</uniprot_id>
      <gene_name>HBE4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01515</protein_accession>
      <name>CYP27A1 protein</name>
      <uniprot_id>A4FV92</uniprot_id>
      <gene_name>CYP27A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01517</protein_accession>
      <name>Cytochrome P450, family 4, subfamily F, polypeptide 2</name>
      <uniprot_id>Q0V896</uniprot_id>
      <gene_name>CYP4F2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01519</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>C5IX91</uniprot_id>
      <gene_name>CYTB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01522</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>C1K0L0</uniprot_id>
      <gene_name>cytb</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01523</protein_accession>
      <name>Hemoglobin, theta 1</name>
      <uniprot_id>A1A4Q7</uniprot_id>
      <gene_name>HBQ1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01525</protein_accession>
      <name>Cytochrome c 2</name>
      <uniprot_id>Q3SZT9</uniprot_id>
      <gene_name>CYCT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01529</protein_accession>
      <name>Cytochrome P450 subfamily IIE polypeptide 1</name>
      <uniprot_id>Q2TBV4</uniprot_id>
      <gene_name>CYP2E1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01534</protein_accession>
      <name>Cytochrome P450 subfamily 2B</name>
      <uniprot_id>Q2KIF3</uniprot_id>
      <gene_name>CYP2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01537</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>C1K0P3</uniprot_id>
      <gene_name>cytb</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01538</protein_accession>
      <name>Cytochrome b561</name>
      <uniprot_id>P10897</uniprot_id>
      <gene_name>CYB561</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01539</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>B8XJW1</uniprot_id>
      <gene_name>cytb</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01545</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>B0F9M4</uniprot_id>
      <gene_name>cytb</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01546</protein_accession>
      <name>Cytochrome P450, family 11, subfamily A, polypeptide 1</name>
      <uniprot_id>A3KMX9</uniprot_id>
      <gene_name>CYP11A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01549</protein_accession>
      <name>Cytochrome P450, family 2, subfamily C, polypeptide 18</name>
      <uniprot_id>Q1JQD1</uniprot_id>
      <gene_name>CYP2C18</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01551</protein_accession>
      <name>Cytochrome b561 domain-containing protein 2</name>
      <uniprot_id>Q5E965</uniprot_id>
      <gene_name>CYB561D2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01554</protein_accession>
      <name>Myoglobin</name>
      <uniprot_id>P02192</uniprot_id>
      <gene_name>MB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01558</protein_accession>
      <name>Hemoglobin fetal subunit beta</name>
      <uniprot_id>P02081</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01561</protein_accession>
      <name>Cytochrome P450, family 2, subfamily c</name>
      <uniprot_id>Q0IIG1</uniprot_id>
      <gene_name>LOC511498</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01563</protein_accession>
      <name>Cytochrome P450, family 4, subfamily A, polypeptide 11</name>
      <uniprot_id>Q148E4</uniprot_id>
      <gene_name>CYP4A11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01564</protein_accession>
      <name>Cytochrome b</name>
      <uniprot_id>C1K0I0</uniprot_id>
      <gene_name>cytb</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01567</protein_accession>
      <name>Microprocessor complex subunit DGCR8</name>
      <uniprot_id>A6QR44</uniprot_id>
      <gene_name>DGCR8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01569</protein_accession>
      <name>Hemoglobin subunit alpha</name>
      <uniprot_id>P01966</uniprot_id>
      <gene_name>HBA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01583</protein_accession>
      <name>Molybdenum cofactor biosynthesis protein 1</name>
      <uniprot_id>Q1JQD7</uniprot_id>
      <gene_name>MOCS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01592</protein_accession>
      <name>LYR motif-containing protein 4</name>
      <uniprot_id>Q0VCG0</uniprot_id>
      <gene_name>LYRM4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01933</protein_accession>
      <name>Ferritin</name>
      <uniprot_id>A1XEB9</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01934</protein_accession>
      <name>Cytosolic Fe-S cluster assembly factor NARFL</name>
      <uniprot_id>A4FV58</uniprot_id>
      <gene_name>NARFL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01935</protein_accession>
      <name>Lactoferrin</name>
      <uniprot_id>Q19KS1</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01936</protein_accession>
      <name>Ubiquinone biosynthesis protein COQ7 homolog</name>
      <uniprot_id>Q2TBW2</uniprot_id>
      <gene_name>COQ7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01937</protein_accession>
      <name>Mitoferrin-1</name>
      <uniprot_id>Q3ZBJ8</uniprot_id>
      <gene_name>SLC25A37</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01938</protein_accession>
      <name>CDGSH iron sulfur domain-containing protein 1</name>
      <uniprot_id>Q3ZBU2</uniprot_id>
      <gene_name>CISD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01939</protein_accession>
      <name>FTH1</name>
      <uniprot_id>A1XEC2</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01940</protein_accession>
      <name>Adrenodoxin-like protein, mitochondrial</name>
      <uniprot_id>Q05B51</uniprot_id>
      <gene_name>FDX1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01941</protein_accession>
      <name>Serotransferrin-like</name>
      <uniprot_id>Q2HJF0</uniprot_id>
      <gene_name>LOC525947</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01942</protein_accession>
      <name>Lactoferrin</name>
      <uniprot_id>B9VPZ5</uniprot_id>
      <gene_name>LF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01943</protein_accession>
      <name>Iron-sulfur cluster assembly 1 homolog, mitochondrial</name>
      <uniprot_id>Q3SZG8</uniprot_id>
      <gene_name>ISCA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01944</protein_accession>
      <name>Glutaredoxin-2, mitochondrial</name>
      <uniprot_id>Q32L67</uniprot_id>
      <gene_name>GLRX2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01945</protein_accession>
      <name>Ferritin</name>
      <uniprot_id>B0JYQ1</uniprot_id>
      <gene_name>FTH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01946</protein_accession>
      <name>CDGSH iron sulfur domain-containing protein 2</name>
      <uniprot_id>Q05B71</uniprot_id>
      <gene_name>CISD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01947</protein_accession>
      <name>Adrenodoxin, mitochondrial</name>
      <uniprot_id>P00257</uniprot_id>
      <gene_name>FDX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01948</protein_accession>
      <name>Ferritin</name>
      <uniprot_id>A1XEA2</uniprot_id>
      <gene_name>FTH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01949</protein_accession>
      <name>Ferritin light chain</name>
      <uniprot_id>O46415</uniprot_id>
      <gene_name>FTL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01950</protein_accession>
      <name>Iron-sulfur cluster assembly 2 homolog, mitochondrial</name>
      <uniprot_id>Q2TBG7</uniprot_id>
      <gene_name>ISCA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01951</protein_accession>
      <name>Lactoferrin</name>
      <uniprot_id>B3VTM3</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01952</protein_accession>
      <name>Cytosolic Fe-S cluster assembly factor NUBP2</name>
      <uniprot_id>Q3MHY6</uniprot_id>
      <gene_name>NUBP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01953</protein_accession>
      <name>ALOX12E protein</name>
      <uniprot_id>A4FV70</uniprot_id>
      <gene_name>ALOX12E</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01954</protein_accession>
      <name>Natural resistance-associated macrophage protein 1</name>
      <uniprot_id>Q27981</uniprot_id>
      <gene_name>SLC11A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01955</protein_accession>
      <name>Cytosolic Fe-S cluster assembly factor NUBP1</name>
      <uniprot_id>Q24K00</uniprot_id>
      <gene_name>NUBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:00 UTC</creation_date>
  <update_date>2020-04-16 20:38:31 UTC</update_date>
  <accession>BMDB0000693</accession>
  <secondary_accessions>
    <accession>BMDB00693</accession>
  </secondary_accessions>
  <name>Heparan sulfate</name>
  <description/>
  <synonyms>
    <synonym>Heparan sulfuric acid</synonym>
    <synonym>Heparan sulphate</synonym>
    <synonym>Heparan sulphuric acid</synonym>
    <synonym>alpha-Idosane</synonym>
    <synonym>Heparan N-sulfate</synonym>
    <synonym>Heparan N-sulphate</synonym>
    <synonym>Heparatan sulfate</synonym>
    <synonym>Heparatan sulphate</synonym>
    <synonym>Heparitin</synonym>
    <synonym>Heparitin monosulfate</synonym>
    <synonym>Heparitin monosulphate</synonym>
    <synonym>Heparitin sulfate</synonym>
    <synonym>Heparitin sulphate</synonym>
    <synonym>HHS 5</synonym>
    <synonym>N-Acetylheparan sulfate</synonym>
    <synonym>N-Acetylheparan sulphate</synonym>
    <synonym>Suleparoid</synonym>
    <synonym>Tavidan</synonym>
    <synonym>(2S,3R,4R,5S,6R)-4-Hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulfooxy)amino]-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulfooxy)oxane-2-carboxylate</synonym>
    <synonym>(2S,3R,4R,5S,6R)-4-Hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulphooxy)amino]-2-[(sulphooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulphooxy)oxane-2-carboxylate</synonym>
    <synonym>(2S,3R,4R,5S,6R)-4-Hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulphooxy)amino]-2-[(sulphooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulphooxy)oxane-2-carboxylic acid</synonym>
  </synonyms>
  <chemical_formula>C14H25NO21S3</chemical_formula>
  <average_molecular_weight>639.52</average_molecular_weight>
  <monisotopic_moleculate_weight>639.008120351</monisotopic_moleculate_weight>
  <iupac_name>(2S,3R,4R,5S,6R)-4-hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulfooxy)amino]-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulfooxy)oxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>(2S,3R,4R,5S,6R)-4-hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulfooxy)amino]-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulfooxy)oxane-2-carboxylic acid</traditional_iupac>
  <cas_registry_number>9050-30-0</cas_registry_number>
  <smiles>CO[C@@H]1O[C@@H](COS(O)(=O)=O)[C@H](O[C@@H]2O[C@@H]([C@H](OC)[C@@H](O)[C@@H]2OS(O)(=O)=O)C(O)=O)[C@@H](O)[C@@H]1NOS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C14H25NO21S3/c1-29-9-7(17)10(35-38(23,24)25)14(34-11(9)12(18)19)33-8-4(3-31-37(20,21)22)32-13(30-2)5(6(8)16)15-36-39(26,27)28/h4-11,13-17H,3H2,1-2H3,(H,18,19)(H,20,21,22)(H,23,24,25)(H,26,27,28)/t4-,5-,6-,7+,8-,9+,10-,11-,13+,14+/m0/s1</inchi>
  <inchikey>AUQASCCBXZRMEG-RHKLHVFKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as disaccharide sulfates. These are disaccharides carrying  one or more sulfate group on a sugar unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Disaccharide sulfates</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>O-glucuronides</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-o-glucuronide</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Disaccharide sulfate</substituent>
      <substituent>Ether</substituent>
      <substituent>Glucuronic acid or derivatives</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>O-glucuronide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-8.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3R,4R,5S,6R)-4-hydroxy-6-{[(2S,3R,4S,5S,6R)-4-hydroxy-6-methoxy-5-[(sulfooxy)amino]-2-[(sulfooxy)methyl]oxan-3-yl]oxy}-3-methoxy-5-(sulfooxy)oxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>639.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>639.008120351</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CO[C@@H]1O[C@@H](COS(O)(=O)=O)[C@H](O[C@@H]2O[C@@H]([C@H](OC)[C@@H](O)[C@@H]2OS(O)(=O)=O)C(O)=O)[C@@H](O)[C@@H]1NOS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H25NO21S3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H25NO21S3/c1-29-9-7(17)10(35-38(23,24)25)14(34-11(9)12(18)19)33-8-4(3-31-37(20,21)22)32-13(30-2)5(6(8)16)15-36-39(26,27)28/h4-11,13-17H,3H2,1-2H3,(H,18,19)(H,20,21,22)(H,23,24,25)(H,26,27,28)/t4-,5-,6-,7+,8-,9+,10-,11-,13+,14+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AUQASCCBXZRMEG-RHKLHVFKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>326.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>121.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>52.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1276030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1276031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1276032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1390969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1390970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1390971</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00925</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022184</foodb_id>
  <chemspider_id/>
  <pdbe_id/>
  <chebi_id/>
  <pubchem_compound_id>53477715</pubchem_compound_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Heparan sulfate</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Meier, Bernd Horst; Meier, Nele.  Manufacture and use of modified adducts of polysaccharides and chitosan or chitin and a process to improve the preparation of polysaccharide-drug conjugates.    PCT Int. Appl.  (2007),     67pp.  CODEN: PIXXD2  WO  2007122269  A1  20071101  CAN 147:487869  AN 2007:1237349  </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00380</protein_accession>
      <name>N-acetylglucosamine-6-sulfatase</name>
      <uniprot_id>Q1LZH9</uniprot_id>
      <gene_name>GNS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01345</protein_accession>
      <name>Cartilage oligomeric matrix protein</name>
      <uniprot_id>P35445</uniprot_id>
      <gene_name>COMP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01349</protein_accession>
      <name>Vascular endothelial growth factor A</name>
      <uniprot_id>P15691</uniprot_id>
      <gene_name>VEGFA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01351</protein_accession>
      <name>Prolargin</name>
      <uniprot_id>Q9GKN8</uniprot_id>
      <gene_name>PRELP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01576</protein_accession>
      <name>Glypican 6</name>
      <uniprot_id>A1L539</uniprot_id>
      <gene_name>GPC6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01577</protein_accession>
      <name>GPC5 protein</name>
      <uniprot_id>A7MB84</uniprot_id>
      <gene_name>GPC5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01578</protein_accession>
      <name>Syndecan-2</name>
      <uniprot_id>Q58DD4</uniprot_id>
      <gene_name>SDC2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01579</protein_accession>
      <name>Syndecan-1</name>
      <uniprot_id>Q08DZ5</uniprot_id>
      <gene_name>SDC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01580</protein_accession>
      <name>Glypican 3</name>
      <uniprot_id>Q3ZBZ6</uniprot_id>
      <gene_name>GPC3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01581</protein_accession>
      <name>Glypican 1</name>
      <uniprot_id>Q2KJ65</uniprot_id>
      <gene_name>GPC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:01 UTC</creation_date>
  <update_date>2020-03-13 16:23:07 UTC</update_date>
  <accession>BMDB0000694</accession>
  <secondary_accessions>
    <accession>BMDB00694</accession>
  </secondary_accessions>
  <name>L-2-Hydroxyglutaric acid</name>
  <description/>
  <synonyms>
    <synonym>(S)-2-Hydroxyglutarate</synonym>
    <synonym>(S)-2-Hydroxyglutaric acid</synonym>
    <synonym>L-2-Hydroxyglutarate</synonym>
    <synonym>(S)-Α-hydroxyglutarate</synonym>
    <synonym>(S)-Α-hydroxyglutaric acid</synonym>
    <synonym>(S)-alpha-Hydroxyglutarate</synonym>
    <synonym>(S)-alpha-Hydroxyglutaric acid</synonym>
    <synonym>2-Hydroxy-(S)-pentanedioate</synonym>
    <synonym>2-Hydroxy-(S)-pentanedioic acid</synonym>
    <synonym>2-Hydroxy-L-glutarate</synonym>
    <synonym>2-Hydroxy-L-glutaric acid</synonym>
    <synonym>L-Α-hydroxyglutarate</synonym>
    <synonym>L-Α-hydroxyglutaric acid</synonym>
    <synonym>L-alpha-Hydroxyglutarate</synonym>
    <synonym>L-alpha-Hydroxyglutaric acid</synonym>
    <synonym>L-2-Hydroxyglutaric acid</synonym>
  </synonyms>
  <chemical_formula>C5H8O5</chemical_formula>
  <average_molecular_weight>148.114</average_molecular_weight>
  <monisotopic_moleculate_weight>148.037173366</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-hydroxypentanedioic acid</iupac_name>
  <traditional_iupac>L-2-hydroxyglutaric acid</traditional_iupac>
  <cas_registry_number>13095-48-2</cas_registry_number>
  <smiles>O[C@@H](CCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/t3-/m0/s1</inchi>
  <inchikey>HWXBTNAVRSUOJR-VKHMYHEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Short-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Short-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxyglutaric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-hydroxypentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>148.114</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>148.037173366</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H](CCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/t3-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HWXBTNAVRSUOJR-VKHMYHEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>29.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1307377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1307378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1307379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1421887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1421888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1421889</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03196</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022185</foodb_id>
  <chemspider_id>388969</chemspider_id>
  <pubchem_compound_id>439939</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>32797</chebi_id>
  <meta_cyc_id>CPD-381</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Alpha-Hydroxyglutaric acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Kobayashi, Hidehiko; Yamaguchi, Koretaka; Yamashita, Takeshi.  a-Hydroxyglutaric acid from glutamic acid.    Jpn. Tokkyo Koho  (1968),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00357</protein_accession>
      <name>L-2-hydroxyglutarate dehydrogenase, mitochondrial</name>
      <uniprot_id>A7MBI3</uniprot_id>
      <gene_name>L2HGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:02 UTC</creation_date>
  <update_date>2020-04-16 17:51:22 UTC</update_date>
  <accession>BMDB0000695</accession>
  <secondary_accessions>
    <accession>BMDB00695</accession>
  </secondary_accessions>
  <name>Ketoleucine</name>
  <description/>
  <synonyms>
    <synonym>2-oxo-4-METHYLPENTANOIC ACID</synonym>
    <synonym>2-Oxoisocaproate</synonym>
    <synonym>4-Methyl-2-oxopentanoate</synonym>
    <synonym>4-Methyl-2-oxovaleric acid</synonym>
    <synonym>alpha-Ketoisocaproic acid</synonym>
    <synonym>2-oxo-4-METHYLPENTANOate</synonym>
    <synonym>2-Oxoisocaproic acid</synonym>
    <synonym>4-Methyl-2-oxopentanoic acid</synonym>
    <synonym>4-Methyl-2-oxovalerate</synonym>
    <synonym>a-Ketoisocaproate</synonym>
    <synonym>a-Ketoisocaproic acid</synonym>
    <synonym>alpha-Ketoisocaproate</synonym>
    <synonym>Α-ketoisocaproate</synonym>
    <synonym>Α-ketoisocaproic acid</synonym>
    <synonym>2-Keto-4-methylvalerate</synonym>
    <synonym>2-Keto-4-methylvaleric acid</synonym>
    <synonym>2-Ketoisocaproate</synonym>
    <synonym>2-Ketoisocaproic acid</synonym>
    <synonym>2-oxo-4-Methylvalerate</synonym>
    <synonym>2-oxo-4-Methylvaleric acid</synonym>
    <synonym>2-Oxoleucine</synonym>
    <synonym>4-Methyl-2-oxo-valerate</synonym>
    <synonym>4-Methyl-2-oxo-valeric acid</synonym>
    <synonym>a-Ketoisocapronate</synonym>
    <synonym>a-Ketoisocapronic acid</synonym>
    <synonym>a-Oxoisocaproate</synonym>
    <synonym>a-Oxoisocaproic acid</synonym>
    <synonym>alpha-Keto-isocaproate</synonym>
    <synonym>alpha-Keto-isocaproic acid</synonym>
    <synonym>alpha-Ketoisocapronate</synonym>
    <synonym>alpha-Ketoisocapronic acid</synonym>
    <synonym>alpha-Oxoisocaproate</synonym>
    <synonym>alpha-Oxoisocaproic acid</synonym>
    <synonym>Ketoisocaproate</synonym>
    <synonym>Ketoisocaproic acid</synonym>
    <synonym>Methyloxovalerate</synonym>
    <synonym>Methyloxovaleric acid</synonym>
    <synonym>Oxoisocaproate</synonym>
    <synonym>Oxoisocaproic acid</synonym>
    <synonym>Keto-leucine</synonym>
  </synonyms>
  <chemical_formula>C6H10O3</chemical_formula>
  <average_molecular_weight>130.1418</average_molecular_weight>
  <monisotopic_moleculate_weight>130.062994186</monisotopic_moleculate_weight>
  <iupac_name>4-methyl-2-oxopentanoic acid</iupac_name>
  <traditional_iupac>ketoisocaproate</traditional_iupac>
  <cas_registry_number>816-66-0</cas_registry_number>
  <smiles>CC(C)CC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)</inchi>
  <inchikey>BKAJNAXTPSGJCU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Short-chain keto acids and derivatives</sub_class>
    <direct_parent>Short-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain keto acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>8 - 10 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>32 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-methyl-2-oxopentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>130.1418</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>130.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BKAJNAXTPSGJCU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438660</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00233</kegg_id>
  <drugbank_id>DB03229</drugbank_id>
  <foodb_id>FDB030510</foodb_id>
  <chemspider_id>69</chemspider_id>
  <pdbe_id/>
  <chebi_id>48430</chebi_id>
  <pubchem_compound_id>70</pubchem_compound_id>
  <meta_cyc_id>2K-4CH3-PENTANOATE</meta_cyc_id>
  <knapsack_id>C00019677</knapsack_id>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>34334</bigg_id>
  <metlin_id>5663</metlin_id>
  <synthesis_reference>Tabuchi, Takeshi; Abe, Matazo.  Fermentative preparation of a-ketoisocaproic acid.    Jpn. Tokkyo Koho  (1970),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:03 UTC</creation_date>
  <update_date>2020-04-16 20:38:32 UTC</update_date>
  <accession>BMDB0000696</accession>
  <secondary_accessions>
    <accession>BMDB00696</accession>
  </secondary_accessions>
  <name>L-Methionine</name>
  <description>L-Methionine, also known as liquimeth or pedameth, belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Methionine is a drug which is used for protein synthesis including the formation of same, l-homocysteine, l-cysteine, taurine, and sulfate. L-Methionine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Methionine exists in all living species, ranging from bacteria to humans. L-Methionine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2S)-2-Amino-4-(methylsulfanyl)butanoic acid</synonym>
    <synonym>(S)-2-Amino-4-(methylthio)butanoic acid</synonym>
    <synonym>(S)-2-Amino-4-(methylthio)butyric acid</synonym>
    <synonym>(S)-Methionine</synonym>
    <synonym>L-(-)-Methionine</synonym>
    <synonym>L-alpha-Amino-gamma-methylmercaptobutyric acid</synonym>
    <synonym>L-Methionin</synonym>
    <synonym>M</synonym>
    <synonym>Met</synonym>
    <synonym>METHIONINE</synonym>
    <synonym>L-2-Amino-4methylthiobutyric acid</synonym>
    <synonym>L-Methionine Z</synonym>
    <synonym>(2S)-2-Amino-4-(methylsulfanyl)butanoate</synonym>
    <synonym>(2S)-2-Amino-4-(methylsulphanyl)butanoate</synonym>
    <synonym>(2S)-2-Amino-4-(methylsulphanyl)butanoic acid</synonym>
    <synonym>(S)-2-Amino-4-(methylthio)butanoate</synonym>
    <synonym>(S)-2-Amino-4-(methylthio)butyrate</synonym>
    <synonym>L-a-Amino-g-methylmercaptobutyrate</synonym>
    <synonym>L-a-Amino-g-methylmercaptobutyric acid</synonym>
    <synonym>L-alpha-Amino-gamma-methylmercaptobutyrate</synonym>
    <synonym>L-Α-amino-γ-methylmercaptobutyrate</synonym>
    <synonym>L-Α-amino-γ-methylmercaptobutyric acid</synonym>
    <synonym>L-2-Amino-4methylthiobutyrate</synonym>
    <synonym>(L)-Methionine</synonym>
    <synonym>(S)-(+)-Methionine</synonym>
    <synonym>(S)-2-Amino-4-(methylthio)-butanoate</synonym>
    <synonym>(S)-2-Amino-4-(methylthio)-butanoic acid</synonym>
    <synonym>2-Amino-4-(methylthio)butyrate</synonym>
    <synonym>2-Amino-4-(methylthio)butyric acid</synonym>
    <synonym>2-Amino-4-methylthiobutanoate</synonym>
    <synonym>2-Amino-4-methylthiobutanoic acid</synonym>
    <synonym>a-Amino-g-methylmercaptobutyrate</synonym>
    <synonym>a-Amino-g-methylmercaptobutyric acid</synonym>
    <synonym>Acimethin</synonym>
    <synonym>alpha-Amino-alpha-aminobutyric acid</synonym>
    <synonym>alpha-Amino-gamma-methylmercaptobutyrate</synonym>
    <synonym>alpha-Amino-gamma-methylmercaptobutyric acid</synonym>
    <synonym>Cymethion</synonym>
    <synonym>g-Methylthio-a-aminobutyrate</synonym>
    <synonym>g-Methylthio-a-aminobutyric acid</synonym>
    <synonym>gamma-Methylthio-alpha-aminobutyrate</synonym>
    <synonym>gamma-Methylthio-alpha-aminobutyric acid</synonym>
    <synonym>H-Met-H</synonym>
    <synonym>H-Met-OH</synonym>
    <synonym>L(-)-Amino-alpha-amino-alpha-aminobutyric acid</synonym>
    <synonym>L(-)-Amino-gamma-methylthiobutyric acid</synonym>
    <synonym>L-2-Amino-4-(methylthio)butyric acid</synonym>
    <synonym>L-2-Amino-4-methylthiobutyric acid</synonym>
    <synonym>L-a-Amino-g-methylthiobutyrate</synonym>
    <synonym>L-a-Amino-g-methylthiobutyric acid</synonym>
    <synonym>L-alpha-Amino-gamma-methylthiobutyrate</synonym>
    <synonym>L-alpha-Amino-gamma-methylthiobutyric acid</synonym>
    <synonym>L-gamma-Methylthio-alpha-aminobutyric acid</synonym>
    <synonym>L-Methioninum</synonym>
    <synonym>Liquimeth</synonym>
    <synonym>Mepron</synonym>
    <synonym>Methilanin</synonym>
    <synonym>Methioninum</synonym>
    <synonym>Metionina</synonym>
    <synonym>Neo-methidin</synonym>
    <synonym>Poly-L-methionine</synonym>
    <synonym>Polymethionine</synonym>
    <synonym>S-Methionine</synonym>
    <synonym>S-Methyl-L-homocysteine</synonym>
    <synonym>Toxin war</synonym>
    <synonym>L-Isomer methionine</synonym>
    <synonym>Methionine, L-isomer</synonym>
    <synonym>Pedameth</synonym>
    <synonym>Methionine, L isomer</synonym>
    <synonym>(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-BETA,BETA-carotene-3,3'-diol</synonym>
    <synonym>Bo-xan</synonym>
    <synonym>e 161b</synonym>
    <synonym>Xanthophyll</synonym>
    <synonym>(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diol</synonym>
    <synonym>(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diol</synonym>
  </synonyms>
  <chemical_formula>C5H11NO2S</chemical_formula>
  <average_molecular_weight>149.211</average_molecular_weight>
  <monisotopic_moleculate_weight>149.051049291</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-(methylsulfanyl)butanoic acid</iupac_name>
  <traditional_iupac>L-methionine</traditional_iupac>
  <cas_registry_number>63-68-3</cas_registry_number>
  <smiles>CSCC[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1</inchi>
  <inchikey>FFEARJCKVFRZRR-BYPYZUCNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Methionine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylthioethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Methionine or derivatives</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thia fatty acid</substituent>
      <substituent>Thioether</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>aspartate family amino acid</external_descriptor>
      <external_descriptor>methionine</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>284 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>56.6 mg/mL</value>
      <source>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.87</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-(methylsulfanyl)butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>149.211</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>149.051049291</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CSCC[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H11NO2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FFEARJCKVFRZRR-BYPYZUCNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Methionine</name>
      <smpdb_id>SMP0119405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2922</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179110</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>20.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>22-29</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>27.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>46-52</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>34+/-4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>18-29</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>54+/-16</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>34+/-10</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.9 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5897.689</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5897.689</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5897.689</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5897.689</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5763.65</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5763.65</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5763.65</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>148.53 +/- 22.45</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>151.61 +/- 8.67</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>168.81 +/- 20.31</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>262.51 +/- 12.18</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>126-275</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>560</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.99+/-0.14</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1.08+/-0.19</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.79+/-0.10</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.85+/-0.14</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>40-395</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>24.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>34.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>47.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>20.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>22-53</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>44.0 (27 - 61)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>This concentration measured after 1 hour of feeding.; The three amino acids (AA), threonine, methionine and Lysine were administered intraruminally in mixtures at dosages of 100, 200, 300, and 400 mmol of each,together with polyethylene glycol (PEG) as a liquid marker.  </comment>
      <references>
        <reference>
          <reference_text>Volden H, Velle W, Harstad OM, Aulie A, Sjaastad OV: Apparent ruminal degradation and rumen escape of lysine, methionine, and threonine administered intraruminally in mixtures to high-yielding cows. J Anim Sci. 1998 Apr;76(4):1232-40.</reference_text>
          <pubmed_id>9581948</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>22 +/- 8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>32 +/- 10</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>47 +/- 19</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>19 +/- 10</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>19 +/- 10</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by GC-MS and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>268+/-102</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>37+/-11</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>26+/-6</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00073</kegg_id>
  <drugbank_id>DB00134</drugbank_id>
  <foodb_id>FDB012683</foodb_id>
  <chemspider_id>5907</chemspider_id>
  <pdbe_id/>
  <chebi_id>16643</chebi_id>
  <pubchem_compound_id>6137</pubchem_compound_id>
  <meta_cyc_id>MET</meta_cyc_id>
  <knapsack_id>C00001379</knapsack_id>
  <wikipedia_id>Methionine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33753</bigg_id>
  <metlin_id>5664</metlin_id>
  <synthesis_reference>Boy, Matthias; Klein, Daniela; Schroeder, Hartwig.  Method for the production and recovery of methionine.    PCT Int. Appl.  (2005),     34 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00174</protein_accession>
      <name>S-adenosylmethionine synthetase</name>
      <uniprot_id>A7E3T7</uniprot_id>
      <gene_name>MAT2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00396</protein_accession>
      <name>Lipoyl synthase, mitochondrial</name>
      <uniprot_id>Q5BIP7</uniprot_id>
      <gene_name>LIAS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00403</protein_accession>
      <name>S-adenosylmethionine synthetase isoform type-1</name>
      <uniprot_id>Q2KJC6</uniprot_id>
      <gene_name>MAT1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00414</protein_accession>
      <name>Methionine synthase</name>
      <uniprot_id>Q4JIJ3</uniprot_id>
      <gene_name>MTR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00547</protein_accession>
      <name>Methionine-R-sulfoxide reductase B1</name>
      <uniprot_id>Q3MHL9</uniprot_id>
      <gene_name>SEPX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00795</protein_accession>
      <name>Methionine aminopeptidase 1</name>
      <uniprot_id>A6QLA4</uniprot_id>
      <gene_name>METAP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00797</protein_accession>
      <name>Methionine aminopeptidase 2</name>
      <uniprot_id>Q3ZC89</uniprot_id>
      <gene_name>METAP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01057</protein_accession>
      <name>Betaine--homocysteine S-methyltransferase 1</name>
      <uniprot_id>Q5I597</uniprot_id>
      <gene_name>BHMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01249</protein_accession>
      <name>Peptide methionine sulfoxide reductase</name>
      <uniprot_id>P54149</uniprot_id>
      <gene_name>MSRA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01250</protein_accession>
      <name>Methionyl-tRNA synthetase, mitochondrial</name>
      <uniprot_id>A6H7E1</uniprot_id>
      <gene_name>MARS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01251</protein_accession>
      <name>Methionyl-tRNA synthetase, cytoplasmic</name>
      <uniprot_id>Q2T9L8</uniprot_id>
      <gene_name>MARS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01585</protein_accession>
      <name>S-adenosylmethionine mitochondrial carrier protein</name>
      <uniprot_id>A6QR09</uniprot_id>
      <gene_name>SLC25A26</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:04 UTC</creation_date>
  <update_date>2020-03-13 16:23:08 UTC</update_date>
  <accession>BMDB0000697</accession>
  <secondary_accessions>
    <accession>BMDB00697</accession>
  </secondary_accessions>
  <name>Isocoproporphyrin</name>
  <description/>
  <synonyms>
    <synonym>3-(Carboxymethyl)-12-ethyl-8,13,17-trimethyl- 21H,23H-porphine-2,7,18-tripropanoate</synonym>
    <synonym>3-(Carboxymethyl)-12-ethyl-8,13,17-trimethyl- 21H,23H-porphine-2,7,18-tripropanoic acid</synonym>
    <synonym>3-[15,20-Bis(2-carboxyethyl)-19-(carboxymethyl)-10-ethyl-5,9,14-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C36H38N4O8</chemical_formula>
  <average_molecular_weight>654.7089</average_molecular_weight>
  <monisotopic_moleculate_weight>654.268964212</monisotopic_moleculate_weight>
  <iupac_name>3-[15,19-bis(2-carboxyethyl)-20-(carboxymethyl)-9-ethyl-5,10,14-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[15,19-bis(2-carboxyethyl)-20-(carboxymethyl)-9-ethyl-5,10,14-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>36548-09-1</cas_registry_number>
  <smiles>CCC1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)/C(CCC(O)=O)=C3C</smiles>
  <inchi>InChI=1S/C36H38N4O8/c1-5-20-17(2)25-13-26-18(3)21(6-9-33(41)42)29(38-26)15-31-23(8-11-35(45)46)24(12-36(47)48)32(40-31)16-30-22(7-10-34(43)44)19(4)27(39-30)14-28(20)37-25/h13-16,37,40H,5-12H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)/b25-13-,26-13-,27-14-,28-14-,29-15-,30-16-,31-15-,32-16-</inchi>
  <inchikey>UHKZSWAPQUEURH-TXUIXYGZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[15,19-bis(2-carboxyethyl)-20-(carboxymethyl)-9-ethyl-5,10,14-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>654.7089</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>654.268964212</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)/C(CCC(O)=O)=C3C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C36H38N4O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C36H38N4O8/c1-5-20-17(2)25-13-26-18(3)21(6-9-33(41)42)29(38-26)15-31-23(8-11-35(45)46)24(12-36(47)48)32(40-31)16-30-22(7-10-34(43)44)19(4)27(39-30)14-28(20)37-25/h13-16,37,40H,5-12H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)/b25-13-,26-13-,27-14-,28-14-,29-15-,30-16-,31-15-,32-16-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UHKZSWAPQUEURH-TXUIXYGZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>206.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>176.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>73.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349404</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB022186</foodb_id>
  <chemspider_id>148480</chemspider_id>
  <pubchem_compound_id/>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Isocoproporphyrin</wikipedia_id>
  <metlin_id>5665</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:05 UTC</creation_date>
  <update_date>2020-04-15 22:14:21 UTC</update_date>
  <accession>BMDB0000698</accession>
  <secondary_accessions>
    <accession>BMDB00698</accession>
  </secondary_accessions>
  <name>Lithocholic acid glycine conjugate</name>
  <description/>
  <synonyms>
    <synonym>Glycolithocholate</synonym>
    <synonym>Lithocholylglycine</synonym>
    <synonym>N-((3-alpha,5-beta)-3-Hydroxy-24-oxocholan-24-yl)glycine</synonym>
    <synonym>Glycolithocholic acid</synonym>
    <synonym>N-((3-a,5-b)-3-Hydroxy-24-oxocholan-24-yl)glycine</synonym>
    <synonym>N-((3-Α,5-β)-3-hydroxy-24-oxocholan-24-yl)glycine</synonym>
    <synonym>Lithocholate glycine conjugate</synonym>
    <synonym>Lithocholic acid glycine conjugic acid</synonym>
    <synonym>3a-Hydroxy-5b-cholanic acid glycine ester</synonym>
    <synonym>3a-Hydroxy-5b-cholanoylglycine</synonym>
    <synonym>3a-Hydroxy-N-(carboxymethyl)-5b-cholan-24-amide</synonym>
    <synonym>3alpha-Hydroxy-5beta-cholan-24-Oate</synonym>
    <synonym>3alpha-Hydroxy-5beta-cholan-24-Oic acid</synonym>
    <synonym>3alpha-Hydroxy-5beta-cholan-24-Oic acid N-(carboxymethyl)amide</synonym>
    <synonym>Lithocholoyglycine</synonym>
    <synonym>N-(3a-Hydroxy-5b-cholan-24-oyl)-glycine</synonym>
    <synonym>N-(3a-Hydroxy-5b-cholanoyl)glycine</synonym>
    <synonym>N-(Carboxymethyl)-3a-hydroxy-5b-cholan-24-amide</synonym>
    <synonym>Glycolithocholic acid, monosodium salt</synonym>
    <synonym>3alpha-Hydroxy-5beta-cholanoylglycine 3-sulfate</synonym>
    <synonym>3alpha-Hydroxy-5beta-cholanoylglycine 3-sulphate</synonym>
    <synonym>3α-Hydroxy-5β-cholanoylglycine 3-sulfate</synonym>
    <synonym>3α-Hydroxy-5β-cholanoylglycine 3-sulphate</synonym>
    <synonym>Glycolithocholic acid 3-sulfate</synonym>
    <synonym>Glycolithocholic acid 3-sulphate</synonym>
    <synonym>Glycolithocholic acid 3alpha-sulfate</synonym>
    <synonym>Glycolithocholic acid 3alpha-sulphate</synonym>
    <synonym>Glycolithocholic acid 3α-sulfate</synonym>
    <synonym>Glycolithocholic acid 3α-sulphate</synonym>
    <synonym>Glycolithocholic acid sulfate</synonym>
    <synonym>Glycolithocholic acid sulphate</synonym>
    <synonym>N-[(3alpha,5beta)-24-Oxo-3-(sulfooxy)cholan-24-yl]glycine</synonym>
    <synonym>N-[(3α,5β)-24-Oxo-3-(sulfooxy)cholan-24-yl]glycine</synonym>
    <synonym>Sulfoglycolithocholic acid</synonym>
    <synonym>Sulfolithocholylglycine</synonym>
  </synonyms>
  <chemical_formula>C26H43NO4</chemical_formula>
  <average_molecular_weight>433.6239</average_molecular_weight>
  <monisotopic_moleculate_weight>433.319208869</monisotopic_moleculate_weight>
  <iupac_name>2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid</iupac_name>
  <traditional_iupac>[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid</traditional_iupac>
  <cas_registry_number>474-74-8</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1</inchi>
  <inchikey>XBSQTYHEGZTYJE-OETIFKLTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Glycinated bile acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monohydroxy bile acids, alcohols and derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Glycinated bile acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monohydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Glycine conjugates</external_descriptor>
      <external_descriptor>N-acylglycine</external_descriptor>
      <external_descriptor>bile acid glycine conjugate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>433.6239</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>433.319208869</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H43NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H43NO4/c1-16(4-9-23(29)27-15-24(30)31)20-7-8-21-19-6-5-17-14-18(28)10-12-25(17,2)22(19)11-13-26(20,21)3/h16-22,28H,4-15H2,1-3H3,(H,27,29)(H,30,31)/t16-,17-,18-,19+,20-,21+,22+,25+,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XBSQTYHEGZTYJE-OETIFKLTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>86.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>120.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>56001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>56002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>56003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>111306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>111307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>111308</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C15557</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022187</foodb_id>
  <chemspider_id>103116</chemspider_id>
  <pubchem_compound_id>115245</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>37998</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5666</metlin_id>
  <synthesis_reference>Momose, Toshiaki; Tsubaki, Takayuki; Iida, Takashi; Nambara, Toshio.  An improved synthesis of taurine- and glycine-conjugated bile acids.    Lipids  (1997),  32(7),  775-778.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:07 UTC</creation_date>
  <update_date>2020-04-14 22:48:08 UTC</update_date>
  <accession>BMDB0000699</accession>
  <secondary_accessions>
    <accession>BMDB00699</accession>
  </secondary_accessions>
  <name>1-Methylnicotinamide</name>
  <description>1-Methylnicotinamide, also known as 1-methylnicotinamide or 1-methylnicotinamide, belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group. 1-Methylnicotinamide is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Methylnicotinamide exists in all living species, ranging from bacteria to humans. 1-Methylnicotinamide participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and 1-methylnicotinamide can be biosynthesized from S-adenosylmethionine and niacinamide; which is catalyzed by the enzyme nicotinamide N-methyltransferase. In addition, 1-Methylnicotinamide can be converted into N1-methyl-2-pyridone-5-carboxamide through the action of the enzyme aldehyde oxidase. In cattle, 1-methylnicotinamide is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway.</description>
  <synonyms>
    <synonym>1-Methylnicotinamide cation</synonym>
    <synonym>3-(Aminocarbonyl)-1-methylpyridinium</synonym>
    <synonym>N(1)-Methylnicotinamide</synonym>
    <synonym>Trigonellinamide</synonym>
    <synonym>1-Methyl-3-carbamoylpyridinium</synonym>
    <synonym>1-Methyl-3-carbamoylpyridinium cation</synonym>
    <synonym>3-Amido-N-methylpyridinium: 1-methyl-3-pyridinecarboxamide</synonym>
    <synonym>3-Carbamoyl-1-methyl-pyridinium</synonym>
    <synonym>I-methyl nicotinamide</synonym>
    <synonym>N'-methylnicotinamide</synonym>
    <synonym>N'Methylnicotinamide</synonym>
    <synonym>N-1-Methylnicotinamide</synonym>
    <synonym>N-Methyl-3-carbamidopyridinium</synonym>
    <synonym>N-Methyl-3-carbamoylpyridinium ion</synonym>
    <synonym>N1-Methylnicotinamide</synonym>
    <synonym>N(1)-Methylnicotinamide chloride</synonym>
    <synonym>N(1)-Methylnicotinamide cyanide</synonym>
    <synonym>N(1)-Methylnicotinamide fluoride</synonym>
    <synonym>N(1)-Methylnicotinamide iodide, 3-(aminocarbonyl-13C)-labeled</synonym>
    <synonym>N(1)-Methylnicotinamide methylsulfate</synonym>
    <synonym>N(1)-Methylnicotinamide perchlorate</synonym>
    <synonym>N(1)-Methylnicotinamide bromide</synonym>
    <synonym>N(1)-Methylnicotinamide iodide</synonym>
    <synonym>N(1)-Methylnicotinamide tetrafluoroborate (1-)</synonym>
    <synonym>Trigonellamide chloride</synonym>
  </synonyms>
  <chemical_formula>C7H9N2O</chemical_formula>
  <average_molecular_weight>137.1592</average_molecular_weight>
  <monisotopic_moleculate_weight>137.07148792</monisotopic_moleculate_weight>
  <iupac_name>3-carbamoyl-1-methylpyridin-1-ium</iupac_name>
  <traditional_iupac>1-methylnicotinamide</traditional_iupac>
  <cas_registry_number>3106-60-3</cas_registry_number>
  <smiles>C[N+]1=CC=CC(=C1)C(N)=O</smiles>
  <inchi>InChI=1S/C7H8N2O/c1-9-4-2-3-6(5-9)7(8)10/h2-5H,1H3,(H-,8,10)/p+1</inchi>
  <inchikey>LDHMAVIPBRSVRG-UHFFFAOYSA-O</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyridinecarboxylic acids and derivatives</sub_class>
    <direct_parent>Nicotinamides</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-methylpyridinium compounds</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Pyridinium derivatives</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-methylpyridinium</substituent>
      <substituent>Nicotinamide</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Pyridinium</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>pyridinium ion</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>855 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-carbamoyl-1-methylpyridin-1-ium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>137.1592</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>137.07148792</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+]1=CC=CC(=C1)C(N)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H9N2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H8N2O/c1-9-4-2-3-6(5-9)7(8)10/h2-5H,1H3,(H-,8,10)/p+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LDHMAVIPBRSVRG-UHFFFAOYSA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>46.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451924</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02918</kegg_id>
  <drugbank_id>DB11710</drugbank_id>
  <foodb_id>FDB022188</foodb_id>
  <chemspider_id>444</chemspider_id>
  <pdbe_id/>
  <chebi_id>16797</chebi_id>
  <pubchem_compound_id>457</pubchem_compound_id>
  <meta_cyc_id>CPD-396</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>1-Methylnicotinamide</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>2226225</bigg_id>
  <metlin_id>5667</metlin_id>
  <synthesis_reference>Nelis, Hans J. C. F.; Airy, Subhash C.; Sinsheimer, J. E.  Comparison of the alkylation of nicotinamide and 4-(p-nitrobenzyl)pyridine for the determination of aliphatic epoxides.    Analytical Chemistry  (1982),  54(2),  213-16.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:08 UTC</creation_date>
  <update_date>2020-03-13 16:23:10 UTC</update_date>
  <accession>BMDB0000700</accession>
  <secondary_accessions>
    <accession>BMDB00700</accession>
  </secondary_accessions>
  <name>Hydroxypropionic acid</name>
  <description/>
  <synonyms>
    <synonym>3-HYDROXY-propanoIC ACID</synonym>
    <synonym>3-Hydroxypropanoic acid</synonym>
    <synonym>beta-Hydroxypropionic acid</synonym>
    <synonym>Hydracrylic acid</synonym>
    <synonym>3-Hydroxypropionate</synonym>
    <synonym>3-Hydroxypropionic acid</synonym>
    <synonym>3-HYDROXY-propanoate</synonym>
    <synonym>3-Hydroxypropanoate</synonym>
    <synonym>b-Hydroxypropionate</synonym>
    <synonym>b-Hydroxypropionic acid</synonym>
    <synonym>beta-Hydroxypropionate</synonym>
    <synonym>Β-hydroxypropionate</synonym>
    <synonym>Β-hydroxypropionic acid</synonym>
    <synonym>Hydracrylate</synonym>
    <synonym>Hydroxypropionate</synonym>
    <synonym>2-Deoxyglycerate</synonym>
    <synonym>2-Deoxyglyceric acid</synonym>
    <synonym>b-Lactate</synonym>
    <synonym>b-Lactic acid</synonym>
    <synonym>beta-Lactate</synonym>
    <synonym>beta-Lactic acid</synonym>
    <synonym>Ethylenelactate</synonym>
    <synonym>Ethylenelactic acid</synonym>
  </synonyms>
  <chemical_formula>C3H6O3</chemical_formula>
  <average_molecular_weight>90.0779</average_molecular_weight>
  <monisotopic_moleculate_weight>90.031694058</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxypropanoic acid</iupac_name>
  <traditional_iupac>hydroxypropionic acid</traditional_iupac>
  <cas_registry_number>503-66-2</cas_registry_number>
  <smiles>OCCC(O)=O</smiles>
  <inchi>InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)</inchi>
  <inchikey>ALRHLSYJTWAHJZ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Beta hydroxy acids and derivatives</sub_class>
    <direct_parent>Beta hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>omega-hydroxy fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>&lt; 25 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxypropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>90.0779</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>90.031694058</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H6O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ALRHLSYJTWAHJZ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>19.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437919</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01013</kegg_id>
  <drugbank_id>DB03688</drugbank_id>
  <foodb_id>FDB030432</foodb_id>
  <chemspider_id>61460</chemspider_id>
  <pdbe_id/>
  <chebi_id>33404</chebi_id>
  <pubchem_compound_id>68152</pubchem_compound_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Hydroxypropanoic acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>53188</bigg_id>
  <metlin_id>5668</metlin_id>
  <synthesis_reference>Suthers, Patrick F.; Cameron, Douglas C.  Production of 3-hydroxypropionic acid in recombinant organisms.    PCT Int. Appl.  (2001),     63 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:09 UTC</creation_date>
  <update_date>2020-03-13 16:23:11 UTC</update_date>
  <accession>BMDB0000701</accession>
  <secondary_accessions>
    <accession>BMDB00701</accession>
  </secondary_accessions>
  <name>Hexanoylglycine</name>
  <description/>
  <synonyms>
    <synonym>Caproylglycine</synonym>
    <synonym>N-(1-Oxohexyl)glycine</synonym>
    <synonym>N-Caproylglycine</synonym>
    <synonym>N-Hexanoyl-glycine</synonym>
    <synonym>N-Hexanoylglycine</synonym>
    <synonym>Hexanoylglycine</synonym>
  </synonyms>
  <chemical_formula>C8H15NO3</chemical_formula>
  <average_molecular_weight>173.2096</average_molecular_weight>
  <monisotopic_moleculate_weight>173.105193351</monisotopic_moleculate_weight>
  <iupac_name>2-hexanamidoacetic acid</iupac_name>
  <traditional_iupac>hexanoylglycine</traditional_iupac>
  <cas_registry_number>24003-67-6</cas_registry_number>
  <smiles>CCCCCC(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C8H15NO3/c1-2-3-4-5-7(10)9-6-8(11)12/h2-6H2,1H3,(H,9,10)(H,11,12)</inchi>
  <inchikey>UPCKIPHSXMXJOX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylglycine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hexanamidoacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>173.2096</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>173.105193351</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCC(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15NO3/c1-2-3-4-5-7(10)9-6-8(11)12/h2-6H2,1H3,(H,9,10)(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UPCKIPHSXMXJOX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37704</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370050</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB022190</foodb_id>
  <chemspider_id>89859</chemspider_id>
  <pdbe_id/>
  <chebi_id>64390</chebi_id>
  <pubchem_compound_id>99463</pubchem_compound_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5669</metlin_id>
  <synthesis_reference>Toth, Eugene; Weiss, Benjamine; Banay-Schwartz, Miriam; Lajtha, Abel.  Effect of glycine derivatives on behavioral changes induced by 3-mercaptopropionic acid or phencyclidine in mice.    Research Communications in Psychology, Psychiatry and Behavior  (1986),  11(1),  1-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:10 UTC</creation_date>
  <update_date>2020-03-13 16:23:11 UTC</update_date>
  <accession>BMDB0000703</accession>
  <secondary_accessions>
    <accession>BMDB00703</accession>
  </secondary_accessions>
  <name>Mandelic acid</name>
  <description/>
  <synonyms>
    <synonym>(S)-2-Hydroxy-2-phenylacetic acid</synonym>
    <synonym>(S)-alpha-Hydroxybenzeneacetic acid</synonym>
    <synonym>(S)-Mandelsaeure</synonym>
    <synonym>L-Mandelic acid</synonym>
    <synonym>(S)-2-Hydroxy-2-phenylacetate</synonym>
    <synonym>(S)-Mandelic acid</synonym>
    <synonym>(S)-a-Hydroxybenzeneacetate</synonym>
    <synonym>(S)-a-Hydroxybenzeneacetic acid</synonym>
    <synonym>(S)-alpha-Hydroxybenzeneacetate</synonym>
    <synonym>(S)-Α-hydroxybenzeneacetate</synonym>
    <synonym>(S)-Α-hydroxybenzeneacetic acid</synonym>
    <synonym>L-Mandelate</synonym>
    <synonym>(S)-Mandelate</synonym>
    <synonym>Mandelate</synonym>
    <synonym>(RS)-Mandelate</synonym>
    <synonym>(RS)-Mandelic acid</synonym>
    <synonym>2-Hydroxy-2-phenylacetate</synonym>
    <synonym>2-Hydroxy-2-phenylacetic acid</synonym>
    <synonym>2-Hydroxy-2-phenylethanoate</synonym>
    <synonym>2-Hydroxy-2-phenylethanoic acid</synonym>
    <synonym>2-Phenyl-2-hydroxyacetate</synonym>
    <synonym>2-Phenyl-2-hydroxyacetic acid</synonym>
    <synonym>2-Phenylglycolate</synonym>
    <synonym>2-Phenylglycolic acid</synonym>
    <synonym>a-Hydroxy-a-toluate</synonym>
    <synonym>a-Hydroxy-a-toluic acid</synonym>
    <synonym>a-Hydroxybenzeneacetate</synonym>
    <synonym>a-Hydroxybenzeneacetic acid</synonym>
    <synonym>a-Hydroxyphenylacetate</synonym>
    <synonym>a-Hydroxyphenylacetic acid</synonym>
    <synonym>Almond acid</synonym>
    <synonym>alpha-Hydroxy-alpha-toluate</synonym>
    <synonym>alpha-Hydroxy-alpha-toluic acid</synonym>
    <synonym>alpha-Hydroxybenzeneacetate</synonym>
    <synonym>alpha-Hydroxybenzeneacetic acid</synonym>
    <synonym>alpha-Hydroxyphenylacetate</synonym>
    <synonym>alpha-Hydroxyphenylacetic acid</synonym>
    <synonym>Amygdalate</synonym>
    <synonym>Amygdalic acid</synonym>
    <synonym>DL-Amygdalate</synonym>
    <synonym>DL-Amygdalic acid</synonym>
    <synonym>DL-Hydroxy(phenyl)acetate</synonym>
    <synonym>DL-Hydroxy(phenyl)acetic acid</synonym>
    <synonym>DL-Mandelate</synonym>
    <synonym>DL-Mandelic acid</synonym>
    <synonym>Paramandelate</synonym>
    <synonym>Paramandelic acid</synonym>
    <synonym>Phenylglycolate</synonym>
    <synonym>Phenylglycolic acid</synonym>
    <synonym>Phenylhydroxyacetate</synonym>
    <synonym>Phenylhydroxyacetic acid</synonym>
    <synonym>Uromaline</synonym>
  </synonyms>
  <chemical_formula>C8H8O3</chemical_formula>
  <average_molecular_weight>152.1473</average_molecular_weight>
  <monisotopic_moleculate_weight>152.047344122</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-hydroxy-2-phenylacetic acid</iupac_name>
  <traditional_iupac>(S)-mandelic acid</traditional_iupac>
  <cas_registry_number>90-64-2</cas_registry_number>
  <smiles>O[C@H](C(O)=O)C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1</inchi>
  <inchikey>IWYDHOAUDWTVEP-ZETCQYMHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class/>
    <direct_parent>Benzene and substituted derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>mandelic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>120 - 122 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>181.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.62</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-hydroxy-2-phenylacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>152.1473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>152.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H](C(O)=O)C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IWYDHOAUDWTVEP-ZETCQYMHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438145</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB03357</drugbank_id>
  <foodb_id>FDB022191</foodb_id>
  <kegg_id>C01984</kegg_id>
  <chemspider_id>388690</chemspider_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <chebi_id>32800</chebi_id>
  <pubchem_compound_id>439616</pubchem_compound_id>
  <meta_cyc_id/>
  <knapsack_id>C00037426</knapsack_id>
  <wikipedia_id>Mandelic acid</wikipedia_id>
  <bigg_id/>
  <metlin_id>5671</metlin_id>
  <synthesis_reference>Chen, Jianfeng; Chen, Hao.  Process for preparation of mandelic acid by membrane separation technology.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2007),  7pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:11 UTC</creation_date>
  <update_date>2020-03-13 16:23:12 UTC</update_date>
  <accession>BMDB0000704</accession>
  <secondary_accessions>
    <accession>BMDB00704</accession>
  </secondary_accessions>
  <name>Isoxanthopterin</name>
  <description>Isoxanthopterin belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one. Isoxanthopterin is possibly soluble (in water) and a moderately basic compound (based on its pKa).</description>
  <synonyms>
    <synonym>2-Amino-4,7-dihydroxypteridine</synonym>
    <synonym>2-Amino-3H,8H-pteridine-4,7-dione</synonym>
    <synonym>2-Aminopteridine-4,7-diol</synonym>
    <synonym>Isoxanthopterin</synonym>
  </synonyms>
  <chemical_formula>C6H5N5O2</chemical_formula>
  <average_molecular_weight>179.1362</average_molecular_weight>
  <monisotopic_moleculate_weight>179.044324429</monisotopic_moleculate_weight>
  <iupac_name>2-amino-1,4,7,8-tetrahydropteridine-4,7-dione</iupac_name>
  <traditional_iupac>2-amino-1,8-dihydropteridine-4,7-dione</traditional_iupac>
  <cas_registry_number>529-69-1</cas_registry_number>
  <smiles>NC1=NC(=O)C2=C(N1)NC(=O)C=N2</smiles>
  <inchi>InChI=1S/C6H5N5O2/c7-6-10-4-3(5(13)11-6)8-1-2(12)9-4/h1H,(H4,7,9,10,11,12,13)</inchi>
  <inchikey>GLKCOBIIZKYKFN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Pterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrazines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pterin</substituent>
      <substituent>Pyrazine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>dihydroxypteridine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>0.005 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-1,4,7,8-tetrahydropteridine-4,7-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>179.1362</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>179.044324429</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=C(N1)NC(=O)C=N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H5N5O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H5N5O2/c7-6-10-4-3(5(13)11-6)8-1-2(12)9-4/h1H,(H4,7,9,10,11,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GLKCOBIIZKYKFN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>108.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156272</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB005583</foodb_id>
  <kegg_id>C03975</kegg_id>
  <chemspider_id>10277</chemspider_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <chebi_id>16713</chebi_id>
  <pubchem_compound_id>10729</pubchem_compound_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <bigg_id/>
  <metlin_id>5672</metlin_id>
  <synthesis_reference>Taylor, Edward C.; Abdulla, Riaz F.; Tanaka, Kunihiko; Jacobi, Peter A.  Pteridines.  XXXVI.  Syntheses of xanthopterin and isoxanthopterin.  Application of N-oxide chemistry to highly functionalized pyrazines and pteridines.  Journal of Organic Chemistry  (1975),  40(16),  2341-7.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:12 UTC</creation_date>
  <update_date>2020-04-14 22:48:09 UTC</update_date>
  <accession>BMDB0000705</accession>
  <secondary_accessions>
    <accession>BMDB00705</accession>
  </secondary_accessions>
  <name>Hexanoylcarnitine</name>
  <description/>
  <synonyms>
    <synonym>3-(Hexanoyloxy)-4-(trimethylammonio)butanoate</synonym>
    <synonym>3-(Hexanoyloxy)-4-(trimethylammonio)butanoic acid</synonym>
    <synonym>Caproylcarnitine</synonym>
    <synonym>Hexanoic acid ester with (3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt</synonym>
    <synonym>Hexanoyl DL-carnitine</synonym>
    <synonym>Hexanoyl-D,L-carnitine</synonym>
    <synonym>Hexanoylcarnitine chloride, (+-)-isomer</synonym>
  </synonyms>
  <chemical_formula>C13H25NO4</chemical_formula>
  <average_molecular_weight>259.3419</average_molecular_weight>
  <monisotopic_moleculate_weight>259.178358293</monisotopic_moleculate_weight>
  <iupac_name>3-(hexanoyloxy)-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>hexanoyl-d,l-carnitine</traditional_iupac>
  <cas_registry_number>6418-78-6</cas_registry_number>
  <smiles>CCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C</smiles>
  <inchi>InChI=1S/C13H25NO4/c1-5-6-7-8-13(17)18-11(9-12(15)16)10-14(2,3)4/h11H,5-10H2,1-4H3</inchi>
  <inchikey>VVPRQWTYSNDTEA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Acyl carnitines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl-carnitine</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>O-acylcarnitine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(hexanoyloxy)-4-(trimethylazaniumyl)butanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>259.3419</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>259.178358293</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H25NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H25NO4/c1-5-6-7-8-13(17)18-11(9-12(15)16)10-14(2,3)4/h11H,5-10H2,1-4H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VVPRQWTYSNDTEA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>91.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>986</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.05+/-0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.02-0.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Sadri H, von Soosten D, Meyer U, Kluess J, Danicke S, Saremi B, Sauerwein H: Plasma amino acids and metabolic profiling of dairy cows in response to a bolus duodenal infusion of leucine. PLoS One. 2017 Apr 28;12(4):e0176647. doi: 10.1371/journal.pone.0176647. eCollection 2017.</reference_text>
          <pubmed_id>28453535</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>0.3+/-0.1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>0.52+/-0.51</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.08+/-0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>0.7+/-0.4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>0.21+/-0.06</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022192</foodb_id>
  <chemspider_id>4932273</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>6426853</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <chebi_id>70749</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5673</metlin_id>
  <synthesis_reference>Strack, Erich; Lorenz, Irmgard.  Synthesis of O-acyl derivatives of carnitine.    Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie  (1966),  343(4-6),  231-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:13 UTC</creation_date>
  <update_date>2020-04-14 22:48:10 UTC</update_date>
  <accession>BMDB0000707</accession>
  <secondary_accessions>
    <accession>BMDB00707</accession>
  </secondary_accessions>
  <name>4-Hydroxyphenylpyruvic acid</name>
  <description>4-Hydroxyphenylpyruvic acid, also known as 4-hydroxy a-oxobenzenepropanoate or (p-hydroxyphenyl)pyruvate, belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. 4-Hydroxyphenylpyruvic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 4-Hydroxyphenylpyruvic acid exists in all living species, ranging from bacteria to humans. 4-Hydroxyphenylpyruvic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(p-Hydroxyphenyl)pyruvic acid</synonym>
    <synonym>3-(4-HYDROXY-phenyl)pyruvIC ACID</synonym>
    <synonym>3-(4-Hydroxyphenyl)pyruvic acid</synonym>
    <synonym>3-(p-Hydroxyphenyl)-2-oxopropanoic acid</synonym>
    <synonym>4-Hydroxy alpha-oxobenzenepropanoic acid</synonym>
    <synonym>p-Hydroxyphenylpyruvic acid</synonym>
    <synonym>4-Hydroxyphenylpyruvate</synonym>
    <synonym>(p-Hydroxyphenyl)pyruvate</synonym>
    <synonym>3-(4-HYDROXY-phenyl)pyruvate</synonym>
    <synonym>3-(4-Hydroxyphenyl)pyruvate</synonym>
    <synonym>3-(p-Hydroxyphenyl)-2-oxopropanoate</synonym>
    <synonym>4-Hydroxy a-oxobenzenepropanoate</synonym>
    <synonym>4-Hydroxy a-oxobenzenepropanoic acid</synonym>
    <synonym>4-Hydroxy alpha-oxobenzenepropanoate</synonym>
    <synonym>4-Hydroxy α-oxobenzenepropanoate</synonym>
    <synonym>4-Hydroxy α-oxobenzenepropanoic acid</synonym>
    <synonym>p-Hydroxyphenylpyruvate</synonym>
    <synonym>(p-Hydroxyphenyl)-pyruvate</synonym>
    <synonym>(p-Hydroxyphenyl)-pyruvic acid</synonym>
    <synonym>3-(4-Hydroxyphenyl)-2-oxo-propanoate</synonym>
    <synonym>3-(4-Hydroxyphenyl)-2-oxo-propanoic acid</synonym>
    <synonym>3-(4-Hydroxyphenyl)-2-oxopropionate</synonym>
    <synonym>3-(4-Hydroxyphenyl)-2-oxopropionic acid</synonym>
    <synonym>3-(p-Hydroxyphenyl)-2-oxopropionate</synonym>
    <synonym>3-(p-Hydroxyphenyl)-2-oxopropionic acid</synonym>
    <synonym>3-(p-Hydroxyphenyl)pyruvate</synonym>
    <synonym>3-(p-Hydroxyphenyl)pyruvic acid</synonym>
    <synonym>4-Hydroxy-a-oxobenzenepropanoate</synonym>
    <synonym>4-Hydroxy-a-oxobenzenepropanoic acid</synonym>
    <synonym>4-Hydroxy-alpha-oxobenzenepropanoate</synonym>
    <synonym>4-Hydroxy-alpha-oxobenzenepropanoic acid</synonym>
    <synonym>4HPPA</synonym>
    <synonym>HPPA</synonym>
    <synonym>Hydroxyphenylpyruvate</synonym>
    <synonym>Hydroxyphenylpyruvic acid</synonym>
    <synonym>p-Hydroxyphenylpyruvic</synonym>
    <synonym>Testacid</synonym>
    <synonym>4-Hydroxyphenylpyruvic acid, ion</synonym>
    <synonym>4-Hydroxyphenylpyruvic acid, sodium salt</synonym>
    <synonym>Para-hydroxyphenylpyruvic acid</synonym>
  </synonyms>
  <chemical_formula>C9H8O4</chemical_formula>
  <average_molecular_weight>180.1574</average_molecular_weight>
  <monisotopic_moleculate_weight>180.042258744</monisotopic_moleculate_weight>
  <iupac_name>3-(4-hydroxyphenyl)-2-oxopropanoic acid</iupac_name>
  <traditional_iupac>4-hydroxyphenylpyruvic acid</traditional_iupac>
  <cas_registry_number>156-39-8</cas_registry_number>
  <smiles>OC(=O)C(=O)CC1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)</inchi>
  <inchikey>KKADPXVIOXHVKN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Phenylpyruvic acid derivatives</sub_class>
    <direct_parent>Phenylpyruvic acid derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Keto acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylpyruvate</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>oxo carboxylic acid</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(4-hydroxyphenyl)-2-oxopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>180.1574</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>180.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C(=O)CC1=CC=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KKADPXVIOXHVKN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>44.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451975</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by UPLC-Q-TOF MS E</comment>
      <references>
        <reference>
          <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
          <pubmed_id>28342601</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB07718</drugbank_id>
  <foodb_id>FDB030506</foodb_id>
  <kegg_id>C01179</kegg_id>
  <chemspider_id>954</chemspider_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <chebi_id>15999</chebi_id>
  <pubchem_compound_id>979</pubchem_compound_id>
  <meta_cyc_id>P-HYDROXY-PHENYLPYRUVATE</meta_cyc_id>
  <knapsack_id>C00007512</knapsack_id>
  <wikipedia_id>4-Hydroxyphenylpyruvic acid</wikipedia_id>
  <bigg_id>37006</bigg_id>
  <metlin_id>5675</metlin_id>
  <synthesis_reference>Billek, Gerhard. p-Hydroxyphenylpyruvic acid. Organic Syntheses (1963), 43 49-54. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
      <pubmed_id>28342601</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00684</protein_accession>
      <name>4-hydroxyphenylpyruvate dioxygenase</name>
      <uniprot_id>Q5EA20</uniprot_id>
      <gene_name>HPD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00859</protein_accession>
      <name>Tyrosine aminotransferase</name>
      <uniprot_id>Q58CZ9</uniprot_id>
      <gene_name>TAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:14 UTC</creation_date>
  <update_date>2020-04-15 22:14:21 UTC</update_date>
  <accession>BMDB0000708</accession>
  <secondary_accessions>
    <accession>BMDB00708</accession>
  </secondary_accessions>
  <name>Glycoursodeoxycholic acid</name>
  <description/>
  <synonyms>
    <synonym>3alpha,7beta-Dihydroxy-5beta-cholanoylglycine</synonym>
    <synonym>Glycine ursodeoxycholic acid</synonym>
    <synonym>Glycylursodeoxycholic acid</synonym>
    <synonym>GUDCA</synonym>
    <synonym>N-(3alpha,7beta-Dihydroxy-5beta-cholan-24-oyl)glycine</synonym>
    <synonym>N-[(3alpha,5beta,7beta)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine</synonym>
    <synonym>Ursodeoxycholylglycine</synonym>
    <synonym>3a,7b-Dihydroxy-5b-cholanoylglycine</synonym>
    <synonym>3Α,7β-dihydroxy-5β-cholanoylglycine</synonym>
    <synonym>Glycine ursodeoxycholate</synonym>
    <synonym>Glycylursodeoxycholate</synonym>
    <synonym>N-(3a,7b-Dihydroxy-5b-cholan-24-oyl)glycine</synonym>
    <synonym>N-(3Α,7β-dihydroxy-5β-cholan-24-oyl)glycine</synonym>
    <synonym>N-[(3a,5b,7b)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine</synonym>
    <synonym>N-[(3Α,5β,7β)-3,7-dihydroxy-24-oxocholan-24-yl]glycine</synonym>
    <synonym>Glycoursodeoxycholate</synonym>
    <synonym>(3beta,5beta,7beta)-3,7-Dihydroxycholan-24-oic acid</synonym>
    <synonym>(3β,5β,7β)-3,7-Dihydroxycholan-24-oic acid</synonym>
    <synonym>3beta,7beta-Dihydroxy-5beta-cholan-24-oic acid</synonym>
    <synonym>3beta,7beta-Dihydroxy-5beta-cholanic acid</synonym>
    <synonym>3beta,7beta-Dihydroxy-5beta-cholanoic acid</synonym>
    <synonym>3beta-Ursodeoxycholic acid</synonym>
    <synonym>3β,7β-Dihydroxy-5β-cholan-24-oic acid</synonym>
    <synonym>3β,7β-Dihydroxy-5β-cholanic acid</synonym>
    <synonym>3β,7β-Dihydroxy-5β-cholanoic acid</synonym>
    <synonym>3β-Ursodeoxycholic acid</synonym>
    <synonym>Isoursodeoxycholic acid</synonym>
  </synonyms>
  <chemical_formula>C26H43NO5</chemical_formula>
  <average_molecular_weight>449.6233</average_molecular_weight>
  <monisotopic_moleculate_weight>449.314123491</monisotopic_moleculate_weight>
  <iupac_name>2-[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid</iupac_name>
  <traditional_iupac>[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid</traditional_iupac>
  <cas_registry_number>64480-66-6</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1</inchi>
  <inchikey>GHCZAUBVMUEKKP-XROMFQGDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Glycinated bile acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Dihydroxy bile acids, alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycinated bile acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>0.00135 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.02</value>
      <source>RODA,A ET AL. (1990)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>449.6233</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>449.314123491</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H43NO5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GHCZAUBVMUEKKP-XROMFQGDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>106.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>122.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>52.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>117882</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>117883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>117884</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022194</foodb_id>
  <chemspider_id>19973534</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>12310288</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <chebi_id>89929</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5676</metlin_id>
  <synthesis_reference>Kanazawa, Teiichi; Shimazaki, Akio; Sato, Tetsuo; Hoshino, Toshio.  Synthesis of ursodeoxycholic acid and its conjugated bile acid.    Proc. Japan Acad.  (1954),  30  391-2.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:16 UTC</creation_date>
  <update_date>2020-03-13 16:23:14 UTC</update_date>
  <accession>BMDB0000709</accession>
  <secondary_accessions>
    <accession>BMDB00709</accession>
  </secondary_accessions>
  <name>L-Cysteinylglycine disulfide</name>
  <description/>
  <synonyms>
    <synonym>L-Cysteinylglycine disulphide</synonym>
    <synonym>(R)-N-(3-((2-Amino-2-carboxyethyl)dithio)-ala)-gly</synonym>
    <synonym>3-[[2-Amino-2-[(carboxymethyl)carbamoyl]ethyl]dithio]-alanine</synonym>
    <synonym>Cystinyl-gly</synonym>
    <synonym>Cystinylglycine</synonym>
    <synonym>L-Cysteinyl-glycine disulfide</synonym>
    <synonym>(2R)-2-Amino-3-({2-amino-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl}disulfanyl)propanoate</synonym>
    <synonym>(2R)-2-Amino-3-({2-amino-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl}disulphanyl)propanoate</synonym>
    <synonym>(2R)-2-Amino-3-({2-amino-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl}disulphanyl)propanoic acid</synonym>
  </synonyms>
  <chemical_formula>C8H15N3O5S2</chemical_formula>
  <average_molecular_weight>297.352</average_molecular_weight>
  <monisotopic_moleculate_weight>297.045311985</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-amino-3-({2-amino-2-[(carboxymethyl)carbamoyl]ethyl}disulfanyl)propanoic acid</iupac_name>
  <traditional_iupac>(2R)-2-amino-3-{[2-amino-2-(carboxymethylcarbamoyl)ethyl]disulfanyl}propanoic acid</traditional_iupac>
  <cas_registry_number>70555-24-7</cas_registry_number>
  <smiles>N[C@@H](CSSCC(N)C(=O)NCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C8H15N3O5S2/c9-4(7(14)11-1-6(12)13)2-17-18-3-5(10)8(15)16/h4-5H,1-3,9-10H2,(H,11,14)(H,12,13)(H,15,16)/t4?,5-/m0/s1</inchi>
  <inchikey>ZHRLECIZINSPKL-AKGZTFGVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Dipeptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkyldisulfides</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>L-cysteine-S-conjugates</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-dipeptide</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Cysteine or derivatives</substituent>
      <substituent>Dialkyldisulfide</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>L-cysteine-s-conjugate</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic disulfide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-amino-3-({2-amino-2-[(carboxymethyl)carbamoyl]ethyl}disulfanyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>297.352</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>297.045311985</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CSSCC(N)C(=O)NCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15N3O5S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15N3O5S2/c9-4(7(14)11-1-6(12)13)2-17-18-3-5(10)8(15)16/h4-5H,1-3,9-10H2,(H,11,14)(H,12,13)(H,15,16)/t4?,5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZHRLECIZINSPKL-AKGZTFGVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>155.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>67.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357522</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022195</foodb_id>
  <chemspider_id>17215992</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>22833544</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <chebi_id>89930</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5677</metlin_id>
  <synthesis_reference>Weygand, Friedrich; Zumach, Gerhard.  Synthesis of cystine peptides by dehydrogenation with vicinal dihalogen derivatives.    Zeitschrift fuer Naturforschung  (1962),  17b  807-10.  CODEN: ZNTFA2  ISSN:0372-9516.  CAN 59:3854  AN 1963:403854</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:17 UTC</creation_date>
  <update_date>2020-04-14 22:48:10 UTC</update_date>
  <accession>BMDB0000710</accession>
  <secondary_accessions>
    <accession>BMDB00710</accession>
  </secondary_accessions>
  <name>4-Hydroxybutyric acid</name>
  <description/>
  <synonyms>
    <synonym>3-Carboxypropoxy acid</synonym>
    <synonym>4-Hydroxy-butyric acid</synonym>
    <synonym>4-Hydroxyalkanoic acid</synonym>
    <synonym>4-Hydroxybutanoate</synonym>
    <synonym>4-Hydroxybutanoic acid</synonym>
    <synonym>4-Hydroxycarboxylic acid</synonym>
    <synonym>Gamma Hydroxybutyric acid</synonym>
    <synonym>gamma-Hydroxybutyric acid</synonym>
    <synonym>GHB</synonym>
    <synonym>Oxy-N-butyric acid</synonym>
    <synonym>Xyrem</synonym>
    <synonym>4-Hydroxy-butyrate</synonym>
    <synonym>4-Hydroxyalkanoate</synonym>
    <synonym>4-Hydroxycarboxylate</synonym>
    <synonym>g Hydroxybutyrate</synonym>
    <synonym>g Hydroxybutyric acid</synonym>
    <synonym>gamma Hydroxybutyrate</synonym>
    <synonym>Γ hydroxybutyrate</synonym>
    <synonym>Γ hydroxybutyric acid</synonym>
    <synonym>g-Hydroxybutyrate</synonym>
    <synonym>g-Hydroxybutyric acid</synonym>
    <synonym>gamma-Hydroxybutyrate</synonym>
    <synonym>Γ-hydroxybutyrate</synonym>
    <synonym>Γ-hydroxybutyric acid</synonym>
    <synonym>Oxy-N-butyrate</synonym>
    <synonym>4-Hydroxybutyrate</synonym>
    <synonym>4-Hydroxy-butanoate</synonym>
    <synonym>4-Hydroxy-butanoic acid</synonym>
    <synonym>4-Hydroxybutyrate sodium</synonym>
    <synonym>4-Hydroxybutyric acid monosodium salt</synonym>
    <synonym>gamma-Hydroxy butyrate</synonym>
    <synonym>gamma-Hydroxy sodium butyrate</synonym>
    <synonym>gamma-Hydroxybutyrate sodium</synonym>
    <synonym>Hydroxybutyric acid</synonym>
  </synonyms>
  <chemical_formula>C4H8O3</chemical_formula>
  <average_molecular_weight>104.1045</average_molecular_weight>
  <monisotopic_moleculate_weight>104.047344122</monisotopic_moleculate_weight>
  <iupac_name>4-hydroxybutanoic acid</iupac_name>
  <traditional_iupac>gamma hydroxybutyric acid</traditional_iupac>
  <cas_registry_number>591-81-1</cas_registry_number>
  <smiles>OCCCC(O)=O</smiles>
  <inchi>InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)</inchi>
  <inchikey>SJZRECIVHVDYJC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>4-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
      <external_descriptor>hydroxybutyric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-hydroxybutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>104.1045</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>104.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SJZRECIVHVDYJC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>23.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32944</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022196</foodb_id>
  <chemspider_id>9984</chemspider_id>
  <kegg_id>C01991</kegg_id>
  <pubchem_compound_id>10413</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <chebi_id>30830</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Oxybate</wikipedia_id>
  <metlin_id>5678</metlin_id>
  <synthesis_reference>Takigawa, Shinichiro; Araya, Shuzo.  Process for the preparation of g-hydroxybutyric acid as a synthetic intermediate.   Jpn. Kokai Tokkyo Koho  (1988),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00595</protein_accession>
      <name>Hydroxyacid-oxoacid transhydrogenase, mitochondrial</name>
      <uniprot_id>A6QP15</uniprot_id>
      <gene_name>ADHFE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:18 UTC</creation_date>
  <update_date>2020-03-13 16:23:15 UTC</update_date>
  <accession>BMDB0000711</accession>
  <secondary_accessions>
    <accession>BMDB00711</accession>
  </secondary_accessions>
  <name>Hydroxyoctanoic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Hydroxycaprylic acid</synonym>
    <synonym>alpha-Hydroxyoctanoic acid</synonym>
    <synonym>2-Hydroxycaprylate</synonym>
    <synonym>a-Hydroxyoctanoate</synonym>
    <synonym>a-Hydroxyoctanoic acid</synonym>
    <synonym>alpha-Hydroxyoctanoate</synonym>
    <synonym>Α-hydroxyoctanoate</synonym>
    <synonym>Α-hydroxyoctanoic acid</synonym>
    <synonym>Hydroxyoctanoate</synonym>
    <synonym>2-Hydroxyoctanoate</synonym>
    <synonym>2-Hydroxyoctanoic acid</synonym>
    <synonym>a-Hydroxy-N-caprylate</synonym>
    <synonym>a-Hydroxy-N-caprylic acid</synonym>
    <synonym>a-Hydroxycaprylate</synonym>
    <synonym>a-Hydroxycaprylic acid</synonym>
    <synonym>alpha-Hydroxy-N-caprylate</synonym>
    <synonym>alpha-Hydroxy-N-caprylic acid</synonym>
    <synonym>alpha-Hydroxycaprylate</synonym>
    <synonym>alpha-Hydroxycaprylic acid</synonym>
    <synonym>DL-2-Hydroxycaprylate</synonym>
    <synonym>DL-2-Hydroxycaprylic acid</synonym>
    <synonym>DL-2-Hydroxyoctanoate</synonym>
    <synonym>DL-2-Hydroxyoctanoic acid</synonym>
    <synonym>alpha-HCA acid</synonym>
    <synonym>2-Hydroxy caprylate</synonym>
  </synonyms>
  <chemical_formula>C8H16O3</chemical_formula>
  <average_molecular_weight>160.2108</average_molecular_weight>
  <monisotopic_moleculate_weight>160.109944378</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxyoctanoic acid</iupac_name>
  <traditional_iupac>hydroxyoctanoate</traditional_iupac>
  <cas_registry_number>617-73-2</cas_registry_number>
  <smiles>CCCCCCC(O)C(O)=O</smiles>
  <inchi>InChI=1S/C8H16O3/c1-2-3-4-5-6-7(9)8(10)11/h7,9H,2-6H2,1H3,(H,10,11)</inchi>
  <inchikey>JKRDADVRIYVCCY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
      <external_descriptor>hydroxy fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>70 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>927 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxyoctanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>160.2108</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>160.109944378</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCC(O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16O3/c1-2-3-4-5-6-7(9)8(10)11/h7,9H,2-6H2,1H3,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JKRDADVRIYVCCY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438654</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022197</foodb_id>
  <chemspider_id>84994</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>94180</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <chebi_id>86543</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5679</metlin_id>
  <synthesis_reference>Sakaki, Keiji; Hara, Shigeki; Itoh, Naotsugu.  Optical resolution of racemic 2-hydroxy octanoic acid using biphasic enzyme membrane reactor.    Desalination  (2002),  149(1-3),  247-252.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:19 UTC</creation_date>
  <update_date>2020-04-15 22:14:22 UTC</update_date>
  <accession>BMDB0000712</accession>
  <secondary_accessions>
    <accession>BMDB00712</accession>
  </secondary_accessions>
  <name>Hexadecanedioic acid mono-L-carnitine ester</name>
  <description/>
  <synonyms>
    <synonym>(15-Carboxypentadecanoyl)carnitine</synonym>
    <synonym>3-[(15-Carboxypentadecanoyl)oxy]-4-(trimethylammonio)butanoate</synonym>
    <synonym>3-[(15-Carboxypentadecanoyl)oxy]-4-(trimethylammonio)butanoic acid</synonym>
    <synonym>Hexadecanedioate mono-L-carnitine ester</synonym>
    <synonym>(R)-3-Carboxy-2-[(15-carboxy-1-oxopentadecyl)oxy]-N,N,N-trimethyl-1-propanaminium inner salt</synonym>
    <synonym>Hexadecanedioate</synonym>
    <synonym>Hexadecanedioic acid</synonym>
  </synonyms>
  <chemical_formula>C23H43NO6</chemical_formula>
  <average_molecular_weight>429.5906</average_molecular_weight>
  <monisotopic_moleculate_weight>429.309038113</monisotopic_moleculate_weight>
  <iupac_name>3-[(15-carboxypentadecanoyl)oxy]-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>3-[(15-carboxypentadecanoyl)oxy]-4-(trimethylammonio)butanoate</traditional_iupac>
  <cas_registry_number>42150-38-9</cas_registry_number>
  <smiles>C[N+](C)(C)CC(CC([O-])=O)OC(=O)CCCCCCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C23H43NO6/c1-24(2,3)19-20(18-22(27)28)30-23(29)17-15-13-11-9-7-5-4-6-8-10-12-14-16-21(25)26/h20H,4-19H2,1-3H3,(H-,25,26,27,28)</inchi>
  <inchikey>UNHCPLSWMNPZTD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Acyl carnitines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl-carnitine</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>O-acylcarnitine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(15-carboxypentadecanoyl)oxy]-4-(trimethylazaniumyl)butanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>429.5906</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>429.309038113</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)CC(CC([O-])=O)OC(=O)CCCCCCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C23H43NO6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C23H43NO6/c1-24(2,3)19-20(18-22(27)28)30-23(29)17-15-13-11-9-7-5-4-6-8-10-12-14-16-21(25)26/h20H,4-19H2,1-3H3,(H-,25,26,27,28)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UNHCPLSWMNPZTD-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>103.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>138.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37712</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022198</foodb_id>
  <kegg_id/>
  <chemspider_id>17215993</chemspider_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <chebi_id>73081</chebi_id>
  <pubchem_compound_id>566787</pubchem_compound_id>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5680</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:20 UTC</creation_date>
  <update_date>2020-04-15 22:14:23 UTC</update_date>
  <accession>BMDB0000713</accession>
  <secondary_accessions>
    <accession>BMDB00713</accession>
  </secondary_accessions>
  <name>Isoallolithocholic acid</name>
  <description/>
  <synonyms>
    <synonym>Isoallolithocholate</synonym>
    <synonym>3b-Hydroxy-5a-cholan-24-Oate</synonym>
    <synonym>3b-Hydroxy-5a-cholan-24-Oic acid</synonym>
    <synonym>3b-Hydroxy-5a-cholanate</synonym>
    <synonym>3b-Hydroxy-5a-cholanic acid</synonym>
    <synonym>3b-Hydroxy-5a-cholanoate</synonym>
    <synonym>3b-Hydroxy-5a-cholanoic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,5S,7S,10R,11S,14R,15R)-5-Hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O3</chemical_formula>
  <average_molecular_weight>376.5726</average_molecular_weight>
  <monisotopic_moleculate_weight>376.297745146</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5S,7S,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5S,7S,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>2276-93-9</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16+,17+,18+,19-,20+,21+,23+,24-/m1/s1</inchi>
  <inchikey>SMEROWZSTRWXGI-XBESLWPFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Monohydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monohydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5S,7S,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>376.5726</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>376.297745146</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16+,17+,18+,19-,20+,21+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SMEROWZSTRWXGI-XBESLWPFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>107.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>45.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330696</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022199</foodb_id>
  <kegg_id/>
  <chemspider_id>85037</chemspider_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <chebi_id/>
  <pubchem_compound_id>94228</pubchem_compound_id>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5681</metlin_id>
  <synthesis_reference>Fernholz, E.; Chakravorty, P. N.  The position of the hydroxyl group in ergosterol and stigmasterol.    Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen  (1934),  67B  2021-6.  CODEN: BDCBAD  ISSN:0365-9488.  CAN 29:10976  AN 1935:10976</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:21 UTC</creation_date>
  <update_date>2020-04-15 22:14:23 UTC</update_date>
  <accession>BMDB0000714</accession>
  <secondary_accessions>
    <accession>BMDB00714</accession>
  </secondary_accessions>
  <name>Hippuric acid</name>
  <description>Hippuric acid, also known as N-benzoylglycine or hippurate, belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine. Hippuric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Hippuric acid is a potentially toxic compound. Hippuric acid has been found to be associated with several diseases known as uremia, ulcerative colitis, colorectal cancer, and eosinophilic esophagitis; also hippuric acid has been linked to the inborn metabolic disorders including tyrosinemia I.</description>
  <synonyms>
    <synonym>Benzamidoacetic acid</synonym>
    <synonym>Benzamidoessigsaeure</synonym>
    <synonym>Benzoylaminoacetic acid</synonym>
    <synonym>Benzoylaminoessigsaeure</synonym>
    <synonym>Hippurate</synonym>
    <synonym>Hippursaeure</synonym>
    <synonym>Phenylcarbonylaminoacetic acid</synonym>
    <synonym>N-Benzoylglycine</synonym>
    <synonym>Benzamidoacetate</synonym>
    <synonym>Benzoylaminoacetate</synonym>
    <synonym>Phenylcarbonylaminoacetate</synonym>
    <synonym>Hippate</synonym>
    <synonym>Hippic acid</synonym>
    <synonym>(Benzoylamino)-acetate</synonym>
    <synonym>(Benzoylamino)-acetic acid</synonym>
    <synonym>2-Benzamidoacetate</synonym>
    <synonym>2-Benzamidoacetic acid</synonym>
    <synonym>Benzoylglycine</synonym>
    <synonym>N-Benzoylglycinate</synonym>
  </synonyms>
  <chemical_formula>C9H9NO3</chemical_formula>
  <average_molecular_weight>179.1727</average_molecular_weight>
  <monisotopic_moleculate_weight>179.058243159</monisotopic_moleculate_weight>
  <iupac_name>2-(phenylformamido)acetic acid</iupac_name>
  <traditional_iupac>hippuric acid</traditional_iupac>
  <cas_registry_number>495-69-2</cas_registry_number>
  <smiles>OC(=O)CNC(=O)C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)</inchi>
  <inchikey>QIAFMBKCNZACKA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>Hippuric acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hippuric acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylglycine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>187 - 191 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>3.75 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.31</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(phenylformamido)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>179.1727</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>179.058243159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CNC(=O)C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H9NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QIAFMBKCNZACKA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451977</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Charolais cows.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>112.76 +/- 33.00</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>65 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>69 +/- 9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>72 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>67 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from 20 healthy Holstein Friesian dairy cows </comment>
      <references>
        <reference>
          <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
          <pubmed_id>23738862</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>227.93 +/- 38.90</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from Danish Holstein-Friesian (n = 456) and Jersey cows (n = 436)</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
          <pubmed_id>23182357</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>165.93 +/- 32.77</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein.</comment>
      <references>
        <reference>
          <reference_text>Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17.</reference_text>
          <pubmed_id>22059599</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB001819</foodb_id>
  <kegg_id>C01586</kegg_id>
  <chemspider_id>451</chemspider_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <chebi_id>18089</chebi_id>
  <pubchem_compound_id>464</pubchem_compound_id>
  <meta_cyc_id>CPD-425</meta_cyc_id>
  <knapsack_id>C00030483</knapsack_id>
  <wikipedia_id>Hippuric_acid</wikipedia_id>
  <bigg_id/>
  <metlin_id>1301</metlin_id>
  <synthesis_reference>Ingersoll, A. W.; Barcock, S. H. Hippuric acid. Organic Syntheses (1932), XII 40-2.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
      <pubmed_id>23182357</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
      <pubmed_id>23738862</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:22 UTC</creation_date>
  <update_date>2020-04-15 21:59:45 UTC</update_date>
  <accession>BMDB0000715</accession>
  <secondary_accessions>
    <accession>BMDB00715</accession>
  </secondary_accessions>
  <name>Kynurenic acid</name>
  <description>Kynurenic acid, also known as kynurenic acid or kynurenic acid, belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Kynurenic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Kynurenic acid exists in all eukaryotes, ranging from yeast to humans. In cattle, kynurenic acid is involved in the metabolic pathway called the tryptophan metabolism pathway. Kynurenic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>4-Hydroxy-2-chinolincarbonsaeure</synonym>
    <synonym>4-Hydroxy-2-quinolinecarboxylic acid</synonym>
    <synonym>4-Hydroxyquinaldic acid</synonym>
    <synonym>4-Hydroxyquinaldinic acid</synonym>
    <synonym>Kynurenate</synonym>
    <synonym>Kynurensaeure</synonym>
    <synonym>4-Hydroxy-2-quinolinecarboxylate</synonym>
    <synonym>4-Hydroxyquinaldate</synonym>
    <synonym>4-Hydroxyquinaldinate</synonym>
    <synonym>2-Carboxy-4-hydroxyquinoline</synonym>
    <synonym>4-Hydroxy-quinaldate</synonym>
    <synonym>4-Hydroxy-quinaldic acid</synonym>
    <synonym>4-Hydroxyquinoline-2-carboxylate</synonym>
    <synonym>4-Hydroxyquinoline-2-carboxylic acid</synonym>
    <synonym>Quinurenic acid</synonym>
    <synonym>Acid, kynurenic</synonym>
  </synonyms>
  <chemical_formula>C10H7NO3</chemical_formula>
  <average_molecular_weight>189.1675</average_molecular_weight>
  <monisotopic_moleculate_weight>189.042593095</monisotopic_moleculate_weight>
  <iupac_name>4-oxo-1,4-dihydroquinoline-2-carboxylic acid</iupac_name>
  <traditional_iupac>acid, kynurenic</traditional_iupac>
  <cas_registry_number>492-27-3</cas_registry_number>
  <smiles>OC(=O)C1=CC(=O)C2=CC=CC=C2N1</smiles>
  <inchi>InChI=1S/C10H7NO3/c12-9-5-8(10(13)14)11-7-4-2-1-3-6(7)9/h1-5H,(H,11,12)(H,13,14)</inchi>
  <inchikey>HCZHHEIFKROPDY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Quinolines and derivatives</class>
    <sub_class>Quinoline carboxylic acids</sub_class>
    <direct_parent>Quinoline carboxylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroquinolines</alternative_parent>
      <alternative_parent>Hydroquinolones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridinecarboxylic acids</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dihydroquinoline</substituent>
      <substituent>Dihydroquinolone</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridine carboxylic acid</substituent>
      <substituent>Pyridine carboxylic acid or derivatives</substituent>
      <substituent>Quinoline-2-carboxylic acid</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>monohydroxyquinoline</external_descriptor>
      <external_descriptor>quinolinemonocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>280 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-oxo-1,4-dihydroquinoline-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>189.1675</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>189.042593095</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1=CC(=O)C2=CC=CC=C2N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H7NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H7NO3/c12-9-5-8(10(13)14)11-7-4-2-1-3-6(7)9/h1-5H,(H,11,12)(H,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HCZHHEIFKROPDY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>52.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445147</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB11937</drugbank_id>
  <foodb_id>FDB022200</foodb_id>
  <kegg_id>C01717</kegg_id>
  <chemspider_id>3712</chemspider_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <chebi_id>18344</chebi_id>
  <pubchem_compound_id>3845</pubchem_compound_id>
  <meta_cyc_id>KYNURENATE</meta_cyc_id>
  <knapsack_id>C00026494</knapsack_id>
  <wikipedia_id>Kynurenic_acid</wikipedia_id>
  <bigg_id>38234</bigg_id>
  <metlin_id>5683</metlin_id>
  <synthesis_reference>Stone, T. W.  Development and therapeutic potential of kynurenic acid and kynurenine derivatives for neuroprotection.    Trends in Pharmacological Sciences  (2000),  21(4),  149-154.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:24 UTC</creation_date>
  <update_date>2020-04-15 22:14:24 UTC</update_date>
  <accession>BMDB0000716</accession>
  <secondary_accessions>
    <accession>BMDB00716</accession>
  </secondary_accessions>
  <name>L-Pipecolic acid</name>
  <description>L-Pipecolic acid, also known as (S)-pipecolate or L-homoproline, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-Pipecolic acid exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Pipecolic acid has been linked to several inborn metabolic disorders including peroxisomal biogenesis defect and adrenoleukodystrophy.</description>
  <synonyms>
    <synonym>(S)-(-)-Pipecolic acid</synonym>
    <synonym>(S)-Pipecolic acid</synonym>
    <synonym>(S)-Piperidine-2-carboxylic acid</synonym>
    <synonym>2-Piperidinecarboxylic acid</synonym>
    <synonym>L-(-)-Pipecolic acid</synonym>
    <synonym>Pipecolic acid</synonym>
    <synonym>Pipecolinic acid</synonym>
    <synonym>(S)-(-)-Pipecolate</synonym>
    <synonym>(S)-Pipecolate</synonym>
    <synonym>(S)-Piperidine-2-carboxylate</synonym>
    <synonym>2-Piperidinecarboxylate</synonym>
    <synonym>L-(-)-Pipecolate</synonym>
    <synonym>Pipecolate</synonym>
    <synonym>Pipecolinate</synonym>
    <synonym>L-Pipecolate</synonym>
    <synonym>(-)-Pipecolate</synonym>
    <synonym>(-)-Pipecolic acid</synonym>
    <synonym>(S)-(-)-2-Piperidinecarboxylate</synonym>
    <synonym>(S)-(-)-2-Piperidinecarboxylic acid</synonym>
    <synonym>(S)-2-Piperidinecarboxylate</synonym>
    <synonym>(S)-2-Piperidinecarboxylic acid</synonym>
    <synonym>(S)-Pipecolinate</synonym>
    <synonym>(S)-Pipecolinic acid</synonym>
    <synonym>L-Homoproline</synonym>
    <synonym>L-Pipecolinate</synonym>
    <synonym>L-Pipecolinic acid</synonym>
    <synonym>L-Piperidine-2-carboxylate</synonym>
    <synonym>L-Piperidine-2-carboxylic acid</synonym>
    <synonym>Pipecolic acid, (+,-)-isomer</synonym>
    <synonym>Pipecolic acid, 14C-labeled CPD, (+,-)-isomer</synonym>
    <synonym>Homopipecolic acid</synonym>
    <synonym>Pipecolic acid, ion(1-), (+,-)-isomer</synonym>
    <synonym>Pipecolic acid, ion(1-), (S)-isomer</synonym>
    <synonym>Pipecolic acid hydrochloride, (+-)-isomer</synonym>
    <synonym>Pipecolic acid, (S)-isomer</synonym>
    <synonym>Pipecolic acid, (R)-isomer</synonym>
    <synonym>Pipecolic acid, ion (1-)</synonym>
    <synonym>Pipecolic acid, monopotassium salt</synonym>
  </synonyms>
  <chemical_formula>C6H11NO2</chemical_formula>
  <average_molecular_weight>129.157</average_molecular_weight>
  <monisotopic_moleculate_weight>129.078978601</monisotopic_moleculate_weight>
  <iupac_name>(2S)-piperidine-2-carboxylic acid</iupac_name>
  <traditional_iupac>L-pipecolic acid</traditional_iupac>
  <cas_registry_number>3105-95-1</cas_registry_number>
  <smiles>OC(=O)[C@@H]1CCCCN1</smiles>
  <inchi>InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1</inchi>
  <inchikey>HXEACLLIILLPRG-YFKPBYRVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Piperidinecarboxylic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Piperidine</substituent>
      <substituent>Piperidinecarboxylic acid</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Piperidine alkaloids</external_descriptor>
      <external_descriptor>pipecolic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>272 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-piperidine-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>129.157</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>129.078978601</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)[C@@H]1CCCCN1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H11NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HXEACLLIILLPRG-YFKPBYRVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>49.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446757</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB000546</foodb_id>
  <kegg_id>C00408</kegg_id>
  <chemspider_id>388365</chemspider_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <chebi_id>30913</chebi_id>
  <pubchem_compound_id>439227</pubchem_compound_id>
  <meta_cyc_id>L-PIPECOLATE</meta_cyc_id>
  <knapsack_id>C00001387</knapsack_id>
  <wikipedia_id>Pipecolic acid</wikipedia_id>
  <bigg_id>34890</bigg_id>
  <metlin_id>5684</metlin_id>
  <synthesis_reference>Kisfaludy, Lajos; Korenczki, Ferenc; Katho, Agnes. Works, Gedeon Richter Ltd., Budapest, Hung. One-step synthesis of L-piperidine-2-carboxylic acid. Synthesis (1982), (2), 163.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00895</protein_accession>
      <name>Peroxisomal sarcosine oxidase</name>
      <uniprot_id>Q29RU9</uniprot_id>
      <gene_name>PIPOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:25 UTC</creation_date>
  <update_date>2020-04-15 22:06:55 UTC</update_date>
  <accession>BMDB0000717</accession>
  <secondary_accessions>
    <accession>BMDB00717</accession>
  </secondary_accessions>
  <name>Isolithocholic acid</name>
  <description/>
  <synonyms>
    <synonym>(3beta,5beta)-3-Hydroxycholan-24-Oic acid</synonym>
    <synonym>3-Epilithocholic acid</synonym>
    <synonym>3beta-Hydroxy-5beta-cholan-24-Oic acid</synonym>
    <synonym>3beta-Lithocholic acid</synonym>
    <synonym>beta-Lithocholanic acid</synonym>
    <synonym>beta-Lithocholic acid</synonym>
    <synonym>(3b,5b)-3-Hydroxycholan-24-Oate</synonym>
    <synonym>(3b,5b)-3-Hydroxycholan-24-Oic acid</synonym>
    <synonym>(3beta,5beta)-3-Hydroxycholan-24-Oate</synonym>
    <synonym>(3Β,5β)-3-hydroxycholan-24-Oate</synonym>
    <synonym>(3Β,5β)-3-hydroxycholan-24-Oic acid</synonym>
    <synonym>3-Epilithocholate</synonym>
    <synonym>3b-Hydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3b-Hydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3beta-Hydroxy-5beta-cholan-24-Oate</synonym>
    <synonym>3Β-hydroxy-5β-cholan-24-Oate</synonym>
    <synonym>3Β-hydroxy-5β-cholan-24-Oic acid</synonym>
    <synonym>3b-Lithocholate</synonym>
    <synonym>3b-Lithocholic acid</synonym>
    <synonym>3beta-Lithocholate</synonym>
    <synonym>3Β-lithocholate</synonym>
    <synonym>3Β-lithocholic acid</synonym>
    <synonym>b-Lithocholanate</synonym>
    <synonym>b-Lithocholanic acid</synonym>
    <synonym>beta-Lithocholanate</synonym>
    <synonym>Β-lithocholanate</synonym>
    <synonym>Β-lithocholanic acid</synonym>
    <synonym>b-Lithocholate</synonym>
    <synonym>b-Lithocholic acid</synonym>
    <synonym>beta-Lithocholate</synonym>
    <synonym>Β-lithocholate</synonym>
    <synonym>Β-lithocholic acid</synonym>
    <synonym>Isolithocholate</synonym>
    <synonym>3b-Hydroxy-5b-cholanate</synonym>
    <synonym>3b-Hydroxy-5b-cholanic acid</synonym>
    <synonym>3b-Hydroxy-5b-cholanoate</synonym>
    <synonym>3b-Hydroxy-5b-cholanoic acid</synonym>
    <synonym>5b-Cholanic acid-3b-ol</synonym>
    <synonym>Acid, isolithocholic</synonym>
    <synonym>Acid, lithocholic</synonym>
    <synonym>Lithocholate</synonym>
    <synonym>Lithocholic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O3</chemical_formula>
  <average_molecular_weight>376.5726</average_molecular_weight>
  <monisotopic_moleculate_weight>376.297745146</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>1534-35-6</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17+,18+,19-,20+,21+,23+,24-/m1/s1</inchi>
  <inchikey>SMEROWZSTRWXGI-WFVDQZAMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Monohydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monohydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>bile acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>376.5726</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>376.297745146</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17+,18+,19-,20+,21+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SMEROWZSTRWXGI-WFVDQZAMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>107.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>45.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>50310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>50311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>50312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>165696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>165697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>165698</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022201</foodb_id>
  <kegg_id>C17658</kegg_id>
  <chemspider_id>144522</chemspider_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <chebi_id>81253</chebi_id>
  <pubchem_compound_id>164853</pubchem_compound_id>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5685</metlin_id>
  <synthesis_reference>Radominska-Pyrek, Anna; Huynh, Triet; Lester, Roger; St. Pyrek, Jan.  Preparation and characterization of 3-monohydroxylated bile acids of different side chain length and configuration at C-3.  Novel approach to the synthesis of 24-norlithocholic acid.    Journal of Lipid Research  (1986),  27(1),  102-13.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:26 UTC</creation_date>
  <update_date>2020-03-13 16:23:18 UTC</update_date>
  <accession>BMDB0000718</accession>
  <secondary_accessions>
    <accession>BMDB00718</accession>
  </secondary_accessions>
  <name>Isovaleric acid</name>
  <description>3-Methylbutanoic acid, also known as isovalerate or 3-methylbutyrate, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. 3-Methylbutanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 3-Methylbutanoic acid exists in all living species, ranging from bacteria to humans. 3-Methylbutanoic acid has been found to be associated with several diseases known as crohn's disease, ulcerative colitis, autism, and nonalcoholic fatty liver disease; also 3-methylbutanoic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.</description>
  <synonyms>
    <synonym>3-Methyl-N-butyric acid</synonym>
    <synonym>3-Methylbutanoic acid</synonym>
    <synonym>3-Methylbuttersaeure</synonym>
    <synonym>3-Methylbutyric acid</synonym>
    <synonym>beta-Methylbutyric acid</synonym>
    <synonym>Delphinic acid</synonym>
    <synonym>Isobutylformic acid</synonym>
    <synonym>Isopentanoic acid</synonym>
    <synonym>Isopropylacetic acid</synonym>
    <synonym>Isovalerate</synonym>
    <synonym>Isovalerianic acid</synonym>
    <synonym>Isovaleriansaeure</synonym>
    <synonym>3-Methyl-N-butyrate</synonym>
    <synonym>3-Methylbutanoate</synonym>
    <synonym>3-Methylbutyrate</synonym>
    <synonym>b-Methylbutyrate</synonym>
    <synonym>b-Methylbutyric acid</synonym>
    <synonym>beta-Methylbutyrate</synonym>
    <synonym>Β-methylbutyrate</synonym>
    <synonym>Β-methylbutyric acid</synonym>
    <synonym>Delphinate</synonym>
    <synonym>Isobutylformate</synonym>
    <synonym>Isopentanoate</synonym>
    <synonym>Isopropylacetate</synonym>
    <synonym>Isovalerianate</synonym>
    <synonym>3-Methyl butyric acid</synonym>
    <synonym>3-Methylbutyric acid: isopropyl-acetate</synonym>
    <synonym>3-Methylbutyric acid: isopropyl-acetic acid</synonym>
    <synonym>3-Methyl-1-butanoic acid</synonym>
    <synonym>Isovaleric acid</synonym>
  </synonyms>
  <chemical_formula>C5H10O2</chemical_formula>
  <average_molecular_weight>102.1317</average_molecular_weight>
  <monisotopic_moleculate_weight>102.068079564</monisotopic_moleculate_weight>
  <iupac_name>3-methylbutanoic acid</iupac_name>
  <traditional_iupac>isovaleric acid</traditional_iupac>
  <cas_registry_number>503-74-2</cas_registry_number>
  <smiles>CC(C)CC(O)=O</smiles>
  <inchi>InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)</inchi>
  <inchikey>GWYFCOCPABKNJV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Methyl-branched fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Branched fatty acids</external_descriptor>
      <external_descriptor>Branched fatty acids</external_descriptor>
      <external_descriptor>branched-chain saturated fatty acid</external_descriptor>
      <external_descriptor>methylbutyric acid</external_descriptor>
      <external_descriptor>short-chain fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-29.3 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>40.7 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.16</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-methylbutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>102.1317</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>102.068079564</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GWYFCOCPABKNJV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>26.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3882</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437956</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0 +/- 0.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.9 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.8 +/- 0.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB001324</foodb_id>
  <kegg_id>C08262</kegg_id>
  <chemspider_id>10001</chemspider_id>
  <drugbank_id>DB03750</drugbank_id>
  <pubchem_compound_id>10430</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28484</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001189</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>3-Methylbutanoic acid</wikipedia_id>
  <metlin_id>109</metlin_id>
  <synthesis_reference>Imada, Yukio; Mizuno, Sumiko; Mikawa, Takashi.  Manufacture of isovaleric acid and 2-methylbutyric acid.    Jpn. Kokai Tokkyo Koho  (1986),     3 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:27 UTC</creation_date>
  <update_date>2020-04-14 22:48:12 UTC</update_date>
  <accession>BMDB0000719</accession>
  <secondary_accessions>
    <accession>BMDB00719</accession>
  </secondary_accessions>
  <name>L-Homoserine</name>
  <description>L-Homoserine belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-Homoserine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Homoserine exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>(2S)-2-Amino-4-hydroxybutanoic acid</synonym>
    <synonym>2-Amino-4-hydroxybutanoic acid</synonym>
    <synonym>2-Amino-4-hydroxybutyric acid</synonym>
    <synonym>Homoserine</synonym>
    <synonym>(2S)-2-Amino-4-hydroxybutanoate</synonym>
    <synonym>2-Amino-4-hydroxybutanoate</synonym>
    <synonym>2-Amino-4-hydroxybutyrate</synonym>
    <synonym>(S)-2-Amino-4-hydroxy-butanoate</synonym>
    <synonym>(S)-2-Amino-4-hydroxy-butanoic acid</synonym>
    <synonym>(S)-2-Amino-4-hydroxybutanoate</synonym>
    <synonym>(S)-2-Amino-4-hydroxybutanoic acid</synonym>
    <synonym>(S)-Homoserine</synonym>
    <synonym>2-Amino-4-hydroxy-butyrate</synonym>
    <synonym>2-Amino-4-hydroxy-butyric acid</synonym>
    <synonym>2-Amino-4-hydroxy-L-butyrate</synonym>
    <synonym>2-Amino-4-hydroxy-L-butyric acid</synonym>
    <synonym>Homoserine L-isomer</synonym>
    <synonym>L Isomer OF homoserine</synonym>
    <synonym>L-Isomer OF homoserine</synonym>
  </synonyms>
  <chemical_formula>C4H9NO3</chemical_formula>
  <average_molecular_weight>119.1192</average_molecular_weight>
  <monisotopic_moleculate_weight>119.058243159</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-hydroxybutanoic acid</iupac_name>
  <traditional_iupac>L-homoserine</traditional_iupac>
  <cas_registry_number>672-15-1</cas_registry_number>
  <smiles>N[C@@H](CCO)C(O)=O</smiles>
  <inchi>InChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1</inchi>
  <inchikey>UKAUYVFTDYCKQA-VKHMYHEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-aminoalcohols</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>homoserine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>203 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-hydroxybutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>119.1192</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>119.058243159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCO)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H9NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UKAUYVFTDYCKQA-VKHMYHEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>83.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>26.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37719</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB006683</foodb_id>
  <kegg_id>C00263</kegg_id>
  <chemspider_id>12126</chemspider_id>
  <drugbank_id>DB04193</drugbank_id>
  <pubchem_compound_id>12647</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15699</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001366</knapsack_id>
  <meta_cyc_id>HOMO-SER</meta_cyc_id>
  <bigg_id>34437</bigg_id>
  <wikipedia_id>Homoserine</wikipedia_id>
  <metlin_id>5687</metlin_id>
  <synthesis_reference>Kokusenya, Yoshio; Matsuoka, Manabu.  Synthesis of amino acids by electrochemical reduction.  I.  Synthesis of L-homoserine by electrochemical reduction of L-asparagine.    Denki Kagaku oyobi Kogyo Butsuri Kagaku  (1987),  55(2),  174-5.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:28 UTC</creation_date>
  <update_date>2020-04-15 22:22:56 UTC</update_date>
  <accession>BMDB0000720</accession>
  <secondary_accessions>
    <accession>BMDB00720</accession>
  </secondary_accessions>
  <name>Levulinic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Acetylpropionic acid</synonym>
    <synonym>3-Ketobutane-1-carboxylic acid</synonym>
    <synonym>4-Ketovaleric acid</synonym>
    <synonym>4-Oxovaleric acid</synonym>
    <synonym>beta-Acetylpropionic acid</synonym>
    <synonym>gamma-Ketovaleric acid</synonym>
    <synonym>LAEVULINIC ACID</synonym>
    <synonym>Laevulinsaeure</synonym>
    <synonym>LEVA</synonym>
    <synonym>Levulic acid</synonym>
    <synonym>Levulinsaeure</synonym>
    <synonym>3-Acetylpropionate</synonym>
    <synonym>3-Ketobutane-1-carboxylate</synonym>
    <synonym>4-Ketovalerate</synonym>
    <synonym>4-Oxovalerate</synonym>
    <synonym>b-Acetylpropionate</synonym>
    <synonym>b-Acetylpropionic acid</synonym>
    <synonym>beta-Acetylpropionate</synonym>
    <synonym>Β-acetylpropionate</synonym>
    <synonym>Β-acetylpropionic acid</synonym>
    <synonym>g-Ketovalerate</synonym>
    <synonym>g-Ketovaleric acid</synonym>
    <synonym>gamma-Ketovalerate</synonym>
    <synonym>Γ-ketovalerate</synonym>
    <synonym>Γ-ketovaleric acid</synonym>
    <synonym>LAEVULINate</synonym>
    <synonym>Levulate</synonym>
    <synonym>Levulinate</synonym>
    <synonym>4-Oxopentanoate</synonym>
    <synonym>4-Oxopentanoic acid</synonym>
    <synonym>Diasporal</synonym>
    <synonym>Levulinic acid, sodium salt</synonym>
    <synonym>Magnesium diasporal</synonym>
    <synonym>Calcium levulate</synonym>
    <synonym>Magnesium levulinate</synonym>
    <synonym>Calcium levulinate</synonym>
    <synonym>Levulinic acid, ammonium salt</synonym>
    <synonym>Levulinic acid, calcium salt</synonym>
    <synonym>Magnesium laevulinate</synonym>
    <synonym>Levulinic acid</synonym>
  </synonyms>
  <chemical_formula>C5H8O3</chemical_formula>
  <average_molecular_weight>116.1152</average_molecular_weight>
  <monisotopic_moleculate_weight>116.047344122</monisotopic_moleculate_weight>
  <iupac_name>4-oxopentanoic acid</iupac_name>
  <traditional_iupac>levulinic acid</traditional_iupac>
  <cas_registry_number>123-76-2</cas_registry_number>
  <smiles>CC(=O)CCC(O)=O</smiles>
  <inchi>InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)</inchi>
  <inchikey>JOOXCMJARBKPKM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Gamma-keto acids and derivatives</sub_class>
    <direct_parent>Gamma-keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Short-chain keto acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Gamma-keto acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain keto acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Oxo fatty acids</external_descriptor>
      <external_descriptor>oxopentanoic acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>30 - 33 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.49</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.069</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-oxopentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>116.1152</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>116.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JOOXCMJARBKPKM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>27.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27919</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>246117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>246118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>246119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>266061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>266062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>266063</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB003296</foodb_id>
  <kegg_id/>
  <chemspider_id>11091</chemspider_id>
  <drugbank_id>DB02239</drugbank_id>
  <pubchem_compound_id>11579</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>45630</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Levulinic_acid</wikipedia_id>
  <metlin_id>2195</metlin_id>
  <synthesis_reference>Cai, Lei; Lu, Xiuyang; He, Long; Xia, Wenli; Ren, Qilong.  Review on preparation methods of levulinic acid, a new platform chemical.    Xiandai Huagong  (2003),  23(4),  14-16.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:29 UTC</creation_date>
  <update_date>2020-03-13 16:23:20 UTC</update_date>
  <accession>BMDB0000721</accession>
  <secondary_accessions>
    <accession>BMDB00721</accession>
  </secondary_accessions>
  <name>Glycylproline</name>
  <description>Glycylproline, also known as gly-pro, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Glycylproline exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Glycylproline has been found to be associated with several diseases known as eosinophilic esophagitis, alzheimer's disease, and colorectal cancer; also glycylproline has been linked to the inborn metabolic disorders including prolidase deficiency.</description>
  <synonyms>
    <synonym>1-(Aminoacetyl)proline</synonym>
    <synonym>1-Glycylproline</synonym>
    <synonym>Gly-L-pro</synonym>
    <synonym>GP</synonym>
    <synonym>N-Glycyl-L-proline</synonym>
    <synonym>N-Glycylproline</synonym>
    <synonym>Glycyl-L-proline</synonym>
    <synonym>(S)-1-(2-Aminoacetyl)pyrrolidine-2-carboxylic acid</synonym>
    <synonym>1-Glycyl-L-proline</synonym>
    <synonym>g-p Dipeptide</synonym>
    <synonym>GP Dipeptide</synonym>
    <synonym>Gly-pro</synonym>
    <synonym>Glycine proline dipeptide</synonym>
    <synonym>Glycine-proline dipeptide</synonym>
    <synonym>Glycyl-proline</synonym>
    <synonym>NSC 97929</synonym>
    <synonym>Glycylproline</synonym>
  </synonyms>
  <chemical_formula>C7H12N2O3</chemical_formula>
  <average_molecular_weight>172.1818</average_molecular_weight>
  <monisotopic_moleculate_weight>172.08479226</monisotopic_moleculate_weight>
  <iupac_name>(2S)-1-(2-aminoacetyl)pyrrolidine-2-carboxylic acid</iupac_name>
  <traditional_iupac>glycylproline</traditional_iupac>
  <cas_registry_number>704-15-4</cas_registry_number>
  <smiles>NCC(=O)N1CCC[C@H]1C(O)=O</smiles>
  <inchi>InChI=1S/C7H12N2O3/c8-4-6(10)9-3-1-2-5(9)7(11)12/h5H,1-4,8H2,(H,11,12)/t5-/m0/s1</inchi>
  <inchikey>KZNQNBZMBZJQJO-YFKPBYRVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Dipeptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>N-acylpyrrolidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Proline and derivatives</alternative_parent>
      <alternative_parent>Pyrrolidine carboxylic acids</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-dipeptide</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>N-acylpyrrolidine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Proline or derivatives</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidine carboxylic acid</substituent>
      <substituent>Pyrrolidine carboxylic acid or derivatives</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dipeptide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>155 - 158 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-1-(2-aminoacetyl)pyrrolidine-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>172.1818</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>172.08479226</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCC(=O)N1CCC[C@H]1C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H12N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H12N2O3/c8-4-6(10)9-3-1-2-5(9)7(11)12/h5H,1-4,8H2,(H,11,12)/t5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KZNQNBZMBZJQJO-YFKPBYRVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>83.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1310737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1310738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1310739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1425223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1425224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1425225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448415</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022202</foodb_id>
  <kegg_id/>
  <chemspider_id>2282246</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>3013625</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>70744</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-10814</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Maruyama, Susumu; Ichimura, Toshiaki; Otsuka, Tatsuo; Yamashita, Eiichi.  Long-lasting antihypertensive agents and glycylproline manufactured from collagen and/or gelatin.    Jpn. Kokai Tokkyo Koho  (2005),     10 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:30 UTC</creation_date>
  <update_date>2020-04-15 22:06:56 UTC</update_date>
  <accession>BMDB0000722</accession>
  <secondary_accessions>
    <accession>BMDB00722</accession>
  </secondary_accessions>
  <name>Lithocholyltaurine</name>
  <description/>
  <synonyms>
    <synonym>2-[(3alpha-Hydroxy-24-oxo-5beta-cholan-24-yl)amino]ethanesulfonic acid</synonym>
    <synonym>2-[[(3a,5b)-3-Hydroxy-24-oxocholan-24-yl]amino]-ethanesulfonate</synonym>
    <synonym>2-[[(3a,5b)-3-Hydroxy-24-oxocholan-24-yl]amino]-ethanesulfonic acid</synonym>
    <synonym>3a-Hydroxy-5b-cholanoyltaurine</synonym>
    <synonym>3a-Hydroxy-N-(2-sulfoethyl)-5b-cholan-24-amide</synonym>
    <synonym>Cholane ethanesulfonic acid deriv.</synonym>
    <synonym>Lithocholic acid taurine conjugate</synonym>
    <synonym>Lithocholic acid taurine conjugic acid</synonym>
    <synonym>N-(3a-Hydroxy-5b-cholan-24-oyl)-taurine</synonym>
    <synonym>Taurolithocholate</synonym>
    <synonym>Taurolithocholic acid</synonym>
    <synonym>Lithocholate, taurine</synonym>
    <synonym>Taurine lithocholate</synonym>
    <synonym>Taurolithocholic acid, monosodium salt</synonym>
    <synonym>Acid, taurolithocholic</synonym>
  </synonyms>
  <chemical_formula>C26H45NO5S</chemical_formula>
  <average_molecular_weight>483.704</average_molecular_weight>
  <monisotopic_moleculate_weight>483.301844245</monisotopic_moleculate_weight>
  <iupac_name>2-[(4R)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid</iupac_name>
  <traditional_iupac>2-[(4R)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid</traditional_iupac>
  <cas_registry_number>516-90-5</cas_registry_number>
  <smiles>C[C@H](CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C</smiles>
  <inchi>InChI=1S/C26H45NO5S/c1-17(4-9-24(29)27-14-15-33(30,31)32)21-7-8-22-20-6-5-18-16-19(28)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23,28H,4-16H2,1-3H3,(H,27,29)(H,30,31,32)/t17-,18?,19-,20?,21?,22?,23?,25+,26-/m1/s1</inchi>
  <inchikey>QBYUNVOYXHFVKC-LVMSMGIASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Taurinated bile acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Alkanesulfonic acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monohydroxy bile acids, alcohols and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonic acids</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfonyls</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkanesulfonic acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monohydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfonyl</substituent>
      <substituent>Taurinated bile acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>212 - 213 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-0.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4R)-4-[(2S,5R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>483.704</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>483.301844245</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](CCC(=O)NCCS(O)(=O)=O)C1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H45NO5S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H45NO5S/c1-17(4-9-24(29)27-14-15-33(30,31)32)21-7-8-22-20-6-5-18-16-19(28)10-12-25(18,2)23(20)11-13-26(21,22)3/h17-23,28H,4-16H2,1-3H3,(H,27,29)(H,30,31,32)/t17-,18?,19-,20?,21?,22?,23?,25+,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QBYUNVOYXHFVKC-LVMSMGIASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>103.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>129.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>55.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>82389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>82390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>82391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>143733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>143734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>143735</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022203</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477716</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>36259</chebi_id>
  <pdbe_id/>
  <kegg_id>C02592</kegg_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Taurolithocholic acid</wikipedia_id>
  <metlin_id>5690</metlin_id>
  <synthesis_reference>Zhang, Jie; Griffiths, William J.; Bergman, Tomas; Sjoevall, Jan.  Derivatization of bile acids with taurine for analysis by fast atom bombardment mass spectrometry with collision-induced fragmentation.    Journal of Lipid Research  (1993),  34(11),  1895-900.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:32 UTC</creation_date>
  <update_date>2020-04-16 20:38:32 UTC</update_date>
  <accession>BMDB0000725</accession>
  <secondary_accessions>
    <accession>BMDB00725</accession>
  </secondary_accessions>
  <name>Hydroxyproline</name>
  <description>4-Hydroxyproline, also known as Hyp or oxaceprol, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 4-Hydroxyproline is a drug which is used in france as a combination product for the treatment of small, superficial wounds. 4-Hydroxyproline exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 4-Hydroxyproline exists in all living species, ranging from bacteria to humans. 4-Hydroxyproline is a potentially toxic compound. 4-Hydroxyproline has been found to be associated with several diseases known as ulcerative colitis, hemodialysis, crohn's disease, and alzheimer's disease; also 4-hydroxyproline has been linked to the inborn metabolic disorders including iminoglycinuria.</description>
  <synonyms>
    <synonym>(2S,4R)-4-Hydroxy-2-pyrrolidinecarboxylic acid</synonym>
    <synonym>(2S,4R)-trans-4-Hydroxyproline</synonym>
    <synonym>delta-Hydroxyproline</synonym>
    <synonym>Hydroxy-L-proline</synonym>
    <synonym>Hydroxyproline</synonym>
    <synonym>Hyp</synonym>
    <synonym>Hypro</synonym>
    <synonym>L-4-Hydroxyproline</synonym>
    <synonym>L-Threo-4-hydroxyproline</synonym>
    <synonym>trans-Hydroxyproline</synonym>
    <synonym>trans-L-Hydroxyproline</synonym>
    <synonym>L-Hydroxyproline</synonym>
    <synonym>trans-4-Hydroxy-L-proline</synonym>
    <synonym>(2S,4R)-4-Hydroxy-2-pyrrolidinecarboxylate</synonym>
    <synonym>Δ-hydroxyproline</synonym>
    <synonym>(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid</synonym>
    <synonym>(4R)-4-Hydroxy-L-proline</synonym>
    <synonym>4-Hydroxy-2-pyrrolidinecarboxylic acid</synonym>
    <synonym>4-Hydroxy-L-proline</synonym>
    <synonym>4-L-Hydroxyproline</synonym>
    <synonym>Hydroxiproline</synonym>
    <synonym>Hydroxy-proline</synonym>
    <synonym>LS-Hydroxyproline</synonym>
    <synonym>Oxaceprol</synonym>
    <synonym>trans-4-Hydroxyproline</synonym>
    <synonym>4 Hydroxyproline</synonym>
    <synonym>Oxyproline</synonym>
    <synonym>(-)-4-Hydroxy-2-pyrrolidinecarboxylic acid</synonym>
    <synonym>(2S,4R)-(-)-4-Hydroxyproline</synonym>
    <synonym>(2S,4R)-4-Hydroxyproline</synonym>
    <synonym>(R)-4-Hydroxy-(S)-proline</synonym>
    <synonym>(R)-4-Hydroxy-L-proline</synonym>
    <synonym>(S)-Hydroxyproline</synonym>
    <synonym>4(R)-Hydroxy-2(S)-pyrrolidinecarboxylic acid</synonym>
    <synonym>4(R)-Hydroxyproline</synonym>
    <synonym>4-Hydroxy-(S)-proline</synonym>
    <synonym>4-trans-Hydroxy-L-proline</synonym>
    <synonym>L-Hypro</synonym>
    <synonym>L-trans-4-Hydroxyproline</synonym>
    <synonym>NSC 46704</synonym>
    <synonym>trans-L-4-Hydroxyproline</synonym>
    <synonym>4-Hydroxyproline</synonym>
  </synonyms>
  <chemical_formula>C5H9NO3</chemical_formula>
  <average_molecular_weight>131.1299</average_molecular_weight>
  <monisotopic_moleculate_weight>131.058243159</monisotopic_moleculate_weight>
  <iupac_name>(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid</iupac_name>
  <traditional_iupac>hypro</traditional_iupac>
  <cas_registry_number>51-35-4</cas_registry_number>
  <smiles>O[C@H]1CN[C@@H](C1)C(O)=O</smiles>
  <inchi>InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1</inchi>
  <inchikey>PMMYEEVYMWASQN-DMTCNVIQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Proline and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrrolidine carboxylic acids</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Proline or derivatives</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidine carboxylic acid</substituent>
      <substituent>Pyrrolidine carboxylic acid or derivatives</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>4-hydroxyproline</external_descriptor>
      <external_descriptor>Other amino acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>131.1299</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>131.058243159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1CN[C@@H](C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H9NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PMMYEEVYMWASQN-DMTCNVIQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>69.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>29.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37723</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>23.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>25+/-5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>51+/-13</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>32+/-11</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.1 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.6 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.9 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.1 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>31+/-11</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>43+/-12</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB013511</foodb_id>
  <kegg_id>C01157</kegg_id>
  <chemspider_id>5605</chemspider_id>
  <drugbank_id>DB08847</drugbank_id>
  <pubchem_compound_id>5810</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18095</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001370</knapsack_id>
  <meta_cyc_id>4-HYDROXY-L-PROLINE</meta_cyc_id>
  <bigg_id>36935</bigg_id>
  <wikipedia_id>Hydroxyproline</wikipedia_id>
  <metlin_id>257</metlin_id>
  <synthesis_reference>Adams, Elijah; Goldstone, Alfred. Hydroxyproline metabolism. II. Enzymic preparation and properties of D1-pyrroline-3-hydroxy-5-carboxylic acid. Journal of Biological Chemistry (1960), 235 3492-8.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Characterization of the biochemical variability of bovine milk using metabolomics</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00668</protein_accession>
      <name>Prolyl 4-hydroxylase subunit alpha-1</name>
      <uniprot_id>Q1RMU3</uniprot_id>
      <gene_name>P4HA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00691</protein_accession>
      <name>Prolyl 4-hydroxylase subunit alpha-3</name>
      <uniprot_id>Q75UG4</uniprot_id>
      <gene_name>P4HA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00799</protein_accession>
      <name>Dipeptidyl peptidase 4</name>
      <uniprot_id>P81425</uniprot_id>
      <gene_name>DPP4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:33 UTC</creation_date>
  <update_date>2020-03-13 16:23:22 UTC</update_date>
  <accession>BMDB0000726</accession>
  <secondary_accessions>
    <accession>BMDB00726</accession>
  </secondary_accessions>
  <name>Isovalerylglutamic acid</name>
  <description/>
  <synonyms>
    <synonym>Isovalerylglutamate</synonym>
    <synonym>N-Isovaleryl-DL-glutamate</synonym>
    <synonym>N-Isovaleryl-DL-glutamic acid</synonym>
    <synonym>N-Isovalerylglutamic acid</synonym>
    <synonym>N-IVGA</synonym>
    <synonym>(2S)-2-[(1-Hydroxy-3-methylbutylidene)amino]pentanedioate</synonym>
  </synonyms>
  <chemical_formula>C10H17NO5</chemical_formula>
  <average_molecular_weight>231.2457</average_molecular_weight>
  <monisotopic_moleculate_weight>231.110672659</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-(3-methylbutanamido)pentanedioic acid</iupac_name>
  <traditional_iupac>isovalerylglutamic acid</traditional_iupac>
  <cas_registry_number>80154-63-8</cas_registry_number>
  <smiles>CC(C)CC(=O)N[C@@H](CCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C10H17NO5/c1-6(2)5-8(12)11-7(10(15)16)3-4-9(13)14/h6-7H,3-5H2,1-2H3,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1</inchi>
  <inchikey>HCVIJONZMYVLAW-ZETCQYMHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Glutamic acid and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Branched fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-(3-methylbutanamido)pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>231.2457</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>231.110672659</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CC(=O)N[C@@H](CCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H17NO5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H17NO5/c1-6(2)5-8(12)11-7(10(15)16)3-4-9(13)14/h6-7H,3-5H2,1-2H3,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HCVIJONZMYVLAW-ZETCQYMHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>103.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311924</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357039</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022204</foodb_id>
  <kegg_id/>
  <chemspider_id>117667</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>133383</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5694</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:34 UTC</creation_date>
  <update_date>2020-03-13 16:23:22 UTC</update_date>
  <accession>BMDB0000727</accession>
  <secondary_accessions>
    <accession>BMDB00727</accession>
  </secondary_accessions>
  <name>L-Threoneopterin</name>
  <description/>
  <synonyms>
    <synonym>2-Amino-6-(L-threo-trihydroxypropyl)-4(3H)-pteridinone</synonym>
    <synonym>L-(+)-Monapterin</synonym>
    <synonym>L-6-(Threo-1',2',3'-trihydroxypropyl)pterin</synonym>
    <synonym>L-Monapterin</synonym>
    <synonym>L-Threo-monapterin</synonym>
    <synonym>L-Threo-neopterin</synonym>
    <synonym>2-Amino-6-(1,2,3-trihydroxypropyl)-4(3H)-pteridinone</synonym>
    <synonym>Neopterin, (erythro-L)-isomer</synonym>
    <synonym>Monapterin</synonym>
    <synonym>Neopterin</synonym>
    <synonym>Neopterin, (threo-L)-isomer</synonym>
    <synonym>2-Amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-4(3H)-pteridinone</synonym>
    <synonym>L-6-(Threo-1’,2’,3’-trihydroxypropyl)pterin</synonym>
  </synonyms>
  <chemical_formula>C9H11N5O4</chemical_formula>
  <average_molecular_weight>253.2147</average_molecular_weight>
  <monisotopic_moleculate_weight>253.081103865</monisotopic_moleculate_weight>
  <iupac_name>2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-4,8-dihydropteridin-4-one</iupac_name>
  <traditional_iupac>2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-8H-pteridin-4-one</traditional_iupac>
  <cas_registry_number>2277-42-1</cas_registry_number>
  <smiles>NC1=NC(=O)C2=NC(=CNC2=N1)[C@H](O)[C@@H](O)CO</smiles>
  <inchi>InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)/t4-,6-/m0/s1</inchi>
  <inchikey>BMQYVXCPAOLZOK-NJGYIYPDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Biopterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrazines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Biopterin</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrazine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>neopterins</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-6-[(1S,2S)-1,2,3-trihydroxypropyl]-4,8-dihydropteridin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>253.2147</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>253.081103865</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=NC(=CNC2=N1)[C@H](O)[C@@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11N5O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)/t4-,6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BMQYVXCPAOLZOK-NJGYIYPDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>152.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>59.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337335</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022205</foodb_id>
  <chemspider_id>389684</chemspider_id>
  <pubchem_compound_id>440842</pubchem_compound_id>
  <kegg_id/>
  <chebi_id>49751</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5695</metlin_id>
  <synthesis_reference>Viscontini, Max; Provenzale, R.; Ohlgart, S.; Mallevialle, J.  Pterin chemistry.  XXXII.  Synthesis of natural D-neopterin and L-monapterin.    Helvetica Chimica Acta  (1970),  53(5),  1202-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:35 UTC</creation_date>
  <update_date>2020-03-13 16:23:23 UTC</update_date>
  <accession>BMDB0000728</accession>
  <secondary_accessions>
    <accession>BMDB00728</accession>
  </secondary_accessions>
  <name>Hydroxypropionic porphyrin III</name>
  <description/>
  <synonyms>
    <synonym>b-Hydroxypropionic acid heptacarboxylic porphyrin III</synonym>
    <synonym>beta-Hydroxypropionic acid heptacarboxylic porphyrin III</synonym>
    <synonym>3-[10,15,20-Tris(2-carboxyethyl)-9,14,19-tris(carboxymethyl)-5-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C39H38N4O14</chemical_formula>
  <average_molecular_weight>786.7374</average_molecular_weight>
  <monisotopic_moleculate_weight>786.238451944</monisotopic_moleculate_weight>
  <iupac_name>3-[10,14,19-tris(2-carboxyethyl)-5,15,20-tris(carboxymethyl)-9-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[10,14,19-tris(2-carboxyethyl)-5,15,20-tris(carboxymethyl)-9-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>163894-03-9</cas_registry_number>
  <smiles>CC1=C(CCC(O)=O)C2=N\C\1=C/C1=C(CC(O)=O)C(CCC(O)=O)=C(N1)\C=C1/N=C(/C=C3\N/C(=C\2)C(CCC(O)=O)=C3CC(O)=O)C(CCC(O)=O)=C1CC(O)=O</smiles>
  <inchi>InChI=1S/C39H38N4O14/c1-17-18(2-6-33(44)45)26-14-27-20(4-8-35(48)49)23(11-38(54)55)31(42-27)16-29-21(5-9-36(50)51)24(12-39(56)57)32(43-29)15-28-19(3-7-34(46)47)22(10-37(52)53)30(41-28)13-25(17)40-26/h13-16,41-42H,2-12H2,1H3,(H,44,45)(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)/b25-13-,26-14-,27-14-,28-15-,29-16-,30-13-,31-16-,32-15-</inchi>
  <inchikey>NGHBDJAOMFYFRP-PKXAPQLQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[10,14,19-tris(2-carboxyethyl)-5,15,20-tris(carboxymethyl)-9-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>786.7374</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>786.238451944</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCC(O)=O)C2=N\C\1=C/C1=C(CC(O)=O)C(CCC(O)=O)=C(N1)\C=C1/N=C(/C=C3\N/C(=C\2)C(CCC(O)=O)=C3CC(O)=O)C(CCC(O)=O)=C1CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C39H38N4O14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C39H38N4O14/c1-17-18(2-6-33(44)45)26-14-27-20(4-8-35(48)49)23(11-38(54)55)31(42-27)16-29-21(5-9-36(50)51)24(12-39(56)57)32(43-29)15-28-19(3-7-34(46)47)22(10-37(52)53)30(41-28)13-25(17)40-26/h13-16,41-42H,2-12H2,1H3,(H,44,45)(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)/b25-13-,26-14-,27-14-,28-15-,29-16-,30-13-,31-16-,32-15-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NGHBDJAOMFYFRP-PKXAPQLQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>318.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>195.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>82.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329865</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022206</foodb_id>
  <chemspider_id>17215996</chemspider_id>
  <pubchem_compound_id/>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <kegg_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5696</metlin_id>
  <synthesis_reference>Luo, Jinli; Lim, Chang Kee.  Isolation and characterization of new porphyrin metabolites in human porphyria cutanea tarda and in rats treated with hexachlorobenzene by HPTLC, HPLC and liquid secondary ion mass spectrometry.    Biomedical Chromatography  (1995),  9(3),  113-22.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:36 UTC</creation_date>
  <update_date>2020-04-14 22:48:13 UTC</update_date>
  <accession>BMDB0000729</accession>
  <secondary_accessions>
    <accession>BMDB00729</accession>
  </secondary_accessions>
  <name>Alpha-Hydroxyisobutyric acid</name>
  <description/>
  <synonyms>
    <synonym>2-Hydroxy-2-methylpropionic acid</synonym>
    <synonym>2-Hydroxy-2-methylpropionsaeure</synonym>
    <synonym>2-Methyl-2-hydroxypropanoic acid</synonym>
    <synonym>2-Methyl-2-hydroxypropionsaeure</synonym>
    <synonym>2-Methyllactic acid</synonym>
    <synonym>Acetonic acid</synonym>
    <synonym>Acide 2-hydroxy-2-methylpropanoique</synonym>
    <synonym>Acido 2-hidroxi-2-metilpropionico</synonym>
    <synonym>alpha-Hydroxy-alpha-methylpropanoic acid</synonym>
    <synonym>alpha-Hydroxy-alpha-methylpropionic acid</synonym>
    <synonym>alpha-Hydroxyisobutanoic acid</synonym>
    <synonym>HIBA</synonym>
    <synonym>Hydroxydimethylacetic acid</synonym>
    <synonym>2-Hydroxy-2-methylpropionate</synonym>
    <synonym>2-Methyl-2-hydroxypropanoate</synonym>
    <synonym>2-Methyllactate</synonym>
    <synonym>Acetonate</synonym>
    <synonym>a-Hydroxy-a-methylpropanoate</synonym>
    <synonym>a-Hydroxy-a-methylpropanoic acid</synonym>
    <synonym>alpha-Hydroxy-alpha-methylpropanoate</synonym>
    <synonym>Α-hydroxy-α-methylpropanoate</synonym>
    <synonym>Α-hydroxy-α-methylpropanoic acid</synonym>
    <synonym>a-Hydroxy-a-methylpropionate</synonym>
    <synonym>a-Hydroxy-a-methylpropionic acid</synonym>
    <synonym>alpha-Hydroxy-alpha-methylpropionate</synonym>
    <synonym>Α-hydroxy-α-methylpropionate</synonym>
    <synonym>Α-hydroxy-α-methylpropionic acid</synonym>
    <synonym>a-Hydroxyisobutanoate</synonym>
    <synonym>a-Hydroxyisobutanoic acid</synonym>
    <synonym>alpha-Hydroxyisobutanoate</synonym>
    <synonym>Α-hydroxyisobutanoate</synonym>
    <synonym>Α-hydroxyisobutanoic acid</synonym>
    <synonym>Hydroxydimethylacetate</synonym>
    <synonym>a-Hydroxyisobutyrate</synonym>
    <synonym>a-Hydroxyisobutyric acid</synonym>
    <synonym>alpha-Hydroxyisobutyrate</synonym>
    <synonym>Α-hydroxyisobutyrate</synonym>
    <synonym>Α-hydroxyisobutyric acid</synonym>
    <synonym>a-Hydroxy-isobutyrate</synonym>
    <synonym>a-Hydroxy-isobutyric acid</synonym>
    <synonym>alpha-Hydroxy-isobutyrate</synonym>
    <synonym>Α-hydroxy-isobutyrate</synonym>
    <synonym>Α-hydroxy-isobutyric acid</synonym>
    <synonym>(CH3)2cohcooh</synonym>
    <synonym>2-Hydroxy-2-methylpropanoate</synonym>
    <synonym>2-Hydroxy-2-methylpropanoic acid</synonym>
    <synonym>2-Hydroxyisobutyrate</synonym>
    <synonym>2-Hydroxyisobutyric acid</synonym>
    <synonym>a-HIB</synonym>
    <synonym>alpha-HIB</synonym>
    <synonym>Hydroxyisobutyrate</synonym>
    <synonym>L-2-Methyllactate</synonym>
    <synonym>L-2-Methyllactic acid</synonym>
    <synonym>2-Hydroxyisobutyric acid, lead salt</synonym>
    <synonym>Lead 2-hydroxyisobutyric acid</synonym>
    <synonym>alpha-Hydroxyisobutyric acid</synonym>
  </synonyms>
  <chemical_formula>C4H8O3</chemical_formula>
  <average_molecular_weight>104.1045</average_molecular_weight>
  <monisotopic_moleculate_weight>104.047344122</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-2-methylpropanoic acid</iupac_name>
  <traditional_iupac>acetonate</traditional_iupac>
  <cas_registry_number>594-61-6</cas_registry_number>
  <smiles>CC(C)(O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)</inchi>
  <inchikey>BWLBGMIXKSTLSX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Alpha hydroxy acids and derivatives</sub_class>
    <direct_parent>Alpha hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>82.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.36</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.039</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-2-methylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>104.1045</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>104.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)(O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BWLBGMIXKSTLSX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>23.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439030</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022207</foodb_id>
  <kegg_id/>
  <chemspider_id>11181</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>11671</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>50129</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>3750</metlin_id>
  <synthesis_reference>Vogl, O.  Synthesis of a-hydroxyisobutyric acid from isobutylene.    Journal of Organic Chemistry  (1958),  23  1488-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:37 UTC</creation_date>
  <update_date>2020-03-13 16:23:24 UTC</update_date>
  <accession>BMDB0000730</accession>
  <secondary_accessions>
    <accession>BMDB00730</accession>
  </secondary_accessions>
  <name>Isobutyrylglycine</name>
  <description/>
  <synonyms>
    <synonym>Isobutanoylglycine</synonym>
    <synonym>N-Isobutanoylglycine</synonym>
    <synonym>N-(1-Methylpropyl)glycine</synonym>
    <synonym>N-Isobutyrylglycine</synonym>
    <synonym>Isobutyrylglycine</synonym>
  </synonyms>
  <chemical_formula>C6H11NO3</chemical_formula>
  <average_molecular_weight>145.1564</average_molecular_weight>
  <monisotopic_moleculate_weight>145.073893223</monisotopic_moleculate_weight>
  <iupac_name>2-(2-methylpropanamido)acetic acid</iupac_name>
  <traditional_iupac>isobutyrylglycine</traditional_iupac>
  <cas_registry_number>15926-18-8</cas_registry_number>
  <smiles>CC(C)C(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C6H11NO3/c1-4(2)6(10)7-3-5(8)9/h4H,3H2,1-2H3,(H,7,10)(H,8,9)</inchi>
  <inchikey>DCICDMMXFIELDF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylglycine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>82.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.085</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(2-methylpropanamido)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>145.1564</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>145.073893223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)C(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H11NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H11NO3/c1-4(2)6(10)7-3-5(8)9/h4H,3H2,1-2H3,(H,7,10)(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DCICDMMXFIELDF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340695</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022208</foodb_id>
  <kegg_id/>
  <chemspider_id>9030891</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>10855600</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>70979</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5698</metlin_id>
  <synthesis_reference>Katz, J.; Lieberman, I.; Barker, H. A.  Formation of propionyl-, butyryl-, and other acylglycines by enzymes of Clostridium kluyveri.    Journal of Biological Chemistry  (1953),  200  431-41.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:38 UTC</creation_date>
  <update_date>2020-03-13 16:23:25 UTC</update_date>
  <accession>BMDB0000731</accession>
  <secondary_accessions>
    <accession>BMDB00731</accession>
  </secondary_accessions>
  <name>Cysteine-S-sulfate</name>
  <description/>
  <synonyms>
    <synonym>Cysteine-S-sulfonate</synonym>
    <synonym>Cysteinyl-S-sulfonate</synonym>
    <synonym>Cysteinyl-S-sulfonic acid</synonym>
    <synonym>L-Cysteine hydrogen sulfate</synonym>
    <synonym>L-Cysteine S-sulfate</synonym>
    <synonym>S-Sulfocysteine</synonym>
    <synonym>S-SulphO-L-cysteine</synonym>
    <synonym>S-Sulphocysteine</synonym>
    <synonym>Cysteine-S-sulfonic acid</synonym>
    <synonym>Cysteine-S-sulphonate</synonym>
    <synonym>Cysteine-S-sulphonic acid</synonym>
    <synonym>Cysteinyl-S-sulphonate</synonym>
    <synonym>Cysteinyl-S-sulphonic acid</synonym>
    <synonym>L-Cysteine hydrogen sulfuric acid</synonym>
    <synonym>L-Cysteine hydrogen sulphate</synonym>
    <synonym>L-Cysteine hydrogen sulphuric acid</synonym>
    <synonym>L-Cysteine S-sulfuric acid</synonym>
    <synonym>L-Cysteine S-sulphate</synonym>
    <synonym>L-Cysteine S-sulphuric acid</synonym>
    <synonym>S-SulfO-L-cysteine</synonym>
    <synonym>Cysteine-S-sulfuric acid</synonym>
    <synonym>Cysteine-S-sulphate</synonym>
    <synonym>Cysteine-S-sulphuric acid</synonym>
    <synonym>Alaninethiosulfuric acid</synonym>
    <synonym>L-Cysteine hydrogen sulfate (ester)</synonym>
    <synonym>L-Cysteine hydrogen sulphate (ester)</synonym>
    <synonym>L-Cysteine-S-sulfonate</synonym>
    <synonym>L-Cysteinesulfonic acid</synonym>
    <synonym>S-Cysteinesulfonic acid</synonym>
    <synonym>S-Sulphocysteine, monosodium salt</synonym>
    <synonym>S-Sulphocysteine ion (1-)</synonym>
  </synonyms>
  <chemical_formula>C3H7NO5S2</chemical_formula>
  <average_molecular_weight>201.221</average_molecular_weight>
  <monisotopic_moleculate_weight>200.976563719</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-amino-3-(sulfosulfanyl)propanoic acid</iupac_name>
  <traditional_iupac>S-sulphocysteine</traditional_iupac>
  <cas_registry_number>1637-71-4</cas_registry_number>
  <smiles>N[C@@H](CSS(O)(=O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H7NO5S2/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1</inchi>
  <inchikey>NOKPBJYHPHHWAN-REOHCLBHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as s-sulfo-l-cysteines. These are s-conjugated L-cysteine where the S-substituent is specified as a sulfo group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>S-sulfo-L-cysteines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>S-alkyl thiosulfates</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>S-alkyl thiosulfate</substituent>
      <substituent>S-sulfo-l-cysteine</substituent>
      <substituent>Sulfenyl compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>S-substituted L-cysteine</external_descriptor>
      <external_descriptor>organic thiosulfate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>170 - 171 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-amino-3-(sulfosulfanyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>201.221</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>200.976563719</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CSS(O)(=O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7NO5S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7NO5S2/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NOKPBJYHPHHWAN-REOHCLBHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>117.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437490</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB031160</foodb_id>
  <chemspider_id>102939</chemspider_id>
  <drugbank_id>DB04370</drugbank_id>
  <kegg_id>C05824</kegg_id>
  <pubchem_compound_id>115015</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>27891</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Ubuka T; Kinuta M; Akagi R; Kiguchi S; Azumi M  Reaction of S-(2-amino-2-carboxyethylsulfonyl)-L-cysteine with sulfite: synthesis of S-sulfo-L-cysteine and L-alanine 3-sulfinic acid and application to the determination of sulfite.    Analytical biochemistry  (1982),  126(2),  273-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:40 UTC</creation_date>
  <update_date>2020-04-15 21:35:31 UTC</update_date>
  <accession>BMDB0000732</accession>
  <secondary_accessions>
    <accession>BMDB00732</accession>
  </secondary_accessions>
  <name>Hydroxykynurenine</name>
  <description>Hydroxykynurenine, also known as hydroxykynurenine, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Hydroxykynurenine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. In cattle, hydroxykynurenine is involved in the metabolic pathway called the tryptophan metabolism pathway.</description>
  <synonyms>
    <synonym>2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid</synonym>
    <synonym>3-(3-Hydroxyanthraniloyl)alanine</synonym>
    <synonym>3-Hydroxy-DL-kynurenine</synonym>
    <synonym>2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoate</synonym>
    <synonym>3-(3-Hydroxyanthraniloyl)-alanine</synonym>
    <synonym>3-Hydroxy-kynurenine</synonym>
    <synonym>3-Hydroxykynurenine</synonym>
    <synonym>DL-3-Hydroxykynurenine</synonym>
    <synonym>Hydroxykinurenine</synonym>
    <synonym>OH-Kynurenine</synonym>
    <synonym>3-Hydroxykynurenine, (DL)-isomer</synonym>
    <synonym>3-Hydroxykynurenine, (D)-isomer</synonym>
    <synonym>3-Hydroxykynurenine, (L)-isomer</synonym>
  </synonyms>
  <chemical_formula>C10H12N2O4</chemical_formula>
  <average_molecular_weight>224.2133</average_molecular_weight>
  <monisotopic_moleculate_weight>224.079706882</monisotopic_moleculate_weight>
  <iupac_name>2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid</iupac_name>
  <traditional_iupac>hydroxykynurenine</traditional_iupac>
  <cas_registry_number>484-78-6</cas_registry_number>
  <smiles>NC(CC(=O)C1=C(N)C(O)=CC=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C10H12N2O4/c11-6(10(15)16)4-8(14)5-2-1-3-7(13)9(5)12/h1-3,6,13H,4,11-12H2,(H,15,16)</inchi>
  <inchikey>VCKPUUFAIGNJHC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Alkyl-phenylketones</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alpha amino acids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Aryl alkyl ketones</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Beta-amino ketones</alternative_parent>
      <alternative_parent>Butyrophenones</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Gamma-keto acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
      <alternative_parent>o-Aminophenols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alkyl-phenylketone</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminophenol</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl alkyl ketone</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Beta-aminoketone</substituent>
      <substituent>Butyrophenone</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Gamma-keto acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Keto acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>O-aminophenol</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>hydroxykynurenine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>217 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>224.2133</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>224.079706882</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CC(=O)C1=C(N)C(O)=CC=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N2O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N2O4/c11-6(10(15)16)4-8(14)5-2-1-3-7(13)9(5)12/h1-3,6,13H,4,11-12H2,(H,15,16)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VCKPUUFAIGNJHC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>126.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>57.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440126</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>87</chemspider_id>
  <chebi_id>1547</chebi_id>
  <pubchem_compound_id>89</pubchem_compound_id>
  <kegg_id>C02794</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022210</foodb_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>3-Hydroxykynurenine</wikipedia_id>
  <metlin_id>5700</metlin_id>
  <synthesis_reference>Kotake, Munio; Sakan, Takeo; Senoh, Shiro.  Amino acids. IV. The synthesis of 3-hydroxykynurenine.    J. Inst. Polytech., Osaka. City Univ.  (1950),  1(No. 2),  35-41.  CAN 46:2639  AN 1952:2639</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:41 UTC</creation_date>
  <update_date>2020-04-15 22:14:25 UTC</update_date>
  <accession>BMDB0000733</accession>
  <secondary_accessions>
    <accession>BMDB00733</accession>
  </secondary_accessions>
  <name>Hyodeoxycholic acid</name>
  <description/>
  <synonyms>
    <synonym>Hyodeoxycholate</synonym>
    <synonym>3a,6a-Dihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,6a-Dihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3a,6a-Dihydroxy-5b-cholanate</synonym>
    <synonym>3a,6a-Dihydroxy-5b-cholanic acid</synonym>
    <synonym>3a,6a-Dihydroxy-5b-cholanoate</synonym>
    <synonym>3a,6a-Dihydroxy-5b-cholanoic acid</synonym>
    <synonym>6a-Hydroxylithocholate</synonym>
    <synonym>6a-Hydroxylithocholic acid</synonym>
    <synonym>7-Deoxyhyocholate</synonym>
    <synonym>7-Deoxyhyocholic acid</synonym>
    <synonym>a-Hyodeoxycholate</synonym>
    <synonym>a-Hyodeoxycholic acid</synonym>
    <synonym>alpha-Hyodeoxycholate</synonym>
    <synonym>alpha-Hyodeoxycholic acid</synonym>
    <synonym>Hyodesoxycholate</synonym>
    <synonym>Hyodesoxycholic acid</synonym>
    <synonym>Iodeoxycholate</synonym>
    <synonym>Iodeoxycholic acid</synonym>
    <synonym>3,6-Dihydroxy-5alpha-cholanoic acid</synonym>
    <synonym>NaHDC compound</synonym>
    <synonym>Hyodeoxycholic acid, (3alpha,5beta,6beta)-isomer</synonym>
    <synonym>Hyodeoxycholic acid, (3alpha,6beta)-isomer</synonym>
    <synonym>Hyodeoxycholic acid, sodium salt</synonym>
    <synonym>Murideoxycholic acid</synonym>
    <synonym>Sodium hyodeoxycholate</synonym>
    <synonym>(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
    <synonym>Hyodeoxycholic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O4</chemical_formula>
  <average_molecular_weight>392.572</average_molecular_weight>
  <monisotopic_moleculate_weight>392.292659768</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>83-49-8</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17-,18+,19+,20?,21+,23-,24-/m1/s1</inchi>
  <inchikey>DGABKXLVXPYZII-CDONHWFASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>6-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>6-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>198.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0598 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.08</value>
      <source>RODA,A ET AL. (1990)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>392.572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.292659768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17-,18+,19+,20?,21+,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DGABKXLVXPYZII-CDONHWFASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344568</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>8139282</chemspider_id>
  <chebi_id/>
  <pubchem_compound_id>9963687</pubchem_compound_id>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB022211</foodb_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Hyodeoxycholic acid</wikipedia_id>
  <metlin_id>5701</metlin_id>
  <synthesis_reference>Eyssen, H. J.; De Pauw, G.; Van Eldere, J. Formation of hyodeoxycholic acid from muricholic acid and hyocholic acid by an unidentified Gram-positive rod termed HDCA-1 isolated from rat intestinal microflora. Applied and Environmental Microbiology (1999),</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:42 UTC</creation_date>
  <update_date>2020-03-13 16:23:26 UTC</update_date>
  <accession>BMDB0000734</accession>
  <secondary_accessions>
    <accession>BMDB00734</accession>
  </secondary_accessions>
  <name>Indoleacrylic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Indoleacrylic acid</synonym>
    <synonym>2-Indolylacrylic acid</synonym>
    <synonym>3-(2-Indolyl)acrylic acid</synonym>
    <synonym>Indole-2-acrylic acid</synonym>
    <synonym>trans-2-Indoleacrylic acid</synonym>
    <synonym>2-Indoleacrylate</synonym>
    <synonym>2-Indolylacrylate</synonym>
    <synonym>3-(2-Indolyl)acrylate</synonym>
    <synonym>Indole-2-acrylate</synonym>
    <synonym>trans-2-Indoleacrylate</synonym>
    <synonym>Indoleacrylate</synonym>
    <synonym>(e)-3-(indol-2-yl)Acrylate</synonym>
    <synonym>3-Indoleacrylate</synonym>
    <synonym>3-Indoleacrylic acid</synonym>
    <synonym>Indoleacrylic acid</synonym>
  </synonyms>
  <chemical_formula>C11H9NO2</chemical_formula>
  <average_molecular_weight>187.1947</average_molecular_weight>
  <monisotopic_moleculate_weight>187.063328537</monisotopic_moleculate_weight>
  <iupac_name>(2E)-3-(1H-indol-2-yl)prop-2-enoic acid</iupac_name>
  <traditional_iupac>(2E)-3-(1H-indol-2-yl)prop-2-enoic acid</traditional_iupac>
  <cas_registry_number>1204-06-4</cas_registry_number>
  <smiles>OC(=O)\C=C\C1=CC2=C(N1)C=CC=C2</smiles>
  <inchi>InChI=1S/C11H9NO2/c13-11(14)6-5-9-7-8-3-1-2-4-10(8)12-9/h1-7,12H,(H,13,14)/b6-5+</inchi>
  <inchikey>SXOUIMVOMIGLHO-AATRIKPKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene  to form 2,3-benzopyrrole.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Indoles</sub_class>
    <direct_parent>Indoles</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indole</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>180 - 186 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-3-(1H-indol-2-yl)prop-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>187.1947</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>187.063328537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)\C=C\C1=CC2=C(N1)C=CC=C2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H9NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H9NO2/c13-11(14)6-5-9-7-8-3-1-2-4-10(8)12-9/h1-7,12H,(H,13,14)/b6-5+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SXOUIMVOMIGLHO-AATRIKPKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>53.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346326</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>10607876</chemspider_id>
  <chebi_id>90333</chebi_id>
  <pubchem_compound_id>15030923</pubchem_compound_id>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB000938</foodb_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00000111</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5702</metlin_id>
  <synthesis_reference>Moffatt, J. S.  Preparation of b-3-indolylacrylic acid.    Journal of the Chemical Society  (1957),     1442-3.;  Bauguess, Lyle C.; Berg, Clarence P.  The availability of indole derivatives for supplementing diets deficient in tryptophan.    Proceedings of the Iowa Academy of Science  (1933),  40  110-11.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:43 UTC</creation_date>
  <update_date>2020-03-13 16:23:27 UTC</update_date>
  <accession>BMDB0000735</accession>
  <secondary_accessions>
    <accession>BMDB00735</accession>
  </secondary_accessions>
  <name>Hydroxyphenylacetylglycine</name>
  <description/>
  <synonyms>
    <synonym>p-Hydroxyphenylacetylglycine</synonym>
    <synonym>4-Hydroxyphenylacetylglycine</synonym>
    <synonym>N-[(4-Hydroxyphenyl)acetyl]-glycine</synonym>
    <synonym>N-[(p-Hydroxyphenyl)acetyl]-glycine</synonym>
    <synonym>[[(4-Hydroxyphenyl)acetyl]amino]acetate</synonym>
    <synonym>[[(4-Hydroxyphenyl)acetyl]amino]acetic acid</synonym>
  </synonyms>
  <chemical_formula>C10H11NO4</chemical_formula>
  <average_molecular_weight>209.1986</average_molecular_weight>
  <monisotopic_moleculate_weight>209.068807845</monisotopic_moleculate_weight>
  <iupac_name>2-[2-(4-hydroxyphenyl)acetamido]acetic acid</iupac_name>
  <traditional_iupac>p-hydroxyphenylacetylglycine</traditional_iupac>
  <cas_registry_number>28116-23-6</cas_registry_number>
  <smiles>OC(=O)CNC(=O)CC1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C10H11NO4/c12-8-3-1-7(2-4-8)5-9(13)11-6-10(14)15/h1-4,12H,5-6H2,(H,11,13)(H,14,15)</inchi>
  <inchikey>CPPDWYIPKSSNNM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylacetamides</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylacetamide</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylglycine</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
      <external_descriptor>monocarboxylic acid amide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[2-(4-hydroxyphenyl)acetamido]acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>209.1986</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>209.068807845</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CNC(=O)CC1=CC=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H11NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H11NO4/c12-8-3-1-7(2-4-8)5-9(13)11-6-10(14)15/h1-4,12H,5-6H2,(H,11,13)(H,14,15)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CPPDWYIPKSSNNM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>86.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>52.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373428</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022212</foodb_id>
  <chemspider_id>389604</chemspider_id>
  <drugbank_id/>
  <kegg_id>C05596</kegg_id>
  <pubchem_compound_id>440732</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28595</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:44 UTC</creation_date>
  <update_date>2020-04-14 22:48:14 UTC</update_date>
  <accession>BMDB0000736</accession>
  <secondary_accessions>
    <accession>BMDB00736</accession>
  </secondary_accessions>
  <name>Isobutyryl-L-carnitine</name>
  <description>Isobutyryl-L-carnitine belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Isobutyryl-L-carnitine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Isobutyryl-L-carnitine has been linked to several inborn metabolic disorders including very long chain acyl-coa dehydrogenase deficiency and short chain acyl-coa dehydrogenase deficiency.</description>
  <synonyms>
    <synonym>(R)-Isobutyrylcarnitine</synonym>
    <synonym>Iso-butyryl-L(-)-carnitin</synonym>
    <synonym>Isobutyryl-carnitine</synonym>
    <synonym>Isobutyryl-L-(-)-carnitine</synonym>
    <synonym>O-Isobutanoyl-(R)-carnitine</synonym>
    <synonym>Isobutyryl-1-carnitine</synonym>
    <synonym>Isobutyrylcarnitine</synonym>
    <synonym>O-Isobutyryl-L-carnitine</synonym>
    <synonym>Isobutyryl-L-carnitine</synonym>
  </synonyms>
  <chemical_formula>C11H21NO4</chemical_formula>
  <average_molecular_weight>231.292</average_molecular_weight>
  <monisotopic_moleculate_weight>231.14705816</monisotopic_moleculate_weight>
  <iupac_name>(3R)-3-[(2-methylpropanoyl)oxy]-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>(3R)-3-[(2-methylpropanoyl)oxy]-4-(trimethylammonio)butanoate</traditional_iupac>
  <cas_registry_number>25518-49-4</cas_registry_number>
  <smiles>CC(C)C(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C</smiles>
  <inchi>InChI=1S/C11H21NO4/c1-8(2)11(15)16-9(6-10(13)14)7-12(3,4)5/h8-9H,6-7H2,1-5H3/t9-/m1/s1</inchi>
  <inchikey>LRCNOZRCYBNMEP-SECBINFHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Acyl carnitines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Branched fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl-carnitine</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>O-acyl-L-carnitine</external_descriptor>
      <external_descriptor>O-isobutyrylcarnitine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R)-3-[(2-methylpropanoyl)oxy]-4-(trimethylazaniumyl)butanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>231.292</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>231.14705816</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)C(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H21NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H21NO4/c1-8(2)11(15)16-9(6-10(13)14)7-12(3,4)5/h8-9H,6-7H2,1-5H3/t9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LRCNOZRCYBNMEP-SECBINFHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>81.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2003</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.4 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.6 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.99 +/- 0.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022213</foodb_id>
  <chemspider_id>147286</chemspider_id>
  <drugbank_id/>
  <kegg_id/>
  <pubchem_compound_id>168379</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>84838</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5704</metlin_id>
  <synthesis_reference>Strack, Erich; Mueller, Detlef M.  Preparation of O-acylcarnitines.    Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie  (1970),  351(1),  95-8.  </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:45 UTC</creation_date>
  <update_date>2020-04-15 22:14:26 UTC</update_date>
  <accession>BMDB0000737</accession>
  <secondary_accessions>
    <accession>BMDB00737</accession>
  </secondary_accessions>
  <name>Heptacarboxylporphyrin I</name>
  <description/>
  <synonyms>
    <synonym>Heptacarboxylic acid porphyrin I</synonym>
    <synonym>Heptaporphyrin</synonym>
    <synonym>3-[9,14,19-Tris(2-carboxyethyl)-10,15,20-tris(carboxymethyl)-5-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C39H38N4O14</chemical_formula>
  <average_molecular_weight>786.7374</average_molecular_weight>
  <monisotopic_moleculate_weight>786.238451944</monisotopic_moleculate_weight>
  <iupac_name>3-[9,14,19-tris(2-carboxyethyl)-10,15,20-tris(carboxymethyl)-5-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[9,14,19-tris(2-carboxyethyl)-10,15,20-tris(carboxymethyl)-5-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>65406-45-3</cas_registry_number>
  <smiles>CC1=C(CCC(O)=O)\C2=C\C3=C(CC(O)=O)C(CCC(O)=O)=C(N3)\C=C3/N=C(/C=C4\N\C(=C/C1=N2)C(CCC(O)=O)=C4CC(O)=O)C(CCC(O)=O)=C3CC(O)=O</smiles>
  <inchi>InChI=1S/C39H38N4O14/c1-17-18(2-6-33(44)45)26-14-30-23(11-38(54)55)20(4-8-35(48)49)28(42-30)16-32-24(12-39(56)57)21(5-9-36(50)51)29(43-32)15-31-22(10-37(52)53)19(3-7-34(46)47)27(41-31)13-25(17)40-26/h13-16,41-42H,2-12H2,1H3,(H,44,45)(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)/b25-13-,26-14-,27-13-,28-16-,29-15-,30-14-,31-15-,32-16-</inchi>
  <inchikey>GWTVAIDNCPVMLP-YBWGHNILSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>208 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[9,14,19-tris(2-carboxyethyl)-10,15,20-tris(carboxymethyl)-5-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>786.7374</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>786.238451944</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCC(O)=O)\C2=C\C3=C(CC(O)=O)C(CCC(O)=O)=C(N3)\C=C3/N=C(/C=C4\N\C(=C/C1=N2)C(CCC(O)=O)=C4CC(O)=O)C(CCC(O)=O)=C3CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C39H38N4O14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C39H38N4O14/c1-17-18(2-6-33(44)45)26-14-30-23(11-38(54)55)20(4-8-35(48)49)28(42-30)16-32-24(12-39(56)57)21(5-9-36(50)51)29(43-32)15-31-22(10-37(52)53)19(3-7-34(46)47)27(41-31)13-25(17)40-26/h13-16,41-42H,2-12H2,1H3,(H,44,45)(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)/b25-13-,26-14-,27-13-,28-16-,29-15-,30-14-,31-15-,32-16-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GWTVAIDNCPVMLP-YBWGHNILSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>318.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>195.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>82.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349713</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>13628138</chemspider_id>
  <chebi_id>89912</chebi_id>
  <pubchem_compound_id/>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB022214</foodb_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5705</metlin_id>
  <synthesis_reference>Ringuet, Michel; Pottier, Roy H.; Kennedy, James C.  Preparation of porphyrin amides as photosensitizing neoplasm inhibitors.    PCT Int. Appl.  (1992),     35 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:47 UTC</creation_date>
  <update_date>2020-04-15 23:55:39 UTC</update_date>
  <accession>BMDB0000738</accession>
  <secondary_accessions>
    <accession>BMDB00738</accession>
  </secondary_accessions>
  <name>Indole</name>
  <description/>
  <synonyms>
    <synonym>2,3-Benzopyrrole</synonym>
    <synonym>indol</synonym>
    <synonym>1-Azaindene</synonym>
    <synonym>1-Benzazole</synonym>
    <synonym>Benzo[b]pyrrole</synonym>
    <synonym>Ketole</synonym>
    <synonym>Indole</synonym>
  </synonyms>
  <chemical_formula>C8H7N</chemical_formula>
  <average_molecular_weight>117.1479</average_molecular_weight>
  <monisotopic_moleculate_weight>117.057849229</monisotopic_moleculate_weight>
  <iupac_name>1H-indole</iupac_name>
  <traditional_iupac>indole</traditional_iupac>
  <cas_registry_number>120-72-9</cas_registry_number>
  <smiles>N1C=CC2=C1C=CC=C2</smiles>
  <inchi>InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H</inchi>
  <inchikey>SIKJAQJRHWYJAI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene  to form 2,3-benzopyrrole.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Indoles</sub_class>
    <direct_parent>Indoles</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>an indole</external_descriptor>
      <external_descriptor>indole</external_descriptor>
      <external_descriptor>polycyclic heteroarene</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>52.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>3.56 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.14</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>16.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1H-indole</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>117.1479</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>117.057849229</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N1C=CC2=C1C=CC=C2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H7N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SIKJAQJRHWYJAI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>15.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448383</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>200 +/- 100</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment> after feeding tryptophane</comment>
      <references>
        <reference>
          <reference_text>Nocerini MR, Honeyfield DC, Carlson JR, Breeze RG: Reduction of 3-methylindole production and prevention of acute bovine pulmonary edema and emphysema with lasalocid. J Anim Sci. 1985 Jan;60(1):232-8.</reference_text>
          <pubmed_id>3972744</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB012008</foodb_id>
  <chemspider_id>776</chemspider_id>
  <drugbank_id>DB04532</drugbank_id>
  <kegg_id>C00463</kegg_id>
  <pubchem_compound_id>798</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16881</chebi_id>
  <meta_cyc_id>INDOLE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001418</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Indole</wikipedia_id>
  <metlin_id>286</metlin_id>
  <synthesis_reference>Grigoleit, Georg; Oberkobusch, Rudolf; Collin, Gerd.  Indole from 2-ethylaniline.    Ger. Offen.  (1973),     6 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:48 UTC</creation_date>
  <update_date>2020-03-13 16:23:29 UTC</update_date>
  <accession>BMDB0000739</accession>
  <secondary_accessions>
    <accession>BMDB00739</accession>
  </secondary_accessions>
  <name>Isodesmosine</name>
  <description/>
  <synonyms>
    <synonym>2-(4-Amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)-3,5-bis(3-amino-3-carboxypropyl)pyridinium</synonym>
    <synonym>2-Amino-6-[3,5-bis(3-amino-4-hydroxy-4-oxobutyl)-2-(4-amino-5-hydroxy-5-oxopentyl)pyridin-1-ium-1-yl]hexanoic acid</synonym>
    <synonym>Ide</synonym>
    <synonym>2-Amino-6-[3,5-bis(3-amino-4-hydroxy-4-oxobutyl)-2-(4-amino-5-hydroxy-5-oxopentyl)pyridin-1-ium-1-yl]hexanoate</synonym>
    <synonym>2-(4-Amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)-3,5-bis(3-amino-3-carboxypropyl)-pyridinium</synonym>
    <synonym>Iso-desmosin</synonym>
  </synonyms>
  <chemical_formula>C24H40N5O8</chemical_formula>
  <average_molecular_weight>526.6031</average_molecular_weight>
  <monisotopic_moleculate_weight>526.287688281</monisotopic_moleculate_weight>
  <iupac_name>3,5-bis(3-amino-3-carboxypropyl)-2-(4-amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)pyridin-1-ium</iupac_name>
  <traditional_iupac>isodesmosine</traditional_iupac>
  <cas_registry_number>991-01-5</cas_registry_number>
  <smiles>NC(CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C24H39N5O8/c25-16(21(30)31)4-1-2-11-29-13-14(7-9-18(27)23(34)35)12-15(8-10-19(28)24(36)37)20(29)6-3-5-17(26)22(32)33/h12-13,16-19H,1-11,25-28H2,(H3-,30,31,32,33,34,35,36,37)/p+1</inchi>
  <inchikey>RGXCTRIQQODGIZ-UHFFFAOYSA-O</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Tetracarboxylic acids and derivatives</sub_class>
    <direct_parent>Tetracarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha amino acids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridinium derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridinium</substituent>
      <substituent>Tetracarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>lysine derivative</external_descriptor>
      <external_descriptor>pyridinium ion</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-4.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3,5-bis(3-amino-3-carboxypropyl)-2-(4-amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)pyridin-1-ium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>526.6031</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>526.287688281</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40N5O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H39N5O8/c25-16(21(30)31)4-1-2-11-29-13-14(7-9-18(27)23(34)35)12-15(8-10-19(28)24(36)37)20(29)6-3-5-17(26)22(32)33/h12-13,16-19H,1-11,25-28H2,(H3-,30,31,32,33,34,35,36,37)/p+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RGXCTRIQQODGIZ-UHFFFAOYSA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>257.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>133.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>56.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>80238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>80239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>80240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>141054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>141055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>141056</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB000467</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>13811</pubchem_compound_id>
  <chemspider_id>13214</chemspider_id>
  <chebi_id>64366</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Isodesmosine</wikipedia_id>
  <metlin_id>5707</metlin_id>
  <synthesis_reference>Thomas, J.; Elsden, D. F.; Partridge, S. M.  Partial structure of two major degradation products from the cross-linkages in elastin.    Nature (London, United Kingdom)  (1963),  200(4907),  651-2.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:49 UTC</creation_date>
  <update_date>2020-04-16 20:40:35 UTC</update_date>
  <accession>BMDB0000740</accession>
  <secondary_accessions>
    <accession>BMDB00740</accession>
  </secondary_accessions>
  <name>Lactulose</name>
  <description/>
  <synonyms>
    <synonym>4-O-beta-D-Galactopyranosyl-D-fructofuranose</synonym>
    <synonym>4-O-beta-D-Galactopyranosyl-D-fructose</synonym>
    <synonym>D-Lactulose</synonym>
    <synonym>Lactulosa</synonym>
    <synonym>Lactulosum</synonym>
    <synonym>Cephulac</synonym>
    <synonym>Chronulac</synonym>
    <synonym>4-O-b-D-Galactopyranosyl-D-fructofuranose</synonym>
    <synonym>4-O-Β-D-galactopyranosyl-D-fructofuranose</synonym>
    <synonym>4-O-b-D-Galactopyranosyl-D-fructose</synonym>
    <synonym>4-O-Β-D-galactopyranosyl-D-fructose</synonym>
    <synonym>(2S,3R,4S,5R,6R)-2-[(2R,3S,4S,5R)-4,5-Dihydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol</synonym>
    <synonym>4-O-beta-delta-Galactopyranosyl-delta-fructofuranose</synonym>
    <synonym>4-O-beta-delta-Galactopyranosyl-delta-fructose</synonym>
    <synonym>Bifiteral</synonym>
    <synonym>delta-Lactulose</synonym>
    <synonym>Normase</synonym>
    <synonym>Amivalex</synonym>
    <synonym>Duphalac</synonym>
  </synonyms>
  <chemical_formula>C12H22O11</chemical_formula>
  <average_molecular_weight>342.2965</average_molecular_weight>
  <monisotopic_moleculate_weight>342.116211546</monisotopic_moleculate_weight>
  <iupac_name>(2S,3R,4S,5R,6R)-2-{[(2R,3S,4S,5R)-4,5-dihydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>lactulose</traditional_iupac>
  <cas_registry_number>4618-18-2</cas_registry_number>
  <smiles>OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C12H22O11/c13-1-4-6(16)7(17)8(18)11(21-4)22-9-5(2-14)23-12(20,3-15)10(9)19/h4-11,13-20H,1-3H2/t4-,5-,6+,7+,8-,9-,10+,11+,12-/m1/s1</inchi>
  <inchikey>JCQLYHFGKNRPGE-FCVZTGTOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>O-glycosyl compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Disaccharides</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>glycosylfructose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3R,4S,5R,6R)-2-{[(2R,3S,4S,5R)-4,5-dihydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>342.2965</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>342.116211546</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H22O11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H22O11/c13-1-4-6(16)7(17)8(18)11(21-4)22-9-5(2-14)23-12(20,3-15)10(9)19/h4-11,13-20H,1-3H2/t4-,5-,6+,7+,8-,9-,10+,11+,12-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JCQLYHFGKNRPGE-FCVZTGTOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>189.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>69258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>69259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>69260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>127491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>127492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>127493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218117</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022215</foodb_id>
  <chemspider_id>10856</chemspider_id>
  <drugbank_id>DB00581</drugbank_id>
  <kegg_id>C07064</kegg_id>
  <pubchem_compound_id>11333</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>6359</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Lactulose</wikipedia_id>
  <metlin_id>916</metlin_id>
  <synthesis_reference>Dalev, P.; Tsoneva, P.  Method for preparation of lactulose from lactose.    Trudove na Nauchnoizsledovatelskiya Khimikofarmatsevtichen Institut  (1982),  12  95-102.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:50 UTC</creation_date>
  <update_date>2020-04-16 20:36:44 UTC</update_date>
  <accession>BMDB0000742</accession>
  <secondary_accessions>
    <accession>BMDB00742</accession>
  </secondary_accessions>
  <name>Homocysteine</name>
  <description>Homocysteine, also known as Hcy or homo-cys, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Homocysteine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Homocysteine exists in all living species, ranging from bacteria to humans. Homocysteine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>Hcy</synonym>
    <synonym>L-2-Amino-4-mercaptobutyric acid</synonym>
    <synonym>L-2-Amino-4-mercaptobutyrate</synonym>
    <synonym>2-Amino-4-mercaptobutyric acid</synonym>
    <synonym>Homocysteine, L isomer</synonym>
    <synonym>L-Isomer homocysteine</synonym>
    <synonym>2 Amino 4 mercaptobutyric acid</synonym>
    <synonym>Homocysteine, L-isomer</synonym>
    <synonym>(S)-2-Amino-4-mercapto-butanoate</synonym>
    <synonym>(S)-2-Amino-4-mercapto-butanoic acid</synonym>
    <synonym>(S)-2-Amino-4-mercaptobutanoic acid</synonym>
    <synonym>(S)-Homocysteine</synonym>
    <synonym>2-Amino-4-mercapto-DL-butyrate</synonym>
    <synonym>2-Amino-4-mercapto-DL-butyric acid</synonym>
    <synonym>2-Amino-4-mercapto-L-butyric acid</synonym>
    <synonym>2-Amino-4-mercapto-butanoate</synonym>
    <synonym>2-Amino-4-mercapto-butanoic acid</synonym>
    <synonym>2-Amino-4-mercapto-butyric acid</synonym>
    <synonym>2-Amino-4-sulfanylbutanoate</synonym>
    <synonym>2-Amino-4-sulfanylbutanoic acid</synonym>
    <synonym>D,L-Homocysteine</synonym>
    <synonym>DL-2-Amino-4-mercapto-butyric acid</synonym>
    <synonym>DL-2-Amino-4-mercaptobutyric acid</synonym>
    <synonym>DL-Homocysteine</synonym>
    <synonym>Homo-cys</synonym>
    <synonym>L-2-Amino-4-mercapto-butyric acid</synonym>
    <synonym>L-Homocysteine</synonym>
    <synonym>2-Amino-4-mercapto-butyrate</synonym>
    <synonym>Homocysteine</synonym>
  </synonyms>
  <chemical_formula>C4H9NO2S</chemical_formula>
  <average_molecular_weight>135.185</average_molecular_weight>
  <monisotopic_moleculate_weight>135.035399227</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-sulfanylbutanoic acid</iupac_name>
  <traditional_iupac>L-homocysteine</traditional_iupac>
  <cas_registry_number>6027-13-0</cas_registry_number>
  <smiles>N[C@@H](CCS)C(O)=O</smiles>
  <inchi>InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m0/s1</inchi>
  <inchikey>FFFHZYDWPBMWHY-VKHMYHEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Thia fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>homocysteine</external_descriptor>
      <external_descriptor>serine family amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>232 - 233 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>148 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-sulfanylbutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>135.185</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>135.035399227</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCS)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H9NO2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FFFHZYDWPBMWHY-VKHMYHEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Homocysteine Degradation</name>
      <smpdb_id>SMP0087201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5211</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00155</kegg_id>
  <foodb_id>FDB001491</foodb_id>
  <chemspider_id>82666</chemspider_id>
  <drugbank_id>DB04422</drugbank_id>
  <chebi_id>17588</chebi_id>
  <pubchem_compound_id>91552</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001365</knapsack_id>
  <meta_cyc_id>HOMO-CYS</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Homocysteine</wikipedia_id>
  <metlin_id>3256</metlin_id>
  <synthesis_reference>Karrenbauer, Michael; Kleemann, Axel; Luessling, Theodor; Schaefer, Fritz.  D,L-Homocysteine (I).    Ger.  (1984),     4 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00414</protein_accession>
      <name>Methionine synthase</name>
      <uniprot_id>Q4JIJ3</uniprot_id>
      <gene_name>MTR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00837</protein_accession>
      <name>Adenosylhomocysteinase</name>
      <uniprot_id>A5PKK6</uniprot_id>
      <gene_name>AHCYL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00838</protein_accession>
      <name>Adenosylhomocysteinase</name>
      <uniprot_id>A6QLP2</uniprot_id>
      <gene_name>AHCYL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01057</protein_accession>
      <name>Betaine--homocysteine S-methyltransferase 1</name>
      <uniprot_id>Q5I597</uniprot_id>
      <gene_name>BHMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01293</protein_accession>
      <name>Adenosylhomocysteinase</name>
      <uniprot_id>Q3MHL4</uniprot_id>
      <gene_name>AHCY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:51 UTC</creation_date>
  <update_date>2020-04-15 22:14:27 UTC</update_date>
  <accession>BMDB0000743</accession>
  <secondary_accessions>
    <accession>BMDB00743</accession>
  </secondary_accessions>
  <name>Hexacarboxylporphyrin I</name>
  <description/>
  <synonyms>
    <synonym>Hexacarboxylic acid prophyrin I</synonym>
    <synonym>Hexacarboxyporphyrin I</synonym>
    <synonym>3-[9,14,19-Tris(2-carboxyethyl)-10,15-bis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C38H38N4O12</chemical_formula>
  <average_molecular_weight>742.7279</average_molecular_weight>
  <monisotopic_moleculate_weight>742.2486227</monisotopic_moleculate_weight>
  <iupac_name>3-[9,14,19-tris(2-carboxyethyl)-10,15-bis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[9,14,19-tris(2-carboxyethyl)-10,15-bis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>73913-56-1</cas_registry_number>
  <smiles>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(CC(O)=O)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4C)/C(CCC(O)=O)=C3CC(O)=O</smiles>
  <inchi>InChI=1S/C38H38N4O12/c1-17-19(3-7-33(43)44)27-13-25-18(2)20(4-8-34(45)46)28(40-25)15-31-24(12-38(53)54)22(6-10-36(49)50)30(42-31)16-32-23(11-37(51)52)21(5-9-35(47)48)29(41-32)14-26(17)39-27/h13-16,40-41H,3-12H2,1-2H3,(H,43,44)(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)/b25-13-,26-14-,27-13-,28-15-,29-14-,30-16-,31-15-,32-16-</inchi>
  <inchikey>AFHLWIUSJBEMJE-ZMXCOFNRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>208 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[9,14,19-tris(2-carboxyethyl)-10,15-bis(carboxymethyl)-5,20-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>742.7279</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>742.2486227</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(CC(O)=O)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4C)/C(CCC(O)=O)=C3CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C38H38N4O12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C38H38N4O12/c1-17-19(3-7-33(43)44)27-13-25-18(2)20(4-8-34(45)46)28(40-25)15-31-24(12-38(53)54)22(6-10-36(49)50)30(42-31)16-32-23(11-37(51)52)21(5-9-35(47)48)29(41-32)14-26(17)39-27/h13-16,40-41H,3-12H2,1-2H3,(H,43,44)(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)/b25-13-,26-14-,27-13-,28-15-,29-14-,30-16-,31-15-,32-16-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AFHLWIUSJBEMJE-ZMXCOFNRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>281.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>188.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>79.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352746</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022216</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id/>
  <chemspider_id>13628139</chemspider_id>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5711</metlin_id>
  <synthesis_reference>Ringuet, Michel; Pottier, Roy H.; Kennedy, James C.  Preparation of porphyrin amides as photosensitizing neoplasm inhibitors.    PCT Int. Appl.  (1992),     35 pp.  CODEN: PIXXD2  WO  9206097  A1  19920416  CAN 117:48227  AN 1992:448227</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:52 UTC</creation_date>
  <update_date>2020-04-14 22:48:15 UTC</update_date>
  <accession>BMDB0000744</accession>
  <secondary_accessions>
    <accession>BMDB00744</accession>
  </secondary_accessions>
  <name>Malic acid</name>
  <description>Malic acid, also known as malate or aepfelsaeure, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Malic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Malic acid exists in all living organisms, ranging from bacteria to humans. In cattle, malic acid is involved in the metabolic pathway called the transfer OF acetyl groups into mitochondria pathway.</description>
  <synonyms>
    <synonym>2-Hydroxybutanedioic acid</synonym>
    <synonym>2-Hydroxyethane-1,2-dicarboxylic acid</synonym>
    <synonym>2-Hydroxysuccinic acid</synonym>
    <synonym>alpha-Hydroxysuccinic acid</synonym>
    <synonym>Aepfelsaeure</synonym>
    <synonym>Apple acid</synonym>
    <synonym>DL-Malic acid</synonym>
    <synonym>e296</synonym>
    <synonym>H2Mal</synonym>
    <synonym>Hydroxybutanedioic acid</synonym>
    <synonym>Hydroxysuccinic acid</synonym>
    <synonym>Malate</synonym>
    <synonym>2-Hydroxybutanedioate</synonym>
    <synonym>2-Hydroxyethane-1,2-dicarboxylate</synonym>
    <synonym>2-Hydroxysuccinate</synonym>
    <synonym>a-Hydroxysuccinate</synonym>
    <synonym>a-Hydroxysuccinic acid</synonym>
    <synonym>alpha-Hydroxysuccinate</synonym>
    <synonym>Α-hydroxysuccinate</synonym>
    <synonym>Α-hydroxysuccinic acid</synonym>
    <synonym>DL-Malate</synonym>
    <synonym>Hydroxybutanedioate</synonym>
    <synonym>Hydroxysuccinate</synonym>
    <synonym>Deoxytetrarate</synonym>
    <synonym>Deoxytetraric acid</synonym>
    <synonym>Musashi-NO-ringosan</synonym>
    <synonym>Pomalus acid</synonym>
    <synonym>R,S-Malate</synonym>
    <synonym>R,S-Malic acid</synonym>
    <synonym>R,SMalate</synonym>
    <synonym>R,SMalic acid</synonym>
    <synonym>Malic acid, disodium salt</synonym>
    <synonym>Malic acid, disodium salt, (R)-isomer</synonym>
    <synonym>Malic acid, disodium salt, (S)-isomer</synonym>
    <synonym>Malic acid, monopotassium salt, (+-)-isomer</synonym>
    <synonym>Malic acid, (R)-isomer</synonym>
    <synonym>Malic acid, calcium salt, (1:1), (S)-isomer</synonym>
    <synonym>Malic acid, magnesium salt (2:1)</synonym>
    <synonym>Calcium (hydroxy-1-malate) hexahydrate</synonym>
    <synonym>Malic acid, potassium salt, (R)-isomer</synonym>
    <synonym>Malic acid, sodium salt, (+-)-isomer</synonym>
  </synonyms>
  <chemical_formula>C4H6O5</chemical_formula>
  <average_molecular_weight>134.0874</average_molecular_weight>
  <monisotopic_moleculate_weight>134.021523302</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxybutanedioic acid</iupac_name>
  <traditional_iupac>malic acid</traditional_iupac>
  <cas_registry_number>6915-15-7</cas_registry_number>
  <smiles>OC(CC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)</inchi>
  <inchikey>BJEPYKJPYRNKOW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Beta hydroxy acids and derivatives</sub_class>
    <direct_parent>Beta hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxydicarboxylic acid</external_descriptor>
      <external_descriptor>C4-dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>131 - 133 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.26</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxybutanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>134.0874</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>134.021523302</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(CC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H6O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BJEPYKJPYRNKOW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>24.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Malate-Aspartate Shuttle</name>
      <smpdb_id>SMP0087204</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37736</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>92.79 +/- 29.23</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8 - 441</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>83.66 +/- 28.83</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>151 +/- 19</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>141 +/- 23</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>142 +/- 17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>144 +/- 15</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>91.15 +/- 26.69</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C03668</kegg_id>
  <foodb_id>FDB008114</foodb_id>
  <drugbank_id>DB12751</drugbank_id>
  <pubchem_compound_id>525</pubchem_compound_id>
  <chemspider_id>510</chemspider_id>
  <chebi_id>6650</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>RS-Malate</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Malic_acid</wikipedia_id>
  <metlin_id>118</metlin_id>
  <synthesis_reference>Weiss, J. M.; Downs, C. R. Preliminary study on the formation of malic acid. Journal of the American Chemical Society (1922), 44 1118-25.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:53 UTC</creation_date>
  <update_date>2020-04-15 21:35:32 UTC</update_date>
  <accession>BMDB0000745</accession>
  <secondary_accessions>
    <accession>BMDB00745</accession>
  </secondary_accessions>
  <name>Homocarnosine</name>
  <description/>
  <synonyms>
    <synonym>(2S)-Homocarnosine</synonym>
    <synonym>(S)-Homocarnosine</synonym>
    <synonym>gamma-Aminobutyryl-L-his</synonym>
    <synonym>N-(4-Aminobutanoyl)-(S)-histidine</synonym>
    <synonym>N-(4-Aminobutyryl)-L-histidine</synonym>
    <synonym>N(alpha)-(4-Aminobutyryl)-L-histidine</synonym>
    <synonym>L-Homocarnosine</synonym>
    <synonym>gamma-Aminobutyryl histidine</synonym>
    <synonym>N-(4-Amino-1-oxobutyryl)histidine</synonym>
    <synonym>g-Aminobutyryl-L-his</synonym>
    <synonym>Γ-aminobutyryl-L-his</synonym>
    <synonym>N(a)-(4-Aminobutyryl)-L-histidine</synonym>
    <synonym>N(Α)-(4-aminobutyryl)-L-histidine</synonym>
    <synonym>g-Aminobutyryl histidine</synonym>
    <synonym>Γ-aminobutyryl histidine</synonym>
    <synonym>g-Aminobutyryl-L-histidine</synonym>
    <synonym>g-Aminobutyrylhistidine</synonym>
    <synonym>gamma-Aminobutyryl-L-histidine</synonym>
    <synonym>gamma-Aminobutyrylhistidine</synonym>
    <synonym>N-(4-Aminobutyryl)-histidine</synonym>
    <synonym>Homocarnosine sulfate</synonym>
  </synonyms>
  <chemical_formula>C10H16N4O3</chemical_formula>
  <average_molecular_weight>240.259</average_molecular_weight>
  <monisotopic_moleculate_weight>240.122240398</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-(4-aminobutanamido)-3-(1H-imidazol-4-yl)propanoic acid</iupac_name>
  <traditional_iupac>(2S)-2-(4-aminobutanamido)-3-(1H-imidazol-4-yl)propanoic acid</traditional_iupac>
  <cas_registry_number>3650-73-5</cas_registry_number>
  <smiles>NCCCC(=O)N[C@@H](CC1=CNC=N1)C(O)=O</smiles>
  <inchi>InChI=1S/C10H16N4O3/c11-3-1-2-9(15)14-8(10(16)17)4-7-5-12-6-13-7/h5-6,8H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)/t8-/m0/s1</inchi>
  <inchikey>CCLQKVKJOGVQLU-QMMMGPOBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Peptidomimetics</class>
    <sub_class>Hybrid peptides</sub_class>
    <direct_parent>Hybrid peptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Gamma amino acids and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Histidine and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolyl carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Gamma amino acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Histidine or derivatives</substituent>
      <substituent>Hybrid peptide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazolyl carboxylic acid derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-histidine derivative</external_descriptor>
      <external_descriptor>N-acyl-L-alpha-amino acid</external_descriptor>
      <external_descriptor>homocarnosine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-(4-aminobutanamido)-3-(1H-imidazol-4-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>240.259</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>240.122240398</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCC(=O)N[C@@H](CC1=CNC=N1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H16N4O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H16N4O3/c11-3-1-2-9(15)14-8(10(16)17)4-7-5-12-6-13-7/h5-6,8H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)/t8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CCLQKVKJOGVQLU-QMMMGPOBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>121.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>59.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437787</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00884</kegg_id>
  <foodb_id>FDB022217</foodb_id>
  <chemspider_id>8418848</chemspider_id>
  <drugbank_id/>
  <chebi_id>85981</chebi_id>
  <pubchem_compound_id>10243361</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-12185</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>270</metlin_id>
  <synthesis_reference>Nagai, Kineshiro; Nagai, Kinuko. Treating inflammatory diseases with homocarnosine. U.S. (1985), 7 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:54 UTC</creation_date>
  <update_date>2020-03-13 16:23:32 UTC</update_date>
  <accession>BMDB0000746</accession>
  <secondary_accessions>
    <accession>BMDB00746</accession>
  </secondary_accessions>
  <name>Hydroxyisocaproic acid</name>
  <description/>
  <synonyms>
    <synonym>(+)-2-Hydroxyisocaproic acid</synonym>
    <synonym>(+)-alpha-Hydroxyisocaproic acid</synonym>
    <synonym>(S)-2-Hydroxyisocaproic acid</synonym>
    <synonym>(S)-Leucic acid</synonym>
    <synonym>2-HYDROXY-4-methyl-pentanoIC ACID</synonym>
    <synonym>L-2-Hydroxy-4-methylvaleric acid</synonym>
    <synonym>L-2-Hydroxyisocaproic acid</synonym>
    <synonym>L-alpha-Hydroxyisocaproic acid</synonym>
    <synonym>L-Leucic acid</synonym>
    <synonym>(+)-2-Hydroxyisocaproate</synonym>
    <synonym>(+)-a-Hydroxyisocaproate</synonym>
    <synonym>(+)-a-Hydroxyisocaproic acid</synonym>
    <synonym>(+)-alpha-Hydroxyisocaproate</synonym>
    <synonym>(+)-Α-hydroxyisocaproate</synonym>
    <synonym>(+)-Α-hydroxyisocaproic acid</synonym>
    <synonym>(S)-2-Hydroxyisocaproate</synonym>
    <synonym>(S)-Leucate</synonym>
    <synonym>2-HYDROXY-4-methyl-pentanoate</synonym>
    <synonym>L-2-Hydroxy-4-methylvalerate</synonym>
    <synonym>L-2-Hydroxyisocaproate</synonym>
    <synonym>L-a-Hydroxyisocaproate</synonym>
    <synonym>L-a-Hydroxyisocaproic acid</synonym>
    <synonym>L-alpha-Hydroxyisocaproate</synonym>
    <synonym>L-Α-hydroxyisocaproate</synonym>
    <synonym>L-Α-hydroxyisocaproic acid</synonym>
    <synonym>L-Leucate</synonym>
    <synonym>Hydroxyisocaproate</synonym>
    <synonym>Hydroxy-isocaproate</synonym>
    <synonym>(2S)-2-Hydroxy-4-methylpentanoate</synonym>
    <synonym>(2S)-2-Hydroxy-4-methylpentanoic acid</synonym>
    <synonym>(S)-2-Hydroxy-4-methyl-pentanoate</synonym>
    <synonym>(S)-2-Hydroxy-4-methyl-pentanoic acid</synonym>
    <synonym>S-2-Hydroxy-4-methylpentanoate</synonym>
    <synonym>S-2-Hydroxy-4-methylpentanoic acid</synonym>
  </synonyms>
  <chemical_formula>C6H12O3</chemical_formula>
  <average_molecular_weight>132.1577</average_molecular_weight>
  <monisotopic_moleculate_weight>132.07864425</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-hydroxy-4-methylpentanoic acid</iupac_name>
  <traditional_iupac>(+)-α-hydroxyisocaproate</traditional_iupac>
  <cas_registry_number>13748-90-8</cas_registry_number>
  <smiles>CC(C)C[C@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t5-/m0/s1</inchi>
  <inchikey>LVRFTAZAXQPQHI-YFKPBYRVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>(2S)-2-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>2-hydroxy-4-methylvaleric acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>78 - 80 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-hydroxy-4-methylpentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.1577</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.07864425</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)C[C@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LVRFTAZAXQPQHI-YFKPBYRVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366135</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022218</foodb_id>
  <chemspider_id>75520</chemspider_id>
  <drugbank_id/>
  <chebi_id>44510</chebi_id>
  <pubchem_compound_id>83697</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>2-Hydroxyisocaproic acid</wikipedia_id>
  <metlin_id>5714</metlin_id>
  <synthesis_reference>Schmidt, E. G.; Peterson, W. H.; Fred, E. B.  The formation of l-leucic acid in the acetone-butyl alcohol fermentation.    Journal of Biological Chemistry  (1924),  61  163-75.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:56 UTC</creation_date>
  <update_date>2020-03-13 16:23:33 UTC</update_date>
  <accession>BMDB0000747</accession>
  <secondary_accessions>
    <accession>BMDB00747</accession>
  </secondary_accessions>
  <name>Isovalerylalanine</name>
  <description/>
  <synonyms>
    <synonym>(2S)-2-(3-Methylbutanamido)propanoic acid</synonym>
    <synonym>Isopentanoylalanine</synonym>
    <synonym>N-Isopentanoyl-L-alanine</synonym>
    <synonym>N-Isopentanoylalanine</synonym>
    <synonym>N-Isovalerylalanine</synonym>
    <synonym>(2S)-2-(3-Methylbutanamido)propanoate</synonym>
    <synonym>N-Isovaleryl-L-alanine</synonym>
    <synonym>Isovalerylalanine</synonym>
  </synonyms>
  <chemical_formula>C8H15NO3</chemical_formula>
  <average_molecular_weight>173.2096</average_molecular_weight>
  <monisotopic_moleculate_weight>173.105193351</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-(3-methylbutanamido)propanoic acid</iupac_name>
  <traditional_iupac>isovalerylalanine</traditional_iupac>
  <cas_registry_number>68219-63-6</cas_registry_number>
  <smiles>CC(C)CC(=O)N[C@@H](C)C(O)=O</smiles>
  <inchi>InChI=1S/C8H15NO3/c1-5(2)4-7(10)9-6(3)8(11)12/h5-6H,4H2,1-3H3,(H,9,10)(H,11,12)/t6-/m0/s1</inchi>
  <inchikey>OJPSNARFDYTAEN-LURJTMIESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alanine and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alanine or derivatives</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-(3-methylbutanamido)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>173.2096</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>173.105193351</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CC(=O)N[C@@H](C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15NO3/c1-5(2)4-7(10)9-6(3)8(11)12/h5-6H,4H2,1-3H3,(H,9,10)(H,11,12)/t6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OJPSNARFDYTAEN-LURJTMIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345258</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022219</foodb_id>
  <chemspider_id>114516</chemspider_id>
  <drugbank_id/>
  <chebi_id>136818</chebi_id>
  <pubchem_compound_id>129285</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5715</metlin_id>
  <synthesis_reference>Chen, Shu-Hui; Lamar, Jason; Guo, Deqi; Kohn, Todd; Yang, Hsiu-Chiung; McGee, James; Timm, David; Erickson, Jon; Yip, Yvonne; May, Patrick; McCarthy, James.  P3 cap modified Phe*-Ala series BACE inhibitors.    Bioorganic &amp; Medicinal Chemistry Letters  (2004),  14(1),  245-250.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:57 UTC</creation_date>
  <update_date>2020-03-13 16:23:33 UTC</update_date>
  <accession>BMDB0000748</accession>
  <secondary_accessions>
    <accession>BMDB00748</accession>
  </secondary_accessions>
  <name>L-3-Phenyllactic acid</name>
  <description/>
  <synonyms>
    <synonym>(R)-Phenyllactate</synonym>
    <synonym>D-3-Phenyllactic acid</synonym>
    <synonym>(R)-3-(Phenyl)lactate</synonym>
    <synonym>(R)-Phenyllactic acid</synonym>
    <synonym>D-3-Phenyllactate</synonym>
    <synonym>(R)-3-(Phenyl)lactic acid</synonym>
    <synonym>L-3-Phenyllactate</synonym>
    <synonym>(-)-2-Hydroxy-3-phenylpropanoate</synonym>
    <synonym>(-)-2-Hydroxy-3-phenylpropanoic acid</synonym>
    <synonym>(-)-2-Hydroxy-3-phenylpropionate</synonym>
    <synonym>(-)-2-Hydroxy-3-phenylpropionic acid</synonym>
    <synonym>(-)-3-Phenyllactate</synonym>
    <synonym>(-)-3-Phenyllactic acid</synonym>
    <synonym>(-)-b-Phenyllactate</synonym>
    <synonym>(-)-b-Phenyllactic acid</synonym>
    <synonym>(-)-beta-Phenyllactate</synonym>
    <synonym>(-)-beta-Phenyllactic acid</synonym>
    <synonym>(2S)-2-Hydroxy-3-phenylpropanoate</synonym>
    <synonym>(2S)-2-Hydroxy-3-phenylpropanoic acid</synonym>
    <synonym>(2S)-2-Hydroxy-3-phenylpropionate</synonym>
    <synonym>(2S)-2-Hydroxy-3-phenylpropionic acid</synonym>
    <synonym>(S)-3-Phenyl-lactate</synonym>
    <synonym>(S)-3-Phenyl-lactic acid</synonym>
    <synonym>(S)-3-Phenyllactic acid</synonym>
    <synonym>(S)-a-Hydroxy-benzenepropanoate</synonym>
    <synonym>(S)-a-Hydroxy-benzenepropanoic acid</synonym>
    <synonym>(S)-alpha-Hydroxy-benzenepropanoate</synonym>
    <synonym>(S)-alpha-Hydroxy-benzenepropanoic acid</synonym>
    <synonym>(S)-b-Phenyllactic</synonym>
    <synonym>(S)-beta-Phenyllactic</synonym>
    <synonym>alpha-Hydroxy-beta-phenyl-propionic acid</synonym>
    <synonym>HFA</synonym>
    <synonym>L-(-)-3-Phenyllactic acid</synonym>
    <synonym>L-2-Hydroxy-3-phenyl-propionic acid</synonym>
    <synonym>L-beta-Phenyllactic acid</synonym>
    <synonym>L-Phenyl lactate</synonym>
    <synonym>Phenyllactic acid</synonym>
    <synonym>(R)-3-Phenyllactate</synonym>
  </synonyms>
  <chemical_formula>C9H10O3</chemical_formula>
  <average_molecular_weight>166.1739</average_molecular_weight>
  <monisotopic_moleculate_weight>166.062994186</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-hydroxy-3-phenylpropanoic acid</iupac_name>
  <traditional_iupac>(R)-phenyllactate</traditional_iupac>
  <cas_registry_number>20312-36-1</cas_registry_number>
  <smiles>O[C@H](CC1=CC=CC=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)/t8-/m1/s1</inchi>
  <inchikey>VOXXWSYKYCBWHO-MRVPVSSYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Phenylpropanoic acids</class>
    <sub_class/>
    <direct_parent>Phenylpropanoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>(2R)-2-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>3-phenyllactic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>121 - 125 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-hydroxy-3-phenylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>166.1739</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>166.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H](CC1=CC=CC=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)/t8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VOXXWSYKYCBWHO-MRVPVSSYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372495</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05607</kegg_id>
  <foodb_id>FDB022220</foodb_id>
  <chemspider_id>558480</chemspider_id>
  <drugbank_id/>
  <chebi_id>32978</chebi_id>
  <pubchem_compound_id>643327</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00000150</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:58 UTC</creation_date>
  <update_date>2020-03-13 16:23:34 UTC</update_date>
  <accession>BMDB0000749</accession>
  <secondary_accessions>
    <accession>BMDB00749</accession>
  </secondary_accessions>
  <name>Mesaconic acid</name>
  <description>Citraconic acid, also known as 2-methylmaleate or methylmaleic acid, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Citraconic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Citraconic acid exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>(e)-2-Methyl-2-butenedioic acid</synonym>
    <synonym>(e)-Citraconic acid</synonym>
    <synonym>2-Methylfumaric acid</synonym>
    <synonym>Citronic acid</synonym>
    <synonym>Methylfumaric acid</synonym>
    <synonym>trans-1-Propene-1,2-dicarboxylic acid</synonym>
    <synonym>trans-2-Methyl-2-butenedioic acid</synonym>
    <synonym>2-Methylfumarate</synonym>
    <synonym>(e)-2-Methyl-2-butenedioate</synonym>
    <synonym>(e)-Citraconate</synonym>
    <synonym>Citronate</synonym>
    <synonym>Methylfumarate</synonym>
    <synonym>trans-1-Propene-1,2-dicarboxylate</synonym>
    <synonym>trans-2-Methyl-2-butenedioate</synonym>
    <synonym>Mesaconate</synonym>
    <synonym>(2E)-2-Methyl-2-butenedioate</synonym>
    <synonym>(2E)-2-Methyl-2-butenedioic acid</synonym>
    <synonym>Citraconic acid, ammonium salt</synonym>
    <synonym>Citraconic acid, sodium salt</synonym>
    <synonym>Citraconic acid</synonym>
    <synonym>Methylmaleic acid</synonym>
    <synonym>Citraconic acid, (e)-isomer</synonym>
    <synonym>Monomethylfumarate</synonym>
    <synonym>(Z)-2-Methyl-2-butenedioic acid</synonym>
    <synonym>Citraconic acid, calcium salt</synonym>
  </synonyms>
  <chemical_formula>C5H6O4</chemical_formula>
  <average_molecular_weight>130.0987</average_molecular_weight>
  <monisotopic_moleculate_weight>130.02660868</monisotopic_moleculate_weight>
  <iupac_name>(2E)-2-methylbut-2-enedioic acid</iupac_name>
  <traditional_iupac>mesaconic acid</traditional_iupac>
  <cas_registry_number>498-24-8</cas_registry_number>
  <smiles>C\C(=C/C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+</inchi>
  <inchikey>HNEGQIOMVPPMNR-NSCUHMNNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Methyl-branched fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>200 - 202 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>26.3 mg/mL at 18 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-2-methylbut-2-enedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>130.0987</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>130.02660868</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C\C(=C/C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H6O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HNEGQIOMVPPMNR-NSCUHMNNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439033</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01732</kegg_id>
  <foodb_id>FDB022221</foodb_id>
  <chemspider_id>10289044</chemspider_id>
  <drugbank_id/>
  <chebi_id>16600</chebi_id>
  <pubchem_compound_id>638129</pubchem_compound_id>
  <pdbe_id>MEZ</pdbe_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id>38272</bigg_id>
  <wikipedia_id>Mesaconic_acid</wikipedia_id>
  <metlin_id>4130</metlin_id>
  <synthesis_reference>Shriner, R. L.; Ford, S. G.; Roll, L. J.  Mesaconic acid.    Organic Syntheses  (1931),  XI  74-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:35:59 UTC</creation_date>
  <update_date>2020-04-15 22:14:28 UTC</update_date>
  <accession>BMDB0000750</accession>
  <secondary_accessions>
    <accession>BMDB00750</accession>
  </secondary_accessions>
  <name>3-Hydroxymandelic acid</name>
  <description>3-Hydroxymandelic acid, also known as m-hydroxymandelate or mhma, belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. 3-Hydroxymandelic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).</description>
  <synonyms>
    <synonym>2-Hydroxy-2-(3-hydroxyphenyl)acetic acid</synonym>
    <synonym>2-Hydroxy-2-(3-hydroxyphenyl)ethanoic acid</synonym>
    <synonym>m-Hydroxymandelic acid</synonym>
    <synonym>2-Hydroxy-2-(3-hydroxyphenyl)acetate</synonym>
    <synonym>2-Hydroxy-2-(3-hydroxyphenyl)ethanoate</synonym>
    <synonym>m-Hydroxymandelate</synonym>
    <synonym>3-Hydroxymandelate</synonym>
    <synonym>3-Hydroxyphenylglycolic acid</synonym>
    <synonym>alpha,3-Dihydroxybenzeneacetic acid</synonym>
    <synonym>DL-3-Hydroxymandelate</synonym>
    <synonym>DL-3-Hydroxymandelic acid</synonym>
    <synonym>DL-Hydroxy(m-hydroxyphenyl)acetic acid</synonym>
    <synonym>Hydroxy(3-hydroxyphenyl)acetic acid</synonym>
    <synonym>m-Hydroxy-(6ci,7ci,8ci)mandelate</synonym>
    <synonym>m-Hydroxy-(6ci,7ci,8ci)mandelic acid</synonym>
    <synonym>Meta-hydroxymandelic acid</synonym>
    <synonym>MHMA</synonym>
  </synonyms>
  <chemical_formula>C8H8O4</chemical_formula>
  <average_molecular_weight>168.1467</average_molecular_weight>
  <monisotopic_moleculate_weight>168.042258744</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-2-(3-hydroxyphenyl)acetic acid</iupac_name>
  <traditional_iupac>MHMA</traditional_iupac>
  <cas_registry_number>17119-15-2</cas_registry_number>
  <smiles>OC(C(O)=O)C1=CC(O)=CC=C1</smiles>
  <inchi>InChI=1S/C8H8O4/c9-6-3-1-2-5(4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)</inchi>
  <inchikey>OLSDAJRAVOVKLG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>1-hydroxy-4-unsubstituted benzenoids</sub_class>
    <direct_parent>1-hydroxy-4-unsubstituted benzenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>31 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-2-(3-hydroxyphenyl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>168.1467</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>168.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(C(O)=O)C1=CC(O)=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H8O4/c9-6-3-1-2-5(4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OLSDAJRAVOVKLG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439255</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022222</foodb_id>
  <chemspider_id>78444</chemspider_id>
  <drugbank_id/>
  <chebi_id>86553</chebi_id>
  <pubchem_compound_id>86957</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>4-Hydroxymandelic acid</wikipedia_id>
  <metlin_id>732</metlin_id>
  <synthesis_reference>Fanali S; Aturki Z  Further study on the use of uncharged beta-cyclodextrin polymer in capillary electrophoresis: enantiomeric separation of some alpha-hydroxy acids.    Electrophoresis  (1995),  16(8),  1505-9.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:00 UTC</creation_date>
  <update_date>2020-03-13 16:23:35 UTC</update_date>
  <accession>BMDB0000751</accession>
  <secondary_accessions>
    <accession>BMDB00751</accession>
  </secondary_accessions>
  <name>L-Threo-2-pentulose</name>
  <description/>
  <synonyms>
    <synonym>L-Lyxulose</synonym>
    <synonym>L-Threo-pent-2-ulose</synonym>
    <synonym>L-Threo-pentulose</synonym>
    <synonym>L-Xul</synonym>
    <synonym>L-Xylulose</synonym>
  </synonyms>
  <chemical_formula>C5H10O5</chemical_formula>
  <average_molecular_weight>150.1299</average_molecular_weight>
  <monisotopic_moleculate_weight>150.05282343</monisotopic_moleculate_weight>
  <iupac_name>(3R,4S)-1,3,4,5-tetrahydroxypentan-2-one</iupac_name>
  <traditional_iupac>xylulose</traditional_iupac>
  <cas_registry_number>527-50-4</cas_registry_number>
  <smiles>OC[C@H](O)[C@@H](O)C(=O)CO</smiles>
  <inchi>InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m0/s1</inchi>
  <inchikey>ZAQJHHRNXZUBTE-WVZVXSGGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Acyloins</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyloin</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>xylulose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4S)-1,3,4,5-tetrahydroxypentan-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>150.1299</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>150.05282343</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H](O)[C@@H](O)C(=O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZAQJHHRNXZUBTE-WVZVXSGGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35761</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id/>
  <foodb_id>FDB022223</foodb_id>
  <pubchem_compound_id>22253</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17399</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Xylulose</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Ashwell, Gilbert; Kanfer, Julian; Burns, J. J.  Mechanism of L-xylulose formation by kidney enzymes.    Journal of Biological Chemistry  (1959),  234  472-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00594</protein_accession>
      <name>L-xylulose reductase</name>
      <uniprot_id>Q1JP75</uniprot_id>
      <gene_name>DCXR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:01 UTC</creation_date>
  <update_date>2020-04-14 22:48:16 UTC</update_date>
  <accession>BMDB0000752</accession>
  <secondary_accessions>
    <accession>BMDB00752</accession>
  </secondary_accessions>
  <name>Methylglutaric acid</name>
  <description/>
  <synonyms>
    <synonym>beta-Methylglutaric acid</synonym>
    <synonym>b-Methylglutarate</synonym>
    <synonym>b-Methylglutaric acid</synonym>
    <synonym>beta-Methylglutarate</synonym>
    <synonym>Β-methylglutarate</synonym>
    <synonym>Β-methylglutaric acid</synonym>
    <synonym>Methylglutarate</synonym>
    <synonym>3-Methyl-glutarate</synonym>
    <synonym>3-Methyl-glutaric acid</synonym>
    <synonym>3-Methylglutarate</synonym>
    <synonym>3-Methylglutaric acid</synonym>
    <synonym>3-Methylpentanedioate</synonym>
    <synonym>3-Methylpentanedioic acid</synonym>
    <synonym>b-Methyl-glutaric acid</synonym>
    <synonym>beta-Methyl-glutaric acid</synonym>
  </synonyms>
  <chemical_formula>C6H10O4</chemical_formula>
  <average_molecular_weight>146.1412</average_molecular_weight>
  <monisotopic_moleculate_weight>146.057908808</monisotopic_moleculate_weight>
  <iupac_name>3-methylpentanedioic acid</iupac_name>
  <traditional_iupac>methylglutaric acid</traditional_iupac>
  <cas_registry_number>626-51-7</cas_registry_number>
  <smiles>CC(CC(O)=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C6H10O4/c1-4(2-5(7)8)3-6(9)10/h4H,2-3H2,1H3,(H,7,8)(H,9,10)</inchi>
  <inchikey>XJMMNTGIMDZPMU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Methyl-branched fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>alpha,omega-dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>80 - 82 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-methylpentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>146.1412</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>146.057908808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(CC(O)=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O4/c1-4(2-5(7)8)3-6(9)10/h4H,2-3H2,1H3,(H,7,8)(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XJMMNTGIMDZPMU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451964</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022224</foodb_id>
  <chemspider_id>11781</chemspider_id>
  <drugbank_id/>
  <chebi_id>68566</chebi_id>
  <pubchem_compound_id>12284</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-516</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5720</metlin_id>
  <synthesis_reference>Komppa, Gust.  b-Methylglutaric acid.    Ann. acad. sci. Fennicae  (1930),  30(Ser. A;No. 9),  5 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:03 UTC</creation_date>
  <update_date>2020-03-13 16:23:36 UTC</update_date>
  <accession>BMDB0000753</accession>
  <secondary_accessions>
    <accession>BMDB00753</accession>
  </secondary_accessions>
  <name>3-Hexanone</name>
  <description/>
  <synonyms>
    <synonym>3-Oxohexane</synonym>
    <synonym>Ethyl N-propyl ketone</synonym>
    <synonym>Ethyl propyl ketone</synonym>
    <synonym>Hexan-3-one</synonym>
  </synonyms>
  <chemical_formula>C6H12O</chemical_formula>
  <average_molecular_weight>100.1589</average_molecular_weight>
  <monisotopic_moleculate_weight>100.088815006</monisotopic_moleculate_weight>
  <iupac_name>hexan-3-one</iupac_name>
  <traditional_iupac>3-hexanone</traditional_iupac>
  <cas_registry_number>589-38-8</cas_registry_number>
  <smiles>CCCC(=O)CC</smiles>
  <inchi>InChI=1S/C6H12O/c1-3-5-6(7)4-2/h3-5H2,1-2H3</inchi>
  <inchikey>PFCHFHIRKBAQGU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as ketones. These are organic compounds  in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Ketones</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Oxygenated hydrocarbons</external_descriptor>
      <external_descriptor>a ketone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-55.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>14.7 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>hexan-3-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>100.1589</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>100.088815006</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCC(=O)CC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O/c1-3-5-6(7)4-2/h3-5H2,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PFCHFHIRKBAQGU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21874</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB030904</foodb_id>
  <chemspider_id>11025</chemspider_id>
  <kegg_id/>
  <phenol_explorer_compound_id/>
  <pubchem_compound_id>11509</pubchem_compound_id>
  <chebi_id>89891</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id>CPD-13223</meta_cyc_id>
  <wikipedia_id>3-Hexanone</wikipedia_id>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>5721</metlin_id>
  <synthesis_reference>Elliott, David J.  Synthesis of higher ketones.    U.S.  (1987),     5 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:04 UTC</creation_date>
  <update_date>2020-04-15 21:59:47 UTC</update_date>
  <accession>BMDB0000754</accession>
  <secondary_accessions>
    <accession>BMDB00754</accession>
  </secondary_accessions>
  <name>3-Hydroxyisovaleric acid</name>
  <description/>
  <synonyms>
    <synonym>3-Hydroxy-3-methylbutyric acid</synonym>
    <synonym>3-Hydroxy-isovaleric acid</synonym>
    <synonym>3-Methyl-3-hydroxybutyric acid</synonym>
    <synonym>3-OH-Isovaleric acid</synonym>
    <synonym>beta-Hydroxy-beta-methylbutyric acid</synonym>
    <synonym>beta-Hydroxyisovaleric acid</synonym>
    <synonym>HMB</synonym>
    <synonym>HMB-D6</synonym>
    <synonym>3-Hydroxy-3-methylbutyrate</synonym>
    <synonym>3-Hydroxy-isovalerate</synonym>
    <synonym>3-Methyl-3-hydroxybutyrate</synonym>
    <synonym>3-OH-Isovalerate</synonym>
    <synonym>b-Hydroxy-b-methylbutyrate</synonym>
    <synonym>b-Hydroxy-b-methylbutyric acid</synonym>
    <synonym>beta-Hydroxy-beta-methylbutyrate</synonym>
    <synonym>Β-hydroxy-β-methylbutyrate</synonym>
    <synonym>Β-hydroxy-β-methylbutyric acid</synonym>
    <synonym>b-Hydroxyisovalerate</synonym>
    <synonym>b-Hydroxyisovaleric acid</synonym>
    <synonym>beta-Hydroxyisovalerate</synonym>
    <synonym>Β-hydroxyisovalerate</synonym>
    <synonym>Β-hydroxyisovaleric acid</synonym>
    <synonym>3-Hydroxyisovalerate</synonym>
    <synonym>3-Hydroxy-3-methyl-butanoate</synonym>
    <synonym>3-Hydroxy-3-methyl-butanoic acid</synonym>
    <synonym>3-Hydroxy-3-methyl-butyric acid</synonym>
    <synonym>3-Hydroxy-3-methylbutanoate</synonym>
    <synonym>3-Hydroxy-3-methylbutanoic acid</synonym>
    <synonym>beta Hydroxy beta methylbutyrate</synonym>
    <synonym>beta-Hydroxy beta-methylbutyrate</synonym>
    <synonym>3-Hydroxyisovaleric acid</synonym>
  </synonyms>
  <chemical_formula>C5H10O3</chemical_formula>
  <average_molecular_weight>118.1311</average_molecular_weight>
  <monisotopic_moleculate_weight>118.062994186</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxy-3-methylbutanoic acid</iupac_name>
  <traditional_iupac>3-hydroxyisovaleric acid</traditional_iupac>
  <cas_registry_number>625-08-1</cas_registry_number>
  <smiles>CC(C)(O)CC(O)=O</smiles>
  <inchi>InChI=1S/C5H10O3/c1-5(2,8)3-4(6)7/h8H,3H2,1-2H3,(H,6,7)</inchi>
  <inchikey>AXFYFNCPONWUHW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>65 - 67 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxy-3-methylbutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>118.1311</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>118.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)(O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O3/c1-5(2,8)3-4(6)7/h8H,3H2,1-2H3,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AXFYFNCPONWUHW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366891</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id>62571</chemspider_id>
  <foodb_id>FDB022225</foodb_id>
  <pubchem_compound_id>69362</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>37084</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Beta-Hydroxy_beta-methylbutyric_acid</wikipedia_id>
  <metlin_id>5722</metlin_id>
  <synthesis_reference>Rudney, Harry.  Biosynthesis of b-hydroxy-b-methylglutaric acid.   Journal of Biological Chemistry  (1957),  227  363-77.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:05 UTC</creation_date>
  <update_date>2020-04-15 21:56:50 UTC</update_date>
  <accession>BMDB0000755</accession>
  <secondary_accessions>
    <accession>BMDB00755</accession>
  </secondary_accessions>
  <name>Hydroxyphenyllactic acid</name>
  <description>3-(4-Hydroxyphenyl)lactic acid, also known as 4-hydroxyphenyllactate or hpla, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. 3-(4-Hydroxyphenyl)lactic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3-(4-Hydroxyphenyl)lactic acid exists in all eukaryotes, ranging from yeast to humans. 3-(4-Hydroxyphenyl)lactic acid is a potentially toxic compound. 3-(4-Hydroxyphenyl)lactic acid has been found to be associated with several diseases known as eosinophilic esophagitis, colorectal cancer, and supradiaphragmatic malignancy; also 3-(4-hydroxyphenyl)lactic acid has been linked to the inborn metabolic disorders including phenylketonuria.</description>
  <synonyms>
    <synonym>2-Hydroxy-3-(4-hydroxyphenyl)propanoate</synonym>
    <synonym>2-Hydroxy-3-(p-hydroxyphenyl)propionic acid</synonym>
    <synonym>4-Hydroxyphenyllactic acid</synonym>
    <synonym>beta-(4-Hydroxyphenyl)lactic acid</synonym>
    <synonym>beta-(p-Hydroxyphenyl)lactic acid</synonym>
    <synonym>DL-p-Hydroxyphenyllactic acid</synonym>
    <synonym>p-Hydroxyphenyl lactic acid</synonym>
    <synonym>4-Hydroxyphenyllactate</synonym>
    <synonym>p-Hydroxyphenyllactate</synonym>
    <synonym>2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid</synonym>
    <synonym>2-Hydroxy-3-(p-hydroxyphenyl)propionate</synonym>
    <synonym>b-(4-Hydroxyphenyl)lactate</synonym>
    <synonym>b-(4-Hydroxyphenyl)lactic acid</synonym>
    <synonym>beta-(4-Hydroxyphenyl)lactate</synonym>
    <synonym>Β-(4-hydroxyphenyl)lactate</synonym>
    <synonym>Β-(4-hydroxyphenyl)lactic acid</synonym>
    <synonym>b-(p-Hydroxyphenyl)lactate</synonym>
    <synonym>b-(p-Hydroxyphenyl)lactic acid</synonym>
    <synonym>beta-(p-Hydroxyphenyl)lactate</synonym>
    <synonym>Β-(p-hydroxyphenyl)lactate</synonym>
    <synonym>Β-(p-hydroxyphenyl)lactic acid</synonym>
    <synonym>DL-p-Hydroxyphenyllactate</synonym>
    <synonym>p-Hydroxyphenyl lactate</synonym>
    <synonym>p-Hydroxyphenyllactic acid</synonym>
    <synonym>Hydroxyphenyllactate</synonym>
    <synonym>3-(4-Hydroxyphenyl)lactate</synonym>
    <synonym>(RS)-3-(4-Hydroxyphenyl)lactate</synonym>
    <synonym>(RS)-3-(4-Hydroxyphenyl)lactic acid</synonym>
    <synonym>3-(4-Hydroxyphenyl)-DL-lactate</synonym>
    <synonym>3-(4-Hydroxyphenyl)-DL-lactic acid</synonym>
    <synonym>3-(p-Hydroxyphenyl)-lactate</synonym>
    <synonym>3-(p-Hydroxyphenyl)-lactic acid</synonym>
    <synonym>a,4-Dihydroxybenzenepropanoate</synonym>
    <synonym>a,4-Dihydroxybenzenepropanoic acid</synonym>
    <synonym>b-(p-Hydroxyphenyl)-DL-lactate</synonym>
    <synonym>b-(p-Hydroxyphenyl)-DL-lactic acid</synonym>
    <synonym>beta-(p-Hydroxyphenyl)-DL-lactate</synonym>
    <synonym>beta-(p-Hydroxyphenyl)-DL-lactic acid</synonym>
    <synonym>DL-3-(4-Hydroxyphenyl)lactate</synonym>
    <synonym>DL-3-(4-Hydroxyphenyl)lactic acid</synonym>
    <synonym>HPLA</synonym>
    <synonym>4-Hydroxyphenyllactic acid, (DL)-isomer</synonym>
    <synonym>Para-hydroxyphenyllactic acid</synonym>
    <synonym>3-(4-Hydroxyphenyl)lactic acid</synonym>
    <synonym>2-Hydroxyphloretate</synonym>
  </synonyms>
  <chemical_formula>C9H10O4</chemical_formula>
  <average_molecular_weight>182.1733</average_molecular_weight>
  <monisotopic_moleculate_weight>182.057908808</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-3-(4-hydroxyphenyl)propanoic acid</iupac_name>
  <traditional_iupac>hydroxyphenyllactic acid</traditional_iupac>
  <cas_registry_number>306-23-0</cas_registry_number>
  <smiles>OC(CC1=CC=C(O)C=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)</inchi>
  <inchikey>JVGVDSSUAVXRDY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Phenylpropanoic acids</class>
    <sub_class/>
    <direct_parent>Phenylpropanoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxy carboxylic acid</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>12.9 mg/mL at 16 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-3-(4-hydroxyphenyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>182.1733</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>182.057908808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(CC1=CC=C(O)C=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JVGVDSSUAVXRDY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440174</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by UPLC-Q-TOF MS E</comment>
      <references>
        <reference>
          <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
          <pubmed_id>28342601</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB019021</foodb_id>
  <chemspider_id>9010</chemspider_id>
  <kegg_id>C03672</kegg_id>
  <phenol_explorer_compound_id>577</phenol_explorer_compound_id>
  <pubchem_compound_id>9378</pubchem_compound_id>
  <chebi_id>17385</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id>4-HYDROXYPHENYLLACTATE</meta_cyc_id>
  <wikipedia_id/>
  <knapsack_id/>
  <bigg_id>2392410</bigg_id>
  <metlin_id>5723</metlin_id>
  <synthesis_reference>Deng, Xi-ling; Wang, Xin-bing; Xiang, Ying; Zhu, Shi-fa.  Synthesis of b-(4-hydroxyphenyl)lactic acid.    Shihezi Daxue Xuebao, Ziran Kexueban  (2005),  23(1),  11-13.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
      <pubmed_id>28342601</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:06 UTC</creation_date>
  <update_date>2020-04-14 22:48:17 UTC</update_date>
  <accession>BMDB0000756</accession>
  <secondary_accessions>
    <accession>BMDB00756</accession>
  </secondary_accessions>
  <name>L-Hexanoylcarnitine</name>
  <description/>
  <synonyms>
    <synonym>(R)-Caproylcarnitine</synonym>
    <synonym>(R)-Hexanoylcarnitine</synonym>
    <synonym>Hexanoyl-L-carnitine</synonym>
    <synonym>L-Hexanoylcarnitine</synonym>
    <synonym>O-Hexanoyl-(R)-carnitine</synonym>
    <synonym>(R)-3-Carboxy-N,N,N-trimethyl-2-[(1-oxohexyl)oxy]-1-propanaminium inner salt</synonym>
    <synonym>Hexanoate</synonym>
    <synonym>Hexanoic acid</synonym>
    <synonym>Hexanoic acid ester with L-(3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt</synonym>
    <synonym>L-Carnitine hexanoyl ester</synonym>
    <synonym>L-Hexanoate</synonym>
    <synonym>L-Hexanoic acid</synonym>
    <synonym>L-Hexanoic acid ester with (3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt</synonym>
    <synonym>C6 Carnitine</synonym>
    <synonym>Hexanoylcarnitine</synonym>
  </synonyms>
  <chemical_formula>C13H25NO4</chemical_formula>
  <average_molecular_weight>259.3419</average_molecular_weight>
  <monisotopic_moleculate_weight>259.178358293</monisotopic_moleculate_weight>
  <iupac_name>(3R)-3-(hexanoyloxy)-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>L-carnitine hexanoyl ester</traditional_iupac>
  <cas_registry_number>22671-29-0</cas_registry_number>
  <smiles>CCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C</smiles>
  <inchi>InChI=1S/C13H25NO4/c1-5-6-7-8-13(17)18-11(9-12(15)16)10-14(2,3)4/h11H,5-10H2,1-4H3/t11-/m1/s1</inchi>
  <inchikey>VVPRQWTYSNDTEA-LLVKDONJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Acyl carnitines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl-carnitine</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fatty acyl carnitines</external_descriptor>
      <external_descriptor>O-acyl-L-carnitine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R)-3-(hexanoyloxy)-4-(trimethylazaniumyl)butanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>259.3419</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>259.178358293</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H25NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H25NO4/c1-5-6-7-8-13(17)18-11(9-12(15)16)10-14(2,3)4/h11H,5-10H2,1-4H3/t11-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VVPRQWTYSNDTEA-LLVKDONJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>91.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1088</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.05+/-0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>0.3+/-0.1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>0.52+/-0.51</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.08+/-0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>0.7+/-0.4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>0.21+/-0.06</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022226</foodb_id>
  <chemspider_id>2497478</chemspider_id>
  <kegg_id/>
  <phenol_explorer_compound_id/>
  <pubchem_compound_id>3246938</pubchem_compound_id>
  <chebi_id>84834</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>3548</metlin_id>
  <synthesis_reference>Nakanishi, Toyofumi; Shimizu, Akira; Arimoto, Masao; Kanai, Michiko.  Synthesis of acylcarnitines for differential diagnosis of metabolic disorders.    Nippon Iyo Masu Supekutoru Gakkai Koenshu  (1993),  18  129-32.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:07 UTC</creation_date>
  <update_date>2020-04-16 20:40:00 UTC</update_date>
  <accession>BMDB0000757</accession>
  <secondary_accessions>
    <accession>BMDB00757</accession>
  </secondary_accessions>
  <name>Glycogen</name>
  <description/>
  <synonyms>
    <synonym>Animal starch</synonym>
    <synonym>Liver starch</synonym>
    <synonym>Lyoglycogen</synonym>
    <synonym>Phytoglycogen</synonym>
  </synonyms>
  <chemical_formula>C24H42O21</chemical_formula>
  <average_molecular_weight>666.5777</average_molecular_weight>
  <monisotopic_moleculate_weight>666.221858406</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-2-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-2-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</traditional_iupac>
  <cas_registry_number>9005-79-2</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](OC[C@H]2O[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]3CO)[C@H](O)[C@@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C24H42O21/c25-1-5-9(28)11(30)16(35)22(41-5)39-4-8-20(45-23-17(36)12(31)10(29)6(2-26)42-23)14(33)18(37)24(43-8)44-19-7(3-27)40-21(38)15(34)13(19)32/h5-38H,1-4H2/t5-,6-,7-,8-,9-,10-,11+,12+,13-,14-,15-,16-,17-,18-,19-,20-,21+,22+,23-,24-/m1/s1</inchi>
  <inchikey>BYSGBSNPRWKUQH-UJDJLXLFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Oligosaccharides</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Oligosaccharide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>glycogens</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>270 - 280 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-8.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-2-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>666.5777</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>666.221858406</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](OC[C@H]2O[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]3CO)[C@H](O)[C@@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H42O21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H42O21/c25-1-5-9(28)11(30)16(35)22(41-5)39-4-8-20(45-23-17(36)12(31)10(29)6(2-26)42-23)14(33)18(37)24(43-8)44-19-7(3-27)40-21(38)15(34)13(19)32/h5-38H,1-4H2/t5-,6-,7-,8-,9-,10-,11+,12+,13-,14-,15-,16-,17-,18-,19-,20-,21+,22+,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BYSGBSNPRWKUQH-UJDJLXLFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>347.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>133.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>61.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1472</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022227</foodb_id>
  <chemspider_id>388322</chemspider_id>
  <kegg_id>C00182</kegg_id>
  <phenol_explorer_compound_id/>
  <pubchem_compound_id>439177</pubchem_compound_id>
  <chebi_id>28087</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <wikipedia_id>Glycogen</wikipedia_id>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>160</metlin_id>
  <synthesis_reference>Parodi A J; Krisman C R; Mordoh J  In vitro synthesis of particulate glycogen from uridine diphosphate glucose. II. Some studies on the growth process.    Archives of biochemistry and biophysics  (1970),  141(1),  219-27.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00643</protein_accession>
      <name>Serine/threonine-protein phosphatase PP1-alpha catalytic subunit</name>
      <uniprot_id>Q3T0E7</uniprot_id>
      <gene_name>PPP1CA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00646</protein_accession>
      <name>Serine/threonine-protein phosphatase PP1-beta catalytic subunit</name>
      <uniprot_id>Q3SWW9</uniprot_id>
      <gene_name>PPP1CB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00649</protein_accession>
      <name>Serine/threonine-protein phosphatase PP1-gamma catalytic subunit</name>
      <uniprot_id>P61287</uniprot_id>
      <gene_name>PPP1CC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00915</protein_accession>
      <name>Phosphatidylinositol 3-kinase regulatory subunit alpha</name>
      <uniprot_id>P23727</uniprot_id>
      <gene_name>PIK3R1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01321</protein_accession>
      <name>Protein phosphatase 1 regulatory subunit 3B</name>
      <uniprot_id>A6QNP3</uniprot_id>
      <gene_name>PPP1R3B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01322</protein_accession>
      <name>Protein phosphatase 1 regulatory subunit 3C</name>
      <uniprot_id>Q0VCR4</uniprot_id>
      <gene_name>PPP1R3C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02147</protein_accession>
      <name>Islet amyloid polypeptide</name>
      <uniprot_id>Q28207</uniprot_id>
      <gene_name>IAPP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:08 UTC</creation_date>
  <update_date>2020-04-15 22:31:50 UTC</update_date>
  <accession>BMDB0000759</accession>
  <secondary_accessions>
    <accession>BMDB00759</accession>
  </secondary_accessions>
  <name>Glycyl-L-leucine</name>
  <description>Glycylleucine, also known as GL or leucylglycine, belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Glycylleucine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule.</description>
  <synonyms>
    <synonym>G-L</synonym>
    <synonym>GL</synonym>
    <synonym>Gly-L-leu</synonym>
    <synonym>Glycyl-L-leucine</synonym>
    <synonym>Glycyl-leucine</synonym>
    <synonym>N-Glycyl-L-leucine</synonym>
    <synonym>Leucylglycine</synonym>
    <synonym>Leu-gly</synonym>
    <synonym>Glycylleucine, (D)-isomer</synonym>
    <synonym>Gly-leu</synonym>
    <synonym>g-L Dipeptide</synonym>
    <synonym>GL Dipeptide</synonym>
    <synonym>Glycine leucine dipeptide</synonym>
    <synonym>Glycine-leucine dipeptide</synonym>
    <synonym>N-Glycylleucine</synonym>
    <synonym>NSC 83257</synonym>
    <synonym>Glycylleucine</synonym>
  </synonyms>
  <chemical_formula>C8H16N2O3</chemical_formula>
  <average_molecular_weight>188.2242</average_molecular_weight>
  <monisotopic_moleculate_weight>188.116092388</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-(2-aminoacetamido)-4-methylpentanoic acid</iupac_name>
  <traditional_iupac>glycyl-L-leucine</traditional_iupac>
  <cas_registry_number>869-19-2</cas_registry_number>
  <smiles>CC(C)C[C@H](NC(=O)CN)C(O)=O</smiles>
  <inchi>InChI=1S/C8H16N2O3/c1-5(2)3-6(8(12)13)10-7(11)4-9/h5-6H,3-4,9H2,1-2H3,(H,10,11)(H,12,13)/t6-/m0/s1</inchi>
  <inchikey>DKEXFJVMVGETOO-LURJTMIESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Peptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Leucine and derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha peptide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Leucine or derivatives</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dipeptide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-(2-aminoacetamido)-4-methylpentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>188.2242</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>188.116092388</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)C[C@H](NC(=O)CN)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16N2O3/c1-5(2)3-6(8(12)13)10-7(11)4-9/h5-6H,3-4,9H2,1-2H3,(H,10,11)(H,12,13)/t6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DKEXFJVMVGETOO-LURJTMIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361058</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022228</foodb_id>
  <chemspider_id>83812</chemspider_id>
  <kegg_id>C02155</kegg_id>
  <phenol_explorer_compound_id/>
  <pubchem_compound_id>92843</pubchem_compound_id>
  <chebi_id>73514</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id>CPD-12312</meta_cyc_id>
  <wikipedia_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>5727</metlin_id>
  <synthesis_reference>Bolster J M; Vaalburg W; Elsinga P H; Woldring M G; Wynberg H  Synthesis of carbon-11 labelled glycine and the dipeptides L-phenylalanylglycine and L-leucylglycine.    International journal of radiation applications and instrumentation. Part A, Applied radiation and isotopes  (1986),  37(9),  985-7.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:10 UTC</creation_date>
  <update_date>2020-04-15 22:14:29 UTC</update_date>
  <accession>BMDB0000760</accession>
  <secondary_accessions>
    <accession>BMDB00760</accession>
  </secondary_accessions>
  <name>Hyocholic acid</name>
  <description/>
  <synonyms>
    <synonym>Hyocholate</synonym>
    <synonym>(4R)-4-[(1S,2R,5R,7R,8R,9S,10S,11S,15R)-5,8,9-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
    <synonym>3a,6a,7a-Trihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,6a,7a-Trihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3a,6a,7a-Trihydroxy-5b-cholanate</synonym>
    <synonym>3a,6a,7a-Trihydroxy-5b-cholanic acid</synonym>
    <synonym>3a,6a,7a-Trihydroxy-5b-cholanoate</synonym>
    <synonym>3a,6a,7a-Trihydroxy-5b-cholanoic acid</synonym>
    <synonym>5b-Cholanic acid-3a,6a,7a-triol</synonym>
    <synonym>6a-Hydroxychenodeoxycholate</synonym>
    <synonym>6a-Hydroxychenodeoxycholic acid</synonym>
    <synonym>a-Hyocholate</synonym>
    <synonym>a-Hyocholic acid</synonym>
    <synonym>alpha-Hyocholate</synonym>
    <synonym>alpha-Hyocholic acid</synonym>
    <synonym>g-Muricholate</synonym>
    <synonym>g-Muricholic acid</synonym>
    <synonym>gamma-Muricholate</synonym>
    <synonym>gamma-Muricholic acid</synonym>
    <synonym>Iocholate</synonym>
    <synonym>Iocholic acid</synonym>
    <synonym>(4R)-4-[(1S,2R,5R,7R,8R,9S,10S,11S,15R)-5,8,9-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]pentanoate</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5R,7R,8R,9S,10S,11S,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5R,7R,8R,9S,10S,11S,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>547-75-1</cas_registry_number>
  <smiles>[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)[C@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15?,16+,17+,18+,20+,21-,22+,23-,24-/m1/s1</inchi>
  <inchikey>DKPMWHFRUGMUKF-NNFRHCBVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>6-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>6-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>0.0184 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.72</value>
      <source>Extrapolated</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5R,7R,8R,9S,10S,11S,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)[C@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15?,16+,17+,18+,20+,21-,22+,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DKPMWHFRUGMUKF-NNFRHCBVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37748</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>59651444</chemspider_id>
  <kegg_id/>
  <foodb_id>FDB022229</foodb_id>
  <pubchem_compound_id>131750324</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Hyocholic acid</wikipedia_id>
  <metlin_id>5728</metlin_id>
  <synthesis_reference>Iida, Takashi; Momose, Toshiaki; Tamura, Toshitake; Matsumoto, Taro; Chang, Frederic C.; Goto, Junichi; Nambara, Toshio.  Potential bile acid metabolites.  14.  Hyocholic and muricholic acid stereoisomers.  Journal of Lipid Research  (1989),  30(8),  1267-79.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:11 UTC</creation_date>
  <update_date>2020-04-15 22:14:30 UTC</update_date>
  <accession>BMDB0000761</accession>
  <secondary_accessions>
    <accession>BMDB00761</accession>
  </secondary_accessions>
  <name>Lithocholic acid</name>
  <description/>
  <synonyms>
    <synonym>(3alpha,5beta)-3-Hydroxycholan-24-Oic acid</synonym>
    <synonym>3alpha-Hydroxy-5beta-cholanate</synonym>
    <synonym>3alpha-Hydroxy-5beta-cholanic acid</synonym>
    <synonym>3alpha-Hydroxy-5beta-cholanoic acid</synonym>
    <synonym>5beta-Cholanic acid-3alpha-ol</synonym>
    <synonym>Lithocholate</synonym>
    <synonym>(3a,5b)-3-Hydroxycholan-24-Oate</synonym>
    <synonym>(3a,5b)-3-Hydroxycholan-24-Oic acid</synonym>
    <synonym>(3alpha,5beta)-3-Hydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5β)-3-hydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5β)-3-hydroxycholan-24-Oic acid</synonym>
    <synonym>3a-Hydroxy-5b-cholanate</synonym>
    <synonym>3a-Hydroxy-5b-cholanic acid</synonym>
    <synonym>3Α-hydroxy-5β-cholanate</synonym>
    <synonym>3Α-hydroxy-5β-cholanic acid</synonym>
    <synonym>3a-Hydroxy-5b-cholanoate</synonym>
    <synonym>3a-Hydroxy-5b-cholanoic acid</synonym>
    <synonym>3alpha-Hydroxy-5beta-cholanoate</synonym>
    <synonym>3Α-hydroxy-5β-cholanoate</synonym>
    <synonym>3Α-hydroxy-5β-cholanoic acid</synonym>
    <synonym>5b-Cholanate-3a-ol</synonym>
    <synonym>5b-Cholanic acid-3a-ol</synonym>
    <synonym>5beta-Cholanate-3alpha-ol</synonym>
    <synonym>5Β-cholanate-3α-ol</synonym>
    <synonym>5Β-cholanic acid-3α-ol</synonym>
    <synonym>Acid, lithocholic</synonym>
  </synonyms>
  <chemical_formula>C24H40O3</chemical_formula>
  <average_molecular_weight>376.5726</average_molecular_weight>
  <monisotopic_moleculate_weight>376.297745146</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>434-13-9</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O</smiles>
  <inchi>InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1</inchi>
  <inchikey>SMEROWZSTRWXGI-HVATVPOCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Monohydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monohydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>Cholane and derivatives</external_descriptor>
      <external_descriptor>bile acid</external_descriptor>
      <external_descriptor>monohydroxy-5beta-cholanic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>376.5726</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>376.297745146</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SMEROWZSTRWXGI-HVATVPOCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>107.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>45.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1223257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1223258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1223259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1338901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1338902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1338903</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022230</foodb_id>
  <chemspider_id>9519</chemspider_id>
  <kegg_id>C03990</kegg_id>
  <phenol_explorer_compound_id/>
  <pubchem_compound_id>9903</pubchem_compound_id>
  <chebi_id>16325</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id>CPD-7235</meta_cyc_id>
  <wikipedia_id>Lithocholic_acid</wikipedia_id>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>209</metlin_id>
  <synthesis_reference>Xu, Zhengbang; Li, Kaixi; Zhao, Huaming.  Synthesis of lithocholic acid by Huang-Min-Lon modification in the presence of crown ether.    Sichuan Daxue Xuebao, Ziran Kexueban  (1992),  29(4),  527-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01586</protein_accession>
      <name>Bile acid receptor</name>
      <uniprot_id>Q3SZL0</uniprot_id>
      <gene_name>NR1H4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:12 UTC</creation_date>
  <update_date>2020-04-16 20:40:41 UTC</update_date>
  <accession>BMDB0000763</accession>
  <secondary_accessions>
    <accession>BMDB00763</accession>
  </secondary_accessions>
  <name>5-Hydroxyindoleacetic acid</name>
  <description>5-5-5-hydroxyindoleacetic acid, also known as 5-5-hydroxyindoleacetic acid or 5-hydroxy-1H-indole-3-acetate, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 5-5-5-hydroxyindoleacetic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 5-5-5-hydroxyindoleacetic acid exists in all living organisms, ranging from bacteria to humans. 5-5-5-hydroxyindoleacetic acid participates in a number of enzymatic reactions, within cattle. In particular, 5-5-5-hydroxyindoleacetic acid can be biosynthesized from 5-hydroxyindoleacetaldehyde through the action of the enzyme aldehyde dehydrogenase, mitochondrial. In addition, 5-5-5-hydroxyindoleacetic acid and S-adenosylmethionine can be converted into 5-methoxyindoleacetate and S-adenosylhomocysteine through its interaction with the enzyme acetylserotonin O-methyltransferase. In cattle, 5-5-hydroxyindoleacetic acid is involved in the metabolic pathway called the tryptophan metabolism pathway.</description>
  <synonyms>
    <synonym>5-HIAA</synonym>
    <synonym>5-Hydroxy-1H-indole-3-acetic acid</synonym>
    <synonym>5-Hydroxyindol-3-ylacetic acid</synonym>
    <synonym>5-Hydroxyindole-3-acetic acid</synonym>
    <synonym>5-Hydroxy-1H-indole-3-acetate</synonym>
    <synonym>5-Hydroxyindol-3-ylacetate</synonym>
    <synonym>5-Hydroxyindole-3-acetate</synonym>
    <synonym>5-Hydroxyindoleacetate</synonym>
    <synonym>Acid, 5-hydroxyindolamine acetic</synonym>
    <synonym>Acid, hydroxyindoleacetic</synonym>
    <synonym>5 Hydroxy 3 indoleacetic acid</synonym>
    <synonym>5-Hydroxy-3-indoleacetic acid</synonym>
    <synonym>Acetic acid, 5-hydroxyindolamine</synonym>
    <synonym>5 Hydroxyindolamine acetic acid</synonym>
    <synonym>5-Hydroxyindolamine acetic acid</synonym>
    <synonym>Acid, 5-hydroxy-3-indoleacetic</synonym>
    <synonym>Hydroxyindoleacetic acid</synonym>
    <synonym>5-Hydroxy-3-indolylacetate</synonym>
    <synonym>5-Hydroxy-iaa</synonym>
    <synonym>5-Hydroxy-indole-3-acetate</synonym>
    <synonym>5-Hydroxy-indole-3-acetic acid</synonym>
    <synonym>5-Hydroxyheteroauxin</synonym>
    <synonym>5-Hydroxyindole acetate</synonym>
    <synonym>5-Oxyindoleacetate</synonym>
    <synonym>5-Oxyindoleacetic acid</synonym>
    <synonym>5HIAA</synonym>
    <synonym>Hydroxyindoleacetate</synonym>
  </synonyms>
  <chemical_formula>C10H9NO3</chemical_formula>
  <average_molecular_weight>191.1834</average_molecular_weight>
  <monisotopic_moleculate_weight>191.058243159</monisotopic_moleculate_weight>
  <iupac_name>2-(5-hydroxy-1H-indol-3-yl)acetic acid</iupac_name>
  <traditional_iupac>hydroxyindoleacetic acid</traditional_iupac>
  <cas_registry_number>54-16-0</cas_registry_number>
  <smiles>OC(=O)CC1=CNC2=C1C=C(O)C=C2</smiles>
  <inchi>InChI=1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)</inchi>
  <inchikey>DUUGKQCEGZLZNO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Indolyl carboxylic acids and derivatives</sub_class>
    <direct_parent>Indole-3-acetic acid derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>3-alkylindoles</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxyindoles</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-alkylindole</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyindole</substituent>
      <substituent>Indole</substituent>
      <substituent>Indole-3-acetic acid derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>indole-3-acetic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>161 - 163 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>24 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-5.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(5-hydroxy-1H-indol-3-yl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>191.1834</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>191.058243159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC1=CNC2=C1C=C(O)C=C2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H9NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DUUGKQCEGZLZNO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>73.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22129</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB001403</foodb_id>
  <chemspider_id>1760</chemspider_id>
  <kegg_id>C05635</kegg_id>
  <phenol_explorer_compound_id/>
  <pubchem_compound_id>1826</pubchem_compound_id>
  <chebi_id>27823</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id>5-HYDROXYINDOLE_ACETATE</meta_cyc_id>
  <wikipedia_id>5-Hydroxyindoleacetic_acid</wikipedia_id>
  <knapsack_id>C00000104</knapsack_id>
  <bigg_id>46167</bigg_id>
  <metlin_id>2975</metlin_id>
  <synthesis_reference>Asero, B.; Colo, V. A.; Vercellone, A. Preparation of 5-hydroxy-3-indoleacetic acid. Farmaco, Edizione Scientifica  (1956),  11  219-20.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:13 UTC</creation_date>
  <update_date>2020-04-14 22:48:19 UTC</update_date>
  <accession>BMDB0000764</accession>
  <secondary_accessions>
    <accession>BMDB00764</accession>
  </secondary_accessions>
  <name>Hydrocinnamic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Phenyl-propionic acid</synonym>
    <synonym>3-Phenylpropanoic acid</synonym>
    <synonym>3-Phenylpropionsaeure</synonym>
    <synonym>3PP</synonym>
    <synonym>Benzenepropanoic acid</synonym>
    <synonym>Benzenepropionic acid</synonym>
    <synonym>Benzylacetic acid</synonym>
    <synonym>beta-Phenylpropionic acid</synonym>
    <synonym>Dihydrocinnamic acid</synonym>
    <synonym>Hydrozimtsaeure</synonym>
    <synonym>Phenylpropanoate</synonym>
    <synonym>3-Phenylpropanoate</synonym>
    <synonym>3-Phenylpropionic acid</synonym>
    <synonym>3-Phenyl-propionate</synonym>
    <synonym>Benzenepropanoate</synonym>
    <synonym>Benzenepropionate</synonym>
    <synonym>Benzylacetate</synonym>
    <synonym>b-Phenylpropionate</synonym>
    <synonym>b-Phenylpropionic acid</synonym>
    <synonym>beta-Phenylpropionate</synonym>
    <synonym>Β-phenylpropionate</synonym>
    <synonym>Β-phenylpropionic acid</synonym>
    <synonym>Dihydrocinnamate</synonym>
    <synonym>Phenylpropanoic acid</synonym>
    <synonym>3-Phenylpropionate</synonym>
    <synonym>Hydrocinnamate</synonym>
    <synonym>3-Phenyl-N-propionate</synonym>
    <synonym>3-Phenyl-N-propionic acid</synonym>
    <synonym>Omega-phenylpropanoate</synonym>
    <synonym>Omega-phenylpropanoic acid</synonym>
    <synonym>W-Phenylpropanoate</synonym>
    <synonym>W-Phenylpropanoic acid</synonym>
    <synonym>3-Phenylpropionic acid, sodium salt</synonym>
    <synonym>3-Phenyl propionic acid</synonym>
    <synonym>Phenylpropionic acid</synonym>
    <synonym>beta-Phenylpropanoic acid</synonym>
    <synonym>Β-phenylpropanoic acid</synonym>
    <synonym>Ω-phenylpropanoic acid</synonym>
    <synonym>HYDROCINNAMIC ACID</synonym>
  </synonyms>
  <chemical_formula>C9H10O2</chemical_formula>
  <average_molecular_weight>150.1745</average_molecular_weight>
  <monisotopic_moleculate_weight>150.068079564</monisotopic_moleculate_weight>
  <iupac_name>3-phenylpropanoic acid</iupac_name>
  <traditional_iupac>3-phenylpropionic acid</traditional_iupac>
  <cas_registry_number>501-52-0</cas_registry_number>
  <smiles>OC(=O)CCC1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)</inchi>
  <inchikey>XMIIGOLPHOKFCH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Phenylpropanoic acids</class>
    <sub_class/>
    <direct_parent>Phenylpropanoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>benzenes</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>45 - 48 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>5.9 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.84</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-phenylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>150.1745</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>150.068079564</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XMIIGOLPHOKFCH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373698</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>626.77 +/- 102.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>374-898</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>523.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>487.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>406.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>633</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>462-859</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>513 +/- 58</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>475 +/- 64</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>411 +/- 115</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>613 +/- 100</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>613 +/- 100</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR and GC-MS</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>396</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>322</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>328</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>446</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>523.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>482.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>410.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>51+/-18</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>626.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB008271</foodb_id>
  <drugbank_id>DB02024</drugbank_id>
  <chemspider_id>10181339</chemspider_id>
  <kegg_id>C05629</kegg_id>
  <pubchem_compound_id>107</pubchem_compound_id>
  <chebi_id>28631</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>3-PHENYLPROPIONATE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Phenylpropanoic_acid</wikipedia_id>
  <metlin_id>4153</metlin_id>
  <synthesis_reference>Muller, August John; Bowers, Joseph Stanton, Jr.; Eubanks, John Robert Ira; Geiger, Carey Cecil; Santobianco, John Gabriel.  Process for preparing hydrocinnamic acid from cinnamaldehyde.    PCT Int. Appl.  (1999),     18 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:15 UTC</creation_date>
  <update_date>2020-04-16 17:54:04 UTC</update_date>
  <accession>BMDB0000765</accession>
  <secondary_accessions>
    <accession>BMDB00765</accession>
  </secondary_accessions>
  <name>Mannitol</name>
  <description>D-Mannitol, also known as mannite or osmitrol, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. D-Mannitol is a drug which is used for the promotion of diuresis before irreversible renal failure becomes established, the reduction of intracranial pressure, the treatment of cerebral edema, and the promotion of urinary excretion of toxic substances. D-Mannitol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Mannitol exists in all living species, ranging from bacteria to humans. D-Mannitol has been found to be associated with several diseases known as eosinophilic esophagitis, aids, and alzheimer's disease; also d-mannitol has been linked to several inborn metabolic disorders including ribose-5-phosphate isomerase deficiency and cytochrome c oxidase deficiency.</description>
  <synonyms>
    <synonym>(2R,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexaol</synonym>
    <synonym>(2R,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexol</synonym>
    <synonym>D-(-)-Mannitol</synonym>
    <synonym>Dulcite</synonym>
    <synonym>e 421</synonym>
    <synonym>e-421</synonym>
    <synonym>e421</synonym>
    <synonym>Manna sugar</synonym>
    <synonym>Mannite</synonym>
    <synonym>Osmitrol</synonym>
    <synonym>D-Mannitol</synonym>
    <synonym>Tobrex</synonym>
    <synonym>Bronchitol</synonym>
    <synonym>1,2,3,4,5,6-Hexanehexol</synonym>
    <synonym>Cordycepate</synonym>
    <synonym>Cordycepic acid</synonym>
    <synonym>Diosmol</synonym>
    <synonym>Hexahydroxyhexane</synonym>
    <synonym>Hexanhexol</synonym>
    <synonym>Invenex</synonym>
    <synonym>Isotol</synonym>
    <synonym>Manicol</synonym>
    <synonym>Maniton S</synonym>
    <synonym>Maniton-S</synonym>
    <synonym>Mannazucker</synonym>
    <synonym>Mannidex</synonym>
    <synonym>Mannigen</synonym>
    <synonym>Mannistol</synonym>
    <synonym>Mannit</synonym>
    <synonym>Mannit p</synonym>
    <synonym>Mannogem 2080</synonym>
    <synonym>Marine crystal</synonym>
    <synonym>Mushroom sugar</synonym>
    <synonym>Osmofundin</synonym>
    <synonym>Osmosal</synonym>
    <synonym>Resectisol</synonym>
    <synonym>SDM No. 35</synonym>
    <synonym>(L)-Mannitol</synonym>
    <synonym>Mannitol</synonym>
  </synonyms>
  <chemical_formula>C6H14O6</chemical_formula>
  <average_molecular_weight>182.1718</average_molecular_weight>
  <monisotopic_moleculate_weight>182.07903818</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol</iupac_name>
  <traditional_iupac>mannitol</traditional_iupac>
  <cas_registry_number>69-65-8</cas_registry_number>
  <smiles>OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO</smiles>
  <inchi>InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1</inchi>
  <inchikey>FBPFZTCFMRRESA-KVTDHHQDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar alcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sugar alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>mannitol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>166 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>216 mg/mL at 25 °C</value>
      <source>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>182.1718</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>182.07903818</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H14O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FBPFZTCFMRRESA-KVTDHHQDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>121.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449871</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449872</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB001982</foodb_id>
  <drugbank_id>DB00742</drugbank_id>
  <chemspider_id>6015</chemspider_id>
  <kegg_id>C00392</kegg_id>
  <pubchem_compound_id>6251</pubchem_compound_id>
  <chebi_id>16899</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001165</knapsack_id>
  <meta_cyc_id>MANNITOL</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Mannitol</wikipedia_id>
  <metlin_id>142</metlin_id>
  <synthesis_reference>Zhang, Chaohui; Wang, Jianping; He, Junlin.  Preparation of mannitol from sucrose with high yield.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2005),     11 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:16 UTC</creation_date>
  <update_date>2020-04-14 22:48:20 UTC</update_date>
  <accession>BMDB0000766</accession>
  <secondary_accessions>
    <accession>BMDB00766</accession>
  </secondary_accessions>
  <name>N-Acetyl-L-alanine</name>
  <description/>
  <synonyms>
    <synonym>(S)-2-(Acetylamino)propanoic acid</synonym>
    <synonym>2-Acetamidopropionic acid</synonym>
    <synonym>Ac-ala-OH</synonym>
    <synonym>Acetylalanine</synonym>
    <synonym>L-N-Acetylalanine</synonym>
    <synonym>N-Acetyl-L-alpha-alanine</synonym>
    <synonym>N-Acetyl-S-alanine</synonym>
    <synonym>N-Acetylalanine</synonym>
    <synonym>(S)-2-(Acetylamino)propanoate</synonym>
    <synonym>2-Acetamidopropionate</synonym>
    <synonym>N-Acetyl-L-a-alanine</synonym>
    <synonym>N-Acetyl-L-α-alanine</synonym>
    <synonym>(S)-(-)-N-Acetylalanine</synonym>
    <synonym>(S)-N-Acetylalanine</synonym>
    <synonym>Acetyl-L-alanine</synonym>
    <synonym>N-Acetyl-(S)-alanine</synonym>
  </synonyms>
  <chemical_formula>C5H9NO3</chemical_formula>
  <average_molecular_weight>131.1299</average_molecular_weight>
  <monisotopic_moleculate_weight>131.058243159</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-acetamidopropanoic acid</iupac_name>
  <traditional_iupac>N-acetylalanine</traditional_iupac>
  <cas_registry_number>97-69-8</cas_registry_number>
  <smiles>C[C@H](NC(C)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H9NO3/c1-3(5(8)9)6-4(2)7/h3H,1-2H3,(H,6,7)(H,8,9)/t3-/m0/s1</inchi>
  <inchikey>KTHDTJVBEPMMGL-VKHMYHEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alanine and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Alanine or derivatives</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-alanine derivative</external_descriptor>
      <external_descriptor>N-acetyl-L-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-acetamidopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>131.1299</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>131.058243159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](NC(C)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H9NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H9NO3/c1-3(5(8)9)6-4(2)7/h3H,1-2H3,(H,6,7)(H,8,9)/t3-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KTHDTJVBEPMMGL-VKHMYHEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>29.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438686</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022231</foodb_id>
  <drugbank_id>DB02518</drugbank_id>
  <chemspider_id>79449</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>88064</pubchem_compound_id>
  <chebi_id>40992</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5733</metlin_id>
  <synthesis_reference>Vanzura, Jiri; Kasafirek, Evzen; Hrabalek, Alexandr; Vinsova, Jarmila; Krepelka, Jiri.  Process for preparing highly pure N-acetyl-L- or -D-alanine. Czech.  (1989),  4 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:17 UTC</creation_date>
  <update_date>2020-04-14 22:48:20 UTC</update_date>
  <accession>BMDB0000767</accession>
  <secondary_accessions>
    <accession>BMDB00767</accession>
  </secondary_accessions>
  <name>Pseudouridine</name>
  <description>Beta-Pseudouridine, also known as p or 5-ribosyluracil, belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others. Beta-Pseudouridine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Beta-Pseudouridine exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>(1S)-1,4-Anhydro-1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-D-ribitol</synonym>
    <synonym>5-(beta-D-Ribofuranosyl)uracil</synonym>
    <synonym>beta-Pseudouridine</synonym>
    <synonym>p</synonym>
    <synonym>Psi-uridine</synonym>
    <synonym>5-(b-D-Ribofuranosyl)uracil</synonym>
    <synonym>5-(Β-D-ribofuranosyl)uracil</synonym>
    <synonym>b-Pseudouridine</synonym>
    <synonym>Β-pseudouridine</synonym>
    <synonym>5-(b-delta-Ribofuranosyl)uracil</synonym>
    <synonym>5-b-D-Ribofuranosyl-uracil</synonym>
    <synonym>5-beta-delta-Ribofuranosyl-uracil</synonym>
    <synonym>5-Ribosyluracil</synonym>
    <synonym>b-D-Pseudouridine</synonym>
    <synonym>beta-delta-Pseudouridine</synonym>
    <synonym>Pseudouridine C</synonym>
    <synonym>Y-uridine</synonym>
    <synonym>5-beta-D-Ribofuranosyl-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>5-Β-D-ribofuranosyl-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>beta-D-Pseudouridine</synonym>
    <synonym>Β-D-pseudouridine</synonym>
    <synonym>Ψ-uridine</synonym>
    <synonym>Pseudouridine</synonym>
  </synonyms>
  <chemical_formula>C9H12N2O6</chemical_formula>
  <average_molecular_weight>244.2014</average_molecular_weight>
  <monisotopic_moleculate_weight>244.069536126</monisotopic_moleculate_weight>
  <iupac_name>5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione</iupac_name>
  <traditional_iupac>β-pseudouridine</traditional_iupac>
  <cas_registry_number>1445-07-4</cas_registry_number>
  <smiles>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)C1=CNC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C9H12N2O6/c12-2-4-5(13)6(14)7(17-4)3-1-10-9(16)11-8(3)15/h1,4-7,12-14H,2H2,(H2,10,11,15,16)/t4-,5-,6-,7+/m1/s1</inchi>
  <inchikey>PTJWIQPHWPFNBW-GBNDHIKLSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Nucleoside and nucleotide analogues</class>
    <sub_class/>
    <direct_parent>Nucleoside and nucleotide analogues</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>pseudouridines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>244.2014</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>244.069536126</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)C1=CNC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H12N2O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H12N2O6/c12-2-4-5(13)6(14)7(17-4)3-1-10-9(16)11-8(3)15/h1,4-7,12-14H,2H2,(H2,10,11,15,16)/t4-,5-,6-,7+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PTJWIQPHWPFNBW-GBNDHIKLSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>128.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>52.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438664</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw whole milk</comment>
      <references>
        <reference>
          <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
          <pubmed_id>6539345</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB031139</foodb_id>
  <drugbank_id/>
  <chemspider_id>14319</chemspider_id>
  <kegg_id>C02067</kegg_id>
  <pubchem_compound_id>15047</pubchem_compound_id>
  <chebi_id>17802</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001508</knapsack_id>
  <meta_cyc_id>CPD-497</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Pseudouridine</wikipedia_id>
  <metlin_id>5734</metlin_id>
  <synthesis_reference>anessian, Stephen; Machaalani, Roger. A highly stereo-controlled and efficient synthesis of a- and b-pseudouridines. Tetrahedron Letters (2003), 44(45), 8321-8323.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
      <pubmed_id>6539345</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00579</protein_accession>
      <name>Pseudouridylate synthase</name>
      <uniprot_id>A6QP68</uniprot_id>
      <gene_name>PUSL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00581</protein_accession>
      <name>Pseudouridylate synthase 7 homolog</name>
      <uniprot_id>Q08DI8</uniprot_id>
      <gene_name>PUS7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00582</protein_accession>
      <name>tRNA pseudouridine synthase 3</name>
      <uniprot_id>Q3SX07</uniprot_id>
      <gene_name>PUS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:19 UTC</creation_date>
  <update_date>2020-04-15 22:14:31 UTC</update_date>
  <accession>BMDB0000768</accession>
  <secondary_accessions>
    <accession>BMDB00768</accession>
  </secondary_accessions>
  <name>N-Acetyl-9-O-lactoylneuraminic acid</name>
  <description/>
  <synonyms>
    <synonym>N-Acetyl-9-O-lactoylneuraminate</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoate</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoate) D-glycero-D-galacto-2-nonulosonate</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoate) D-glycero-D-galacto-2-nonulosonic acid</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-9-(2-hydroxypropanoic acid</synonym>
    <synonym>9-O-Lactoyl-N-acetylneuraminic acid</synonym>
    <synonym>Neu5,8ac29</synonym>
    <synonym>Neu5ac9LT</synonym>
    <synonym>(2S,4S,5R,6R)-6-[(1R,2R)-1,2-Dihydroxy-3-[(2-hydroxypropanoyl)oxy]propyl]-2,4-dihydroxy-5-[(1-hydroxyethylidene)amino]oxane-2-carboxylate</synonym>
    <synonym>N-Acetyl-9-O-lactoylneuraminic acid</synonym>
  </synonyms>
  <chemical_formula>C14H23NO11</chemical_formula>
  <average_molecular_weight>381.3325</average_molecular_weight>
  <monisotopic_moleculate_weight>381.127110583</monisotopic_moleculate_weight>
  <iupac_name>(2S,4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-[(2-hydroxypropanoyl)oxy]propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>(2S,4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-[(2-hydroxypropanoyl)oxy]propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid</traditional_iupac>
  <cas_registry_number>92935-30-3</cas_registry_number>
  <smiles>CC(O)C(=O)OC[C@@H](O)[C@@H](O)[C@@H]1O[C@@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C14H23NO11/c1-5(16)12(21)25-4-8(19)10(20)11-9(15-6(2)17)7(18)3-14(24,26-11)13(22)23/h5,7-11,16,18-20,24H,3-4H2,1-2H3,(H,15,17)(H,22,23)/t5?,7-,8+,9+,10+,11+,14-/m0/s1</inchi>
  <inchikey>XXNWSGSWDRDYLR-NVZZXFSUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alanine and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Alanine or derivatives</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-alanine derivative</external_descriptor>
      <external_descriptor>N-acetyl-L-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-[(2-hydroxypropanoyl)oxy]propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>381.3325</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>381.127110583</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(O)C(=O)OC[C@@H](O)[C@@H](O)[C@@H]1O[C@@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H23NO11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H23NO11/c1-5(16)12(21)25-4-8(19)10(20)11-9(15-6(2)17)7(18)3-14(24,26-11)13(22)23/h5,7-11,16,18-20,24H,3-4H2,1-2H3,(H,15,17)(H,22,23)/t5?,7-,8+,9+,10+,11+,14-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XXNWSGSWDRDYLR-NVZZXFSUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>203.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344958</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022232</foodb_id>
  <chemspider_id>166877</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>192236</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5735</metlin_id>
  <synthesis_reference>Kleineidam, Reinhard G.; Hofmann, Olaf; Reuter, Gerd; Schauer, Roland.  Indications for the enzymic synthesis of 9-O-lactoyl-N-acetylneuraminic acid in equine liver.    Glycoconjugate Journal  (1993),  10(1),  116-19.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:20 UTC</creation_date>
  <update_date>2020-04-15 22:20:36 UTC</update_date>
  <accession>BMDB0000770</accession>
  <secondary_accessions>
    <accession>BMDB00770</accession>
  </secondary_accessions>
  <name>N-Glycoloylganglioside GM2</name>
  <description/>
  <synonyms>
    <synonym>Ganglioside aii</synonym>
    <synonym>N-Glycoloyl-ganglioside GM2</synonym>
    <synonym>N-Glycoloyl-GM2</synonym>
    <synonym>NeuGc-GM2</synonym>
    <synonym>N-[(2S,3S)-3-Hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}nonadecan-2-yl]octadecanimidate</synonym>
  </synonyms>
  <chemical_formula>C43H85NO8</chemical_formula>
  <average_molecular_weight>744.1369</average_molecular_weight>
  <monisotopic_moleculate_weight>743.627518701</monisotopic_moleculate_weight>
  <iupac_name>N-[(2S,3S)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}nonadecan-2-yl]octadecanamide</iupac_name>
  <traditional_iupac>N-[(2S,3S)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}nonadecan-2-yl]octadecanamide</traditional_iupac>
  <cas_registry_number/>
  <smiles>CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@H](O)CCCCCCCCCCCCCCCC</smiles>
  <inchi>InChI=1S/C43H85NO8/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-39(47)44-36(35-51-43-42(50)41(49)40(48)38(34-45)52-43)37(46)32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h36-38,40-43,45-46,48-50H,3-35H2,1-2H3,(H,44,47)/t36-,37-,38+,40+,41-,42+,43+/m0/s1</inchi>
  <inchikey>SYMIJCRAJBNLEL-YPQBUIQASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Sphingolipids</class>
    <sub_class>Glycosphingolipids</sub_class>
    <direct_parent>Glycosphingolipids</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Alkyl glycosides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Fatty acyl glycosides of mono- and disaccharides</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl glycoside</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty acyl glycoside</substituent>
      <substituent>Fatty acyl glycoside of mono- or disaccharide</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosphingolipid</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>8.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>10.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[(2S,3S)-3-hydroxy-1-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}nonadecan-2-yl]octadecanamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>744.1369</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>743.627518701</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@H](O)CCCCCCCCCCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C43H85NO8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C43H85NO8/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-39(47)44-36(35-51-43-42(50)41(49)40(48)38(34-45)52-43)37(46)32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h36-38,40-43,45-46,48-50H,3-35H2,1-2H3,(H,44,47)/t36-,37-,38+,40+,41-,42+,43+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SYMIJCRAJBNLEL-YPQBUIQASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>148.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>211.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>95.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01808</kegg_id>
  <foodb_id>FDB022233</foodb_id>
  <chemspider_id>393427</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>445946</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id>GM2</pdbe_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5737</metlin_id>
  <synthesis_reference>Schmidt, Richard; Castro-Palomino, Julio C.; Doll, Andreas; Ritter, Gerd; Old, Lloyd J.  Preparation of ganglioside GM2.    PCT Int. Appl.  (1997),     27 pp.  CODEN: PIXXD2  WO  9730061  A1  19970821  CAN 127:248363  AN 1997:568133</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:21 UTC</creation_date>
  <update_date>2020-04-14 22:48:21 UTC</update_date>
  <accession>BMDB0000772</accession>
  <secondary_accessions>
    <accession>BMDB00772</accession>
  </secondary_accessions>
  <name>Nonadecanoic acid</name>
  <description>Nonadecanoic acid, also known as N-nonadecanoate or nonadecylate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Nonadecanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Nonadecanoic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>19:00</synonym>
    <synonym>C19:0</synonym>
    <synonym>N-Nonadecanoic acid</synonym>
    <synonym>Nonadecylic acid</synonym>
    <synonym>N-Nonadecanoate</synonym>
    <synonym>Nonadecylate</synonym>
    <synonym>Nonadecanoate</synonym>
    <synonym>N-Nonadecylate</synonym>
    <synonym>N-Nonadecylic acid</synonym>
    <synonym>FA(19:0)</synonym>
    <synonym>Nonadecanoic acid</synonym>
  </synonyms>
  <chemical_formula>C19H38O2</chemical_formula>
  <average_molecular_weight>298.5038</average_molecular_weight>
  <monisotopic_moleculate_weight>298.28718046</monisotopic_moleculate_weight>
  <iupac_name>nonadecanoic acid</iupac_name>
  <traditional_iupac>nonadecanoic acid</traditional_iupac>
  <cas_registry_number>646-30-0</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C19H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21/h2-18H2,1H3,(H,20,21)</inchi>
  <inchikey>ISYWECDDZWTKFF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>69.4 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>8.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>nonadecanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>298.5038</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>298.28718046</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H38O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21/h2-18H2,1H3,(H,20,21)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ISYWECDDZWTKFF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>90.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>151026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>151027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>151028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3261</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>66.23</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>91.79</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>2537.19</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>3976.6</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>1483.57</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>1097.61</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>7537.59</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Calf-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>7537.59</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. With growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>7396.89</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Without growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>7477.29</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Yearling-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk. Meta-Analysis</comment>
      <references>
        <reference>
          <reference_text>Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.</reference_text>
          <pubmed_id>19038946</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Pasteurized milk with 3.9% fat, organic, by GC-FID</comment>
      <references>
        <reference>
          <reference_text>Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026.</reference_text>
          <pubmed_id>29570652</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
          <pubmed_id>14168161</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB004043</foodb_id>
  <drugbank_id/>
  <chemspider_id>12071</chemspider_id>
  <kegg_id>C16535</kegg_id>
  <pubchem_compound_id>12591</pubchem_compound_id>
  <chebi_id>39246</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Nonadecylic_acid</wikipedia_id>
  <metlin_id>5738</metlin_id>
  <synthesis_reference>Lee, Donald G.; Lamb, Shannon E.; Chang, Victor S. Carboxylic acids from the oxidation of terminal alkenes by permanganate: nonadecanoic acid. Organic Syntheses (1981), 60 11-14.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
      <pubmed_id>14168161</pubmed_id>
    </reference>
    <reference>
      <reference_text>Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026.</reference_text>
      <pubmed_id>29570652</pubmed_id>
    </reference>
    <reference>
      <reference_text>Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.</reference_text>
      <pubmed_id>19038946</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:22 UTC</creation_date>
  <update_date>2020-03-13 16:23:44 UTC</update_date>
  <accession>BMDB0000773</accession>
  <secondary_accessions>
    <accession>BMDB00773</accession>
  </secondary_accessions>
  <name>N-Acetyl-a-neuraminic acid</name>
  <description/>
  <synonyms>
    <synonym>alpha-Neu5ac</synonym>
    <synonym>O-SIALIC ACID</synonym>
    <synonym>a-Neu5ac</synonym>
    <synonym>Α-neu5ac</synonym>
    <synonym>O-SIALate</synonym>
    <synonym>N-Acetyl-a-neuraminate</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosonate</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-D-glycero-a-D-galacto-2-nonulopyranosonic acid</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-delta-glycero-alpha-delta-galacto-2-nonulopyranosonate</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-delta-glycero-alpha-delta-galacto-2-nonulopyranosonic acid</synonym>
    <synonym>5-Acetamido-3,5-dideoxy-a-D-glycero-D-galacto-nonulopyranosonate</synonym>
    <synonym>5-Acetamido-3,5-dideoxy-a-D-glycero-D-galacto-nonulopyranosonic acid</synonym>
    <synonym>5-Acetamido-3,5-dideoxy-alpha-delta-glycero-delta-galacto-nonulopyranosonate</synonym>
    <synonym>5-Acetamido-3,5-dideoxy-alpha-delta-glycero-delta-galacto-nonulopyranosonic acid</synonym>
    <synonym>N-Acetyl-a-D-neuraminate</synonym>
    <synonym>N-Acetyl-a-D-neuraminic acid</synonym>
    <synonym>N-Acetyl-alpha-delta-neuraminate</synonym>
    <synonym>N-Acetyl-alpha-delta-neuraminic acid</synonym>
    <synonym>N-Acetyl-alpha-neuraminate</synonym>
    <synonym>PolySia</synonym>
    <synonym>Polysialic acid</synonym>
    <synonym>N-Acetyl-alpha-neuraminic acid</synonym>
    <synonym>N-Acetyl-α-neuraminate</synonym>
    <synonym>N-Acetyl-α-neuraminic acid</synonym>
    <synonym>N-Acetyl-a-neuraminic acid</synonym>
    <synonym>Acid, N-acetylneuraminic</synonym>
    <synonym>Acid, sialic</synonym>
    <synonym>N Acetylneuraminic acid</synonym>
    <synonym>N-Acetylneuraminic acid</synonym>
    <synonym>Sialic acid</synonym>
  </synonyms>
  <chemical_formula>C11H19NO9</chemical_formula>
  <average_molecular_weight>309.2699</average_molecular_weight>
  <monisotopic_moleculate_weight>309.105981211</monisotopic_moleculate_weight>
  <iupac_name>(2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>N-acetylneuraminic acid</traditional_iupac>
  <cas_registry_number>21646-00-4</cas_registry_number>
  <smiles>[H][C@]1(O[C@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO</smiles>
  <inchi>InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1</inchi>
  <inchikey>SQVRNKJHWKZAKO-YRMXFSIDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>N-acylneuraminic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>C-glucuronides</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Neuraminic acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>C-glucuronide</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acylneuraminic acid</substituent>
      <substituent>Neuraminic acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acetylneuraminic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>309.2699</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>309.105981211</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(O[C@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H19NO9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SQVRNKJHWKZAKO-YRMXFSIDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>176.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>63.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34894</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB03721</drugbank_id>
  <chemspider_id>392681</chemspider_id>
  <chebi_id>49026</chebi_id>
  <pubchem_compound_id>444885</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id>C19909</kegg_id>
  <foodb_id>FDB022234</foodb_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5739</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Baumberger, Franz; Vasella, Andrea. , Synthesis of N-acetylneuraminic acid and N-acetyl-4-epineuraminic acid. Helvetica Chimica Acta (1986), 69(5), 1205-15.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:23 UTC</creation_date>
  <update_date>2020-04-15 23:26:42 UTC</update_date>
  <accession>BMDB0000774</accession>
  <secondary_accessions>
    <accession>BMDB00774</accession>
  </secondary_accessions>
  <name>Pregnenolone sulfate</name>
  <description/>
  <synonyms>
    <synonym>Pregnenolone sulfuric acid</synonym>
    <synonym>Pregnenolone sulphate</synonym>
    <synonym>Pregnenolone sulphuric acid</synonym>
    <synonym>5-Pregnen-3b-sulfate-20-one</synonym>
    <synonym>5-Pregnen-3b-sulphate-20-one</synonym>
    <synonym>Pregn-5-en-20-on-3b-yl sulfurate</synonym>
    <synonym>Pregn-5-en-20-on-3b-yl sulfuric acid</synonym>
    <synonym>Pregn-5-en-20-one-3b-yl sulfate</synonym>
    <synonym>Pregn-5-en-20-one-3b-yl sulphate</synonym>
    <synonym>Pregnenolone 3-sulfate</synonym>
    <synonym>Pregnenolone 3-sulphate</synonym>
    <synonym>Pregnenolone 3b-sulfate</synonym>
    <synonym>Pregnenolone 3b-sulphate</synonym>
    <synonym>Pregnenolone hydrogen sulfate</synonym>
    <synonym>Pregnenolone hydrogen sulphate</synonym>
    <synonym>Pregnenolone monosulfate</synonym>
    <synonym>Pregnenolone monosulphate</synonym>
    <synonym>[(1S,2R,10S,11S,14S,15S)-14-Acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulfonate</synonym>
    <synonym>[(1S,2R,10S,11S,14S,15S)-14-Acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulphonate</synonym>
    <synonym>[(1S,2R,10S,11S,14S,15S)-14-Acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulphonic acid</synonym>
  </synonyms>
  <chemical_formula>C21H32O5S</chemical_formula>
  <average_molecular_weight>396.541</average_molecular_weight>
  <monisotopic_moleculate_weight>396.197044824</monisotopic_moleculate_weight>
  <iupac_name>[(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid</iupac_name>
  <traditional_iupac>[(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid</traditional_iupac>
  <cas_registry_number>1247-64-9</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(CC[C@]12C)OS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C21H32O5S/c1-13(22)17-6-7-18-16-5-4-14-12-15(26-27(23,24)25)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19H,5-12H2,1-3H3,(H,23,24,25)/t15?,16-,17+,18-,19-,20-,21+/m0/s1</inchi>
  <inchikey>DIJBBUIOWGGQOP-OZIWPBGVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Sulfated steroids</sub_class>
    <direct_parent>Sulfated steroids</direct_parent>
    <alternative_parents>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Pregnane steroids</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>20-oxosteroid</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfated steroid skeleton</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>396.541</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>396.197044824</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(CC[C@]12C)OS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H32O5S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H32O5S/c1-13(22)17-6-7-18-16-5-4-14-12-15(26-27(23,24)25)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19H,5-12H2,1-3H3,(H,23,24,25)/t15?,16-,17+,18-,19-,20-,21+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DIJBBUIOWGGQOP-OZIWPBGVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>103.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>43.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>94857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>94858</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>94859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158988</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158990</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022235</foodb_id>
  <drugbank_id/>
  <chemspider_id>17216005</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>20845972</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id>2705327</bigg_id>
  <wikipedia_id>Pregnenolone sulfate</wikipedia_id>
  <metlin_id>5740</metlin_id>
  <synthesis_reference>Killinger, Donald W.; Solomon, Samuel.  Synthesis of pregnenolone sulfate, dehydroisoandrosterone sulfate, 17a-hydroxypregnenolone sulfate, and pregn-5-enetriol by the normal human adrenal gland.    Journal of Clinical Endocrinology and Metabolism  (1965),  25(2),  290-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:24 UTC</creation_date>
  <update_date>2020-04-14 22:48:22 UTC</update_date>
  <accession>BMDB0000779</accession>
  <secondary_accessions>
    <accession>BMDB00779</accession>
  </secondary_accessions>
  <name>Phenyllactic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Hydroxy-3-phenylpropionic acid</synonym>
    <synonym>beta-Phenyllactic acid</synonym>
    <synonym>DL-3-Phenyllactic acid</synonym>
    <synonym>DL-beta-Phenyllactic acid</synonym>
    <synonym>2-Hydroxy-3-phenylpropionate</synonym>
    <synonym>b-Phenyllactate</synonym>
    <synonym>b-Phenyllactic acid</synonym>
    <synonym>beta-Phenyllactate</synonym>
    <synonym>Β-phenyllactate</synonym>
    <synonym>Β-phenyllactic acid</synonym>
    <synonym>DL-3-Phenyllactate</synonym>
    <synonym>DL-b-Phenyllactate</synonym>
    <synonym>DL-b-Phenyllactic acid</synonym>
    <synonym>DL-beta-Phenyllactate</synonym>
    <synonym>DL-Β-phenyllactate</synonym>
    <synonym>DL-Β-phenyllactic acid</synonym>
    <synonym>Phenyllactate</synonym>
    <synonym>3-Phenyllactate</synonym>
    <synonym>3-Phenyllactic acid, monosodium salt</synonym>
    <synonym>3-Phenyllactic acid, (D)-isomer</synonym>
    <synonym>3-Phenyllactic acid, (L)-isomer</synonym>
    <synonym>3-Phenyllactic acid, (DL)-isomer</synonym>
    <synonym>3-Phenyllactic acid, calcium salt</synonym>
    <synonym>3-Phenyllactic acid</synonym>
  </synonyms>
  <chemical_formula>C9H10O3</chemical_formula>
  <average_molecular_weight>166.1739</average_molecular_weight>
  <monisotopic_moleculate_weight>166.062994186</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-3-phenylpropanoic acid</iupac_name>
  <traditional_iupac>β-phenyllactic acid</traditional_iupac>
  <cas_registry_number>828-01-3</cas_registry_number>
  <smiles>OC(CC1=CC=CC=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)</inchi>
  <inchikey>VOXXWSYKYCBWHO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Phenylpropanoic acids</class>
    <sub_class/>
    <direct_parent>Phenylpropanoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxy monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>98 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.83</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-3-phenylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>166.1739</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>166.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(CC1=CC=CC=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VOXXWSYKYCBWHO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438681</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>8.6 +/- 2.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Khan RI, Onodera R, Amin MR, Mohammed N: Production of tyrosine and other aromatic compounds from phenylalanine by rumen microorganisms. Amino Acids. 1999;17(4):335-46.</reference_text>
          <pubmed_id>10707763</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022236</foodb_id>
  <drugbank_id/>
  <chemspider_id>3715</chemspider_id>
  <kegg_id>C01479</kegg_id>
  <pubchem_compound_id>3848</pubchem_compound_id>
  <chebi_id>25998</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-7999</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5745</metlin_id>
  <synthesis_reference>Yu, Jian Ming; Xue, Fen.  A method of synthesis of phenyllactic acid and substituted phenyllactic acids.    Chinese Chemical Letters  (1993),  4(8),  673-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:26 UTC</creation_date>
  <update_date>2020-03-13 16:23:46 UTC</update_date>
  <accession>BMDB0000780</accession>
  <secondary_accessions>
    <accession>BMDB00780</accession>
  </secondary_accessions>
  <name>Porphinehexacarboxylic acid</name>
  <description/>
  <synonyms>
    <synonym>Porphinehexacarboxylate</synonym>
    <synonym>21H,23H-Porphinehexacarboxylate</synonym>
    <synonym>21H,23H-Porphinehexacarboxylic acid</synonym>
    <synonym>3,8-Bis(carboxymethyl)-13,17-dimethyl-2,7,12,18-porphinetetrapropionate</synonym>
    <synonym>3,8-Bis(carboxymethyl)-13,17-dimethyl-2,7,12,18-porphinetetrapropionic acid</synonym>
    <synonym>3-[10,15,20-Tris(2-carboxyethyl)-14,19-bis(carboxymethyl)-5,9-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C38H38N4O12</chemical_formula>
  <average_molecular_weight>742.7279</average_molecular_weight>
  <monisotopic_moleculate_weight>742.2486227</monisotopic_moleculate_weight>
  <iupac_name>3-[9,15,19-tris(2-carboxyethyl)-5,20-bis(carboxymethyl)-10,14-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[9,15,19-tris(2-carboxyethyl)-5,20-bis(carboxymethyl)-10,14-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>28100-67-6</cas_registry_number>
  <smiles>CC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C)=C5CCC(O)=O)C(CCC(O)=O)=C4CC(O)=O)C(CCC(O)=O)=C3CC(O)=O)=C1CCC(O)=O</smiles>
  <inchi>InChI=1S/C38H38N4O12/c1-17-19(3-7-33(43)44)27-14-29-21(5-9-35(47)48)24(12-38(53)54)32(41-29)16-30-22(6-10-36(49)50)23(11-37(51)52)31(42-30)15-28-20(4-8-34(45)46)18(2)26(40-28)13-25(17)39-27/h13-16,40-41H,3-12H2,1-2H3,(H,43,44)(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-16-,31-15-,32-16-</inchi>
  <inchikey>VQFYONCZECTVOH-JWLKGTHFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[9,15,19-tris(2-carboxyethyl)-5,20-bis(carboxymethyl)-10,14-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>742.7279</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>742.2486227</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C)=C5CCC(O)=O)C(CCC(O)=O)=C4CC(O)=O)C(CCC(O)=O)=C3CC(O)=O)=C1CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C38H38N4O12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C38H38N4O12/c1-17-19(3-7-33(43)44)27-14-29-21(5-9-35(47)48)24(12-38(53)54)32(41-29)16-30-22(6-10-36(49)50)23(11-37(51)52)31(42-30)15-28-20(4-8-34(45)46)18(2)26(40-28)13-25(17)39-27/h13-16,40-41H,3-12H2,1-2H3,(H,43,44)(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-16-,31-15-,32-16-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VQFYONCZECTVOH-JWLKGTHFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>281.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>188.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>79.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337863</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022237</foodb_id>
  <chemspider_id>13628144</chemspider_id>
  <pubchem_compound_id/>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5746</metlin_id>
  <synthesis_reference>Jackson, A. H.; Sancovich, H. A.; Ferramola, A. M.; Evans, N.; Games, D. E.; Matlin, S. A.; Elder, G. H.; Smith, S. G.  Macrocyclic intermediates in the biosynthesis of porphyrins.    Philosophical Transactions of the Royal Society of London, Series B:  Biological Sciences  (1976),  273(924),  191-206.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:27 UTC</creation_date>
  <update_date>2020-03-13 16:23:47 UTC</update_date>
  <accession>BMDB0000781</accession>
  <secondary_accessions>
    <accession>BMDB00781</accession>
  </secondary_accessions>
  <name>N-Acetylgalactosamine 4-sulphate</name>
  <description/>
  <synonyms>
    <synonym>N-Acetyl-beta-D-galactosamine 4-sulphate</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-4-O-sulfO-beta-D-galactopyranose</synonym>
    <synonym>2-Deoxy-2-acetamido-beta-D-galactose-4-sulfate</synonym>
    <synonym>beta-D-GalpNAc4S</synonym>
    <synonym>N-Acetyl-beta-D-galactosamine 4-sulfuric acid</synonym>
    <synonym>N-Acetyl-b-D-galactosamine 4-sulfate</synonym>
    <synonym>N-Acetyl-b-D-galactosamine 4-sulfuric acid</synonym>
    <synonym>N-Acetyl-b-D-galactosamine 4-sulphate</synonym>
    <synonym>N-Acetyl-b-D-galactosamine 4-sulphuric acid</synonym>
    <synonym>N-Acetyl-beta-D-galactosamine 4-sulfate</synonym>
    <synonym>N-Acetyl-beta-D-galactosamine 4-sulphuric acid</synonym>
    <synonym>N-Acetyl-β-D-galactosamine 4-sulfate</synonym>
    <synonym>N-Acetyl-β-D-galactosamine 4-sulfuric acid</synonym>
    <synonym>N-Acetyl-β-D-galactosamine 4-sulphate</synonym>
    <synonym>N-Acetyl-β-D-galactosamine 4-sulphuric acid</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-4-O-sulfO-b-D-galactopyranose</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-4-O-sulfO-β-D-galactopyranose</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-4-O-sulphO-b-D-galactopyranose</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-4-O-sulphO-beta-D-galactopyranose</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-4-O-sulphO-β-D-galactopyranose</synonym>
    <synonym>2-Deoxy-2-acetamido-b-D-galactose-4-sulfate</synonym>
    <synonym>2-Deoxy-2-acetamido-b-D-galactose-4-sulfuric acid</synonym>
    <synonym>2-Deoxy-2-acetamido-b-D-galactose-4-sulphate</synonym>
    <synonym>2-Deoxy-2-acetamido-b-D-galactose-4-sulphuric acid</synonym>
    <synonym>2-Deoxy-2-acetamido-beta-D-galactose-4-sulfuric acid</synonym>
    <synonym>2-Deoxy-2-acetamido-beta-D-galactose-4-sulphate</synonym>
    <synonym>2-Deoxy-2-acetamido-beta-D-galactose-4-sulphuric acid</synonym>
    <synonym>2-Deoxy-2-acetamido-β-D-galactose-4-sulfate</synonym>
    <synonym>2-Deoxy-2-acetamido-β-D-galactose-4-sulfuric acid</synonym>
    <synonym>2-Deoxy-2-acetamido-β-D-galactose-4-sulphate</synonym>
    <synonym>2-Deoxy-2-acetamido-β-D-galactose-4-sulphuric acid</synonym>
    <synonym>b-D-GalpNAc4S</synonym>
    <synonym>Β-D-galpnac4S</synonym>
    <synonym>N-Acetylgalactosamine 4-sulfate</synonym>
    <synonym>N-Acetylgalactosamine 4-sulfuric acid</synonym>
    <synonym>N-Acetylgalactosamine 4-sulphuric acid</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-D-galactose 4-(hydrogen sulfate)</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-D-galactose 4-(hydrogen sulphate)</synonym>
    <synonym>GalNAc4S</synonym>
    <synonym>N-Acetyl-D-galactosamine 4-sulfate</synonym>
    <synonym>N-Acetyl-D-galactosamine 4-sulphate</synonym>
    <synonym>N-Acetylgalactosamine-4-sulfate</synonym>
    <synonym>N-Acetylgalactosamine-4-sulphate</synonym>
    <synonym>NAG-4-S</synonym>
    <synonym>N-[(2R,3R,4R,5R,6R)-2,4-Dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-3-yl]ethanimidate</synonym>
    <synonym>N-[(2R,3R,4R,5R,6R)-2,4-Dihydroxy-6-(hydroxymethyl)-5-(sulphooxy)oxan-3-yl]ethanimidate</synonym>
    <synonym>N-[(2R,3R,4R,5R,6R)-2,4-Dihydroxy-6-(hydroxymethyl)-5-(sulphooxy)oxan-3-yl]ethanimidic acid</synonym>
  </synonyms>
  <chemical_formula>C8H15NO9S</chemical_formula>
  <average_molecular_weight>301.271</average_molecular_weight>
  <monisotopic_moleculate_weight>301.046751773</monisotopic_moleculate_weight>
  <iupac_name>[(2R,3R,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid</iupac_name>
  <traditional_iupac>[(2R,3R,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid</traditional_iupac>
  <cas_registry_number>45233-43-0</cas_registry_number>
  <smiles>CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS(O)(=O)=O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C8H15NO9S/c1-3(11)9-5-6(12)7(18-19(14,15)16)4(2-10)17-8(5)13/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H,14,15,16)/t4-,5-,6-,7+,8-/m1/s1</inchi>
  <inchikey>WHCJUIFHMJFEFZ-UIAUGNHASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Acylaminosugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharide sulfates</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Acylaminosugar</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide sulfate</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(2R,3R,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxidanesulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>301.271</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>301.046751773</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](OS(O)(=O)=O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15NO9S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15NO9S/c1-3(11)9-5-6(12)7(18-19(14,15)16)4(2-10)17-8(5)13/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H,14,15,16)/t4-,5-,6-,7+,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WHCJUIFHMJFEFZ-UIAUGNHASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>162.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>57.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280325</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022238</foodb_id>
  <drugbank_id>DB01872</drugbank_id>
  <chemspider_id>393546</chemspider_id>
  <kegg_id>C16265</kegg_id>
  <pubchem_compound_id>446101</pubchem_compound_id>
  <chebi_id>44391</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-12516</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5747</metlin_id>
  <synthesis_reference>Skelton, Timothy P.; Hooper, Lora V.; Srivastava, Vandana; Hindsgaul, Ole; Baenziger, Jacques U.  Characterization of a sulfotransferase responsible for the 4-O-sulfation of terminal b-N-acetyl-D-galactosamine on asparagine-linked oligosaccharides of glycoprotein hormones.    Journal of Biological Chemistry  (1991),  266(26),  17142-50.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:28 UTC</creation_date>
  <update_date>2020-03-13 16:23:47 UTC</update_date>
  <accession>BMDB0000782</accession>
  <secondary_accessions>
    <accession>BMDB00782</accession>
  </secondary_accessions>
  <name>Octadecanedioic acid</name>
  <description/>
  <synonyms>
    <synonym>1,16-Hexadecanedicarboxylic acid</synonym>
    <synonym>1,18-Octadecadioic acid</synonym>
    <synonym>1,18-Octadecanedioic acid</synonym>
    <synonym>Octadecane-1,18-dioic acid</synonym>
    <synonym>1,16-Hexadecanedicarboxylate</synonym>
    <synonym>1,18-Octadecadioate</synonym>
    <synonym>1,18-Octadecanedioate</synonym>
    <synonym>Octadecane-1,18-dioate</synonym>
    <synonym>Octadecanedioate</synonym>
  </synonyms>
  <chemical_formula>C18H34O4</chemical_formula>
  <average_molecular_weight>314.4602</average_molecular_weight>
  <monisotopic_moleculate_weight>314.245709576</monisotopic_moleculate_weight>
  <iupac_name>octadecanedioic acid</iupac_name>
  <traditional_iupac>octadecanedioic acid</traditional_iupac>
  <cas_registry_number>871-70-5</cas_registry_number>
  <smiles>OC(=O)CCCCCCCCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C18H34O4/c19-17(20)15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(21)22/h1-16H2,(H,19,20)(H,21,22)</inchi>
  <inchikey>BNJOQKFENDDGSC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>octadecanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>314.4602</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>314.245709576</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCCCCCCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H34O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H34O4/c19-17(20)15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(21)22/h1-16H2,(H,19,20)(H,21,22)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BNJOQKFENDDGSC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>87.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450232</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022239</foodb_id>
  <pubchem_compound_id>70095</pubchem_compound_id>
  <chemspider_id>63283</chemspider_id>
  <pdbe_id/>
  <kegg_id/>
  <chebi_id>133086</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5748</metlin_id>
  <synthesis_reference>Drake, Nathan L.; Melamed, Sidney.  Tetratriacontanoic acid and related compounds.    Journal of the American Chemical Society  (1948),  70  364-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:29 UTC</creation_date>
  <update_date>2020-03-13 16:23:48 UTC</update_date>
  <accession>BMDB0000783</accession>
  <secondary_accessions>
    <accession>BMDB00783</accession>
  </secondary_accessions>
  <name>Propionylglycine</name>
  <description/>
  <synonyms>
    <synonym>2-Propanamidoacetic acid</synonym>
    <synonym>N-Propionyl-glycine</synonym>
    <synonym>N-Propionylglycine</synonym>
    <synonym>Propanamidoacetic acid</synonym>
    <synonym>Propanoylglycine</synonym>
    <synonym>Propionylaminoacetic acid</synonym>
    <synonym>2-Propanamidoacetate</synonym>
    <synonym>Propanamidoacetate</synonym>
    <synonym>Propionylaminoacetate</synonym>
  </synonyms>
  <chemical_formula>C5H9NO3</chemical_formula>
  <average_molecular_weight>131.1299</average_molecular_weight>
  <monisotopic_moleculate_weight>131.058243159</monisotopic_moleculate_weight>
  <iupac_name>2-propanamidoacetic acid</iupac_name>
  <traditional_iupac>propionylglycine</traditional_iupac>
  <cas_registry_number>21709-90-0</cas_registry_number>
  <smiles>CCC(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C5H9NO3/c1-2-4(7)6-3-5(8)9/h2-3H2,1H3,(H,6,7)(H,8,9)</inchi>
  <inchikey>WOMAZEJKVZLLFE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-propanamidoacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>131.1299</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>131.058243159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H9NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H9NO3/c1-2-4(7)6-3-5(8)9/h2-3H2,1H3,(H,6,7)(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WOMAZEJKVZLLFE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292919</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333252</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022240</foodb_id>
  <pubchem_compound_id>98681</pubchem_compound_id>
  <chemspider_id>89122</chemspider_id>
  <pdbe_id/>
  <kegg_id/>
  <chebi_id>89836</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5749</metlin_id>
  <synthesis_reference>Katz, J.; Lieberman, I.; Barker, H. A.  Formation of propionyl-, butyryl-, and other acylglycines by enzymes of Clostridium kluyveri.    Journal of Biological Chemistry  (1953),  200  431-41.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:30 UTC</creation_date>
  <update_date>2020-04-16 17:54:05 UTC</update_date>
  <accession>BMDB0000784</accession>
  <secondary_accessions>
    <accession>BMDB00784</accession>
  </secondary_accessions>
  <name>Azelaic acid</name>
  <description/>
  <synonyms>
    <synonym>1,7-Dicarboxyheptane</synonym>
    <synonym>1,7-Heptanedicarboxylic acid</synonym>
    <synonym>1,9-Nonanedioic acid</synonym>
    <synonym>Acide azelaique</synonym>
    <synonym>Acidum azelaicum</synonym>
    <synonym>Anchoic acid</synonym>
    <synonym>Azelainsaeure</synonym>
    <synonym>Azelex</synonym>
    <synonym>Finacea</synonym>
    <synonym>Lepargylic acid</synonym>
    <synonym>N-Nonanedioic acid</synonym>
    <synonym>Nonandisaeure</synonym>
    <synonym>Skinoren</synonym>
    <synonym>Nonanedioic acid</synonym>
    <synonym>1,7-Heptanedicarboxylate</synonym>
    <synonym>1,9-Nonanedioate</synonym>
    <synonym>Anchoate</synonym>
    <synonym>Lepargylate</synonym>
    <synonym>N-Nonanedioate</synonym>
    <synonym>Nonanedioate</synonym>
    <synonym>Azelaate</synonym>
    <synonym>Azalaic acid</synonym>
    <synonym>Azelaicacidtech</synonym>
    <synonym>Azelainic acid</synonym>
    <synonym>Azelate</synonym>
    <synonym>Emerox 1110</synonym>
    <synonym>Emerox 1144</synonym>
    <synonym>Emery'S L-110</synonym>
    <synonym>Finevin</synonym>
    <synonym>Heptanedicarboxylic acid</synonym>
    <synonym>Nonanedioic acid azelaic acid</synonym>
    <synonym>Nonanedioic acid homopolymer</synonym>
    <synonym>Poly(azelaic anhydride)</synonym>
    <synonym>Polyazelaic anhydride</synonym>
    <synonym>Skinorem</synonym>
    <synonym>Azelaic acid, dilithium salt</synonym>
    <synonym>Azelaic acid, dipotassium salt</synonym>
    <synonym>Azelaic acid, disodium salt</synonym>
    <synonym>Azelaic acid, monosodium salt</synonym>
    <synonym>Azelaic acid, potassium salt</synonym>
    <synonym>Azelaic acid, sodium salt</synonym>
    <synonym>Monosodium azelate</synonym>
  </synonyms>
  <chemical_formula>C9H16O4</chemical_formula>
  <average_molecular_weight>188.2209</average_molecular_weight>
  <monisotopic_moleculate_weight>188.104859</monisotopic_moleculate_weight>
  <iupac_name>nonanedioic acid</iupac_name>
  <traditional_iupac>azelaic acid</traditional_iupac>
  <cas_registry_number>123-99-9</cas_registry_number>
  <smiles>OC(=O)CCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)</inchi>
  <inchikey>BDJRBEYXGGNYIS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>alpha,omega-dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>106.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>2.4 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.57</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>nonanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>188.2209</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>188.104859</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H16O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BDJRBEYXGGNYIS-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440160</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB00548</drugbank_id>
  <foodb_id>FDB012192</foodb_id>
  <pubchem_compound_id>2266</pubchem_compound_id>
  <chemspider_id>2179</chemspider_id>
  <pdbe_id/>
  <kegg_id>C08261</kegg_id>
  <chebi_id>48131</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00045634</knapsack_id>
  <meta_cyc_id>CPD0-1265</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Azelaic_Acid</wikipedia_id>
  <metlin_id>5750</metlin_id>
  <synthesis_reference>Chen, Song; Yan, Jinlong.  Synthesis of azelaic acid by chemical oxidation with oleic acid.    Pige Huagong  (2003),  20(6),  31-35.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:31 UTC</creation_date>
  <update_date>2020-03-13 16:23:49 UTC</update_date>
  <accession>BMDB0000785</accession>
  <secondary_accessions>
    <accession>BMDB00785</accession>
  </secondary_accessions>
  <name>N-Acetyl-7-O-acetylneuraminic acid</name>
  <description/>
  <synonyms>
    <synonym>N-Acetyl-7-O-acetylneuraminate</synonym>
    <synonym>7-Acetate 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonate</synonym>
    <synonym>7-Acetate 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid</synonym>
    <synonym>7-Acetate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonate</synonym>
    <synonym>7-Acetate 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid</synonym>
    <synonym>7-O-Acetyl-N-acetylneuraminate</synonym>
    <synonym>7-O-Acetyl-N-acetylneuraminic acid</synonym>
    <synonym>Neu5,7ac2</synonym>
    <synonym>(2S,4S,5R,6R)-6-[(1R,2R)-1-(Acetyloxy)-2,3-dihydroxypropyl]-2,4-dihydroxy-5-[(1-hydroxyethylidene)amino]oxane-2-carboxylate</synonym>
  </synonyms>
  <chemical_formula>C13H21NO10</chemical_formula>
  <average_molecular_weight>351.3065</average_molecular_weight>
  <monisotopic_moleculate_weight>351.116545897</monisotopic_moleculate_weight>
  <iupac_name>(2S,4S,5R,6R)-6-[(1R,2R)-1-(acetyloxy)-2,3-dihydroxypropyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>(2S,4S,5R,6R)-6-[(1R,2R)-1-(acetyloxy)-2,3-dihydroxypropyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid</traditional_iupac>
  <cas_registry_number>18529-63-0</cas_registry_number>
  <smiles>CC(=O)N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](OC(C)=O)[C@H](O)CO)C(O)=O</smiles>
  <inchi>InChI=1S/C13H21NO10/c1-5(16)14-9-7(18)3-13(22,12(20)21)24-11(9)10(8(19)4-15)23-6(2)17/h7-11,15,18-19,22H,3-4H2,1-2H3,(H,14,16)(H,20,21)/t7-,8+,9+,10+,11+,13-/m0/s1</inchi>
  <inchikey>DUOKWMWKFGDUDQ-GRRZBWEESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>N-acylneuraminic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>C-glucuronides</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Neuraminic acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>C-glucuronide</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>N-acylneuraminic acid</substituent>
      <substituent>Neuraminic acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,4S,5R,6R)-6-[(1R,2R)-1-(acetyloxy)-2,3-dihydroxypropyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>351.3065</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>351.116545897</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](OC(C)=O)[C@H](O)CO)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H21NO10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H21NO10/c1-5(16)14-9-7(18)3-13(22,12(20)21)24-11(9)10(8(19)4-15)23-6(2)17/h7-11,15,18-19,22H,3-4H2,1-2H3,(H,14,16)(H,20,21)/t7-,8+,9+,10+,11+,13-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DUOKWMWKFGDUDQ-GRRZBWEESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>182.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337476</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022241</foodb_id>
  <chemspider_id>17216006</chemspider_id>
  <pubchem_compound_id>12315523</pubchem_compound_id>
  <kegg_id>C04016</kegg_id>
  <pdbe_id/>
  <chebi_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5751</metlin_id>
  <synthesis_reference>Diaz, Sandra; Higa, Herman H.; Hayes, Bradley K.; Varki, Ajit.  O-Acetylation and de-O-acetylation of sialic acids.  7- and 9-O-acetylation of a2,6-linked sialic acids on endogenous N-linked glycans in rat liver Golgi vesicles.    Journal of Biological Chemistry  (1989),  264(32),  19416-26.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:34 UTC</creation_date>
  <update_date>2020-04-14 22:48:23 UTC</update_date>
  <accession>BMDB0000788</accession>
  <secondary_accessions>
    <accession>BMDB00788</accession>
  </secondary_accessions>
  <name>Orotidine</name>
  <description/>
  <synonyms>
    <synonym>3-Ribofuranosylorotic acid</synonym>
    <synonym>6-Carboxyuridine</synonym>
    <synonym>3-Ribofuranosylorotate</synonym>
    <synonym>Orotic acid riboside</synonym>
    <synonym>Orotidine, ammonium salt</synonym>
  </synonyms>
  <chemical_formula>C10H12N2O8</chemical_formula>
  <average_molecular_weight>288.2109</average_molecular_weight>
  <monisotopic_moleculate_weight>288.05936537</monisotopic_moleculate_weight>
  <iupac_name>3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid</iupac_name>
  <traditional_iupac>orotidine</traditional_iupac>
  <cas_registry_number>314-50-1</cas_registry_number>
  <smiles>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C(=O)NC(=O)C=C1C(O)=O</smiles>
  <inchi>InChI=1S/C10H12N2O8/c13-2-4-6(15)7(16)8(20-4)12-3(9(17)18)1-5(14)11-10(12)19/h1,4,6-8,13,15-16H,2H2,(H,17,18)(H,11,14,19)/t4-,6-,7-,8-/m1/s1</inchi>
  <inchikey>FKCRAVPPBFWEJD-XVFCMESISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleosides</class>
    <sub_class/>
    <direct_parent>Pyrimidine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidine carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidinecarboxylic acids</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydropyrimidine carboxylic acid derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine nucleoside</substituent>
      <substituent>Pyrimidine-6-carboxylic acid</substituent>
      <substituent>Pyrimidine-6-carboxylic acid or derivatives</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>nucleoside</external_descriptor>
      <external_descriptor>pyrimidinemonocarboxylic acid</external_descriptor>
      <external_descriptor>uridines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>&gt; 400 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>288.2109</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>288.05936537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C(=O)NC(=O)C=C1C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N2O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N2O8/c13-2-4-6(15)7(16)8(20-4)12-3(9(17)18)1-5(14)11-10(12)19/h1,4,6-8,13,15-16H,2H2,(H,17,18)(H,11,14,19)/t4-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FKCRAVPPBFWEJD-XVFCMESISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>156.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>59.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359733</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB012085</foodb_id>
  <chemspider_id>83729</chemspider_id>
  <pubchem_compound_id>92751</pubchem_compound_id>
  <kegg_id>C01103</kegg_id>
  <chebi_id>25722</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Orotidine</wikipedia_id>
  <metlin_id>5754</metlin_id>
  <synthesis_reference>Curra, William V.; Angle, Robert B.  Synthesis of orotidine.    Tetrahedron Letters  (1963),   (8),  533-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:35 UTC</creation_date>
  <update_date>2020-04-15 22:14:32 UTC</update_date>
  <accession>BMDB0000789</accession>
  <secondary_accessions>
    <accession>BMDB00789</accession>
  </secondary_accessions>
  <name>Pentacarboxylporphyrin I</name>
  <description/>
  <synonyms>
    <synonym>21H,23H-Porphinepentacarboxylate</synonym>
    <synonym>21H,23H-Porphinepentacarboxylic acid</synonym>
    <synonym>3-(Carboxymethyl)-8,13,17-trimethyl-2,7,12,18-porphinetetrapropionate</synonym>
    <synonym>3-(Carboxymethyl)-8,13,17-trimethyl-2,7,12,18-porphinetetrapropionic acid</synonym>
    <synonym>Pentacarboxylic acid porphyrin I</synonym>
    <synonym>Pentacarboxyporphyrin I</synonym>
    <synonym>3-[10,14,19-Tris(2-carboxyethyl)-15-(carboxymethyl)-5,9,20-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6(24),7,9,11,13,15,17,19-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C37H38N4O10</chemical_formula>
  <average_molecular_weight>698.7184</average_molecular_weight>
  <monisotopic_moleculate_weight>698.258793456</monisotopic_moleculate_weight>
  <iupac_name>3-[10,15,20-tris(2-carboxyethyl)-19-(carboxymethyl)-5,9,14-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6,8(23),9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[10,15,20-tris(2-carboxyethyl)-19-(carboxymethyl)-5,9,14-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6,8(23),9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>28100-78-9</cas_registry_number>
  <smiles>CC1=C(CCC(O)=O)/C2=C/C3=C(CCC(O)=O)C(CC(O)=O)=C(N3)\C=C3/N=C(/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)C(C)=C3CCC(O)=O</smiles>
  <inchi>InChI=1S/C37H38N4O10/c1-17-20(4-8-33(42)43)28-14-27-19(3)22(6-10-35(46)47)30(40-27)16-32-24(12-37(50)51)23(7-11-36(48)49)31(41-32)15-29-21(5-9-34(44)45)18(2)26(39-29)13-25(17)38-28/h13-16,39,41H,4-12H2,1-3H3,(H,42,43)(H,44,45)(H,46,47)(H,48,49)(H,50,51)/b25-13-,26-13-,27-14-,28-14-,29-15-,30-16-,31-15-,32-16-</inchi>
  <inchikey>YDYIPLSPVWGSRD-TXUIXYGZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[10,15,20-tris(2-carboxyethyl)-19-(carboxymethyl)-5,9,14-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6,8(23),9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>698.7184</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>698.258793456</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCC(O)=O)/C2=C/C3=C(CCC(O)=O)C(CC(O)=O)=C(N3)\C=C3/N=C(/C=C4\N=C(\C=C\1/N\2)C(C)=C4CCC(O)=O)C(C)=C3CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C37H38N4O10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C37H38N4O10/c1-17-20(4-8-33(42)43)28-14-27-19(3)22(6-10-35(46)47)30(40-27)16-32-24(12-37(50)51)23(7-11-36(48)49)31(41-32)15-29-21(5-9-34(44)45)18(2)26(39-29)13-25(17)38-28/h13-16,39,41H,4-12H2,1-3H3,(H,42,43)(H,44,45)(H,46,47)(H,48,49)(H,50,51)/b25-13-,26-13-,27-14-,28-14-,29-15-,30-16-,31-15-,32-16-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YDYIPLSPVWGSRD-TXUIXYGZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>243.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>182.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>76.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350376</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022244</foodb_id>
  <chemspider_id>147620</chemspider_id>
  <pubchem_compound_id/>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5755</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:36 UTC</creation_date>
  <update_date>2020-03-13 16:23:51 UTC</update_date>
  <accession>BMDB0000790</accession>
  <secondary_accessions>
    <accession>BMDB00790</accession>
  </secondary_accessions>
  <name>N-Palmitoylsphingosine</name>
  <description/>
  <synonyms>
    <synonym>D-erythro-C16-Ceramide</synonym>
    <synonym>D-erythro-D4-Ceramide</synonym>
    <synonym>N-Palmitoyl 4-sphingenine</synonym>
    <synonym>N-Palmitoyl-D-sphingosine</synonym>
    <synonym>[R-[R*,s*-(e)]]-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-hexadecanamide</synonym>
    <synonym>C(16)-Ceramide</synonym>
    <synonym>C16-Ceramide</synonym>
    <synonym>C16-Palmitoylceramide</synonym>
    <synonym>N-Palmitoylsphingosine, (r*,s*-(e))-(+-)</synonym>
    <synonym>N-Palmitoylsphingosine, R-(r*,s*-(e))</synonym>
    <synonym>NFA(C16)cer</synonym>
    <synonym>PCer CPD</synonym>
    <synonym>Palmitoylceramide</synonym>
    <synonym>N-(1,3-Dihydroxyoctadec-4-en-2-yl)hexadecanimidate</synonym>
    <synonym>N-Palmitoylsphingosine</synonym>
    <synonym>C16-0(Palmitoyl)ceramide</synonym>
    <synonym>Ceramide-C16</synonym>
  </synonyms>
  <chemical_formula>C34H67NO3</chemical_formula>
  <average_molecular_weight>537.9007</average_molecular_weight>
  <monisotopic_moleculate_weight>537.512095015</monisotopic_moleculate_weight>
  <iupac_name>N-[(4E)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide</iupac_name>
  <traditional_iupac>N-[(4E)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide</traditional_iupac>
  <cas_registry_number/>
  <smiles>CCCCCCCCCCCCCCCC(=O)NC(CO)C(O)\C=C\CCCCCCCCCCCCC</smiles>
  <inchi>InChI=1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/b29-27+</inchi>
  <inchikey>YDNKGFDKKRUKPY-ORIPQNMZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain ceramides. These are ceramides bearing a long chain fatty acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Sphingolipids</class>
    <sub_class>Ceramides</sub_class>
    <direct_parent>Long-chain ceramides</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain ceramide</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>9.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>10.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[(4E)-1,3-dihydroxyoctadec-4-en-2-yl]hexadecanamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>537.9007</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>537.512095015</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCC(=O)NC(CO)C(O)\C=C\CCCCCCCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C34H67NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/b29-27+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YDNKGFDKKRUKPY-ORIPQNMZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>69.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>165.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>73.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>30</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id>5353456</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Duclos, R. I.  The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog.    Chemistry and Physics of Lipids  (2001),  111(2),  111-138.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:37 UTC</creation_date>
  <update_date>2020-04-14 22:48:24 UTC</update_date>
  <accession>BMDB0000791</accession>
  <secondary_accessions>
    <accession>BMDB00791</accession>
  </secondary_accessions>
  <name>L-Octanoylcarnitine</name>
  <description>L-Octanoylcarnitine belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Thus, L-octanoylcarnitine is considered to be a fatty ester lipid molecule. L-Octanoylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. L-Octanoylcarnitine has been found to be associated with several diseases known as pregnancy, colorectal cancer, and ulcerative colitis; also l-octanoylcarnitine has been linked to several inborn metabolic disorders including celiac disease and very long chain acyl-coa dehydrogenase deficiency.</description>
  <synonyms>
    <synonym>L-Octanoyl-L-carnitine</synonym>
    <synonym>O-Octanoyl-(R)-carnitine</synonym>
    <synonym>O-Octanoyl-R-carnitine</synonym>
    <synonym>(-)-Octanoylcarnitine</synonym>
    <synonym>L-Carnitine octanoyl ester</synonym>
    <synonym>L-O-Octanoylcarnitine</synonym>
    <synonym>Octanoic acid ester with L-(3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt</synonym>
    <synonym>Octanoyl-L-carnitine</synonym>
    <synonym>Octanoylcarnitine</synonym>
    <synonym>Octanoylcarnitine chloride, (R)-isomer</synonym>
    <synonym>Octanoylcarnitine, (R)-isomer</synonym>
    <synonym>Octanoylcarnitine chloride</synonym>
    <synonym>Octanoylcarnitine chloride, (+-)-isomer</synonym>
    <synonym>Octanoylcarnitine, (+-)-isomer</synonym>
    <synonym>C8-Carnitine</synonym>
    <synonym>L-Octanoylcarnitine</synonym>
  </synonyms>
  <chemical_formula>C15H29NO4</chemical_formula>
  <average_molecular_weight>287.3951</average_molecular_weight>
  <monisotopic_moleculate_weight>287.209658421</monisotopic_moleculate_weight>
  <iupac_name>(3R)-3-(octanoyloxy)-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>L-octanoylcarnitine</traditional_iupac>
  <cas_registry_number>25243-95-2</cas_registry_number>
  <smiles>CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C</smiles>
  <inchi>InChI=1S/C15H29NO4/c1-5-6-7-8-9-10-15(19)20-13(11-14(17)18)12-16(2,3)4/h13H,5-12H2,1-4H3/t13-/m1/s1</inchi>
  <inchikey>CXTATJFJDMJMIY-CYBMUJFWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Acyl carnitines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl-carnitine</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fatty acyl carnitines</external_descriptor>
      <external_descriptor>Fatty acyl carnitines</external_descriptor>
      <external_descriptor>O-acyl-L-carnitine</external_descriptor>
      <external_descriptor>O-octanoylcarnitine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R)-3-(octanoyloxy)-4-(trimethylazaniumyl)butanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>287.3951</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>287.209658421</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H29NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H29NO4/c1-5-6-7-8-9-10-15(19)20-13(11-14(17)18)12-16(2,3)4/h13H,5-12H2,1-4H3/t13-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CXTATJFJDMJMIY-CYBMUJFWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>100.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1128</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.02+/-0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>0.09+/-0.02</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>0.26+/-0.32</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.014+/-0.003</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>0.27+/-0.24</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>0.06+/-0.01</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022246</foodb_id>
  <pubchem_compound_id>11953814</pubchem_compound_id>
  <chemspider_id>10128115</chemspider_id>
  <pdbe_id/>
  <kegg_id>C02838</kegg_id>
  <chebi_id>18102</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>L-OCTANOYLCARNITINE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Duhr, Edward F.; Mauro, J. Matthew; Clennan, Edward L.; Barden, Roland E.  The synthesis and biological activity of thiolcarnitine and its thiolesters.    Lipids  (1983),  18(5),  382-6.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00244</protein_accession>
      <name>Peroxisomal carnitine O-octanoyltransferase</name>
      <uniprot_id>O19094</uniprot_id>
      <gene_name>CROT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:38 UTC</creation_date>
  <update_date>2020-03-13 16:23:52 UTC</update_date>
  <accession>BMDB0000792</accession>
  <secondary_accessions>
    <accession>BMDB00792</accession>
  </secondary_accessions>
  <name>Sebacic acid</name>
  <description/>
  <synonyms>
    <synonym>1,10-Decanedioic acid</synonym>
    <synonym>1,8-Dicarboxyoctane</synonym>
    <synonym>Decanedioic acid</synonym>
    <synonym>Sebacinsaeure</synonym>
    <synonym>1,10-Decanedioate</synonym>
    <synonym>Decanedioate</synonym>
    <synonym>Sebacate</synonym>
    <synonym>Sebacic acid, monocadmium salt</synonym>
    <synonym>Sebacic acid, aluminum salt</synonym>
    <synonym>Sebacic acid, sodium salt</synonym>
    <synonym>1,8-Octanedicarboxylate</synonym>
    <synonym>1,8-Octanedicarboxylic acid</synonym>
    <synonym>4,7-Dioxosebacic acid</synonym>
    <synonym>4-Oxodecanedioate</synonym>
    <synonym>4-Oxodecanedioic acid</synonym>
    <synonym>Acide sebacique</synonym>
    <synonym>Decanedicarboxylic acid</synonym>
    <synonym>Dicarboxylic acid C10</synonym>
    <synonym>Ipomic acid</synonym>
    <synonym>N-Decanedioate</synonym>
    <synonym>N-Decanedioic acid</synonym>
    <synonym>Sebacic acids</synonym>
    <synonym>Sebacinsaure</synonym>
    <synonym>Seracic acid</synonym>
  </synonyms>
  <chemical_formula>C10H18O4</chemical_formula>
  <average_molecular_weight>202.2475</average_molecular_weight>
  <monisotopic_moleculate_weight>202.120509064</monisotopic_moleculate_weight>
  <iupac_name>decanedioic acid</iupac_name>
  <traditional_iupac>sebacic acid</traditional_iupac>
  <cas_registry_number>111-20-6</cas_registry_number>
  <smiles>OC(=O)CCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)</inchi>
  <inchikey>CXMXRPHRNRROMY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>alpha,omega-dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>130.8 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>decanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>202.2475</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>202.120509064</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H18O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CXMXRPHRNRROMY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452101</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB07645</drugbank_id>
  <foodb_id>FDB022247</foodb_id>
  <pubchem_compound_id>5192</pubchem_compound_id>
  <chemspider_id>5004</chemspider_id>
  <pdbe_id/>
  <kegg_id>C08277</kegg_id>
  <chebi_id>41865</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001202</knapsack_id>
  <meta_cyc_id>CPD-3623</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Sebacic_acid</wikipedia_id>
  <metlin_id>4240</metlin_id>
  <synthesis_reference>Li, Aimin; Jiang, Zhenmao; Cai, Jianguo; Zhang, Xiao; Shi, Hongyan; Zhou, Jiayan; Zhang, Quanxing; Long, Chao; Liu, Fuqiang; Chen, Jinlong.  Environmental friendly method for producing sebacic acid using anion exchangers and polymer adsorbents.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2005),     5 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:39 UTC</creation_date>
  <update_date>2020-03-13 16:23:52 UTC</update_date>
  <accession>BMDB0000793</accession>
  <secondary_accessions>
    <accession>BMDB00793</accession>
  </secondary_accessions>
  <name>Monoiodothyronine</name>
  <description/>
  <synonyms>
    <synonym>3-Iodothyronine</synonym>
    <synonym>3-Monoiodothyronine</synonym>
    <synonym>3-T1</synonym>
    <synonym>Iodo-thyronine</synonym>
    <synonym>O-(4-Hydroxyphenyl)-3-iodotyrosine</synonym>
    <synonym>3-Monoiodothyronine, (L-tyr)-isomer</synonym>
    <synonym>3-Monoiodothyronine, 125I-labeled, (L-tyr)-isomer</synonym>
    <synonym>3-Monoiodothyronine, (DL-tyr)-isomer</synonym>
    <synonym>(2R)-2-Amino-3-[4-(4-hydroxyphenoxy)-3-iodophenyl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C15H14INO4</chemical_formula>
  <average_molecular_weight>399.1804</average_molecular_weight>
  <monisotopic_moleculate_weight>398.996751361</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-amino-3-[4-(4-hydroxyphenoxy)-3-iodophenyl]propanoic acid</iupac_name>
  <traditional_iupac>(2R)-2-amino-3-[4-(4-hydroxyphenoxy)-3-iodophenyl]propanoic acid</traditional_iupac>
  <cas_registry_number>29354-16-3</cas_registry_number>
  <smiles>N[C@H](CC1=CC(I)=C(OC2=CC=C(O)C=C2)C=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C15H14INO4/c16-12-7-9(8-13(17)15(19)20)1-6-14(12)21-11-4-2-10(18)3-5-11/h1-7,13,18H,8,17H2,(H,19,20)/t13-/m1/s1</inchi>
  <inchikey>SXQVOFSDWXYIRP-CYBMUJFWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Phenylalanine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aryl iodides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>D-alpha-amino acids</alternative_parent>
      <alternative_parent>Diarylethers</alternative_parent>
      <alternative_parent>Diphenylethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Iodobenzenes</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organoiodides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenol ethers</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Aryl iodide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>D-alpha-amino acid</substituent>
      <substituent>Diaryl ether</substituent>
      <substituent>Diphenylether</substituent>
      <substituent>Ether</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Iodobenzene</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organoiodide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-amino-3-[4-(4-hydroxyphenoxy)-3-iodophenyl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>399.1804</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>398.996751361</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@H](CC1=CC(I)=C(OC2=CC=C(O)C=C2)C=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H14INO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H14INO4/c16-12-7-9(8-13(17)15(19)20)1-6-14(12)21-11-4-2-10(18)3-5-11/h1-7,13,18H,8,17H2,(H,19,20)/t13-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SXQVOFSDWXYIRP-CYBMUJFWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335232</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022248</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477717</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5758</metlin_id>
  <synthesis_reference>Blanquet, Paul; Mounier, Jean; Meyniel, Gaston.  Formation of iodothyronine from diiodotyrosine, caused by ultrasonic vibrations.    Compt. rend.  (1958),  246  2058-60.  CAN 52:80697  AN 1958:80697</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:40 UTC</creation_date>
  <update_date>2020-03-13 16:23:53 UTC</update_date>
  <accession>BMDB0000794</accession>
  <secondary_accessions>
    <accession>BMDB00794</accession>
  </secondary_accessions>
  <name>N-Acetyl-9-O-acetylneuraminic acid</name>
  <description/>
  <synonyms>
    <synonym>9-Anana</synonym>
    <synonym>9-O-Acetyl-N-acetylneuraminic acid</synonym>
    <synonym>9-O-Acetylsialic acid</synonym>
    <synonym>9-O-Acetyl-N-acetylneuraminate</synonym>
    <synonym>9-O-Acetylsialate</synonym>
    <synonym>N-Acetyl-9-O-acetylneuraminate</synonym>
    <synonym>N,9-O-Diacetylneuraminate</synonym>
    <synonym>N,9-O-Diacetylneuraminic acid</synonym>
    <synonym>Neu5,9ac2</synonym>
  </synonyms>
  <chemical_formula>C13H21NO10</chemical_formula>
  <average_molecular_weight>351.3065</average_molecular_weight>
  <monisotopic_moleculate_weight>351.116545897</monisotopic_moleculate_weight>
  <iupac_name>(2S,4S,5R,6R)-6-[(1R,2R)-3-(acetyloxy)-1,2-dihydroxypropyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>9-O-acetylsialic acid</traditional_iupac>
  <cas_registry_number>55717-54-9</cas_registry_number>
  <smiles>CC(=O)N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)COC(C)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C13H21NO10/c1-5(15)14-9-7(17)3-13(22,12(20)21)24-11(9)10(19)8(18)4-23-6(2)16/h7-11,17-19,22H,3-4H2,1-2H3,(H,14,15)(H,20,21)/t7-,8+,9+,10+,11+,13-/m0/s1</inchi>
  <inchikey>NYWZBRWKDRMPAS-GRRZBWEESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Neuraminic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>C-glucuronides</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>C-glucuronide</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Neuraminic acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acetyl-O-acetylneuraminic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,4S,5R,6R)-6-[(1R,2R)-3-(acetyloxy)-1,2-dihydroxypropyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>351.3065</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>351.116545897</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)COC(C)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H21NO10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H21NO10/c1-5(15)14-9-7(17)3-13(22,12(20)21)24-11(9)10(19)8(18)4-23-6(2)16/h7-11,17-19,22H,3-4H2,1-2H3,(H,14,15)(H,20,21)/t7-,8+,9+,10+,11+,13-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NYWZBRWKDRMPAS-GRRZBWEESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>182.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363507</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022249</foodb_id>
  <chemspider_id>110484</chemspider_id>
  <pubchem_compound_id>123962</pubchem_compound_id>
  <kegg_id/>
  <chebi_id>21500</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5759</metlin_id>
  <synthesis_reference>Forstner, Michael; Freytag, Katharina; Paschke, Eduard.  A simple, one-step synthesis of N-acetyl-9-O-acetylneuraminic acid by enzymic transesterification mediated by porcine pancreas lipase in pyridine.    Carbohydrate Research  (1989),  193  294-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:42 UTC</creation_date>
  <update_date>2020-04-16 17:53:15 UTC</update_date>
  <accession>BMDB0000795</accession>
  <secondary_accessions>
    <accession>BMDB00795</accession>
  </secondary_accessions>
  <name>Pristanic acid</name>
  <description>Pristanic acid, also known as pristanic acid or pristanic acid, belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Pristanic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Pristanic acid can be biosynthesized from pristanal through its interaction with the enzyme fatty aldehyde dehydrogenase. In cattle, pristanic acid is involved in the metabolic pathway called the phytanic Acid peroxisomal oxidation pathway.</description>
  <synonyms>
    <synonym>2,6,10,14-Tetramethyl-pentadecansaeure</synonym>
    <synonym>2,6,10,14-Tetramethylpentadecylic acid</synonym>
    <synonym>Acide pristanique</synonym>
    <synonym>Acido pristanico</synonym>
    <synonym>Pristaninsaeure</synonym>
    <synonym>2,6,10,14-Tetramethylpentadecylate</synonym>
    <synonym>Pristanate</synonym>
    <synonym>(2S)-Pristanic acid</synonym>
    <synonym>(2S,6R,10R)-2,6,10,14-Tetramethylpentadecanoate</synonym>
    <synonym>(2S,6R,10R)-2,6,10,14-Tetramethylpentadecanoic acid</synonym>
    <synonym>(2S,6R,10R)-Pristanic acid</synonym>
    <synonym>2,6,10,14-Tetramethylpentadecanoate</synonym>
    <synonym>2,6,10,14-Tetramethylpentadecanoic acid</synonym>
    <synonym>Pristanate:(2S,6R,10R)-pristanate</synonym>
  </synonyms>
  <chemical_formula>C19H38O2</chemical_formula>
  <average_molecular_weight>298.511</average_molecular_weight>
  <monisotopic_moleculate_weight>298.287180464</monisotopic_moleculate_weight>
  <iupac_name>2,6,10,14-tetramethylpentadecanoic acid</iupac_name>
  <traditional_iupac>pristanic acid</traditional_iupac>
  <cas_registry_number>1189-37-3</cas_registry_number>
  <smiles>CC(C)CCCC(C)CCCC(C)CCCC(C)C(O)=O</smiles>
  <inchi>InChI=1S/C19H38O2/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19(20)21/h15-18H,6-14H2,1-5H3,(H,20,21)</inchi>
  <inchikey>PAHGJZDQXIOYTH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Diterpenoids</sub_class>
    <direct_parent>Acyclic diterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyclic diterpenoid</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Acyclic diterpenoids</external_descriptor>
      <external_descriptor>branched-chain saturated fatty acid</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>methyl-branched fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,6,10,14-tetramethylpentadecanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>298.511</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>298.287180464</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CCCC(C)CCCC(C)CCCC(C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H38O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H38O2/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19(20)21/h15-18H,6-14H2,1-5H3,(H,20,21)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PAHGJZDQXIOYTH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>90.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242829</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB012993</foodb_id>
  <chemspider_id>110458</chemspider_id>
  <pubchem_compound_id>123929</pubchem_compound_id>
  <kegg_id/>
  <chebi_id>51340</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id>PRISTANATE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>2364527</bigg_id>
  <wikipedia_id>Pristanic acid</wikipedia_id>
  <metlin_id>5760</metlin_id>
  <synthesis_reference>Nakajima, Kenji; Sato, Akio.  Microbial oxidation of isoprenoid hydrocarbons.  Part II.  Production of pristanol and pristanic acid from pristane by Nocardia sp. BPM 1613.    Nippon Nogei Kagaku Kaishi  (1981),  55(9),  825-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:43 UTC</creation_date>
  <update_date>2020-03-13 16:23:54 UTC</update_date>
  <accession>BMDB0000796</accession>
  <secondary_accessions>
    <accession>BMDB00796</accession>
  </secondary_accessions>
  <name>N-Acetyl-4-O-acetylneuraminic acid</name>
  <description/>
  <synonyms>
    <synonym>N-Acetyl-4-O-acetylneuraminate</synonym>
    <synonym>(2S,4S,5R,6R)-4-(Acetyloxy)-2-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate</synonym>
  </synonyms>
  <chemical_formula>C13H21NO10</chemical_formula>
  <average_molecular_weight>351.308</average_molecular_weight>
  <monisotopic_moleculate_weight>351.11654588</monisotopic_moleculate_weight>
  <iupac_name>(2S,4S,5R,6R)-4-(acetyloxy)-2-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>neu4,5ac2</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H]C(O)(CO)[C@@]([H])(O)[C@]1([H])O[C@@](O)(C[C@]([H])(OC(C)=O)[C@@]1([H])N=C(C)O)C(O)=O</smiles>
  <inchi>InChI=1S/C13H21NO10/c1-5(16)14-9-8(23-6(2)17)3-13(22,12(20)21)24-11(9)10(19)7(18)4-15/h7-11,15,18-19,22H,3-4H2,1-2H3,(H,14,16)(H,20,21)/t7?,8-,9+,10+,11+,13-/m0/s1</inchi>
  <inchikey>LVBIMVQYUKOENY-QLEAHAHXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Neuraminic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>C-glucuronides</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>C-glucuronide</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Neuraminic acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,4S,5R,6R)-4-(acetyloxy)-2-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>351.308</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>351.11654588</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]C(O)(CO)[C@@]([H])(O)[C@]1([H])O[C@@](O)(C[C@]([H])(OC(C)=O)[C@@]1([H])N=C(C)O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H21NO10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H21NO10/c1-5(16)14-9-8(23-6(2)17)3-13(22,12(20)21)24-11(9)10(19)7(18)4-15/h7-11,15,18-19,22H,3-4H2,1-2H3,(H,14,16)(H,20,21)/t7?,8-,9+,10+,11+,13-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LVBIMVQYUKOENY-QLEAHAHXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>186.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>73.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1269463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1269464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1269465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1384486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1384487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1384488</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <kegg_id/>
  <pubchem_compound_id>25201413</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Ogura, Haruo; Furuhata, Kimio; Sato, Shingo; Anazawa, Katsuko; Shidori, Yoshiyasu; Ito, Masayoshi.  A process for preparation of N-acetyl-4-O-acetylneuraminic acid, a ganglioside intermediate.    Jpn. Kokai Tokkyo Koho  (1988),     7 pp.  CODEN: JKXXAF  JP  63044587  A  19880225  Showa.   CAN 109:110857  AN 1988:510857  </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:44 UTC</creation_date>
  <update_date>2020-04-15 22:07:00 UTC</update_date>
  <accession>BMDB0000797</accession>
  <secondary_accessions>
    <accession>BMDB00797</accession>
  </secondary_accessions>
  <name>SAICAR</name>
  <description/>
  <synonyms>
    <synonym>(2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinic acid</synonym>
    <synonym>(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate</synonym>
    <synonym>1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole</synonym>
    <synonym>1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole</synonym>
    <synonym>5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole</synonym>
    <synonym>Succino-aicar</synonym>
    <synonym>Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphate</synonym>
    <synonym>Succinylaminoimidazolecarboxamide ribose-5'-phosphate</synonym>
    <synonym>(2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinate</synonym>
    <synonym>(2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinic acid</synonym>
    <synonym>(2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinate</synonym>
    <synonym>(2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinate</synonym>
    <synonym>(2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinic acid</synonym>
    <synonym>(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinic acid</synonym>
    <synonym>Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphoric acid</synonym>
    <synonym>Succinylaminoimidazolecarboxamide ribose-5'-phosphoric acid</synonym>
    <synonym>(S)-2-(5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate</synonym>
    <synonym>(S)-2-(5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinic acid</synonym>
    <synonym>(S)-2-(5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinate</synonym>
    <synonym>(S)-2-(5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinic acid</synonym>
    <synonym>(S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinate</synonym>
    <synonym>1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole' 1-(5'-phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole</synonym>
    <synonym>5'-Phosphoribosyl-4-(N-succinocarbozamide)-5-aminoimidazole</synonym>
    <synonym>5-Amino-4-imidazole-N-succinocarboxamide ribonucleotide</synonym>
    <synonym>L-N-[(5-Amino-1-b-D-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)</synonym>
    <synonym>L-N-[(5-Amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)</synonym>
    <synonym>N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphate</synonym>
    <synonym>N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartate</synonym>
    <synonym>N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartic acid</synonym>
    <synonym>Phosphoribosylaminoimidazolesuccinocarboxamide</synonym>
    <synonym>N-(5-Amino-1-beta-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic acid 5'-phosphate</synonym>
    <synonym>5'-Phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole</synonym>
    <synonym>SAICAR, (D)-isomer</synonym>
    <synonym>SAICAribotide</synonym>
    <synonym>Succinylaminoimidazole carboxamide ribotide</synonym>
    <synonym>SAICA ribotide</synonym>
    <synonym>Succinylaminoimidazolecarboxamide ribose-5’-phosphate</synonym>
  </synonyms>
  <chemical_formula>C13H19N4O12P</chemical_formula>
  <average_molecular_weight>454.2833</average_molecular_weight>
  <monisotopic_moleculate_weight>454.073708604</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-4-yl}formamido)butanedioic acid</iupac_name>
  <traditional_iupac>saicar</traditional_iupac>
  <cas_registry_number>3031-95-6</cas_registry_number>
  <smiles>NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](CC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C13H19N4O12P/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27)/t4-,5+,8+,9+,12+/m0/s1</inchi>
  <inchikey>NAQGHJTUZRHGAC-ZZZDFHIKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Imidazole ribonucleosides and ribonucleotides</class>
    <sub_class>1-ribosyl-imidazolecarboxamides</sub_class>
    <direct_parent>1-ribosyl-imidazolecarboxamides</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>2-heteroaryl carboxamides</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminoimidazoles</alternative_parent>
      <alternative_parent>Aspartic acid and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbonylimidazoles</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolyl carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>1-ribosyl-imidazolecarboxamide</substituent>
      <substituent>2-heteroaryl carboxamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminoimidazole</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Aspartic acid or derivatives</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazole-4-carbonyl group</substituent>
      <substituent>Imidazolyl carboxylic acid derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>1-(phosphoribosyl)imidazolecarboxamide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-4-yl}formamido)butanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>454.2833</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>454.073708604</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](CC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H19N4O12P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H19N4O12P/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27)/t4-,5+,8+,9+,12+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NAQGHJTUZRHGAC-ZZZDFHIKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>263.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>90.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175211</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022251</foodb_id>
  <chemspider_id>141175</chemspider_id>
  <kegg_id>C04823</kegg_id>
  <pubchem_compound_id>160666</pubchem_compound_id>
  <chebi_id>18319</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id>P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>44624</bigg_id>
  <wikipedia_id>Phosphoribosylaminoimidazolesuccinocarboxamide</wikipedia_id>
  <metlin_id>5762</metlin_id>
  <synthesis_reference>Shaw, Gordon; Thomas, Peter S.; Patey, Carole A. H.; Thomas, Susan E.  Purines, pyrimidines and imidazoles.  Part 50.  Inhibition of adenylosuccinate AMP-lyase no. 4.3.2.2. by derivatives of N-(5-amino-1-b-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic acid 5'-phosphate (SAICAR) and virazole 5'-phosphate.    Journal of the Chemical Society, Perkin Transactions 1:  Organic and Bio-Organic Chemistry (1972-1999)  (1979),   (6),  1415-24.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:45 UTC</creation_date>
  <update_date>2020-03-13 16:23:55 UTC</update_date>
  <accession>BMDB0000798</accession>
  <secondary_accessions>
    <accession>BMDB00798</accession>
  </secondary_accessions>
  <name>Oenanthic ether</name>
  <description/>
  <synonyms>
    <synonym>Enanthic acid ethyl ester</synonym>
    <synonym>Ethyl enanthate</synonym>
    <synonym>Grape oil</synonym>
    <synonym>Heptanoic acid ethyl ester</synonym>
    <synonym>Wine oil</synonym>
    <synonym>Enanthate ethyl ester</synonym>
    <synonym>Ethyl enanthic acid</synonym>
    <synonym>Heptanoate ethyl ester</synonym>
    <synonym>Cognac oil</synonym>
    <synonym>Enanthylic ether</synonym>
    <synonym>Ethyl heptanoate</synonym>
    <synonym>Ethyl heptanoic acid</synonym>
    <synonym>Ethyl heptoate</synonym>
    <synonym>Ethyl heptoic acid</synonym>
    <synonym>Ethyl heptylate</synonym>
    <synonym>Ethyl N-heptanoate</synonym>
    <synonym>Ethyl N-heptanoic acid</synonym>
    <synonym>Ethyl oenanthate</synonym>
    <synonym>Ethyl oenanthylate</synonym>
    <synonym>Heptanoic acid, ethyl ester</synonym>
    <synonym>Oenanthic ether</synonym>
  </synonyms>
  <chemical_formula>C9H18O2</chemical_formula>
  <average_molecular_weight>158.238</average_molecular_weight>
  <monisotopic_moleculate_weight>158.13067982</monisotopic_moleculate_weight>
  <iupac_name>ethyl heptanoate</iupac_name>
  <traditional_iupac>wine oil</traditional_iupac>
  <cas_registry_number>106-30-9</cas_registry_number>
  <smiles>CCCCCCC(=O)OCC</smiles>
  <inchi>InChI=1S/C9H18O2/c1-3-5-6-7-8-9(10)11-4-2/h3-8H2,1-2H3</inchi>
  <inchikey>TVQGDYNRXLTQAP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Fatty acid esters</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>fatty acid ethyl ester</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-66.1 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.29 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>ethyl heptanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>158.238</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>158.13067982</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCC(=O)OCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H18O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H18O2/c1-3-5-6-7-8-9(10)11-4-2/h3-8H2,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>TVQGDYNRXLTQAP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>26.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17515</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB008200</foodb_id>
  <pubchem_compound_id>7797</pubchem_compound_id>
  <chemspider_id>7509</chemspider_id>
  <pdbe_id/>
  <kegg_id/>
  <chebi_id>86618</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Ethyl_heptanoate</wikipedia_id>
  <metlin_id>5763</metlin_id>
  <synthesis_reference>Gogichaishvili, E. A.  Conditions of formation and accumulation of ethyl enanthate.    Tr. Inst. Sadovodstva, Vinogradarstva i Vinodeliya, Akad. Sel'skokhoz. Nauk Gruz. SSR  (1961),  13  413-18.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:46 UTC</creation_date>
  <update_date>2020-04-16 17:53:16 UTC</update_date>
  <accession>BMDB0000801</accession>
  <secondary_accessions>
    <accession>BMDB00801</accession>
  </secondary_accessions>
  <name>Phytanic acid</name>
  <description>Phytanic acid, also known as phytanate or acid, phytanic, belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Phytanic acid is possibly soluble (in water) and a very weakly acidic compound (based on its pKa). In cattle, phytanic acid is involved in the metabolic pathway called the phytanic Acid peroxisomal oxidation pathway. Phytanic acid is a potentially toxic compound. Phytanic acid has been found to be associated with several diseases known as cerebrotendinous xanthomatosis, rhizomelic chondrodysplasia punctata, and pseudoneonatal adrenoleukodystrophy; also phytanic acid has been linked to several inborn metabolic disorders including adrenoleukodystrophy and peroxisomal biogenesis defect.</description>
  <synonyms>
    <synonym>3,7,11,15-Tetramethyl hexadecanoic acid</synonym>
    <synonym>3,7,11,15-Tetramethyl-hexadecanoic acid</synonym>
    <synonym>3,7,11,15-Tetramethyl-hexadecansaeure</synonym>
    <synonym>3,7,11,15-Tetramethylhexadecanoic acid</synonym>
    <synonym>3,7,11,15-Tetramethyl hexadecanoate</synonym>
    <synonym>3,7,11,15-Tetramethyl-hexadecanoate</synonym>
    <synonym>3,7,11,15-Tetramethylhexadecanoate</synonym>
    <synonym>Phytanate</synonym>
    <synonym>3,7,11,15-Tetramethylhexadecoanoate</synonym>
    <synonym>3,7,11,15-Tetramethylhexadecoanoic acid</synonym>
    <synonym>Phytanoate</synonym>
    <synonym>Phytanoic acid</synonym>
    <synonym>Acid, phytanic</synonym>
  </synonyms>
  <chemical_formula>C20H40O2</chemical_formula>
  <average_molecular_weight>312.5304</average_molecular_weight>
  <monisotopic_moleculate_weight>312.302830524</monisotopic_moleculate_weight>
  <iupac_name>3,7,11,15-tetramethylhexadecanoic acid</iupac_name>
  <traditional_iupac>phytanic acid</traditional_iupac>
  <cas_registry_number>14721-66-5</cas_registry_number>
  <smiles>CC(C)CCCC(C)CCCC(C)CCCC(C)CC(O)=O</smiles>
  <inchi>InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)</inchi>
  <inchikey>RLCKHJSFHOZMDR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Diterpenoids</sub_class>
    <direct_parent>Acyclic diterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyclic diterpenoid</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Acyclic diterpenoids</external_descriptor>
      <external_descriptor>branched-chain saturated fatty acid</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>methyl-branched fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3,7,11,15-tetramethylhexadecanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>312.5304</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>312.302830524</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CCCC(C)CCCC(C)CCCC(C)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H40O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RLCKHJSFHOZMDR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>95.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>41.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19090</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
          <pubmed_id>14168161</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022252</foodb_id>
  <chemspider_id>25001</chemspider_id>
  <kegg_id>C01607</kegg_id>
  <pubchem_compound_id>26840</pubchem_compound_id>
  <chebi_id>16285</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>37991</bigg_id>
  <wikipedia_id>Phytanic acid</wikipedia_id>
  <metlin_id>5765</metlin_id>
  <synthesis_reference>Karrer, P.; Epprecht, A.; Konig, Hans.  General method of preparation for 2-methyl-3-alkylnaphthoquinones. Constitution and vitamin K activity.    Helvetica Chimica Acta  (1940),  23  272-83.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
      <pubmed_id>14168161</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:48 UTC</creation_date>
  <update_date>2020-04-15 22:14:33 UTC</update_date>
  <accession>BMDB0000802</accession>
  <secondary_accessions>
    <accession>BMDB00802</accession>
  </secondary_accessions>
  <name>Pterin</name>
  <description/>
  <synonyms>
    <synonym>2-Amino-4-hydroxypteridine</synonym>
    <synonym>2-Amino-4-oxopteridine</synonym>
    <synonym>2-Amino-4-hydroxyaminopteridine</synonym>
    <synonym>AHAPT</synonym>
    <synonym>2-Amino-1H-pteridin-4-one</synonym>
    <synonym>2-Amino-3H-pteridin-4-one</synonym>
    <synonym>2-Amino-4(1H)-pteridinone</synonym>
    <synonym>2-Amino-4(3H)-pteridinone</synonym>
    <synonym>2-Amino-4-pteridinol</synonym>
    <synonym>2-Amino-4-pteridone</synonym>
    <synonym>2-Amino-quinonoid dihydropterin</synonym>
    <synonym>2-Aminopteridin-4-one</synonym>
    <synonym>4-oxo-2-Aminopteridine</synonym>
    <synonym>4-Oxopterin</synonym>
    <synonym>Pteridoxamine</synonym>
    <synonym>Pterine</synonym>
  </synonyms>
  <chemical_formula>C6H5N5O</chemical_formula>
  <average_molecular_weight>163.1368</average_molecular_weight>
  <monisotopic_moleculate_weight>163.049409807</monisotopic_moleculate_weight>
  <iupac_name>2-amino-3,4-dihydropteridin-4-one</iupac_name>
  <traditional_iupac>2-amino-4-oxopteridine</traditional_iupac>
  <cas_registry_number>2236-60-4</cas_registry_number>
  <smiles>NC1=NC2=NC=CN=C2C(=O)N1</smiles>
  <inchi>InChI=1S/C6H5N5O/c7-6-10-4-3(5(12)11-6)8-1-2-9-4/h1-2H,(H3,7,9,10,11,12)</inchi>
  <inchikey>HNXQXTQTPAJEJL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Pterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrazines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pterin</substituent>
      <substituent>Pyrazine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a pterin</external_descriptor>
      <external_descriptor>pterin</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>0.175 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-3,4-dihydropteridin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>163.1368</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>163.049409807</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=NC=CN=C2C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H5N5O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H5N5O/c7-6-10-4-3(5(12)11-6)8-1-2-9-4/h1-2H,(H3,7,9,10,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HNXQXTQTPAJEJL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>93.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451982</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB005613</foodb_id>
  <chemspider_id>65806</chemspider_id>
  <kegg_id>C00715</kegg_id>
  <pubchem_compound_id>73000</pubchem_compound_id>
  <chebi_id>18265</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id>2-AMINO-4-HYDROXYPTERIDINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Pterin</wikipedia_id>
  <metlin_id>5766</metlin_id>
  <synthesis_reference>Taylor, Edward C.; Kobylecki, Ryszard. Pteridines. 43. A facile synthesis of 6-chloropterin and 2,4-diamino-6-chloropteridine. Journal of Organic Chemistry (1978), 43(4), 680-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00414</protein_accession>
      <name>Methionine synthase</name>
      <uniprot_id>Q4JIJ3</uniprot_id>
      <gene_name>MTR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:49 UTC</creation_date>
  <update_date>2020-03-13 16:23:57 UTC</update_date>
  <accession>BMDB0000803</accession>
  <secondary_accessions>
    <accession>BMDB00803</accession>
  </secondary_accessions>
  <name>Beta-N-Acetylglucosamine</name>
  <description/>
  <synonyms>
    <synonym>2-Acetamido-2-deoxy-D-glucose</synonym>
    <synonym>2-Acetylamino-2-deoxy-D-glucose</synonym>
    <synonym>Acetylglucosamine</synonym>
    <synonym>BetaGlcNAc</synonym>
    <synonym>GlcNAc-beta</synonym>
    <synonym>N-Acetyl-D-glucosamine</synonym>
    <synonym>N-Acetylglucosamine</synonym>
    <synonym>GlcNAc-b</synonym>
    <synonym>GlcNAc-β</synonym>
    <synonym>b-N-Acetylglucosamine</synonym>
    <synonym>Β-N-acetylglucosamine</synonym>
    <synonym>N-Acetyl-b-D-glucosamine</synonym>
    <synonym>N-Acetyl-β-D-glucosamine</synonym>
    <synonym>N Acetyl D glucosamine</synonym>
    <synonym>2 Acetamido 2 deoxyglucose</synonym>
    <synonym>2 Acetamido 2 deoxy D glucose</synonym>
    <synonym>2-Acetamido-2-deoxyglucose</synonym>
    <synonym>2-Acetamido-2-deoxy-b-D-glucose</synonym>
    <synonym>2-Acetamido-2-deoxy-beta-D-glucose</synonym>
    <synonym>2-Acetamido-2-deoxy-beta-delta-glucose</synonym>
    <synonym>b-N-Acetyl-D-glucosamine</synonym>
    <synonym>beta-N-Acetyl-D-glucosamine</synonym>
    <synonym>beta-N-Acetyl-delta-glucosamine</synonym>
    <synonym>N-Acetyl-beta-D-glucosamine</synonym>
    <synonym>N-Acetyl glucosamine</synonym>
  </synonyms>
  <chemical_formula>C8H15NO6</chemical_formula>
  <average_molecular_weight>221.2078</average_molecular_weight>
  <monisotopic_moleculate_weight>221.089937217</monisotopic_moleculate_weight>
  <iupac_name>N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide</iupac_name>
  <traditional_iupac>N-acetyl-D-glucosamine</traditional_iupac>
  <cas_registry_number>14131-68-1</cas_registry_number>
  <smiles>CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8-/m1/s1</inchi>
  <inchikey>OVRNDRQMDRJTHS-FMDGEEDCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Acylaminosugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Acylaminosugar</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acetyl-D-glucosamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>221.2078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>221.089937217</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15NO6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OVRNDRQMDRJTHS-FMDGEEDCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>119.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336063</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB031025</foodb_id>
  <chemspider_id>22563</chemspider_id>
  <kegg_id>C03878</kegg_id>
  <pubchem_compound_id>24139</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28009</chebi_id>
  <meta_cyc_id/>
  <wikipedia_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5767</metlin_id>
  <synthesis_reference>Kuk, J. H.; Jung, W. J.; Jo, G. H.; Kim, Y. C.; Kim, K. Y.; Park, R. D.  Production of N-acetyl-b-D-glucosamine from chitin by Aeromonas sp. GJ-18 crude enzyme.    Applied Microbiology and Biotechnology  (2005),  68(3),  384-389.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00424</protein_accession>
      <name>Hyaluronidase-2</name>
      <uniprot_id>Q8SQG8</uniprot_id>
      <gene_name>HYAL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00425</protein_accession>
      <name>Hyaluronidase-1</name>
      <uniprot_id>Q5E985</uniprot_id>
      <gene_name>HYAL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:50 UTC</creation_date>
  <update_date>2020-04-16 20:37:23 UTC</update_date>
  <accession>BMDB0000805</accession>
  <secondary_accessions>
    <accession>BMDB00805</accession>
  </secondary_accessions>
  <name>Pyrrolidonecarboxylic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Pyrrolidone-5-carboxylic acid</synonym>
    <synonym>5-oxo-DL-Proline</synonym>
    <synonym>5-Pyrrolidone-2-carboxylic acid</synonym>
    <synonym>Glp</synonym>
    <synonym>Pyroglutamate</synonym>
    <synonym>Pyroglutamic acid</synonym>
    <synonym>2-Pyrrolidone-5-carboxylate</synonym>
    <synonym>5-Pyrrolidone-2-carboxylate</synonym>
    <synonym>Pyrrolidonecarboxylate</synonym>
    <synonym>(+)-2-Pyrrolidone-5-carboxylate</synonym>
    <synonym>(+)-2-Pyrrolidone-5-carboxylic acid</synonym>
    <synonym>(+)-Pyroglutamate</synonym>
    <synonym>(+)-Pyroglutamic acid</synonym>
    <synonym>(2R)-2-Carboxy-5-pyrrolidinone</synonym>
    <synonym>(R)-(+)-2-Pyrrolidone-5-carboxylate</synonym>
    <synonym>(R)-(+)-2-Pyrrolidone-5-carboxylic acid</synonym>
    <synonym>(R)-2-Pyrrolidone-5-carboxylate</synonym>
    <synonym>(R)-2-Pyrrolidone-5-carboxylic acid</synonym>
    <synonym>(R)-5-Oxopyrrolidine-2-carboxylate</synonym>
    <synonym>(R)-5-Oxopyrrolidine-2-carboxylic acid</synonym>
    <synonym>5-oxo-D-Proline</synonym>
    <synonym>D-2-Pyrrolidone-5-carboxylic</synonym>
    <synonym>D-5-Pyrrolidone-2-carboxylate</synonym>
    <synonym>D-5-Pyrrolidone-2-carboxylic acid</synonym>
    <synonym>D-Pyroglutamate</synonym>
    <synonym>D-Pyroglutamic acid</synonym>
    <synonym>5-Ketoproline</synonym>
    <synonym>5-Oxoproline</synonym>
    <synonym>Pidolate, magnesium</synonym>
    <synonym>Pidolic acid</synonym>
    <synonym>5-Oxopyrrolidine-2-carboxylic acid</synonym>
    <synonym>Magnesium pidolate</synonym>
    <synonym>Pyrrolidonecarboxylic acid</synonym>
  </synonyms>
  <chemical_formula>C5H7NO3</chemical_formula>
  <average_molecular_weight>129.114</average_molecular_weight>
  <monisotopic_moleculate_weight>129.042593095</monisotopic_moleculate_weight>
  <iupac_name>5-oxopyrrolidine-2-carboxylic acid</iupac_name>
  <traditional_iupac>pyroglutamate</traditional_iupac>
  <cas_registry_number>149-87-1</cas_registry_number>
  <smiles>OC(=O)C1CCC(=O)N1</smiles>
  <inchi>InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)</inchi>
  <inchikey>ODHCTXKNWHHXJC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Proline and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxoprolines</alternative_parent>
      <alternative_parent>Pyrrolidine carboxylic acids</alternative_parent>
      <alternative_parent>Pyrrolidine-2-ones</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-pyrrolidone</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxoproline</substituent>
      <substituent>Proline or derivatives</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidine carboxylic acid</substituent>
      <substituent>Pyrrolidine carboxylic acid or derivatives</substituent>
      <substituent>Pyrrolidone</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>oxoproline</external_descriptor>
      <external_descriptor>pyrrolidin-2-ones</external_descriptor>
      <external_descriptor>pyrrolidinemonocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-oxopyrrolidine-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>129.114</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>129.042593095</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1CCC(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H7NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ODHCTXKNWHHXJC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>45</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451901</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <kegg_id/>
  <pubchem_compound_id>499</pubchem_compound_id>
  <chebi_id>16010</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Pyroglutamic_acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Meister, Alton; Bukenberger, Martha W.  Enzymic conversion of D-glutamic acid to D-pyrrolidonecarboxylic acid by mammalian tissues.    Nature (London, United Kingdom)  (1962),  194  557-9. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:51 UTC</creation_date>
  <update_date>2020-04-15 22:32:40 UTC</update_date>
  <accession>BMDB0000806</accession>
  <secondary_accessions>
    <accession>BMDB00806</accession>
  </secondary_accessions>
  <name>Myristic acid</name>
  <description>Myristic acid, also known as 14 or tetradecanoate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Myristic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Myristic acid exists in all living species, ranging from bacteria to humans. Myristic acid participates in a number of enzymatic reactions, within cattle. In particular, Myristic acid can be biosynthesized from trans-tetra-dec-2-enoic acid through the action of the enzyme fatty acid synthase. enoyl reductase domain. In addition, Myristic acid and malonic acid can be converted into 3-oxohexadecanoic acid through the action of the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In cattle, myristic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway. Myristic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Tetradecanecarboxylic acid</synonym>
    <synonym>14</synonym>
    <synonym>14:0</synonym>
    <synonym>14:00</synonym>
    <synonym>Acide tetradecanoique</synonym>
    <synonym>C14</synonym>
    <synonym>CH3-[CH2]12-COOH</synonym>
    <synonym>Myristinsaeure</synonym>
    <synonym>N-Tetradecan-1-Oic acid</synonym>
    <synonym>N-Tetradecanoic acid</synonym>
    <synonym>N-Tetradecoic acid</synonym>
    <synonym>Tetradecoic acid</synonym>
    <synonym>Tetradecanoate</synonym>
    <synonym>1-Tetradecanecarboxylate</synonym>
    <synonym>N-Tetradecan-1-Oate</synonym>
    <synonym>N-Tetradecanoate</synonym>
    <synonym>N-Tetradecoate</synonym>
    <synonym>Tetradecoate</synonym>
    <synonym>Tetradecanoic acid</synonym>
    <synonym>Myristate</synonym>
    <synonym>1-Tridecanecarboxylate</synonym>
    <synonym>1-Tridecanecarboxylic acid</synonym>
    <synonym>Crodacid</synonym>
    <synonym>Myristic acid pure</synonym>
    <synonym>Myristoate</synonym>
    <synonym>Myristoic acid</synonym>
    <synonym>Tetradecanoic (myristic) acid</synonym>
    <synonym>Acid, tetradecanoic</synonym>
    <synonym>Acid, myristic</synonym>
    <synonym>FA(14:0)</synonym>
  </synonyms>
  <chemical_formula>C14H28O2</chemical_formula>
  <average_molecular_weight>228.3709</average_molecular_weight>
  <monisotopic_moleculate_weight>228.20893014</monisotopic_moleculate_weight>
  <iupac_name>tetradecanoic acid</iupac_name>
  <traditional_iupac>myristic acid</traditional_iupac>
  <cas_registry_number>544-63-8</cas_registry_number>
  <smiles>CCCCCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)</inchi>
  <inchikey>TUNFSRHWOTWDNC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Saturated fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>53.9 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.00107 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.11</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>tetradecanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>228.3709</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>228.20893014</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H28O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>TUNFSRHWOTWDNC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>67.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>30.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373910</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed barley silage diet with flaxseed for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed hay for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed hay with flaxseed for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>5136.47</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>4775.21</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>104050.78</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>132744.23</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>115186.7</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>120872.0989</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>151726.86</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Calf-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>140692.18</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. With growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>147041.5</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Without growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>138051.74</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Yearling-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed barley silage diet for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by infra-red spectroscopy and silieic acid columns</comment>
      <references>
        <reference>
          <reference_text>Laura Evans, Stuart Patton, R.D. McCarthy. Fatty Acid Composition of the Lipid Fractions from Bovine Serum Lipoproteins. J. Dairy Science (1961) 44(3) 475-482   doi: 10.3168/jds.S0022-0302(61)89765-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1926.69</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1445.0177</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16814.752</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16157.93</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15107.00</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.5 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14.4 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17.5 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35.64 +/- 6.48</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk from a Danish Holstein herd by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>41.48 +/- 6.48</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised whole milk (3.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17.52 +/- 1.14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised semi skimmed milk (1.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.14 +/- 0.65</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised skimmed milk (0.1% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30.39 +/- 0.20</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17953.243 +/- 5254.608</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
          <pubmed_id>16899705</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>39.585 +/- 0.59</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Catrienus De Jong Herman T. Badings. Determination of free fatty acids in milk and cheese procedures for extraction, clean up, and capillary gas chromatographic analysis. Journal of High Resolution Chromatography Volume 13, Issue 2, 1990</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>84.5 +/- 26.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Fat content of plain milk wasn't specified in the reference. 3.25% is an estimate.</comment>
      <references>
        <reference>
          <reference_text>Lu CY, Wu HL, Chen SH, Kou HS, Wu SM: Simple and sensitive analysis of long-chain free fatty acids in milk by fluorogenic derivatization and high-performance liquid chromatography. J Agric Food Chem. 2002 Jan 2;50(1):71-3.</reference_text>
          <pubmed_id>11754544</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>53.5 +/- 15.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Fat content of low-fat milk wasn't specified in the reference. 1-2% is an estimate.</comment>
      <references>
        <reference>
          <reference_text>Lu CY, Wu HL, Chen SH, Kou HS, Wu SM: Simple and sensitive analysis of long-chain free fatty acids in milk by fluorogenic derivatization and high-performance liquid chromatography. J Agric Food Chem. 2002 Jan 2;50(1):71-3.</reference_text>
          <pubmed_id>11754544</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
          <pubmed_id>14168161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19660.990 +/- 4291.263</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19004.164 +/- 3809.591</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6874.78</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6568.26</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1445.0177</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Oocyte</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by CP9010 autosampler onto a capillary column within a CP9001 gas chromatograph in slaughtered cow ovaries.</comment>
      <references>
        <reference>
          <reference_text>McEvoy TG, Coull GD, Broadbent PJ, Hutchinson JS, Speake BK: Fatty acid composition of lipids in immature cattle, pig and sheep oocytes with intact zona pellucida. J Reprod Fertil. 2000 Jan;118(1):163-70.</reference_text>
          <pubmed_id>10793638</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>3.3 +/- 0.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>3.3 +/- 0.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by FAMEs/GC–MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB08231</drugbank_id>
  <foodb_id>FDB031009</foodb_id>
  <chemspider_id>10539</chemspider_id>
  <kegg_id>C06424</kegg_id>
  <pubchem_compound_id>11005</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28875</chebi_id>
  <meta_cyc_id>CPD-7836</meta_cyc_id>
  <wikipedia_id>Myristic_acid</wikipedia_id>
  <knapsack_id>C00001228</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>215851</bigg_id>
  <metlin_id>196</metlin_id>
  <synthesis_reference>Greaves, W. S.; Linstead, R. P.; Shephard, B. R.; Thomas, S. L. S.; Weedon, B. C. L.  Anodic syntheses. I. New syntheses of stearic, myristic, and other acids.    Journal of the Chemical Society  (1950),     3326-30.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
      <pubmed_id>16899705</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
      <pubmed_id>14168161</pubmed_id>
    </reference>
    <reference>
      <reference_text>van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.</reference_text>
      <pubmed_id>28219465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
    </reference>
    <reference>
      <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00116</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 4</name>
      <uniprot_id>Q8SPU8</uniprot_id>
      <gene_name>DHRS4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:52 UTC</creation_date>
  <update_date>2020-04-14 22:48:25 UTC</update_date>
  <accession>BMDB0000807</accession>
  <secondary_accessions>
    <accession>BMDB00807</accession>
  </secondary_accessions>
  <name>3-Phosphoglyceric acid</name>
  <description>3-Phosphoglyceric acid, also known as glycerate 3-phosphate or 3-PG, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. 3-Phosphoglyceric acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Phosphoglyceric acid exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>3-(Dihydrogen phosphate)glycerate</synonym>
    <synonym>3-(Dihydrogen phosphate)glyceric acid</synonym>
    <synonym>3-Phosphoglycerate</synonym>
    <synonym>DL-Glycerate 3-phosphate</synonym>
    <synonym>Glycerate 3-phosphate</synonym>
    <synonym>Glycerate 3-phosphates</synonym>
    <synonym>Glyceric acid 3-phosphate</synonym>
    <synonym>3-(Dihydrogen phosphoric acid)glyceric acid</synonym>
    <synonym>DL-Glyceric acid 3-phosphoric acid</synonym>
    <synonym>Glyceric acid 3-phosphoric acid</synonym>
    <synonym>Glyceric acid 3-phosphates</synonym>
    <synonym>3-Glycerophosphorate</synonym>
    <synonym>3-Glycerophosphoric acid</synonym>
    <synonym>3-p-D-Glycerate</synonym>
    <synonym>3-p-Glycerate</synonym>
    <synonym>3-PG</synonym>
    <synonym>3-PGA</synonym>
    <synonym>3-Phospho-(R)-glycerate</synonym>
    <synonym>3-Phospho-D-glycerate</synonym>
    <synonym>3-Phospho-glycerate</synonym>
    <synonym>3-Phospho-glyceric acid</synonym>
    <synonym>D-(-)-3-Phosphoglyceric acid</synonym>
    <synonym>D-Glycerate 3-phosphate</synonym>
    <synonym>G3P</synonym>
    <synonym>Glycerate-3-p</synonym>
    <synonym>Phosphoglycerate</synonym>
    <synonym>3-Phosphoglycerate, trisodium salt</synonym>
    <synonym>3-Phosphoglycerate, (R)-isomer</synonym>
    <synonym>3-Phosphoglycerate, monosodium salt</synonym>
  </synonyms>
  <chemical_formula>C3H7O7P</chemical_formula>
  <average_molecular_weight>186.0572</average_molecular_weight>
  <monisotopic_moleculate_weight>185.99293909</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-3-(phosphonooxy)propanoic acid</iupac_name>
  <traditional_iupac>phosphoglycerate</traditional_iupac>
  <cas_registry_number>820-11-1</cas_registry_number>
  <smiles>OC(COP(O)(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)</inchi>
  <inchikey>OSJPPGNTCRNQQC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glyceric_acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>monophosphoglyceric acid</external_descriptor>
      <external_descriptor>tetronic acid derivative</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-3-(phosphonooxy)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>186.0572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>185.99293909</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(COP(O)(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OSJPPGNTCRNQQC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>124.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451920</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fermented milk, by capillary electrophoresis-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
          <pubmed_id>26686724</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022255</foodb_id>
  <chemspider_id>704</chemspider_id>
  <kegg_id>C00597</kegg_id>
  <pubchem_compound_id>724</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17050</chebi_id>
  <meta_cyc_id/>
  <wikipedia_id>3-Phosphoglyceric_acid</wikipedia_id>
  <knapsack_id>C00007286</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34230</bigg_id>
  <metlin_id>150</metlin_id>
  <synthesis_reference>Jakoby, Wm. B.; Brummond, Dewey O.; Ochoa, Severo.  Formation of 3-phosphoglyceric acid by carbon dioxide fixation with spinach-leaf enzymes.    Journal of Biological Chemistry  (1956),  218  811-22.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
      <pubmed_id>26686724</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00919</protein_accession>
      <name>Phosphoglycerate mutase 2</name>
      <uniprot_id>Q32KV0</uniprot_id>
      <gene_name>PGAM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00920</protein_accession>
      <name>Bisphosphoglycerate mutase</name>
      <uniprot_id>Q3T014</uniprot_id>
      <gene_name>BPGM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00921</protein_accession>
      <name>Phosphoglycerate mutase 1</name>
      <uniprot_id>Q3SZ62</uniprot_id>
      <gene_name>PGAM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01072</protein_accession>
      <name>D-3-phosphoglycerate dehydrogenase</name>
      <uniprot_id>Q5EAD2</uniprot_id>
      <gene_name>PHGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01150</protein_accession>
      <name>Phosphoglycerate kinase</name>
      <uniprot_id>Q58DJ6</uniprot_id>
      <gene_name>PGK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01160</protein_accession>
      <name>Phosphoglycerate kinase 1</name>
      <uniprot_id>Q3T0P6</uniprot_id>
      <gene_name>PGK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01168</protein_accession>
      <name>Phosphoglycerate kinase</name>
      <uniprot_id>Q32KN6</uniprot_id>
      <gene_name>PGK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01248</protein_accession>
      <name>Phosphoglycerate kinase</name>
      <uniprot_id>Q862Q5</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:53 UTC</creation_date>
  <update_date>2020-03-13 16:23:59 UTC</update_date>
  <accession>BMDB0000808</accession>
  <secondary_accessions>
    <accession>BMDB00808</accession>
  </secondary_accessions>
  <name>N-Butyrylglycine</name>
  <description/>
  <synonyms>
    <synonym>2-Butanamidoacetic acid</synonym>
    <synonym>2-Butyramidoacetic acid</synonym>
    <synonym>Butanamidoacetic acid</synonym>
    <synonym>Butyramidoacetic acid</synonym>
    <synonym>N-(1-Oxobutyl)glycine</synonym>
    <synonym>N-Butyryl-glycine</synonym>
    <synonym>2-Butanamidoacetate</synonym>
    <synonym>2-Butyramidoacetate</synonym>
    <synonym>Butanamidoacetate</synonym>
    <synonym>Butyramidoacetate</synonym>
    <synonym>N-Butanoylglycine</synonym>
    <synonym>Butyrylglycine</synonym>
    <synonym>N-Butyrylglycine</synonym>
  </synonyms>
  <chemical_formula>C6H11NO3</chemical_formula>
  <average_molecular_weight>145.1564</average_molecular_weight>
  <monisotopic_moleculate_weight>145.073893223</monisotopic_moleculate_weight>
  <iupac_name>2-butanamidoacetic acid</iupac_name>
  <traditional_iupac>butyrylglycine</traditional_iupac>
  <cas_registry_number>20208-73-5</cas_registry_number>
  <smiles>CCCC(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C6H11NO3/c1-2-3-5(8)7-4-6(9)10/h2-4H2,1H3,(H,7,8)(H,9,10)</inchi>
  <inchikey>WPSSBBPLVMTKRN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-butanamidoacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>145.1564</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>145.073893223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCC(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H11NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H11NO3/c1-2-3-5(8)7-4-6(9)10/h2-4H2,1H3,(H,7,8)(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WPSSBBPLVMTKRN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339651</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022256</foodb_id>
  <chemspider_id>79766</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>88412</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>89963</chebi_id>
  <meta_cyc_id/>
  <wikipedia_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5772</metlin_id>
  <synthesis_reference>Bondi, S.; Eissler, F.  Lipoproteins and the Fatty Degeneration of Cells.    Biochemische Zeitschrift  (1910),  23  499-513.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:54 UTC</creation_date>
  <update_date>2020-03-13 16:23:59 UTC</update_date>
  <accession>BMDB0000809</accession>
  <secondary_accessions>
    <accession>BMDB00809</accession>
  </secondary_accessions>
  <name>N-Glycoloylganglioside GM1</name>
  <description/>
  <synonyms>
    <synonym>GM1 Ganglioside</synonym>
    <synonym>(2S,4S,5R)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4E)-3-hydroxy-2-[(1-hydroxyicosylidene)amino]icos-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-3-hydroxy-5-{[(2S,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate</synonym>
  </synonyms>
  <chemical_formula>C77H139N3O30</chemical_formula>
  <average_molecular_weight>1586.9297</average_molecular_weight>
  <monisotopic_moleculate_weight>1585.944340123</monisotopic_moleculate_weight>
  <iupac_name>(2S,4S,5R)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4E)-3-hydroxy-2-icosanamidoicos-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-6-methyloxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>(2S,4S,5R)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4E)-3-hydroxy-2-icosanamidoicos-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-6-methyloxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>CCCCCCCCCCCCCCCCCCCC(=O)N[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](C)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H]3NC(C)=O)[C@H](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)C(O3)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]2O)[C@H](O)[C@H]1O)[C@@H](O)\C=C\CCCCCCCCCCCCCCC</smiles>
  <inchi>InChI=1S/C77H139N3O30/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-56(90)80-49(50(87)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2)45-101-73-65(97)63(95)68(55(44-84)105-73)107-75-66(98)71(110-77(76(99)100)40-51(88)57(78-47(4)85)70(109-77)59(91)52(89)41-81)67(46(3)102-75)106-72-58(79-48(5)86)69(61(93)54(43-83)103-72)108-74-64(96)62(94)60(92)53(42-82)104-74/h36,38,46,49-55,57-75,81-84,87-89,91-98H,6-35,37,39-45H2,1-5H3,(H,78,85)(H,79,86)(H,80,90)(H,99,100)/b38-36+/t46-,49-,50+,51+,52-,53-,54-,55-,57-,58-,59-,60+,61+,62+,63-,64-,65-,66-,67+,68-,69-,70?,71-,72+,73-,74+,75+,77+/m1/s1</inchi>
  <inchikey>WHRNXVBQVRYAKH-MBNVEIDWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Sphingolipids</class>
    <sub_class>Glycosphingolipids</sub_class>
    <direct_parent>Glycosyl-N-acylsphingosines</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alkyl glycosides</alternative_parent>
      <alternative_parent>C-glucuronides</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketals</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>N-acylneuraminic acids</alternative_parent>
      <alternative_parent>Neuraminic acids</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Oligosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl glycoside</substituent>
      <substituent>C-glucuronide</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty acyl glycoside</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Glycosyl-n-acylsphingosine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketal</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-acylneuraminic acid</substituent>
      <substituent>N-acylneuraminic acid or derivatives</substituent>
      <substituent>Neuraminic acid</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Oligosaccharide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,4S,5R)-2-{[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-{[(2R,3S,4E)-3-hydroxy-2-icosanamidoicos-4-en-1-yl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-5-{[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-6-methyloxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1586.9297</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1585.944340123</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCCCCCC(=O)N[C@H](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](C)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H]3NC(C)=O)[C@H](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)C(O3)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]2O)[C@H](O)[C@H]1O)[C@@H](O)\C=C\CCCCCCCCCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C77H139N3O30</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C77H139N3O30/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-56(90)80-49(50(87)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2)45-101-73-65(97)63(95)68(55(44-84)105-73)107-75-66(98)71(110-77(76(99)100)40-51(88)57(78-47(4)85)70(109-77)59(91)52(89)41-81)67(46(3)102-75)106-72-58(79-48(5)86)69(61(93)54(43-83)103-72)108-74-64(96)62(94)60(92)53(42-82)104-74/h36,38,46,49-55,57-75,81-84,87-89,91-98H,6-35,37,39-45H2,1-5H3,(H,78,85)(H,79,86)(H,80,90)(H,99,100)/b38-36+/t46-,49-,50+,51+,52-,53-,54-,55-,57-,58-,59-,60+,61+,62+,63-,64-,65-,66-,67+,68-,69-,70?,71-,72+,73-,74+,75+,77+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WHRNXVBQVRYAKH-MBNVEIDWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>520.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>392.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>177.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>30</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022257</foodb_id>
  <chemspider_id>17216009</chemspider_id>
  <pubchem_compound_id>22833548</pubchem_compound_id>
  <kegg_id>C01808</kegg_id>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Hirabayashi, Yoshio; Nakao, Toru; Matsumoto, Makoto; Obata, Kunihiko; Ando, Susumu.  Improved method for large-scale purification of brain gangliosides by Q-Sepharose column chromatography.  Immunochemical detection of C-series polysialogangliosides in adult bovine brains.    Journal of Chromatography  (1988),  445(2),  377-84.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:56 UTC</creation_date>
  <update_date>2020-03-13 16:24:00 UTC</update_date>
  <accession>BMDB0000810</accession>
  <secondary_accessions>
    <accession>BMDB00810</accession>
  </secondary_accessions>
  <name>Dimethylprotoporphyrin IX dimethyl ester</name>
  <description/>
  <synonyms>
    <synonym>Dimethyl 3,8,13,17-tetramethyl-7,12-divinyl-21H,23H-porphine-2,18-dipropionate</synonym>
    <synonym>Dimethyl 7,12-diethenyl-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoate</synonym>
    <synonym>Dimethyl 7,12-diethenyl-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoic acid</synonym>
    <synonym>Dimethyl protoporphyrin IX</synonym>
    <synonym>Protoporphyrin dimethyl ester</synonym>
    <synonym>Protoporphyrin IX di-me ester</synonym>
    <synonym>Protoporphyrin IX dimethyl ester</synonym>
    <synonym>Methyl 3-[10,15-diethenyl-20-(3-methoxy-3-oxopropyl)-5,9,14,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid</synonym>
  </synonyms>
  <chemical_formula>C36H38N4O4</chemical_formula>
  <average_molecular_weight>590.7113</average_molecular_weight>
  <monisotopic_moleculate_weight>590.289305724</monisotopic_moleculate_weight>
  <iupac_name>methyl 3-[9,14-diethenyl-20-(3-methoxy-3-oxopropyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoate</iupac_name>
  <traditional_iupac>methyl 3-[9,14-diethenyl-20-(3-methoxy-3-oxopropyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoate</traditional_iupac>
  <cas_registry_number>5522-66-7</cas_registry_number>
  <smiles>COC(=O)CCC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(CCC(=O)OC)=C5C)C(C)=C4C=C)C(C)=C3C=C)=C1C</smiles>
  <inchi>InChI=1S/C36H38N4O4/c1-9-23-19(3)27-15-28-21(5)25(11-13-35(41)43-7)33(39-28)18-34-26(12-14-36(42)44-8)22(6)30(40-34)17-32-24(10-2)20(4)29(38-32)16-31(23)37-27/h9-10,15-18,37,40H,1-2,11-14H2,3-8H3/b27-15-,28-15-,29-16-,30-17-,31-16-,32-17-,33-18-,34-18-</inchi>
  <inchikey>WASRLAPXOHTNAX-MFBGAUBSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>8.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>methyl 3-[9,14-diethenyl-20-(3-methoxy-3-oxopropyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>590.7113</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>590.289305724</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC(=O)CCC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(CCC(=O)OC)=C5C)C(C)=C4C=C)C(C)=C3C=C)=C1C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C36H38N4O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C36H38N4O4/c1-9-23-19(3)27-15-28-21(5)25(11-13-35(41)43-7)33(39-28)18-34-26(12-14-36(42)44-8)22(6)30(40-34)17-32-24(10-2)20(4)29(38-32)16-31(23)37-27/h9-10,15-18,37,40H,1-2,11-14H2,3-8H3/b27-15-,28-15-,29-16-,30-17-,31-16-,32-17-,33-18-,34-18-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WASRLAPXOHTNAX-MFBGAUBSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>109.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>173.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>70.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360162</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022258</foodb_id>
  <chemspider_id>10229562</chemspider_id>
  <pubchem_compound_id/>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5774</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Jun, Ri Chol; Jin, Pak Song.  Separation and purification of protoporphyrin IX.    Choson Minjujuui Inmin Konghwaguk Kwahagwon Tongbo  (1998),   (6),  50-53.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:57 UTC</creation_date>
  <update_date>2020-04-15 22:14:34 UTC</update_date>
  <accession>BMDB0000811</accession>
  <secondary_accessions>
    <accession>BMDB00811</accession>
  </secondary_accessions>
  <name>Murocholic acid</name>
  <description/>
  <synonyms>
    <synonym>3alpha,6beta-Dihydroxy-5beta-cholanic acid</synonym>
    <synonym>6beta-Hydroxylithocholate</synonym>
    <synonym>6beta-Hydroxylithocholic acid</synonym>
    <synonym>Murideoxycholate</synonym>
    <synonym>3a,6b-Dihydroxy-5b-cholanate</synonym>
    <synonym>3a,6b-Dihydroxy-5b-cholanic acid</synonym>
    <synonym>3alpha,6beta-Dihydroxy-5beta-cholanate</synonym>
    <synonym>3Α,6β-dihydroxy-5β-cholanate</synonym>
    <synonym>3Α,6β-dihydroxy-5β-cholanic acid</synonym>
    <synonym>6b-Hydroxylithocholate</synonym>
    <synonym>6b-Hydroxylithocholic acid</synonym>
    <synonym>6Β-hydroxylithocholate</synonym>
    <synonym>6Β-hydroxylithocholic acid</synonym>
    <synonym>Murideoxycholic acid</synonym>
    <synonym>Murocholate</synonym>
    <synonym>3a,6b-Dihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,6b-Dihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3a,6b-Dihydroxy-5b-cholanoate</synonym>
    <synonym>3a,6b-Dihydroxy-5b-cholanoic acid</synonym>
    <synonym>3a,6b-Dihydroxycholanoate</synonym>
    <synonym>3a,6b-Dihydroxycholanoic acid</synonym>
    <synonym>3,6-Dihydroxy-5alpha-cholanoic acid</synonym>
    <synonym>NaHDC compound</synonym>
    <synonym>Hyodeoxycholic acid</synonym>
    <synonym>Hyodeoxycholic acid, (3alpha,5beta,6beta)-isomer</synonym>
    <synonym>Hyodeoxycholic acid, (3alpha,6beta)-isomer</synonym>
    <synonym>Hyodeoxycholic acid, sodium salt</synonym>
    <synonym>Hyodesoxycholic acid</synonym>
    <synonym>Sodium hyodeoxycholate</synonym>
    <synonym>Murocholic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O4</chemical_formula>
  <average_molecular_weight>392.572</average_molecular_weight>
  <monisotopic_moleculate_weight>392.292659768</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5R,7R,8R,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5R,7R,8R,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>668-49-5</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17-,18+,19+,20+,21-,23-,24-/m1/s1</inchi>
  <inchikey>DGABKXLVXPYZII-PLYQRAMGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>6-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>6-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>6beta-hydroxy steroid</external_descriptor>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>logp</kind>
      <value>3.08</value>
      <source>RODA,A ET AL. (1990)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5R,7R,8R,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>392.572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.292659768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17-,18+,19+,20+,21-,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DGABKXLVXPYZII-PLYQRAMGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354495</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022259</foodb_id>
  <chemspider_id>4446909</chemspider_id>
  <pubchem_compound_id>5283821</pubchem_compound_id>
  <kegg_id>C15515</kegg_id>
  <pdbe_id/>
  <chebi_id>52030</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5775</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Mitropoulos, K. A.; Myant, Nicolas B.  Formation of lithocholic acid, chenodeoxycholic acid and other bile acids from 3b-hydroxychol-5-enoic acid in vitro and in vivo.    Biochimica et Biophysica Acta, Lipids and Lipid Metabolism  (1967),  144(2),  430-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:58 UTC</creation_date>
  <update_date>2020-04-16 20:40:38 UTC</update_date>
  <accession>BMDB0000812</accession>
  <secondary_accessions>
    <accession>BMDB00812</accession>
  </secondary_accessions>
  <name>N-Acetyl-L-aspartic acid</name>
  <description/>
  <synonyms>
    <synonym>(S)-2-(Acetylamino)butanedioic acid</synonym>
    <synonym>(S)-2-(Acetylamino)succinic acid</synonym>
    <synonym>Acetyl-L-aspartic acid</synonym>
    <synonym>Acetylaspartic acid</synonym>
    <synonym>L-N-Acetylaspartic acid</synonym>
    <synonym>N-Acetylaspartic acid</synonym>
    <synonym>NAA</synonym>
    <synonym>(S)-2-(Acetylamino)butanedioate</synonym>
    <synonym>(S)-2-(Acetylamino)succinate</synonym>
    <synonym>Acetyl-L-aspartate</synonym>
    <synonym>Acetylaspartate</synonym>
    <synonym>L-N-Acetylaspartate</synonym>
    <synonym>N-Acetylaspartate</synonym>
    <synonym>N-Acetyl-L-aspartate</synonym>
    <synonym>(2S)-2-Acetamidobutanedioate</synonym>
    <synonym>(2S)-2-Acetamidobutanedioic acid</synonym>
    <synonym>N-Acetyl-S-aspartate</synonym>
    <synonym>N-Acetyl-S-aspartic acid</synonym>
    <synonym>N-Acetyl aspartate</synonym>
    <synonym>N-Acetylaspartate, monopotassium salt</synonym>
    <synonym>Acetyl aspartic acid</synonym>
  </synonyms>
  <chemical_formula>C6H9NO5</chemical_formula>
  <average_molecular_weight>175.1394</average_molecular_weight>
  <monisotopic_moleculate_weight>175.048072403</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-acetamidobutanedioic acid</iupac_name>
  <traditional_iupac>acetyl-L-aspartic acid</traditional_iupac>
  <cas_registry_number>997-55-7</cas_registry_number>
  <smiles>CC(=O)N[C@@H](CC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H9NO5/c1-3(8)7-4(6(11)12)2-5(9)10/h4H,2H2,1H3,(H,7,8)(H,9,10)(H,11,12)/t4-/m0/s1</inchi>
  <inchikey>OTCCIMWXFLJLIA-BYPYZUCNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Aspartic acid and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Aspartic acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acetyl-L-amino acid</external_descriptor>
      <external_descriptor>N-acyl-L-aspartic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>137 - 140 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>675 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-acetamidobutanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>175.1394</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>175.048072403</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H](CC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H9NO5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H9NO5/c1-3(8)7-4(6(11)12)2-5(9)10/h4H,2H2,1H3,(H,7,8)(H,9,10)(H,11,12)/t4-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OTCCIMWXFLJLIA-BYPYZUCNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>103.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451915</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022260</foodb_id>
  <chemspider_id>58576</chemspider_id>
  <kegg_id>C01042</kegg_id>
  <pubchem_compound_id>65065</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>21547</chebi_id>
  <meta_cyc_id>CPD-420</meta_cyc_id>
  <wikipedia_id>N-acetylaspartic_acid</wikipedia_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>36685</bigg_id>
  <metlin_id>5776</metlin_id>
  <synthesis_reference>Montoro, Fernando; Calatayud, Jose; Vilar, Angel.  N-Acetyl-L-aspartic acid.    Span.  (1983),     5 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:36:59 UTC</creation_date>
  <update_date>2020-03-13 16:24:01 UTC</update_date>
  <accession>BMDB0000814</accession>
  <secondary_accessions>
    <accession>BMDB00814</accession>
  </secondary_accessions>
  <name>N-Acetylglucosamine 6-sulfate</name>
  <description/>
  <synonyms>
    <synonym>(6S)GlcNAcb</synonym>
    <synonym>(6S)GlcNAcbeta</synonym>
    <synonym>4[6OSO3]glcnacbeta</synonym>
    <synonym>6-O-SulfO-N-acetyl-beta-D-glucosamine</synonym>
    <synonym>beta-D-GlcNAc6S</synonym>
    <synonym>beta-D-GlcpNAc6S</synonym>
    <synonym>N-Acetyl-D-glucosamine 6-sulfate</synonym>
    <synonym>N-Acetylglucosamine 6-sulfic acid</synonym>
    <synonym>6-O-SulfO-N-acetyl-b-D-glucosamine</synonym>
    <synonym>6-O-SulfO-N-acetyl-β-D-glucosamine</synonym>
    <synonym>6-O-SulphO-N-acetyl-b-D-glucosamine</synonym>
    <synonym>6-O-SulphO-N-acetyl-beta-D-glucosamine</synonym>
    <synonym>6-O-SulphO-N-acetyl-β-D-glucosamine</synonym>
    <synonym>b-D-GlcNAc6S</synonym>
    <synonym>Β-D-glcnac6S</synonym>
    <synonym>b-D-GlcpNAc6S</synonym>
    <synonym>Β-D-glcpnac6S</synonym>
    <synonym>N-Acetyl-D-glucosamine 6-sulfuric acid</synonym>
    <synonym>N-Acetyl-D-glucosamine 6-sulphate</synonym>
    <synonym>N-Acetyl-D-glucosamine 6-sulphuric acid</synonym>
    <synonym>N-Acetylglucosamine 6-sulfuric acid</synonym>
    <synonym>N-Acetylglucosamine 6-sulphate</synonym>
    <synonym>N-Acetylglucosamine 6-sulphuric acid</synonym>
    <synonym>Aga-6-S</synonym>
    <synonym>N-Acetyl-glucosamine 6-(hydrogen sulfate)</synonym>
    <synonym>N-Acetyl-glucosamine 6-(hydrogen sulphate)</synonym>
    <synonym>N-Acetylglucosamine-6-sulfate</synonym>
    <synonym>GlcNAc-6-O-sulfate</synonym>
    <synonym>N-Acetyl-b-D-glucosamine 6-sulfate</synonym>
    <synonym>N-Acetyl-b-D-glucosamine 6-sulfuric acid</synonym>
    <synonym>N-Acetyl-b-D-glucosamine 6-sulphate</synonym>
    <synonym>N-Acetyl-b-D-glucosamine 6-sulphuric acid</synonym>
    <synonym>N-Acetyl-beta-D-glucosamine 6-sulfuric acid</synonym>
    <synonym>N-Acetyl-beta-D-glucosamine 6-sulphate</synonym>
    <synonym>N-Acetyl-beta-D-glucosamine 6-sulphuric acid</synonym>
    <synonym>N-Acetyl-β-D-glucosamine 6-sulfate</synonym>
    <synonym>N-Acetyl-β-D-glucosamine 6-sulfuric acid</synonym>
    <synonym>N-Acetyl-β-D-glucosamine 6-sulphate</synonym>
    <synonym>N-Acetyl-β-D-glucosamine 6-sulphuric acid</synonym>
    <synonym>N-Acetylglucosamine 6-sulfate</synonym>
  </synonyms>
  <chemical_formula>C8H15NO9S</chemical_formula>
  <average_molecular_weight>301.271</average_molecular_weight>
  <monisotopic_moleculate_weight>301.046751773</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R,6R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}sulfonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R,6R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxysulfonic acid</traditional_iupac>
  <cas_registry_number>10356-99-7</cas_registry_number>
  <smiles>CC(=O)N[C@H]1[C@H](O)O[C@H](COS(O)(=O)=O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C8H15NO9S/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H,14,15,16)/t4-,5-,6-,7-,8-/m1/s1</inchi>
  <inchikey>WJFVEEAIYIOATH-FMDGEEDCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Acylaminosugars</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharide sulfates</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Acylaminosugar</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide sulfate</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>amino monosaccharide</external_descriptor>
      <external_descriptor>glucosamine sulfate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R,6R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>301.271</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>301.046751773</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@H]1[C@H](O)O[C@H](COS(O)(=O)=O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15NO9S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15NO9S/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H,14,15,16)/t4-,5-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WJFVEEAIYIOATH-FMDGEEDCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>162.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>57.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>50340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>50341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>50342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175124</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022261</foodb_id>
  <chemspider_id>389219</chemspider_id>
  <pubchem_compound_id>440235</pubchem_compound_id>
  <kegg_id>C04132</kegg_id>
  <pdbe_id/>
  <chebi_id>28132</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5778</metlin_id>
  <meta_cyc_id>CPD-13665</meta_cyc_id>
  <synthesis_reference>Saito, Tomoo; Noguchi, Junzo; Komatsu, Kiroku.  The esterification of carbohydrates in concentrated sul-furic acid. III.  The synthesis of 2-amino-2-deoxy-D-glucose O-sulfate, 2-acetamido-2-deoxy-D-glucose-6-sulfate and its calcium and barium salts.    Nippon Kagaku Zasshi  (1961),  82  472-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:00 UTC</creation_date>
  <update_date>2020-03-13 16:24:02 UTC</update_date>
  <accession>BMDB0000815</accession>
  <secondary_accessions>
    <accession>BMDB00815</accession>
  </secondary_accessions>
  <name>Pseudouroporphyrin</name>
  <description/>
  <synonyms>
    <synonym>21H,23H-Porphine-2,3,7,8,12,13,17-heptacarboxylate</synonym>
    <synonym>21H,23H-Porphine-2,3,7,8,12,13,17-heptacarboxylic acid</synonym>
    <synonym>3,8,13-Tris(carboxymethyl)-17-methyl-2,7,12,18-porphinetetrapropionate</synonym>
    <synonym>3,8,13-Tris(carboxymethyl)-17-methyl-2,7,12,18-porphinetetrapropionic acid</synonym>
    <synonym>Heptacarboxylic porphyrin: 3,8,13-tris(carboxymethyl)-17-methyl-21H,23H-porphine-2,7,12,18-tetrapropanoate</synonym>
    <synonym>Heptacarboxylic porphyrin: 3,8,13-tris(carboxymethyl)-17-methyl-21H,23H-porphine-2,7,12,18-tetrapropanoic acid</synonym>
    <synonym>Phyriaporphyrin</synonym>
    <synonym>3-[10,15,20-Tris(2-carboxyethyl)-9,14,19-tris(carboxymethyl)-5-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C39H38N4O14</chemical_formula>
  <average_molecular_weight>786.7374</average_molecular_weight>
  <monisotopic_moleculate_weight>786.238451944</monisotopic_moleculate_weight>
  <iupac_name>3-[9,15,19-tris(2-carboxyethyl)-5,10,20-tris(carboxymethyl)-14-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[9,15,19-tris(2-carboxyethyl)-5,10,20-tris(carboxymethyl)-14-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>25744-38-1</cas_registry_number>
  <smiles>CC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(CC(O)=O)=C5CCC(O)=O)C(CC(O)=O)=C4CCC(O)=O)C(CC(O)=O)=C3CCC(O)=O)=C1CCC(O)=O</smiles>
  <inchi>InChI=1S/C39H38N4O14/c1-17-18(2-6-33(44)45)26-14-27-20(4-8-35(48)49)23(11-38(54)55)31(42-27)16-29-21(5-9-36(50)51)24(12-39(56)57)32(43-29)15-28-19(3-7-34(46)47)22(10-37(52)53)30(41-28)13-25(17)40-26/h13-16,40,43H,2-12H2,1H3,(H,44,45)(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)/b25-13-,26-14-,27-14-,28-15-,29-16-,30-13-,31-16-,32-15-</inchi>
  <inchikey>QNZLBNVYKHQNCQ-PKXAPQLQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[9,15,19-tris(2-carboxyethyl)-5,10,20-tris(carboxymethyl)-14-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>786.7374</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>786.238451944</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(CC(O)=O)=C5CCC(O)=O)C(CC(O)=O)=C4CCC(O)=O)C(CC(O)=O)=C3CCC(O)=O)=C1CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C39H38N4O14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C39H38N4O14/c1-17-18(2-6-33(44)45)26-14-27-20(4-8-35(48)49)23(11-38(54)55)31(42-27)16-29-21(5-9-36(50)51)24(12-39(56)57)32(43-29)15-28-19(3-7-34(46)47)22(10-37(52)53)30(41-28)13-25(17)40-26/h13-16,40,43H,2-12H2,1H3,(H,44,45)(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)/b25-13-,26-14-,27-14-,28-15-,29-16-,30-13-,31-16-,32-15-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QNZLBNVYKHQNCQ-PKXAPQLQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>318.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>195.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>82.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338814</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022262</foodb_id>
  <chemspider_id>17216012</chemspider_id>
  <pubchem_compound_id/>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5779</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>del C. Batlle, Alcira M.; Grinstein, Moises.  Porphyrin biosynthesis. I. Erythrocyte preparations.    Biochimica et Biophysica Acta, General Subjects  (1964),  82(1),  1-12.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:02 UTC</creation_date>
  <update_date>2020-04-16 20:40:00 UTC</update_date>
  <accession>BMDB0000816</accession>
  <secondary_accessions>
    <accession>BMDB00816</accession>
  </secondary_accessions>
  <name>Phosphoglycolic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Phosphoglycolate</synonym>
    <synonym>2-Phosphoglycolic acid</synonym>
    <synonym>Phosphoglycolate</synonym>
    <synonym>2-Phosphoglicolate</synonym>
    <synonym>Glycolate-2-p</synonym>
    <synonym>(Phosphonooxy)-acetate</synonym>
    <synonym>(Phosphonooxy)-acetic acid</synonym>
    <synonym>(Phosphonooxy)acetate</synonym>
    <synonym>(Phosphonooxy)acetic acid</synonym>
    <synonym>2-Phosphonatoglycolate</synonym>
    <synonym>Glycolic acid di-H phosphate</synonym>
    <synonym>Glycolic acid dihydrogen phosphate</synonym>
    <synonym>Glycolic acid phosphate</synonym>
    <synonym>Glycophosphorate</synonym>
    <synonym>Glycophosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C2H5O6P</chemical_formula>
  <average_molecular_weight>156.0313</average_molecular_weight>
  <monisotopic_moleculate_weight>155.982374404</monisotopic_moleculate_weight>
  <iupac_name>2-(phosphonooxy)acetic acid</iupac_name>
  <traditional_iupac>phosphoglycolate</traditional_iupac>
  <cas_registry_number/>
  <smiles>OC(=O)COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C2H5O6P/c3-2(4)1-8-9(5,6)7/h1H2,(H,3,4)(H2,5,6,7)</inchi>
  <inchikey>ASCFNMCAHFUBCO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic phosphoric acids and derivatives</class>
    <sub_class>Phosphate esters</sub_class>
    <direct_parent>Monoalkyl phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>carboxyalkyl phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(phosphonooxy)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>156.0313</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>155.982374404</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H5O6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H5O6P/c3-2(4)1-8-9(5,6)7/h1H2,(H,3,4)(H2,5,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ASCFNMCAHFUBCO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>104.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30937</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB02726</drugbank_id>
  <pdbe_id/>
  <chemspider_id/>
  <kegg_id>C00988</kegg_id>
  <pubchem_compound_id>529</pubchem_compound_id>
  <foodb_id>FDB030360</foodb_id>
  <chebi_id>17150</chebi_id>
  <knapsack_id>C00007561</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Courtois, Jean.  Action of periodic acid on hexosediphosphoric acid.    Compt. rend.  (1941),  212  1172-4.  CAN 38:22678  AN 1944:22678</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00090</protein_accession>
      <name>Phosphoglycolate phosphatase</name>
      <uniprot_id>Q2T9S4</uniprot_id>
      <gene_name>PGP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:03 UTC</creation_date>
  <update_date>2020-03-13 16:24:03 UTC</update_date>
  <accession>BMDB0000817</accession>
  <secondary_accessions>
    <accession>BMDB00817</accession>
  </secondary_accessions>
  <name>Orinapterin</name>
  <description/>
  <synonyms>
    <synonym>6-(L-Threo-1,2-dihydroxypropyl)-pterin</synonym>
    <synonym>Ciliapterin</synonym>
    <synonym>L-Dictyopterin</synonym>
    <synonym>L-Threo-1-(2-amino-4-hydroxy-6-pteridinyl)-1,2-propanediol</synonym>
    <synonym>L-Threo-biopterin</synonym>
    <synonym>[S-(R*,r*)]-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone</synonym>
    <synonym>2-Amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinone</synonym>
    <synonym>Dictyopterin</synonym>
    <synonym>Biopterin</synonym>
  </synonyms>
  <chemical_formula>C9H11N5O3</chemical_formula>
  <average_molecular_weight>237.2153</average_molecular_weight>
  <monisotopic_moleculate_weight>237.086189243</monisotopic_moleculate_weight>
  <iupac_name>2-amino-6-[(1S,2S)-1,2-dihydroxypropyl]-1,4-dihydropteridin-4-one</iupac_name>
  <traditional_iupac>2-amino-6-[(1S,2S)-1,2-dihydroxypropyl]-1H-pteridin-4-one</traditional_iupac>
  <cas_registry_number>13039-82-2</cas_registry_number>
  <smiles>C[C@H](O)[C@@H](O)C1=NC2=C(NC(N)=NC2=O)N=C1</smiles>
  <inchi>InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6+/m0/s1</inchi>
  <inchikey>LHQIJBMDNUYRAM-BBIVZNJYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Biopterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrazines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Biopterin</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrazine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>biopterins</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-6-[(1S,2S)-1,2-dihydroxypropyl]-1,4-dihydropteridin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>237.2153</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>237.086189243</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](O)[C@@H](O)C1=NC2=C(NC(N)=NC2=O)N=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11N5O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LHQIJBMDNUYRAM-BBIVZNJYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>133.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>58.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288944</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37783</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <phenol_explorer_compound_id/>
  <chemspider_id>13628150</chemspider_id>
  <foodb_id>FDB022264</foodb_id>
  <pubchem_compound_id>12646210</pubchem_compound_id>
  <drugbank_id/>
  <kegg_id/>
  <chebi_id>74688</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>CPD-15311</meta_cyc_id>
  <wikipedia_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>5781</metlin_id>
  <synthesis_reference>Sugimoto, Takashi; Matsuura, Sadao.  The convenient syntheses of biopterin and its three optical isomers.    Bulletin of the Chemical Society of Japan  (1975),  48(12),  3767-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:04 UTC</creation_date>
  <update_date>2020-04-15 22:27:59 UTC</update_date>
  <accession>BMDB0000819</accession>
  <secondary_accessions>
    <accession>BMDB00819</accession>
  </secondary_accessions>
  <name>Normetanephrine</name>
  <description>Normetanephrine, also known as normetanephrine, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Normetanephrine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Normetanephrine participates in a number of enzymatic reactions, within cattle. In particular, Normetanephrine can be converted into 3-methoxy-4-hydroxyphenylglycolaldehyde through the action of the enzyme amine oxidase [flavin-containing] a. In addition, Normetanephrine and pyrocatechol can be biosynthesized from norepinephrine and guaiacol through the action of the enzyme catechol O-methyltransferase. In cattle, normetanephrine is involved in the metabolic pathway called the tyrosine metabolism pathway.</description>
  <synonyms>
    <synonym>(+/-)-normetanephrine</synonym>
    <synonym>(+/-)-alpha-(aminomethyl)-4-hydroxy-3-methoxy-benzenemethanol</synonym>
    <synonym>3-Methoxy-noradrenaline</synonym>
    <synonym>3-O-Methyl-noradrenaline</synonym>
    <synonym>4-(2-Amino-1-hydroxyethyl)-2-methoxyphenol</synonym>
    <synonym>alpha-(Aminomethyl)-4-hydroxy-3-methoxy-benzenemethanol</synonym>
    <synonym>DL-N-Normetanephrine</synonym>
    <synonym>DL-Normetanephrine</synonym>
    <synonym>L-Normetanephrine</synonym>
    <synonym>m-O-Methylnorepinephrine</synonym>
    <synonym>N111</synonym>
    <synonym>Normetadrenaline</synonym>
    <synonym>O-Methylnoradrenaline</synonym>
    <synonym>3 Methoxynoradrenaline</synonym>
    <synonym>3-Methoxynoradrenaline</synonym>
  </synonyms>
  <chemical_formula>C9H13NO3</chemical_formula>
  <average_molecular_weight>183.2044</average_molecular_weight>
  <monisotopic_moleculate_weight>183.089543287</monisotopic_moleculate_weight>
  <iupac_name>4-(2-amino-1-hydroxyethyl)-2-methoxyphenol</iupac_name>
  <traditional_iupac>(+/-)-normetanephrine</traditional_iupac>
  <cas_registry_number>97-31-4</cas_registry_number>
  <smiles>COC1=CC(=CC=C1O)C(O)CN</smiles>
  <inchi>InChI=1S/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3</inchi>
  <inchikey>YNYAYWLBAHXHLL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Methoxyphenols</sub_class>
    <direct_parent>Methoxyphenols</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Amine</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a guaiacol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>204 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.05</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-(2-amino-1-hydroxyethyl)-2-methoxyphenol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>183.2044</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>183.089543287</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC(=CC=C1O)C(O)CN</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YNYAYWLBAHXHLL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>75.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>48.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345465</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022265</foodb_id>
  <chemspider_id>1200</chemspider_id>
  <kegg_id>C05589</kegg_id>
  <pubchem_compound_id>1237</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>144308</chebi_id>
  <meta_cyc_id/>
  <wikipedia_id>Normetanephrine</wikipedia_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>46080</bigg_id>
  <metlin_id>66</metlin_id>
  <synthesis_reference>Sejbal, Jan; Krecek, Vaclav.  Method of preparing normetanephrine.    Czech.  (1992),  4 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:05 UTC</creation_date>
  <update_date>2020-04-16 17:52:19 UTC</update_date>
  <accession>BMDB0000820</accession>
  <secondary_accessions>
    <accession>BMDB00820</accession>
  </secondary_accessions>
  <name>Propyl alcohol</name>
  <description>1-Propanol, also known as N-propyl alcohol or ethylcarbinol, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). Thus, 1-propanol is considered to be a fatty alcohol lipid molecule. 1-Propanol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 1-Propanol exists in all living species, ranging from bacteria to humans. In cattle, 1-propanol is involved in the metabolic pathway called the sulfate/sulfite metabolism pathway. 1-Propanol has been found to be associated with several diseases known as ulcerative colitis, crohn's disease, irritable bowel syndrome, and nonalcoholic fatty liver disease; also 1-propanol has been linked to the inborn metabolic disorders including celiac disease.</description>
  <synonyms>
    <synonym>1-Hydroxypropane</synonym>
    <synonym>1-Propanol</synonym>
    <synonym>Ethyl carbinol</synonym>
    <synonym>Ethylcarbinol</synonym>
    <synonym>N-Propan-1-ol</synonym>
    <synonym>N-Propanol</synonym>
    <synonym>N-Propyl alcohol</synonym>
    <synonym>N-Propylalkohol</synonym>
    <synonym>Optal</synonym>
    <synonym>Osmosol extra</synonym>
    <synonym>Propane-1-ol</synonym>
    <synonym>Propanol</synonym>
    <synonym>Propanol-1</synonym>
    <synonym>UN 1274</synonym>
    <synonym>Propan-1-ol</synonym>
    <synonym>1-Propyl alcohol</synonym>
    <synonym>Hydroxypropane</synonym>
    <synonym>Propanole</synonym>
    <synonym>Propanolen</synonym>
    <synonym>Propylan-propyl alcohol</synonym>
    <synonym>Propylic alcohol</synonym>
    <synonym>1 Propanol</synonym>
    <synonym>Alcohol, propyl</synonym>
    <synonym>N Propanol</synonym>
    <synonym>Propyl alcohol</synonym>
  </synonyms>
  <chemical_formula>C3H8O</chemical_formula>
  <average_molecular_weight>60.095</average_molecular_weight>
  <monisotopic_moleculate_weight>60.057514878</monisotopic_moleculate_weight>
  <iupac_name>propan-1-ol</iupac_name>
  <traditional_iupac>propanol</traditional_iupac>
  <cas_registry_number>71-23-8</cas_registry_number>
  <smiles>CCCO</smiles>
  <inchi>InChI=1S/C3H8O/c1-2-3-4/h4H,2-3H2,1H3</inchi>
  <inchikey>BDERNNFJNOPAEC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Primary alcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fatty alcohols</external_descriptor>
      <external_descriptor>a primary alcohol</external_descriptor>
      <external_descriptor>a short-chain alcohol</external_descriptor>
      <external_descriptor>propan-1-ols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-126.1 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.25</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>16.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>propan-1-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>60.095</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>60.057514878</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H8O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H8O/c1-2-3-4/h4H,2-3H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BDERNNFJNOPAEC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>17.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>7.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Sulfate/Sulfite Metabolism</name>
      <smpdb_id>SMP0087216</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22792</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9.75 +/- 6.48</concentration_value>
      <concentration_units>mg/100g dry matter content</concentration_units>
      <comment>Italian raw milk</comment>
      <references>
        <reference>
          <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13.1 +/- 5.41</concentration_value>
      <concentration_units>mg/100g dry matter content</concentration_units>
      <comment>Slovenian raw milk</comment>
      <references>
        <reference>
          <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB03175</drugbank_id>
  <foodb_id>FDB031044</foodb_id>
  <chemspider_id>1004</chemspider_id>
  <kegg_id>C05979</kegg_id>
  <pubchem_compound_id>1031</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28831</chebi_id>
  <meta_cyc_id>PROPANOL</meta_cyc_id>
  <wikipedia_id>Propan-1-ol</wikipedia_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5783</metlin_id>
  <synthesis_reference>Ito, Kenji; Katao, Masaaki.  Process for manufacturing propylene oxide and propyl alcohol.    Jpn. Kokai Tokkyo Koho  (2003),     4 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:06 UTC</creation_date>
  <update_date>2020-03-13 16:24:05 UTC</update_date>
  <accession>BMDB0000821</accession>
  <secondary_accessions>
    <accession>BMDB00821</accession>
  </secondary_accessions>
  <name>Phenylacetylglycine</name>
  <description>N-Phenylacetylglycine, also known as phenaceturic acid or phenacetate, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Phenylacetylglycine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Phenylacetylglycine exists in all eukaryotes, ranging from yeast to humans.</description>
  <synonyms>
    <synonym>N-Phenacetylglycine</synonym>
    <synonym>N-Phenylacetylglycine</synonym>
    <synonym>Phenaceturic acid</synonym>
    <synonym>Phenacetylglycine</synonym>
    <synonym>Phenacetate</synonym>
    <synonym>Phenacetic acid</synonym>
    <synonym>((Phenylacetyl)amino)acetic acid</synonym>
    <synonym>N-(Phenylacetyl)-glycine</synonym>
    <synonym>N-(Phenylacetyl)glycine</synonym>
    <synonym>PAA</synonym>
    <synonym>PAG</synonym>
    <synonym>Phenaceturate</synonym>
    <synonym>Phenylacetyl glycine</synonym>
    <synonym>[(Phenylacetyl)amino]acetate</synonym>
    <synonym>[(Phenylacetyl)amino]acetic acid</synonym>
    <synonym>Phenylacetylglycine</synonym>
  </synonyms>
  <chemical_formula>C10H11NO3</chemical_formula>
  <average_molecular_weight>193.1992</average_molecular_weight>
  <monisotopic_moleculate_weight>193.073893223</monisotopic_moleculate_weight>
  <iupac_name>2-(2-phenylacetamido)acetic acid</iupac_name>
  <traditional_iupac>phenylacetylglycine</traditional_iupac>
  <cas_registry_number>500-98-1</cas_registry_number>
  <smiles>OC(=O)CNC(=O)CC1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)</inchi>
  <inchikey>UTYVDVLMYQPLQB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylglycine</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
      <external_descriptor>monocarboxylic acid amide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>7.3 mg/mL at 11 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(2-phenylacetamido)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>193.1992</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>193.073893223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CNC(=O)CC1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H11NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UTYVDVLMYQPLQB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1499</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C05598</kegg_id>
  <foodb_id>FDB022266</foodb_id>
  <drugbank_id/>
  <chemspider_id>61452</chemspider_id>
  <pubchem_compound_id>68144</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>27480</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <wikipedia_id/>
  <bigg_id/>
  <metlin_id>4237</metlin_id>
  <meta_cyc_id>CPD-11715</meta_cyc_id>
  <synthesis_reference>Ford, Jared H.  Convenient synthesis of phenaceturic acid.    Journal of the American Chemical Society  (1949),  71  3842.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:07 UTC</creation_date>
  <update_date>2020-04-15 22:37:15 UTC</update_date>
  <accession>BMDB0000822</accession>
  <secondary_accessions>
    <accession>BMDB00822</accession>
  </secondary_accessions>
  <name>p-Hydroxymandelic acid</name>
  <description/>
  <synonyms>
    <synonym>4-Hydroxyphenylglycolic acid</synonym>
    <synonym>4-Hydroxymandelic acid</synonym>
    <synonym>4-Hydroxyphenylglycolate</synonym>
    <synonym>4-Hydroxymandelate</synonym>
    <synonym>p-Hydroxymandelate</synonym>
    <synonym>(+/-)-alpha,4-dihydroxy-benzeneacetate</synonym>
    <synonym>(+/-)-alpha,4-dihydroxy-benzeneacetic acid</synonym>
    <synonym>(R)-4-Hydroxymandelate</synonym>
    <synonym>(RS)-p-Hydroxymandelate</synonym>
    <synonym>(RS)-p-Hydroxymandelic acid</synonym>
    <synonym>(S)-4-Hydroxymandelate</synonym>
    <synonym>2-(4-Hydroxyphenyl)-2-hydroxyacetate</synonym>
    <synonym>2-(4-Hydroxyphenyl)-2-hydroxyacetic acid</synonym>
    <synonym>3-Dimethylallyl-4-hydroxymandelate</synonym>
    <synonym>3-Dimethylallyl-4-hydroxymandelic acid</synonym>
    <synonym>4-Hydroxy-DL-mandelate</synonym>
    <synonym>4-Hydroxy-DL-mandelic acid</synonym>
    <synonym>alpha,4-Dihydroxy-benzeneacetate</synonym>
    <synonym>alpha,4-Dihydroxy-benzeneacetic acid</synonym>
    <synonym>alpha,4-Dihydroxybenzeneacetate</synonym>
    <synonym>alpha,4-Dihydroxybenzeneacetic acid</synonym>
    <synonym>D-4-Hydroxymandelate</synonym>
    <synonym>D-p-Hydroxymandelate</synonym>
    <synonym>delta-4-Hydroxymandelate</synonym>
    <synonym>delta-p-Hydroxymandelate</synonym>
    <synonym>DL-4-Hydroxymandelate</synonym>
    <synonym>DL-4-Hydroxymandelic acid</synonym>
    <synonym>DL-p-Hydroxymandelate</synonym>
    <synonym>DL-p-Hydroxymandelic acid</synonym>
    <synonym>DL-p-Hydroxyphenylglycolate</synonym>
    <synonym>DL-p-Hydroxyphenylglycolic acid</synonym>
    <synonym>Hydroxy(4-hydroxyphenyl)acetate</synonym>
    <synonym>Hydroxy(4-hydroxyphenyl)acetic acid</synonym>
    <synonym>L-4-Hydroxymandelate</synonym>
    <synonym>L-p-Hydroxymandelate</synonym>
    <synonym>p-Hydroxy-mandelate</synonym>
    <synonym>p-Hydroxy-mandelic acid</synonym>
    <synonym>p-Hydroxyphenylglycolate</synonym>
    <synonym>p-Hydroxyphenylglycolic acid</synonym>
    <synonym>Para-hydroxymandelic acid</synonym>
    <synonym>4-Hydroxymandelic acid, (D)-isomer</synonym>
    <synonym>Pisolithin b</synonym>
  </synonyms>
  <chemical_formula>C8H8O4</chemical_formula>
  <average_molecular_weight>168.1467</average_molecular_weight>
  <monisotopic_moleculate_weight>168.042258744</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-2-(4-hydroxyphenyl)acetic acid</iupac_name>
  <traditional_iupac>4-hydroxymandelic acid</traditional_iupac>
  <cas_registry_number>1198-84-1</cas_registry_number>
  <smiles>OC(C(O)=O)C1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)</inchi>
  <inchikey>YHXHKYRQLYQUIH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>1-hydroxy-2-unsubstituted benzenoids</sub_class>
    <direct_parent>1-hydroxy-2-unsubstituted benzenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxy carboxylic acid</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>103 - 106 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-2-(4-hydroxyphenyl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>168.1467</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>168.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(C(O)=O)C1=CC=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H8O4/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YHXHKYRQLYQUIH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19576</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>321</chemspider_id>
  <pubchem_compound_id>328</pubchem_compound_id>
  <foodb_id>FDB022267</foodb_id>
  <kegg_id>C11527</kegg_id>
  <chebi_id>16388</chebi_id>
  <phenol_explorer_compound_id/>
  <drugbank_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>4-Hydroxymandelic acid</wikipedia_id>
  <metlin_id>5785</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Wang, Bing; Zhang, Guofeng.  Synthesis and purity determination of p-hydroxymandelic acid.    Qingdao Daxue Xuebao, Gongcheng Jishuban  (1999),  14(1),  14-16.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:08 UTC</creation_date>
  <update_date>2020-04-14 22:48:27 UTC</update_date>
  <accession>BMDB0000824</accession>
  <secondary_accessions>
    <accession>BMDB00824</accession>
  </secondary_accessions>
  <name>Propionylcarnitine</name>
  <description>Propionylcarnitine belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Thus, propionylcarnitine is considered to be a fatty ester lipid molecule. Propionylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Propionylcarnitine participates in a number of enzymatic reactions, within cattle. In particular, Propionylcarnitine can be biosynthesized from propionyl-CoA and L-carnitine; which is mediated by the enzyme carnitine O-acetyltransferase. In addition, Propionylcarnitine can be biosynthesized from propionyl-CoA and L-carnitine through its interaction with the enzyme carnitine O-acetyltransferase. In cattle, propionylcarnitine is involved in the metabolic pathway called the oxidation OF branched-chain fatty acids pathway. Propionylcarnitine is a potentially toxic compound. Propionylcarnitine has been found to be associated with several diseases known as crohn's disease, eosinophilic esophagitis, and obesity; also propionylcarnitine has been linked to several inborn metabolic disorders including propionic acidemia and celiac disease.</description>
  <synonyms>
    <synonym>3-Carboxy-N,N,N-trimethyl-2-(1-oxopropoxy)-1-propanaminium inner salt</synonym>
    <synonym>O-Propionylcarnitine</synonym>
    <synonym>Propionyl carnitine</synonym>
    <synonym>(+/-)-propionylcarnitine chloride</synonym>
    <synonym>(3-Carboxy-2-hydroxypropyl)trimethyl-hydroxide ammonium inner salt</synonym>
    <synonym>L-Propionylcarnitine</synonym>
    <synonym>O-Propanoylcarnitine</synonym>
    <synonym>Propionyl-carnitine</synonym>
    <synonym>Propionyl-L-carnitine</synonym>
    <synonym>Propionylcarnitine, (+-)-isomer</synonym>
    <synonym>Propionylcarnitine, (R)-isomer</synonym>
  </synonyms>
  <chemical_formula>C10H19NO4</chemical_formula>
  <average_molecular_weight>217.2622</average_molecular_weight>
  <monisotopic_moleculate_weight>217.131408101</monisotopic_moleculate_weight>
  <iupac_name>3-(propanoyloxy)-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>propionyl-L-carnitine</traditional_iupac>
  <cas_registry_number>17298-37-2</cas_registry_number>
  <smiles>CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C</smiles>
  <inchi>InChI=1S/C10H19NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h8H,5-7H2,1-4H3</inchi>
  <inchikey>UFAHZIUFPNSHSL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Acyl carnitines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl-carnitine</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fatty acyl carnitines</external_descriptor>
      <external_descriptor>O-acylcarnitine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(propanoyloxy)-4-(trimethylazaniumyl)butanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>217.2622</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>217.131408101</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(=O)OC(CC([O-])=O)C[N+](C)(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H19NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H19NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h8H,5-7H2,1-4H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UFAHZIUFPNSHSL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>77.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.06 +/- 0.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by DFI-MS/MS (P180) 4 week before parturition</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.2+/-0.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by ESI-MS/MS in male Charolais x Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Weikard R, Altmaier E, Suhre K, Weinberger KM, Hammon HM, Albrecht E, Setoguchi K, Takasuga A, Kuhn C: Metabolomic profiles indicate distinct physiological pathways affected by two loci with major divergent effect on Bos taurus growth and lipid deposition. Physiol Genomics. 2010 Oct;42A(2):79-88. doi: 10.1152/physiolgenomics.00120.2010. Epub 2010 Jul 20.</reference_text>
          <pubmed_id>20647382</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>3+/-1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>6+/-2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.1 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.4 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.93 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.016 +/- 0.006</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.016</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.011</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.023</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.017</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.017 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.01 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.02 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.02 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.036 +/- 0.006</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.09+/-0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>7+/-2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>0.6+/-0.2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <phenol_explorer_compound_id/>
  <chemspider_id>96904</chemspider_id>
  <foodb_id>FDB022268</foodb_id>
  <pubchem_compound_id>107738</pubchem_compound_id>
  <drugbank_id/>
  <kegg_id>C03017</kegg_id>
  <chebi_id>28867</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <knapsack_id/>
  <bigg_id>1862604</bigg_id>
  <metlin_id>5787</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
      <pubmed_id>28342601</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:09 UTC</creation_date>
  <update_date>2020-03-13 16:24:06 UTC</update_date>
  <accession>BMDB0000825</accession>
  <secondary_accessions>
    <accession>BMDB00825</accession>
  </secondary_accessions>
  <name>3'-Sialyllactose</name>
  <description>3'-Sialyllactose belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. 3'-Sialyllactose is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).</description>
  <synonyms>
    <synonym>(2&gt;3')-a-sialyllactose</synonym>
    <synonym>(2&gt;3')-alpha-sialyllactose</synonym>
    <synonym>3'-(N-Acetyl-a-neuraminosyl)lactose</synonym>
    <synonym>3'-(N-Acetyl-alpha-neuraminosyl)lactose</synonym>
    <synonym>3'-a-Sialyllactose</synonym>
    <synonym>3'-alpha-Sialyllactose</synonym>
    <synonym>3'-Monosialyllactose</synonym>
    <synonym>3'-N-Acetylneuraminyl-D-lactose</synonym>
    <synonym>3'-N-Acetylneuraminyl-delta-lactose</synonym>
    <synonym>3'-Sialyl-D-lactose</synonym>
    <synonym>3'-Sialyl-delta-lactose</synonym>
    <synonym>32-N-Acetyl-a-neuraminyllactose</synonym>
    <synonym>32-N-Acetyl-alpha-neuraminyllactose</synonym>
    <synonym>a-Neu5ac-(2&gt;3)-b-D-gal-(1&gt;4)-D-GLC</synonym>
    <synonym>a2,3-Sialyllactose</synonym>
    <synonym>alpha-Neu5ac-(2&gt;3)-beta-D-gal-(1&gt;4)-D-GLC</synonym>
    <synonym>alpha-Neu5ac-(2&gt;3)-beta-delta-gal-(1&gt;4)-delta-GLC</synonym>
    <synonym>N-Acetylneuraminoyllactose</synonym>
    <synonym>N-Acetylneuraminyl-2-3-galactopyranosyl-1-4-glucopyranose</synonym>
    <synonym>(2S,4S,5R,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate</synonym>
    <synonym>3'-Sialyllactose</synonym>
  </synonyms>
  <chemical_formula>C23H39NO19</chemical_formula>
  <average_molecular_weight>633.5511</average_molecular_weight>
  <monisotopic_moleculate_weight>633.211628071</monisotopic_moleculate_weight>
  <iupac_name>(2S,4S,5R,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>(2S,4S,5R,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</traditional_iupac>
  <cas_registry_number>35890-38-1</cas_registry_number>
  <smiles>[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO</smiles>
  <inchi>InChI=1S/C23H39NO19/c1-7(29)24-13-8(30)2-23(22(38)39,42-19(13)15(35)10(32)4-26)43-20-16(36)12(6-28)40-21(17(20)37)41-18(11(33)5-27)14(34)9(31)3-25/h3,8-21,26-28,30-37H,2,4-6H2,1H3,(H,24,29)(H,38,39)/t8-,9-,10+,11+,12+,13+,14+,15+,16-,17+,18+,19+,20-,21-,23-/m0/s1</inchi>
  <inchikey>OIZGSVFYNBZVIK-FHHHURIISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>N-acylneuraminic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alkyl glycosides</alternative_parent>
      <alternative_parent>Alpha-hydroxyaldehydes</alternative_parent>
      <alternative_parent>Beta-hydroxy aldehydes</alternative_parent>
      <alternative_parent>C-glucuronides</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketals</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Neuraminic acids</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Oligosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl glycoside</substituent>
      <substituent>Alpha-hydroxyaldehyde</substituent>
      <substituent>Beta-hydroxy aldehyde</substituent>
      <substituent>C-glucuronide</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty acyl glycoside</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketal</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acylneuraminic acid</substituent>
      <substituent>Neuraminic acid</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Oligosaccharide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,4S,5R,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>633.5511</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>633.211628071</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C23H39NO19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C23H39NO19/c1-7(29)24-13-8(30)2-23(22(38)39,42-19(13)15(35)10(32)4-26)43-20-16(36)12(6-28)40-21(17(20)37)41-18(11(33)5-27)14(34)9(31)3-25/h3,8-21,26-28,30-37H,2,4-6H2,1H3,(H,24,29)(H,38,39)/t8-,9-,10+,11+,12+,13+,14+,15+,16-,17+,18+,19+,20-,21-,23-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OIZGSVFYNBZVIK-FHHHURIISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>342.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>130.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>58.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345690</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value>150</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gopal PK, Gill HS: Oligosaccharides and glycoconjugates in bovine milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S69-74.</reference_text>
          <pubmed_id>11242449</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1131.716 +/- 42.617</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk collected 0-2 days before parturition</comment>
      <references>
        <reference>
          <reference_text>Nakamura T, Kawase H, Kimura K, Watanabe Y, Ohtani M, Arai I, Urashima T: Concentrations of sialyloligosaccharides in bovine colostrum and milk during the prepartum and early lactation. J Dairy Sci. 2003 Apr;86(4):1315-20. doi: 10.3168/jds.S0022-0302(03)73715-1.</reference_text>
          <pubmed_id>12741556</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>55.244 - 78.920</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Average over the milking season </comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB021795</foodb_id>
  <drugbank_id/>
  <chemspider_id>110445</chemspider_id>
  <pubchem_compound_id>123914</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <wikipedia_id/>
  <bigg_id/>
  <metlin_id>5788</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Masuda, Mika; Kawase, Yuuji; Kawase, Mitsuo.  Enzymic synthesis of (a2-3) sialyllactose using a membrane reactor.    Seibutsu Kogaku Kaishi  (2001),  79(9),  345-348.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Nakamura T, Kawase H, Kimura K, Watanabe Y, Ohtani M, Arai I, Urashima T: Concentrations of sialyloligosaccharides in bovine colostrum and milk during the prepartum and early lactation. J Dairy Sci. 2003 Apr;86(4):1315-20. doi: 10.3168/jds.S0022-0302(03)73715-1.</reference_text>
      <pubmed_id>12741556</pubmed_id>
    </reference>
    <reference>
      <reference_text>International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:11 UTC</creation_date>
  <update_date>2020-04-16 17:52:20 UTC</update_date>
  <accession>BMDB0000826</accession>
  <secondary_accessions>
    <accession>BMDB00826</accession>
  </secondary_accessions>
  <name>Pentadecanoic acid</name>
  <description>Pentadecanoic acid, also known as C15 or N-pentadecanoate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Pentadecanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Pentadecanoic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>15:00</synonym>
    <synonym>C15</synonym>
    <synonym>C15:0</synonym>
    <synonym>N-Pentadecanoic acid</synonym>
    <synonym>Pentadecylic acid</synonym>
    <synonym>N-Pentadecanoate</synonym>
    <synonym>Pentadecylate</synonym>
    <synonym>Pentadecanoate</synonym>
    <synonym>N-Pentadecylate</synonym>
    <synonym>N-Pentadecylic acid</synonym>
    <synonym>Pentadecyclate</synonym>
    <synonym>Pentadecyclic acid</synonym>
    <synonym>FA(15:0)</synonym>
    <synonym>Pentadecanoic acid</synonym>
  </synonyms>
  <chemical_formula>C15H30O2</chemical_formula>
  <average_molecular_weight>242.3975</average_molecular_weight>
  <monisotopic_moleculate_weight>242.224580204</monisotopic_moleculate_weight>
  <iupac_name>pentadecanoic acid</iupac_name>
  <traditional_iupac>pentadecanoic acid</traditional_iupac>
  <cas_registry_number>1002-84-2</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C15H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(16)17/h2-14H2,1H3,(H,16,17)</inchi>
  <inchikey>WQEPLUUGTLDZJY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>52.3 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>pentadecanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>242.3975</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>242.224580204</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H30O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(16)17/h2-14H2,1H3,(H,16,17)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WQEPLUUGTLDZJY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>44595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>44596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>44597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285858</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440409</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>706.86</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>655.62</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>20699.51</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>23355.11</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>16808.0116</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>17909.55</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>17450.68</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Calf-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>20792.29</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. With growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>21254.34</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Without growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>24938.38</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Yearling-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1526.42</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, konventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1443.91</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>453.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skimmed, konventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>825.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skimmed, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
          <pubmed_id>1779072</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1650.179 +/- 412.545</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
          <pubmed_id>16899705</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>This is a duplicate concentration of concentration_id 8166, unpexported by An Chi on Aug 20, 2018</comment>
      <references>
        <reference>
          <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples have been collected from Heifer cows.</comment>
      <references>
        <reference>
          <reference_text>Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub  2013 Jun 5.</reference_text>
          <pubmed_id>23871026</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1.5 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1.5 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by FAMEs/GC–MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C16537</kegg_id>
  <foodb_id>FDB010033</foodb_id>
  <drugbank_id/>
  <chemspider_id>13249</chemspider_id>
  <pubchem_compound_id>13849</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>42504</chebi_id>
  <knapsack_id>C00007423</knapsack_id>
  <phenol_explorer_compound_id/>
  <wikipedia_id>Pentadecanoic_acid</wikipedia_id>
  <bigg_id>215864</bigg_id>
  <metlin_id>5789</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
      <pubmed_id>16899705</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
      <pubmed_id>1779072</pubmed_id>
    </reference>
    <reference>
      <reference_text>Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.</reference_text>
      <pubmed_id>20855010</pubmed_id>
    </reference>
    <reference>
      <reference_text>Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93.</reference_text>
      <pubmed_id>5409465</pubmed_id>
    </reference>
    <reference>
      <reference_text>van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.</reference_text>
      <pubmed_id>28219465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.</reference_text>
      <pubmed_id>19038946</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:12 UTC</creation_date>
  <update_date>2020-04-16 20:40:01 UTC</update_date>
  <accession>BMDB0000827</accession>
  <secondary_accessions>
    <accession>BMDB00827</accession>
  </secondary_accessions>
  <name>Stearic acid</name>
  <description>Stearic acid, also known as stearate or 18:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Stearic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Stearic acid exists in all living species, ranging from bacteria to humans. Stearic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>18:0</synonym>
    <synonym>Acide octadecanoique</synonym>
    <synonym>Acide stearique</synonym>
    <synonym>C18:0</synonym>
    <synonym>CH3-[CH2]16-COOH</synonym>
    <synonym>N-Octadecanoic acid</synonym>
    <synonym>Octadecansaeure</synonym>
    <synonym>Octadecoic acid</synonym>
    <synonym>Oktadekansaeure</synonym>
    <synonym>Stearinsaeure</synonym>
    <synonym>Stearate</synonym>
    <synonym>N-Octadecanoate</synonym>
    <synonym>Octadecoate</synonym>
    <synonym>Octadecanoic acid</synonym>
    <synonym>Octadecanoate</synonym>
    <synonym>1-Heptadecanecarboxylate</synonym>
    <synonym>1-Heptadecanecarboxylic acid</synonym>
    <synonym>Stearex beads</synonym>
    <synonym>Stearic acid cherry</synonym>
    <synonym>Stearophanate</synonym>
    <synonym>Stearophanic acid</synonym>
    <synonym>Calcium stearate</synonym>
    <synonym>Aluminum tristearate</synonym>
    <synonym>Ammonium stearate</synonym>
    <synonym>Zinc stearate</synonym>
    <synonym>Magnesium stearate</synonym>
    <synonym>Sodium stearate</synonym>
    <synonym>Aluminum monostearate</synonym>
    <synonym>FA(18:0)</synonym>
  </synonyms>
  <chemical_formula>C18H36O2</chemical_formula>
  <average_molecular_weight>284.4772</average_molecular_weight>
  <monisotopic_moleculate_weight>284.271530396</monisotopic_moleculate_weight>
  <iupac_name>octadecanoic acid</iupac_name>
  <traditional_iupac>stearic acid</traditional_iupac>
  <cas_registry_number>57-11-4</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)</inchi>
  <inchikey>QIQXTHQIDYTFRH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Saturated fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>saturated fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>68.8 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.000597 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>8.23</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>8.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>octadecanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>284.4772</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>284.271530396</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H36O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QIQXTHQIDYTFRH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Plasmalogen Synthesis</name>
      <smpdb_id>SMP0087264</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440441</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>32663.0746</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>27546.67</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>798686.15</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>821695.38</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>299512.0171</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>273535.1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>295489.41</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Calf-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>322697.21</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. With growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>298498.44</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Without growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>330184.63</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Yearling-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed barley silage diet for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed barley silage diet with flaxseed for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed hay for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed hay with flaxseed for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.021 +/- 0.011</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by ESI-MS/MS in male Charolais x Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Widmann P, Reverter A, Weikard R, Suhre K, Hammon HM, Albrecht E, Kuehn C: Systems biology analysis merging phenotype, metabolomic and genomic data identifies Non-SMC Condensin I Complex, Subunit G (NCAPG) and cellular maintenance processes as major contributors to genetic variability in bovine feed efficiency. PLoS One. 2015 Apr 15;10(4):e0124574. doi: 10.1371/journal.pone.0124574. eCollection 2015.</reference_text>
          <pubmed_id>25875852</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by infra-red spectroscopy and silieic acid columns</comment>
      <references>
        <reference>
          <reference_text>Laura Evans, Stuart Patton, R.D. McCarthy. Fatty Acid Composition of the Lipid Fractions from Bovine Serum Lipoproteins. J. Dairy Science (1961) 44(3) 475-482   doi: 10.3168/jds.S0022-0302(61)89765-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by ESI-MS/MS in male Charolais x Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Weikard R, Altmaier E, Suhre K, Weinberger KM, Hammon HM, Albrecht E, Setoguchi K, Takasuga A, Kuhn C: Metabolomic profiles indicate distinct physiological pathways affected by two loci with major divergent effect on Bos taurus growth and lipid deposition. Physiol Genomics. 2010 Oct;42A(2):79-88. doi: 10.1152/physiolgenomics.00120.2010. Epub 2010 Jul 20.</reference_text>
          <pubmed_id>20647382</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.53 +/- 0.12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6046.18</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11.5 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4569.79</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1054.566</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1968.523</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1054.566</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12338.423</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12197.81</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10897.18</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35.90 +/- 5.72</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk from a Danish Holstein herd by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30.18 +/- 1.56</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised whole milk (3.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12.36 +/- 1.17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised semi skimmed milk (1.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.78 +/- 0.26</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised skimmed milk (0.1% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>24.33 +/- 0.08</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
          <pubmed_id>1779072</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19685.247 +/- 8436.534</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
          <pubmed_id>16899705</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>49.319 +/- 0.34</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Catrienus De Jong Herman T. Badings. Determination of free fatty acids in milk and cheese procedures for extraction, clean up, and capillary gas chromatographic analysis. Journal of High Resolution Chromatography Volume 13, Issue 2, 1990</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>130 +/- 22.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Fat content of plain milk wasn't specified in the reference. 3.25% is an estimate.</comment>
      <references>
        <reference>
          <reference_text>Lu CY, Wu HL, Chen SH, Kou HS, Wu SM: Simple and sensitive analysis of long-chain free fatty acids in milk by fluorogenic derivatization and high-performance liquid chromatography. J Agric Food Chem. 2002 Jan 2;50(1):71-3.</reference_text>
          <pubmed_id>11754544</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>78.2 +/- 9.0</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Fat content of low-fat milk wasn't specified in the reference. 1-2% is an estimate.</comment>
      <references>
        <reference>
          <reference_text>Lu CY, Wu HL, Chen SH, Kou HS, Wu SM: Simple and sensitive analysis of long-chain free fatty acids in milk by fluorogenic derivatization and high-performance liquid chromatography. J Agric Food Chem. 2002 Jan 2;50(1):71-3.</reference_text>
          <pubmed_id>11754544</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12936.0194 +/- 3901.897</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11846.300 +/- 3655.832</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10194.139</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>84716.807</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>99480.732</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>121626.619</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples have been collected from Heifer cows.</comment>
      <references>
        <reference>
          <reference_text>Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub  2013 Jun 5.</reference_text>
          <pubmed_id>23871026</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Oocyte</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by CP9010 autosampler onto a capillary column within a CP9001 gas chromatograph in slaughtered cow ovaries.</comment>
      <references>
        <reference>
          <reference_text>McEvoy TG, Coull GD, Broadbent PJ, Hutchinson JS, Speake BK: Fatty acid composition of lipids in immature cattle, pig and sheep oocytes with intact zona pellucida. J Reprod Fertil. 2000 Jan;118(1):163-70.</reference_text>
          <pubmed_id>10793638</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>185.6 +/- 27.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>186.0 +/- 27.0</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by FAMEs/GC–MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01530</kegg_id>
  <foodb_id>FDB031183</foodb_id>
  <drugbank_id>DB03193</drugbank_id>
  <chemspider_id>5091</chemspider_id>
  <pubchem_compound_id>5281</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28842</chebi_id>
  <knapsack_id>C00001238</knapsack_id>
  <phenol_explorer_compound_id/>
  <wikipedia_id>Stearic_acid</wikipedia_id>
  <bigg_id>37799</bigg_id>
  <metlin_id>189</metlin_id>
  <meta_cyc_id>STEARIC_ACID</meta_cyc_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
      <pubmed_id>16899705</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.</reference_text>
      <pubmed_id>1779072</pubmed_id>
    </reference>
    <reference>
      <reference_text>Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.</reference_text>
      <pubmed_id>20855010</pubmed_id>
    </reference>
    <reference>
      <reference_text>Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93.</reference_text>
      <pubmed_id>5409465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.</reference_text>
      <pubmed_id>19038946</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
    </reference>
    <reference>
      <reference_text>Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568   doi: 10.1016/0958-6946(96)85309-X</reference_text>
    </reference>
    <reference>
      <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:13 UTC</creation_date>
  <update_date>2020-04-14 22:48:27 UTC</update_date>
  <accession>BMDB0000828</accession>
  <secondary_accessions>
    <accession>BMDB00828</accession>
  </secondary_accessions>
  <name>Ureidosuccinic acid</name>
  <description>Ureidosuccinic acid, also known as L-ureidosuccinate or carbamyl-L-aspartate, belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Ureidosuccinic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Ureidosuccinic acid exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>Carbamyl-L-aspartic acid</synonym>
    <synonym>L-Ureidosuccinic acid</synonym>
    <synonym>N-(Aminocarbonyl)-L-aspartic acid</synonym>
    <synonym>N-Carbamoyl-L-aspartate</synonym>
    <synonym>N-Carbamoyl-S-aspartic acid</synonym>
    <synonym>Carbamyl-L-aspartate</synonym>
    <synonym>L-Ureidosuccinate</synonym>
    <synonym>N-(Aminocarbonyl)-L-aspartate</synonym>
    <synonym>N-Carbamoyl-L-aspartic acid</synonym>
    <synonym>N-Carbamoyl-S-aspartate</synonym>
    <synonym>Ureidosuccinate</synonym>
    <synonym>2-Ureidobutanedioate</synonym>
    <synonym>2-Ureidobutanedioic acid</synonym>
    <synonym>Carbamoylaspartic acid</synonym>
    <synonym>Carbamylaspartic acid</synonym>
    <synonym>L-N-Carbamoylaspartic acid</synonym>
    <synonym>N-Carbamoylaspartate</synonym>
    <synonym>N-Carbamoylaspartic acid</synonym>
    <synonym>NCD</synonym>
    <synonym>Carbamyl-DL-aspartate</synonym>
    <synonym>Ureidosuccinic acid, (D)-isomer</synonym>
    <synonym>Ureidosuccinic acid, maganeese (+2), (1:1) salt</synonym>
    <synonym>Ureidosuccinic acid, zinc (1:1) salt, (L)-isomer</synonym>
    <synonym>N-Carbamoyl-D-aspartic acid</synonym>
    <synonym>Ureidosuccinic acid, (L)-isomer</synonym>
    <synonym>Ureidosuccinic acid, cobalt (+2), (1:1) salt,(L)-isomer</synonym>
  </synonyms>
  <chemical_formula>C5H8N2O5</chemical_formula>
  <average_molecular_weight>176.1274</average_molecular_weight>
  <monisotopic_moleculate_weight>176.043321376</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-(carbamoylamino)butanedioic acid</iupac_name>
  <traditional_iupac>carbamylaspartic acid</traditional_iupac>
  <cas_registry_number>13184-27-5</cas_registry_number>
  <smiles>NC(=O)N[C@@H](CC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H8N2O5/c6-5(12)7-2(4(10)11)1-3(8)9/h2H,1H2,(H,8,9)(H,10,11)(H3,6,7,12)/t2-/m0/s1</inchi>
  <inchikey>HLKXYZVTANABHZ-REOHCLBHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Aspartic acid and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Isoureas</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Aspartic acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Isourea</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-aspartic acid derivative</external_descriptor>
      <external_descriptor>N-carbamoyl-L-amino acid</external_descriptor>
      <external_descriptor>N-carbamoylaspartic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>174 - 175 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>3.7 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-(carbamoylamino)butanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>176.1274</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>176.043321376</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)N[C@@H](CC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8N2O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8N2O5/c6-5(12)7-2(4(10)11)1-3(8)9/h2H,1H2,(H,8,9)(H,10,11)(H3,6,7,12)/t2-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HLKXYZVTANABHZ-REOHCLBHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>129.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437404</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fermented milk, by capillary electrophoresis-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
          <pubmed_id>26686724</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00438</kegg_id>
  <foodb_id>FDB031033</foodb_id>
  <drugbank_id>DB04252</drugbank_id>
  <chemspider_id>84022</chemspider_id>
  <pubchem_compound_id>93072</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15859</chebi_id>
  <knapsack_id>C00007265</knapsack_id>
  <phenol_explorer_compound_id/>
  <wikipedia_id>Carbamoyl_aspartic_acid</wikipedia_id>
  <bigg_id>34984</bigg_id>
  <metlin_id>5791</metlin_id>
  <meta_cyc_id>CARBAMYUL-L-ASPARTATE</meta_cyc_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
      <pubmed_id>26686724</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:14 UTC</creation_date>
  <update_date>2020-03-13 16:24:08 UTC</update_date>
  <accession>BMDB0000829</accession>
  <secondary_accessions>
    <accession>BMDB00829</accession>
  </secondary_accessions>
  <name>N-Stearoylsphingosine</name>
  <description/>
  <synonyms>
    <synonym>N-(1,3-Dihydroxyoctadec-4-en-2-yl)octadecanimidate</synonym>
  </synonyms>
  <chemical_formula>C36H71NO3</chemical_formula>
  <average_molecular_weight>565.968</average_molecular_weight>
  <monisotopic_moleculate_weight>565.54339515</monisotopic_moleculate_weight>
  <iupac_name>N-(1,3-dihydroxyoctadec-4-en-2-yl)octadecanamide</iupac_name>
  <traditional_iupac>N-(1,3-dihydroxyoctadec-4-en-2-yl)octadecanamide</traditional_iupac>
  <cas_registry_number>2304-81-6</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCCCC(=O)NC(CO)C(O)C=CCCCCCCCCCCCCC</smiles>
  <inchi>InChI=1S/C36H71NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38-39H,3-28,30,32-33H2,1-2H3,(H,37,40)</inchi>
  <inchikey>VODZWWMEJITOND-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Sphingolipids</class>
    <sub_class>Ceramides</sub_class>
    <direct_parent>Ceramides</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ceramide</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>9.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>11.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-(1,3-dihydroxyoctadec-4-en-2-yl)octadecanamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>565.968</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>565.54339515</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCCCC(=O)NC(CO)C(O)C=CCCCCCCCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C36H71NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C36H71NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38-39H,3-28,30,32-33H2,1-2H3,(H,37,40)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VODZWWMEJITOND-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>69.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>174.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>77.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>681415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>681416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>681417</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022270</foodb_id>
  <drugbank_id/>
  <chemspider_id>2843374</chemspider_id>
  <pubchem_compound_id>3607830</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <wikipedia_id/>
  <bigg_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Julina, Radomir; Herzig, Thomas; Bernet, Bruno; Vasella, Andrea.  Enantioselective synthesis of D-erythro-sphingosine and of ceramide.    Helvetica Chimica Acta  (1986),  69(2),  368-73. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:15 UTC</creation_date>
  <update_date>2020-04-16 20:40:01 UTC</update_date>
  <accession>BMDB0000830</accession>
  <secondary_accessions>
    <accession>BMDB00830</accession>
  </secondary_accessions>
  <name>Neuraminic acid</name>
  <description/>
  <synonyms>
    <synonym>Neuraminate</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonate</synonym>
    <synonym>5-(Acetylamino)-3,5-dideoxy-beta-L-erythro-2-nonulopyranosonic acid</synonym>
    <synonym>O-Sialate</synonym>
    <synonym>O-Sialic acid</synonym>
    <synonym>b-Neuraminate</synonym>
    <synonym>b-Neuraminic acid</synonym>
    <synonym>beta-Neuraminate</synonym>
    <synonym>Β-neuraminate</synonym>
    <synonym>Β-neuraminic acid</synonym>
  </synonyms>
  <chemical_formula>C9H17NO8</chemical_formula>
  <average_molecular_weight>267.2332</average_molecular_weight>
  <monisotopic_moleculate_weight>267.095416525</monisotopic_moleculate_weight>
  <iupac_name>(2S,4S,5R,6R)-5-amino-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>β-neuraminic acid</traditional_iupac>
  <cas_registry_number>114-04-5</cas_registry_number>
  <smiles>N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O</smiles>
  <inchi>InChI=1S/C9H17NO8/c10-5-3(12)1-9(17,8(15)16)18-7(5)6(14)4(13)2-11/h3-7,11-14,17H,1-2,10H2,(H,15,16)/t3-,4+,5+,6+,7+,9-/m0/s1</inchi>
  <inchikey>CERZMXAJYMMUDR-YOQZMRDMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Neuraminic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>1,3-aminoalcohols</alternative_parent>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminosaccharides</alternative_parent>
      <alternative_parent>C-glucuronides</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Delta amino acids and derivatives</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>1,3-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Amino saccharide</substituent>
      <substituent>C-glucuronide</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Delta amino acid or derivatives</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Neuraminic acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>5-amino-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>180.0 - 182.0 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,4S,5R,6R)-5-amino-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>267.2332</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>267.095416525</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H17NO8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H17NO8/c10-5-3(12)1-9(17,8(15)16)18-7(5)6(14)4(13)2-11/h3-7,11-14,17H,1-2,10H2,(H,15,16)/t3-,4+,5+,6+,7+,9-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CERZMXAJYMMUDR-YOQZMRDMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>173.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37792</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46847</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>153195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>153196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>153197</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C06469</kegg_id>
  <foodb_id>FDB022271</foodb_id>
  <drugbank_id/>
  <chemspider_id>447972</chemspider_id>
  <pubchem_compound_id>513472</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>49022</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <wikipedia_id>Neuraminic acid</wikipedia_id>
  <bigg_id/>
  <metlin_id>3394</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:16 UTC</creation_date>
  <update_date>2020-03-13 16:24:09 UTC</update_date>
  <accession>BMDB0000831</accession>
  <secondary_accessions>
    <accession>BMDB00831</accession>
  </secondary_accessions>
  <name>N-Lignoceroylsphingosine</name>
  <description/>
  <synonyms>
    <synonym>N-(1,3-Dihydroxyoctadec-4-en-2-yl)tetracosanimidate</synonym>
  </synonyms>
  <chemical_formula>C42H83NO3</chemical_formula>
  <average_molecular_weight>650.13</average_molecular_weight>
  <monisotopic_moleculate_weight>649.637295537</monisotopic_moleculate_weight>
  <iupac_name>N-(1,3-dihydroxyoctadec-4-en-2-yl)tetracosanamide</iupac_name>
  <traditional_iupac>N-(1,3-dihydroxyoctadec-4-en-2-yl)tetracosanamide</traditional_iupac>
  <cas_registry_number>34435-05-7</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(CO)C(O)C=CCCCCCCCCCCCCC</smiles>
  <inchi>InChI=1S/C42H83NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-42(46)43-40(39-44)41(45)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,40-41,44-45H,3-34,36,38-39H2,1-2H3,(H,43,46)</inchi>
  <inchikey>ZJVVOYPTFQEGPH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as ceramides. These are lipid molecules containing a sphingosine in which the amine group is linked to a fatty acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Sphingolipids</class>
    <sub_class>Ceramides</sub_class>
    <direct_parent>Ceramides</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ceramide</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>10.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>14.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-(1,3-dihydroxyoctadec-4-en-2-yl)tetracosanamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>650.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>649.637295537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(CO)C(O)C=CCCCCCCCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C42H83NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C42H83NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-42(46)43-40(39-44)41(45)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h35,37,40-41,44-45H,3-34,36,38-39H2,1-2H3,(H,43,46)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZJVVOYPTFQEGPH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>69.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>202.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>90.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>640132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>640133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>640134</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>2558952</chemspider_id>
  <foodb_id>FDB022272</foodb_id>
  <pubchem_compound_id>3311013</pubchem_compound_id>
  <kegg_id/>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Shoyama, Yukihiro; Okabe, Hikaru; Kishimoto, Yasuo; Costello, Catherine.  Total synthesis of stereospecific sphingosine and ceramide.    Journal of Lipid Research  (1978),  19(2),  250-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:17 UTC</creation_date>
  <update_date>2020-03-13 16:24:10 UTC</update_date>
  <accession>BMDB0000832</accession>
  <secondary_accessions>
    <accession>BMDB00832</accession>
  </secondary_accessions>
  <name>Capryloylglycine</name>
  <description/>
  <synonyms>
    <synonym>2-Octanamidoacetic acid</synonym>
    <synonym>Caprylylglycine</synonym>
    <synonym>N-(1-Oxooctyl)glycine</synonym>
    <synonym>2-Octanamidoacetate</synonym>
    <synonym>Capryloyl glycine</synonym>
    <synonym>Lipacide C 8g</synonym>
    <synonym>N-(1-Oxooctyl)-glycine</synonym>
    <synonym>N-Octanoyl-glycine</synonym>
    <synonym>N-Octanoylglycine</synonym>
  </synonyms>
  <chemical_formula>C10H19NO3</chemical_formula>
  <average_molecular_weight>201.2628</average_molecular_weight>
  <monisotopic_moleculate_weight>201.136493479</monisotopic_moleculate_weight>
  <iupac_name>2-octanamidoacetic acid</iupac_name>
  <traditional_iupac>N-octanoylglycine</traditional_iupac>
  <cas_registry_number>14246-53-8</cas_registry_number>
  <smiles>CCCCCCCC(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C10H19NO3/c1-2-3-4-5-6-7-9(12)11-8-10(13)14/h2-8H2,1H3,(H,11,12)(H,13,14)</inchi>
  <inchikey>SAVLIIGUQOSOEP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylglycine</external_descriptor>
      <external_descriptor>fatty amide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-octanamidoacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>201.2628</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>201.136493479</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCC(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H19NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H19NO3/c1-2-3-4-5-6-7-9(12)11-8-10(13)14/h2-8H2,1H3,(H,11,12)(H,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SAVLIIGUQOSOEP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>53.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351054</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>76040</chemspider_id>
  <foodb_id>FDB022273</foodb_id>
  <pubchem_compound_id>84290</pubchem_compound_id>
  <kegg_id/>
  <drugbank_id/>
  <chebi_id>74099</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5795</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:19 UTC</creation_date>
  <update_date>2020-04-15 22:32:42 UTC</update_date>
  <accession>BMDB0000833</accession>
  <secondary_accessions>
    <accession>BMDB00833</accession>
  </secondary_accessions>
  <name>N-Glycolylneuraminic acid</name>
  <description/>
  <synonyms>
    <synonym>GcNeu</synonym>
    <synonym>N-Glycolyl-beta-neuraminic acid</synonym>
    <synonym>Neu5GC</synonym>
    <synonym>NeuGc</synonym>
    <synonym>NGNA</synonym>
    <synonym>N-Glycolyl-b-neuraminate</synonym>
    <synonym>N-Glycolyl-b-neuraminic acid</synonym>
    <synonym>N-Glycolyl-beta-neuraminate</synonym>
    <synonym>N-Glycolyl-β-neuraminate</synonym>
    <synonym>N-Glycolyl-β-neuraminic acid</synonym>
    <synonym>N-Glycolylneuraminate</synonym>
    <synonym>3,5-Dideoxy-5-((hydroxyacetyl)amino)-D-glycero-D-galacto-2-nonulosonate</synonym>
    <synonym>3,5-Dideoxy-5-((hydroxyacetyl)amino)-D-glycero-D-galacto-2-nonulosonic acid</synonym>
    <synonym>N-Glycoloyl-neuraminate</synonym>
    <synonym>N-Glycoloylneuraminate</synonym>
    <synonym>N-Glycoloylneuraminic acid</synonym>
    <synonym>N-Glycolyl-5-neuraminate</synonym>
    <synonym>N-Glycolyl-5-neuraminic acid</synonym>
    <synonym>N-Glycolylneuraminic acid, (alpha-D-gal)-isomer</synonym>
    <synonym>N-Glycoloyl-b-neuraminate</synonym>
    <synonym>N-Glycoloyl-b-neuraminic acid</synonym>
    <synonym>N-Glycoloyl-beta-neuraminate</synonym>
    <synonym>N-Glycoloyl-β-neuraminate</synonym>
    <synonym>N-Glycoloyl-β-neuraminic acid</synonym>
    <synonym>N-Glycolylneuraminic acid</synonym>
  </synonyms>
  <chemical_formula>C11H19NO10</chemical_formula>
  <average_molecular_weight>325.2693</average_molecular_weight>
  <monisotopic_moleculate_weight>325.100895833</monisotopic_moleculate_weight>
  <iupac_name>(2S,4S,5R,6R)-2,4-dihydroxy-5-(2-hydroxyacetamido)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>N-glycolylneuraminic acid</traditional_iupac>
  <cas_registry_number>1113-83-3</cas_registry_number>
  <smiles>OC[C@@H](O)[C@@H](O)[C@@H]1O[C@@](O)(C[C@H](O)[C@H]1NC(=O)CO)C(O)=O</smiles>
  <inchi>InChI=1S/C11H19NO10/c13-2-5(16)8(18)9-7(12-6(17)3-14)4(15)1-11(21,22-9)10(19)20/h4-5,7-9,13-16,18,21H,1-3H2,(H,12,17)(H,19,20)/t4-,5+,7+,8+,9+,11-/m0/s1</inchi>
  <inchikey>FDJKUWYYUZCUJX-AJKRCSPLSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Neuraminic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>C-glucuronides</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>C-glucuronide</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Neuraminic acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylneuraminic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,4S,5R,6R)-2,4-dihydroxy-5-(2-hydroxyacetamido)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>325.2693</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>325.100895833</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)[C@@H](O)[C@@H]1O[C@@](O)(C[C@H](O)[C@H]1NC(=O)CO)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H19NO10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H19NO10/c13-2-5(16)8(18)9-7(12-6(17)3-14)4(15)1-11(21,22-9)10(19)20/h4-5,7-9,13-16,18,21H,1-3H2,(H,12,17)(H,19,20)/t4-,5+,7+,8+,9+,11-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FDJKUWYYUZCUJX-AJKRCSPLSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>197.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>65.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446235</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>110352</chemspider_id>
  <foodb_id>FDB001165</foodb_id>
  <pubchem_compound_id>123802</pubchem_compound_id>
  <kegg_id>C03410</kegg_id>
  <drugbank_id/>
  <chebi_id>62084</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>N-Glycolylneuraminic_acid</wikipedia_id>
  <metlin_id>3580</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:20 UTC</creation_date>
  <update_date>2020-03-13 16:24:11 UTC</update_date>
  <accession>BMDB0000839</accession>
  <secondary_accessions>
    <accession>BMDB00839</accession>
  </secondary_accessions>
  <name>Pentaporphyrin I</name>
  <description/>
  <synonyms>
    <synonym>(+)-Isoboldine</synonym>
    <synonym>2,10-Dimethoxy-6a-aporphine-1,9-diol</synonym>
    <synonym>2,10-Dimethoxy-6alpha-aporphine-1,9-diol</synonym>
    <synonym>21H,23H-Porphin</synonym>
    <synonym>21H,23H-Porphine</synonym>
    <synonym>D-Isoboldine</synonym>
    <synonym>delta-Isoboldine</synonym>
    <synonym>Isoboldine</synonym>
    <synonym>Porphine</synonym>
    <synonym>Prolmon</synonym>
    <synonym>Protoporphyrin disodium</synonym>
  </synonyms>
  <chemical_formula>C20H14N4</chemical_formula>
  <average_molecular_weight>310.352</average_molecular_weight>
  <monisotopic_moleculate_weight>310.121846468</monisotopic_moleculate_weight>
  <iupac_name>21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3,5,7,9,11,13(22),14,16,18(21),19-undecaene</iupac_name>
  <traditional_iupac>porphin</traditional_iupac>
  <cas_registry_number>3019-51-0</cas_registry_number>
  <smiles>N1C2=CC=C1\C=C1\C=CC(\C=C3\C=CC(\C=C4/N\C(\C=C4)=C/2)=N3)=N1</smiles>
  <inchi>InChI=1S/C20H14N4/c1-2-14-10-16-5-6-18(23-16)12-20-8-7-19(24-20)11-17-4-3-15(22-17)9-13(1)21-14/h1-12,21-22H/b13-9-,14-10-,15-9-,16-10-,17-11-,18-12-,19-11-,20-12-</inchi>
  <inchikey>JZRYQZJSTWVBBD-CEVVSZFKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3,5,7,9,11,13(22),14,16,18(21),19-undecaene</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>310.352</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>310.121846468</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N1C2=CC=C1\C=C1\C=CC(\C=C3\C=CC(\C=C4/N\C(\C=C4)=C/2)=N3)=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H14N4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H14N4/c1-2-14-10-16-5-6-18(23-16)12-20-8-7-19(24-20)11-17-4-3-15(22-17)9-13(1)21-14/h1-12,21-22H/b13-9-,14-10-,15-9-,16-10-,17-11-,18-12-,19-11-,20-12-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JZRYQZJSTWVBBD-CEVVSZFKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>92.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326745</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>60231</chemspider_id>
  <foodb_id>FDB002225</foodb_id>
  <pubchem_compound_id/>
  <kegg_id>C09541</kegg_id>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001869</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5802</metlin_id>
  <synthesis_reference>Kametani, Tetsuji; Sugahara, Tokuji; Yagi, Haruhiko; Fukumoto, Keiichiro.  Synthesis of heterocyclic compounds.  CCCXIV.  Biogenetic type syntheses of aporphine alkaloids, isoboldine and glaucine.    Tetrahedron  (1969),  25(17),  3667-73.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:22 UTC</creation_date>
  <update_date>2020-03-13 16:24:11 UTC</update_date>
  <accession>BMDB0000840</accession>
  <secondary_accessions>
    <accession>BMDB00840</accession>
  </secondary_accessions>
  <name>Salicyluric acid</name>
  <description>Salicylurate, also known as salicyloylglycine or O-hydroxyhippate, belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine. Salicylurate exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Salicylurate exists in all eukaryotes, ranging from yeast to humans.</description>
  <synonyms>
    <synonym>N-(2-Hydroxybenzoyl)-glycine</synonym>
    <synonym>N-Salicyloylglycine</synonym>
    <synonym>O-Hydroxyhippuric acid</synonym>
    <synonym>Salicyloylglycine</synonym>
    <synonym>Salicylurate</synonym>
    <synonym>O-Hydroxyhippate</synonym>
    <synonym>O-Hydroxyhippic acid</synonym>
    <synonym>Salicylate</synonym>
    <synonym>Salicylic acid</synonym>
    <synonym>((2-Hydroxybenzoyl)amino)acetic acid</synonym>
    <synonym>(2-Hydroxybenzoyl)glycine</synonym>
    <synonym>2-Hydroxybenzoylaminoacetate</synonym>
    <synonym>2-Hydroxybenzoylaminoacetic acid</synonym>
    <synonym>2-Hydroxybenzoylglycine</synonym>
    <synonym>2-Hydroxyhippurate</synonym>
    <synonym>2-Hydroxyhippuric acid</synonym>
    <synonym>N-O-Hydroxybenzoylglycine</synonym>
    <synonym>O-Hydroxy-hippurate</synonym>
    <synonym>O-Hydroxy-hippuric acid</synonym>
    <synonym>O-Hydroxyhippurate</synonym>
    <synonym>Ortho-hydroxyhippurate</synonym>
    <synonym>Ortho-hydroxyhippuric acid</synonym>
    <synonym>Salicylglycine</synonym>
    <synonym>[(2-Hydroxybenzoyl)amino]acetate</synonym>
    <synonym>[(2-Hydroxybenzoyl)amino]acetic acid</synonym>
    <synonym>Salicylurate, monosodium salt</synonym>
    <synonym>N-(O-Hydroxybenzoyl)glycine</synonym>
    <synonym>N-(2-Hydroxybenzoyl)glycine</synonym>
    <synonym>Salicyluric acid</synonym>
  </synonyms>
  <chemical_formula>C9H9NO4</chemical_formula>
  <average_molecular_weight>195.1721</average_molecular_weight>
  <monisotopic_moleculate_weight>195.053157781</monisotopic_moleculate_weight>
  <iupac_name>2-[(2-hydroxyphenyl)formamido]acetic acid</iupac_name>
  <traditional_iupac>salicyluric acid</traditional_iupac>
  <cas_registry_number>487-54-7</cas_registry_number>
  <smiles>OC(=O)CNC(=O)C1=C(O)C=CC=C1</smiles>
  <inchi>InChI=1S/C9H9NO4/c11-7-4-2-1-3-6(7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)</inchi>
  <inchikey>ONJSZLXSECQROL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>Hippuric acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Salicylamides</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hippuric acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Salicylamide</substituent>
      <substituent>Salicylic acid or derivatives</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acyl-amino acid</external_descriptor>
      <external_descriptor>N-acylglycine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>168 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.95</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(2-hydroxyphenyl)formamido]acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>195.1721</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>195.053157781</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CNC(=O)C1=C(O)C=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H9NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H9NO4/c11-7-4-2-1-3-6(7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ONJSZLXSECQROL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>86.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>48.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438669</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>9835</chemspider_id>
  <foodb_id>FDB010505</foodb_id>
  <pubchem_compound_id>10253</pubchem_compound_id>
  <kegg_id>C07588</kegg_id>
  <drugbank_id/>
  <chebi_id>9008</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Salicyluric_acid</wikipedia_id>
  <metlin_id>617</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:23 UTC</creation_date>
  <update_date>2020-03-13 16:24:12 UTC</update_date>
  <accession>BMDB0000841</accession>
  <secondary_accessions>
    <accession>BMDB00841</accession>
  </secondary_accessions>
  <name>N-Acetylgalactosamine 6-sulfate</name>
  <description/>
  <synonyms>
    <synonym>N-Acetylgalactosamine 6-sulfuric acid</synonym>
    <synonym>N-Acetylgalactosamine 6-sulphate</synonym>
    <synonym>N-Acetylgalactosamine 6-sulphuric acid</synonym>
    <synonym>N-Acetyl-chondrosamine 6-(hydrogen sulfate)</synonym>
    <synonym>N-Acetyl-chondrosamine 6-(hydrogen sulphate)</synonym>
    <synonym>Nag-6-S</synonym>
    <synonym>N-[(2R,3R,4R,5R)-3,4,5-Trihydroxy-1-oxo-6-(sulfooxy)hexan-2-yl]ethanimidate</synonym>
    <synonym>N-[(2R,3R,4R,5R)-3,4,5-Trihydroxy-1-oxo-6-(sulphooxy)hexan-2-yl]ethanimidate</synonym>
    <synonym>N-[(2R,3R,4R,5R)-3,4,5-Trihydroxy-1-oxo-6-(sulphooxy)hexan-2-yl]ethanimidic acid</synonym>
    <synonym>N-Acetylgalactosamine 6-sulfate</synonym>
  </synonyms>
  <chemical_formula>C8H15NO9S</chemical_formula>
  <average_molecular_weight>301.271</average_molecular_weight>
  <monisotopic_moleculate_weight>301.046751773</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3R,4R,5R)-5-acetamido-2,3,4-trihydroxy-6-oxohexyl]oxy}sulfonic acid</iupac_name>
  <traditional_iupac>[(2R,3R,4R,5R)-5-acetamido-2,3,4-trihydroxy-6-oxohexyl]oxysulfonic acid</traditional_iupac>
  <cas_registry_number>10357-00-3</cas_registry_number>
  <smiles>CC(=O)N[C@@H](C=O)[C@@H](O)[C@@H](O)[C@H](O)COS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C8H15NO9S/c1-4(11)9-5(2-10)7(13)8(14)6(12)3-18-19(15,16)17/h2,5-8,12-14H,3H2,1H3,(H,9,11)(H,15,16,17)/t5-,6+,7+,8-/m0/s1</inchi>
  <inchikey>NHZWETQZLORZIR-OSMVPFSASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharide sulfates. These are monosaccharides that contain a sulfate group linked to the sugar moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharide sulfates</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Aminosaccharides</alternative_parent>
      <alternative_parent>Beta-hydroxy aldehydes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Amino saccharide</substituent>
      <substituent>Beta-hydroxy aldehyde</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide sulfate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3R,4R,5R)-5-acetamido-2,3,4-trihydroxy-6-oxohexyl]oxy}sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>301.271</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>301.046751773</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H](C=O)[C@@H](O)[C@@H](O)[C@H](O)COS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15NO9S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15NO9S/c1-4(11)9-5(2-10)7(13)8(14)6(12)3-18-19(15,16)17/h2,5-8,12-14H,3H2,1H3,(H,9,11)(H,15,16,17)/t5-,6+,7+,8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NHZWETQZLORZIR-OSMVPFSASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>170.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>58.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37796</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360003</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>167877</chemspider_id>
  <foodb_id>FDB022274</foodb_id>
  <pubchem_compound_id>193456</pubchem_compound_id>
  <kegg_id/>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5804</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:24 UTC</creation_date>
  <update_date>2020-03-13 16:24:13 UTC</update_date>
  <accession>BMDB0000842</accession>
  <secondary_accessions>
    <accession>BMDB00842</accession>
  </secondary_accessions>
  <name>Quinaldic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Carboxyquinoline</synonym>
    <synonym>2-Chinolincarbonsaeure</synonym>
    <synonym>2-Quinolinecarboxylate</synonym>
    <synonym>2-Quinolinecarboxylic acid</synonym>
    <synonym>Chinaldinsaeure</synonym>
    <synonym>Quinaldate</synonym>
    <synonym>Quinaldinic acid</synonym>
    <synonym>Quinoline-2-carboxylic acid</synonym>
    <synonym>Quinaldinate</synonym>
    <synonym>Quinoline-2-carboxylate</synonym>
    <synonym>2-Quinolinylcarboxylate</synonym>
    <synonym>2-Quinolinylcarboxylic acid</synonym>
    <synonym>Quinolin-2-carboxylate</synonym>
    <synonym>Quinolin-2-carboxylic acid</synonym>
    <synonym>Quinaldic acid</synonym>
  </synonyms>
  <chemical_formula>C10H7NO2</chemical_formula>
  <average_molecular_weight>173.1681</average_molecular_weight>
  <monisotopic_moleculate_weight>173.047678473</monisotopic_moleculate_weight>
  <iupac_name>quinoline-2-carboxylic acid</iupac_name>
  <traditional_iupac>quinaldic acid</traditional_iupac>
  <cas_registry_number>93-10-7</cas_registry_number>
  <smiles>OC(=O)C1=NC2=C(C=CC=C2)C=C1</smiles>
  <inchi>InChI=1S/C10H7NO2/c12-10(13)9-6-5-7-3-1-2-4-8(7)11-9/h1-6H,(H,12,13)</inchi>
  <inchikey>LOAUVZALPPNFOQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Quinolines and derivatives</class>
    <sub_class>Quinoline carboxylic acids</sub_class>
    <direct_parent>Quinoline carboxylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridinecarboxylic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridine carboxylic acid</substituent>
      <substituent>Pyridine carboxylic acid or derivatives</substituent>
      <substituent>Quinoline-2-carboxylic acid</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>quinolinemonocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>156 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>14.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>quinoline-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>173.1681</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>173.047678473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1=NC2=C(C=CC=C2)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H7NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H7NO2/c12-10(13)9-6-5-7-3-1-2-4-8(7)11-9/h1-6H,(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LOAUVZALPPNFOQ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>50.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>263394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>263395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>263396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>283323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>283324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>283325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451980</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>6857</chemspider_id>
  <foodb_id>FDB022275</foodb_id>
  <pubchem_compound_id>7124</pubchem_compound_id>
  <kegg_id>C06325</kegg_id>
  <drugbank_id>DB02428</drugbank_id>
  <chebi_id>18386</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5805</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:25 UTC</creation_date>
  <update_date>2020-03-13 16:24:13 UTC</update_date>
  <accession>BMDB0000843</accession>
  <secondary_accessions>
    <accession>BMDB00843</accession>
  </secondary_accessions>
  <name>N-Acetylgalactosamine 4,6-disulfate</name>
  <description/>
  <synonyms>
    <synonym>N-Acetylgalactosamine 4,6-disulfuric acid</synonym>
    <synonym>N-Acetylgalactosamine 4,6-disulphate</synonym>
    <synonym>N-Acetylgalactosamine 4,6-disulphuric acid</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-D-galactose 4,6-bis</synonym>
    <synonym>2-Acetamido-2-deoxy-D-galactose 4,6-bissulfate</synonym>
    <synonym>2-Acetamido-2-deoxy-D-galactose 4,6-bissulphate</synonym>
    <synonym>N-Acetyl-chondrosamine 4,6-disulfate</synonym>
    <synonym>N-Acetyl-chondrosamine 4,6-disulphate</synonym>
    <synonym>N-Acetylgalactosamine 4,6-bisulfate</synonym>
    <synonym>N-Acetylgalactosamine 4,6-bisulphate</synonym>
    <synonym>Nagabs</synonym>
    <synonym>N-[(3R,4R,5R,6R)-2,4-Dihydroxy-5-(sulfooxy)-6-[(sulfooxy)methyl]oxan-3-yl]ethanimidate</synonym>
    <synonym>N-[(3R,4R,5R,6R)-2,4-Dihydroxy-5-(sulphooxy)-6-[(sulphooxy)methyl]oxan-3-yl]ethanimidate</synonym>
    <synonym>N-[(3R,4R,5R,6R)-2,4-Dihydroxy-5-(sulphooxy)-6-[(sulphooxy)methyl]oxan-3-yl]ethanimidic acid</synonym>
  </synonyms>
  <chemical_formula>C8H15NO12S2</chemical_formula>
  <average_molecular_weight>381.334</average_molecular_weight>
  <monisotopic_moleculate_weight>381.003566329</monisotopic_moleculate_weight>
  <iupac_name>[(2R,3R,4R,5R)-5-acetamido-4,6-dihydroxy-2-[(sulfooxy)methyl]oxan-3-yl]oxidanesulfonic acid</iupac_name>
  <traditional_iupac>[(2R,3R,4R,5R)-5-acetamido-4,6-dihydroxy-2-[(sulfooxy)methyl]oxan-3-yl]oxidanesulfonic acid</traditional_iupac>
  <cas_registry_number>52510-51-7</cas_registry_number>
  <smiles>CC(=O)N[C@H]1C(O)O[C@H](COS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C8H15NO12S2/c1-3(10)9-5-6(11)7(21-23(16,17)18)4(20-8(5)12)2-19-22(13,14)15/h4-8,11-12H,2H2,1H3,(H,9,10)(H,13,14,15)(H,16,17,18)/t4-,5-,6-,7+,8?/m1/s1</inchi>
  <inchikey>KWDXXNWKTRGMDM-IYWGXSQHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Acylaminosugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharide sulfates</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Acylaminosugar</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide sulfate</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-2.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(2R,3R,4R,5R)-5-acetamido-4,6-dihydroxy-2-[(sulfooxy)methyl]oxan-3-yl]oxidanesulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>381.334</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>381.003566329</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@H]1C(O)O[C@H](COS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15NO12S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15NO12S2/c1-3(10)9-5-6(11)7(21-23(16,17)18)4(20-8(5)12)2-19-22(13,14)15/h4-8,11-12H,2H2,1H3,(H,9,10)(H,13,14,15)(H,16,17,18)/t4-,5-,6-,7+,8?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KWDXXNWKTRGMDM-IYWGXSQHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>205.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>67.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345414</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>17216013</chemspider_id>
  <foodb_id>FDB022276</foodb_id>
  <pubchem_compound_id>22833549</pubchem_compound_id>
  <kegg_id/>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5806</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:26 UTC</creation_date>
  <update_date>2020-04-16 20:39:44 UTC</update_date>
  <accession>BMDB0000845</accession>
  <secondary_accessions>
    <accession>BMDB00845</accession>
  </secondary_accessions>
  <name>Neopterin</name>
  <description/>
  <synonyms>
    <synonym>6-(D-Erythro-1,2,3-trihydroxypropyl)pterin</synonym>
    <synonym>6-D-Erythro-neopterin</synonym>
    <synonym>D-Erythro-neopterin</synonym>
    <synonym>D-Neopterin</synonym>
    <synonym>Neopterine</synonym>
    <synonym>[S-(R*,s*)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridin-4-ON</synonym>
    <synonym>[S-(R*,s*)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridin-4-one</synonym>
    <synonym>[S-(R*,s*)]-2-amino-6-(1,2,3-trihydroxypropyl)-1H-pteridine-4-one</synonym>
    <synonym>Monapterin</synonym>
    <synonym>Neopterin, (r*, r*)-isomer</synonym>
    <synonym>Umanopterin</synonym>
    <synonym>Neopterin, (erythro-D)-isomer</synonym>
    <synonym>2-Amino-6-(1,2,3-trihydroxypropyl)-4(3H)-pteridinone</synonym>
    <synonym>Neopterin, (erythro-L)-isomer</synonym>
    <synonym>Neopterin, (threo-D)-isomer</synonym>
    <synonym>Neopterin, (threo-L)-isomer</synonym>
  </synonyms>
  <chemical_formula>C9H11N5O4</chemical_formula>
  <average_molecular_weight>253.2147</average_molecular_weight>
  <monisotopic_moleculate_weight>253.081103865</monisotopic_moleculate_weight>
  <iupac_name>2-amino-6-(1,2,3-trihydroxypropyl)-3,4-dihydropteridin-4-one</iupac_name>
  <traditional_iupac>2-amino-6-(1,2,3-trihydroxypropyl)-3H-pteridin-4-one</traditional_iupac>
  <cas_registry_number>2009-64-5</cas_registry_number>
  <smiles>NC1=NC2=C(N=C(C=N2)C(O)C(O)CO)C(=O)N1</smiles>
  <inchi>InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)</inchi>
  <inchikey>BMQYVXCPAOLZOK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Biopterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrazines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Biopterin</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrazine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-6-(1,2,3-trihydroxypropyl)-3,4-dihydropteridin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>253.2147</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>253.081103865</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=C(C=N2)C(O)C(O)CO)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11N5O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BMQYVXCPAOLZOK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>153.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pterine Biosynthesis</name>
      <smpdb_id>SMP0087250</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14362</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB005562</foodb_id>
  <chemspider_id>4300</chemspider_id>
  <kegg_id>C05926</kegg_id>
  <pubchem_compound_id>4455</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Neopterin</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>248</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:27 UTC</creation_date>
  <update_date>2020-04-16 20:39:21 UTC</update_date>
  <accession>BMDB0000847</accession>
  <secondary_accessions>
    <accession>BMDB00847</accession>
  </secondary_accessions>
  <name>Pelargonic acid</name>
  <description>Nonanoic acid, also known as pelargon or nonanoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Nonanoic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Nonanoic acid exists in all living species, ranging from bacteria to humans. Nonanoic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Nonanoic acid</synonym>
    <synonym>1-Octanecarboxylic acid</synonym>
    <synonym>CH3-[CH2]7-COOH</synonym>
    <synonym>N-Nonanoic acid</synonym>
    <synonym>Nonanoate</synonym>
    <synonym>Nonansaeure</synonym>
    <synonym>Nonoic acid</synonym>
    <synonym>Nonylic acid</synonym>
    <synonym>Pelargic acid</synonym>
    <synonym>Pelargon</synonym>
    <synonym>Pelargonsaeure</synonym>
    <synonym>Pergonic acid</synonym>
    <synonym>1-Nonanoate</synonym>
    <synonym>1-Octanecarboxylate</synonym>
    <synonym>N-Nonanoate</synonym>
    <synonym>Nonanoic acid</synonym>
    <synonym>Nonoate</synonym>
    <synonym>Nonylate</synonym>
    <synonym>Pelargate</synonym>
    <synonym>Pergonate</synonym>
    <synonym>Pelargonate</synonym>
    <synonym>Cirrasol 185a</synonym>
    <synonym>Emery 1202</synonym>
    <synonym>Emery'S L-114</synonym>
    <synonym>Emfac 1202</synonym>
    <synonym>Hexacid C-9</synonym>
    <synonym>N-Nonoate</synonym>
    <synonym>N-Nonoic acid</synonym>
    <synonym>N-Nonylate</synonym>
    <synonym>N-Nonylic acid</synonym>
    <synonym>N-Pelargonate</synonym>
    <synonym>N-Pelargonic acid</synonym>
    <synonym>Pelargonic acid, calcium salt</synonym>
    <synonym>Potassium nonanoate</synonym>
    <synonym>Pelargonic acid, cadmium salt</synonym>
    <synonym>Pelargonic acid, sodium salt</synonym>
    <synonym>Pelargonic acid, zinc salt</synonym>
    <synonym>Pelargonic acid, aluminum salt</synonym>
    <synonym>Pelargonic acid, potassium salt</synonym>
    <synonym>FA(9:0)</synonym>
    <synonym>Pelargonic acid</synonym>
  </synonyms>
  <chemical_formula>C9H18O2</chemical_formula>
  <average_molecular_weight>158.238</average_molecular_weight>
  <monisotopic_moleculate_weight>158.13067982</monisotopic_moleculate_weight>
  <iupac_name>nonanoic acid</iupac_name>
  <traditional_iupac>nonanoic acid</traditional_iupac>
  <cas_registry_number>112-05-0</cas_registry_number>
  <smiles>CCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11)</inchi>
  <inchikey>FBUKVWPVBMHYJY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>medium-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>12.3 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.284 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.42</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>nonanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>158.238</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>158.13067982</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H18O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FBUKVWPVBMHYJY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>44.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438670</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.251 +/- 0.001</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.468 +/- 0.012</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.568 +/- 0.014</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.64 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB003306</foodb_id>
  <chemspider_id>7866</chemspider_id>
  <kegg_id>C01601</kegg_id>
  <pubchem_compound_id>8158</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>29019</chebi_id>
  <drugbank_id/>
  <meta_cyc_id>CPD-8505</meta_cyc_id>
  <knapsack_id>C00030829</knapsack_id>
  <wikipedia_id>Nonanoic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5810</metlin_id>
  <synthesis_reference>Yu, Zhongjiang; Wang, Jinglin; Shi, Zhiming.  Industrial process for producing azelaic acid and nonanoic acid.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2007),     8pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:28 UTC</creation_date>
  <update_date>2020-04-14 22:48:28 UTC</update_date>
  <accession>BMDB0000848</accession>
  <secondary_accessions>
    <accession>BMDB00848</accession>
  </secondary_accessions>
  <name>Stearoylcarnitine</name>
  <description>Stearoylcarnitine, also known as acylcarnitine C18:0, belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Thus, stearoylcarnitine is considered to be a fatty ester lipid molecule. Stearoylcarnitine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, stearoylcarnitine is involved in the metabolic pathway called the mitochondrial Beta-oxidation OF long chain saturated fatty acids pathway.</description>
  <synonyms>
    <synonym>(-)-Stearoylcarnitine</synonym>
    <synonym>(R)-Octadecanoylcarnitine</synonym>
    <synonym>(R)-Stearoylcarnitine</synonym>
    <synonym>Acylcarnitine C18:0</synonym>
    <synonym>L-Stearoylcarnitine</synonym>
    <synonym>O-Octadecanoyl-(R)-carnitine</synonym>
    <synonym>O-Octadecanoyl-R-carnitine</synonym>
    <synonym>O-Stearoyl-L-carnitine</synonym>
    <synonym>Octadecanoylcarnitine</synonym>
    <synonym>3-(Octadecanoyloxy)-4-(trimethylammonio)butanoate</synonym>
    <synonym>O-Octadecanoylcarnitine</synonym>
    <synonym>3-(Octadecanoyloxy)-4-(trimethylammonio)butanoic acid</synonym>
    <synonym>(R)-3-Carboxy-N,N,N-trimethyl-2-[(1-oxooctadecyl)oxy]-1-propanaminium inner salt</synonym>
    <synonym>L-(3-Carboxy-2-hydroxypropyl)trimethyl-ammonium stearate hydroxide inner salt</synonym>
    <synonym>L-Stearic acid ester with (3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt</synonym>
    <synonym>Octadecanoyl-L-carnitine</synonym>
    <synonym>Stearoyl-L-carnitine</synonym>
    <synonym>Stearoylcarnitine</synonym>
  </synonyms>
  <chemical_formula>C25H49NO4</chemical_formula>
  <average_molecular_weight>427.67</average_molecular_weight>
  <monisotopic_moleculate_weight>427.366159062</monisotopic_moleculate_weight>
  <iupac_name>(3R)-3-(octadecanoyloxy)-4-(trimethylazaniumyl)butanoate</iupac_name>
  <traditional_iupac>stearoylcarnitine</traditional_iupac>
  <cas_registry_number>25597-09-5</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C</smiles>
  <inchi>InChI=1S/C25H49NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h23H,5-22H2,1-4H3/t23-/m1/s1</inchi>
  <inchikey>FNPHNLNTJNMAEE-HSZRJFAPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Acyl carnitines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl-carnitine</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fatty acyl carnitines</external_descriptor>
      <external_descriptor>O-acyl-L-carnitine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R)-3-(octadecanoyloxy)-4-(trimethylazaniumyl)butanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>427.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>427.366159062</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H49NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C25H49NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h23H,5-22H2,1-4H3/t23-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FNPHNLNTJNMAEE-HSZRJFAPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>146.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>54.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218123</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.021+/-0.008</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>0.008+/-0.001</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>0.02+/-0.01</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.0067+/-0.0021</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>0.006+/-0.002</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>0.02+/-0.01</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022278</foodb_id>
  <chemspider_id/>
  <kegg_id/>
  <pubchem_compound_id>52922056</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>84644</chebi_id>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>1585824</bigg_id>
  <metlin_id>5811</metlin_id>
  <synthesis_reference>Zhou, Qingzhong.  Synthesis of branched-chain analogs of stearoyl carnitine and tests for their abilities to inhibited protein kinase C.    Beijing Daxue Xuebao, Ziran Kexueban  (1992),  28(2),  143-9. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:30 UTC</creation_date>
  <update_date>2020-04-15 22:28:01 UTC</update_date>
  <accession>BMDB0000849</accession>
  <secondary_accessions>
    <accession>BMDB00849</accession>
  </secondary_accessions>
  <name>Rhamnose</name>
  <description>L-Fucose, also known as L-rha or 6-deoxymannose, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. L-Fucose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. L-Fucose exists in all living organisms, ranging from bacteria to humans. L-Fucose can be converted into fucose 1-phosphate; which is mediated by the enzyme L-fucose kinase. In cattle, L-fucose is involved in the metabolic pathway called the fructose and mannose degradation pathway.</description>
  <synonyms>
    <synonym>6-Deoxy-L-mannose</synonym>
    <synonym>L-(+)-Rhamnose</synonym>
    <synonym>L-Mannomethylose</synonym>
    <synonym>L-Rha</synonym>
    <synonym>L-Rhamnose</synonym>
    <synonym>L-Rhamnopyranose</synonym>
    <synonym>6-Deoxy-L(+)-mannose</synonym>
    <synonym>6-Deoxy-L-mannopyranose</synonym>
    <synonym>6-Deoxy-mannose</synonym>
    <synonym>6-Deoxyhexopyranose</synonym>
    <synonym>6-Deoxyhexose</synonym>
    <synonym>6-Deoxymannose</synonym>
    <synonym>Isodulcit</synonym>
    <synonym>Isodulcitol</synonym>
    <synonym>L(+)-Rhamnose</synonym>
    <synonym>L(+)-Rhamnose monohydrate</synonym>
    <synonym>L-(+)-Rhamnose 1-hydrate</synonym>
    <synonym>L-(+)-Rhamnose hydrate = 6-deoxy-L-mannose monohydrate</synonym>
    <synonym>L-(+)-Rhamnose monohydrate</synonym>
    <synonym>L-Rhamnose for biochemistry</synonym>
    <synonym>L-Rhamnose monohydrate</synonym>
    <synonym>Locaose</synonym>
    <synonym>mono(6-Deoxy-b-L-mannopyranosyl) ester</synonym>
    <synonym>mono(6-Deoxy-beta-L-mannopyranosyl) ester</synonym>
    <synonym>p-(6-Deoxy-b-L-mannopyranosyl) ester</synonym>
    <synonym>p-(6-Deoxy-beta-L-mannopyranosyl) ester</synonym>
    <synonym>Rhamnopyranose</synonym>
    <synonym>Rhamnosemonohydrate</synonym>
    <synonym>UDP-Rhamnose</synonym>
    <synonym>Uridine 5-pyrophosphate</synonym>
    <synonym>Uridine diphosphate rhamnose</synonym>
    <synonym>Deoxymannose</synonym>
    <synonym>Rhamnose, L isomer</synonym>
    <synonym>Rhamnose, L-isomer</synonym>
    <synonym>Rhamnose</synonym>
  </synonyms>
  <chemical_formula>C6H12O5</chemical_formula>
  <average_molecular_weight>164.1565</average_molecular_weight>
  <monisotopic_moleculate_weight>164.068473494</monisotopic_moleculate_weight>
  <iupac_name>(3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>L-(+)-rhamnose</traditional_iupac>
  <cas_registry_number>3615-41-6</cas_registry_number>
  <smiles>C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3-,4+,5+,6?/m0/s1</inchi>
  <inchikey>SHZGCJCMOBCMKK-JFNONXLTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxy sugars</external_descriptor>
      <external_descriptor>L-rhamnose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>122 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>164.1565</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>164.068473494</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3-,4+,5+,6?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SHZGCJCMOBCMKK-JFNONXLTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>90.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439212</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB001176</foodb_id>
  <chemspider_id>23642</chemspider_id>
  <kegg_id>C00507</kegg_id>
  <pubchem_compound_id>25310</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>62346</chebi_id>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Rhamnose</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5812</metlin_id>
  <synthesis_reference>Sanchez Miguel Cambronero,  Ruiz Pedro Antonio Garcia. Process for obtaining L-rhamnose of high purity from rhamnoglucosides. 1997, Patent ES2103205A1 (https://patents.google.com/patent/ES2103205A1/en)</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:31 UTC</creation_date>
  <update_date>2020-04-16 17:54:07 UTC</update_date>
  <accession>BMDB0000851</accession>
  <secondary_accessions>
    <accession>BMDB00851</accession>
  </secondary_accessions>
  <name>Pyridinoline</name>
  <description/>
  <synonyms>
    <synonym>(+)-Pyridinoline</synonym>
    <synonym>1-(2S)-(+)-Pyridinoline</synonym>
    <synonym>4-((2S)-2-Amino-2-carboxyethyl)-1-((2R,5S)-5-amino-5-carboxy-2-hydroxypentyl)-3-((3S)-3-amino-3-carboxypropyl)-5-hydroxy-pyridinium inner salt</synonym>
    <synonym>Hydroxylysylpyridinoline</synonym>
    <synonym>Hydroxylysyl pyridinoline</synonym>
    <synonym>Pyridinoline</synonym>
  </synonyms>
  <chemical_formula>C18H28N4O8</chemical_formula>
  <average_molecular_weight>428.4369</average_molecular_weight>
  <monisotopic_moleculate_weight>428.190713892</monisotopic_moleculate_weight>
  <iupac_name>4-[(2S)-2-amino-2-carboxyethyl]-3-[(3S)-3-amino-3-carboxypropyl]-1-[(2R,5S)-5-amino-5-carboxylato-2-hydroxypentyl]-5-hydroxypyridin-1-ium</iupac_name>
  <traditional_iupac>4-[(2S)-2-amino-2-carboxyethyl]-3-[(3S)-3-amino-3-carboxypropyl]-1-[(2R,5S)-5-amino-5-carboxylato-2-hydroxypentyl]-5-hydroxypyridin-1-ium</traditional_iupac>
  <cas_registry_number>63800-01-1</cas_registry_number>
  <smiles>N[C@@H](CCC1=C[N+](C[C@H](O)CC[C@H](N)C([O-])=O)=CC(O)=C1C[C@H](N)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C18H28N4O8/c19-12(16(25)26)3-1-9-6-22(7-10(23)2-4-13(20)17(27)28)8-15(24)11(9)5-14(21)18(29)30/h6,8,10,12-14,23H,1-5,7,19-21H2,(H3-,24,25,26,27,28,29,30)/t10-,12+,13+,14+/m1/s1</inchi>
  <inchikey>LCYXYLLJXMAEMT-SAXRGWBVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyridines</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridinium derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyridine</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridinium</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-[(2S)-2-amino-2-carboxyethyl]-3-[(3S)-3-amino-3-carboxypropyl]-1-[(2R,5S)-5-amino-5-carboxylato-2-hydroxypentyl]-5-hydroxypyridin-1-ium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>428.4369</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>428.190713892</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCC1=C[N+](C[C@H](O)CC[C@H](N)C([O-])=O)=CC(O)=C1C[C@H](N)C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H28N4O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H28N4O8/c19-12(16(25)26)3-1-9-6-22(7-10(23)2-4-13(20)17(27)28)8-15(24)11(9)5-14(21)18(29)30/h6,8,10,12-14,23H,1-5,7,19-21H2,(H3-,24,25,26,27,28,29,30)/t10-,12+,13+,14+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LCYXYLLJXMAEMT-SAXRGWBVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>237.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>114.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>43.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>119022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>119023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>119024</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB010805</foodb_id>
  <chemspider_id>94798</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>105068</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>88539</chebi_id>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Pyridinoline</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5814</metlin_id>
  <synthesis_reference>Allevi, Pietro; Cribiu, Riccardo; Giannini, Elios; Anastasia, Mario.  Practical syntheses of pyridinolines, important amino acidic biomarkers of collagen health.    Journal of Organic Chemistry  (2007),  72(9),  3478-3483.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:32 UTC</creation_date>
  <update_date>2020-03-13 16:24:16 UTC</update_date>
  <accession>BMDB0000853</accession>
  <secondary_accessions>
    <accession>BMDB00853</accession>
  </secondary_accessions>
  <name>N-Acetyl-b-D-galactosamine</name>
  <description/>
  <synonyms>
    <synonym>2-Acetamido-2-deoxy-beta-D-galactopyranoside</synonym>
    <synonym>beta-GalNAc</synonym>
    <synonym>BGalNAc</synonym>
    <synonym>2-Acetamido-2-deoxy-b-D-galactopyranoside</synonym>
    <synonym>2-Acetamido-2-deoxy-β-D-galactopyranoside</synonym>
    <synonym>b-GalNAc</synonym>
    <synonym>Β-galnac</synonym>
    <synonym>2-Deoxy-2-acetamido-b-D-galactopyranose</synonym>
    <synonym>2-Deoxy-2-acetamido-beta-D-galactopyranose</synonym>
    <synonym>2-Deoxy-2-acetamido-beta-delta-galactopyranose</synonym>
    <synonym>b-D-2-Acetamido-2-deoxy-galactopyranose</synonym>
    <synonym>b-N-Acetyl-D-galactosamine</synonym>
    <synonym>b-N-Acetylgalactosamine</synonym>
    <synonym>beta-D-2-Acetamido-2-deoxy-galactopyranose</synonym>
    <synonym>beta-delta-2-Acetamido-2-deoxy-galactopyranose</synonym>
    <synonym>beta-N-Acetyl-D-galactosamine</synonym>
    <synonym>beta-N-Acetyl-delta-galactosamine</synonym>
    <synonym>beta-N-Acetylgalactosamine</synonym>
    <synonym>2 Acetamido 2 D galactopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-D-galactose</synonym>
    <synonym>2 Acetamido 2 deoxy D galactose</synonym>
    <synonym>2-Acetamido-2-D-galactopyranose</synonym>
    <synonym>Acetylgalactosamine</synonym>
    <synonym>2 Acetamido 2 deoxygalactose</synonym>
    <synonym>N-Acetyl-D-galactosamine</synonym>
    <synonym>2-Acetamido-2-deoxygalactose</synonym>
    <synonym>N Acetyl D galactosamine</synonym>
    <synonym>N-Acetyl-β-D-galactosamine</synonym>
    <synonym>N-Acetyl-b-D-galactosamine</synonym>
  </synonyms>
  <chemical_formula>C8H15NO6</chemical_formula>
  <average_molecular_weight>221.2078</average_molecular_weight>
  <monisotopic_moleculate_weight>221.089937217</monisotopic_moleculate_weight>
  <iupac_name>N-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide</iupac_name>
  <traditional_iupac>N-acetyl-β-D-galactosamine</traditional_iupac>
  <cas_registry_number>14131-60-3</cas_registry_number>
  <smiles>CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8-/m1/s1</inchi>
  <inchikey>OVRNDRQMDRJTHS-JAJWTYFOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>N-acyl-alpha-hexosamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acetyl-D-galactosamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[(2R,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>221.2078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>221.089937217</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15NO6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OVRNDRQMDRJTHS-JAJWTYFOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>119.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29827</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB031024</foodb_id>
  <chemspider_id>389452</chemspider_id>
  <kegg_id>C05021</kegg_id>
  <pubchem_compound_id>440552</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28497</chebi_id>
  <drugbank_id/>
  <meta_cyc_id>CPD-12557</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5816</metlin_id>
  <synthesis_reference>Chaplin, David; Crout, David H. G.; Bornemann, Stephen; Hutchinson, David W.; Khan, Riaz.  Conversion of 2-acetamido-2-deoxy-b-D-glucopyranose (N-acetylglucosamine) into 2-acetamido-2-deoxy-b-D-galactopyranose (N-acetylgalactosamine using a biotransformation to generate a selectively deprotected substrate for SN2 inversion.    Journal of the Chemical Society, Perkin Transactions 1:  Organic and Bio-Organic Chemistry (1972-1999)  (1992),   (2),  235-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:33 UTC</creation_date>
  <update_date>2020-03-13 16:24:17 UTC</update_date>
  <accession>BMDB0000854</accession>
  <secondary_accessions>
    <accession>BMDB00854</accession>
  </secondary_accessions>
  <name>Formiminoglutamic acid</name>
  <description>Formiminoglutamic acid, also known as N-formimino-L-glutamate or formiminoglutamic acid, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Formiminoglutamic acid is possibly soluble (in water) and a very strong basic compound (based on its pKa). Formiminoglutamic acid exists in all living organisms, ranging from bacteria to humans. Formiminoglutamic acid participates in a number of enzymatic reactions, within cattle. In particular, Formiminoglutamic acid can be biosynthesized from 4-imidazolone-5-propionic acid through the action of the enzyme probable imidazolonepropionase. In addition, Tetrahydrofolic acid and formiminoglutamic acid can be converted into 5-formiminotetrahydrofolic acid and L-glutamic acid; which is mediated by the enzyme formimidoyltransferase-cyclodeaminase. In cattle, formiminoglutamic acid is involved in the metabolic pathway called the histidine metabolism pathway.</description>
  <synonyms>
    <synonym>N-Formimidoyl-L-glutamate</synonym>
    <synonym>N-Formimino-L-glutamate</synonym>
    <synonym>N-Formimidoyl-L-glutamic acid</synonym>
    <synonym>N-Formimino-L-glutamic acid</synonym>
    <synonym>Formiminoglutamate</synonym>
    <synonym>Formimino-glu</synonym>
    <synonym>Formimino-L-glutamate</synonym>
    <synonym>Formimino-L-glutamic acid</synonym>
    <synonym>N-(Iminomethyl)-L-glutamic acid</synonym>
    <synonym>N-Formimidoyl-glutamic acid</synonym>
    <synonym>N-Formimino-glutamate</synonym>
    <synonym>Acid, formiminoglutamic</synonym>
    <synonym>FIGLU</synonym>
  </synonyms>
  <chemical_formula>C6H10N2O4</chemical_formula>
  <average_molecular_weight>174.1546</average_molecular_weight>
  <monisotopic_moleculate_weight>174.064056818</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-methanimidamidopentanedioic acid</iupac_name>
  <traditional_iupac>N-formimino-L-glutamate</traditional_iupac>
  <cas_registry_number>816-90-0</cas_registry_number>
  <smiles>OC(=O)CC[C@H](NC=N)C(O)=O</smiles>
  <inchi>InChI=1S/C6H10N2O4/c7-3-8-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H2,7,8)(H,9,10)(H,11,12)/t4-/m0/s1</inchi>
  <inchikey>NRXIKWMTVXPVEF-BYPYZUCNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Glutamic acid and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxamidines</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Formamidines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amidine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid amidine</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Formamidine</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-glutamic acid derivative</external_descriptor>
      <external_descriptor>dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-methanimidamidopentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>174.1546</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>174.064056818</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC[C@H](NC=N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10N2O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10N2O4/c7-3-8-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H2,7,8)(H,9,10)(H,11,12)/t4-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NRXIKWMTVXPVEF-BYPYZUCNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>110.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>48.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177266</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022280</foodb_id>
  <chemspider_id>388370</chemspider_id>
  <kegg_id>C00439</kegg_id>
  <pubchem_compound_id>439233</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>7274</chebi_id>
  <drugbank_id/>
  <meta_cyc_id>N-FORMIMINO-L-GLUTAMATE</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Formiminoglutamic acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34986</bigg_id>
  <metlin_id>5817</metlin_id>
  <synthesis_reference>Tabor, Herbert; Rabinowitz, Jesse C. Insts. Formiminoglycine, formimino-L-aspartic acid, and formimino-L-glutamic acid.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00578</protein_accession>
      <name>Probable imidazolonepropionase</name>
      <uniprot_id>A5PJV3</uniprot_id>
      <gene_name>AMDHD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:34 UTC</creation_date>
  <update_date>2020-04-14 22:48:28 UTC</update_date>
  <accession>BMDB0000855</accession>
  <secondary_accessions>
    <accession>BMDB00855</accession>
  </secondary_accessions>
  <name>Nicotinamide riboside</name>
  <description>Nicotinamide riboside, also known as N-ribosylnicotinamide or SRT-647, belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). Nicotinamide riboside is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinamide riboside exists in all living species, ranging from bacteria to humans. Nicotinamide riboside participates in a number of enzymatic reactions, within cattle. In particular, Nicotinamide riboside and phosphoric acid can be biosynthesized from niacinamide and ribose-1-arsenate; which is mediated by the enzyme purine nucleoside phosphorylase. In addition, Nicotinamide riboside can be converted into nicotinamide ribotide; which is catalyzed by the enzyme cytosolic purine 5'-nucleotidase. In cattle, nicotinamide riboside is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway.</description>
  <synonyms>
    <synonym>1-(beta-D-Ribofuranosyl)nicotinamide</synonym>
    <synonym>beta-Nicotinamide D-riboside</synonym>
    <synonym>Nicotinamide ribonucleoside</synonym>
    <synonym>Nicotinamide ribose</synonym>
    <synonym>Nicotinamide-beta-riboside</synonym>
    <synonym>N-Ribosylnicotinamide</synonym>
    <synonym>1-(b-D-Ribofuranosyl)nicotinamide</synonym>
    <synonym>1-(Β-D-ribofuranosyl)nicotinamide</synonym>
    <synonym>b-Nicotinamide D-riboside</synonym>
    <synonym>Β-nicotinamide D-riboside</synonym>
    <synonym>Nicotinamide-b-riboside</synonym>
    <synonym>Nicotinamide-β-riboside</synonym>
    <synonym>1-b-D-Ribosyl-3-pyridinecarboxamide</synonym>
    <synonym>1-beta-D-Ribosyl-3-pyridinecarboxamide</synonym>
    <synonym>1-beta-delta-Ribosyl-3-pyridinecarboxamide</synonym>
    <synonym>3-(Aminocarbonyl)-1-beta-D-ribofuranosyl-pyridinium</synonym>
    <synonym>3-(Aminocarbonyl)-1-beta-delta-ribofuranosyl-pyridinium</synonym>
    <synonym>Ribosylnicotinamide</synonym>
    <synonym>SRT-647</synonym>
    <synonym>SRT 647</synonym>
  </synonyms>
  <chemical_formula>C11H15N2O5</chemical_formula>
  <average_molecular_weight>255.2472</average_molecular_weight>
  <monisotopic_moleculate_weight>255.0980966</monisotopic_moleculate_weight>
  <iupac_name>3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium</iupac_name>
  <traditional_iupac>3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium</traditional_iupac>
  <cas_registry_number>1341-23-7</cas_registry_number>
  <smiles>NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C11H14N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11/h1-4,7-9,11,14-16H,5H2,(H-,12,17)/p+1/t7-,8-,9-,11-/m1/s1</inchi>
  <inchikey>JLEBZPBDRKPWTD-TURQNECASA-O</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Glycosylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Nicotinamides</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Pyridinium derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Nicotinamide</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridine carboxylic acid or derivatives</substituent>
      <substituent>Pyridinium</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-glycosylnicotinamide</external_descriptor>
      <external_descriptor>pyridine nucleoside</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>255.2472</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>255.0980966</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H15N2O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H14N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11/h1-4,7-9,11,14-16H,5H2,(H-,12,17)/p+1/t7-,8-,9-,11-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JLEBZPBDRKPWTD-TURQNECASA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>116.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33166</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022281</foodb_id>
  <chemspider_id>388956</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>439924</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id>C03150</kegg_id>
  <chebi_id>15927</chebi_id>
  <wikipedia_id>Nicotinamide riboside</wikipedia_id>
  <knapsack_id/>
  <meta_cyc_id>NICOTINAMIDE_RIBOSE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>41300</bigg_id>
  <metlin_id>5818</metlin_id>
  <synthesis_reference>Franchetti, Palmarisa; Pasqualini, Michela; Petrelli, Riccardo; Ricciutelli, Massimo; Vita, Patrizia; Cappellacci, Loredana.  Stereoselective synthesis of nicotinamide b-riboside and nucleoside analogs. Bioorganic &amp; Medicinal Chemistry Letters  (2004),  14(18),  4655-4658  Yang, T, Chan NY, Sauve AA. Syntheses of nicotinamide riboside and deriviatives.. J. Med Chem. 50:6458-61 (2007)..</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:36 UTC</creation_date>
  <update_date>2020-03-13 16:24:18 UTC</update_date>
  <accession>BMDB0000856</accession>
  <secondary_accessions>
    <accession>BMDB00856</accession>
  </secondary_accessions>
  <name>N-a-Acetylcitrulline</name>
  <description/>
  <synonyms>
    <synonym>2-(Acetylamino)-5-[(aminocarbonyl)amino]pentanoic acid</synonym>
    <synonym>2-(Acetylamino)-5-[(aminocarbonyl)amino]pentanoate</synonym>
    <synonym>(2S)-2-(acetylamino)-5-[(Aminocarbonyl)amino]pentanoate</synonym>
    <synonym>(2S)-2-(acetylamino)-5-[(Aminocarbonyl)amino]pentanoic acid</synonym>
    <synonym>(2S)-2-acetamido-5-(carbamoylamino)Pentanoate</synonym>
    <synonym>(2S)-2-acetamido-5-(carbamoylamino)Pentanoic acid</synonym>
    <synonym>(S)-2-acetamido-5-Ureidopentanoate</synonym>
    <synonym>(S)-2-acetamido-5-Ureidopentanoic acid</synonym>
    <synonym>a-N-Acetylcitrulline</synonym>
    <synonym>alpha-N-Acetylcitrulline</synonym>
    <synonym>N-Acetyl citrulline</synonym>
    <synonym>N-Acetyl-L-citrulline</synonym>
    <synonym>N-alpha-Acetylcitrulline</synonym>
    <synonym>N2-Acetyl-N5-carbamoyl-L-ornithine</synonym>
    <synonym>Na-acetyl-L-citrulline</synonym>
    <synonym>OLN</synonym>
    <synonym>N-a-Acetylcitrulline</synonym>
    <synonym>N-Α-acetylcitrulline</synonym>
  </synonyms>
  <chemical_formula>C8H15N3O4</chemical_formula>
  <average_molecular_weight>217.2224</average_molecular_weight>
  <monisotopic_moleculate_weight>217.106255983</monisotopic_moleculate_weight>
  <iupac_name>5-(carbamoylamino)-2-acetamidopentanoic acid</iupac_name>
  <traditional_iupac>N-acetylcitrulline</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(=O)NC(CCCNC(N)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C8H15N3O4/c1-5(12)11-6(7(13)14)3-2-4-10-8(9)15/h6H,2-4H2,1H3,(H,11,12)(H,13,14)(H3,9,10,15)</inchi>
  <inchikey>WMQMIOYQXNRROC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonic acid derivative</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Urea</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acetyl-amino acid</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
      <external_descriptor>ureas</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-(carbamoylamino)-2-acetamidopentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>217.2224</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>217.106255983</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)NC(CCCNC(N)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15N3O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15N3O4/c1-5(12)11-6(7(13)14)3-2-4-10-8(9)15/h6H,2-4H2,1H3,(H,11,12)(H,13,14)(H3,9,10,15)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WMQMIOYQXNRROC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>121.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13855</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022282</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>11506771</pubchem_compound_id>
  <chebi_id>49006</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference>Shi, Dashuang; Morizono, Hiroki; Yu, Xiaolin; Roth, Lauren; Caldovic, Ljubica; Allewell, Norma M.; Malamy, Michael H.; Tuchman, Mendel.  Crystal Structure of N-Acetylornithine Transcarbamylase from Xanthomonas campestris: A novel enzyme in a new arginine biosynthetic pathway found in several eubacteria.    Journal of Biological Chemistry  (2005),  280(15),  14366-14369.    (Biosynthetic preparation)</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:37 UTC</creation_date>
  <update_date>2020-03-13 16:24:18 UTC</update_date>
  <accession>BMDB0000857</accession>
  <secondary_accessions>
    <accession>BMDB00857</accession>
  </secondary_accessions>
  <name>Pimelic acid</name>
  <description/>
  <synonyms>
    <synonym>1,5-Pentanedicarboxylic acid</synonym>
    <synonym>6-Carboxyhexanoic acid</synonym>
    <synonym>Heptanedioic acid</synonym>
    <synonym>Pimelate</synonym>
    <synonym>6-Carboxyhexanoate</synonym>
    <synonym>1,5-Pentanedicarboxylate</synonym>
    <synonym>Heptanedioate</synonym>
    <synonym>Acid, pimelic</synonym>
    <synonym>Acids, pimelic</synonym>
    <synonym>Pimelic acids</synonym>
    <synonym>1,7-Heptanedioate</synonym>
    <synonym>1,7-Heptanedioic acid</synonym>
    <synonym>Heptandioate</synonym>
    <synonym>Heptandioic acid</synonym>
    <synonym>Heptane-1,7-dioate</synonym>
    <synonym>Heptane-1,7-dioic acid</synonym>
    <synonym>Pilerate</synonym>
    <synonym>Pileric acid</synonym>
  </synonyms>
  <chemical_formula>C7H12O4</chemical_formula>
  <average_molecular_weight>160.1678</average_molecular_weight>
  <monisotopic_moleculate_weight>160.073558872</monisotopic_moleculate_weight>
  <iupac_name>heptanedioic acid</iupac_name>
  <traditional_iupac>pimelic acid</traditional_iupac>
  <cas_registry_number>111-16-0</cas_registry_number>
  <smiles>OC(=O)CCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11)</inchi>
  <inchikey>WLJVNTCWHIRURA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>alpha,omega-dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>103 - 106 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>50.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.61</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>heptanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>160.1678</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>160.073558872</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H12O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WLJVNTCWHIRURA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>259400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>279338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438314</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02656</kegg_id>
  <chemspider_id>376</chemspider_id>
  <foodb_id>FDB022283</foodb_id>
  <pubchem_compound_id>385</pubchem_compound_id>
  <chebi_id>30531</chebi_id>
  <pdbe_id/>
  <drugbank_id>DB01856</drugbank_id>
  <meta_cyc_id>CPD-205</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001199</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Pimelic_acid</wikipedia_id>
  <metlin_id>3280</metlin_id>
  <synthesis_reference>Murib, Jawad H.; Kahn, John H.  Production of pimelic acid by carbonylation of e-caprolactone using excess water.    U.S.  (1989),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:38 UTC</creation_date>
  <update_date>2020-03-13 16:24:19 UTC</update_date>
  <accession>BMDB0000858</accession>
  <secondary_accessions>
    <accession>BMDB00858</accession>
  </secondary_accessions>
  <name>Monomethyl glutaric acid</name>
  <description/>
  <synonyms>
    <synonym>4-(Methoxycarbonyl)butyric acid</synonym>
    <synonym>4-Methoxycarbonylbutanoic acid</synonym>
    <synonym>Monomethyl glutarate</synonym>
    <synonym>4-(Methoxycarbonyl)butyrate</synonym>
    <synonym>4-Methoxycarbonylbutanoate</synonym>
    <synonym>2-Methyleneglutarate</synonym>
    <synonym>4-Carboxybutanoate</synonym>
    <synonym>4-Carboxybutanoic acid</synonym>
    <synonym>4-Carboxybutanoic acid methyl ester</synonym>
    <synonym>5-Methoxy-5-oxopentanoate</synonym>
    <synonym>5-Methoxy-5-oxopentanoic acid</synonym>
    <synonym>Glutaric acid methyl ester</synonym>
    <synonym>Glutaric acid methyl half ester</synonym>
    <synonym>Glutaric acid monomethyl ester</synonym>
    <synonym>Glutaric acid monomethylester</synonym>
    <synonym>Methyl glutarate</synonym>
    <synonym>Methyl glutarate,mono</synonym>
    <synonym>Methyl hydrogen glutarate</synonym>
    <synonym>mono-Methyl glutarate</synonym>
    <synonym>Monomethyl ester OF glutarate</synonym>
    <synonym>Monomethyl ester OF glutaric acid</synonym>
    <synonym>Pentanedioate</synonym>
    <synonym>Pentanedioic acid</synonym>
    <synonym>Pentanedioic acid monomethyl ester</synonym>
  </synonyms>
  <chemical_formula>C6H10O4</chemical_formula>
  <average_molecular_weight>146.1412</average_molecular_weight>
  <monisotopic_moleculate_weight>146.057908808</monisotopic_moleculate_weight>
  <iupac_name>5-methoxy-5-oxopentanoic acid</iupac_name>
  <traditional_iupac>glutaric acid monomethyl ester</traditional_iupac>
  <cas_registry_number>1501-27-5</cas_registry_number>
  <smiles>COC(=O)CCCC(O)=O</smiles>
  <inchi>InChI=1S/C6H10O4/c1-10-6(9)4-2-3-5(7)8/h2-4H2,1H3,(H,7,8)</inchi>
  <inchikey>IBMRTYCHDPMBFN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <direct_parent>Fatty acid methyl esters</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl esters</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid methyl ester</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methyl ester</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dicarboxylic acid monoester</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>150 - 151 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-methoxy-5-oxopentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>146.1412</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>146.057908808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC(=O)CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O4/c1-10-6(9)4-2-3-5(7)8/h2-4H2,1H3,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IBMRTYCHDPMBFN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440161</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022284</foodb_id>
  <chemspider_id>66550</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>73917</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id/>
  <chebi_id>86396</chebi_id>
  <wikipedia_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5821</metlin_id>
  <synthesis_reference>Yajima, Tatsuhiko; Suzuki, Takamasa.  Oxidation reaction of liquid dimethyl glutarate exposed to low-temperature oxygen plasma.    Journal of Photopolymer Science and Technology  (2005),  18(2),  233-236.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:39 UTC</creation_date>
  <update_date>2020-03-13 16:24:19 UTC</update_date>
  <accession>BMDB0000859</accession>
  <secondary_accessions>
    <accession>BMDB00859</accession>
  </secondary_accessions>
  <name>Methylhippuric acid</name>
  <description/>
  <synonyms>
    <synonym>Hippurate methyl ester</synonym>
    <synonym>Hippuric acid methyl ester</synonym>
    <synonym>N-Benzoyl-glycine methyl ester</synonym>
    <synonym>N-Benzoylglycine methyl ester</synonym>
    <synonym>Hippate methyl ester</synonym>
    <synonym>Hippic acid methyl ester</synonym>
    <synonym>Methyl hippuric acid</synonym>
    <synonym>Methylhippate</synonym>
    <synonym>Methylhippic acid</synonym>
    <synonym>Methyl (benzoylamino)acetate</synonym>
    <synonym>Methyl benzoylaminoacetate</synonym>
    <synonym>Methyl benzoylglycinate</synonym>
    <synonym>Methyl N-benzoylglycinate</synonym>
    <synonym>Methyl hippurate</synonym>
  </synonyms>
  <chemical_formula>C10H11NO3</chemical_formula>
  <average_molecular_weight>193.1992</average_molecular_weight>
  <monisotopic_moleculate_weight>193.073893223</monisotopic_moleculate_weight>
  <iupac_name>methyl 2-(phenylformamido)acetate</iupac_name>
  <traditional_iupac>methyl (phenylformamido)acetate</traditional_iupac>
  <cas_registry_number>1205-08-9</cas_registry_number>
  <smiles>COC(=O)CNC(=O)C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C10H11NO3/c1-14-9(12)7-11-10(13)8-5-3-2-4-6-8/h2-6H,7H2,1H3,(H,11,13)</inchi>
  <inchikey>XTKVNQKOTKPCKM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha amino acid esters</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl esters</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid ester</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methyl ester</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>glycine derivative</external_descriptor>
      <external_descriptor>methyl ester</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>methyl 2-(phenylformamido)acetate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>193.1992</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>193.073893223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC(=O)CNC(=O)C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H11NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H11NO3/c1-14-9(12)7-11-10(13)8-5-3-2-4-6-8/h2-6H,7H2,1H3,(H,11,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XTKVNQKOTKPCKM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>55.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451259</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022285</foodb_id>
  <chemspider_id>13907</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>14566</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id/>
  <chebi_id>70869</chebi_id>
  <wikipedia_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5822</metlin_id>
  <synthesis_reference>Rinderknecht, Heinrich; Niemann, Carl.  Esterification of acylated a-amino acids.    Journal of the American Chemical Society  (1948),  70  2605-6. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:40 UTC</creation_date>
  <update_date>2020-03-13 16:24:20 UTC</update_date>
  <accession>BMDB0000860</accession>
  <secondary_accessions>
    <accession>BMDB00860</accession>
  </secondary_accessions>
  <name>Phenylpropionylglycine</name>
  <description/>
  <synonyms>
    <synonym>2-[(1-Hydroxy-3-phenylpropylidene)amino]acetate</synonym>
    <synonym>(3-Phenyl-propionylamino)-acetate</synonym>
    <synonym>(3-Phenyl-propionylamino)-acetic acid</synonym>
    <synonym>(3-Phenylpropionyl)glycine</synonym>
    <synonym>N-(3-Phenyl-propionyl)-glycine</synonym>
    <synonym>N-(3-Phenylpropanoyl)glycine</synonym>
    <synonym>3-Phenylpropionylglycine</synonym>
  </synonyms>
  <chemical_formula>C11H13NO3</chemical_formula>
  <average_molecular_weight>207.2258</average_molecular_weight>
  <monisotopic_moleculate_weight>207.089543287</monisotopic_moleculate_weight>
  <iupac_name>2-(3-phenylpropanamido)acetic acid</iupac_name>
  <traditional_iupac>phenylpropionylglycine</traditional_iupac>
  <cas_registry_number>56613-60-6</cas_registry_number>
  <smiles>OC(=O)CNC(=O)CCC1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C11H13NO3/c13-10(12-8-11(14)15)7-6-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)(H,14,15)</inchi>
  <inchikey>YEIQSAXUPKPPBN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty amides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(3-phenylpropanamido)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>207.2258</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>207.089543287</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CNC(=O)CCC1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H13NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H13NO3/c13-10(12-8-11(14)15)7-6-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)(H,14,15)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YEIQSAXUPKPPBN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350853</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022286</foodb_id>
  <chemspider_id>134261</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>152323</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id/>
  <chebi_id>266653</chebi_id>
  <wikipedia_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5823</metlin_id>
  <synthesis_reference>Geurts, Muriel; Poupaert, Jacques H.; Scriba, Gerhard K. E.; Lambert, Didier M.  N-(Benzyloxycarbonyl)glycine Esters and Amides as New Anticonvulsants.    Journal of Medicinal Chemistry  (1998),  41(1),  24-30.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:41 UTC</creation_date>
  <update_date>2020-04-16 20:39:21 UTC</update_date>
  <accession>BMDB0000863</accession>
  <secondary_accessions>
    <accession>BMDB00863</accession>
  </secondary_accessions>
  <name>Isopropyl alcohol</name>
  <description>Isopropyl alcohol, also known as isopropanol or avantin, belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). Isopropyl alcohol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Isopropyl alcohol exists in all living species, ranging from bacteria to humans. Isopropyl alcohol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Methylethanol</synonym>
    <synonym>1-Methylethyl alcohol</synonym>
    <synonym>2-Hydroxypropane</synonym>
    <synonym>2-Propanol</synonym>
    <synonym>I-propanol</synonym>
    <synonym>I-propylalkohol</synonym>
    <synonym>IPA</synonym>
    <synonym>Isopropanol</synonym>
    <synonym>Isopropylalkohol</synonym>
    <synonym>Sec-propanol</synonym>
    <synonym>Isopro</synonym>
    <synonym>2-Propyl alcohol</synonym>
    <synonym>Alcojel</synonym>
    <synonym>Alkolave</synonym>
    <synonym>Avantin</synonym>
    <synonym>Avantine</synonym>
    <synonym>Hartosol</synonym>
    <synonym>Lavaco</synonym>
    <synonym>Petrohol</synonym>
    <synonym>Takineocol</synonym>
    <synonym>Alcohol, isopropyl</synonym>
    <synonym>Alcohol, rubbing</synonym>
    <synonym>Rubbing alcohol</synonym>
    <synonym>2 Propanol</synonym>
    <synonym>ISOPROPYL alcohol</synonym>
  </synonyms>
  <chemical_formula>C3H8O</chemical_formula>
  <average_molecular_weight>60.095</average_molecular_weight>
  <monisotopic_moleculate_weight>60.057514878</monisotopic_moleculate_weight>
  <iupac_name>propan-2-ol</iupac_name>
  <traditional_iupac>isopropyl alcohol</traditional_iupac>
  <cas_registry_number>67-63-0</cas_registry_number>
  <smiles>CC(C)O</smiles>
  <inchi>InChI=1S/C3H8O/c1-3(2)4/h3-4H,1-2H3</inchi>
  <inchikey>KFZMGEQAYNKOFK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Secondary alcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>secondary alcohol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.05</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>17.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>propan-2-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>60.095</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>60.057514878</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H8O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H8O/c1-3(2)4/h3-4H,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KFZMGEQAYNKOFK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>17.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>7.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>67</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16270</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2+/-1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.7 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.7 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.9 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>44.1 +/- 27.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Graulet B, Richard C, Robert JC: Methionine availability in plasma of dairy cows supplemented with methionine hydroxy analog isopropyl ester. J Dairy Sci. 2005 Oct;88(10):3640-9. doi: 10.3168/jds.S0022-0302(05)73049-6.</reference_text>
          <pubmed_id>16162538</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>14-70</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>103+/-45</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB008282</foodb_id>
  <chemspider_id>3644</chemspider_id>
  <drugbank_id>DB02325</drugbank_id>
  <pubchem_compound_id>3776</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id>C01845</kegg_id>
  <chebi_id>17824</chebi_id>
  <wikipedia_id>Isopropyl_Alcohol</wikipedia_id>
  <knapsack_id>C00048438</knapsack_id>
  <meta_cyc_id>ISO-PROPANOL</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>4192</metlin_id>
  <synthesis_reference>Gu, Xiaoyan; Wu, Xiaolan; Ma, Guangyu.  Process for preparation of hyper pure isopropyl alcohol.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2005),     6 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:43 UTC</creation_date>
  <update_date>2020-04-15 22:14:36 UTC</update_date>
  <accession>BMDB0000865</accession>
  <secondary_accessions>
    <accession>BMDB00865</accession>
  </secondary_accessions>
  <name>Muricholic acid</name>
  <description/>
  <synonyms>
    <synonym>Muricholate</synonym>
    <synonym>(3alpha,5beta)-3,6,7-Trihydroxy-cholan-24-Oate</synonym>
    <synonym>(3alpha,5beta)-3,6,7-Trihydroxy-cholan-24-Oic acid</synonym>
    <synonym>3,6,7-Trihydroxy-5-cholanoate</synonym>
    <synonym>3,6,7-Trihydroxy-5-cholanoic acid</synonym>
    <synonym>3alpha,6alpha,7beta-Trihydroxy-5beta-cholanoate</synonym>
    <synonym>3alpha,6alpha,7beta-Trihydroxy-5beta-cholanoic acid</synonym>
    <synonym>Hyocholic acid</synonym>
    <synonym>Trihydroxy-5alpha-cholanoate</synonym>
    <synonym>Trihydroxy-5alpha-cholanoic acid</synonym>
    <synonym>3 alpha,6 alpha,7 beta-Trihydroxy-5 beta-cholanoic acid</synonym>
    <synonym>alpha-Muricholic acid</synonym>
    <synonym>beta-Muricholic acid</synonym>
    <synonym>Muricholic acid, (3alpha,5alpha,6alpha,7alpha)-isomer</synonym>
    <synonym>Muricholic acid, (3alpha,5beta,6alpha,7alpha)-isomer</synonym>
    <synonym>Muricholic acid, (3alpha,5beta,6alpha,7beta)-isomer</synonym>
    <synonym>Muricholic acid, (3alpha,5beta,6beta,7alpha)-isomer</synonym>
    <synonym>Muricholic acid, (3alpha,5beta,6beta,7beta)-isomer</synonym>
    <synonym>Muricholic acid, sodium salt</synonym>
    <synonym>Omega-muricholic acid</synonym>
    <synonym>Trihydroxy-5 alpha-cholanoic acid</synonym>
    <synonym>Muricholic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2R,5R,7R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2R,5R,7R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>39016-49-4</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])C(O)C(O)[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21?,22?,23-,24-/m1/s1</inchi>
  <inchikey>DKPMWHFRUGMUKF-JDDNAIEOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>6-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>6-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>logp</kind>
      <value>2.72</value>
      <source>Extrapolated</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2R,5R,7R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])C(O)C(O)[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21?,22?,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DKPMWHFRUGMUKF-JDDNAIEOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370887</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <drugbank_id/>
  <chemspider_id>106701</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>119473</pubchem_compound_id>
  <chebi_id>134216</chebi_id>
  <knapsack_id/>
  <wikipedia_id>Muricholic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5826</metlin_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <synthesis_reference>Aranda G; Bertranne M; Fetizon M; Infante R  Synthesis of 6 alpha-tritiated beta-muricholic acid for use as a molecular probe.    Steroids  (1992),  57(4),  205-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:44 UTC</creation_date>
  <update_date>2020-03-13 16:24:22 UTC</update_date>
  <accession>BMDB0000866</accession>
  <secondary_accessions>
    <accession>BMDB00866</accession>
  </secondary_accessions>
  <name>N-Acetyl-L-tyrosine</name>
  <description/>
  <synonyms>
    <synonym>N-Acetyl-4-hydroxyphenylalanine</synonym>
    <synonym>N-Acetyltyrosine</synonym>
    <synonym>(2S)-2-Acetylamino-3-(4-hydroxyphenyl)propanoate</synonym>
    <synonym>(2S)-2-Acetylamino-3-(4-hydroxyphenyl)propanoic acid</synonym>
    <synonym>L-N-Acetyl-tyrosine</synonym>
    <synonym>L-N-Acetyltyrosine</synonym>
    <synonym>N-Acetyl-tyrosine</synonym>
    <synonym>N-Acetyltyrosine, (DL)-isomer</synonym>
    <synonym>Acetyl-L-tyrosine</synonym>
    <synonym>N-Acetyltyrosine, (D)-isomer</synonym>
  </synonyms>
  <chemical_formula>C11H13NO4</chemical_formula>
  <average_molecular_weight>223.2252</average_molecular_weight>
  <monisotopic_moleculate_weight>223.084457909</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoic acid</iupac_name>
  <traditional_iupac>acetyl-L-tyrosine</traditional_iupac>
  <cas_registry_number>537-55-3</cas_registry_number>
  <smiles>CC(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C11H13NO4/c1-7(13)12-10(11(15)16)6-8-2-4-9(14)5-3-8/h2-5,10,14H,6H2,1H3,(H,12,13)(H,15,16)/t10-/m0/s1</inchi>
  <inchikey>CAHKINHBCWCHCF-JTQLQIEISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Tyrosine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalanine and derivatives</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tyrosine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-tyrosine derivative</external_descriptor>
      <external_descriptor>N-acetyl-L-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>149 - 152 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>297 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-acetamido-3-(4-hydroxyphenyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>223.2252</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>223.084457909</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H13NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H13NO4/c1-7(13)12-10(11(15)16)6-8-2-4-9(14)5-3-8/h2-5,10,14H,6H2,1H3,(H,12,13)(H,15,16)/t10-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CAHKINHBCWCHCF-JTQLQIEISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>86.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>56.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>247830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>247831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>247832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>267771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>267772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>267773</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01657</kegg_id>
  <foodb_id>FDB022288</foodb_id>
  <chemspider_id>61606</chemspider_id>
  <drugbank_id>DB11102</drugbank_id>
  <chebi_id>21563</chebi_id>
  <pubchem_compound_id>68310</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Liu, Aifu.  Preparation of N-acetyl-L-tyrosine.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2005),     5 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:45 UTC</creation_date>
  <update_date>2020-04-14 22:48:29 UTC</update_date>
  <accession>BMDB0000867</accession>
  <secondary_accessions>
    <accession>BMDB00867</accession>
  </secondary_accessions>
  <name>Ribonic acid</name>
  <description/>
  <synonyms>
    <synonym>D-Ribonic acid</synonym>
    <synonym>D-Ribonate</synonym>
    <synonym>Ribonate</synonym>
    <synonym>2,3,4,5-Tetrahydroxypentanoic acid</synonym>
    <synonym>Ribonic acid</synonym>
  </synonyms>
  <chemical_formula>C5H10O6</chemical_formula>
  <average_molecular_weight>166.1293</average_molecular_weight>
  <monisotopic_moleculate_weight>166.047738052</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4R)-2,3,4,5-tetrahydroxypentanoic acid</iupac_name>
  <traditional_iupac>ribonic acid</traditional_iupac>
  <cas_registry_number>642-98-8</cas_registry_number>
  <smiles>OC[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H10O6/c6-1-2(7)3(8)4(9)5(10)11/h2-4,6-9H,1H2,(H,10,11)/t2-,3-,4-/m1/s1</inchi>
  <inchikey>QXKAIJAYHKCRRA-BXXZVTAOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
      <substituent>Sugar acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>ribonic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R,4R)-2,3,4,5-tetrahydroxypentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>166.1293</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>166.047738052</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O6/c6-1-2(7)3(8)4(9)5(10)11/h2-4,6-9H,1H2,(H,10,11)/t2-,3-,4-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QXKAIJAYHKCRRA-BXXZVTAOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>161646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>161647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>161648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>97014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>97015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>97016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37814</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01685</kegg_id>
  <foodb_id>FDB022289</foodb_id>
  <chemspider_id>4574162</chemspider_id>
  <drugbank_id/>
  <chebi_id>21077</chebi_id>
  <pubchem_compound_id>5460677</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>3290</metlin_id>
  <synthesis_reference>Lockwood, L. B.  Pentoic acids from pentoses.    (1949),     US  2463784  19490308  CAN 43:20773  AN 1949:20773    CAPLUS</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:46 UTC</creation_date>
  <update_date>2020-03-13 16:24:23 UTC</update_date>
  <accession>BMDB0000868</accession>
  <secondary_accessions>
    <accession>BMDB00868</accession>
  </secondary_accessions>
  <name>Xylulose 5-phosphate</name>
  <description/>
  <synonyms>
    <synonym>5-O-Phosphono-D-threo-pentos-2-ulose</synonym>
    <synonym>5-O-Phosphono-D-xylulose</synonym>
    <synonym>D-Xylulose-5-phosphate</synonym>
    <synonym>D-Xylulose-5-phosphoric acid</synonym>
    <synonym>Xylulose 5-phosphoric acid</synonym>
    <synonym>D-Xylulose 5-phosphate</synonym>
    <synonym>D-Xylulose 5-PO4</synonym>
    <synonym>D-Xylulose-5-p</synonym>
    <synonym>Xu-5-p</synonym>
    <synonym>Xylulose-p</synonym>
    <synonym>Xylulose-phosphate</synonym>
    <synonym>Xylulose-5-phosphate</synonym>
    <synonym>Xylulose-5-phosphate, (D)-isomer</synonym>
  </synonyms>
  <chemical_formula>C5H11O8P</chemical_formula>
  <average_molecular_weight>230.1098</average_molecular_weight>
  <monisotopic_moleculate_weight>230.01915384</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>ribulose-5-phosphate</traditional_iupac>
  <cas_registry_number>4212-65-1</cas_registry_number>
  <smiles>OCC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/t4-,5-/m1/s1</inchi>
  <inchikey>FNZLKVNUWIIPSJ-RFZPGFLSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Acyloins</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyloin</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>xylulose 5-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>230.1098</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>230.01915384</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H11O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/t4-,5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FNZLKVNUWIIPSJ-RFZPGFLSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>144.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31444</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00231</kegg_id>
  <foodb_id>FDB030802</foodb_id>
  <chemspider_id>388330</chemspider_id>
  <drugbank_id>DB04034</drugbank_id>
  <chebi_id>16332</chebi_id>
  <pubchem_compound_id>439190</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00019693</knapsack_id>
  <meta_cyc_id/>
  <bigg_id>34329</bigg_id>
  <wikipedia_id>Xylulose 5-phosphate</wikipedia_id>
  <metlin_id>5829</metlin_id>
  <synthesis_reference>Shaeri, Jobin; Wohlgemuth, Roland; Woodley, John M.  Semiquantitative Process Screening for the Biocatalytic Synthesis of D-Xylulose-5-phosphate.    Organic Process Research &amp; Development  (2006),  10(3),  605-610.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00607</protein_accession>
      <name>Transketolase-like protein 1</name>
      <uniprot_id>Q2NL26</uniprot_id>
      <gene_name>TKTL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00608</protein_accession>
      <name>Transketolase-like protein 2</name>
      <uniprot_id>Q2NKZ4</uniprot_id>
      <gene_name>TKTL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00609</protein_accession>
      <name>Transketolase</name>
      <uniprot_id>Q6B855</uniprot_id>
      <gene_name>TKT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:47 UTC</creation_date>
  <update_date>2020-03-13 16:24:23 UTC</update_date>
  <accession>BMDB0000869</accession>
  <secondary_accessions>
    <accession>BMDB00869</accession>
  </secondary_accessions>
  <name>Uroporphyrin II</name>
  <description/>
  <synonyms>
    <synonym>Isouroporphyrin (II) octamethyl ester</synonym>
    <synonym>Uroporphyrin I octamethyl ester</synonym>
    <synonym>Methyl 9,19-bis(2-methoxy-2-oxoethyl)-5,10,14,15,20-pentakis(3-methoxy-3-oxopropyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaene-4-carboxylic acid</synonym>
  </synonyms>
  <chemical_formula>C48H54N4O16</chemical_formula>
  <average_molecular_weight>942.9596</average_molecular_weight>
  <monisotopic_moleculate_weight>942.3534817</monisotopic_moleculate_weight>
  <iupac_name>methyl 9,19-bis(2-methoxy-2-oxoethyl)-5,10,14,15,20-pentakis(3-methoxy-3-oxopropyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaene-4-carboxylate</iupac_name>
  <traditional_iupac>uroporphyrin II</traditional_iupac>
  <cas_registry_number>531-42-0</cas_registry_number>
  <smiles>COC(=O)CCC1=C(CCC(=O)OC)/C2=C/C3=N/C(=C\C4=C(C(=O)OC)C(CCC(=O)OC)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(=O)OC)=C4CC(=O)OC)/C(CCC(=O)OC)=C3CC(=O)OC</smiles>
  <inchi>InChI=1S/C48H54N4O16/c1-61-40(53)14-9-25-26(10-15-41(54)62-2)33-22-37-31(20-46(59)67-7)28(12-17-43(56)64-4)35(51-37)24-39-47(48(60)68-8)29(13-18-44(57)65-5)36(52-39)23-38-30(19-45(58)66-6)27(11-16-42(55)63-3)34(50-38)21-32(25)49-33/h21-24,49,52H,9-20H2,1-8H3/b32-21-,33-22-,34-21-,35-24-,36-23-,37-22-,38-23-,39-24-</inchi>
  <inchikey>JXFYRPWVBHUVFB-BGKHBZPASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>methyl 9,19-bis(2-methoxy-2-oxoethyl)-5,10,14,15,20-pentakis(3-methoxy-3-oxopropyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaene-4-carboxylate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>942.9596</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>942.3534817</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC(=O)CCC1=C(CCC(=O)OC)/C2=C/C3=N/C(=C\C4=C(C(=O)OC)C(CCC(=O)OC)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(=O)OC)=C4CC(=O)OC)/C(CCC(=O)OC)=C3CC(=O)OC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C48H54N4O16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C48H54N4O16/c1-61-40(53)14-9-25-26(10-15-41(54)62-2)33-22-37-31(20-46(59)67-7)28(12-17-43(56)64-4)35(51-37)24-39-47(48(60)68-8)29(13-18-44(57)65-5)36(52-39)23-38-30(19-45(58)66-6)27(11-16-42(55)63-3)34(50-38)21-32(25)49-33/h21-24,49,52H,9-20H2,1-8H3/b32-21-,33-22-,34-21-,35-24-,36-23-,37-22-,38-23-,39-24-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JXFYRPWVBHUVFB-BGKHBZPASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>267.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>240.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>102.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353559</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022291</foodb_id>
  <chemspider_id>4575518</chemspider_id>
  <drugbank_id/>
  <chebi_id/>
  <pubchem_compound_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5830</metlin_id>
  <synthesis_reference>Arsenault, G. P.; Bullock, E.; MacDonald, S. F.  Pyrromethanes and porphyrins therefrom.    Journal of the American Chemical Society  (1960),  82  4384-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:48 UTC</creation_date>
  <update_date>2020-04-16 20:40:02 UTC</update_date>
  <accession>BMDB0000870</accession>
  <secondary_accessions>
    <accession>BMDB00870</accession>
  </secondary_accessions>
  <name>Histamine</name>
  <description>Histamine, also known as eramin or ceplene, belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group. Histamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Histamine exists in all living species, ranging from bacteria to humans. Histamine participates in a number of enzymatic reactions, within cattle. In particular, Histamine can be converted into histamine; which is mediated by the enzyme histamine H2 receptor. In addition, Histamine can be converted into histamine; which is mediated by the enzyme histamine H2 receptor. In cattle, histamine is involved in the metabolic pathway called the intracellular signalling through histamine H2 receptor and histamine pathway. Histamine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1H-Imidazole-4-ethanamine</synonym>
    <synonym>2-(4-Imidazolyl)ethylamine</synonym>
    <synonym>2-(1H-Imidazol-4-yl)ethanamine</synonym>
    <synonym>2-(1H-Imidazol-4-yl)ethylamine</synonym>
    <synonym>2-(1H-Imidazol-5-yl)ethanamine</synonym>
    <synonym>2-(1H-Imidazol-5-yl)ethylamine</synonym>
    <synonym>2-(4-Imidazolyl)ethanamine</synonym>
    <synonym>2-Imidazol-4-yl-ethylamine</synonym>
    <synonym>2-Imidazol-4-ylethylamine</synonym>
    <synonym>4-(2-Aminoethyl)-1H-imidazole</synonym>
    <synonym>4-(2-Aminoethyl)imidazole</synonym>
    <synonym>4-Imidazoleethylamine</synonym>
    <synonym>5-Imidazoleethylamine</synonym>
    <synonym>b-Imidazolyl-4-ethylamine</synonym>
    <synonym>beta-Aminoethylglyoxaline</synonym>
    <synonym>beta-Aminoethylimidazole</synonym>
    <synonym>beta-Aminothethylglyoxaline</synonym>
    <synonym>beta-Imidazolyl-4-ethylamine</synonym>
    <synonym>Eramin</synonym>
    <synonym>Ergamine</synonym>
    <synonym>Ergotidine</synonym>
    <synonym>HSM</synonym>
    <synonym>2-(3H-Imidazol-4-yl)ethylamine</synonym>
    <synonym>Imidazole-4-ethylamine</synonym>
    <synonym>Β-imidazolyl-4-ethylamine</synonym>
    <synonym>Histamine</synonym>
  </synonyms>
  <chemical_formula>C5H9N3</chemical_formula>
  <average_molecular_weight>111.1451</average_molecular_weight>
  <monisotopic_moleculate_weight>111.079647303</monisotopic_moleculate_weight>
  <iupac_name>2-(1H-imidazol-4-yl)ethan-1-amine</iupac_name>
  <traditional_iupac>histamine</traditional_iupac>
  <cas_registry_number>51-45-6</cas_registry_number>
  <smiles>NCCC1=CNC=N1</smiles>
  <inchi>InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)</inchi>
  <inchikey>NTYJJOPFIAHURM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>2-arylethylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-arylethylamine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>Histamine</external_descriptor>
      <external_descriptor>aralkylamino compound</external_descriptor>
      <external_descriptor>imidazoles</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>86 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.7</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(1H-imidazol-4-yl)ethan-1-amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>111.1451</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>111.079647303</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCC1=CNC=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H9N3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NTYJJOPFIAHURM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fc Epsilon Receptor I Signaling in Mast Cells</name>
      <smpdb_id>SMP0108186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gastric Acid Production</name>
      <smpdb_id>SMP0119381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histamine H1 Receptor Activation</name>
      <smpdb_id>SMP0108002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Histamine H2 Receptor and Histamine</name>
      <smpdb_id>SMP0107995</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451933</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>25+/-16</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>17+/-4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.938</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Aurand LW, Moore PA, Jones EE: Effect of histamine on bovine milk fatty acids. J Anim Sci. 1980 May;50(5):783-92.</reference_text>
          <pubmed_id>7190139</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.229</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Cows infected with mastitis</comment>
      <references>
        <reference>
          <reference_text>Aurand LW, Moore PA, Jones EE: Effect of histamine on bovine milk fatty acids. J Anim Sci. 1980 May;50(5):783-92.</reference_text>
          <pubmed_id>7190139</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>5.07 +/- 6.37</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>5.07 +/- 6.37</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>57+/-43</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>23+/-6</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00388</kegg_id>
  <foodb_id>FDB012596</foodb_id>
  <chemspider_id>753</chemspider_id>
  <drugbank_id>DB05381</drugbank_id>
  <chebi_id>18295</chebi_id>
  <pubchem_compound_id>774</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001414</knapsack_id>
  <meta_cyc_id>HISTAMINE</meta_cyc_id>
  <bigg_id>1810403</bigg_id>
  <wikipedia_id>Histamine</wikipedia_id>
  <metlin_id>68</metlin_id>
  <synthesis_reference>Pyman, Frank L. 2-Thiol-4(5)-b-aminoethylglyoxaline (2-thiolhistamine). Journal of the Chemical Society (1930), 98-100.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Aurand LW, Moore PA, Jones EE: Effect of histamine on bovine milk fatty acids. J Anim Sci. 1980 May;50(5):783-92.</reference_text>
      <pubmed_id>7190139</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00122</protein_accession>
      <name>Histamine N-methyltransferase</name>
      <uniprot_id>Q58DV7</uniprot_id>
      <gene_name>HNMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00561</protein_accession>
      <name>Histidine decarboxylase</name>
      <uniprot_id>Q5EA83</uniprot_id>
      <gene_name>HDC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01811</protein_accession>
      <name>Synaptic vesicular amine transporter</name>
      <uniprot_id>Q27963</uniprot_id>
      <gene_name>SLC18A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01812</protein_accession>
      <name>HRH1 protein</name>
      <uniprot_id>A5D795</uniprot_id>
      <gene_name>HRH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01813</protein_accession>
      <name>Histamine H1 receptor</name>
      <uniprot_id>P30546</uniprot_id>
      <gene_name>HRH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:50 UTC</creation_date>
  <update_date>2020-03-13 16:24:24 UTC</update_date>
  <accession>BMDB0000871</accession>
  <secondary_accessions>
    <accession>BMDB00871</accession>
  </secondary_accessions>
  <name>5alpha-Cholestanone</name>
  <description/>
  <synonyms>
    <synonym>5a-Cholestanone</synonym>
    <synonym>5Α-cholestanone</synonym>
    <synonym>(5a,17b)-17-Octylandrostan-3-one</synonym>
    <synonym>(5alpha)-Cholestan-3-one</synonym>
    <synonym>(5alpha)-Cholestanone</synonym>
    <synonym>5a(H)-Cholestan-3-one</synonym>
    <synonym>5a-Cholestan-3-one</synonym>
    <synonym>5alpha-Cholestane-3-one</synonym>
    <synonym>5alpha-Coprostanone</synonym>
    <synonym>Coprostanone, (5alpha)-isomer</synonym>
    <synonym>Coprostanone, (5beta)-isomer</synonym>
    <synonym>Coprostanone</synonym>
    <synonym>5-alpha-Cholestan-3-one</synonym>
  </synonyms>
  <chemical_formula>C27H46O</chemical_formula>
  <average_molecular_weight>386.6535</average_molecular_weight>
  <monisotopic_moleculate_weight>386.354866094</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one</iupac_name>
  <traditional_iupac>(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one</traditional_iupac>
  <cas_registry_number>566-88-1</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</smiles>
  <inchi>InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-20,22-25H,6-17H2,1-5H3/t19-,20+,22+,23-,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>PESKGJQREUXSRR-UXIWKSIVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-oxo-5-alpha-steroids</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-oxo-5-alpha-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-oxo steroid</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>128 - 130 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>386.6535</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>386.354866094</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H46O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-20,22-25H,6-17H2,1-5H3/t19-,20+,22+,23-,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PESKGJQREUXSRR-UXIWKSIVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>118.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>50.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339780</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03238</kegg_id>
  <foodb_id>FDB022292</foodb_id>
  <chemspider_id>83174</chemspider_id>
  <drugbank_id/>
  <chebi_id>17762</chebi_id>
  <pubchem_compound_id>92128</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5832</metlin_id>
  <synthesis_reference>Cargill, D. I.  The separation of cholesterol from related stanols and stanones by thin-layer chromatography.    Analyst  (1962),  87  865-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:51 UTC</creation_date>
  <update_date>2020-03-13 16:24:25 UTC</update_date>
  <accession>BMDB0000872</accession>
  <secondary_accessions>
    <accession>BMDB00872</accession>
  </secondary_accessions>
  <name>Tetradecanedioic acid</name>
  <description/>
  <synonyms>
    <synonym>1,12-Dodecanedicarboxylic acid</synonym>
    <synonym>1,14-Tetradecanedioic acid</synonym>
    <synonym>Dodecamethylenedicarboxylic acid</synonym>
    <synonym>NSC 9504</synonym>
    <synonym>Tetradecane-1,14-dioic acid</synonym>
    <synonym>1,12-Dodecanedicarboxylate</synonym>
    <synonym>1,14-Tetradecanedioate</synonym>
    <synonym>Dodecamethylenedicarboxylate</synonym>
    <synonym>Tetradecane-1,14-dioate</synonym>
    <synonym>Tetradecanedioate</synonym>
    <synonym>Tetradecanedicarboxylate</synonym>
    <synonym>Tetradecanedicarboxylic acid</synonym>
  </synonyms>
  <chemical_formula>C14H26O4</chemical_formula>
  <average_molecular_weight>258.3538</average_molecular_weight>
  <monisotopic_moleculate_weight>258.18310932</monisotopic_moleculate_weight>
  <iupac_name>tetradecanedioic acid</iupac_name>
  <traditional_iupac>tetradecanedioic acid</traditional_iupac>
  <cas_registry_number>821-38-5</cas_registry_number>
  <smiles>OC(=O)CCCCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C14H26O4/c15-13(16)11-9-7-5-3-1-2-4-6-8-10-12-14(17)18/h1-12H2,(H,15,16)(H,17,18)</inchi>
  <inchikey>HQHCYKULIHKCEB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>alpha,omega-dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>0.2 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>tetradecanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>258.3538</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>258.18310932</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H26O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H26O4/c15-13(16)11-9-7-5-3-1-2-4-6-8-10-12-14(17)18/h1-12H2,(H,15,16)(H,17,18)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HQHCYKULIHKCEB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>69.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362316</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022293</foodb_id>
  <chemspider_id>12630</chemspider_id>
  <drugbank_id/>
  <chebi_id>76308</chebi_id>
  <pubchem_compound_id>13185</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5833</metlin_id>
  <synthesis_reference>Chen, Yuandong; Hao, Xiuzhen.  Method for producing tetradecanedioic acid by bioconversion of n-tetradecane.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2002),     10 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:52 UTC</creation_date>
  <update_date>2020-03-13 16:24:25 UTC</update_date>
  <accession>BMDB0000873</accession>
  <secondary_accessions>
    <accession>BMDB00873</accession>
  </secondary_accessions>
  <name>4-Methylcatechol</name>
  <description/>
  <synonyms>
    <synonym>1,2-Dihydroxy-4-methylbenzene</synonym>
    <synonym>2-Hydroxy-4-methylphenol</synonym>
    <synonym>3,4-Dihydroxytoluene</synonym>
    <synonym>4-Methyl-1,2-benzenediol</synonym>
    <synonym>4-Methyl-1,2-dihydroxybenzene</synonym>
    <synonym>4-Methylpyrocatechol</synonym>
    <synonym>Homocatechol</synonym>
    <synonym>Homopyrocatechol</synonym>
    <synonym>p-Methylcatechol</synonym>
    <synonym>p-Methylpyrocatechol</synonym>
    <synonym>Toluene-3,4-diol</synonym>
    <synonym>1-Methyl-3,4-dihydroxybenzene</synonym>
    <synonym>4-Methyl-pyrocatechol</synonym>
    <synonym>4-Methylcatehol</synonym>
    <synonym>4-Metylcatechol</synonym>
    <synonym>5-Methylcatechol</synonym>
  </synonyms>
  <chemical_formula>C7H8O2</chemical_formula>
  <average_molecular_weight>124.1372</average_molecular_weight>
  <monisotopic_moleculate_weight>124.0524295</monisotopic_moleculate_weight>
  <iupac_name>4-methylbenzene-1,2-diol</iupac_name>
  <traditional_iupac>4-methyl-1,2-benzenediol</traditional_iupac>
  <cas_registry_number>452-86-8</cas_registry_number>
  <smiles>CC1=CC=C(O)C(O)=C1</smiles>
  <inchi>InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3</inchi>
  <inchikey>ZBCATMYQYDCTIZ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Benzenediols</sub_class>
    <direct_parent>Catechols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Meta cresols</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Para cresols</alternative_parent>
      <alternative_parent>Toluenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Catechol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>M-cresol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>P-cresol</substituent>
      <substituent>Toluene</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a catechol</external_descriptor>
      <external_descriptor>methylcatechol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>65 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.37</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-methylbenzene-1,2-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>124.1372</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>124.0524295</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CC=C(O)C(O)=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H8O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZBCATMYQYDCTIZ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440173</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C06730</kegg_id>
  <foodb_id>FDB008861</foodb_id>
  <chemspider_id>9564</chemspider_id>
  <drugbank_id>DB04120</drugbank_id>
  <chebi_id>17254</chebi_id>
  <pubchem_compound_id>9958</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id>704</phenol_explorer_compound_id>
  <knapsack_id>C00002660</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>4-Methylcatechol</wikipedia_id>
  <metlin_id>5834</metlin_id>
  <synthesis_reference>Liang, Zesheng; Zhang, Ying; Wu, Baojun; Zhang, Mingsen; Wang, Xiu'en.  Preparation of 4-methylcatechol with good yield and selectivity.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2001),     6 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:53 UTC</creation_date>
  <update_date>2020-04-15 22:14:37 UTC</update_date>
  <accession>BMDB0000874</accession>
  <secondary_accessions>
    <accession>BMDB00874</accession>
  </secondary_accessions>
  <name>Tauroursodeoxycholic acid</name>
  <description/>
  <synonyms>
    <synonym>Tauroursodeoxycholate</synonym>
    <synonym>2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl) amino)ethanesulfonate</synonym>
    <synonym>2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl) amino)ethanesulfonic acid</synonym>
    <synonym>2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl)amino)-ethanesulfonate</synonym>
    <synonym>2-(((3-alpha,5-beta,7-beta)-3,7-Dihydroxy-24-oxocholan-24-yl)amino)-ethanesulfonic acid</synonym>
    <synonym>3a,7b-Dihydroxy-5b-cholanoyltaurine</synonym>
    <synonym>N-(3-alpha,7-beta-Dihydroxy-5-beta-cholan-24-oyl)-taurine</synonym>
    <synonym>TUDCA</synonym>
    <synonym>UR 906</synonym>
    <synonym>Ursodeoxycholyltaurine</synonym>
    <synonym>Tauroursodeoxycholic acid, monosodium salt, (3alpha,5beta,7alpha)-isomer</synonym>
    <synonym>Tauroursodeoxycholic acid, (3alpha,5alpha,7alpha)-isomer</synonym>
    <synonym>Tauroursodeoxycholic acid, monosodium salt, (3alpha,7alpha)-isomer</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-N-(2-sulfoethyl)pentanimidate</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-N-(2-sulphoethyl)pentanimidate</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-N-(2-sulphoethyl)pentanimidic acid</synonym>
  </synonyms>
  <chemical_formula>C26H45NO6S</chemical_formula>
  <average_molecular_weight>499.704</average_molecular_weight>
  <monisotopic_moleculate_weight>499.296758867</monisotopic_moleculate_weight>
  <iupac_name>2-[(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid</iupac_name>
  <traditional_iupac>2-[(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethanesulfonic acid</traditional_iupac>
  <cas_registry_number>14605-22-2</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(=O)NCCS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)CC2C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17?,18-,19-,20+,21+,22+,24+,25+,26-/m1/s1</inchi>
  <inchikey>BHTRKEVKTKCXOH-VSHSPWMTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Taurinated bile acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Alkanesulfonic acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Dihydroxy bile acids, alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonic acids</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfonyls</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkanesulfonic acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfonyl</substituent>
      <substituent>Taurinated bile acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-0.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4R)-4-[(1S,2S,5R,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>499.704</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>499.296758867</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(=O)NCCS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)CC2C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H45NO6S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17?,18-,19-,20+,21+,22+,24+,25+,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHTRKEVKTKCXOH-VSHSPWMTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>123.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>130.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>56.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37818</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022294</foodb_id>
  <kegg_id/>
  <pubchem_compound_id>12443252</pubchem_compound_id>
  <chemspider_id>25949321</chemspider_id>
  <chebi_id/>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Tauroursodeoxycholic acid</wikipedia_id>
  <metlin_id>5835</metlin_id>
  <synthesis_reference>Zhuo, Chao; Feng, Wei; Wu, Da-jun; Xiong, Zhi-gang.  Synthesis of tauroursodeoxycholic acid.    Hecheng Huaxue  (2002),  10(5),  444-446.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:54 UTC</creation_date>
  <update_date>2020-04-14 22:48:30 UTC</update_date>
  <accession>BMDB0000875</accession>
  <secondary_accessions>
    <accession>BMDB00875</accession>
  </secondary_accessions>
  <name>Trigonelline</name>
  <description/>
  <synonyms>
    <synonym>1-Methyl-1,2-dihydropyridine-3-carboxylate</synonym>
  </synonyms>
  <chemical_formula>C7H9NO2</chemical_formula>
  <average_molecular_weight>139.154</average_molecular_weight>
  <monisotopic_moleculate_weight>139.063328534</monisotopic_moleculate_weight>
  <iupac_name>1-methyl-1,2-dihydropyridine-3-carboxylic acid</iupac_name>
  <traditional_iupac>trigonellin</traditional_iupac>
  <cas_registry_number/>
  <smiles>CN1CC(=CC=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C7H9NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-4H,5H2,1H3,(H,9,10)</inchi>
  <inchikey>YCABHAGDPZAUBJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydropyridinecarboxylic acids and derivatives. Dihydropyridinecarboxylic acids and derivatives are compounds containing a dihydropyridine moiety bearing a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Hydropyridines</sub_class>
    <direct_parent>Dihydropyridinecarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Allylamines</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Enamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Allylamine</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dihydropyridinecarboxylic acid derivative</substituent>
      <substituent>Enamine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-methyl-1,2-dihydropyridine-3-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>139.154</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>139.063328534</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1CC(=CC=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H9NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H9NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-4H,5H2,1H3,(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YCABHAGDPZAUBJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1296853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1296854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1296855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1411495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1411496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1411497</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id>21276947</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Trigonelline</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Sarett, Herbert P.; Perlzweig, William A.; Levy, Edward D.  Synthesis and excretion of trigonelline.    Journal of Biological Chemistry  (1940),  135  483-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:55 UTC</creation_date>
  <update_date>2020-04-16 20:39:22 UTC</update_date>
  <accession>BMDB0000876</accession>
  <secondary_accessions>
    <accession>BMDB00876</accession>
  </secondary_accessions>
  <name>Vitamin D3</name>
  <description>Vitamin D3 belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. Vitamin D3 exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule.</description>
  <synonyms>
    <synonym>(+)-Vitamin D3</synonym>
    <synonym>(3beta,Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-ol</synonym>
    <synonym>(5E,7E)-9,10-Secocholesta-5,7,10-trien-3-ol</synonym>
    <synonym>3-beta,Z,7E-9,10-Secocholestr-5,7,10(19)-trien-3-ol</synonym>
    <synonym>9,10-Secocholesta-5,7,10(19)-trien-3-beta-ol</synonym>
    <synonym>9,10-Secocholesta-5,7,10(19)-trien-3-ol</synonym>
    <synonym>9,10-Secocholesta-5,7,10-trien-3-ol</synonym>
    <synonym>Arachitol</synonym>
    <synonym>Calciol</synonym>
    <synonym>CC</synonym>
    <synonym>Cholecalciferol</synonym>
    <synonym>Cholecalciferol D3</synonym>
    <synonym>Colecalciferol</synonym>
    <synonym>D3-Vigantol</synonym>
    <synonym>Delsterol</synonym>
    <synonym>Deparal</synonym>
    <synonym>Devaron</synonym>
    <synonym>Ebivit</synonym>
    <synonym>FeraCol</synonym>
    <synonym>Granuvit D3</synonym>
    <synonym>micro-Dee</synonym>
    <synonym>Oleovitamin D3</synonym>
    <synonym>Provitina</synonym>
    <synonym>Quintox</synonym>
    <synonym>Ricketon</synonym>
    <synonym>Trivitan</synonym>
    <synonym>Vi-de3</synonym>
    <synonym>VidDe-3-hydrosol</synonym>
    <synonym>Videkhol</synonym>
    <synonym>Vigantol</synonym>
    <synonym>Vigorsan</synonym>
    <synonym>Vitinc dan-dee-3</synonym>
    <synonym>(3 beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-ol</synonym>
    <synonym>Cholecalciferols</synonym>
    <synonym>Vitamin D 3</synonym>
  </synonyms>
  <chemical_formula>C27H44O</chemical_formula>
  <average_molecular_weight>384.6377</average_molecular_weight>
  <monisotopic_moleculate_weight>384.33921603</monisotopic_moleculate_weight>
  <iupac_name>(1S,3Z)-3-{2-[(1R,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol</iupac_name>
  <traditional_iupac>rampage</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(C)CCC[C@@H](C)[C@H]1CCC2\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C</smiles>
  <inchi>InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26?,27-/m1/s1</inchi>
  <inchikey>QYSXJUFSXHHAJI-QWSSABAFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Vitamin D and derivatives</sub_class>
    <direct_parent>Vitamin D and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Triterpenoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,3Z)-3-{2-[(1R,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>384.6377</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>384.33921603</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CCC[C@@H](C)[C@H]1CCC2\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H44O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26?,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QYSXJUFSXHHAJI-QWSSABAFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>123.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>49.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1522</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00013</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1266&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00013</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1266&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000182</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, s</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1266&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00198</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1266&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000182</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1266&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0026</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1266&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000234</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1266&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000208</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1266&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0147 +/- 0.0002</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.019 +/- 0.001</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0435 +/- 0.0002</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.015 +/- 0.001</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00052</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Pirjo H. Mattila, Vieno I. Piironen, Esko J. Uusi-Rauva, and Pekka E. Koivistoinen. 1995. Contents of Cholecalciferol, Ergocalciferol, and Their 25-Hydroxylated Metabolites in Milk Products and Raw Meat and Liver As Determined by HPLC. J. Agric. Food Chem. 43 (9), pp 2394–2399</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id>10883523</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Cholecalciferol</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Nemoto, Hideo; Kurobe, Hiroshi; Fukumoto, Keiichiro; Kametani, Tetsuji. A modified synthesis of the (+)-8a-phenylsulfonyl-des-AB-cholestane via an intramolecular nucleophilic attack to epoxide - a total synthesis of vitamin D3. Heterocycles (1985), 23(3),</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Pirjo H. Mattila, Vieno I. Piironen, Esko J. Uusi-Rauva, and Pekka E. Koivistoinen. 1995. Contents of Cholecalciferol, Ergocalciferol, and Their 25-Hydroxylated Metabolites in Milk Products and Raw Meat and Liver As Determined by HPLC. J. Agric. Food Chem. 43 (9), pp 2394–2399</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1266&amp;2</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01912</protein_accession>
      <name>Vitamin D3 receptor</name>
      <uniprot_id>Q28037</uniprot_id>
      <gene_name>VDR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01913</protein_accession>
      <name>Vitamin D3 receptor</name>
      <uniprot_id>Q19MM0</uniprot_id>
      <gene_name>VDR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:57 UTC</creation_date>
  <update_date>2020-03-19 22:02:03 UTC</update_date>
  <accession>BMDB0000877</accession>
  <secondary_accessions>
    <accession>BMDB00877</accession>
  </secondary_accessions>
  <name>Umanopterin</name>
  <description/>
  <synonyms>
    <synonym>2-Amino-6-(1,2,3-trihydroxypropyl)-4(3H)-pteridinone</synonym>
    <synonym>Neopterin, (threo-D)-isomer</synonym>
    <synonym>Neopterin</synonym>
    <synonym>Neopterin, (r*, r*)-isomer</synonym>
    <synonym>Monapterin</synonym>
    <synonym>Neopterin, (erythro-D)-isomer</synonym>
    <synonym>2-Amino-6-[(1R,2R)-1,2,3-trihydroxypropyl]-4(3H)-pteridinone</synonym>
    <synonym>6-D-Threo-monapterin</synonym>
    <synonym>D-(-)-Monapterin</synonym>
    <synonym>D-6-(Threo-1',2',3'-trihydroxypropyl)pterin</synonym>
    <synonym>D-6-(Threo-1’,2’,3’-trihydroxypropyl)pterin</synonym>
    <synonym>D-Monapterin</synonym>
    <synonym>D-Threo-monapterin</synonym>
    <synonym>D-Threo-neopterin</synonym>
    <synonym>Umanopterin</synonym>
  </synonyms>
  <chemical_formula>C9H11N5O4</chemical_formula>
  <average_molecular_weight>253.2147</average_molecular_weight>
  <monisotopic_moleculate_weight>253.081103865</monisotopic_moleculate_weight>
  <iupac_name>2-amino-6-[(1R,2R)-1,2,3-trihydroxypropyl]-4,8-dihydropteridin-4-one</iupac_name>
  <traditional_iupac>2-amino-6-[(1R,2R)-1,2,3-trihydroxypropyl]-8H-pteridin-4-one</traditional_iupac>
  <cas_registry_number>10162-32-0</cas_registry_number>
  <smiles>NC1=NC(=O)C2=NC(=CNC2=N1)[C@@H](O)[C@H](O)CO</smiles>
  <inchi>InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)/t4-,6-/m1/s1</inchi>
  <inchikey>BMQYVXCPAOLZOK-INEUFUBQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Biopterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrazines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Biopterin</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrazine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>neopterins</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>8.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-6-[(1R,2R)-1,2,3-trihydroxypropyl]-4,8-dihydropteridin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>253.2147</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>253.081103865</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=NC(=CNC2=N1)[C@@H](O)[C@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11N5O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h1,4,6,15-17H,2H2,(H3,10,11,13,14,18)/t4-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BMQYVXCPAOLZOK-INEUFUBQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>152.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>59.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>252708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>252709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>252710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>272649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>272650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>272651</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id>DB02385</drugbank_id>
  <foodb_id>FDB022295</foodb_id>
  <chemspider_id>392507</chemspider_id>
  <pubchem_compound_id>135460965</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Taylor, Edward C.; Jacobi, Peter A.  Pteridines.  XXXVII.  A total synthesis of L-erythro-biopterin and some related 6-(polyhydroxyalkyl)pterins.    Journal of the American Chemical Society  (1976),  98(8),  2301-7. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:58 UTC</creation_date>
  <update_date>2020-03-13 16:24:28 UTC</update_date>
  <accession>BMDB0000878</accession>
  <secondary_accessions>
    <accession>BMDB00878</accession>
  </secondary_accessions>
  <name>Ergosterol</name>
  <description/>
  <synonyms>
    <synonym>Xanthurenate</synonym>
    <synonym>8-Hydroxykynurenic acid</synonym>
    <synonym>Gametocyte activating factor (gaf)</synonym>
    <synonym>4,8-Dihydroxy-2-quinolinecarboxylate</synonym>
    <synonym>4,8-Dihydroxy-2-quinolinecarboxylic acid</synonym>
    <synonym>4,8-Dihydroxy-quinaldate</synonym>
    <synonym>4,8-Dihydroxy-quinaldic acid</synonym>
    <synonym>4,8-Dihydroxyquinaldate</synonym>
    <synonym>4,8-Dihydroxyquinaldic acid</synonym>
    <synonym>4,8-Dihydroxyquinaldinate</synonym>
    <synonym>4,8-Dihydroxyquinaldinic acid</synonym>
    <synonym>4,8-Dihydroxyquinoline-2-carboxylate</synonym>
    <synonym>4,8-Dihydroxyquinoline-2-carboxylic acid</synonym>
    <synonym>4-Oxoxanthurenic acid</synonym>
    <synonym>8-Hydroxykynurenate</synonym>
    <synonym>Oxoxanthurenate</synonym>
    <synonym>Xanthurate</synonym>
    <synonym>Xanthuric acid</synonym>
    <synonym>(22E)-Ergosta-5,7,22-trien-3-ol</synonym>
    <synonym>(24R)-Ergosta-5,7,22-trien-3b-ol</synonym>
    <synonym>(3beta)-Ergosta-5,7,22-trien-3-ol</synonym>
    <synonym>(3beta,22E)-Ergosta-5,7,22-trien-3-ol</synonym>
    <synonym>(3beta,2E)-Ergosta-5,7,22-trien-3-ol</synonym>
    <synonym>24-Methylcholesta-5,7,22-trien-3b-ol</synonym>
    <synonym>24-Methylcholesta-5,7,22-trien-3beta-ol</synonym>
    <synonym>24a-Methyl-22E-dehydrocholesterol</synonym>
    <synonym>24alpha-Methyl-22E-dehydrocholestero</synonym>
    <synonym>24R-Methylcholesta-5,7,22E-trien-3b-ol</synonym>
    <synonym>24R-Methylcholesta-5,7,22E-trien-3beta-ol</synonym>
    <synonym>Ergosta-5,7,22-trien-3-ol</synonym>
    <synonym>Ergosterin</synonym>
    <synonym>Provitamine D2</synonym>
  </synonyms>
  <chemical_formula>C28H44O</chemical_formula>
  <average_molecular_weight>396.6484</average_molecular_weight>
  <monisotopic_moleculate_weight>396.33921603</monisotopic_moleculate_weight>
  <iupac_name>(2R,5S,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol</iupac_name>
  <traditional_iupac>(2R,5S,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol</traditional_iupac>
  <cas_registry_number>59-00-7</cas_registry_number>
  <smiles>CC(C)[C@@H](C)\C=C\[C@@H](C)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C</smiles>
  <inchi>InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24?,25?,26?,27-,28+/m0/s1</inchi>
  <inchikey>DNVPQKQSNYMLRS-KQYMERMZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Quinolines and derivatives</class>
    <sub_class>Quinoline carboxylic acids</sub_class>
    <direct_parent>Quinoline carboxylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>8-hydroxyquinolines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroquinolines</alternative_parent>
      <alternative_parent>Hydroquinolones</alternative_parent>
      <alternative_parent>Hydroxyquinolines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridinecarboxylic acids</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>8-hydroxyquinoline</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dihydroquinoline</substituent>
      <substituent>Dihydroquinolone</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyquinoline</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridine carboxylic acid</substituent>
      <substituent>Pyridine carboxylic acid or derivatives</substituent>
      <substituent>Quinoline-2-carboxylic acid</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dihydroxyquinoline</external_descriptor>
      <external_descriptor>quinolinemonocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>170 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>16 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,5S,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>396.6484</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>396.33921603</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)[C@@H](C)\C=C\[C@@H](C)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C28H44O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24?,25?,26?,27-,28+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DNVPQKQSNYMLRS-KQYMERMZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>127.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>49.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>241399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>241400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>241401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>243454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>243455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>243456</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02470</kegg_id>
  <phenol_explorer_compound_id/>
  <chemspider_id>5497</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB022297</foodb_id>
  <pubchem_compound_id>5699</pubchem_compound_id>
  <chebi_id>10072</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id>XANTHURENATE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Xanthurenic_acid</wikipedia_id>
  <metlin_id>5841</metlin_id>
  <synthesis_reference>He, Xiuping; Zhang, Borun; Tan, Huarong. Overexpression of a sterol C-24(28) reductase increases ergosterol production in Saccharomyces cerevisiae.   Biotechnology Letters  (2003),  25(10),  773-778.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:37:59 UTC</creation_date>
  <update_date>2020-03-13 16:24:29 UTC</update_date>
  <accession>BMDB0000879</accession>
  <secondary_accessions>
    <accession>BMDB00879</accession>
  </secondary_accessions>
  <name>Tetrahydrodeoxycorticosterone</name>
  <description/>
  <synonyms>
    <synonym>5alpha-THDOC</synonym>
    <synonym>3alpha,21-Dihydroxy-5alpha-pregnan-20-one</synonym>
    <synonym>5a-THDOC</synonym>
    <synonym>5Α-thdoc</synonym>
    <synonym>3a,21-Dihydroxy-5a-pregnan-20-one</synonym>
    <synonym>3Α,21-dihydroxy-5α-pregnan-20-one</synonym>
    <synonym>3alpha,21-Dihydroxy-5beta-pregnan-20-one</synonym>
    <synonym>5-alpha-THDOC</synonym>
    <synonym>Allotetrahydrodeoxycorticosterone</synonym>
    <synonym>Deoxycorticosterone-21-aminopropane</synonym>
    <synonym>Tetrahydro-11-deoxycorticosterone</synonym>
    <synonym>3 alpha,21-Dihydroxy-5 beta-pregnan-20-one</synonym>
    <synonym>3 alpha,5 beta-Tetrahydrodeoxycorticosterone</synonym>
    <synonym>3 beta,5 alpha-Tetrahydrodeoxycorticosterone</synonym>
    <synonym>3,21-Dihydroxypregnan-20-one</synonym>
    <synonym>5alpha-Pregnan-3alpha,21-diol-20-one</synonym>
    <synonym>5alpha-Pregnane-3alpha,21-diol-20-one</synonym>
    <synonym>THDOC</synonym>
    <synonym>Pregnane-3,21-diol-20-one</synonym>
    <synonym>Tetrahydrodeoxycorticosterone, (3alpha,5alpha)-isomer</synonym>
    <synonym>Tetrahydrodeoxycorticosterone, (3beta,5alpha)-isomer</synonym>
    <synonym>Tetrahydrodesoxycorticosterone</synonym>
  </synonyms>
  <chemical_formula>C21H34O3</chemical_formula>
  <average_molecular_weight>334.4929</average_molecular_weight>
  <monisotopic_moleculate_weight>334.250794954</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one</iupac_name>
  <traditional_iupac>tetrahydrodeoxycorticosterone</traditional_iupac>
  <cas_registry_number>567-03-3</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H34O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13-18,22-23H,3-12H2,1-2H3/t13-,14+,15-,16-,17-,18+,20-,21-/m0/s1</inchi>
  <inchikey>CYKYBWRSLLXBOW-GDYGHMJCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>21-hydroxy steroid</external_descriptor>
      <external_descriptor>Glycine conjugates</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>334.4929</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>334.250794954</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H34O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H34O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13-18,22-23H,3-12H2,1-2H3/t13-,14+,15-,16-,17-,18+,20-,21-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CYKYBWRSLLXBOW-GDYGHMJCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>94.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>72549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>72550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>72551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>131508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>131509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>131510</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C13713</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022296</foodb_id>
  <chemspider_id>91953</chemspider_id>
  <pubchem_compound_id>101771</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>805752</chebi_id>
  <meta_cyc_id/>
  <wikipedia_id>Tetrahydrodeoxycorticosterone</wikipedia_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>5840</metlin_id>
  <synthesis_reference>Holland, Herbert L.; Ninniss, Ronald W.; Brown, Frances M. Stereochemistry of hydrogen loss during C-21 dehydroxylation of tetrahydrodeoxycorticosterone by Eubacterium lentum. Canadian Journal of Chemistry (1989), 67(10), 1590-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:00 UTC</creation_date>
  <update_date>2020-04-15 21:56:55 UTC</update_date>
  <accession>BMDB0000881</accession>
  <secondary_accessions>
    <accession>BMDB00881</accession>
  </secondary_accessions>
  <name>Xanthurenic acid</name>
  <description>Xanthurenic acid, also known as xanthurenic acid, belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Xanthurenic acid exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Xanthurenic acid exists in all living species, ranging from bacteria to humans. In cattle, xanthurenic acid is involved in the metabolic pathway called the tryptophan metabolism pathway.</description>
  <synonyms>
    <synonym>Xanthurenate</synonym>
    <synonym>8-Hydroxykynurenic acid</synonym>
    <synonym>Gametocyte activating factor (gaf)</synonym>
    <synonym>4,8-Dihydroxy-2-quinolinecarboxylate</synonym>
    <synonym>4,8-Dihydroxy-2-quinolinecarboxylic acid</synonym>
    <synonym>4,8-Dihydroxy-quinaldate</synonym>
    <synonym>4,8-Dihydroxy-quinaldic acid</synonym>
    <synonym>4,8-Dihydroxyquinaldate</synonym>
    <synonym>4,8-Dihydroxyquinaldic acid</synonym>
    <synonym>4,8-Dihydroxyquinaldinate</synonym>
    <synonym>4,8-Dihydroxyquinaldinic acid</synonym>
    <synonym>4,8-Dihydroxyquinoline-2-carboxylate</synonym>
    <synonym>4,8-Dihydroxyquinoline-2-carboxylic acid</synonym>
    <synonym>4-Oxoxanthurenic acid</synonym>
    <synonym>8-Hydroxykynurenate</synonym>
    <synonym>Oxoxanthurenate</synonym>
    <synonym>Xanthurate</synonym>
    <synonym>Xanthuric acid</synonym>
  </synonyms>
  <chemical_formula>C10H7NO4</chemical_formula>
  <average_molecular_weight>205.1669</average_molecular_weight>
  <monisotopic_moleculate_weight>205.037507717</monisotopic_moleculate_weight>
  <iupac_name>4,8-dihydroxyquinoline-2-carboxylic acid</iupac_name>
  <traditional_iupac>xanthurenic acid</traditional_iupac>
  <cas_registry_number>59-00-7</cas_registry_number>
  <smiles>OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1</smiles>
  <inchi>InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)</inchi>
  <inchikey>FBZONXHGGPHHIY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Quinolines and derivatives</class>
    <sub_class>Quinoline carboxylic acids</sub_class>
    <direct_parent>Quinoline carboxylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>8-hydroxyquinolines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroquinolines</alternative_parent>
      <alternative_parent>Hydroquinolones</alternative_parent>
      <alternative_parent>Hydroxyquinolines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridinecarboxylic acids</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>8-hydroxyquinoline</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dihydroquinoline</substituent>
      <substituent>Dihydroquinolone</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyquinoline</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridine carboxylic acid</substituent>
      <substituent>Pyridine carboxylic acid or derivatives</substituent>
      <substituent>Quinoline-2-carboxylic acid</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dihydroxyquinoline</external_descriptor>
      <external_descriptor>quinolinemonocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>289 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4,8-dihydroxyquinoline-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>205.1669</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>205.037507717</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H7NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FBZONXHGGPHHIY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>90.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4704</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438601</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02470</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022297</foodb_id>
  <chemspider_id>5497</chemspider_id>
  <pubchem_compound_id>5699</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>10072</chebi_id>
  <meta_cyc_id>XANTHURENATE</meta_cyc_id>
  <wikipedia_id>Xanthurenic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>5841</metlin_id>
  <synthesis_reference>Furst, Arthur; Olsen, Carl J. A convenient synthesis of xanthurenic acid. Journal of Organic Chemistry (1951), 16 412-14.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:01 UTC</creation_date>
  <update_date>2020-04-16 20:39:05 UTC</update_date>
  <accession>BMDB0000883</accession>
  <secondary_accessions>
    <accession>BMDB00883</accession>
  </secondary_accessions>
  <name>L-Valine</name>
  <description>L-Valine, also known as (S)-valine or L-valin, belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Valine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Valine exists in all living species, ranging from bacteria to humans. L-Valine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2S)-2-Amino-3-methylbutanoic acid</synonym>
    <synonym>(S)-Valine</synonym>
    <synonym>2-Amino-3-methylbutyric acid</synonym>
    <synonym>L-(+)-alpha-Aminoisovaleric acid</synonym>
    <synonym>L-alpha-Amino-beta-methylbutyric acid</synonym>
    <synonym>L-Valin</synonym>
    <synonym>V</synonym>
    <synonym>Val</synonym>
    <synonym>VALINE</synonym>
    <synonym>(2S)-2-Amino-3-methylbutanoate</synonym>
    <synonym>2-Amino-3-methylbutyrate</synonym>
    <synonym>L-(+)-a-Aminoisovalerate</synonym>
    <synonym>L-(+)-a-Aminoisovaleric acid</synonym>
    <synonym>L-(+)-alpha-Aminoisovalerate</synonym>
    <synonym>L-(+)-Α-aminoisovalerate</synonym>
    <synonym>L-(+)-Α-aminoisovaleric acid</synonym>
    <synonym>L-a-Amino-b-methylbutyrate</synonym>
    <synonym>L-a-Amino-b-methylbutyric acid</synonym>
    <synonym>L-alpha-Amino-beta-methylbutyrate</synonym>
    <synonym>L-Α-amino-β-methylbutyrate</synonym>
    <synonym>L-Α-amino-β-methylbutyric acid</synonym>
    <synonym>(S)-2-Amino-3-methyl-butanoate</synonym>
    <synonym>(S)-2-Amino-3-methyl-butanoic acid</synonym>
    <synonym>(S)-2-Amino-3-methylbutanoate</synonym>
    <synonym>(S)-2-Amino-3-methylbutanoic acid</synonym>
    <synonym>(S)-2-Amino-3-methylbutyrate</synonym>
    <synonym>(S)-2-Amino-3-methylbutyric acid</synonym>
    <synonym>(S)-a-Amino-b-methylbutyrate</synonym>
    <synonym>(S)-a-Amino-b-methylbutyric acid</synonym>
    <synonym>(S)-alpha-Amino-beta-methylbutyrate</synonym>
    <synonym>(S)-alpha-Amino-beta-methylbutyric acid</synonym>
    <synonym>2-Amino-3-methylbutanoate</synonym>
    <synonym>2-Amino-3-methylbutanoic acid</synonym>
    <synonym>L Valine</synonym>
  </synonyms>
  <chemical_formula>C5H11NO2</chemical_formula>
  <average_molecular_weight>117.1463</average_molecular_weight>
  <monisotopic_moleculate_weight>117.078978601</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-methylbutanoic acid</iupac_name>
  <traditional_iupac>L-valine</traditional_iupac>
  <cas_registry_number>72-18-4</cas_registry_number>
  <smiles>CC(C)[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1</inchi>
  <inchikey>KZSNJWFQEVHDMF-BYPYZUCNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Valine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Valine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
      <external_descriptor>pyruvate family amino acid</external_descriptor>
      <external_descriptor>valine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>295 - 300 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>58.5 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.26</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-methylbutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>117.1463</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>117.078978601</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H11NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KZSNJWFQEVHDMF-BYPYZUCNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>29.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Valine</name>
      <smpdb_id>SMP0119417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178808</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 24 male 17-22-month-old Charolais beef cattles.</comment>
      <references>
        <reference>
          <reference_text>Graham SF, Ruiz-Aracama A, Lommen A, Cannizzo FT, Biolatti B, Elliott CT, Mooney MH: Use of NMR metabolomic plasma profiling methodologies to identify illicit growth-promoting administrations. Anal Bioanal Chem. 2012 Apr;403(2):573-82. doi: 10.1007/s00216-012-5815-z. Epub 2012 Feb 28.</reference_text>
          <pubmed_id>22370585</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>169.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by GC/MS</comment>
      <references>
        <reference>
          <reference_text>Allison GG, Horton RA, Rees Stevens P, Jackman R, Moorby JM: Changes in plasma metabolites and muscle glycogen are correlated to bovine spongiform encephalopathy in infected dairy cattle. Res Vet Sci. 2007 Aug;83(1):40-6. doi: 10.1016/j.rvsc.2006.11.008. Epub 2007 Jan  2.</reference_text>
          <pubmed_id>17197001</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>7212 +/- 2861</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Abdullah BASOGLU, Nuri BASPINAR, Alparslan COSKUN. NMR-based metabolomic evaluation in dairy cows with displaced abomasum. Turk J Vet Anim Sci (2014) 38(3):325-330</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 54 Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
          <pubmed_id>23394630</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>262-322</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>160</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>166-180</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>226-244</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>356+/-34</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>408+/-73</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>270+/-62</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11.27 +/- 3.98</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2 - 11</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5 - 29</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20487.203</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20487.203</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20487.203</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20487.203</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20487.203</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20487.203</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20487.203</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16.7 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.92 +/- 1.59</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk  from markets</comment>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.55 +/- 2.14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>111.25 +/- 11.56</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>115.1 +/- 15.63</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>268.81 +/- 19.22</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>71-288</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>550</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>76.65 +/- 5.44</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1.95+/-0.27</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 14 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>2.73+/-0.49</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 21 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>0.71+/-0.08</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 3 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>1.10+/-0.15</concentration_value>
      <concentration_units>umol/g tissue</concentration_units>
      <comment>Detected by NMR in beef muscle (longissimus dorsi) matured for 7 days.</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>57-83</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kodani Y, Miyakawa T, Komatsu T, Tanokura M: NMR-based metabolomics for simultaneously evaluating multiple determinants of primary beef quality in Japanese Black cattle. Sci Rep. 2017 May 2;7(1):1297. doi: 10.1038/s41598-017-01272-8.</reference_text>
          <pubmed_id>28465593</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>332-876</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2.27</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Bhatia SK, Pradhan K, Singh R: Microbial transaminase activities and their relationship with bovine rumen metabolites. J Dairy Sci. 1979 Mar;62(3):441-6. doi: 10.3168/jds.S0022-0302(79)83264-6.</reference_text>
          <pubmed_id>447894</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>133.8 +/- 49.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>71-593</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>132</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>188.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>247.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>133.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>55-194</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in male Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hanne Christine Bertram, Niels Bastian Kristensen, Mogens Vestergaard, SÃ¸ren Krogh Jensen, Jakob Sehested, Niels Christian Nielsen, Anders Malmendal. Metabolic characterization of rumen epithelial tissue from dairy calves fed different starter diets using 1H NMR spectroscopy. Livestock Science (2008) 120:127-134   doi: 10.1016/j.livsci.2008.05.001</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>139 +/- 34</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>199 +/- 60</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>248 +/- 55</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>144 +/- 72</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>143 +/- 52</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR, GC-MS and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>109</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>166</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>173</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>109</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>848+/-295</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>278+/-49</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>50</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Sexton TJ, Amann RP, Flipse RJ: Free amino acids and protein in rete testis fluid, vas deferens plasma, accessory sex gland fluid, and seminal plasma of the conscious bull. J Dairy Sci. 1971 Mar;54(3):412-6. doi: 10.3168/jds.s0022-0302(71)85854-x.</reference_text>
          <pubmed_id>5096119</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>197+/-37</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB004905</foodb_id>
  <chemspider_id>6050</chemspider_id>
  <pubchem_compound_id>6287</pubchem_compound_id>
  <kegg_id>C00183</kegg_id>
  <pdbe_id/>
  <chebi_id>16414</chebi_id>
  <drugbank_id>DB00161</drugbank_id>
  <meta_cyc_id>VAL</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001398</knapsack_id>
  <bigg_id>34167</bigg_id>
  <wikipedia_id>L-valine</wikipedia_id>
  <metlin_id>5842</metlin_id>
  <synthesis_reference>Kinoshita, Shukuo; Udaka, Shigezo.  L-Valine production by fermentation.    (1962),     2 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00226</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>A4IFQ7</uniprot_id>
      <gene_name>BCAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00227</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase, mitochondrial</name>
      <uniprot_id>Q5EA40</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00228</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>Q0V8J6</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00229</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>Q5E9U7</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:03 UTC</creation_date>
  <update_date>2020-04-14 22:48:30 UTC</update_date>
  <accession>BMDB0000884</accession>
  <secondary_accessions>
    <accession>BMDB00884</accession>
  </secondary_accessions>
  <name>Ribothymidine</name>
  <description>Ribothymidine, also known as 5-methyl-uridine or thymine riboside, belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. Ribothymidine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Ribothymidine exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>1-(beta-D-Ribofuranosyl)thymine</synonym>
    <synonym>Ribosylthymidine</synonym>
    <synonym>t</synonym>
    <synonym>Thymine riboside</synonym>
    <synonym>1-(b-D-Ribofuranosyl)thymine</synonym>
    <synonym>1-(Β-D-ribofuranosyl)thymine</synonym>
    <synonym>1-b-D-Ribofuranosylthymine</synonym>
    <synonym>1-beta-delta-Ribofuranosylthymine</synonym>
    <synonym>5-Methyl-1-beta-D-ribofuranosyl-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>5-Methyl-1-beta-delta-ribofuranosyl-2,4(1H,3H)-pyrimidinedione</synonym>
    <synonym>5-Methyl-uridine</synonym>
    <synonym>5-Methyluridine</synonym>
    <synonym>b-D-Ribofuranoside thymine-1</synonym>
    <synonym>beta-D-Ribofuranoside</synonym>
    <synonym>beta-delta-Ribofuranoside</synonym>
    <synonym>beta-delta-Ribofuranoside thymine-1</synonym>
    <synonym>Ribosylthymine</synonym>
    <synonym>Thymine ribofuranoside</synonym>
    <synonym>Thymine ribonucleoside</synonym>
    <synonym>Thymine-1 beta-D-ribofuranosylthymine</synonym>
    <synonym>Thymine-1 beta-delta-ribofuranosylthymine</synonym>
  </synonyms>
  <chemical_formula>C10H14N2O6</chemical_formula>
  <average_molecular_weight>258.228</average_molecular_weight>
  <monisotopic_moleculate_weight>258.08518619</monisotopic_moleculate_weight>
  <iupac_name>1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione</iupac_name>
  <traditional_iupac>thymidin</traditional_iupac>
  <cas_registry_number>1463-10-1</cas_registry_number>
  <smiles>CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)NC1=O</smiles>
  <inchi>InChI=1S/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7-,9-/m1/s1</inchi>
  <inchikey>DWRXFEITVBNRMK-JXOAFFINSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleosides</class>
    <sub_class/>
    <direct_parent>Pyrimidine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine nucleoside</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>methyluridine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>183 - 187 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>258.228</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>258.08518619</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H14N2O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7-,9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DWRXFEITVBNRMK-JXOAFFINSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>119.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>56.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338886</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022298</foodb_id>
  <chemspider_id>393058</chemspider_id>
  <pubchem_compound_id>445408</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id>45996</chebi_id>
  <drugbank_id/>
  <meta_cyc_id>CPD-15123</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>5-methyluridine</wikipedia_id>
  <metlin_id>5843</metlin_id>
  <synthesis_reference>Maruyama, Shogo; Kumon, Satoru.  5-Methyluridine manufacture with microorganism.    Jpn. Kokai Tokkyo Koho  (1996),     6 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:04 UTC</creation_date>
  <update_date>2020-03-20 18:31:28 UTC</update_date>
  <accession>BMDB0000885</accession>
  <secondary_accessions>
    <accession>BMDB0062599</accession>
    <accession>BMDB00885</accession>
    <accession>BMDB62599</accession>
  </secondary_accessions>
  <name>CE(16:0)</name>
  <description>Ce(16:0), also known as CE or hexadecanoate, belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety. Thus, ce(16:0) is considered to be a sterol lipid molecule. Ce(16:0) exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Ce(16:0) exists in all eukaryotes, ranging from yeast to humans. Ce(16:0) has been linked to the inborn metabolic disorders including hypercholesterolemia.</description>
  <synonyms>
    <synonym>Cholesterol Ester(16:0)</synonym>
    <synonym>1-Palmitoyl-cholesterol</synonym>
    <synonym>Cholesteryl 1-hexadecanoic acid</synonym>
    <synonym>Cholesterol Ester(16:0/0:0)</synonym>
    <synonym>16:0 Cholesterol ester</synonym>
    <synonym>Cholesterol 1-hexadecanoate</synonym>
    <synonym>CE(16:0)</synonym>
    <synonym>CE(16:0/0:0)</synonym>
    <synonym>Cholesterol 1-hexadecanoic acid</synonym>
    <synonym>Cholesterol 1-palmitoic acid</synonym>
    <synonym>Cholesterol 1-palmitoate</synonym>
    <synonym>Cholesteryl 1-palmitoate</synonym>
    <synonym>Cholesteryl 1-hexadecanoate</synonym>
    <synonym>1-Hexadecanoyl-cholesterol</synonym>
    <synonym>Cholesteryl 1-palmitoic acid</synonym>
    <synonym>(3beta)-Cholest-5-en-3-ol hexadecanoate</synonym>
    <synonym>CE</synonym>
    <synonym>Cholesterol palmitate</synonym>
    <synonym>Cholesteryl hexadecanoate</synonym>
    <synonym>Hexadecanoic acid, cholesteryl ester</synonym>
    <synonym>Palmitic acid cholesteryl ester</synonym>
    <synonym>(3b)-Cholest-5-en-3-ol hexadecanoate</synonym>
    <synonym>(3b)-Cholest-5-en-3-ol hexadecanoic acid</synonym>
    <synonym>(3beta)-Cholest-5-en-3-ol hexadecanoic acid</synonym>
    <synonym>(3β)-cholest-5-en-3-ol hexadecanoate</synonym>
    <synonym>(3β)-cholest-5-en-3-ol hexadecanoic acid</synonym>
    <synonym>Cholesterol palmitic acid</synonym>
    <synonym>Cholesteryl hexadecanoic acid</synonym>
    <synonym>Hexadecanoate, cholesteryl ester</synonym>
    <synonym>Palmitate cholesteryl ester</synonym>
    <synonym>Cholest-5-en-3-yl palmitate</synonym>
    <synonym>Cholest-5-ene-3-beta-yl palmitate</synonym>
    <synonym>Cholesteryl palmitate</synonym>
    <synonym>Cholesteryl palmitic acid</synonym>
    <synonym>Hexadecanoate</synonym>
    <synonym>Hexadecanoic acid</synonym>
    <synonym>Hexadecanoic acid cholesteryl ester</synonym>
    <synonym>5-Cholesten-3beta-ol stearate</synonym>
    <synonym>5-Cholesten-3β-ol stearate</synonym>
    <synonym>Cholest-5-en-3beta-ol stearate</synonym>
    <synonym>Cholest-5-en-3β-ol stearate</synonym>
    <synonym>Cholesterol hexadecanoate</synonym>
  </synonyms>
  <chemical_formula>C43H76O2</chemical_formula>
  <average_molecular_weight>625.0623</average_molecular_weight>
  <monisotopic_moleculate_weight>624.584531676</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl hexadecanoate</iupac_name>
  <traditional_iupac>(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl hexadecanoate</traditional_iupac>
  <cas_registry_number>601-34-3</cas_registry_number>
  <smiles>[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@]([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCCCCCCCCCC</smiles>
  <inchi>InChI=1S/C43H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h24,33-34,36-40H,7-23,25-32H2,1-6H3/t34-,36+,37+,38-,39+,40+,42+,43-/m1/s1</inchi>
  <inchikey>BBJQPKLGPMQWBU-JADYGXMDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Steroid esters</sub_class>
    <direct_parent>Cholesteryl esters</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Cholesterols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cholestane-skeleton</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesteryl ester</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Cholesteryl esters</external_descriptor>
      <external_descriptor>Steryl esters</external_descriptor>
      <external_descriptor>cholesterol ester</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>75 - 77 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>10.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>14.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl hexadecanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>625.0623</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>624.584531676</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@]([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCCCCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C43H76O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C43H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h24,33-34,36-40H,7-23,25-32H2,1-6H3/t34-,36+,37+,38-,39+,40+,42+,43-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BBJQPKLGPMQWBU-JADYGXMDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>26.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>194.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>85.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182984</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.5 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.6 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.7 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.4 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>107.9 +/- 69.77</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>107 +/- 70</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by FAMEs/GC–MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022299</foodb_id>
  <chemspider_id>215725</chemspider_id>
  <pubchem_compound_id>246520</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id>C11251</kegg_id>
  <chebi_id>3663</chebi_id>
  <drugbank_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5844</metlin_id>
  <synthesis_reference>Mahadevan, V.; Lundberg, W. O.  Preparation of cholesteryl esters of long-chain fatty acids.    Journal of the American Oil Chemists' Society  (1960),  37  685.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:05 UTC</creation_date>
  <update_date>2020-04-16 20:37:00 UTC</update_date>
  <accession>BMDB0000887</accession>
  <secondary_accessions>
    <accession>BMDB00887</accession>
  </secondary_accessions>
  <name>Hemin</name>
  <description/>
  <synonyms>
    <synonym>Chloro(protoporphyrinato)iron(III)</synonym>
    <synonym>Chloro[3,7,12,17-tetramethyl-8,13-divinylporphyrin-2,18-dipropanoato(2-)]iron(III)</synonym>
    <synonym>Haemin</synonym>
    <synonym>Hemine</synonym>
    <synonym>Protohemin</synonym>
    <synonym>Normosang</synonym>
    <synonym>Chloro(protoporphyrinato)iron</synonym>
    <synonym>Chloroprotoferriheme</synonym>
    <synonym>Chloroprotohemin</synonym>
    <synonym>Chloroprotoporphyrin IX iron</synonym>
    <synonym>Ferric hemin</synonym>
    <synonym>Ferriheme</synonym>
    <synonym>Ferriporphyrin chloride</synonym>
    <synonym>Ferriprotoporphyrin</synonym>
    <synonym>Ferriprotoporphyrin IX</synonym>
    <synonym>Ferriprotoporphyrin IX chloride</synonym>
    <synonym>Hamin</synonym>
    <synonym>Hemin chloride</synonym>
    <synonym>Hemin IX</synonym>
    <synonym>Hemin porcine</synonym>
    <synonym>Hemin ultra-pure</synonym>
    <synonym>Iron(III) protoporphyrin chloride</synonym>
    <synonym>Panhematin</synonym>
    <synonym>Protoferriheme</synonym>
    <synonym>Protohemin chloride</synonym>
    <synonym>Protohemin IX</synonym>
    <synonym>Teichmann'S crystals</synonym>
  </synonyms>
  <chemical_formula>C34H32ClFeN4O4</chemical_formula>
  <average_molecular_weight>651.94</average_molecular_weight>
  <monisotopic_moleculate_weight>651.146150372</monisotopic_moleculate_weight>
  <iupac_name>3-[5-(2-carboxyethyl)-1-chloro-14,19-diethenyl-4,10,15,20-tetramethyl-2lambda4,22,23lambda4,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2(6),3(24),4,7,9,11,13(23),14,16,18,20-undecaen-9-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[5-(2-carboxyethyl)-1-chloro-14,19-diethenyl-4,10,15,20-tetramethyl-2lambda4,22,23lambda4,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2(6),3(24),4,7,9,11,13(23),14,16,18,20-undecaen-9-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>16009-13-5</cas_registry_number>
  <smiles>CC1=C(CCC(O)=O)C2=CC3=[N]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N]7[Fe]4(Cl)(N2C1=C8)N56)C(C)=C3CCC(O)=O</smiles>
  <inchi>InChI=1S/C34H34N4O4.ClH.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);1H;/q;;+3/p-3/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;;</inchi>
  <inchikey>BTIJJDXEELBZFS-HXFTUNQESA-K</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as metalloporphyrins. These are polycyclic compounds containing a porphyrin moiety and a metal atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Metallotetrapyrroles</sub_class>
    <direct_parent>Metalloporphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[5-(2-carboxyethyl)-1-chloro-14,19-diethenyl-4,10,15,20-tetramethyl-2lambda4,22,23lambda4,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2(6),3(24),4,7,9,11,13(23),14,16,18,20-undecaen-9-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>651.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>651.146150372</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCC(O)=O)C2=CC3=[N]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N]7[Fe]4(Cl)(N2C1=C8)N56)C(C)=C3CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C34H32ClFeN4O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C34H34N4O4.ClH.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);1H;/q;;+3/p-3/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;;</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BTIJJDXEELBZFS-HXFTUNQESA-K</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>121.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>182.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>71.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333675</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB005746</foodb_id>
  <chemspider_id>401223</chemspider_id>
  <pubchem_compound_id/>
  <kegg_id>C06767</kegg_id>
  <pdbe_id/>
  <chebi_id>50385</chebi_id>
  <drugbank_id>DB03404</drugbank_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Hemin</wikipedia_id>
  <metlin_id>5845</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:06 UTC</creation_date>
  <update_date>2020-03-13 16:24:32 UTC</update_date>
  <accession>BMDB0000888</accession>
  <secondary_accessions>
    <accession>BMDB00888</accession>
  </secondary_accessions>
  <name>Undecanedioic acid</name>
  <description/>
  <synonyms>
    <synonym>1,11-Undecanedioic acid</synonym>
    <synonym>1,9-Nonanedicarboxylic acid</synonym>
    <synonym>Hendecanedioic acid</synonym>
    <synonym>Undecanedionic acid</synonym>
    <synonym>1,11-Undecanedioate</synonym>
    <synonym>1,9-Nonanedicarboxylate</synonym>
    <synonym>Hendecanedioate</synonym>
    <synonym>Undecanedionate</synonym>
    <synonym>Undecanedioate</synonym>
  </synonyms>
  <chemical_formula>C11H20O4</chemical_formula>
  <average_molecular_weight>216.2741</average_molecular_weight>
  <monisotopic_moleculate_weight>216.136159128</monisotopic_moleculate_weight>
  <iupac_name>undecanedioic acid</iupac_name>
  <traditional_iupac>undecanedioic acid</traditional_iupac>
  <cas_registry_number>1852-04-6</cas_registry_number>
  <smiles>OC(=O)CCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C11H20O4/c12-10(13)8-6-4-2-1-3-5-7-9-11(14)15/h1-9H2,(H,12,13)(H,14,15)</inchi>
  <inchikey>LWBHHRRTOZQPDM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>alpha,omega-dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>108 - 110 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>5.1 mg/mL</value>
      <source>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>undecanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>216.2741</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>216.136159128</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H20O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H20O4/c12-10(13)8-6-4-2-1-3-5-7-9-11(14)15/h1-9H2,(H,12,13)(H,14,15)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LWBHHRRTOZQPDM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>55.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340116</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022300</foodb_id>
  <chemspider_id>15037</chemspider_id>
  <pubchem_compound_id>15816</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id/>
  <chebi_id>73713</chebi_id>
  <drugbank_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5846</metlin_id>
  <synthesis_reference>Durham, Lois J.; McLeod, Donald J.; Cason, James.  Hendecanedioic acid.    Organic Syntheses  (1958),  38  34-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:07 UTC</creation_date>
  <update_date>2020-04-15 22:14:38 UTC</update_date>
  <accession>BMDB0000889</accession>
  <secondary_accessions>
    <accession>BMDB00889</accession>
  </secondary_accessions>
  <name>Tauroursocholic acid</name>
  <description/>
  <synonyms>
    <synonym>Tauroursocholate</synonym>
    <synonym>Ursocholyltaurine</synonym>
    <synonym>(4R)-N-(2-Sulfoethyl)-4-[(2S,5R,7S,9S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanimidate</synonym>
    <synonym>(4R)-N-(2-Sulphoethyl)-4-[(2S,5R,7S,9S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanimidate</synonym>
    <synonym>(4R)-N-(2-Sulphoethyl)-4-[(2S,5R,7S,9S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanimidic acid</synonym>
  </synonyms>
  <chemical_formula>C26H45NO7S</chemical_formula>
  <average_molecular_weight>515.703</average_molecular_weight>
  <monisotopic_moleculate_weight>515.291673489</monisotopic_moleculate_weight>
  <iupac_name>2-[(4R)-4-[(2S,5R,7S,9S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid</iupac_name>
  <traditional_iupac>2-[(4R)-4-[(2S,5R,7S,9S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethanesulfonic acid</traditional_iupac>
  <cas_registry_number>86386-60-9</cas_registry_number>
  <smiles>[H][C@@]12C[C@H](O)CC[C@]1(C)C1C[C@H](O)[C@]3(C)[C@H](CCC3C1[C@@H](O)C2)[C@H](C)CCC(=O)NCCS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19?,20?,21+,22+,24?,25+,26-/m1/s1</inchi>
  <inchikey>WBWWGRHZICKQGZ-TZLUGCQQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Taurinated bile acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Alkanesulfonic acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonic acids</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfonyls</alternative_parent>
      <alternative_parent>Trihydroxy bile acids, alcohols and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkanesulfonic acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfonyl</substituent>
      <substituent>Taurinated bile acid</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4R)-4-[(2S,5R,7S,9S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>515.703</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>515.291673489</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@H](O)CC[C@]1(C)C1C[C@H](O)[C@]3(C)[C@H](CCC3C1[C@@H](O)C2)[C@H](C)CCC(=O)NCCS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H45NO7S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16+,17-,18-,19?,20?,21+,22+,24?,25+,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WBWWGRHZICKQGZ-TZLUGCQQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>144.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>132.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>57.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338682</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022301</foodb_id>
  <chemspider_id>13628160</chemspider_id>
  <pubchem_compound_id>21252258</pubchem_compound_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5847</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Dayal, B.; Rapole, K. R.; Salen, G.; Shefer, S.; Tint, G. S.; Wilson, S. R.  Microwave-induced rapid synthesis of bile acid conjugates.    Synlett  (1995),   (8),  861-2.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:08 UTC</creation_date>
  <update_date>2020-03-13 16:24:33 UTC</update_date>
  <accession>BMDB0000890</accession>
  <secondary_accessions>
    <accession>BMDB00890</accession>
  </secondary_accessions>
  <name>Uroporphyrin IV</name>
  <description/>
  <synonyms>
    <synonym>3,8,13,17-Tetrakis(carboxymethyl)-2,7,12,18-porphinetetrapropionate</synonym>
    <synonym>3,8,13,17-Tetrakis(carboxymethyl)-2,7,12,18-porphinetetrapropionic acid</synonym>
    <synonym>3-[9,15,20-Tris(2-carboxyethyl)-5,10,14,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C40H38N4O16</chemical_formula>
  <average_molecular_weight>830.7469</average_molecular_weight>
  <monisotopic_moleculate_weight>830.228281188</monisotopic_moleculate_weight>
  <iupac_name>3-[10,15,19-tris(2-carboxyethyl)-5,9,14,20-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[10,15,19-tris(2-carboxyethyl)-5,9,14,20-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>613-02-5</cas_registry_number>
  <smiles>OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CC(O)=O)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CC(O)=O)=C4CCC(O)=O)/C(CCC(O)=O)=C3CC(O)=O</smiles>
  <inchi>InChI=1S/C40H38N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-27-19(3-7-35(49)50)23(11-39(57)58)31(43-27)16-32-24(12-40(59)60)20(4-8-36(51)52)28(44-32)15-30-22(10-38(55)56)18(2-6-34(47)48)26(42-30)13-25(17)41-29/h13-16,41,44H,1-12H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-</inchi>
  <inchikey>AJLMJIKELQBUTG-UJJXFSCMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>300 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[10,15,19-tris(2-carboxyethyl)-5,9,14,20-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>830.7469</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>830.228281188</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CC(O)=O)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CC(O)=O)=C4CCC(O)=O)/C(CCC(O)=O)=C3CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C40H38N4O16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C40H38N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-27-19(3-7-35(49)50)23(11-39(57)58)31(43-27)16-32-24(12-40(59)60)20(4-8-36(51)52)28(44-32)15-30-22(10-38(55)56)18(2-6-34(47)48)26(42-30)13-25(17)41-29/h13-16,41,44H,1-12H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AJLMJIKELQBUTG-UJJXFSCMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>355.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>201.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>84.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362937</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022302</foodb_id>
  <chemspider_id>13628161</chemspider_id>
  <pubchem_compound_id/>
  <kegg_id/>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5848</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>MacDonald, S. F.; Michl, K. H.  The synthesis of the uroporphyrins II and IV.    Canadian Journal of Chemistry  (1956),  34  1768-81.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:10 UTC</creation_date>
  <update_date>2020-04-16 20:39:22 UTC</update_date>
  <accession>BMDB0000892</accession>
  <secondary_accessions>
    <accession>BMDB00892</accession>
  </secondary_accessions>
  <name>Valeric acid</name>
  <description>Pentanoic acid, also known as valerate or N-pentanoate, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Pentanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Pentanoic acid exists in all living species, ranging from bacteria to humans. Pentanoic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Butanecarboxylic acid</synonym>
    <synonym>CH3-[CH2]3-COOH</synonym>
    <synonym>N-BuCOOH</synonym>
    <synonym>N-Pentanoate</synonym>
    <synonym>N-Pentanoic acid</synonym>
    <synonym>N-Valeric acid</synonym>
    <synonym>Pentanoate</synonym>
    <synonym>Pentanoic acid</synonym>
    <synonym>Pentoic acid</synonym>
    <synonym>Propylacetic acid</synonym>
    <synonym>Valerate</synonym>
    <synonym>Valerianic acid</synonym>
    <synonym>Valeriansaeure</synonym>
    <synonym>Valeric acid, normal</synonym>
    <synonym>1-Butanecarboxylate</synonym>
    <synonym>N-Valerate</synonym>
    <synonym>Pentoate</synonym>
    <synonym>Propylacetate</synonym>
    <synonym>Valerianate</synonym>
    <synonym>Valerate, normal</synonym>
    <synonym>1-Pentanoate</synonym>
    <synonym>1-Pentanoic acid</synonym>
    <synonym>Butanecarboxylate</synonym>
    <synonym>Butanecarboxylic acid</synonym>
    <synonym>Kyselina valerova</synonym>
    <synonym>N-C4H9COOH</synonym>
    <synonym>Valeriansaure</synonym>
    <synonym>Valeric acid normal</synonym>
    <synonym>N-Pentanoic acid, ammonium salt</synonym>
    <synonym>N-Pentanoic acid, potassium salt</synonym>
    <synonym>N-Pentanoic acid, sodium salt</synonym>
    <synonym>N-Pentanoic acid, zinc salt</synonym>
    <synonym>N-Pentanoic acid, maganese (+2) salt</synonym>
    <synonym>N-Pentanoic acid, 11C-labeled</synonym>
    <synonym>Lithium pentanoate</synonym>
    <synonym>N-Pentanoic acid, 11C-labeled sodium salt</synonym>
    <synonym>Valeric acid</synonym>
  </synonyms>
  <chemical_formula>C5H10O2</chemical_formula>
  <average_molecular_weight>102.1317</average_molecular_weight>
  <monisotopic_moleculate_weight>102.068079564</monisotopic_moleculate_weight>
  <iupac_name>pentanoic acid</iupac_name>
  <traditional_iupac>N-valeric acid</traditional_iupac>
  <cas_registry_number>109-52-4</cas_registry_number>
  <smiles>CCCCC(O)=O</smiles>
  <inchi>InChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7)</inchi>
  <inchikey>NQPDZGIKBAWPEJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Straight chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Saturated fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>short-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-34 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>24.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.39</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>102.1317</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>102.068079564</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O2/c1-2-3-4-5(6)7/h2-4H2,1H3,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NQPDZGIKBAWPEJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>26.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4792</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438633</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.50 +/- 3.19</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.9 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.0 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.18 +/- 0.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.91 +/- 0.13</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.47 +/- 2.84</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.1 (0 - 0.4)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.44 +/- 2.61</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.2 (0.1 - 0.5)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.3 (0.1 - 0.6)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.5 (0.7 - 2.7)</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.5%</comment>
      <references>
        <reference>
          <reference_text>Harper, W. J., Gould, I. A. and Hankinson, C. L. 1961. Observations on the free volatile acids in milk. J. Dairy Sci. 44, 1764-1765</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2865.03 +/- 2943.19</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1500-5000</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>764-1768</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2932 +/- 433</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>4033 +/- 557</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>3000 +/- 807</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>3044 +/- 1092</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2030</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2510</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2700</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1410</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1450 +/- 330</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>O'Grady L, Doherty ML, Mulligan FJ: Subacute ruminal acidosis (SARA) in grazing Irish dairy cows. Vet J. 2008 Apr;176(1):44-9. doi: 10.1016/j.tvjl.2007.12.017. Epub 2008 Mar 6.</reference_text>
          <pubmed_id>18328751</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2739+/-677</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB003230</foodb_id>
  <chemspider_id>7701</chemspider_id>
  <pubchem_compound_id>7991</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id>C00803</kegg_id>
  <chebi_id>17418</chebi_id>
  <drugbank_id>DB02406</drugbank_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001208</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Valeric acid</wikipedia_id>
  <metlin_id>110</metlin_id>
  <synthesis_reference>Ruiz, Maria Olga; Cabezas, Jose Luis; Escudero, Isabel; Coca, Jose.  Valeric acid extraction with tri-n-butyl phosphate impregnated in a macroporous resin: II. Studies in fixed bed columns.    Journal of Chemical Technology and Biotechnology  (2006),  81(3),  275-281.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:11 UTC</creation_date>
  <update_date>2020-04-14 22:48:31 UTC</update_date>
  <accession>BMDB0000893</accession>
  <secondary_accessions>
    <accession>BMDB00893</accession>
  </secondary_accessions>
  <name>Suberic acid</name>
  <description/>
  <synonyms>
    <synonym>1,6-Dicarboxyhexane</synonym>
    <synonym>1,6-Hexanedicarboxylic acid</synonym>
    <synonym>1,8-Octanedioic acid</synonym>
    <synonym>Cork acid</synonym>
    <synonym>Hexamethylenedicarboxylic acid</synonym>
    <synonym>Korksaeure</synonym>
    <synonym>Octane-1,8-dioic acid</synonym>
    <synonym>Octanedioic acid</synonym>
    <synonym>Oktandisaeure</synonym>
    <synonym>Suberinsaeure</synonym>
    <synonym>1,6-Hexanedicarboxylate</synonym>
    <synonym>1,8-Octanedioate</synonym>
    <synonym>Hexamethylenedicarboxylate</synonym>
    <synonym>Octane-1,8-dioate</synonym>
    <synonym>Octanedioate</synonym>
    <synonym>Suberate</synonym>
    <synonym>Suberic acid, manganese (+2) (1:1) salt</synonym>
    <synonym>Suberic acid, disodium salt</synonym>
    <synonym>Suberic acid, cadmium (1:1) salt</synonym>
    <synonym>Suberic acid, monosodium salt</synonym>
    <synonym>Suberic acid, dipotassium salt</synonym>
    <synonym>Suberic acid</synonym>
  </synonyms>
  <chemical_formula>C8H14O4</chemical_formula>
  <average_molecular_weight>174.1944</average_molecular_weight>
  <monisotopic_moleculate_weight>174.089208936</monisotopic_moleculate_weight>
  <iupac_name>octanedioic acid</iupac_name>
  <traditional_iupac>suberic acid</traditional_iupac>
  <cas_registry_number>505-48-6</cas_registry_number>
  <smiles>OC(=O)CCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C8H14O4/c9-7(10)5-3-1-2-4-6-8(11)12/h1-6H2,(H,9,10)(H,11,12)</inchi>
  <inchikey>TYFQFVWCELRYAO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>alpha,omega-dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>144 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>11.9 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>octanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>174.1944</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>174.089208936</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H14O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H14O4/c9-7(10)5-3-1-2-4-6-8(11)12/h1-6H2,(H,9,10)(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>TYFQFVWCELRYAO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4796</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438427</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB003340</foodb_id>
  <chemspider_id>10025</chemspider_id>
  <pubchem_compound_id>10457</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id>C08278</kegg_id>
  <chebi_id>9300</chebi_id>
  <drugbank_id/>
  <meta_cyc_id>CPD0-1264</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001204</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Suberic_acid</wikipedia_id>
  <metlin_id>4243</metlin_id>
  <synthesis_reference>Ayorinde, Folahan O.; Osman, Gamal; Shepard, Robert L.; Powers, Fiona T.  Synthesis of azelaic acid and suberic acid from Vernonia galamensis oil.    JAOCS, J. Am. Oil Chem. Soc.  (1988),  65(11),  1774-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:12 UTC</creation_date>
  <update_date>2020-03-13 16:24:34 UTC</update_date>
  <accession>BMDB0000894</accession>
  <secondary_accessions>
    <accession>BMDB00894</accession>
  </secondary_accessions>
  <name>Vinylacetylglycine</name>
  <description/>
  <synonyms>
    <synonym>2-(But-3-enamido)acetic acid</synonym>
    <synonym>2-(But-3-enamido)acetate</synonym>
  </synonyms>
  <chemical_formula>C6H9NO3</chemical_formula>
  <average_molecular_weight>143.1406</average_molecular_weight>
  <monisotopic_moleculate_weight>143.058243159</monisotopic_moleculate_weight>
  <iupac_name>2-(but-3-enamido)acetic acid</iupac_name>
  <traditional_iupac>but-3-enamidoacetic acid</traditional_iupac>
  <cas_registry_number>73122-61-9</cas_registry_number>
  <smiles>OC(=O)CNC(=O)CC=C</smiles>
  <inchi>InChI=1S/C6H9NO3/c1-2-3-5(8)7-4-6(9)10/h2H,1,3-4H2,(H,7,8)(H,9,10)</inchi>
  <inchikey>UKISAGFGRDHYFO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylglycine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(but-3-enamido)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>143.1406</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>143.058243159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CNC(=O)CC=C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H9NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H9NO3/c1-2-3-5(8)7-4-6(9)10/h2H,1,3-4H2,(H,7,8)(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UKISAGFGRDHYFO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356961</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <pubchem_compound_id>53477718</pubchem_compound_id>
  <chemspider_id>27976741</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB022303</foodb_id>
  <pdbe_id/>
  <chebi_id>74435</chebi_id>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>5851</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:13 UTC</creation_date>
  <update_date>2020-04-16 20:40:02 UTC</update_date>
  <accession>BMDB0000895</accession>
  <secondary_accessions>
    <accession>BMDB00895</accession>
  </secondary_accessions>
  <name>Acetylcholine</name>
  <description/>
  <synonyms>
    <synonym>ACh</synonym>
    <synonym>Azetylcholin</synonym>
    <synonym>Choline acetate</synonym>
    <synonym>O-Acetylcholine</synonym>
    <synonym>Choline acetic acid</synonym>
    <synonym>Acetylcholine iodide</synonym>
    <synonym>Acetylcholine perchlorate</synonym>
    <synonym>Acetylcholine sulfate (1:1)</synonym>
    <synonym>Bromoacetylcholine</synonym>
    <synonym>Cusi, acetilcolina</synonym>
    <synonym>Iodide, acetylcholine</synonym>
    <synonym>2-(Acetyloxy)-N,N,N-trimethylethanaminium</synonym>
    <synonym>Acetilcolina cusi</synonym>
    <synonym>Acetylcholine fluoride</synonym>
    <synonym>Acetylcholine L tartrate</synonym>
    <synonym>Acetylcholine picrate</synonym>
    <synonym>Chloroacetylcholine</synonym>
    <synonym>Miochol</synonym>
    <synonym>Perchlorate, acetylcholine</synonym>
    <synonym>Acetylcholine L-tartrate</synonym>
    <synonym>Acetylcholine picrate (1:1)</synonym>
    <synonym>Hydroxide, acetylcholine</synonym>
    <synonym>Acetylcholine bromide</synonym>
    <synonym>Acetylcholine chloride</synonym>
    <synonym>Acetylcholine hydroxide</synonym>
    <synonym>Bromide, acetylcholine</synonym>
    <synonym>Fluoride, acetylcholine</synonym>
    <synonym>L-Tartrate, acetylcholine</synonym>
    <synonym>Acetyl choline ion</synonym>
    <synonym>Acetylcholine cation</synonym>
    <synonym>Acetylcholinium: acetyl-choline</synonym>
    <synonym>Choline acetate (ester)</synonym>
    <synonym>Bournonville brand OF acetylcholine chloride</synonym>
    <synonym>Iolab brand OF acetylcholine chloride</synonym>
    <synonym>Alcon brand OF acetylcholine chloride</synonym>
    <synonym>Ciba vision brand OF acetylcholine chloride</synonym>
    <synonym>Acetylcholine</synonym>
  </synonyms>
  <chemical_formula>C7H16NO2</chemical_formula>
  <average_molecular_weight>146.2074</average_molecular_weight>
  <monisotopic_moleculate_weight>146.118103761</monisotopic_moleculate_weight>
  <iupac_name>[2-(acetyloxy)ethyl]trimethylazanium</iupac_name>
  <traditional_iupac>acetylcholine</traditional_iupac>
  <cas_registry_number>51-84-3</cas_registry_number>
  <smiles>CC(=O)OCC[N+](C)(C)C</smiles>
  <inchi>InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1</inchi>
  <inchikey>OIPILFWXSMYKGL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Quaternary ammonium salts</sub_class>
    <direct_parent>Acyl cholines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl choline</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Acetylcholine</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>acetate ester</external_descriptor>
      <external_descriptor>acylcholine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>148 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[2-(acetyloxy)ethyl]trimethylazanium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>146.2074</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>146.118103761</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)OCC[N+](C)(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H16NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OIPILFWXSMYKGL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>26.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Gastric Acid Production</name>
      <smpdb_id>SMP0119381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451954</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01996</kegg_id>
  <drugbank_id>DB03128</drugbank_id>
  <foodb_id>FDB012191</foodb_id>
  <chemspider_id>182</chemspider_id>
  <pubchem_compound_id>187</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15355</chebi_id>
  <meta_cyc_id>ACETYLCHOLINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>38868</bigg_id>
  <wikipedia_id>Acetylcholine</wikipedia_id>
  <metlin_id>57</metlin_id>
  <synthesis_reference>Szutowicz, Andrzej.  Acetylcholine synthesis in synaptosomes.    Postepy Biochemii  (1979),  25(1),  59-84.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00529</protein_accession>
      <name>Acetylcholinesterase</name>
      <uniprot_id>P23795</uniprot_id>
      <gene_name>ACHE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:14 UTC</creation_date>
  <update_date>2020-04-15 22:07:08 UTC</update_date>
  <accession>BMDB0000896</accession>
  <secondary_accessions>
    <accession>BMDB00896</accession>
  </secondary_accessions>
  <name>Taurodeoxycholic acid</name>
  <description/>
  <synonyms>
    <synonym>Taurodeoxycholate</synonym>
    <synonym>Acid, taurodeoxycholic</synonym>
    <synonym>Deoxycholate, taurine</synonym>
    <synonym>Sodium taurodeoxycholate</synonym>
    <synonym>Taurine deoxycholate</synonym>
    <synonym>Deoxycholyltaurine</synonym>
    <synonym>Taurodeoxycholate, sodium</synonym>
    <synonym>Deoxytaurocholate</synonym>
    <synonym>Deoxytaurocholic acid</synonym>
    <synonym>N-(3a,12a-Dihydroxy-5b-cholan-24-oyl)-taurine</synonym>
    <synonym>Sodium taurodeoxylate</synonym>
    <synonym>Taurodeoxycholic acid sodium salt</synonym>
    <synonym>Taurodeoxycholic acid sodium salt hydrate</synonym>
    <synonym>Taurodesoxycholate</synonym>
    <synonym>Taurodesoxycholic acid</synonym>
    <synonym>Tudcabil</synonym>
  </synonyms>
  <chemical_formula>C26H45NO6S</chemical_formula>
  <average_molecular_weight>499.704</average_molecular_weight>
  <monisotopic_moleculate_weight>499.296758867</monisotopic_moleculate_weight>
  <iupac_name>2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid</iupac_name>
  <traditional_iupac>2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid</traditional_iupac>
  <cas_registry_number>516-50-7</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C26H45NO6S/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-/m1/s1</inchi>
  <inchikey>AWDRATDZQPNJFN-VAYUFCLWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Taurinated bile acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Alkanesulfonic acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Dihydroxy bile acids, alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonic acids</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfonyls</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkanesulfonic acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfonyl</substituent>
      <substituent>Taurinated bile acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Taurine conjugates</external_descriptor>
      <external_descriptor>bile acid taurine conjugate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>204 - 208 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>41 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-0.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>499.704</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>499.296758867</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H45NO6S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H45NO6S/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AWDRATDZQPNJFN-VAYUFCLWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>123.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>130.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>56.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438666</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05463</kegg_id>
  <pubchem_compound_id>2733768</pubchem_compound_id>
  <chemspider_id>2015539</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB022304</foodb_id>
  <pdbe_id/>
  <chebi_id>9410</chebi_id>
  <meta_cyc_id/>
  <wikipedia_id>Taurodeoxycholic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>5853</metlin_id>
  <synthesis_reference>Parenti, Massimo.  Preparation of tauroursodesoxycholic acid dihydrate.    Eur. Pat. Appl.  (1990),     3 pp.  CODEN: EPXXDW  EP  400695  A2  19901205  CAN 114:82269  AN 1991:82269</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:15 UTC</creation_date>
  <update_date>2020-04-15 22:37:15 UTC</update_date>
  <accession>BMDB0000897</accession>
  <secondary_accessions>
    <accession>BMDB00897</accession>
  </secondary_accessions>
  <name>7-Methylguanine</name>
  <description/>
  <synonyms>
    <synonym>2-Amino-1,7-dihydro-7-methyl-6H-purin-6-one</synonym>
    <synonym>2-Amino-7-methylhypoxanthine</synonym>
    <synonym>N(7)-Methylguanine</synonym>
    <synonym>2-Amino-1,7-dihydroxy-7-methyl-6H-purine-6-one</synonym>
    <synonym>2-Amino-6-hydroxy-7-methylpurine</synonym>
    <synonym>7-Methyl-guanine</synonym>
    <synonym>7-Methyl-guanine (8ci)</synonym>
    <synonym>N-Methylguanine</synonym>
    <synonym>N7-Methylguanine</synonym>
    <synonym>7-Methylguanine, 14C-labeled</synonym>
    <synonym>N2-Methylguanine</synonym>
    <synonym>N7-Me-g</synonym>
    <synonym>N(2)-Methylguanine</synonym>
    <synonym>7-Methylguanine</synonym>
  </synonyms>
  <chemical_formula>C6H7N5O</chemical_formula>
  <average_molecular_weight>165.1527</average_molecular_weight>
  <monisotopic_moleculate_weight>165.065059871</monisotopic_moleculate_weight>
  <iupac_name>2-amino-7-methyl-6,7-dihydro-3H-purin-6-one</iupac_name>
  <traditional_iupac>2-amino-7-methylhypoxanthine</traditional_iupac>
  <cas_registry_number>578-76-7</cas_registry_number>
  <smiles>CN1C=NC2=C1C(=O)N=C(N)N2</smiles>
  <inchi>InChI=1S/C6H7N5O/c1-11-2-8-4-3(11)5(12)10-6(7)9-4/h2H,1H3,(H3,7,9,10,12)</inchi>
  <inchikey>FZWGECJQACGGTI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Hypoxanthines</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>7-methylguanine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>370 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-7-methyl-6,7-dihydro-3H-purin-6-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>165.1527</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>165.065059871</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C=NC2=C1C(=O)N=C(N)N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H7N5O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H7N5O/c1-11-2-8-4-3(11)5(12)10-6(7)9-4/h2H,1H3,(H3,7,9,10,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FZWGECJQACGGTI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>85.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446520</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02242</kegg_id>
  <pubchem_compound_id>11361</pubchem_compound_id>
  <chemspider_id>10883</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB022305</foodb_id>
  <pdbe_id/>
  <chebi_id>28664</chebi_id>
  <meta_cyc_id>CPD0-2377</meta_cyc_id>
  <wikipedia_id>7-Methylguanine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Adams, Benjamin L.  De-D-ribosylation of 7-alkylpurine D-ribonucleosides by a reduction-displacement procedure.  Conversion of 7-methylguanosine into 7-methylguanine.    Nucleic Acid Chem.  (1978),  2  615-17.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:16 UTC</creation_date>
  <update_date>2020-04-16 17:50:51 UTC</update_date>
  <accession>BMDB0000898</accession>
  <secondary_accessions>
    <accession>BMDB00898</accession>
  </secondary_accessions>
  <name>1-Methylhistamine</name>
  <description>1-1-1-methylhistamine belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group. 1-1-1-methylhistamine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 1-1-1-methylhistamine exists in all living organisms, ranging from bacteria to humans. 1-1-1-methylhistamine participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and 1-1-methylhistamine can be biosynthesized from S-adenosylmethionine and histamine through its interaction with the enzyme histamine N-methyltransferase. In addition, 1-1-1-methylhistamine can be converted into methylimidazole acetaldehyde through the action of the enzyme amine oxidase [flavin-containing] a. In cattle, 1-1-methylhistamine is involved in the metabolic pathway called the histidine metabolism pathway. 1-1-1-methylhistamine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Methyl-1H-imidazole-4-ethanamine</synonym>
    <synonym>1-Methyl-4-(2-aminoethyl)imidazole</synonym>
    <synonym>3-Methylhistamine</synonym>
    <synonym>4-(1-Aminoethyl)-1-methyl-1H-imidazole</synonym>
    <synonym>Methylhistamine</synonym>
    <synonym>N-Methylhistamine</synonym>
    <synonym>N(1)-Methylhistamine</synonym>
    <synonym>Ntau-methylhistamine</synonym>
    <synonym>tele-Methylhistamine</synonym>
    <synonym>tele-Methylhistamine dihydrochloride</synonym>
    <synonym>1-Methyl-4-(beta-aminoethyl)imidazole</synonym>
    <synonym>1,4-Methylhistamine</synonym>
    <synonym>N-tele Methylhistamine</synonym>
    <synonym>1-Methyl-4-(b-aminoethyl)imidazole</synonym>
    <synonym>1-Methyl-4-histamine</synonym>
    <synonym>2-(1-Methyl-1H-imidazol-4-yl)ethanamine</synonym>
    <synonym>2-(1-Methyl-1H-imidazol-4-yl)ethylamine</synonym>
    <synonym>4-(2-Aminoethyl)-1-methyl-imidazole</synonym>
    <synonym>4-(2-Aminoethyl)-1-methylimidazole</synonym>
    <synonym>H137</synonym>
    <synonym>N( 1)-Methylhistamine</synonym>
    <synonym>N(T)-Methylhistamine</synonym>
    <synonym>N-tele-Methylhistamine</synonym>
    <synonym>N-Telle-methylhistamine</synonym>
    <synonym>N1-Methylhistamine</synonym>
    <synonym>NT-Methylhistamine</synonym>
  </synonyms>
  <chemical_formula>C6H11N3</chemical_formula>
  <average_molecular_weight>125.1716</average_molecular_weight>
  <monisotopic_moleculate_weight>125.095297367</monisotopic_moleculate_weight>
  <iupac_name>2-(1-methyl-1H-imidazol-4-yl)ethan-1-amine</iupac_name>
  <traditional_iupac>methylhistamine</traditional_iupac>
  <cas_registry_number>501-75-7</cas_registry_number>
  <smiles>CN1C=NC(CCN)=C1</smiles>
  <inchi>InChI=1S/C6H11N3/c1-9-4-6(2-3-7)8-5-9/h4-5H,2-3,7H2,1H3</inchi>
  <inchikey>FHQDWPCFSJMNCT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>2-arylethylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-arylethylamine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>imidazoles</external_descriptor>
      <external_descriptor>primary amino compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(1-methyl-1H-imidazol-4-yl)ethan-1-amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>125.1716</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>125.095297367</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C=NC(CCN)=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H11N3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H11N3/c1-9-4-6(2-3-7)8-5-9/h4-5H,2-3,7H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FHQDWPCFSJMNCT-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>43.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>36.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447966</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05127</kegg_id>
  <pubchem_compound_id>3614</pubchem_compound_id>
  <chemspider_id>3488</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB022306</foodb_id>
  <pdbe_id/>
  <chebi_id>29009</chebi_id>
  <meta_cyc_id>N-METHYL-HISTAMINE</meta_cyc_id>
  <wikipedia_id>Methylhistamine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>45171</bigg_id>
  <metlin_id>5854</metlin_id>
  <synthesis_reference>Rothschild, Zuleika; Schayer, Richard W.  Synthesis and metabolism of a histamine metabolite, 1-methyl-4-(b-aminoethyl)imidazole.    Biochimica et Biophysica Acta  (1958),  30  23-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:18 UTC</creation_date>
  <update_date>2020-04-15 22:35:36 UTC</update_date>
  <accession>BMDB0000899</accession>
  <secondary_accessions>
    <accession>BMDB00899</accession>
  </secondary_accessions>
  <name>Androstanedione</name>
  <description>Androstanedione belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, androstanedione is considered to be a steroid lipid molecule. Androstanedione exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Androstanedione exists in all living organisms, ranging from bacteria to humans. Androstanedione participates in a number of enzymatic reactions, within cattle. In particular, Androstanedione can be biosynthesized from androstenedione; which is mediated by the enzyme 3-oxo-5-alpha-steroid 4-dehydrogenase 1. In addition, Androstanedione can be converted into androsterone; which is catalyzed by the enzyme aldo-keto reductase family 1 member C4. In cattle, androstanedione is involved in the metabolic pathway called the androstenedione metabolism pathway.</description>
  <synonyms>
    <synonym>5alpha-Androstan-3,17-dione</synonym>
    <synonym>5a-Androstan-3,17-dione</synonym>
    <synonym>5Α-androstan-3,17-dione</synonym>
    <synonym>(5a)-Androstane-3,17-dione</synonym>
    <synonym>5-alpha-Androstane-3,17-dione</synonym>
    <synonym>5a-Androsta-3,17-dione</synonym>
    <synonym>5a-Androstane-3, 17-dione</synonym>
    <synonym>5a-Androstane-3,17-dione</synonym>
    <synonym>5a-Androstanedione</synonym>
    <synonym>5alpha-Androstane-3,17-dione</synonym>
    <synonym>Androstane-3,17-dione</synonym>
    <synonym>Androstane-3,7-dione</synonym>
    <synonym>Androstane-3,17-dione, (2-3(H)-labeled, (2beta,5beta))-isomer</synonym>
    <synonym>Androstane-3,17-dione, (4-(3)H-labeled, (4alpha,5beta))-isomer</synonym>
    <synonym>Androstane-3,17-dione, (2-3(H)-labeled, (2alpha,5beta))-isomer</synonym>
    <synonym>Androstane-3,17-dione, (4-(3)H-labeled, (4beta,5beta))-isomer</synonym>
    <synonym>Androstane-3,17-dione, (5beta)-isomer</synonym>
    <synonym>3,17-Dioxy-5 alpha-androstane</synonym>
    <synonym>5 alpha-Androstanedione</synonym>
    <synonym>5 beta-Androstane-3,17-dione</synonym>
    <synonym>5 alpha-Androstane-3,17-dione</synonym>
    <synonym>Androstane-3,17-dione, (5alpha)-isomer</synonym>
  </synonyms>
  <chemical_formula>C19H28O2</chemical_formula>
  <average_molecular_weight>288.4244</average_molecular_weight>
  <monisotopic_moleculate_weight>288.20893014</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-dione</iupac_name>
  <traditional_iupac>(1S,2S,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-dione</traditional_iupac>
  <cas_registry_number>846-46-8</cas_registry_number>
  <smiles>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1</inchi>
  <inchikey>RAJWOBJTTGJROA-WZNAKSSCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo-5-alpha-steroids</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-oxo-5-alpha-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>androstane-3,17-dione</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>133.5 - 134.0 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>288.4244</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>288.20893014</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H28O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RAJWOBJTTGJROA-WZNAKSSCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>34.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>82.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androstenedione Metabolism</name>
      <smpdb_id>SMP0087271</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>247581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>247582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>247583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>267522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>267523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>267524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450091</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00674</kegg_id>
  <pubchem_compound_id>222865</pubchem_compound_id>
  <chemspider_id>193520</chemspider_id>
  <drugbank_id>DB01561</drugbank_id>
  <foodb_id>FDB022307</foodb_id>
  <pdbe_id/>
  <chebi_id>15994</chebi_id>
  <meta_cyc_id>CPD-342</meta_cyc_id>
  <wikipedia_id>Androstanedione</wikipedia_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>42505</bigg_id>
  <metlin_id>5855</metlin_id>
  <synthesis_reference>Marker, Russell E.; Kamm, Oliver; Jones, David M.; Oakwood, Thomas S.  Sterols. VIII. Preparation of androstanedione from allopregnanediol.    Journal of the American Chemical Society  (1937),  59  614-16.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:19 UTC</creation_date>
  <update_date>2020-04-16 20:38:35 UTC</update_date>
  <accession>BMDB0000900</accession>
  <secondary_accessions>
    <accession>BMDB00900</accession>
  </secondary_accessions>
  <name>Ergocalciferol</name>
  <description>Ergocalciferol, also known as vitamin D2 or viosterol, belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. Thus, ergocalciferol is considered to be a secosteroid lipid molecule. Ergocalciferol is a drug which is used for use in the management of hypocalcemia and its clinical manifestations in patients with hypoparathyroidism, as well as for the treatment of familial hypophosphatemia (vitamin d resistant rickets). this drug has also been used in the treatment of nutritional rickets or osteomalacia, vitamin d dependent rickets, rickets or osteomalacia secondary to long-term high dose anticonvulsant therapy, early renal osteodystrophy, osteoporosis (in conjunction with calcium), and hypophosphatemia associated with fanconi syndrome (with treatment of acidosis). Ergocalciferol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Ergocalciferol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(3beta,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol</synonym>
    <synonym>(5Z,7E,22E)-(3S)-9,10-Seco-5,7,10(19),22-ergostatetraen-3-ol</synonym>
    <synonym>(5Z,7E,22E)-(3S)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol</synonym>
    <synonym>Activated ergosterol</synonym>
    <synonym>Calciferol</synonym>
    <synonym>Ercalciol</synonym>
    <synonym>Ergocalciferolum</synonym>
    <synonym>Oleovitamin D2</synonym>
    <synonym>Viosterol</synonym>
    <synonym>Vitamina D2</synonym>
    <synonym>Vitamin D2</synonym>
    <synonym>Drisdol</synonym>
    <synonym>(3b,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol</synonym>
    <synonym>(3Β,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol</synonym>
    <synonym>(+)-Vitamin D2</synonym>
    <synonym>(5E,7E,22E)-9,10-Secoergosta-5,7,10,22-tetraen-3-ol</synonym>
    <synonym>22-Tetraen 3beta 9,10,secoergosta-5,7,10(19)-ol</synonym>
    <synonym>4-Methylene-3-[2-[tetrahydro-7a-methyl-1-(1,4,5-trimethyl-2-hexenyl)-4(3ah)-indanylidene]ethylidene]-cyclohexanol</synonym>
    <synonym>9,10-Secoergosta-5,7,10(19),22-tetraen-3b-ol</synonym>
    <synonym>beta-Ol</synonym>
    <synonym>Buco-D</synonym>
    <synonym>Calciferon 2</synonym>
    <synonym>Condacaps</synonym>
    <synonym>Condocaps</synonym>
    <synonym>Condol</synonym>
    <synonym>Crtron</synonym>
    <synonym>Crystallina</synonym>
    <synonym>D-Arthin</synonym>
    <synonym>D-Tracetten</synonym>
    <synonym>Daral</synonym>
    <synonym>Davitamon D</synonym>
    <synonym>Davitin</synonym>
    <synonym>De-rat concentrate</synonym>
    <synonym>Decaps</synonym>
    <synonym>Dee-osterol</synonym>
    <synonym>Dee-ron</synonym>
    <synonym>Dee-ronal</synonym>
    <synonym>Dee-roual</synonym>
    <synonym>delta-Arthin</synonym>
    <synonym>delta-Tracetten</synonym>
    <synonym>Deltalin</synonym>
    <synonym>Deratol</synonym>
    <synonym>Detalup</synonym>
    <synonym>Diactol</synonym>
    <synonym>Divit urto</synonym>
    <synonym>Doral</synonym>
    <synonym>Ergocalciferol oil</synonym>
    <synonym>Ergorone</synonym>
    <synonym>Ergosterol activated</synonym>
    <synonym>Ergosterol irradiated</synonym>
    <synonym>Ertron</synonym>
    <synonym>Fortodyl</synonym>
    <synonym>Geltabs</synonym>
    <synonym>Hi-deratol</synonym>
    <synonym>Infron</synonym>
    <synonym>Irradiated ergosta-5,7,22-trien-3beta-ol</synonym>
    <synonym>Metadee</synonym>
    <synonym>Mina D2</synonym>
    <synonym>Mulsiferol</synonym>
    <synonym>Mykostin</synonym>
    <synonym>Novovitamin-D</synonym>
    <synonym>Oleovitamin D</synonym>
    <synonym>Osteil</synonym>
    <synonym>Ostelin</synonym>
    <synonym>Radiostol</synonym>
    <synonym>Radstein</synonym>
    <synonym>Radsterin</synonym>
    <synonym>Rodine C</synonym>
    <synonym>Shock-ferol</synonym>
    <synonym>Shock-ferol sterogyl</synonym>
    <synonym>Sterogyl</synonym>
    <synonym>Synthetic vitamin D</synonym>
    <synonym>Uvesterol D</synonym>
    <synonym>Uvesterol-D</synonym>
    <synonym>Vio D</synonym>
    <synonym>Vio-D</synonym>
    <synonym>Viostdrol</synonym>
    <synonym>Viosterol in oil</synonym>
    <synonym>Vitavel-D</synonym>
    <synonym>Calciferols</synonym>
    <synonym>Ergocalciferols</synonym>
    <synonym>D2, Vitamin</synonym>
    <synonym>Vitamin D 2</synonym>
    <synonym>Ergocalciferol</synonym>
  </synonyms>
  <chemical_formula>C28H44O</chemical_formula>
  <average_molecular_weight>396.6484</average_molecular_weight>
  <monisotopic_moleculate_weight>396.33921603</monisotopic_moleculate_weight>
  <iupac_name>(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol</iupac_name>
  <traditional_iupac>ergocalciferol</traditional_iupac>
  <cas_registry_number>50-14-6</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)\C=C\[C@H](C)C(C)C</smiles>
  <inchi>InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1</inchi>
  <inchikey>MECHNRXZTMCUDQ-RKHKHRCZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Vitamin D and derivatives</sub_class>
    <direct_parent>Vitamin D and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Triterpenoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fat-soluble vitamins</external_descriptor>
      <external_descriptor>Vitamin D2 and derivatives</external_descriptor>
      <external_descriptor>Vitamin D2 and derivatives</external_descriptor>
      <external_descriptor>hydroxy seco-steroid</external_descriptor>
      <external_descriptor>seco-ergostane</external_descriptor>
      <external_descriptor>vitamin D</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>116.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.05 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>396.6484</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>396.33921603</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)\C=C\[C@H](C)C(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C28H44O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MECHNRXZTMCUDQ-RKHKHRCZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>128.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>50.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>254724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>254725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>254726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>274665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>274666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>274667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448217</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000126</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=33&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000126</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1154&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000176</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, s</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1049&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00192</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1066&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000176</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1048&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00252</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1265&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000227</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=6&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000202</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1266&amp;2</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0003 +/- 0.0001</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0003 +/- 0.0002</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0003 +/- 0.0001</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0003 +/- 0.0001</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000504</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Pirjo H. Mattila, Vieno I. Piironen, Esko J. Uusi-Rauva, and Pekka E. Koivistoinen. 1995. Contents of Cholecalciferol, Ergocalciferol, and Their 25-Hydroxylated Metabolites in Milk Products and Raw Meat and Liver As Determined by HPLC. J. Agric. Food Chem. 43 (9), pp 2394–2399</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C05441</kegg_id>
  <pubchem_compound_id>5280793</pubchem_compound_id>
  <chemspider_id>4444351</chemspider_id>
  <drugbank_id>DB00153</drugbank_id>
  <foodb_id>FDB012811</foodb_id>
  <pdbe_id/>
  <chebi_id>28934</chebi_id>
  <meta_cyc_id>VITAMIN_D2</meta_cyc_id>
  <wikipedia_id>Ergocalciferol</wikipedia_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>2289183</bigg_id>
  <metlin_id>5856</metlin_id>
  <synthesis_reference>Okabe, Masami. Vitamin D2 from ergosterol (9,10-secoergosta-5,7,10(19),22-tetraen-3-ol,(3b)- from ergosta-5,7,22-trien-3-ol,(3b)-). Organic Syntheses (1999), 76 275-286.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Pirjo H. Mattila, Vieno I. Piironen, Esko J. Uusi-Rauva, and Pekka E. Koivistoinen. 1995. Contents of Cholecalciferol, Ergocalciferol, and Their 25-Hydroxylated Metabolites in Milk Products and Raw Meat and Liver As Determined by HPLC. J. Agric. Food Chem. 43 (9), pp 2394–2399</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=33&amp;2</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1154&amp;2</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1049&amp;2</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1066&amp;2</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1048&amp;2</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1265&amp;2</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=6&amp;2</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1266&amp;2</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:20 UTC</creation_date>
  <update_date>2020-04-15 22:28:04 UTC</update_date>
  <accession>BMDB0000901</accession>
  <secondary_accessions>
    <accession>BMDB00901</accession>
  </secondary_accessions>
  <name>Valproic acid glucuronide</name>
  <description/>
  <synonyms>
    <synonym>Valproate glucuronide</synonym>
    <synonym>1-(2-Propylpentanoate</synonym>
    <synonym>1-(2-Propylpentanoate) beta-D-glucopyranuronate</synonym>
    <synonym>1-(2-Propylpentanoate) beta-D-glucopyranuronic acid</synonym>
    <synonym>1-(2-Propylpentanoate) beta-delta-glucopyranuronate</synonym>
    <synonym>1-(2-Propylpentanoate) beta-delta-glucopyranuronic acid</synonym>
    <synonym>1-(2-Propylpentanoic acid</synonym>
    <synonym>1-O-Valproyl-b-D-glucopyranuronic acid</synonym>
    <synonym>1-O-Valproyl-beta-delta-glucopyranuronic acid</synonym>
    <synonym>3,4,5-Trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylate</synonym>
    <synonym>3,4,5-Trihydroxy-6-(2-propyl-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid</synonym>
    <synonym>Dipropylacetate glucuronide</synonym>
    <synonym>Myproate</synonym>
    <synonym>Myproic acid</synonym>
    <synonym>Valproate</synonym>
    <synonym>Valproic acid</synonym>
    <synonym>VPA-g</synonym>
    <synonym>VPAG</synonym>
  </synonyms>
  <chemical_formula>C14H24O8</chemical_formula>
  <average_molecular_weight>320.3356</average_molecular_weight>
  <monisotopic_moleculate_weight>320.147117744</monisotopic_moleculate_weight>
  <iupac_name>(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid</traditional_iupac>
  <cas_registry_number>60113-83-9</cas_registry_number>
  <smiles>CCCC(CCC)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O</smiles>
  <inchi>InChI=1S/C14H24O8/c1-3-5-7(6-4-2)13(20)22-14-10(17)8(15)9(16)11(21-14)12(18)19/h7-11,14-17H,3-6H2,1-2H3,(H,18,19)/t8-,9-,10+,11-,14-/m0/s1</inchi>
  <inchikey>XXKSYIHWRBBHIC-JVWRJRKNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>O-glucuronides</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-o-glucuronide</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid ester</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>O-glucuronide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-propylpentanoyl)oxy]oxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>320.3356</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>320.147117744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCC(CCC)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H24O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H24O8/c1-3-5-7(6-4-2)13(20)22-14-10(17)8(15)9(16)11(21-14)12(18)19/h7-11,14-17H,3-6H2,1-2H3,(H,18,19)/t8-,9-,10+,11-,14-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XXKSYIHWRBBHIC-JVWRJRKNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>133.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>68109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>68110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>68111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>126066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>126067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>126068</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <pubchem_compound_id>88111</pubchem_compound_id>
  <chemspider_id/>
  <drugbank_id/>
  <foodb_id>FDB022308</foodb_id>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>2991</metlin_id>
  <synthesis_reference>Yamamura, Naotoshi; Muramatsu, Shigeki; Suzuki, Kanae; Uchiyama, Minoru; Nakajima, Eiichi. High-yield, enzymic synthesis of 14C- or 3H-labeled 1-O-valproyl-b-D-glucopyranuronic acid, the main metabolite of valproic acid in human. Radioisotopes (1999), 48(</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:21 UTC</creation_date>
  <update_date>2020-04-16 20:39:06 UTC</update_date>
  <accession>BMDB0000902</accession>
  <secondary_accessions>
    <accession>BMDB00902</accession>
  </secondary_accessions>
  <name>NAD</name>
  <description/>
  <synonyms>
    <synonym>Codehydrogenase I</synonym>
    <synonym>Coenzyme I</synonym>
    <synonym>Cozymase I</synonym>
    <synonym>Diphosphopyridine nucleotide</synonym>
    <synonym>DPN</synonym>
    <synonym>Nadide</synonym>
    <synonym>NICOTINAMIDE-adenine-dinucleotide</synonym>
    <synonym>Adenine dinucleotide, dihydronicotinamide</synonym>
    <synonym>NAD</synonym>
    <synonym>Nicotinamide-adenine dinucleotide</synonym>
    <synonym>Nucleotide, diphosphopyridine</synonym>
    <synonym>Dihydronicotinamide adenine dinucleotide</synonym>
    <synonym>NADH</synonym>
    <synonym>Nicotinamide adenine dinucleotide</synonym>
    <synonym>Dinucleotide, nicotinamide-adenine</synonym>
    <synonym>Dinucleotide, dihydronicotinamide adenine</synonym>
    <synonym>Adenine-nicotinamide dinucleotide</synonym>
    <synonym>NAD+</synonym>
    <synonym>Oxidized diphosphopyridine nucleotide</synonym>
    <synonym>beta-Diphosphopyridine nucleotide</synonym>
    <synonym>beta-NAD</synonym>
    <synonym>beta-NAD+</synonym>
    <synonym>beta-Nicotinamide adenine dinucleotide</synonym>
    <synonym>beta-Nicotinamide adenine dinucleotide hydrate</synonym>
    <synonym>β-Diphosphopyridine nucleotide</synonym>
    <synonym>β-NAD</synonym>
    <synonym>β-NAD+</synonym>
    <synonym>β-Nicotinamide adenine dinucleotide</synonym>
    <synonym>β-Nicotinamide adenine dinucleotide hydrate</synonym>
  </synonyms>
  <chemical_formula>C21H27N7O14P2</chemical_formula>
  <average_molecular_weight>663.4251</average_molecular_weight>
  <monisotopic_moleculate_weight>663.109121631</monisotopic_moleculate_weight>
  <iupac_name>1-[(2R,3R,4S,5R)-5-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono}oxy)(hydroxy)phosphoryl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1lambda5-pyridin-1-ylium</iupac_name>
  <traditional_iupac>1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1lambda5-pyridin-1-ylium</traditional_iupac>
  <cas_registry_number>53-84-9</cas_registry_number>
  <smiles>NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1</inchi>
  <inchikey>BAWFJGJZGIEFAR-NNYOXOHSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Nicotinamide nucleotides</alternative_parent>
      <alternative_parent>Nicotinamides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Pyridinium derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Nicotinamide</substituent>
      <substituent>Nicotinamide-nucleotide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridine nucleotide</substituent>
      <substituent>Pyridinium</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>NAD</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>140.0 - 142.0 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>752.5 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(2R,3R,4S,5R)-5-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono}oxy)(hydroxy)phosphoryl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-(C-hydroxycarbonimidoyl)-1lambda5-pyridin-1-ylium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>663.4251</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>663.109121631</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H27N7O14P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BAWFJGJZGIEFAR-NNYOXOHSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>322.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>151.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>58.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Androstenedione Metabolism</name>
      <smpdb_id>SMP0087271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Butyrate Metabolism</name>
      <smpdb_id>SMP0087185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Caffeine Metabolism</name>
      <smpdb_id>SMP0087186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis</name>
      <smpdb_id>SMP0072032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:0)</name>
      <smpdb_id>SMP0077151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:0)</name>
      <smpdb_id>SMP0077153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:0)</name>
      <smpdb_id>SMP0077171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:0)</name>
      <smpdb_id>SMP0077173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077189</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077190</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077191</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077197</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077198</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077199</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077200</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077201</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077202</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077203</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077204</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077205</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077206</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077207</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077208</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077209</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077210</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077211</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077212</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077213</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077214</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077215</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077216</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077217</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077218</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077219</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077220</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077221</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077222</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077223</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077224</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077225</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077226</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077227</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077228</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077229</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077230</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077231</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077232</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077233</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077234</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077235</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077237</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077238</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077239</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077240</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077241</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077242</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077243</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077244</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077245</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077246</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077247</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077248</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077249</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077250</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077251</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077252</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077253</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077254</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077255</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077256</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077257</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077258</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077259</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077261</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077263</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077264</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077265</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077266</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077267</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077268</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077269</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077272</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077274</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077275</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077276</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077277</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077278</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077279</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077280</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077281</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077282</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077283</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077284</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077285</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077286</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077287</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077288</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077289</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077290</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077291</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077292</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077293</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077294</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077295</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077296</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077297</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077298</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:0)</name>
      <smpdb_id>SMP0077299</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077300</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077301</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077302</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077303</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077304</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077305</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077306</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077307</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077308</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077309</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:0)</name>
      <smpdb_id>SMP0077310</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077311</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:0)</name>
      <smpdb_id>SMP0077312</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077313</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077314</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077315</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077316</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077317</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077318</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077319</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077320</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077321</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077322</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077323</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077324</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077325</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077326</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077327</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077328</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077329</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077330</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077331</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077332</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077333</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077334</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077335</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077336</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077337</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077338</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077339</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077340</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077341</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077342</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077343</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077344</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077345</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077346</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077347</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077348</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077349</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077350</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077351</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077352</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077353</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077354</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077355</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077356</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077359</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077365</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077366</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077367</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077368</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077369</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077370</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077371</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077373</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077374</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077375</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077376</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077377</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077378</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077379</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077381</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077382</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077383</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077384</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077385</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077386</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077387</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077388</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077389</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077390</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077391</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077392</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077393</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077394</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077395</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077396</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077397</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077398</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077399</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077400</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077401</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077402</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077403</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077404</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077405</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077406</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077407</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077408</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077409</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077410</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077411</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077412</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077413</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077414</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077415</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077416</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077417</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077418</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077419</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077420</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077421</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077422</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077423</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077424</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077425</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077426</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077427</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077428</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077429</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077430</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077431</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077432</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077433</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077434</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077435</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077437</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077439</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077440</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077441</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077442</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077444</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077445</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077446</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077447</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077448</smpdb_id>
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    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077449</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077450</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077451</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077452</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077453</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077454</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077455</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077456</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077457</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077458</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077459</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077460</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077461</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077462</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077463</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077464</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077465</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077470</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077471</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077472</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077474</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077475</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077476</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077477</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077478</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077479</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077480</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077481</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077482</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077483</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077484</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077485</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077486</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077487</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077488</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077489</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077490</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077491</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077492</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077493</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077494</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077495</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077496</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077497</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077498</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077499</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077500</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077501</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077502</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077503</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077504</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077505</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077506</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077507</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077508</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077509</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077510</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077511</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077512</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077513</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077514</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077515</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077516</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077517</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077518</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077519</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077520</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077521</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077522</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077524</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077525</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077526</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077599</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077600</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077601</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077602</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077603</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077604</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077605</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077606</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077607</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077608</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077609</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077610</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077611</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077612</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077613</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077614</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077615</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077616</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077617</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077618</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077619</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077620</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077621</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077622</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077623</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077625</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077626</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077627</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077628</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077629</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077630</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077635</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077636</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077637</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077638</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077639</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077640</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077641</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077645</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077649</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077650</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077651</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077652</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077653</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077654</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077655</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077656</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077657</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077658</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077659</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077660</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077661</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077662</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077663</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077664</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077665</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077670</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077672</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077673</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077674</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077675</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077676</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077677</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077678</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077679</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077680</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077681</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077682</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077683</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077684</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077685</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077688</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077689</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077690</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077691</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077692</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077693</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077694</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077695</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077696</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077697</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077698</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077699</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077700</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077701</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077702</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077703</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077704</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077705</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077706</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077707</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077708</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077709</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077710</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077712</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077714</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077715</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077716</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077720</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077722</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077723</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077724</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077725</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077726</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077727</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077729</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077730</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077731</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077732</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077733</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077734</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077735</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077736</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077737</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077738</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077739</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077740</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077741</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077742</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077743</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077744</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077745</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077746</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077747</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077748</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077749</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077750</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077751</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077752</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077753</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077754</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077755</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077756</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077757</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077758</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077760</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077761</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077762</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077763</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077766</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077767</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077768</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077771</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077772</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077773</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077774</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077781</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077783</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077793</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077801</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077802</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077803</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077804</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077805</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077809</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077810</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077811</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077812</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077813</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077814</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077815</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077816</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077817</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077819</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077820</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077822</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077825</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077829</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077831</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077832</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077833</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077834</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077835</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077836</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077837</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077839</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077840</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077841</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077842</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077843</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077845</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077846</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077847</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077848</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077850</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077851</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077852</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077853</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077854</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077855</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077857</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077858</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077863</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077864</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077891</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077892</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077894</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077895</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077898</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077900</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077901</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077902</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077903</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077904</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077905</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077906</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077907</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077908</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077909</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077910</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077911</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077912</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077913</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077914</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077915</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077916</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077917</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077918</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077919</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077920</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077921</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077922</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077923</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077924</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077925</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077926</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077927</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077928</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077929</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077930</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077932</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077933</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077934</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077935</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077936</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077937</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077938</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077939</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077940</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077941</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077942</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077943</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077944</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077945</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077946</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077947</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077948</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077949</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077950</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077951</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077952</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077953</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077954</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077955</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077956</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077958</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077960</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077985</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/16:0)</name>
      <smpdb_id>SMP0078130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:0)</name>
      <smpdb_id>SMP0078132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078215</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078216</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:0)</name>
      <smpdb_id>SMP0078219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078223</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078225</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078233</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078234</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078235</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078245</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078252</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078253</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078254</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078255</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078256</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078257</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078258</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078262</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078264</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078265</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078266</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078267</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078268</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078270</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078272</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078273</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078274</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078275</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078276</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078277</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078279</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078280</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078281</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078282</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078283</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078284</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078287</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078288</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078289</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078290</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078293</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078294</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078295</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078296</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078297</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078298</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078299</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078300</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078301</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078302</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078303</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078304</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078305</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078306</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078307</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078308</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078309</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078310</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078311</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078312</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078313</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078314</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078315</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078316</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078317</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078318</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078319</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078320</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078321</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078322</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078323</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078324</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078325</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078326</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078327</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078328</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078329</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078330</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078331</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078332</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078333</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078334</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078336</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078337</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078338</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078342</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078343</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078348</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078350</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078351</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078352</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078353</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078354</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078355</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078356</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078357</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078358</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078359</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078360</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078361</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078362</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078363</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078364</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078365</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078366</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078367</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078368</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078369</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078370</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078371</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078372</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078373</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078374</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078375</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078376</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078377</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078378</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078379</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078380</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078381</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078382</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078386</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078388</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078389</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078390</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078391</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078393</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078394</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078395</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078396</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078397</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078398</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078399</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078400</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078406</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078407</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078408</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078421</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078422</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078423</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078424</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078425</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078426</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078427</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078428</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078429</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078430</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078431</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078432</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078433</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078434</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078435</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078436</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078437</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078438</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078439</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078440</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078441</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078442</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078443</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078444</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078445</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078446</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078447</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078448</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078449</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078450</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078451</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078452</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078453</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078454</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078455</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078457</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078458</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078459</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078460</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078462</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078463</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078464</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078465</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078466</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078467</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078468</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078469</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078470</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078471</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078472</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078473</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078474</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078475</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078476</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078478</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078479</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078480</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078481</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078482</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078483</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078484</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078485</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078486</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078487</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078488</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078489</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078490</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078491</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078492</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078493</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078494</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078495</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078496</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078498</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078499</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078500</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078501</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078502</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078503</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078504</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078506</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078507</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078508</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078509</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078510</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078516</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078517</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078518</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078519</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078520</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078521</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078530</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078531</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078532</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078533</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078534</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078605</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078606</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078607</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078608</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078609</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078610</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078612</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078614</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078615</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078616</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078617</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078618</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078619</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078620</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078621</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078622</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078623</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078624</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078625</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078626</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078627</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078628</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078629</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078630</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078631</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078632</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078633</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078634</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078635</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078636</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078637</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078638</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078639</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078640</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078641</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078642</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078644</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078654</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078656</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078657</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078658</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078659</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078660</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078661</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078662</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078664</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078665</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078666</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078667</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078668</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078669</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078670</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078671</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078672</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078673</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078674</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078675</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078676</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078677</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078678</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078679</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078680</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078681</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078682</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078683</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078684</smpdb_id>
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      <smpdb_id>SMP0078685</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078767</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078768</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078769</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078770</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078771</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078772</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078773</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078774</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078775</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078776</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078777</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078778</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078779</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078780</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078781</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078782</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078783</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078784</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078785</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078786</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078787</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078788</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078789</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078790</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078792</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078794</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078795</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078796</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078797</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078798</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078800</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078802</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078804</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078805</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078806</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078807</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078808</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078809</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078810</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078811</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078812</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078813</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078814</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078815</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078816</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078817</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078818</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078819</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078820</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078821</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078822</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078823</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078824</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078825</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078826</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078828</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078830</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078831</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078832</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078834</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078835</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078840</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078841</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078842</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078843</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078844</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078845</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078846</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078848</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078849</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078850</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078851</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078852</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078853</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078854</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078855</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078856</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078858</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078859</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078860</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078861</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078862</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078864</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078870</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078875</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078876</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078877</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078878</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078879</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078885</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078890</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078917</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078918</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078919</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078920</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <smpdb_id>SMP0078992</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079140</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079141</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079142</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079143</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079144</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079145</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079146</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079147</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079148</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079149</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079150</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0079152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079159</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079166</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079169</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079171</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079174</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079175</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079176</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079178</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079179</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079180</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079181</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079184</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079185</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079186</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079187</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079190</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079191</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079192</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079193</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079194</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079195</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079196</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079197</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079198</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079199</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079200</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079201</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079202</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079203</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079204</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079205</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079206</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079207</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079208</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079209</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079210</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079211</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079212</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079214</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079215</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079216</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079217</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079218</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079219</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079220</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079221</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079222</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079223</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079224</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079225</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079226</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079227</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079228</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079229</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079230</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079231</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079232</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079233</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079234</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079235</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079236</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079237</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079238</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079239</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079240</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079241</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079242</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079243</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079244</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079245</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079246</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079247</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079248</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079249</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079250</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079251</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079252</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079253</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079254</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079255</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079256</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079257</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079258</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079259</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079260</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079261</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079262</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079263</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079264</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079265</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079266</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079267</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079268</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079269</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079270</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079271</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079272</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079273</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079274</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079275</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079276</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079277</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079278</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079279</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079280</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079281</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079282</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079283</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079284</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079285</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079286</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079287</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079288</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079289</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079290</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079291</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079297</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079299</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079300</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079305</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079306</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079431</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079432</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079433</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079434</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079435</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079436</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079437</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079438</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079440</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079441</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079442</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079443</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079444</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079445</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079448</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079449</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079450</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079451</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079454</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079464</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079465</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079466</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079467</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079468</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079469</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079470</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079474</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079475</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079477</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079478</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079479</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079481</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079482</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079485</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079486</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079488</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079489</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079490</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079491</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079492</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079493</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079494</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079495</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079496</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079497</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079498</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079499</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079500</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079502</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079503</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079504</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079505</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079506</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079507</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079508</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079509</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079510</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079511</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079512</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079513</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079514</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079515</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079516</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079519</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079520</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079521</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079522</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079523</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079527</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079531</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079533</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079534</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079535</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079536</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079537</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079538</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079549</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079562</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079563</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079564</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079565</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079566</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079567</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079568</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079570</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079572</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079573</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079574</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079575</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079576</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079584</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079585</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079586</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079587</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079588</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079589</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079590</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0079603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0079604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079650</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079651</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079656</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079659</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079664</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079714</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079717</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079761</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079762</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079785</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079789</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079852</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080044</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080116</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080119</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080120</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080228</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080232</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080235</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080237</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080238</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080239</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080240</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080241</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080242</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080244</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080246</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080250</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080251</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080252</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080262</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080263</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080287</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080288</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080298</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080299</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis</name>
      <smpdb_id>SMP0071338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/10:0)</name>
      <smpdb_id>SMP0108241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/12:0)</name>
      <smpdb_id>SMP0108483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/13:0)</name>
      <smpdb_id>SMP0108481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/14:0)</name>
      <smpdb_id>SMP0108477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/15:0)</name>
      <smpdb_id>SMP0108517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/16:0)</name>
      <smpdb_id>SMP0108480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/17:0)</name>
      <smpdb_id>SMP0108472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/18:0)</name>
      <smpdb_id>SMP0108485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/19:0)</name>
      <smpdb_id>SMP0108526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/8:0)</name>
      <smpdb_id>SMP0108478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-13:0)</name>
      <smpdb_id>SMP0108541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-15:0)</name>
      <smpdb_id>SMP0108542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-17:0)</name>
      <smpdb_id>SMP0108543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-21:0)</name>
      <smpdb_id>SMP0108544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-25:0)</name>
      <smpdb_id>SMP0108545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-12:0)</name>
      <smpdb_id>SMP0108546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-13:0)</name>
      <smpdb_id>SMP0108547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-14:0)</name>
      <smpdb_id>SMP0108548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-15:0)</name>
      <smpdb_id>SMP0108549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-16:0)</name>
      <smpdb_id>SMP0108550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-17:0)</name>
      <smpdb_id>SMP0108551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-18:0)</name>
      <smpdb_id>SMP0108552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-19:0)</name>
      <smpdb_id>SMP0108553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-20:0)</name>
      <smpdb_id>SMP0108554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-21:0)</name>
      <smpdb_id>SMP0108555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-22:0)</name>
      <smpdb_id>SMP0108556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-24:0)</name>
      <smpdb_id>SMP0108557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/12:0)</name>
      <smpdb_id>SMP0108470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/13:0)</name>
      <smpdb_id>SMP0108512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/14:0)</name>
      <smpdb_id>SMP0108445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/15:0)</name>
      <smpdb_id>SMP0108471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0108558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0108559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0108560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0108561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0108562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0108563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0108564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0108565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0108566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0108567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0108568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0108569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0108570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0108571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0108572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0108573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0108574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/13:0)</name>
      <smpdb_id>SMP0108460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/15:0)</name>
      <smpdb_id>SMP0108469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/16:0)</name>
      <smpdb_id>SMP0108463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/8:0)</name>
      <smpdb_id>SMP0108451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0108575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0108576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0108577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0108578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0108579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0108580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0108581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0108582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0108583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0108584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0108585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0108586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0108587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0108588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0108589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0108590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0108591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/13:0)</name>
      <smpdb_id>SMP0108534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/14:0)</name>
      <smpdb_id>SMP0108525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/15:0)</name>
      <smpdb_id>SMP0108522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/17:0)</name>
      <smpdb_id>SMP0108488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/18:0)</name>
      <smpdb_id>SMP0108489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/19:0)</name>
      <smpdb_id>SMP0108447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0108592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0108593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0108594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0108595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0108596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0108597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0108598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0108599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0108600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0108601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0108602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0108603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0108604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0108605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0108606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0108607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0108608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/15:0)</name>
      <smpdb_id>SMP0108476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/17:0)</name>
      <smpdb_id>SMP0108461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/18:0)</name>
      <smpdb_id>SMP0108523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/8:0)</name>
      <smpdb_id>SMP0108494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0108609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0108610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0108611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0108612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0108613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0108614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0108615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0108616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0108617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0108618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0108619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0108620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0108621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0108622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0108623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0108624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0108625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/12:0)</name>
      <smpdb_id>SMP0108479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/14:0)</name>
      <smpdb_id>SMP0108468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/15:0)</name>
      <smpdb_id>SMP0108507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/16:0)</name>
      <smpdb_id>SMP0108467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/17:0)</name>
      <smpdb_id>SMP0108458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/18:0)</name>
      <smpdb_id>SMP0108518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/8:0)</name>
      <smpdb_id>SMP0108504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0108626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0108627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0108628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0108629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0108630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0108631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0108632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0108633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0108634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0108635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0108636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0108637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0108638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0108639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0108640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0108641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0108642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/12:0)</name>
      <smpdb_id>SMP0108465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/13:0)</name>
      <smpdb_id>SMP0108456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/17:0)</name>
      <smpdb_id>SMP0108506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0108643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0108644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0108645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0108646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0108647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0108648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0108649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0108650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0108651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0108652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0108653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0108654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0108655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0108656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0108657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0108658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0108659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/12:0)</name>
      <smpdb_id>SMP0108495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/13:0)</name>
      <smpdb_id>SMP0108492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/17:0)</name>
      <smpdb_id>SMP0108452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/18:0)</name>
      <smpdb_id>SMP0108448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/19:0)</name>
      <smpdb_id>SMP0108503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/8:0)</name>
      <smpdb_id>SMP0108466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0108660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0108661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0108662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0108663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0108664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0108665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0108666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0108667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0108668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0108669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0108670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0108671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0108672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0108673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0108674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0108675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0108676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/12:0)</name>
      <smpdb_id>SMP0108511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/13:0)</name>
      <smpdb_id>SMP0108473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/15:0)</name>
      <smpdb_id>SMP0108533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/16:0)</name>
      <smpdb_id>SMP0108496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/17:0)</name>
      <smpdb_id>SMP0108521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/19:0)</name>
      <smpdb_id>SMP0108514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0108677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0108678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0108679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-21:0)</name>
      <smpdb_id>SMP0108680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-25:0)</name>
      <smpdb_id>SMP0108681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0108682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0108683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0108684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0108685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0108686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0108687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0108688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0108689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-20:0)</name>
      <smpdb_id>SMP0108690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-21:0)</name>
      <smpdb_id>SMP0108691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-22:0)</name>
      <smpdb_id>SMP0108692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-24:0)</name>
      <smpdb_id>SMP0108693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-13:0)</name>
      <smpdb_id>SMP0108694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-15:0)</name>
      <smpdb_id>SMP0108695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-17:0)</name>
      <smpdb_id>SMP0108696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0108697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0108698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-12:0)</name>
      <smpdb_id>SMP0108699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-13:0)</name>
      <smpdb_id>SMP0108700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-14:0)</name>
      <smpdb_id>SMP0108701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-15:0)</name>
      <smpdb_id>SMP0108702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-16:0)</name>
      <smpdb_id>SMP0108703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-17:0)</name>
      <smpdb_id>SMP0108704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-18:0)</name>
      <smpdb_id>SMP0108705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0108706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0108707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0108708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0108709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0108710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0108711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0108712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0108713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0108714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0108715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0108716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0108717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0108718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0108719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0108720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0108721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0108722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0108723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0108724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0108725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0108726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0108727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0108728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0108729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0108730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0108731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0108732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0108733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0108734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0108735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0108736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0108737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0108738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0108739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0108740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0108741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0108742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0108743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0108744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/17:0)</name>
      <smpdb_id>SMP0108457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/8:0)</name>
      <smpdb_id>SMP0108519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0108745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0108746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0108747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0108748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0108749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0108750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0108751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0108752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0108753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0108754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0108755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0108756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0108757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0108759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0111848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0108761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0108763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0108765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0108767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0108768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0108770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0108772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0108774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0108775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0108777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0108778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0108779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0108780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0108781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0108782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0108783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0108784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0108785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0108786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0108787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0108788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0108789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0108790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0108791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0108792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0108793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0108794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0108795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0108796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0108797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0108798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0108799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0108800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0108801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0108802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0108803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0108804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0108805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0108806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0108807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0108808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0108809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0108810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0108811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0108812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0108813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0108814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0108815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0108816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0108817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0108818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0108819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0108820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0108821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0108822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0108823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0108824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0108825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0108826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0108827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0108828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0108829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0108830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0108831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0108832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0108833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0108834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0108835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0108836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0108837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0108838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0108839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0108840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0108841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0108842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0108843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0108844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0108845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0108846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0108847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0108848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0108849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0108850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0108851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0108852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0108853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0108854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0108855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0108856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0108857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0108858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0108859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0108860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0108861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0108862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0108863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0108864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0108865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0108866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0108867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0108868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0108869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0108870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0108871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0108872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0108873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0108874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0108875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0108876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0108877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0108878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0108879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0108880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0108881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0108882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0108883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0108884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0108885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0108886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0108887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0108888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0108889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0108890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0108891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0108892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0108893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0108894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0108895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0108896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0108897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0108898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0108899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0108900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0108901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0108902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0108903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0108904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0108905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0108906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0108907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0108908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0108909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0108910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0108911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0108912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/a-25:0)</name>
      <smpdb_id>SMP0108913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0108914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0108915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0108916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/a-25:0)</name>
      <smpdb_id>SMP0108917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0108918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0108919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-24:0/a-25:0)</name>
      <smpdb_id>SMP0108920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0108921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(12:0/12:0/12:0)</name>
      <smpdb_id>SMP0108243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/14:0)</name>
      <smpdb_id>SMP0072652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/14:1(9Z))</name>
      <smpdb_id>SMP0072653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/15:0)</name>
      <smpdb_id>SMP0072654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/16:0)</name>
      <smpdb_id>SMP0072655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/16:1(9Z))</name>
      <smpdb_id>SMP0072656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:0)</name>
      <smpdb_id>SMP0072657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:1(11Z))</name>
      <smpdb_id>SMP0072658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:1(9Z))</name>
      <smpdb_id>SMP0072659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:0)</name>
      <smpdb_id>SMP0072664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:1(11Z))</name>
      <smpdb_id>SMP0072665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:0)</name>
      <smpdb_id>SMP0072672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:1(13Z))</name>
      <smpdb_id>SMP0072673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/24:0)</name>
      <smpdb_id>SMP0072679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/24:1(15Z))</name>
      <smpdb_id>SMP0072680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0072681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0072682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0072683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0072684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0072685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/15:0)</name>
      <smpdb_id>SMP0072709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/16:0)</name>
      <smpdb_id>SMP0072710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/16:1(9Z))</name>
      <smpdb_id>SMP0072711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:0)</name>
      <smpdb_id>SMP0072712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:1(11Z))</name>
      <smpdb_id>SMP0072713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:1(9Z))</name>
      <smpdb_id>SMP0072714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:0)</name>
      <smpdb_id>SMP0072719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:1(11Z))</name>
      <smpdb_id>SMP0072720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:0)</name>
      <smpdb_id>SMP0072727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:1(13Z))</name>
      <smpdb_id>SMP0072728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/24:0)</name>
      <smpdb_id>SMP0072734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/24:1(15Z))</name>
      <smpdb_id>SMP0072735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/16:0)</name>
      <smpdb_id>SMP0072736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0072737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:0)</name>
      <smpdb_id>SMP0072738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0072739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0072740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:0)</name>
      <smpdb_id>SMP0072745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0072746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:0)</name>
      <smpdb_id>SMP0072753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0072754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/24:0)</name>
      <smpdb_id>SMP0072760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0072761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0072762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0072763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:0)</name>
      <smpdb_id>SMP0072787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0072788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0072789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:0)</name>
      <smpdb_id>SMP0072794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0072795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:0)</name>
      <smpdb_id>SMP0072802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0072803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/24:0)</name>
      <smpdb_id>SMP0072809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0072810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0072817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0072825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0072832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0072860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0072868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0072875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0072880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0072888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0072895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0072899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0072907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0072914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0072917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0072925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0072932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:0)</name>
      <smpdb_id>SMP0072934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0072935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:0)</name>
      <smpdb_id>SMP0072942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0072943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/24:0)</name>
      <smpdb_id>SMP0072949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0072950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0072958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0072965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0072973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0072980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0072987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0072994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:0)</name>
      <smpdb_id>SMP0073042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0073043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/24:0)</name>
      <smpdb_id>SMP0073049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0073050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0073057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:0/24:0)</name>
      <smpdb_id>SMP0073084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0073085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0073087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0073088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0073089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/15:0)</name>
      <smpdb_id>SMP0073115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/16:0)</name>
      <smpdb_id>SMP0073116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/16:1(9Z))</name>
      <smpdb_id>SMP0073117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:0)</name>
      <smpdb_id>SMP0073118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:1(11Z))</name>
      <smpdb_id>SMP0073119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:1(9Z))</name>
      <smpdb_id>SMP0073120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:0)</name>
      <smpdb_id>SMP0073125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:1(11Z))</name>
      <smpdb_id>SMP0073126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:0)</name>
      <smpdb_id>SMP0073133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:1(13Z))</name>
      <smpdb_id>SMP0073134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/24:0)</name>
      <smpdb_id>SMP0073140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/24:1(15Z))</name>
      <smpdb_id>SMP0073141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/16:0)</name>
      <smpdb_id>SMP0073142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:0)</name>
      <smpdb_id>SMP0073144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:0)</name>
      <smpdb_id>SMP0073151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:0)</name>
      <smpdb_id>SMP0073159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/24:0)</name>
      <smpdb_id>SMP0073166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0073193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0073194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0073195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:0)</name>
      <smpdb_id>SMP0073200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0073201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:0)</name>
      <smpdb_id>SMP0073208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0073209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/24:0)</name>
      <smpdb_id>SMP0073215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0073216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0073223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:0)</name>
      <smpdb_id>SMP0073340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0073341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:0)</name>
      <smpdb_id>SMP0073348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0073349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/24:0)</name>
      <smpdb_id>SMP0073355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0073356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0073393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0073400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:0)</name>
      <smpdb_id>SMP0073448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0073449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/24:0)</name>
      <smpdb_id>SMP0073455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0073456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0073463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/24:0/24:0)</name>
      <smpdb_id>SMP0073490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0073491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/15:0)</name>
      <smpdb_id>SMP0073493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/16:0)</name>
      <smpdb_id>SMP0073494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/16:1(9Z))</name>
      <smpdb_id>SMP0073495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:0)</name>
      <smpdb_id>SMP0073496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:1(11Z))</name>
      <smpdb_id>SMP0073497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:1(9Z))</name>
      <smpdb_id>SMP0073498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:0)</name>
      <smpdb_id>SMP0073503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:1(11Z))</name>
      <smpdb_id>SMP0073504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:0)</name>
      <smpdb_id>SMP0073511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:1(13Z))</name>
      <smpdb_id>SMP0073512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/24:0)</name>
      <smpdb_id>SMP0073518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/24:1(15Z))</name>
      <smpdb_id>SMP0073519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/16:0)</name>
      <smpdb_id>SMP0073520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:0)</name>
      <smpdb_id>SMP0073522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:0)</name>
      <smpdb_id>SMP0073529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:0)</name>
      <smpdb_id>SMP0073537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/24:0)</name>
      <smpdb_id>SMP0073544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:0)</name>
      <smpdb_id>SMP0073571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0073572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0073573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:0)</name>
      <smpdb_id>SMP0073578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0073579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:0)</name>
      <smpdb_id>SMP0073586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0073587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/24:0)</name>
      <smpdb_id>SMP0073593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0073594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0073601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:0)</name>
      <smpdb_id>SMP0073718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0073719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:0)</name>
      <smpdb_id>SMP0073726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0073727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/24:0)</name>
      <smpdb_id>SMP0073733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0073734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0073771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0073778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:0)</name>
      <smpdb_id>SMP0073826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0073827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/24:0)</name>
      <smpdb_id>SMP0073833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0073834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0073841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/24:0/24:0)</name>
      <smpdb_id>SMP0073868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0073869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:0)</name>
      <smpdb_id>SMP0073871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:0)</name>
      <smpdb_id>SMP0073873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:0)</name>
      <smpdb_id>SMP0073880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:0)</name>
      <smpdb_id>SMP0073888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/24:0)</name>
      <smpdb_id>SMP0073895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:0)</name>
      <smpdb_id>SMP0073922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0073923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0073924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:0)</name>
      <smpdb_id>SMP0073929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0073930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:0)</name>
      <smpdb_id>SMP0073937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0073938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/24:0)</name>
      <smpdb_id>SMP0073944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0073945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0073952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:0)</name>
      <smpdb_id>SMP0074069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:0)</name>
      <smpdb_id>SMP0074077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/24:0)</name>
      <smpdb_id>SMP0074084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0074122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0074129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:0)</name>
      <smpdb_id>SMP0074177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0074178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/24:0)</name>
      <smpdb_id>SMP0074184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0074185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0074192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:0/24:0)</name>
      <smpdb_id>SMP0074219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0074220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0074222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0074223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0074247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0074248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0074249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:0)</name>
      <smpdb_id>SMP0074254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0074255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:0)</name>
      <smpdb_id>SMP0074262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0074263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/24:0)</name>
      <smpdb_id>SMP0074269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0074270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0074277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:0)</name>
      <smpdb_id>SMP0074394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:0)</name>
      <smpdb_id>SMP0074402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/24:0)</name>
      <smpdb_id>SMP0074409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0074447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0074454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:0)</name>
      <smpdb_id>SMP0074502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0074503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/24:0)</name>
      <smpdb_id>SMP0074509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0074510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0074517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/24:0/24:0)</name>
      <smpdb_id>SMP0074544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0074545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:0)</name>
      <smpdb_id>SMP0074547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0074548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0074549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:0)</name>
      <smpdb_id>SMP0074554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0074555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:0)</name>
      <smpdb_id>SMP0074562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0074563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/24:0)</name>
      <smpdb_id>SMP0074569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0074570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0074577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:0)</name>
      <smpdb_id>SMP0074695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:0)</name>
      <smpdb_id>SMP0074703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/24:0)</name>
      <smpdb_id>SMP0074710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0074748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0074756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:0)</name>
      <smpdb_id>SMP0074804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0074805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/24:0)</name>
      <smpdb_id>SMP0074811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0074812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0074819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/24:0/24:0)</name>
      <smpdb_id>SMP0074846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0074847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0074855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:0)</name>
      <smpdb_id>SMP0074972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:0)</name>
      <smpdb_id>SMP0074980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/24:0)</name>
      <smpdb_id>SMP0074988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0075126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0075127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0075131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0075139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0075146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0075148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0075380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0076011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0076012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0076020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0076027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:0)</name>
      <smpdb_id>SMP0076029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0076030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:0)</name>
      <smpdb_id>SMP0076037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0076038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/24:0)</name>
      <smpdb_id>SMP0076044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0076045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0076053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0076060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/20:0)</name>
      <smpdb_id>SMP0108262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/21:0)</name>
      <smpdb_id>SMP0108257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/22:0)</name>
      <smpdb_id>SMP0108278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/a-21:0)</name>
      <smpdb_id>SMP0108922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/a-25:0)</name>
      <smpdb_id>SMP0108923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-21:0)</name>
      <smpdb_id>SMP0108924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-22:0)</name>
      <smpdb_id>SMP0108925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-24:0)</name>
      <smpdb_id>SMP0108926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/21:0)</name>
      <smpdb_id>SMP0108277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/22:0)</name>
      <smpdb_id>SMP0108311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0108927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0108928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0108929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0108930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0108931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0108932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0108933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/10:0)</name>
      <smpdb_id>SMP0108328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/12:0)</name>
      <smpdb_id>SMP0108244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/13:0)</name>
      <smpdb_id>SMP0108317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/14:0)</name>
      <smpdb_id>SMP0108266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/15:0)</name>
      <smpdb_id>SMP0108275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/16:0)</name>
      <smpdb_id>SMP0108332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/17:0)</name>
      <smpdb_id>SMP0108292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/18:0)</name>
      <smpdb_id>SMP0108327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/21:0)</name>
      <smpdb_id>SMP0108305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/22:0)</name>
      <smpdb_id>SMP0108316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/8:0)</name>
      <smpdb_id>SMP0108301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0108934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0108935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0108936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0108937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0108938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0108939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0108940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0108941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0108942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0108943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0108944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0108945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0108946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0108947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0108948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0108949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0108950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/10:0)</name>
      <smpdb_id>SMP0108279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/12:0)</name>
      <smpdb_id>SMP0108261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/13:0)</name>
      <smpdb_id>SMP0108286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/14:0)</name>
      <smpdb_id>SMP0108255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/15:0)</name>
      <smpdb_id>SMP0108252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/16:0)</name>
      <smpdb_id>SMP0108299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/17:0)</name>
      <smpdb_id>SMP0108308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/18:0)</name>
      <smpdb_id>SMP0108282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/22:0)</name>
      <smpdb_id>SMP0108265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/8:0)</name>
      <smpdb_id>SMP0108319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0108951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0108952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0108953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0108954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0108955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0108956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0108957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0108958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0108959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0108960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0108961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0108962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0108963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0108964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0108965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0108966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0108967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0108968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/13:0)</name>
      <smpdb_id>SMP0108969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/14:0)</name>
      <smpdb_id>SMP0108970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/15:0)</name>
      <smpdb_id>SMP0108971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/16:0)</name>
      <smpdb_id>SMP0108972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/17:0)</name>
      <smpdb_id>SMP0108973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/18:0)</name>
      <smpdb_id>SMP0108974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/8:0)</name>
      <smpdb_id>SMP0108975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-13:0)</name>
      <smpdb_id>SMP0108976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-15:0)</name>
      <smpdb_id>SMP0108977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-17:0)</name>
      <smpdb_id>SMP0108978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0108979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0108980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0108981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0108982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0108983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0108984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0108985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0108986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0108987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0108988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0108989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0108990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0108991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0108992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/12:0)</name>
      <smpdb_id>SMP0108993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/13:0)</name>
      <smpdb_id>SMP0108994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/14:0)</name>
      <smpdb_id>SMP0108995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/15:0)</name>
      <smpdb_id>SMP0108996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/16:0)</name>
      <smpdb_id>SMP0108997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/17:0)</name>
      <smpdb_id>SMP0108998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/18:0)</name>
      <smpdb_id>SMP0108999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/8:0)</name>
      <smpdb_id>SMP0109000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-13:0)</name>
      <smpdb_id>SMP0109001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-15:0)</name>
      <smpdb_id>SMP0109002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-17:0)</name>
      <smpdb_id>SMP0109003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0109021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0109022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0109023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0109024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0109025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0109026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0109027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/8:0)</name>
      <smpdb_id>SMP0109028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0109029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0109030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0109031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0109032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0109033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0109034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0109035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0109036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0109037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0109038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-19:0)</name>
      <smpdb_id>SMP0109039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0109043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0109044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0109045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0109046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0109047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0109048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0109049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/8:0)</name>
      <smpdb_id>SMP0109050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0109051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0109052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0109053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0109054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0109055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0109056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0109057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0109058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0109059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0109060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-19:0)</name>
      <smpdb_id>SMP0109061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0109064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0109065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0109066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0109067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0109068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0109069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0109070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/8:0)</name>
      <smpdb_id>SMP0109071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0109072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0109073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0109074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0109075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0109076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0109078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0109079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0109080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0109081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0109082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-19:0)</name>
      <smpdb_id>SMP0109083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/10:0)</name>
      <smpdb_id>SMP0108330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/14:0)</name>
      <smpdb_id>SMP0108290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/17:0)</name>
      <smpdb_id>SMP0108312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/19:0)</name>
      <smpdb_id>SMP0108270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/21:0)</name>
      <smpdb_id>SMP0108300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/22:0)</name>
      <smpdb_id>SMP0108259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/10:0)</name>
      <smpdb_id>SMP0108320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/12:0)</name>
      <smpdb_id>SMP0108331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/13:0)</name>
      <smpdb_id>SMP0108318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/16:0)</name>
      <smpdb_id>SMP0108293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/17:0)</name>
      <smpdb_id>SMP0108304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/18:0)</name>
      <smpdb_id>SMP0108297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/19:0)</name>
      <smpdb_id>SMP0108288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/21:0)</name>
      <smpdb_id>SMP0108322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/22:0)</name>
      <smpdb_id>SMP0108314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/8:0)</name>
      <smpdb_id>SMP0108263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/10:0)</name>
      <smpdb_id>SMP0108256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/13:0)</name>
      <smpdb_id>SMP0108326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/15:0)</name>
      <smpdb_id>SMP0108250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/16:0)</name>
      <smpdb_id>SMP0108247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/21:0)</name>
      <smpdb_id>SMP0108313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/22:0)</name>
      <smpdb_id>SMP0108283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/8:0)</name>
      <smpdb_id>SMP0108276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/12:0)</name>
      <smpdb_id>SMP0108248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/13:0)</name>
      <smpdb_id>SMP0108295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/19:0)</name>
      <smpdb_id>SMP0108249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/21:0)</name>
      <smpdb_id>SMP0108271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/10:0)</name>
      <smpdb_id>SMP0108267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/12:0)</name>
      <smpdb_id>SMP0108324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/17:0)</name>
      <smpdb_id>SMP0108284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/21:0)</name>
      <smpdb_id>SMP0108306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/10:0)</name>
      <smpdb_id>SMP0108274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/19:0)</name>
      <smpdb_id>SMP0108269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/21:0)</name>
      <smpdb_id>SMP0108251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/13:0)</name>
      <smpdb_id>SMP0108289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/14:0)</name>
      <smpdb_id>SMP0108253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/16:0)</name>
      <smpdb_id>SMP0108302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/17:0)</name>
      <smpdb_id>SMP0108254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/19:0)</name>
      <smpdb_id>SMP0108264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/21:0)</name>
      <smpdb_id>SMP0108281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/22:0)</name>
      <smpdb_id>SMP0108294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/8:0)</name>
      <smpdb_id>SMP0108296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/10:0)</name>
      <smpdb_id>SMP0108315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/13:0)</name>
      <smpdb_id>SMP0108307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/17:0)</name>
      <smpdb_id>SMP0108273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/21:0)</name>
      <smpdb_id>SMP0108323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/8:0)</name>
      <smpdb_id>SMP0108287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/13:0)</name>
      <smpdb_id>SMP0108291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/15:0)</name>
      <smpdb_id>SMP0108272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/18:0)</name>
      <smpdb_id>SMP0108258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0109204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0109205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0109206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0109207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0109208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0109209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0109210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0109211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0109212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0109213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/10:0)</name>
      <smpdb_id>SMP0108309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/12:0)</name>
      <smpdb_id>SMP0108333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/13:0)</name>
      <smpdb_id>SMP0108329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/17:0)</name>
      <smpdb_id>SMP0108303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/19:0)</name>
      <smpdb_id>SMP0108321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:0)</name>
      <smpdb_id>SMP0076182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0076183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/21:0)</name>
      <smpdb_id>SMP0108390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:0)</name>
      <smpdb_id>SMP0076190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0076191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/24:0)</name>
      <smpdb_id>SMP0076197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0076198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/8:0)</name>
      <smpdb_id>SMP0108268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-13:0)</name>
      <smpdb_id>SMP0109214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-15:0)</name>
      <smpdb_id>SMP0109215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-17:0)</name>
      <smpdb_id>SMP0109216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0109217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0109218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-12:0)</name>
      <smpdb_id>SMP0109219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-13:0)</name>
      <smpdb_id>SMP0109220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-14:0)</name>
      <smpdb_id>SMP0109221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-15:0)</name>
      <smpdb_id>SMP0109222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-16:0)</name>
      <smpdb_id>SMP0109223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-17:0)</name>
      <smpdb_id>SMP0109224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-18:0)</name>
      <smpdb_id>SMP0109225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0109226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0109227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0109228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0109229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0109230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0076206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0076213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/21:0)</name>
      <smpdb_id>SMP0108389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/22:0)</name>
      <smpdb_id>SMP0108370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0109231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0109232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0109233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0109234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0109235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0109236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0109237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0109238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0109239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0109240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0109241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0109242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0109243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0109244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0109245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0109246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0109247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:0)</name>
      <smpdb_id>SMP0076290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/24:0)</name>
      <smpdb_id>SMP0076297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/24:0/24:0)</name>
      <smpdb_id>SMP0076332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/10:0)</name>
      <smpdb_id>SMP0108298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/14:0)</name>
      <smpdb_id>SMP0108246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/15:0)</name>
      <smpdb_id>SMP0108285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/16:0)</name>
      <smpdb_id>SMP0108280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/19:0)</name>
      <smpdb_id>SMP0108310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/21:0)</name>
      <smpdb_id>SMP0108245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/22:0)</name>
      <smpdb_id>SMP0108260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/8:0)</name>
      <smpdb_id>SMP0108325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0109330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0109370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0109371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0109372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0109373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0109374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0109375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0109376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0109377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0109378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0109379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0109380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0109381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0109382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0109383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0109384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0109385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0109386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0109387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0109388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0109389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0109390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0109391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0109392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0109393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0109394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0109395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0109396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0109397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0109398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0109400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0109401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0109402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0109403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0109404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0109405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0109406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0109407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0109408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0109409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0109410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0109411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0109412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0109413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0109414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0109415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0109416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0109417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0109418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0109419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0109420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0109421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0109422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0109423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0109424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0109425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0109426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0076342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0076349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/10:0)</name>
      <smpdb_id>SMP0108335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/12:0)</name>
      <smpdb_id>SMP0108363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/13:0)</name>
      <smpdb_id>SMP0108339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/17:0)</name>
      <smpdb_id>SMP0108349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/18:0)</name>
      <smpdb_id>SMP0108337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/22:0)</name>
      <smpdb_id>SMP0108367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/12:0)</name>
      <smpdb_id>SMP0108361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/13:0)</name>
      <smpdb_id>SMP0108351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/14:0)</name>
      <smpdb_id>SMP0108344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/15:0)</name>
      <smpdb_id>SMP0108371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/16:0)</name>
      <smpdb_id>SMP0108383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/18:0)</name>
      <smpdb_id>SMP0108387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/22:0)</name>
      <smpdb_id>SMP0108366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0109440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/13:0)</name>
      <smpdb_id>SMP0108368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/16:0)</name>
      <smpdb_id>SMP0108380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/17:0)</name>
      <smpdb_id>SMP0108345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/18:0)</name>
      <smpdb_id>SMP0108341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/22:0)</name>
      <smpdb_id>SMP0108388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/10:0)</name>
      <smpdb_id>SMP0108347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/13:0)</name>
      <smpdb_id>SMP0108342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/14:0)</name>
      <smpdb_id>SMP0108338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/16:0)</name>
      <smpdb_id>SMP0108346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/17:0)</name>
      <smpdb_id>SMP0108352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/18:0)</name>
      <smpdb_id>SMP0108386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/22:0)</name>
      <smpdb_id>SMP0108334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/8:0)</name>
      <smpdb_id>SMP0108365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/10:0)</name>
      <smpdb_id>SMP0108372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/13:0)</name>
      <smpdb_id>SMP0108358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/14:0)</name>
      <smpdb_id>SMP0108375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/15:0)</name>
      <smpdb_id>SMP0108348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/17:0)</name>
      <smpdb_id>SMP0108384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/18:0)</name>
      <smpdb_id>SMP0108369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/22:0)</name>
      <smpdb_id>SMP0108392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/8:0)</name>
      <smpdb_id>SMP0108354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/10:0)</name>
      <smpdb_id>SMP0108350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/15:0)</name>
      <smpdb_id>SMP0108355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/16:0)</name>
      <smpdb_id>SMP0108381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/17:0)</name>
      <smpdb_id>SMP0108364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/18:0)</name>
      <smpdb_id>SMP0108356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/22:0)</name>
      <smpdb_id>SMP0108385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/12:0)</name>
      <smpdb_id>SMP0108376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/17:0)</name>
      <smpdb_id>SMP0108393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/8:0)</name>
      <smpdb_id>SMP0108377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/17:0)</name>
      <smpdb_id>SMP0108396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/18:0)</name>
      <smpdb_id>SMP0108399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/10:0)</name>
      <smpdb_id>SMP0108340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/12:0)</name>
      <smpdb_id>SMP0108374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/13:0)</name>
      <smpdb_id>SMP0108336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/14:0)</name>
      <smpdb_id>SMP0108373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/15:0)</name>
      <smpdb_id>SMP0108382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/16:0)</name>
      <smpdb_id>SMP0108391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/17:0)</name>
      <smpdb_id>SMP0108397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/18:0)</name>
      <smpdb_id>SMP0108398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/22:0)</name>
      <smpdb_id>SMP0108400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/8:0)</name>
      <smpdb_id>SMP0108343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0109556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0109557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0109558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0109559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0109560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0109561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0109562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0109563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0109564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0109565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0109566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0109567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0109568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0109569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0109570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0109571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0109572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/17:0)</name>
      <smpdb_id>SMP0108395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/18:0)</name>
      <smpdb_id>SMP0108394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/22:0)</name>
      <smpdb_id>SMP0108401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/10:0)</name>
      <smpdb_id>SMP0108360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/12:0)</name>
      <smpdb_id>SMP0108357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/13:0)</name>
      <smpdb_id>SMP0108353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/16:0)</name>
      <smpdb_id>SMP0108359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/18:0)</name>
      <smpdb_id>SMP0108378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/22:0)</name>
      <smpdb_id>SMP0108362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/8:0)</name>
      <smpdb_id>SMP0108379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0109694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0109695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0109696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0109697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0109698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0109699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0109700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0109701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0109702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0109703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0109704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0109705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0109706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0109707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0109708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0109709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0109710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0109711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0109712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0109713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0109714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0109715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0109716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0109717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0109718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0109719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0109720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0109721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0109722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0109723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0109724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0109725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0109726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0109727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0109728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0109729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0109730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0109731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0109732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0109733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0109734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0109735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0109736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0109737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0109738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0109739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0109740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0109741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0109742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0109743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0109744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0109745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0109746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0109747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0109748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0109749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/10:0)</name>
      <smpdb_id>SMP0108437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/12:0)</name>
      <smpdb_id>SMP0108408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/13:0)</name>
      <smpdb_id>SMP0108423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/12:0)</name>
      <smpdb_id>SMP0108405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/13:0)</name>
      <smpdb_id>SMP0108403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/14:0)</name>
      <smpdb_id>SMP0108414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/15:0)</name>
      <smpdb_id>SMP0108426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/18:0)</name>
      <smpdb_id>SMP0108407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/8:0)</name>
      <smpdb_id>SMP0108420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0109763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/13:0)</name>
      <smpdb_id>SMP0108436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/15:0)</name>
      <smpdb_id>SMP0108428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/16:0)</name>
      <smpdb_id>SMP0108430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/17:0)</name>
      <smpdb_id>SMP0108419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/18:0)</name>
      <smpdb_id>SMP0108413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/8:0)</name>
      <smpdb_id>SMP0108411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/10:0)</name>
      <smpdb_id>SMP0108440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/13:0)</name>
      <smpdb_id>SMP0108422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/10:0)</name>
      <smpdb_id>SMP0108425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/8:0)</name>
      <smpdb_id>SMP0108410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/10:0)</name>
      <smpdb_id>SMP0108404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/12:0)</name>
      <smpdb_id>SMP0108406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/10:0)</name>
      <smpdb_id>SMP0108439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/12:0)</name>
      <smpdb_id>SMP0108402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/14:0)</name>
      <smpdb_id>SMP0108415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/15:0)</name>
      <smpdb_id>SMP0108434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/16:0)</name>
      <smpdb_id>SMP0108412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/17:0)</name>
      <smpdb_id>SMP0108431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/8:0)</name>
      <smpdb_id>SMP0108409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/10:0)</name>
      <smpdb_id>SMP0108421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/17:0)</name>
      <smpdb_id>SMP0108417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/8:0)</name>
      <smpdb_id>SMP0108432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/10:0)</name>
      <smpdb_id>SMP0108424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/12:0)</name>
      <smpdb_id>SMP0108435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/13:0)</name>
      <smpdb_id>SMP0108433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/17:0)</name>
      <smpdb_id>SMP0108438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:0)</name>
      <smpdb_id>SMP0076986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/24:0)</name>
      <smpdb_id>SMP0076993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/8:0)</name>
      <smpdb_id>SMP0108441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0077001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/24:0/24:0)</name>
      <smpdb_id>SMP0077028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/10:0)</name>
      <smpdb_id>SMP0108416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/14:0)</name>
      <smpdb_id>SMP0108418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/16:0)</name>
      <smpdb_id>SMP0108427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/8:0)</name>
      <smpdb_id>SMP0108429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0108540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0077031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0077037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:0/24:0/24:0)</name>
      <smpdb_id>SMP0077147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:1(15Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/10:0)</name>
      <smpdb_id>SMP0108443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/12:0)</name>
      <smpdb_id>SMP0108502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/16:0)</name>
      <smpdb_id>SMP0108450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/18:0)</name>
      <smpdb_id>SMP0108535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0110069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0110070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/12:0)</name>
      <smpdb_id>SMP0108459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/13:0)</name>
      <smpdb_id>SMP0108498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/14:0)</name>
      <smpdb_id>SMP0108462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/15:0)</name>
      <smpdb_id>SMP0108442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/17:0)</name>
      <smpdb_id>SMP0108464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/19:0)</name>
      <smpdb_id>SMP0108499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0110086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0110087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/10:0)</name>
      <smpdb_id>SMP0108455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/12:0)</name>
      <smpdb_id>SMP0108475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/14:0)</name>
      <smpdb_id>SMP0108532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/15:0)</name>
      <smpdb_id>SMP0108529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/17:0)</name>
      <smpdb_id>SMP0108491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/18:0)</name>
      <smpdb_id>SMP0108510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0110103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0110104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/12:0)</name>
      <smpdb_id>SMP0108486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/15:0)</name>
      <smpdb_id>SMP0108528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/17:0)</name>
      <smpdb_id>SMP0108505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0110120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0110121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/13:0)</name>
      <smpdb_id>SMP0108513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/14:0)</name>
      <smpdb_id>SMP0108449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/15:0)</name>
      <smpdb_id>SMP0108493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/16:0)</name>
      <smpdb_id>SMP0108500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/18:0)</name>
      <smpdb_id>SMP0108474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/19:0)</name>
      <smpdb_id>SMP0108446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0110137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0110138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/12:0)</name>
      <smpdb_id>SMP0108516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/16:0)</name>
      <smpdb_id>SMP0108530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/17:0)</name>
      <smpdb_id>SMP0108509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0110154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0110155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/13:0)</name>
      <smpdb_id>SMP0108524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/15:0)</name>
      <smpdb_id>SMP0108501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/17:0)</name>
      <smpdb_id>SMP0108453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/18:0)</name>
      <smpdb_id>SMP0108520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0110171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0110172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/10:0)</name>
      <smpdb_id>SMP0108482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/12:0)</name>
      <smpdb_id>SMP0108444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/14:0)</name>
      <smpdb_id>SMP0108497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/15:0)</name>
      <smpdb_id>SMP0108487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/17:0)</name>
      <smpdb_id>SMP0108484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/18:0)</name>
      <smpdb_id>SMP0108531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/19:0)</name>
      <smpdb_id>SMP0108538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0110185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0110186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0110187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0110188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0110189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0110190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0110191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0110192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0110193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0110194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0110195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-20:0)</name>
      <smpdb_id>SMP0110196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/12:0)</name>
      <smpdb_id>SMP0108508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/13:0)</name>
      <smpdb_id>SMP0108539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/14:0)</name>
      <smpdb_id>SMP0108515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/15:0)</name>
      <smpdb_id>SMP0108454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/16:0)</name>
      <smpdb_id>SMP0108490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/17:0)</name>
      <smpdb_id>SMP0108527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/18:0)</name>
      <smpdb_id>SMP0108537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/19:0)</name>
      <smpdb_id>SMP0108536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/8:0)</name>
      <smpdb_id>SMP0108242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0110197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0110198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0110199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0110200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0110201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0110202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0110203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0110204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0110205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0110206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0110207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0110208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0110209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0110210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0110211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0110212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0110213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0110217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0110218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0110223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0110233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0110234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0110248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0110249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0110262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0110263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0110264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0110265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0110266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0110267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0110268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0110269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0110270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0110271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0110272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0110273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0110274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0110275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/12:0)</name>
      <smpdb_id>SMP0110367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/13:0)</name>
      <smpdb_id>SMP0110368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/14:0)</name>
      <smpdb_id>SMP0110369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/15:0)</name>
      <smpdb_id>SMP0110370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/16:0)</name>
      <smpdb_id>SMP0110371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/17:0)</name>
      <smpdb_id>SMP0110372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/18:0)</name>
      <smpdb_id>SMP0110373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0110377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/13:0)</name>
      <smpdb_id>SMP0110390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/14:0)</name>
      <smpdb_id>SMP0110391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/15:0)</name>
      <smpdb_id>SMP0110392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/16:0)</name>
      <smpdb_id>SMP0110393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/17:0)</name>
      <smpdb_id>SMP0110394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/18:0)</name>
      <smpdb_id>SMP0110395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0110399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/14:0)</name>
      <smpdb_id>SMP0110412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/15:0)</name>
      <smpdb_id>SMP0110413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/16:0)</name>
      <smpdb_id>SMP0110414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/17:0)</name>
      <smpdb_id>SMP0110415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/18:0)</name>
      <smpdb_id>SMP0110416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0110420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/15:0)</name>
      <smpdb_id>SMP0110433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/16:0)</name>
      <smpdb_id>SMP0110434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/17:0)</name>
      <smpdb_id>SMP0110435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/18:0)</name>
      <smpdb_id>SMP0110436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0110440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/16:0)</name>
      <smpdb_id>SMP0110453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/17:0)</name>
      <smpdb_id>SMP0110454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/18:0)</name>
      <smpdb_id>SMP0110455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0110459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/17:0)</name>
      <smpdb_id>SMP0110472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/18:0)</name>
      <smpdb_id>SMP0110473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0110477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/18:0)</name>
      <smpdb_id>SMP0110490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0110494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0110510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0110524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0110538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0110551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/13:0)</name>
      <smpdb_id>SMP0110552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/14:0)</name>
      <smpdb_id>SMP0110553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/15:0)</name>
      <smpdb_id>SMP0110554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/16:0)</name>
      <smpdb_id>SMP0110555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/17:0)</name>
      <smpdb_id>SMP0110556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/18:0)</name>
      <smpdb_id>SMP0110557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-13:0)</name>
      <smpdb_id>SMP0110558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-15:0)</name>
      <smpdb_id>SMP0110559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-17:0)</name>
      <smpdb_id>SMP0110560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0110561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0110562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0110563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0110564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0110565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0110566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0110567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0110568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0110569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0110570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0110571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0110572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0110573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0110574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/a-13:0)</name>
      <smpdb_id>SMP0110630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/12:0)</name>
      <smpdb_id>SMP0110667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/13:0)</name>
      <smpdb_id>SMP0110668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/14:0)</name>
      <smpdb_id>SMP0110669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/15:0)</name>
      <smpdb_id>SMP0110670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/16:0)</name>
      <smpdb_id>SMP0110671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/17:0)</name>
      <smpdb_id>SMP0110672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/18:0)</name>
      <smpdb_id>SMP0110673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/13:0)</name>
      <smpdb_id>SMP0110689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/14:0)</name>
      <smpdb_id>SMP0110690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/15:0)</name>
      <smpdb_id>SMP0110691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/16:0)</name>
      <smpdb_id>SMP0110692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/17:0)</name>
      <smpdb_id>SMP0110693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/18:0)</name>
      <smpdb_id>SMP0110694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/14:0)</name>
      <smpdb_id>SMP0110710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/15:0)</name>
      <smpdb_id>SMP0110711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/16:0)</name>
      <smpdb_id>SMP0110712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/17:0)</name>
      <smpdb_id>SMP0110713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/18:0)</name>
      <smpdb_id>SMP0110714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/15:0)</name>
      <smpdb_id>SMP0110730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/16:0)</name>
      <smpdb_id>SMP0110731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/17:0)</name>
      <smpdb_id>SMP0110732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/18:0)</name>
      <smpdb_id>SMP0110733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/16:0)</name>
      <smpdb_id>SMP0110749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/17:0)</name>
      <smpdb_id>SMP0110750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/18:0)</name>
      <smpdb_id>SMP0110751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/17:0)</name>
      <smpdb_id>SMP0110767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/18:0)</name>
      <smpdb_id>SMP0110768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/18:0)</name>
      <smpdb_id>SMP0110784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0110807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/10:0)</name>
      <smpdb_id>SMP0110842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/12:0)</name>
      <smpdb_id>SMP0110843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/13:0)</name>
      <smpdb_id>SMP0110844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/14:0)</name>
      <smpdb_id>SMP0110845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/15:0)</name>
      <smpdb_id>SMP0110846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/16:0)</name>
      <smpdb_id>SMP0110847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/17:0)</name>
      <smpdb_id>SMP0110848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/18:0)</name>
      <smpdb_id>SMP0110849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-13:0)</name>
      <smpdb_id>SMP0110850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-15:0)</name>
      <smpdb_id>SMP0110851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-17:0)</name>
      <smpdb_id>SMP0110852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0110952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0110953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0110954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0110955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0110956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0110957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0110958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0110959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0110960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0110961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0110962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0110963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0110964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0110965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0110966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0110967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0110968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0110972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0110973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0110974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0110975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0110976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0110977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0110978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0110979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0110980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0110981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0110982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0110983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0110984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0110985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0110986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0110987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0110988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0110991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0110992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0110993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0110994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0110995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0110996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0110997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0110998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0110999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0111000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0111001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0111002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0111003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0111004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0111005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0111006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0111007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/12:0)</name>
      <smpdb_id>SMP0111009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/13:0)</name>
      <smpdb_id>SMP0111010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/14:0)</name>
      <smpdb_id>SMP0111011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/15:0)</name>
      <smpdb_id>SMP0111012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/16:0)</name>
      <smpdb_id>SMP0111013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/17:0)</name>
      <smpdb_id>SMP0111014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/18:0)</name>
      <smpdb_id>SMP0111015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/19:0)</name>
      <smpdb_id>SMP0111016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0111027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0111028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0111029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/13:0)</name>
      <smpdb_id>SMP0111031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/14:0)</name>
      <smpdb_id>SMP0111032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/15:0)</name>
      <smpdb_id>SMP0111033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/16:0)</name>
      <smpdb_id>SMP0111034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/17:0)</name>
      <smpdb_id>SMP0111035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/18:0)</name>
      <smpdb_id>SMP0111036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/19:0)</name>
      <smpdb_id>SMP0111037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0111048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0111049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0111050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/14:0)</name>
      <smpdb_id>SMP0111052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/15:0)</name>
      <smpdb_id>SMP0111053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/16:0)</name>
      <smpdb_id>SMP0111054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/17:0)</name>
      <smpdb_id>SMP0111055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/18:0)</name>
      <smpdb_id>SMP0111056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/19:0)</name>
      <smpdb_id>SMP0111057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0111068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0111069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0111070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/15:0)</name>
      <smpdb_id>SMP0111072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/16:0)</name>
      <smpdb_id>SMP0111073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/17:0)</name>
      <smpdb_id>SMP0111074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/18:0)</name>
      <smpdb_id>SMP0111075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/19:0)</name>
      <smpdb_id>SMP0111076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0111087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0111088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0111089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/16:0)</name>
      <smpdb_id>SMP0111091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/17:0)</name>
      <smpdb_id>SMP0111092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/18:0)</name>
      <smpdb_id>SMP0111093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/19:0)</name>
      <smpdb_id>SMP0111094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0111105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0111106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0111107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/17:0)</name>
      <smpdb_id>SMP0111109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/18:0)</name>
      <smpdb_id>SMP0111110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/19:0)</name>
      <smpdb_id>SMP0111111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0111122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0111123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0111124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/18:0)</name>
      <smpdb_id>SMP0111126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/19:0)</name>
      <smpdb_id>SMP0111127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0111138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0111139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0111140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/19:0)</name>
      <smpdb_id>SMP0111142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0111143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0111144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0111145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0111146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0111147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0111148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0111149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0111150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0111151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0111152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0111153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0111164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0111165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0111166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0111177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0111178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0111179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0111189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0111190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0111191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0111200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0111201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0111202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0111210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0111211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0111212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0111219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0111220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0111221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0111227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0111228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0111229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0111234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0111235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0111236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0111240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0111241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0111242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0111245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0111246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0111247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/12:0)</name>
      <smpdb_id>SMP0111249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/13:0)</name>
      <smpdb_id>SMP0111250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/14:0)</name>
      <smpdb_id>SMP0111251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/15:0)</name>
      <smpdb_id>SMP0111252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/16:0)</name>
      <smpdb_id>SMP0111253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/17:0)</name>
      <smpdb_id>SMP0111254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/18:0)</name>
      <smpdb_id>SMP0111255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-13:0)</name>
      <smpdb_id>SMP0111256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-15:0)</name>
      <smpdb_id>SMP0111257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-17:0)</name>
      <smpdb_id>SMP0111258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-12:0)</name>
      <smpdb_id>SMP0111259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-13:0)</name>
      <smpdb_id>SMP0111260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-14:0)</name>
      <smpdb_id>SMP0111261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-15:0)</name>
      <smpdb_id>SMP0111262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-16:0)</name>
      <smpdb_id>SMP0111263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-17:0)</name>
      <smpdb_id>SMP0111264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-18:0)</name>
      <smpdb_id>SMP0111265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0111266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0111267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0111268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0111269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0111270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0111271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0111272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/12:0)</name>
      <smpdb_id>SMP0111276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/13:0)</name>
      <smpdb_id>SMP0111277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/14:0)</name>
      <smpdb_id>SMP0111278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/15:0)</name>
      <smpdb_id>SMP0111279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/16:0)</name>
      <smpdb_id>SMP0111280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/17:0)</name>
      <smpdb_id>SMP0111281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/18:0)</name>
      <smpdb_id>SMP0111282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0111293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/13:0)</name>
      <smpdb_id>SMP0111295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/14:0)</name>
      <smpdb_id>SMP0111296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/15:0)</name>
      <smpdb_id>SMP0111297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/16:0)</name>
      <smpdb_id>SMP0111298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/17:0)</name>
      <smpdb_id>SMP0111299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/18:0)</name>
      <smpdb_id>SMP0111300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0111311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/14:0)</name>
      <smpdb_id>SMP0111313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/15:0)</name>
      <smpdb_id>SMP0111314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/16:0)</name>
      <smpdb_id>SMP0111315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/17:0)</name>
      <smpdb_id>SMP0111316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/18:0)</name>
      <smpdb_id>SMP0111317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0111328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/15:0)</name>
      <smpdb_id>SMP0111330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/16:0)</name>
      <smpdb_id>SMP0111331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/17:0)</name>
      <smpdb_id>SMP0111332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/18:0)</name>
      <smpdb_id>SMP0111333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0111344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/16:0)</name>
      <smpdb_id>SMP0111346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/17:0)</name>
      <smpdb_id>SMP0111347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/18:0)</name>
      <smpdb_id>SMP0111348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0111359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/17:0)</name>
      <smpdb_id>SMP0111361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/18:0)</name>
      <smpdb_id>SMP0111362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0111373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/18:0)</name>
      <smpdb_id>SMP0111375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0111386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0111398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0111409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0111419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0111428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0111436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0111443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0111449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0111454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0111458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0111461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0111463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0111464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0111465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0111466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0111467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0111468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0111469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0111470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0111471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0111472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0111473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0111474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0111475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0111476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0111477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0111478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0111479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0111480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0111481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0111482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/12:0)</name>
      <smpdb_id>SMP0111486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/13:0)</name>
      <smpdb_id>SMP0111487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/14:0)</name>
      <smpdb_id>SMP0111488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/15:0)</name>
      <smpdb_id>SMP0111489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/16:0)</name>
      <smpdb_id>SMP0111490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/17:0)</name>
      <smpdb_id>SMP0111491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/18:0)</name>
      <smpdb_id>SMP0111492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/13:0)</name>
      <smpdb_id>SMP0111504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/14:0)</name>
      <smpdb_id>SMP0111505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/15:0)</name>
      <smpdb_id>SMP0111506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/16:0)</name>
      <smpdb_id>SMP0111507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/17:0)</name>
      <smpdb_id>SMP0111508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/18:0)</name>
      <smpdb_id>SMP0111509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/14:0)</name>
      <smpdb_id>SMP0111521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/15:0)</name>
      <smpdb_id>SMP0111522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/16:0)</name>
      <smpdb_id>SMP0111523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/17:0)</name>
      <smpdb_id>SMP0111524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/18:0)</name>
      <smpdb_id>SMP0111525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/15:0)</name>
      <smpdb_id>SMP0111537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/16:0)</name>
      <smpdb_id>SMP0111538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/17:0)</name>
      <smpdb_id>SMP0111539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/18:0)</name>
      <smpdb_id>SMP0111540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/16:0)</name>
      <smpdb_id>SMP0111552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/17:0)</name>
      <smpdb_id>SMP0111553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/18:0)</name>
      <smpdb_id>SMP0111554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/17:0)</name>
      <smpdb_id>SMP0111566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/18:0)</name>
      <smpdb_id>SMP0111567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/18:0)</name>
      <smpdb_id>SMP0111579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0111656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0111657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0111658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0111659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0111660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0111661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0111662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0111663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0111664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0111665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0111666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0111667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0111668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0111669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0111670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0111671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0111672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/12:0)</name>
      <smpdb_id>SMP0111676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/13:0)</name>
      <smpdb_id>SMP0111677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/14:0)</name>
      <smpdb_id>SMP0111678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/15:0)</name>
      <smpdb_id>SMP0111679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/16:0)</name>
      <smpdb_id>SMP0111680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/17:0)</name>
      <smpdb_id>SMP0111681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/18:0)</name>
      <smpdb_id>SMP0111682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/13:0)</name>
      <smpdb_id>SMP0111693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/14:0)</name>
      <smpdb_id>SMP0111694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/15:0)</name>
      <smpdb_id>SMP0111695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/16:0)</name>
      <smpdb_id>SMP0111696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/17:0)</name>
      <smpdb_id>SMP0111697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/18:0)</name>
      <smpdb_id>SMP0111698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/14:0)</name>
      <smpdb_id>SMP0111709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/15:0)</name>
      <smpdb_id>SMP0111710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/16:0)</name>
      <smpdb_id>SMP0111711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/17:0)</name>
      <smpdb_id>SMP0111712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/18:0)</name>
      <smpdb_id>SMP0111713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/15:0)</name>
      <smpdb_id>SMP0111724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/16:0)</name>
      <smpdb_id>SMP0111725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/17:0)</name>
      <smpdb_id>SMP0111726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/18:0)</name>
      <smpdb_id>SMP0111727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/16:0)</name>
      <smpdb_id>SMP0111738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/17:0)</name>
      <smpdb_id>SMP0111739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/18:0)</name>
      <smpdb_id>SMP0111740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/17:0)</name>
      <smpdb_id>SMP0111751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/18:0)</name>
      <smpdb_id>SMP0111752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/18:0)</name>
      <smpdb_id>SMP0111763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0111829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0111830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0111831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0111832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0111833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0111834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0111835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0111836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0111837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0111838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0111839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0111840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0111841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0111842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0111843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0111844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0111845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ethanol Degradation</name>
      <smpdb_id>SMP0087192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Elongation in Mitochondria</name>
      <smpdb_id>SMP0087194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glucose-Alanine Cycle</name>
      <smpdb_id>SMP0087221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerol Phosphate Shuttle</name>
      <smpdb_id>SMP0087199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ketone Body Metabolism</name>
      <smpdb_id>SMP0087202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Malate-Aspartate Shuttle</name>
      <smpdb_id>SMP0087204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Electron Transport Chain</name>
      <smpdb_id>SMP0087261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pterine Biosynthesis</name>
      <smpdb_id>SMP0087250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Retinol Metabolism</name>
      <smpdb_id>SMP0087260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Selenoamino Acid Metabolism</name>
      <smpdb_id>SMP0087161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroidogenesis</name>
      <smpdb_id>SMP0087238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Succinate Signalling</name>
      <smpdb_id>SMP0120941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Threonine and 2-Oxobutanoate Degradation</name>
      <smpdb_id>SMP0087262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>117684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>117685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>117686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448512</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>347+/-99</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>641+/-127</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>15-611</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>515+/-70</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>151+/-22</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00003</kegg_id>
  <drugbank_id>DB14128</drugbank_id>
  <foodb_id>FDB022309</foodb_id>
  <chemspider_id>5682</chemspider_id>
  <pubchem_compound_id>5892</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>44215</chebi_id>
  <meta_cyc_id>NAD</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007256</knapsack_id>
  <bigg_id/>
  <wikipedia_id>NAD</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Hughes, N. A.; Kenner, G. W.; Todd, Alexander. Codehydrogenases. III. Synthesis of diphosphopyridine nucleotide (cozymase) and triphosphopyridine nucleotide. Journal of the Chemical Society (1957), 3733-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00022</protein_accession>
      <name>Nitric oxide synthase, endothelial</name>
      <uniprot_id>P29473</uniprot_id>
      <gene_name>NOS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00066</protein_accession>
      <name>Cytochrome b5 reductase 4</name>
      <uniprot_id>Q32LH7</uniprot_id>
      <gene_name>CYB5R4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00069</protein_accession>
      <name>Nitric oxide synthase, inducible</name>
      <uniprot_id>Q27995</uniprot_id>
      <gene_name>NOS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00071</protein_accession>
      <name>3-ketodihydrosphingosine reductase</name>
      <uniprot_id>Q2KIJ5</uniprot_id>
      <gene_name>KDSR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00097</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial</name>
      <uniprot_id>P42026</uniprot_id>
      <gene_name>NDUFS7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00099</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial</name>
      <uniprot_id>P17694</uniprot_id>
      <gene_name>NDUFS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00105</protein_accession>
      <name>Nicotinamide mononucleotide adenylyltransferase 1</name>
      <uniprot_id>Q0VD50</uniprot_id>
      <gene_name>NMNAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00106</protein_accession>
      <name>Nicotinamide mononucleotide adenylyltransferase 2</name>
      <uniprot_id>Q0VC59</uniprot_id>
      <gene_name>NMNAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00116</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 4</name>
      <uniprot_id>Q8SPU8</uniprot_id>
      <gene_name>DHRS4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00127</protein_accession>
      <name>Deoxyhypusine synthase</name>
      <uniprot_id>Q6EWQ6</uniprot_id>
      <gene_name>DHPS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00154</protein_accession>
      <name>Glyceraldehyde-3-phosphate dehydrogenase</name>
      <uniprot_id>P10096</uniprot_id>
      <gene_name>GAPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00209</protein_accession>
      <name>Glyceraldehyde-3-phosphate dehydrogenase, testis-specific</name>
      <uniprot_id>Q2KJE5</uniprot_id>
      <gene_name>GAPDHS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00259</protein_accession>
      <name>Lambda-crystallin homolog</name>
      <uniprot_id>Q8SPX7</uniprot_id>
      <gene_name>CRYL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00260</protein_accession>
      <name>Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial</name>
      <uniprot_id>Q07536</uniprot_id>
      <gene_name>ALDH6A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00261</protein_accession>
      <name>Squalene synthetase</name>
      <uniprot_id>Q32KR6</uniprot_id>
      <gene_name>FDFT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00262</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IX89</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00263</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>P03887</uniprot_id>
      <gene_name>MT-ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00266</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IXE1</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00267</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>B1NZU0</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00270</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q3L5H4</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00272</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1NZ26</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00273</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] flavoprotein 2, mitochondrial</name>
      <uniprot_id>P04394</uniprot_id>
      <gene_name>NDUFV2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00275</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0B8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00276</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>B1P0I6</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00286</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0J6</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00287</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4L</name>
      <uniprot_id>Q3L5T0</uniprot_id>
      <gene_name>ND4L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00288</protein_accession>
      <name>NADH dehydrogenase subunit 4</name>
      <uniprot_id>C5IX88</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00289</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q3L5J7</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00291</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>B1P078</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00292</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>B1P0N6</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00294</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P092</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00296</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>P03924</uniprot_id>
      <gene_name>MT-ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00298</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0N5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00301</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>B1NZ92</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00302</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>A4ZI01</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00303</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>P03920</uniprot_id>
      <gene_name>MT-ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00305</protein_accession>
      <name>NADH-ubiquinone oxidoreductase 75 kDa subunit, mitochondrial</name>
      <uniprot_id>P15690</uniprot_id>
      <gene_name>NDUFS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00307</protein_accession>
      <name>NADH dehydrogenase subunit 4</name>
      <uniprot_id>C5IX62</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00310</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>B1P044</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00312</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>B1P0M6</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00313</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0M2</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00318</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IX37</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00319</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>P03910</uniprot_id>
      <gene_name>MT-ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00321</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P027</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00326</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4L</name>
      <uniprot_id>P03902</uniprot_id>
      <gene_name>MT-ND4L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00329</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial</name>
      <uniprot_id>P23709</uniprot_id>
      <gene_name>NDUFS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00331</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>B1NZ38</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00336</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>P03898</uniprot_id>
      <gene_name>MT-ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00337</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>P03892</uniprot_id>
      <gene_name>MT-ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00340</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>B1P0L9</uniprot_id>
      <gene_name>ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00343</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1NZY8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00345</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 8, mitochondrial</name>
      <uniprot_id>P42028</uniprot_id>
      <gene_name>NDUFS8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00347</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IXC8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00348</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial</name>
      <uniprot_id>P25708</uniprot_id>
      <gene_name>NDUFV1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00349</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1NZB7</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00368</protein_accession>
      <name>Fatty acid synthase</name>
      <uniprot_id>Q71SP7</uniprot_id>
      <gene_name>FASN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00374</protein_accession>
      <name>Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrial</name>
      <uniprot_id>Q0P5C2</uniprot_id>
      <gene_name>MTHFD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00383</protein_accession>
      <name>Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase</name>
      <uniprot_id>Q148L6</uniprot_id>
      <gene_name>DHDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00448</protein_accession>
      <name>Isocitrate dehydrogenase [NADP], mitochondrial</name>
      <uniprot_id>Q04467</uniprot_id>
      <gene_name>IDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00454</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit gamma, mitochondrial</name>
      <uniprot_id>Q58CP0</uniprot_id>
      <gene_name>IDH3G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00471</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial</name>
      <uniprot_id>O77784</uniprot_id>
      <gene_name>IDH3B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00512</protein_accession>
      <name>Peroxisomal NADH pyrophosphatase NUDT12</name>
      <uniprot_id>Q29RH3</uniprot_id>
      <gene_name>NUDT12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00516</protein_accession>
      <name>Isocitrate dehydrogenase [NADP] cytoplasmic</name>
      <uniprot_id>Q9XSG3</uniprot_id>
      <gene_name>IDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00521</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit alpha, mitochondrial</name>
      <uniprot_id>P41563</uniprot_id>
      <gene_name>IDH3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00550</protein_accession>
      <name>3-hydroxyisobutyrate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q2HJD7</uniprot_id>
      <gene_name>HIBADH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00573</protein_accession>
      <name>L-lactate dehydrogenase A-like 6B</name>
      <uniprot_id>Q3T056</uniprot_id>
      <gene_name>LDHAL6B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00574</protein_accession>
      <name>L-lactate dehydrogenase B chain</name>
      <uniprot_id>Q5E9B1</uniprot_id>
      <gene_name>LDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00575</protein_accession>
      <name>L-lactate dehydrogenase A chain</name>
      <uniprot_id>P19858</uniprot_id>
      <gene_name>LDHA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00576</protein_accession>
      <name>L-lactate dehydrogenase</name>
      <uniprot_id>B0JYN3</uniprot_id>
      <gene_name>LDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00577</protein_accession>
      <name>L-lactate dehydrogenase</name>
      <uniprot_id>Q2KJG0</uniprot_id>
      <gene_name>LDHC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00585</protein_accession>
      <name>Flavin reductase</name>
      <uniprot_id>P52556</uniprot_id>
      <gene_name>BLVRB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00593</protein_accession>
      <name>4-trimethylaminobutyraldehyde dehydrogenase</name>
      <uniprot_id>Q2KJH9</uniprot_id>
      <gene_name>ALDH9A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00594</protein_accession>
      <name>L-xylulose reductase</name>
      <uniprot_id>Q1JP75</uniprot_id>
      <gene_name>DCXR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00597</protein_accession>
      <name>Dihydropteridine reductase</name>
      <uniprot_id>Q3T0Z7</uniprot_id>
      <gene_name>QDPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00601</protein_accession>
      <name>Retinal dehydrogenase 1</name>
      <uniprot_id>P48644</uniprot_id>
      <gene_name>ALDH1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00602</protein_accession>
      <name>Carbonyl reductase [NADPH] 1</name>
      <uniprot_id>Q3SZD7</uniprot_id>
      <gene_name>CBR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00606</protein_accession>
      <name>Hydroxysteroid 17-beta dehydrogenase 6</name>
      <uniprot_id>Q3T001</uniprot_id>
      <gene_name>HSD17B6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00616</protein_accession>
      <name>Malate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q32LG3</uniprot_id>
      <gene_name>MDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00620</protein_accession>
      <name>Malate dehydrogenase, cytoplasmic</name>
      <uniprot_id>Q3T145</uniprot_id>
      <gene_name>MDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00621</protein_accession>
      <name>Malate dehydrogenase</name>
      <uniprot_id>Q0QF29</uniprot_id>
      <gene_name>MDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00630</protein_accession>
      <name>Corticosteroid 11-beta-dehydrogenase isozyme 2</name>
      <uniprot_id>O77667</uniprot_id>
      <gene_name>HSD11B2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00631</protein_accession>
      <name>Alpha-aminoadipic semialdehyde synthase, mitochondrial</name>
      <uniprot_id>A8E657</uniprot_id>
      <gene_name>AASS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00677</protein_accession>
      <name>Aldehyde oxidase</name>
      <uniprot_id>P48034</uniprot_id>
      <gene_name>AOX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00689</protein_accession>
      <name>Dihydropyrimidine dehydrogenase [NADP+]</name>
      <uniprot_id>Q28007</uniprot_id>
      <gene_name>DPYD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00694</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q0QES8</uniprot_id>
      <gene_name>GAPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00784</protein_accession>
      <name>Sorbitol dehydrogenase</name>
      <uniprot_id>Q58D31</uniprot_id>
      <gene_name>SORD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00798</protein_accession>
      <name>Aldose reductase</name>
      <uniprot_id>P16116</uniprot_id>
      <gene_name>AKR1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00830</protein_accession>
      <name>Ecto-ADP-ribosyltransferase 5</name>
      <uniprot_id>Q0VC22</uniprot_id>
      <gene_name>ART5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00832</protein_accession>
      <name>Poly [ADP-ribose] polymerase 1</name>
      <uniprot_id>P18493</uniprot_id>
      <gene_name>PARP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00837</protein_accession>
      <name>Adenosylhomocysteinase</name>
      <uniprot_id>A5PKK6</uniprot_id>
      <gene_name>AHCYL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00838</protein_accession>
      <name>Adenosylhomocysteinase</name>
      <uniprot_id>A6QLP2</uniprot_id>
      <gene_name>AHCYL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00852</protein_accession>
      <name>Glutamine-dependent NAD(+) synthetase</name>
      <uniprot_id>Q3ZBF0</uniprot_id>
      <gene_name>NADSYN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00856</protein_accession>
      <name>Glutamate dehydrogenase 1, mitochondrial</name>
      <uniprot_id>P00366</uniprot_id>
      <gene_name>GLUD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00860</protein_accession>
      <name>Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial</name>
      <uniprot_id>A7YWE4</uniprot_id>
      <gene_name>ALDH4A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00866</protein_accession>
      <name>NADH-cytochrome b5 reductase 1</name>
      <uniprot_id>Q3MHW9</uniprot_id>
      <gene_name>CYB5R1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00886</protein_accession>
      <name>Oxidoreductase NAD-binding domain-containing protein 1</name>
      <uniprot_id>Q58DM7</uniprot_id>
      <gene_name>OXNAD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00893</protein_accession>
      <name>NADPH--cytochrome P450 reductase</name>
      <uniprot_id>Q3SYT8</uniprot_id>
      <gene_name>POR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00899</protein_accession>
      <name>NADH-cytochrome b5 reductase 3</name>
      <uniprot_id>P07514</uniprot_id>
      <gene_name>CYB5R3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00906</protein_accession>
      <name>Methylenetetrahydrofolate reductase</name>
      <uniprot_id>Q5I598</uniprot_id>
      <gene_name>MTHFR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00927</protein_accession>
      <name>Estradiol 17-beta-dehydrogenase 12</name>
      <uniprot_id>Q5E9H7</uniprot_id>
      <gene_name>HSD17B12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00931</protein_accession>
      <name>Glycerol-3-phosphate dehydrogenase [NAD+], cytoplasmic</name>
      <uniprot_id>Q5EA88</uniprot_id>
      <gene_name>GPD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00954</protein_accession>
      <name>Alpha-aminoadipic semialdehyde dehydrogenase</name>
      <uniprot_id>Q2KJC9</uniprot_id>
      <gene_name>ALDH7A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00961</protein_accession>
      <name>3-hydroxyacyl-CoA dehydrogenase type-2</name>
      <uniprot_id>O02691</uniprot_id>
      <gene_name>HSD17B10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00986</protein_accession>
      <name>Aldehyde dehydrogenase, dimeric NADP-preferring</name>
      <uniprot_id>P30907</uniprot_id>
      <gene_name>ALDH3A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00988</protein_accession>
      <name>Aldehyde dehydrogenase X, mitochondrial</name>
      <uniprot_id>P52476</uniprot_id>
      <gene_name>ALDH1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00989</protein_accession>
      <name>Aldehyde dehydrogenase family 3 member B1</name>
      <uniprot_id>Q1JPA0</uniprot_id>
      <gene_name>ALDH3B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00990</protein_accession>
      <name>Aldehyde dehydrogenase, mitochondrial</name>
      <uniprot_id>P20000</uniprot_id>
      <gene_name>ALDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00991</protein_accession>
      <name>Alcohol dehydrogenase class-3</name>
      <uniprot_id>Q3ZC42</uniprot_id>
      <gene_name>ADH5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00992</protein_accession>
      <name>Glucose-6-phosphate 1-dehydrogenase</name>
      <uniprot_id>Q0P587</uniprot_id>
      <gene_name>H6PD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00994</protein_accession>
      <name>Fatty acyl-CoA reductase 2</name>
      <uniprot_id>Q0P5J1</uniprot_id>
      <gene_name>FAR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01000</protein_accession>
      <name>Trans-2-enoyl-CoA reductase, mitochondrial</name>
      <uniprot_id>Q7YS70</uniprot_id>
      <gene_name>MECR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01001</protein_accession>
      <name>NAD(P) transhydrogenase, mitochondrial</name>
      <uniprot_id>P11024</uniprot_id>
      <gene_name>NNT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01002</protein_accession>
      <name>Inosine-5'-monophosphate dehydrogenase 2</name>
      <uniprot_id>Q3SWY3</uniprot_id>
      <gene_name>IMPDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01003</protein_accession>
      <name>Inosine-5'-monophosphate dehydrogenase</name>
      <uniprot_id>A0JNA3</uniprot_id>
      <gene_name>IMPDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01007</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 7C</name>
      <uniprot_id>Q1RMJ5</uniprot_id>
      <gene_name>DHRS7C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01008</protein_accession>
      <name>Carbonyl reductase 4</name>
      <uniprot_id>A4IFA7</uniprot_id>
      <gene_name>CBR4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01009</protein_accession>
      <name>3-hydroxybutyrate dehydrogenase type 2</name>
      <uniprot_id>Q3T046</uniprot_id>
      <gene_name>BDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01010</protein_accession>
      <name>D-beta-hydroxybutyrate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q02337</uniprot_id>
      <gene_name>BDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01011</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 7B</name>
      <uniprot_id>Q3T0R4</uniprot_id>
      <gene_name>DHRS7B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01012</protein_accession>
      <name>Hydroxysteroid dehydrogenase-like protein 2</name>
      <uniprot_id>A4FUZ6</uniprot_id>
      <gene_name>HSDL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01013</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 12</name>
      <uniprot_id>A6QP05</uniprot_id>
      <gene_name>DHRS12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01014</protein_accession>
      <name>Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating</name>
      <uniprot_id>Q3ZBE9</uniprot_id>
      <gene_name>NSDHL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01015</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 13</name>
      <uniprot_id>Q17QU7</uniprot_id>
      <gene_name>DHRS13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01016</protein_accession>
      <name>Pyrroline-5-carboxylate reductase 3</name>
      <uniprot_id>Q58D08</uniprot_id>
      <gene_name>PYCRL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01017</protein_accession>
      <name>15-hydroxyprostaglandin dehydrogenase [NAD+]</name>
      <uniprot_id>Q3T0C2</uniprot_id>
      <gene_name>HPGD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01018</protein_accession>
      <name>Pyrroline-5-carboxylate reductase 2</name>
      <uniprot_id>Q17QJ7</uniprot_id>
      <gene_name>PYCR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01019</protein_accession>
      <name>Dehydrogenase/reductase SDR family member 9</name>
      <uniprot_id>Q8HYR6</uniprot_id>
      <gene_name>DHRS9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01020</protein_accession>
      <name>Nuclear protein NP60</name>
      <uniprot_id>A4FUF0</uniprot_id>
      <gene_name>NP60</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01021</protein_accession>
      <name>Putative malate dehydrogenase 1B</name>
      <uniprot_id>A3KMX7</uniprot_id>
      <gene_name>MDH1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01022</protein_accession>
      <name>3 beta-hydroxysteroid dehydrogenase/Delta 5--&gt;4-isomerase</name>
      <uniprot_id>P14893</uniprot_id>
      <gene_name>HSD3B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01023</protein_accession>
      <name>Nucleoredoxin</name>
      <uniprot_id>A6QLU8</uniprot_id>
      <gene_name>NXN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01024</protein_accession>
      <name>Pyrroline-5-carboxylate reductase 1, mitochondrial</name>
      <uniprot_id>Q58DT4</uniprot_id>
      <gene_name>PYCR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01025</protein_accession>
      <name>Aldehyde dehydrogenase family 8 member A1</name>
      <uniprot_id>Q0P5F9</uniprot_id>
      <gene_name>ALDH8A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01026</protein_accession>
      <name>Inositol-3-phosphate synthase 1</name>
      <uniprot_id>Q2NL29</uniprot_id>
      <gene_name>ISYNA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01027</protein_accession>
      <name>Prostaglandin reductase 1</name>
      <uniprot_id>Q3SZJ4</uniprot_id>
      <gene_name>PTGR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01028</protein_accession>
      <name>Short chain dehydrogenase/reductase family 42E member 1</name>
      <uniprot_id>Q32L94</uniprot_id>
      <gene_name>SDR42E1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01029</protein_accession>
      <name>Prostaglandin reductase 2</name>
      <uniprot_id>Q32L99</uniprot_id>
      <gene_name>PTGR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01030</protein_accession>
      <name>17-beta-hydroxysteroid dehydrogenase 14</name>
      <uniprot_id>Q9MYP6</uniprot_id>
      <gene_name>HSD17B14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01339</protein_accession>
      <name>NDUFS7 protein</name>
      <uniprot_id>A8WFQ0</uniprot_id>
      <gene_name>NDUFS7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02120</protein_accession>
      <name>CYB5RL protein</name>
      <uniprot_id>A6QP65</uniprot_id>
      <gene_name>CYB5RL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02124</protein_accession>
      <name>CYB5R3 protein</name>
      <uniprot_id>A6H7G0</uniprot_id>
      <gene_name>CYB5R3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02254</protein_accession>
      <name>SIRT6 protein</name>
      <uniprot_id>A5D7K6</uniprot_id>
      <gene_name>SIRT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02255</protein_accession>
      <name>GPD1L protein</name>
      <uniprot_id>A6QQR7</uniprot_id>
      <gene_name>GPD1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02256</protein_accession>
      <name>P2X purinoceptor</name>
      <uniprot_id>O18952</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02257</protein_accession>
      <name>ND4</name>
      <uniprot_id>A1XEE4</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02258</protein_accession>
      <name>Sirtuin-like protein 2</name>
      <uniprot_id>B2CZT3</uniprot_id>
      <gene_name>SIRT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02259</protein_accession>
      <name>SIRT2 protein</name>
      <uniprot_id>A6QP26</uniprot_id>
      <gene_name>SIRT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02260</protein_accession>
      <name>C-terminal-binding protein 2</name>
      <uniprot_id>Q0VCQ1</uniprot_id>
      <gene_name>CTBP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:22 UTC</creation_date>
  <update_date>2020-03-13 16:24:39 UTC</update_date>
  <accession>BMDB0000903</accession>
  <secondary_accessions>
    <accession>BMDB00903</accession>
  </secondary_accessions>
  <name>Tetrahydrocortisone</name>
  <description>Tetrahydrocortisone belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Tetrahydrocortisone exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Tetrahydrocortisone can be converted into 17a,21-dihydroxy-5b-pregnane-3,11,20-trione through its interaction with the enzyme aldo-keto reductase family 1 member C4. In cattle, tetrahydrocortisone is involved in the metabolic pathway called the steroidogenesis pathway.</description>
  <synonyms>
    <synonym>(3a,5b)-3,17,21-Trihydroxy-pregnane-11,20-dione</synonym>
    <synonym>3,17-Dihydroxy-17-hydroxyacetyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-11-one</synonym>
    <synonym>3a,17,21-Trihydroxy-5a-pregnane-11,20-dione</synonym>
    <synonym>3a,17,21-Trihydroxy-5b-pregnane-11,20-dione</synonym>
    <synonym>3alpha,17,21-Trihydroxy-5beta-pregnane-11,20-dione</synonym>
    <synonym>3alpha,17,21-Trihydroxypregnane-11,20-dione</synonym>
    <synonym>3b,17,21-Trihydroxy-5a-pregnane-11,20-dione</synonym>
    <synonym>5a-Pregnan-3b,17a,21-triol-11,20-dion</synonym>
    <synonym>Ba 2681</synonym>
    <synonym>Tetrahydro e</synonym>
    <synonym>Tetrahydro-cortisone</synonym>
    <synonym>Tetrahydrocompound e</synonym>
    <synonym>Tetrahydrocortison</synonym>
    <synonym>Urocortisone</synonym>
  </synonyms>
  <chemical_formula>C21H32O5</chemical_formula>
  <average_molecular_weight>364.4758</average_molecular_weight>
  <monisotopic_moleculate_weight>364.224974134</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one</iupac_name>
  <traditional_iupac>(1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one</traditional_iupac>
  <cas_registry_number>53-05-4</cas_registry_number>
  <smiles>[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H32O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-15,18,22-23,26H,3-11H2,1-2H3/t12-,13-,14-,15-,18+,19-,20-,21-/m0/s1</inchi>
  <inchikey>SYGWGHVTLUBCEM-SDYDLROXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>11-oxosteroids</alternative_parent>
      <alternative_parent>17-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>11-oxosteroid</substituent>
      <substituent>17-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>190 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>364.4758</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>364.224974134</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H32O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H32O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-15,18,22-23,26H,3-11H2,1-2H3/t12-,13-,14-,15-,18+,19-,20-,21-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SYGWGHVTLUBCEM-SDYDLROXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>96.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroidogenesis</name>
      <smpdb_id>SMP0087238</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342915</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022310</foodb_id>
  <drugbank_id/>
  <chemspider_id>16735652</chemspider_id>
  <pubchem_compound_id>12444617</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Tetrahydrocortisone</wikipedia_id>
  <metlin_id>1915</metlin_id>
  <synthesis_reference>Baggett, Billy; Kinsella, Ralph A., Jr.; Doisy, Edward A.  Hydrolysis of conjugates of urinary corticoids with b-glucuronidase. II. The isolation and determination of tetrahydrocortisone.    Journal of Biological Chemistry  (1953),  203  1013-22.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:23 UTC</creation_date>
  <update_date>2020-04-16 20:40:03 UTC</update_date>
  <accession>BMDB0000904</accession>
  <secondary_accessions>
    <accession>BMDB00904</accession>
  </secondary_accessions>
  <name>Citrulline</name>
  <description>Citrulline, also known as Cit or δ-ureidonorvaline, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Citrulline is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Citrulline exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Citrulline exists in all living species, ranging from bacteria to humans. Citrulline participates in a number of enzymatic reactions, within cattle. In particular, Citrulline can be biosynthesized from carbamoyl phosphate and ornithine through its interaction with the enzyme ornithine carbamoyltransferase, mitochondrial. In addition, Citrulline and L-aspartic acid can be converted into argininosuccinic acid; which is catalyzed by the enzyme argininosuccinate synthase. In cattle, citrulline is involved in the metabolic pathway called the urea cycle pathway. Citrulline is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(S)-2-Amino-5-ureidopentanoic acid</synonym>
    <synonym>2-Amino-5-ureidovaleric acid</synonym>
    <synonym>alpha-Amino-delta-ureidovaleric acid</synonym>
    <synonym>Cit</synonym>
    <synonym>delta-Ureidonorvaline</synonym>
    <synonym>L-2-Amino-5-ureidovaleric acid</synonym>
    <synonym>N(5)-(Aminocarbonyl)-L-ornithine</synonym>
    <synonym>N5-(Aminocarbonyl)ornithine</synonym>
    <synonym>N5-Carbamoylornithine</synonym>
    <synonym>N(delta)-Carbamylornithine</synonym>
    <synonym>(S)-2-Amino-5-ureidopentanoate</synonym>
    <synonym>2-Amino-5-ureidovalerate</synonym>
    <synonym>a-Amino-delta-ureidovalerate</synonym>
    <synonym>a-Amino-delta-ureidovaleric acid</synonym>
    <synonym>alpha-Amino-delta-ureidovalerate</synonym>
    <synonym>Α-amino-δ-ureidovalerate</synonym>
    <synonym>Α-amino-δ-ureidovaleric acid</synonym>
    <synonym>Δ-ureidonorvaline</synonym>
    <synonym>L-2-Amino-5-ureidovalerate</synonym>
    <synonym>N(Δ)-carbamylornithine</synonym>
    <synonym>a-Amino-δ-ureidovalerate</synonym>
    <synonym>a-Amino-δ-ureidovaleric acid</synonym>
    <synonym>(2S)-2-Amino-5-(carbamoylamino)pentanoate</synonym>
    <synonym>(2S)-2-Amino-5-(carbamoylamino)pentanoic acid</synonym>
    <synonym>(S)-2-Amino-5-(aminocarbonyl)aminopentanoate</synonym>
    <synonym>(S)-2-Amino-5-(aminocarbonyl)aminopentanoic acid</synonym>
    <synonym>2-Amino-5-uredovalerate</synonym>
    <synonym>2-Amino-5-uredovaleric acid</synonym>
    <synonym>a-Amino-D-ureidovalerate</synonym>
    <synonym>a-Amino-D-ureidovaleric acid</synonym>
    <synonym>alpha-Amino-gamma-ureidovalerate</synonym>
    <synonym>alpha-Amino-gamma-ureidovaleric acid</synonym>
    <synonym>Amino-ureidovalerate</synonym>
    <synonym>Amino-ureidovaleric acid</synonym>
    <synonym>CIR</synonym>
    <synonym>Cytrulline</synonym>
    <synonym>D-Ureidonorvaline</synonym>
    <synonym>DL-Citrulline</synonym>
    <synonym>Gammaureidonorvaline</synonym>
    <synonym>H-Cit-OH</synonym>
    <synonym>L(+)-2-Amino-5-ureidovalerate</synonym>
    <synonym>L(+)-2-Amino-5-ureidovaleric acid</synonym>
    <synonym>L(+)-Citrulline</synonym>
    <synonym>L-2-Amino-5-ureido-valerate</synonym>
    <synonym>L-2-Amino-5-ureido-valeric acid</synonym>
    <synonym>L-Citrulline</synonym>
    <synonym>L-Cytrulline</synonym>
    <synonym>L-N5-Carbamoyl-ornithine</synonym>
    <synonym>N()-Carbamylornithine</synonym>
    <synonym>N(5)-(Aminocarbonyl)-DL-ornithine</synonym>
    <synonym>N-Carbamylornithine</synonym>
    <synonym>N5-(Aminocarbonyl)-L-ornithine</synonym>
    <synonym>N5-(Aminocarbonyl)-ornithine</synonym>
    <synonym>N5-Carbamoyl-L-ornithine</synonym>
    <synonym>N5-Carbamylornithine</synonym>
    <synonym>ND-Carbamylornithine</synonym>
    <synonym>Ndelta-carbamy-ornithine</synonym>
    <synonym>Ndelta-carbamylornithine</synonym>
    <synonym>Ngamma-carbamylornithine</synonym>
    <synonym>Sitrulline</synonym>
    <synonym>Ureidonorvaline</synonym>
    <synonym>Ureidovalerate</synonym>
    <synonym>Ureidovaleric acid</synonym>
  </synonyms>
  <chemical_formula>C6H13N3O3</chemical_formula>
  <average_molecular_weight>175.1857</average_molecular_weight>
  <monisotopic_moleculate_weight>175.095691297</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-5-(carbamoylamino)pentanoic acid</iupac_name>
  <traditional_iupac>L-citrulline</traditional_iupac>
  <cas_registry_number>372-75-8</cas_registry_number>
  <smiles>N[C@@H](CCCNC(N)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1</inchi>
  <inchikey>RHGKLRLOHDJJDR-BYPYZUCNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Isoureas</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Isourea</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>citrulline</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>235.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>212 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.19</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-5-(carbamoylamino)pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>175.1857</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>175.095691297</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCCNC(N)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13N3O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RHGKLRLOHDJJDR-BYPYZUCNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nitric Oxide Signaling Pathway</name>
      <smpdb_id>SMP0108206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4858</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4843</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>59.5-68.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>55.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wessels RH, Titgemeyer EC, St Jean G: Effect of amino acid supplementation on whole-body protein turnover in Holstein steers. J Anim Sci. 1997 Nov;75(11):3066-73.</reference_text>
          <pubmed_id>9374324</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>120-177</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Chromatography with spectrophotometric detection</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Barej W: Plasma amino acid indices and urinary 3-methyl histidine excretion in dairy cows in early lactation. Ann Rech Vet. 1986;17(2):153-7.</reference_text>
          <pubmed_id>3535614</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>71-84</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>88+/-15</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>20+/-5</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>34+/-12</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.9 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.7 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>59-111</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>36.8 +/- 20.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>37 +/- 20</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>184+/-74</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>31+/-14</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>19+/-7</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00327</kegg_id>
  <foodb_id>FDB011841</foodb_id>
  <drugbank_id>DB00155</drugbank_id>
  <chemspider_id>9367</chemspider_id>
  <pubchem_compound_id>9750</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16349</chebi_id>
  <meta_cyc_id>L-CITRULLINE</meta_cyc_id>
  <knapsack_id>C00001348</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34627</bigg_id>
  <wikipedia_id>Citrulline</wikipedia_id>
  <metlin_id>16</metlin_id>
  <synthesis_reference>Kakimoto, Toshio; Shibatani, Takeji; Nishimura, Noriyuki; Chibata, Ichiro. Enzymic production of L-citrulline by Pseudomonas putida. Applied Microbiology (1971), 22(6), 992-9.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00022</protein_accession>
      <name>Nitric oxide synthase, endothelial</name>
      <uniprot_id>P29473</uniprot_id>
      <gene_name>NOS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00069</protein_accession>
      <name>Nitric oxide synthase, inducible</name>
      <uniprot_id>Q27995</uniprot_id>
      <gene_name>NOS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00237</protein_accession>
      <name>Argininosuccinate synthase</name>
      <uniprot_id>P14568</uniprot_id>
      <gene_name>ASS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00611</protein_accession>
      <name>N(G),N(G)-dimethylarginine dimethylaminohydrolase 2</name>
      <uniprot_id>Q3SX44</uniprot_id>
      <gene_name>DDAH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00612</protein_accession>
      <name>N(G),N(G)-dimethylarginine dimethylaminohydrolase 1</name>
      <uniprot_id>P56965</uniprot_id>
      <gene_name>DDAH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00953</protein_accession>
      <name>Ornithine carbamoyltransferase, mitochondrial</name>
      <uniprot_id>Q9N1U7</uniprot_id>
      <gene_name>OTC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:24 UTC</creation_date>
  <update_date>2020-04-15 22:32:46 UTC</update_date>
  <accession>BMDB0000905</accession>
  <secondary_accessions>
    <accession>BMDB00905</accession>
  </secondary_accessions>
  <name>Deoxyadenosine monophosphate</name>
  <description/>
  <synonyms>
    <synonym>2'-dAMP</synonym>
    <synonym>2'-Deoxy-5'-adenosine monophosphate</synonym>
    <synonym>2'-Deoxy-AMP</synonym>
    <synonym>2'-Deoxyadenosine 5'-(dihydrogen phosphate)</synonym>
    <synonym>2'-Deoxyadenosine 5'-phosphate</synonym>
    <synonym>2'-Deoxyadenosine monophosphate</synonym>
    <synonym>2'-DEOXYADENOSINE-5'-monophosphATE</synonym>
    <synonym>2'-Deoxyadenylic acid</synonym>
    <synonym>dAMP</synonym>
    <synonym>Deoxy-5'-adenylic acid</synonym>
    <synonym>Deoxy-AMP</synonym>
    <synonym>Deoxyadenosine 5'-monophosphate</synonym>
    <synonym>Deoxyadenosine 5'-phosphate</synonym>
    <synonym>Deoxyadenylic acid</synonym>
    <synonym>2'-Deoxyadenosine 5'-monophosphate</synonym>
    <synonym>2'-Deoxy-5'-adenosine monophosphoric acid</synonym>
    <synonym>2'-Deoxyadenosine 5'-(dihydrogen phosphoric acid)</synonym>
    <synonym>2'-Deoxyadenosine 5'-phosphoric acid</synonym>
    <synonym>2'-Deoxyadenosine monophosphoric acid</synonym>
    <synonym>2'-DEOXYADENOSINE-5'-monophosphoric acid</synonym>
    <synonym>2'-Deoxyadenylate</synonym>
    <synonym>Deoxy-5'-adenylate</synonym>
    <synonym>Deoxyadenosine 5'-monophosphoric acid</synonym>
    <synonym>Deoxyadenosine 5'-phosphoric acid</synonym>
    <synonym>Deoxyadenylate</synonym>
    <synonym>2'-Deoxyadenosine 5'-monophosphoric acid</synonym>
    <synonym>Deoxyadenosine monophosphoric acid</synonym>
    <synonym>2'-Deoxy-5'-adenylate</synonym>
    <synonym>2'-Deoxy-5'-adenylic acid</synonym>
    <synonym>2'-Deoxy-adenosine 5'-phosphorate</synonym>
    <synonym>2'-Deoxy-adenosine 5'-phosphoric acid</synonym>
    <synonym>2'-Deoxyadenosine-5'-phosphate</synonym>
    <synonym>Deoxyadenosine-phosphate</synonym>
    <synonym>PdA</synonym>
    <synonym>2'-Deoxy-5'-adenosine monophosphate, ammonium salt</synonym>
    <synonym>2'-Deoxy-5'-adenosine monophosphate, disodium salt</synonym>
    <synonym>2'Deoxy-5'-AMP</synonym>
    <synonym>dAMP CPD</synonym>
  </synonyms>
  <chemical_formula>C10H14N5O6P</chemical_formula>
  <average_molecular_weight>331.2218</average_molecular_weight>
  <monisotopic_moleculate_weight>331.068169717</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>DAMP</traditional_iupac>
  <cas_registry_number>653-63-4</cas_registry_number>
  <smiles>NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1</smiles>
  <inchi>InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1</inchi>
  <inchikey>KHWCHTKSEGGWEX-RRKCRQDMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group  linked to the ribose moiety lacking a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine deoxyribonucleotides</sub_class>
    <direct_parent>Purine 2'-deoxyribonucleoside monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine 2'-deoxyribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2'-deoxyadenosine 5'-phosphate</external_descriptor>
      <external_descriptor>Deoxyribonucleotides</external_descriptor>
      <external_descriptor>purine 2'-deoxyribonucleoside 5'-monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>148 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>331.2218</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>331.068169717</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H14N5O6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KHWCHTKSEGGWEX-RRKCRQDMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>165.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4871</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447971</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00360</kegg_id>
  <foodb_id>FDB022311</foodb_id>
  <drugbank_id/>
  <chemspider_id>12079</chemspider_id>
  <pubchem_compound_id>12599</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17713</chebi_id>
  <meta_cyc_id>DAMP</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>34735</bigg_id>
  <wikipedia_id>Deoxyadenosine_monophosphate</wikipedia_id>
  <metlin_id>3461</metlin_id>
  <synthesis_reference>Scarano, E.  Incorporation of adenine-C14 into deoxyadenylic acid.    Bollettino - Societa Italiana di Biologia Sperimentale  (1958),  34  1620-1.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:26 UTC</creation_date>
  <update_date>2020-04-16 17:51:26 UTC</update_date>
  <accession>BMDB0000906</accession>
  <secondary_accessions>
    <accession>BMDB00906</accession>
  </secondary_accessions>
  <name>Trimethylamine</name>
  <description>Trimethylamine, also known as (CH3)3N or NME3, belongs to the class of organic compounds known as trialkylamines. These are organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen. Trimethylamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Trimethylamine exists in all living organisms, ranging from bacteria to humans. Trimethylamine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(CH3)3N</synonym>
    <synonym>N(CH3)3</synonym>
    <synonym>N,N,N-Trimethylamine</synonym>
    <synonym>N,N-Dimethylmethanamine</synonym>
    <synonym>NMe3</synonym>
    <synonym>TMA</synonym>
    <synonym>Tridimethylaminomethane</synonym>
    <synonym>Trimethylamin</synonym>
    <synonym>Dimethylmethaneamine</synonym>
    <synonym>N,N-Dimethyl-methanamine</synonym>
    <synonym>N-Trimethylamine</synonym>
    <synonym>Trimethylamine anhydrous</synonym>
    <synonym>Trimethylamine aqueous solution</synonym>
    <synonym>HI OF trimethylamine</synonym>
    <synonym>HCL OF Trimethylamine</synonym>
    <synonym>HBR OF Trimethylamine</synonym>
  </synonyms>
  <chemical_formula>C3H9N</chemical_formula>
  <average_molecular_weight>59.1103</average_molecular_weight>
  <monisotopic_moleculate_weight>59.073499293</monisotopic_moleculate_weight>
  <iupac_name>trimethylamine</iupac_name>
  <traditional_iupac>trimethylamine</traditional_iupac>
  <cas_registry_number>75-50-3</cas_registry_number>
  <smiles>CN(C)C</smiles>
  <inchi>InChI=1S/C3H9N/c1-4(2)3/h1-3H3</inchi>
  <inchikey>GETQZCLCWQTVFV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trialkylamines. These are organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>Trialkylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>methylamines</external_descriptor>
      <external_descriptor>tertiary amine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-117.1 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>890.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.16</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>trimethylamine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>59.1103</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>59.073499293</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H9N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H9N/c1-4(2)3/h1-3H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GETQZCLCWQTVFV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>3.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>19.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>7.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>240162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>242217</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 54 Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
          <pubmed_id>23394630</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in lactating Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
          <pubmed_id>23394630</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in mid-lactating primiparous Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Zhao S, Zhao J, Bu D, Sun P, Wang J, Dong Z: Metabolomics analysis reveals large effect of roughage types on rumen microbial metabolic profile in dairy cows. Lett Appl Microbiol. 2014 Jul;59(1):79-85. doi: 10.1111/lam.12247. Epub 2014 Apr  4.</reference_text>
          <pubmed_id>24617926</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>1114</chemspider_id>
  <foodb_id>FDB011944</foodb_id>
  <kegg_id>C00565</kegg_id>
  <pubchem_compound_id>1146</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>18139</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001433</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Trimethylamine</wikipedia_id>
  <metlin_id>3772</metlin_id>
  <meta_cyc_id>TRIMETHYLAMINE</meta_cyc_id>
  <synthesis_reference>Hirohata, Saneo; Tanba, Kiyonobu; Inoue, Kenichi.  Preparation of trimethylamine by zeolite-catalyzed reaction of methanol and ammonia.    Jpn. Kokai Tokkyo Koho  (2006),     5pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
      <pubmed_id>23394630</pubmed_id>
    </reference>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:27 UTC</creation_date>
  <update_date>2020-04-15 22:14:42 UTC</update_date>
  <accession>BMDB0000907</accession>
  <secondary_accessions>
    <accession>BMDB00907</accession>
  </secondary_accessions>
  <name>Sulfolithocholic acid</name>
  <description/>
  <synonyms>
    <synonym>Sulfolithocholate</synonym>
    <synonym>Sulpholithocholate</synonym>
    <synonym>Sulpholithocholic acid</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,10R,11S,14R,15R)-2,15-Dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,10R,11S,14R,15R)-2,15-Dimethyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoate</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,10R,11S,14R,15R)-2,15-Dimethyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O6S</chemical_formula>
  <average_molecular_weight>456.636</average_molecular_weight>
  <monisotopic_moleculate_weight>456.254559702</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>34669-57-3</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](CC[C@]12C)OS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C24H40O6S/c1-15(4-9-22(25)26)19-7-8-20-18-6-5-16-14-17(30-31(27,28)29)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21H,4-14H2,1-3H3,(H,25,26)(H,27,28,29)/t15-,16?,17-,18+,19-,20+,21+,23+,24-/m1/s1</inchi>
  <inchikey>AXDXVEYHEODSPN-YPLGJCPNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Sulfated steroids</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Bile acid, alcohol, or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfated steroid skeleton</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>456.636</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>456.254559702</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](CC[C@]12C)OS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O6S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O6S/c1-15(4-9-22(25)26)19-7-8-20-18-6-5-16-14-17(30-31(27,28)29)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21H,4-14H2,1-3H3,(H,25,26)(H,27,28,29)/t15-,16?,17-,18+,19-,20+,21+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AXDXVEYHEODSPN-YPLGJCPNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>100.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>117.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>98295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>98296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>98297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>163191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>163192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>163193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1599</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022312</foodb_id>
  <drugbank_id/>
  <chemspider_id/>
  <pubchem_compound_id>10253562</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Mills, Charles O.; Milkiewicz, Piotr; Molloy, David P.; Baxter, Debbie J.; Elias, Elwyn.  Synthesis, physical and biological properties of lithocholyl-lysyl-fluorescein: a fluorescent monohydroxy bile salt analog with cholestatic properties.    Biochimica et Biophysica Acta, General Subjects  (1997),  1336(3),  485-496.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:28 UTC</creation_date>
  <update_date>2020-04-15 22:14:43 UTC</update_date>
  <accession>BMDB0000908</accession>
  <secondary_accessions>
    <accession>BMDB00908</accession>
  </secondary_accessions>
  <name>5alpha-Cholestanol</name>
  <description/>
  <synonyms>
    <synonym>(3beta,5alpha)-Cholestan-3-ol</synonym>
    <synonym>Cholestanol</synonym>
    <synonym>Dihydrocholesterol</synonym>
    <synonym>Zymostanol</synonym>
    <synonym>(3b,5a)-Cholestan-3-ol</synonym>
    <synonym>(3Β,5α)-cholestan-3-ol</synonym>
    <synonym>5a-Cholestanol</synonym>
    <synonym>5Α-cholestanol</synonym>
    <synonym>5 alpha Cholestan 3 beta ol</synonym>
    <synonym>5 beta Cholestan 3 beta ol</synonym>
    <synonym>5 beta-Cholestan-3 beta-ol</synonym>
    <synonym>beta Cholestanol</synonym>
    <synonym>beta-Ol, 5 beta-cholestan-3</synonym>
    <synonym>5 alpha Cholestan 3 alpha ol</synonym>
    <synonym>5 alpha-Cholestan-3 beta-ol</synonym>
    <synonym>Cholestan 3 ol</synonym>
    <synonym>Cholestanol, (3alpha, 5beta)-isomer</synonym>
    <synonym>Coprosterol</synonym>
    <synonym>beta-Cholestanol</synonym>
    <synonym>5 beta-Cholestan-3 alpha-ol</synonym>
    <synonym>Coprostanol</synonym>
    <synonym>5 alpha-Cholestan-3 alpha-ol</synonym>
    <synonym>Cholestan-3-ol</synonym>
    <synonym>beta-Cholestan-3 beta-ol, 5</synonym>
    <synonym>3b-Hydroxy-5a-cholestane</synonym>
    <synonym>3b-Hydroxycholestane</synonym>
    <synonym>5a-Cholestan-3b-ol</synonym>
    <synonym>5a-Dihydrocholesterol</synonym>
    <synonym>Cholestan-3b-ol</synonym>
    <synonym>Dihydrocholesterin</synonym>
    <synonym>Epicholestanol</synonym>
    <synonym>5alpha-Cholestanol</synonym>
  </synonyms>
  <chemical_formula>C27H48O</chemical_formula>
  <average_molecular_weight>388.6694</average_molecular_weight>
  <monisotopic_moleculate_weight>388.370516158</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol</iupac_name>
  <traditional_iupac>(1S,2S,5S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol</traditional_iupac>
  <cas_registry_number>80-97-7</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</smiles>
  <inchi>InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>QYIXCDOBOSTCEI-QCYZZNICSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3beta-hydroxy steroid</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>cholestanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>140.0 - 142.0 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>388.6694</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>388.370516158</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H48O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QYIXCDOBOSTCEI-QCYZZNICSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>119.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1541</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB012122</foodb_id>
  <drugbank_id/>
  <chemspider_id>6413</chemspider_id>
  <pubchem_compound_id>6665</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>86570</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5864</metlin_id>
  <synthesis_reference>Bruce, W. F.; Ralls, J. O.  Dihydrocholesterol (b-cholestanol).    Organic Syntheses  (1937),  17  45-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:29 UTC</creation_date>
  <update_date>2020-03-13 16:24:43 UTC</update_date>
  <accession>BMDB0000909</accession>
  <secondary_accessions>
    <accession>BMDB00909</accession>
  </secondary_accessions>
  <name>trans-4-Hydroxycyclohexylacetic acid</name>
  <description/>
  <synonyms>
    <synonym>trans-4-Hydroxycyclohexylacetate</synonym>
    <synonym>4-Hydroxy-cyclohexyl acetic acid ester</synonym>
    <synonym>4-Hydroxycyclohexyl acetate</synonym>
    <synonym>2-[(1R,4R)-4-Hydroxycyclohexyl]acetate</synonym>
  </synonyms>
  <chemical_formula>C8H14O3</chemical_formula>
  <average_molecular_weight>158.195</average_molecular_weight>
  <monisotopic_moleculate_weight>158.094294314</monisotopic_moleculate_weight>
  <iupac_name>2-[(1r,4r)-4-hydroxycyclohexyl]acetic acid</iupac_name>
  <traditional_iupac>[(1r,4r)-4-hydroxycyclohexyl]acetic acid</traditional_iupac>
  <cas_registry_number>68592-23-4</cas_registry_number>
  <smiles>O[C@H]1CC[C@H](CC(O)=O)CC1</smiles>
  <inchi>InChI=1S/C8H14O3/c9-7-3-1-6(2-4-7)5-8(10)11/h6-7,9H,1-5H2,(H,10,11)/t6-,7-</inchi>
  <inchikey>ALTAAUJNHYWOGS-LJGSYFOKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Cyclohexanols</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclohexanol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(1r,4r)-4-hydroxycyclohexyl]acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>158.195</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>158.094294314</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1CC[C@H](CC(O)=O)CC1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H14O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H14O3/c9-7-3-1-6(2-4-7)5-8(10)11/h6-7,9H,1-5H2,(H,10,11)/t6-,7-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ALTAAUJNHYWOGS-LJGSYFOKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>63549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>63550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>63551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>120513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>120514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>120515</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022313</foodb_id>
  <drugbank_id/>
  <chemspider_id>17216021</chemspider_id>
  <pubchem_compound_id/>
  <pdbe_id/>
  <chebi_id>88508</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5865</metlin_id>
  <synthesis_reference>Ungnade, Herbert E.; Morriss, Francis V. Hydrogenation of phenolic acids. Journal of the American Chemical Society (1948), 70 1898-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:31 UTC</creation_date>
  <update_date>2020-03-13 16:24:43 UTC</update_date>
  <accession>BMDB0000910</accession>
  <secondary_accessions>
    <accession>BMDB00910</accession>
  </secondary_accessions>
  <name>Tridecanoic acid</name>
  <description>Tridecanoic acid, also known as N-tridecanoate or C13:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Tridecanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Tridecanoic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>C13:0</synonym>
    <synonym>N-TRIDECANOIC ACID</synonym>
    <synonym>N-Tridecoic acid</synonym>
    <synonym>Tridecylic acid</synonym>
    <synonym>N-TRIDECANOate</synonym>
    <synonym>N-Tridecoate</synonym>
    <synonym>Tridecylate</synonym>
    <synonym>Tridecanoate</synonym>
    <synonym>(S)-2-Aminotridecanoate</synonym>
    <synonym>(S)-2-Aminotridecanoic acid</synonym>
    <synonym>2S-Amino-tridecanoate</synonym>
    <synonym>2S-Amino-tridecanoic acid</synonym>
  </synonyms>
  <chemical_formula>C13H26O2</chemical_formula>
  <average_molecular_weight>214.3443</average_molecular_weight>
  <monisotopic_moleculate_weight>214.193280076</monisotopic_moleculate_weight>
  <iupac_name>tridecanoic acid</iupac_name>
  <traditional_iupac>tridecanoic acid</traditional_iupac>
  <cas_registry_number>638-53-9</cas_registry_number>
  <smiles>CCCCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C13H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13(14)15/h2-12H2,1H3,(H,14,15)</inchi>
  <inchikey>SZHOJFHSIKHZHA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>44.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.033 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>tridecanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>214.3443</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>214.193280076</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H26O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13(14)15/h2-12H2,1H3,(H,14,15)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SZHOJFHSIKHZHA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>63.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>27.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440414</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.284 +/- 0.003</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk. Meta-Analysis</comment>
      <references>
        <reference>
          <reference_text>Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.</reference_text>
          <pubmed_id>19038946</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.388 +/- 0.002</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.415 +/- 0.012</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.351 +/- 0.012</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93.</reference_text>
          <pubmed_id>5409465</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
          <pubmed_id>14168161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB010409</foodb_id>
  <chemspider_id>12013</chemspider_id>
  <kegg_id>C17076</kegg_id>
  <pubchem_compound_id>12530</pubchem_compound_id>
  <chebi_id>45919</chebi_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <drugbank_id>DB02448</drugbank_id>
  <meta_cyc_id/>
  <knapsack_id>C00007422</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Tridecylic acid</wikipedia_id>
  <metlin_id>5866</metlin_id>
  <synthesis_reference>Kehoe, Lawrence J.; Schell, Raymond A.  n-Heptanoic and n-tridecanoic acids from olefins, carbon monoxide and water.    Ger. Offen.  (1970),     17 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
      <pubmed_id>14168161</pubmed_id>
    </reference>
    <reference>
      <reference_text>Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93.</reference_text>
      <pubmed_id>5409465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.</reference_text>
      <pubmed_id>19038946</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:32 UTC</creation_date>
  <update_date>2020-04-14 22:48:34 UTC</update_date>
  <accession>BMDB0000912</accession>
  <secondary_accessions>
    <accession>BMDB00912</accession>
  </secondary_accessions>
  <name>Succinyladenosine</name>
  <description/>
  <synonyms>
    <synonym>(S)-N-(1,2-Dicarboxyethyl)-adenosine</synonym>
    <synonym>6-(1,2-Dicarboxyethylamino)-9-beta-D-ribofuranosylpurine</synonym>
    <synonym>N-(9-beta-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartic acid</synonym>
    <synonym>N-9-Ribofuranosyl-9H-purin-6-yl-aspartic acid</synonym>
    <synonym>Succinoadenosine</synonym>
    <synonym>6-(1,2-Dicarboxyethylamino)-9-b-D-ribofuranosylpurine</synonym>
    <synonym>6-(1,2-Dicarboxyethylamino)-9-β-D-ribofuranosylpurine</synonym>
    <synonym>N-(9-b-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartate</synonym>
    <synonym>N-(9-b-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartic acid</synonym>
    <synonym>N-(9-beta-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartate</synonym>
    <synonym>N-(9-Β-D-ribofuranosyl-9H-purin-6-yl)-L-aspartate</synonym>
    <synonym>N-(9-Β-D-ribofuranosyl-9H-purin-6-yl)-L-aspartic acid</synonym>
    <synonym>N-9-Ribofuranosyl-9H-purin-6-yl-aspartate</synonym>
    <synonym>6-(1,2-Dicarboxyethylamino)-9-beta-delta-ribofuranosylpurine</synonym>
    <synonym>N-(9-beta-delta-Ribofuranosyl-9H-purin-6-yl)-L-aspartate</synonym>
    <synonym>N-(9-beta-delta-Ribofuranosyl-9H-purin-6-yl)-L-aspartic acid</synonym>
  </synonyms>
  <chemical_formula>C14H17N5O8</chemical_formula>
  <average_molecular_weight>383.3135</average_molecular_weight>
  <monisotopic_moleculate_weight>383.107712545</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-yl}amino)butanedioic acid</iupac_name>
  <traditional_iupac>atp - adenosine triphosphate</traditional_iupac>
  <cas_registry_number>4542-23-8</cas_registry_number>
  <smiles>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N[C@@H](CC(O)=O)C(O)=O)N=CN=C12</smiles>
  <inchi>InChI=1S/C14H17N5O8/c20-2-6-9(23)10(24)13(27-6)19-4-17-8-11(15-3-16-12(8)19)18-5(14(25)26)1-7(21)22/h3-6,9-10,13,20,23-24H,1-2H2,(H,21,22)(H,25,26)(H,15,16,18)/t5-,6+,9+,10+,13+/m0/s1</inchi>
  <inchikey>VKGZCEJTCKHMRL-VWJPMABRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleosides</class>
    <sub_class/>
    <direct_parent>Purine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-alkylaminopurines</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aspartic acid and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-alkylaminopurine</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Aspartic acid or derivatives</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleoside</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-aspartic acid derivative</external_descriptor>
      <external_descriptor>adenosines</external_descriptor>
      <external_descriptor>amino dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>233 - 238 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-yl}amino)butanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>383.3135</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>383.107712545</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N[C@@H](CC(O)=O)C(O)=O)N=CN=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H17N5O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H17N5O8/c20-2-6-9(23)10(24)13(27-6)19-4-17-8-11(15-3-16-12(8)19)18-5(14(25)26)1-7(21)22/h3-6,9-10,13,20,23-24H,1-2H2,(H,21,22)(H,25,26)(H,15,16,18)/t5-,6+,9+,10+,13+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VKGZCEJTCKHMRL-VWJPMABRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>200.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>85.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>55317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>55318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>55319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>110448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>110449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>110450</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>17216022</chemspider_id>
  <foodb_id>FDB022314</foodb_id>
  <kegg_id/>
  <pubchem_compound_id>20849086</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>71169</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5867</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Buck, Ildiko; Reese, Colin B.  An unambiguous synthesis of adenylosuccinic acid and its constituent nucleoside.    Journal of the Chemical Society, Perkin Transactions 1:  Organic and Bio-Organic Chemistry (1972-1999)  (1990),   (11),  2937-42.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:33 UTC</creation_date>
  <update_date>2020-03-13 16:24:44 UTC</update_date>
  <accession>BMDB0000913</accession>
  <secondary_accessions>
    <accession>BMDB00913</accession>
  </secondary_accessions>
  <name>Vanillactic acid</name>
  <description/>
  <synonyms>
    <synonym>Vanillactate</synonym>
    <synonym>3-(3-Methoxy-4-hydroxyphenyl)lactate</synonym>
    <synonym>3-(3-Methoxy-4-hydroxyphenyl)lactic acid</synonym>
    <synonym>3-(4-Hydroxy-3-methoxyphenyl)-lactate</synonym>
    <synonym>3-(4-Hydroxy-3-methoxyphenyl)-lactic acid</synonym>
    <synonym>3-(4-Hydroxy-3-methoxyphenyl)lactate</synonym>
    <synonym>3-(4-Hydroxy-3-methoxyphenyl)lactic acid</synonym>
    <synonym>3-Methoxy-4-hydroxyphenyllactate</synonym>
    <synonym>3-Methoxy-4-hydroxyphenyllactic acid</synonym>
    <synonym>4-Hydroxy-3-methoxyphenyllactic acid</synonym>
    <synonym>b-(4-Hydroxy-3-methoxyphenyl)lactate</synonym>
    <synonym>b-(4-Hydroxy-3-methoxyphenyl)lactic acid</synonym>
    <synonym>beta-(4-Hydroxy-3-methoxyphenyl)lactate</synonym>
    <synonym>beta-(4-Hydroxy-3-methoxyphenyl)lactic acid</synonym>
    <synonym>Vanillyllactate</synonym>
    <synonym>Vanillyllactic acid</synonym>
    <synonym>VLA</synonym>
    <synonym>Vanillylactic acid</synonym>
    <synonym>2-Hydroxy-3-(4-hydroxy-3-methoxyphenyl)propanoate</synonym>
    <synonym>Vanillactic acid</synonym>
  </synonyms>
  <chemical_formula>C10H12O5</chemical_formula>
  <average_molecular_weight>212.1993</average_molecular_weight>
  <monisotopic_moleculate_weight>212.068473494</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propanoic acid</iupac_name>
  <traditional_iupac>vanillactic acid</traditional_iupac>
  <cas_registry_number>2475-56-1</cas_registry_number>
  <smiles>COC1=CC(CC(O)C(O)=O)=CC=C1O</smiles>
  <inchi>InChI=1S/C10H12O5/c1-15-9-5-6(2-3-7(9)11)4-8(12)10(13)14/h2-3,5,8,11-12H,4H2,1H3,(H,13,14)</inchi>
  <inchikey>SVYIZYRTOYHQRE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Phenylpropanoic acids</class>
    <sub_class/>
    <direct_parent>Phenylpropanoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>212.1993</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>212.068473494</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC(CC(O)C(O)=O)=CC=C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12O5/c1-15-9-5-6(2-3-7(9)11)4-8(12)10(13)14/h2-3,5,8,11-12H,4H2,1H3,(H,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SVYIZYRTOYHQRE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>86.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345033</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022315</foodb_id>
  <chemspider_id>141152</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>160637</pubchem_compound_id>
  <chebi_id>1240674</chebi_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5868</metlin_id>
  <synthesis_reference>Wong, Henry N. C.; Xu, Zun Le; Chang, Hson Mou; Lee, Chi Ming.  Compounds from Danshen.  6.  A modified synthesis of (±)-b-aryllactic acids.    Synthesis  (1992),   (8),  793-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:34 UTC</creation_date>
  <update_date>2020-04-15 22:14:43 UTC</update_date>
  <accession>BMDB0000916</accession>
  <secondary_accessions>
    <accession>BMDB00916</accession>
  </secondary_accessions>
  <name>Uroporphyrin III</name>
  <description>Uroporphyrin III belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure. Uroporphyrin III is possibly soluble (in water) and a weakly acidic compound (based on its pKa). Uroporphyrin III exists in all living species, ranging from bacteria to humans. In cattle, uroporphyrin iii is involved in the metabolic pathway called the porphyrin metabolism pathway. Uroporphyrin III is a potentially toxic compound.</description>
  <synonyms>
    <synonym>3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropionic acid</synonym>
    <synonym>3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropionate</synonym>
    <synonym>3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropanoate</synonym>
    <synonym>3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropanoic acid</synonym>
    <synonym>3,8,13,17-Tetramethyl-2,7,12,18-porphinetetrapropionate</synonym>
    <synonym>3,8,13,17-Tetramethyl-2,7,12,18-porphinetetrapropionic acid</synonym>
    <synonym>Coproporphyrin III</synonym>
  </synonyms>
  <chemical_formula>C40H38N4O16</chemical_formula>
  <average_molecular_weight>830.7469</average_molecular_weight>
  <monisotopic_moleculate_weight>830.228281188</monisotopic_moleculate_weight>
  <iupac_name>3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>18273-06-8</cas_registry_number>
  <smiles>OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4CC(O)=O)/C(CC(O)=O)=C3CCC(O)=O</smiles>
  <inchi>InChI=1S/C40H38N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-27-19(3-7-35(49)50)22(10-38(55)56)30(43-27)15-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)16-31-23(11-39(57)58)18(2-6-34(47)48)26(42-31)13-25(17)41-29/h13-16,41,44H,1-12H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-</inchi>
  <inchikey>VZVFNUAIRVUCEW-UJJXFSCMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>830.7469</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>830.228281188</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4CC(O)=O)/C(CC(O)=O)=C3CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C40H38N4O16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C40H38N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-27-19(3-7-35(49)50)22(10-38(55)56)30(43-27)15-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)16-31-23(11-39(57)58)18(2-6-34(47)48)26(42-31)13-25(17)41-29/h13-16,41,44H,1-12H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VZVFNUAIRVUCEW-UJJXFSCMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>355.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>201.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>85.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367914</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB005664</foodb_id>
  <chemspider_id>16736727</chemspider_id>
  <kegg_id>C02469</kegg_id>
  <pubchem_compound_id/>
  <chebi_id>15436</chebi_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5870</metlin_id>
  <synthesis_reference>Kajiwara, Masahiro; Mizutani, Minoru; Kojima, Ichiro.  Manufacture of uroporphyrin III with Arthrobacter.    Jpn. Kokai Tokkyo Koho  (1993),     7 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:35 UTC</creation_date>
  <update_date>2020-04-15 22:14:44 UTC</update_date>
  <accession>BMDB0000917</accession>
  <secondary_accessions>
    <accession>BMDB00917</accession>
  </secondary_accessions>
  <name>Ursocholic acid</name>
  <description/>
  <synonyms>
    <synonym>(3alpha,5beta,7beta,12alpha)-3,7,12-Trihydroxycholan-24-Oic acid</synonym>
    <synonym>3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-Oic acid</synonym>
    <synonym>3alpha,7beta,12alpha-Trihydroxy-5beta-cholanic acid</synonym>
    <synonym>7-Epicholic acid</synonym>
    <synonym>7beta-Hydroxyisocholic acid</synonym>
    <synonym>(3a,5b,7b,12a)-3,7,12-Trihydroxycholan-24-Oate</synonym>
    <synonym>(3a,5b,7b,12a)-3,7,12-Trihydroxycholan-24-Oic acid</synonym>
    <synonym>(3alpha,5beta,7beta,12alpha)-3,7,12-Trihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5β,7β,12α)-3,7,12-trihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5β,7β,12α)-3,7,12-trihydroxycholan-24-Oic acid</synonym>
    <synonym>3a,7b,12a-Trihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,7b,12a-Trihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-Oate</synonym>
    <synonym>3Α,7β,12α-trihydroxy-5β-cholan-24-Oate</synonym>
    <synonym>3Α,7β,12α-trihydroxy-5β-cholan-24-Oic acid</synonym>
    <synonym>3a,7b,12a-Trihydroxy-5b-cholanate</synonym>
    <synonym>3a,7b,12a-Trihydroxy-5b-cholanic acid</synonym>
    <synonym>3alpha,7beta,12alpha-Trihydroxy-5beta-cholanate</synonym>
    <synonym>3Α,7β,12α-trihydroxy-5β-cholanate</synonym>
    <synonym>3Α,7β,12α-trihydroxy-5β-cholanic acid</synonym>
    <synonym>7-Epicholate</synonym>
    <synonym>7b-Hydroxyisocholate</synonym>
    <synonym>7b-Hydroxyisocholic acid</synonym>
    <synonym>7beta-Hydroxyisocholate</synonym>
    <synonym>7Β-hydroxyisocholate</synonym>
    <synonym>7Β-hydroxyisocholic acid</synonym>
    <synonym>Ursocholate</synonym>
    <synonym>3a,7b,12a-Trihydroxy-5b-cholanoate</synonym>
    <synonym>3a,7b,12a-Trihydroxy-5b-cholanoic acid</synonym>
    <synonym>3a,7b,12a-Trihydroxycholanate</synonym>
    <synonym>3a,7b,12a-Trihydroxycholanic acid</synonym>
    <synonym>3 alpha,7 beta,12 alpha-Trihydroxy-5 beta-cholan-24-Oic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O5</chemical_formula>
  <average_molecular_weight>408.5714</average_molecular_weight>
  <monisotopic_moleculate_weight>408.28757439</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>ursocholic acid</traditional_iupac>
  <cas_registry_number>2955-27-3</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1</inchi>
  <inchikey>BHQCQFFYRZLCQQ-UTLSPDKDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Trihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>bile acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>408.5714</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>408.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHQCQFFYRZLCQQ-UTLSPDKDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>110.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>93740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>157565</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022316</foodb_id>
  <chemspider_id>109088</chemspider_id>
  <kegg_id>C17644</kegg_id>
  <pubchem_compound_id>122340</pubchem_compound_id>
  <chebi_id>81240</chebi_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5871</metlin_id>
  <synthesis_reference>Terada, Masaki; Sato, Manabu; Horie, Yoshiaki; Takatsu, Mitsumune; Minami, Junichi.  Production of ursocholic acid.    Jpn. Kokai Tokkyo Koho  (1986),     9 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:36 UTC</creation_date>
  <update_date>2020-04-16 17:53:18 UTC</update_date>
  <accession>BMDB0000918</accession>
  <secondary_accessions>
    <accession>BMDB00918</accession>
  </secondary_accessions>
  <name>CE(18:1(9Z))</name>
  <description>Ce(18:1(9Z)), also known as ce(18:1) or oleoylcholesterol, belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety. Thus, ce(18:1(9Z)) is considered to be a sterol lipid molecule. Ce(18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.</description>
  <synonyms>
    <synonym>1-Oleoyl-cholesterol</synonym>
    <synonym>18:1(9Z) Cholesterol ester</synonym>
    <synonym>3beta-Hydroxy-5-cholestene 3-oleate</synonym>
    <synonym>5-Cholesten-3b-ol 3-oleate</synonym>
    <synonym>CE(18:1)</synonym>
    <synonym>CE(18:1/0:0)</synonym>
    <synonym>CE(18:1n9/0:0)</synonym>
    <synonym>CE(18:1W9/0:0)</synonym>
    <synonym>Cholest-5-en-3-beta-yl oleate</synonym>
    <synonym>Cholest-5-en-3-ol (3b)-(Z)-9-octadecenoate</synonym>
    <synonym>Cholest-5-en-3-ol (3b)-(Z)-9-octadecenoic acid</synonym>
    <synonym>Cholest-5-en-3b-yl</synonym>
    <synonym>Cholesterol 1-(9Z-octadecenoate</synonym>
    <synonym>Cholesterol 1-(9Z-octadecenoate)</synonym>
    <synonym>Cholesterol 1-(9Z-octadecenoic acid</synonym>
    <synonym>Cholesterol 1-(9Z-octadecenoic acid)</synonym>
    <synonym>Cholesterol 3beta-oleate</synonym>
    <synonym>Cholesterol ester(18:1)</synonym>
    <synonym>Cholesterol ester(18:1/0:0)</synonym>
    <synonym>Cholesterol ester(18:1n9/0:0)</synonym>
    <synonym>Cholesterol ester(18:1W9/0:0)</synonym>
    <synonym>Cholesteroyl-oleate</synonym>
    <synonym>Cholesteryl 1-oleoate</synonym>
    <synonym>Cholesteryl 1-oleoic acid</synonym>
    <synonym>Cholesteryl cis-9-octadecenoate</synonym>
    <synonym>Cholesteryl cis-9-octadecenoic acid</synonym>
    <synonym>Cholesteryl oleate</synonym>
    <synonym>Cholesteryl oleate-9,10-3H</synonym>
    <synonym>Cholesteryl oleate-9,10-t2</synonym>
    <synonym>Cholesteryl oleic ester</synonym>
    <synonym>Cholesteryl [9,10-3H]oleate</synonym>
    <synonym>Cholesteryl-beta-D-glucoside</synonym>
    <synonym>Cholesteryl-beta-delta-glucoside</synonym>
    <synonym>Oleic acid cholesteryl ester</synonym>
    <synonym>Oleoylcholesterol</synonym>
    <synonym>Cholesteryl 1-(9Z-octadecenoate)</synonym>
    <synonym>Cholesterol 1-oleoic acid</synonym>
    <synonym>Cholesteryl 1-(9Z-octadecenoic acid)</synonym>
    <synonym>Cholesterol 1-oleoate</synonym>
    <synonym>1-(9Z-Octadecenoyl)-cholesterol</synonym>
    <synonym>CE(18:1(9Z))</synonym>
  </synonyms>
  <chemical_formula>C45H78O2</chemical_formula>
  <average_molecular_weight>651.117</average_molecular_weight>
  <monisotopic_moleculate_weight>650.600181752</monisotopic_moleculate_weight>
  <iupac_name>(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-octadec-9-enoate</iupac_name>
  <traditional_iupac>(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-octadec-9-enoate</traditional_iupac>
  <cas_registry_number>303-43-5</cas_registry_number>
  <smiles>CCCCCCCC\C=C/CCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C</smiles>
  <inchi>InChI=1S/C45H78O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h14-15,26,35-36,38-42H,7-13,16-25,27-34H2,1-6H3/b15-14-/t36-,38+,39?,40?,41?,42?,44+,45-/m1/s1</inchi>
  <inchikey>RJECHNNFRHZQKU-DVPYOPPASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Steroid esters</sub_class>
    <direct_parent>Cholesteryl esters</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Cholesterols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cholestane-skeleton</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesteryl ester</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>10.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-8.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>14.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-octadec-9-enoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>651.117</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>650.600181752</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCC\C=C/CCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C45H78O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C45H78O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h14-15,26,35-36,38-42H,7-13,16-25,27-34H2,1-6H3/b15-14-/t36-,38+,39?,40?,41?,42?,44+,45-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RJECHNNFRHZQKU-DVPYOPPASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>26.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>204.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>87.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>33041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>884812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>884813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>884814</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>23.5 +/- 15.68</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>23.5 +/- 15.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by FAMEs/GC–MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022317</foodb_id>
  <chemspider_id>26263151</chemspider_id>
  <kegg_id>C14641</kegg_id>
  <pubchem_compound_id>50938266</pubchem_compound_id>
  <chebi_id>46898</chebi_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5872</metlin_id>
  <synthesis_reference>Sripada P K  Synthesis of single- and double-13C-labeled cholesterol oleate.    Chemistry and physics of lipids  (1988),  48(1-2),  147-51.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:38 UTC</creation_date>
  <update_date>2020-03-13 16:24:46 UTC</update_date>
  <accession>BMDB0000920</accession>
  <secondary_accessions>
    <accession>BMDB00920</accession>
  </secondary_accessions>
  <name>11a-Hydroxyprogesterone</name>
  <description/>
  <synonyms>
    <synonym>11-Hydroxyprogesterone</synonym>
    <synonym>11a-Hydroxy-pregn-4-ene-3,20-dione</synonym>
    <synonym>11a-Hydroxy-progesterone</synonym>
    <synonym>11a-Hydroxypregn-4-ene-3,20-dione</synonym>
    <synonym>4-Pregnene-11a-ol-3,20-dione</synonym>
    <synonym>Pregn-4-en-11a-ol-3,20-dione</synonym>
    <synonym>11Α-hydroxyprogesterone</synonym>
    <synonym>11a-Hydroxyprogesterone</synonym>
  </synonyms>
  <chemical_formula>C21H30O3</chemical_formula>
  <average_molecular_weight>330.4611</average_molecular_weight>
  <monisotopic_moleculate_weight>330.219494826</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10S,11S,15S,17R)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10S,11S,15S,17R)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</traditional_iupac>
  <cas_registry_number>312-90-3</cas_registry_number>
  <smiles>[H][C@@]12CCC(C(C)=O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16?,17-,18+,19+,20-,21+/m0/s1</inchi>
  <inchikey>BFZHCUBIASXHPK-ODYOLWGQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Pregnane steroids</sub_class>
    <direct_parent>Gluco/mineralocorticoids, progestogins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>11-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>11-alpha-hydroxysteroid</substituent>
      <substituent>11-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>222 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.05 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.36</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10S,11S,15S,17R)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>330.4611</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>330.219494826</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(C(C)=O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H30O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16?,17-,18+,19+,20-,21+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BFZHCUBIASXHPK-ODYOLWGQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>94.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359511</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022318</foodb_id>
  <chemspider_id>389106</chemspider_id>
  <kegg_id>C03747</kegg_id>
  <pubchem_compound_id>440105</pubchem_compound_id>
  <chebi_id>16076</chebi_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5873</metlin_id>
  <synthesis_reference>11b-Hydroxylation of steroids.    (1957),     GB  769999  19570313  CAN 51:64205  AN 1957:64205</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:39 UTC</creation_date>
  <update_date>2020-04-15 22:02:54 UTC</update_date>
  <accession>BMDB0000921</accession>
  <secondary_accessions>
    <accession>BMDB00921</accession>
  </secondary_accessions>
  <name>Cholestenone</name>
  <description/>
  <synonyms>
    <synonym>4-Cholesten-3-one</synonym>
    <synonym>(17b)-17-Octylandrost-4-en-3-one</synonym>
    <synonym>3-Oxocholest-4-ene</synonym>
    <synonym>Cholest-4-en-3-one</synonym>
    <synonym>D4-Cholesten-3-one</synonym>
    <synonym>D4-Cholestenone</synonym>
    <synonym>(+)-4-Cholesten-3-one</synonym>
    <synonym>(17beta)-17-Octylandrost-4-en-3-one</synonym>
    <synonym>(17Β)-17-octylandrost-4-en-3-one</synonym>
    <synonym>4-Cholestenone</synonym>
    <synonym>Cholesterone</synonym>
    <synonym>delta4-Cholesten-3-one</synonym>
    <synonym>delta4-Cholestenone</synonym>
    <synonym>Δ4-cholesten-3-one</synonym>
    <synonym>Δ4-cholestenone</synonym>
  </synonyms>
  <chemical_formula>C27H44O</chemical_formula>
  <average_molecular_weight>384.6377</average_molecular_weight>
  <monisotopic_moleculate_weight>384.33921603</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</traditional_iupac>
  <cas_registry_number>601-57-0</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</smiles>
  <inchi>InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h17-19,22-25H,6-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>NYOXRYYXRWJDKP-GYKMGIIDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-oxo Delta(4)-steroid</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>cholestanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>79 - 82 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>384.6377</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>384.33921603</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H44O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h17-19,22-25H,6-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NYOXRYYXRWJDKP-GYKMGIIDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>119.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>49.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336813</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022319</foodb_id>
  <chemspider_id>82602</chemspider_id>
  <kegg_id>C00599</kegg_id>
  <pubchem_compound_id>91477</pubchem_compound_id>
  <chebi_id>16175</chebi_id>
  <phenol_explorer_compound_id/>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id>CPD-323</meta_cyc_id>
  <knapsack_id>C00036093</knapsack_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>3898</metlin_id>
  <synthesis_reference>Mori, Susumu.  Steroids. IX. A new synthesis of cholestenone and the addition of hypochlorous acid to cholesterol.    Nippon Kagaku Kaishi (1921-47)  (1952),  Pure Chem. Sect. 73  547-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:40 UTC</creation_date>
  <update_date>2020-04-15 22:14:45 UTC</update_date>
  <accession>BMDB0000922</accession>
  <secondary_accessions>
    <accession>BMDB00922</accession>
  </secondary_accessions>
  <name>Taurallocholic acid</name>
  <description/>
  <synonyms>
    <synonym>(2S)-2-Amino-3-(1H-indol-3-yl)propanoic acid</synonym>
    <synonym>(S)-alpha-Amino-1H-indole-3-propanoic acid</synonym>
    <synonym>(S)-alpha-Amino-beta-(3-indolyl)-propionic acid</synonym>
    <synonym>(S)-Tryptophan</synonym>
    <synonym>L-(-)-Tryptophan</synonym>
    <synonym>L-beta-3-Indolylalanine</synonym>
    <synonym>Trp</synonym>
    <synonym>Tryptophan</synonym>
    <synonym>W</synonym>
    <synonym>(2S)-2-Amino-3-(1H-indol-3-yl)propanoate</synonym>
    <synonym>(S)-a-Amino-1H-indole-3-propanoate</synonym>
    <synonym>(S)-a-Amino-1H-indole-3-propanoic acid</synonym>
    <synonym>(S)-alpha-Amino-1H-indole-3-propanoate</synonym>
    <synonym>(S)-Α-amino-1H-indole-3-propanoate</synonym>
    <synonym>(S)-Α-amino-1H-indole-3-propanoic acid</synonym>
    <synonym>(S)-a-Amino-b-(3-indolyl)-propionate</synonym>
    <synonym>(S)-a-Amino-b-(3-indolyl)-propionic acid</synonym>
    <synonym>(S)-alpha-Amino-beta-(3-indolyl)-propionate</synonym>
    <synonym>(S)-Α-amino-β-(3-indolyl)-propionate</synonym>
    <synonym>(S)-Α-amino-β-(3-indolyl)-propionic acid</synonym>
    <synonym>L-b-3-Indolylalanine</synonym>
    <synonym>L-Β-3-indolylalanine</synonym>
    <synonym>(-)-Tryptophan</synonym>
    <synonym>(L)-Tryptophan</synonym>
    <synonym>(S)-1H-Indole-3-alanine</synonym>
    <synonym>(S)-2-Amino-3-(3-indolyl)propionic acid</synonym>
    <synonym>(S)-a-Amino-b-indolepropionate</synonym>
    <synonym>(S)-a-Amino-b-indolepropionic acid</synonym>
    <synonym>(S)-a-Aminoindole-3-propionate</synonym>
    <synonym>(S)-a-Aminoindole-3-propionic acid</synonym>
    <synonym>(S)-alpha-Amino-beta-indolepropionate</synonym>
    <synonym>(S)-alpha-Amino-beta-indolepropionic acid</synonym>
    <synonym>(S)-alpha-Aminoindole-3-propionate</synonym>
    <synonym>(S)-alpha-Aminoindole-3-propionic acid</synonym>
    <synonym>1-beta-3-Indolylalanine</synonym>
    <synonym>1beta-3-Indolylalanine</synonym>
    <synonym>1H-Indole-3-alanine</synonym>
    <synonym>2-Amino-3-indolylpropanoate</synonym>
    <synonym>2-Amino-3-indolylpropanoic acid</synonym>
    <synonym>3-(1H-indol-3-yl)-L-Alanine</synonym>
    <synonym>3-indol-3-Ylalanine</synonym>
    <synonym>Alpha'-amino-3-indolepropionic acid</synonym>
    <synonym>alpha-Aminoindole-3-propionic acid</synonym>
    <synonym>Ardeytropin</synonym>
    <synonym>H-TRP-OH</synonym>
    <synonym>Indole-3-alanine</synonym>
    <synonym>Kalma</synonym>
    <synonym>L-alpha-Amino-3-indolepropionic acid</synonym>
    <synonym>L-alpha-Aminoindole-3-propionic acid</synonym>
    <synonym>L-Tryptofan</synonym>
    <synonym>L-Tryptophane</synonym>
    <synonym>Lopac-T-0254</synonym>
    <synonym>Lyphan</synonym>
    <synonym>Optimax</synonym>
    <synonym>Pacitron</synonym>
    <synonym>Sedanoct</synonym>
    <synonym>Triptofano</synonym>
    <synonym>Trofan</synonym>
    <synonym>Tryptacin</synonym>
    <synonym>Tryptan</synonym>
    <synonym>Tryptophane</synonym>
    <synonym>Tryptophanum</synonym>
    <synonym>Ardeydorm</synonym>
    <synonym>L Tryptophan</synonym>
    <synonym>L-Tryptophan-ratiopharm</synonym>
    <synonym>Merck brand OF tryptophan</synonym>
    <synonym>Niddapharm brand OF tryptophan</synonym>
    <synonym>ICN brand OF tryptophan</synonym>
    <synonym>Levotryptophan</synonym>
    <synonym>PMS Tryptophan</synonym>
    <synonym>PMS-Tryptophan</synonym>
    <synonym>Ratiopharm brand OF tryptophan</synonym>
    <synonym>Esparma brand OF tryptophan</synonym>
    <synonym>Ratio-tryptophan</synonym>
    <synonym>L Tryptophan ratiopharm</synonym>
    <synonym>Naturruhe</synonym>
    <synonym>Tryptophan metabolism alterations</synonym>
    <synonym>Ardeypharm brand OF tryptophan</synonym>
    <synonym>Kalma brand OF tryptophan</synonym>
    <synonym>Pharmascience brand OF tryptophan</synonym>
    <synonym>Upsher-smith brand OF tryptophan</synonym>
    <synonym>Ratio tryptophan</synonym>
    <synonym>Taurallocholate</synonym>
  </synonyms>
  <chemical_formula>C26H45NO7S</chemical_formula>
  <average_molecular_weight>515.703</average_molecular_weight>
  <monisotopic_moleculate_weight>515.291673489</monisotopic_moleculate_weight>
  <iupac_name>2-[(4R)-4-[(2S,5R,7R,9R,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid</iupac_name>
  <traditional_iupac>2-[(4R)-4-[(2S,5R,7R,9R,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethanesulfonic acid</traditional_iupac>
  <cas_registry_number>73-22-3</cas_registry_number>
  <smiles>[H][C@]12C[C@H](O)CC[C@]1(C)C1C[C@H](O)[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[C@H](C)CCC(=O)NCCS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16-,17-,18-,19?,20?,21-,22+,24?,25+,26-/m1/s1</inchi>
  <inchikey>WBWWGRHZICKQGZ-ZKUTWGMOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Indolyl carboxylic acids and derivatives</sub_class>
    <direct_parent>Indolyl carboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alkylindoles</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alkylindole</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indole</substituent>
      <substituent>Indolyl carboxylic acid derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>erythrose 4-phosphate/phosphoenolpyruvate family amino acid</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
      <external_descriptor>tryptophan</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4R)-4-[(2S,5R,7R,9R,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>515.703</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>515.291673489</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]12C[C@H](O)CC[C@]1(C)C1C[C@H](O)[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[C@H](C)CCC(=O)NCCS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H45NO7S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H45NO7S/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34)/t15-,16-,17-,18-,19?,20?,21-,22+,24?,25+,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WBWWGRHZICKQGZ-ZKUTWGMOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>144.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>132.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>57.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355752</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00078</kegg_id>
  <foodb_id>FDB002250</foodb_id>
  <chemspider_id>6066</chemspider_id>
  <phenol_explorer_compound_id/>
  <drugbank_id>DB00150</drugbank_id>
  <pubchem_compound_id>6305</pubchem_compound_id>
  <chebi_id>16828</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00001396</knapsack_id>
  <meta_cyc_id>TRP</meta_cyc_id>
  <bigg_id>33772</bigg_id>
  <wikipedia_id>Tryptophan</wikipedia_id>
  <metlin_id>5879</metlin_id>
  <synthesis_reference>Shaw, Roger; Elliott, William H.  Bile acids.  LXI.  Synthesis and properties of conjugates of 5a-bile acids.    Lipids  (1980),  15(10),  805-10.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:41 UTC</creation_date>
  <update_date>2020-04-15 21:56:58 UTC</update_date>
  <accession>BMDB0000925</accession>
  <secondary_accessions>
    <accession>BMDB00925</accession>
  </secondary_accessions>
  <name>Trimethylamine N-oxide</name>
  <description>Trimethylamine N-oxide, also known as (CH3)3no or tmao, belongs to the class of organic compounds known as trialkyl amine oxides. These are hydrocarbyl derivatives of the aminoxide anion, with the general formula R3N+[O-] or R3N=O, where R is an alkyl group. Trimethylamine N-oxide exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Trimethylamine N-oxide exists in all living organisms, ranging from bacteria to humans. Trimethylamine N-oxide is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(CH3)3NO</synonym>
    <synonym>Me3n(+)O(-)</synonym>
    <synonym>Me3n(O)</synonym>
    <synonym>N(CH3)3O</synonym>
    <synonym>TMAO</synonym>
    <synonym>Trimethylamine oxide</synonym>
    <synonym>Trimethylaminoxid</synonym>
    <synonym>Trimethyloxamine</synonym>
    <synonym>N,N-Dimethylmethanamine N-oxide</synonym>
    <synonym>TMA-oxide</synonym>
    <synonym>Trimethylamine-N-oxide</synonym>
    <synonym>Triox</synonym>
    <synonym>Trimethylammonium oxide</synonym>
  </synonyms>
  <chemical_formula>C3H9NO</chemical_formula>
  <average_molecular_weight>75.1097</average_molecular_weight>
  <monisotopic_moleculate_weight>75.068413915</monisotopic_moleculate_weight>
  <iupac_name>N,N-dimethylmethanamine oxide</iupac_name>
  <traditional_iupac>trimethylamine-n-oxide</traditional_iupac>
  <cas_registry_number>1184-78-7</cas_registry_number>
  <smiles>C[N+](C)(C)[O-]</smiles>
  <inchi>InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3</inchi>
  <inchikey>UYPYRKYUKCHHIB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as trialkyl amine oxides. These are hydrocarbyl derivatives of the aminoxide anion, with the general formula R3N+[O-] or R3N=O, where R is an alkyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Aminoxides</sub_class>
    <direct_parent>Trialkyl amine oxides</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Trisubstituted amine oxides and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-oxide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Trialkyl amine oxide</substituent>
      <substituent>Trisubstituted n-oxide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-oxide</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>95 - 99 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>454 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N,N-dimethylmethanamine oxide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>75.1097</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>75.068413915</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)[O-]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H9NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H9NO/c1-4(2,3)5/h1-3H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UYPYRKYUKCHHIB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>23.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>22.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448169</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in lactating Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 54 Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21.</reference_text>
          <pubmed_id>23394630</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>6+/-3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>14+/-5</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>43 - 46</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>14+/-4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>11+/-5</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Urine samples were from 32 Holstein cows that were fed crude protein.</comment>
      <references>
        <reference>
          <reference_text>Bertram HC, Yde CC, Zhang X, Kristensen NB: Effect of dietary nitrogen content on the urine metabolite profile of dairy cows assessed by nuclear magnetic resonance (NMR)-based metabolomics. J Agric Food Chem. 2011 Dec 14;59(23):12499-505. doi: 10.1021/jf204201f. Epub 2011 Nov 17.</reference_text>
          <pubmed_id>22059599</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB010413</foodb_id>
  <pubchem_compound_id>1145</pubchem_compound_id>
  <chemspider_id>1113</chemspider_id>
  <kegg_id>C01104</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>15724</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Trimethylamine_oxide</wikipedia_id>
  <metlin_id>5876</metlin_id>
  <meta_cyc_id>TRIMENTHLAMINE-N-O</meta_cyc_id>
  <synthesis_reference>Hazard, Rene; Cheymol, Jean; Chabrier, Pierre.  Trimethylamine oxide.    (1962),     1 p.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:42 UTC</creation_date>
  <update_date>2020-03-13 16:24:48 UTC</update_date>
  <accession>BMDB0000927</accession>
  <secondary_accessions>
    <accession>BMDB00927</accession>
  </secondary_accessions>
  <name>Valerylglycine</name>
  <description/>
  <synonyms>
    <synonym>N-N-Valerylglycine</synonym>
    <synonym>N-Pentanoylglycine</synonym>
    <synonym>N-Valeryl-glycine</synonym>
    <synonym>2-[(1-Hydroxypentylidene)amino]acetate</synonym>
  </synonyms>
  <chemical_formula>C7H13NO3</chemical_formula>
  <average_molecular_weight>159.183</average_molecular_weight>
  <monisotopic_moleculate_weight>159.089543287</monisotopic_moleculate_weight>
  <iupac_name>2-pentanamidoacetic acid</iupac_name>
  <traditional_iupac>valerylglycine</traditional_iupac>
  <cas_registry_number>24003-66-5</cas_registry_number>
  <smiles>CCCCC(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C7H13NO3/c1-2-3-4-6(9)8-5-7(10)11/h2-5H2,1H3,(H,8,9)(H,10,11)</inchi>
  <inchikey>NYZBWOSRZJKQAI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-pentanamidoacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>159.183</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>159.089543287</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H13NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H13NO3/c1-2-3-4-6(9)8-5-7(10)11/h2-5H2,1H3,(H,8,9)(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NYZBWOSRZJKQAI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1548</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022321</foodb_id>
  <pubchem_compound_id>4737557</pubchem_compound_id>
  <chemspider_id>3924818</chemspider_id>
  <kegg_id/>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5878</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Katz, J.; Lieberman, I.; Barker, H. A.  Formation of propionyl-, butyryl-, and other acylglycines by enzymes of Clostridium kluyveri.    Journal of Biological Chemistry  (1953),  200  431-41.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:43 UTC</creation_date>
  <update_date>2020-04-16 20:39:07 UTC</update_date>
  <accession>BMDB0000929</accession>
  <secondary_accessions>
    <accession>BMDB00929</accession>
  </secondary_accessions>
  <name>L-Tryptophan</name>
  <description>L-Tryptophan, also known as Trp or W, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. L-Tryptophan exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Tryptophan exists in all living species, ranging from bacteria to humans. L-Tryptophan participates in a number of enzymatic reactions, within cattle. In particular, L-Tryptophan can be converted into n'-formylkynurenine; which is catalyzed by the enzyme tryptophan 2,3-dioxygenase. In addition, L-Tryptophan and tetrahydrobiopterin can be converted into 5-hydroxy-L-tryptophan and 4a-hydroxytetrahydrobiopterin through the action of the enzyme tryptophan 5-hydroxylase 1. In cattle, L-tryptophan is involved in the metabolic pathway called the tryptophan metabolism pathway. L-Tryptophan is a potentially toxic compound. L-Tryptophan has been found to be associated with several diseases known as pancreatic cancer, tryptophanuria with dwarfism, crohn's disease, and alzheimer's disease; also l-tryptophan has been linked to the inborn metabolic disorders including hartnup disease.</description>
  <synonyms>
    <synonym>(2S)-2-Amino-3-(1H-indol-3-yl)propanoic acid</synonym>
    <synonym>(S)-alpha-Amino-1H-indole-3-propanoic acid</synonym>
    <synonym>(S)-alpha-Amino-beta-(3-indolyl)-propionic acid</synonym>
    <synonym>(S)-Tryptophan</synonym>
    <synonym>L-(-)-Tryptophan</synonym>
    <synonym>L-beta-3-Indolylalanine</synonym>
    <synonym>Trp</synonym>
    <synonym>Tryptophan</synonym>
    <synonym>W</synonym>
    <synonym>(2S)-2-Amino-3-(1H-indol-3-yl)propanoate</synonym>
    <synonym>(S)-a-Amino-1H-indole-3-propanoate</synonym>
    <synonym>(S)-a-Amino-1H-indole-3-propanoic acid</synonym>
    <synonym>(S)-alpha-Amino-1H-indole-3-propanoate</synonym>
    <synonym>(S)-Α-amino-1H-indole-3-propanoate</synonym>
    <synonym>(S)-Α-amino-1H-indole-3-propanoic acid</synonym>
    <synonym>(S)-a-Amino-b-(3-indolyl)-propionate</synonym>
    <synonym>(S)-a-Amino-b-(3-indolyl)-propionic acid</synonym>
    <synonym>(S)-alpha-Amino-beta-(3-indolyl)-propionate</synonym>
    <synonym>(S)-Α-amino-β-(3-indolyl)-propionate</synonym>
    <synonym>(S)-Α-amino-β-(3-indolyl)-propionic acid</synonym>
    <synonym>L-b-3-Indolylalanine</synonym>
    <synonym>L-Β-3-indolylalanine</synonym>
    <synonym>(-)-Tryptophan</synonym>
    <synonym>(L)-Tryptophan</synonym>
    <synonym>(S)-1H-Indole-3-alanine</synonym>
    <synonym>(S)-2-Amino-3-(3-indolyl)propionic acid</synonym>
    <synonym>(S)-a-Amino-b-indolepropionate</synonym>
    <synonym>(S)-a-Amino-b-indolepropionic acid</synonym>
    <synonym>(S)-a-Aminoindole-3-propionate</synonym>
    <synonym>(S)-a-Aminoindole-3-propionic acid</synonym>
    <synonym>(S)-alpha-Amino-beta-indolepropionate</synonym>
    <synonym>(S)-alpha-Amino-beta-indolepropionic acid</synonym>
    <synonym>(S)-alpha-Aminoindole-3-propionate</synonym>
    <synonym>(S)-alpha-Aminoindole-3-propionic acid</synonym>
    <synonym>1-beta-3-Indolylalanine</synonym>
    <synonym>1beta-3-Indolylalanine</synonym>
    <synonym>1H-Indole-3-alanine</synonym>
    <synonym>2-Amino-3-indolylpropanoate</synonym>
    <synonym>2-Amino-3-indolylpropanoic acid</synonym>
    <synonym>3-(1H-indol-3-yl)-L-Alanine</synonym>
    <synonym>3-indol-3-Ylalanine</synonym>
    <synonym>Alpha'-amino-3-indolepropionic acid</synonym>
    <synonym>alpha-Aminoindole-3-propionic acid</synonym>
    <synonym>Ardeytropin</synonym>
    <synonym>H-TRP-OH</synonym>
    <synonym>Indole-3-alanine</synonym>
    <synonym>Kalma</synonym>
    <synonym>L-alpha-Amino-3-indolepropionic acid</synonym>
    <synonym>L-alpha-Aminoindole-3-propionic acid</synonym>
    <synonym>L-Tryptofan</synonym>
    <synonym>L-Tryptophane</synonym>
    <synonym>Lopac-T-0254</synonym>
    <synonym>Lyphan</synonym>
    <synonym>Optimax</synonym>
    <synonym>Pacitron</synonym>
    <synonym>Sedanoct</synonym>
    <synonym>Triptofano</synonym>
    <synonym>Trofan</synonym>
    <synonym>Tryptacin</synonym>
    <synonym>Tryptan</synonym>
    <synonym>Tryptophane</synonym>
    <synonym>Tryptophanum</synonym>
    <synonym>Ardeydorm</synonym>
    <synonym>L Tryptophan</synonym>
    <synonym>L-Tryptophan-ratiopharm</synonym>
    <synonym>Merck brand OF tryptophan</synonym>
    <synonym>Niddapharm brand OF tryptophan</synonym>
    <synonym>ICN brand OF tryptophan</synonym>
    <synonym>Levotryptophan</synonym>
    <synonym>PMS Tryptophan</synonym>
    <synonym>PMS-Tryptophan</synonym>
    <synonym>Ratiopharm brand OF tryptophan</synonym>
    <synonym>Esparma brand OF tryptophan</synonym>
    <synonym>Ratio-tryptophan</synonym>
    <synonym>L Tryptophan ratiopharm</synonym>
    <synonym>Naturruhe</synonym>
    <synonym>Tryptophan metabolism alterations</synonym>
    <synonym>Ardeypharm brand OF tryptophan</synonym>
    <synonym>Kalma brand OF tryptophan</synonym>
    <synonym>Pharmascience brand OF tryptophan</synonym>
    <synonym>Upsher-smith brand OF tryptophan</synonym>
    <synonym>Ratio tryptophan</synonym>
  </synonyms>
  <chemical_formula>C11H12N2O2</chemical_formula>
  <average_molecular_weight>204.2252</average_molecular_weight>
  <monisotopic_moleculate_weight>204.089877638</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid</iupac_name>
  <traditional_iupac>L-tryptophan</traditional_iupac>
  <cas_registry_number>73-22-3</cas_registry_number>
  <smiles>N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O</smiles>
  <inchi>InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1</inchi>
  <inchikey>QIVBCDIJIAJPQS-VIFPVBQESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Indolyl carboxylic acids and derivatives</sub_class>
    <direct_parent>Indolyl carboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alkylindoles</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alkylindole</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indole</substituent>
      <substituent>Indolyl carboxylic acid derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Common amino acids</external_descriptor>
      <external_descriptor>L-alpha-amino acid</external_descriptor>
      <external_descriptor>erythrose 4-phosphate/phosphoenolpyruvate family amino acid</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
      <external_descriptor>tryptophan</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>204.2252</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>204.089877638</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H12N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QIVBCDIJIAJPQS-VIFPVBQESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>79.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>56.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Protein Synthesis: Tryptophan</name>
      <smpdb_id>SMP0119414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30704</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4911</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>37-42</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Ion exchange chromatography with fluorometric detection</comment>
      <references>
        <reference>
          <reference_text>Greenwood RH, Titgemeyer EC, Stokka GL, Drouillard JS, Loest CA: Effects of L-carnitine on nitrogen retention and blood metabolites of growing steers and performance of finishing steers. J Anim Sci. 2001 Jan;79(1):254-60. doi: 10.2527/2001.791254x.</reference_text>
          <pubmed_id>11204708</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>22-25</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010.</reference_text>
          <pubmed_id>28036059</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>47+/-7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by DFI-MS/MS (P180) in periparturient Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Hailemariam D, Mandal R, Saleem F, Dunn SM, Wishart DS, Ametaj BN: Identification of predictive biomarkers of disease state in transition dairy cows. J Dairy Sci. 2014 May;97(5):2680-93. doi: 10.3168/jds.2013-6803. Epub 2014 Mar 13.</reference_text>
          <pubmed_id>24630653</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>44+/-7</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>19+/-5</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1 - 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2301.381</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2301.381</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.2 +/- 1.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from Brown Swiss cows during late lactation</comment>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
          <pubmed_id>23931703</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.1 +/- 0.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from Brown Swiss cows during early lactation</comment>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
          <pubmed_id>23931703</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2301.381</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.0 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2301.381</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.18 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.1 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2252.415</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2252.415</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2252.415</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>50</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>35-95</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>9.26 +/- 3.06</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>4.41</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>6.59</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>9.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>8.68</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By direct flow injection MS/MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>4-12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>5 - 8</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Wadud S, Onodera R, Or-Rashid MM, Amin MR: Determination of histidine and related compounds in rumen fluid by liquid chromatography. J AOAC Int. 2000 Jan-Feb;83(1):8-15.</reference_text>
          <pubmed_id>10692998</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>7 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>10 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>17 +/- 9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>11 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>11 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by NMR, GC-MS and DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>24+/-14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>21+/-3</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>18+/-4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB002250</foodb_id>
  <pubchem_compound_id>6305</pubchem_compound_id>
  <chemspider_id>6066</chemspider_id>
  <kegg_id>C00078</kegg_id>
  <drugbank_id>DB00150</drugbank_id>
  <pdbe_id/>
  <chebi_id>16828</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001396</knapsack_id>
  <bigg_id>33772</bigg_id>
  <wikipedia_id>Tryptophan</wikipedia_id>
  <metlin_id>5879</metlin_id>
  <meta_cyc_id>TRP</meta_cyc_id>
  <synthesis_reference>Amir-Heidari, Bagher; Thirlway, Jenny; Micklefield, Jason. Stereochemical course of tryptophan dehydrogenation during biosynthesis of the calcium-dependent lipopeptide antibiotics. Organic Letters  (2007),  9(8),  1513-1516.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Nurnberger N, Sigl G, Gronwald W, Wiedemann S, Dettmer K, Oefner PJ: Correlations between milk and plasma levels of amino and carboxylic acids in dairy cows. J Proteome Res. 2013 Nov 1;12(11):5223-32. doi: 10.1021/pr4006537. Epub 2013 Aug  23.</reference_text>
      <pubmed_id>23931703</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00012</protein_accession>
      <name>Tryptophan 2,3-dioxygenase</name>
      <uniprot_id>Q2KIQ5</uniprot_id>
      <gene_name>TDO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00928</protein_accession>
      <name>Tryptophanyl-tRNA synthetase, cytoplasmic</name>
      <uniprot_id>P17248</uniprot_id>
      <gene_name>WARS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00929</protein_accession>
      <name>Tryptophanyl-tRNA synthetase, mitochondrial</name>
      <uniprot_id>Q3T099</uniprot_id>
      <gene_name>WARS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02160</protein_accession>
      <name>Blood-brain barrier large neutral amino acid transporter</name>
      <uniprot_id>Q9TU26</uniprot_id>
      <gene_name>LAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:44 UTC</creation_date>
  <update_date>2020-03-13 16:24:49 UTC</update_date>
  <accession>BMDB0000930</accession>
  <secondary_accessions>
    <accession>BMDB00930</accession>
  </secondary_accessions>
  <name>trans-Cinnamic acid</name>
  <description>trans-Cinnamic acid, also known as (2E)-3-phenylacrylate or (e)-cinnamate, belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. trans-Cinnamic acid exists as a solid, possibly soluble (in water), and a weakly acidic compound (based on its pKa) molecule. trans-Cinnamic acid exists in all living species, ranging from bacteria to humans. trans-Cinnamic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2E)-3-Phenyl-2-propenoic acid</synonym>
    <synonym>(2E)-3-Phenylacrylic acid</synonym>
    <synonym>(e)-3-Phenyl-2-propenoic acid</synonym>
    <synonym>(e)-Cinnamate</synonym>
    <synonym>(e)-Cinnamic acid</synonym>
    <synonym>Benzeneacrylic acid</synonym>
    <synonym>PHENYLETHYLENECARBOXYLIC ACID</synonym>
    <synonym>trans-3-Phenylacrylic acid</synonym>
    <synonym>trans-beta-Carboxystyrene</synonym>
    <synonym>trans-Cinnamate</synonym>
    <synonym>trans-Zimtsaeure</synonym>
    <synonym>(2E)-3-Phenyl-2-propenoate</synonym>
    <synonym>(2E)-3-Phenylacrylate</synonym>
    <synonym>(e)-3-Phenyl-2-propenoate</synonym>
    <synonym>Benzeneacrylate</synonym>
    <synonym>PHENYLETHYLENECARBOXYLate</synonym>
    <synonym>trans-3-Phenylacrylate</synonym>
    <synonym>trans-b-Carboxystyrene</synonym>
    <synonym>trans-Β-carboxystyrene</synonym>
    <synonym>(2E)-2-Phenyl-2-propenoate</synonym>
    <synonym>(2E)-2-Phenyl-2-propenoic acid</synonym>
    <synonym>(e)-3-Phenylacrylate</synonym>
    <synonym>(e)-3-Phenylacrylic acid</synonym>
    <synonym>(e)-3-Phenylprop-2-enoate</synonym>
    <synonym>(e)-3-Phenylprop-2-enoic acid</synonym>
    <synonym>trans-3-Phenyl-2-propenoate</synonym>
    <synonym>trans-3-Phenyl-2-propenoic acid</synonym>
    <synonym>Cinnamic acid, 14C-labeled CPD</synonym>
    <synonym>Cinnamic acid, 2-(14)C-labeled CPD</synonym>
    <synonym>Cinnamic acid, 3-(14)C-labeled CPD</synonym>
    <synonym>Cinnamic acid, (Z)-isomer</synonym>
    <synonym>Cinnamic acid, 2-(13)C-labeled CPD</synonym>
    <synonym>Cinnamic acid, 3H-labeled CPD (e)-isomer</synonym>
    <synonym>Cinnamic acid, 3H-labeled CPD (Z)-isomer</synonym>
    <synonym>Cinnamic acid, ion(1-)-(e)-isomer</synonym>
    <synonym>Cinnamic acid, sodium salt</synonym>
    <synonym>Cinnamic acid, sodium salt(e)-isomer</synonym>
    <synonym>Cinnamic acid, sodium salt(Z)-isomer</synonym>
    <synonym>Cinnamic acid, (trans)-(e)-isomer</synonym>
    <synonym>Cinnamic acid, 14C-labeled CPD (e)-isomer</synonym>
    <synonym>Cinnamic acid, ion(1-)</synonym>
    <synonym>Cinnamic acid, nickel (+2) salt</synonym>
    <synonym>Cinnamic acid, potassium salt</synonym>
    <synonym>Cinnamic acid, zinc salt(e)-isomer</synonym>
    <synonym>Cinnamic acid, 13C-labeled CPD</synonym>
    <synonym>Cinnamic acid</synonym>
    <synonym>(2E)-3-Phenylprop-2-enoic acid</synonym>
    <synonym>(2E)-Cinnamic acid</synonym>
    <synonym>3-Phenyl-(e)-2-propenoic acid</synonym>
    <synonym>3-Phenyl-2-propenoic acid</synonym>
    <synonym>3-Phenylacrylic acid</synonym>
    <synonym>Phenylacrylic acid</synonym>
    <synonym>beta-Phenylacrylic acid</synonym>
    <synonym>Β-phenylacrylic acid</synonym>
    <synonym>trans-Cinnamic acid</synonym>
  </synonyms>
  <chemical_formula>C9H8O2</chemical_formula>
  <average_molecular_weight>148.1586</average_molecular_weight>
  <monisotopic_moleculate_weight>148.0524295</monisotopic_moleculate_weight>
  <iupac_name>(2E)-3-phenylprop-2-enoic acid</iupac_name>
  <traditional_iupac>cinnamic acid</traditional_iupac>
  <cas_registry_number>140-10-3</cas_registry_number>
  <smiles>OC(=O)\C=C\C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+</inchi>
  <inchikey>WBYWAXJHAXSJNI-VOTSOKGWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Cinnamic acids and derivatives</class>
    <sub_class>Cinnamic acids</sub_class>
    <direct_parent>Cinnamic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cinnamic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Styrene</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Monolignols</external_descriptor>
      <external_descriptor>cinnamic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>133 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.546 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.13</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-3-phenylprop-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>148.1586</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>148.0524295</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)\C=C\C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H8O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WBYWAXJHAXSJNI-VOTSOKGWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37847</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4924</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447953</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fermented milk, by capillary electrophoresis-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
          <pubmed_id>26686724</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB012052</foodb_id>
  <pubchem_compound_id>444539</pubchem_compound_id>
  <chemspider_id>392447</chemspider_id>
  <kegg_id>C10438</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>35697</chebi_id>
  <phenol_explorer_compound_id>549</phenol_explorer_compound_id>
  <knapsack_id>C00029961</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Cinnamic_acid</wikipedia_id>
  <metlin_id>5880</metlin_id>
  <meta_cyc_id>CPD-674</meta_cyc_id>
  <synthesis_reference>Zhu, Min; Shentu, Chao; Zhou, Zhong Shi.  Microwave-assisted base-free synthesis of trans-cinnamic acids using hypervalent iodonium salts.    Chinese Chemical Letters  (2007),  18(3),  272-274.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
      <pubmed_id>26686724</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:46 UTC</creation_date>
  <update_date>2020-04-15 22:14:46 UTC</update_date>
  <accession>BMDB0000932</accession>
  <secondary_accessions>
    <accession>BMDB00932</accession>
  </secondary_accessions>
  <name>Tauro-b-muricholic acid</name>
  <description/>
  <synonyms>
    <synonym>Tauro-b-muricholate</synonym>
    <synonym>N-(3a,6b,7b-Trihydroxy-5b-cholan-24-oyl)-taurine</synonym>
    <synonym>Tauro-beta-muricholate</synonym>
    <synonym>Tauro-beta-muricholic acid</synonym>
    <synonym>T-alpha-MC</synonym>
    <synonym>T-beta-MC</synonym>
    <synonym>Tauro-alpha-muricholate</synonym>
    <synonym>Tauro-alpha-muricholic acid</synonym>
    <synonym>Tauromuricholate</synonym>
    <synonym>Tauromuricholic acid</synonym>
    <synonym>Tauromuricholic acid, (3alpha,5beta,6beta,7alpha)-isomer</synonym>
    <synonym>(4R)-N-(2-Sulfoethyl)-4-[(2R,5R,7R,8S,9R,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanimidate</synonym>
    <synonym>(4R)-N-(2-Sulphoethyl)-4-[(2R,5R,7R,8S,9R,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanimidate</synonym>
    <synonym>(4R)-N-(2-Sulphoethyl)-4-[(2R,5R,7R,8S,9R,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanimidic acid</synonym>
  </synonyms>
  <chemical_formula>C26H45NO7S</chemical_formula>
  <average_molecular_weight>515.703</average_molecular_weight>
  <monisotopic_moleculate_weight>515.291673489</monisotopic_moleculate_weight>
  <iupac_name>2-[(4R)-4-[(2R,5R,7R,8S,9R,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid</iupac_name>
  <traditional_iupac>2-[(4R)-4-[(2R,5R,7R,8S,9R,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethanesulfonic acid</traditional_iupac>
  <cas_registry_number>25696-60-0</cas_registry_number>
  <smiles>[H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)[C@H](CCC3C1[C@@H](O)[C@H]2O)[C@H](C)CCC(=O)NCCS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C26H45NO7S/c1-15(4-7-21(29)27-12-13-35(32,33)34)17-5-6-18-22-19(9-11-25(17,18)2)26(3)10-8-16(28)14-20(26)23(30)24(22)31/h15-20,22-24,28,30-31H,4-14H2,1-3H3,(H,27,29)(H,32,33,34)/t15-,16-,17-,18?,19?,20+,22?,23+,24-,25-,26-/m1/s1</inchi>
  <inchikey>XSOLDPYUICCHJX-OEYGYFRSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Taurinated bile acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>6-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Alkanesulfonic acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonic acids</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfonyls</alternative_parent>
      <alternative_parent>Trihydroxy bile acids, alcohols and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>6-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkanesulfonic acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfonyl</substituent>
      <substituent>Taurinated bile acid</substituent>
      <substituent>Trihydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.098</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-0.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.084</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4R)-4-[(2R,5R,7R,8S,9R,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>515.703</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>515.291673489</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)[C@H](CCC3C1[C@@H](O)[C@H]2O)[C@H](C)CCC(=O)NCCS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H45NO7S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H45NO7S/c1-15(4-7-21(29)27-12-13-35(32,33)34)17-5-6-18-22-19(9-11-25(17,18)2)26(3)10-8-16(28)14-20(26)23(30)24(22)31/h15-20,22-24,28,30-31H,4-14H2,1-3H3,(H,27,29)(H,32,33,34)/t15-,16-,17-,18?,19?,20+,22?,23+,24-,25-,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XSOLDPYUICCHJX-OEYGYFRSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>144.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>131.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>57.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361047</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>147312</chemspider_id>
  <pubchem_compound_id>168408</pubchem_compound_id>
  <foodb_id>FDB022322</foodb_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5881</metlin_id>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:47 UTC</creation_date>
  <update_date>2020-03-13 16:24:51 UTC</update_date>
  <accession>BMDB0000933</accession>
  <secondary_accessions>
    <accession>BMDB00933</accession>
  </secondary_accessions>
  <name>Traumatic acid</name>
  <description/>
  <synonyms>
    <synonym>(2E)-Dodecenedioic acid</synonym>
    <synonym>2E-Dodecenedioic acid</synonym>
    <synonym>Dodec-2-enedioic acid</synonym>
    <synonym>trans-2-Dodecenedioic acid</synonym>
    <synonym>(2E)-Dodecenedioate</synonym>
    <synonym>2E-Dodecenedioate</synonym>
    <synonym>Dodec-2-enedioate</synonym>
    <synonym>trans-2-Dodecenedioate</synonym>
    <synonym>Traumatate</synonym>
    <synonym>(Z)-2-Dodecenedioate</synonym>
    <synonym>(Z)-2-Dodecenedioic acid</synonym>
    <synonym>1-Decene-1,10-dicarboxylic acid</synonym>
    <synonym>2-Dodecendioate</synonym>
    <synonym>2-Dodecendioic acid</synonym>
    <synonym>2-Dodecenedioate</synonym>
    <synonym>2-Dodecenedioic acid</synonym>
    <synonym>Dodec-2C-enedioate</synonym>
    <synonym>Dodec-2C-enedioic acid</synonym>
    <synonym>Dodec-2t-enedioate</synonym>
    <synonym>Dodec-2t-enedioic acid</synonym>
    <synonym>Dodecanedioate</synonym>
    <synonym>Dodecanedioic acid</synonym>
    <synonym>Dodecanedioic acid-2-ene</synonym>
    <synonym>trans-Traumatate</synonym>
    <synonym>trans-Traumatic acid</synonym>
    <synonym>2-Dodecene-1,12-dicarboxylic acid</synonym>
  </synonyms>
  <chemical_formula>C12H20O4</chemical_formula>
  <average_molecular_weight>228.2848</average_molecular_weight>
  <monisotopic_moleculate_weight>228.136159128</monisotopic_moleculate_weight>
  <iupac_name>(2E)-dodec-2-enedioic acid</iupac_name>
  <traditional_iupac>traumatic acid</traditional_iupac>
  <cas_registry_number>6402-36-4</cas_registry_number>
  <smiles>OC(=O)CCCCCCCC\C=C\C(O)=O</smiles>
  <inchi>InChI=1S/C12H20O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h7,9H,1-6,8,10H2,(H,13,14)(H,15,16)/b9-7+</inchi>
  <inchikey>MAZWDMBCPDUFDJ-VQHVLOKHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>165.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-dodec-2-enedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>228.2848</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>228.136159128</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCCCCCC\C=C\C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H20O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H20O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h7,9H,1-6,8,10H2,(H,13,14)(H,15,16)/b9-7+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MAZWDMBCPDUFDJ-VQHVLOKHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>61.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367023</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022323</foodb_id>
  <pubchem_compound_id>5283028</pubchem_compound_id>
  <chemspider_id>4446155</chemspider_id>
  <kegg_id>C16308</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>545687</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Traumatic acid</wikipedia_id>
  <metlin_id>5882</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Dupont, G.; Dulou, R.; Quantin, P.  Polycarboxylic acids and their derivatives.    (1952),     FR  1018186  19521229  CAN 52:6571  AN 1958:6571</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:48 UTC</creation_date>
  <update_date>2020-03-13 16:24:51 UTC</update_date>
  <accession>BMDB0000934</accession>
  <secondary_accessions>
    <accession>BMDB00934</accession>
  </secondary_accessions>
  <name>Uridine diphosphate acetylgalactosamine 4-sulfate</name>
  <description/>
  <synonyms>
    <synonym>Uridine diphosphate acetylgalactosamine 4-sulphate</synonym>
    <synonym>Uridine diphosphoric acid acetylgalactosamine 4-sulfuric acid</synonym>
    <synonym>Uridine diphosphoric acid acetylgalactosamine 4-sulphuric acid</synonym>
    <synonym>UDP Acetylgalactosamine-4-sulfate</synonym>
    <synonym>UDP Acetylgalactosamine-4-sulphate</synonym>
    <synonym>UDP-GalNAc-S</synonym>
    <synonym>UDP-N-Acetylgalactosamine 4-sulfate</synonym>
    <synonym>UDP-N-Acetylgalactosamine 4-sulphate</synonym>
    <synonym>UDP-N-Acetylgalactosamine-4-sulfate</synonym>
    <synonym>UDP-N-Acetylgalactosamine-4-sulphate</synonym>
    <synonym>Uridine diphosphate acetylgalactosamine-4-sulfate</synonym>
    <synonym>Uridine diphosphate acetylgalactosamine-4-sulphate</synonym>
    <synonym>Uridine diphosphate-N-acetylgalactosamine 4-sulfate</synonym>
    <synonym>Uridine diphosphate-N-acetylgalactosamine 4-sulphate</synonym>
    <synonym>[({[(2R,3S,4R,5R)-3-[({[(2R,3R,4R,5R)-5-amino-1,2,4-trihydroxy-6,7-dioxooctan-3-yl]oxy}sulfonyl)oxy]-4-hydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonate</synonym>
    <synonym>[({[(2R,3S,4R,5R)-3-[({[(2R,3R,4R,5R)-5-amino-1,2,4-trihydroxy-6,7-dioxooctan-3-yl]oxy}sulphonyl)oxy]-4-hydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonate</synonym>
    <synonym>[({[(2R,3S,4R,5R)-3-[({[(2R,3R,4R,5R)-5-amino-1,2,4-trihydroxy-6,7-dioxooctan-3-yl]oxy}sulphonyl)oxy]-4-hydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</synonym>
  </synonyms>
  <chemical_formula>C17H27N3O20P2S</chemical_formula>
  <average_molecular_weight>687.417</average_molecular_weight>
  <monisotopic_moleculate_weight>687.038384033</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-3-[({[(2R,3R,4R,5R)-5-amino-1,2,4-trihydroxy-6,7-dioxooctan-3-yl]oxy}sulfonyl)oxy]-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-4-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>{[(2R,3S,4R,5R)-3-({[(2R,3R,4R,5R)-5-amino-1,2,4-trihydroxy-6,7-dioxooctan-3-yl]oxysulfonyl}oxy)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-4-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>3863-56-7</cas_registry_number>
  <smiles>CC(=O)C(=O)[C@H](N)[C@@H](O)[C@@H](OS(=O)(=O)O[C@@H]1[C@@H](COP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O)[C@H](O)CO</smiles>
  <inchi>InChI=1S/C17H27N3O20P2S/c1-6(22)11(25)10(18)12(26)14(7(23)4-21)38-43(34,35)39-15-8(5-36-42(32,33)40-41(29,30)31)37-16(13(15)27)20-3-2-9(24)19-17(20)28/h2-3,7-8,10,12-16,21,23,26-27H,4-5,18H2,1H3,(H,32,33)(H,19,24,28)(H2,29,30,31)/t7-,8-,10+,12-,13-,14+,15-,16-/m1/s1</inchi>
  <inchikey>MVHRGUAARHOHCJ-JANKDUHBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine nucleotide sugars</sub_class>
    <direct_parent>Pyrimidine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Glucuronic acid derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Pyrimidine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glucuronic acid or derivatives</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine nucleotide sugar</substituent>
      <substituent>Pyrimidine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>UDP-sugar</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-3-[({[(2R,3R,4R,5R)-5-amino-1,2,4-trihydroxy-6,7-dioxooctan-3-yl]oxy}sulfonyl)oxy]-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-4-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>687.417</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>687.038384033</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)C(=O)[C@H](N)[C@@H](O)[C@@H](OS(=O)(=O)O[C@@H]1[C@@H](COP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O)[C@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C17H27N3O20P2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C17H27N3O20P2S/c1-6(22)11(25)10(18)12(26)14(7(23)4-21)38-43(34,35)39-15-8(5-36-42(32,33)40-41(29,30)31)37-16(13(15)27)20-3-2-9(24)19-17(20)28/h2-3,7-8,10,12-16,21,23,26-27H,4-5,18H2,1H3,(H,32,33)(H,19,24,28)(H2,29,30,31)/t7-,8-,10+,12-,13-,14+,15-,16-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MVHRGUAARHOHCJ-JANKDUHBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>365.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>129.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>55.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353451</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022324</foodb_id>
  <chemspider_id>17216024</chemspider_id>
  <pubchem_compound_id>22833553</pubchem_compound_id>
  <kegg_id>C04426</kegg_id>
  <chebi_id/>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5883</metlin_id>
  <synthesis_reference>Leznicki, Antoni J.; Bialkowski, Karol.  Improved high-performance liquid chromatographic method for N-acetylgalactosamine-4-sulfate sulfatase (arylsulfatase B) activity determination using uridine diphospho-N-acetylgalactosamine-4-sulfate.    Journal of Chromatography, B: Biomedical Sciences and Applications  (1997),  696(2),  193-202.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:49 UTC</creation_date>
  <update_date>2020-04-15 22:14:47 UTC</update_date>
  <accession>BMDB0000935</accession>
  <secondary_accessions>
    <accession>BMDB00935</accession>
  </secondary_accessions>
  <name>Uridine diphosphate glucuronic acid</name>
  <description/>
  <synonyms>
    <synonym>UDP-alpha-D-Glucuronate</synonym>
    <synonym>UDP-D-Glucuronate</synonym>
    <synonym>UDP-Glucuronate</synonym>
    <synonym>UDPglucuronate</synonym>
    <synonym>URIDINE-5'-diphosphATE-glucuronIC ACID</synonym>
    <synonym>UDP-a-D-Glucuronate</synonym>
    <synonym>UDP-a-D-Glucuronic acid</synonym>
    <synonym>UDP-alpha-D-Glucuronic acid</synonym>
    <synonym>UDP-Α-D-glucuronate</synonym>
    <synonym>UDP-Α-D-glucuronic acid</synonym>
    <synonym>UDP-D-Glucuronic acid</synonym>
    <synonym>UDP-Glucuronic acid</synonym>
    <synonym>UDPglucuronic acid</synonym>
    <synonym>URIDINE-5'-diphosphate-glucuronate</synonym>
    <synonym>URIDINE-5'-diphosphoric acid-glucuronic acid</synonym>
    <synonym>Uridine diphosphate glucuronate</synonym>
    <synonym>Uridine diphosphoric acid glucuronic acid</synonym>
    <synonym>a-D-Glucopyranuronic acid 1-&gt;5'-ester with uridine 5'-(trihydrogen pyrophosphate)</synonym>
    <synonym>a-D-Glucopyranuronic acid ester with uridine 5'-pyrophosphate</synonym>
    <synonym>alpha-D-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphate)</synonym>
    <synonym>alpha-delta-Glucopyranuronic acid 1-&gt;5'-ester with uridine 5'-(trihydrogen pyrophosphate)</synonym>
    <synonym>alpha-delta-Glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphate)</synonym>
    <synonym>alpha-delta-Glucopyranuronic acid ester with uridine 5'-pyrophosphate</synonym>
    <synonym>Glucopyranuronic acid 1-ester with uridine 5'-pyrophosphate</synonym>
    <synonym>UDP Glucuronate</synonym>
    <synonym>UDP Glucuronic acid</synonym>
    <synonym>UDP-alpha-delta-Glucuronate</synonym>
    <synonym>UDP-delta-Glucuronate</synonym>
    <synonym>UDP-delta-Glucuronic acid</synonym>
    <synonym>UDP-GlcUA</synonym>
    <synonym>UDPGA</synonym>
    <synonym>UGA</synonym>
    <synonym>Uridine 5'-diphospho-a-D-glucuronate</synonym>
    <synonym>Uridine 5'-diphospho-a-D-glucuronic acid</synonym>
    <synonym>Uridine 5'-diphospho-alpha-delta-glucuronate</synonym>
    <synonym>Uridine 5'-diphospho-alpha-delta-glucuronic acid</synonym>
    <synonym>Uridine 5'-diphospho-glucuronic acid</synonym>
    <synonym>Uridine 5'-diphosphoglucuronate</synonym>
    <synonym>Uridine 5'-diphosphoglucuronic acid</synonym>
    <synonym>Uridine 5'-[3-(D-glucopyranosyloxyuronic acid) dihydrogen diphosphate]</synonym>
    <synonym>Uridine diphosphate-glucuronate</synonym>
    <synonym>Uridine diphospho-D-glucuronate</synonym>
    <synonym>Uridine diphospho-D-glucuronic acid</synonym>
    <synonym>Uridine diphospho-delta-glucuronate</synonym>
    <synonym>Uridine diphospho-delta-glucuronic acid</synonym>
    <synonym>Uridine diphosphoglucuronate</synonym>
    <synonym>Uridine diphosphoglucuronic acid</synonym>
    <synonym>Uridine pyrophosphoglucuronate</synonym>
    <synonym>Uridine pyrophosphoglucuronic acid</synonym>
    <synonym>Uridinediphosphoglucuronic acid</synonym>
    <synonym>Acid, UDP glucuronic</synonym>
    <synonym>Acid, uridine diphosphoglucuronic</synonym>
    <synonym>Glucuronic acid, UDP</synonym>
    <synonym>Diphosphoglucuronic acid, uridine</synonym>
  </synonyms>
  <chemical_formula>C15H22N2O18P2</chemical_formula>
  <average_molecular_weight>580.2853</average_molecular_weight>
  <monisotopic_moleculate_weight>580.034284934</monisotopic_moleculate_weight>
  <iupac_name>(2S,3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>udp-α-D-glucuronic acid</traditional_iupac>
  <cas_registry_number>2616-64-0</cas_registry_number>
  <smiles>O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C15H22N2O18P2/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26)/t4-,6-,7+,8+,9-,10-,11+,12-,14-/m1/s1</inchi>
  <inchikey>HDYANYHVCAPMJV-LXQIFKJMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Lactones</class>
    <sub_class>Gamma butyrolactones</sub_class>
    <direct_parent>Gamma butyrolactones</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Gamma butyrolactone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>butan-4-olide</external_descriptor>
      <external_descriptor>diol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>580.2853</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>580.034284934</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H22N2O18P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H22N2O18P2/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26)/t4-,6-,7+,8+,9-,10-,11+,12-,14-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HDYANYHVCAPMJV-LXQIFKJMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>308.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>106.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>45.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Androstenedione Metabolism</name>
      <smpdb_id>SMP0087271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5143</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB031240</foodb_id>
  <chemspider_id>16522</chemspider_id>
  <pubchem_compound_id>17473</pubchem_compound_id>
  <kegg_id>C00167</kegg_id>
  <chebi_id>17200</chebi_id>
  <drugbank_id>DB03041</drugbank_id>
  <pdbe_id/>
  <knapsack_id>C00007238</knapsack_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>34117</bigg_id>
  <wikipedia_id>Uridine_diphosphate_glucuronic_acid</wikipedia_id>
  <metlin_id>5884</metlin_id>
  <synthesis_reference>Simon, Ethan S.; Grabowski, Sven; Whitesides, George M. Convenient syntheses of cytidine 5'-triphosphate, guanosine 5'-triphosphate, and uridine 5'-triphosphate and their use in the preparation of UDP-glucose, UDP-glucuronic acid, and GDP-mannose. J. Org. Chem., 1990, 55 (6), pp 1834–1841 DOI: 10.1021/jo00293a030</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00845</protein_accession>
      <name>Exostosin-2</name>
      <uniprot_id>O77783</uniprot_id>
      <gene_name>EXT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00846</protein_accession>
      <name>Hyaluronan synthase 2</name>
      <uniprot_id>O97711</uniprot_id>
      <gene_name>HAS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00847</protein_accession>
      <name>Exostosin-1</name>
      <uniprot_id>A5D7I4</uniprot_id>
      <gene_name>EXT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00848</protein_accession>
      <name>UDP-glucose 6-dehydrogenase</name>
      <uniprot_id>P12378</uniprot_id>
      <gene_name>UGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00849</protein_accession>
      <name>UDP-glucuronosyltransferase 3A1</name>
      <uniprot_id>Q1LZI1</uniprot_id>
      <gene_name>UGT3A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:50 UTC</creation_date>
  <update_date>2020-04-15 22:14:47 UTC</update_date>
  <accession>BMDB0000936</accession>
  <secondary_accessions>
    <accession>BMDB00936</accession>
  </secondary_accessions>
  <name>Uroporphyrin I</name>
  <description>Uroporphyrin I belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure. Uroporphyrin I is possibly soluble (in water) and a weakly acidic compound (based on its pKa). Uroporphyrin I exists in all eukaryotes, ranging from yeast to humans. In cattle, uroporphyrin i is involved in the metabolic pathway called the porphyrin metabolism pathway. Uroporphyrin I is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2,7,12,17-Porphinetetrapropionic acid</synonym>
    <synonym>3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropionic acid</synonym>
    <synonym>2,7,12,17-Porphinetetrapropionate</synonym>
    <synonym>3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropionate</synonym>
    <synonym>3,3',3'',3'''-(3,8,13,18-tetrakis-carboxymethyl-21H,23H-porphine-2,7,12,17-tetrayl)-tetrakis-propionate</synonym>
    <synonym>3,3',3'',3'''-(3,8,13,18-tetrakis-carboxymethyl-21H,23H-porphine-2,7,12,17-tetrayl)-tetrakis-propionic acid</synonym>
    <synonym>3,3',3'',3'''-(3,8,13,18-tetrakis-carboxymethyl-porphyrin-2,7,12,17-tetrayl)-tetra-propionate</synonym>
    <synonym>3,3',3'',3'''-(3,8,13,18-tetrakis-carboxymethyl-porphyrin-2,7,12,17-tetrayl)-tetra-propionic acid</synonym>
    <synonym>3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropanoate</synonym>
    <synonym>3,8,13,18-Tetrakis(carboxymethyl)porphyrin-2,7,12,17-tetrapropanoic acid</synonym>
    <synonym>3-[7,12,17-Tris-(2-carboxy-ethyl)-3,8,13,18-tetrakis-carboxymethyl-22,24-dihydro-porphin-2-yl]-propionate</synonym>
    <synonym>3-[7,12,17-Tris-(2-carboxy-ethyl)-3,8,13,18-tetrakis-carboxymethyl-22,24-dihydro-porphin-2-yl]-propionic acid</synonym>
  </synonyms>
  <chemical_formula>C40H38N4O16</chemical_formula>
  <average_molecular_weight>830.7469</average_molecular_weight>
  <monisotopic_moleculate_weight>830.228281188</monisotopic_moleculate_weight>
  <iupac_name>3-[9,14,19-tris(2-carboxyethyl)-5,10,15,20-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>uroporphyrin I</traditional_iupac>
  <cas_registry_number>607-14-7</cas_registry_number>
  <smiles>OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CC(O)=O)=C4CCC(O)=O)/C(CC(O)=O)=C3CCC(O)=O</smiles>
  <inchi>InChI=1S/C40H38N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-26-19(3-7-35(49)50)23(11-39(57)58)31(43-26)16-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)15-27-18(2-6-34(47)48)22(10-38(55)56)30(42-27)13-25(17)41-29/h13-16,41,44H,1-12H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b25-13-,26-14-,27-15-,28-16-,29-14-,30-13-,31-16-,32-15-</inchi>
  <inchikey>DAFUFNRZWDWXJP-JRHDEHKPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[9,14,19-tris(2-carboxyethyl)-5,10,15,20-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>830.7469</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>830.228281188</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CC(O)=O)=C4CCC(O)=O)/C(CC(O)=O)=C3CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C40H38N4O16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C40H38N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-26-19(3-7-35(49)50)23(11-39(57)58)31(43-26)16-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)15-27-18(2-6-34(47)48)22(10-38(55)56)30(42-27)13-25(17)41-29/h13-16,41,44H,1-12H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b25-13-,26-14-,27-15-,28-16-,29-14-,30-13-,31-16-,32-15-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DAFUFNRZWDWXJP-JRHDEHKPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>355.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>201.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>84.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16816</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022326</foodb_id>
  <chemspider_id>16736725</chemspider_id>
  <pubchem_compound_id/>
  <kegg_id>C05767</kegg_id>
  <chebi_id>27484</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5885</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:51 UTC</creation_date>
  <update_date>2020-04-16 20:40:03 UTC</update_date>
  <accession>BMDB0000939</accession>
  <secondary_accessions>
    <accession>BMDB00939</accession>
  </secondary_accessions>
  <name>S-Adenosylhomocysteine</name>
  <description>S-Adenosylhomocysteine, also known as adenosyl-homo-cys or adohcy, belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. S-Adenosylhomocysteine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. S-Adenosylhomocysteine exists in all living species, ranging from bacteria to humans. S-Adenosylhomocysteine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(2S)-2-Amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid</synonym>
    <synonym>2-S-Adenosyl-L-homocysteine</synonym>
    <synonym>Adenosyl-L-homocysteine</synonym>
    <synonym>Adenosylhomocysteine</synonym>
    <synonym>AdoHcy</synonym>
    <synonym>S-(5'-Adenosyl)-L-homocysteine</synonym>
    <synonym>S-[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl]-L-homocysteine</synonym>
    <synonym>SAH</synonym>
    <synonym>(2S)-2-Amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoate</synonym>
    <synonym>(2S)-2-Amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulphanyl)butanoate</synonym>
    <synonym>(2S)-2-Amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulphanyl)butanoic acid</synonym>
    <synonym>S-[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl]-L-homocysteine</synonym>
    <synonym>S-[1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl]-L-homocysteine</synonym>
    <synonym>(S)-5'-(S)-(3-Amino-3-carboxypropyl)-5'-thioadenosine</synonym>
    <synonym>5'-Deoxy-S-adenosyl-L-homocysteine</synonym>
    <synonym>5'-S-(3-Amino-3-carboxypropyl)-5'-thio-L-adenosine</synonym>
    <synonym>Adenosyl-homo-cys</synonym>
    <synonym>Adenosylhomo-cys</synonym>
    <synonym>Formycinylhomocysteine</synonym>
    <synonym>L-5'-S-(3-Amino-3-carboxypropyl)-5'-thior-adenosine</synonym>
    <synonym>L-S-Adenosyl-homocysteine</synonym>
    <synonym>L-S-Adenosylhomocysteine</synonym>
    <synonym>S-(5'-Deoxyadenosin-5'-yl)-L-homocysteine</synonym>
    <synonym>S-(5'-Deoxyadenosine-5')-L-homocysteine</synonym>
    <synonym>S-Adenosyl-homocysteine</synonym>
    <synonym>S-Adenosyl-L-homocysteine</synonym>
    <synonym>Adenosylhomocysteine, S</synonym>
    <synonym>S Adenosylhomocysteine</synonym>
  </synonyms>
  <chemical_formula>C14H20N6O5S</chemical_formula>
  <average_molecular_weight>384.411</average_molecular_weight>
  <monisotopic_moleculate_weight>384.12158847</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid</iupac_name>
  <traditional_iupac>S-adenosyl-L-homocysteine</traditional_iupac>
  <cas_registry_number>979-92-0</cas_registry_number>
  <smiles>N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=O</smiles>
  <inchi>InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1</inchi>
  <inchikey>ZJUKTBDSGOFHSH-WFMPWKQPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Lactones</class>
    <sub_class>Gamma butyrolactones</sub_class>
    <direct_parent>Gamma butyrolactones</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Gamma butyrolactone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>butan-4-olide</external_descriptor>
      <external_descriptor>diol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>384.411</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>384.12158847</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H20N6O5S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZJUKTBDSGOFHSH-WFMPWKQPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>182.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>92.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis</name>
      <smpdb_id>SMP0072037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:0)</name>
      <smpdb_id>SMP0080430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0080431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/15:0)</name>
      <smpdb_id>SMP0080432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:0)</name>
      <smpdb_id>SMP0080433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0080434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:0)</name>
      <smpdb_id>SMP0080435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0080436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0080437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:0)</name>
      <smpdb_id>SMP0080442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0080443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:0)</name>
      <smpdb_id>SMP0080450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0080451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:0)</name>
      <smpdb_id>SMP0080457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0080458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0080459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0080460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0080461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/15:0)</name>
      <smpdb_id>SMP0080487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:0)</name>
      <smpdb_id>SMP0080488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0080489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:0)</name>
      <smpdb_id>SMP0080490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0080491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0080492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:0)</name>
      <smpdb_id>SMP0080497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0080498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:0)</name>
      <smpdb_id>SMP0080505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0080506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:0)</name>
      <smpdb_id>SMP0080512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0080513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:0)</name>
      <smpdb_id>SMP0080514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0080515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:0)</name>
      <smpdb_id>SMP0080516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0080517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0080518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:0)</name>
      <smpdb_id>SMP0080523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0080524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:0)</name>
      <smpdb_id>SMP0080531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0080532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:0)</name>
      <smpdb_id>SMP0080538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0080539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:0)</name>
      <smpdb_id>SMP0080565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0080566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0080567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:0)</name>
      <smpdb_id>SMP0080572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0080573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:0)</name>
      <smpdb_id>SMP0080580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0080581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:0)</name>
      <smpdb_id>SMP0080587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0080588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0080595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:0)</name>
      <smpdb_id>SMP0080712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0080713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:0)</name>
      <smpdb_id>SMP0080720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0080721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:0)</name>
      <smpdb_id>SMP0080727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0080728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0080765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0080772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:0)</name>
      <smpdb_id>SMP0080820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0080821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:0)</name>
      <smpdb_id>SMP0080827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0080828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0080835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:0)</name>
      <smpdb_id>SMP0080864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0080865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ubiquinone Biosynthesis</name>
      <smpdb_id>SMP0087215</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438820</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB031150</foodb_id>
  <chemspider_id>388301</chemspider_id>
  <pubchem_compound_id>439155</pubchem_compound_id>
  <kegg_id>C00021</kegg_id>
  <chebi_id>16680</chebi_id>
  <drugbank_id>DB01752</drugbank_id>
  <pdbe_id/>
  <knapsack_id>C00007230</knapsack_id>
  <meta_cyc_id>ADENOSYL-HOMO-CYS</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33543</bigg_id>
  <wikipedia_id>S-Adenosyl-L-homocysteine</wikipedia_id>
  <metlin_id>296</metlin_id>
  <synthesis_reference>Holy, Antonin; Rosenberg, Ivan. Studies on S-adenosyl-L-homocysteine hydrolase. Part XV. An improved synthesis of S-adenosyl-L-homocysteine and related compounds. Collection of Czechoslovak Chemical Communications (1985), 50(7), 1514-18.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00100</protein_accession>
      <name>Phenylethanolamine N-methyltransferase</name>
      <uniprot_id>P10938</uniprot_id>
      <gene_name>PNMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00122</protein_accession>
      <name>Histamine N-methyltransferase</name>
      <uniprot_id>Q58DV7</uniprot_id>
      <gene_name>HNMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00395</protein_accession>
      <name>Histone-lysine N-methyltransferase SUV39H2</name>
      <uniprot_id>Q32PH7</uniprot_id>
      <gene_name>SUV39H2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00397</protein_accession>
      <name>Protein-L-isoaspartate(D-aspartate) O-methyltransferase</name>
      <uniprot_id>P15246</uniprot_id>
      <gene_name>PCMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00398</protein_accession>
      <name>Histone-lysine N-methyltransferase SETD8</name>
      <uniprot_id>Q2YDJ8</uniprot_id>
      <gene_name>SETD8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00399</protein_accession>
      <name>Diphthine synthase</name>
      <uniprot_id>Q5E982</uniprot_id>
      <gene_name>DPH5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00400</protein_accession>
      <name>Putative histone-lysine N-methyltransferase PRDM6</name>
      <uniprot_id>A6QPM3</uniprot_id>
      <gene_name>PRDM6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00402</protein_accession>
      <name>EHMT1 protein</name>
      <uniprot_id>A5PK11</uniprot_id>
      <gene_name>EHMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00405</protein_accession>
      <name>Ubiquinone biosynthesis methyltransferase COQ5, mitochondrial</name>
      <uniprot_id>Q0P5A2</uniprot_id>
      <gene_name>COQ5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00406</protein_accession>
      <name>Protein arginine N-methyltransferase 7</name>
      <uniprot_id>A6QQV6</uniprot_id>
      <gene_name>PRMT7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00409</protein_accession>
      <name>Thiopurine S-methyltransferase</name>
      <uniprot_id>Q17QQ2</uniprot_id>
      <gene_name>TPMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00410</protein_accession>
      <name>Hydroxyindole O-methyltransferase</name>
      <uniprot_id>P10950</uniprot_id>
      <gene_name>ASMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00411</protein_accession>
      <name>Protein arginine N-methyltransferase 5</name>
      <uniprot_id>A7YW45</uniprot_id>
      <gene_name>PRMT5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00412</protein_accession>
      <name>Guanidinoacetate N-methyltransferase</name>
      <uniprot_id>Q2TBQ3</uniprot_id>
      <gene_name>GAMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00413</protein_accession>
      <name>Hexaprenyldihydroxybenzoate methyltransferase, mitochondrial</name>
      <uniprot_id>Q3T131</uniprot_id>
      <gene_name>COQ3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00416</protein_accession>
      <name>Protein arginine N-methyltransferase 6</name>
      <uniprot_id>Q5E9L5</uniprot_id>
      <gene_name>PRMT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00417</protein_accession>
      <name>Histone-lysine N-methyltransferase SUV39H1</name>
      <uniprot_id>Q2NL30</uniprot_id>
      <gene_name>SUV39H1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00418</protein_accession>
      <name>Histone-lysine N-methyltransferase EZH1</name>
      <uniprot_id>A7E2Z2</uniprot_id>
      <gene_name>EZH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00419</protein_accession>
      <name>Histone-lysine N-methyltransferase SUV420H1</name>
      <uniprot_id>Q29RP8</uniprot_id>
      <gene_name>SUV420H1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00420</protein_accession>
      <name>Phosphatidylethanolamine N-methyltransferase</name>
      <uniprot_id>Q7YRH6</uniprot_id>
      <gene_name>PEMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00421</protein_accession>
      <name>Catechol O-methyltransferase</name>
      <uniprot_id>A7MBI7</uniprot_id>
      <gene_name>COMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00422</protein_accession>
      <name>Histone-lysine N-methyltransferase SETMAR</name>
      <uniprot_id>Q0VD24</uniprot_id>
      <gene_name>SETMAR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00837</protein_accession>
      <name>Adenosylhomocysteinase</name>
      <uniprot_id>A5PKK6</uniprot_id>
      <gene_name>AHCYL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00838</protein_accession>
      <name>Adenosylhomocysteinase</name>
      <uniprot_id>A6QLP2</uniprot_id>
      <gene_name>AHCYL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01293</protein_accession>
      <name>Adenosylhomocysteinase</name>
      <uniprot_id>Q3MHL4</uniprot_id>
      <gene_name>AHCY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:53 UTC</creation_date>
  <update_date>2020-03-13 16:24:53 UTC</update_date>
  <accession>BMDB0000940</accession>
  <secondary_accessions>
    <accession>BMDB00940</accession>
  </secondary_accessions>
  <name>Threonolactone</name>
  <description/>
  <synonyms>
    <synonym>L-Threonic acid-1,4-lactone</synonym>
    <synonym>Threonic acid-1,4-lactone</synonym>
    <synonym>L-Threonate-1,4-lactone</synonym>
    <synonym>Threonate-1,4-lactone</synonym>
    <synonym>3,4-Bis[(trimethylsilyl)oxy]dihydro-cis-2(3H)-furanone</synonym>
    <synonym>Bis-TMS-threono-1,4-lactone</synonym>
    <synonym>cis-Dihydro-3,4-bis[(trimethylsilyl)oxy]-2(3H)-furanone</synonym>
    <synonym>Di-TMS-threono-1,4-lactone</synonym>
  </synonyms>
  <chemical_formula>C4H6O4</chemical_formula>
  <average_molecular_weight>118.088</average_molecular_weight>
  <monisotopic_moleculate_weight>118.02660868</monisotopic_moleculate_weight>
  <iupac_name>(3R,4S)-3,4-dihydroxyoxolan-2-one</iupac_name>
  <traditional_iupac>(3R,4S)-3,4-dihydroxyoxolan-2-one</traditional_iupac>
  <cas_registry_number>21730-93-8</cas_registry_number>
  <smiles>O[C@H]1COC(=O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3+/m0/s1</inchi>
  <inchikey>SGMJBNSHAZVGMC-STHAYSLISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Lactones</class>
    <sub_class>Gamma butyrolactones</sub_class>
    <direct_parent>Gamma butyrolactones</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Gamma butyrolactone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>butan-4-olide</external_descriptor>
      <external_descriptor>diol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4S)-3,4-dihydroxyoxolan-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>118.088</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>118.02660868</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1COC(=O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H6O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SGMJBNSHAZVGMC-STHAYSLISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>22.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367446</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022328</foodb_id>
  <chemspider_id>2006913</chemspider_id>
  <pubchem_compound_id>2724794</pubchem_compound_id>
  <kegg_id/>
  <chebi_id>71176</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5888</metlin_id>
  <synthesis_reference>Nakaminami, Gen; Edo, Haruo; Nakagawa, Masazumi.  Syntheses of L-threose and methyl di-O-acetyl-L-threuronate from (+)-tartaric acid.    Bulletin of the Chemical Society of Japan  (1973),  46(1),  266-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:54 UTC</creation_date>
  <update_date>2020-03-13 16:24:54 UTC</update_date>
  <accession>BMDB0000941</accession>
  <secondary_accessions>
    <accession>BMDB00941</accession>
  </secondary_accessions>
  <name>Cholest-5-ene</name>
  <description/>
  <synonyms>
    <synonym>5-Cholestene</synonym>
    <synonym>D5-Cholestene</synonym>
    <synonym>Cholest-5-ene</synonym>
  </synonyms>
  <chemical_formula>C27H46</chemical_formula>
  <average_molecular_weight>370.6541</average_molecular_weight>
  <monisotopic_moleculate_weight>370.359951472</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene</iupac_name>
  <traditional_iupac>cholest-5-ene</traditional_iupac>
  <cas_registry_number>570-74-1</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CCCC[C@]12C</smiles>
  <inchi>InChI=1S/C27H46/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h12,19-20,22-25H,6-11,13-18H2,1-5H3/t20-,22+,23-,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>DTGDZMYNKLTSKC-HKQCOZBKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholestane steroids. These are steroids with a structure containing the 27-carbon cholestane skeleton.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholestane steroids</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclic olefins</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Polycyclic hydrocarbons</alternative_parent>
      <alternative_parent>Unsaturated aliphatic hydrocarbons</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholestane-skeleton</substituent>
      <substituent>Cyclic olefin</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon</substituent>
      <substituent>Olefin</substituent>
      <substituent>Polycyclic hydrocarbon</substituent>
      <substituent>Unsaturated aliphatic hydrocarbon</substituent>
      <substituent>Unsaturated hydrocarbon</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>cholestanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>8.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>370.6541</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>370.359951472</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CCCC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H46/c1-19(2)9-8-10-20(3)23-14-15-24-22-13-12-21-11-6-7-17-26(21,4)25(22)16-18-27(23,24)5/h12,19-20,22-25H,6-11,13-18H2,1-5H3/t20-,22+,23-,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DTGDZMYNKLTSKC-HKQCOZBKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>118.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>49.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352239</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022329</foodb_id>
  <chemspider_id>389543</chemspider_id>
  <pubchem_compound_id>440663</pubchem_compound_id>
  <kegg_id>C05416</kegg_id>
  <chebi_id>28810</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5889</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Baker, Robert H.; Squire, Edward N.  Derived steroids. I. Cholesteryl ketones.    Journal of the American Chemical Society  (1948),  70  1487-90.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:55 UTC</creation_date>
  <update_date>2020-03-13 16:24:54 UTC</update_date>
  <accession>BMDB0000942</accession>
  <secondary_accessions>
    <accession>BMDB00942</accession>
  </secondary_accessions>
  <name>Tetrahydroneopterin</name>
  <description/>
  <synonyms>
    <synonym>1-(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)-1,2,3-propanetriol</synonym>
    <synonym>5,6,7,8-Tetrahydroneopterin</synonym>
    <synonym>Tetrahydro-D-monapterin</synonym>
    <synonym>Tetrahydroneopterin</synonym>
  </synonyms>
  <chemical_formula>C9H15N5O4</chemical_formula>
  <average_molecular_weight>257.2465</average_molecular_weight>
  <monisotopic_moleculate_weight>257.112403993</monisotopic_moleculate_weight>
  <iupac_name>2-amino-6-(1,2,3-trihydroxypropyl)-1,4,5,6,7,8-hexahydropteridin-4-one</iupac_name>
  <traditional_iupac>2-amino-6-(1,2,3-trihydroxypropyl)-5,6,7,8-tetrahydro-1H-pteridin-4-one</traditional_iupac>
  <cas_registry_number>25976-00-5</cas_registry_number>
  <smiles>NC1=NC(=O)C2=C(NCC(N2)C(O)C(O)CO)N1</smiles>
  <inchi>InChI=1S/C9H15N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h3-4,6,12,15-17H,1-2H2,(H4,10,11,13,14,18)</inchi>
  <inchikey>XHIXPVCTDRNTTC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Biopterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>1,3-aminoalcohols</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>1,3-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Biopterin</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-6-(1,2,3-trihydroxypropyl)-1,4,5,6,7,8-hexahydropteridin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>257.2465</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>257.112403993</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=C(NCC(N2)C(O)C(O)CO)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H15N5O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H15N5O4/c10-9-13-7-5(8(18)14-9)12-3(1-11-7)6(17)4(16)2-15/h3-4,6,12,15-17H,1-2H2,(H4,10,11,13,14,18)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XHIXPVCTDRNTTC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>152.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>69.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369480</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022330</foodb_id>
  <chemspider_id>141864</chemspider_id>
  <pubchem_compound_id>161510</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5890</metlin_id>
  <synthesis_reference>Schircks, Bernhard; Bieri, Jost H.; Viscontini, Max.  On pterin chemistry.  Part 55.  Preparation and characterization of pure 5,6,7,8-tetrahydro-L-neopterin and 5,6,7,8-tetrahydro-D-monapterin.    Helvetica Chimica Acta  (1976),  59(1),  248-52.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:56 UTC</creation_date>
  <update_date>2020-04-14 22:48:39 UTC</update_date>
  <accession>BMDB0000943</accession>
  <secondary_accessions>
    <accession>BMDB00943</accession>
  </secondary_accessions>
  <name>Threonic acid</name>
  <description>Threonic acid, also known as threonate or clarimem, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Threonic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).</description>
  <synonyms>
    <synonym>Threonate</synonym>
    <synonym>(R*,s*)-2,3,4-trihydroxy-butanoate</synonym>
    <synonym>(R*,s*)-2,3,4-trihydroxy-butanoic acid</synonym>
    <synonym>Threo-2,3,4-trihydroxybutyrate</synonym>
    <synonym>Threo-2,3,4-trihydroxybutyric acid</synonym>
    <synonym>Magnesium threonate</synonym>
    <synonym>Calcium threonate</synonym>
    <synonym>Threonic acid, (R-(r*,s*))-isomer</synonym>
    <synonym>2,3,4-Trihydroxy-(threo)-butanoic acid</synonym>
    <synonym>Calcium L-threonate</synonym>
    <synonym>Threonic acid, (r*,r*)-isomer</synonym>
    <synonym>ClariMem</synonym>
    <synonym>L-TAMS compound</synonym>
    <synonym>L-Threonic acid magnesium salt</synonym>
    <synonym>MMFS-01</synonym>
    <synonym>D-Threonate</synonym>
    <synonym>Threonic acid</synonym>
  </synonyms>
  <chemical_formula>C4H8O5</chemical_formula>
  <average_molecular_weight>136.1033</average_molecular_weight>
  <monisotopic_moleculate_weight>136.037173366</monisotopic_moleculate_weight>
  <iupac_name>(2S,3R)-2,3,4-trihydroxybutanoic acid</iupac_name>
  <traditional_iupac>threonic acid</traditional_iupac>
  <cas_registry_number>3909-12-4</cas_registry_number>
  <smiles>OC[C@@H](O)[C@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m1/s1</inchi>
  <inchikey>JPIJQSOTBSSVTP-GBXIJSLDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
      <substituent>Sugar acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>threonic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>53 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3R)-2,3,4-trihydroxybutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>136.1033</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>136.037173366</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)[C@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JPIJQSOTBSSVTP-GBXIJSLDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>26.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333987</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
          <pubmed_id>25108860</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022331</foodb_id>
  <chemspider_id>133224</chemspider_id>
  <pubchem_compound_id>151152</pubchem_compound_id>
  <kegg_id>C01620</kegg_id>
  <chebi_id>49059</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>38497</bigg_id>
  <wikipedia_id>Threonic acid</wikipedia_id>
  <metlin_id>5891</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Song J Z; Huang D P; Tian S J; Sun Z P  Determination of L-threonate in calcium L-threonate preparations by capillary electrophoresis with indirect UV detection.    Electrophoresis  (1999),  20(9),  1850-5.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.</reference_text>
      <pubmed_id>25108860</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:57 UTC</creation_date>
  <update_date>2020-04-16 17:52:21 UTC</update_date>
  <accession>BMDB0000944</accession>
  <secondary_accessions>
    <accession>BMDB00944</accession>
  </secondary_accessions>
  <name>Behenic acid</name>
  <description>Behenic acid, also known as docosanoate or 1-docosanoic acid, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Behenic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Behenic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Docosanoic acid</synonym>
    <synonym>Behensaeure</synonym>
    <synonym>CH3-[CH2]20-COOH</synonym>
    <synonym>Docosanic acid</synonym>
    <synonym>Docosanoate</synonym>
    <synonym>Docosansaeure</synonym>
    <synonym>Docosoic acid</synonym>
    <synonym>Dokosansaeure</synonym>
    <synonym>N-Docosanoic acid</synonym>
    <synonym>1-Docosanoate</synonym>
    <synonym>Docosanate</synonym>
    <synonym>Docosanoic acid</synonym>
    <synonym>Docosoate</synonym>
    <synonym>N-Docosanoate</synonym>
    <synonym>Behenate</synonym>
    <synonym>FA(22:0)</synonym>
    <synonym>Behenic acid</synonym>
  </synonyms>
  <chemical_formula>C22H44O2</chemical_formula>
  <average_molecular_weight>340.5836</average_molecular_weight>
  <monisotopic_moleculate_weight>340.334130652</monisotopic_moleculate_weight>
  <iupac_name>docosanoic acid</iupac_name>
  <traditional_iupac>behenic acid</traditional_iupac>
  <cas_registry_number>112-85-6</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C22H44O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H,23,24)</inchi>
  <inchikey>UKMSUNONTOPOIO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Very long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Very long-chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Saturated fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>81 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1.6e-05 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>9.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>8.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>docosanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>340.5836</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>340.334130652</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C22H44O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C22H44O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H,23,24)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UKMSUNONTOPOIO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>104.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373919</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373921</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373922</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440420</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>77.4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>80.45</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>1111.86</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>1340.49</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>520.11</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>481</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>293.614</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples have been collected from Heifer cows.</comment>
      <references>
        <reference>
          <reference_text>Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub  2013 Jun 5.</reference_text>
          <pubmed_id>23871026</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Oocyte</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by CP9010 autosampler onto a capillary column within a CP9001 gas chromatograph in slaughtered cow ovaries.</comment>
      <references>
        <reference>
          <reference_text>McEvoy TG, Coull GD, Broadbent PJ, Hutchinson JS, Speake BK: Fatty acid composition of lipids in immature cattle, pig and sheep oocytes with intact zona pellucida. J Reprod Fertil. 2000 Jan;118(1):163-70.</reference_text>
          <pubmed_id>10793638</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB005830</foodb_id>
  <chemspider_id>7923</chemspider_id>
  <pubchem_compound_id>8215</pubchem_compound_id>
  <kegg_id>C08281</kegg_id>
  <chebi_id>28941</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id>C00001211</knapsack_id>
  <wikipedia_id>Behenic acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <metlin_id>260</metlin_id>
  <synthesis_reference>Lu, Jianmin; Li, He; Yang, Yiping; Du, Baoshan.  Preparation of behenic acid from erucic acid by hydrogenation at ordinary pressure.    Zhongguo Youzhi  (1997),  22(5),  57-58.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Tang C, Zhang K, Zhan T, Zhao Q, Zhang J: Metabolic Characterization of Dairy Cows Treated with Gossypol by Blood Biochemistry and Body Fluid Untargeted Metabolome Analyses. J Agric Food Chem. 2017 Oct 25;65(42):9369-9378. doi: 10.1021/acs.jafc.7b03544. Epub 2017 Oct 17.</reference_text>
      <pubmed_id>28965405</pubmed_id>
    </reference>
    <reference>
      <reference_text>Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.</reference_text>
      <pubmed_id>19038946</pubmed_id>
    </reference>
    <reference>
      <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:38:59 UTC</creation_date>
  <update_date>2020-04-16 20:40:48 UTC</update_date>
  <accession>BMDB0000946</accession>
  <secondary_accessions>
    <accession>BMDB00946</accession>
  </secondary_accessions>
  <name>Ursodeoxycholic acid</name>
  <description/>
  <synonyms>
    <synonym>(3alpha,5beta,7beta)-3,7-Dihydroxycholan-24-Oic acid</synonym>
    <synonym>3alpha,7beta-Dihydroxy-5beta-cholan-24-Oic acid</synonym>
    <synonym>Actigall</synonym>
    <synonym>Ursodeoxycholate</synonym>
    <synonym>Ursodiol</synonym>
    <synonym>Urso</synonym>
    <synonym>(3a,5b,7b)-3,7-Dihydroxycholan-24-Oate</synonym>
    <synonym>(3a,5b,7b)-3,7-Dihydroxycholan-24-Oic acid</synonym>
    <synonym>(3alpha,5beta,7beta)-3,7-Dihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5β,7β)-3,7-dihydroxycholan-24-Oate</synonym>
    <synonym>(3Α,5β,7β)-3,7-dihydroxycholan-24-Oic acid</synonym>
    <synonym>3a,7b-Dihydroxy-5b-cholan-24-Oate</synonym>
    <synonym>3a,7b-Dihydroxy-5b-cholan-24-Oic acid</synonym>
    <synonym>3alpha,7beta-Dihydroxy-5beta-cholan-24-Oate</synonym>
    <synonym>3Α,7β-dihydroxy-5β-cholan-24-Oate</synonym>
    <synonym>3Α,7β-dihydroxy-5β-cholan-24-Oic acid</synonym>
    <synonym>3 alpha,7 beta-Dihydroxy-5 beta-cholan-24-Oic acid</synonym>
    <synonym>Acid, deoxyursocholic</synonym>
    <synonym>Acid, ursacholic</synonym>
    <synonym>Acid, ursodeoxycholic</synonym>
    <synonym>Cholit-ursan</synonym>
    <synonym>Cholofalk</synonym>
    <synonym>Delursan</synonym>
    <synonym>Deoxyursocholic acid</synonym>
    <synonym>Ursochol</synonym>
    <synonym>Ursogal</synonym>
    <synonym>Ursolite</synonym>
    <synonym>Ursolvan</synonym>
    <synonym>Urso heumann</synonym>
    <synonym>Ursobilane</synonym>
    <synonym>Ursofalk</synonym>
    <synonym>Destolit</synonym>
    <synonym>Sodium ursodeoxycholate</synonym>
    <synonym>Ursacholic acid</synonym>
    <synonym>Ursodeoxycholate, sodium</synonym>
    <synonym>3 alpha,7 beta Dihydroxy 5 beta cholan 24 Oic acid</synonym>
    <synonym>Urdox</synonym>
    <synonym>(3a,5b,7b)-3,7-Dihydroxy-cholan-24-Oate</synonym>
    <synonym>(3a,5b,7b)-3,7-Dihydroxy-cholan-24-Oic acid</synonym>
    <synonym>3,7-Dihydroxycholan-24-Oic acid</synonym>
    <synonym>3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acid</synonym>
    <synonym>3-alpha,7-beta-Dihydroxycholanic acid</synonym>
    <synonym>3-alpha,7-beta-Dioxycholanic acid</synonym>
    <synonym>Antigall</synonym>
    <synonym>Urosdesoxycholate</synonym>
    <synonym>Urosdesoxycholic acid</synonym>
    <synonym>Ursodeoxycholicacid</synonym>
    <synonym>Ursodexycholate</synonym>
    <synonym>Ursodexycholic acid</synonym>
    <synonym>Aventis brand OF ursodeoxycholic acid</synonym>
    <synonym>Axcan brand OF ursodeoxycholic acid</synonym>
    <synonym>Falk brand OF ursodeoxycholic acid</synonym>
    <synonym>Farmasa brand OF ursodeoxycholic acid</synonym>
    <synonym>Galen brand OF ursodeoxycholic acid</synonym>
    <synonym>Orphan brand OF ursodeoxycholic acid</synonym>
    <synonym>Antigen brand OF ursodeoxycholic acid</synonym>
    <synonym>CP Brand OF ursodeoxycholic acid</synonym>
    <synonym>Heumann brand OF ursodeoxycholic acid</synonym>
    <synonym>Niddapharm brand OF ursodeoxycholic acid</synonym>
    <synonym>Norgine brand OF ursodeoxycholic acid</synonym>
    <synonym>Sanofi synthelabo brand OF ursodeoxycholic acid</synonym>
    <synonym>Estedi brand OF ursodeoxycholic acid</synonym>
    <synonym>Provalis brand OF ursodeoxycholic acid</synonym>
    <synonym>Tramedico brand OF ursodeoxycholic acid</synonym>
    <synonym>Vita brand OF ursodeoxycholic acid</synonym>
    <synonym>Zambon brand OF ursodeoxycholic acid</synonym>
  </synonyms>
  <chemical_formula>C24H40O4</chemical_formula>
  <average_molecular_weight>392.572</average_molecular_weight>
  <monisotopic_moleculate_weight>392.292659768</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</traditional_iupac>
  <cas_registry_number>128-13-2</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O</smiles>
  <inchi>InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1</inchi>
  <inchikey>RUDATBOHQWOJDD-UZVSRGJWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-alpha-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>C24 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>Cholane and derivatives</external_descriptor>
      <external_descriptor>bile acid</external_descriptor>
      <external_descriptor>dihydroxy-5beta-cholanic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>392.572</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>392.292659768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RUDATBOHQWOJDD-UZVSRGJWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>69930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>69931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>69932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451338</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022332</foodb_id>
  <chemspider_id>29131</chemspider_id>
  <pubchem_compound_id>31401</pubchem_compound_id>
  <kegg_id>C07880</kegg_id>
  <chebi_id>9907</chebi_id>
  <drugbank_id>DB01586</drugbank_id>
  <pdbe_id/>
  <knapsack_id>C00032464</knapsack_id>
  <wikipedia_id>Ursodiol</wikipedia_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <metlin_id>5893</metlin_id>
  <synthesis_reference>Sawada, Haruji; Kulprecha, Songsri; Nilubol, Naline; Yoshida, Toshiomi; Kinoshita, Shinichi; Taguchi, Hisaharu. Microbial production of ursodeoxycholic acid from lithocholic acid by Fusarium equiseti M41. Applied and Environmental Microbiology (1982), 44(</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:00 UTC</creation_date>
  <update_date>2020-03-13 16:24:56 UTC</update_date>
  <accession>BMDB0000947</accession>
  <secondary_accessions>
    <accession>BMDB00947</accession>
  </secondary_accessions>
  <name>Undecanoic acid</name>
  <description>Undecanoic acid, also known as N-undecylic acid or N-undecanoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Undecanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Undecanoic acid exists in all eukaryotes, ranging from yeast to humans. Undecanoic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Decanecarboxylic acid</synonym>
    <synonym>CH3-[CH2]9-COOH</synonym>
    <synonym>Hendecanoic acid</synonym>
    <synonym>N-Undecanoic acid</synonym>
    <synonym>N-Undecoic acid</synonym>
    <synonym>N-Undecylic acid</synonym>
    <synonym>UDA</synonym>
    <synonym>Undecoic acid</synonym>
    <synonym>Undecylic acid</synonym>
    <synonym>Undekansaeure</synonym>
    <synonym>1-Decanecarboxylate</synonym>
    <synonym>Hendecanoate</synonym>
    <synonym>N-Undecanoate</synonym>
    <synonym>N-Undecoate</synonym>
    <synonym>N-Undecylate</synonym>
    <synonym>Undecoate</synonym>
    <synonym>Undecylate</synonym>
    <synonym>Undecanoate</synonym>
    <synonym>1N-Undecoic acid</synonym>
    <synonym>FA(11:0)</synonym>
    <synonym>Undecanoic acid</synonym>
  </synonyms>
  <chemical_formula>C11H22O2</chemical_formula>
  <average_molecular_weight>186.2912</average_molecular_weight>
  <monisotopic_moleculate_weight>186.161979948</monisotopic_moleculate_weight>
  <iupac_name>undecanoic acid</iupac_name>
  <traditional_iupac>undecanoic acid</traditional_iupac>
  <cas_registry_number>112-37-8</cas_registry_number>
  <smiles>CCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)</inchi>
  <inchikey>ZDPHROOEEOARMN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>medium-chain fatty acid</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>28.6 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0522 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.42</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>undecanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>186.2912</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>186.161979948</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H22O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZDPHROOEEOARMN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37858</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2847</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4944</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181912</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.38 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk. Meta-Analysis</comment>
      <references>
        <reference>
          <reference_text>Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.</reference_text>
          <pubmed_id>19038946</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.51 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.516 +/- 0.014</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.45 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93.</reference_text>
          <pubmed_id>5409465</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
          <pubmed_id>14168161</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB000700</foodb_id>
  <chemspider_id>7888</chemspider_id>
  <pubchem_compound_id>8180</pubchem_compound_id>
  <kegg_id>C17715</kegg_id>
  <chebi_id>32368</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id>C00007421</knapsack_id>
  <wikipedia_id>Undecylic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <metlin_id>5894</metlin_id>
  <synthesis_reference>Schreyer, Gerd; Schwarze, Werner; Weigert, Wolfgang.  Carboxylic acids by oxidation of vicinal diols.    Ger. Offen.  (1972),     10 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
      <pubmed_id>14168161</pubmed_id>
    </reference>
    <reference>
      <reference_text>Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93.</reference_text>
      <pubmed_id>5409465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.</reference_text>
      <pubmed_id>19038946</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:01 UTC</creation_date>
  <update_date>2020-03-13 16:24:57 UTC</update_date>
  <accession>BMDB0000949</accession>
  <secondary_accessions>
    <accession>BMDB00949</accession>
  </secondary_accessions>
  <name>Tetrahydrocortisol</name>
  <description>Tetrahydrocortisol belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Tetrahydrocortisol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Tetrahydrocortisol can be converted into dihydrocortisol; which is mediated by the enzyme aldo-keto reductase family 1 member C4. In cattle, tetrahydrocortisol is involved in the metabolic pathway called the steroidogenesis pathway. Tetrahydrocortisol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>Taurochenodeoxycholic acid</synonym>
    <synonym>Chenodeoxycholoyltaurine</synonym>
    <synonym>Taurochenodeoxycholate</synonym>
    <synonym>Taurochenodesoxycholate</synonym>
    <synonym>Taurine chenodeoxycholate</synonym>
    <synonym>Taurine chenodeoxycholic acid</synonym>
    <synonym>12-Deoxycholyltaurine</synonym>
    <synonym>12-Desoxycholyltaurine</synonym>
    <synonym>3a,7a-Dihydroxy-N-(2-sulfoethyl)-5b-cholan-24-amide</synonym>
    <synonym>Chenodeoxycholyltaurine</synonym>
    <synonym>Chenyltaurine</synonym>
    <synonym>N-(3a,7a-Dihydroxy-5b-cholan-24-oyl)-taurine</synonym>
    <synonym>Acid, taurochenodeoxycholic</synonym>
    <synonym>Chenodeoxycholate, taurine</synonym>
    <synonym>2-Hydroxy-1-(3,11,17-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanone</synonym>
    <synonym>3a,11b,17,21-Tetrahydroxy-5b-pregnan-20-one</synonym>
    <synonym>3b,11b,17,21-Tetrahydroxy-5b-pregnan-20-one</synonym>
    <synonym>3b,11b,17a,21-Tetrahydroxy-5b-pregnan-20-ON</synonym>
    <synonym>5b-Tetrahydrocortisol</synonym>
    <synonym>Dihydrocortison</synonym>
    <synonym>tetrahydro-Cortisol</synonym>
    <synonym>Urocortisol</synonym>
  </synonyms>
  <chemical_formula>C21H34O5</chemical_formula>
  <average_molecular_weight>366.4917</average_molecular_weight>
  <monisotopic_moleculate_weight>366.240624198</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one</iupac_name>
  <traditional_iupac>2-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethanone</traditional_iupac>
  <cas_registry_number>516-35-8</cas_registry_number>
  <smiles>C[C@]12C[C@H](O)C3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@]2(O)C(=O)CO</smiles>
  <inchi>InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12?,13-,14?,15?,16+,18?,19+,20+,21+/m1/s1</inchi>
  <inchikey>AODPIQQILQLWGS-OBRSLYEHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Taurinated bile acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Alkanesulfonic acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Dihydroxy bile acids, alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonic acids</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfonyls</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkanesulfonic acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfonyl</substituent>
      <substituent>Taurinated bile acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C26 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>Taurine conjugates</external_descriptor>
      <external_descriptor>Taurine conjugates</external_descriptor>
      <external_descriptor>bile acid taurine conjugate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-1-[(2S,5R,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>366.4917</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>366.240624198</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@]12C[C@H](O)C3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@]2(O)C(=O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H34O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12?,13-,14?,15?,16+,18?,19+,20+,21+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AODPIQQILQLWGS-OBRSLYEHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>97.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroidogenesis</name>
      <smpdb_id>SMP0087238</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>83814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>83815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>83816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145508</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022335</foodb_id>
  <drugbank_id>DB08833</drugbank_id>
  <chemspider_id>343282</chemspider_id>
  <pubchem_compound_id>387316</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id>C05465</kegg_id>
  <chebi_id>16525</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>45864</bigg_id>
  <wikipedia_id/>
  <metlin_id>5897</metlin_id>
  <meta_cyc_id>CHENODEOXYCHOLOYLTAURINE</meta_cyc_id>
  <synthesis_reference>Gould, David H.; Oliveto, Eugene P.  17a-Hydroxycorticosterone and intermediates.    (1957),     US  2783254  19570226  CAN 51:62564  AN 1957:62564</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:02 UTC</creation_date>
  <update_date>2020-03-13 16:24:57 UTC</update_date>
  <accession>BMDB0000950</accession>
  <secondary_accessions>
    <accession>BMDB00950</accession>
  </secondary_accessions>
  <name>Cer(d18:1/23:0)</name>
  <description/>
  <synonyms>
    <synonym>Ceramide</synonym>
    <synonym>N-(Tricosanoyl)-sphing-4-enine</synonym>
    <synonym>Ceramide(D18:1/23:0)</synonym>
    <synonym>N-(Tricosanoyl)-sphingosine</synonym>
    <synonym>N-(Tricosanoyl)-D-erythro-sphingosine</synonym>
    <synonym>N-(Tricosanoyl)-4-sphingenine</synonym>
    <synonym>N-(Tricosanoyl)-D-sphingosine</synonym>
    <synonym>N-(Tricosanoyl)-sphingenine</synonym>
    <synonym>N-(Tricosanoyl)-erythro-4-sphingenine</synonym>
    <synonym>N-[(2S)-1,3-Dihydroxyoctadec-4-en-2-yl]tricosanimidate</synonym>
  </synonyms>
  <chemical_formula>C41H81NO3</chemical_formula>
  <average_molecular_weight>636.103</average_molecular_weight>
  <monisotopic_moleculate_weight>635.621645472</monisotopic_moleculate_weight>
  <iupac_name>N-[(2S,4E)-1,3-dihydroxyoctadec-4-en-2-yl]tricosanamide</iupac_name>
  <traditional_iupac>N-[(2S,4E)-1,3-dihydroxyoctadec-4-en-2-yl]tricosanamide</traditional_iupac>
  <cas_registry_number/>
  <smiles>CCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)C(O)\C=C\CCCCCCCCCCCCC</smiles>
  <inchi>InChI=1S/C41H81NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-27-29-31-33-35-37-41(45)42-39(38-43)40(44)36-34-32-30-28-26-24-16-14-12-10-8-6-4-2/h34,36,39-40,43-44H,3-33,35,37-38H2,1-2H3,(H,42,45)/b36-34+/t39-,40?/m0/s1</inchi>
  <inchikey>NAJHAHQNQCNWOP-ZEUAYCHYSA-N</inchikey>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>10.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>13.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[(2S,4E)-1,3-dihydroxyoctadec-4-en-2-yl]tricosanamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>636.103</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>635.621645472</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO)C(O)\C=C\CCCCCCCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C41H81NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C41H81NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-27-29-31-33-35-37-41(45)42-39(38-43)40(44)36-34-32-30-28-26-24-16-14-12-10-8-6-4-2/h34,36,39-40,43-44H,3-33,35,37-38H2,1-2H3,(H,42,45)/b36-34+/t39-,40?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NAJHAHQNQCNWOP-ZEUAYCHYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>69.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>197.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>87.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1305388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1305389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1305390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1419913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1419914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1419915</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id/>
  <kegg_id/>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Gaudin, K.; Lesellier, E.; Chaminade, P.; Ferrier, D.; Baillet, A.; Tchapla, A.  Retention behaviour of ceramides in sub-critical fluid chromatography in comparison with non-aqueous reversed-phase liquid chromatography.    Journal of Chromatography, A  (2000),  883(1+2),  211-222</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:04 UTC</creation_date>
  <update_date>2020-04-14 22:48:40 UTC</update_date>
  <accession>BMDB0000951</accession>
  <secondary_accessions>
    <accession>BMDB00951</accession>
  </secondary_accessions>
  <name>Taurochenodesoxycholic acid</name>
  <description/>
  <synonyms>
    <synonym>Taurochenodesoxycholate</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]-N-(2-sulfoethyl)pentanimidate</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]-N-(2-sulphoethyl)pentanimidate</synonym>
    <synonym>(4R)-4-[(1S,2S,5R,7S,10R,11S,14R,15R)-5,9-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]-N-(2-sulphoethyl)pentanimidic acid</synonym>
  </synonyms>
  <chemical_formula>C26H45NO6S</chemical_formula>
  <average_molecular_weight>499.71</average_molecular_weight>
  <monisotopic_moleculate_weight>499.296759347</monisotopic_moleculate_weight>
  <iupac_name>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-N-(2-sulfoethyl)pentanimidic acid</iupac_name>
  <traditional_iupac>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-N-(2-sulfoethyl)pentanimidic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@](C)(CCC(O)=NCCS(O)(=O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C([H])(O)C[C@]4([H])C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C</smiles>
  <inchi>InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22?,24+,25+,26-/m1/s1</inchi>
  <inchikey>BHTRKEVKTKCXOH-VLYLQVOASA-N</inchikey>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-N-(2-sulfoethyl)pentanimidic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>499.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>499.296759347</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](C)(CCC(O)=NCCS(O)(=O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C([H])(O)C[C@]4([H])C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H45NO6S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H45NO6S/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17+,18-,19-,20+,21+,22?,24+,25+,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHTRKEVKTKCXOH-VLYLQVOASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>127.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>131.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>56.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1252963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1252964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1252965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1368199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1368200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1368201</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id/>
  <pubchem_compound_id>25200521</pubchem_compound_id>
  <drugbank_id/>
  <foodb_id/>
  <phenol_explorer_compound_id/>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Karbach Ia I; Rybak P G  Synthesis of conjugated bile acids.    Ukrainskii biokhimicheskii zhurnal  (1979),  51(1),  76-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:05 UTC</creation_date>
  <update_date>2020-03-13 16:24:59 UTC</update_date>
  <accession>BMDB0000953</accession>
  <secondary_accessions>
    <accession>BMDB00953</accession>
  </secondary_accessions>
  <name>Suberylglycine</name>
  <description/>
  <synonyms>
    <synonym>Suberylglycin</synonym>
    <synonym>7-[(Carboxymethyl)-C-hydroxycarbonimidoyl]heptanoate</synonym>
    <synonym>Suberylglycine</synonym>
  </synonyms>
  <chemical_formula>C10H17NO5</chemical_formula>
  <average_molecular_weight>231.2457</average_molecular_weight>
  <monisotopic_moleculate_weight>231.110672659</monisotopic_moleculate_weight>
  <iupac_name>7-[(carboxymethyl)carbamoyl]heptanoic acid</iupac_name>
  <traditional_iupac>7-(carboxymethylcarbamoyl)heptanoic acid</traditional_iupac>
  <cas_registry_number>60317-54-6</cas_registry_number>
  <smiles>OC(=O)CCCCCCC(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C10H17NO5/c12-8(11-7-10(15)16)5-3-1-2-4-6-9(13)14/h1-7H2,(H,11,12)(H,13,14)(H,15,16)</inchi>
  <inchikey>HXATVKDSYDWTCX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>7-[(carboxymethyl)carbamoyl]heptanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>231.2457</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>231.110672659</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCCCCC(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H17NO5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H17NO5/c12-8(11-7-10(15)16)5-3-1-2-4-6-9(13)14/h1-7H2,(H,11,12)(H,13,14)(H,15,16)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HXATVKDSYDWTCX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>103.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>361929</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022336</foodb_id>
  <chemspider_id>4956295</chemspider_id>
  <pubchem_compound_id>6453952</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <metlin_id>5899</metlin_id>
  <synthesis_reference>Gregersen, Niels; Gron, Ida; Rasmussen, Karsten; Kolvraa, Steen.  Gas chromatographic mass spectrometric identification of N-dicarboxylmonoglycines.    Biomedical Mass Spectrometry  (1978),  5(1),  80-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:06 UTC</creation_date>
  <update_date>2020-04-15 22:34:12 UTC</update_date>
  <accession>BMDB0000954</accession>
  <secondary_accessions>
    <accession>BMDB00954</accession>
  </secondary_accessions>
  <name>trans-Ferulic acid</name>
  <description/>
  <synonyms>
    <synonym>(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid</synonym>
    <synonym>(e)-4'-Hydroxy-3'-methoxycinnamic acid</synonym>
    <synonym>(e)-4-Hydroxy-3-methoxycinnamic acid</synonym>
    <synonym>(e)-Ferulic acid</synonym>
    <synonym>3-(4-Hydroxy-3-methoxyphenyl)propenoic acid</synonym>
    <synonym>3-Methoxy-4-hydroxy-trans-cinnamic acid</synonym>
    <synonym>4-Hydroxy-3-methoxycinnamic acid</synonym>
    <synonym>trans-4-Hydroxy-3-methoxycinnamic acid</synonym>
    <synonym>trans-Ferulic acid</synonym>
    <synonym>3-Methoxy-4-hydroxy-trans-cinnamate</synonym>
    <synonym>4-Hydroxy-3-methoxycinnamate</synonym>
    <synonym>(e)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate</synonym>
    <synonym>(e)-4'-Hydroxy-3'-methoxycinnamate</synonym>
    <synonym>(e)-4-Hydroxy-3-methoxycinnamate</synonym>
    <synonym>(e)-Ferulate</synonym>
    <synonym>3-(4-Hydroxy-3-methoxyphenyl)propenoate</synonym>
    <synonym>trans-4-Hydroxy-3-methoxycinnamate</synonym>
    <synonym>trans-Ferulate</synonym>
    <synonym>Ferulate</synonym>
    <synonym>8,8'-Diferulic acid</synonym>
    <synonym>Ferulic acid, (e)-isomer</synonym>
    <synonym>Ferulic acid, monosodium salt</synonym>
    <synonym>Sodium ferulate</synonym>
    <synonym>Ferulic acid, (Z)-isomer</synonym>
    <synonym>(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate</synonym>
    <synonym>(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid</synonym>
    <synonym>(e)-4-Hydroxy-3-methoxy-cinnamate</synonym>
    <synonym>(e)-4-Hydroxy-3-methoxy-cinnamic acid</synonym>
    <synonym>(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-acrylic acid</synonym>
    <synonym>(2E)-3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoic acid</synonym>
    <synonym>(e)-3-(4-Hydroxy-3-methoxyphenyl)acrylic acid</synonym>
    <synonym>Fumalic acid</synonym>
    <synonym>3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid</synonym>
    <synonym>3-(4-Hydroxy-3-methoxyphenyl)acrylic acid</synonym>
    <synonym>3-Methoxy-4-hydroxycinnamic acid</synonym>
    <synonym>4'-Hydroxy-3'-methoxycinnamic acid</synonym>
    <synonym>Coniferic acid</synonym>
    <synonym>Ferulaic acid</synonym>
    <synonym>Ferulic acid</synonym>
  </synonyms>
  <chemical_formula>C10H10O4</chemical_formula>
  <average_molecular_weight>194.184</average_molecular_weight>
  <monisotopic_moleculate_weight>194.057908808</monisotopic_moleculate_weight>
  <iupac_name>(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid</iupac_name>
  <traditional_iupac>ferulic acid</traditional_iupac>
  <cas_registry_number>537-98-4</cas_registry_number>
  <smiles>COC1=C(O)C=CC(\C=C\C(O)=O)=C1</smiles>
  <inchi>InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+</inchi>
  <inchikey>KSEBMYQBYZTDHS-HWKANZROSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Cinnamic acids and derivatives</class>
    <sub_class>Hydroxycinnamic acids and derivatives</sub_class>
    <direct_parent>Hydroxycinnamic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cinnamic acids</alternative_parent>
      <alternative_parent>Coumaric acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cinnamic acid</substituent>
      <substituent>Coumaric acid or derivatives</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxycinnamic acid</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Styrene</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Coniferyl alcohol derivatives</external_descriptor>
      <external_descriptor>ferulic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>168 - 171 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.51</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>194.184</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>194.057908808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=C(O)C=CC(\C=C\C(O)=O)=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H10O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KSEBMYQBYZTDHS-HWKANZROSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439796</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01494</kegg_id>
  <foodb_id>FDB012802</foodb_id>
  <chemspider_id>393368</chemspider_id>
  <drugbank_id>DB07767</drugbank_id>
  <chebi_id>17620</chebi_id>
  <pubchem_compound_id>445858</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id>499</phenol_explorer_compound_id>
  <knapsack_id>C00002743</knapsack_id>
  <meta_cyc_id>FERULIC-ACID</meta_cyc_id>
  <wikipedia_id>Ferulic_Acid</wikipedia_id>
  <bigg_id/>
  <metlin_id>4156</metlin_id>
  <synthesis_reference>Ou, Shiyi; Zhang, Jing; Bao, Huiyan; Zhang, Ning; Li, Aijun.  Method for preparing oligosaccharide and trans-ferulic acid.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2003),     8 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:07 UTC</creation_date>
  <update_date>2020-04-15 22:29:52 UTC</update_date>
  <accession>BMDB0000957</accession>
  <secondary_accessions>
    <accession>BMDB00957</accession>
  </secondary_accessions>
  <name>Pyrocatechol</name>
  <description>Pyrocatechol, also known as 1,2-benzenediol or 2-hydroxyphenol, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Pyrocatechol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Pyrocatechol exists in all living organisms, ranging from bacteria to humans. Pyrocatechol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.</description>
  <synonyms>
    <synonym>1,2-Benzenediol</synonym>
    <synonym>1,2-Dihydroxybenzene</synonym>
    <synonym>2-Hydroxyphenol</synonym>
    <synonym>alpha-Hydroxyphenol</synonym>
    <synonym>Brenzcatechin</synonym>
    <synonym>O-Benzenediol</synonym>
    <synonym>O-Hydroxyphenol</synonym>
    <synonym>Pyrocatechin</synonym>
    <synonym>a-Hydroxyphenol</synonym>
    <synonym>Α-hydroxyphenol</synonym>
    <synonym>Catechol</synonym>
    <synonym>Durafur developer C</synonym>
    <synonym>Fouramine PCH</synonym>
    <synonym>Fourrine 68</synonym>
    <synonym>O-Dihydroxybenzene</synonym>
    <synonym>O-Dioxybenzene</synonym>
    <synonym>O-Hydroquinone</synonym>
    <synonym>O-Phenylenediol</synonym>
    <synonym>Oxyphenate</synonym>
    <synonym>Oxyphenic acid</synonym>
    <synonym>Pelagol grey C</synonym>
    <synonym>Phthalhydroquinone</synonym>
    <synonym>Phthalic alcohol</synonym>
    <synonym>Pyrocatechine</synonym>
    <synonym>1,3-Dihydroxybenzene</synonym>
    <synonym>Catechol dipotassium salt</synonym>
    <synonym>Catechol, 14C-labeled CPD</synonym>
    <synonym>Catechol sodium salt</synonym>
  </synonyms>
  <chemical_formula>C6H6O2</chemical_formula>
  <average_molecular_weight>110.1106</average_molecular_weight>
  <monisotopic_moleculate_weight>110.036779436</monisotopic_moleculate_weight>
  <iupac_name>benzene-1,2-diol</iupac_name>
  <traditional_iupac>catechol</traditional_iupac>
  <cas_registry_number>120-80-9</cas_registry_number>
  <smiles>OC1=CC=CC=C1O</smiles>
  <inchi>InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H</inchi>
  <inchikey>YCIMNLLNPGFGHC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Benzenediols</sub_class>
    <direct_parent>Catechols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Catechol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a catechol</external_descriptor>
      <external_descriptor>catechols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>105 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>461.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.88</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>benzene-1,2-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>110.1106</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>110.036779436</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC1=CC=CC=C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H6O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YCIMNLLNPGFGHC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440140</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C15571</kegg_id>
  <foodb_id>FDB001512</foodb_id>
  <chemspider_id>13837760</chemspider_id>
  <drugbank_id>DB02232</drugbank_id>
  <chebi_id>18135</chebi_id>
  <pubchem_compound_id>289</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id>654</phenol_explorer_compound_id>
  <knapsack_id>C00002644</knapsack_id>
  <meta_cyc_id>CATECHOL</meta_cyc_id>
  <wikipedia_id>Catechol</wikipedia_id>
  <bigg_id/>
  <metlin_id>282</metlin_id>
  <synthesis_reference>Lauterbach, Manfred; Zimmermann, Volker; Jaeger, Guenter; Radig, Wolfram; Adam, Johannes; Blady, Regina.  Extraction and purification of pyrocatechol.    Ger. (East)  (1986),     4 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00383</protein_accession>
      <name>Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase</name>
      <uniprot_id>Q148L6</uniprot_id>
      <gene_name>DHDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00421</protein_accession>
      <name>Catechol O-methyltransferase</name>
      <uniprot_id>A7MBI7</uniprot_id>
      <gene_name>COMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:08 UTC</creation_date>
  <update_date>2020-03-13 16:25:00 UTC</update_date>
  <accession>BMDB0000958</accession>
  <secondary_accessions>
    <accession>BMDB00958</accession>
  </secondary_accessions>
  <name>trans-Aconitic acid</name>
  <description/>
  <synonyms>
    <synonym>(1E)-1-Propene-1,2,3-tricarboxylic acid</synonym>
    <synonym>(e)-1-Propene-1,2,3-tricarboxylic acid</synonym>
    <synonym>(1E)-1-Propene-1,2,3-tricarboxylate</synonym>
    <synonym>(e)-1-Propene-1,2,3-tricarboxylate</synonym>
    <synonym>trans-Aconitate</synonym>
    <synonym>(1E)-Prop-1-ene-1,2,3-tricarboxylic</synonym>
    <synonym>(1E)1-Propene-1,2,3-tricarboxylate</synonym>
    <synonym>(1E)1-Propene-1,2,3-tricarboxylic acid</synonym>
    <synonym>(e)-Aconitic acid</synonym>
    <synonym>1-Propene-1-trans-2,3-tricarboxylic acid</synonym>
    <synonym>1-trans-Propene-1,2,3-tricarboxylic acid</synonym>
    <synonym>Acid</synonym>
    <synonym>TRA</synonym>
    <synonym>trans-1-Propene-1,2,3-tricarboxylic acid</synonym>
    <synonym>trans-Propene-1,2,3-tricarboxylic acid</synonym>
    <synonym>Acid, aconitic</synonym>
    <synonym>Acid, adonic</synonym>
    <synonym>Acid, carboxyglutaconic</synonym>
    <synonym>Acid, citridic</synonym>
    <synonym>Adonic acid</synonym>
    <synonym>Achilleic acid</synonym>
    <synonym>Acid, acontic</synonym>
    <synonym>Acid, pyrocitric</synonym>
    <synonym>Carboxyglutaconic acid</synonym>
    <synonym>Equisetic acid</synonym>
    <synonym>Pyrocitric acid</synonym>
    <synonym>Acid, achilleic</synonym>
    <synonym>Acid, equisetic</synonym>
    <synonym>Aconitate</synonym>
    <synonym>Citridic acid</synonym>
    <synonym>Citridinic acid</synonym>
    <synonym>Acid, citridinic</synonym>
    <synonym>Aconitic acid</synonym>
    <synonym>Acontic acid</synonym>
  </synonyms>
  <chemical_formula>C6H6O6</chemical_formula>
  <average_molecular_weight>174.1082</average_molecular_weight>
  <monisotopic_moleculate_weight>174.016437924</monisotopic_moleculate_weight>
  <iupac_name>(1E)-prop-1-ene-1,2,3-tricarboxylic acid</iupac_name>
  <traditional_iupac>trans aconitic acid</traditional_iupac>
  <cas_registry_number>4023-65-8</cas_registry_number>
  <smiles>OC(=O)C\C(=C/C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1+</inchi>
  <inchikey>GTZCVFVGUGFEME-HNQUOIGGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Tricarboxylic acids and derivatives</sub_class>
    <direct_parent>Tricarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aconitic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>187 - 191 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>472.5 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1E)-prop-1-ene-1,2,3-tricarboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>174.1082</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>174.016437924</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C\C(=C/C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H6O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GTZCVFVGUGFEME-HNQUOIGGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>111.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439246</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>7000</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Russell JB, Van Soest PJ: In vitro ruminal fermentation of organic acids common in forage. Appl Environ Microbiol. 1984 Jan;47(1):155-9.</reference_text>
          <pubmed_id>6696413</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02341</kegg_id>
  <foodb_id>FDB008305</foodb_id>
  <chemspider_id>392201</chemspider_id>
  <drugbank_id/>
  <chebi_id>32806</chebi_id>
  <pubchem_compound_id>444212</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-225</meta_cyc_id>
  <wikipedia_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Gutierrez, Eddie N.; Lamberti, Vincent.  Preparation of aconitic acid.    U.S.  (1978),     5 pp.  CODEN: USXXAM  US  4123459  19781031  CAN 90:103423  AN 1979:103423</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00559</protein_accession>
      <name>RecQ protein-like (DNA helicase Q1-like)</name>
      <uniprot_id>A0JN36</uniprot_id>
      <gene_name>RECQL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00560</protein_accession>
      <name>Polymerase (DNA-directed), delta interacting protein 3</name>
      <uniprot_id>A7YW33</uniprot_id>
      <gene_name>POLDIP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01637</protein_accession>
      <name>Solute carrier family 7 (Cationic amino acid transporter, y+ system), member 3</name>
      <uniprot_id>A0JNF2</uniprot_id>
      <gene_name>SLC7A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01638</protein_accession>
      <name>HNRNPD protein</name>
      <uniprot_id>A6H6Y0</uniprot_id>
      <gene_name>HNRNPD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01639</protein_accession>
      <name>MGC139164 protein</name>
      <uniprot_id>A6QNP6</uniprot_id>
      <gene_name>MGC139164</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01640</protein_accession>
      <name>Zinc finger protein 775</name>
      <uniprot_id>A0JNI3</uniprot_id>
      <gene_name>ZNF775</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01641</protein_accession>
      <name>ZNF404 protein</name>
      <uniprot_id>A6QQ61</uniprot_id>
      <gene_name>ZNF404</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01642</protein_accession>
      <name>N6AMT1 protein</name>
      <uniprot_id>A4FV35</uniprot_id>
      <gene_name>N6AMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01643</protein_accession>
      <name>Solute carrier family 10 (Sodium/bile acid cotransporter family), member 4</name>
      <uniprot_id>A0JNQ1</uniprot_id>
      <gene_name>SLC10A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01644</protein_accession>
      <name>DEAD (Asp-Glu-Ala-Asp) box polypeptide 1</name>
      <uniprot_id>A7E3W7</uniprot_id>
      <gene_name>DDX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01645</protein_accession>
      <name>SUPV3L1 protein</name>
      <uniprot_id>A6QP28</uniprot_id>
      <gene_name>SUPV3L1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01646</protein_accession>
      <name>RAVER1 protein</name>
      <uniprot_id>A4FUZ2</uniprot_id>
      <gene_name>RAVER1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01647</protein_accession>
      <name>ZNF14 protein</name>
      <uniprot_id>A2VE73</uniprot_id>
      <gene_name>ZNF14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01648</protein_accession>
      <name>LOC100124511 protein</name>
      <uniprot_id>A1A4K0</uniprot_id>
      <gene_name>LOC100124511</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01649</protein_accession>
      <name>DDX24 protein</name>
      <uniprot_id>A6H7B6</uniprot_id>
      <gene_name>DDX24</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01650</protein_accession>
      <name>LBR protein</name>
      <uniprot_id>A6QQV8</uniprot_id>
      <gene_name>LBR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01651</protein_accession>
      <name>ZNF773 protein</name>
      <uniprot_id>A6QPU7</uniprot_id>
      <gene_name>ZNF773</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01652</protein_accession>
      <name>LOC516156 protein</name>
      <uniprot_id>A6QNX0</uniprot_id>
      <gene_name>LOC516156</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01653</protein_accession>
      <name>G-rich RNA sequence binding factor 1</name>
      <uniprot_id>A0JNI7</uniprot_id>
      <gene_name>GRSF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01654</protein_accession>
      <name>ZBTB44 protein</name>
      <uniprot_id>A6QNQ1</uniprot_id>
      <gene_name>ZBTB44</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01655</protein_accession>
      <name>PABPN1 protein</name>
      <uniprot_id>A2VE34</uniprot_id>
      <gene_name>PABPN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01656</protein_accession>
      <name>MATR3 protein</name>
      <uniprot_id>A4IF82</uniprot_id>
      <gene_name>MATR3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01657</protein_accession>
      <name>FtsJ homolog 1 (E. coli)</name>
      <uniprot_id>A0JNB8</uniprot_id>
      <gene_name>FTSJ1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01658</protein_accession>
      <name>ZFP3 protein</name>
      <uniprot_id>A5PJK9</uniprot_id>
      <gene_name>ZFP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01659</protein_accession>
      <name>Zinc finger protein 577</name>
      <uniprot_id>A1L563</uniprot_id>
      <gene_name>ZNF577</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01660</protein_accession>
      <name>ZNF266 protein</name>
      <uniprot_id>A6QNY8</uniprot_id>
      <gene_name>ZNF266</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01661</protein_accession>
      <name>RBM43 protein</name>
      <uniprot_id>A6H711</uniprot_id>
      <gene_name>RBM43</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01662</protein_accession>
      <name>EGL nine (C.elegans) homolog 2</name>
      <uniprot_id>A7E3S2</uniprot_id>
      <gene_name>EGLN2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01663</protein_accession>
      <name>FIZ1 protein</name>
      <uniprot_id>A6QNZ1</uniprot_id>
      <gene_name>FIZ1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01664</protein_accession>
      <name>SF3B2 protein</name>
      <uniprot_id>A4FV01</uniprot_id>
      <gene_name>SF3B2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01665</protein_accession>
      <name>DDX41 protein</name>
      <uniprot_id>A3KN07</uniprot_id>
      <gene_name>DDX41</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01666</protein_accession>
      <name>SLC7A7 protein</name>
      <uniprot_id>A6QPX4</uniprot_id>
      <gene_name>SLC7A7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01667</protein_accession>
      <name>LOC100125388 protein</name>
      <uniprot_id>A6QQC1</uniprot_id>
      <gene_name>LOC100125388</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01668</protein_accession>
      <name>Solute carrier family 1 member 4</name>
      <uniprot_id>A5HSH2</uniprot_id>
      <gene_name>SLC1A4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01669</protein_accession>
      <name>Boule</name>
      <uniprot_id>A7UEB3</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01670</protein_accession>
      <name>IKAROS family zinc finger 2 (Helios)</name>
      <uniprot_id>A0JNA9</uniprot_id>
      <gene_name>IKZF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01671</protein_accession>
      <name>Gamma-aminobutyric acid (GABA) A receptor, beta 3</name>
      <uniprot_id>A1L501</uniprot_id>
      <gene_name>GABRB3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01672</protein_accession>
      <name>ZNF268 protein</name>
      <uniprot_id>A4IFT8</uniprot_id>
      <gene_name>ZNF268</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01673</protein_accession>
      <name>THAP6 protein</name>
      <uniprot_id>A6QR02</uniprot_id>
      <gene_name>THAP6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01674</protein_accession>
      <name>RBM17 protein</name>
      <uniprot_id>A7MB77</uniprot_id>
      <gene_name>RBM17</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01675</protein_accession>
      <name>Putative uncharacterized protein DKFZp686F02235</name>
      <uniprot_id>A5D9E0</uniprot_id>
      <gene_name>DKFZp686F02235</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01676</protein_accession>
      <name>Zinc finger protein LOC509810</name>
      <uniprot_id>A0JN57</uniprot_id>
      <gene_name>LOC509810</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01677</protein_accession>
      <name>THAP8 protein</name>
      <uniprot_id>A6QQY1</uniprot_id>
      <gene_name>THAP8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01678</protein_accession>
      <name>EXOSC10 protein</name>
      <uniprot_id>A7E323</uniprot_id>
      <gene_name>EXOSC10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01679</protein_accession>
      <name>Trinucleotide repeat containing 4</name>
      <uniprot_id>A1L544</uniprot_id>
      <gene_name>TNRC4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01680</protein_accession>
      <name>POGK protein</name>
      <uniprot_id>A5PJT5</uniprot_id>
      <gene_name>POGK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01681</protein_accession>
      <name>SART3 protein</name>
      <uniprot_id>A7MB01</uniprot_id>
      <gene_name>SART3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01682</protein_accession>
      <name>ZNF583 protein</name>
      <uniprot_id>A3KN44</uniprot_id>
      <gene_name>ZNF583</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01683</protein_accession>
      <name>DDX17 protein</name>
      <uniprot_id>A7E396</uniprot_id>
      <gene_name>DDX17</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01684</protein_accession>
      <name>ZCCHC9 protein</name>
      <uniprot_id>A6H756</uniprot_id>
      <gene_name>ZCCHC9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01685</protein_accession>
      <name>ZNF565 protein</name>
      <uniprot_id>A6QNV5</uniprot_id>
      <gene_name>ZNF565</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01686</protein_accession>
      <name>ZNF774 protein</name>
      <uniprot_id>A6QNQ4</uniprot_id>
      <gene_name>ZNF774</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01687</protein_accession>
      <name>Zinc finger protein 688</name>
      <uniprot_id>A2VDY1</uniprot_id>
      <gene_name>ZNF688</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01688</protein_accession>
      <name>SFRS9 protein</name>
      <uniprot_id>A4FUC6</uniprot_id>
      <gene_name>SFRS9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01689</protein_accession>
      <name>MGC155143 protein</name>
      <uniprot_id>A5D7M1</uniprot_id>
      <gene_name>MGC155143</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01690</protein_accession>
      <name>MYEF2 protein</name>
      <uniprot_id>A6QQP0</uniprot_id>
      <gene_name>MYEF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01691</protein_accession>
      <name>WBSCR1 protein</name>
      <uniprot_id>A7MBG9</uniprot_id>
      <gene_name>WBSCR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01692</protein_accession>
      <name>ZC3H10 protein</name>
      <uniprot_id>A5D7H8</uniprot_id>
      <gene_name>ZC3H10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01693</protein_accession>
      <name>LARP4 protein</name>
      <uniprot_id>A7MB26</uniprot_id>
      <gene_name>LARP4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01694</protein_accession>
      <name>DDX20 protein</name>
      <uniprot_id>A7MB49</uniprot_id>
      <gene_name>DDX20</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01695</protein_accession>
      <name>SAFB protein</name>
      <uniprot_id>A5PJP2</uniprot_id>
      <gene_name>SAFB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01696</protein_accession>
      <name>PLAGL1 protein</name>
      <uniprot_id>A6QQH3</uniprot_id>
      <gene_name>PLAGL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01697</protein_accession>
      <name>RBM24 protein</name>
      <uniprot_id>A6QPJ1</uniprot_id>
      <gene_name>RBM24</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01698</protein_accession>
      <name>Solute carrier family 27 (Fatty acid transporter), member 1</name>
      <uniprot_id>A4IFM2</uniprot_id>
      <gene_name>SLC27A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01699</protein_accession>
      <name>ANG2 protein</name>
      <uniprot_id>A6H6X2</uniprot_id>
      <gene_name>ANG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01700</protein_accession>
      <name>ZNF432 protein</name>
      <uniprot_id>A7E361</uniprot_id>
      <gene_name>ZNF432</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01701</protein_accession>
      <name>ZNF226 protein</name>
      <uniprot_id>A7E325</uniprot_id>
      <gene_name>ZNF226</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01702</protein_accession>
      <name>HNRPDL protein</name>
      <uniprot_id>A4IF81</uniprot_id>
      <gene_name>HNRPDL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01703</protein_accession>
      <name>Zinc finger protein 238</name>
      <uniprot_id>A0JN76</uniprot_id>
      <gene_name>ZNF238</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01704</protein_accession>
      <name>Y-linked zinc finger protein</name>
      <uniprot_id>A1XCL6</uniprot_id>
      <gene_name>ZFY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01705</protein_accession>
      <name>ZNF771 protein</name>
      <uniprot_id>A7E347</uniprot_id>
      <gene_name>ZNF771</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01706</protein_accession>
      <name>ZNF667 protein</name>
      <uniprot_id>A6QNL4</uniprot_id>
      <gene_name>ZNF667</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01707</protein_accession>
      <name>NARS2 protein</name>
      <uniprot_id>A5PJC3</uniprot_id>
      <gene_name>NARS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01708</protein_accession>
      <name>Heterogeneous nuclear ribonucleoprotein A0</name>
      <uniprot_id>A1L532</uniprot_id>
      <gene_name>HNRPA0</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01709</protein_accession>
      <name>Heterogeneous nuclear ribonucleoprotein H2</name>
      <uniprot_id>A5D9B4</uniprot_id>
      <gene_name>HNRPH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01710</protein_accession>
      <name>EGLN3 protein</name>
      <uniprot_id>A7MBA0</uniprot_id>
      <gene_name>EGLN3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01711</protein_accession>
      <name>LOC522449 protein</name>
      <uniprot_id>A4IFN3</uniprot_id>
      <gene_name>LOC522449</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01712</protein_accession>
      <name>PRDM9 protein</name>
      <uniprot_id>A6QNW2</uniprot_id>
      <gene_name>PRDM9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01713</protein_accession>
      <name>METTL5 protein</name>
      <uniprot_id>A5PJE9</uniprot_id>
      <gene_name>METTL5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01714</protein_accession>
      <name>Muscleblind-like 2</name>
      <uniprot_id>A1L584</uniprot_id>
      <gene_name>MBNL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01715</protein_accession>
      <name>LOC407241 protein</name>
      <uniprot_id>A6QL89</uniprot_id>
      <gene_name>LOC407241</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01716</protein_accession>
      <name>RECQL4 protein</name>
      <uniprot_id>A5D786</uniprot_id>
      <gene_name>RECQL4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01717</protein_accession>
      <name>SKIV2L2 protein</name>
      <uniprot_id>A6H714</uniprot_id>
      <gene_name>SKIV2L2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01718</protein_accession>
      <name>MGC139239 protein</name>
      <uniprot_id>A4FUW9</uniprot_id>
      <gene_name>MGC139239</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01719</protein_accession>
      <name>LEPREL1 protein</name>
      <uniprot_id>A6QLY3</uniprot_id>
      <gene_name>LEPREL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01720</protein_accession>
      <name>MGC157163 protein</name>
      <uniprot_id>A7MBK4</uniprot_id>
      <gene_name>MGC157163</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01721</protein_accession>
      <name>THAP7 protein</name>
      <uniprot_id>A4IFT9</uniprot_id>
      <gene_name>THAP7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01722</protein_accession>
      <name>TDRD7 protein</name>
      <uniprot_id>A6QLE1</uniprot_id>
      <gene_name>TDRD7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01723</protein_accession>
      <name>Gamma-aminobutyric acid (GABA) A receptor, delta</name>
      <uniprot_id>A2VE38</uniprot_id>
      <gene_name>GABRD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01724</protein_accession>
      <name>SLC7A13 protein</name>
      <uniprot_id>A7E3E3</uniprot_id>
      <gene_name>SLC7A13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01725</protein_accession>
      <name>ZNF423 protein</name>
      <uniprot_id>A6QNQ0</uniprot_id>
      <gene_name>ZNF423</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01726</protein_accession>
      <name>SLC7A10 protein</name>
      <uniprot_id>A6QQF2</uniprot_id>
      <gene_name>SLC7A10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01727</protein_accession>
      <name>DHX15 protein</name>
      <uniprot_id>A5D7D9</uniprot_id>
      <gene_name>DHX15</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01728</protein_accession>
      <name>SAFB protein</name>
      <uniprot_id>A7E314</uniprot_id>
      <gene_name>SAFB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01729</protein_accession>
      <name>ZNF674 protein</name>
      <uniprot_id>A6QP08</uniprot_id>
      <gene_name>ZNF674</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01730</protein_accession>
      <name>ZNF383 protein</name>
      <uniprot_id>A6QQH4</uniprot_id>
      <gene_name>ZNF383</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01731</protein_accession>
      <name>Kruppel-like factor 15</name>
      <uniprot_id>A2VE49</uniprot_id>
      <gene_name>LOC407241</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01732</protein_accession>
      <name>BRUNOL4 protein</name>
      <uniprot_id>A6H776</uniprot_id>
      <gene_name>BRUNOL4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01733</protein_accession>
      <name>DDX17 protein</name>
      <uniprot_id>A7E307</uniprot_id>
      <gene_name>DDX17</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01734</protein_accession>
      <name>HNRNPUL1 protein</name>
      <uniprot_id>A4FUC2</uniprot_id>
      <gene_name>HNRNPUL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01735</protein_accession>
      <name>AlaRS</name>
      <uniprot_id>A0A2Q9</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01736</protein_accession>
      <name>LOC100125413 protein</name>
      <uniprot_id>A6QQI0</uniprot_id>
      <gene_name>LOC100125413</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01737</protein_accession>
      <name>ZNF48 protein</name>
      <uniprot_id>A6QQT2</uniprot_id>
      <gene_name>ZNF48</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01738</protein_accession>
      <name>Solute carrier family 7 member 5</name>
      <uniprot_id>A7Y463</uniprot_id>
      <gene_name>SLC7A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01739</protein_accession>
      <name>FANCM protein</name>
      <uniprot_id>A6QPF2</uniprot_id>
      <gene_name>FANCM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01740</protein_accession>
      <name>ZC3H11A protein</name>
      <uniprot_id>A5PKI2</uniprot_id>
      <gene_name>ZC3H11A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01741</protein_accession>
      <name>CSTF2 protein</name>
      <uniprot_id>A1A4I6</uniprot_id>
      <gene_name>CSTF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01742</protein_accession>
      <name>LOC539976 protein</name>
      <uniprot_id>A4FUY3</uniprot_id>
      <gene_name>LOC539976</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01743</protein_accession>
      <name>MGC157324 protein</name>
      <uniprot_id>A4IFV3</uniprot_id>
      <gene_name>MGC157324</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01744</protein_accession>
      <name>MGC138914 protein</name>
      <uniprot_id>A4IFD5</uniprot_id>
      <gene_name>MGC138914</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01745</protein_accession>
      <name>LOC510904 protein</name>
      <uniprot_id>A6QPP6</uniprot_id>
      <gene_name>LOC510904</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01746</protein_accession>
      <name>Zinc finger and BTB domain containing 5</name>
      <uniprot_id>A0JN94</uniprot_id>
      <gene_name>ZBTB5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01747</protein_accession>
      <name>Zinc finger, CCHC domain containing 10</name>
      <uniprot_id>A7E3S6</uniprot_id>
      <gene_name>ZCCHC10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01748</protein_accession>
      <name>Solute carrier family 1 member 5</name>
      <uniprot_id>A5HSH3</uniprot_id>
      <gene_name>SLC1A5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01749</protein_accession>
      <name>ACIN1 protein</name>
      <uniprot_id>A4FUB9</uniprot_id>
      <gene_name>ACIN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01750</protein_accession>
      <name>VEZF1 protein</name>
      <uniprot_id>A6QQ84</uniprot_id>
      <gene_name>VEZF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01751</protein_accession>
      <name>ZNF131 protein</name>
      <uniprot_id>A6QR64</uniprot_id>
      <gene_name>ZNF131</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01752</protein_accession>
      <name>HNRNPR protein</name>
      <uniprot_id>A3KMV6</uniprot_id>
      <gene_name>HNRNPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01753</protein_accession>
      <name>MBNL2 protein</name>
      <uniprot_id>A5PKK4</uniprot_id>
      <gene_name>MBNL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01754</protein_accession>
      <name>RNASE2 protein</name>
      <uniprot_id>A5PJY7</uniprot_id>
      <gene_name>RNASE2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01755</protein_accession>
      <name>SFRS4 protein</name>
      <uniprot_id>A7MB38</uniprot_id>
      <gene_name>SFRS4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01756</protein_accession>
      <name>MKRN1 protein</name>
      <uniprot_id>A2VDX6</uniprot_id>
      <gene_name>MKRN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01757</protein_accession>
      <name>ZNF304 protein</name>
      <uniprot_id>A6QLF1</uniprot_id>
      <gene_name>ZNF304</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01758</protein_accession>
      <name>LOC100125304 protein</name>
      <uniprot_id>A4IFL9</uniprot_id>
      <gene_name>LOC100125304</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01759</protein_accession>
      <name>LOC100124429 protein</name>
      <uniprot_id>A7MB20</uniprot_id>
      <gene_name>LOC100124429</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01760</protein_accession>
      <name>Heterogeneous nuclear ribonucleoprotein D</name>
      <uniprot_id>A5D9H5</uniprot_id>
      <gene_name>HNRPD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01761</protein_accession>
      <name>ZNF784 protein</name>
      <uniprot_id>A5PJI8</uniprot_id>
      <gene_name>ZNF784</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01762</protein_accession>
      <name>ZFP36L1 protein</name>
      <uniprot_id>A7MB98</uniprot_id>
      <gene_name>ZFP36L1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01763</protein_accession>
      <name>Transporter</name>
      <uniprot_id>A1A4L2</uniprot_id>
      <gene_name>SLC6A20</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01764</protein_accession>
      <name>FTSJD2 protein</name>
      <uniprot_id>A2VE39</uniprot_id>
      <gene_name>FTSJD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01765</protein_accession>
      <name>RP9 protein</name>
      <uniprot_id>A7E3C9</uniprot_id>
      <gene_name>RP9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01766</protein_accession>
      <name>MBNL1 protein</name>
      <uniprot_id>A5PJM0</uniprot_id>
      <gene_name>MBNL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01767</protein_accession>
      <name>ZNF346 protein</name>
      <uniprot_id>A7YWD0</uniprot_id>
      <gene_name>ZNF346</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01768</protein_accession>
      <name>SFRS5 protein</name>
      <uniprot_id>A6H7B7</uniprot_id>
      <gene_name>SFRS5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01769</protein_accession>
      <name>DHX40 protein</name>
      <uniprot_id>A6QQF4</uniprot_id>
      <gene_name>DHX40</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01770</protein_accession>
      <name>Solute carrier family 7 member 8</name>
      <uniprot_id>A7Y461</uniprot_id>
      <gene_name>SLC7A8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01771</protein_accession>
      <name>PHF1 protein</name>
      <uniprot_id>A6H7D5</uniprot_id>
      <gene_name>PHF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01772</protein_accession>
      <name>DDX23 protein</name>
      <uniprot_id>A6QLB2</uniprot_id>
      <gene_name>DDX23</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01773</protein_accession>
      <name>ZNF777 protein</name>
      <uniprot_id>A6QPN3</uniprot_id>
      <gene_name>ZNF777</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01774</protein_accession>
      <name>ZNF484 protein</name>
      <uniprot_id>A7E3C3</uniprot_id>
      <gene_name>ZNF484</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01775</protein_accession>
      <name>DDX31 protein</name>
      <uniprot_id>A6QP73</uniprot_id>
      <gene_name>DDX31</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01776</protein_accession>
      <name>ZFP64 protein</name>
      <uniprot_id>A5PKJ0</uniprot_id>
      <gene_name>ZFP64</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01777</protein_accession>
      <name>ZFP2 protein</name>
      <uniprot_id>A5D7K3</uniprot_id>
      <gene_name>ZFP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01778</protein_accession>
      <name>KLF10 protein</name>
      <uniprot_id>A6QQG6</uniprot_id>
      <gene_name>KLF10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01779</protein_accession>
      <name>GRSF1 protein</name>
      <uniprot_id>A6QPB2</uniprot_id>
      <gene_name>GRSF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01780</protein_accession>
      <name>Unkempt homolog (Drosophila)</name>
      <uniprot_id>A1A4K6</uniprot_id>
      <gene_name>UNK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01781</protein_accession>
      <name>PIAS3 protein</name>
      <uniprot_id>A6QQU9</uniprot_id>
      <gene_name>PIAS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01782</protein_accession>
      <name>BOLL protein</name>
      <uniprot_id>A6QPF5</uniprot_id>
      <gene_name>BOLL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01783</protein_accession>
      <name>ZNF8 protein</name>
      <uniprot_id>A4IFV7</uniprot_id>
      <gene_name>ZNF8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01784</protein_accession>
      <name>Zinc finger, CCHC domain containing 3</name>
      <uniprot_id>A1A4J3</uniprot_id>
      <gene_name>ZCCHC3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01785</protein_accession>
      <name>PLOD2 protein</name>
      <uniprot_id>A7MB83</uniprot_id>
      <gene_name>PLOD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01786</protein_accession>
      <name>Heterogeneous nuclear ribonucleoprotein U (Scaffold attachment factor A)</name>
      <uniprot_id>A2VDN7</uniprot_id>
      <gene_name>HNRNPU</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01787</protein_accession>
      <name>AARS protein</name>
      <uniprot_id>A6QLT9</uniprot_id>
      <gene_name>AARS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01788</protein_accession>
      <name>ZNF180 protein</name>
      <uniprot_id>A6QP07</uniprot_id>
      <gene_name>ZNF180</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01789</protein_accession>
      <name>PABPN1 protein</name>
      <uniprot_id>A3KN10</uniprot_id>
      <gene_name>PABPN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01790</protein_accession>
      <name>MGC157082 protein</name>
      <uniprot_id>A6QQQ5</uniprot_id>
      <gene_name>MGC157082</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01791</protein_accession>
      <name>LGP2 protein</name>
      <uniprot_id>A6H764</uniprot_id>
      <gene_name>LGP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01792</protein_accession>
      <name>ZNF200 protein</name>
      <uniprot_id>A4IF67</uniprot_id>
      <gene_name>ZNF200</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01793</protein_accession>
      <name>ZNF582 protein</name>
      <uniprot_id>A6QLH7</uniprot_id>
      <gene_name>ZNF582</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01794</protein_accession>
      <name>ZNF391 protein</name>
      <uniprot_id>A6QPV7</uniprot_id>
      <gene_name>ZNF391</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01795</protein_accession>
      <name>PPIL4 protein</name>
      <uniprot_id>A6QP53</uniprot_id>
      <gene_name>PPIL4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01796</protein_accession>
      <name>Putative uncharacterized protein</name>
      <uniprot_id>A6QNZ9</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01797</protein_accession>
      <name>DEK protein</name>
      <uniprot_id>A5PJQ1</uniprot_id>
      <gene_name>DEK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01798</protein_accession>
      <name>ZNF689 protein</name>
      <uniprot_id>A4IFR4</uniprot_id>
      <gene_name>ZNF689</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01799</protein_accession>
      <name>CUGBP1 protein</name>
      <uniprot_id>A7MB95</uniprot_id>
      <gene_name>CUGBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01800</protein_accession>
      <name>GPATCH3 protein</name>
      <uniprot_id>A5PKC9</uniprot_id>
      <gene_name>GPATCH3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01801</protein_accession>
      <name>DEAD (Asp-Glu-Ala-Asp) box polypeptide 49</name>
      <uniprot_id>A1L507</uniprot_id>
      <gene_name>DDX49</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01802</protein_accession>
      <name>ZNF502 protein</name>
      <uniprot_id>A6QR50</uniprot_id>
      <gene_name>ZNF502</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01803</protein_accession>
      <name>LOC100124497 protein</name>
      <uniprot_id>A6QPF7</uniprot_id>
      <gene_name>LOC100124497</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01804</protein_accession>
      <name>Zinc finger protein 93 homolog</name>
      <uniprot_id>A1L537</uniprot_id>
      <gene_name>ZNF235</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01805</protein_accession>
      <name>MGC152083 protein</name>
      <uniprot_id>A6QNU7</uniprot_id>
      <gene_name>MGC152083</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01806</protein_accession>
      <name>ZNF189 protein</name>
      <uniprot_id>A5PJY6</uniprot_id>
      <gene_name>ZNF189</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01807</protein_accession>
      <name>P4HA1 protein</name>
      <uniprot_id>A6QL77</uniprot_id>
      <gene_name>P4HA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01808</protein_accession>
      <name>ZNF554 protein</name>
      <uniprot_id>A6QNX1</uniprot_id>
      <gene_name>ZNF554</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01809</protein_accession>
      <name>Zinc finger protein 264</name>
      <uniprot_id>A6MHW2</uniprot_id>
      <gene_name>Zfp264</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01810</protein_accession>
      <name>SKIV2L2 protein</name>
      <uniprot_id>A5PJZ8</uniprot_id>
      <gene_name>SKIV2L2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:09 UTC</creation_date>
  <update_date>2020-03-13 16:25:01 UTC</update_date>
  <accession>BMDB0000959</accession>
  <secondary_accessions>
    <accession>BMDB00959</accession>
  </secondary_accessions>
  <name>Tiglylglycine</name>
  <description/>
  <synonyms>
    <synonym>N-Tiglylglycine</synonym>
    <synonym>(e)-N-(2-Methyl-1-oxo-2-butenyl)-glycine</synonym>
    <synonym>N-((e)-2-Methyl-but-2-enoyl)-glycine</synonym>
    <synonym>N-Tigloylglycine</synonym>
  </synonyms>
  <chemical_formula>C7H11NO3</chemical_formula>
  <average_molecular_weight>157.1671</average_molecular_weight>
  <monisotopic_moleculate_weight>157.073893223</monisotopic_moleculate_weight>
  <iupac_name>2-[(2E)-2-methylbut-2-enamido]acetic acid</iupac_name>
  <traditional_iupac>[(2E)-2-methylbut-2-enamido]acetic acid</traditional_iupac>
  <cas_registry_number>35842-45-6</cas_registry_number>
  <smiles>C\C=C(/C)C(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C7H11NO3/c1-3-5(2)7(11)8-4-6(9)10/h3H,4H2,1-2H3,(H,8,11)(H,9,10)/b5-3+</inchi>
  <inchikey>WRUSVQOKJIDBLP-HWKANZROSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylglycine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(2E)-2-methylbut-2-enamido]acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>157.1671</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>157.073893223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C\C=C(/C)C(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H11NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H11NO3/c1-3-5(2)7(11)8-4-6(9)10/h3H,4H2,1-2H3,(H,8,11)(H,9,10)/b5-3+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WRUSVQOKJIDBLP-HWKANZROSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448177</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022337</foodb_id>
  <chemspider_id>4945715</chemspider_id>
  <drugbank_id/>
  <chebi_id>73018</chebi_id>
  <pubchem_compound_id>6441567</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <bigg_id/>
  <metlin_id>4246</metlin_id>
  <synthesis_reference>Riordan, James M.; Stammer, Charles H.  Synthesis of unsaturated azlactones from N-acylamino acids.    Journal of Organic Chemistry  (1974),  39(5),  654-9.; Carter, S. M. Bonham; Watson, D. G.; Midgley, J. M.; Logan, R. W.  Synthesis and characterization of acyl glycines. Their measurement in single blood spots by gas chromatography-mass spectrometry to diagnose inborn errors of metabolism.    Journal of Chromatography, B: Biomedical Applications  (1996),  677(1),  29-35.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:10 UTC</creation_date>
  <update_date>2020-03-13 16:25:01 UTC</update_date>
  <accession>BMDB0000960</accession>
  <secondary_accessions>
    <accession>BMDB00960</accession>
  </secondary_accessions>
  <name>dGDP</name>
  <description/>
  <synonyms>
    <synonym>2'-Deoxyguanosine 5'-diphosphate</synonym>
    <synonym>Deoxyguanosine diphosphate</synonym>
    <synonym>2'-Deoxyguanosine 5'-diphosphoric acid</synonym>
    <synonym>Deoxyguanosine diphosphoric acid</synonym>
    <synonym>2'-Deoxy-GDP</synonym>
    <synonym>2'-Deoxyguanosine-5'-diphosphate</synonym>
    <synonym>5'-dGDP</synonym>
    <synonym>Deoxyguanosine 5'-diphosphate</synonym>
    <synonym>Deoxyguanosine-diphosphate</synonym>
  </synonyms>
  <chemical_formula>C10H15N5O10P2</chemical_formula>
  <average_molecular_weight>427.2011</average_molecular_weight>
  <monisotopic_moleculate_weight>427.029414749</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>dGDP</traditional_iupac>
  <cas_registry_number>3493-09-2</cas_registry_number>
  <smiles>NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O2)C(=O)N1</smiles>
  <inchi>InChI=1S/C10H15N5O10P2/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(24-6)2-23-27(21,22)25-26(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1</inchi>
  <inchikey>CIKGWCTVFSRMJU-KVQBGUIXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Cinnamic acids and derivatives</class>
    <sub_class>Hydroxycinnamic acids and derivatives</sub_class>
    <direct_parent>Hydroxycinnamic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cinnamic acids</alternative_parent>
      <alternative_parent>Coumaric acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cinnamic acid</substituent>
      <substituent>Coumaric acid or derivatives</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxycinnamic acid</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Styrene</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>ferulic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>5.5 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>427.2011</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>427.029414749</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O2)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H15N5O10P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H15N5O10P2/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(24-6)2-23-27(21,22)25-26(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CIKGWCTVFSRMJU-KVQBGUIXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>228.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451918</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00361</kegg_id>
  <foodb_id>FDB022338</foodb_id>
  <chemspider_id>388359</chemspider_id>
  <drugbank_id>DB03491</drugbank_id>
  <chebi_id>28862</chebi_id>
  <pubchem_compound_id>439220</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00019355</knapsack_id>
  <meta_cyc_id>DGDP</meta_cyc_id>
  <wikipedia_id>Deoxyguanosine_diphosphate</wikipedia_id>
  <bigg_id>34741</bigg_id>
  <metlin_id>5906</metlin_id>
  <synthesis_reference>Klenow, Hans; Lichtler, Eleanor; Andersen, Bjorn.  Adenine deoxyriboside polyphosphates.    Acta Chemica Scandinavica  (1956),  10  159-60</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:12 UTC</creation_date>
  <update_date>2020-04-15 22:35:37 UTC</update_date>
  <accession>BMDB0000961</accession>
  <secondary_accessions>
    <accession>BMDB00961</accession>
  </secondary_accessions>
  <name>Farnesyl pyrophosphate</name>
  <description>Farnesyl pyrophosphate, also known as farnesyl pyrophosphate or farnesyl-PP, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Farnesyl pyrophosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Farnesyl pyrophosphate exists in all living species, ranging from bacteria to humans. In cattle, farnesyl pyrophosphate is involved in the metabolic pathway called the porphyrin metabolism pathway.</description>
  <synonyms>
    <synonym>(2E,6E)-Farnesol diphosphate</synonym>
    <synonym>(2E,6E)-Farnesyl diphosphate</synonym>
    <synonym>(2E,6E)-Farnesyl pyrophosphate</synonym>
    <synonym>(all-e)-Farnesyl diphosphate</synonym>
    <synonym>(e,e)-Farnesyl pyrophosphate</synonym>
    <synonym>2-trans,6-trans-Farnesyl pyrophosphate</synonym>
    <synonym>all-trans-Farnesyl pyrophosphate</synonym>
    <synonym>Farnesyl diphosphate</synonym>
    <synonym>trans,trans-Farnesyl diphosphate</synonym>
    <synonym>trans-trans-Farnesyl diphosphate</synonym>
    <synonym>2-trans,6-trans-Farnesyl diphosphate</synonym>
    <synonym>(2E,6E)-Farnesol diphosphoric acid</synonym>
    <synonym>(2E,6E)-Farnesyl diphosphoric acid</synonym>
    <synonym>(2E,6E)-Farnesyl pyrophosphoric acid</synonym>
    <synonym>(all-e)-Farnesyl diphosphoric acid</synonym>
    <synonym>(e,e)-Farnesyl pyrophosphoric acid</synonym>
    <synonym>2-trans,6-trans-Farnesyl pyrophosphoric acid</synonym>
    <synonym>all-trans-Farnesyl pyrophosphoric acid</synonym>
    <synonym>Farnesyl diphosphoric acid</synonym>
    <synonym>trans,trans-Farnesyl diphosphoric acid</synonym>
    <synonym>trans-trans-Farnesyl diphosphoric acid</synonym>
    <synonym>2-trans,6-trans-Farnesyl diphosphoric acid</synonym>
    <synonym>Farnesyl pyrophosphoric acid</synonym>
    <synonym>(e,e)-Farnesyl diphosphate</synonym>
    <synonym>Farnesyl-PP</synonym>
    <synonym>trans-Farnesyl pyrophosphate</synonym>
    <synonym>trans-trans-Farnesyl pyrophosphate</synonym>
    <synonym>Farnesyl pyrophosphate, (e,e)-isomer</synonym>
    <synonym>Farnesyl pyrophosphate, (e,Z)-isomer</synonym>
    <synonym>Farnesyl pyrophosphate, (Z,e)-isomer</synonym>
    <synonym>Farnesyl pyrophosphate, (Z,Z)-isomer</synonym>
    <synonym>Farnesylpyrophosphate</synonym>
  </synonyms>
  <chemical_formula>C15H28O7P2</chemical_formula>
  <average_molecular_weight>382.33</average_molecular_weight>
  <monisotopic_moleculate_weight>382.131027238</monisotopic_moleculate_weight>
  <iupac_name>{[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[hydroxy([(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy)phosphoryl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>13058-04-3</cas_registry_number>
  <smiles>[H]OP(=O)(O[H])OP(=O)(O[H])OC\C=C(/C)CC\C=C(/C)CCC=C(C)C</smiles>
  <inchi>InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+</inchi>
  <inchikey>VWFJDQUYCIWHTN-YFVJMOTDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Sesquiterpenoids</sub_class>
    <direct_parent>Sesquiterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Isoprenoid phosphates</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Farsesane sesquiterpenoid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isoprenoid phosphate</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Sesquiterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Acyclic farnesane sesquiterpenoids</external_descriptor>
      <external_descriptor>Acyclic farnesane sesquiterpenoids</external_descriptor>
      <external_descriptor>Farnesenes</external_descriptor>
      <external_descriptor>farnesyl diphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>382.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>382.131027238</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]OP(=O)(O[H])OP(=O)(O[H])OC\C=C(/C)CC\C=C(/C)CCC=C(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H28O7P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VWFJDQUYCIWHTN-YFVJMOTDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>96.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31492</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00448</kegg_id>
  <foodb_id>FDB022339</foodb_id>
  <chemspider_id>393270</chemspider_id>
  <drugbank_id>DB07780</drugbank_id>
  <chebi_id>17407</chebi_id>
  <pubchem_compound_id>445713</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007268</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Farnesyl pyrophosphate</wikipedia_id>
  <bigg_id>35006</bigg_id>
  <metlin_id>403</metlin_id>
  <synthesis_reference>Castillo-Bocanegra, Rafael.  Synthesis and biological activity of farnesyl pyrophosphate analogs. University of California, San Francisco., 1977 - Farnesol  p.364</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00261</protein_accession>
      <name>Squalene synthetase</name>
      <uniprot_id>Q32KR6</uniprot_id>
      <gene_name>FDFT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00940</protein_accession>
      <name>Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha</name>
      <uniprot_id>P29702</uniprot_id>
      <gene_name>FNTA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00941</protein_accession>
      <name>Protein farnesyltransferase subunit beta</name>
      <uniprot_id>P49355</uniprot_id>
      <gene_name>FNTB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:13 UTC</creation_date>
  <update_date>2020-04-15 22:26:04 UTC</update_date>
  <accession>BMDB0000962</accession>
  <secondary_accessions>
    <accession>BMDB00962</accession>
  </secondary_accessions>
  <name>Lipoamide</name>
  <description>Lipoamidee, also known as lipoamidee or lipoamidee, belongs to the class of organic compounds known as lipoamidees. Lipoamidees are compounds containing a lipoamidee moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring. Thus, lipoamidee is considered to be a fatty amide lipid molecule. Lipoamidee exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Lipoamidee exists in all living species, ranging from bacteria to humans. In cattle, lipoamidee is involved in the metabolic pathway called the citric Acid cycle pathway.</description>
  <synonyms>
    <synonym>1,2-Dithiolane-3-pentanamide</synonym>
    <synonym>alpha-Lipoic acid amide</synonym>
    <synonym>Lipoacin</synonym>
    <synonym>Thioctamide</synonym>
    <synonym>Thioctic acid amide</synonym>
    <synonym>Vitamin N</synonym>
    <synonym>a-Lipoate amide</synonym>
    <synonym>a-Lipoic acid amide</synonym>
    <synonym>alpha-Lipoate amide</synonym>
    <synonym>Α-lipoate amide</synonym>
    <synonym>Α-lipoic acid amide</synonym>
    <synonym>Thioctate amide</synonym>
    <synonym>5-(1,2-Dithiolan-3-yl)-pentanamide</synonym>
    <synonym>5-(1,2-Dithiolan-3-yl)pentanamide</synonym>
    <synonym>5-(1,2-Dithiolan-3-yl)valeramide</synonym>
    <synonym>5-(Dithiolan-3-yl)valeramide</synonym>
    <synonym>alpha-Lipoate</synonym>
    <synonym>alpha-Lipoic acid</synonym>
    <synonym>DL-6-Thioctic amide</synonym>
    <synonym>DL-Lipoamide</synonym>
    <synonym>Lipamide</synonym>
    <synonym>Lipoamid</synonym>
    <synonym>Lipoicin</synonym>
    <synonym>Lipozyme</synonym>
    <synonym>Lypoaran</synonym>
    <synonym>Pathoclon</synonym>
    <synonym>Thioami</synonym>
    <synonym>Thioctamid</synonym>
    <synonym>Thiotomin</synonym>
    <synonym>Ticolin</synonym>
    <synonym>1,2-Dithiolane-3-valeramide</synonym>
    <synonym>6,8-Thioctic amide</synonym>
    <synonym>alpha-Lipoic amide</synonym>
    <synonym>Lipoamide, (+-)-isomer</synonym>
  </synonyms>
  <chemical_formula>C8H15NOS2</chemical_formula>
  <average_molecular_weight>205.341</average_molecular_weight>
  <monisotopic_moleculate_weight>205.059505487</monisotopic_moleculate_weight>
  <iupac_name>5-(1,2-dithiolan-3-yl)pentanamide</iupac_name>
  <traditional_iupac>lipoamide</traditional_iupac>
  <cas_registry_number>940-69-2</cas_registry_number>
  <smiles>NC(=O)CCCCC1CCSS1</smiles>
  <inchi>InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)</inchi>
  <inchikey>FCCDDURTIIUXBY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as lipoamides. Lipoamides are compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Dithiolanes</class>
    <sub_class>Lipoamides</sub_class>
    <direct_parent>Lipoamides</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-dithiolanes</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Fatty amides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic disulfides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-dithiolane</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lipoamide</substituent>
      <substituent>Organic disulfide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Primary amides</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>dithiolanes</external_descriptor>
      <external_descriptor>monocarboxylic acid amide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>126.0 - 129.0 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>16.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-(1,2-dithiolan-3-yl)pentanamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>205.341</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>205.059505487</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)CCCCC1CCSS1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15NOS2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FCCDDURTIIUXBY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>43.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>56.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1368</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4988</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451974</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022340</foodb_id>
  <drugbank_id/>
  <chemspider_id>840</chemspider_id>
  <kegg_id>C00248</kegg_id>
  <pubchem_compound_id>863</pubchem_compound_id>
  <chebi_id>17460</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>34384</bigg_id>
  <wikipedia_id>Lipoamide</wikipedia_id>
  <metlin_id>3372</metlin_id>
  <meta_cyc_id>LIPOAMIDE</meta_cyc_id>
  <synthesis_reference>Xu, Yaming; Li, Zhitian; Gu, Yunlong. Synthesis of thioctamide. Faming Zhuanli Shenqing Gongkai Shuomingshu (1997), 5 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:15 UTC</creation_date>
  <update_date>2020-03-13 16:25:03 UTC</update_date>
  <accession>BMDB0000963</accession>
  <secondary_accessions>
    <accession>BMDB00963</accession>
  </secondary_accessions>
  <name>5-Methylthioribose 1-phosphate</name>
  <description/>
  <synonyms>
    <synonym>5-Methylthioribose 1-phosphoric acid</synonym>
    <synonym>{[(3R,4S,5R)-3,4-dihydroxy-5-[(methylsulfanyl)methyl]oxolan-2-yl]oxy}phosphonate</synonym>
    <synonym>{[(3R,4S,5R)-3,4-dihydroxy-5-[(methylsulphanyl)methyl]oxolan-2-yl]oxy}phosphonate</synonym>
    <synonym>{[(3R,4S,5R)-3,4-dihydroxy-5-[(methylsulphanyl)methyl]oxolan-2-yl]oxy}phosphonic acid</synonym>
  </synonyms>
  <chemical_formula>C6H13O7PS</chemical_formula>
  <average_molecular_weight>260.2</average_molecular_weight>
  <monisotopic_moleculate_weight>260.011960931</monisotopic_moleculate_weight>
  <iupac_name>{[(3R,4S,5R)-3,4-dihydroxy-5-[(methylsulfanyl)methyl]oxolan-2-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>5-methylthioribose 1-phosphate</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@]1(O)[C@@]([H])(O)C([H])(OP(O)(O)=O)O[C@@]1([H])CSC</smiles>
  <inchi>InChI=1S/C6H13O7PS/c1-15-2-3-4(7)5(8)6(12-3)13-14(9,10)11/h3-8H,2H2,1H3,(H2,9,10,11)/t3-,4+,5+,6?/m0/s1</inchi>
  <inchikey>JTFITTQBRJDSTL-JMSAOHGTSA-N</inchikey>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(3R,4S,5R)-3,4-dihydroxy-5-[(methylsulfanyl)methyl]oxolan-2-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>260.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>260.011960931</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(O)[C@@]([H])(O)C([H])(OP(O)(O)=O)O[C@@]1([H])CSC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O7PS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O7PS/c1-15-2-3-4(7)5(8)6(12-3)13-14(9,10)11/h3-8H,2H2,1H3,(H2,9,10,11)/t3-,4+,5+,6?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JTFITTQBRJDSTL-JMSAOHGTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>116.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1262143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1262144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1262145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1377256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1377257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1377258</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <pubchem_compound_id>60205003</pubchem_compound_id>
  <chemspider_id/>
  <foodb_id/>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Della Ragione, Fulvio; Carteni-Farina, Maria; Gragnaniello, Vincenzo; Schettino, Maria Irene; Zappia, Vincenzo.  Purification and characterization of 5'-deoxy-5'-methylthioadenosine phosphorylase from human placenta.    Journal of Biological Chemistry  (1986),  261(26),  12324-9. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01077</protein_accession>
      <name>Methylthioribose-1-phosphate isomerase</name>
      <uniprot_id>Q2NL31</uniprot_id>
      <gene_name>MRI1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:16 UTC</creation_date>
  <update_date>2020-04-16 21:05:27 UTC</update_date>
  <accession>BMDB0000965</accession>
  <secondary_accessions>
    <accession>BMDB00965</accession>
  </secondary_accessions>
  <name>Hypotaurine</name>
  <description>Hypotaurine belongs to the class of organic compounds known as sulfinic acids. Sulfinic acids are compounds containing a sulfinic acid functional group, with the general structure RS(=O)OH (R = organyl, not H). Hypotaurine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Hypotaurine exists in all living species, ranging from bacteria to humans. Hypotaurine participates in a number of enzymatic reactions, within cattle. In particular, Hypotaurine can be biosynthesized from cysteamine through the action of the enzyme 2-aminoethanethiol dioxygenase. In addition, Hypotaurine can be biosynthesized from 3-sulfinoalanine; which is catalyzed by the enzyme cysteine sulfinic acid decarboxylase. In cattle, hypotaurine is involved in the metabolic pathway called the taurine and hypotaurine metabolism pathway.</description>
  <synonyms>
    <synonym>2-Aminoethanesulfinic acid</synonym>
    <synonym>2-Aminoethanesulfinate</synonym>
    <synonym>2-Aminoethanesulphinate</synonym>
    <synonym>2-Aminoethanesulphinic acid</synonym>
    <synonym>2-Amino-ethanesulfinate</synonym>
    <synonym>2-Amino-ethanesulfinic acid</synonym>
    <synonym>2-Aminoethylsulfinate</synonym>
    <synonym>2-Aminoethylsulfinic acid</synonym>
    <synonym>Cystaminesulfinate</synonym>
    <synonym>Cystaminesulfinic acid</synonym>
  </synonyms>
  <chemical_formula>C2H7NO2S</chemical_formula>
  <average_molecular_weight>109.147</average_molecular_weight>
  <monisotopic_moleculate_weight>109.019749163</monisotopic_moleculate_weight>
  <iupac_name>2-aminoethane-1-sulfinic acid</iupac_name>
  <traditional_iupac>hypotaurine</traditional_iupac>
  <cas_registry_number>300-84-5</cas_registry_number>
  <smiles>NCCS(O)=O</smiles>
  <inchi>InChI=1S/C2H7NO2S/c3-1-2-6(4)5/h1-3H2,(H,4,5)</inchi>
  <inchikey>VVIUBCNYACGLLV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sulfinic acids. Sulfinic acids are compounds containing a sulfinic acid functional group, with the general structure RS(=O)OH (R = organyl, not H).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Sulfinic acids and derivatives</class>
    <sub_class>Sulfinic acids</sub_class>
    <direct_parent>Sulfinic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkanesulfinic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfur compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkanesulfinic acid</substituent>
      <substituent>Alkanesulfinic acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Sulfinic acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aminosulfinic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-aminoethane-1-sulfinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>109.147</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>109.019749163</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCS(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H7NO2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H7NO2S/c3-1-2-6(4)5/h1-3H2,(H,4,5)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VVIUBCNYACGLLV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>23.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Taurine and Hypotaurine Metabolism</name>
      <smpdb_id>SMP0087214</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>4999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182908</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022342</foodb_id>
  <drugbank_id/>
  <chemspider_id>96959</chemspider_id>
  <kegg_id>C00519</kegg_id>
  <pubchem_compound_id>107812</pubchem_compound_id>
  <chebi_id>16668</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>35230</bigg_id>
  <wikipedia_id>Hypotaurine</wikipedia_id>
  <metlin_id>281</metlin_id>
  <meta_cyc_id>HYPOTAURINE</meta_cyc_id>
  <synthesis_reference>Owen, Terence C.; Wilbraham, A. C. Convenient preparation and characterization of hypotaurine. Journal of the Chemical Society (1965), (Jan.), 826-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:17 UTC</creation_date>
  <update_date>2020-04-14 22:48:41 UTC</update_date>
  <accession>BMDB0000968</accession>
  <secondary_accessions>
    <accession>BMDB00968</accession>
  </secondary_accessions>
  <name>1D-Myo-inositol 1,4-bisphosphate</name>
  <description>1D-Myo-1d-1d-myo-inositol 1,4-bisphosphate belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety. 1D-Myo-1d-1d-myo-inositol 1,4-bisphosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 1D-Myo-1d-1d-myo-inositol 1,4-bisphosphate exists in all eukaryotes, ranging from yeast to humans. 1D-Myo-1d-1d-myo-inositol 1,4-bisphosphate participates in a number of enzymatic reactions, within cattle. In particular, 1D-Myo-1d-1d-myo-inositol 1,4-bisphosphate can be biosynthesized from inositol 1,4,5-trisphosphate through the action of the enzyme phosphatidylinositol 4,5-bisphosphate 5-phosphatase a. In addition, 1D-Myo-1d-1d-myo-inositol 1,4-bisphosphate can be converted into D-myo-inositol 4-phosphate through the action of the enzyme inositol polyphosphate 1-phosphatase. In cattle, 111d-myo-1d-1d-myo-inositol 1,4-bisphosphate is involved in the metabolic pathway called the inositol phosphate metabolism pathway.</description>
  <synonyms>
    <synonym>D-MYO-inositol-1,4-bisphosphATE</synonym>
    <synonym>Inositol 1,4-bisphosphate</synonym>
    <synonym>Myo-inositol 1,4-bisphosphate</synonym>
    <synonym>D-MYO-inositol-1,4-bisphosphoric acid</synonym>
    <synonym>Inositol 1,4-bisphosphoric acid</synonym>
    <synonym>Myo-inositol 1,4-bisphosphoric acid</synonym>
    <synonym>D-Myo-inositol 1,4-bisphosphoric acid</synonym>
    <synonym>1D-Myo-inositol 1,4-bisphosphoric acid</synonym>
    <synonym>D-myo-Inositol 1,4-bisphosphate</synonym>
  </synonyms>
  <chemical_formula>C6H14O12P2</chemical_formula>
  <average_molecular_weight>340.1157</average_molecular_weight>
  <monisotopic_moleculate_weight>339.996048936</monisotopic_moleculate_weight>
  <iupac_name>{[(1R,2R,3R,4R,5R,6S)-2,3,5,6-tetrahydroxy-4-(phosphonooxy)cyclohexyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(1R,2R,3R,4R,5R,6S)-2,3,5,6-tetrahydroxy-4-(phosphonooxy)cyclohexyl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>74465-19-3</cas_registry_number>
  <smiles>O[C@H]1[C@@H](O)[C@@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C6H14O12P2/c7-1-2(8)6(18-20(14,15)16)4(10)3(9)5(1)17-19(11,12)13/h1-10H,(H2,11,12,13)(H2,14,15,16)/t1-,2-,3-,4+,5+,6+/m1/s1</inchi>
  <inchikey>PELZSPZCXGTUMR-RTPHHQFDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Inositol phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclohexanols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Cyclohexanol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Inositol phosphate</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>myo-inositol bisphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(1R,2R,3R,4R,5R,6S)-2,3,5,6-tetrahydroxy-4-(phosphonooxy)cyclohexyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>340.1157</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>339.996048936</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@@H](O)[C@@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H14O12P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H14O12P2/c7-1-2(8)6(18-20(14,15)16)4(10)3(9)5(1)17-19(11,12)13/h1-10H,(H2,11,12,13)(H2,14,15,16)/t1-,2-,3-,4+,5+,6+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PELZSPZCXGTUMR-RTPHHQFDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>214.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>57.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087256</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180842</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022343</foodb_id>
  <drugbank_id>DB03158</drugbank_id>
  <chemspider_id>17216032</chemspider_id>
  <kegg_id>C01220</kegg_id>
  <pubchem_compound_id/>
  <chebi_id>17816</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007484</knapsack_id>
  <bigg_id>37109</bigg_id>
  <wikipedia_id/>
  <metlin_id>5911</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Auchus, Richard J.; Kaiser, Susan L.; Majerus, Philip W.  Synthesis of inositol 1,2-(cyclic)-4,5-trisphosphate.    Proceedings of the National Academy of Sciences of the United States of America  (1987),  84(5),  1206-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00461</protein_accession>
      <name>Inositol polyphosphate 1-phosphatase</name>
      <uniprot_id>P21327</uniprot_id>
      <gene_name>INPP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:18 UTC</creation_date>
  <update_date>2020-03-13 16:25:04 UTC</update_date>
  <accession>BMDB0000969</accession>
  <secondary_accessions>
    <accession>BMDB00969</accession>
  </secondary_accessions>
  <name>1,25-Dihydroxyvitamin D3-26,23-lactone</name>
  <description/>
  <synonyms>
    <synonym>1,25-Dihydroxycholecalciferol-26-23-lactone</synonym>
    <synonym>1,25-Lactone</synonym>
    <synonym>1alpha,25-Dihydroxyvitamin D3-26,23-lactone</synonym>
    <synonym>23S,25R)-1a,25-Dihydroxyvitamin D3 26,23-lactone</synonym>
    <synonym>Calcitriol lactone</synonym>
    <synonym>Calcitriol-26,23-lactone</synonym>
    <synonym>1 alpha,25-Dihydroxyvitamin D3-26,23-lactone</synonym>
    <synonym>23(S),25(R)-1,25(OH)2D3-26,23-Lactone</synonym>
    <synonym>(23S,25R)-1a,25-Dihydroxyvitamin D3 26,23-lactone / (23S,25R)-1a,25-dihydroxycholecalciferol 26,23-lactone</synonym>
    <synonym>(23S,25R)-1Α,25-dihydroxyvitamin D3 26,23-lactone / (23S,25R)-1α,25-dihydroxycholecalciferol 26,23-lactone</synonym>
    <synonym>1,25-Dihydroxyvitamin D3-26,23-lactone</synonym>
  </synonyms>
  <chemical_formula>C27H40O5</chemical_formula>
  <average_molecular_weight>444.6035</average_molecular_weight>
  <monisotopic_moleculate_weight>444.28757439</monisotopic_moleculate_weight>
  <iupac_name>(3R,5S)-5-[(2R)-2-[(1R,3aS,4E,7aR)-4-{2-[(1Z,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]propyl]-3-hydroxy-3-methyloxolan-2-one</iupac_name>
  <traditional_iupac>1,25-lactone</traditional_iupac>
  <cas_registry_number>81203-50-1</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C)[C@H](C)C[C@H]1C[C@@](C)(O)C(=O)O1</smiles>
  <inchi>InChI=1S/C27H40O5/c1-16(12-21-15-27(4,31)25(30)32-21)22-9-10-23-18(6-5-11-26(22,23)3)7-8-19-13-20(28)14-24(29)17(19)2/h7-8,16,20-24,28-29,31H,2,5-6,9-15H2,1,3-4H3/b18-7+,19-8-/t16-,20-,21+,22-,23+,24+,26-,27-/m1/s1</inchi>
  <inchikey>WMYIVSWWSRCZFA-RWVJFQLJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Vitamin D and derivatives</sub_class>
    <direct_parent>Vitamin D and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Gamma butyrolactones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Steroid lactones</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Triterpenoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Gamma butyrolactone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Steroid lactone</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Vitamin D3 and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,5S)-5-[(2R)-2-[(1R,3aS,4E,7aR)-4-{2-[(1Z,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]propyl]-3-hydroxy-3-methyloxolan-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>444.6035</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>444.28757439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C)[C@H](C)C[C@H]1C[C@@](C)(O)C(=O)O1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H40O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H40O5/c1-16(12-21-15-27(4,31)25(30)32-21)22-9-10-23-18(6-5-11-26(22,23)3)7-8-19-13-20(28)14-24(29)17(19)2/h7-8,16,20-24,28-29,31H,2,5-6,9-15H2,1,3-4H3/b18-7+,19-8-/t16-,20-,21+,22-,23+,24+,26-,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WMYIVSWWSRCZFA-RWVJFQLJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>86.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>126.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343419</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022344</foodb_id>
  <drugbank_id/>
  <chemspider_id>4942850</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>6438368</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Baggiolini, Enrico G.; Uskokovic, Milan R.; Wovkulich, Peter M.  Process for the preparation of 1a,23,25-trihydroxycholecalciferol-26-oic acid 23,26-lactone.    U.S.  (1986),     10 pp. Cont.-in-part of U.S. Ser. No. 461,835, abandoned.  CODEN: USXXAM  US  4632784  A  19861230  CAN 107:59328  AN 1987:459328</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:19 UTC</creation_date>
  <update_date>2020-03-13 16:25:05 UTC</update_date>
  <accession>BMDB0000972</accession>
  <secondary_accessions>
    <accession>BMDB00972</accession>
  </secondary_accessions>
  <name>N10-Formyl-THF</name>
  <description/>
  <synonyms>
    <synonym>10-Formyl-THF</synonym>
    <synonym>10-Formyltetrahydrofolic acid</synonym>
    <synonym>10-Formyl-(6Rs)-tetrahydrofolic acid</synonym>
    <synonym>10-Formyl-H4pteglu1</synonym>
    <synonym>10-Formyl-tetrahydrofolate</synonym>
    <synonym>10-Formyltetrahydropteroylglutamate</synonym>
    <synonym>10-Formyltetrahydropteroylglutamic acid</synonym>
    <synonym>10-FTHF</synonym>
    <synonym>N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-glutamate</synonym>
    <synonym>N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-glutamic acid</synonym>
    <synonym>N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-L-glutamate</synonym>
    <synonym>N-[p-[N-[(2-Amino-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]formamido]benzoyl]-L-glutamic acid</synonym>
    <synonym>N10-Formyl-5,6,7,8-tetrahydrofolate</synonym>
    <synonym>N10-Formyl-5,6,7,8-tetrahydrofolic acid</synonym>
    <synonym>N10-Formyl-H4F</synonym>
    <synonym>N10-Formyl-THF</synonym>
    <synonym>N10-Formyltetrahydrofolate</synonym>
    <synonym>N10-Formyltetrahydrofolic acid</synonym>
    <synonym>N10-Formyltetrahydropteroylglutamate</synonym>
  </synonyms>
  <chemical_formula>C20H23N7O7</chemical_formula>
  <average_molecular_weight>473.4393</average_molecular_weight>
  <monisotopic_moleculate_weight>473.165896125</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-[(4-{N-[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid</iupac_name>
  <traditional_iupac>(2S)-2-[(4-{N-[(2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid</traditional_iupac>
  <cas_registry_number>2800-34-2</cas_registry_number>
  <smiles>NC1=NC(=O)C2=C(NCC(CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1</smiles>
  <inchi>InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11?,13-/m0/s1</inchi>
  <inchikey>AUFGTPPARQZWDO-YUZLPWPTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Tetrahydrofolic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Acylaminobenzoic acid and derivatives</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Anilides</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Glutamic acid and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hippuric acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acylaminobenzoic acid or derivatives</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Anilide</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzamide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoic acid or derivatives</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hippuric acid</substituent>
      <substituent>Hippuric acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
      <substituent>Tetrahydrofolic acid</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-[(4-{N-[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl)methyl]formamido}phenyl)formamido]pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>473.4393</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>473.165896125</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=C(NCC(CN(C=O)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N2)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H23N7O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,11,13,23H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t11?,13-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AUFGTPPARQZWDO-YUZLPWPTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>215.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>124.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37871</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182495</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB030256</foodb_id>
  <drugbank_id/>
  <chemspider_id>109092</chemspider_id>
  <kegg_id>C00234</kegg_id>
  <pubchem_compound_id>122347</pubchem_compound_id>
  <chebi_id>15637</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>34337</bigg_id>
  <wikipedia_id>10-Formyltetrahydrofolate</wikipedia_id>
  <metlin_id>5912</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Denis V; Daignan-Fornier B  Synthesis of glutamine, glycine and 10-formyl tetrahydrofolate is coregulated with purine biosynthesis in Saccharomyces cerevisiae.    Molecular &amp; general genetics : MGG  (1998),  259(3),  246-55. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00118</protein_accession>
      <name>Monofunctional C1-tetrahydrofolate synthase, mitochondrial</name>
      <uniprot_id>Q0VCR7</uniprot_id>
      <gene_name>MTHFD1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00598</protein_accession>
      <name>Bifunctional purine biosynthesis protein PURH</name>
      <uniprot_id>Q0VCK0</uniprot_id>
      <gene_name>ATIC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00599</protein_accession>
      <name>Methionyl-tRNA formyltransferase, mitochondrial</name>
      <uniprot_id>O77480</uniprot_id>
      <gene_name>MTFMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00600</protein_accession>
      <name>Trifunctional purine biosynthetic protein adenosine-3</name>
      <uniprot_id>Q59A32</uniprot_id>
      <gene_name>GART</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:20 UTC</creation_date>
  <update_date>2020-04-14 22:48:43 UTC</update_date>
  <accession>BMDB0000973</accession>
  <secondary_accessions>
    <accession>BMDB00973</accession>
  </secondary_accessions>
  <name>Hydrogen phosphate</name>
  <description>Phosphoric acid, also known as phosphate or [po(OH)3], belongs to the class of inorganic compounds known as non-metal phosphates. These are inorganic non-metallic compounds containing a phosphate as its largest oxoanion. Phosphoric acid exists as a solid, possibly soluble (in water), and a moderately acidic compound (based on its pKa) molecule. Phosphoric acid exists in all living species, ranging from bacteria to humans. Phosphoric acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>[PO(OH)3]</synonym>
    <synonym>Acide phosphorique</synonym>
    <synonym>Acidum phosphoricum</synonym>
    <synonym>H3PO4</synonym>
    <synonym>Orthophosphoric acid</synonym>
    <synonym>Phosphorsaeureloesungen</synonym>
    <synonym>Phosphorsaeure</synonym>
    <synonym>Phosphoric acid</synonym>
    <synonym>Orthophosphate</synonym>
    <synonym>Phosphate</synonym>
    <synonym>Diphosphate tetrasodium</synonym>
    <synonym>Marphos</synonym>
    <synonym>NFB</synonym>
    <synonym>ortho- Phosphoric acid</synonym>
    <synonym>Phosphoric acid (acd/name 4.0)</synonym>
    <synonym>Sodium pyrophosphate</synonym>
    <synonym>Sodium pyrophosphate decahydrate</synonym>
    <synonym>Sodium pyrophosphate decahydrate biochemica</synonym>
    <synonym>Sonac</synonym>
    <synonym>Tetra-sodium pyrophosphate</synonym>
    <synonym>Tetrasodium pyrophosphate 10-hydrate</synonym>
    <synonym>Tetrasodium pyrophosphate decahydrate</synonym>
    <synonym>White phosphoric acid</synonym>
    <synonym>K-Etchant</synonym>
    <synonym>Uni-etch</synonym>
    <synonym>Concise etchant</synonym>
    <synonym>Condact</synonym>
    <synonym>Hydrogen phosphoric acid</synonym>
    <synonym>Dihydrogen phosphate</synonym>
    <synonym>Hydrogen phosphate</synonym>
  </synonyms>
  <chemical_formula>H3O4P</chemical_formula>
  <average_molecular_weight>97.9952</average_molecular_weight>
  <monisotopic_moleculate_weight>97.976895096</monisotopic_moleculate_weight>
  <iupac_name>phosphoric acid</iupac_name>
  <traditional_iupac>phosphoric acid</traditional_iupac>
  <cas_registry_number>7664-38-2</cas_registry_number>
  <smiles>OP(O)(O)=O</smiles>
  <inchi>InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)</inchi>
  <inchikey>NBIIXXVUZAFLBC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as non-metal phosphates. These are inorganic non-metallic compounds containing a phosphate as its largest oxoanion.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Non-metal oxoanionic compounds</class>
    <sub_class>Non-metal phosphates</sub_class>
    <direct_parent>Non-metal phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Inorganic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Inorganic oxide</substituent>
      <substituent>Non-metal phosphate</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>phosphoric acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>phosphoric acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>97.9952</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>97.976895096</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>H3O4P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NBIIXXVUZAFLBC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>14.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>5.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183023</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00009</kegg_id>
  <drugbank_id>DB09394</drugbank_id>
  <foodb_id>FDB013380</foodb_id>
  <pubchem_compound_id>1004</pubchem_compound_id>
  <chemspider_id/>
  <chebi_id>26078</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00007408</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Phosphoric_Acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Rosso, Janina A.; Rodriguez Nieto, Felipe J.; Gonzalez, Monica C.; Martire, Daniel O.  Reactions of phosphate radicals with substituted benzenes.    Journal of Photochemistry and Photobiology, A: Chemistry  (1998),  116(1),  21-25.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP02584</protein_accession>
      <name>Alpha-1-syntrophin</name>
      <uniprot_id>Q0P5E6</uniprot_id>
      <gene_name>SNTA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02585</protein_accession>
      <name>Clathrin interactor 1</name>
      <uniprot_id>A7Z035</uniprot_id>
      <gene_name>CLINT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:21 UTC</creation_date>
  <update_date>2020-04-16 17:51:27 UTC</update_date>
  <accession>BMDB0000975</accession>
  <secondary_accessions>
    <accession>BMDB00975</accession>
  </secondary_accessions>
  <name>Trehalose</name>
  <description>Trehalose, also known as alpha-D-trehalose or (GLC)2, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Trehalose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Trehalose exists in all living species, ranging from bacteria to humans. Trehalose can be converted into Beta-D-glucose and Alpha-D-glucose; which is mediated by the enzyme trehalase. In cattle, trehalose is involved in the metabolic pathway called the trehalose degradation pathway.</description>
  <synonyms>
    <synonym>(GLC)2</synonym>
    <synonym>alpha,Alpha'-trehalose</synonym>
    <synonym>alpha-D-GLCP-(11)-alpha-D-GLCP</synonym>
    <synonym>alpha-D-Glucopyranosyl-alpha-D-glucopyranoside</synonym>
    <synonym>alpha-D-Trehalose</synonym>
    <synonym>alpha-Trehalose</synonym>
    <synonym>D-(+)-Trehalose</synonym>
    <synonym>Ergot sugar</synonym>
    <synonym>Mycose</synonym>
    <synonym>a,Alpha'-trehalose</synonym>
    <synonym>Α,alpha'-trehalose</synonym>
    <synonym>a-D-GLCP-(11)-a-D-GLCP</synonym>
    <synonym>Α-D-GLCP-(11)-α-D-GLCP</synonym>
    <synonym>a-D-Glucopyranosyl-a-D-glucopyranoside</synonym>
    <synonym>Α-D-glucopyranosyl-α-D-glucopyranoside</synonym>
    <synonym>a-D-Trehalose</synonym>
    <synonym>Α-D-trehalose</synonym>
    <synonym>a-Trehalose</synonym>
    <synonym>Α-trehalose</synonym>
    <synonym>alpha,alpha-Trehalose</synonym>
    <synonym>D-Trehalose-anhydrous</synonym>
    <synonym>delta-Trehalose-anhydrous</synonym>
    <synonym>D-Trehalose</synonym>
    <synonym>Natural trehalose</synonym>
    <synonym>O-D-Glucopyranosyl-(1→1)-D-glucopyranoside</synonym>
    <synonym>alpha,Alpha'-D-trehalose</synonym>
    <synonym>alpha-D-Glucopyranosyl alpha-D-glucopyranoside</synonym>
    <synonym>Α,α'-D-trehalose</synonym>
    <synonym>Α,α-trehalose</synonym>
    <synonym>Α,α’-D-trehalose</synonym>
    <synonym>Α-D-glucopyranosyl α-D-glucopyranoside</synonym>
    <synonym>Trehalose</synonym>
  </synonyms>
  <chemical_formula>C12H22O11</chemical_formula>
  <average_molecular_weight>342.2965</average_molecular_weight>
  <monisotopic_moleculate_weight>342.116211546</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>α,α'-trehalose</traditional_iupac>
  <cas_registry_number>99-20-7</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C12H22O11/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1</inchi>
  <inchikey>HDTRYLNUVZCQOY-LIZSDCNHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>O-glycosyl compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Disaccharides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Disaccharides</external_descriptor>
      <external_descriptor>trehalose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>203 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-4.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>342.2965</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>342.116211546</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H22O11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H22O11/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HDTRYLNUVZCQOY-LIZSDCNHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>189.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Trehalose Degradation</name>
      <smpdb_id>SMP0087263</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180847</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37872</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01083</kegg_id>
  <pubchem_compound_id>7427</pubchem_compound_id>
  <chemspider_id>7149</chemspider_id>
  <foodb_id>FDB001114</foodb_id>
  <drugbank_id>DB12310</drugbank_id>
  <pdbe_id/>
  <chebi_id>16551</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001152</knapsack_id>
  <meta_cyc_id>TREHALOSE</meta_cyc_id>
  <bigg_id>36774</bigg_id>
  <wikipedia_id>Trehalose</wikipedia_id>
  <metlin_id>5913</metlin_id>
  <synthesis_reference>Murao, Sawao; Nagano, Hiroto; Ogura, Sei; Nishino, Toyokazu. Enzymic synthesis of trehalose from maltose. Agricultural and Biological Chemistry (1985), 49(7), 2113-18.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:23 UTC</creation_date>
  <update_date>2020-03-13 16:25:07 UTC</update_date>
  <accession>BMDB0000977</accession>
  <secondary_accessions>
    <accession>BMDB00977</accession>
  </secondary_accessions>
  <name>3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid</name>
  <description>3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid, also known as 3-hexaprenyl-4-hydroxy-5-methoxybenzoic acid, belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. 2-polyprenyl-6-methoxyphenols are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group. 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. In cattle, 3-hexaprenyl-4-hydroxy-5-methoxybenzoic acid is involved in the metabolic pathway called ubiquinone biosynthesis pathway.</description>
  <synonyms>
    <synonym>3-Hexaprenyl-4-hydroxy-5-methoxybenzoate</synonym>
    <synonym>3-Methoxy-4-hydroxy-5-hexaprenylbenzoate</synonym>
    <synonym>3-Methoxy-4-hydroxy-5-hexaprenylbenzoic acid</synonym>
    <synonym>3-MHHB</synonym>
    <synonym>Hexaprenyl-4-hydroxy-5-methoxybenzoate</synonym>
    <synonym>Hexaprenyl-4-hydroxy-5-methoxybenzoic acid</synonym>
  </synonyms>
  <chemical_formula>C38H56O4</chemical_formula>
  <average_molecular_weight>576.8488</average_molecular_weight>
  <monisotopic_moleculate_weight>576.41786028</monisotopic_moleculate_weight>
  <iupac_name>3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4-hydroxy-5-methoxybenzoic acid</iupac_name>
  <traditional_iupac>3-mhhb</traditional_iupac>
  <cas_registry_number>66551-60-8</cas_registry_number>
  <smiles>COC1=CC(=CC(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C1O)C(O)=O</smiles>
  <inchi>InChI=1S/C38H56O4/c1-28(2)14-9-15-29(3)16-10-17-30(4)18-11-19-31(5)20-12-21-32(6)22-13-23-33(7)24-25-34-26-35(38(40)41)27-36(42-8)37(34)39/h14,16,18,20,22,24,26-27,39H,9-13,15,17,19,21,23,25H2,1-8H3,(H,40,41)/b29-16+,30-18+,31-20+,32-22+,33-24+</inchi>
  <inchikey>YSZSVGFMAJXGMQ-FRICUITQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. 2-polyprenyl-6-methoxyphenols are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Polyprenylphenols</sub_class>
    <direct_parent>2-polyprenyl-6-methoxyphenols</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxybenzoic acid derivatives</alternative_parent>
      <alternative_parent>M-methoxybenzoic acids and derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Sesterterpenoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-polyprenyl-6-methoxyphenol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoic acid or derivatives</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxybenzoic acid</substituent>
      <substituent>M-methoxybenzoic acid or derivatives</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Sesterterpenoid</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ubiquinones</external_descriptor>
      <external_descriptor>methoxybenzoic acid</external_descriptor>
      <external_descriptor>monohydroxybenzoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>8.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>11.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4-hydroxy-5-methoxybenzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>576.8488</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>576.41786028</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC(=CC(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C1O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C38H56O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C38H56O4/c1-28(2)14-9-15-29(3)16-10-17-30(4)18-11-19-31(5)20-12-21-32(6)22-13-23-33(7)24-25-34-26-35(38(40)41)27-36(42-8)37(34)39/h14,16,18,20,22,24,26-27,39H,9-13,15,17,19,21,23,25H2,1-8H3,(H,40,41)/b29-16+,30-18+,31-20+,32-22+,33-24+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YSZSVGFMAJXGMQ-FRICUITQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>185.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>72.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ubiquinone Biosynthesis</name>
      <smpdb_id>SMP0087215</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182336</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022347</foodb_id>
  <drugbank_id/>
  <chemspider_id>4444339</chemspider_id>
  <kegg_id>C05313</kegg_id>
  <pubchem_compound_id>5280776</pubchem_compound_id>
  <chebi_id>16835</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5915</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:24 UTC</creation_date>
  <update_date>2020-03-13 16:25:07 UTC</update_date>
  <accession>BMDB0000978</accession>
  <secondary_accessions>
    <accession>BMDB00978</accession>
  </secondary_accessions>
  <name>4-(2-Aminophenyl)-2,4-dioxobutanoic acid</name>
  <description>4-(2-Aminophenyl)-2,4-dioxobutanoic acid belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 4-(2-Aminophenyl)-2,4-dioxobutanoic acid is possibly soluble (in water) and a strong basic compound (based on its pKa). 4-(2-Aminophenyl)-2,4-dioxobutanoic acid exists in all living species, ranging from bacteria to humans. 4-(2-Aminophenyl)-2,4-dioxobutanoic acid and L-glutamic acid can be biosynthesized from L-kynurenine and oxoglutaric acid; which is catalyzed by the enzyme kynurenine/alpha-aminoadipate aminotransferase, mitochondrial. In cattle, 4-(2-aminophenyl)-2,4-dioxobutanoic acid is involved in the metabolic pathway called the tryptophan metabolism pathway.</description>
  <synonyms>
    <synonym>4-(2-Aminophenyl)-2,4-dioxobutanoate</synonym>
    <synonym>4-(2-Aminophenyl)-2,4-dioxo-butanoate</synonym>
    <synonym>4-(2-Aminophenyl)-2,4-dioxo-butanoic acid</synonym>
    <synonym>2-Amino-alpha,gamma-dioxobenzenebutanoic acid</synonym>
    <synonym>2-Amino-α,γ-dioxobenzenebutanoic acid</synonym>
    <synonym>4-(2-Aminophenyl)-2,4-dioxobutanoic acid</synonym>
  </synonyms>
  <chemical_formula>C10H9NO4</chemical_formula>
  <average_molecular_weight>207.1828</average_molecular_weight>
  <monisotopic_moleculate_weight>207.053157781</monisotopic_moleculate_weight>
  <iupac_name>4-(2-aminophenyl)-2,4-dioxobutanoic acid</iupac_name>
  <traditional_iupac>4-(2-aminophenyl)-2,4-dioxobutanoic acid</traditional_iupac>
  <cas_registry_number>90924-76-8</cas_registry_number>
  <smiles>NC1=C(C=CC=C1)C(=O)CC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C10H9NO4/c11-7-4-2-1-3-6(7)8(12)5-9(13)10(14)15/h1-4H,5,11H2,(H,14,15)</inchi>
  <inchikey>CAOVWYZQMPNAFJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Alkyl-phenylketones</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Aryl alkyl ketones</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Beta-diketones</alternative_parent>
      <alternative_parent>Butyrophenones</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Gamma-keto acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>1,3-diketone</substituent>
      <substituent>Alkyl-phenylketone</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl alkyl ketone</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Butyrophenone</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Gamma-keto acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Keto acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>4-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>aromatic ketone</external_descriptor>
      <external_descriptor>beta-diketone</external_descriptor>
      <external_descriptor>dioxo monocarboxylic acid</external_descriptor>
      <external_descriptor>substituted aniline</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-(2-aminophenyl)-2,4-dioxobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>207.1828</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>207.053157781</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=C(C=CC=C1)C(=O)CC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H9NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H9NO4/c11-7-4-2-1-3-6(7)8(12)5-9(13)10(14)15/h1-4H,5,11H2,(H,14,15)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CAOVWYZQMPNAFJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>52.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34393</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022348</foodb_id>
  <kegg_id>C01252</kegg_id>
  <chemspider_id>459</chemspider_id>
  <pubchem_compound_id>472</pubchem_compound_id>
  <chebi_id>17442</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>37199</bigg_id>
  <wikipedia_id/>
  <metlin_id>5916</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:25 UTC</creation_date>
  <update_date>2020-03-13 16:25:08 UTC</update_date>
  <accession>BMDB0000980</accession>
  <secondary_accessions>
    <accession>BMDB00980</accession>
  </secondary_accessions>
  <name>Dihydroneopterin triphosphate</name>
  <description/>
  <synonyms>
    <synonym>2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate</synonym>
    <synonym>6-(L-Erythro-1,2-dihydroxy-3-triphosphooxypropyl)-7,8-dihydropterin</synonym>
    <synonym>6-(L-Erythro-1,2-dihydroxypropyl 3-triphosphate)-7,8-dihydropterin</synonym>
    <synonym>6-[(1S,2R)-1,2-Dihydroxy-3-triphosphooxypropyl]-7,8-dihydropterin</synonym>
    <synonym>2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphoric acid</synonym>
    <synonym>6-(L-Erythro-1,2-dihydroxypropyl 3-triphosphoric acid)-7,8-dihydropterin</synonym>
    <synonym>Dihydroneopterin triphosphoric acid</synonym>
    <synonym>2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl) dihydropteridine triphosphate</synonym>
    <synonym>7,8-Dihydroneopterin 3'-triphosphate</synonym>
    <synonym>7,8-Dihydroneopterin triphosphate</synonym>
    <synonym>Dihydroneopterin triphosphate, (S-(r*,s*))-isomer</synonym>
    <synonym>Dihydro-neopterin triphosphate</synonym>
  </synonyms>
  <chemical_formula>C9H16N5O13P3</chemical_formula>
  <average_molecular_weight>495.1703</average_molecular_weight>
  <monisotopic_moleculate_weight>494.995745159</monisotopic_moleculate_weight>
  <iupac_name>{[({[(2R,3S)-3-(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)-2,3-dihydroxypropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>{[(2R,3S)-3-(2-amino-4-oxo-7,8-dihydro-3H-pteridin-6-yl)-2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>20574-65-6</cas_registry_number>
  <smiles>NC1=NC2=C(N=C(CN2)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(=O)N1</smiles>
  <inchi>InChI=1S/C9H16N5O13P3/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-25-29(21,22)27-30(23,24)26-28(18,19)20/h4,6,15-16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H4,10,11,13,14,17)/t4-,6+/m1/s1</inchi>
  <inchikey>DGGUVLXVLHAAGT-XINAWCOVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Biopterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Ketimines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Biopterin</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imine</substituent>
      <substituent>Ketimine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dihydropterin</external_descriptor>
      <external_descriptor>neopterins</external_descriptor>
      <external_descriptor>pterin phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[({[(2R,3S)-3-(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)-2,3-dihydroxypropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>495.1703</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>494.995745159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=C(CN2)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H16N5O13P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H16N5O13P3/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-25-29(21,22)27-30(23,24)26-28(18,19)20/h4,6,15-16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H4,10,11,13,14,17)/t4-,6+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DGGUVLXVLHAAGT-XINAWCOVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>292.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>102.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pterine Biosynthesis</name>
      <smpdb_id>SMP0087250</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19919</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31633</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB030620</foodb_id>
  <kegg_id>C04895</kegg_id>
  <chemspider_id>108735</chemspider_id>
  <pubchem_compound_id>121885</pubchem_compound_id>
  <chebi_id>18372</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007510</knapsack_id>
  <bigg_id>44843</bigg_id>
  <wikipedia_id>7,8-Dihydroneopterin triphosphate</wikipedia_id>
  <metlin_id>5917</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Ferre, Juan; Naylor, Edwin W.; Jacobson, K. Bruce.  Repetitive recycling of guanosine triphosphate cyclohydrolase I for synthesis of dihydroneopterin triphosphate.    Analytical Biochemistry  (1989),  176(1),  15-18.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:26 UTC</creation_date>
  <update_date>2020-03-13 16:25:08 UTC</update_date>
  <accession>BMDB0000981</accession>
  <secondary_accessions>
    <accession>BMDB00981</accession>
  </secondary_accessions>
  <name>4a-Methyl-5a-cholesta-8,24-dien-3-one</name>
  <description/>
  <synonyms>
    <synonym>(4alpha,5alpha)-4-Methylcholesta-8,24-dien-3-one</synonym>
    <synonym>3-Keto-4alpha-methyl-zymosterol</synonym>
    <synonym>3-Keto-4alpha-methylzymosterol</synonym>
    <synonym>4alpha-Methyl-(5alpha)-cholesta-8,24-dien-3-one</synonym>
    <synonym>(4a,5a)-4-Methylcholesta-8,24-dien-3-one</synonym>
    <synonym>(4Α,5α)-4-methylcholesta-8,24-dien-3-one</synonym>
    <synonym>3-Keto-4a-methyl-zymosterol</synonym>
    <synonym>3-Keto-4α-methyl-zymosterol</synonym>
    <synonym>3-Keto-4a-methylzymosterol</synonym>
    <synonym>3-Keto-4α-methylzymosterol</synonym>
    <synonym>4a-Methyl-(5a)-cholesta-8,24-dien-3-one</synonym>
    <synonym>4Α-methyl-(5α)-cholesta-8,24-dien-3-one</synonym>
    <synonym>4alpha-Methyl-5alpha-cholesta-8,24-dien-3-one</synonym>
  </synonyms>
  <chemical_formula>C28H44O</chemical_formula>
  <average_molecular_weight>396.6484</average_molecular_weight>
  <monisotopic_moleculate_weight>396.33921603</monisotopic_moleculate_weight>
  <iupac_name>(2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one</iupac_name>
  <traditional_iupac>(2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one</traditional_iupac>
  <cas_registry_number>7377-73-3</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C</smiles>
  <inchi>InChI=1S/C28H44O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h8,19-20,22-24H,7,9-17H2,1-6H3/t19-,20+,22-,23+,24+,27-,28+/m1/s1</inchi>
  <inchikey>DBPZYKHQDWKORQ-SINUOACOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-oxo-5-alpha-steroids</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-oxo-5-alpha-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>396.6484</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>396.33921603</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C28H44O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C28H44O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h8,19-20,22-24H,7,9-17H2,1-6H3/t19-,20+,22-,23+,24+,27-,28+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DBPZYKHQDWKORQ-SINUOACOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>124.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>50.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354741</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022350</foodb_id>
  <chemspider_id>20059529</chemspider_id>
  <pubchem_compound_id>22298939</pubchem_compound_id>
  <chebi_id>136486</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5918</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Barton, Derek H. R.; Harrison, David Miles; Moss, G. P.; Widdowson, David A.  Biosynthesis of steroids and terpenoids.  II.  Role of 24-methylene derivatives in the biosynthesis of steroids and terpenoids.    Journal of the Chemical Society [Section] C:  Organic  (1970),   (6),  775-85.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:28 UTC</creation_date>
  <update_date>2020-03-13 16:25:09 UTC</update_date>
  <accession>BMDB0000982</accession>
  <secondary_accessions>
    <accession>BMDB00982</accession>
  </secondary_accessions>
  <name>5-Methylcytidine</name>
  <description/>
  <synonyms>
    <synonym>5-Methyl-cytidine</synonym>
    <synonym>5-Methylcytidine</synonym>
  </synonyms>
  <chemical_formula>C10H15N3O5</chemical_formula>
  <average_molecular_weight>257.2432</average_molecular_weight>
  <monisotopic_moleculate_weight>257.101170605</monisotopic_moleculate_weight>
  <iupac_name>4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2-dihydropyrimidin-2-one</iupac_name>
  <traditional_iupac>5-methylcytidine</traditional_iupac>
  <cas_registry_number>2140-61-6</cas_registry_number>
  <smiles>CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N=C1N</smiles>
  <inchi>InChI=1S/C10H15N3O5/c1-4-2-13(10(17)12-8(4)11)9-7(16)6(15)5(3-14)18-9/h2,5-7,9,14-16H,3H2,1H3,(H2,11,12,17)/t5-,6-,7-,9-/m1/s1</inchi>
  <inchikey>ZAYHVCMSTBRABG-JXOAFFINSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleosides</class>
    <sub_class/>
    <direct_parent>Pyrimidine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine nucleoside</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>methylcytidine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>213 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.01</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2-dihydropyrimidin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>257.2432</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>257.101170605</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N=C1N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H15N3O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H15N3O5/c1-4-2-13(10(17)12-8(4)11)9-7(16)6(15)5(3-14)18-9/h2,5-7,9,14-16H,3H2,1H3,(H2,11,12,17)/t5-,6-,7-,9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZAYHVCMSTBRABG-JXOAFFINSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>128.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>58.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345366</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022351</foodb_id>
  <kegg_id/>
  <chemspider_id>83877</chemspider_id>
  <pubchem_compound_id>92918</pubchem_compound_id>
  <chebi_id>20607</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>5-Methylcytidine</wikipedia_id>
  <metlin_id>5919</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Mastronicolis S K; Kapoulas V M; Kroger H  The isolation of antibodies specific for 5-methyl-cytidine-bovine serum albumin.    Zeitschrift fur Naturforschung. Section C: Biosciences  (1981),  36(5-6),  459-63.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:29 UTC</creation_date>
  <update_date>2020-03-13 16:25:09 UTC</update_date>
  <accession>BMDB0000985</accession>
  <secondary_accessions>
    <accession>BMDB00985</accession>
  </secondary_accessions>
  <name>Dihydrolipoamide</name>
  <description>Dihydrolipoamide belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine. Thus, dihydrolipoamide is considered to be a fatty amide lipid molecule. Dihydrolipoamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dihydrolipoamide exists in all living species, ranging from bacteria to humans. Dihydrolipoamide participates in a number of enzymatic reactions, within cattle. In particular, Dihydrolipoamide can be converted into lipoamide; which is catalyzed by the enzyme dihydrolipoyl dehydrogenase E3. In addition, Dihydrolipoamide can be biosynthesized from S-(3-methylbutanoyl)-dihydrolipoamide-e; which is mediated by the enzyme lipoamide acyltransferase component OF branched-chain alpha-keto acid dehydrogenase complex, mitochondrial. In cattle, dihydrolipoamide is involved in the metabolic pathway called the valine, leucine, and isoleucine degradation pathway.</description>
  <synonyms>
    <synonym>6,8-Dimercaptooctanamide</synonym>
    <synonym>Dihydrothioctamide</synonym>
    <synonym>6,8-Bis-sulfanyloctanamide</synonym>
    <synonym>6,8-Dimercapto-octanamide</synonym>
    <synonym>6,8-Disulfanyloctanamide</synonym>
    <synonym>Dihydrolipoamide, (+-)-isomer</synonym>
  </synonyms>
  <chemical_formula>C8H17NOS2</chemical_formula>
  <average_molecular_weight>207.357</average_molecular_weight>
  <monisotopic_moleculate_weight>207.075155551</monisotopic_moleculate_weight>
  <iupac_name>6,8-disulfanyloctanimidic acid</iupac_name>
  <traditional_iupac>dihydrothioctamide</traditional_iupac>
  <cas_registry_number>3884-47-7</cas_registry_number>
  <smiles>OC(=N)CCCCC(S)CCS</smiles>
  <inchi>InChI=1S/C8H17NOS2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H2,9,10)</inchi>
  <inchikey>VLYUGYAKYZETRF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty amides</sub_class>
    <direct_parent>Fatty amides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>dithiol</external_descriptor>
      <external_descriptor>monocarboxylic acid amide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>6.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6,8-disulfanyloctanimidic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>207.357</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>207.075155551</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=N)CCCCC(S)CCS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H17NOS2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H17NOS2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H2,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VLYUGYAKYZETRF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>44.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29809</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022352</foodb_id>
  <kegg_id>C00579</kegg_id>
  <chemspider_id>643</chemspider_id>
  <pubchem_compound_id>663</pubchem_compound_id>
  <chebi_id>17694</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>35406</bigg_id>
  <wikipedia_id>Dihydrolipoamide</wikipedia_id>
  <metlin_id>5920</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Weitzman, P. D. J.; Hewson, Janet K.; Parker, M. G.  Preparation of dihydrolipoamide by electrolytic reduction.    FEBS Letters  (1974),  43(1),  101-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:30 UTC</creation_date>
  <update_date>2020-03-13 16:25:10 UTC</update_date>
  <accession>BMDB0000988</accession>
  <secondary_accessions>
    <accession>BMDB00988</accession>
  </secondary_accessions>
  <name>S-Adenosylmethioninamine</name>
  <description/>
  <synonyms>
    <synonym>(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium</synonym>
    <synonym>(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium cation</synonym>
    <synonym>(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium salt</synonym>
    <synonym>[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulfonium</synonym>
    <synonym>S-Adenosyl-(5')-3-methylthiopropylamine</synonym>
    <synonym>S-Adenosyl-3-methylthiopropylamine</synonym>
    <synonym>S-Adenosyl 3-(methylthio)propylamine</synonym>
    <synonym>S-Adenosyl 3-(methylsulfanyl)propylamine</synonym>
    <synonym>Decarboxy-adomet</synonym>
    <synonym>(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulphonium</synonym>
    <synonym>(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulphonium cation</synonym>
    <synonym>(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulphonium salt</synonym>
    <synonym>[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulfonium</synonym>
    <synonym>[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulphonium</synonym>
    <synonym>[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulphonium</synonym>
    <synonym>[1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulfonium</synonym>
    <synonym>[1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl](3-aminopropyl)(methyl)sulphonium</synonym>
    <synonym>S-Adenosyl 3-(methylsulphanyl)propylamine</synonym>
    <synonym>S--Adenosylmethioninamine</synonym>
    <synonym>(5-Deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt</synonym>
    <synonym>DAdoMet</synonym>
    <synonym>Decarboxylated adomet</synonym>
    <synonym>Decarboxylated S-adenosylmethionine</synonym>
    <synonym>Decarboxylated sam</synonym>
    <synonym>S-Adenosyl-L-methioninamine</synonym>
    <synonym>S-5'-Deoxyadenosyl-(5')-3-methylthiopropylamine</synonym>
    <synonym>S-Adenosyl(5')-3-methylthiopropylamine</synonym>
  </synonyms>
  <chemical_formula>C14H23N6O3S</chemical_formula>
  <average_molecular_weight>355.436</average_molecular_weight>
  <monisotopic_moleculate_weight>355.155234322</monisotopic_moleculate_weight>
  <iupac_name>{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-aminopropyl)methylsulfanium</iupac_name>
  <traditional_iupac>decarboxylated sam</traditional_iupac>
  <cas_registry_number>22365-13-5</cas_registry_number>
  <smiles>C[S+](CCCN)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/t8-,10-,11-,14-,24?/m1/s1</inchi>
  <inchikey>ZUNBITIXDCPNSD-LSRJEVITSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides  in which the ribose is thio-substituted at the 5'position by a S-alkyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>5'-deoxyribonucleosides</class>
    <sub_class>5'-deoxy-5'-thionucleosides</sub_class>
    <direct_parent>5'-deoxy-5'-thionucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfur compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>5'-deoxy-5'-thionucleoside</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>adenosines</external_descriptor>
      <external_descriptor>sulfonium compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-aminopropyl)methylsulfanium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>355.436</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>355.155234322</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[S+](CCCN)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H23N6O3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/t8-,10-,11-,14-,24?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZUNBITIXDCPNSD-LSRJEVITSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>145.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>90.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317658</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022353</foodb_id>
  <kegg_id>C01137</kegg_id>
  <chemspider_id>388529</chemspider_id>
  <pubchem_compound_id>439415</pubchem_compound_id>
  <chebi_id>15625</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>36895</bigg_id>
  <wikipedia_id>S-Adenosylmethioninamine</wikipedia_id>
  <metlin_id>3501</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Pegg, Anthony E.  Assay of aminopropyltransferases.    Methods in Enzymology  (1983),  94(Polyamines),  260-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00126</protein_accession>
      <name>Spermine synthase</name>
      <uniprot_id>Q3SZA5</uniprot_id>
      <gene_name>SMS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:31 UTC</creation_date>
  <update_date>2020-04-16 20:40:04 UTC</update_date>
  <accession>BMDB0000990</accession>
  <secondary_accessions>
    <accession>BMDB00990</accession>
  </secondary_accessions>
  <name>Acetaldehyde</name>
  <description>Acetaldehyde, also known as ethanal, belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms. Acetaldehyde exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Acetaldehyde exists in all living species, ranging from bacteria to humans. Acetaldehyde is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Acetaldehyde has been found to be associated with several diseases known as nonalcoholic fatty liver disease, ulcerative colitis, alcoholism, and crohn's disease; also acetaldehyde has been linked to the inborn metabolic disorders including aldehyde dehydrogenase deficiency.</description>
  <synonyms>
    <synonym>Acetaldehyd</synonym>
    <synonym>Acetaldehydes</synonym>
    <synonym>Acetic aldehyde</synonym>
    <synonym>Azetaldehyd</synonym>
    <synonym>Ethanal</synonym>
    <synonym>Ethyl aldehyde</synonym>
    <synonym>Aldehyde</synonym>
  </synonyms>
  <chemical_formula>C2H4O</chemical_formula>
  <average_molecular_weight>44.0526</average_molecular_weight>
  <monisotopic_moleculate_weight>44.02621475</monisotopic_moleculate_weight>
  <iupac_name>acetaldehyde</iupac_name>
  <traditional_iupac>acetaldehyde</traditional_iupac>
  <cas_registry_number>75-07-0</cas_registry_number>
  <smiles>CC=O</smiles>
  <inchi>InChI=1S/C2H4O/c1-2-3/h2H,1H3</inchi>
  <inchikey>IKHGUXGNUITLKF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as short-chain aldehydes. These are an aldehyde with a chain length containing between 2 and 5 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Short-chain aldehydes</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Short-chain aldehyde</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aldehyde</external_descriptor>
      <external_descriptor>an &lt;i&gt;n&lt;/i&gt;-alkanal</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-123 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.34</value>
      <source>TSCATS</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>16.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>acetaldehyde</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>44.0526</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>44.02621475</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H4O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H4O/c1-2-3/h2H,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IKHGUXGNUITLKF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>11.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>4.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ethanol Degradation</name>
      <smpdb_id>SMP0087192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22672</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.01 +/- 2.89</concentration_value>
      <concentration_units>mg/100g dry matter content</concentration_units>
      <comment>Italian raw milk</comment>
      <references>
        <reference>
          <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.44 +/- 1.47</concentration_value>
      <concentration_units>mg/100g dry matter content</concentration_units>
      <comment>Slovenian raw milk</comment>
      <references>
        <reference>
          <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0638 +/- 0.0365</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>In raw milk samples for diets based on grass silage</comment>
      <references>
        <reference>
          <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
          <pubmed_id>12463694</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0788 +/- 0.0498</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>In raw milk samples for diets based on maize silage</comment>
      <references>
        <reference>
          <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
          <pubmed_id>12463694</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0900 +/- 0.0521</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>In raw milk samples for diets based on hay</comment>
      <references>
        <reference>
          <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
          <pubmed_id>12463694</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB008297</foodb_id>
  <kegg_id>C00084</kegg_id>
  <chemspider_id>172</chemspider_id>
  <pubchem_compound_id>177</pubchem_compound_id>
  <chebi_id>15343</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007392</knapsack_id>
  <bigg_id>33792</bigg_id>
  <wikipedia_id>Acetaldehyde</wikipedia_id>
  <metlin_id>3200</metlin_id>
  <meta_cyc_id>ACETALD</meta_cyc_id>
  <synthesis_reference>Wertheim, E. Laboratory preparation of acetaldehyde. Journal of the American Chemical Society (1922), 44 2658-9.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
      <pubmed_id>12463694</pubmed_id>
    </reference>
    <reference>
      <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00107</protein_accession>
      <name>Putative deoxyribose-phosphate aldolase</name>
      <uniprot_id>Q3T0V9</uniprot_id>
      <gene_name>DERA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00593</protein_accession>
      <name>4-trimethylaminobutyraldehyde dehydrogenase</name>
      <uniprot_id>Q2KJH9</uniprot_id>
      <gene_name>ALDH9A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00601</protein_accession>
      <name>Retinal dehydrogenase 1</name>
      <uniprot_id>P48644</uniprot_id>
      <gene_name>ALDH1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00677</protein_accession>
      <name>Aldehyde oxidase</name>
      <uniprot_id>P48034</uniprot_id>
      <gene_name>AOX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00986</protein_accession>
      <name>Aldehyde dehydrogenase, dimeric NADP-preferring</name>
      <uniprot_id>P30907</uniprot_id>
      <gene_name>ALDH3A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00987</protein_accession>
      <name>Alcohol dehydrogenase [NADP+]</name>
      <uniprot_id>Q3ZCJ2</uniprot_id>
      <gene_name>AKR1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00988</protein_accession>
      <name>Aldehyde dehydrogenase X, mitochondrial</name>
      <uniprot_id>P52476</uniprot_id>
      <gene_name>ALDH1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00989</protein_accession>
      <name>Aldehyde dehydrogenase family 3 member B1</name>
      <uniprot_id>Q1JPA0</uniprot_id>
      <gene_name>ALDH3B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00990</protein_accession>
      <name>Aldehyde dehydrogenase, mitochondrial</name>
      <uniprot_id>P20000</uniprot_id>
      <gene_name>ALDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00991</protein_accession>
      <name>Alcohol dehydrogenase class-3</name>
      <uniprot_id>Q3ZC42</uniprot_id>
      <gene_name>ADH5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02243</protein_accession>
      <name>OTU domain, ubiquitin aldehyde binding 1</name>
      <uniprot_id>Q3T0Y1</uniprot_id>
      <gene_name>OTUB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02244</protein_accession>
      <name>OTU domain, ubiquitin aldehyde binding 2</name>
      <uniprot_id>Q5E9Y3</uniprot_id>
      <gene_name>OTUB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:32 UTC</creation_date>
  <update_date>2020-03-13 16:25:11 UTC</update_date>
  <accession>BMDB0000991</accession>
  <secondary_accessions>
    <accession>BMDB00991</accession>
  </secondary_accessions>
  <name>DL-2-Aminooctanoic acid</name>
  <description>DL-2-Aminooctanoic acid, also known as a-aminocaprylate or alpha-aminocaprylic acid, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). DL-2-Aminooctanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule.</description>
  <synonyms>
    <synonym>(+-)-2-Aminooctanoic acid</synonym>
    <synonym>(+/-)-2-aminooctanoic acid</synonym>
    <synonym>2-Amino-DL-caprylic acid</synonym>
    <synonym>2-Aminocaprylic acid</synonym>
    <synonym>alpha-Aminocaprylic acid</synonym>
    <synonym>alpha-Aminooctanoic acid</synonym>
    <synonym>D,L-2-Aminooctanoic acid</synonym>
    <synonym>DL-2-Aminocaprylic acid</synonym>
    <synonym>DL-alpha-Amino-N-caprylic acid</synonym>
    <synonym>DL-alpha-Aminocaprylic acid</synonym>
    <synonym>NSC 20147</synonym>
    <synonym>(+-)-2-Aminooctanoate</synonym>
    <synonym>(+/-)-2-aminooctanoate</synonym>
    <synonym>2-Amino-DL-caprylate</synonym>
    <synonym>2-Aminocaprylate</synonym>
    <synonym>a-Aminocaprylate</synonym>
    <synonym>a-Aminocaprylic acid</synonym>
    <synonym>alpha-Aminocaprylate</synonym>
    <synonym>Α-aminocaprylate</synonym>
    <synonym>Α-aminocaprylic acid</synonym>
    <synonym>a-Aminooctanoate</synonym>
    <synonym>a-Aminooctanoic acid</synonym>
    <synonym>alpha-Aminooctanoate</synonym>
    <synonym>Α-aminooctanoate</synonym>
    <synonym>Α-aminooctanoic acid</synonym>
    <synonym>D,L-2-Aminooctanoate</synonym>
    <synonym>DL-2-Aminocaprylate</synonym>
    <synonym>DL-a-Amino-N-caprylate</synonym>
    <synonym>DL-a-Amino-N-caprylic acid</synonym>
    <synonym>DL-alpha-Amino-N-caprylate</synonym>
    <synonym>DL-Α-amino-N-caprylate</synonym>
    <synonym>DL-Α-amino-N-caprylic acid</synonym>
    <synonym>DL-a-Aminocaprylate</synonym>
    <synonym>DL-a-Aminocaprylic acid</synonym>
    <synonym>DL-alpha-Aminocaprylate</synonym>
    <synonym>DL-Α-aminocaprylate</synonym>
    <synonym>DL-Α-aminocaprylic acid</synonym>
    <synonym>DL-2-Aminooctanoate</synonym>
    <synonym>(+/-)-2-amino-octanoate</synonym>
    <synonym>(+/-)-2-amino-octanoic acid</synonym>
    <synonym>2-Amino-DL-octanoate</synonym>
    <synonym>2-Amino-DL-octanoic acid</synonym>
    <synonym>2-Aminooctanoate</synonym>
    <synonym>2-Aminooctanoic acid</synonym>
    <synonym>DL-2-Amino-octanoate</synonym>
    <synonym>DL-2-Aminooctanoic acid</synonym>
  </synonyms>
  <chemical_formula>C8H17NO2</chemical_formula>
  <average_molecular_weight>159.2261</average_molecular_weight>
  <monisotopic_moleculate_weight>159.125928793</monisotopic_moleculate_weight>
  <iupac_name>2-aminooctanoic acid</iupac_name>
  <traditional_iupac>(+-)-2-aminooctanoic acid</traditional_iupac>
  <cas_registry_number>644-90-6</cas_registry_number>
  <smiles>CCCCCCC(N)C(O)=O</smiles>
  <inchi>InChI=1S/C8H17NO2/c1-2-3-4-5-6-7(9)8(10)11/h7H,2-6,9H2,1H3,(H,10,11)</inchi>
  <inchikey>AKVBCGQVQXPRLD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>alpha-amino fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>194 - 196 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>19 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-aminooctanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>159.2261</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>159.125928793</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCC(N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H17NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H17NO2/c1-2-3-4-5-6-7(9)8(10)11/h7H,2-6,9H2,1H3,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AKVBCGQVQXPRLD-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>325309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>325310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>325311</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022354</foodb_id>
  <kegg_id/>
  <chemspider_id>62727</chemspider_id>
  <pubchem_compound_id>69522</pubchem_compound_id>
  <chebi_id>75145</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5923</metlin_id>
  <meta_cyc_id>CPD-3687</meta_cyc_id>
  <synthesis_reference>Abderhalden, E.  Specific action of enzymes. A contribution to the question of the possibility of determining by means of enzymes whether amino acids of definite configuration occur in nature and especially as constituents of proteins.    Z. physiol. Chem.  (1923),  130  205-7.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:36 UTC</creation_date>
  <update_date>2020-03-13 16:25:11 UTC</update_date>
  <accession>BMDB0000992</accession>
  <secondary_accessions>
    <accession>BMDB00992</accession>
  </secondary_accessions>
  <name>3-Succinoylpyridine</name>
  <description/>
  <synonyms>
    <synonym>4-oxo-4-(3-Pyridyl)-butanoic acid</synonym>
    <synonym>4-oxo-4-(3-Pyridyl)-butyric acid</synonym>
    <synonym>4-oxo-4-(Pyridin-3-yl)butyric acid</synonym>
    <synonym>gamma-oxo-3-Pyridinebutanoic acid</synonym>
    <synonym>gamma-oxo-3-Pyridinebutyric acid</synonym>
    <synonym>4-oxo-4-(Pyridin-3-yl)butanoate</synonym>
    <synonym>4-oxo-4-(3-Pyridyl)-butanoate</synonym>
    <synonym>4-oxo-4-(3-Pyridyl)-butyrate</synonym>
    <synonym>4-oxo-4-(Pyridin-3-yl)butyrate</synonym>
    <synonym>g-oxo-3-Pyridinebutanoate</synonym>
    <synonym>g-oxo-3-Pyridinebutanoic acid</synonym>
    <synonym>gamma-oxo-3-Pyridinebutanoate</synonym>
    <synonym>Γ-oxo-3-pyridinebutanoate</synonym>
    <synonym>Γ-oxo-3-pyridinebutanoic acid</synonym>
    <synonym>g-oxo-3-Pyridinebutyrate</synonym>
    <synonym>g-oxo-3-Pyridinebutyric acid</synonym>
    <synonym>gamma-oxo-3-Pyridinebutyrate</synonym>
    <synonym>Γ-oxo-3-pyridinebutyrate</synonym>
    <synonym>Γ-oxo-3-pyridinebutyric acid</synonym>
    <synonym>4-oxo-4-(Pyridin-3-yl)butanoic acid</synonym>
    <synonym>4-OPC4a</synonym>
    <synonym>4-oxo-4-(3-Pyridyl)butyric acid</synonym>
    <synonym>4-oxo-4-(3-Pyridyl)butanoic acid</synonym>
    <synonym>3-Succinoylpyridine</synonym>
  </synonyms>
  <chemical_formula>C9H9NO3</chemical_formula>
  <average_molecular_weight>179.1727</average_molecular_weight>
  <monisotopic_moleculate_weight>179.058243159</monisotopic_moleculate_weight>
  <iupac_name>4-oxo-4-(pyridin-3-yl)butanoic acid</iupac_name>
  <traditional_iupac>3-succinoylpyridine</traditional_iupac>
  <cas_registry_number>4192-31-8</cas_registry_number>
  <smiles>OC(=O)CCC(=O)C1=CC=CN=C1</smiles>
  <inchi>InChI=1S/C9H9NO3/c11-8(3-4-9(12)13)7-2-1-5-10-6-7/h1-2,5-6H,3-4H2,(H,12,13)</inchi>
  <inchikey>JGSUNMCABQUBOY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Gamma-keto acids and derivatives</sub_class>
    <direct_parent>Gamma-keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Aryl alkyl ketones</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridines and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Aryl alkyl ketone</substituent>
      <substituent>Aryl ketone</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Gamma-keto acid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aromatic ketone</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
      <external_descriptor>pyridines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-oxo-4-(pyridin-3-yl)butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>179.1727</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>179.058243159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC(=O)C1=CC=CN=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H9NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H9NO3/c11-8(3-4-9(12)13)7-2-1-5-10-6-7/h1-2,5-6H,3-4H2,(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JGSUNMCABQUBOY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>67.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334620</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C19569</kegg_id>
  <chemspider_id>424</chemspider_id>
  <foodb_id>FDB022355</foodb_id>
  <pubchem_compound_id>437</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>66951</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD-14094</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5924</metlin_id>
  <synthesis_reference>Schwartz, Sorell L.; McKennis, Herbert, Jr.  The degradation of the pyrrolidine ring of (-)-nicotine in vitro. Formation of g-(3-pyridyl)-g-oxobutyric acid.    Journal of Biological Chemistry  (1963),  238  1807-12.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:37 UTC</creation_date>
  <update_date>2020-03-13 16:25:12 UTC</update_date>
  <accession>BMDB0000994</accession>
  <secondary_accessions>
    <accession>BMDB00994</accession>
  </secondary_accessions>
  <name>Dolichyl phosphate D-mannose</name>
  <description/>
  <synonyms>
    <synonym>Dolichyl phosphoric acid D-mannose</synonym>
    <synonym>Dolichol phosphate mannose</synonym>
    <synonym>Dolichyl D-mannosyl phosphate</synonym>
    <synonym>DPM</synonym>
    <synonym>{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonate</synonym>
  </synonyms>
  <chemical_formula>C6H13O9P</chemical_formula>
  <average_molecular_weight>260.1358</average_molecular_weight>
  <monisotopic_moleculate_weight>260.029718526</monisotopic_moleculate_weight>
  <iupac_name>{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>dolichyl phosphate D-mannose</traditional_iupac>
  <cas_registry_number>908211-94-9</cas_registry_number>
  <smiles>OC[C@H]1O[C@@H](OP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6+/m1/s1</inchi>
  <inchikey>HXXFSFRBOHSIMQ-PQMKYFCFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharide phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>260.1358</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>260.029718526</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@@H](OP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HXXFSFRBOHSIMQ-PQMKYFCFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>156.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37881</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357588</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03862</kegg_id>
  <chemspider_id>2496902</chemspider_id>
  <foodb_id>FDB022356</foodb_id>
  <pubchem_compound_id>3246168</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>1220424</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>1809321</bigg_id>
  <wikipedia_id/>
  <metlin_id>5925</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:38 UTC</creation_date>
  <update_date>2020-03-13 16:25:12 UTC</update_date>
  <accession>BMDB0000995</accession>
  <secondary_accessions>
    <accession>BMDB00995</accession>
  </secondary_accessions>
  <name>16-Dehydroprogesterone</name>
  <description/>
  <synonyms>
    <synonym>3,20-Dioxopregna-4,16-diene</synonym>
    <synonym>Delta(4,16)-Pregnadiene-3,20-dione</synonym>
    <synonym>16,17-Didehydroprogesterone</synonym>
    <synonym>Δ(4,16)-pregnadiene-3,20-dione</synonym>
    <synonym>4,16-Pregnadiene-3,20-dione</synonym>
    <synonym>D16-Progesterone</synonym>
    <synonym>D4,16-Pregnadiene-3,20-dione</synonym>
    <synonym>Delta.16-progesterone</synonym>
    <synonym>Delta4,16-Pregnadiene-3,20-dione</synonym>
    <synonym>Pregna-4,16-diene-3,20-dione</synonym>
    <synonym>delta(16)-Progesterone</synonym>
    <synonym>16-Dehydroprogesterone</synonym>
  </synonyms>
  <chemical_formula>C21H28O2</chemical_formula>
  <average_molecular_weight>312.4458</average_molecular_weight>
  <monisotopic_moleculate_weight>312.20893014</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10R,11S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,13-dien-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10R,11S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,13-dien-5-one</traditional_iupac>
  <cas_registry_number>1096-38-4</cas_registry_number>
  <smiles>[H][C@@]12CC=C(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h6,12,16,18-19H,4-5,7-11H2,1-3H3/t16-,18-,19-,20-,21+/m0/s1</inchi>
  <inchikey>VRRHHTISESGZFN-RKFFNLMFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Oxosteroids</sub_class>
    <direct_parent>20-oxosteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>3-oxosteroids</alternative_parent>
      <alternative_parent>Androgens and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>20-oxosteroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Androstane-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>20-oxo steroid</external_descriptor>
      <external_descriptor>3-oxo Delta(4)-steroid</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
      <external_descriptor>enone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>185 - 187 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10R,11S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,13-dien-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>312.4458</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>312.20893014</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC=C(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H28O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h6,12,16,18-19H,4-5,7-11H2,1-3H3/t16-,18-,19-,20-,21+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VRRHHTISESGZFN-RKFFNLMFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>34.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>93.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352449</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03207</kegg_id>
  <chemspider_id>92118</chemspider_id>
  <foodb_id>FDB022357</foodb_id>
  <pubchem_compound_id>101964</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>18204</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5926</metlin_id>
  <synthesis_reference>Johnson, William S.  Intermediates in total synthesis of 16-dehydroprogesterone.    U.S.  (1973),     15 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:39 UTC</creation_date>
  <update_date>2020-04-14 22:48:43 UTC</update_date>
  <accession>BMDB0000996</accession>
  <secondary_accessions>
    <accession>BMDB00996</accession>
  </secondary_accessions>
  <name>3-Sulfinoalanine</name>
  <description>3-Sulfinoalanine, also known as cysteine-S-dioxide or cysteine sulfinate, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 3-Sulfinoalanine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 3-Sulfinoalanine exists in all living species, ranging from bacteria to humans. 3-Sulfinoalanine participates in a number of enzymatic reactions, within cattle. In particular, 3-Sulfinoalanine can be biosynthesized from L-cysteine; which is mediated by the enzyme cysteine dioxygenase type 1. Furthermore, 3-Sulfinoalanine can be converted into hypotaurine through the action of the enzyme cysteine sulfinic acid decarboxylase. Furthermore, 3-Sulfinoalanine and oxoglutaric acid can be converted into 3-sulfinylpyruvic acid and L-glutamic acid through its interaction with the enzyme aspartate aminotransferase, cytoplasmic. Finally, 3-Sulfinoalanine can be biosynthesized from L-cysteine through its interaction with the enzyme cysteine dioxygenase type 1. In cattle, 3-sulfinoalanine is involved in a couple of metabolic pathways, which include the taurine and hypotaurine metabolism pathway and the cysteine metabolism pathway.</description>
  <synonyms>
    <synonym>(2R)-2-Amino-3-sulfinopropanoic acid</synonym>
    <synonym>3-Sulphino-L-alanine</synonym>
    <synonym>L-Cysteinesulfinic acid</synonym>
    <synonym>(2R)-2-Amino-3-sulfinopropanoate</synonym>
    <synonym>(2R)-2-Amino-3-sulphinopropanoate</synonym>
    <synonym>(2R)-2-Amino-3-sulphinopropanoic acid</synonym>
    <synonym>3-Sulfino-L-alanine</synonym>
    <synonym>L-Cysteinesulfinate</synonym>
    <synonym>L-Cysteinesulphinate</synonym>
    <synonym>L-Cysteinesulphinic acid</synonym>
    <synonym>3-Sulphinoalanine</synonym>
    <synonym>3-Sulfinato-L-alaninic acid</synonym>
    <synonym>3-Sulphinato-L-alaninate</synonym>
    <synonym>3-Sulphinato-L-alaninic acid</synonym>
    <synonym>Cysteine hydrogen sulfite ester</synonym>
    <synonym>Alanine 3-sulfinic acid</synonym>
    <synonym>Cysteine sulfinate</synonym>
    <synonym>Cysteine sulfinic acid</synonym>
    <synonym>3-Sulfinato-L-alaninate</synonym>
    <synonym>Alanine-3-sulfinic acid</synonym>
    <synonym>Alaninesulfinic acid</synonym>
    <synonym>Cysteinesulfinate</synonym>
    <synonym>Cysteinesulfinic acid</synonym>
    <synonym>L-2-Amino-3-sulfinopropionic acid</synonym>
    <synonym>3-Sulfinoalanine</synonym>
  </synonyms>
  <chemical_formula>C3H7NO4S</chemical_formula>
  <average_molecular_weight>153.157</average_molecular_weight>
  <monisotopic_moleculate_weight>153.009578407</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-amino-3-[(R)-sulfino]propanoic acid</iupac_name>
  <traditional_iupac>3-sulfinoalanine</traditional_iupac>
  <cas_registry_number>1115-65-7</cas_registry_number>
  <smiles>N[C@@H](CS(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1</inchi>
  <inchikey>ADVPTQAUNPRNPO-REOHCLBHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkanesulfinic acids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfur compounds</alternative_parent>
      <alternative_parent>Sulfinic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkanesulfinic acid</substituent>
      <substituent>Alkanesulfinic acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Sulfinic acid</substituent>
      <substituent>Sulfinic acid derivative</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>S-substituted L-cysteine</external_descriptor>
      <external_descriptor>organosulfinic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-amino-3-[(R)-sulfino]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>153.157</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>153.009578407</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CS(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7NO4S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ADVPTQAUNPRNPO-REOHCLBHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>100.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Taurine and Hypotaurine Metabolism</name>
      <smpdb_id>SMP0087214</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>48102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>263424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>263425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>263426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>283353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>283354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>283355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451893</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00606</kegg_id>
  <chemspider_id>1266065</chemspider_id>
  <foodb_id>FDB022358</foodb_id>
  <pubchem_compound_id>1549098</pubchem_compound_id>
  <drugbank_id>DB02153</drugbank_id>
  <chebi_id>16345</chebi_id>
  <pdbe_id>CSD</pdbe_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Cysteine_sulfinic_acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Kissman, Henry M.; Baker, B. R.  Preparation of various amides of p-methoxy-L-phenylalanine.    Journal of Medicinal &amp; Pharmaceutical Chemistry  (1960),  2  415-23.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00683</protein_accession>
      <name>Cysteine dioxygenase type 1</name>
      <uniprot_id>Q3SZU4</uniprot_id>
      <gene_name>CDO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:41 UTC</creation_date>
  <update_date>2020-03-13 16:25:14 UTC</update_date>
  <accession>BMDB0000998</accession>
  <secondary_accessions>
    <accession>BMDB00998</accession>
  </secondary_accessions>
  <name>dCTP</name>
  <description/>
  <synonyms>
    <synonym>2'-Deoxycytidine 5'-triphosphate</synonym>
    <synonym>Deoxycytidine 5'-triphosphate</synonym>
    <synonym>Deoxycytidine triphosphate</synonym>
    <synonym>2'-Deoxycytidine 5'-triphosphoric acid</synonym>
    <synonym>Deoxycytidine 5'-triphosphoric acid</synonym>
    <synonym>Deoxycytidine triphosphoric acid</synonym>
    <synonym>2'-Deoxycytidine-5'-triphosphate</synonym>
    <synonym>Deoxy-CTP</synonym>
    <synonym>Deoxycytidine-triphosphate</synonym>
    <synonym>2'-Deoxycytidine 5'-triphosphate, 3H-labeled</synonym>
    <synonym>2'-Deoxycytidine 5'-triphosphate, p-(32)p-labeled</synonym>
    <synonym>2'-Deoxycytidine 5'-triphosphate, magnesium salt</synonym>
    <synonym>2'-Deoxycytidine 5'-triphosphate, p''-(32)p-labeled</synonym>
  </synonyms>
  <chemical_formula>C9H16N3O13P3</chemical_formula>
  <average_molecular_weight>467.1569</average_molecular_weight>
  <monisotopic_moleculate_weight>466.989597149</monisotopic_moleculate_weight>
  <iupac_name>({[({[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</iupac_name>
  <traditional_iupac>dCTP</traditional_iupac>
  <cas_registry_number>2056-98-6</cas_registry_number>
  <smiles>NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1</smiles>
  <inchi>InChI=1S/C9H16N3O13P3/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(23-8)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,13H,3-4H2,(H,18,19)(H,20,21)(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1</inchi>
  <inchikey>RGWHQCVHVJXOKC-SHYZEUOFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside triphosphates. These are pyrimidine nucleotides with a triphosphate group  linked to the ribose moiety lacking a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine deoxyribonucleotides</sub_class>
    <direct_parent>Pyrimidine 2'-deoxyribonucleoside triphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside triphosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2'-deoxycytidine phosphate</external_descriptor>
      <external_descriptor>Deoxyribonucleotides</external_descriptor>
      <external_descriptor>pyrimidine 2'-deoxyribonucleoside 5'-triphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>({[({[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>467.1569</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>466.989597149</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H16N3O13P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H16N3O13P3/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(23-8)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,13H,3-4H2,(H,18,19)(H,20,21)(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RGWHQCVHVJXOKC-SHYZEUOFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>247.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>85.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32662</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00458</kegg_id>
  <chemspider_id>58601</chemspider_id>
  <foodb_id>FDB022359</foodb_id>
  <pubchem_compound_id>65091</pubchem_compound_id>
  <drugbank_id>DB03258</drugbank_id>
  <chebi_id>16311</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>35027</bigg_id>
  <wikipedia_id>Deoxycytidine triphosphate</wikipedia_id>
  <metlin_id>5929</metlin_id>
  <synthesis_reference>Hinz M; Gottschling D; Eritja R; Seliger H  Synthesis and properties of 2'-deoxycytidine triphosphate carrying c-myc tag sequence.    Nucleosides, nucleotides &amp; nucleic acids  (2000),  19(10-12),  1543-52.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00613</protein_accession>
      <name>dCTP pyrophosphatase 1</name>
      <uniprot_id>Q32KY6</uniprot_id>
      <gene_name>DCTPP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:42 UTC</creation_date>
  <update_date>2020-03-13 16:25:14 UTC</update_date>
  <accession>BMDB0000999</accession>
  <secondary_accessions>
    <accession>BMDB00999</accession>
  </secondary_accessions>
  <name>Phosphoribosylformylglycineamidine</name>
  <description/>
  <synonyms>
    <synonym>1-(5'-Phosphoribosyl)-N-formylglycinamidine</synonym>
    <synonym>5'-Phosphoribosylformylglycinamidine</synonym>
    <synonym>2-(Formamido)-N1-(5-phospho-D-ribosyl)acetamidine</synonym>
    <synonym>5'-Phosphoribosyl-N-formyl glycineamidine</synonym>
    <synonym>FGAM</synonym>
    <synonym>N-(2-Amino-2-iminoethyl)-N-(5-O-phosphono-b-D-ribofuranosyl)-formamide</synonym>
    <synonym>N-(2-Amino-2-iminoethyl)-N-(5-O-phosphono-beta-delta-ribofuranosyl)-formamide</synonym>
    <synonym>1-(5’-phosphoribosyl)-N-formylglycinamidine</synonym>
    <synonym>2-(Formamido)-N1-(5'-phosphoribosyl)acetamidine</synonym>
    <synonym>2-(Formamido)-N1-(5’-phosphoribosyl)acetamidine</synonym>
    <synonym>2-Formamido-N(1)-(5-O-phosphonato-D-ribosyl)acetamidine</synonym>
    <synonym>5'-Phosphoribosyl-alpha-N-formylglycineamidine</synonym>
    <synonym>5'-Phosphoribosyl-α-N-formylglycineamidine</synonym>
    <synonym>5’-phosphoribosyl-N-formyl glycineamidine</synonym>
    <synonym>5’-phosphoribosyl-N-formylglycinamidine</synonym>
    <synonym>5’-phosphoribosyl-α-N-formylglycineamidine</synonym>
    <synonym>5’-phosphoribosylformylglycinamidine</synonym>
    <synonym>N-[2-Imino-2-[(5-O-phosphono-beta-D-ribofuranosyl)amino]ethyl]formamide</synonym>
    <synonym>N-[2-Imino-2-[(5-O-phosphono-β-D-ribofuranosyl)amino]ethyl]formamide</synonym>
    <synonym>Phosphoribosylformylglycineamidine</synonym>
    <synonym>Formylglycinamidine ribonucleotide</synonym>
    <synonym>Phosphoribosylformylglycinamidine</synonym>
    <synonym>5'-Phosphoribosyl-N-formylglycinamidine</synonym>
  </synonyms>
  <chemical_formula>C8H16N3O8P</chemical_formula>
  <average_molecular_weight>313.2017</average_molecular_weight>
  <monisotopic_moleculate_weight>313.067501015</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoethanimidamido)oxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoethanimidamido)oxolan-2-yl]methoxyphosphonic acid</traditional_iupac>
  <cas_registry_number>6157-85-3</cas_registry_number>
  <smiles>O[C@H]1[C@@H](O)[C@H](NC(=N)CNC=O)O[C@@H]1COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C8H16N3O8P/c9-5(1-10-3-12)11-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H2,9,11)(H,10,12)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1</inchi>
  <inchikey>PMCOGCVKOAOZQM-XVFCMESISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxamidines</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amidine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid amidine</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>7.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoethanimidamido)oxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>313.2017</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>313.067501015</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@@H](O)[C@H](NC(=N)CNC=O)O[C@@H]1COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16N3O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16N3O8P/c9-5(1-10-3-12)11-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H2,9,11)(H,10,12)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PMCOGCVKOAOZQM-XVFCMESISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>181.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32707</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022360</foodb_id>
  <kegg_id>C04640</kegg_id>
  <drugbank_id/>
  <pubchem_compound_id>440417</pubchem_compound_id>
  <chemspider_id>7830994</chemspider_id>
  <chebi_id>18413</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>5-PHOSPHORIBOSYL-N-FORMYLGLYCINEAMIDINE</meta_cyc_id>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>5930</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:43 UTC</creation_date>
  <update_date>2020-03-13 16:25:15 UTC</update_date>
  <accession>BMDB0001000</accession>
  <secondary_accessions>
    <accession>BMDB01000</accession>
  </secondary_accessions>
  <name>dUDP</name>
  <description/>
  <synonyms>
    <synonym>2'-Deoxyuridine 5'-diphosphate</synonym>
    <synonym>2'-Deoxyuridine 5'-diphosphoric acid</synonym>
    <synonym>2'-Deoxyuridine-5'-diphosphate</synonym>
    <synonym>Deoxyuridine-diphosphate</synonym>
  </synonyms>
  <chemical_formula>C9H14N2O11P2</chemical_formula>
  <average_molecular_weight>388.1618</average_molecular_weight>
  <monisotopic_moleculate_weight>388.007282324</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>dUDP</traditional_iupac>
  <cas_registry_number>4208-67-7</cas_registry_number>
  <smiles>O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C9H14N2O11P2/c12-5-3-8(11-2-1-7(13)10-9(11)14)21-6(5)4-20-24(18,19)22-23(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,18,19)(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1</inchi>
  <inchikey>QHWZTVCCBMIIKE-SHYZEUOFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside diphosphates. These are pyrimidine nucleotides with a diphosphate group  linked to the ribose moiety lacking a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine deoxyribonucleotides</sub_class>
    <direct_parent>Pyrimidine 2'-deoxyribonucleoside diphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside diphosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxyribonucleotides</external_descriptor>
      <external_descriptor>deoxyuridine phosphate</external_descriptor>
      <external_descriptor>pyrimidine 2'-deoxyribonucleoside 5'-diphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>388.1618</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>388.007282324</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H14N2O11P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H14N2O11P2/c12-5-3-8(11-2-1-7(13)10-9(11)14)21-6(5)4-20-24(18,19)22-23(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,18,19)(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QHWZTVCCBMIIKE-SHYZEUOFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>192.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181766</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01346</kegg_id>
  <chemspider_id>128553</chemspider_id>
  <foodb_id>FDB022361</foodb_id>
  <pubchem_compound_id>145729</pubchem_compound_id>
  <drugbank_id>DB03413</drugbank_id>
  <chebi_id>28850</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>37403</bigg_id>
  <wikipedia_id/>
  <metlin_id>5931</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:44 UTC</creation_date>
  <update_date>2020-04-15 22:29:53 UTC</update_date>
  <accession>BMDB0001003</accession>
  <secondary_accessions>
    <accession>BMDB01003</accession>
  </secondary_accessions>
  <name>Adenosine phosphosulfate</name>
  <description/>
  <synonyms>
    <synonym>Adenosine 5'-phosphosulfate</synonym>
    <synonym>ADENOSINE-5'-phosphosulfATE</synonym>
    <synonym>Adenylylsulfate</synonym>
    <synonym>APS</synonym>
    <synonym>5'-Adenylyl sulfate</synonym>
    <synonym>Adenosine 5'-phosphosulfuric acid</synonym>
    <synonym>Adenosine 5'-phosphosulphate</synonym>
    <synonym>Adenosine 5'-phosphosulphuric acid</synonym>
    <synonym>ADENOSINE-5'-phosphosulfuric acid</synonym>
    <synonym>ADENOSINE-5'-phosphosulphate</synonym>
    <synonym>ADENOSINE-5'-phosphosulphuric acid</synonym>
    <synonym>Adenylylsulfuric acid</synonym>
    <synonym>Adenylylsulphate</synonym>
    <synonym>Adenylylsulphuric acid</synonym>
    <synonym>5'-Adenylyl sulfuric acid</synonym>
    <synonym>5'-Adenylyl sulphate</synonym>
    <synonym>5'-Adenylyl sulphuric acid</synonym>
    <synonym>Adenosine phosphosulfuric acid</synonym>
    <synonym>Adenosine phosphosulphate</synonym>
    <synonym>Adenosine phosphosulphuric acid</synonym>
    <synonym>Adenosine 5'-sulphatophosphate</synonym>
    <synonym>Adenosine sulfatophosphate</synonym>
    <synonym>Adenylic acid monoanhydride with sulfurate</synonym>
    <synonym>Adenylic acid monoanhydride with sulfuric acid</synonym>
    <synonym>Adenylyl sulfate</synonym>
    <synonym>Adenylyl sulphate</synonym>
    <synonym>Adenylyl-sulfate</synonym>
    <synonym>Adenylyl-sulphate</synonym>
    <synonym>AMPS</synonym>
    <synonym>Phosphosulfate</synonym>
    <synonym>Phosphosulphate</synonym>
    <synonym>Sulfatophosphate</synonym>
    <synonym>5'-Phosphosulfate, adenosine</synonym>
    <synonym>Adenosine 5' phosphosulfate</synonym>
    <synonym>Phospho adenylsulfate</synonym>
    <synonym>Phospho-adenylsulfate</synonym>
    <synonym>Phosphosulfate, adenosine</synonym>
    <synonym>Sulfate, adenylyl</synonym>
  </synonyms>
  <chemical_formula>C10H14N5O10PS</chemical_formula>
  <average_molecular_weight>427.284</average_molecular_weight>
  <monisotopic_moleculate_weight>427.019898895</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid</iupac_name>
  <traditional_iupac>adenosine phosphosulfate</traditional_iupac>
  <cas_registry_number>485-84-7</cas_registry_number>
  <smiles>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C10H14N5O10PS/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-26(18,19)25-27(20,21)22/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H2,11,12,13)(H,20,21,22)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>IRLPACMLTUPBCL-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic sulfuric acids and derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>acyl monophosphate</external_descriptor>
      <external_descriptor>acyl sulfate</external_descriptor>
      <external_descriptor>adenosine 5'-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>427.284</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>427.019898895</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H14N5O10PS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H14N5O10PS/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-26(18,19)25-27(20,21)22/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H2,11,12,13)(H,20,21,22)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IRLPACMLTUPBCL-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>229.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Sulfate/Sulfite Metabolism</name>
      <smpdb_id>SMP0087216</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1572</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00224</kegg_id>
  <chemspider_id>9821</chemspider_id>
  <foodb_id>FDB022362</foodb_id>
  <pubchem_compound_id>10238</pubchem_compound_id>
  <drugbank_id>DB03708</drugbank_id>
  <chebi_id>17709</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00007445</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>34307</bigg_id>
  <wikipedia_id/>
  <metlin_id>5933</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:45 UTC</creation_date>
  <update_date>2020-03-13 16:25:16 UTC</update_date>
  <accession>BMDB0001004</accession>
  <secondary_accessions>
    <accession>BMDB01004</accession>
  </secondary_accessions>
  <name>Oxoamide</name>
  <description/>
  <synonyms>
    <synonym>4-(3-Pyridyl)-4-oxo-N-methylbutyramide</synonym>
    <synonym>4-oxo-4-(3-Pyridyl)-N-methylbutanamide</synonym>
    <synonym>gamma-(3-Pyridyl)-gamma-oxo-N-methylbutyramide</synonym>
    <synonym>N-Methyl-gamma-oxo-3-pyridinebutanamide</synonym>
    <synonym>N-Methyl-4-oxo-4-(pyridin-3-yl)butanimidate</synonym>
    <synonym>Oxoamide</synonym>
  </synonyms>
  <chemical_formula>C10H12N2O2</chemical_formula>
  <average_molecular_weight>192.2145</average_molecular_weight>
  <monisotopic_moleculate_weight>192.089877638</monisotopic_moleculate_weight>
  <iupac_name>N-methyl-4-oxo-4-(pyridin-3-yl)butanamide</iupac_name>
  <traditional_iupac>N-methyl-4-oxo-4-(pyridin-3-yl)butanamide</traditional_iupac>
  <cas_registry_number>713-05-3</cas_registry_number>
  <smiles>CNC(=O)CCC(=O)C1=CN=CC=C1</smiles>
  <inchi>InChI=1S/C10H12N2O2/c1-11-10(14)5-4-9(13)8-3-2-6-12-7-8/h2-3,6-7H,4-5H2,1H3,(H,11,14)</inchi>
  <inchikey>WOOSCPWOYYLIHS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Aryl alkyl ketones</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridines and derivatives</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Aryl alkyl ketone</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>logp</kind>
      <value>-0.69</value>
      <source>LI,NY &amp; GORROD,JW (1992)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-methyl-4-oxo-4-(pyridin-3-yl)butanamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>192.2145</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>192.089877638</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CNC(=O)CCC(=O)C1=CN=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N2O2/c1-11-10(14)5-4-9(13)8-3-2-6-12-7-8/h2-3,6-7H,4-5H2,1H3,(H,11,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WOOSCPWOYYLIHS-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>59.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11562</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>423</chemspider_id>
  <foodb_id>FDB022363</foodb_id>
  <pubchem_compound_id>436</pubchem_compound_id>
  <kegg_id/>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5934</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:46 UTC</creation_date>
  <update_date>2020-03-13 16:25:16 UTC</update_date>
  <accession>BMDB0001005</accession>
  <secondary_accessions>
    <accession>BMDB01005</accession>
  </secondary_accessions>
  <name>(S)-Ureidoglycolic acid</name>
  <description/>
  <synonyms>
    <synonym>(-)-Ureidoglycolate</synonym>
    <synonym>(S)-Ureidoglycolate</synonym>
    <synonym>(-)-Ureidoglycolic acid</synonym>
    <synonym>(S)-[(Aminocarbonyl)amino]hydroxy-acetic acid</synonym>
    <synonym>S-(-)-Ureidoglycolic acid</synonym>
    <synonym>Ureidoglycolate</synonym>
  </synonyms>
  <chemical_formula>C3H6N2O4</chemical_formula>
  <average_molecular_weight>134.0907</average_molecular_weight>
  <monisotopic_moleculate_weight>134.03275669</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-(carbamoylamino)-2-hydroxyacetic acid</iupac_name>
  <traditional_iupac>ureidoglycolate</traditional_iupac>
  <cas_registry_number>7424-03-5</cas_registry_number>
  <smiles>NC(=O)N[C@@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H6N2O4/c4-3(9)5-1(6)2(7)8/h1,6H,(H,7,8)(H3,4,5,9)/t1-/m0/s1</inchi>
  <inchikey>NWZYYCVIOKVTII-SFOWXEAESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids. N-carbamoyl-alpha amino acids are compounds containing an alpha amino acid which bears an carbamoyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-carbamoyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkanolamines</alternative_parent>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkanolamine</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonic acid derivative</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-carbamoyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Urea</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>ureidoglycolic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-(carbamoylamino)-2-hydroxyacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>134.0907</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>134.03275669</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)N[C@@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H6N2O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H6N2O4/c4-3(9)5-1(6)2(7)8/h1,6H,(H,7,8)(H3,4,5,9)/t1-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NWZYYCVIOKVTII-SFOWXEAESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>112.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35752</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>388403</chemspider_id>
  <foodb_id>FDB022364</foodb_id>
  <pubchem_compound_id>439269</pubchem_compound_id>
  <kegg_id>C00603</kegg_id>
  <drugbank_id/>
  <chebi_id>15412</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007466</knapsack_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5935</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00801</protein_accession>
      <name>Probable allantoicase</name>
      <uniprot_id>Q2KIG4</uniprot_id>
      <gene_name>ALLC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:47 UTC</creation_date>
  <update_date>2020-03-13 16:25:17 UTC</update_date>
  <accession>BMDB0001007</accession>
  <secondary_accessions>
    <accession>BMDB01007</accession>
  </secondary_accessions>
  <name>3-Pyridinebutanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Pyridinebutanoate</synonym>
    <synonym>4-(3-Pyridyl)-butanoate</synonym>
    <synonym>4-(3-Pyridyl)-butanoic acid</synonym>
    <synonym>4-3-Pyridyl-butanoate</synonym>
    <synonym>4-3-Pyridyl-butanoic acid</synonym>
    <synonym>4-Pyridin-3-ylbutanoate</synonym>
    <synonym>4-Pyridin-3-ylbutanoic acid</synonym>
    <synonym>4-(Pyridin-3-yl)butanoate</synonym>
  </synonyms>
  <chemical_formula>C9H11NO2</chemical_formula>
  <average_molecular_weight>165.1891</average_molecular_weight>
  <monisotopic_moleculate_weight>165.078978601</monisotopic_moleculate_weight>
  <iupac_name>4-(pyridin-3-yl)butanoic acid</iupac_name>
  <traditional_iupac>4-(pyridin-3-yl)butanoic acid</traditional_iupac>
  <cas_registry_number>477251-67-5</cas_registry_number>
  <smiles>OC(=O)CCCC1=CC=CN=C1</smiles>
  <inchi>InChI=1S/C9H11NO2/c11-9(12)5-1-3-8-4-2-6-10-7-8/h2,4,6-7H,1,3,5H2,(H,11,12)</inchi>
  <inchikey>MFYZACBRKCFXDV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class/>
    <direct_parent>Pyridines and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-(pyridin-3-yl)butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>165.1891</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>165.078978601</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCC1=CC=CN=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11NO2/c11-9(12)5-1-3-8-4-2-6-10-7-8/h2,4,6-7H,1,3,5H2,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MFYZACBRKCFXDV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>50.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>44.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354096</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>112</chemspider_id>
  <foodb_id>FDB022365</foodb_id>
  <pubchem_compound_id>114</pubchem_compound_id>
  <kegg_id/>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:49 UTC</creation_date>
  <update_date>2020-04-16 20:37:24 UTC</update_date>
  <accession>BMDB0001008</accession>
  <secondary_accessions>
    <accession>BMDB01008</accession>
  </secondary_accessions>
  <name>Biliverdin</name>
  <description/>
  <synonyms>
    <synonym>Biliverdin IX</synonym>
    <synonym>1,3,6,7-Tetramethyl-4,5-dicarboxyethyl-2,8-divinylbilenone</synonym>
    <synonym>Biliverdin IX alpha</synonym>
    <synonym>Biliverdine</synonym>
    <synonym>Dehydrobilirubin</synonym>
    <synonym>Protobiliverdin IX</synonym>
    <synonym>Uteroverdine</synonym>
    <synonym>IX, biliverdin</synonym>
    <synonym>IX alpha, biliverdin</synonym>
    <synonym>Ooecyan</synonym>
    <synonym>alpha, Biliverdin IX</synonym>
  </synonyms>
  <chemical_formula>C33H34N4O6</chemical_formula>
  <average_molecular_weight>582.6463</average_molecular_weight>
  <monisotopic_moleculate_weight>582.24783484</monisotopic_moleculate_weight>
  <iupac_name>3-(2-{[(2Z,5E)-3-(2-carboxyethyl)-5-[(3-ethenyl-4-methyl-2-oxo-2H-pyrrol-5-yl)methylidene]-4-methyl-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid</iupac_name>
  <traditional_iupac>3-(2-{[(2Z,5E)-3-(2-carboxyethyl)-5-[(4-ethenyl-3-methyl-5-oxopyrrol-2-yl)methylidene]-4-methyl-1H-pyrrol-2-ylidene]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N\C(=C\C2=NC(=O)C(C=C)=C2C)C(C)=C1CCC(O)=O</smiles>
  <inchi>InChI=1S/C33H34N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-15,34-35H,1-2,9-12H2,3-6H3,(H,37,42)(H,38,39)(H,40,41)/b24-13+,27-14-,28-15-</inchi>
  <inchikey>RCNSAJSGRJSBKK-YKSNQIBWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Bilirubins</sub_class>
    <direct_parent>Bilirubins</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Dipyrrins</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>N-acylimines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrrolines</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Bilirubin skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Dipyrrin</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>N-acylimine</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Pyrroline</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>7.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(2-{[(2Z,5E)-3-(2-carboxyethyl)-5-[(3-ethenyl-4-methyl-2-oxo-2H-pyrrol-5-yl)methylidene]-4-methyl-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>582.6463</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>582.24783484</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N\C(=C\C2=NC(=O)C(C=C)=C2C)C(C)=C1CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C33H34N4O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C33H34N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-15,34-35H,1-2,9-12H2,3-6H3,(H,37,42)(H,38,39)(H,40,41)/b24-13+,27-14-,28-15-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RCNSAJSGRJSBKK-YKSNQIBWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>160.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>169.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>64.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182847</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37889</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id/>
  <drugbank_id/>
  <chemspider_id/>
  <pubchem_compound_id>5353439</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Biliverdin</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Mora, Maria E.; Bari, Sara E.; Awruch, Josefina; Delfino, Jose M. On how the conformation of biliverdins influences their reduction to bilirubins: A biological and molecular modeling study.      Bioorganic &amp; Medicinal Chemistry  (2003),  11(21),  4661-467</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00070</protein_accession>
      <name>Heme oxygenase 1</name>
      <uniprot_id>Q5E9F2</uniprot_id>
      <gene_name>HMOX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00102</protein_accession>
      <name>Prostaglandin-H2 D-isomerase</name>
      <uniprot_id>O02853</uniprot_id>
      <gene_name>PTGDS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00585</protein_accession>
      <name>Flavin reductase</name>
      <uniprot_id>P52556</uniprot_id>
      <gene_name>BLVRB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:50 UTC</creation_date>
  <update_date>2020-04-14 22:48:45 UTC</update_date>
  <accession>BMDB0001009</accession>
  <secondary_accessions>
    <accession>BMDB01009</accession>
  </secondary_accessions>
  <name>N-Methylnicotinium</name>
  <description/>
  <synonyms>
    <synonym>1-Methyl-3-(1-methyl-2-pyrrolidinyl)-pyridinium</synonym>
    <synonym>N-Methylnicotinium acetate</synonym>
    <synonym>N-Methylnicotinium ion</synonym>
    <synonym>Nicotine isomethiodide</synonym>
    <synonym>Nicotine isomethonium ion</synonym>
    <synonym>N-Methylnicotinium acetate, (R)-isomer</synonym>
    <synonym>N-Methylnicotinium acetate, (S)-isomer</synonym>
    <synonym>N-Methylnicotinium bromide</synonym>
    <synonym>N-Methylnicotinium, (R)-isomer</synonym>
    <synonym>N-Methylnicotinium, (S)-isomer</synonym>
    <synonym>N-Methylnicotinium, (iodide(S))-isomer, 3H-labeled</synonym>
    <synonym>N-Methylnicotinium, bromide(S)-isomer</synonym>
    <synonym>N-Methylnicotinium, iodide(R)-isomer</synonym>
    <synonym>N-Methylnicotinium, iodide(S)-isomer</synonym>
    <synonym>N-Methylnicotinium</synonym>
  </synonyms>
  <chemical_formula>C11H17N2</chemical_formula>
  <average_molecular_weight>177.2661</average_molecular_weight>
  <monisotopic_moleculate_weight>177.139173554</monisotopic_moleculate_weight>
  <iupac_name>1-methyl-3-(1-methylpyrrolidin-2-yl)pyridin-1-ium</iupac_name>
  <traditional_iupac>nicotine isomethonium ion</traditional_iupac>
  <cas_registry_number>24554-05-0</cas_registry_number>
  <smiles>CN1CCCC1C1=CC=C[N+](C)=C1</smiles>
  <inchi>InChI=1S/C11H17N2/c1-12-7-3-5-10(9-12)11-6-4-8-13(11)2/h3,5,7,9,11H,4,6,8H2,1-2H3/q+1</inchi>
  <inchikey>HIOROZIUERMMRQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyrrolidinylpyridines</sub_class>
    <direct_parent>Pyrrolidinylpyridines</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-alkylpyrrolidines</alternative_parent>
      <alternative_parent>N-methylpyridinium compounds</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridinium derivatives</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-alkylpyrrolidine</substituent>
      <substituent>N-methylpyridinium</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridinium</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidinylpyridine</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-methyl-3-(1-methylpyrrolidin-2-yl)pyridin-1-ium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>177.2661</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>177.139173554</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1CCCC1C1=CC=C[N+](C)=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H17N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H17N2/c1-12-7-3-5-10(9-12)11-6-4-8-13(11)2/h3,5,7,9,11H,4,6,8H2,1-2H3/q+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HIOROZIUERMMRQ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>7.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>55.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>109499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>176948</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>417</chemspider_id>
  <foodb_id>FDB022367</foodb_id>
  <pubchem_compound_id>430</pubchem_compound_id>
  <kegg_id/>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>1533</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:51 UTC</creation_date>
  <update_date>2020-04-15 22:14:50 UTC</update_date>
  <accession>BMDB0001010</accession>
  <secondary_accessions>
    <accession>BMDB01010</accession>
  </secondary_accessions>
  <name>Nicotine imine</name>
  <description/>
  <synonyms>
    <synonym>(S)-1-(Methylene-11C)-2-(3-pyridinyl)-pyrrolidium</synonym>
    <synonym>(S)-1-(Methylene-11C)-2-(3-pyridinyl)pyrrolidinium</synonym>
    <synonym>11C-Nicotine imine</synonym>
    <synonym>Nicotine iminium</synonym>
    <synonym>Nicotine-delta 1'-(5')-iminium</synonym>
    <synonym>Nicotine delta 1'(5)' iminium ion</synonym>
  </synonyms>
  <chemical_formula>C10H13N2</chemical_formula>
  <average_molecular_weight>161.2236</average_molecular_weight>
  <monisotopic_moleculate_weight>161.107873426</monisotopic_moleculate_weight>
  <iupac_name>1-methyl-2-(pyridin-3-yl)-3,4-dihydro-2H-pyrrol-1-ium</iupac_name>
  <traditional_iupac>1-methyl-2-(pyridin-3-yl)-3,4-dihydro-2H-pyrrol-1-ium</traditional_iupac>
  <cas_registry_number>74710-78-4</cas_registry_number>
  <smiles>C[N+]1=CCCC1C1=CC=CN=C1</smiles>
  <inchi>InChI=1S/C10H13N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6-8,10H,3,5H2,1H3/q+1</inchi>
  <inchikey>GTQXYYYOJZZJHL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Alkaloids and derivatives</super_class>
    <class/>
    <sub_class/>
    <direct_parent>Alkaloids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridines and derivatives</alternative_parent>
      <alternative_parent>Pyrrolines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyrroline</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-methyl-2-(pyridin-3-yl)-3,4-dihydro-2H-pyrrol-1-ium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>161.2236</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>161.107873426</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+]1=CCCC1C1=CC=CN=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H13N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H13N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6-8,10H,3,5H2,1H3/q+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GTQXYYYOJZZJHL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>15.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>59.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>108344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175541</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>418</chemspider_id>
  <foodb_id>FDB022368</foodb_id>
  <pubchem_compound_id>431</pubchem_compound_id>
  <kegg_id/>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5940</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:52 UTC</creation_date>
  <update_date>2020-03-13 16:25:19 UTC</update_date>
  <accession>BMDB0001011</accession>
  <secondary_accessions>
    <accession>BMDB01011</accession>
  </secondary_accessions>
  <name>Methacrylyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>2-Methylprop-2-enoyl-CoA</synonym>
    <synonym>2-Methylprop-2-enoyl-coenzyme A</synonym>
    <synonym>Methacrylyl CoA</synonym>
    <synonym>Methacrylyl coenzyme A</synonym>
    <synonym>Methacrylyl-coenzyme A</synonym>
    <synonym>Methylacrylyl-CoA</synonym>
    <synonym>Methylacrylyl-coenzyme A</synonym>
    <synonym>S-(2-Methyl-2-propenoate</synonym>
    <synonym>S-(2-Methyl-2-propenoate) CoA</synonym>
    <synonym>S-(2-Methyl-2-propenoate) coenzyme A</synonym>
    <synonym>S-(2-Methyl-2-propenoic acid</synonym>
  </synonyms>
  <chemical_formula>C25H40N7O17P3S</chemical_formula>
  <average_molecular_weight>835.608</average_molecular_weight>
  <monisotopic_moleculate_weight>835.141423115</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylprop-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylprop-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>6008-91-9</cas_registry_number>
  <smiles>CC(=C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C25H40N7O17P3S/c1-13(2)24(37)53-8-7-27-15(33)5-6-28-22(36)19(35)25(3,4)10-46-52(43,44)49-51(41,42)45-9-14-18(48-50(38,39)40)17(34)23(47-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-12,14,17-19,23,34-35H,1,5-10H2,2-4H3,(H,27,33)(H,28,36)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,17-,18-,19?,23-/m1/s1</inchi>
  <inchikey>NPALUEYCDZWBOV-NNYIDDMCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylprop-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>835.608</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>835.141423115</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H40N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C25H40N7O17P3S/c1-13(2)24(37)53-8-7-27-15(33)5-6-28-22(36)19(35)25(3,4)10-46-52(43,44)49-51(41,42)45-9-14-18(48-50(38,39)40)17(34)23(47-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-12,14,17-19,23,34-35H,1,5-10H2,2-4H3,(H,27,33)(H,28,36)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,17-,18-,19?,23-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NPALUEYCDZWBOV-NNYIDDMCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>181.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>73.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30613</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>389035</chemspider_id>
  <foodb_id>FDB022369</foodb_id>
  <pubchem_compound_id>440021</pubchem_compound_id>
  <kegg_id>C03460</kegg_id>
  <drugbank_id/>
  <chebi_id>27754</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>41895</bigg_id>
  <wikipedia_id>Methacrylyl-CoA</wikipedia_id>
  <metlin_id>5941</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Hawes, John W.; Harper, Edwin T. Synthesis of methacrylyl-CoA and (R)- and (S)-3-hydroxyisobutyryl-CoA. Methods in Enzymology (2</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00894</protein_accession>
      <name>Isobutyryl-CoA dehydrogenase, mitochondrial</name>
      <uniprot_id>Q0NXR6</uniprot_id>
      <gene_name>ACAD8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:53 UTC</creation_date>
  <update_date>2020-04-15 22:14:51 UTC</update_date>
  <accession>BMDB0001013</accession>
  <secondary_accessions>
    <accession>BMDB01013</accession>
  </secondary_accessions>
  <name>Cotinineglucuronide</name>
  <description/>
  <synonyms>
    <synonym>alpha-D-Xylopyranosyl ester</synonym>
    <synonym>alpha-delta-Xylopyranosyl ester</synonym>
    <synonym>UDP Xylose</synonym>
    <synonym>UDP-alpha</synonym>
    <synonym>UDP-delta-Xylose</synonym>
    <synonym>Uridine diphosphate xylose</synonym>
    <synonym>1-b-D-Glucopyranuronosyl-3-(1-methyl-5-oxo-2-pyrrolidinyl)- pyridinium</synonym>
    <synonym>1-beta-delta-Glucopyranuronosyl-3-(1-methyl-5-oxo-2-pyrrolidinyl)- pyridinium</synonym>
    <synonym>Cotinine-glucuronide</synonym>
    <synonym>Cotinine-N-glucuronide</synonym>
  </synonyms>
  <chemical_formula>C16H20N2O7</chemical_formula>
  <average_molecular_weight>352.3392</average_molecular_weight>
  <monisotopic_moleculate_weight>352.127051004</monisotopic_moleculate_weight>
  <iupac_name>1-(6-carboxylato-3,4,5-trihydroxyoxan-2-yl)-3-(1-methyl-5-oxopyrrolidin-2-yl)-1λ⁵-pyridin-1-ylium</iupac_name>
  <traditional_iupac>1-(6-carboxylato-3,4,5-trihydroxyoxan-2-yl)-3-(1-methyl-5-oxopyrrolidin-2-yl)-1λ⁵-pyridin-1-ylium</traditional_iupac>
  <cas_registry_number>3616-06-6</cas_registry_number>
  <smiles>CN1C(CCC1=O)C1=C[N+](=CC=C1)C1OC(C(O)C(O)C1O)C([O-])=O</smiles>
  <inchi>InChI=1S/C16H20N2O7/c1-17-9(4-5-10(17)19)8-3-2-6-18(7-8)15-13(22)11(20)12(21)14(25-15)16(23)24/h2-3,6-7,9,11-15,20-22H,4-5H2,1H3</inchi>
  <inchikey>XWZCZWKUGIQPJD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group  linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine ribonucleotides</sub_class>
    <direct_parent>Pyrimidine ribonucleoside diphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-(6-carboxylato-3,4,5-trihydroxyoxan-2-yl)-3-(1-methyl-5-oxopyrrolidin-2-yl)-1λ⁵-pyridin-1-ylium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>352.3392</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>352.127051004</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C(CCC1=O)C1=C[N+](=CC=C1)C1OC(C(O)C(O)C1O)C([O-])=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H20N2O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H20N2O7/c1-17-9(4-5-10(17)19)8-3-2-6-18(7-8)15-13(22)11(20)12(21)14(25-15)16(23)24/h2-3,6-7,9,11-15,20-22H,4-5H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XWZCZWKUGIQPJD-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>134.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>93.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>87282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>87283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>87284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>149754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>149755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>149756</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>388324</chemspider_id>
  <foodb_id>FDB005661</foodb_id>
  <kegg_id>C00190</kegg_id>
  <pubchem_compound_id>439179</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16082</chebi_id>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>34192</bigg_id>
  <wikipedia_id/>
  <metlin_id>5948</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:54 UTC</creation_date>
  <update_date>2020-03-13 16:25:20 UTC</update_date>
  <accession>BMDB0001014</accession>
  <secondary_accessions>
    <accession>BMDB01014</accession>
  </secondary_accessions>
  <name>4-Imidazolone-5-propionic acid</name>
  <description>4-Imidazolone-5-propionic acid, also known as 4-imidazolone-5-propionic acid, belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. 4-Imidazolone-5-propionic acid is possibly soluble (in water) and a strong basic compound (based on its pKa). 4-Imidazolone-5-propionic acid exists in all living organisms, ranging from bacteria to humans. 4-Imidazolone-5-propionic acid participates in a number of enzymatic reactions, within cattle. In particular, 4-Imidazolone-5-propionic acid can be converted into urocanic acid; which is catalyzed by the enzyme urocanate hydratase. In addition, 4-Imidazolone-5-propionic acid can be converted into formiminoglutamic acid through its interaction with the enzyme probable imidazolonepropionase. In cattle, 4-imidazolone-5-propionic acid is involved in the metabolic pathway called the histidine metabolism pathway.</description>
  <synonyms>
    <synonym>4,5-Dihydro-4-oxo-5-imidazolepropanoate</synonym>
    <synonym>4,5-Dihydro-5-oxo-1H-imidazole-4-propanoic acid</synonym>
    <synonym>4-Imidazolone-5-propanoate</synonym>
    <synonym>Imidazol-4-one-5-propionic acid</synonym>
    <synonym>4,5-Dihydro-4-oxo-5-imidazolepropanoic acid</synonym>
    <synonym>4,5-Dihydro-5-oxo-1H-imidazole-4-propanoate</synonym>
    <synonym>4-Imidazolone-5-propanoic acid</synonym>
    <synonym>Imidazol-4-one-5-propionate</synonym>
    <synonym>4-Imidazolone-5-propionate</synonym>
    <synonym>(S)-3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoate</synonym>
    <synonym>(S)-3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoic acid</synonym>
    <synonym>3-(4-oxo-4,5-Dihydro-1H-imidazol-5-yl)propanoate</synonym>
    <synonym>3-(4-oxo-4,5-Dihydro-1H-imidazol-5-yl)propanoic acid</synonym>
    <synonym>3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoate</synonym>
    <synonym>3-(5-oxo-4,5-Dihydro-3H-imidazol-4-yl)propanoic acid</synonym>
    <synonym>Imidazolone propionate</synonym>
    <synonym>Imidazolone propionic acid</synonym>
    <synonym>Imidazolonepropanoate</synonym>
    <synonym>Imidazolonepropanoic acid</synonym>
  </synonyms>
  <chemical_formula>C6H8N2O3</chemical_formula>
  <average_molecular_weight>156.1393</average_molecular_weight>
  <monisotopic_moleculate_weight>156.053492132</monisotopic_moleculate_weight>
  <iupac_name>3-(5-oxo-4,5-dihydro-1H-imidazol-4-yl)propanoic acid</iupac_name>
  <traditional_iupac>3-(5-oxo-1,4-dihydroimidazol-4-yl)propanoic acid</traditional_iupac>
  <cas_registry_number>17340-16-8</cas_registry_number>
  <smiles>OC(=O)CCC1N=CNC1=O</smiles>
  <inchi>InChI=1S/C6H8N2O3/c9-5(10)2-1-4-6(11)8-3-7-4/h3-4H,1-2H2,(H,9,10)(H,7,8,11)</inchi>
  <inchikey>HEXMLHKQVUFYME-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Azoles</class>
    <sub_class>Imidazoles</sub_class>
    <direct_parent>Imidazolyl carboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazolyl carboxylic acid derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>imidazolone</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(5-oxo-4,5-dihydro-1H-imidazol-4-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>156.1393</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>156.053492132</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC1N=CNC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H8N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H8N2O3/c9-5(10)2-1-4-6(11)8-3-7-4/h3-4H,1-2H2,(H,9,10)(H,7,8,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HEXMLHKQVUFYME-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>78.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354567</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022371</foodb_id>
  <chemspider_id>125</chemspider_id>
  <pubchem_compound_id>128</pubchem_compound_id>
  <kegg_id>C03680</kegg_id>
  <drugbank_id/>
  <chebi_id>27384</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Imidazol-4-one-5-propionic acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>42318</bigg_id>
  <metlin_id>319</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:56 UTC</creation_date>
  <update_date>2020-04-15 22:07:14 UTC</update_date>
  <accession>BMDB0001015</accession>
  <secondary_accessions>
    <accession>BMDB01015</accession>
  </secondary_accessions>
  <name>N-Formyl-L-methionine</name>
  <description>N-Formyl-L-methionine, also known as fmet or for-met-OH, belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Formyl-L-methionine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).</description>
  <synonyms>
    <synonym>FMet</synonym>
    <synonym>For-met-OH</synonym>
    <synonym>Formyl-L-methionine</synonym>
    <synonym>Formylmethionine</synonym>
    <synonym>N-Formyl-methionine</synonym>
    <synonym>(2R)-2-[(Hydroxymethylidene)amino]-4-(methylsulfanyl)butanoate</synonym>
    <synonym>(2R)-2-[(Hydroxymethylidene)amino]-4-(methylsulphanyl)butanoate</synonym>
    <synonym>(2R)-2-[(Hydroxymethylidene)amino]-4-(methylsulphanyl)butanoic acid</synonym>
  </synonyms>
  <chemical_formula>C6H11NO3S</chemical_formula>
  <average_molecular_weight>177.221</average_molecular_weight>
  <monisotopic_moleculate_weight>177.045963913</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-formamido-4-(methylsulfanyl)butanoic acid</iupac_name>
  <traditional_iupac>N-formylmethionine</traditional_iupac>
  <cas_registry_number>4289-98-9</cas_registry_number>
  <smiles>CSCC[C@@H](NC=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H11NO3S/c1-11-3-2-5(6(9)10)7-4-8/h4-5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m1/s1</inchi>
  <inchikey>PYUSHNKNPOHWEZ-RXMQYKEDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Methionine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylthioethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-formyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methionine or derivatives</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-formyl-alpha amino acid or derivatives</substituent>
      <substituent>N-formyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thia fatty acid</substituent>
      <substituent>Thioether</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-formamido-4-(methylsulfanyl)butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>177.221</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>177.045963913</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CSCC[C@@H](NC=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H11NO3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H11NO3S/c1-11-3-2-5(6(9)10)7-4-8/h4-5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PYUSHNKNPOHWEZ-RXMQYKEDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1573</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022372</foodb_id>
  <pubchem_compound_id>6995182</pubchem_compound_id>
  <chemspider_id>5363142</chemspider_id>
  <kegg_id>C03145</kegg_id>
  <chebi_id>16552</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>N-FORMYLMETHIONINE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5945</metlin_id>
  <pdbe_id/>
  <synthesis_reference>Milligan D L; Koshland D E Jr  The amino terminus of the aspartate chemoreceptor is formylmethionine.    The Journal of biological chemistry  (1990),  265(8),  4455-60.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:57 UTC</creation_date>
  <update_date>2020-03-13 16:25:21 UTC</update_date>
  <accession>BMDB0001016</accession>
  <secondary_accessions>
    <accession>BMDB01016</accession>
  </secondary_accessions>
  <name>D-4'-Phosphopantothenate</name>
  <description>D-4'-Phosphopantothenate belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom. D-4'-Phosphopantothenate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). D-4'-Phosphopantothenate exists in all living species, ranging from bacteria to humans. D-4'-Phosphopantothenate participates in a number of enzymatic reactions, within cattle. In particular, D-4'-Phosphopantothenate can be biosynthesized from pantothenic acid; which is mediated by the enzyme pantothenate kinase 1. In addition, Cytidine triphosphate, D-D-d-4'-phosphopantothenate, and L-cysteine can be converted into cytidine monophosphate and 4'-phosphopantothenoylcysteine; which is mediated by the enzyme phosphopantothenate--cysteine ligase. In cattle, D-D-d-4'-phosphopantothenate is involved in the metabolic pathway called pantothenate and CoA biosynthesis pathway.</description>
  <synonyms>
    <synonym>D-4'-Phosphopantothenic acid</synonym>
    <synonym>4'-Phosphopantothenate</synonym>
    <synonym>Phosphopantothenic acid</synonym>
    <synonym>Phosphopantothenic acid, calcium salt (2:1)</synonym>
    <synonym>Phosphopantothenic acid, calcium salt, (R)-isomer</synonym>
    <synonym>(R)-4'-Phosphopantothenate</synonym>
    <synonym>4'-P-Pantothenate</synonym>
  </synonyms>
  <chemical_formula>C9H18NO8P</chemical_formula>
  <average_molecular_weight>299.2149</average_molecular_weight>
  <monisotopic_moleculate_weight>299.077003069</monisotopic_moleculate_weight>
  <iupac_name>3-{2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido}propanoic acid</iupac_name>
  <traditional_iupac>3-{2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido}propanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(C)(COP(O)(O)=O)C(O)C(O)=NCCC(O)=O</smiles>
  <inchi>InChI=1S/C9H18NO8P/c1-9(2,5-18-19(15,16)17)7(13)8(14)10-4-3-6(11)12/h7,13H,3-5H2,1-2H3,(H,10,14)(H,11,12)(H2,15,16,17)</inchi>
  <inchikey>XHFVGHPGDLDEQO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Beta amino acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-{2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido}propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>299.2149</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>299.077003069</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)(COP(O)(O)=O)C(O)C(O)=NCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H18NO8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H18NO8P/c1-9(2,5-18-19(15,16)17)7(13)8(14)10-4-3-6(11)12/h7,13H,3-5H2,1-2H3,(H,10,14)(H,11,12)(H2,15,16,17)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XHFVGHPGDLDEQO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>153.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>62.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pantothenate and CoA Biosynthesis</name>
      <smpdb_id>SMP0087207</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30226</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022373</foodb_id>
  <pubchem_compound_id>131</pubchem_compound_id>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:58 UTC</creation_date>
  <update_date>2020-04-16 20:39:10 UTC</update_date>
  <accession>BMDB0001018</accession>
  <secondary_accessions>
    <accession>BMDB01018</accession>
  </secondary_accessions>
  <name>UDP-D-Xylose</name>
  <description>UDP-D-Xylose belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. UDP-D-Xylose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. UDP-D-Xylose can be biosynthesized from uridine diphosphate glucuronic acid; which is catalyzed by the enzyme UDP-glucuronic acid decarboxylase 1. In cattle, UDP-D-xylose is involved in the metabolic pathway called the nucleotide sugars metabolism pathway.</description>
  <synonyms>
    <synonym>alpha-D-Xylopyranosyl ester</synonym>
    <synonym>alpha-delta-Xylopyranosyl ester</synonym>
    <synonym>UDP Xylose</synonym>
    <synonym>UDP-alpha</synonym>
    <synonym>UDP-delta-Xylose</synonym>
    <synonym>Uridine diphosphate xylose</synonym>
  </synonyms>
  <chemical_formula>C14H22N2O16P2</chemical_formula>
  <average_molecular_weight>536.2758</average_molecular_weight>
  <monisotopic_moleculate_weight>536.04445569</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({hydroxy[(3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyphosphoryl}oxy)phosphinic acid</traditional_iupac>
  <cas_registry_number>3616-06-6</cas_registry_number>
  <smiles>O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OC2OC[C@@H](O)[C@H](O)[C@H]2O)OC([C@@H]1O)N1C=CC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C14H22N2O16P2/c17-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)16-2-1-7(18)15-14(16)23/h1-2,5-6,8-13,17,19-22H,3-4H2,(H,24,25)(H,26,27)(H,15,18,23)/t5-,6-,8+,9-,10-,11-,12?,13?/m1/s1</inchi>
  <inchikey>DQQDLYVHOTZLOR-QDHANXEVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Methionine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylthioethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>N-formyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methionine or derivatives</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>N-formyl-alpha amino acid or derivatives</substituent>
      <substituent>N-formyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thia fatty acid</substituent>
      <substituent>Thioether</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-methionine derivative</external_descriptor>
      <external_descriptor>N-formyl amino acid</external_descriptor>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>proteinogenic amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>144.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.96</value>
      <source>NARURKAR,MM &amp; MITRA,AK (1988)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>536.2758</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>536.04445569</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OC2OC[C@@H](O)[C@H](O)[C@H]2O)OC([C@@H]1O)N1C=CC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H22N2O16P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H22N2O16P2/c17-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)16-2-1-7(18)15-14(16)23/h1-2,5-6,8-13,17,19-22H,3-4H2,(H,24,25)(H,26,27)(H,15,18,23)/t5-,6-,8+,9-,10-,11-,12?,13?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DQQDLYVHOTZLOR-QDHANXEVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>271.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>100.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>42.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37894</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB005661</foodb_id>
  <chemspider_id>388324</chemspider_id>
  <pubchem_compound_id>439179</pubchem_compound_id>
  <kegg_id>C00190</kegg_id>
  <drugbank_id/>
  <chebi_id>16082</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>34192</bigg_id>
  <metlin_id>5948</metlin_id>
  <synthesis_reference>Ernst, Christiane; Klaffke, Werner. Chemical Synthesis of Uridine Diphospho-D-xylose and UDP-L-arabinose. Journal of Organic Chemistry (2003), 68(14), 5780-5783.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00439</protein_accession>
      <name>Xylosyltransferase 2</name>
      <uniprot_id>Q5QQ49</uniprot_id>
      <gene_name>XYLT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00845</protein_accession>
      <name>Exostosin-2</name>
      <uniprot_id>O77783</uniprot_id>
      <gene_name>EXT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00846</protein_accession>
      <name>Hyaluronan synthase 2</name>
      <uniprot_id>O97711</uniprot_id>
      <gene_name>HAS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00847</protein_accession>
      <name>Exostosin-1</name>
      <uniprot_id>A5D7I4</uniprot_id>
      <gene_name>EXT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:39:59 UTC</creation_date>
  <update_date>2020-04-15 22:07:16 UTC</update_date>
  <accession>BMDB0001020</accession>
  <secondary_accessions>
    <accession>BMDB01020</accession>
  </secondary_accessions>
  <name>N,N-Dimethylaniline</name>
  <description/>
  <synonyms>
    <synonym>Dimethylaminobenzene</synonym>
    <synonym>Dimethylaniline</synonym>
    <synonym>Dimethylphenylamine</synonym>
    <synonym>N,N-Dimethyl-N-phenylamine</synonym>
    <synonym>N,N-Dimethylbenzenamine</synonym>
    <synonym>N,N-Dimethylbenzeneamine</synonym>
    <synonym>N,N-Dimethylphenylamine</synonym>
    <synonym>N,N-(Dimethylamino)benzene</synonym>
    <synonym>N,N-Dimethyl-benzenamine</synonym>
    <synonym>N,N-Dimethylaniline sulfate (1:1)</synonym>
    <synonym>N,N-Dimethylaniline hydrochloride</synonym>
    <synonym>N,N-Dimethylaniline hydroiodide</synonym>
  </synonyms>
  <chemical_formula>C8H11N</chemical_formula>
  <average_molecular_weight>121.1796</average_molecular_weight>
  <monisotopic_moleculate_weight>121.089149357</monisotopic_moleculate_weight>
  <iupac_name>N,N-dimethylaniline</iupac_name>
  <traditional_iupac>dimethylaniline</traditional_iupac>
  <cas_registry_number>121-69-7</cas_registry_number>
  <smiles>CN(C)C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C8H11N/c1-9(2)8-6-4-3-5-7-8/h3-7H,1-2H3</inchi>
  <inchikey>JLTDJTHDQAWBAV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>Dialkylarylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Dialkylarylamine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>dimethylaniline</external_descriptor>
      <external_descriptor>tertiary amine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>2.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1.45 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.31</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N,N-dimethylaniline</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>121.1796</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>121.089149357</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN(C)C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H11N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H11N/c1-9(2)8-6-4-3-5-7-8/h3-7H,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JLTDJTHDQAWBAV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>3.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1391</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448245</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB005128</foodb_id>
  <chemspider_id>924</chemspider_id>
  <pubchem_compound_id>949</pubchem_compound_id>
  <kegg_id>C02846</kegg_id>
  <drugbank_id/>
  <chebi_id>16269</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>NN-DIMETHYLANILINE</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Dimethylaniline</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5949</metlin_id>
  <synthesis_reference>Li, Guo-tao; Guan, Nai-jia; Zhang, Huai-bin; Liu, Shu-quan.  Synthesis of N, N-dimethylaniline by aniline and methanol over b zeolite catalyst.    Shiyou Huagong  (2002),  31(2),  81-83.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00119</protein_accession>
      <name>Dimethylaniline monooxygenase [N-oxide-forming] 3</name>
      <uniprot_id>Q8HYJ9</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:00 UTC</creation_date>
  <update_date>2020-03-13 16:25:23 UTC</update_date>
  <accession>BMDB0001021</accession>
  <secondary_accessions>
    <accession>BMDB01021</accession>
  </secondary_accessions>
  <name>Malyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>(3S)-3-Carboxy-3-hydroxypropanoyl-CoA</synonym>
    <synonym>(3S)-3-Carboxy-3-hydroxypropanoyl-coenzyme A</synonym>
    <synonym>(3S)-3-Carboxy-3-hydroxypropionyl-CoA</synonym>
    <synonym>(3S)-3-Carboxy-3-hydroxypropionyl-coenzyme A</synonym>
    <synonym>L-Malyl-CoA</synonym>
    <synonym>L-Malyl-coenzyme A</synonym>
    <synonym>Malyl-coenzyme A</synonym>
    <synonym>S-(3-Carboxy-3-hydroxypropanoate</synonym>
    <synonym>S-(3-Carboxy-3-hydroxypropanoate) CoA</synonym>
    <synonym>S-(3-Carboxy-3-hydroxypropanoate) coenzyme A</synonym>
    <synonym>S-(3-Carboxy-3-hydroxypropanoic acid</synonym>
  </synonyms>
  <chemical_formula>C25H40N7O20P3S</chemical_formula>
  <average_molecular_weight>883.606</average_molecular_weight>
  <monisotopic_moleculate_weight>883.126166981</monisotopic_moleculate_weight>
  <iupac_name>(2S)-4-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-2-hydroxy-4-oxobutanoic acid</iupac_name>
  <traditional_iupac>(2S)-4-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-2-hydroxy-4-oxobutanoic acid</traditional_iupac>
  <cas_registry_number>2043-93-8</cas_registry_number>
  <smiles>CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)C[C@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C25H40N7O20P3S/c1-25(2,19(37)22(38)28-4-3-14(34)27-5-6-56-15(35)7-12(33)24(39)40)9-49-55(46,47)52-54(44,45)48-8-13-18(51-53(41,42)43)17(36)23(50-13)32-11-31-16-20(26)29-10-30-21(16)32/h10-13,17-19,23,33,36-37H,3-9H2,1-2H3,(H,27,34)(H,28,38)(H,39,40)(H,44,45)(H,46,47)(H2,26,29,30)(H2,41,42,43)/t12-,13+,17+,18+,19?,23+/m0/s1</inchi>
  <inchikey>HJQWLHMLMCDAEL-NALABAGVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thia fatty acid</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-4-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-2-hydroxy-4-oxobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>883.606</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>883.126166981</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)C[C@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H40N7O20P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C25H40N7O20P3S/c1-25(2,19(37)22(38)28-4-3-14(34)27-5-6-56-15(35)7-12(33)24(39)40)9-49-55(46,47)52-54(44,45)48-8-13-18(51-53(41,42)43)17(36)23(50-13)32-11-31-16-20(26)29-10-30-21(16)32/h10-13,17-19,23,33,36-37H,3-9H2,1-2H3,(H,27,34)(H,28,38)(H,39,40)(H,44,45)(H,46,47)(H2,26,29,30)(H2,41,42,43)/t12-,13+,17+,18+,19?,23+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HJQWLHMLMCDAEL-NALABAGVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>421.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>184.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>76.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369582</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022374</foodb_id>
  <chemspider_id>389276</chemspider_id>
  <pubchem_compound_id>440302</pubchem_compound_id>
  <kegg_id>C04348</kegg_id>
  <drugbank_id/>
  <chebi_id>15454</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>5950</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:01 UTC</creation_date>
  <update_date>2020-04-16 17:51:29 UTC</update_date>
  <accession>BMDB0001022</accession>
  <secondary_accessions>
    <accession>BMDB01022</accession>
  </secondary_accessions>
  <name>Succinyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>CoA S-(Hydrogen succinate)</synonym>
    <synonym>CoA S-Succinate</synonym>
    <synonym>coenzyme A S-(Hydrogen succinate)</synonym>
    <synonym>coenzyme A S-Succinate</synonym>
    <synonym>S-(Hydrogen butanedioate</synonym>
    <synonym>S-(Hydrogen butanedioate) CoA</synonym>
    <synonym>S-(Hydrogen butanedioate) coenzyme A</synonym>
    <synonym>S-(Hydrogen butanedioic acid</synonym>
    <synonym>S-Succinoylcoenzyme A</synonym>
    <synonym>Suc-CO-a</synonym>
    <synonym>Suc-CoA</synonym>
    <synonym>Succ-CoA</synonym>
    <synonym>Succ-coenzyme A</synonym>
    <synonym>Succ-S-CoA</synonym>
    <synonym>Succ-S-coenzyme A</synonym>
    <synonym>Succino-1-yl-coenzyme A</synonym>
    <synonym>Succinyl CoA</synonym>
    <synonym>Succinyl coenzyme A</synonym>
    <synonym>Succinyl-S-CoA</synonym>
    <synonym>Succinyl-S-coenzyme A</synonym>
    <synonym>Succinylcoenzyme A</synonym>
    <synonym>Succinyl-coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C25H40N7O19P3S</chemical_formula>
  <average_molecular_weight>867.607</average_molecular_weight>
  <monisotopic_moleculate_weight>867.131252359</monisotopic_moleculate_weight>
  <iupac_name>4-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-4-oxobutanoic acid</iupac_name>
  <traditional_iupac>4-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-4-oxobutanoic acid</traditional_iupac>
  <cas_registry_number>604-98-8</cas_registry_number>
  <smiles>CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O</smiles>
  <inchi>InChI=1S/C25H40N7O19P3S/c1-25(2,20(38)23(39)28-6-5-14(33)27-7-8-55-16(36)4-3-15(34)35)10-48-54(45,46)51-53(43,44)47-9-13-19(50-52(40,41)42)18(37)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,37-38H,3-10H2,1-2H3,(H,27,33)(H,28,39)(H,34,35)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t13-,18-,19-,20?,24-/m1/s1</inchi>
  <inchikey>VNOYUJKHFWYWIR-FZEDXVDRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thia fatty acid</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-4-oxobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>867.607</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>867.131252359</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H40N7O19P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C25H40N7O19P3S/c1-25(2,20(38)23(39)28-6-5-14(33)27-7-8-55-16(36)4-3-15(34)35)10-48-54(45,46)51-53(43,44)47-9-13-19(50-52(40,41)42)18(37)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,37-38H,3-10H2,1-2H3,(H,27,33)(H,28,39)(H,34,35)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t13-,18-,19-,20?,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VNOYUJKHFWYWIR-FZEDXVDRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>400.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>183.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>74.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Butyrate Metabolism</name>
      <smpdb_id>SMP0087185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ketone Body Metabolism</name>
      <smpdb_id>SMP0087202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Threonine and 2-Oxobutanoate Degradation</name>
      <smpdb_id>SMP0087262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>53163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>53164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>53165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>127023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>127024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>127025</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022375</foodb_id>
  <chemspider_id>388307</chemspider_id>
  <pubchem_compound_id>439161</pubchem_compound_id>
  <kegg_id>C00091</kegg_id>
  <drugbank_id/>
  <chebi_id>15380</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Succinyl-CoA</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33820</bigg_id>
  <metlin_id>5951</metlin_id>
  <synthesis_reference>Wollemann, M.  Mechanism of the succinyl-coenzyme A synthesis in brain extracts.    Acta Physiologica Academiae Scientiarum Hungaricae  (1959),  16  153-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00623</protein_accession>
      <name>Methylmalonyl-CoA mutase, mitochondrial</name>
      <uniprot_id>Q9GK13</uniprot_id>
      <gene_name>MUT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00624</protein_accession>
      <name>5-aminolevulinate synthase, nonspecific, mitochondrial</name>
      <uniprot_id>A6QLI6</uniprot_id>
      <gene_name>ALAS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00625</protein_accession>
      <name>Succinyl-CoA ligase [ADP-forming] subunit beta, mitochondrial</name>
      <uniprot_id>Q148D5</uniprot_id>
      <gene_name>SUCLA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00626</protein_accession>
      <name>Succinyl-CoA ligase [GDP-forming] subunit alpha, mitochondrial</name>
      <uniprot_id>Q58DR8</uniprot_id>
      <gene_name>SUCLG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00627</protein_accession>
      <name>Succinyl-CoA ligase [GDP-forming] subunit beta, mitochondrial</name>
      <uniprot_id>Q3MHX5</uniprot_id>
      <gene_name>SUCLG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00628</protein_accession>
      <name>Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial</name>
      <uniprot_id>P11179</uniprot_id>
      <gene_name>DLST</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00629</protein_accession>
      <name>5-aminolevulinate synthase, erythroid-specific, mitochondrial</name>
      <uniprot_id>Q3ZC31</uniprot_id>
      <gene_name>ALAS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:02 UTC</creation_date>
  <update_date>2020-04-15 22:35:40 UTC</update_date>
  <accession>BMDB0001023</accession>
  <secondary_accessions>
    <accession>BMDB01023</accession>
  </secondary_accessions>
  <name>4,4-Dimethylcholesta-8,14,24-trienol</name>
  <description/>
  <synonyms>
    <synonym>4,4-Dimechol-8,14,24-trienol</synonym>
    <synonym>4,4-Dimethylcholesta-8(9),14,24-trien-3beta-ol</synonym>
    <synonym>4,4-Dimethylcholesta-8(9),14,24-trien-3b-ol</synonym>
    <synonym>4,4-Dimethylcholesta-8(9),14,24-trien-3β-ol</synonym>
    <synonym>(3beta,5alpha)-4,4-Dimethyl-cholesta-8,14,24-trien-3-ol</synonym>
    <synonym>(3beta,5alpha)-4,4-Dimethylcholesta-8,14,24-trien-3-ol</synonym>
    <synonym>4,4'-Dimethyl cholesta-8,14,24-triene-3-beta-ol</synonym>
    <synonym>4,4-Dimethyl-5-alpha-cholesta-8,14,24-trien-3-beta-ol</synonym>
    <synonym>4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3-ol</synonym>
    <synonym>4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol</synonym>
    <synonym>4,4-Dimethyl-cholesta-8,14,24-trienol</synonym>
    <synonym>FF-MAS</synonym>
    <synonym>Follicular fluid meiosis activating sterol</synonym>
  </synonyms>
  <chemical_formula>C29H46O</chemical_formula>
  <average_molecular_weight>410.6749</average_molecular_weight>
  <monisotopic_moleculate_weight>410.354866094</monisotopic_moleculate_weight>
  <iupac_name>(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol</iupac_name>
  <traditional_iupac>(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol</traditional_iupac>
  <cas_registry_number>64284-64-6</cas_registry_number>
  <smiles>C[C@H](CCC=C(C)C)[C@H]1CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3</smiles>
  <inchi>InChI=1S/C29H46O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,13,20,22,25-26,30H,8,10-12,14-18H2,1-7H3/t20-,22-,25+,26+,28-,29-/m1/s1</inchi>
  <inchikey>LFQXEZVYNCBVDO-PBJLWWPKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3beta-sterol</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>410.6749</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>410.354866094</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](CCC=C(C)C)[C@H]1CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C29H46O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C29H46O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,13,20,22,25-26,30H,8,10-12,14-18H2,1-7H3/t20-,22-,25+,26+,28-,29-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LFQXEZVYNCBVDO-PBJLWWPKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>130.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>52.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180653</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022376</foodb_id>
  <chemspider_id>391478</chemspider_id>
  <pubchem_compound_id>443212</pubchem_compound_id>
  <kegg_id>C11455</kegg_id>
  <drugbank_id/>
  <chebi_id>17813</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>1454719</bigg_id>
  <metlin_id>5952</metlin_id>
  <synthesis_reference>Ruan B; Wilson W K; Schroepfer G J Jr  An alternative synthesis of 4,4-dimethyl-5 alpha-cholesta-8,14,24-trien-3 beta-ol, an intermediate in sterol biosynthesis and a reported activator of meiosis and of nuclear orphan receptor LXR alpha.    Bioorganic &amp; medicinal chemistry letters  (1998),  8(3),  233-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:04 UTC</creation_date>
  <update_date>2020-03-13 16:25:24 UTC</update_date>
  <accession>BMDB0001024</accession>
  <secondary_accessions>
    <accession>BMDB01024</accession>
  </secondary_accessions>
  <name>Phosphohydroxypyruvic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Phosphohydroxypyruvic acid</synonym>
    <synonym>Hydroxypyruvic acid phosphate</synonym>
    <synonym>3-Phosphonooxypyruvic acid</synonym>
    <synonym>3-Phosphohydroxypyruvate</synonym>
    <synonym>3-Phosphooxypyruvate</synonym>
    <synonym>Hydroxypyruvate phosphate</synonym>
    <synonym>Hydroxypyruvic acid phosphoric acid</synonym>
    <synonym>3-Phosphonooxypyruvate</synonym>
    <synonym>3-Phosphooxypyruvic acid</synonym>
    <synonym>Phosphohydroxypyruvate</synonym>
    <synonym>2-oxo-3-(Phosphonooxy)-propanoate</synonym>
    <synonym>2-oxo-3-(Phosphonooxy)-propanoic acid</synonym>
    <synonym>3-Phosphonatooxypyruvate</synonym>
  </synonyms>
  <chemical_formula>C3H5O7P</chemical_formula>
  <average_molecular_weight>184.0414</average_molecular_weight>
  <monisotopic_moleculate_weight>183.977289026</monisotopic_moleculate_weight>
  <iupac_name>2-oxo-3-(phosphonooxy)propanoic acid</iupac_name>
  <traditional_iupac>phosphohydroxypyruvate</traditional_iupac>
  <cas_registry_number>3913-50-6</cas_registry_number>
  <smiles>OC(=O)C(=O)COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9)</inchi>
  <inchikey>LFLUCDOSQPJJBE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Glycerone phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycerone phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Keto acid</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>carboxyalkyl phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-oxo-3-(phosphonooxy)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>184.0414</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>183.977289026</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C(=O)COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H5O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LFLUCDOSQPJJBE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>121.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37896</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022377</foodb_id>
  <kegg_id>C03232</kegg_id>
  <pubchem_compound_id>105</pubchem_compound_id>
  <chemspider_id>103</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>30933</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00019657</knapsack_id>
  <bigg_id>41453</bigg_id>
  <wikipedia_id>Phosphohydroxypyruvic acid</wikipedia_id>
  <metlin_id>484</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:05 UTC</creation_date>
  <update_date>2020-03-13 16:25:25 UTC</update_date>
  <accession>BMDB0001028</accession>
  <secondary_accessions>
    <accession>BMDB01028</accession>
  </secondary_accessions>
  <name>25-Azacholesterol</name>
  <description/>
  <synonyms>
    <synonym>(3beta)-24-(Dimethylamino)-chol-5-en-3-ol</synonym>
    <synonym>24-(Dimethylamino)chol-5-en-3beta-ol</synonym>
    <synonym>24-(Dimethylamino)chol-5-en-3 beta-ol</synonym>
  </synonyms>
  <chemical_formula>C26H45NO</chemical_formula>
  <average_molecular_weight>387.6416</average_molecular_weight>
  <monisotopic_moleculate_weight>387.350115067</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-5-(dimethylamino)pentan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol</iupac_name>
  <traditional_iupac>25-azacholesterol</traditional_iupac>
  <cas_registry_number>1973-61-1</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCN(C)C</smiles>
  <inchi>InChI=1S/C26H45NO/c1-18(7-6-16-27(4)5)22-10-11-23-21-9-8-19-17-20(28)12-14-25(19,2)24(21)13-15-26(22,23)3/h8,18,20-24,28H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26-/m1/s1</inchi>
  <inchikey>RZPPEFJMRVRCDD-XSLNCIIRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 25-azasteroids and derivatives. These are azasteroids where the carbon atom at position 25 is replaced by a nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Azasteroids and derivatives</sub_class>
    <direct_parent>25-azasteroids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>25-azasteroid</substituent>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-5-(dimethylamino)pentan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>387.6416</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>387.350115067</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCN(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H45NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H45NO/c1-18(7-6-16-27(4)5)22-10-11-23-21-9-8-19-17-20(28)12-14-25(19,2)24(21)13-15-26(22,23)3/h8,18,20-24,28H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RZPPEFJMRVRCDD-XSLNCIIRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>23.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>120.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>50.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347130</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022378</foodb_id>
  <kegg_id/>
  <pubchem_compound_id>164906</pubchem_compound_id>
  <chemspider_id>144573</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5954</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:06 UTC</creation_date>
  <update_date>2020-03-13 16:25:25 UTC</update_date>
  <accession>BMDB0001030</accession>
  <secondary_accessions>
    <accession>BMDB01030</accession>
  </secondary_accessions>
  <name>3'-Ketolactose</name>
  <description/>
  <synonyms>
    <synonym>3'-Dehydro-beta-D-galactosyl-beta-D-glucopyranoside</synonym>
    <synonym>3'-Dehydro-beta-delta-galactosyl-beta-delta-glucopyranoside</synonym>
    <synonym>4-O-(beta-D-Xylo-hexopyranosyl-3-ulose)-D-glucopyranose</synonym>
    <synonym>4-O-beta-D-Xylo-hexopyranos-3-ulos-1-yl-D-glucose</synonym>
  </synonyms>
  <chemical_formula>C12H20O11</chemical_formula>
  <average_molecular_weight>340.2806</average_molecular_weight>
  <monisotopic_moleculate_weight>340.100561482</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-one</iupac_name>
  <traditional_iupac>3-ketolactose</traditional_iupac>
  <cas_registry_number>15990-62-2</cas_registry_number>
  <smiles>OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)C(=O)[C@H]1O</smiles>
  <inchi>InChI=1S/C12H20O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-5,7-15,17-20H,1-2H2/t3-,4-,5+,7-,8-,9-,10-,11?,12+/m1/s1</inchi>
  <inchikey>HKKHTABTHSUDBP-ILXILVFVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as disaccharides. Disaccharides are compounds containing two carbohydrate moieties linked to each to each other through a glycosidic bond, no set of three or more glycosidically linked carbohydrate units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Disaccharides</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>340.2806</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>340.100561482</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)C(=O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H20O11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H20O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-5,7-15,17-20H,1-2H2/t3-,4-,5+,7-,8-,9-,10-,11?,12+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HKKHTABTHSUDBP-ILXILVFVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>186.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>67.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>30.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>365358</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022379</foodb_id>
  <kegg_id>C05403</kegg_id>
  <pubchem_compound_id>440659</pubchem_compound_id>
  <chemspider_id>389539</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:07 UTC</creation_date>
  <update_date>2020-03-13 16:25:26 UTC</update_date>
  <accession>BMDB0001031</accession>
  <secondary_accessions>
    <accession>BMDB01031</accession>
  </secondary_accessions>
  <name>Deoxyribose 5-phosphate</name>
  <description>Deoxyribose 5-phosphate, also known as 2-deoxyribose-5-P, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. Deoxyribose 5-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Deoxyribose 5-phosphate exists in all eukaryotes, ranging from yeast to humans. Deoxyribose 5-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Deoxyribose 5-phosphate can be biosynthesized from D-glyceraldehyde 3-phosphate and acetaldehyde through its interaction with the enzyme putative deoxyribose-phosphate aldolase. In addition, Deoxyribose 5-phosphate and adenosine diphosphate can be biosynthesized from deoxyribose 1-phosphate and adenosine triphosphate; which is mediated by the enzyme ribokinase. In cattle, deoxyribose 5-phosphate is involved in the metabolic pathway called the pentose phosphate pathway.</description>
  <synonyms>
    <synonym>Deoxyribose 5-phosphoric acid</synonym>
    <synonym>2-Deoxy-alpha-D-ribose 5-phosphate</synonym>
    <synonym>2-Deoxy-alpha-delta-ribose 5-phosphate</synonym>
    <synonym>2-Deoxy-D-ribose 5-phosphate</synonym>
    <synonym>2-Deoxy-D-ribose-5-phosphate</synonym>
    <synonym>2-Deoxyribose 5-phosphate</synonym>
    <synonym>2-Deoxyribose-5-p</synonym>
    <synonym>2-Deoxyribose-5-phosphate</synonym>
    <synonym>Deoxy-ribose-5P</synonym>
    <synonym>Deoxyribose-5-p</synonym>
    <synonym>Deoxyribose-5-phosphate</synonym>
  </synonyms>
  <chemical_formula>C5H11O7P</chemical_formula>
  <average_molecular_weight>214.1104</average_molecular_weight>
  <monisotopic_moleculate_weight>214.024239218</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,5R)-3,5-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>deoxyribose-5-phosphate</traditional_iupac>
  <cas_registry_number>102916-66-5</cas_registry_number>
  <smiles>O[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1</smiles>
  <inchi>InChI=1S/C5H11O7P/c6-3-1-5(7)12-4(3)2-11-13(8,9)10/h3-7H,1-2H2,(H2,8,9,10)/t3-,4+,5+/m0/s1</inchi>
  <inchikey>KKZFLSZAWCYPOC-VPENINKCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-deoxy-D-ribofuranose 5-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,5R)-3,5-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>214.1104</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>214.024239218</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H11O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H11O7P/c6-3-1-5(7)12-4(3)2-11-13(8,9)10/h3-7H,1-2H2,(H2,8,9,10)/t3-,4+,5+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KKZFLSZAWCYPOC-VPENINKCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>116.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37899</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022380</foodb_id>
  <kegg_id>C00673</kegg_id>
  <pubchem_compound_id>45934311</pubchem_compound_id>
  <chemspider_id>25057464</chemspider_id>
  <drugbank_id/>
  <pdbe_id>AAB</pdbe_id>
  <chebi_id>16132</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>35666</bigg_id>
  <wikipedia_id/>
  <metlin_id>5956</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Method of preparing 2-deoxyribose 5-phosphate US Patent #7270992</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00107</protein_accession>
      <name>Putative deoxyribose-phosphate aldolase</name>
      <uniprot_id>Q3T0V9</uniprot_id>
      <gene_name>DERA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:08 UTC</creation_date>
  <update_date>2020-04-14 22:48:47 UTC</update_date>
  <accession>BMDB0001032</accession>
  <secondary_accessions>
    <accession>BMDB01032</accession>
  </secondary_accessions>
  <name>DHEA sulfate</name>
  <description>Dehydroepiandrosterone sulfate, also known as Dehydroepiandrosterone sulfate or dehydroepiandrosterone sulfate, belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. Dehydroepiandrosterone sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dehydroepiandrosterone sulfate participates in a number of enzymatic reactions, within cattle. In particular, Adenosine 3',5'-diphosphate and dehydroepiandrosterone sulfate can be biosynthesized from phosphoadenosine phosphosulfate and dehydroepiandrosterone through the action of the enzyme sulfotransferase family cytosolic 2B member 1. In addition, Dehydroepiandrosterone sulfate can be converted into dehydroepiandrosterone and sulfate through the action of the enzyme steryl-sulfatase. In cattle, dehydroepiandrosterone sulfate is involved in the metabolic pathway called the androgen and estrogen metabolism pathway. Dehydroepiandrosterone sulfate is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(3-beta)-3-(Sulfooxy)androst-5-en-17-one</synonym>
    <synonym>17-Ketoandrost-5-en-3beta-yl sulfate</synonym>
    <synonym>17-Oxoandrost-5-en-3beta-yl hydrogen sulphate</synonym>
    <synonym>3-O-Sulfodehydroepiandrosterone</synonym>
    <synonym>3beta-Hydroxyandrost-5-en-17-one 3-sulfate</synonym>
    <synonym>Androst-5-en-17-on-3beta-yl sulfuric acid</synonym>
    <synonym>Dehydroepiandrosterone 3-sulfate</synonym>
    <synonym>Dehydroepiandrosterone monosulfate</synonym>
    <synonym>Dehydroepiandrosterone sulphate</synonym>
    <synonym>Dehydroisoandrosterone sulfate</synonym>
    <synonym>Dehydroisoandrosterone-3-sulfate</synonym>
    <synonym>DHEA sulfate</synonym>
    <synonym>DHEA-S</synonym>
    <synonym>DHEAS</synonym>
    <synonym>Prasterone sulfate</synonym>
    <synonym>(3-b)-3-(Sulfooxy)androst-5-en-17-one</synonym>
    <synonym>(3-b)-3-(Sulphooxy)androst-5-en-17-one</synonym>
    <synonym>(3-beta)-3-(Sulphooxy)androst-5-en-17-one</synonym>
    <synonym>(3-Β)-3-(sulfooxy)androst-5-en-17-one</synonym>
    <synonym>(3-Β)-3-(sulphooxy)androst-5-en-17-one</synonym>
    <synonym>17-Ketoandrost-5-en-3b-yl sulfate</synonym>
    <synonym>17-Ketoandrost-5-en-3b-yl sulfuric acid</synonym>
    <synonym>17-Ketoandrost-5-en-3b-yl sulphate</synonym>
    <synonym>17-Ketoandrost-5-en-3b-yl sulphuric acid</synonym>
    <synonym>17-Ketoandrost-5-en-3beta-yl sulfuric acid</synonym>
    <synonym>17-Ketoandrost-5-en-3beta-yl sulphate</synonym>
    <synonym>17-Ketoandrost-5-en-3beta-yl sulphuric acid</synonym>
    <synonym>17-Ketoandrost-5-en-3β-yl sulfate</synonym>
    <synonym>17-Ketoandrost-5-en-3β-yl sulfuric acid</synonym>
    <synonym>17-Ketoandrost-5-en-3β-yl sulphate</synonym>
    <synonym>17-Ketoandrost-5-en-3β-yl sulphuric acid</synonym>
    <synonym>17-Oxoandrost-5-en-3b-yl hydrogen sulfate</synonym>
    <synonym>17-Oxoandrost-5-en-3b-yl hydrogen sulfuric acid</synonym>
    <synonym>17-Oxoandrost-5-en-3b-yl hydrogen sulphate</synonym>
    <synonym>17-Oxoandrost-5-en-3b-yl hydrogen sulphuric acid</synonym>
    <synonym>17-Oxoandrost-5-en-3beta-yl hydrogen sulfate</synonym>
    <synonym>17-Oxoandrost-5-en-3beta-yl hydrogen sulfuric acid</synonym>
    <synonym>17-Oxoandrost-5-en-3beta-yl hydrogen sulphuric acid</synonym>
    <synonym>17-Oxoandrost-5-en-3β-yl hydrogen sulfate</synonym>
    <synonym>17-Oxoandrost-5-en-3β-yl hydrogen sulfuric acid</synonym>
    <synonym>17-Oxoandrost-5-en-3β-yl hydrogen sulphate</synonym>
    <synonym>17-Oxoandrost-5-en-3β-yl hydrogen sulphuric acid</synonym>
    <synonym>3-O-Sulphodehydroepiandrosterone</synonym>
    <synonym>3b-Hydroxyandrost-5-en-17-one 3-sulfate</synonym>
    <synonym>3b-Hydroxyandrost-5-en-17-one 3-sulfuric acid</synonym>
    <synonym>3b-Hydroxyandrost-5-en-17-one 3-sulphate</synonym>
    <synonym>3b-Hydroxyandrost-5-en-17-one 3-sulphuric acid</synonym>
    <synonym>3beta-Hydroxyandrost-5-en-17-one 3-sulfuric acid</synonym>
    <synonym>3beta-Hydroxyandrost-5-en-17-one 3-sulphate</synonym>
    <synonym>3beta-Hydroxyandrost-5-en-17-one 3-sulphuric acid</synonym>
    <synonym>3Β-hydroxyandrost-5-en-17-one 3-sulfate</synonym>
    <synonym>3Β-hydroxyandrost-5-en-17-one 3-sulfuric acid</synonym>
    <synonym>3Β-hydroxyandrost-5-en-17-one 3-sulphate</synonym>
    <synonym>3Β-hydroxyandrost-5-en-17-one 3-sulphuric acid</synonym>
    <synonym>Androst-5-en-17-on-3b-yl sulfate</synonym>
    <synonym>Androst-5-en-17-on-3b-yl sulfuric acid</synonym>
    <synonym>Androst-5-en-17-on-3b-yl sulphate</synonym>
    <synonym>Androst-5-en-17-on-3b-yl sulphuric acid</synonym>
    <synonym>Androst-5-en-17-on-3beta-yl sulfate</synonym>
    <synonym>Androst-5-en-17-on-3beta-yl sulphate</synonym>
    <synonym>Androst-5-en-17-on-3beta-yl sulphuric acid</synonym>
    <synonym>Androst-5-en-17-on-3β-yl sulfate</synonym>
    <synonym>Androst-5-en-17-on-3β-yl sulfuric acid</synonym>
    <synonym>Androst-5-en-17-on-3β-yl sulphate</synonym>
    <synonym>Androst-5-en-17-on-3β-yl sulphuric acid</synonym>
    <synonym>Dehydroepiandrosterone 3-sulfuric acid</synonym>
    <synonym>Dehydroepiandrosterone 3-sulphate</synonym>
    <synonym>Dehydroepiandrosterone 3-sulphuric acid</synonym>
    <synonym>Dehydroepiandrosterone monosulfuric acid</synonym>
    <synonym>Dehydroepiandrosterone monosulphate</synonym>
    <synonym>Dehydroepiandrosterone monosulphuric acid</synonym>
    <synonym>Dehydroepiandrosterone sulfuric acid</synonym>
    <synonym>Dehydroepiandrosterone sulphuric acid</synonym>
    <synonym>Dehydroisoandrosterone sulfuric acid</synonym>
    <synonym>Dehydroisoandrosterone sulphate</synonym>
    <synonym>Dehydroisoandrosterone sulphuric acid</synonym>
    <synonym>Dehydroisoandrosterone-3-sulfuric acid</synonym>
    <synonym>Dehydroisoandrosterone-3-sulphate</synonym>
    <synonym>Dehydroisoandrosterone-3-sulphuric acid</synonym>
    <synonym>DHEA sulfuric acid</synonym>
    <synonym>DHEA sulphate</synonym>
    <synonym>DHEA sulphuric acid</synonym>
    <synonym>Prasterone sulfuric acid</synonym>
    <synonym>Prasterone sulphate</synonym>
    <synonym>Prasterone sulphuric acid</synonym>
    <synonym>(3beta)-3-(Sulfooxy)-androst-5-en-17-one</synonym>
    <synonym>17-Oxoandrost-5-en-3-yl hydrogen sulfate</synonym>
    <synonym>17-Oxoandrost-5-en-3-yl hydrogen sulphate</synonym>
    <synonym>3-b-Hydroxyandrost-5-en-17-one 3-sulfate</synonym>
    <synonym>3-b-Hydroxyandrost-5-en-17-one 3-sulphate</synonym>
    <synonym>3-beta-Hydroxyandrost-5-en-17-one 3-sulfate</synonym>
    <synonym>3-beta-Hydroxyandrost-5-en-17-one 3-sulphate</synonym>
    <synonym>3b-Hydroxy-androst-5-en-17-one hydrogen sulfate</synonym>
    <synonym>3b-Hydroxy-androst-5-en-17-one hydrogen sulphate</synonym>
    <synonym>3beta-Hydroxy-androst-5-en-17-one hydrogen sulfate</synonym>
    <synonym>3beta-Hydroxy-androst-5-en-17-one hydrogen sulphate</synonym>
    <synonym>Dehydroepiandrosterone-3-sulfate</synonym>
    <synonym>Dehydroepiandrosterone-3-sulphate</synonym>
    <synonym>Formylisoglutamic acid</synonym>
    <synonym>Prasterone-3-sulfate</synonym>
    <synonym>Prasterone-3-sulphate</synonym>
    <synonym>DHA sulfate</synonym>
    <synonym>Sulfate, dehydroisoandrosterone</synonym>
    <synonym>Sulfate, prasterone</synonym>
    <synonym>Sulfate, dhea</synonym>
    <synonym>Sulfate, dehydroepiandrosterone</synonym>
    <synonym>Sulfate, dha</synonym>
  </synonyms>
  <chemical_formula>C19H28O5S</chemical_formula>
  <average_molecular_weight>368.488</average_molecular_weight>
  <monisotopic_moleculate_weight>368.165744696</monisotopic_moleculate_weight>
  <iupac_name>[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid</iupac_name>
  <traditional_iupac>[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid</traditional_iupac>
  <cas_registry_number>651-48-9</cas_registry_number>
  <smiles>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1</inchi>
  <inchikey>CZWCKYRVOZZJNM-USOAJAOKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Sulfated steroids</sub_class>
    <direct_parent>Sulfated steroids</direct_parent>
    <alternative_parents>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Androstane steroids</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-oxosteroid</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Androstane-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfated steroid skeleton</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17-oxo steroid</external_descriptor>
      <external_descriptor>Androgens</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>Sulfates</external_descriptor>
      <external_descriptor>steroid sulfate</external_descriptor>
      <external_descriptor>sulfates</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>368.488</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>368.165744696</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H28O5S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CZWCKYRVOZZJNM-USOAJAOKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>94.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>78474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>78475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>78476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>138825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>138826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>138827</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022381</foodb_id>
  <kegg_id>C04555</kegg_id>
  <pubchem_compound_id>12594</pubchem_compound_id>
  <chemspider_id>12074</chemspider_id>
  <drugbank_id>DB05804</drugbank_id>
  <pdbe_id/>
  <chebi_id>16814</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>44038</bigg_id>
  <wikipedia_id>Dehydroepiandrosterone_sulfate</wikipedia_id>
  <metlin_id>4095</metlin_id>
  <meta_cyc_id>DEHYDRO-EPIANDROSTERONE-SULFATE</meta_cyc_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:09 UTC</creation_date>
  <update_date>2020-04-14 22:48:47 UTC</update_date>
  <accession>BMDB0001033</accession>
  <secondary_accessions>
    <accession>BMDB01033</accession>
  </secondary_accessions>
  <name>Hydrogen sulfite</name>
  <description/>
  <synonyms>
    <synonym>[SO(OH)2]</synonym>
    <synonym>Acide sulfureux</synonym>
    <synonym>Acido sulfuroso</synonym>
    <synonym>H2SO3</synonym>
    <synonym>S(O)(OH)2</synonym>
    <synonym>Schweflige saeure</synonym>
    <synonym>Sulphurous acid</synonym>
    <synonym>Sulfurous acid</synonym>
    <synonym>Acide sulphureux</synonym>
    <synonym>Acido sulphuroso</synonym>
    <synonym>Sulphite</synonym>
    <synonym>Sulfur dioxide solution</synonym>
    <synonym>Sulfuric(IV) acid (H2SO3)</synonym>
    <synonym>Hydrogen sulfite</synonym>
    <synonym>Sulfite</synonym>
  </synonyms>
  <chemical_formula>H2O3S</chemical_formula>
  <average_molecular_weight>82.079</average_molecular_weight>
  <monisotopic_moleculate_weight>81.97246462</monisotopic_moleculate_weight>
  <iupac_name>sulfurous acid</iupac_name>
  <traditional_iupac>sulfurous acid</traditional_iupac>
  <cas_registry_number>14265-45-3</cas_registry_number>
  <smiles>OS(O)=O</smiles>
  <inchi>InChI=1S/H2O3S/c1-4(2)3/h(H2,1,2,3)</inchi>
  <inchikey>LSNNMFCWUKXFEE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as non-metal sulfites. These are inorganic non-metallic compounds containing a sulfite as its largest oxoanion.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Non-metal oxoanionic compounds</class>
    <sub_class>Non-metal sulfites</sub_class>
    <direct_parent>Non-metal sulfites</direct_parent>
    <alternative_parents>
      <alternative_parent>Inorganic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Inorganic oxide</substituent>
      <substituent>Non-metal sulfite</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>sulfur oxoacid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>sulfurous acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>82.079</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>81.97246462</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OS(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>H2O3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/H2O3S/c1-4(2)3/h(H2,1,2,3)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LSNNMFCWUKXFEE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>12.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>5.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218076</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>50</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>McAdam PA, O'Dell GD: Mineral profile of blood plasma of lactating dairy cows. J Dairy Sci. 1982 Jul;65(7):1219-26. doi: 10.3168/jds.S0022-0302(82)82333-3.</reference_text>
          <pubmed_id>7108016</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB013391</foodb_id>
  <kegg_id>C00094</kegg_id>
  <chemspider_id>1069</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>1100</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>48854</chebi_id>
  <knapsack_id>C00019662</knapsack_id>
  <wikipedia_id>Sulfite</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Wilkinson, Peter M.; Doldersum, Bert; Cramers, Peter H. M. R.; Van Dierendonck, Laurent L.  The kinetics of uncatalyzed sodium sulfite oxidation.    Chemical Engineering Science  (1993),  48(5),  933-41.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:11 UTC</creation_date>
  <update_date>2020-03-13 16:25:28 UTC</update_date>
  <accession>BMDB0001035</accession>
  <secondary_accessions>
    <accession>BMDB01035</accession>
  </secondary_accessions>
  <name>Angiotensin II</name>
  <description/>
  <synonyms>
    <synonym>5-Isoleucine-angiotensin II</synonym>
    <synonym>5-L-Isoleucineangiotensin II</synonym>
    <synonym>Angiotensin</synonym>
    <synonym>Angiotensin II (human)</synonym>
    <synonym>Angiotensin II (mouse)</synonym>
    <synonym>Angiotonin</synonym>
    <synonym>Asp-arg-val-tyr-ile-his-pro-phe</synonym>
    <synonym>Human angiotensin II</synonym>
    <synonym>Hypertensin</synonym>
    <synonym>Isoleucine(5)-angiotensin II</synonym>
    <synonym>N-(1-(N-(N-(N-(N-(N(2)-L-alpha-Aspartyl-L-arginyl)-L-valyl)-L-tyrosyl)-L-isoleucyl)-L-histidyl)-L-prolyl)-L-phenylalanine</synonym>
    <synonym>Delivert</synonym>
    <synonym>N-(1-(N-(N-(N-(N-(N(2)-L-a-Aspartyl-L-arginyl)-L-valyl)-L-tyrosyl)-L-isoleucyl)-L-histidyl)-L-prolyl)-L-phenylalanine</synonym>
    <synonym>N-(1-(N-(N-(N-(N-(N(2)-L-Α-aspartyl-L-arginyl)-L-valyl)-L-tyrosyl)-L-isoleucyl)-L-histidyl)-L-prolyl)-L-phenylalanine</synonym>
    <synonym>1-8-Angiotensin I</synonym>
    <synonym>1-L-Aspasaginyl-5-L-valyl angiotensin octapeptide</synonym>
    <synonym>Ang II</synonym>
    <synonym>Angiotensin 2</synonym>
    <synonym>Ile(5)-angiotensin II</synonym>
    <synonym>II, 5-L-isoleucine angiotensin</synonym>
    <synonym>Isoleucyl(5)-angiotensin II</synonym>
    <synonym>Angiotensin II, 5-L-isoleucine</synonym>
    <synonym>Valyl(5)-angiotensin II</synonym>
    <synonym>ANG-(1-8)octapeptide</synonym>
    <synonym>Isoleucine(5)-angiotensin</synonym>
    <synonym>5 L Isoleucine angiotensin II</synonym>
    <synonym>5-L-Isoleucine angiotensin II</synonym>
    <synonym>Angiotensin-(1-8) octapeptide</synonym>
  </synonyms>
  <chemical_formula>C50H71N13O12</chemical_formula>
  <average_molecular_weight>1046.1786</average_molecular_weight>
  <monisotopic_moleculate_weight>1045.534514801</monisotopic_moleculate_weight>
  <iupac_name>(3S)-3-amino-3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(diaminomethylidene)amino]butyl]carbamoyl}propanoic acid</iupac_name>
  <traditional_iupac>(3S)-3-amino-3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-3-(3H-imidazol-4-yl)-1-oxopropan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(diaminomethylidene)amino]butyl]carbamoyl}propanoic acid</traditional_iupac>
  <cas_registry_number>11128-99-7</cas_registry_number>
  <smiles>CC[C@H](C)[C@H](NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C50H71N13O12/c1-5-28(4)41(47(72)59-36(23-31-25-54-26-56-31)48(73)63-20-10-14-38(63)45(70)60-37(49(74)75)22-29-11-7-6-8-12-29)62-44(69)35(21-30-15-17-32(64)18-16-30)58-46(71)40(27(2)3)61-43(68)34(13-9-19-55-50(52)53)57-42(67)33(51)24-39(65)66/h6-8,11-12,15-18,25-28,33-38,40-41,64H,5,9-10,13-14,19-24,51H2,1-4H3,(H,54,56)(H,57,67)(H,58,71)(H,59,72)(H,60,70)(H,61,68)(H,62,69)(H,65,66)(H,74,75)(H4,52,53,55)/t28-,33-,34-,35-,36-,37-,38-,40-,41-/m0/s1</inchi>
  <inchikey>CZGUSIXMZVURDU-JZXHSEFVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Oligopeptides</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aspartic acid and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Guanidines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Histidine and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolyl carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Isoleucine and derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>N-acylpyrrolidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalanine and derivatives</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
      <alternative_parent>Proline and derivatives</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrrolidinecarboxamides</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tyrosine and derivatives</alternative_parent>
      <alternative_parent>Valine and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-oligopeptide</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Aspartic acid or derivatives</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Histidine or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazolyl carboxylic acid derivative</substituent>
      <substituent>Isoleucine or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>N-acylpyrrolidine</substituent>
      <substituent>N-substituted-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Proline or derivatives</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidine carboxylic acid or derivatives</substituent>
      <substituent>Pyrrolidine-2-carboxamide</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
      <substituent>Tyrosine or derivatives</substituent>
      <substituent>Valine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Angiotensin [KO:K09821]</external_descriptor>
      <external_descriptor>angiotensin II</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3S)-3-amino-3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S,2S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(diaminomethylidene)amino]butyl]carbamoyl}propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1046.1786</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1045.534514801</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC[C@H](C)[C@H](NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C50H71N13O12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C50H71N13O12/c1-5-28(4)41(47(72)59-36(23-31-25-54-26-56-31)48(73)63-20-10-14-38(63)45(70)60-37(49(74)75)22-29-11-7-6-8-12-29)62-44(69)35(21-30-15-17-32(64)18-16-30)58-46(71)40(27(2)3)61-43(68)34(13-9-19-55-50(52)53)57-42(67)33(51)24-39(65)66/h6-8,11-12,15-18,25-28,33-38,40-41,64H,5,9-10,13-14,19-24,51H2,1-4H3,(H,54,56)(H,57,67)(H,58,71)(H,59,72)(H,60,70)(H,61,68)(H,62,69)(H,65,66)(H,74,75)(H4,52,53,55)/t28-,33-,34-,35-,36-,37-,38-,40-,41-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CZGUSIXMZVURDU-JZXHSEFVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>408.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>269.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>107.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Angiotensin Metabolism</name>
      <smpdb_id>SMP0119379</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>106899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>106900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>106901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>173748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>173749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>173750</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022383</foodb_id>
  <kegg_id>C02135</kegg_id>
  <pubchem_compound_id>172198</pubchem_compound_id>
  <chemspider_id>150504</chemspider_id>
  <drugbank_id>DB11842</drugbank_id>
  <pdbe_id/>
  <chebi_id>2719</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Angiotensin</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01005</protein_accession>
      <name>Angiotensin-converting enzyme</name>
      <uniprot_id>P12820</uniprot_id>
      <gene_name>ACE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01006</protein_accession>
      <name>Protein tyrosine phosphatase type IVA 3</name>
      <uniprot_id>A2VDT1</uniprot_id>
      <gene_name>PTP4A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02251</protein_accession>
      <name>Type-1 angiotensin II receptor</name>
      <uniprot_id>P25104</uniprot_id>
      <gene_name>AGTR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02252</protein_accession>
      <name>Angiotensin II receptor-associated protein</name>
      <uniprot_id>Q17QI4</uniprot_id>
      <gene_name>AGTRAP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:12 UTC</creation_date>
  <update_date>2020-03-13 16:25:28 UTC</update_date>
  <accession>BMDB0001036</accession>
  <secondary_accessions>
    <accession>BMDB01036</accession>
  </secondary_accessions>
  <name>Angiotensin III</name>
  <description/>
  <synonyms>
    <synonym>Des-asp-1-angiotensin II</synonym>
    <synonym>Angiotensin II, des-asp</synonym>
    <synonym>Des asp angiotensin II</synonym>
    <synonym>Des aspartyl angiotensin II</synonym>
    <synonym>Des-asp angiotensin II</synonym>
    <synonym>Des-aspartyl-angiotensin II</synonym>
    <synonym>(2S)-2-({[(2S)-1-[(2S)-2-{[(2S,3S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-3-(1H-imidazol-5-yl)propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-phenylpropanoate</synonym>
    <synonym>Angiotensin III</synonym>
  </synonyms>
  <chemical_formula>C46H66N12O9</chemical_formula>
  <average_molecular_weight>931.0912</average_molecular_weight>
  <monisotopic_moleculate_weight>930.50757177</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-[(diaminomethylidene)amino]pentanamido]-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid</iupac_name>
  <traditional_iupac>(2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-[(diaminomethylidene)amino]pentanamido]-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]-3-(3H-imidazol-4-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid</traditional_iupac>
  <cas_registry_number>12687-51-3</cas_registry_number>
  <smiles>CC[C@H](C)[C@H](NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H](NC(=O)[C@@H](N)CCCN=C(N)N)C(C)C)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C46H66N12O9/c1-5-27(4)38(57-40(61)33(21-29-15-17-31(59)18-16-29)53-42(63)37(26(2)3)56-39(60)32(47)13-9-19-51-46(48)49)43(64)54-34(23-30-24-50-25-52-30)44(65)58-20-10-14-36(58)41(62)55-35(45(66)67)22-28-11-7-6-8-12-28/h6-8,11-12,15-18,24-27,32-38,59H,5,9-10,13-14,19-23,47H2,1-4H3,(H,50,52)(H,53,63)(H,54,64)(H,55,62)(H,56,60)(H,57,61)(H,66,67)(H4,48,49,51)/t27-,32-,33-,34-,35-,36-,37-,38-/m0/s1</inchi>
  <inchikey>QMMRCKSBBNJCMR-KMZPNFOHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Oligopeptides</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Guanidines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Histidine and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolyl carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Isoleucine and derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>N-acylpyrrolidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalanine and derivatives</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
      <alternative_parent>Proline and derivatives</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrrolidinecarboxamides</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tyrosine and derivatives</alternative_parent>
      <alternative_parent>Valine and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-oligopeptide</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Histidine or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazolyl carboxylic acid derivative</substituent>
      <substituent>Isoleucine or derivatives</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>N-acylpyrrolidine</substituent>
      <substituent>N-substituted-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Proline or derivatives</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidine carboxylic acid or derivatives</substituent>
      <substituent>Pyrrolidine-2-carboxamide</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
      <substituent>Tyrosine or derivatives</substituent>
      <substituent>Valine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>11.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-[(diaminomethylidene)amino]pentanamido]-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>931.0912</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>930.50757177</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC[C@H](C)[C@H](NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H](NC(=O)[C@@H](N)CCCN=C(N)N)C(C)C)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C46H66N12O9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C46H66N12O9/c1-5-27(4)38(57-40(61)33(21-29-15-17-31(59)18-16-29)53-42(63)37(26(2)3)56-39(60)32(47)13-9-19-51-46(48)49)43(64)54-34(23-30-24-50-25-52-30)44(65)58-20-10-14-36(58)41(62)55-35(45(66)67)22-28-11-7-6-8-12-28/h6-8,11-12,15-18,24-27,32-38,59H,5,9-10,13-14,19-23,47H2,1-4H3,(H,50,52)(H,53,63)(H,54,64)(H,55,62)(H,56,60)(H,57,61)(H,66,67)(H4,48,49,51)/t27-,32-,33-,34-,35-,36-,37-,38-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QMMRCKSBBNJCMR-KMZPNFOHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>342.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>246.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>98.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326613</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022384</foodb_id>
  <chemspider_id>2339529</chemspider_id>
  <kegg_id>C15848</kegg_id>
  <drugbank_id/>
  <pubchem_compound_id>3082042</pubchem_compound_id>
  <chebi_id>1183270</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Angiotensin</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:13 UTC</creation_date>
  <update_date>2020-03-13 16:25:29 UTC</update_date>
  <accession>BMDB0001038</accession>
  <secondary_accessions>
    <accession>BMDB01038</accession>
  </secondary_accessions>
  <name>Angiotensin IV</name>
  <description/>
  <synonyms>
    <synonym>(3-8)-5-Isoleucine-angiotensin II</synonym>
    <synonym>(Des(asp1,arg2)-ile5)angiotensin II</synonym>
    <synonym>(Ile5)-angiotensin II (3-8)</synonym>
    <synonym>(Isoleucine5)-angiotensin II hexapeptide</synonym>
    <synonym>1-De-asp-2-de-arg-5-ile-angiotensin II</synonym>
    <synonym>3-L-Isoleucine-angiotensin IV</synonym>
    <synonym>5-Isoleucine-angiotensin II 3-8-hexapeptide</synonym>
    <synonym>Huamn angiotensin (3-8)</synonym>
    <synonym>Human angiotensin hexapeptide (3-8)</synonym>
    <synonym>Human angiotensin IV</synonym>
    <synonym>Ile3-angiotensin IV</synonym>
    <synonym>Nle-angiv</synonym>
    <synonym>Val-tyr-ile-his-pro-phe</synonym>
    <synonym>Angiotensin II (3-8)</synonym>
    <synonym>(a)II(3-8)</synonym>
    <synonym>(2S)-2-({[(2S)-1-[(2S)-2-{[(2S,3S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxy-3-methylpentylidene]amino}-3-(1H-imidazol-5-yl)propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-phenylpropanoate</synonym>
    <synonym>Angiotensin IV</synonym>
  </synonyms>
  <chemical_formula>C40H54N8O8</chemical_formula>
  <average_molecular_weight>774.9056</average_molecular_weight>
  <monisotopic_moleculate_weight>774.406460744</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid</iupac_name>
  <traditional_iupac>(2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]-3-(3H-imidazol-4-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid</traditional_iupac>
  <cas_registry_number>12676-15-2</cas_registry_number>
  <smiles>CC[C@H](C)[C@H](NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H](N)C(C)C)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C40H54N8O8/c1-5-24(4)34(47-35(50)29(44-37(52)33(41)23(2)3)18-26-13-15-28(49)16-14-26)38(53)45-30(20-27-21-42-22-43-27)39(54)48-17-9-12-32(48)36(51)46-31(40(55)56)19-25-10-7-6-8-11-25/h6-8,10-11,13-16,21-24,29-34,49H,5,9,12,17-20,41H2,1-4H3,(H,42,43)(H,44,52)(H,45,53)(H,46,51)(H,47,50)(H,55,56)/t24-,29-,30-,31-,32-,33-,34-/m0/s1</inchi>
  <inchikey>QSBGWDDCOJYQGY-KOQODJNWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Oligopeptides</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Histidine and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolyl carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Isoleucine and derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>N-acylpyrrolidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalanine and derivatives</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
      <alternative_parent>Proline and derivatives</alternative_parent>
      <alternative_parent>Pyrrolidinecarboxamides</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tyrosine and derivatives</alternative_parent>
      <alternative_parent>Valine and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-oligopeptide</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Histidine or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazolyl carboxylic acid derivative</substituent>
      <substituent>Isoleucine or derivatives</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>N-acylpyrrolidine</substituent>
      <substituent>N-substituted-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Proline or derivatives</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidine carboxylic acid or derivatives</substituent>
      <substituent>Pyrrolidine-2-carboxamide</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
      <substituent>Tyrosine or derivatives</substituent>
      <substituent>Valine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-methylpentanamido]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>774.9056</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>774.406460744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC[C@H](C)[C@H](NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H](N)C(C)C)C(=O)N[C@@H](CC1=CN=CN1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C40H54N8O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C40H54N8O8/c1-5-24(4)34(47-35(50)29(44-37(52)33(41)23(2)3)18-26-13-15-28(49)16-14-26)38(53)45-30(20-27-21-42-22-43-27)39(54)48-17-9-12-32(48)36(51)46-31(40(55)56)19-25-10-7-6-8-11-25/h6-8,10-11,13-16,21-24,29-34,49H,5,9,12,17-20,41H2,1-4H3,(H,42,43)(H,44,52)(H,45,53)(H,46,51)(H,47,50)(H,55,56)/t24-,29-,30-,31-,32-,33-,34-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QSBGWDDCOJYQGY-KOQODJNWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>248.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>206.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>81.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>64293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327210</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022385</foodb_id>
  <kegg_id>C15849</kegg_id>
  <pubchem_compound_id>123814</pubchem_compound_id>
  <chemspider_id>110363</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>528953</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:14 UTC</creation_date>
  <update_date>2020-03-13 16:25:29 UTC</update_date>
  <accession>BMDB0001039</accession>
  <secondary_accessions>
    <accession>BMDB01039</accession>
  </secondary_accessions>
  <name>Hydroxide</name>
  <description/>
  <synonyms>
    <synonym>HYDROXIDE ion</synonym>
    <synonym>OH(-)</synonym>
    <synonym>Hydridooxygenate(1-)</synonym>
    <synonym>Hydrogen oxide</synonym>
    <synonym>Hydroxide anion</synonym>
    <synonym>Hydroxide ion(1-)</synonym>
    <synonym>Hydroxide(1-)</synonym>
    <synonym>Hydroxy</synonym>
    <synonym>Hydroxy anion</synonym>
    <synonym>Hydroxy ion</synonym>
    <synonym>Hydroxyl</synonym>
    <synonym>Hydroxyl anion</synonym>
    <synonym>Hydroxyl ion</synonym>
    <synonym>Hydroxyl ion (OH1-)</synonym>
    <synonym>Hydroxyl radical</synonym>
    <synonym>Hydroxyl radicals</synonym>
    <synonym>OH</synonym>
    <synonym>Oxidanide</synonym>
    <synonym>Oxygen ion (O1-)</synonym>
    <synonym>Water ion(1-)</synonym>
  </synonyms>
  <chemical_formula>HO</chemical_formula>
  <average_molecular_weight>17.0073</average_molecular_weight>
  <monisotopic_moleculate_weight>17.002739654</monisotopic_moleculate_weight>
  <iupac_name>hydroxide</iupac_name>
  <traditional_iupac>hydroxide</traditional_iupac>
  <cas_registry_number>14280-30-9</cas_registry_number>
  <smiles>[OH-]</smiles>
  <inchi>InChI=1S/H2O/h1H2/p-1</inchi>
  <inchikey>XLYOFNOQVPJJNP-UHFFFAOYSA-M</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as non-metal hydroxides. These are inorganic non-metallic compounds containing the hydroxide group as its largest oxoanion.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Non-metal oxoanionic compounds</class>
    <sub_class>Non-metal hydroxides</sub_class>
    <direct_parent>Non-metal hydroxides</direct_parent>
    <alternative_parents>
      <alternative_parent>Inorganic hydrides</alternative_parent>
      <alternative_parent>Inorganic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Inorganic hydride</substituent>
      <substituent>Inorganic oxide</substituent>
      <substituent>Non-metal hydroxide</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>an anion</external_descriptor>
      <external_descriptor>oxygen hydride</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>hydroxide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>17.0073</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>17.002739654</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[OH-]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>HO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/H2O/h1H2/p-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XLYOFNOQVPJJNP-UHFFFAOYSA-M</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>13.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>55734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>55735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>55736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>110946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>110947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>110948</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01328</kegg_id>
  <chemspider_id>936</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB022386</foodb_id>
  <pubchem_compound_id>961</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16234</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>37371</bigg_id>
  <wikipedia_id>Hydroxide</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Revzin, G. E.; Lavrent'eva, V. G.; Revzina, T. V.; Kashina, N. I.  Preparation of hydroxides slightly soluble in water.    U.S.S.R.  (1967),     CODEN: URXXAF  SU  196735  19670531  CAN 68:4526  AN 1968:4526</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00438</protein_accession>
      <name>Alpha-1-antiproteinase</name>
      <uniprot_id>P34955</uniprot_id>
      <gene_name>SERPINA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00439</protein_accession>
      <name>Xylosyltransferase 2</name>
      <uniprot_id>Q5QQ49</uniprot_id>
      <gene_name>XYLT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:15 UTC</creation_date>
  <update_date>2020-03-13 16:25:30 UTC</update_date>
  <accession>BMDB0001041</accession>
  <secondary_accessions>
    <accession>BMDB01041</accession>
  </secondary_accessions>
  <name>2-Methylbutyryl-CoA</name>
  <description/>
  <synonyms>
    <synonym>(S)-2-Methylbutyryl-CoA</synonym>
    <synonym>(S)-2-Methylbutyryl-coenzyme A</synonym>
    <synonym>2-Methylbutanoyl-CoA</synonym>
    <synonym>2-Methylbutanoyl-coenzyme A</synonym>
    <synonym>2-Methylbutyryl-coenzyme A</synonym>
    <synonym>3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-{[3-({2-[(2-methylbutanoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-4-oxobutyl] dihydrogen diphosphate}</synonym>
    <synonym>a-Methylbutyryl-CoA</synonym>
    <synonym>alpha-Methylbutyryl-CoA</synonym>
    <synonym>alpha-Methylbutyryl-coenzyme A</synonym>
    <synonym>Methylbutanoyl-CoA</synonym>
    <synonym>Methylbutanoyl-coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C26H44N7O17P3S</chemical_formula>
  <average_molecular_weight>851.651</average_molecular_weight>
  <monisotopic_moleculate_weight>851.172723243</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylbutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylbutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>6712-02-3</cas_registry_number>
  <smiles>CCC(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C26H44N7O17P3S/c1-5-14(2)25(38)54-9-8-28-16(34)6-7-29-23(37)20(36)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-19(49-51(39,40)41)18(35)24(48-15)33-13-32-17-21(27)30-12-31-22(17)33/h12-15,18-20,24,35-36H,5-11H2,1-4H3,(H,28,34)(H,29,37)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t14?,15-,18-,19-,20?,24-/m1/s1</inchi>
  <inchikey>LYNVNYDEQMMNMZ-PCLZRLGGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylbutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>851.651</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>851.172723243</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H44N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H44N7O17P3S/c1-5-14(2)25(38)54-9-8-28-16(34)6-7-29-23(37)20(36)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-19(49-51(39,40)41)18(35)24(48-15)33-13-32-17-21(27)30-12-31-22(17)33/h12-15,18-20,24,35-36H,5-11H2,1-4H3,(H,28,34)(H,29,37)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t14?,15-,18-,19-,20?,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LYNVNYDEQMMNMZ-PCLZRLGGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>186.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>76.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344691</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01033</kegg_id>
  <chemspider_id>388491</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB022387</foodb_id>
  <pubchem_compound_id>439371</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15477</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>36663</bigg_id>
  <wikipedia_id>2-Methylbutyryl-CoA</wikipedia_id>
  <metlin_id>5960</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:16 UTC</creation_date>
  <update_date>2020-04-16 20:40:04 UTC</update_date>
  <accession>BMDB0001043</accession>
  <secondary_accessions>
    <accession>BMDB0060102</accession>
    <accession>BMDB01043</accession>
    <accession>BMDB60102</accession>
  </secondary_accessions>
  <name>Arachidonic acid</name>
  <description>Arachidonic acid, also known as arachidonate or AA, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Arachidonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Arachidonic acid exists in all living organisms, ranging from bacteria to humans. Arachidonic acid has been found to be associated with several diseases known as colorectal cancer, hypertension, bladder infections, and gestational diabetes; also arachidonic acid has been linked to the inborn metabolic disorders including isovaleric acidemia.</description>
  <synonyms>
    <synonym>(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid</synonym>
    <synonym>(5Z,8Z,11Z,14Z)-Icosatetraenoic acid</synonym>
    <synonym>AA</synonym>
    <synonym>all-cis-5,8,11,14-Eicosatetraenoic acid</synonym>
    <synonym>ARA</synonym>
    <synonym>Arachidonate</synonym>
    <synonym>Arachidonsaeure</synonym>
    <synonym>cis-5,8,11,14-Eicosatetraenoic acid</synonym>
    <synonym>cis-Delta(5,8,11,14)-Eicosatetraenoic acid</synonym>
    <synonym>5Z,8Z,11Z,14Z-Eicosatetraenoic acid</synonym>
    <synonym>(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid</synonym>
    <synonym>(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoate</synonym>
    <synonym>(5Z,8Z,11Z,14Z)-Icosatetraenoate</synonym>
    <synonym>all-cis-5,8,11,14-Eicosatetraenoate</synonym>
    <synonym>cis-5,8,11,14-Eicosatetraenoate</synonym>
    <synonym>cis-delta(5,8,11,14)-Eicosatetraenoate</synonym>
    <synonym>cis-Δ(5,8,11,14)-eicosatetraenoate</synonym>
    <synonym>cis-Δ(5,8,11,14)-eicosatetraenoic acid</synonym>
    <synonym>5Z,8Z,11Z,14Z-Eicosatetraenoate</synonym>
    <synonym>(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoate</synonym>
    <synonym>(all-Z)-5,8,11,14-Eicosatetraenoate</synonym>
    <synonym>(all-Z)-5,8,11,14-Eicosatetraenoic acid</synonym>
    <synonym>5,8,11,14-all-cis-Eicosatetraenoate</synonym>
    <synonym>5,8,11,14-all-cis-Eicosatetraenoic acid</synonym>
    <synonym>5,8,11,14-Eicosatetraenoate</synonym>
    <synonym>5,8,11,14-Eicosatetraenoic acid</synonym>
    <synonym>5-cis,8-cis,11-cis,14-cis-Eicosatetraenoate</synonym>
    <synonym>5-cis,8-cis,11-cis,14-cis-Eicosatetraenoic acid</synonym>
    <synonym>cis-D5,8,11,14-Eicosatetraenoate</synonym>
    <synonym>cis-D5,8,11,14-Eicosatetraenoic acid</synonym>
    <synonym>Immunocytophyte</synonym>
    <synonym>Arachidonate, sodium</synonym>
    <synonym>Arachidonic acid, (all-Z)-isomer, 3H-labeled</synonym>
    <synonym>Arachidonic acid, ammonium salt, (all-Z)-isomer</synonym>
    <synonym>Arachidonic acid, cerium salt, (all-Z)-isomer</synonym>
    <synonym>Arachidonic acid, sodium salt</synonym>
    <synonym>Arachidonic acid, sodium salt, (all-Z)-isomer</synonym>
    <synonym>Vitamin F</synonym>
    <synonym>Arachidonic acid, cesium salt, (all-Z)-isomer</synonym>
    <synonym>Arachidonic acid, lithium salt, (all-Z)-isomer</synonym>
    <synonym>Arachidonic acid, potassium salt, (all-Z)-isomer</synonym>
    <synonym>Sodium arachidonate</synonym>
    <synonym>Arachidonic acid, (all-Z)-isomer, 1-(14)C-labeled</synonym>
    <synonym>Arachidonic acid, zinc salt, (all-Z)-isomer</synonym>
    <synonym>FA(20:4(5Z,8Z,11Z,14Z))</synonym>
    <synonym>FA(20:4n6)</synonym>
  </synonyms>
  <chemical_formula>C20H32O2</chemical_formula>
  <average_molecular_weight>304.4669</average_molecular_weight>
  <monisotopic_moleculate_weight>304.240230268</monisotopic_moleculate_weight>
  <iupac_name>(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid</iupac_name>
  <traditional_iupac>arachidonic acid</traditional_iupac>
  <cas_registry_number>506-32-1</cas_registry_number>
  <smiles>CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-</inchi>
  <inchikey>YZXBAPSDXZZRGB-DOFZRALJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Polyunsaturated fatty acids</external_descriptor>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>icosa-5,8,11,14-tetraenoic acid</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>omega-6 fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>logp</kind>
      <value>6.98</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>304.4669</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>304.240230268</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H32O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YZXBAPSDXZZRGB-DOFZRALJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>99.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alpha Linolenic Acid and Linoleic Acid Metabolism</name>
      <smpdb_id>SMP0087171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fc Epsilon Receptor I Signaling in Mast Cells</name>
      <smpdb_id>SMP0108186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>GnRH Signaling Pathway</name>
      <smpdb_id>SMP0120925</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373988</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440465</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>692.62</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>953.93</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>310.94</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>899.7</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>872.71</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>1345.14</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed barley silage diet for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed barley silage diet with flaxseed for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed hay for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed hay with flaxseed for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>656.886</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1313.772</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1642.215</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1116.706 +/- 459.820</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2594.698 +/- 624.0414</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2463.321 +/- 525.509</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>952.484 +/- 328.443</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples have been collected from Heifer cows.</comment>
      <references>
        <reference>
          <reference_text>Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub  2013 Jun 5.</reference_text>
          <pubmed_id>23871026</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Oocyte</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by CP9010 autosampler onto a capillary column within a CP9001 gas chromatograph in slaughtered cow ovaries.</comment>
      <references>
        <reference>
          <reference_text>McEvoy TG, Coull GD, Broadbent PJ, Hutchinson JS, Speake BK: Fatty acid composition of lipids in immature cattle, pig and sheep oocytes with intact zona pellucida. J Reprod Fertil. 2000 Jan;118(1):163-70.</reference_text>
          <pubmed_id>10793638</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00219</kegg_id>
  <chemspider_id>392692</chemspider_id>
  <drugbank_id>DB04557</drugbank_id>
  <foodb_id>FDB011872</foodb_id>
  <pubchem_compound_id>444899</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15843</chebi_id>
  <meta_cyc_id>ARACHIDONIC_ACID</meta_cyc_id>
  <knapsack_id>C00000388</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>1586189</bigg_id>
  <wikipedia_id>Arachidonic_acid</wikipedia_id>
  <metlin_id>193</metlin_id>
  <synthesis_reference>Dai, Chuanchao; Yuan, Zhilin; Wang, Anqi.  Production of arachidonic acid and eicosapentaenoic acid with organic wastewater of soybean products.    Zhongguo Youzhi  (2004),  29(5),  31-33.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.</reference_text>
      <pubmed_id>28219465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
    </reference>
    <reference>
      <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00826</protein_accession>
      <name>Secretory phospholipase A2 receptor</name>
      <uniprot_id>P49259</uniprot_id>
      <gene_name>PLA2R1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02545</protein_accession>
      <name>SNCA protein</name>
      <uniprot_id>A6QQ08</uniprot_id>
      <gene_name>SNCA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02546</protein_accession>
      <name>Arachidonate 5-lipoxygenase-activating protein</name>
      <uniprot_id>Q148F2</uniprot_id>
      <gene_name>ALOX5AP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:18 UTC</creation_date>
  <update_date>2020-03-13 16:25:31 UTC</update_date>
  <accession>BMDB0001044</accession>
  <secondary_accessions>
    <accession>BMDB01044</accession>
  </secondary_accessions>
  <name>2'-Deoxyguanosine 5'-monophosphate</name>
  <description/>
  <synonyms>
    <synonym>2'-Deoxy-GMP</synonym>
    <synonym>2'-Deoxyguanosine 5'-(dihydrogen phosphate)</synonym>
    <synonym>2'-Deoxyguanosine 5'-phosphate</synonym>
    <synonym>2'-Deoxyguanylic acid</synonym>
    <synonym>2'-dGMP</synonym>
    <synonym>Deoxy-GMP</synonym>
    <synonym>Deoxyguanosine 5'-monophosphate</synonym>
    <synonym>Deoxyguanosine 5'-phosphate</synonym>
    <synonym>Deoxyguanosine monophosphate</synonym>
    <synonym>Deoxyguanylic acid</synonym>
    <synonym>dGMP</synonym>
    <synonym>2'-Deoxyguanosine 5'-(dihydrogen phosphoric acid)</synonym>
    <synonym>2'-Deoxyguanosine 5'-phosphoric acid</synonym>
    <synonym>2'-Deoxyguanylate</synonym>
    <synonym>Deoxyguanosine 5'-monophosphoric acid</synonym>
    <synonym>Deoxyguanosine 5'-phosphoric acid</synonym>
    <synonym>Deoxyguanosine monophosphoric acid</synonym>
    <synonym>Deoxyguanylate</synonym>
    <synonym>2'-Deoxyguanosine 5'-monophosphoric acid</synonym>
    <synonym>2'-Deoxy-5'-GMP</synonym>
    <synonym>2'-Deoxy-5'-guanylate</synonym>
    <synonym>2'-Deoxy-5'-guanylic acid</synonym>
    <synonym>2'-Deoxy-guanosine 5'-(dihydrogen phosphate)</synonym>
    <synonym>2'-Deoxy-guanosine 5'-phosphate</synonym>
    <synonym>2'-Deoxy-guanosine phosphate</synonym>
    <synonym>2'-Deoxyguanosine-5'-phosphate</synonym>
    <synonym>2'-DG-5'-MP</synonym>
    <synonym>Deoxyguanosine-phosphate</synonym>
    <synonym>Guanine riboside</synonym>
    <synonym>2'-Deoxyguanosine 5'-phosphate, ion (1+)</synonym>
    <synonym>2'-Deoxyguanosine 5'-phosphate, disodium salt</synonym>
  </synonyms>
  <chemical_formula>C10H14N5O7P</chemical_formula>
  <average_molecular_weight>347.2212</average_molecular_weight>
  <monisotopic_moleculate_weight>347.063084339</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>deoxyguanylate</traditional_iupac>
  <cas_registry_number>902-04-5</cas_registry_number>
  <smiles>NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)N1</smiles>
  <inchi>InChI=1S/C10H14N5O7P/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(22-6)2-21-23(18,19)20/h3-6,16H,1-2H2,(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1</inchi>
  <inchikey>LTFMZDNNPPEQNG-KVQBGUIXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group  linked to the ribose moiety lacking a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine deoxyribonucleotides</sub_class>
    <direct_parent>Purine 2'-deoxyribonucleoside monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Purines and purine derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine 2'-deoxyribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxyribonucleotides</external_descriptor>
      <external_descriptor>deoxyguanosine phosphate</external_descriptor>
      <external_descriptor>guanyl deoxyribonucleotide</external_descriptor>
      <external_descriptor>purine 2'-deoxyribonucleoside 5'-monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>347.2212</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>347.063084339</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H14N5O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H14N5O7P/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(22-6)2-21-23(18,19)20/h3-6,16H,1-2H2,(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LTFMZDNNPPEQNG-KVQBGUIXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>181.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>73.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448113</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00362</kegg_id>
  <chemspider_id>58570</chemspider_id>
  <drugbank_id>DB04457</drugbank_id>
  <foodb_id>FDB022388</foodb_id>
  <pubchem_compound_id>65059</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16192</chebi_id>
  <meta_cyc_id>DGMP</meta_cyc_id>
  <knapsack_id>C00019356</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34744</bigg_id>
  <wikipedia_id>Deoxyguanosine_monophosphate</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Reichard, Peter.  Formation of deoxyguanosine 5'-phosphate from guanosine 5'-phosphate with enzymes from chick embryos.    Biochimica et Biophysica Acta  (1960),  41  368-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:19 UTC</creation_date>
  <update_date>2020-03-13 16:25:31 UTC</update_date>
  <accession>BMDB0001045</accession>
  <secondary_accessions>
    <accession>BMDB01045</accession>
  </secondary_accessions>
  <name>Enkephalin L</name>
  <description/>
  <synonyms>
    <synonym>Leucine- enkephalin</synonym>
    <synonym>Leu-enkephalin</synonym>
    <synonym>Leucine enkephalin</synonym>
    <synonym>[5-Leucine]enkephalin</synonym>
    <synonym>[Leu 5]enkephalin</synonym>
    <synonym>[Leu5]-enkephalin</synonym>
    <synonym>[Leu]enkephalin</synonym>
    <synonym>Enkephalin, 5-leucine</synonym>
    <synonym>Leu enkephalin</synonym>
    <synonym>5 Leucine enkephalin</synonym>
    <synonym>Enkephalin, leucine</synonym>
    <synonym>Leu(5)-enkephalin</synonym>
    <synonym>5-Leucine enkephalin</synonym>
    <synonym>(2S)-2-{[(2S)-2-({2-[(2-{[(2S)-2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-4-methylpentanoate</synonym>
  </synonyms>
  <chemical_formula>C28H37N5O7</chemical_formula>
  <average_molecular_weight>555.6227</average_molecular_weight>
  <monisotopic_moleculate_weight>555.269298563</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanoic acid</iupac_name>
  <traditional_iupac>(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanoic acid</traditional_iupac>
  <cas_registry_number>14-18-6</cas_registry_number>
  <smiles>CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC1=CC=C(O)C=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22-,23-/m0/s1</inchi>
  <inchikey>URLZCHNOLZSCCA-VABKMULXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Oligopeptides</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty amides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Leucine and derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalanine and derivatives</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tyrosine and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-oligopeptide</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Leucine or derivatives</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>N-substituted-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tyrosine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>7.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-methylpentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>555.6227</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>555.269298563</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)C[C@H](NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC1=CC=C(O)C=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C28H37N5O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C28H37N5O7/c1-17(2)12-23(28(39)40)33-27(38)22(14-18-6-4-3-5-7-18)32-25(36)16-30-24(35)15-31-26(37)21(29)13-19-8-10-20(34)11-9-19/h3-11,17,21-23,34H,12-16,29H2,1-2H3,(H,30,35)(H,31,37)(H,32,36)(H,33,38)(H,39,40)/t21-,22-,23-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>URLZCHNOLZSCCA-VABKMULXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>199.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>145.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>57.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351456</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id>406229</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB022389</foodb_id>
  <pubchem_compound_id>461776</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>103389</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:20 UTC</creation_date>
  <update_date>2020-04-16 20:36:55 UTC</update_date>
  <accession>BMDB0001046</accession>
  <secondary_accessions>
    <accession>BMDB01046</accession>
  </secondary_accessions>
  <name>Cotinine</name>
  <description/>
  <synonyms>
    <synonym>Cotinine(15% OF the dose)</synonym>
    <synonym>(-)-Cotinine</synonym>
    <synonym>(S)-(-)-Cotinine</synonym>
    <synonym>(S)-Cotinine</synonym>
    <synonym>Cotinina</synonym>
    <synonym>Cotininum</synonym>
    <synonym>S-(-)-Cotinine</synonym>
  </synonyms>
  <chemical_formula>C10H12N2O</chemical_formula>
  <average_molecular_weight>176.2151</average_molecular_weight>
  <monisotopic_moleculate_weight>176.094963016</monisotopic_moleculate_weight>
  <iupac_name>1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one</iupac_name>
  <traditional_iupac>(-)-cotinine</traditional_iupac>
  <cas_registry_number>486-56-6</cas_registry_number>
  <smiles>CN1C(CCC1=O)C1=CN=CC=C1</smiles>
  <inchi>InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3</inchi>
  <inchikey>UIKROCXWUNQSPJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyrrolidinylpyridines</sub_class>
    <direct_parent>Pyrrolidinylpyridines</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>N-alkylpyrrolidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrrolidine-2-ones</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-pyrrolidone</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>N-alkylpyrrolidine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidinylpyridine</substituent>
      <substituent>Pyrrolidone</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>41 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.07</value>
      <source>LI,NY &amp; GORROD,JW (1992)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>176.2151</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>176.094963016</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C(CCC1=O)C1=CN=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UIKROCXWUNQSPJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>33.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>49.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>8326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>14998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452421</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id>395</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB004716</foodb_id>
  <pubchem_compound_id>408</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>127762</chebi_id>
  <meta_cyc_id/>
  <knapsack_id>C00034470</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Cotinine</wikipedia_id>
  <metlin_id>1531</metlin_id>
  <synthesis_reference>Rolf, David; Goon, David J. W.; Michelson, Robert H.  Preparation of cotinine by reacting nicotine with bromide and bromate.    U.S.  (1997),     5 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:21 UTC</creation_date>
  <update_date>2020-03-13 16:25:32 UTC</update_date>
  <accession>BMDB0001047</accession>
  <secondary_accessions>
    <accession>BMDB01047</accession>
  </secondary_accessions>
  <name>D-Fructose 2,6-bisphosphate</name>
  <description>D-D-d-fructose 2,6-bisphosphate, also known as d-fructose 2,6-bisphosphate, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. D-D-d-fructose 2,6-bisphosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). D-D-d-fructose 2,6-bisphosphate exists in all living species, ranging from bacteria to humans. D-D-d-fructose 2,6-bisphosphate can be converted into fructose 6-phosphate; which is mediated by the enzyme 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1. In cattle, D-d-fructose 2,6-bisphosphate is involved in the metabolic pathway called the fructose and mannose degradation pathway.</description>
  <synonyms>
    <synonym>2,6-Di-O-phosphono-beta-D-fructofuranose</synonym>
    <synonym>2,6-Di-O-phosphono-b-D-fructofuranose</synonym>
    <synonym>2,6-Di-O-phosphono-β-D-fructofuranose</synonym>
    <synonym>D-Fructose 2,6-bisphosphoric acid</synonym>
    <synonym>b-D-Fructose 2,6-bisphosphate</synonym>
    <synonym>beta-D-Fructose 2,6-bisphosphate</synonym>
    <synonym>Fru 2,6-P2, fructose 2,6-diphosphate</synonym>
    <synonym>Fructose 2,6-bisphosphate</synonym>
    <synonym>Fructose 2,6-biphosphate</synonym>
    <synonym>Fructose 2,6-diphosphate</synonym>
    <synonym>Phosphofructokinase activation factor</synonym>
    <synonym>Phosphofructokinase activator</synonym>
    <synonym>Fructose-2,6-diphosphate</synonym>
  </synonyms>
  <chemical_formula>C6H14O12P2</chemical_formula>
  <average_molecular_weight>340.1157</average_molecular_weight>
  <monisotopic_moleculate_weight>339.996048936</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>fructose-2,6-diphosphate</traditional_iupac>
  <cas_registry_number>79082-92-1</cas_registry_number>
  <smiles>OC[C@@]1(OP(O)(O)=O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H14O12P2/c7-2-6(18-20(13,14)15)5(9)4(8)3(17-6)1-16-19(10,11)12/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1</inchi>
  <inchikey>YXWOAJXNVLXPMU-ZXXMMSQZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D-fructofuranose 2,6-bisphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>340.1157</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>339.996048936</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@]1(OP(O)(O)=O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H14O12P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H14O12P2/c7-2-6(18-20(13,14)15)5(9)4(8)3(17-6)1-16-19(10,11)12/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YXWOAJXNVLXPMU-ZXXMMSQZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>203.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>58.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99646</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00665</kegg_id>
  <chemspider_id>94762</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB022390</foodb_id>
  <pubchem_compound_id>105021</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28602</chebi_id>
  <meta_cyc_id/>
  <knapsack_id>C00007441</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35645</bigg_id>
  <wikipedia_id>Fructose_2,6-bisphosphate</wikipedia_id>
  <metlin_id>5964</metlin_id>
  <synthesis_reference>Shulman, Hagit; Makarov, Carina; Ogawa, Anthony K.; Romesberg, Floyd; Keinan, Ehud. Chemically Reactive Immunogens Lead to Functional Convergence of the Immune Response. Journal of the American Chemical Society (2000), 122(44), 10743-10753.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00140</protein_accession>
      <name>6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 1</name>
      <uniprot_id>P49872</uniprot_id>
      <gene_name>PFKFB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00155</protein_accession>
      <name>6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 3</name>
      <uniprot_id>Q28901</uniprot_id>
      <gene_name>PFKFB3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00162</protein_accession>
      <name>6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 2</name>
      <uniprot_id>P26285</uniprot_id>
      <gene_name>PFKFB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01129</protein_accession>
      <name>Probable fructose-2,6-bisphosphatase TIGAR</name>
      <uniprot_id>Q1JQA7</uniprot_id>
      <gene_name>TIGAR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:22 UTC</creation_date>
  <update_date>2020-04-15 22:23:07 UTC</update_date>
  <accession>BMDB0001049</accession>
  <secondary_accessions>
    <accession>BMDB01049</accession>
  </secondary_accessions>
  <name>Gamma-Glutamylcysteine</name>
  <description/>
  <synonyms>
    <synonym>5-L-Glutamyl-L-cysteine</synonym>
    <synonym>gamma-Glu-cys</synonym>
    <synonym>gamma-L-Glutamyl-L-cysteine</synonym>
    <synonym>L-gamma-Glutamylcysteine</synonym>
    <synonym>g-Glu-cys</synonym>
    <synonym>Γ-glu-cys</synonym>
    <synonym>g-L-Glutamyl-L-cysteine</synonym>
    <synonym>Γ-L-glutamyl-L-cysteine</synonym>
    <synonym>L-g-Glutamylcysteine</synonym>
    <synonym>L-Γ-glutamylcysteine</synonym>
    <synonym>g-Glutamylcysteine</synonym>
    <synonym>Γ-glutamylcysteine</synonym>
    <synonym>Γ-L-glu-L-cys</synonym>
    <synonym>L-Γ-glutamyl-L-cysteine</synonym>
    <synonym>N-Γ-glutamylcysteine</synonym>
    <synonym>N-L-Γ-glutamylcysteine</synonym>
    <synonym>N-L-Γ-glutamyl-L-cysteine</synonym>
    <synonym>gamma-L-Glu-L-cys</synonym>
    <synonym>L-gamma-Glutamyl-L-cysteine</synonym>
    <synonym>N-gamma-Glutamylcysteine</synonym>
    <synonym>N-L-gamma-Glutamylcysteine</synonym>
    <synonym>N-L-gamma-Glutamyl-L-cysteine</synonym>
    <synonym>5-L-Glutamylcysteine</synonym>
    <synonym>H-gamma-Glu-cys-OH</synonym>
    <synonym>L-g-Glutamyl-L-cysteine</synonym>
    <synonym>N-Γ-L-glutamyl-L-cysteine</synonym>
    <synonym>gamma-Glutamylcysteine</synonym>
  </synonyms>
  <chemical_formula>C8H14N2O5S</chemical_formula>
  <average_molecular_weight>250.272</average_molecular_weight>
  <monisotopic_moleculate_weight>250.062342258</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid</iupac_name>
  <traditional_iupac>gamma-glutamylcysteine</traditional_iupac>
  <cas_registry_number>636-58-8</cas_registry_number>
  <smiles>N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1</inchi>
  <inchikey>RITKHVBHSGLULN-WHFBIAKZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cysteine and derivatives</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Cysteine or derivatives</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>gamma-glutamylcysteine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>250.272</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>250.062342258</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H14N2O5S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RITKHVBHSGLULN-WHFBIAKZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>129.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>56.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutathione Metabolism</name>
      <smpdb_id>SMP0087167</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179318</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00669</kegg_id>
  <chemspider_id>110467</chemspider_id>
  <drugbank_id>DB03408</drugbank_id>
  <foodb_id>FDB003603</foodb_id>
  <pubchem_compound_id>123938</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17515</chebi_id>
  <meta_cyc_id>L-GAMMA-GLUTAMYLCYSTEINE</meta_cyc_id>
  <knapsack_id>C00007507</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35655</bigg_id>
  <wikipedia_id>Gamma-Glutamylcysteine</wikipedia_id>
  <metlin_id>5966</metlin_id>
  <synthesis_reference>Bridge, Wallace John; Zarka, Martin Hani. Enzymic production of g-glutamylcysteine. PCT Int. Appl. (2006), 76pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00197</protein_accession>
      <name>Glutathione synthetase</name>
      <uniprot_id>Q5EAC2</uniprot_id>
      <gene_name>GSS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:23 UTC</creation_date>
  <update_date>2020-03-13 16:25:33 UTC</update_date>
  <accession>BMDB0001050</accession>
  <secondary_accessions>
    <accession>BMDB01050</accession>
  </secondary_accessions>
  <name>Hypochlorite</name>
  <description/>
  <synonyms>
    <synonym>[ClOH]</synonym>
    <synonym>Chlor(I)-saeure</synonym>
    <synonym>HClO</synonym>
    <synonym>HOCl</synonym>
    <synonym>Hypochloric acid</synonym>
    <synonym>Hypochlorige saeure</synonym>
    <synonym>Hypochlate</synonym>
    <synonym>Hypochlic acid</synonym>
    <synonym>Hypochlorous acids</synonym>
    <synonym>Hypochlorite</synonym>
  </synonyms>
  <chemical_formula>ClHO</chemical_formula>
  <average_molecular_weight>52.46</average_molecular_weight>
  <monisotopic_moleculate_weight>51.971592361</monisotopic_moleculate_weight>
  <iupac_name>hypochlorous acid</iupac_name>
  <traditional_iupac>hypochlorous acid</traditional_iupac>
  <cas_registry_number>14380-61-1</cas_registry_number>
  <smiles>OCl</smiles>
  <inchi>InChI=1S/ClHO/c1-2/h2H</inchi>
  <inchikey>QWPPOHNGKGFGJK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as non-metal hypochlorites. These are inorganic non-metallic compounds containing a hypochlorite as its largest oxoanion.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Non-metal oxoanionic compounds</class>
    <sub_class>Non-metal hypochlorites</sub_class>
    <direct_parent>Non-metal hypochlorites</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Non-metal hypochlorite</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>an inorganic compound</external_descriptor>
      <external_descriptor>chlorine oxoacid</external_descriptor>
      <external_descriptor>reactive oxygen species</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-5.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>hypochlorous acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>52.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>51.971592361</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCl</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>ClHO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/ClHO/c1-2/h2H</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QWPPOHNGKGFGJK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>8.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>3.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>36791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33269</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33271</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C19697</kegg_id>
  <chemspider_id/>
  <foodb_id>FDB022391</foodb_id>
  <pubchem_compound_id>24341</pubchem_compound_id>
  <chebi_id>24757</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Hypochlorous acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Taylor, M. C. Hypochlorites. (1926), US 1609328 19261207 CAN 21:2408 AN 1927:2408</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:24 UTC</creation_date>
  <update_date>2020-04-15 22:23:08 UTC</update_date>
  <accession>BMDB0001051</accession>
  <secondary_accessions>
    <accession>BMDB01051</accession>
  </secondary_accessions>
  <name>Glyceraldehyde</name>
  <description>Glyceraldehyde, also known as aldotriose or glycerose, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. Glyceraldehyde exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Glyceraldehyde exists in all living species, ranging from bacteria to humans. Glyceraldehyde is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(+-)-Glyceraldehyde</synonym>
    <synonym>2,3-Dihydroxypropanal</synonym>
    <synonym>2,3-Dihydroxypropionaldehyde</synonym>
    <synonym>Aldotriose</synonym>
    <synonym>alpha,beta-Dihydroxypropionaldehyde</synonym>
    <synonym>DL-Glyceraldehyde</synonym>
    <synonym>Gliceraldehido</synonym>
    <synonym>Glyceraldehyd</synonym>
    <synonym>Glyceric aldehyde</synonym>
    <synonym>Glycerinaldehyd</synonym>
    <synonym>Glycerinaldehyde</synonym>
    <synonym>Glycerinformal</synonym>
    <synonym>Glycerose</synonym>
    <synonym>Glyzerinaldehyd</synonym>
    <synonym>a,b-Dihydroxypropionaldehyde</synonym>
    <synonym>Α,β-dihydroxypropionaldehyde</synonym>
    <synonym>(+/-)-2,3-dihydroxy-propanal</synonym>
    <synonym>(+/-)-glyceraldehyde</synonym>
    <synonym>D-(+)-Glyceraldehyde</synonym>
    <synonym>D-2,3-Dihydroxypropanal</synonym>
    <synonym>D-2,3-Dihydroxypropionaldehyde</synonym>
    <synonym>D-Aldotriose</synonym>
    <synonym>D-Glyceraldehyde</synonym>
    <synonym>D-Glycerose</synonym>
    <synonym>delta-(+)-Glyceraldehyde</synonym>
    <synonym>delta-2,3-Dihydroxypropanal</synonym>
    <synonym>delta-2,3-Dihydroxypropionaldehyde</synonym>
    <synonym>delta-Aldotriose</synonym>
    <synonym>delta-Glyceraldehyde</synonym>
    <synonym>delta-Glycerose</synonym>
    <synonym>Dihydroxypropionaldehyde</synonym>
  </synonyms>
  <chemical_formula>C3H6O3</chemical_formula>
  <average_molecular_weight>90.0779</average_molecular_weight>
  <monisotopic_moleculate_weight>90.031694058</monisotopic_moleculate_weight>
  <iupac_name>2,3-dihydroxypropanal</iupac_name>
  <traditional_iupac>(+/-)-glyceraldehyde</traditional_iupac>
  <cas_registry_number>56-82-6</cas_registry_number>
  <smiles>OCC(O)C=O</smiles>
  <inchi>InChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2</inchi>
  <inchikey>MNQZXJOMYWMBOU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharides</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Alpha-hydroxyaldehydes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain aldehydes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxyaldehyde</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain aldehyde</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>DL-glyceraldehyde</external_descriptor>
      <external_descriptor>aldotriose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>145 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>17 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,3-dihydroxypropanal</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>90.0779</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>90.031694058</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(O)C=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H6O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MNQZXJOMYWMBOU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>19.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440063</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By GC-TOFMS and UPLC-QTOFMS</comment>
      <references>
        <reference>
          <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
          <pubmed_id>27999311</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02154</kegg_id>
  <foodb_id>FDB022392</foodb_id>
  <chemspider_id>731</chemspider_id>
  <pubchem_compound_id>751</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>5445</chebi_id>
  <knapsack_id>C00007413</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35402</bigg_id>
  <wikipedia_id>Glyceraldehyde</wikipedia_id>
  <metlin_id>4176</metlin_id>
  <meta_cyc_id>CPD0-1551</meta_cyc_id>
  <synthesis_reference>Wan, Xin-Jun; Song, Ming-You; Wu, Rong; Chu, Dao-Bao.  Synthesis of glyceraldehyde by indirect electrooxidation.    Yingyong Huaxue  (2003),  20(6),  578-581.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
      <pubmed_id>27999311</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:26 UTC</creation_date>
  <update_date>2020-03-13 16:25:35 UTC</update_date>
  <accession>BMDB0001052</accession>
  <secondary_accessions>
    <accession>BMDB01052</accession>
  </secondary_accessions>
  <name>(S)-3-Hydroxyisobutyryl-CoA</name>
  <description/>
  <synonyms>
    <synonym>(S)-3-Hydroxyisobutyryl-coenzyme A</synonym>
    <synonym>3-Hydroxy-2-methylpropanoyl-CoA</synonym>
    <synonym>3-Hydroxy-2-methylpropanoyl-coenzyme A</synonym>
    <synonym>3-Hydroxy-2-methylpropionyl-CoA</synonym>
    <synonym>3-Hydroxy-2-methylpropionyl-coenzyme A</synonym>
    <synonym>3-Hydroxy-isobutyryl-CoA</synonym>
    <synonym>3-Hydroxy-isobutyryl-coenzyme A</synonym>
    <synonym>3-Hydroxyisobutyryl-CoA</synonym>
    <synonym>3-Hydroxyisobutyryl-coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C25H42N7O18P3S</chemical_formula>
  <average_molecular_weight>853.623</average_molecular_weight>
  <monisotopic_moleculate_weight>853.151987801</monisotopic_moleculate_weight>
  <iupac_name>{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>319440-43-2</cas_registry_number>
  <smiles>CC(CO)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12</smiles>
  <inchi>InChI=1S/C25H42N7O18P3S/c1-13(8-33)24(38)54-7-6-27-15(34)4-5-28-22(37)19(36)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-18(49-51(39,40)41)17(35)23(48-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-14,17-19,23,33,35-36H,4-10H2,1-3H3,(H,27,34)(H,28,37)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)</inchi>
  <inchikey>WWEOGFZEFHPUAM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>853.623</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>853.151987801</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(CO)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H42N7O18P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C25H42N7O18P3S/c1-13(8-33)24(38)54-7-6-27-15(34)4-5-28-22(37)19(36)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-18(49-51(39,40)41)17(35)23(48-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-14,17-19,23,33,35-36H,4-10H2,1-3H3,(H,27,34)(H,28,37)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WWEOGFZEFHPUAM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>383.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>183.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>74.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29941</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C06000</kegg_id>
  <chemspider_id>86</chemspider_id>
  <foodb_id>FDB022393</foodb_id>
  <pubchem_compound_id>88</pubchem_compound_id>
  <chebi_id>28259</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>47176</bigg_id>
  <wikipedia_id/>
  <metlin_id>453</metlin_id>
  <synthesis_reference>Hawes, John W.; Harper, Edwin T.  Synthesis of methacrylyl-CoA and (R)- and (S)-3-hydroxyisobutyryl-CoA.    Methods in Enzymology  (2000),  324(Branched-Chain Amino Acids),  73-79.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00549</protein_accession>
      <name>3-hydroxyisobutyryl-CoA hydrolase, mitochondrial</name>
      <uniprot_id>Q2HJ73</uniprot_id>
      <gene_name>HIBCH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:27 UTC</creation_date>
  <update_date>2020-03-13 16:25:35 UTC</update_date>
  <accession>BMDB0001054</accession>
  <secondary_accessions>
    <accession>BMDB01054</accession>
  </secondary_accessions>
  <name>Dolichyl b-D-glucosyl phosphate</name>
  <description/>
  <synonyms>
    <synonym>Dolichyl b-D-glucosyl phosphoric acid</synonym>
    <synonym>Dolichol monophosphate glucose</synonym>
    <synonym>Dolichyl b-delta-glucosyl phosphate</synonym>
    <synonym>Dolichyl beta-D-glucosyl phosphate</synonym>
    <synonym>Dolichyl beta-delta-glucosyl phosphate</synonym>
    <synonym>Dolichyl monophosphate glucose</synonym>
    <synonym>Dolichyl phosphate glucose</synonym>
    <synonym>Dolichylphosphoryl glucose</synonym>
  </synonyms>
  <chemical_formula>C21H39O9P</chemical_formula>
  <average_molecular_weight>466.5027</average_molecular_weight>
  <monisotopic_moleculate_weight>466.233169358</monisotopic_moleculate_weight>
  <iupac_name>{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}({[(6Z)-3,7,11-trimethyldodeca-6,10-dien-1-yl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>dolichyl phosphate glucose</traditional_iupac>
  <cas_registry_number>220496-27-5</cas_registry_number>
  <smiles>OC[C@H]1O[C@@H](OP(=O)(O)OCCC(C)CC\C=C(\C)CCC=C(C)C)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C21H39O9P/c1-14(2)7-5-8-15(3)9-6-10-16(4)11-12-28-31(26,27)30-21-20(25)19(24)18(23)17(13-22)29-21/h7,9,16-25H,5-6,8,10-13H2,1-4H3,(H,26,27)/b15-9-/t16?,17-,18-,19+,20-,21+/m1/s1</inchi>
  <inchikey>RHJMCOLWMXJOGE-ZTZGTLKASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Sesquiterpenoids</sub_class>
    <direct_parent>Sesquiterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Dialkyl phosphates</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Dialkyl phosphate</substituent>
      <substituent>Farsesane sesquiterpenoid</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sesquiterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}({[(6Z)-3,7,11-trimethyldodeca-6,10-dien-1-yl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>466.5027</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>466.233169358</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@@H](OP(=O)(O)OCCC(C)CC\C=C(\C)CCC=C(C)C)[C@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H39O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H39O9P/c1-14(2)7-5-8-15(3)9-6-10-16(4)11-12-28-31(26,27)30-21-20(25)19(24)18(23)17(13-22)29-21/h7,9,16-25H,5-6,8,10-13H2,1-4H3,(H,26,27)/b15-9-/t16?,17-,18-,19+,20-,21+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RHJMCOLWMXJOGE-ZTZGTLKASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>145.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>117.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>48.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360747</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01246</kegg_id>
  <chemspider_id>17216044</chemspider_id>
  <foodb_id>FDB022394</foodb_id>
  <pubchem_compound_id>22833557</pubchem_compound_id>
  <chebi_id>15812</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>1809280</bigg_id>
  <wikipedia_id/>
  <metlin_id>5969</metlin_id>
  <synthesis_reference>Rush, Jeffrey S.; Van Leyen, Klaus; Ouerfelli, Ouathek; Wolucka, Beata; Waechter, Charles J.  Transbilayer movement of Glc-P-dolichol and its function as a glucosyl donor: protein-mediated transport of a water-soluble analog into sealed ER vesicles from pig brain.    Glycobiology  (1998),  8(12),  1195-1205.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:28 UTC</creation_date>
  <update_date>2020-04-15 22:14:53 UTC</update_date>
  <accession>BMDB0001056</accession>
  <secondary_accessions>
    <accession>BMDB01056</accession>
  </secondary_accessions>
  <name>Dihydrofolic acid</name>
  <description>Dihydrofolic acid, also known as Dihydrofolic acid or dihydrofolic acid, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Dihydrofolic acid is possibly soluble (in water) and a strong basic compound (based on its pKa). Dihydrofolic acid exists in all eukaryotes, ranging from yeast to humans. Dihydrofolic acid participates in a number of enzymatic reactions, within cattle. In particular, Dihydrofolic acid can be biosynthesized from tetrahydrofolic acid; which is catalyzed by the enzyme dihydrofolic acid reductase. In addition, Dihydrofolic acid can be converted into folic acid; which is mediated by the enzyme dihydrofolic acid reductase. In cattle, dihydrofolic acid is involved in the metabolic pathway called the folate metabolism pathway.</description>
  <synonyms>
    <synonym>7,8-Dihydrofolate</synonym>
    <synonym>7,8-Dihydrofolic acid</synonym>
    <synonym>7,8-Dihydropteroylglutamate</synonym>
    <synonym>Dihydrofolate</synonym>
    <synonym>N-(7,8-Dihydropteroyl)-L-glutamic acid</synonym>
    <synonym>7,8-Dihydropteroylglutamic acid</synonym>
    <synonym>N-(7,8-Dihydropteroyl)-L-glutamate</synonym>
    <synonym>7,8-Dihydro-L-folic acid</synonym>
    <synonym>H2PteGlu</synonym>
    <synonym>H2PteGlu1</synonym>
    <synonym>L-N-[p-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-glutamic acid</synonym>
    <synonym>N-(4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid</synonym>
    <synonym>N-(4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid</synonym>
    <synonym>N-[4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid</synonym>
    <synonym>N-[4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid</synonym>
    <synonym>Vitamin b9</synonym>
    <synonym>Dihydrofolate, (D)-isomer</synonym>
  </synonyms>
  <chemical_formula>C19H21N7O6</chemical_formula>
  <average_molecular_weight>443.4133</average_molecular_weight>
  <monisotopic_moleculate_weight>443.155331439</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-[(4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</iupac_name>
  <traditional_iupac>dihydrofolic acid</traditional_iupac>
  <cas_registry_number>4033-27-6</cas_registry_number>
  <smiles>NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=N2)N1</smiles>
  <inchi>InChI=1S/C19H21N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1</inchi>
  <inchikey>OZRNSSUDZOLUSN-LBPRGKRZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Glutamic acid and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminobenzamides</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hippuric acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Ketimines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalkylamines</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pterins and derivatives</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Aminobenzamide</substituent>
      <substituent>Aminobenzoic acid or derivatives</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzamide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoic acid or derivatives</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hippuric acid</substituent>
      <substituent>Hippuric acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imine</substituent>
      <substituent>Ketimine</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylalkylamine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pteridine</substituent>
      <substituent>Pterin</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dihydrofolic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-[(4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>443.4133</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>443.155331439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=N2)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H21N7O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H21N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OZRNSSUDZOLUSN-LBPRGKRZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>207.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>120.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>44.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22988</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29788</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00415</kegg_id>
  <chemspider_id>89228</chemspider_id>
  <foodb_id>FDB022395</foodb_id>
  <pubchem_compound_id>98792</pubchem_compound_id>
  <chebi_id>15633</chebi_id>
  <drugbank_id>DB02015</drugbank_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id>C00007248</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34911</bigg_id>
  <wikipedia_id>Dihydrofolic acid</wikipedia_id>
  <metlin_id>5970</metlin_id>
  <synthesis_reference>Smith, Karin; Scrimgeour, K. G.; Huennekens, F. M.  Folic acid coenzymes and one-carbon metabolism. XV. Synthesis of a new form of dihydrofolate.    Biochemical and Biophysical Research Communications  (1963),  11(5),  388-92.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00536</protein_accession>
      <name>Thymidylate synthase</name>
      <uniprot_id>Q2TA32</uniprot_id>
      <gene_name>TYMS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00821</protein_accession>
      <name>Dihydrofolate reductase</name>
      <uniprot_id>P00376</uniprot_id>
      <gene_name>DHFR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:29 UTC</creation_date>
  <update_date>2020-03-13 16:25:36 UTC</update_date>
  <accession>BMDB0001057</accession>
  <secondary_accessions>
    <accession>BMDB01057</accession>
  </secondary_accessions>
  <name>3-Methylglutaconyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>3-Methylglutaconyl-coenzyme A</synonym>
    <synonym>trans-3-Methylglutaconyl-CoA</synonym>
    <synonym>trans-3-Methylglutaconyl-coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C27H42N7O19P3S</chemical_formula>
  <average_molecular_weight>893.644</average_molecular_weight>
  <monisotopic_moleculate_weight>893.146902423</monisotopic_moleculate_weight>
  <iupac_name>(3E)-5-{[2-(3-{3-[({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-3-methyl-5-oxopent-3-enoic acid</iupac_name>
  <traditional_iupac>(3E)-5-({2-[3-(3-{[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-3-methyl-5-oxopent-3-enoic acid</traditional_iupac>
  <cas_registry_number>6247-73-0</cas_registry_number>
  <smiles>C\C(CC(O)=O)=C/C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12</smiles>
  <inchi>InChI=1S/C27H42N7O19P3S/c1-14(8-17(36)37)9-18(38)57-7-6-29-16(35)4-5-30-25(41)22(40)27(2,3)11-50-56(47,48)53-55(45,46)49-10-15-21(52-54(42,43)44)20(39)26(51-15)34-13-33-19-23(28)31-12-32-24(19)34/h9,12-13,15,20-22,26,39-40H,4-8,10-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,45,46)(H,47,48)(H2,28,31,32)(H2,42,43,44)/b14-9+</inchi>
  <inchikey>GXKSHRDAHFLWPN-NTEUORMPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3E)-5-{[2-(3-{3-[({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-3-methyl-5-oxopent-3-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>893.644</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>893.146902423</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C\C(CC(O)=O)=C/C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H42N7O19P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H42N7O19P3S/c1-14(8-17(36)37)9-18(38)57-7-6-29-16(35)4-5-30-25(41)22(40)27(2,3)11-50-56(47,48)53-55(45,46)49-10-15-21(52-54(42,43)44)20(39)26(51-15)34-13-33-19-23(28)31-12-32-24(19)34/h9,12-13,15,20-22,26,39-40H,4-8,10-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,45,46)(H,47,48)(H2,28,31,32)(H2,42,43,44)/b14-9+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GXKSHRDAHFLWPN-NTEUORMPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>400.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>193.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>78.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338517</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03231</kegg_id>
  <chemspider_id>11471767</chemspider_id>
  <foodb_id>FDB022396</foodb_id>
  <pubchem_compound_id>5462214</pubchem_compound_id>
  <chebi_id>15488</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>41450</bigg_id>
  <wikipedia_id>3-Methylglutaconyl-CoA</wikipedia_id>
  <metlin_id>5971</metlin_id>
  <synthesis_reference>Hermans-Lokkerbol, Ank; van der Heijden, Robert; Verpoorte, Robert.  Isocratic high-performance liquid chromatography of coenzyme A esters involved in the metabolism of 3S-hydroxy-3-methylglutaryl-coenzyme A. Detection of related enzyme activities in Catharanthus roseus plant cell cultures.    Journal of Chromatography, A  (1996),  752(1+2),  123-130.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:30 UTC</creation_date>
  <update_date>2020-04-14 22:48:49 UTC</update_date>
  <accession>BMDB0001058</accession>
  <secondary_accessions>
    <accession>BMDB01058</accession>
  </secondary_accessions>
  <name>Fructose 1,6-bisphosphate</name>
  <description>Fructose 1,6-bisphosphate belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. Fructose 1,6-bisphosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).</description>
  <synonyms>
    <synonym>1,6-Di-O-phosphono-beta-D-fructofuranose</synonym>
    <synonym>BETA FRUCTOSE 1,6-diphosphATE</synonym>
    <synonym>beta-D-Fructose 1,6-bisphosphate</synonym>
    <synonym>Fosfructose</synonym>
    <synonym>1,6-Di-O-phosphono-b-D-fructofuranose</synonym>
    <synonym>1,6-Di-O-phosphono-β-D-fructofuranose</synonym>
    <synonym>b FRUCTOSE 1,6-diphosphate</synonym>
    <synonym>b FRUCTOSE 1,6-diphosphoric acid</synonym>
    <synonym>beta FRUCTOSE 1,6-diphosphoric acid</synonym>
    <synonym>Β fructose 1,6-diphosphate</synonym>
    <synonym>Β fructose 1,6-diphosphoric acid</synonym>
    <synonym>b-D-Fructose 1,6-bisphosphate</synonym>
    <synonym>b-D-Fructose 1,6-bisphosphoric acid</synonym>
    <synonym>beta-D-Fructose 1,6-bisphosphoric acid</synonym>
    <synonym>Β-D-fructose 1,6-bisphosphate</synonym>
    <synonym>Β-D-fructose 1,6-bisphosphoric acid</synonym>
    <synonym>Fructose 1,6-bisphosphoric acid</synonym>
    <synonym>Fructose-1,6-diphosphate</synonym>
    <synonym>Fructose-1,6-diphosphate, calcium salt</synonym>
    <synonym>Fructose-1,6-diphosphate, disodium salt</synonym>
    <synonym>Fructose-1,6-diphosphate, trisodium salt</synonym>
    <synonym>Fructose-1,6-diphosphate, 2-(18)O-labeled</synonym>
    <synonym>Fructose-1,6-diphosphate, calcium (1:2) salt</synonym>
    <synonym>Fructose-1,6-diphosphate, monosodium salt</synonym>
    <synonym>Strontium fructose 1,6-diphosphate</synonym>
    <synonym>SR-FDP</synonym>
    <synonym>Fructose 1,6-diphosphate</synonym>
    <synonym>Fructose-1,6-diphosphate, (L)-isomer</synonym>
    <synonym>Fructose-1,6-diphosphate, (alpha-D)-isomer</synonym>
    <synonym>Fructose-1,6-diphosphate, barium (1:2) salt</synonym>
    <synonym>Fructose-1,6-diphosphate, sodium salt, monohydrate</synonym>
    <synonym>Fructose-1,6-diphosphate, tetrasodium salt</synonym>
    <synonym>Strontium fructose-1,6-diphosphate</synonym>
    <synonym>Fructose-1,6-diphosphate magnesium salt</synonym>
    <synonym>Fructose-1,6-diphosphate, (beta-D)-isomer</synonym>
    <synonym>Fructose-1,6-diphosphate, tetrapotassium salt</synonym>
    <synonym>D-Fructose 1,6-biphosphate</synonym>
    <synonym>D-Fructose 1,6-bisphosphate</synonym>
    <synonym>D-Fructose 1,6-diphosphate</synonym>
    <synonym>Diphosphofructose</synonym>
    <synonym>Fructose 1,6-bis(dihydrogen phosphate)</synonym>
    <synonym>beta-D-Fructofuranose 1,6-bisphosphate</synonym>
    <synonym>beta-D-Fructofuranose 1,6-diphosphate</synonym>
    <synonym>beta-D-Fructose 1,6-diphosphate</synonym>
    <synonym>Β-D-fructofuranose 1,6-bisphosphate</synonym>
    <synonym>Β-D-fructofuranose 1,6-diphosphate</synonym>
    <synonym>Β-D-fructose 1,6-diphosphate</synonym>
    <synonym>Fructose 1,6-bisphosphate</synonym>
    <synonym>b-D-Fructofuranose 1,6-bisphosphate</synonym>
    <synonym>b-D-Fructofuranose 1,6-bisphosphoric acid</synonym>
    <synonym>beta-D-Fructofuranose 1,6-bisphosphoric acid</synonym>
    <synonym>Β-D-fructofuranose 1,6-bisphosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C6H14O12P2</chemical_formula>
  <average_molecular_weight>340.1157</average_molecular_weight>
  <monisotopic_moleculate_weight>339.996048936</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxyphosphonic acid</traditional_iupac>
  <cas_registry_number>34693-15-7</cas_registry_number>
  <smiles>O[C@H]1[C@H](O)[C@@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6-/m1/s1</inchi>
  <inchikey>RNBGYGVWRKECFJ-ARQDHWQXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D-fructofuranose 1,6-bisphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>340.1157</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>339.996048936</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@H](O)[C@@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H14O12P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RNBGYGVWRKECFJ-ARQDHWQXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>203.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>58.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>36588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>48214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31753</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fermented milk, by capillary electrophoresis-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
          <pubmed_id>26686724</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C05378</kegg_id>
  <chemspider_id>9848</chemspider_id>
  <foodb_id>FDB022397</foodb_id>
  <pubchem_compound_id>10267</pubchem_compound_id>
  <chebi_id>28013</chebi_id>
  <drugbank_id>DB04551</drugbank_id>
  <pdbe_id>BFP</pdbe_id>
  <meta_cyc_id>FRUCTOSE-16-DIPHOSPHATE</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Fructose 1,6-bisphosphate</wikipedia_id>
  <metlin_id>147</metlin_id>
  <synthesis_reference>Yan, Weiqun.  Method for producing fructose-1,6-diphosphate (FDP).    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2005),   7 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Hagi T, Kobayashi M, Nomura M: Metabolome analysis of milk fermented by gamma-aminobutyric acid-producing Lactococcus lactis. J Dairy Sci. 2016 Feb;99(2):994-1001. doi: 10.3168/jds.2015-9945. Epub 2015 Dec 10.</reference_text>
      <pubmed_id>26686724</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00150</protein_accession>
      <name>Fructose-1,6-bisphosphatase isozyme 2</name>
      <uniprot_id>Q2KJJ9</uniprot_id>
      <gene_name>FBP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00176</protein_accession>
      <name>Fructose-1,6-bisphosphatase 1</name>
      <uniprot_id>Q3SZB7</uniprot_id>
      <gene_name>FBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00479</protein_accession>
      <name>6-phosphofructokinase, liver type</name>
      <uniprot_id>A1A4J1</uniprot_id>
      <gene_name>PFKL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00523</protein_accession>
      <name>6-phosphofructokinase, muscle type</name>
      <uniprot_id>Q0IIG5</uniprot_id>
      <gene_name>PFKM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00531</protein_accession>
      <name>Fructose-bisphosphate aldolase</name>
      <uniprot_id>A6QLL8</uniprot_id>
      <gene_name>ALDOA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00532</protein_accession>
      <name>Fructose-bisphosphate aldolase</name>
      <uniprot_id>Q3ZBY4</uniprot_id>
      <gene_name>ALDOC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00533</protein_accession>
      <name>Fructose-bisphosphate aldolase</name>
      <uniprot_id>A5PK73</uniprot_id>
      <gene_name>ALDOB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00534</protein_accession>
      <name>Fructose-bisphosphate aldolase B</name>
      <uniprot_id>Q3T0S5</uniprot_id>
      <gene_name>ALDOB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:31 UTC</creation_date>
  <update_date>2020-03-13 16:25:37 UTC</update_date>
  <accession>BMDB0001059</accession>
  <secondary_accessions>
    <accession>BMDB01059</accession>
  </secondary_accessions>
  <name>Inositol 1,3,4,5-tetraphosphate</name>
  <description>Inositol 1,3,4,5-tetraphosphate, also known as inositol 1,3,4,5-tetraphosphate, belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety. Inositol 1,3,4,5-tetraphosphate is possibly soluble (in water) and an extremely strong acidic compound (based on its pKa). Inositol 1,3,4,5-tetraphosphate participates in a number of enzymatic reactions, within cattle. In particular, Inositol 1,3,4,5-tetraphosphate can be converted into inositol 1,4,5-trisphosphate through its interaction with the enzyme multiple inositol polyphosphate phosphatase 1. In addition, Inositol 1,3,4,5-tetraphosphate can be biosynthesized from inositol 1,4,5-trisphosphate through its interaction with the enzyme inositol-trisphosphate 3-kinase a. In cattle, inositol 1,3,4,5-tetraphosphate is involved in the metabolic pathway called the inositol metabolism pathway.</description>
  <synonyms>
    <synonym>Inositol 1,3,4,5-tetraphosphoric acid</synonym>
    <synonym>1,3,4,5-Tetrakis(dihydrogen phosphate) myo-inositol</synonym>
    <synonym>1D-Myo-inositol 1,3,4,5-tetrakis(dihydrogen phosphate)</synonym>
    <synonym>1D-Myo-inositol 1,3,4,5-tetrakisphosphate</synonym>
    <synonym>D-Myo-inositol 1,3,4,5-tetrakisphosphate</synonym>
    <synonym>Inositol 1,3,4,5-tetrakis(phosphate)</synonym>
    <synonym>Inositol 1,3,4,5-tetrakisphosphate</synonym>
    <synonym>Inositol-(1,3,4,5)-tetrakisphosphate</synonym>
    <synonym>Inositol-1,3,4,5-tetrakisphosphate</synonym>
    <synonym>Inositol-1,3,4,5-tetraphosphate</synonym>
    <synonym>Ins-1,3,4,5-P4</synonym>
    <synonym>Myo-inositol 1,3,4,5-tetrakis(phosphate)</synonym>
    <synonym>Myo-inositol 1,3,4,5-tetraphosphate</synonym>
    <synonym>Myo-inositol, 1,3,4,5-tetrakis(dihydrogen phosphate)</synonym>
    <synonym>Myo-inositol-1,3,4,5-tetrakisphosphate</synonym>
    <synonym>[(2R,3S,5S,6S)-3,5-Dihydroxy-2,4,6-triphosphonooxycyclohexyl] dihydrogen phosphate</synonym>
    <synonym>Inositol-1,3,4,5-tetrakisphosphate, DL-isomer</synonym>
    <synonym>Ins(1,3,4,5)p(4)</synonym>
    <synonym>Inositol-1,3,4,5-tetrakisphosphate, D-isomer</synonym>
    <synonym>Ins(1,3,4,5)P4</synonym>
  </synonyms>
  <chemical_formula>C6H16O18P4</chemical_formula>
  <average_molecular_weight>500.0755</average_molecular_weight>
  <monisotopic_moleculate_weight>499.928709756</monisotopic_moleculate_weight>
  <iupac_name>{[(2S,3R,5S,6S)-2,6-dihydroxy-3,4,5-tris(phosphonooxy)cyclohexyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2S,3R,5S,6S)-2,6-dihydroxy-3,4,5-tris(phosphonooxy)cyclohexyl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>102850-29-3</cas_registry_number>
  <smiles>O[C@H]1C(OP(O)(O)=O)[C@H](O)[C@@H](OP(O)(O)=O)C(OP(O)(O)=O)[C@H]1OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C6H16O18P4/c7-1-3(21-25(9,10)11)2(8)5(23-27(15,16)17)6(24-28(18,19)20)4(1)22-26(12,13)14/h1-8H,(H2,9,10,11)(H2,12,13,14)(H2,15,16,17)(H2,18,19,20)/t1-,2-,3?,4-,5+,6?/m0/s1</inchi>
  <inchikey>CIPFCGZLFXVXBG-FTSGZOCFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Inositol phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclohexanols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Cyclohexanol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Inositol phosphate</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2S,3R,5S,6S)-2,6-dihydroxy-3,4,5-tris(phosphonooxy)cyclohexyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>500.0755</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>499.928709756</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1C(OP(O)(O)=O)[C@H](O)[C@@H](OP(O)(O)=O)C(OP(O)(O)=O)[C@H]1OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H16O18P4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H16O18P4/c7-1-3(21-25(9,10)11)2(8)5(23-27(15,16)17)6(24-28(18,19)20)4(1)22-26(12,13)14/h1-8H,(H2,9,10,11)(H2,12,13,14)(H2,15,16,17)(H2,18,19,20)/t1-,2-,3?,4-,5+,6?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CIPFCGZLFXVXBG-FTSGZOCFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>307.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087256</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327414</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01272</kegg_id>
  <chemspider_id>96919</chemspider_id>
  <foodb_id>FDB022398</foodb_id>
  <pubchem_compound_id>107758</pubchem_compound_id>
  <chebi_id>16783</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>37244</bigg_id>
  <wikipedia_id/>
  <metlin_id>5973</metlin_id>
  <synthesis_reference>DeSolms, S. Jane; Vacca, Joseph P.; Huff, Joel R.  The total synthesis of (±)-myo-inositol-1,3,4-triphosphate, (±)-myo-inositol-2,4,5-triphosphate and (±)-myo-inositol-1,3,4,5-tetraphosphate.    Tetrahedron Letters  (1987),  28(39),  4503-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00089</protein_accession>
      <name>Inositol-tetrakisphosphate 1-kinase</name>
      <uniprot_id>P0C0T1</uniprot_id>
      <gene_name>ITPK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:33 UTC</creation_date>
  <update_date>2020-03-13 16:25:38 UTC</update_date>
  <accession>BMDB0001060</accession>
  <secondary_accessions>
    <accession>BMDB01060</accession>
  </secondary_accessions>
  <name>Ubiquinol</name>
  <description>Ubiquinol 8 belongs to the class of organic compounds known as polyprenyl quinols. Polyprenyl quinols are compounds containing a polyisoprene chain attached to a quinol(hydroquinone) at the second ring position. Ubiquinol 8 is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Ubiquinol 8 exists in all living species, ranging from bacteria to humans. Ubiquinol 8 participates in a number of enzymatic reactions, within cattle. In particular, Ubiquinol 8 and dihydroxyacetone phosphate can be biosynthesized from coenzyme Q10 and glycerol 3-phosphate; which is mediated by the enzyme glycerol-3-phosphate dehydrogenase, mitochondrial. In addition, Ubiquinol 8 and fumaric acid can be biosynthesized from coenzyme Q10 and succinic acid through its interaction with the enzyme succinate dehydrogenase. In cattle, ubiquinol 8 is involved in the metabolic pathway called the mitochondrial electron transport chain pathway.</description>
  <synonyms>
    <synonym>Reduced coenzyme Q8</synonym>
    <synonym>Ubiquinol(8)</synonym>
    <synonym>Ubiquinol-8</synonym>
  </synonyms>
  <chemical_formula>C49H76O4</chemical_formula>
  <average_molecular_weight>729.1253</average_molecular_weight>
  <monisotopic_moleculate_weight>728.57436092</monisotopic_moleculate_weight>
  <iupac_name>2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]benzene-1,4-diol</iupac_name>
  <traditional_iupac>ubiquinol-8</traditional_iupac>
  <cas_registry_number>74075-00-6</cas_registry_number>
  <smiles>COC1=C(OC)C(O)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(C)=C1O</smiles>
  <inchi>InChI=1S/C49H76O4/c1-36(2)20-13-21-37(3)22-14-23-38(4)24-15-25-39(5)26-16-27-40(6)28-17-29-41(7)30-18-31-42(8)32-19-33-43(9)34-35-45-44(10)46(50)48(52-11)49(53-12)47(45)51/h20,22,24,26,28,30,32,34,50-51H,13-19,21,23,25,27,29,31,33,35H2,1-12H3/b37-22+,38-24+,39-26+,40-28+,41-30+,42-32+,43-34+</inchi>
  <inchikey>LOJUQFSPYHMHEO-SGHXUWJISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as polyprenyl quinols. Polyprenyl quinols are compounds containing a polyisoprene chain attached to a quinol(hydroquinone) at the second ring position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Quinone and hydroquinone lipids</sub_class>
    <direct_parent>Polyprenyl quinols</direct_parent>
    <alternative_parents>
      <alternative_parent>2-polyprenyl-6-methoxyphenols</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Dimethoxybenzenes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroquinones</alternative_parent>
      <alternative_parent>Meta cresols</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>Ortho cresols</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Tetraterpenoids</alternative_parent>
      <alternative_parent>Toluenes</alternative_parent>
      <alternative_parent>Ubiquinols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-polyprenyl-6-methoxyphenol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Dimethoxybenzene</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroquinone</substituent>
      <substituent>M-cresol</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>O-cresol</substituent>
      <substituent>O-dimethoxybenzene</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Polyprenylbenzoquinol</substituent>
      <substituent>Polyprenylphenol</substituent>
      <substituent>Tetraterpenoid</substituent>
      <substituent>Toluene</substituent>
      <substituent>Ubiquinol skeleton</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>polyprenylhydroquinone</external_descriptor>
      <external_descriptor>ubiquinol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>9.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>14.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]benzene-1,4-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>729.1253</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>728.57436092</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=C(OC)C(O)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(C)=C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C49H76O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C49H76O4/c1-36(2)20-13-21-37(3)22-14-23-38(4)24-15-25-39(5)26-16-27-40(6)28-17-29-41(7)30-18-31-42(8)32-19-33-43(9)34-35-45-44(10)46(50)48(52-11)49(53-12)47(45)51/h20,22,24,26,28,30,32,34,50-51H,13-19,21,23,25,27,29,31,33,35H2,1-12H3/b37-22+,38-24+,39-26+,40-28+,41-30+,42-32+,43-34+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LOJUQFSPYHMHEO-SGHXUWJISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>58.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>238.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>94.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1256260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1256261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1256262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1371439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1371440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1371441</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022399</foodb_id>
  <chemspider_id>24603698</chemspider_id>
  <pubchem_compound_id>25074411</pubchem_compound_id>
  <chebi_id>61682</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id>CPD-9956</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5974</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00097</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial</name>
      <uniprot_id>P42026</uniprot_id>
      <gene_name>NDUFS7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00099</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial</name>
      <uniprot_id>P17694</uniprot_id>
      <gene_name>NDUFS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00262</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IX89</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00263</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>P03887</uniprot_id>
      <gene_name>MT-ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00264</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q45LU7</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00265</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q6JTG2</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00266</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IXE1</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00267</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>B1NZU0</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00268</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45M50</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00269</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MI0</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00270</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q3L5H4</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00271</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45LG6</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00272</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1NZ26</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00273</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] flavoprotein 2, mitochondrial</name>
      <uniprot_id>P04394</uniprot_id>
      <gene_name>NDUFV2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00274</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q8HBP4</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00275</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0B8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00276</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>B1P0I6</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00277</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q6JTH0</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00278</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q45MJ0</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00279</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q85EA2</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00280</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q7JAL5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00281</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q8HC63</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00282</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q6QTH1</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00283</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q45MC5</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00284</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>Q7JAS5</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00285</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q8HC24</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00286</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0J6</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00287</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4L</name>
      <uniprot_id>Q3L5T0</uniprot_id>
      <gene_name>ND4L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00288</protein_accession>
      <name>NADH dehydrogenase subunit 4</name>
      <uniprot_id>C5IX88</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00289</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q3L5J7</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00290</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>Q85UJ0</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00291</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>B1P078</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00292</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>B1P0N6</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00293</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>Q7JAS9</uniprot_id>
      <gene_name>ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00294</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P092</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00295</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q45MX4</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00296</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>P03924</uniprot_id>
      <gene_name>MT-ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00297</protein_accession>
      <name>Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial</name>
      <uniprot_id>Q3T189</uniprot_id>
      <gene_name>SDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00298</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0N5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00299</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q6JTD6</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00300</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45LK5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00301</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>B1NZ92</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00302</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>A4ZI01</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00303</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>P03920</uniprot_id>
      <gene_name>MT-ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00304</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q85E90</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00305</protein_accession>
      <name>NADH-ubiquinone oxidoreductase 75 kDa subunit, mitochondrial</name>
      <uniprot_id>P15690</uniprot_id>
      <gene_name>NDUFS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00306</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q45M46</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00307</protein_accession>
      <name>NADH dehydrogenase subunit 4</name>
      <uniprot_id>C5IX62</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00308</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q45MC9</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00309</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45LU6</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00310</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>B1P044</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00311</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q45LV6</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00312</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>B1P0M6</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00313</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0M2</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00314</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q6QTH0</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00315</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q85BD6</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00316</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q6JTD5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00317</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4L</name>
      <uniprot_id>Q7JAS8</uniprot_id>
      <gene_name>ND4L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00318</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IX37</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00319</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>P03910</uniprot_id>
      <gene_name>MT-ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00320</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q45M85</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00321</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P027</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00322</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q8HAW7</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00323</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q6JTE4</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00324</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>Q45LU9</uniprot_id>
      <gene_name>ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00325</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MC8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00326</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4L</name>
      <uniprot_id>P03902</uniprot_id>
      <gene_name>MT-ND4L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00327</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45LV9</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00328</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q85BS9</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00329</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial</name>
      <uniprot_id>P23709</uniprot_id>
      <gene_name>NDUFS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00330</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q7JAT5</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00331</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>B1NZ38</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00332</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MW0</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00333</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q8HQD4</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00334</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q7JAS7</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00335</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MP5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00336</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>P03898</uniprot_id>
      <gene_name>MT-ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00337</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>P03892</uniprot_id>
      <gene_name>MT-ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00338</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q8HBM0</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00339</protein_accession>
      <name>Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial</name>
      <uniprot_id>P31039</uniprot_id>
      <gene_name>SDHA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00340</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>B1P0L9</uniprot_id>
      <gene_name>ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00341</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q7JAT6</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00342</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MA2</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00343</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1NZY8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00344</protein_accession>
      <name>Electron transfer flavoprotein-ubiquinone oxidoreductase, mitochondrial</name>
      <uniprot_id>Q2KIG0</uniprot_id>
      <gene_name>ETFDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00345</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 8, mitochondrial</name>
      <uniprot_id>P42028</uniprot_id>
      <gene_name>NDUFS8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00346</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q45MY2</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00347</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IXC8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00348</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial</name>
      <uniprot_id>P25708</uniprot_id>
      <gene_name>NDUFV1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00349</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1NZB7</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00350</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>Q85UI9</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00351</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>Q6QTG4</uniprot_id>
      <gene_name>ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00352</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q45LS1</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:34 UTC</creation_date>
  <update_date>2020-03-13 16:25:38 UTC</update_date>
  <accession>BMDB0001061</accession>
  <secondary_accessions>
    <accession>BMDB01061</accession>
  </secondary_accessions>
  <name>Iodate</name>
  <description/>
  <synonyms>
    <synonym>Iodic acid</synonym>
    <synonym>[IO3](-)</synonym>
    <synonym>IO3(-)</synonym>
    <synonym>Iodate (I2O62-)</synonym>
    <synonym>Iodate (io3(1-))</synonym>
    <synonym>Iodate anion</synonym>
    <synonym>Iodate ion</synonym>
    <synonym>Iodate ion (io31-)</synonym>
    <synonym>Iodate(1-)</synonym>
    <synonym>Iodic acid (hio3) ion(1-)</synonym>
    <synonym>Trioxidoiodate(1-)</synonym>
  </synonyms>
  <chemical_formula>H3IO3</chemical_formula>
  <average_molecular_weight>177.924</average_molecular_weight>
  <monisotopic_moleculate_weight>177.91159</monisotopic_moleculate_weight>
  <iupac_name>trihydroxyiodanediium</iupac_name>
  <traditional_iupac>trihydroxyiodanediium</traditional_iupac>
  <cas_registry_number>15454-31-6</cas_registry_number>
  <smiles>O[I++](O)O</smiles>
  <inchi>InChI=1S/H3IO3/c2-1(3)4/h2-4H/q+2</inchi>
  <inchikey>VNFOOPCKMZASMJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as other non-metal halides. These are inorganic compounds containing 'other non-metals' and halogen.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Other non-metal halides</class>
    <sub_class/>
    <direct_parent>Other non-metal halides</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Other non-metal halide</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>iupac</kind>
      <value>trihydroxyiodanediium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>177.924</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>177.91159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[I++](O)O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>H3IO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/H3IO3/c2-1(3)4/h2-4H/q+2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VNFOOPCKMZASMJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>21.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022400</foodb_id>
  <chemspider_id>76615</chemspider_id>
  <pubchem_compound_id>84927</pubchem_compound_id>
  <chebi_id>29226</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Iodate</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Scrabal, A.; Gruber, Josef.  Halogenoxy compounds. XII. Kinetics of the formation of iodate from iodine in presence of triiodide ion.    Monatshefte fuer Chemie  (1917),  37  535-48. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:35 UTC</creation_date>
  <update_date>2020-03-13 16:25:39 UTC</update_date>
  <accession>BMDB0001062</accession>
  <secondary_accessions>
    <accession>BMDB01062</accession>
  </secondary_accessions>
  <name>N-Acetyl-D-Glucosamine 6-Phosphate</name>
  <description>N-Acetyl-D-glucosamine 6-phosphate, also known as N-acetyl-D-glucosamine-6-p or n-acetyl-d-glucosamine 6-phosphate, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetyl-D-glucosamine 6-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-D-glucosamine 6-phosphate exists in all living species, ranging from bacteria to humans. N-Acetyl-D-glucosamine 6-phosphate participates in a number of enzymatic reactions, within cattle. In particular, N-Acetyl-D-glucosamine 6-phosphate can be biosynthesized from N-acetyl-D-glucosamine through its interaction with the enzyme N-acetyl-D-glucosamine kinase. In addition, N-Acetyl-D-glucosamine 6-phosphate can be converted into glucosamine 6-phosphate and acetic acid through the action of the enzyme putative N-acetyl-d-glucosamine 6-phosphatehosphate deacetylase. In cattle, N-acetyl-D-glucosamine 6-phosphate is involved in the metabolic pathway called the amino sugar metabolism pathway.</description>
  <synonyms>
    <synonym>2-Acetamido-2-deoxy-6-O-phosphono-D-glucopyranose</synonym>
    <synonym>N-Acetyl-D-glucosamine 6-phosphoric acid</synonym>
    <synonym>N-Acetyl-D-glucosamine-6-p</synonym>
    <synonym>N-Acetyl-D-glucosamine-6-phosphate</synonym>
    <synonym>N-Acetyl-glucosamine-6-p</synonym>
    <synonym>N-Acetyl-glucosamine-6-phosphate</synonym>
    <synonym>N-Acetylglucosamine-6-p</synonym>
    <synonym>N-Acetylglucosamine 6-phosphate</synonym>
    <synonym>GlcNAc6p</synonym>
  </synonyms>
  <chemical_formula>C8H16NO9P</chemical_formula>
  <average_molecular_weight>301.1877</average_molecular_weight>
  <monisotopic_moleculate_weight>301.056267627</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxyphosphonic acid</traditional_iupac>
  <cas_registry_number>18191-20-3</cas_registry_number>
  <smiles>CC(=O)N[C@H]1C(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C8H16NO9P/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H2,14,15,16)/t4-,5-,6-,7-,8?/m1/s1</inchi>
  <inchikey>BRGMHAYQAZFZDJ-RTRLPJTCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Acylaminosugars</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hexose phosphates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Acylaminosugar</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acyl-D-glucosamine 6-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>301.1877</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>301.056267627</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@H]1C(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16NO9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16NO9P/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H2,14,15,16)/t4-,5-,6-,7-,8?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BRGMHAYQAZFZDJ-RTRLPJTCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>165.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>57.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437268</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00357</kegg_id>
  <foodb_id>FDB022401</foodb_id>
  <chemspider_id>389821</chemspider_id>
  <pubchem_compound_id>440996</pubchem_compound_id>
  <chebi_id>15784</chebi_id>
  <drugbank_id>DB03951</drugbank_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00019661</knapsack_id>
  <bigg_id>34733</bigg_id>
  <wikipedia_id/>
  <metlin_id>5975</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00938</protein_accession>
      <name>Putative N-acetylglucosamine-6-phosphate deacetylase</name>
      <uniprot_id>A7MBC0</uniprot_id>
      <gene_name>AMDHD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:36 UTC</creation_date>
  <update_date>2020-03-13 16:25:39 UTC</update_date>
  <accession>BMDB0001063</accession>
  <secondary_accessions>
    <accession>BMDB01063</accession>
  </secondary_accessions>
  <name>3-Hexaprenyl-4,5-Dihydroxybenzoic acid</name>
  <description>3-Hexaprenyl-4,5-dihydroxybenzoic acid, also known as 3-hexaprenyl-4,5-dihydroxybenzoic acid or 3-hexaprenyl-4,5-dihydroxybenzoic acid, belongs to the class of organic compounds known as polyprenylbenzene-1,2-diols. Polyprenylbenzene-1,2-diols are compounds containing a polyisoprene chain attached to a catechol group. 3-Hexaprenyl-4,5-dihydroxybenzoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Hexaprenyl-4,5-dihydroxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. In cattle, 3-hexaprenyl-4,5-dihydroxybenzoic acid is involved in the metabolic pathway called ubiquinone biosynthesis pathway.</description>
  <synonyms>
    <synonym>3-Hexaprenyl-4,5-dihydroxybenzoate</synonym>
    <synonym>3,4-Dihydroxy-5-hexaprenylbenzoate</synonym>
    <synonym>3,4-Dihydroxy-5-hexaprenylbenzoic acid</synonym>
    <synonym>Dhhpba</synonym>
  </synonyms>
  <chemical_formula>C37H54O4</chemical_formula>
  <average_molecular_weight>562.8223</average_molecular_weight>
  <monisotopic_moleculate_weight>562.402210216</monisotopic_moleculate_weight>
  <iupac_name>3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4,5-dihydroxybenzoic acid</iupac_name>
  <traditional_iupac>dhhpba</traditional_iupac>
  <cas_registry_number>63975-40-6</cas_registry_number>
  <smiles>CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(O)C(O)=CC(=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C37H54O4/c1-27(2)13-8-14-28(3)15-9-16-29(4)17-10-18-30(5)19-11-20-31(6)21-12-22-32(7)23-24-33-25-34(37(40)41)26-35(38)36(33)39/h13,15,17,19,21,23,25-26,38-39H,8-12,14,16,18,20,22,24H2,1-7H3,(H,40,41)/b28-15+,29-17+,30-19+,31-21+,32-23+</inchi>
  <inchikey>VEPICJBQCOUQPI-IRVXXIIISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as polyprenylbenzene-1,2-diols. Polyprenylbenzene-1,2-diols are compounds containing a polyisoprene chain attached to a catechol group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Polyprenylphenols</sub_class>
    <direct_parent>Polyprenylbenzene-1,2-diols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Catechols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxybenzoic acid derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Sesterterpenoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoic acid or derivatives</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Catechol</substituent>
      <substituent>Dihydroxybenzoic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxybenzoic acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Polyprenylbenzene-1,2-diol</substituent>
      <substituent>Sesterterpenoid</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ubiquinones</external_descriptor>
      <external_descriptor>dihydroxybenzoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>8.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>11.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4,5-dihydroxybenzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>562.8223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>562.402210216</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(O)C(O)=CC(=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C37H54O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C37H54O4/c1-27(2)13-8-14-28(3)15-9-16-29(4)17-10-18-30(5)19-11-20-31(6)21-12-22-32(7)23-24-33-25-34(37(40)41)26-35(38)36(33)39/h13,15,17,19,21,23,25-26,38-39H,8-12,14,16,18,20,22,24H2,1-7H3,(H,40,41)/b28-15+,29-17+,30-19+,31-21+,32-23+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VEPICJBQCOUQPI-IRVXXIIISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>180.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>70.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ubiquinone Biosynthesis</name>
      <smpdb_id>SMP0087215</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180704</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05200</kegg_id>
  <foodb_id>FDB022402</foodb_id>
  <chemspider_id>4444330</chemspider_id>
  <pubchem_compound_id>5280760</pubchem_compound_id>
  <chebi_id>18081</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5976</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00413</protein_accession>
      <name>Hexaprenyldihydroxybenzoate methyltransferase, mitochondrial</name>
      <uniprot_id>Q3T131</uniprot_id>
      <gene_name>COQ3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:37 UTC</creation_date>
  <update_date>2020-03-13 16:25:40 UTC</update_date>
  <accession>BMDB0001064</accession>
  <secondary_accessions>
    <accession>BMDB01064</accession>
  </secondary_accessions>
  <name>Linoleoyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>(9Z,12Z)-Octadecadienoyl-CoA</synonym>
    <synonym>(9Z,12Z)-Octadecadienoyl-coenzyme A</synonym>
    <synonym>Linoleoyl-coenzyme A</synonym>
    <synonym>Linoleoyl-coenzyme A, (e,Z)-isomer</synonym>
    <synonym>Linoleoyl-coenzyme A, octadecadienoate-1-(14)C-labeled, (Z,Z)-isomer</synonym>
    <synonym>coenzyme A, S-9,12-Octadecadienoate, (Z,Z)</synonym>
    <synonym>Linoleoyl-coenzyme A, (e,e)-isomer</synonym>
    <synonym>Linoleoyl-coenzyme A, (Z,Z)-isomer</synonym>
  </synonyms>
  <chemical_formula>C39H66N7O17P3S</chemical_formula>
  <average_molecular_weight>1029.964</average_molecular_weight>
  <monisotopic_moleculate_weight>1029.344873947</monisotopic_moleculate_weight>
  <iupac_name>{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9E,12E)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9E,12E)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>CCCCC\C=C\C\C=C\CCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12</smiles>
  <inchi>InChI=1S/C39H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h8-9,11-12,26-28,32-34,38,49-50H,4-7,10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b9-8+,12-11+</inchi>
  <inchikey>YECLLIMZHNYFCK-MVKOLZDDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Long-chain fatty acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>2,3,4-saturated fatty acyl CoAs</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9E,12E)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1029.964</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1029.344873947</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC\C=C\C\C=C\CCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C39H66N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C39H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h8-9,11-12,26-28,32-34,38,49-50H,4-7,10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b9-8+,12-11+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YECLLIMZHNYFCK-MVKOLZDDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>248.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>101.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334878</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <chemspider_id/>
  <pubchem_compound_id>5462164</pubchem_compound_id>
  <chebi_id/>
  <kegg_id/>
  <pdbe_id/>
  <foodb_id>FDB022403</foodb_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Kawaguchi, Akihiko; Yoshimura, Tsutomu; Okuda, Shigenobu.  A new method for the preparation of acyl-CoA thioesters.    Journal of Biochemistry (Tokyo, Japan)  (1981),  89(2),  337-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:38 UTC</creation_date>
  <update_date>2020-04-15 22:35:41 UTC</update_date>
  <accession>BMDB0001065</accession>
  <secondary_accessions>
    <accession>BMDB01065</accession>
  </secondary_accessions>
  <name>2-Hydroxyphenethylamine</name>
  <description>2-Hydroxyphenethylamine, also known as beta-phenylethanolamine or 2-amino-1-phenylethanol, belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. 2-Hydroxyphenethylamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 2-Hydroxyphenethylamine exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>2-Amino-1-phenylethanol</synonym>
    <synonym>2-Hydroxy-2-phenylethylamine</synonym>
    <synonym>2-Phenyl-2-hydroxyethylamine</synonym>
    <synonym>alpha-(Aminomethyl)benzyl alcohol</synonym>
    <synonym>beta-Hydroxy-beta-phenylethylamine</synonym>
    <synonym>beta-Hydroxyphenethylamine</synonym>
    <synonym>beta-Phenethanolamine</synonym>
    <synonym>beta-Phenylethanolamine</synonym>
    <synonym>Bisnorephedrine</synonym>
    <synonym>Phenethanolamine</synonym>
    <synonym>a-(Aminomethyl)benzyl alcohol</synonym>
    <synonym>Α-(aminomethyl)benzyl alcohol</synonym>
    <synonym>b-Hydroxy-b-phenylethylamine</synonym>
    <synonym>Β-hydroxy-β-phenylethylamine</synonym>
    <synonym>b-Hydroxyphenethylamine</synonym>
    <synonym>Β-hydroxyphenethylamine</synonym>
    <synonym>b-Phenethanolamine</synonym>
    <synonym>Β-phenethanolamine</synonym>
    <synonym>b-Phenylethanolamine</synonym>
    <synonym>Β-phenylethanolamine</synonym>
    <synonym>2-Amino-1-phenyl-1-ethanol</synonym>
    <synonym>2-Amino-1-phenylethanol-1</synonym>
    <synonym>beta-Hydroxy-beta-phenyl-ethylamine</synonym>
    <synonym>beta-Hydroxy-phenethylamine</synonym>
    <synonym>beta-Hydroxyphenylethylamine</synonym>
    <synonym>DL-beta-Phenyl-beta-hydroxyethylamine</synonym>
    <synonym>Hydroxyethylamine</synonym>
    <synonym>Phenylethanolamine</synonym>
    <synonym>beta Phenylethanolamine</synonym>
    <synonym>2 Hydroxyphenethylamine</synonym>
    <synonym>2 Phenylethanolamine</synonym>
    <synonym>2-Phenylethanolamine</synonym>
    <synonym>beta Hydroxyphenethylamine</synonym>
    <synonym>2-Hydroxyphenethylamine</synonym>
  </synonyms>
  <chemical_formula>C8H11NO</chemical_formula>
  <average_molecular_weight>137.179</average_molecular_weight>
  <monisotopic_moleculate_weight>137.084063979</monisotopic_moleculate_weight>
  <iupac_name>2-amino-1-phenylethan-1-ol</iupac_name>
  <traditional_iupac>β phenylethanolamine</traditional_iupac>
  <cas_registry_number>7568-93-6</cas_registry_number>
  <smiles>NCC(O)C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2</inchi>
  <inchikey>ULSIYEODSMZIPX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>Aralkylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>phenylethanolamines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>56.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>45.8 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-1-phenylethan-1-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>137.179</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>137.084063979</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCC(O)C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H11NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ULSIYEODSMZIPX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>46.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352002</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02735</kegg_id>
  <foodb_id>FDB022404</foodb_id>
  <chemspider_id>975</chemspider_id>
  <pubchem_compound_id>1000</pubchem_compound_id>
  <chebi_id>16343</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id>PHENYLETHANOLAMINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Phenylethanolamine</wikipedia_id>
  <metlin_id>59</metlin_id>
  <synthesis_reference>Ye, Qizhuang.  Syntheses of conformationally defined analogs of tyramine and phenylethanolamine and their biological evaluations at central dopamine receptors and the active site of phenylethanolamine N-methyltransferase.    (1988),     152 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00100</protein_accession>
      <name>Phenylethanolamine N-methyltransferase</name>
      <uniprot_id>P10938</uniprot_id>
      <gene_name>PNMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:39 UTC</creation_date>
  <update_date>2020-03-13 16:25:41 UTC</update_date>
  <accession>BMDB0001066</accession>
  <secondary_accessions>
    <accession>BMDB01066</accession>
  </secondary_accessions>
  <name>S-Lactoylglutathione</name>
  <description/>
  <synonyms>
    <synonym>S-D-Lactoylglutathione</synonym>
    <synonym>(R)-S-Lactoylglutathione</synonym>
    <synonym>D-Lactoylglutathione</synonym>
    <synonym>delta-Lactoylglutathione</synonym>
    <synonym>N-(N-L-gamma-Glutamyl-S-(2-hydroxy-1-oxopropyl)-L-cysteinyl)-glycine</synonym>
    <synonym>S-D-Lactoyl-glutathione</synonym>
    <synonym>S-delta-Lactoyl-glutathione</synonym>
    <synonym>S-delta-Lactoylglutathione</synonym>
    <synonym>S-Lactate glutathione</synonym>
    <synonym>S-Lactateglutathione</synonym>
    <synonym>S-Lactoyl-glutathione</synonym>
    <synonym>S-Lactylglutathione</synonym>
    <synonym>S-[(2R)-2-Hydroxypropanoyl]-gamma-L-glutamyl-L-cysteinylglycine</synonym>
  </synonyms>
  <chemical_formula>C13H21N3O8S</chemical_formula>
  <average_molecular_weight>379.386</average_molecular_weight>
  <monisotopic_moleculate_weight>379.104935353</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid</iupac_name>
  <traditional_iupac>S-lactoylglutathione</traditional_iupac>
  <cas_registry_number>25138-66-3</cas_registry_number>
  <smiles>C[C@@H](O)C(=O)SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C13H21N3O8S/c1-6(17)13(24)25-5-8(11(21)15-4-10(19)20)16-9(18)3-2-7(14)12(22)23/h6-8,17H,2-5,14H2,1H3,(H,15,21)(H,16,18)(H,19,20)(H,22,23)/t6-,7+,8+/m1/s1</inchi>
  <inchikey>VDYDCVUWILIYQF-CSMHCCOUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Oligopeptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cysteine and derivatives</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Gamma-glutamyl peptides</alternative_parent>
      <alternative_parent>Glutamine and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>S-(2-hydroxyacyl)glutathiones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-oligopeptide</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Cysteine or derivatives</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Gamma-glutamyl alpha peptide</substituent>
      <substituent>Glutamine or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-substituted-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>S-(2-hydroxyacyl)glutathione</substituent>
      <substituent>S-acylglutathione</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>glutathione derivative</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>379.386</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>379.104935353</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](O)C(=O)SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H21N3O8S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H21N3O8S/c1-6(17)13(24)25-5-8(11(21)15-4-10(19)20)16-9(18)3-2-7(14)12(22)23/h6-8,17H,2-5,14H2,1H3,(H,15,21)(H,16,18)(H,19,20)(H,22,23)/t6-,7+,8+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VDYDCVUWILIYQF-CSMHCCOUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>196.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyruvaldehyde Degradation</name>
      <smpdb_id>SMP0087210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448134</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03451</kegg_id>
  <foodb_id>FDB022405</foodb_id>
  <chemspider_id>389032</chemspider_id>
  <pubchem_compound_id>440018</pubchem_compound_id>
  <chebi_id>15694</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id>S-LACTOYL-GLUTATHIONE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00019550</knapsack_id>
  <bigg_id>41876</bigg_id>
  <wikipedia_id/>
  <metlin_id>5979</metlin_id>
  <synthesis_reference>Liu, Yan; Hama, Hideki; Fujita, Yasuya; Kondo, Akihiko; Inoue, Yoshiharu; Kimura, Akira; Fukuda H.  Production of S-lactoylglutathione by high activity whole cell biocatalysts prepared by permeabilization of recombinant Saccharomyces cerevisiae with alcohols.  Biotechnol Bioeng. 1999 Jul 5;64(1):54-60.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:41 UTC</creation_date>
  <update_date>2020-04-14 22:48:50 UTC</update_date>
  <accession>BMDB0001067</accession>
  <secondary_accessions>
    <accession>BMDB01067</accession>
  </secondary_accessions>
  <name>N-Acetylaspartylglutamic acid</name>
  <description/>
  <synonyms>
    <synonym>N-Acetylaspartylglutamate</synonym>
    <synonym>2-({3-carboxy-1-hydroxy-2-[(1-hydroxyethylidene)amino]propylidene}amino)pentanedioate</synonym>
    <synonym>a-Spaglumic acid</synonym>
    <synonym>Acetyl-a-L-aspartylglutamic acid</synonym>
    <synonym>Acetyl-alpha-L-aspartylglutamic acid</synonym>
    <synonym>alpha-Spaglumic acid</synonym>
    <synonym>Isospaglumic acid</synonym>
    <synonym>N-(N-Acetylaspartyl)glutamic acid</synonym>
    <synonym>N-Acetyl-a-aspartylglutamic acid</synonym>
    <synonym>N-Acetyl-a-L-aspartyl-L-glutamic acid</synonym>
    <synonym>N-Acetyl-alpha-aspartylglutamic acid</synonym>
    <synonym>N-Acetyl-alpha-L-aspartyl-L-glutamic acid</synonym>
    <synonym>N-Acetyl-L-aspartyl-L-glutamic acid</synonym>
    <synonym>NAAG</synonym>
  </synonyms>
  <chemical_formula>C11H16N2O8</chemical_formula>
  <average_molecular_weight>304.2533</average_molecular_weight>
  <monisotopic_moleculate_weight>304.090665498</monisotopic_moleculate_weight>
  <iupac_name>2-(3-carboxy-2-acetamidopropanamido)pentanedioic acid</iupac_name>
  <traditional_iupac>2-(3-carboxy-2-acetamidopropanamido)pentanedioic acid</traditional_iupac>
  <cas_registry_number>3106-85-2</cas_registry_number>
  <smiles>CC(=O)NC(CC(O)=O)C(=O)NC(CCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C11H16N2O8/c1-5(14)12-7(4-9(17)18)10(19)13-6(11(20)21)2-3-8(15)16/h6-7H,2-4H2,1H3,(H,12,14)(H,13,19)(H,15,16)(H,17,18)(H,20,21)</inchi>
  <inchikey>OPVPGKGADVGKTG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Dipeptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Aspartic acid and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Glutamic acid and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-dipeptide</substituent>
      <substituent>Aspartic acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-substituted-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(3-carboxy-2-acetamidopropanamido)pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>304.2533</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>304.090665498</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)NC(CC(O)=O)C(=O)NC(CCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H16N2O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H16N2O8/c1-5(14)12-7(4-9(17)18)10(19)13-6(11(20)21)2-3-8(15)16/h6-7H,2-4H2,1H3,(H,12,14)(H,13,19)(H,15,16)(H,17,18)(H,20,21)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OPVPGKGADVGKTG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>170.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>64.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364821</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022406</foodb_id>
  <chemspider_id>5065</chemspider_id>
  <pubchem_compound_id>5255</pubchem_compound_id>
  <chebi_id>95120</chebi_id>
  <pdbe_id/>
  <kegg_id>C12270</kegg_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>N-Acetylaspartylglutamic acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Marchetti, Enzo; Mattalia, Gabriele; Curatolo, Francesco; Bergesi, Giuseppe.  Structure and synthesis of the natural dipeptides N-acetyl-b-L-aspartyl-L-glutamic acid and its isomer N-acetyl-a-L-aspartyl-L-glutamic acid.    Annali di Chimica (Rome, Italy)  (1967),  57(6),  624-31.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:42 UTC</creation_date>
  <update_date>2020-04-15 22:00:09 UTC</update_date>
  <accession>BMDB0001068</accession>
  <secondary_accessions>
    <accession>BMDB01068</accession>
  </secondary_accessions>
  <name>D-Sedoheptulose 7-phosphate</name>
  <description>D-D-d-sedoheptulose 7-phosphate, also known as D-sedoheptulose-7-P, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. D-D-d-sedoheptulose 7-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). D-D-d-sedoheptulose 7-phosphate exists in all eukaryotes, ranging from yeast to humans. D-D-d-sedoheptulose 7-phosphate participates in a number of enzymatic reactions, within cattle. In particular, D-Glyceraldehyde 3-phosphate and D-d-sedoheptulose 7-phosphate can be converted into D-ribose 5-phosphate and xylulose 5-phosphate through its interaction with the enzyme transketolase. Furthermore, D-Glyceraldehyde 3-phosphate and D-d-sedoheptulose 7-phosphate can be biosynthesized from D-erythrose 4-phosphate and fructose 6-phosphate; which is mediated by the enzyme transaldolase. Furthermore, D-Glyceraldehyde 3-phosphate and D-d-sedoheptulose 7-phosphate can be biosynthesized from D-erythrose 4-phosphate and fructose 6-phosphate through its interaction with the enzyme transaldolase. Finally, D-Glyceraldehyde 3-phosphate and D-d-sedoheptulose 7-phosphate can be converted into D-ribose 5-phosphate and xylulose 5-phosphate; which is catalyzed by the enzyme transketolase. In cattle, D-d-sedoheptulose 7-phosphate is involved in a couple of metabolic pathways, which include the pentose phosphate pathway and cancer (via the Warburg effect).</description>
  <synonyms>
    <synonym>D-Sedoheptulose 7-phosphoric acid</synonym>
    <synonym>Sedoheptulose 7-phosphate</synonym>
    <synonym>Heptulose-7-phosphate</synonym>
    <synonym>Sedoheptulose 7-phosphoric acid(2-)</synonym>
  </synonyms>
  <chemical_formula>C7H15O10P</chemical_formula>
  <average_molecular_weight>290.1618</average_molecular_weight>
  <monisotopic_moleculate_weight>290.040283212</monisotopic_moleculate_weight>
  <iupac_name>[(2,3,4,5,7-pentahydroxy-6-oxoheptyl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>sedoheptulose 7-phosphate</traditional_iupac>
  <cas_registry_number/>
  <smiles>OCC(=O)C(O)C(O)C(O)C(O)COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C7H15O10P/c8-1-3(9)5(11)7(13)6(12)4(10)2-17-18(14,15)16/h4-8,10-13H,1-2H2,(H2,14,15,16)</inchi>
  <inchikey>JDTUMPKOJBQPKX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharide phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Acyloins</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Heptoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyloin</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Heptose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(2,3,4,5,7-pentahydroxy-6-oxoheptyl)oxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>290.1618</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>290.040283212</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(=O)C(O)C(O)C(O)C(O)COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H15O10P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H15O10P/c8-1-3(9)5(11)7(13)6(12)4(10)2-17-18(14,15)16/h4-8,10-13H,1-2H2,(H2,14,15,16)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JDTUMPKOJBQPKX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>184.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31267</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <pubchem_compound_id>616</pubchem_compound_id>
  <chemspider_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id>C05382</kegg_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <pdbe_id/>
  <chebi_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00103</protein_accession>
      <name>Transaldolase</name>
      <uniprot_id>Q2TBL6</uniprot_id>
      <gene_name>TALDO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00104</protein_accession>
      <name>Transaldolase</name>
      <uniprot_id>Q58DR3</uniprot_id>
      <gene_name>TALDO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00607</protein_accession>
      <name>Transketolase-like protein 1</name>
      <uniprot_id>Q2NL26</uniprot_id>
      <gene_name>TKTL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00608</protein_accession>
      <name>Transketolase-like protein 2</name>
      <uniprot_id>Q2NKZ4</uniprot_id>
      <gene_name>TKTL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00609</protein_accession>
      <name>Transketolase</name>
      <uniprot_id>Q6B855</uniprot_id>
      <gene_name>TKT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:43 UTC</creation_date>
  <update_date>2020-03-13 16:25:43 UTC</update_date>
  <accession>BMDB0001069</accession>
  <secondary_accessions>
    <accession>BMDB01069</accession>
  </secondary_accessions>
  <name>2-Phenylaminoadenosine</name>
  <description/>
  <synonyms>
    <synonym>6-Amino-2-phenylamino-9-b-D-ribofuranosyl-9H-purine</synonym>
    <synonym>6-Amino-2-phenylamino-9-beta-delta-ribofuranosyl-9H-purine</synonym>
    <synonym>2-Phenylaminoadenosine</synonym>
  </synonyms>
  <chemical_formula>C16H18N6O4</chemical_formula>
  <average_molecular_weight>358.3519</average_molecular_weight>
  <monisotopic_moleculate_weight>358.138953094</monisotopic_moleculate_weight>
  <iupac_name>2-[6-amino-2-(phenylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol</iupac_name>
  <traditional_iupac>2-[6-amino-2-(phenylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol</traditional_iupac>
  <cas_registry_number>53296-10-9</cas_registry_number>
  <smiles>NC1=C2N=CN(C3OC(CO)C(O)C3O)C2=NC(NC2=CC=CC=C2)=N1</smiles>
  <inchi>InChI=1S/C16H18N6O4/c17-13-10-14(21-16(20-13)19-8-4-2-1-3-5-8)22(7-18-10)15-12(25)11(24)9(6-23)26-15/h1-5,7,9,11-12,15,23-25H,6H2,(H3,17,19,20,21)</inchi>
  <inchikey>SCNILGOVBBRMBK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleosides</class>
    <sub_class/>
    <direct_parent>Purine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleoside</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.028</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[6-amino-2-(phenylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>358.3519</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>358.138953094</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=C2N=CN(C3OC(CO)C(O)C3O)C2=NC(NC2=CC=CC=C2)=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H18N6O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H18N6O4/c17-13-10-14(21-16(20-13)19-8-4-2-1-3-5-8)22(7-18-10)15-12(25)11(24)9(6-23)26-15/h1-5,7,9,11-12,15,23-25H,6H2,(H3,17,19,20,21)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SCNILGOVBBRMBK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>151.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>91.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356835</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022408</foodb_id>
  <chemspider_id>1528</chemspider_id>
  <pubchem_compound_id>1585</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>91804</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5981</metlin_id>
  <synthesis_reference>Omura, Kiyoshi; Marumoto, Ryuji; Furukawa, Yoshiyasu.  Synthesis of 2-phenylaminoadenosine from imidazole nucleosides.    Chemical &amp; Pharmaceutical Bulletin  (1981),  29(7),  1870-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:44 UTC</creation_date>
  <update_date>2020-04-15 22:00:09 UTC</update_date>
  <accession>BMDB0001070</accession>
  <secondary_accessions>
    <accession>BMDB01070</accession>
  </secondary_accessions>
  <name>Octanoyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>Capryloyl-CoA</synonym>
    <synonym>Capryloyl-coenzyme A</synonym>
    <synonym>Octanoyl-coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C29H50N7O17P3S</chemical_formula>
  <average_molecular_weight>893.73</average_molecular_weight>
  <monisotopic_moleculate_weight>893.219673435</monisotopic_moleculate_weight>
  <iupac_name>{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-(octanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>octanoyl-coenzyme A</traditional_iupac>
  <cas_registry_number>1264-52-4</cas_registry_number>
  <smiles>CCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12</smiles>
  <inchi>InChI=1S/C29H50N7O17P3S/c1-4-5-6-7-8-9-20(38)57-13-12-31-19(37)10-11-32-27(41)24(40)29(2,3)15-50-56(47,48)53-55(45,46)49-14-18-23(52-54(42,43)44)22(39)28(51-18)36-17-35-21-25(30)33-16-34-26(21)36/h16-18,22-24,28,39-40H,4-15H2,1-3H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)</inchi>
  <inchikey>KQMZYOXOBSXMII-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>2,3,4-saturated fatty acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Medium-chain fatty acyl CoAs</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-(octanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>893.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>893.219673435</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C29H50N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C29H50N7O17P3S/c1-4-5-6-7-8-9-20(38)57-13-12-31-19(37)10-11-32-27(41)24(40)29(2,3)15-50-56(47,48)53-55(45,46)49-14-18-23(52-54(42,43)44)22(39)28(51-18)36-17-35-21-25(30)33-16-34-26(21)36/h16-18,22-24,28,39-40H,4-15H2,1-3H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KQMZYOXOBSXMII-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>199.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>83.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36070</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01944</kegg_id>
  <foodb_id>FDB022409</foodb_id>
  <chemspider_id>371</chemspider_id>
  <pubchem_compound_id>380</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>15533</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id>38747</bigg_id>
  <wikipedia_id>Octanoyl-CoA</wikipedia_id>
  <metlin_id>5982</metlin_id>
  <synthesis_reference>Milne, K. G.; Mehlert, A.; Ferguson, M. A. J.  The use of Pseudomonas acyl-CoA synthetase to form acyl-CoAs from dicarboxylic fatty acids.    Biochimica et Biophysica Acta, Molecular and Cell Biology of Lipids  (2001),  1531(1-2),  1-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00244</protein_accession>
      <name>Peroxisomal carnitine O-octanoyltransferase</name>
      <uniprot_id>O19094</uniprot_id>
      <gene_name>CROT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:45 UTC</creation_date>
  <update_date>2020-04-16 20:38:36 UTC</update_date>
  <accession>BMDB0001072</accession>
  <secondary_accessions>
    <accession>BMDB01072</accession>
  </secondary_accessions>
  <name>Coenzyme Q10</name>
  <description>Coenzyme Coenzyme coenzyme Coenzyme q101010, also known as Coenzyme coenzyme Coenzyme q1010 or coenzyme Q10, belongs to the class of organic compounds known as ubicoenzyme Coenzyme q10uinones. These are coenzyme Coenzyme coenzyme Coenzyme q1010 derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzocoenzyme Coenzyme q10uinone) moiety to which an isoprenyl group is attached at ring position 2(or 6). Coenzyme Coenzyme coenzyme Coenzyme q101010 is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Coenzyme Coenzyme coenzyme Coenzyme q101010 exists in all living species, ranging from bacteria to humans. Coenzyme Coenzyme coenzyme Coenzyme q101010 participates in a number of enzymatic reactions, within cattle. In particular, Coenzyme Coenzyme coenzyme Coenzyme q101010 and glycerol 3-phosphate can be converted into ubicoenzyme Coenzyme q10uinol 8 and dihydroxyacetone phosphate through its interaction with the enzyme glycerol-3-phosphate dehydrogenase, mitochondrial. In addition, Coenzyme Coenzyme coenzyme Coenzyme q101010 and succinic acid can be converted into ubicoenzyme Coenzyme q10uinol 8 and fumaric acid through the action of the enzyme succinate dehydrogenase. In cattle, coenzyme Coenzyme coenzyme Coenzyme q101010 is involved in the metabolic pathway called the mitochondrial electron transport chain pathway.</description>
  <synonyms>
    <synonym>2-((all-e)-3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-p-benzoquinone</synonym>
    <synonym>2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-Decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methyl-1,4-benzoquinone</synonym>
    <synonym>Adelir</synonym>
    <synonym>all-trans-Ubiquinone</synonym>
    <synonym>CoQ</synonym>
    <synonym>CoQ10</synonym>
    <synonym>Q</synonym>
    <synonym>Q 199</synonym>
    <synonym>Q10</synonym>
    <synonym>Ubidecarenone</synonym>
    <synonym>Ubiquinone</synonym>
    <synonym>Ubiquinone 10</synonym>
    <synonym>Ubiquinone 50</synonym>
    <synonym>UBIQUINONE-10</synonym>
    <synonym>CoQ 10</synonym>
    <synonym>2,3-Dimethoxy-5-methyl-6-decaprenylbenzoquinone</synonym>
    <synonym>Bio-quinone Q10</synonym>
    <synonym>Ubiquinone Q10</synonym>
    <synonym>Q-Ter</synonym>
    <synonym>CO-Enzyme Q10</synonym>
    <synonym>(all-e)-2,3-Dimethoxy-5-methyl-6-(3,7,11,15,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaenyl)-2,5-cyclohexadiene-1,4-dione</synonym>
    <synonym>(all-e)-2-(3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione</synonym>
    <synonym>2-(3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-5,6-dimethoxy-3-methyl-p-benzoquinone</synonym>
    <synonym>2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl]-5,6-dimethoxy-3-methyl- 2,5-cyclohexadiene-1,4-dione</synonym>
    <synonym>4-Ethyl-5-fluoropyrimidine</synonym>
    <synonym>Aqua Q 10l10</synonym>
    <synonym>Aqua Q10</synonym>
    <synonym>Bio-quinon</synonym>
    <synonym>Ensorb</synonym>
    <synonym>Kaneka Q10</synonym>
    <synonym>Kudesan</synonym>
    <synonym>Li-Q-sorb</synonym>
    <synonym>Liquid-Q</synonym>
    <synonym>Neuquinon</synonym>
    <synonym>Neuquinone</synonym>
    <synonym>PureSorb Q 40</synonym>
    <synonym>Q 10AA</synonym>
    <synonym>Q-Gel</synonym>
    <synonym>Q-Gel 100</synonym>
    <synonym>Unbiquinone</synonym>
    <synonym>Unispheres Q 10</synonym>
    <synonym>Coenzyme Q10</synonym>
  </synonyms>
  <chemical_formula>C59H90O4</chemical_formula>
  <average_molecular_weight>863.3435</average_molecular_weight>
  <monisotopic_moleculate_weight>862.683911368</monisotopic_moleculate_weight>
  <iupac_name>2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione</iupac_name>
  <traditional_iupac>coenzyme-Q10</traditional_iupac>
  <cas_registry_number>303-98-0</cas_registry_number>
  <smiles>COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O</smiles>
  <inchi>InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+</inchi>
  <inchikey>ACTIUHUUMQJHFO-UPTCCGCDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Quinone and hydroquinone lipids</sub_class>
    <direct_parent>Ubiquinones</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>P-benzoquinones</alternative_parent>
      <alternative_parent>Polyprenylbenzoquinones</alternative_parent>
      <alternative_parent>Polyterpenoids</alternative_parent>
      <alternative_parent>Vinylogous esters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>P-benzoquinone</substituent>
      <substituent>Polyprenylbenzoquinone</substituent>
      <substituent>Polyterpenoid</substituent>
      <substituent>Quinone</substituent>
      <substituent>Ubiquinone skeleton</substituent>
      <substituent>Vinylogous ester</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Coenzymes</external_descriptor>
      <external_descriptor>Ubiquinones</external_descriptor>
      <external_descriptor>ubiquinones</external_descriptor>
      <external_descriptor>ubiquinones</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>9.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>17.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>863.3435</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>862.683911368</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C59H90O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ACTIUHUUMQJHFO-UPTCCGCDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>52.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>286.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>112.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35020</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C11378</kegg_id>
  <foodb_id>FDB013228</foodb_id>
  <chemspider_id/>
  <drugbank_id>DB09270</drugbank_id>
  <pubchem_compound_id>5281915</pubchem_compound_id>
  <chebi_id>46245</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00002866</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Coenzyme_Q10</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Seo, Myung-Ji; Im, Eun-Mi; Hur, Jin-Haeng; Nam, Jung-Yeon; Hyun, Chang-Gu; Pyun, Yu-Ryang; Kim, Soon-Ok.  Production of coenzyme Q10 by recombinant E. coli harboring the decaprenyl diphosphate synthase gene from Sinorhizobium meliloti.    Journal of Microbiology and Biotechnology  (2006),  16(6),  933-938.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:46 UTC</creation_date>
  <update_date>2020-04-14 22:48:50 UTC</update_date>
  <accession>BMDB0001076</accession>
  <secondary_accessions>
    <accession>BMDB01076</accession>
  </secondary_accessions>
  <name>Fructose 1-phosphate</name>
  <description>Fructose 1-phosphate, also known as D-fructose-1-P, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Fructose 1-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Fructose 1-phosphate exists in all living organisms, ranging from bacteria to humans. Fructose 1-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Fructose 1-phosphate can be biosynthesized from D-fructose through the action of the enzyme ketohexokinase. In addition, Fructose 1-phosphate can be converted into dihydroxyacetone phosphate and glyceraldehyde; which is catalyzed by the enzyme fructose-bisphosphate aldolase a. In cattle, fructose 1-phosphate is involved in the metabolic pathway called the fructose and mannose degradation pathway.</description>
  <synonyms>
    <synonym>beta-D-Fructose 1-phosphate</synonym>
    <synonym>b-D-Fructose 1-phosphate</synonym>
    <synonym>b-D-Fructose 1-phosphoric acid</synonym>
    <synonym>beta-D-Fructose 1-phosphoric acid</synonym>
    <synonym>Β-D-fructose 1-phosphate</synonym>
    <synonym>Β-D-fructose 1-phosphoric acid</synonym>
    <synonym>Fructose 1-phosphoric acid</synonym>
    <synonym>D-Fructose 1-phosphate</synonym>
    <synonym>D-Fructose-1-p</synonym>
    <synonym>D-Fructose-1-phosphate</synonym>
    <synonym>Fructose-1-p</synonym>
    <synonym>Fructose-1-phosphate</synonym>
    <synonym>b-D-Fructofuranose 1-phosphate</synonym>
    <synonym>b-D-Fructofuranose 1-phosphoric acid</synonym>
    <synonym>beta-D-Fructofuranose 1-phosphoric acid</synonym>
    <synonym>Β-D-fructofuranose 1-phosphate</synonym>
    <synonym>Β-D-fructofuranose 1-phosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C6H13O9P</chemical_formula>
  <average_molecular_weight>260.1358</average_molecular_weight>
  <monisotopic_moleculate_weight>260.029718526</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxyphosphonic acid</traditional_iupac>
  <cas_registry_number>15978-08-2</cas_registry_number>
  <smiles>OC[C@H]1O[C@](O)(COP(O)(O)=O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H13O9P/c7-1-3-4(8)5(9)6(10,15-3)2-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1</inchi>
  <inchikey>RHKKZBWRNHGJEZ-ARQDHWQXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>260.1358</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>260.029718526</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@](O)(COP(O)(O)=O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O9P/c7-1-3-4(8)5(9)6(10,15-3)2-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RHKKZBWRNHGJEZ-ARQDHWQXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>156.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35212</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01094</kegg_id>
  <foodb_id>FDB022410</foodb_id>
  <chemspider_id>8575807</chemspider_id>
  <pubchem_compound_id>10400369</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>139419</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>FRU1P</meta_cyc_id>
  <bigg_id>40936</bigg_id>
  <wikipedia_id>Fructose 1-phosphate</wikipedia_id>
  <metlin_id>378</metlin_id>
  <synthesis_reference>Hara, Yoshito.  Ion exchange separation of fructose 1-phosphate by using borate as the eluant.    Journal of Biochemistry (Tokyo, Japan)  (1959),  46  571-3.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:48 UTC</creation_date>
  <update_date>2020-04-15 22:35:42 UTC</update_date>
  <accession>BMDB0001078</accession>
  <secondary_accessions>
    <accession>BMDB01078</accession>
  </secondary_accessions>
  <name>Mannose 6-phosphate</name>
  <description>Mannose 6-phosphate, also known as alpha-D-mannose-6-p or mannose 6-phosphate, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Mannose 6-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Mannose 6-phosphate exists in all eukaryotes, ranging from yeast to humans. Mannose 6-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Mannose 6-phosphate can be converted into fructose 6-phosphate; which is catalyzed by the enzyme mannose 6-phosphate isomerase. In addition, Mannose 6-phosphate can be biosynthesized from D-mannose through the action of the enzyme hexokinase-1. In cattle, mannose 6-phosphate is involved in the metabolic pathway called the fructose and mannose degradation pathway.</description>
  <synonyms>
    <synonym>Mannose 6-phosphoric acid</synonym>
    <synonym>alpha-D-Mannose-6-p</synonym>
    <synonym>alpha-D-Mannose-6-phosphate</synonym>
    <synonym>alpha-delta-Mannose-6-p</synonym>
    <synonym>alpha-delta-Mannose-6-phosphate</synonym>
    <synonym>D-Mannose 6-phosphate</synonym>
    <synonym>delta-Mannose 6-phosphate</synonym>
    <synonym>Man-6-p</synonym>
    <synonym>Mannose-6-phosphate</synonym>
    <synonym>Mannose-6-phosphate dilithium salt</synonym>
    <synonym>Mannose-6-phosphate disodium salt</synonym>
    <synonym>Mannose-6-phosphate sodium salt, (D)-isomer</synonym>
  </synonyms>
  <chemical_formula>C6H13O9P</chemical_formula>
  <average_molecular_weight>260.1358</average_molecular_weight>
  <monisotopic_moleculate_weight>260.029718526</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4S,5S,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>mannose 6 phosphate</traditional_iupac>
  <cas_registry_number>3672-15-9</cas_registry_number>
  <smiles>O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6-/m1/s1</inchi>
  <inchikey>NBSCHQHZLSJFNQ-RWOPYEJCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D-mannopyranose 6-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4S,5S,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>260.1358</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>260.029718526</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5+,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NBSCHQHZLSJFNQ-RWOPYEJCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>156.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181949</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00275</kegg_id>
  <foodb_id>FDB022411</foodb_id>
  <chemspider_id>388338</chemspider_id>
  <pubchem_compound_id>439198</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>49728</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id>34471</bigg_id>
  <wikipedia_id>Mannose 6-phosphate</wikipedia_id>
  <metlin_id>5987</metlin_id>
  <synthesis_reference>Pascual, C.; Herrera, L.  Use of permeabilized yeast cells as a system of enzyme immobilization.  Its use for the preparation of mannose 6-phosphate.    Folia Microbiologica (Prague, Czech Republic)  (1981),  26(2),  103-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01106</protein_accession>
      <name>Mannose-6-phosphate isomerase</name>
      <uniprot_id>Q3SZI0</uniprot_id>
      <gene_name>MPI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01899</protein_accession>
      <name>Cation-dependent mannose-6-phosphate receptor</name>
      <uniprot_id>P11456</uniprot_id>
      <gene_name>M6PR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01906</protein_accession>
      <name>Mannose 6 phosphate receptor binding protein 1</name>
      <uniprot_id>Q3SX32</uniprot_id>
      <gene_name>M6PRBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01911</protein_accession>
      <name>Cation-independent mannose-6-phosphate receptor</name>
      <uniprot_id>P08169</uniprot_id>
      <gene_name>IGF2R</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:49 UTC</creation_date>
  <update_date>2020-04-15 22:14:55 UTC</update_date>
  <accession>BMDB0001080</accession>
  <secondary_accessions>
    <accession>BMDB01080</accession>
  </secondary_accessions>
  <name>4-Aminobutyraldehyde</name>
  <description>4-Aminobutanal belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. 4-Aminobutanal is possibly soluble (in water) and a very strong basic compound (based on its pKa). 4-Aminobutanal exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>4-Amino-butyraldehyde</synonym>
    <synonym>4-Amino-butanal</synonym>
    <synonym>4-Aminobutanal</synonym>
    <synonym>4-Ammoniobutanal</synonym>
    <synonym>gamma-Aminobutyraldehyde</synonym>
    <synonym>4-Aminobutyraldehyde</synonym>
  </synonyms>
  <chemical_formula>C4H9NO</chemical_formula>
  <average_molecular_weight>87.1204</average_molecular_weight>
  <monisotopic_moleculate_weight>87.068413915</monisotopic_moleculate_weight>
  <iupac_name>4-aminobutanal</iupac_name>
  <traditional_iupac>ω-aminoaldehyde</traditional_iupac>
  <cas_registry_number>4390-05-0</cas_registry_number>
  <smiles>NCCCC=O</smiles>
  <inchi>InChI=1S/C4H9NO/c5-3-1-2-4-6/h4H,1-3,5H2</inchi>
  <inchikey>DZQLQEYLEYWJIB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Alpha-hydrogen aldehydes</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydrogen aldehyde</substituent>
      <substituent>Amine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aminobutanal</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-aminobutanal</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>87.1204</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>87.068413915</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCC=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H9NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H9NO/c5-3-1-2-4-6/h4H,1-3,5H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DZQLQEYLEYWJIB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>43.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>24.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32521</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02903</kegg_id>
  <foodb_id>FDB022412</foodb_id>
  <chemspider_id>115</chemspider_id>
  <pubchem_compound_id>118</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>17769</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00019656</knapsack_id>
  <meta_cyc_id/>
  <bigg_id>35337</bigg_id>
  <wikipedia_id/>
  <metlin_id>3225</metlin_id>
  <synthesis_reference>Asakura, Tadashi; Takada, Koji; Ikeda, Yoshitaka; Matsuda, Makoto.  Preparation of 4-aminobutyraldehyde and its properties on ion exchange chromatography.    Jikeikai Medical Journal  (1988),  35(1),  23-31.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:50 UTC</creation_date>
  <update_date>2020-03-13 16:25:46 UTC</update_date>
  <accession>BMDB0001081</accession>
  <secondary_accessions>
    <accession>BMDB01081</accession>
  </secondary_accessions>
  <name>(N-acetylneuraminosyl(a2-6)lactosamine)</name>
  <description>(N-Acetylneuraminosyl(a2-6)lactosamine), also known as a-neunac-(2-&gt;6)-b-D-gal-(1-&gt;4)-b-D-glcnac or 6-sialyllactosamine, belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety (N-Acetylneuraminosyl(a2-6)lactosamine) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa).</description>
  <synonyms>
    <synonym>(2R,4S,5R,6R)-5-Acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</synonym>
    <synonym>(N-Acetylneuraminosyl(alpha2-6)lactosamine)</synonym>
    <synonym>6'-Sialyllactosamine</synonym>
    <synonym>6-Sialyllactosamine</synonym>
    <synonym>alpha-N-Acetylneuraminyl-2,6-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine</synonym>
    <synonym>alpha-N-Acetylneuraminyl-2,6-beta-delta-galactosyl-1,4-N-acetyl-beta-delta-glucosamine</synonym>
    <synonym>alpha-NeuNAc-(2-&gt;6)-beta-D-gal-(1-&gt;4)-beta-D-glcnac</synonym>
    <synonym>alpha-NeupNAc-(2-&gt;6)-beta-D-galp-(1-&gt;4)-beta-D-glcpnac</synonym>
    <synonym>N-Acetylneuraminosyl(alpha2-6)lactosamine</synonym>
    <synonym>Neu5aca2-6galb1-4glcnacb</synonym>
    <synonym>Neuac-lact</synonym>
    <synonym>NeuAcalpha2,6galbeta1,4glcnac</synonym>
    <synonym>Neuacalpha2,6galnacbeta1,4glcnac</synonym>
    <synonym>Neuacalpha2-6galbeta1-4glcnacbeta</synonym>
    <synonym>O-(N-Acetyl-a-neuraminosyl)-(2-&gt;6)-O-b-D-galactopyranosyl-(1-&gt;4)-2-(acetylamino)-2-deoxy-b-D-glucopyranose</synonym>
    <synonym>O-(N-Acetyl-alpha-neuraminosyl)-(26)-O-beta-D-galactopyranosyl-(1-&gt;-4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranose</synonym>
    <synonym>O-(N-Acetyl-alpha-neuraminosyl)-(2-&gt;6)-O-beta-delta-galactopyranosyl-(1-&gt;-4)-2-(acetylamino)-2-deoxy-beta-delta-glucopyranose</synonym>
    <synonym>(2R,4S,5R,6R)-5-Acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate</synonym>
    <synonym>(N-Acetylneuraminosyl(α2-6)lactosamine)</synonym>
    <synonym>a-N-Acetylneuraminyl-2,6-b-D-galactosyl-1,4-N-acetyl-b-D-glucosamine</synonym>
    <synonym>Α-N-acetylneuraminyl-2,6-β-D-galactosyl-1,4-N-acetyl-β-D-glucosamine</synonym>
    <synonym>a-N-Acetylneuraminyl-2,6-b-delta-galactosyl-1,4-N-acetyl-b-delta-glucosamine</synonym>
    <synonym>Α-N-acetylneuraminyl-2,6-β-δ-galactosyl-1,4-N-acetyl-β-δ-glucosamine</synonym>
    <synonym>a-NeuNAc-(2-&gt;6)-b-D-gal-(1-&gt;4)-b-D-glcnac</synonym>
    <synonym>Α-neunac-(2-&gt;6)-β-D-gal-(1-&gt;4)-β-D-glcnac</synonym>
    <synonym>a-NeupNAc-(2-&gt;6)-b-D-galp-(1-&gt;4)-b-D-glcpnac</synonym>
    <synonym>Α-neupnac-(2-&gt;6)-β-D-galp-(1-&gt;4)-β-D-glcpnac</synonym>
    <synonym>N-Acetylneuraminosyl(a2-6)lactosamine</synonym>
    <synonym>N-Acetylneuraminosyl(α2-6)lactosamine</synonym>
    <synonym>O-(N-Acetyl-a-neuraminosyl)-(26)-O-b-D-galactopyranosyl-(1-&gt;-4)-2-(acetylamino)-2-deoxy-b-D-glucopyranose</synonym>
    <synonym>O-(N-Acetyl-α-neuraminosyl)-(26)-O-β-D-galactopyranosyl-(1-&gt;-4)-2-(acetylamino)-2-deoxy-β-D-glucopyranose</synonym>
    <synonym>O-(N-Acetyl-a-neuraminosyl)-(2-&gt;6)-O-b-delta-galactopyranosyl-(1-&gt;-4)-2-(acetylamino)-2-deoxy-b-delta-glucopyranose</synonym>
    <synonym>O-(N-Acetyl-α-neuraminosyl)-(2-&gt;6)-O-β-δ-galactopyranosyl-(1-&gt;-4)-2-(acetylamino)-2-deoxy-β-δ-glucopyranose</synonym>
    <synonym>Neu5acbeta2-6galbeta1-4glcnacbeta</synonym>
    <synonym>O-(N-Acetyl-alpha-neuraminosyl)-(2-&gt;6)-O-beta-D-galactopyranosyl-(1-&gt;4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranose</synonym>
    <synonym>O-(N-Acetyl-alpha-neuraminosyl)-(2-&gt;6)-O-beta-delta-galactopyranosyl-(1-&gt;4)-2-(acetylamino)-2-deoxy-beta-delta-glucopyranose</synonym>
    <synonym>a-N-Acetylneuraminyl-(2-&gt;6)-b-D-galactosyl-(1-&gt;4)-N-acetyl-b-D-glucosamine</synonym>
    <synonym>Α-N-acetylneuraminyl-(2-&gt;6)-β-D-galactosyl-(1-&gt;4)-N-acetyl-β-D-glucosamine</synonym>
  </synonyms>
  <chemical_formula>C25H42N2O19</chemical_formula>
  <average_molecular_weight>674.603</average_molecular_weight>
  <monisotopic_moleculate_weight>674.238177172</monisotopic_moleculate_weight>
  <iupac_name>(2R,4S,5R,6R)-5-acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>6-sialyllactosamine</traditional_iupac>
  <cas_registry_number>64364-50-7</cas_registry_number>
  <smiles>[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)[C@H](O)CO</smiles>
  <inchi>InChI=1S/C25H42N2O19/c1-7(30)26-13-9(32)3-25(24(40)41,46-21(13)15(34)10(33)4-28)42-6-12-16(35)18(37)19(38)23(44-12)45-20-11(5-29)43-22(39)14(17(20)36)27-8(2)31/h9-23,28-29,32-39H,3-6H2,1-2H3,(H,26,30)(H,27,31)(H,40,41)/t9-,10+,11+,12+,13+,14+,15+,16-,17+,18-,19+,20+,21+,22+,23-,25+/m0/s1</inchi>
  <inchikey>RPSBVJXBTXEJJG-LURNZOHQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleosides</class>
    <sub_class/>
    <direct_parent>Purine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleoside</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,4S,5R,6R)-5-acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>674.603</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>674.238177172</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)[C@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H42N2O19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C25H42N2O19/c1-7(30)26-13-9(32)3-25(24(40)41,46-21(13)15(34)10(33)4-28)42-6-12-16(35)18(37)19(38)23(44-12)45-20-11(5-29)43-22(39)14(17(20)36)27-8(2)31/h9-23,28-29,32-39H,3-6H2,1-2H3,(H,26,30)(H,27,31)(H,40,41)/t9-,10+,11+,12+,13+,14+,15+,16-,17+,18-,19+,20+,21+,22+,23-,25+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RPSBVJXBTXEJJG-LURNZOHQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>343.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>139.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>63.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368373</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13.341 - 17.788</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Average over the milking season </comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C04886</kegg_id>
  <foodb_id>FDB022413</foodb_id>
  <chemspider_id>111381</chemspider_id>
  <pubchem_compound_id>125128</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>17725</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>ALPHA-N-ACETYLNEURAMINYL-26-BETA</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5990</metlin_id>
  <synthesis_reference>Dall'Olio F  The sialyl-alpha2,6-lactosaminyl-structure: biosynthesis and functional role.    Glycoconjugate journal  (2000),  17(10),  669-76.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:51 UTC</creation_date>
  <update_date>2020-03-13 16:25:46 UTC</update_date>
  <accession>BMDB0001083</accession>
  <secondary_accessions>
    <accession>BMDB01083</accession>
  </secondary_accessions>
  <name>Adenosyl cobyrinic acid a,c diamide</name>
  <description/>
  <synonyms>
    <synonym>Adenosyl cobyrinate a,c diamide</synonym>
    <synonym>Adenosyl cobyrinate diamide</synonym>
    <synonym>Adenosylcobyrinic acid a,c-diamide</synonym>
    <synonym>Adenosyl cobyrinic acid diamide</synonym>
    <synonym>Adenosylcobyrinate a,c-diamide</synonym>
    <synonym>Adenosylcob(III)yrinate a,c-diamide</synonym>
    <synonym>Adenosyl cobyrinic acid a,c diamide</synonym>
  </synonyms>
  <chemical_formula>C55H73CoN11O15</chemical_formula>
  <average_molecular_weight>1187.166</average_molecular_weight>
  <monisotopic_moleculate_weight>1186.461960915</monisotopic_moleculate_weight>
  <iupac_name>{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(1R,2R,3S,4S,6Z,8S,9S,11Z,14S,18R,19R)-3,8-bis(carbamoylmethyl)-4,9,14,18-tetrakis(2-carboxyethyl)-19-(carboxymethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1^{2,5}.1^{7,10}.1^{12,15}]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium</iupac_name>
  <traditional_iupac>{[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(1R,2R,3S,4S,6Z,8S,9S,11Z,14S,18R,19R)-3,8-bis(carbamoylmethyl)-4,9,14,18-tetrakis(2-carboxyethyl)-19-(carboxymethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1^{2,5}.1^{7,10}.1^{12,15}]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@]12[C@H](CC(O)=O)[C@@](C)(CCC(O)=O)\C(N1[Co+]C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)=C(C)\C1=N\C(=C/C3=N/C(=C(C)\C4=N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(O)=O)/[C@@](C)(CC(N)=O)[C@@H]3CCC(O)=O)\C(C)(C)[C@@H]1CCC(O)=O</smiles>
  <inchi>InChI=1S/C45H62N6O12.C10H12N5O3.Co/c1-21-36-24(10-13-32(56)57)41(3,4)28(49-36)18-27-23(9-12-31(54)55)43(6,19-29(46)52)39(48-27)22(2)37-25(11-14-33(58)59)44(7,20-30(47)53)45(8,51-37)40-26(17-35(62)63)42(5,38(21)50-40)16-15-34(60)61;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h18,23-26,40H,9-17,19-20H2,1-8H3,(H10,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-1/t23-,24-,25-,26+,40-,42-,43+,44+,45+;4-,6-,7-,10-;/m11./s1</inchi>
  <inchikey>OCNLJCZKGHKJGF-NQYRMHKHSA-M</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as precorrins. These are intermediates formed by methylation at one or more of the four rings prior to the formation of the macrocyclic corrin ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Corrinoids</sub_class>
    <direct_parent>Precorrins</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>5'-deoxyribonucleosides</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbene-type 1,3-dipolar compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty amides</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Ketimines</alternative_parent>
      <alternative_parent>Metallotetrapyrroles</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic cobalt salts</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentacarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Pyrrolidines</alternative_parent>
      <alternative_parent>Pyrrolines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>5'-deoxyribonucleoside</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbene-type 1,3-dipolar compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Imine</substituent>
      <substituent>Ketimine</substituent>
      <substituent>Metallotetrapyrrole skeleton</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic cobalt salt</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organic transition metal salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentacarboxylic acid or derivatives</substituent>
      <substituent>Precorrin</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Purine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrroline</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>cobalt corrinoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-9.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}[(1R,2R,3S,4S,6Z,8S,9S,11Z,14S,18R,19R)-3,8-bis(carbamoylmethyl)-4,9,14,18-tetrakis(2-carboxyethyl)-19-(carboxymethyl)-2,3,6,8,13,13,16,18-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1^{2,5}.1^{7,10}.1^{12,15}]tricosa-5(23),6,10(22),11,15(21),16-hexaen-20-yl]cobaltylium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1187.166</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1186.461960915</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]12[C@H](CC(O)=O)[C@@](C)(CCC(O)=O)\C(N1[Co+]C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)=C(C)\C1=N\C(=C/C3=N/C(=C(C)\C4=N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(O)=O)/[C@@](C)(CC(N)=O)[C@@H]3CCC(O)=O)\C(C)(C)[C@@H]1CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C55H73CoN11O15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C45H62N6O12.C10H12N5O3.Co/c1-21-36-24(10-13-32(56)57)41(3,4)28(49-36)18-27-23(9-12-31(54)55)43(6,19-29(46)52)39(48-27)22(2)37-25(11-14-33(58)59)44(7,20-30(47)53)45(8,51-37)40-26(17-35(62)63)42(5,38(21)50-40)16-15-34(60)61;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/h18,23-26,40H,9-17,19-20H2,1-8H3,(H10,46,47,48,49,50,51,52,53,54,55,56,57,58,59,60,61,62,63);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-1/t23-,24-,25-,26+,40-,42-,43+,44+,45+;4-,6-,7-,10-;/m11./s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OCNLJCZKGHKJGF-NQYRMHKHSA-M</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>432.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>288.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>118.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022414</foodb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <pdbe_id/>
  <chebi_id>2482</chebi_id>
  <drugbank_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00537</protein_accession>
      <name>Cob(I)yrinic acid a,c-diamide adenosyltransferase, mitochondrial</name>
      <uniprot_id>Q58D49</uniprot_id>
      <gene_name>MMAB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:52 UTC</creation_date>
  <update_date>2020-04-15 21:56:19 UTC</update_date>
  <accession>BMDB0001084</accession>
  <secondary_accessions>
    <accession>BMDB01084</accession>
  </secondary_accessions>
  <name>D-1-Piperideine-2-carboxylic acid</name>
  <description/>
  <synonyms>
    <synonym>1,2-Didehydropiperidine-2-carboxylate</synonym>
    <synonym>Delta(1)-Piperidine-2-carboxylic acid</synonym>
    <synonym>1-Piperideine-2-carboxylate</synonym>
    <synonym>1,2-Didehydropiperidine-2-carboxylic acid</synonym>
    <synonym>delta(1)-Piperidine-2-carboxylate</synonym>
    <synonym>Δ(1)-piperidine-2-carboxylate</synonym>
    <synonym>Δ(1)-piperidine-2-carboxylic acid</synonym>
    <synonym>D-1-Piperideine-2-carboxylate</synonym>
    <synonym>delta(1)-Piperideine-2-carboxylate</synonym>
    <synonym>Delta1-Piperideine-2-carboxylate</synonym>
    <synonym>1-p-2-CA</synonym>
    <synonym>delta 1-Piperideine-2-carboxylate</synonym>
    <synonym>delta1-Piperideine-2-carboxylic acid</synonym>
    <synonym>Δ1-piperideine-2-carboxylate</synonym>
    <synonym>Δ1-piperideine-2-carboxylic acid</synonym>
    <synonym>3,4,5,6-Tetrahydro-2-pyridinecarboxylate</synonym>
    <synonym>3,4,5,6-Tetrahydro-2-pyridinecarboxylic acid</synonym>
    <synonym>D-1-Piperideine-2-carboxylic acid</synonym>
    <synonym>delta1-Pipecolic acid</synonym>
    <synonym>delta1-Piperidine-2-carboxylate</synonym>
    <synonym>delta1-Piperidine-2-carboxylic acid</synonym>
    <synonym>Δ1-pipecolic acid</synonym>
    <synonym>Δ1-piperidine-2-carboxylate</synonym>
    <synonym>Δ1-piperidine-2-carboxylic acid</synonym>
    <synonym>P2C</synonym>
    <synonym>1-Piperideine-2-carboxylic acid</synonym>
  </synonyms>
  <chemical_formula>C6H9NO2</chemical_formula>
  <average_molecular_weight>127.1412</average_molecular_weight>
  <monisotopic_moleculate_weight>127.063328537</monisotopic_moleculate_weight>
  <iupac_name>3,4,5,6-tetrahydropyridine-2-carboxylic acid</iupac_name>
  <traditional_iupac>1-piperideine-2-carboxylate</traditional_iupac>
  <cas_registry_number>2756-89-0</cas_registry_number>
  <smiles>OC(=O)C1=NCCCC1</smiles>
  <inchi>InChI=1S/C6H9NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H2,(H,8,9)</inchi>
  <inchikey>GEJXSVNGWOSZPC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydropyridines. These are derivatives of  pyridine in which two double bonds in the pyridine moiety are reduced by adding four hydrogen atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Hydropyridines</sub_class>
    <direct_parent>Tetrahydropyridines</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketimines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Ketimine</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Tetrahydropyridine</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>piperidinemonocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3,4,5,6-tetrahydropyridine-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>127.1412</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>127.063328537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1=NCCCC1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H9NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H9NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H2,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GEJXSVNGWOSZPC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>49.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37919</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337770</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04092</kegg_id>
  <foodb_id>FDB022415</foodb_id>
  <pubchem_compound_id>1194</pubchem_compound_id>
  <chemspider_id>1157</chemspider_id>
  <pdbe_id/>
  <chebi_id>30912</chebi_id>
  <drugbank_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>35015</bigg_id>
  <wikipedia_id/>
  <metlin_id>5992</metlin_id>
  <synthesis_reference>Noguchi, Yuichi; Kanda, Kiyoo; Hosoda, Taku; Akiyama, Katsumi.  D1-Piperidine-2-carboxylic acid isolation from fermentatin broth.    Jpn. Tokkyo Koho  (1971),     5 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:54 UTC</creation_date>
  <update_date>2020-04-16 17:54:09 UTC</update_date>
  <accession>BMDB0001085</accession>
  <secondary_accessions>
    <accession>BMDB01085</accession>
  </secondary_accessions>
  <name>Leukotriene B4</name>
  <description/>
  <synonyms>
    <synonym>(5S,12R,6Z,8E,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoic acid</synonym>
    <synonym>(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acid</synonym>
    <synonym>(S-(R*,s*-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid</synonym>
    <synonym>5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-eicosatetraenoic acid</synonym>
    <synonym>5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-icosatetraenoic acid</synonym>
    <synonym>5,12-Dihete</synonym>
    <synonym>5,12-Hete</synonym>
    <synonym>5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid</synonym>
    <synonym>LTB4</synonym>
    <synonym>(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate</synonym>
    <synonym>(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoate</synonym>
    <synonym>(5S,12R,6Z,8E,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoate</synonym>
    <synonym>(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoate</synonym>
    <synonym>(S-(R*,s*-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenoate</synonym>
    <synonym>5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-eicosatetraenoate</synonym>
    <synonym>5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-icosatetraenoate</synonym>
    <synonym>5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoate</synonym>
    <synonym>(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acid</synonym>
    <synonym>(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoic acid</synonym>
    <synonym>5,12 HETE</synonym>
    <synonym>5,12 DiHETE</synonym>
    <synonym>Leukotriene b-4</synonym>
    <synonym>Leukotrienes b</synonym>
    <synonym>b-4, Leukotriene</synonym>
    <synonym>Leukotriene b 4</synonym>
    <synonym>Leukotriene b</synonym>
    <synonym>5,12-Dihydroxy-6,10-trans -8,14-cis -eicosatetraenoate</synonym>
    <synonym>5,12-Dihydroxy-6,10-trans -8,14-cis -eicosatetraenoic acid</synonym>
    <synonym>Leukotriene b4 ethanol solution</synonym>
    <synonym>(+)-Leukotriene b4</synonym>
    <synonym>(5S,12R)-Leukotriene b4</synonym>
    <synonym>5(S),12(R)-Dihydroxy-6-cis,8,10-trans,14-cis-eicosatetraenoic acid</synonym>
    <synonym>Leucotriene b4</synonym>
    <synonym>cis-Leukotriene b4</synonym>
    <synonym>Leukotriene B4</synonym>
  </synonyms>
  <chemical_formula>C20H32O4</chemical_formula>
  <average_molecular_weight>336.4657</average_molecular_weight>
  <monisotopic_moleculate_weight>336.230059512</monisotopic_moleculate_weight>
  <iupac_name>(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid</iupac_name>
  <traditional_iupac>leukotriene B4</traditional_iupac>
  <cas_registry_number>71160-24-2</cas_registry_number>
  <smiles>CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1</inchi>
  <inchikey>VNYSSYRCGWBHLG-AMOLWHMGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Leukotrienes</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Hydroxyeicosatetraenoic acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Hydroxyeicosatetraenoic acid</substituent>
      <substituent>Leukotriene</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Leukotrienes</external_descriptor>
      <external_descriptor>Leukotrienes</external_descriptor>
      <external_descriptor>dihydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>hydroxy fatty acid</external_descriptor>
      <external_descriptor>leukotriene</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>polyunsaturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>336.4657</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>336.230059512</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H32O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VNYSSYRCGWBHLG-AMOLWHMGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>102.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440658</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02165</kegg_id>
  <foodb_id/>
  <pubchem_compound_id>5280492</pubchem_compound_id>
  <chemspider_id/>
  <pdbe_id/>
  <chebi_id>15647</chebi_id>
  <drugbank_id>DB12961</drugbank_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Leukotriene_B4</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Han, Chao Qi; DiTullio, Dennis; Wang, Yi Fong; Sih, Charles J. A chemoenzymatic synthesis of leukotriene B4. Journal of Organic Chemistry (1986), 51(8), 1253-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00610</protein_accession>
      <name>Leukotriene A-4 hydrolase</name>
      <uniprot_id>Q3SZH7</uniprot_id>
      <gene_name>LTA4H</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01891</protein_accession>
      <name>Leukotriene B4 receptor 1</name>
      <uniprot_id>Q3T181</uniprot_id>
      <gene_name>LTB4R</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:55 UTC</creation_date>
  <update_date>2020-03-13 16:25:48 UTC</update_date>
  <accession>BMDB0001086</accession>
  <secondary_accessions>
    <accession>BMDB01086</accession>
  </secondary_accessions>
  <name>Uroporphyrinogen III</name>
  <description>Uroporphyrinogen III, also known as uroporphyrinogen III, belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure. Uroporphyrinogen III is possibly soluble (in water) and a weakly acidic compound (based on its pKa). Uroporphyrinogen III exists in all living species, ranging from bacteria to humans. In cattle, uroporphyrinogen iii is involved in the metabolic pathway called the porphyrin metabolism pathway.</description>
  <synonyms>
    <synonym>3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-21H,23H-porphine-2,7,12,18-tetrapropanoic acid</synonym>
    <synonym>3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropionic acid</synonym>
    <synonym>Uro'gen III</synonym>
    <synonym>3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-21H,23H-porphine-2,7,12,18-tetrapropanoate</synonym>
    <synonym>3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropionate</synonym>
    <synonym>3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-2,7,12,18-porphinetetrapropionate</synonym>
    <synonym>3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-2,7,12,18-porphinetetrapropionic acid</synonym>
    <synonym>3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoate</synonym>
    <synonym>3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoic acid</synonym>
    <synonym>Urogen III</synonym>
    <synonym>Uroporphyrinogen-III</synonym>
    <synonym>Uroporphyrinogens</synonym>
  </synonyms>
  <chemical_formula>C40H44N4O16</chemical_formula>
  <average_molecular_weight>836.7946</average_molecular_weight>
  <monisotopic_moleculate_weight>836.27523138</monisotopic_moleculate_weight>
  <iupac_name>3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>uroporphyrinogen-III</traditional_iupac>
  <cas_registry_number>1976-85-8</cas_registry_number>
  <smiles>OC(=O)CCC1=C2CC3=C(CCC(O)=O)C(CC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=C(CC5=C(CC(O)=O)C(CCC(O)=O)=C(CC(N2)=C1CC(O)=O)N5)N4)N3</smiles>
  <inchi>InChI=1S/C40H44N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-27-19(3-7-35(49)50)22(10-38(55)56)30(43-27)15-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)16-31-23(11-39(57)58)18(2-6-34(47)48)26(42-31)13-25(17)41-29/h41-44H,1-16H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)</inchi>
  <inchikey>HUHWZXWWOFSFKF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Porphyrin</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>uroporphyrinogen</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>836.7946</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>836.27523138</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC1=C2CC3=C(CCC(O)=O)C(CC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=C(CC5=C(CC(O)=O)C(CCC(O)=O)=C(CC(N2)=C1CC(O)=O)N5)N4)N3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C40H44N4O16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C40H44N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-27-19(3-7-35(49)50)22(10-38(55)56)30(43-27)15-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)16-31-23(11-39(57)58)18(2-6-34(47)48)26(42-31)13-25(17)41-29/h41-44H,1-16H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HUHWZXWWOFSFKF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>361.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>206.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>81.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36145</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01051</kegg_id>
  <foodb_id>FDB031250</foodb_id>
  <pubchem_compound_id>1179</pubchem_compound_id>
  <chemspider_id>1146</chemspider_id>
  <pdbe_id/>
  <chebi_id>15437</chebi_id>
  <drugbank_id/>
  <knapsack_id>C00007373</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>36704</bigg_id>
  <wikipedia_id>Uroporphyrinogen III</wikipedia_id>
  <metlin_id>79</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:56 UTC</creation_date>
  <update_date>2020-03-13 16:25:48 UTC</update_date>
  <accession>BMDB0001087</accession>
  <secondary_accessions>
    <accession>BMDB01087</accession>
  </secondary_accessions>
  <name>5-Methylthioribose</name>
  <description/>
  <synonyms>
    <synonym>S-Methyl-5-thio-D-ribose</synonym>
    <synonym>5-Deoxy-5-(methylthio)ribose</synonym>
    <synonym>5-Methylthio-D-ribose</synonym>
    <synonym>S(5)-Methyl-5-thio-D-ribose</synonym>
    <synonym>S5-Methyl-5-thio-D-ribose</synonym>
    <synonym>5-Methylthioribose</synonym>
    <synonym>5-S-Methyl-5-thio-D-ribose</synonym>
    <synonym>5-S-Methyl-5-thio-beta-D-ribofuranose</synonym>
    <synonym>5-S-Methyl-5-thio-β-D-ribofuranose</synonym>
    <synonym>S-Methyl-5-thio-D-ribofuranose</synonym>
  </synonyms>
  <chemical_formula>C6H12O4S</chemical_formula>
  <average_molecular_weight>180.222</average_molecular_weight>
  <monisotopic_moleculate_weight>180.045629562</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4S,5S)-5-[(methylsulfanyl)methyl]oxolane-2,3,4-triol</iupac_name>
  <traditional_iupac>5-methylthio-D-ribose</traditional_iupac>
  <cas_registry_number>23656-67-9</cas_registry_number>
  <smiles>CSC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H12O4S/c1-11-2-3-4(7)5(8)6(9)10-3/h3-9H,2H2,1H3/t3-,4-,5-,6-/m1/s1</inchi>
  <inchikey>OLVVOVIFTBSBBH-KVTDHHQDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentoses</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Dialkylthioethers</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thioether</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R,4S,5S)-5-[(methylsulfanyl)methyl]oxolane-2,3,4-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>180.222</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>180.045629562</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CSC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O4S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O4S/c1-11-2-3-4(7)5(8)6(9)10-3/h3-9H,2H2,1H3/t3-,4-,5-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OLVVOVIFTBSBBH-KVTDHHQDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>69.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37921</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35146</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022418</foodb_id>
  <kegg_id>C03089</kegg_id>
  <chemspider_id>388938</chemspider_id>
  <pubchem_compound_id>439904</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16895</chebi_id>
  <knapsack_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD-560</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5995</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:57 UTC</creation_date>
  <update_date>2020-04-15 22:00:11 UTC</update_date>
  <accession>BMDB0001088</accession>
  <secondary_accessions>
    <accession>BMDB01088</accession>
  </secondary_accessions>
  <name>Butyryl-CoA</name>
  <description/>
  <synonyms>
    <synonym>Butanoyl-CoA</synonym>
    <synonym>Butanoyl-coenzyme A</synonym>
    <synonym>Butyryl-coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C25H42N7O17P3S</chemical_formula>
  <average_molecular_weight>837.624</average_molecular_weight>
  <monisotopic_moleculate_weight>837.157073179</monisotopic_moleculate_weight>
  <iupac_name>{[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(butanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>butyryl-coa</traditional_iupac>
  <cas_registry_number>2140-48-9</cas_registry_number>
  <smiles>CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C25H42N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h12-14,18-20,24,35-36H,4-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)</inchi>
  <inchikey>CRFNGMNYKDXRTN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Leukotrienes</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Hydroxyeicosatetraenoic acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Hydroxyeicosatetraenoic acid</substituent>
      <substituent>Leukotriene</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Leukotrienes</external_descriptor>
      <external_descriptor>dihydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>hydroxy fatty acid</external_descriptor>
      <external_descriptor>leukotriene</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>polyunsaturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(butanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>837.624</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>837.157073179</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H42N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C25H42N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h12-14,18-20,24,35-36H,4-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CRFNGMNYKDXRTN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>181.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>75.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182796</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183146</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>3.40 +/- 0.78</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Ash R, Baird GD: Activation of volatile fatty acids in bovine liver and rumen epithelium. Evidence for control by autoregulation. Biochem J. 1973 Oct;136(2):311-9.</reference_text>
          <pubmed_id>4359516</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022419</foodb_id>
  <kegg_id>C00136</kegg_id>
  <chemspider_id>260</chemspider_id>
  <pubchem_compound_id>265</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>57371</chebi_id>
  <knapsack_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>33988</bigg_id>
  <wikipedia_id>Butyryl-CoA</wikipedia_id>
  <metlin_id>5996</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00788</protein_accession>
      <name>Short-chain specific acyl-CoA dehydrogenase, mitochondrial</name>
      <uniprot_id>Q3ZBF6</uniprot_id>
      <gene_name>ACADS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:40:58 UTC</creation_date>
  <update_date>2020-03-13 16:25:49 UTC</update_date>
  <accession>BMDB0001090</accession>
  <secondary_accessions>
    <accession>BMDB01090</accession>
  </secondary_accessions>
  <name>5-Diphosphomevalonic acid</name>
  <description/>
  <synonyms>
    <synonym>(R)-5-Diphosphomevalonate</synonym>
    <synonym>5-Diphosphomevalonate</synonym>
    <synonym>5-Diphosphomevalonic acid</synonym>
    <synonym>Mevalonate 5-diphosphate</synonym>
    <synonym>Mevalonate pyrophosphate</synonym>
    <synonym>Mevalonate-diphosphate</synonym>
    <synonym>(3R)-3-Hydroxy-5-[[hydroxy(phosphonooxy)phosphinyl]oxy]-3-methylpentanoic acid</synonym>
    <synonym>(R)-Diphosphomevalonic acid</synonym>
    <synonym>5-Pyrophosphomevalonic acid</synonym>
    <synonym>Mevalonic 5-pyrophosphate</synonym>
    <synonym>Mevalonic acid 5-diphosphate</synonym>
    <synonym>Mevalonic acid 5-pyrophosphate</synonym>
    <synonym>Mevalonic acid pyrophosphate</synonym>
    <synonym>Pyrophosphomevalonic acid</synonym>
    <synonym>(3R)-3-Hydroxy-5-[[hydroxy(phosphonooxy)phosphinyl]oxy]-3-methylpentanoate</synonym>
    <synonym>(R)-Diphosphomevalonate</synonym>
    <synonym>5-Pyrophosphomevalonate</synonym>
    <synonym>Mevalonate 5-pyrophosphate</synonym>
    <synonym>Mevalonic 5-pyrophosphic acid</synonym>
    <synonym>Mevalonic acid 5-diphosphic acid</synonym>
    <synonym>Mevalonic acid 5-pyrophosphic acid</synonym>
    <synonym>Mevalonic acid pyrophosphic acid</synonym>
    <synonym>Pyrophosphomevalonate</synonym>
    <synonym>(R)-5-Diphosphomevalonic acid</synonym>
  </synonyms>
  <chemical_formula>C6H14O10P2</chemical_formula>
  <average_molecular_weight>308.1169</average_molecular_weight>
  <monisotopic_moleculate_weight>308.006219692</monisotopic_moleculate_weight>
  <iupac_name>(3R)-3-hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoic acid</iupac_name>
  <traditional_iupac>mevalonate-diphosphate</traditional_iupac>
  <cas_registry_number>956-46-7</cas_registry_number>
  <smiles>C[C@@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C6H14O10P2/c1-6(9,4-5(7)8)2-3-15-18(13,14)16-17(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H,13,14)(H2,10,11,12)/t6-/m1/s1</inchi>
  <inchikey>SIGQQUBJQXSAMW-ZCFIWIBFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organic oxoanionic compounds</class>
    <sub_class>Organic pyrophosphates</sub_class>
    <direct_parent>Organic pyrophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
      <external_descriptor>carboxyalkyl phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R)-3-hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>308.1169</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>308.006219692</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H14O10P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H14O10P2/c1-6(9,4-5(7)8)2-3-15-18(13,14)16-17(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H,13,14)(H2,10,11,12)/t6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SIGQQUBJQXSAMW-ZCFIWIBFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>170.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>56.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37922</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180644</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01143</kegg_id>
  <foodb_id>FDB031002</foodb_id>
  <chemspider_id>388531</chemspider_id>
  <pubchem_compound_id>439418</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15899</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007615</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00101</protein_accession>
      <name>Diphosphomevalonate decarboxylase</name>
      <uniprot_id>Q0P570</uniprot_id>
      <gene_name>MVD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:00 UTC</creation_date>
  <update_date>2020-03-13 16:25:50 UTC</update_date>
  <accession>BMDB0001091</accession>
  <secondary_accessions>
    <accession>BMDB01091</accession>
  </secondary_accessions>
  <name>3-Hydroxyquinine</name>
  <description/>
  <synonyms>
    <synonym>3-Hydroxyquinidine</synonym>
    <synonym>3-Hydroxyquinidine, (8alpha,9R)-isomer</synonym>
    <synonym>3-Hydroxyquinidine, (3alpha,9S)-isomer</synonym>
    <synonym>6'-Methoxycinchonan-3,9-diol</synonym>
    <synonym>3-Hydroxyquinine</synonym>
  </synonyms>
  <chemical_formula>C20H24N2O3</chemical_formula>
  <average_molecular_weight>340.4162</average_molecular_weight>
  <monisotopic_moleculate_weight>340.178692644</monisotopic_moleculate_weight>
  <iupac_name>(3S,4R,6S)-3-ethenyl-6-[(R)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol</iupac_name>
  <traditional_iupac>3-hydroxyquinidine</traditional_iupac>
  <cas_registry_number>53467-23-5</cas_registry_number>
  <smiles>[H][C@]12CCN(C[C@]1(O)C=C)[C@@]([H])(C2)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12</smiles>
  <inchi>InChI=1S/C20H24N2O3/c1-3-20(24)12-22-9-7-13(20)10-18(22)19(23)15-6-8-21-17-5-4-14(25-2)11-16(15)17/h3-6,8,11,13,18-19,23-24H,1,7,9-10,12H2,2H3/t13-,18+,19-,20-/m1/s1</inchi>
  <inchikey>BSRUJCFCZKMFMB-ZNYHDOEXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Alkaloids and derivatives</super_class>
    <class>Cinchona alkaloids</class>
    <sub_class/>
    <direct_parent>Cinchona alkaloids</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>4-quinolinemethanols</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Piperidines</alternative_parent>
      <alternative_parent>Pyridines and derivatives</alternative_parent>
      <alternative_parent>Quinuclidines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>4-quinolinemethanol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Amine</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Cinchonan-skeleton</substituent>
      <substituent>Ether</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Piperidine</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Quinoline</substituent>
      <substituent>Quinuclidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3S,4R,6S)-3-ethenyl-6-[(R)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>340.4162</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>340.178692644</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]12CCN(C[C@]1(O)C=C)[C@@]([H])(C2)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H24N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H24N2O3/c1-3-20(24)12-22-9-7-13(20)10-18(22)19(23)15-6-8-21-17-5-4-14(25-2)11-16(15)17/h3-6,8,11,13,18-19,23-24H,1,7,9-10,12H2,2H3/t13-,18+,19-,20-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BSRUJCFCZKMFMB-ZNYHDOEXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>65.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>95.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15858</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343578</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C07344</kegg_id>
  <foodb_id>FDB022421</foodb_id>
  <pubchem_compound_id>441264</pubchem_compound_id>
  <chemspider_id>138373</chemspider_id>
  <pdbe_id/>
  <chebi_id>17685</chebi_id>
  <drugbank_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>3-HYDROXYQUININE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>2234</metlin_id>
  <synthesis_reference>Carroll, F. Ivy; Abraham, Philip; Gaetano, Kevan; Mascarella, S. Wayne; Wohl, Ronald A.; Lind, Joan; Petzoldt, Karl.  (3S)-3-hydroxyquinidine, the major biotransformation product of quinidine. Synthesis and conformational studies. X-Ray molecular structure of (3S)-3-hydroxyquinidine methanesuiphonate. J. Chem. Soc., Perkin Trans. 1, 1991, 12, 3017-3026</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:01 UTC</creation_date>
  <update_date>2020-03-13 16:25:51 UTC</update_date>
  <accession>BMDB0001093</accession>
  <secondary_accessions>
    <accession>BMDB01093</accession>
  </secondary_accessions>
  <name>5a-Cholesta-8,24-dien-3-one</name>
  <description/>
  <synonyms>
    <synonym>5alpha-Cholesta-8,24-dien-3-one</synonym>
  </synonyms>
  <chemical_formula>C27H42O</chemical_formula>
  <average_molecular_weight>382.6218</average_molecular_weight>
  <monisotopic_moleculate_weight>382.323565966</monisotopic_moleculate_weight>
  <iupac_name>(2S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one</iupac_name>
  <traditional_iupac>5a-cholesta-8,24-dien-3-one</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@]12CC[C@H]([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CCC2CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,19-20,23-24H,6,8-17H2,1-5H3/t19-,20?,23-,24+,26+,27-/m1/s1</inchi>
  <inchikey>AUNLIRXIJAVBNM-YBXLEUBGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-oxosteroids</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-oxosteroid</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>382.6218</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>382.323565966</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H]([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CCC2CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H42O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,19-20,23-24H,6,8-17H2,1-5H3/t19-,20?,23-,24+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AUNLIRXIJAVBNM-YBXLEUBGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>120.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>48.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>339747</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id>17216058</chemspider_id>
  <foodb_id>FDB022422</foodb_id>
  <pubchem_compound_id>22833560</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5999</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:03 UTC</creation_date>
  <update_date>2020-03-13 16:25:51 UTC</update_date>
  <accession>BMDB0001094</accession>
  <secondary_accessions>
    <accession>BMDB01094</accession>
  </secondary_accessions>
  <name>Octaprenyl diphosphate</name>
  <description/>
  <synonyms>
    <synonym>(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-OCTAMETHYLDOTRIACONTA-2,6,10,14,18,22,26,30-octaenyl trihydrogen diphosphATE</synonym>
    <synonym>all-trans-Octaprenyl pyrophosphate</synonym>
    <synonym>Farnesylfarnesylgeraniol</synonym>
    <synonym>(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-OCTAMETHYLDOTRIACONTA-2,6,10,14,18,22,26,30-octaenyl trihydrogen diphosphoric acid</synonym>
    <synonym>all-trans-Octaprenyl pyrophosphoric acid</synonym>
    <synonym>Octaprenyl diphosphoric acid</synonym>
    <synonym>all-trans-Octaprenyl diphosphate</synonym>
    <synonym>Octaprenyl pyrophosphate</synonym>
    <synonym>OPP</synonym>
  </synonyms>
  <chemical_formula>C40H68O7P2</chemical_formula>
  <average_molecular_weight>722.9112</average_molecular_weight>
  <monisotopic_moleculate_weight>722.444027554</monisotopic_moleculate_weight>
  <iupac_name>{[hydroxy({[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>octaprenyl pyrophosphate</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C40H68O7P2/c1-33(2)17-10-18-34(3)19-11-20-35(4)21-12-22-36(5)23-13-24-37(6)25-14-26-38(7)27-15-28-39(8)29-16-30-40(9)31-32-46-49(44,45)47-48(41,42)43/h17,19,21,23,25,27,29,31H,10-16,18,20,22,24,26,28,30,32H2,1-9H3,(H,44,45)(H2,41,42,43)/b34-19+,35-21+,36-23+,37-25+,38-27+,39-29+,40-31+</inchi>
  <inchikey>IKKLDISSULFFQO-DJMILUHSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetraterpenoids. These are terpenoid molecules containing 10 consecutively linked isoprene units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Tetraterpenoids</sub_class>
    <direct_parent>Tetraterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Bactoprenol diphosphates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Isoprenoid phosphates</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Polyprenyl diphosphates</alternative_parent>
      <alternative_parent>Polyprenyl monophosphates</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Bactoprenol diphosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isoprenoid phosphate</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyprenyl diphosphate</substituent>
      <substituent>Polyprenyl monophosphate</substituent>
      <substituent>Polyprenyl phosphate skeleton</substituent>
      <substituent>Tetraterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C40 isoprenoids (tetraterpenes)</external_descriptor>
      <external_descriptor>C40 isoprenoids (tetraterpenes)</external_descriptor>
      <external_descriptor>Polyterpenoids</external_descriptor>
      <external_descriptor>all-trans-polyprenyl diphosphate</external_descriptor>
      <external_descriptor>octaprenyl diphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>11.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[hydroxy({[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>722.9112</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>722.444027554</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C40H68O7P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C40H68O7P2/c1-33(2)17-10-18-34(3)19-11-20-35(4)21-12-22-36(5)23-13-24-37(6)25-14-26-38(7)27-15-28-39(8)29-16-30-40(9)31-32-46-49(44,45)47-48(41,42)43/h17,19,21,23,25,27,29,31H,10-16,18,20,22,24,26,28,30,32H2,1-9H3,(H,44,45)(H2,41,42,43)/b34-19+,35-21+,36-23+,37-25+,38-27+,39-29+,40-31+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IKKLDISSULFFQO-DJMILUHSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>215.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>86.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>59767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30943</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04146</kegg_id>
  <chemspider_id>4444251</chemspider_id>
  <foodb_id>FDB022423</foodb_id>
  <pubchem_compound_id>5280651</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16275</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6000</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:04 UTC</creation_date>
  <update_date>2020-04-16 20:37:56 UTC</update_date>
  <accession>BMDB0001095</accession>
  <secondary_accessions>
    <accession>BMDB01095</accession>
  </secondary_accessions>
  <name>GDP-L-fucose</name>
  <description>GDP-L-Fucose, also known as GDP fucose or fucose, GDP, belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. GDP-L-Fucose is possibly soluble (in water) and a moderately basic compound (based on its pKa). GDP-L-Fucose exists in all living organisms, ranging from bacteria to humans. GDP-L-Fucose participates in a number of enzymatic reactions, within cattle. In particular, GDP-L-Fucose can be converted into GDP-4-dehydro-6-deoxy-D-mannose through the action of the enzyme GDP-L-fucose synthase. In addition, GDP-L-Fucose can be biosynthesized from fucose 1-phosphate; which is mediated by the enzyme fucose-1-phosphate guanylyltransferase. In cattle, GDP-L-fucose is involved in the metabolic pathway called the fructose and mannose degradation pathway.</description>
  <synonyms>
    <synonym>(6-Deoxy-beta-L-galactopyranosyl) ester</synonym>
    <synonym>GDP Fucose</synonym>
    <synonym>GDP-beta-L-Fucose</synonym>
    <synonym>Guanosine diphosphate fucose</synonym>
    <synonym>Guanosine diphosphofucose</synonym>
    <synonym>Diphosphate fucose, guanosine</synonym>
    <synonym>Diphosphofucose, guanosine</synonym>
    <synonym>Fucose, GDP</synonym>
    <synonym>Fucose, guanosine diphosphate</synonym>
    <synonym>GDP-Fucose</synonym>
    <synonym>GDP-Β-L-fucose</synonym>
    <synonym>Guanosine 5'-diphosphate L-fucose</synonym>
    <synonym>Guanosine 5'-diphospho-fucose</synonym>
    <synonym>Guanosine 5'-diphosphofucose</synonym>
    <synonym>Guanosine 5’-diphosphate L-fucose</synonym>
    <synonym>Guanosine 5’-diphospho-fucose</synonym>
    <synonym>Guanosine 5’-diphosphofucose</synonym>
    <synonym>GDP-L-fucose</synonym>
  </synonyms>
  <chemical_formula>C16H25N5O15P2</chemical_formula>
  <average_molecular_weight>589.3417</average_molecular_weight>
  <monisotopic_moleculate_weight>589.082238179</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>gdp-L-fucose</traditional_iupac>
  <cas_registry_number>15839-70-0</cas_registry_number>
  <smiles>C[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5+,7+,8+,9+,10+,11-,14+,15?/m0/s1</inchi>
  <inchikey>LQEBEXMHBLQMDB-QIXZNPMTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine nucleotide sugars</sub_class>
    <direct_parent>Purine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>GDP-fucose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>589.3417</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>589.082238179</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H25N5O15P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5+,7+,8+,9+,10+,11-,14+,15?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LQEBEXMHBLQMDB-QIXZNPMTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>307.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>116.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37924</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34051</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0 - 67.400</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44.</reference_text>
          <pubmed_id>7196410</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00325</kegg_id>
  <chemspider_id>388350</chemspider_id>
  <foodb_id>FDB030882</foodb_id>
  <pubchem_compound_id>439211</pubchem_compound_id>
  <pdbe_id>GFB</pdbe_id>
  <chebi_id>17009</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007245</knapsack_id>
  <meta_cyc_id/>
  <bigg_id>34623</bigg_id>
  <wikipedia_id/>
  <metlin_id>6001</metlin_id>
  <synthesis_reference>Yamamoto, Kenji; Maruyama, Takashi; Kumagai, Hidehiko; Tochikura, Tatsurokuro; Seno, Taiko; Yamaguchi, Hideo.  Preparation of GDP-L-fucose by using microbial enzymes.    Agricultural and Biological Chemistry  (1984),  48(3),  823-4.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44.</reference_text>
      <pubmed_id>7196410</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01324</protein_accession>
      <name>Alpha-(1,6)-fucosyltransferase</name>
      <uniprot_id>Q9N0W2</uniprot_id>
      <gene_name>FUT8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01325</protein_accession>
      <name>Galactoside 3(4)-L-fucosyltransferase</name>
      <uniprot_id>Q11126</uniprot_id>
      <gene_name>FUT3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01326</protein_accession>
      <name>Galactoside 2-alpha-L-fucosyltransferase 2</name>
      <uniprot_id>Q28113</uniprot_id>
      <gene_name>FUT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:05 UTC</creation_date>
  <update_date>2020-04-15 22:32:50 UTC</update_date>
  <accession>BMDB0001096</accession>
  <secondary_accessions>
    <accession>BMDB01096</accession>
  </secondary_accessions>
  <name>Carbamoylphosphate</name>
  <description/>
  <synonyms>
    <synonym>Aminocarbonyl dihydrogen phosphate</synonym>
    <synonym>Carbamic phosphoric monoanhydride</synonym>
    <synonym>Carbamyl phosphate</synonym>
    <synonym>Monocarbamoyl phosphate</synonym>
    <synonym>PHOSPHORIC ACID mono(formamide)ester</synonym>
    <synonym>Aminocarbonyl dihydrogen phosphoric acid</synonym>
    <synonym>Carbamyl phosphoric acid</synonym>
    <synonym>Monocarbamoyl phosphoric acid</synonym>
    <synonym>PHOSPHate mono(formamide)ester</synonym>
    <synonym>Carbamoyl phosphoric acid</synonym>
    <synonym>Carbamic acid monoanhydride with phosphorate</synonym>
    <synonym>Carbamic acid monoanhydride with phosphoric acid</synonym>
    <synonym>Carbamoyl-p</synonym>
    <synonym>Carbamoyl-phosphate</synonym>
    <synonym>Carbamoylphosphate</synonym>
    <synonym>Carbamyl-phosphate</synonym>
    <synonym>Phosphate, carbamyl</synonym>
    <synonym>Carbamyl phosphate, dilithium</synonym>
    <synonym>Dilithium carbamyl phosphate</synonym>
    <synonym>Phosphate, dilithium carbamyl</synonym>
    <synonym>Phosphate, carbamoyl</synonym>
  </synonyms>
  <chemical_formula>CH4NO5P</chemical_formula>
  <average_molecular_weight>141.0199</average_molecular_weight>
  <monisotopic_moleculate_weight>140.982708755</monisotopic_moleculate_weight>
  <iupac_name>(carbamoyloxy)phosphonic acid</iupac_name>
  <traditional_iupac>carbamoyl-phosphate</traditional_iupac>
  <cas_registry_number>590-55-6</cas_registry_number>
  <smiles>NC(=O)OP(O)(O)=O</smiles>
  <inchi>InChI=1S/CH4NO5P/c2-1(3)7-8(4,5)6/h(H2,2,3)(H2,4,5,6)</inchi>
  <inchikey>FFQKYPRQEYGKAF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as organic phosphoric acids and derivatives. These are organic compounds containing phosphoric acid or a derivative thereof.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic phosphoric acids and derivatives</class>
    <sub_class/>
    <direct_parent>Organic phosphoric acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboximidic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>acyl monophosphate</external_descriptor>
      <external_descriptor>one-carbon compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(carbamoyloxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>141.0199</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>140.982708755</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>CH4NO5P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/CH4NO5P/c2-1(3)7-8(4,5)6/h(H2,2,3)(H2,4,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FFQKYPRQEYGKAF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>109.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>22.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21934</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00169</kegg_id>
  <chemspider_id>272</chemspider_id>
  <foodb_id>FDB022424</foodb_id>
  <pubchem_compound_id>278</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17672</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007513</knapsack_id>
  <meta_cyc_id/>
  <bigg_id>34125</bigg_id>
  <wikipedia_id>Carbamoyl phosphate</wikipedia_id>
  <metlin_id>6002</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00953</protein_accession>
      <name>Ornithine carbamoyltransferase, mitochondrial</name>
      <uniprot_id>Q9N1U7</uniprot_id>
      <gene_name>OTC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:06 UTC</creation_date>
  <update_date>2020-04-15 22:26:08 UTC</update_date>
  <accession>BMDB0001097</accession>
  <secondary_accessions>
    <accession>BMDB01097</accession>
  </secondary_accessions>
  <name>Protoporphyrinogen IX</name>
  <description/>
  <synonyms>
    <synonym>7,12-Diethenyl-3,8,13,17-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,18-dipropanoic acid</synonym>
    <synonym>7,12-Diethenyl-3,8,13,17-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,18-dipropanoate</synonym>
    <synonym>5,10,15,20,22,24-Hexahydro protoporphyrin IX deriv.</synonym>
    <synonym>7,12-Diethenyl-5,10,15,20,22,24-hexahydro-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoate</synonym>
    <synonym>7,12-Diethenyl-5,10,15,20,22,24-hexahydro-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoic acid</synonym>
    <synonym>Protoporphyrinogen</synonym>
    <synonym>Protoporphyrinogen-IX</synonym>
  </synonyms>
  <chemical_formula>C34H40N4O4</chemical_formula>
  <average_molecular_weight>568.7058</average_molecular_weight>
  <monisotopic_moleculate_weight>568.304955788</monisotopic_moleculate_weight>
  <iupac_name>3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>7412-77-3</cas_registry_number>
  <smiles>CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(C=C)=C(CC5=C(C)C(CCC(O)=O)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3</smiles>
  <inchi>InChI=1S/C34H40N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,35-38H,1-2,9-16H2,3-6H3,(H,39,40)(H,41,42)</inchi>
  <inchikey>UHSGPDMIQQYNAX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Porphyrin</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>porphyrinogens</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>568.7058</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>568.304955788</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C2CC3=C(C)C(C=C)=C(CC4=C(C)C(C=C)=C(CC5=C(C)C(CCC(O)=O)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C34H40N4O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C34H40N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,35-38H,1-2,9-16H2,3-6H3,(H,39,40)(H,41,42)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UHSGPDMIQQYNAX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>137.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>169.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>64.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33148</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01079</kegg_id>
  <chemspider_id>108741</chemspider_id>
  <foodb_id>FDB022425</foodb_id>
  <pubchem_compound_id>121893</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15435</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007371</knapsack_id>
  <meta_cyc_id/>
  <bigg_id>36764</bigg_id>
  <wikipedia_id>Protoporphyrinogen IX</wikipedia_id>
  <metlin_id>6003</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00527</protein_accession>
      <name>Protoporphyrinogen oxidase</name>
      <uniprot_id>P56602</uniprot_id>
      <gene_name>PPOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:07 UTC</creation_date>
  <update_date>2020-03-13 16:25:53 UTC</update_date>
  <accession>BMDB0001101</accession>
  <secondary_accessions>
    <accession>BMDB01101</accession>
  </secondary_accessions>
  <name>p-Anisic acid</name>
  <description/>
  <synonyms>
    <synonym>4-Anisic acid</synonym>
    <synonym>Anisic acid</synonym>
    <synonym>Draconic acid</synonym>
    <synonym>p-Methoxybenzoic acid</synonym>
    <synonym>4-Methoxybenzoic acid</synonym>
    <synonym>4-Anisate</synonym>
    <synonym>Anisate</synonym>
    <synonym>Draconate</synonym>
    <synonym>p-Methoxybenzoate</synonym>
    <synonym>4-Methoxybenzoate</synonym>
    <synonym>p-Anisate</synonym>
    <synonym>4-Anisic acid, copper (+2) salt</synonym>
    <synonym>4-Anisic acid, 14C-carboxy</synonym>
    <synonym>4-Anisic acid, potassium salt</synonym>
    <synonym>4-Anisic acid, sodium salt</synonym>
    <synonym>Para-anisic acid</synonym>
    <synonym>p-Anisic acid</synonym>
  </synonyms>
  <chemical_formula>C8H8O3</chemical_formula>
  <average_molecular_weight>152.1473</average_molecular_weight>
  <monisotopic_moleculate_weight>152.047344122</monisotopic_moleculate_weight>
  <iupac_name>4-methoxybenzoic acid</iupac_name>
  <traditional_iupac>P-anisic acid</traditional_iupac>
  <cas_registry_number>100-09-4</cas_registry_number>
  <smiles>COC1=CC=C(C=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10)</inchi>
  <inchikey>ZEYHEAKUIGZSGI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>P-methoxybenzoic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>P-methoxybenzoic acid or derivatives</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>methoxybenzoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>185 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.53 mg/mL at 37 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.96</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-methoxybenzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>152.1473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>152.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC=C(C=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZEYHEAKUIGZSGI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>46.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437283</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02519</kegg_id>
  <chemspider_id>10181338</chemspider_id>
  <foodb_id>FDB010587</foodb_id>
  <pubchem_compound_id>7478</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>40813</chebi_id>
  <drugbank_id>DB02795</drugbank_id>
  <phenol_explorer_compound_id>425</phenol_explorer_compound_id>
  <knapsack_id>C00029536</knapsack_id>
  <meta_cyc_id>CPD-1076</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>P-Anisic_acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:08 UTC</creation_date>
  <update_date>2020-04-14 22:48:51 UTC</update_date>
  <accession>BMDB0001104</accession>
  <secondary_accessions>
    <accession>BMDB01104</accession>
  </secondary_accessions>
  <name>N-Acetyl-b-glucosaminylamine</name>
  <description/>
  <synonyms>
    <synonym>N-Acetyl-b-D-glucosaminylamine</synonym>
    <synonym>N-Acetyl-beta-D-glucosaminylamine</synonym>
    <synonym>N-Acetyl-beta-delta-glucosaminylamine</synonym>
    <synonym>N-Acetyl-beta-glucosaminylamine</synonym>
    <synonym>N-[2-Amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanamide</synonym>
  </synonyms>
  <chemical_formula>C8H16N2O5</chemical_formula>
  <average_molecular_weight>220.223</average_molecular_weight>
  <monisotopic_moleculate_weight>220.105921632</monisotopic_moleculate_weight>
  <iupac_name>N-[(2R,3R,4R,5S,6R)-2-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide</iupac_name>
  <traditional_iupac>N-acetyl-β-D-glucosaminylamine</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(=O)N[C@H]1[C@H](N)O[C@H](CO)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C8H16N2O5/c1-3(12)10-5-7(14)6(13)4(2-11)15-8(5)9/h4-8,11,13-14H,2,9H2,1H3,(H,10,12)/t4-,5-,6-,7-,8-/m1/s1</inchi>
  <inchikey>MCGXOCXFFNKASF-FMDGEEDCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hemiaminals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hemiaminal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>glucosaminylamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[(2R,3R,4R,5S,6R)-2-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>220.223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>220.105921632</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@H]1[C@H](N)O[C@H](CO)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16N2O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16N2O5/c1-3(12)10-5-7(14)6(13)4(2-11)15-8(5)9/h4-8,11,13-14H,2,9H2,1H3,(H,10,12)/t4-,5-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MCGXOCXFFNKASF-FMDGEEDCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>125.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>48.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34630</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01239</kegg_id>
  <chemspider_id>388560</chemspider_id>
  <foodb_id>FDB031028</foodb_id>
  <pubchem_compound_id>439454</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15947</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>N-ACETYL-BETA-GLUCOSAMINYLAMINE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6006</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:10 UTC</creation_date>
  <update_date>2020-03-13 16:25:54 UTC</update_date>
  <accession>BMDB0001106</accession>
  <secondary_accessions>
    <accession>BMDB01106</accession>
  </secondary_accessions>
  <name>3-Aminopropionaldehyde</name>
  <description>3-Aminopropionaldehyde, also known as 3-aminopropanal, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. 3-Aminopropionaldehyde is possibly soluble (in water) and a very strong basic compound (based on its pKa). 3-Aminopropionaldehyde exists in all living species, ranging from bacteria to humans. 3-Aminopropionaldehyde participates in a number of enzymatic reactions, within cattle. In particular, 3-Aminopropionaldehyde can be converted into beta-alanine through the action of the enzyme aldehyde dehydrogenase, mitochondrial. In addition, 3-Aminopropionaldehyde can be biosynthesized from 1,3-diaminopropane through its interaction with the enzyme membrane primary amine oxidase. In cattle, 3-aminopropionaldehyde is involved in the metabolic pathway called the beta-alanine metabolism pathway.</description>
  <synonyms>
    <synonym>beta-Aminopropion aldehyde</synonym>
    <synonym>b-Aminopropion aldehyde</synonym>
    <synonym>Β-aminopropion aldehyde</synonym>
    <synonym>3-Aminopropanal</synonym>
  </synonyms>
  <chemical_formula>C3H7NO</chemical_formula>
  <average_molecular_weight>73.0938</average_molecular_weight>
  <monisotopic_moleculate_weight>73.052763851</monisotopic_moleculate_weight>
  <iupac_name>3-aminopropanal</iupac_name>
  <traditional_iupac>3-aminopropanal</traditional_iupac>
  <cas_registry_number>352-92-1</cas_registry_number>
  <smiles>NCCC=O</smiles>
  <inchi>InChI=1S/C3H7NO/c4-2-1-3-5/h3H,1-2,4H2</inchi>
  <inchikey>PCXDJQZLDDHMGX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Alpha-hydrogen aldehydes</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydrogen aldehyde</substituent>
      <substituent>Amine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>propanals</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-aminopropanal</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>73.0938</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>73.052763851</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCC=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7NO/c4-2-1-3-5/h3H,1-2,4H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PCXDJQZLDDHMGX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>43.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>19.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>7.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21730</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By GC-TOFMS and UPLC-QTOFMS</comment>
      <references>
        <reference>
          <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
          <pubmed_id>27999311</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C05665</kegg_id>
  <chemspider_id>74</chemspider_id>
  <foodb_id>FDB030407</foodb_id>
  <pubchem_compound_id>75</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18090</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id>46232</bigg_id>
  <wikipedia_id/>
  <metlin_id>6007</metlin_id>
  <synthesis_reference>Bott, Kaspar.  Amidomethylation of trichloroethylene and acetylene:  syntheses of N-protected a-chloro-b-alanines and b-aminopropanals.    Journal of the Chemical Society [Section] D:  Chemical Communications  (1969),   (22),  1304.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
      <pubmed_id>27999311</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:11 UTC</creation_date>
  <update_date>2020-03-13 16:25:55 UTC</update_date>
  <accession>BMDB0001107</accession>
  <secondary_accessions>
    <accession>BMDB01107</accession>
  </secondary_accessions>
  <name>7-Methylguanosine</name>
  <description/>
  <synonyms>
    <synonym>G</synonym>
    <synonym>m7g</synonym>
    <synonym>N(7)-Methylguanosine</synonym>
    <synonym>2-Amino-6,9-dihydro-7-methyl-6-oxo-9-beta-D-ribofuranosyl-1H-purinium</synonym>
    <synonym>2-Amino-6,9-dihydro-7-methyl-6-oxo-9-beta-delta-ribofuranosyl-1H-purinium</synonym>
    <synonym>N(2)-Methylguanosine</synonym>
    <synonym>2-Methylguanosine</synonym>
  </synonyms>
  <chemical_formula>C11H16N5O5</chemical_formula>
  <average_molecular_weight>298.2752</average_molecular_weight>
  <monisotopic_moleculate_weight>298.115143647</monisotopic_moleculate_weight>
  <iupac_name>2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-6-oxo-6,7-dihydro-3H-9lambda5-purin-9-ylium</iupac_name>
  <traditional_iupac>2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-6-oxo-3H-9lambda5-purin-9-ylium</traditional_iupac>
  <cas_registry_number>20244-86-4</cas_registry_number>
  <smiles>CN1C=[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(=O)N=C(N)N2</smiles>
  <inchi>InChI=1S/C11H15N5O5/c1-15-3-16(8-5(15)9(20)14-11(12)13-8)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2-,12,13,14,20)/p+1/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>OGHAROSJZRTIOK-KQYNXXCUSA-O</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleosides</class>
    <sub_class/>
    <direct_parent>Purine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleoside</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>methylguanosine</external_descriptor>
      <external_descriptor>organic cation</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>155 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>6.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-6-oxo-6,7-dihydro-3H-9lambda5-purin-9-ylium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>298.2752</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>298.115143647</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C=[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(=O)N=C(N)N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H16N5O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H15N5O5/c1-15-3-16(8-5(15)9(20)14-11(12)13-8)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2-,12,13,14,20)/p+1/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OGHAROSJZRTIOK-KQYNXXCUSA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>146.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>69.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271040</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id>DB03493</drugbank_id>
  <foodb_id>FDB022428</foodb_id>
  <chemspider_id>393054</chemspider_id>
  <pubchem_compound_id>445404</pubchem_compound_id>
  <chebi_id>20794</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD0-1041</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>7-Methylguanosine</wikipedia_id>
  <metlin_id>6008</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00942</protein_accession>
      <name>Protein argonaute-2</name>
      <uniprot_id>Q6QME8</uniprot_id>
      <gene_name>EIF2C2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:12 UTC</creation_date>
  <update_date>2020-03-13 16:25:55 UTC</update_date>
  <accession>BMDB0001109</accession>
  <secondary_accessions>
    <accession>BMDB01109</accession>
  </secondary_accessions>
  <name>Glucosamine-1P</name>
  <description/>
  <synonyms>
    <synonym>alpha-D-Glucosamine 1-phosphate</synonym>
    <synonym>alpha-D-Glucosamine 1P</synonym>
    <synonym>alpha-delta-Glucosamine 1-phosphate</synonym>
    <synonym>alpha-delta-Glucosamine 1P</synonym>
  </synonyms>
  <chemical_formula>C6H14NO8P</chemical_formula>
  <average_molecular_weight>259.151</average_molecular_weight>
  <monisotopic_moleculate_weight>259.045702941</monisotopic_moleculate_weight>
  <iupac_name>{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>glucosamine-1P</traditional_iupac>
  <cas_registry_number/>
  <smiles>N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C6H14NO8P/c7-3-5(10)4(9)2(1-8)14-6(3)15-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1</inchi>
  <inchikey>YMJBYRVFGYXULK-UKFBFLRUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharide phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Aminosaccharides</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino saccharide</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>259.151</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>259.045702941</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H14NO8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H14NO8P/c7-3-5(10)4(9)2(1-8)14-6(3)15-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YMJBYRVFGYXULK-UKFBFLRUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>162.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>48.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363444</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB022429</foodb_id>
  <chemspider_id>8140645</chemspider_id>
  <pubchem_compound_id>9965052</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6009</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:13 UTC</creation_date>
  <update_date>2020-04-16 17:51:30 UTC</update_date>
  <accession>BMDB0001112</accession>
  <secondary_accessions>
    <accession>BMDB01112</accession>
  </secondary_accessions>
  <name>D-Glyceraldehyde 3-phosphate</name>
  <description/>
  <synonyms>
    <synonym>2-Hydroxy-3-(phosphonooxy)propanal</synonym>
    <synonym>3-Phosphoglyceraldehyde</synonym>
    <synonym>DL-Glyceraldehyde 3-phosphate</synonym>
    <synonym>GAP</synonym>
    <synonym>Gliceraldehido-3-fosfato</synonym>
    <synonym>Glyceraldehyde 3-(dihydrogen phosphate)</synonym>
    <synonym>Glyceraldehyde-3-phosphate</synonym>
    <synonym>Glycerinaldehyd-3-phosphat</synonym>
    <synonym>Glyzerinaldehyd-3-phosphat</synonym>
    <synonym>DL-Glyceraldehyde 3-phosphoric acid</synonym>
    <synonym>Glyceraldehyde 3-(dihydrogen phosphoric acid)</synonym>
    <synonym>Glyceraldehyde-3-phosphoric acid</synonym>
    <synonym>Glyceraldehyde 3-phosphoric acid</synonym>
    <synonym>D-Glyceraldehyde 3-phosphoric acid</synonym>
    <synonym>2-Hydroxy-3-(phosphonooxy)-propanal</synonym>
    <synonym>D-Glyceraldehyde-3-p</synonym>
    <synonym>Glyceraldehyde-3-p</synonym>
    <synonym>Glyceraldehyde-p</synonym>
    <synonym>Glyceraldehyde-phosphate</synonym>
    <synonym>3 Phosphoglyceraldehyde</synonym>
    <synonym>Glyceraldehyde 3 phosphate</synonym>
    <synonym>Glyceraldehyde 3-phosphate</synonym>
  </synonyms>
  <chemical_formula>C3H7O6P</chemical_formula>
  <average_molecular_weight>170.0578</average_molecular_weight>
  <monisotopic_moleculate_weight>169.998024468</monisotopic_moleculate_weight>
  <iupac_name>(2-hydroxy-3-oxopropoxy)phosphonic acid</iupac_name>
  <traditional_iupac>glyceraldehyde 3 phosphate</traditional_iupac>
  <cas_registry_number>591-59-3</cas_registry_number>
  <smiles>OC(COP(O)(O)=O)C=O</smiles>
  <inchi>InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)</inchi>
  <inchikey>LXJXRIRHZLFYRP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glyceraldehyde-3-phosphates. Glyceraldehyde-3-phosphates are compounds containing a glyceraldehyde substituted at position O3 by a phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Glyceraldehyde-3-phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxyaldehydes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-hydroxyaldehyde</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Glyceraldehyde-3-phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aldehyde</external_descriptor>
      <external_descriptor>aldotriose phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2-hydroxy-3-oxopropoxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>170.0578</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>169.998024468</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(COP(O)(O)=O)C=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7O6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h1,3,5H,2H2,(H2,6,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LXJXRIRHZLFYRP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>104.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerol Phosphate Shuttle</name>
      <smpdb_id>SMP0087199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Electron Transport Chain</name>
      <smpdb_id>SMP0087261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439169</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00661</kegg_id>
  <chemspider_id>709</chemspider_id>
  <pubchem_compound_id>729</pubchem_compound_id>
  <foodb_id>FDB001619</foodb_id>
  <chebi_id>17138</chebi_id>
  <knapsack_id>C00007285</knapsack_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD0-2032</meta_cyc_id>
  <bigg_id>35637</bigg_id>
  <wikipedia_id>3-phosphoglyceraldehyde</wikipedia_id>
  <metlin_id>3294</metlin_id>
  <synthesis_reference>Ballou, Clinton E.; Fischer, Hermann O. L. The synthesis of D-glyceraldehyde 3-phosphate. Journal of the American Chemical Society (1955), 77 3329-31.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00107</protein_accession>
      <name>Putative deoxyribose-phosphate aldolase</name>
      <uniprot_id>Q3T0V9</uniprot_id>
      <gene_name>DERA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00154</protein_accession>
      <name>Glyceraldehyde-3-phosphate dehydrogenase</name>
      <uniprot_id>P10096</uniprot_id>
      <gene_name>GAPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00209</protein_accession>
      <name>Glyceraldehyde-3-phosphate dehydrogenase, testis-specific</name>
      <uniprot_id>Q2KJE5</uniprot_id>
      <gene_name>GAPDHS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00531</protein_accession>
      <name>Fructose-bisphosphate aldolase</name>
      <uniprot_id>A6QLL8</uniprot_id>
      <gene_name>ALDOA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00532</protein_accession>
      <name>Fructose-bisphosphate aldolase</name>
      <uniprot_id>Q3ZBY4</uniprot_id>
      <gene_name>ALDOC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00533</protein_accession>
      <name>Fructose-bisphosphate aldolase</name>
      <uniprot_id>A5PK73</uniprot_id>
      <gene_name>ALDOB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00534</protein_accession>
      <name>Fructose-bisphosphate aldolase B</name>
      <uniprot_id>Q3T0S5</uniprot_id>
      <gene_name>ALDOB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00692</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q9XSN4</uniprot_id>
      <gene_name>GAPDL17</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00693</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q862K5</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00694</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q0QES8</uniprot_id>
      <gene_name>GAPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00695</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q4H0Z3</uniprot_id>
      <gene_name>gapdh</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00696</protein_accession>
      <name>Triosephosphate isomerase</name>
      <uniprot_id>Q5E956</uniprot_id>
      <gene_name>TPI1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00697</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q712W6</uniprot_id>
      <gene_name>GAPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:14 UTC</creation_date>
  <update_date>2020-03-13 16:25:56 UTC</update_date>
  <accession>BMDB0001113</accession>
  <secondary_accessions>
    <accession>BMDB01113</accession>
  </secondary_accessions>
  <name>Isovaleryl-CoA</name>
  <description/>
  <synonyms>
    <synonym>3-Methylbutanoyl-CoA</synonym>
    <synonym>3-Methylbutanoyl-coenzyme A</synonym>
    <synonym>3-Methylbutyryl-CoA</synonym>
    <synonym>3-Methylbutyryl-coenzyme A</synonym>
    <synonym>Isovaleryl CoA</synonym>
    <synonym>Isovaleryl coenzyme A</synonym>
    <synonym>Isovaleryl-coenzyme A</synonym>
    <synonym>S-(3-Methylbutanoate</synonym>
    <synonym>S-(3-Methylbutanoate) coenzyme A</synonym>
    <synonym>S-(3-Methylbutanoic acid</synonym>
    <synonym>S-Isovalerate CoA</synonym>
    <synonym>S-Isovalerate coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C26H44N7O17P3S</chemical_formula>
  <average_molecular_weight>851.651</average_molecular_weight>
  <monisotopic_moleculate_weight>851.172723243</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-methylbutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-methylbutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>6244-91-3</cas_registry_number>
  <smiles>CC(C)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C26H44N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h12-15,19-21,25,36-37H,5-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21?,25-/m1/s1</inchi>
  <inchikey>UYVZIWWBJMYRCD-TVCSPYKZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-methylbutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>851.651</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>851.172723243</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H44N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H44N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h12-15,19-21,25,36-37H,5-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21?,25-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UYVZIWWBJMYRCD-TVCSPYKZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>185.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>76.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>83121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>83122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>83123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144650</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02939</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022430</foodb_id>
  <chemspider_id>388897</chemspider_id>
  <pubchem_compound_id>439855</pubchem_compound_id>
  <chebi_id>15487</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>40861</bigg_id>
  <wikipedia_id>Isovaleryl-CoA</wikipedia_id>
  <metlin_id>451</metlin_id>
  <synthesis_reference>Valentin, Henry E.; Steinbuechel, Alexander.  Application of enzymically synthesized short-chain-length hydroxy fatty acid coenzyme A thioesters for assay of polyhydroxyalkanoic acid synthases.    Applied Microbiology and Biotechnology  (1994),  40(5),  699-709.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00428</protein_accession>
      <name>Isovaleryl-CoA dehydrogenase, mitochondrial</name>
      <uniprot_id>Q3SZI8</uniprot_id>
      <gene_name>IVD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:16 UTC</creation_date>
  <update_date>2020-04-15 20:44:54 UTC</update_date>
  <accession>BMDB0001114</accession>
  <secondary_accessions>
    <accession>BMDB01114</accession>
  </secondary_accessions>
  <name>Stearoyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>C18:0-CoA</synonym>
    <synonym>C18:0-coenzyme A</synonym>
    <synonym>Octadecanoyl-CoA</synonym>
    <synonym>Octadecanoyl-coenzyme A</synonym>
    <synonym>S-Stearoyl-CoA</synonym>
    <synonym>S-Stearoylcoenzyme A</synonym>
    <synonym>Stearoyl-coenzyme A</synonym>
    <synonym>Stearyl coenzyme A</synonym>
    <synonym>Stearyl-CoA</synonym>
  </synonyms>
  <chemical_formula>C39H70N7O17P3S</chemical_formula>
  <average_molecular_weight>1033.996</average_molecular_weight>
  <monisotopic_moleculate_weight>1033.376174075</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-[(2-{[2-(octadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>stearoyl-coa</traditional_iupac>
  <cas_registry_number>362-66-3</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C39H70N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h26-28,32-34,38,49-50H,4-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/t28-,32-,33-,34+,38-/m1/s1</inchi>
  <inchikey>SIARJEKBADXQJG-LFZQUHGESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Long-chain fatty acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>2,3,4-saturated fatty acyl CoAs</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Amino acids and derivatives</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>11,12-saturated fatty acyl-CoA</external_descriptor>
      <external_descriptor>long-chain fatty acyl-CoA</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-[(2-{[2-(octadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1033.996</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1033.376174075</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C39H70N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C39H70N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h26-28,32-34,38,49-50H,4-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/t28-,32-,33-,34+,38-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SIARJEKBADXQJG-LFZQUHGESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>245.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>106.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36923</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36924</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>39371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>39372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>39373</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <kegg_id>C00412</kegg_id>
  <drugbank_id/>
  <pubchem_compound_id>94140</pubchem_compound_id>
  <chebi_id>15541</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Stearoyl-CoA</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Boiron F; Heape M A; Cassagne C  Assay of stearoyl-CoA synthesis in microsomes from normal and Trembler mouse sciatic nerves.    Neuroscience letters  (1984),  48(1),  7-12.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00670</protein_accession>
      <name>Acyl-CoA desaturase</name>
      <uniprot_id>Q9TT94</uniprot_id>
      <gene_name>SCD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00829</protein_accession>
      <name>Stearoyl-CoA desaturase 5</name>
      <uniprot_id>Q2KIA4</uniprot_id>
      <gene_name>SCD5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:17 UTC</creation_date>
  <update_date>2020-03-13 16:25:57 UTC</update_date>
  <accession>BMDB0001117</accession>
  <secondary_accessions>
    <accession>BMDB01117</accession>
  </secondary_accessions>
  <name>4-Phosphopantothenoylcysteine</name>
  <description>4'-Phosphopantothenoylcysteine, also known as 4'-phosphopantothenoylcysteine, belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. 4'-Phosphopantothenoylcysteine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 4'-Phosphopantothenoylcysteine exists in all living species, ranging from bacteria to humans. 4'-Phosphopantothenoylcysteine participates in a number of enzymatic reactions, within cattle. In particular, Cytidine monophosphate and 4'-phosphopantothenoylcysteine can be biosynthesized from cytidine triphosphate, D-4'-phosphopantothenate, and L-cysteine; which is mediated by the enzyme phosphopantothenate--cysteine ligase. In addition, 4'-Phosphopantothenoylcysteine can be converted into pantetheine 4'-phosphate; which is mediated by the enzyme phosphopantothenoylcysteine decarboxylase. In cattle, 4'-phosphopantothenoylcysteine is involved in the metabolic pathway called pantothenate and CoA biosynthesis pathway.</description>
  <synonyms>
    <synonym>(R)-4'-Phosphopantothenoyl-L-cysteine</synonym>
    <synonym>N-((R)-4'-Phosphopantothenoyl)-L-cysteine</synonym>
    <synonym>N-[(R)-4'-Phosphopantothenoyl]-L-cysteine</synonym>
    <synonym>(R)-4'-Phospho-N-pantothenoyl-L-cysteine</synonym>
    <synonym>(R)-N-[N-[2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-b-alanyl]-L-cysteine</synonym>
    <synonym>(R)-N-[N-[2-Hydroxy-3,3-dimethyl-1-oxo-4-(phosphonooxy)butyl]-beta-alanyl]-L-cysteine</synonym>
    <synonym>4'-p-N-Pantothenoylcysteine</synonym>
    <synonym>4'-Phospho-N-pantothenoylcysteine</synonym>
    <synonym>4'-Phosphopantothenoyl-L-cysteine</synonym>
    <synonym>4-p-N-Pantothenoylcysteine</synonym>
    <synonym>N-((R)-4-Phosphopantothenoyl)-L-cysteine</synonym>
    <synonym>Pantothenoylcysteine 4'-phosphate</synonym>
    <synonym>Pantothenylcysteine 4'-phosphate</synonym>
    <synonym>4'-Phosphopantothenoylcysteine</synonym>
  </synonyms>
  <chemical_formula>C12H23N2O9PS</chemical_formula>
  <average_molecular_weight>402.358</average_molecular_weight>
  <monisotopic_moleculate_weight>402.086187546</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-{3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanamido}-3-sulfanylpropanoic acid</iupac_name>
  <traditional_iupac>(2R)-2-{3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanamido}-3-sulfanylpropanoic acid</traditional_iupac>
  <cas_registry_number>7196-09-0</cas_registry_number>
  <smiles>CC(C)(COP(O)(O)=O)[C@@H](O)C(=O)NCCC(=O)N[C@@H](CS)C(O)=O</smiles>
  <inchi>InChI=1S/C12H23N2O9PS/c1-12(2,6-23-24(20,21)22)9(16)10(17)13-4-3-8(15)14-7(5-25)11(18)19/h7,9,16,25H,3-6H2,1-2H3,(H,13,17)(H,14,15)(H,18,19)(H2,20,21,22)/t7-,9-/m0/s1</inchi>
  <inchikey>XQYALQVLCNHCFT-CBAPKCEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Peptidomimetics</class>
    <sub_class>Hybrid peptides</sub_class>
    <direct_parent>Hybrid peptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cysteine and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cysteine or derivatives</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hybrid peptide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-cysteine derivative</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-{3-[(2R)-2-hydroxy-3-methyl-3-[(phosphonooxy)methyl]butanamido]propanamido}-3-sulfanylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>402.358</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>402.086187546</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)(COP(O)(O)=O)[C@@H](O)C(=O)NCCC(=O)N[C@@H](CS)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H23N2O9PS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H23N2O9PS/c1-12(2,6-23-24(20,21)22)9(16)10(17)13-4-3-8(15)14-7(5-25)11(18)19/h7,9,16,25H,3-6H2,1-2H3,(H,13,17)(H,14,15)(H,18,19)(H2,20,21,22)/t7-,9-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XQYALQVLCNHCFT-CBAPKCEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>182.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>87.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pantothenate and CoA Biosynthesis</name>
      <smpdb_id>SMP0087207</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29854</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04352</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022432</foodb_id>
  <chemspider_id>389278</chemspider_id>
  <pubchem_compound_id>440304</pubchem_compound_id>
  <chebi_id>15769</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00019633</knapsack_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>43650</bigg_id>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:18 UTC</creation_date>
  <update_date>2020-03-13 16:25:58 UTC</update_date>
  <accession>BMDB0001119</accession>
  <secondary_accessions>
    <accession>BMDB01119</accession>
  </secondary_accessions>
  <name>4-Hydroxy-4-(3-pyridyl)-butanoic acid</name>
  <description/>
  <synonyms>
    <synonym>4-Hydroxy-4-(3-pyridyl)-butanoate</synonym>
    <synonym>4-(3-Pyridyl)-4-hydroxybutyrate</synonym>
    <synonym>4-(3-Pyridyl)-4-hydroxybutyric acid</synonym>
    <synonym>gamma-(3-Pyridyl)-gamma-hydroxybutyrate</synonym>
    <synonym>gamma-(3-Pyridyl)-gamma-hydroxybutyric acid</synonym>
    <synonym>4-HOPC4a</synonym>
    <synonym>4-Hydroxy-4-(3-pyridyl)butanoic acid</synonym>
    <synonym>4-Hydroxy-4-(3-pyridyl)butyric acid</synonym>
    <synonym>g-Hydroxy-3-pyridinebutanoate</synonym>
    <synonym>g-Hydroxy-3-pyridinebutanoic acid</synonym>
    <synonym>gamma-Hydroxy-3-pyridinebutanoic acid</synonym>
    <synonym>Γ-hydroxy-3-pyridinebutanoate</synonym>
    <synonym>Γ-hydroxy-3-pyridinebutanoic acid</synonym>
  </synonyms>
  <chemical_formula>C9H11NO3</chemical_formula>
  <average_molecular_weight>181.1885</average_molecular_weight>
  <monisotopic_moleculate_weight>181.073893223</monisotopic_moleculate_weight>
  <iupac_name>4-hydroxy-4-(pyridin-3-yl)butanoic acid</iupac_name>
  <traditional_iupac>4-hydroxy-4-(pyridin-3-yl)butanoic acid</traditional_iupac>
  <cas_registry_number>15569-97-8</cas_registry_number>
  <smiles>OC(CCC(O)=O)C1=CC=CN=C1</smiles>
  <inchi>InChI=1S/C9H11NO3/c11-8(3-4-9(12)13)7-2-1-5-10-6-7/h1-2,5-6,8,11H,3-4H2,(H,12,13)</inchi>
  <inchikey>STZOZPPVGWNSMC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class/>
    <direct_parent>Pyridines and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>pyridines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-hydroxy-4-(pyridin-3-yl)butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>181.1885</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>181.073893223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(CCC(O)=O)C1=CC=CN=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11NO3/c11-8(3-4-9(12)13)7-2-1-5-10-6-7/h1-2,5-6,8,11H,3-4H2,(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>STZOZPPVGWNSMC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>70.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37932</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C19579</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022433</foodb_id>
  <chemspider_id>425</chemspider_id>
  <pubchem_compound_id>438</pubchem_compound_id>
  <chebi_id>82573</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6015</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:19 UTC</creation_date>
  <update_date>2020-04-16 17:51:30 UTC</update_date>
  <accession>BMDB0001120</accession>
  <secondary_accessions>
    <accession>BMDB01120</accession>
  </secondary_accessions>
  <name>Dimethylallylpyrophosphate</name>
  <description/>
  <synonyms>
    <synonym>2-Isopentenyl diphosphate</synonym>
    <synonym>3,3-Dimethylallyl pyrophosphate</synonym>
    <synonym>3-Methylbut-2-enyl phosphono hydrogen phosphate</synonym>
    <synonym>delta-Prenyl diphosphate</synonym>
    <synonym>delta2-Isopentenyl diphosphate</synonym>
    <synonym>Dimethylallyl diphosphate</synonym>
    <synonym>Dimethylallyl pyrophosphate</synonym>
    <synonym>DMAPP</synonym>
    <synonym>Monoprenyl diphosphate</synonym>
    <synonym>Prenol pyrophosphate</synonym>
    <synonym>Prenyl diphosphate</synonym>
    <synonym>2-Isopentenyl diphosphoric acid</synonym>
    <synonym>3,3-Dimethylallyl pyrophosphoric acid</synonym>
    <synonym>3-Methylbut-2-enyl phosphono hydrogen phosphoric acid</synonym>
    <synonym>delta-Prenyl diphosphoric acid</synonym>
    <synonym>Δ-prenyl diphosphate</synonym>
    <synonym>Δ-prenyl diphosphoric acid</synonym>
    <synonym>delta2-Isopentenyl diphosphoric acid</synonym>
    <synonym>Δ2-isopentenyl diphosphate</synonym>
    <synonym>Δ2-isopentenyl diphosphoric acid</synonym>
    <synonym>Dimethylallyl diphosphoric acid</synonym>
    <synonym>Dimethylallyl pyrophosphoric acid</synonym>
    <synonym>Monoprenyl diphosphoric acid</synonym>
    <synonym>Prenol pyrophosphoric acid</synonym>
    <synonym>Prenyl diphosphoric acid</synonym>
    <synonym>Dimethylallylpyrophosphoric acid</synonym>
    <synonym>1,1-Dimethyl-4-phenylpiperazinium iodide</synonym>
    <synonym>3-Methyl-2-buten-1-ol pyrophosphate</synonym>
    <synonym>3-Methyl-2-buten-1-ol trihydrogen pyrophosphate</synonym>
    <synonym>3-Methyl-2-butenyl pyrophosphate</synonym>
    <synonym>3-Methylbut-2-enyl pyrophosphate</synonym>
    <synonym>Delta2-Isopentenyl-diphosphate</synonym>
    <synonym>Dimethylallyl-diphosphate</synonym>
    <synonym>Dimethylallyl-PP</synonym>
    <synonym>Dimethylallyl-ppi</synonym>
    <synonym>Dimethylallyl-pyrophosphate</synonym>
    <synonym>Diphosphoric acid mono(3-methyl-2-butenyl) ester</synonym>
    <synonym>DMPP</synonym>
    <synonym>IPE</synonym>
    <synonym>Prenyl-diphosphate</synonym>
    <synonym>3,3-Dimethylallyl pyrophosphate, (14)C-labeled</synonym>
    <synonym>DMADP CPD</synonym>
  </synonyms>
  <chemical_formula>C5H12O7P2</chemical_formula>
  <average_molecular_weight>246.0921</average_molecular_weight>
  <monisotopic_moleculate_weight>246.005825762</monisotopic_moleculate_weight>
  <iupac_name>({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid</iupac_name>
  <traditional_iupac>dimethylallyl diphosphate</traditional_iupac>
  <cas_registry_number>358-72-5</cas_registry_number>
  <smiles>CC(C)=CCO[P@](O)(=O)OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)</inchi>
  <inchikey>CBIDRCWHNCKSTO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Isoprenoid phosphates</sub_class>
    <direct_parent>Isoprenoid phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isoprenoid phosphate</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C5 isoprenoids (hemiterpenes)</external_descriptor>
      <external_descriptor>C5 isoprenoids (hemiterpenes)</external_descriptor>
      <external_descriptor>prenol phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>234 - 238 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>246.0921</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>246.005825762</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)=CCO[P@](O)(=O)OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H12O7P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CBIDRCWHNCKSTO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>49.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20858</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22411</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00235</kegg_id>
  <drugbank_id>DB01785</drugbank_id>
  <foodb_id>FDB022434</foodb_id>
  <chemspider_id>627</chemspider_id>
  <pubchem_compound_id>647</pubchem_compound_id>
  <chebi_id>16057</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00007294</knapsack_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>131960</bigg_id>
  <wikipedia_id>Dimethylallyl pyrophosphate</wikipedia_id>
  <metlin_id>6016</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00451</protein_accession>
      <name>Isopentenyl-diphosphate Delta-isomerase 1</name>
      <uniprot_id>Q1LZ95</uniprot_id>
      <gene_name>IDI1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00864</protein_accession>
      <name>Farnesyl pyrophosphate synthetase</name>
      <uniprot_id>Q8WMY2</uniprot_id>
      <gene_name>FDPS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00865</protein_accession>
      <name>Geranylgeranyl pyrophosphate synthetase</name>
      <uniprot_id>P56966</uniprot_id>
      <gene_name>GGPS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:20 UTC</creation_date>
  <update_date>2020-03-13 16:25:59 UTC</update_date>
  <accession>BMDB0001121</accession>
  <secondary_accessions>
    <accession>BMDB01121</accession>
  </secondary_accessions>
  <name>N-Acetyl-D-mannosamine 6-phosphate</name>
  <description>N-Acetyl-D-mannosamine 6-phosphate, also known as n-acetyl-d-mannosamine 6-phosphate or N-acetyl-D-mannosamine-6-p, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetyl-D-mannosamine 6-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-D-mannosamine 6-phosphate exists in all living organisms, ranging from bacteria to humans. N-Acetyl-D-mannosamine 6-phosphate participates in a number of enzymatic reactions, within cattle. In particular, N-Acetyl-D-mannosamine 6-phosphate can be biosynthesized from N-acetylmannosamine; which is mediated by the enzyme bifunctional UDP-N-acetyl glucosamine 2-epimerase / N-acetylmannosamine kinase. In addition, N-Acetyl-D-mannosamine 6-phosphate and phosphoenolpyruvic acid can be converted into N-acetylneuraminate 9-phosphate; which is catalyzed by the enzyme sialic acid synthase. In cattle, N-acetyl-D-mannosamine 6-phosphate is involved in the metabolic pathway called the amino sugar metabolism pathway.</description>
  <synonyms>
    <synonym>2-(Acetylamino)-2-deoxy-6-O-phosphono-alpha-D-mannopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-6-O-phosphono-alpha-D-mannopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-6-O-phosphono-alpha-D-mannose</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-6-O-phosphono-a-D-mannopyranose</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-6-O-phosphono-α-D-mannopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-6-O-phosphono-a-D-mannopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-6-O-phosphono-α-D-mannopyranose</synonym>
    <synonym>2-Acetamido-2-deoxy-6-O-phosphono-a-D-mannose</synonym>
    <synonym>2-Acetamido-2-deoxy-6-O-phosphono-α-D-mannose</synonym>
    <synonym>N-Acetyl-D-mannosamine 6-phosphoric acid</synonym>
    <synonym>ManNAc-6-p</synonym>
    <synonym>N-Acetyl-D-mannosamine-6-p</synonym>
    <synonym>N-Acetyl-D-mannosamine-6-phosphate</synonym>
    <synonym>N-Acetylmannosamine-6-p</synonym>
    <synonym>2-Acetamido-2-deoxy-mannose-6-phosphate</synonym>
  </synonyms>
  <chemical_formula>C8H16NO9P</chemical_formula>
  <average_molecular_weight>301.1877</average_molecular_weight>
  <monisotopic_moleculate_weight>301.056267627</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5S,6S)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5S,6S)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxyphosphonic acid</traditional_iupac>
  <cas_registry_number>873185-52-5</cas_registry_number>
  <smiles>CC(=O)N[C@@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C8H16NO9P/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H2,14,15,16)/t4-,5+,6-,7-,8+/m1/s1</inchi>
  <inchikey>BRGMHAYQAZFZDJ-UOLFYFMNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Acylaminosugars</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hexose phosphates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Acylaminosugar</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acetyl-D-mannosamine 6-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5S,6S)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>301.1877</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>301.056267627</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16NO9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16NO9P/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H2,14,15,16)/t4-,5+,6-,7-,8+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BRGMHAYQAZFZDJ-UOLFYFMNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>165.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>57.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34549</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04257</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022435</foodb_id>
  <chemspider_id>389249</chemspider_id>
  <pdbe_id>BMX</pdbe_id>
  <chebi_id>62165</chebi_id>
  <pubchem_compound_id>440273</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>43459</bigg_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:21 UTC</creation_date>
  <update_date>2020-03-13 16:26:00 UTC</update_date>
  <accession>BMDB0001122</accession>
  <secondary_accessions>
    <accession>BMDB01122</accession>
  </secondary_accessions>
  <name>N-Methylformamide</name>
  <description/>
  <synonyms>
    <synonym>HCONHCH3</synonym>
    <synonym>Methylformamide</synonym>
    <synonym>Monomethylformamide</synonym>
    <synonym>N-Methyl-formamide</synonym>
    <synonym>N-Monomethylformamide</synonym>
    <synonym>NMF</synonym>
    <synonym>N-Methylformamide</synonym>
  </synonyms>
  <chemical_formula>C2H5NO</chemical_formula>
  <average_molecular_weight>59.0672</average_molecular_weight>
  <monisotopic_moleculate_weight>59.037113787</monisotopic_moleculate_weight>
  <iupac_name>N-methylformamide</iupac_name>
  <traditional_iupac>methylformamide</traditional_iupac>
  <cas_registry_number>123-39-7</cas_registry_number>
  <smiles>CNC=O</smiles>
  <inchi>InChI=1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)</inchi>
  <inchikey>ATHHXGZTWNVVOU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboximidic acids and derivatives</class>
    <sub_class>Carboximidic acids</sub_class>
    <direct_parent>Carboximidic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>formamides</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-3.8 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.97</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>16.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-methylformamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>59.0672</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>59.037113787</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CNC=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H5NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H5NO/c1-3-2-4/h2H,1H3,(H,3,4)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ATHHXGZTWNVVOU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>29.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>14.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>5.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>52856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>144056</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C11489</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022436</foodb_id>
  <chemspider_id/>
  <pdbe_id/>
  <chebi_id>7438</chebi_id>
  <pubchem_compound_id>31254</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>N-Methylformamide</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:22 UTC</creation_date>
  <update_date>2020-04-15 22:00:13 UTC</update_date>
  <accession>BMDB0001123</accession>
  <secondary_accessions>
    <accession>BMDB01123</accession>
  </secondary_accessions>
  <name>2-Aminobenzoic acid</name>
  <description>2-Aminobenzoic acid, also known as 2-aminobenzoic acid or 2-aminobenzoic acid, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. 2-Aminobenzoic acid exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. 2-Aminobenzoic acid exists in all living species, ranging from bacteria to humans. 2-Aminobenzoic acid participates in a number of enzymatic reactions, within cattle. In particular, 2-Aminobenzoic acid and formic acid can be biosynthesized from formyl2-aminobenzoic acid; which is mediated by the enzyme kynurenine formamidase. In addition, 2-Aminobenzoic acid and L-alanine can be biosynthesized from L-kynurenine through the action of the enzyme kynureninase. In cattle, 2-aminobenzoic acid is involved in the metabolic pathway called the tryptophan metabolism pathway. 2-Aminobenzoic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2-Aminobenzoesaeure</synonym>
    <synonym>2-Carboxyaniline</synonym>
    <synonym>O-Aminobenzoesaeure</synonym>
    <synonym>O-Aminobenzoic acid</synonym>
    <synonym>O-Carboxyaniline</synonym>
    <synonym>Vitamin L1</synonym>
    <synonym>Anthranilic acid</synonym>
    <synonym>2-Aminobenzoate</synonym>
    <synonym>O-Aminobenzoate</synonym>
    <synonym>Anthranilate</synonym>
    <synonym>Anthranilic acid, cadmium salt</synonym>
    <synonym>Anthranilic acid, calcium (2:1) salt</synonym>
    <synonym>Anthranilic acid, monolithium salt</synonym>
    <synonym>Sodium anthranilate</synonym>
    <synonym>Anthranilic acid, dihydrochloride</synonym>
    <synonym>Anthranilic acid, hydrochloride</synonym>
    <synonym>Anthranilic acid, monosodium salt</synonym>
    <synonym>1-Amino-2-carboxybenzene</synonym>
    <synonym>2-Amino-benzoate</synonym>
    <synonym>2-Amino-benzoic acid</synonym>
    <synonym>2-Aminophenylacetate</synonym>
    <synonym>2-Aminophenylacetic acid</synonym>
    <synonym>Anthranate</synonym>
    <synonym>Anthranic acid</synonym>
    <synonym>Anthranilic acid GR</synonym>
    <synonym>Carboxyaniline</synonym>
    <synonym>H-2-Abz-OH</synonym>
    <synonym>Kyselina anthranilova</synonym>
    <synonym>Kyselina O-aminobenzoova</synonym>
    <synonym>O-Amino-benzoate</synonym>
    <synonym>O-Amino-benzoic acid</synonym>
    <synonym>O-Anthranilate</synonym>
    <synonym>O-Anthranilic acid</synonym>
    <synonym>Ortho-amidobenzoate</synonym>
    <synonym>Ortho-amidobenzoic acid</synonym>
    <synonym>Ortho-aminobenzoate</synonym>
    <synonym>Ortho-aminobenzoic acid</synonym>
    <synonym>Vitamin L</synonym>
  </synonyms>
  <chemical_formula>C7H7NO2</chemical_formula>
  <average_molecular_weight>137.136</average_molecular_weight>
  <monisotopic_moleculate_weight>137.047678473</monisotopic_moleculate_weight>
  <iupac_name>2-aminobenzoic acid</iupac_name>
  <traditional_iupac>2-aminobenzoic acid</traditional_iupac>
  <cas_registry_number>118-92-3</cas_registry_number>
  <smiles>NC1=CC=CC=C1C(O)=O</smiles>
  <inchi>InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)</inchi>
  <inchikey>RWZYAGGXGHYGMB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>Aminobenzoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminobenzoic acid</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aminobenzoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>146.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>3.5 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.21</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-aminobenzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>137.136</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>137.047678473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=CC=CC=C1C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H7NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RWZYAGGXGHYGMB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37934</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00108</kegg_id>
  <drugbank_id>DB04166</drugbank_id>
  <foodb_id>FDB000896</foodb_id>
  <chemspider_id>222</chemspider_id>
  <pdbe_id/>
  <chebi_id>30754</chebi_id>
  <pubchem_compound_id>227</pubchem_compound_id>
  <knapsack_id>C00007382</knapsack_id>
  <meta_cyc_id>ANTHRANILATE</meta_cyc_id>
  <wikipedia_id>Anthranilic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33883</bigg_id>
  <metlin_id>6018</metlin_id>
  <synthesis_reference>Wang, Chengyin; Yang, Jisheng; Wang, Honghai.  Production of o-aminobenzoic acid from by-product o-nitrobenzoic acid.    Huaxue Shijie  (1999),  40(5),  274-277.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:24 UTC</creation_date>
  <update_date>2020-03-13 16:26:01 UTC</update_date>
  <accession>BMDB0001124</accession>
  <secondary_accessions>
    <accession>BMDB01124</accession>
  </secondary_accessions>
  <name>Trehalose 6-phosphate</name>
  <description/>
  <synonyms>
    <synonym>alpha,Alpha'-trehalose 6-phosphate</synonym>
    <synonym>alpha-D-Glucopyranosyl alpha-D-glucopyranoside 6-(dihydrogen phosphate)</synonym>
    <synonym>a,Alpha'-trehalose 6-phosphate</synonym>
    <synonym>a,Alpha'-trehalose 6-phosphoric acid</synonym>
    <synonym>alpha,Alpha'-trehalose 6-phosphoric acid</synonym>
    <synonym>Α,alpha'-trehalose 6-phosphate</synonym>
    <synonym>Α,alpha'-trehalose 6-phosphoric acid</synonym>
    <synonym>a-D-Glucopyranosyl a-D-glucopyranoside 6-(dihydrogen phosphate)</synonym>
    <synonym>a-D-Glucopyranosyl a-D-glucopyranoside 6-(dihydrogen phosphoric acid)</synonym>
    <synonym>alpha-D-Glucopyranosyl alpha-D-glucopyranoside 6-(dihydrogen phosphoric acid)</synonym>
    <synonym>Α-D-glucopyranosyl α-D-glucopyranoside 6-(dihydrogen phosphate)</synonym>
    <synonym>Α-D-glucopyranosyl α-D-glucopyranoside 6-(dihydrogen phosphoric acid)</synonym>
    <synonym>Trehalose 6-phosphoric acid</synonym>
    <synonym>Trehalose-6-phosphate</synonym>
  </synonyms>
  <chemical_formula>C12H23O14P</chemical_formula>
  <average_molecular_weight>422.2764</average_molecular_weight>
  <monisotopic_moleculate_weight>422.082541956</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>α,α'-trehalose 6-phosphate</traditional_iupac>
  <cas_registry_number>4484-88-2</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](O[C@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C12H23O14P/c13-1-3-5(14)7(16)9(18)11(24-3)26-12-10(19)8(17)6(15)4(25-12)2-23-27(20,21)22/h3-19H,1-2H2,(H2,20,21,22)/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1</inchi>
  <inchikey>LABSPYBHMPDTEL-LIZSDCNHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as disaccharide phosphates. These are disaccharides carrying  one or more phosphate group on a sugar unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Disaccharide phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Disaccharide phosphate</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>trehalose phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>422.2764</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>422.082541956</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](O[C@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H23O14P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H23O14P/c13-1-3-5(14)7(16)9(18)11(24-3)26-12-10(19)8(17)6(15)4(25-12)2-23-27(20,21)22/h3-19H,1-2H2,(H2,20,21,22)/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LABSPYBHMPDTEL-LIZSDCNHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>236.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447295</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00689</kegg_id>
  <drugbank_id>DB02430</drugbank_id>
  <foodb_id>FDB022437</foodb_id>
  <chemspider_id>109086</chemspider_id>
  <pdbe_id/>
  <chebi_id>18283</chebi_id>
  <pubchem_compound_id>122336</pubchem_compound_id>
  <knapsack_id>C00007451</knapsack_id>
  <meta_cyc_id>TREHALOSE-6P</meta_cyc_id>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6019</metlin_id>
  <synthesis_reference>MacDonald, Donald L.; Wong, Roger Y. K.  Chemical synthesis of trehalose 6-phosphate.    Biochimica et Biophysica Acta, General Subjects  (1964),  86(2),  390-2.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:25 UTC</creation_date>
  <update_date>2020-03-13 16:26:01 UTC</update_date>
  <accession>BMDB0001125</accession>
  <secondary_accessions>
    <accession>BMDB01125</accession>
  </secondary_accessions>
  <name>Inositol cyclic phosphate</name>
  <description/>
  <synonyms>
    <synonym>D-Myo-inositol 1,2-cyclic phosphate</synonym>
    <synonym>Myo-inositol 1,2-cyclic phosphate</synonym>
    <synonym>1D-Myo-inositol 1,2-cyclic phosphate</synonym>
    <synonym>D-Myo-inositol 1,2-cyclic phosphoric acid</synonym>
    <synonym>Myo-inositol 1,2-cyclic phosphoric acid</synonym>
    <synonym>1D-Myo-inositol 1,2-cyclic phosphoric acid</synonym>
    <synonym>Inositol cyclic phosphoric acid</synonym>
    <synonym>Inositol 1,2-cyclic phosphate</synonym>
    <synonym>Inositol cyclic-1,2-monophosphate</synonym>
    <synonym>Inositol cyclic phosphate, (D)-isomer</synonym>
    <synonym>Myoinositol 1,2-cyclic phosphate</synonym>
    <synonym>Inositol cyclic phosphate</synonym>
  </synonyms>
  <chemical_formula>C6H11O8P</chemical_formula>
  <average_molecular_weight>242.1205</average_molecular_weight>
  <monisotopic_moleculate_weight>242.01915384</monisotopic_moleculate_weight>
  <iupac_name>(3aR,4R,5S,6S,7R,7aS)-2,4,5,6,7-pentahydroxy-hexahydro-2H-1,3,2λ⁵-benzodioxaphosphol-2-one</iupac_name>
  <traditional_iupac>inositol 1,2-cyclic phosphate</traditional_iupac>
  <cas_registry_number>43119-57-9</cas_registry_number>
  <smiles>O[C@H]1[C@H]2OP(O)(=O)O[C@H]2[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H11O8P/c7-1-2(8)4(10)6-5(3(1)9)13-15(11,12)14-6/h1-10H,(H,11,12)/t1-,2-,3+,4+,5-,6+/m0/s1</inchi>
  <inchikey>SXHMVNXROAUURW-FTYOSCRSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as organic phosphoric acids and derivatives. These are organic compounds containing phosphoric acid or a derivative thereof.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic phosphoric acids and derivatives</class>
    <sub_class/>
    <direct_parent>Organic phosphoric acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclitols and derivatives</alternative_parent>
      <alternative_parent>Dioxaphospholanes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3_dioxaphospholane</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclitol or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>myo-inositol cyclic phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3aR,4R,5S,6S,7R,7aS)-2,4,5,6,7-pentahydroxy-hexahydro-2H-1,3,2λ⁵-benzodioxaphosphol-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>242.1205</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>242.01915384</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@H]2OP(O)(=O)O[C@H]2[C@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H11O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H11O8P/c7-1-2(8)4(10)6-5(3(1)9)13-15(11,12)14-6/h1-10H,(H,11,12)/t1-,2-,3+,4+,5-,6+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SXHMVNXROAUURW-FTYOSCRSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>136.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37936</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346521</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04299</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022438</foodb_id>
  <chemspider_id>109081</chemspider_id>
  <pdbe_id/>
  <chebi_id>18426</chebi_id>
  <pubchem_compound_id>122331</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6020</metlin_id>
  <synthesis_reference>Connolly T M; Wilson D B; Bross T E; Majerus P W  Isolation and characterization of the inositol cyclic phosphate products of phosphoinositide cleavage by phospholipase C. Metabolism in cell-free extracts.    The Journal of biological chemistry  (1986),  261(1),  122-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:26 UTC</creation_date>
  <update_date>2020-04-14 22:48:52 UTC</update_date>
  <accession>BMDB0001126</accession>
  <secondary_accessions>
    <accession>BMDB01126</accession>
  </secondary_accessions>
  <name>Nornicotine</name>
  <description/>
  <synonyms>
    <synonym>(+-)-1'-Demethyl-nicotine</synonym>
    <synonym>(+-)-1'-Demethylnicotine</synonym>
    <synonym>(+-)-3-(2-Pyrrolidinyl)pyridine</synonym>
    <synonym>(+-)-Nornicotine</synonym>
    <synonym>(R)-3-(Pyrrolidin-2-yl)pyridine</synonym>
    <synonym>(R,S)-Nornicotine</synonym>
    <synonym>(S)-2-(3-Pyridyl)pyrrolidine</synonym>
    <synonym>2-(3-Pyridyl)pyrrolidine</synonym>
    <synonym>3-(2-Pyrrolidinyl)pyridine</synonym>
    <synonym>DL-Norcitine</synonym>
    <synonym>L-Nor-nicotine</synonym>
    <synonym>Nornicotin</synonym>
    <synonym>S-(-)-Nornicotine</synonym>
    <synonym>Nornicotine tartrate, (S)-(R-(r*,r*))-isomer</synonym>
    <synonym>Nornicotine, (R)-isomer</synonym>
    <synonym>Nornicotine, (S)-isomer</synonym>
  </synonyms>
  <chemical_formula>C9H12N2</chemical_formula>
  <average_molecular_weight>148.205</average_molecular_weight>
  <monisotopic_moleculate_weight>148.100048394</monisotopic_moleculate_weight>
  <iupac_name>3-(pyrrolidin-2-yl)pyridine</iupac_name>
  <traditional_iupac>(+-)-nornicotine</traditional_iupac>
  <cas_registry_number>494-97-3</cas_registry_number>
  <smiles>C1CNC(C1)C1=CC=CN=C1</smiles>
  <inchi>InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2</inchi>
  <inchikey>MYKUKUCHPMASKF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyrrolidinylpyridines</sub_class>
    <direct_parent>Pyrrolidinylpyridines</direct_parent>
    <alternative_parents>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrrolidines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidinylpyridine</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Pyridine alkaloids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>boiling_point</kind>
      <value>270 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.17</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(pyrrolidin-2-yl)pyridine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>148.205</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>148.100048394</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C1CNC(C1)C1=CC=CN=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H12N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MYKUKUCHPMASKF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>24.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>44.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>152958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>152959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>152960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444079</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C06524</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022439</foodb_id>
  <chemspider_id>21108497</chemspider_id>
  <pdbe_id/>
  <chebi_id>28313</chebi_id>
  <pubchem_compound_id>412</pubchem_compound_id>
  <knapsack_id>C00042792</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Nornicotine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>1534</metlin_id>
  <synthesis_reference>Papadopoulos, Nick M.  Formation of nornicotine and other metabolites from nicotine in vitro and in vivo.    Canadian Journal of Biochemistry and Physiology  (1964),  42(4),  435-42.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:27 UTC</creation_date>
  <update_date>2020-03-13 16:26:02 UTC</update_date>
  <accession>BMDB0001127</accession>
  <secondary_accessions>
    <accession>BMDB01127</accession>
  </secondary_accessions>
  <name>6-Phosphonoglucono-D-lactone</name>
  <description>6-Phosphonoglucono-D-lactone, also known as 6-phosphonoglucono-d-lactone or 6-PGDL, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. 6-Phosphonoglucono-D-lactone is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Phosphonoglucono-D-lactone exists in all living species, ranging from bacteria to humans. 6-Phosphonoglucono-D-lactone participates in a number of enzymatic reactions, within cattle. In particular, 6-Phosphonoglucono-D-lactone can be converted into 6-phosphogluconic acid through the action of the enzyme 6-phosphogluconolactonase. In addition, 6-Phosphonoglucono-D-lactone can be biosynthesized from Beta-D-glucose 6-phosphate; which is mediated by the enzyme glucose-6-phosphate 1-dehydrogenase. In cattle, 6-phosphonoglucono-D-lactone is involved in the metabolic pathway called cancer (via the Warburg effect).</description>
  <synonyms>
    <synonym>6-Phospho-D-glucono-1,5-lactone</synonym>
    <synonym>6-Phosphonoglucono-delta-lactone</synonym>
    <synonym>[(2R,3S,4S,5R)-3,4,5-Trihydroxy-6-oxotetrahydro-2H-pyran-2-yl]methyl dihydrogen phosphate</synonym>
    <synonym>D-Gluconic acid, delta-lactone, 6-(dihydrogen phosphate)</synonym>
    <synonym>D-Glucono-1,5-lactone 6-phosphate</synonym>
    <synonym>6-Phosphonoglucono-δ-lactone</synonym>
    <synonym>[(2R,3S,4S,5R)-3,4,5-Trihydroxy-6-oxotetrahydro-2H-pyran-2-yl]methyl dihydrogen phosphoric acid</synonym>
    <synonym>D-Gluconate, delta-lactone, 6-(dihydrogen phosphate)</synonym>
    <synonym>D-Gluconate, δ-lactone, 6-(dihydrogen phosphate)</synonym>
    <synonym>D-Gluconic acid, delta-lactone, 6-(dihydrogen phosphoric acid)</synonym>
    <synonym>D-Gluconic acid, δ-lactone, 6-(dihydrogen phosphoric acid)</synonym>
    <synonym>D-Glucono-1,5-lactone 6-phosphoric acid</synonym>
    <synonym>6-(Dihydrogen phosphate)-(8ci)-D-gluconic acid delta-lactone</synonym>
    <synonym>6-(Dihydrogen phosphate)-(9ci)-D-gluconic acid delta-lactone</synonym>
    <synonym>6-(Dihydrogen phosphate)-D-gluconic acid delta-lactone</synonym>
    <synonym>6-PGDL</synonym>
    <synonym>6-Phosphoglucono-delta-lactone</synonym>
    <synonym>6-Phosphogluconolactone</synonym>
    <synonym>D-6-Phospho-glucono-delta-lactone</synonym>
    <synonym>D-6-Phosphoglucono-delta-lactone</synonym>
    <synonym>D-Glucono-delta-lactone-6-phosphate</synonym>
    <synonym>delta-Gluconolactone 6-phosphate</synonym>
    <synonym>p-Gluconolactone</synonym>
  </synonyms>
  <chemical_formula>C6H11O9P</chemical_formula>
  <average_molecular_weight>258.1199</average_molecular_weight>
  <monisotopic_moleculate_weight>258.014068462</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>6-phosphogluconolactone</traditional_iupac>
  <cas_registry_number>2641-81-8</cas_registry_number>
  <smiles>O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)OC(=O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H11O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-5,7-9H,1H2,(H2,11,12,13)/t2-,3-,4+,5-/m1/s1</inchi>
  <inchikey>IJOJIVNDFQSGAB-SQOUGZDYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Delta valerolactones</alternative_parent>
      <alternative_parent>Gluconolactones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Delta valerolactone</substituent>
      <substituent>Delta_valerolactone</substituent>
      <substituent>Gluconolactone</substituent>
      <substituent>Hexose phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactone</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aldonolactone phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>258.1199</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>258.014068462</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)OC(=O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H11O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H11O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-5,7-9H,1H2,(H2,11,12,13)/t2-,3-,4+,5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IJOJIVNDFQSGAB-SQOUGZDYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>153.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37937</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01236</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB030612</foodb_id>
  <chemspider_id>388559</chemspider_id>
  <pdbe_id/>
  <chebi_id>16938</chebi_id>
  <pubchem_compound_id>439452</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>37157</bigg_id>
  <metlin_id>6022</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01229</protein_accession>
      <name>6-phosphogluconolactonase</name>
      <uniprot_id>Q2TBQ8</uniprot_id>
      <gene_name>PGLS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:28 UTC</creation_date>
  <update_date>2020-03-13 16:26:03 UTC</update_date>
  <accession>BMDB0001128</accession>
  <secondary_accessions>
    <accession>BMDB01128</accession>
  </secondary_accessions>
  <name>5-Phosphoribosylamine</name>
  <description/>
  <synonyms>
    <synonym>5-Phospho-D-ribosylamine</synonym>
    <synonym>5-Phosphoribosyl-1-amine</synonym>
    <synonym>5-Phospho-beta-D-ribosylamine</synonym>
    <synonym>5-Phospho-b-D-ribosylamine</synonym>
    <synonym>5-Phospho-β-D-ribosylamine</synonym>
    <synonym>5-p-beta-D-Ribosyl-amine</synonym>
    <synonym>5-p-beta-delta-Ribosyl-amine</synonym>
    <synonym>5-Phospho-beta-D-ribosyl-amine</synonym>
    <synonym>5-Phospho-beta-delta-ribosyl-amine</synonym>
    <synonym>5-Phospho-beta-delta-ribosylamine</synonym>
    <synonym>5-Phospho-delta-ribosylamine</synonym>
    <synonym>PRA</synonym>
  </synonyms>
  <chemical_formula>C5H12NO7P</chemical_formula>
  <average_molecular_weight>229.125</average_molecular_weight>
  <monisotopic_moleculate_weight>229.035138255</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-amino-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>5-phospho-β-D-ribosylamine</traditional_iupac>
  <cas_registry_number/>
  <smiles>N[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C5H12NO7P/c6-5-4(8)3(7)2(13-5)1-12-14(9,10)11/h2-5,7-8H,1,6H2,(H2,9,10,11)/t2-,3-,4-,5-/m1/s1</inchi>
  <inchikey>SKCBPEVYGOQGJN-TXICZTDVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Hemiaminals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hemiaminal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>5-phospho-D-ribosylamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-amino-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>229.125</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>229.035138255</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H12NO7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H12NO7P/c6-5-4(8)3(7)2(13-5)1-12-14(9,10)11/h2-5,7-8H,1,6H2,(H2,9,10,11)/t2-,3-,4-,5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SKCBPEVYGOQGJN-TXICZTDVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>142.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37938</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03090</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022441</foodb_id>
  <chemspider_id>388939</chemspider_id>
  <pdbe_id/>
  <chebi_id>37737</chebi_id>
  <pubchem_compound_id>439905</pubchem_compound_id>
  <knapsack_id>C00007377</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Phosphoribosylamine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>41182</bigg_id>
  <metlin_id>6023</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00600</protein_accession>
      <name>Trifunctional purine biosynthetic protein adenosine-3</name>
      <uniprot_id>Q59A32</uniprot_id>
      <gene_name>GART</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:29 UTC</creation_date>
  <update_date>2020-04-16 17:51:31 UTC</update_date>
  <accession>BMDB0001129</accession>
  <secondary_accessions>
    <accession>BMDB01129</accession>
  </secondary_accessions>
  <name>N-Acetylmannosamine</name>
  <description>N-Acetylmannosamine, also known as mannac, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetylmannosamine is possibly soluble (in water) and a moderately basic compound (based on its pKa). N-Acetylmannosamine participates in a number of enzymatic reactions, within cattle. In particular, N-Acetylmannosamine can be biosynthesized from N-acetyl-D-glucosamine through its interaction with the enzyme N-acylglucosamine 2-epimerase. In addition, N-Acetylmannosamine and uridine 5'-diphosphate can be biosynthesized from uridine diphosphate-N-acetylglucosamine; which is mediated by the enzyme bifunctional UDP-N-acetyl glucosamine 2-epimerase / N-acetylmannosamine kinase. In cattle, N-acetylmannosamine is involved in the metabolic pathway called the amino sugar metabolism pathway.</description>
  <synonyms>
    <synonym>2-Acetamido-2-deoxy-D-mannose</synonym>
    <synonym>ManNAc</synonym>
    <synonym>N-Acetylmannosamine, (D)-isomer</synonym>
    <synonym>N-Acetylmannosamine, (L)-isomer</synonym>
  </synonyms>
  <chemical_formula>C8H15NO6</chemical_formula>
  <average_molecular_weight>221.2078</average_molecular_weight>
  <monisotopic_moleculate_weight>221.089937217</monisotopic_moleculate_weight>
  <iupac_name>N-[(3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid</iupac_name>
  <traditional_iupac>N-acetylmannosamine</traditional_iupac>
  <cas_registry_number>3615-17-6</cas_registry_number>
  <smiles>[H]C1(O)O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@]1([H])N=C(C)O</smiles>
  <inchi>InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5+,6-,7-,8?/m1/s1</inchi>
  <inchikey>OVRNDRQMDRJTHS-ZTVVOAFPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Acylaminosugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Acylaminosugar</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Amino sugars</external_descriptor>
      <external_descriptor>N-acetyl-hexosamine</external_descriptor>
      <external_descriptor>N-acetylmannosamine</external_descriptor>
      <external_descriptor>N-acyl-D-mannosamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[(3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>221.2078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>221.089937217</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]C1(O)O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@]1([H])N=C(C)O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15NO6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5+,6-,7-,8?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OVRNDRQMDRJTHS-ZTVVOAFPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>122.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36163</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Mottram HR, Evershed RP: Elucidation of the composition of bovine milk fat triacylglycerols using high-performance liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry. J Chromatogr A. 2001 Aug 17;926(2):239-53.</reference_text>
          <pubmed_id>11556330</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00645</kegg_id>
  <chemspider_id/>
  <foodb_id/>
  <pubchem_compound_id/>
  <chebi_id>63153</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id>C00019583</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>N-Acetylmannosamine</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Satoh, Chiyoko; Akio, Kiyomoto. Nitrogen-containing sugars. I. Synthesis of 2-acetamido-2-deoxy-D-mannose from 1-deoxy-1-nitro-D-mannitol pentaacetate. Chemical &amp; Pharmaceutical Bulletin (1964), 12(5), 615-19.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mottram HR, Evershed RP: Elucidation of the composition of bovine milk fat triacylglycerols using high-performance liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry. J Chromatogr A. 2001 Aug 17;926(2):239-53.</reference_text>
      <pubmed_id>11556330</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00109</protein_accession>
      <name>N-acetylneuraminate lyase</name>
      <uniprot_id>Q29RY9</uniprot_id>
      <gene_name>NPL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:30 UTC</creation_date>
  <update_date>2020-03-13 16:26:04 UTC</update_date>
  <accession>BMDB0001131</accession>
  <secondary_accessions>
    <accession>BMDB01131</accession>
  </secondary_accessions>
  <name>Iminoaspartic acid</name>
  <description/>
  <synonyms>
    <synonym>Iminoaspartate</synonym>
    <synonym>Iminosuccinate</synonym>
    <synonym>Iminosuccinic acid</synonym>
    <synonym>alpha-Iminosuccinate</synonym>
    <synonym>Imino-butanedioate</synonym>
    <synonym>Imino-butanedioic acid</synonym>
  </synonyms>
  <chemical_formula>C4H5NO4</chemical_formula>
  <average_molecular_weight>131.0868</average_molecular_weight>
  <monisotopic_moleculate_weight>131.021857653</monisotopic_moleculate_weight>
  <iupac_name>2-iminobutanedioic acid</iupac_name>
  <traditional_iupac>iminosuccinic acid</traditional_iupac>
  <cas_registry_number>79067-61-1</cas_registry_number>
  <smiles>OC(=O)CC(=N)C(O)=O</smiles>
  <inchi>InChI=1S/C4H5NO4/c5-2(4(8)9)1-3(6)7/h5H,1H2,(H,6,7)(H,8,9)</inchi>
  <inchikey>NMUOATVLLQEYHI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Dicarboxylic acids and derivatives</sub_class>
    <direct_parent>Dicarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketimines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Ketimine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C4-dicarboxylic acid</external_descriptor>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>aspartic acid derivative</external_descriptor>
      <external_descriptor>ketimine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-iminobutanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>131.0868</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>131.021857653</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC(=N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H5NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H5NO4/c5-2(4(8)9)1-3(6)7/h5H,1H2,(H,6,7)(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NMUOATVLLQEYHI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>98.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>36.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34825</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05840</kegg_id>
  <foodb_id>FDB022443</foodb_id>
  <drugbank_id/>
  <chemspider_id>13628208</chemspider_id>
  <pdbe_id/>
  <chebi_id>50616</chebi_id>
  <pubchem_compound_id>796</pubchem_compound_id>
  <knapsack_id>C00007565</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Iminosuccinic acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6025</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:32 UTC</creation_date>
  <update_date>2020-03-13 16:26:04 UTC</update_date>
  <accession>BMDB0001132</accession>
  <secondary_accessions>
    <accession>BMDB01132</accession>
  </secondary_accessions>
  <name>Nicotinic acid mononucleotide</name>
  <description>Nicotinic acid mononucleotide, also known as beta-nicotinate D-ribonucleotide or deamido-NMN, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. Nicotinic acid mononucleotide is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Nicotinic acid mononucleotide exists in all eukaryotes, ranging from yeast to humans. Nicotinic acid mononucleotide participates in a number of enzymatic reactions, within cattle. In particular, Nicotinic acid mononucleotide can be biosynthesized from nicotinate D-ribonucleoside through the action of the enzyme nicotinamide riboside kinase 1. In addition, Nicotinic acid mononucleotide can be converted into nicotinate D-ribonucleoside; which is mediated by the enzyme cytosolic purine 5'-nucleotidase. In cattle, nicotinic acid mononucleotide is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway.</description>
  <synonyms>
    <synonym>Nicotinate mononucleotide</synonym>
    <synonym>3-Carboxy-1-(5-O-phosphono-b-D-ribofuranosyl)-pyridinium inner salt</synonym>
    <synonym>3-Carboxy-1-(5-O-phosphono-beta-D-ribofuranosyl)-pyridinium inner salt</synonym>
    <synonym>3-Carboxy-1-(5-O-phosphono-beta-delta-ribofuranosyl)-pyridinium inner salt</synonym>
    <synonym>3-Carboxy-1-beta-D-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt</synonym>
    <synonym>3-Carboxy-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-phosphate inner salt</synonym>
    <synonym>3-Pyridinecarboxylic acid mononucleotide</synonym>
    <synonym>beta-Nicotinate D-ribonucleotide</synonym>
    <synonym>beta-Nicotinic acid mononucleotide</synonym>
    <synonym>Deamido nicotinamide ribonucleotide</synonym>
    <synonym>Deamido-nicotinamide mononucleotide</synonym>
    <synonym>Deamido-NMN</synonym>
    <synonym>NaMN</synonym>
    <synonym>Nicotinate D-ribonucleoside</synonym>
    <synonym>Nicotinate D-ribonucleotide</synonym>
    <synonym>Nicotinate nucleotide</synonym>
    <synonym>Nicotinate ribonucleotide</synonym>
    <synonym>Nicotinate-D-ribonucleotide</synonym>
    <synonym>Nicotinate-delta-ribonucleotide</synonym>
    <synonym>Nicotinic acid ribonucleotide</synonym>
    <synonym>Nicotinic acid ribotide</synonym>
    <synonym>Nicotinic mononucleotide</synonym>
  </synonyms>
  <chemical_formula>C11H16NO9P</chemical_formula>
  <average_molecular_weight>337.2198</average_molecular_weight>
  <monisotopic_moleculate_weight>337.056267627</monisotopic_moleculate_weight>
  <iupac_name>3-carboxy-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2,3-dihydro-1λ⁵-pyridin-1-ylium</iupac_name>
  <traditional_iupac>3-carboxy-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2,3-dihydro-1λ⁵-pyridin-1-ylium</traditional_iupac>
  <cas_registry_number>321-02-8</cas_registry_number>
  <smiles>O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)([O-])=O)[N+]1=CC=CC(C1)C(O)=O</smiles>
  <inchi>InChI=1S/C11H16NO9P/c13-8-7(5-20-22(17,18)19)21-10(9(8)14)12-3-1-2-6(4-12)11(15)16/h1-3,6-10,13-14H,4-5H2,(H2-,15,16,17,18,19)/t6?,7-,8-,9-,10-/m1/s1</inchi>
  <inchikey>OGCWVIVNTBZPBW-BHRXDNSCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Alkyl phosphates</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-carboxy-1-[(2R,3R,4S,5R)-5-[(hydrogen phosphonatooxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2,3-dihydro-1λ⁵-pyridin-1-ylium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>337.2198</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>337.056267627</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)([O-])=O)[N+]1=CC=CC(C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H16NO9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H16NO9P/c13-8-7(5-20-22(17,18)19)21-10(9(8)14)12-3-1-2-6(4-12)11(15)16/h1-3,6-10,13-14H,4-5H2,(H2-,15,16,17,18,19)/t6?,7-,8-,9-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OGCWVIVNTBZPBW-BHRXDNSCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>159.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>80.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182573</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022444</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>53477721</pubchem_compound_id>
  <chebi_id>15763</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id>C01185</kegg_id>
  <bigg_id>37018</bigg_id>
  <wikipedia_id/>
  <metlin_id>6026</metlin_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00105</protein_accession>
      <name>Nicotinamide mononucleotide adenylyltransferase 1</name>
      <uniprot_id>Q0VD50</uniprot_id>
      <gene_name>NMNAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00106</protein_accession>
      <name>Nicotinamide mononucleotide adenylyltransferase 2</name>
      <uniprot_id>Q0VC59</uniprot_id>
      <gene_name>NMNAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00635</protein_accession>
      <name>Nicotinate phosphoribosyltransferase</name>
      <uniprot_id>A5PK51</uniprot_id>
      <gene_name>NAPRT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00636</protein_accession>
      <name>Nicotinate-nucleotide pyrophosphorylase [carboxylating]</name>
      <uniprot_id>Q3T063</uniprot_id>
      <gene_name>QPRT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:33 UTC</creation_date>
  <update_date>2020-04-15 22:28:11 UTC</update_date>
  <accession>BMDB0001134</accession>
  <secondary_accessions>
    <accession>BMDB01134</accession>
  </secondary_accessions>
  <name>Phosphoadenosine phosphosulfate</name>
  <description/>
  <synonyms>
    <synonym>3'-Phosphoadenosine 5'-phosphosulfate</synonym>
    <synonym>3'-Phosphoadenylyl sulfate</synonym>
    <synonym>PAPS</synonym>
    <synonym>3'-Phospho-5'-adenylyl sulfate</synonym>
    <synonym>3'-Phosphoadenosine 5'-phosphosulfuric acid</synonym>
    <synonym>3'-Phosphoadenosine 5'-phosphosulphate</synonym>
    <synonym>3'-Phosphoadenosine 5'-phosphosulphuric acid</synonym>
    <synonym>3'-Phosphoadenylyl sulfuric acid</synonym>
    <synonym>3'-Phosphoadenylyl sulphate</synonym>
    <synonym>3'-Phosphoadenylyl sulphuric acid</synonym>
    <synonym>3'-Phospho-5'-adenylyl sulfuric acid</synonym>
    <synonym>3'-Phospho-5'-adenylyl sulphate</synonym>
    <synonym>3'-Phospho-5'-adenylyl sulphuric acid</synonym>
    <synonym>Phosphoadenosine phosphosulfuric acid</synonym>
    <synonym>Phosphoadenosine phosphosulphate</synonym>
    <synonym>Phosphoadenosine phosphosulphuric acid</synonym>
    <synonym>3'-Phosphoadenosine-5'-phosphosulfate</synonym>
    <synonym>3'-Phosphoadenosine-5'-phosphosulphate</synonym>
    <synonym>3'-Phosphoadenylyl-sulfate</synonym>
    <synonym>3'-Phosphoadenylyl-sulphate</synonym>
    <synonym>5-Phosphoadenosine 3-phosphosulfate</synonym>
    <synonym>5-Phosphoadenosine 3-phosphosulphate</synonym>
    <synonym>Adenosine 3' phosphate 5' phosphosulfate</synonym>
    <synonym>Adenosine-3'-phosphate-5'-phosphosulfate</synonym>
    <synonym>Phosphosulfate, phosphoadenosine</synonym>
  </synonyms>
  <chemical_formula>C10H15N5O13P2S</chemical_formula>
  <average_molecular_weight>507.264</average_molecular_weight>
  <monisotopic_moleculate_weight>506.986229305</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid</iupac_name>
  <traditional_iupac>3'-phosphoadenylyl sulfate</traditional_iupac>
  <cas_registry_number>482-67-7</cas_registry_number>
  <smiles>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](OP(O)(O)=O)[C@H]1O</smiles>
  <inchi>InChI=1S/C10H15N5O13P2S/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(27-29(17,18)19)4(26-10)1-25-30(20,21)28-31(22,23)24/h2-4,6-7,10,16H,1H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)(H,22,23,24)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>GACDQMDRPRGCTN-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside 3',5'-bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside 3',5'-bisphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic sulfuric acids and derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Coenzymes</external_descriptor>
      <external_descriptor>acyl sulfate</external_descriptor>
      <external_descriptor>adenosine bisphosphate</external_descriptor>
      <external_descriptor>purine ribonucleoside bisphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>507.264</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>506.986229305</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](OP(O)(O)=O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H15N5O13P2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H15N5O13P2S/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(27-29(17,18)19)4(26-10)1-25-30(20,21)28-31(22,23)24/h2-4,6-7,10,16H,1H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)(H,22,23,24)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GACDQMDRPRGCTN-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>275.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>94.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sulfate/Sulfite Metabolism</name>
      <smpdb_id>SMP0087216</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33970</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00053</kegg_id>
  <foodb_id>FDB022445</foodb_id>
  <drugbank_id>DB02902</drugbank_id>
  <chemspider_id>9799</chemspider_id>
  <pdbe_id/>
  <chebi_id>17980</chebi_id>
  <pubchem_compound_id>10214</pubchem_compound_id>
  <knapsack_id>C00007446</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>3'-Phosphoadenosine-5'-phosphosulfate</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33679</bigg_id>
  <metlin_id>6028</metlin_id>
  <synthesis_reference>Lin, Chun-Hung; Shen, Gwo-Jenn; Garcia-Junceda, Eduardo; Wong, Chi-Huey. Enzymic Synthesis and Regeneration of 3'-Phosphoadenosine 5'-Phosphosulfate (PAPS) for Regioselective Sulfation of Oligosaccharides. J. Am. Chem. Soc., 1995, 117 (30), pp 8031-8032</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00080</protein_accession>
      <name>Galactosylceramide sulfotransferase</name>
      <uniprot_id>A6QNK1</uniprot_id>
      <gene_name>GAL3ST1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00375</protein_accession>
      <name>Protein-tyrosine sulfotransferase 2</name>
      <uniprot_id>Q3SYY2</uniprot_id>
      <gene_name>TPST2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00376</protein_accession>
      <name>Sulfotransferase 1A1</name>
      <uniprot_id>P50227</uniprot_id>
      <gene_name>SULT1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00377</protein_accession>
      <name>Bifunctional heparan sulfate N-deacetylase/N-sulfotransferase 2</name>
      <uniprot_id>O97583</uniprot_id>
      <gene_name>NDST2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00378</protein_accession>
      <name>Estrogen sulfotransferase</name>
      <uniprot_id>P19217</uniprot_id>
      <gene_name>SULT1E1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:34 UTC</creation_date>
  <update_date>2020-03-13 16:26:05 UTC</update_date>
  <accession>BMDB0001137</accession>
  <secondary_accessions>
    <accession>BMDB01137</accession>
  </secondary_accessions>
  <name>Hydroxymethylbilane</name>
  <description>Hydroxymethylbilane, also known as hydroxymethylbilane, belongs to the class of organic compounds known as tetrapyrroles and derivatives. These are polycyclic aromatic compounds containing four pyrrole rings joined by one-carbon units linking position 2 of one pyrrole ring to position 5 of the next. Hydroxymethylbilane is possibly soluble (in water) and a weakly acidic compound (based on its pKa). Hydroxymethylbilane exists in all living species, ranging from bacteria to humans. In cattle, hydroxymethylbilane is involved in the metabolic pathway called the porphyrin metabolism pathway.</description>
  <synonyms>
    <synonym>(Hydroxymethyl)bilane</synonym>
    <synonym>3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,22,23,24-hexahydro-19-(hydroxymethyl)-21H-biline-2,7,12,17-tetrapropanoic acid</synonym>
    <synonym>3,8,13,18-Tetrakis(carboxymethyl)-5,10,15,22,23,24-hexahydro-19-(hydroxymethyl)-21H-biline-2,7,12,17-tetrapropanoate</synonym>
    <synonym>3,8,13,18-Tetrakis(carboxymethyl)-19-(hydroxymethyl)bilane-2,7,12,17-tetrapropanoate</synonym>
    <synonym>3,8,13,18-Tetrakis(carboxymethyl)-19-(hydroxymethyl)bilane-2,7,12,17-tetrapropanoic acid</synonym>
    <synonym>3-[2-[[4-(2-Carboxyethyl)-5-[[4-(2-carboxyethyl)-5-[[4-(2-carboxyethyl)-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-5-(hydroxymethyl)-1H-pyrrol-3-yl]propanoate</synonym>
    <synonym>3-[2-[[4-(2-Carboxyethyl)-5-[[4-(2-carboxyethyl)-5-[[4-(2-carboxyethyl)-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-5-(hydroxymethyl)-1H-pyrrol-3-yl]propanoic acid</synonym>
    <synonym>Preuroporphyrinogen</synonym>
  </synonyms>
  <chemical_formula>C40H46N4O17</chemical_formula>
  <average_molecular_weight>854.8098</average_molecular_weight>
  <monisotopic_moleculate_weight>854.285796066</monisotopic_moleculate_weight>
  <iupac_name>3-(2-{[4-(2-carboxyethyl)-5-{[4-(2-carboxyethyl)-5-{[4-(2-carboxyethyl)-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-4-(carboxymethyl)-5-(hydroxymethyl)-1H-pyrrol-3-yl)propanoic acid</iupac_name>
  <traditional_iupac>hydroxymethylbilane</traditional_iupac>
  <cas_registry_number>73023-76-4</cas_registry_number>
  <smiles>OCC1=C(CC(O)=O)C(CCC(O)=O)=C(CC2=C(CC(O)=O)C(CCC(O)=O)=C(CC3=C(CC(O)=O)C(CCC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=CN4)N3)N2)N1</smiles>
  <inchi>InChI=1S/C40H46N4O17/c45-17-32-25(12-40(60)61)21(4-8-36(52)53)29(44-32)15-31-24(11-39(58)59)20(3-7-35(50)51)28(43-31)14-30-23(10-38(56)57)19(2-6-34(48)49)27(42-30)13-26-22(9-37(54)55)18(16-41-26)1-5-33(46)47/h16,41-45H,1-15,17H2,(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)(H,58,59)(H,60,61)</inchi>
  <inchikey>WDFJYRZCZIUBPR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrapyrroles and derivatives. These are polycyclic aromatic compounds containing four pyrrole rings joined by one-carbon units linking position 2 of one pyrrole ring to position 5 of the next.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class/>
    <direct_parent>Tetrapyrroles and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
      <substituent>Tetrapyrrole skeleton</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>bilanes</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(2-{[4-(2-carboxyethyl)-5-{[4-(2-carboxyethyl)-5-{[4-(2-carboxyethyl)-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-4-(carboxymethyl)-5-(hydroxymethyl)-1H-pyrrol-3-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>854.8098</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>854.285796066</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC1=C(CC(O)=O)C(CCC(O)=O)=C(CC2=C(CC(O)=O)C(CCC(O)=O)=C(CC3=C(CC(O)=O)C(CCC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=CN4)N3)N2)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C40H46N4O17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C40H46N4O17/c45-17-32-25(12-40(60)61)21(4-8-36(52)53)29(44-32)15-31-24(11-39(58)59)20(3-7-35(50)51)28(43-31)14-30-23(10-38(56)57)19(2-6-34(48)49)27(42-30)13-26-22(9-37(54)55)18(16-41-26)1-5-33(46)47/h16,41-45H,1-15,17H2,(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)(H,58,59)(H,60,61)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WDFJYRZCZIUBPR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>381.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>209.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>85.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22561</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01024</kegg_id>
  <foodb_id>FDB022446</foodb_id>
  <drugbank_id/>
  <chemspider_id>767</chemspider_id>
  <pdbe_id/>
  <chebi_id>16645</chebi_id>
  <pubchem_compound_id>788</pubchem_compound_id>
  <knapsack_id>C00007374</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Hydroxymethylbilane</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>36648</bigg_id>
  <metlin_id>3699</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00110</protein_accession>
      <name>Porphobilinogen deaminase</name>
      <uniprot_id>Q2KIN5</uniprot_id>
      <gene_name>HMBS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:35 UTC</creation_date>
  <update_date>2020-04-15 22:14:57 UTC</update_date>
  <accession>BMDB0001138</accession>
  <secondary_accessions>
    <accession>BMDB01138</accession>
  </secondary_accessions>
  <name>N-Acetylglutamic acid</name>
  <description/>
  <synonyms>
    <synonym>(S)-2-(Acetylamino)pentanedioic acid</synonym>
    <synonym>Ac-glu-OH</synonym>
    <synonym>Acetyl-L-glutamic acid</synonym>
    <synonym>Acetylglutamic acid</synonym>
    <synonym>L-N-Acetylglutamic acid</synonym>
    <synonym>N-Ac-glu-OH</synonym>
    <synonym>N-ACETYL-L-glutamATE</synonym>
    <synonym>N-Acetylglutamic acid</synonym>
    <synonym>(S)-2-(Acetylamino)pentanedioate</synonym>
    <synonym>Acetyl-L-glutamate</synonym>
    <synonym>Acetylglutamate</synonym>
    <synonym>L-N-Acetylglutamate</synonym>
    <synonym>N-Acetylglutamate</synonym>
    <synonym>N-Acetylglutamic acid semialdehyde</synonym>
    <synonym>N-Acetylglutamate, potassium salt, (L)-isomer</synonym>
    <synonym>N-Acetylglutamate, (D)-isomer</synonym>
    <synonym>N-Acetylglutamate, calcium salt (1:1), (L)-isomer</synonym>
    <synonym>N-Acetylglutamate, dipotassium salt, (L)-isomer</synonym>
    <synonym>N-Acetylglutamate, disodium salt, (L)-isomer</synonym>
    <synonym>N-Acetylglutamate, calcium salt, (L)-isomer</synonym>
    <synonym>N-Acetylglutamate, magnesium salt, (L)-isomer</synonym>
    <synonym>Sodium N-acetylglutamate</synonym>
    <synonym>N-Acetylglutamate, (DL)-isomer</synonym>
    <synonym>N-Acetylglutamate, monosodium salt, (L)-isomer</synonym>
    <synonym>N-Acetyl-L-glutaminic acid</synonym>
    <synonym>alpha-(N-Acetyl)-L-glutamic acid</synonym>
    <synonym>Α-(N-acetyl)-L-glutamic acid</synonym>
    <synonym>NAcGlu</synonym>
    <synonym>N-Acetyl-L-glutamic acid</synonym>
  </synonyms>
  <chemical_formula>C7H11NO5</chemical_formula>
  <average_molecular_weight>189.1659</average_molecular_weight>
  <monisotopic_moleculate_weight>189.063722467</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-acetamidopentanedioic acid</iupac_name>
  <traditional_iupac>N-acetyl-L-glutamate</traditional_iupac>
  <cas_registry_number>1188-37-0</cas_registry_number>
  <smiles>CC(=O)N[C@@H](CCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1</inchi>
  <inchikey>RFMMMVDNIPUKGG-YFKPBYRVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Glutamic acid and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acetyl-L-amino acid</external_descriptor>
      <external_descriptor>N-acyl-L-glutamic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>199 - 201 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>52 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-acetamidopentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>189.1659</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>189.063722467</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H](CCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H11NO5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RFMMMVDNIPUKGG-YFKPBYRVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>103.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451941</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00624</kegg_id>
  <foodb_id>FDB031019</foodb_id>
  <drugbank_id>DB04075</drugbank_id>
  <chemspider_id>64077</chemspider_id>
  <pdbe_id/>
  <chebi_id>17533</chebi_id>
  <pubchem_compound_id>70914</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id>ACETYL-GLU</meta_cyc_id>
  <wikipedia_id>N-Acetylglutamic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>hang, Xiaolin; Yang, Qiyong; Sun, Yuesheng.  Preparation of N-acetyl-L-glutamic acid.    Huaxue Shijie  (2002),  43(7),  363-365.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:36 UTC</creation_date>
  <update_date>2020-04-15 22:35:43 UTC</update_date>
  <accession>BMDB0001139</accession>
  <secondary_accessions>
    <accession>BMDB01139</accession>
  </secondary_accessions>
  <name>Prostaglandin F2a</name>
  <description/>
  <synonyms>
    <synonym>(+)-Prostaglandin F2a</synonym>
    <synonym>(5Z,13E)-(15S)-9-alpha,11-alpha,15-Trihydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-9-alpha,11-alpha,15-Trihydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E,15S)-9a,11a,15-Trihydroxyprosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,13E,15S)-9a,11a,15-Trihydroxyprosta-5,13-dien-1-Oic acid</synonym>
    <synonym>(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxy-prosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxy-prosta-5,13-dien-1-Oic acid</synonym>
    <synonym>(9alpha,11alpha,15)-Trihydroxyprosta-(5Z,13E)-dien-1-Oate</synonym>
    <synonym>(9alpha,11alpha,15)-Trihydroxyprosta-(5Z,13E)-dien-1-Oic acid</synonym>
    <synonym>7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoate</synonym>
    <synonym>7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid</synonym>
    <synonym>9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-Oate</synonym>
    <synonym>9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-Oic acid</synonym>
    <synonym>9,11,15-Trihydroxyprosta-5Z,13E-dien-1-Oate</synonym>
    <synonym>9,11,15-Trihydroxyprosta-5Z,13E-dien-1-Oic acid</synonym>
    <synonym>9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoate</synonym>
    <synonym>9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoic acid</synonym>
    <synonym>9a,11a-PGF2</synonym>
    <synonym>9a,11a-PGF2a</synonym>
    <synonym>Amoglandin</synonym>
    <synonym>Cyclosin</synonym>
    <synonym>Dinifertin</synonym>
    <synonym>Dinoprost</synonym>
    <synonym>Enzaprost</synonym>
    <synonym>Enzaprost F</synonym>
    <synonym>F2a Isoprostane</synonym>
    <synonym>Glandin N</synonym>
    <synonym>L-PGF2-alpha</synonym>
    <synonym>L-Prostaglandin F2-alpha</synonym>
    <synonym>Panacelan</synonym>
    <synonym>PGF2a</synonym>
    <synonym>Prostaglandin F2</synonym>
    <synonym>Prostamate</synonym>
    <synonym>Prostarmon F</synonym>
    <synonym>Prostin F 2 alpha</synonym>
    <synonym>Protamodin</synonym>
    <synonym>9alpha,11beta PGF2</synonym>
    <synonym>9alpha,11beta-PGF2</synonym>
    <synonym>Estrofan</synonym>
    <synonym>F2 alpha, Prostaglandin</synonym>
    <synonym>F2alpha, Prostaglandin</synonym>
    <synonym>PGF2</synonym>
    <synonym>PGF2 alpha</synonym>
    <synonym>PGF2alpha</synonym>
    <synonym>Prostaglandin F2 alpha</synonym>
    <synonym>Prostaglandin F2alpha</synonym>
    <synonym>alpha, PGF2</synonym>
  </synonyms>
  <chemical_formula>C20H34O5</chemical_formula>
  <average_molecular_weight>354.481</average_molecular_weight>
  <monisotopic_moleculate_weight>354.240624198</monisotopic_moleculate_weight>
  <iupac_name>(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid</iupac_name>
  <traditional_iupac>5-trans-PGF2α</traditional_iupac>
  <cas_registry_number>551-11-1</cas_registry_number>
  <smiles>CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4+,13-12+/t15-,16+,17+,18-,19+/m0/s1</inchi>
  <inchikey>PXGPLTODNUVGFL-UAAPODJFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Prostaglandins and related compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclopentanols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclopentanol</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Prostaglandin skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Prostaglandins</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>30 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.39</value>
      <source>BODOR,H &amp; HUANG,M (1992)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>354.481</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>354.240624198</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H34O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4+,13-12+/t15-,16+,17+,18-,19+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PXGPLTODNUVGFL-UAAPODJFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>100.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>41.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37944</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438315</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00639</kegg_id>
  <foodb_id>FDB022448</foodb_id>
  <drugbank_id/>
  <chemspider_id>4446204</chemspider_id>
  <pdbe_id/>
  <chebi_id>15553</chebi_id>
  <pubchem_compound_id>5283078</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Prostaglandin F2alpha</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35568</bigg_id>
  <metlin_id>6032</metlin_id>
  <synthesis_reference>Chen, Shaoqing; Janda, Kim D.  Total synthesis of naturally occurring prostaglandin F2a on a non-crosslinked polystyrene support.    Tetrahedron Letters  (1998),  39(23),  3943-3946.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00602</protein_accession>
      <name>Carbonyl reductase [NADPH] 1</name>
      <uniprot_id>Q3SZD7</uniprot_id>
      <gene_name>CBR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:37 UTC</creation_date>
  <update_date>2020-04-16 17:52:22 UTC</update_date>
  <accession>BMDB0001140</accession>
  <secondary_accessions>
    <accession>BMDB01140</accession>
  </secondary_accessions>
  <name>Octanal</name>
  <description/>
  <synonyms>
    <synonym>1-Caprylaldehyde</synonym>
    <synonym>1-Octaldehyde</synonym>
    <synonym>1-Octanal</synonym>
    <synonym>1-Octylaldehyde</synonym>
    <synonym>Aldehyde C-8</synonym>
    <synonym>C-8 Aldehyde</synonym>
    <synonym>Caprylaldehyd</synonym>
    <synonym>Caprylaldehyde</synonym>
    <synonym>Caprylic aldehyde</synonym>
    <synonym>Kaprylaldehyd</synonym>
    <synonym>N-Caprylaldehyde</synonym>
    <synonym>N-Octaldehyde</synonym>
    <synonym>N-Octanal</synonym>
    <synonym>N-Octyl aldehyde</synonym>
    <synonym>N-Octylal</synonym>
    <synonym>Octan-1-al</synonym>
    <synonym>Octanaldehyde</synonym>
    <synonym>Octanoic aldehyde</synonym>
    <synonym>Octylaldehyd</synonym>
    <synonym>Octylaldehyde</synonym>
    <synonym>Oktanal</synonym>
    <synonym>Oktylaldehyd</synonym>
    <synonym>Aldehyde C8</synonym>
    <synonym>Antifoam-LF</synonym>
    <synonym>Octaldehyde</synonym>
    <synonym>Octanal</synonym>
  </synonyms>
  <chemical_formula>C8H16O</chemical_formula>
  <average_molecular_weight>128.212</average_molecular_weight>
  <monisotopic_moleculate_weight>128.120115134</monisotopic_moleculate_weight>
  <iupac_name>octanal</iupac_name>
  <traditional_iupac>octanal</traditional_iupac>
  <cas_registry_number>124-13-0</cas_registry_number>
  <smiles>CCCCCCCC=O</smiles>
  <inchi>InChI=1S/C8H16O/c1-2-3-4-5-6-7-8-9/h8H,2-7H2,1H3</inchi>
  <inchikey>NUJGJRNETVAIRJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Medium-chain aldehydes</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydrogen aldehydes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydrogen aldehyde</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain aldehyde</substituent>
      <substituent>Organic oxide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fatty aldehydes</external_descriptor>
      <external_descriptor>Fatty aldehydes</external_descriptor>
      <external_descriptor>an &lt;i&gt;n&lt;/i&gt;-alkanal</external_descriptor>
      <external_descriptor>fatty aldehyde</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-23 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.56 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>17.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>octanal</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>128.212</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>128.120115134</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCC=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16O/c1-2-3-4-5-6-7-8-9/h8H,2-7H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NUJGJRNETVAIRJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22771</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples have been collected from Heifer cows.</comment>
      <references>
        <reference>
          <reference_text>Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub  2013 Jun 5.</reference_text>
          <pubmed_id>23871026</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01545</kegg_id>
  <foodb_id>FDB003339</foodb_id>
  <drugbank_id/>
  <chemspider_id>441</chemspider_id>
  <pdbe_id/>
  <chebi_id>17935</chebi_id>
  <pubchem_compound_id>454</pubchem_compound_id>
  <knapsack_id>C00030880</knapsack_id>
  <meta_cyc_id>CPD-371</meta_cyc_id>
  <wikipedia_id>Octanal</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6033</metlin_id>
  <synthesis_reference>Yokoyama, Toshiharu; Matsuyama, Naoko; Maki, Takao.  Preparation of aldehydes.    Jpn. Kokai Tokkyo Koho  (1992),     6 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:39 UTC</creation_date>
  <update_date>2020-03-13 16:26:08 UTC</update_date>
  <accession>BMDB0001142</accession>
  <secondary_accessions>
    <accession>BMDB01142</accession>
  </secondary_accessions>
  <name>FMNH</name>
  <description/>
  <synonyms>
    <synonym>1,5-Dihydroriboflavin 5'-(dihydrogen phosphate)</synonym>
    <synonym>Flavin mononucleotide (reduced)</synonym>
    <synonym>FMNH</synonym>
    <synonym>Reduced FMN</synonym>
    <synonym>1,5-Dihydroriboflavin 5'-(dihydrogen phosphoric acid)</synonym>
    <synonym>Reduced flavin mononucleotide</synonym>
    <synonym>Flavin mononucleotide hydroquinone</synonym>
  </synonyms>
  <chemical_formula>C17H23N4O9P</chemical_formula>
  <average_molecular_weight>458.3597</average_molecular_weight>
  <monisotopic_moleculate_weight>458.120264866</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>fmnh(.)</traditional_iupac>
  <cas_registry_number>5666-16-0</cas_registry_number>
  <smiles>CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=C(N2)C(=O)NC(=O)N1</smiles>
  <inchi>InChI=1S/C17H23N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,18,22-24H,5-6H2,1-2H3,(H2,27,28,29)(H2,19,20,25,26)/t11-,12+,14-/m0/s1</inchi>
  <inchikey>YTNIXZGTHTVJBW-SCRDCRAPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Flavin nucleotides</class>
    <sub_class/>
    <direct_parent>Flavin nucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyldiarylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Flavins</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary amines</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alkyldiarylamine</substituent>
      <substituent>Amine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Flavin</substituent>
      <substituent>Flavin nucleotide</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Pteridine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>flavin mononucleotide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>458.3597</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>458.120264866</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=C(N2)C(=O)NC(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C17H23N4O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C17H23N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,18,22-24H,5-6H2,1-2H3,(H2,27,28,29)(H2,19,20,25,26)/t11-,12+,14-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YTNIXZGTHTVJBW-SCRDCRAPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>200.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>118.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>42.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31720</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022449</foodb_id>
  <chemspider_id>393046</chemspider_id>
  <drugbank_id/>
  <chebi_id>16048</chebi_id>
  <pubchem_compound_id>445395</pubchem_compound_id>
  <kegg_id>C01847</kegg_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>FMNH2</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6034</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:40 UTC</creation_date>
  <update_date>2020-03-13 16:26:08 UTC</update_date>
  <accession>BMDB0001143</accession>
  <secondary_accessions>
    <accession>BMDB01143</accession>
  </secondary_accessions>
  <name>Inositol 1,3,4-trisphosphate</name>
  <description/>
  <synonyms>
    <synonym>(1S,3S,4S)-1,3,4-TRIPHOSPHO-myo-inositol</synonym>
    <synonym>D-Myo-inositol 1,3,4-trisphosphate</synonym>
    <synonym>D-Myo-inositol 1,3,4-trisphosphoric acid</synonym>
    <synonym>Inositol 1,3,4-trisphosphoric acid</synonym>
    <synonym>1,3,4-Itp</synonym>
    <synonym>1D-Myo-inositol 1,3,4-trisphosphate</synonym>
    <synonym>I3S</synonym>
    <synonym>Inositol 1,3,4-triphosphate</synonym>
    <synonym>Myo-inositol 1,3,4-trisphosphate</synonym>
    <synonym>Inositol 1,3,4-trisphosphate, (D)-isomer</synonym>
  </synonyms>
  <chemical_formula>C6H15O15P3</chemical_formula>
  <average_molecular_weight>420.0956</average_molecular_weight>
  <monisotopic_moleculate_weight>419.962379346</monisotopic_moleculate_weight>
  <iupac_name>{[(1S,2R,3R,4S,5S,6S)-2,3,5-trihydroxy-4,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>inositol 1,3,4-trisphosphate</traditional_iupac>
  <cas_registry_number>98102-63-7</cas_registry_number>
  <smiles>O[C@@H]1[C@@H](O)[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@@H](O)[C@H]1OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C6H15O15P3/c7-1-2(8)5(20-23(13,14)15)6(21-24(16,17)18)3(9)4(1)19-22(10,11)12/h1-9H,(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)/t1-,2-,3+,4+,5+,6+/m1/s1</inchi>
  <inchikey>MMWCIQZXVOZEGG-MLQGYMEPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Inositol phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclohexanols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Cyclohexanol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Inositol phosphate</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>myo-inositol trisphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(1S,2R,3R,4S,5S,6S)-2,3,5-trihydroxy-4,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>420.0956</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>419.962379346</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]1[C@@H](O)[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@@H](O)[C@H]1OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H15O15P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H15O15P3/c7-1-2(8)5(20-23(13,14)15)6(21-24(16,17)18)3(9)4(1)19-22(10,11)12/h1-9H,(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)/t1-,2-,3+,4+,5+,6+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MMWCIQZXVOZEGG-MLQGYMEPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>260.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Succinate Signalling During Inflammation</name>
      <smpdb_id>SMP0120886</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182871</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183221</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022450</foodb_id>
  <chemspider_id>388561</chemspider_id>
  <drugbank_id>DB01729</drugbank_id>
  <chebi_id>18228</chebi_id>
  <pubchem_compound_id>439455</pubchem_compound_id>
  <kegg_id>C01243</kegg_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id>37172</bigg_id>
  <wikipedia_id/>
  <metlin_id>6035</metlin_id>
  <synthesis_reference>Marecek J F; Estevez V A; Prestwich G D  New tetherable derivatives of myo-inositol 2,4,5- and 1,3,4-trisphosphates.    Carbohydrate research  (1992),  234 65-73.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00089</protein_accession>
      <name>Inositol-tetrakisphosphate 1-kinase</name>
      <uniprot_id>P0C0T1</uniprot_id>
      <gene_name>ITPK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:41 UTC</creation_date>
  <update_date>2020-03-13 16:26:09 UTC</update_date>
  <accession>BMDB0001147</accession>
  <secondary_accessions>
    <accession>BMDB01147</accession>
  </secondary_accessions>
  <name>Aminomalonic acid</name>
  <description>Aminomalonic acid, also known as aminomalonate or amino-propanedioate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Aminomalonic acid is possibly soluble (in water) and a very strong basic compound (based on its pKa). Aminomalonic acid exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>2-Aminomalonic acid</synonym>
    <synonym>Aminomalonate</synonym>
    <synonym>2-Aminomalonate</synonym>
    <synonym>a-Aminomalonic acid</synonym>
    <synonym>alpha-Aminomalonic acid</synonym>
    <synonym>Amino-malonic acid</synonym>
    <synonym>Amino-propanedioate</synonym>
    <synonym>Amino-propanedioic acid</synonym>
    <synonym>Aminopropanedioate</synonym>
    <synonym>Aminopropanedioic acid</synonym>
  </synonyms>
  <chemical_formula>C3H5NO4</chemical_formula>
  <average_molecular_weight>119.0761</average_molecular_weight>
  <monisotopic_moleculate_weight>119.021857653</monisotopic_moleculate_weight>
  <iupac_name>2-aminopropanedioic acid</iupac_name>
  <traditional_iupac>aminomalonic acid</traditional_iupac>
  <cas_registry_number>1068-84-4</cas_registry_number>
  <smiles>NC(C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H5NO4/c4-1(2(5)6)3(7)8/h1H,4H2,(H,5,6)(H,7,8)</inchi>
  <inchikey>JINBYESILADKFW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-dicarbonyl compounds</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>amino dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-aminopropanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>119.0761</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>119.021857653</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H5NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H5NO4/c4-1(2(5)6)3(7)8/h1H,4H2,(H,5,6)(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JINBYESILADKFW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>100.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>21.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33628</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by GC-TOF/MS</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
          <pubmed_id>29197344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022451</foodb_id>
  <chemspider_id>90998</chemspider_id>
  <drugbank_id>DB02289</drugbank_id>
  <chebi_id>17475</chebi_id>
  <pubchem_compound_id>100714</pubchem_compound_id>
  <kegg_id>C00872</kegg_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>AMINOMALONATE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Matthew, Margaret; Neuberger, A.  Aminomalonate.    I.U.B. (Intern. Union Biochem.) Symp. Ser.  (1963),  Volume Date 1962,  30  243-51.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
      <pubmed_id>29197344</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:42 UTC</creation_date>
  <update_date>2020-04-16 20:39:22 UTC</update_date>
  <accession>BMDB0001149</accession>
  <secondary_accessions>
    <accession>BMDB01149</accession>
  </secondary_accessions>
  <name>5-Aminolevulinic acid</name>
  <description/>
  <synonyms>
    <synonym>5-ALA</synonym>
    <synonym>5-Amino-4-oxopentanoate</synonym>
    <synonym>5-Amino-4-oxovaleric acid</synonym>
    <synonym>5-Aminolevulinate</synonym>
    <synonym>Aminolevulinic acid</synonym>
    <synonym>DALA</synonym>
    <synonym>delta-ALA</synonym>
    <synonym>delta-Aminolevulinic acid</synonym>
    <synonym>5-Amino-4-oxopentanoic acid</synonym>
    <synonym>5-Amino-4-oxovalerate</synonym>
    <synonym>Aminolevulinate</synonym>
    <synonym>Δ-ala</synonym>
    <synonym>delta-Aminolevulinate</synonym>
    <synonym>Δ-aminolevulinate</synonym>
    <synonym>Δ-aminolevulinic acid</synonym>
    <synonym>5-Amino-4-oxo-pentanoate</synonym>
    <synonym>5-Amino-4-oxo-pentanoic acid</synonym>
    <synonym>5-Amino-levulinate</synonym>
    <synonym>5-Amino-levulinic acid</synonym>
    <synonym>5-Aminolaevulinate</synonym>
    <synonym>5-Aminolaevulinic acid</synonym>
    <synonym>Aladerm</synonym>
    <synonym>Amino-levulinic acid</synonym>
    <synonym>Kerastick</synonym>
    <synonym>5 Aminolevulinate</synonym>
    <synonym>Acid, Delta-aminolevulinic</synonym>
    <synonym>Levulan</synonym>
    <synonym>5 Aminolaevulinate</synonym>
    <synonym>Acid hydrochloride, aminolevulinic</synonym>
    <synonym>Bertek brand OF aminolevulinic acid hydrochloride</synonym>
    <synonym>Hydrochloride, aminolevulinic acid</synonym>
    <synonym>Acid, aminolevulinic</synonym>
    <synonym>Aminolevulinic acid hydrochloride</synonym>
    <synonym>Delta Aminolevulinic acid</synonym>
  </synonyms>
  <chemical_formula>C5H9NO3</chemical_formula>
  <average_molecular_weight>131.1299</average_molecular_weight>
  <monisotopic_moleculate_weight>131.058243159</monisotopic_moleculate_weight>
  <iupac_name>5-amino-4-oxopentanoic acid</iupac_name>
  <traditional_iupac>aminolevulinic acid</traditional_iupac>
  <cas_registry_number>106-60-5</cas_registry_number>
  <smiles>NCC(=O)CCC(O)=O</smiles>
  <inchi>InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)</inchi>
  <inchikey>ZGXJTSGNIOSYLO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Delta amino acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-amino ketones</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Gamma-keto acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Short-chain keto acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-aminoketone</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Delta amino acid or derivatives</substituent>
      <substituent>Gamma-keto acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Keto acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Short-chain keto acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>4-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>delta-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>156 - 158 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000 mg/mL at 25 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>7.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-amino-4-oxopentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>131.1299</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>131.058243159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCC(=O)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H9NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZGXJTSGNIOSYLO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>704</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37948</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022452</foodb_id>
  <chemspider_id>134</chemspider_id>
  <drugbank_id>DB00855</drugbank_id>
  <chebi_id>17549</chebi_id>
  <pubchem_compound_id>137</pubchem_compound_id>
  <kegg_id>C00430</kegg_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007378</knapsack_id>
  <meta_cyc_id/>
  <bigg_id>34963</bigg_id>
  <wikipedia_id>Aminolevulinic_acid</wikipedia_id>
  <metlin_id>6037</metlin_id>
  <synthesis_reference>Goli?ski J., D?browski Z., Obukowicz B., Kami?ski J., Be?dowicz M., Kwa?ny M.: "Synthesis of 5-aminolevulinic acid (5-ALA)", ICRI Annual Report '99, 2000, 119-122.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00111</protein_accession>
      <name>Delta-aminolevulinic acid dehydratase</name>
      <uniprot_id>Q2KIL3</uniprot_id>
      <gene_name>ALAD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00112</protein_accession>
      <name>Delta-aminolevulinic acid dehydratase</name>
      <uniprot_id>Q58DK5</uniprot_id>
      <gene_name>ALAD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00624</protein_accession>
      <name>5-aminolevulinate synthase, nonspecific, mitochondrial</name>
      <uniprot_id>A6QLI6</uniprot_id>
      <gene_name>ALAS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00629</protein_accession>
      <name>5-aminolevulinate synthase, erythroid-specific, mitochondrial</name>
      <uniprot_id>Q3ZC31</uniprot_id>
      <gene_name>ALAS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00681</protein_accession>
      <name>Cytoplasmic aconitate hydratase</name>
      <uniprot_id>Q0VCU1</uniprot_id>
      <gene_name>ACO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:43 UTC</creation_date>
  <update_date>2020-03-13 16:26:10 UTC</update_date>
  <accession>BMDB0001151</accession>
  <secondary_accessions>
    <accession>BMDB01151</accession>
  </secondary_accessions>
  <name>Allose</name>
  <description/>
  <synonyms>
    <synonym>beta-D-Allopyranose</synonym>
    <synonym>beta-D-Allose</synonym>
    <synonym>beta-delta-Allopyranose</synonym>
    <synonym>beta-delta-Allose</synonym>
    <synonym>D-Allose</synonym>
    <synonym>delta-Allose</synonym>
    <synonym>DL-Allose</synonym>
  </synonyms>
  <chemical_formula>C6H12O6</chemical_formula>
  <average_molecular_weight>180.1559</average_molecular_weight>
  <monisotopic_moleculate_weight>180.063388116</monisotopic_moleculate_weight>
  <iupac_name>(3S,4S,5R,6S)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>(D)-allose</traditional_iupac>
  <cas_registry_number>6038-51-3</cas_registry_number>
  <smiles>[H][C@@]1(CO)OC(O)[C@@]([H])(O)[C@@]([H])(O)[C@@]1([H])O</smiles>
  <inchi>InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5-,6?/m0/s1</inchi>
  <inchikey>WQZGKKKJIJFFOK-HOWGCPQDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-allose</external_descriptor>
      <external_descriptor>allopyranose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>128.0 - 128.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3S,4S,5R,6S)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>180.1559</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>180.063388116</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CO)OC(O)[C@@]([H])(O)[C@@]([H])(O)[C@@]1([H])O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5-,6?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WQZGKKKJIJFFOK-HOWGCPQDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>110.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362775</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>763.813 +/- 751.731</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01487</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022453</foodb_id>
  <chemspider_id>13076841</chemspider_id>
  <pubchem_compound_id>12285879</pubchem_compound_id>
  <chebi_id>37741</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Allose</wikipedia_id>
  <metlin_id>348</metlin_id>
  <synthesis_reference>Menavuvu Buetusiwa Thomas; Poonperm Wayoon; Leang Khim; Noguchi Naoki; Okada Hiromi; Morimoto Kenji; Granstrom Tom Birger; Takada Goro; Izumori Ken  Efficient biosynthesis of D-allose from D-psicose by cross-linked recombinant L-rhamnose isomerase: separation of product by ethanol crystallization.    Journal of bioscience and bioengineering  (2006),  101(4),  340-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:44 UTC</creation_date>
  <update_date>2020-03-13 16:26:10 UTC</update_date>
  <accession>BMDB0001155</accession>
  <secondary_accessions>
    <accession>BMDB01155</accession>
  </secondary_accessions>
  <name>Diadenosine triphosphate</name>
  <description/>
  <synonyms>
    <synonym>Diadenosine triphosphoric acid</synonym>
    <synonym>Adenosine (5')triphospho(5')adenosine</synonym>
    <synonym>Adenosine 5'-triphosphate 5'-adenosine</synonym>
    <synonym>Adenosine(3)triphosphate adenosine</synonym>
    <synonym>Adenosine(5')triphospho(5')adenosine</synonym>
    <synonym>Bis(adenosine)-5'-triphosphate</synonym>
    <synonym>p(1),p(3)-Bis(5'-adenosyl) trihydrogen triphosphate</synonym>
    <synonym>p(1),p(3)-Bis(5'-adenosyl) triphosphate</synonym>
    <synonym>p(1)-p(3)-Bis(5'-adenosyl) triphosphate</synonym>
    <synonym>P1,P3-Bis(5'-adenosyl) triphosphate</synonym>
    <synonym>Ap3a</synonym>
    <synonym>5'Ap3a</synonym>
    <synonym>p(1),(P3)-Bis(5'-adenosyl)triphosphate</synonym>
    <synonym>ApppA</synonym>
  </synonyms>
  <chemical_formula>C20H27N10O16P3</chemical_formula>
  <average_molecular_weight>756.4071</average_molecular_weight>
  <monisotopic_moleculate_weight>756.081934402</monisotopic_moleculate_weight>
  <iupac_name>{[(2S,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid</iupac_name>
  <traditional_iupac>[(2S,3R,4S,5S)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphinic acid</traditional_iupac>
  <cas_registry_number>56432-02-1</cas_registry_number>
  <smiles>NC1=C2N=CN([C@H]3O[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@H](O)[C@@H]3O)C2=NC=N1</smiles>
  <inchi>InChI=1S/C20H27N10O16P3/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(43-19)1-41-47(35,36)45-49(39,40)46-48(37,38)42-2-8-12(32)14(34)20(44-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H2,21,23,25)(H2,22,24,26)/t7-,8+,11-,12+,13-,14+,19-,20+</inchi>
  <inchikey>QCICUPZZLIQAPA-WGIMJHEJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Very long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Very long-chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
      <external_descriptor>very long-chain fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-9.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2S,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>756.4071</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>756.081934402</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=C2N=CN([C@H]3O[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@H](O)[C@@H]3O)C2=NC=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H27N10O16P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H27N10O16P3/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(43-19)1-41-47(35,36)45-49(39,40)46-48(37,38)42-2-8-12(32)14(34)20(44-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H2,21,23,25)(H2,22,24,26)/t7-,8+,11-,12+,13-,14+,19-,20+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QCICUPZZLIQAPA-WGIMJHEJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>387.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>155.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>62.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>71828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30454</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022454</foodb_id>
  <chemspider_id/>
  <drugbank_id/>
  <chebi_id>27775</chebi_id>
  <pubchem_compound_id>14464643</pubchem_compound_id>
  <kegg_id>C06197</kegg_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:46 UTC</creation_date>
  <update_date>2020-03-13 16:26:11 UTC</update_date>
  <accession>BMDB0001157</accession>
  <secondary_accessions>
    <accession>BMDB01157</accession>
  </secondary_accessions>
  <name>2-Methylacetoacetyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>2-Methyl-3-acetoacetyl-CoA</synonym>
    <synonym>2-Methyl-3-acetoacetyl-coenzyme A</synonym>
    <synonym>2-Methylacetoacetyl-coenzyme A</synonym>
    <synonym>alpha-Methylacetoacetyl-CoA</synonym>
    <synonym>alpha-Methylacetoacetyl-coenzyme A</synonym>
    <synonym>S-(2-Methyl-3-oxobutanoate</synonym>
    <synonym>S-(2-Methyl-3-oxobutanoate) CoA</synonym>
    <synonym>S-(2-Methyl-3-oxobutanoate) coenzyme A</synonym>
    <synonym>S-(2-Methyl-3-oxobutanoic acid</synonym>
  </synonyms>
  <chemical_formula>C26H42N7O18P3S</chemical_formula>
  <average_molecular_weight>865.634</average_molecular_weight>
  <monisotopic_moleculate_weight>865.151987801</monisotopic_moleculate_weight>
  <iupac_name>{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methyl-3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>2-methylacetoacetyl-coa</traditional_iupac>
  <cas_registry_number>6712-01-2</cas_registry_number>
  <smiles>CC(C(C)=O)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12</smiles>
  <inchi>InChI=1S/C26H42N7O18P3S/c1-13(14(2)34)25(39)55-8-7-28-16(35)5-6-29-23(38)20(37)26(3,4)10-48-54(45,46)51-53(43,44)47-9-15-19(50-52(40,41)42)18(36)24(49-15)33-12-32-17-21(27)30-11-31-22(17)33/h11-13,15,18-20,24,36-37H,5-10H2,1-4H3,(H,28,35)(H,29,38)(H,43,44)(H,45,46)(H2,27,30,31)(H2,40,41,42)</inchi>
  <inchikey>NHNODHRSCRALBF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>3-oxo-acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-dicarbonyl compounds</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methyl-3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>865.634</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>865.151987801</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C(C)=O)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H42N7O18P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H42N7O18P3S/c1-13(14(2)34)25(39)55-8-7-28-16(35)5-6-29-23(38)20(37)26(3,4)10-48-54(45,46)51-53(43,44)47-9-15-19(50-52(40,41)42)18(36)24(49-15)33-12-32-17-21(27)30-11-31-22(17)33/h11-13,15,18-20,24,36-37H,5-10H2,1-4H3,(H,28,35)(H,29,38)(H,43,44)(H,45,46)(H2,27,30,31)(H2,40,41,42)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NHNODHRSCRALBF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>380.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>186.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>76.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451853</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022455</foodb_id>
  <chemspider_id>52</chemspider_id>
  <drugbank_id/>
  <chebi_id>15476</chebi_id>
  <pubchem_compound_id>53</pubchem_compound_id>
  <kegg_id>C03344</kegg_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id>41671</bigg_id>
  <wikipedia_id>2-Methylacetoacetyl-CoA</wikipedia_id>
  <metlin_id>6040</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00961</protein_accession>
      <name>3-hydroxyacyl-CoA dehydrogenase type-2</name>
      <uniprot_id>O02691</uniprot_id>
      <gene_name>HSD17B10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:47 UTC</creation_date>
  <update_date>2020-04-16 17:52:23 UTC</update_date>
  <accession>BMDB0001160</accession>
  <secondary_accessions>
    <accession>BMDB01160</accession>
  </secondary_accessions>
  <name>Tricosanoic acid</name>
  <description>Tricosanoic acid, also known as N-tricosanoate or 22FA, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Tricosanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Tricosanoic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>N-Tricosanoic acid</synonym>
    <synonym>N-Tricosanoate</synonym>
    <synonym>Tricosanoate</synonym>
    <synonym>22FA</synonym>
    <synonym>F23</synonym>
    <synonym>Tricosanoic acid, aluminum salt</synonym>
    <synonym>Tricosanoic acid, calcium salt</synonym>
    <synonym>Tricosanoic acid, lead salt</synonym>
    <synonym>Tricosylate</synonym>
    <synonym>Tricosanoic acid</synonym>
  </synonyms>
  <chemical_formula>C23H46O2</chemical_formula>
  <average_molecular_weight>354.6101</average_molecular_weight>
  <monisotopic_moleculate_weight>354.349780716</monisotopic_moleculate_weight>
  <iupac_name>tricosanoic acid</iupac_name>
  <traditional_iupac>tricosanoic acid</traditional_iupac>
  <cas_registry_number>2433-96-7</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCCCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C23H46O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23(24)25/h2-22H2,1H3,(H,24,25)</inchi>
  <inchikey>XEZVDURJDFGERA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Very long-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Very long-chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Straight chain fatty acids</external_descriptor>
      <external_descriptor>straight-chain saturated fatty acid</external_descriptor>
      <external_descriptor>very long-chain fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>77.0 - 79.0 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>9.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>9.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>tricosanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>354.6101</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>354.349780716</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCCCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C23H46O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C23H46O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23(24)25/h2-22H2,1H3,(H,24,25)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XEZVDURJDFGERA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>49.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285988</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>286451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373944</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440433</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk. Meta-Analysis</comment>
      <references>
        <reference>
          <reference_text>Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.</reference_text>
          <pubmed_id>19038946</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
          <pubmed_id>14168161</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples have been collected from Heifer cows.</comment>
      <references>
        <reference>
          <reference_text>Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub  2013 Jun 5.</reference_text>
          <pubmed_id>23871026</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB002894</foodb_id>
  <chemspider_id>16170</chemspider_id>
  <drugbank_id>DB03500</drugbank_id>
  <chebi_id>42394</chebi_id>
  <pubchem_compound_id>17085</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-7834</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Tricosylic acid</wikipedia_id>
  <metlin_id>4211</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54.</reference_text>
      <pubmed_id>14168161</pubmed_id>
    </reference>
    <reference>
      <reference_text>Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.</reference_text>
      <pubmed_id>19038946</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:48 UTC</creation_date>
  <update_date>2020-04-14 22:48:55 UTC</update_date>
  <accession>BMDB0001161</accession>
  <secondary_accessions>
    <accession>BMDB01161</accession>
  </secondary_accessions>
  <name>4-Trimethylammoniobutanoic acid</name>
  <description/>
  <synonyms>
    <synonym>4-Trimethylammoniobutanoate</synonym>
    <synonym>Butyrobetaine</synonym>
    <synonym>gamma-Butyrobetaine</synonym>
    <synonym>Butyro-betaine</synonym>
    <synonym>g-Butyrobetaine</synonym>
    <synonym>Γ-butyrobetaine</synonym>
    <synonym>Deoxy-carnitine</synonym>
    <synonym>Deoxycarnitine</synonym>
    <synonym>4-N-Trimethylammonium butyrate</synonym>
    <synonym>4-Trimethylaminobutyrate</synonym>
    <synonym>4-(N-trimethylamino)Butyrate</synonym>
    <synonym>4-Butyrobetaine</synonym>
    <synonym>Actinine</synonym>
  </synonyms>
  <chemical_formula>C7H16NO2</chemical_formula>
  <average_molecular_weight>146.2074</average_molecular_weight>
  <monisotopic_moleculate_weight>146.118103761</monisotopic_moleculate_weight>
  <iupac_name>(3-carboxypropyl)trimethylazanium</iupac_name>
  <traditional_iupac>4-trimethylaminobutyrate</traditional_iupac>
  <cas_registry_number/>
  <smiles>C[N+](C)(C)CCCC(O)=O</smiles>
  <inchi>InChI=1S/C7H15NO2/c1-8(2,3)6-4-5-7(9)10/h4-6H2,1-3H3/p+1</inchi>
  <inchikey>JHPNVNIEXXLNTR-UHFFFAOYSA-O</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Straight chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>quaternary ammonium ion</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3-carboxypropyl)trimethylazanium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>146.2074</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>146.118103761</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H16NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H15NO2/c1-8(2,3)6-4-5-7(9)10/h4-6H2,1-3H3/p+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JHPNVNIEXXLNTR-UHFFFAOYSA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290547</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01181</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022456</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>134</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>1941</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Kawamura, Masao; Akutsu, Seiichi; Fukuda, Hirosuke; Hata, Hiroyuki; Morishita, Tsuyoshi; Kano, Kenji; Nishimori, Hirokuni.  Manufacture of g-butyrobetaine by fermentation.    Jpn. Kokai Tokkyo Koho  (1987),     6 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00593</protein_accession>
      <name>4-trimethylaminobutyraldehyde dehydrogenase</name>
      <uniprot_id>Q2KJH9</uniprot_id>
      <gene_name>ALDH9A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:49 UTC</creation_date>
  <update_date>2020-03-13 16:26:12 UTC</update_date>
  <accession>BMDB0001162</accession>
  <secondary_accessions>
    <accession>BMDB01162</accession>
  </secondary_accessions>
  <name>Heme O</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C49H58FeN4O5</chemical_formula>
  <average_molecular_weight>838.854</average_molecular_weight>
  <monisotopic_moleculate_weight>838.375663119</monisotopic_moleculate_weight>
  <iupac_name>3-[(11Z,16Z)-20-(2-carboxyethyl)-15-ethenyl-10-[(4E,8E)-1-hydroxy-5,9,13-trimethyltetradeca-4,8,12-trien-1-yl]-5,9,14,19-tetramethyl-21,23,24,25-tetraaza-22-ferrahexacyclo[9.9.3.1³,⁶.1¹³,¹⁶.0⁸,²³.0¹⁸,²¹]pentacosa-1(20),2,4,6(25),7,9,11,13(24),14,16,18-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[(11Z,16Z)-20-(2-carboxyethyl)-15-ethenyl-10-[(4E,8E)-1-hydroxy-5,9,13-trimethyltetradeca-4,8,12-trien-1-yl]-5,9,14,19-tetramethyl-21,23,24,25-tetraaza-22-ferrahexacyclo[9.9.3.1³,⁶.1¹³,¹⁶.0⁸,²³.0¹⁸,²¹]pentacosa-1(20),2,4,6(25),7,9,11,13(24),14,16,18-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>137397-56-9</cas_registry_number>
  <smiles>CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C5/C=C6\N=C(\C=C\1/N\2[Fe]N45)C(C)=C6C=C)/C(CCC(O)=O)=C3C</smiles>
  <inchi>InChI=1S/C49H60N4O5.Fe/c1-10-35-31(6)40-26-45-49(46(54)19-13-18-30(5)17-12-16-29(4)15-11-14-28(2)3)34(9)41(53-45)24-38-32(7)36(20-22-47(55)56)43(51-38)27-44-37(21-23-48(57)58)33(8)39(52-44)25-42(35)50-40;/h10,14,16,18,24-27,46,54H,1,11-13,15,17,19-23H2,2-9H3,(H4,50,51,52,53,55,56,57,58);/q;+2/p-2/b29-16+,30-18+,38-24-,39-25-,40-26-,41-24-,42-25-,43-27-,44-27-,45-26-;</inchi>
  <inchikey>FISPASSVCDRERW-KVGORYHISA-L</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Metallotetrapyrroles</sub_class>
    <direct_parent>Metallotetrapyrroles</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>11.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(11Z,16Z)-20-(2-carboxyethyl)-15-ethenyl-10-[(4E,8E)-1-hydroxy-5,9,13-trimethyltetradeca-4,8,12-trien-1-yl]-5,9,14,19-tetramethyl-21,23,24,25-tetraaza-22-ferrahexacyclo[9.9.3.1³,⁶.1¹³,¹⁶.0⁸,²³.0¹⁸,²¹]pentacosa-1(20),2,4,6(25),7,9,11,13(24),14,16,18-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>838.854</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>838.375663119</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C5/C=C6\N=C(\C=C\1/N\2[Fe]N45)C(C)=C6C=C)/C(CCC(O)=O)=C3C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C49H58FeN4O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C49H60N4O5.Fe/c1-10-35-31(6)40-26-45-49(46(54)19-13-18-30(5)17-12-16-29(4)15-11-14-28(2)3)34(9)41(53-45)24-38-32(7)36(20-22-47(55)56)43(51-38)27-44-37(21-23-48(57)58)33(8)39(52-44)25-42(35)50-40;/h10,14,16,18,24-27,46,54H,1,11-13,15,17,19-23H2,2-9H3,(H4,50,51,52,53,55,56,57,58);/q;+2/p-2/b29-16+,30-18+,38-24-,39-25-,40-26-,41-24-,42-25-,43-27-,44-27-,45-26-;</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FISPASSVCDRERW-KVGORYHISA-L</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>130.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>237.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>96.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30418</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022457</foodb_id>
  <chemspider_id>3571849</chemspider_id>
  <pubchem_compound_id/>
  <kegg_id>C15672</kegg_id>
  <chebi_id>24480</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Heme O</wikipedia_id>
  <metlin_id>6044</metlin_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:50 UTC</creation_date>
  <update_date>2020-03-13 16:26:13 UTC</update_date>
  <accession>BMDB0001163</accession>
  <secondary_accessions>
    <accession>BMDB01163</accession>
  </secondary_accessions>
  <name>Guanosine diphosphate mannose</name>
  <description>Guanosine diphosphate mannose, also known as guanosine diphosphate mannose or guanosine diphosphate mannose, belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. Guanosine diphosphate mannose is possibly soluble (in water) and a strong basic compound (based on its pKa). Guanosine diphosphate mannose exists in all living species, ranging from bacteria to humans. Guanosine diphosphate mannose participates in a number of enzymatic reactions, within cattle. In particular, Guanosine diphosphate mannose can be biosynthesized from D-mannose 1-phosphate; which is catalyzed by the enzyme mannose-1-phosphate guanyltransferase beta. In addition, Guanosine diphosphate mannose can be converted into GDP-4-dehydro-6-deoxy-D-mannose; which is mediated by the enzyme GDP-mannose 4,6 dehydratase. In cattle, guanosine diphosphate mannose is involved in the metabolic pathway called the fructose and mannose degradation pathway.</description>
  <synonyms>
    <synonym>GDP-D-Mannose</synonym>
    <synonym>GDPmannose</synonym>
    <synonym>Guanosine 5'-(trihydrogen diphosphate), mono-alpha-D-mannopyranosyl ester</synonym>
    <synonym>Guanosine diphosphomannose</synonym>
    <synonym>Guanosine pyrophosphate mannose</synonym>
    <synonym>GDP-alpha-D-Mannose</synonym>
    <synonym>Guanosine 5'-(trihydrogen diphosphate), mono-a-D-mannopyranosyl ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen diphosphate), mono-α-D-mannopyranosyl ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen diphosphoric acid), mono-a-D-mannopyranosyl ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen diphosphoric acid), mono-alpha-D-mannopyranosyl ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen diphosphoric acid), mono-α-D-mannopyranosyl ester</synonym>
    <synonym>Guanosine pyrophosphoric acid mannose</synonym>
    <synonym>GDP-a-D-Mannose</synonym>
    <synonym>GDP-Α-D-mannose</synonym>
    <synonym>Guanosine diphosphoric acid mannose</synonym>
    <synonym>GDP Mannose</synonym>
    <synonym>GDP-Glucose</synonym>
    <synonym>GDP-Mannose</synonym>
    <synonym>Pyrophosphate mannose, guanosine</synonym>
    <synonym>Diphosphomannose, guanosine</synonym>
    <synonym>Mannose, guanosine diphosphate</synonym>
    <synonym>Diphosphate mannose, guanosine</synonym>
    <synonym>Mannose, guanosine pyrophosphate</synonym>
    <synonym>Mannose, GDP</synonym>
    <synonym>Guanosine 5'-(trihydrogen diphosphate) p'-mannosyl ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen pyrophosphate) mono-D-mannosyl ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen pyrophosphate) monomannopyranosyl ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen pyrophosphate) monomannosyl ester</synonym>
    <synonym>Guanosine 5'-diphosphate D-mannose</synonym>
    <synonym>Guanosine 5'-pyrophosphate D-mannosyl ester</synonym>
    <synonym>Guanosine 5'-pyrophosphate alpha-D-mannosyl ester</synonym>
    <synonym>Guanosine 5'-pyrophosphate α-D-mannosyl ester</synonym>
    <synonym>Guanosine 5’-(trihydrogen diphosphate) p’-mannosyl ester</synonym>
    <synonym>Guanosine 5’-(trihydrogen pyrophosphate) mono-D-mannosyl ester</synonym>
    <synonym>Guanosine 5’-(trihydrogen pyrophosphate) monomannopyranosyl ester</synonym>
    <synonym>Guanosine 5’-(trihydrogen pyrophosphate) monomannosyl ester</synonym>
    <synonym>Guanosine 5’-diphosphate D-mannose</synonym>
    <synonym>Guanosine 5’-pyrophosphate D-mannosyl ester</synonym>
    <synonym>Guanosine 5’-pyrophosphate α-D-mannosyl ester</synonym>
    <synonym>Guanosine diphosphate mannose</synonym>
  </synonyms>
  <chemical_formula>C16H25N5O16P2</chemical_formula>
  <average_molecular_weight>605.3411</average_molecular_weight>
  <monisotopic_moleculate_weight>605.077152801</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>guanosine diphosphomannose</traditional_iupac>
  <cas_registry_number>3123-67-9</cas_registry_number>
  <smiles>NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C(=O)N1</smiles>
  <inchi>InChI=1S/C16H25N5O16P2/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28)/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1</inchi>
  <inchikey>MVMSCBBUIHUTGJ-GDJBGNAASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine nucleotide sugars</sub_class>
    <direct_parent>Purine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purines and purine derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>GDP-D-mannose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>605.3411</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>605.077152801</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H25N5O16P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H25N5O16P2/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28)/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MVMSCBBUIHUTGJ-GDJBGNAASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>327.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>118.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>48.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37952</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB030881</foodb_id>
  <kegg_id>C00096</kegg_id>
  <chemspider_id>17372</chemspider_id>
  <pubchem_compound_id>18396</pubchem_compound_id>
  <chebi_id>15820</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>GDP-MANNOSE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007246</knapsack_id>
  <bigg_id>1460457</bigg_id>
  <wikipedia_id>Guanosine diphosphate mannose</wikipedia_id>
  <metlin_id>6045</metlin_id>
  <synthesis_reference>Huang, Gang-Liang; Liu, Xiang; Zhang, Hou-Cheng; Wang, Peng-George.  A facile two-step chemo-enzymatic synthesis of GDP-mannose.    Letters in Organic Chemistry  (2006),  3(9),  668-669.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00806</protein_accession>
      <name>Dolichol-phosphate mannosyltransferase</name>
      <uniprot_id>Q1JQ93</uniprot_id>
      <gene_name>DPM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01119</protein_accession>
      <name>Mannose-1-phosphate guanyltransferase beta</name>
      <uniprot_id>Q2YDJ9</uniprot_id>
      <gene_name>GMPPB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:51 UTC</creation_date>
  <update_date>2020-03-13 16:26:13 UTC</update_date>
  <accession>BMDB0001164</accession>
  <secondary_accessions>
    <accession>BMDB01164</accession>
  </secondary_accessions>
  <name>trans-1,2-Dihydrobenzene-1,2-diol</name>
  <description/>
  <synonyms>
    <synonym>Arene diol</synonym>
    <synonym>cis-3,5-Cyclohexadiene-1,2-diol solution</synonym>
    <synonym>Racemic mixture OF (+)- and (-)-1,2-dihydroxy-1,2-dihydrobenzene</synonym>
    <synonym>Rel-(1R,2R)-cyclohexa-3,5-diene-1,2-diol</synonym>
    <synonym>trans-(+-)-3,5-Cyclohexadiene-1,2-diol</synonym>
    <synonym>trans-3,5-Cyclohexadiene-1,2-diol</synonym>
    <synonym>trans-1,2-Dihydrobenzene-1,2-diol</synonym>
  </synonyms>
  <chemical_formula>C6H8O2</chemical_formula>
  <average_molecular_weight>112.1265</average_molecular_weight>
  <monisotopic_moleculate_weight>112.0524295</monisotopic_moleculate_weight>
  <iupac_name>(1R,2R)-cyclohexa-3,5-diene-1,2-diol</iupac_name>
  <traditional_iupac>arene diol</traditional_iupac>
  <cas_registry_number>103302-38-1</cas_registry_number>
  <smiles>O[C@@H]1C=CC=C[C@H]1O</smiles>
  <inchi>InChI=1S/C6H8O2/c7-5-3-1-2-4-6(5)8/h1-8H/t5-,6-/m1/s1</inchi>
  <inchikey>YDRSQRPHLBEPTP-PHDIDXHHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>1,2-diols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>trans-cyclohexa-3,5-diene-1,2-diol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1R,2R)-cyclohexa-3,5-diene-1,2-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>112.1265</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>112.0524295</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]1C=CC=C[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H8O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H8O2/c7-5-3-1-2-4-6(5)8/h1-8H/t5-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YDRSQRPHLBEPTP-PHDIDXHHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347700</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022458</foodb_id>
  <kegg_id>C04221</kegg_id>
  <chemspider_id>131491</chemspider_id>
  <pubchem_compound_id>149186</pubchem_compound_id>
  <chebi_id>10702</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6046</metlin_id>
  <synthesis_reference>Sato, Tokuro; Fukuyama, Tomitaro; Suzuki, Taeko; Yoshikawa, Haruhisa.  1,2-Dihydro-1,2-dihydroxybenzene and several other substances in the metabolism of benzene.    Journal of Biochemistry (Tokyo, Japan)  (1963),  53  23-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00383</protein_accession>
      <name>Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase</name>
      <uniprot_id>Q148L6</uniprot_id>
      <gene_name>DHDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:53 UTC</creation_date>
  <update_date>2020-04-15 22:29:56 UTC</update_date>
  <accession>BMDB0001165</accession>
  <secondary_accessions>
    <accession>BMDB01165</accession>
  </secondary_accessions>
  <name>Keratan</name>
  <description/>
  <synonyms>
    <synonym>Keratan 6'-sulfate</synonym>
    <synonym>Keratan 6'-sulphate</synonym>
    <synonym>Keratan sulfate</synonym>
    <synonym>Keratan sulphate</synonym>
    <synonym>Kerato 6'-sulfate</synonym>
    <synonym>Kerato 6'-sulphate</synonym>
    <synonym>Kerato sulfate</synonym>
    <synonym>Kerato sulphate</synonym>
    <synonym>N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulfooxy)methyl]oxan-3-yl]ethanimidate</synonym>
    <synonym>N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulphooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulphooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulphooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulphooxy)methyl]oxan-3-yl]ethanimidate</synonym>
    <synonym>N-[(2S,3R,4S,6S)-2-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-{[(2R,3S,4R,5R,6S)-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulphooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulphooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-6-[(sulphooxy)methyl]oxan-4-yl]oxy}-4-hydroxy-6-[(sulphooxy)methyl]oxan-3-yl]ethanimidic acid</synonym>
    <synonym>Keratosulfate</synonym>
    <synonym>Sulfate, keratan</synonym>
  </synonyms>
  <chemical_formula>C28H48N2O32S4</chemical_formula>
  <average_molecular_weight>1052.935</average_molecular_weight>
  <monisotopic_moleculate_weight>1052.10730021</monisotopic_moleculate_weight>
  <iupac_name>{[(2S,4S,5R,6S)-5-acetamido-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxyoxan-2-yl]methoxy}sulfonic acid</iupac_name>
  <traditional_iupac>[(2S,4S,5R,6S)-5-acetamido-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxyoxan-2-yl]methoxysulfonic acid</traditional_iupac>
  <cas_registry_number>69992-87-6</cas_registry_number>
  <smiles>CC(=O)N[C@@H]1[C@@H](O)C[C@@H](COS(O)(=O)=O)O[C@H]1O[C@H]1[C@@H](O)[C@@H](COS(O)(=O)=O)O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@H](O[C@@H]3[C@@H](O)[C@H](O)O[C@H](COS(O)(=O)=O)[C@@H]3O)O[C@@H]2COS(O)(=O)=O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C28H48N2O32S4/c1-8(31)29-15-11(33)3-10(4-52-63(40,41)42)56-26(15)62-24-18(35)13(6-54-65(46,47)48)58-28(21(24)38)60-22-14(7-55-66(49,50)51)59-27(16(19(22)36)30-9(2)32)61-23-17(34)12(5-53-64(43,44)45)57-25(39)20(23)37/h10-28,33-39H,3-7H2,1-2H3,(H,29,31)(H,30,32)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)/t10-,11-,12+,13+,14+,15+,16+,17-,18-,19+,20+,21+,22+,23-,24-,25+,26-,27-,28-/m0/s1</inchi>
  <inchikey>KXCLCNHUUKTANI-RBIYJLQWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligosaccharide sulfates. These are carbohydrates containing between 3 and 9 sugar units, one of which bear one or more sulfate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Oligosaccharide sulfates</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Oligosaccharide sulfate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2S,4S,5R,6S)-5-acetamido-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-[(sulfooxy)methyl]-6-{[(2R,3R,4S,5S,6R)-2,3,5-trihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-[(sulfooxy)methyl]oxan-4-yl]oxy}-4-hydroxyoxan-2-yl]methoxy}sulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1052.935</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1052.10730021</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H]1[C@@H](O)C[C@@H](COS(O)(=O)=O)O[C@H]1O[C@H]1[C@@H](O)[C@@H](COS(O)(=O)=O)O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@H](O[C@@H]3[C@@H](O)[C@H](O)O[C@H](COS(O)(=O)=O)[C@@H]3O)O[C@@H]2COS(O)(=O)=O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C28H48N2O32S4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C28H48N2O32S4/c1-8(31)29-15-11(33)3-10(4-52-63(40,41)42)56-26(15)62-24-18(35)13(6-54-65(46,47)48)58-28(21(24)38)60-22-14(7-55-66(49,50)51)59-27(16(19(22)36)30-9(2)32)61-23-17(34)12(5-53-64(43,44)45)57-25(39)20(23)37/h10-28,33-39H,3-7H2,1-2H3,(H,29,31)(H,30,32)(H,40,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)/t10-,11-,12+,13+,14+,15+,16+,17-,18-,19+,20+,21+,22+,23-,24-,25+,26-,27-,28-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KXCLCNHUUKTANI-RBIYJLQWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>518.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>194.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>92.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336495</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022459</foodb_id>
  <kegg_id>C00573</kegg_id>
  <chemspider_id>394000</chemspider_id>
  <pubchem_compound_id>446715</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP02245</protein_accession>
      <name>Fibromodulin</name>
      <uniprot_id>P13605</uniprot_id>
      <gene_name>FMOD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02246</protein_accession>
      <name>Keratocan</name>
      <uniprot_id>O62702</uniprot_id>
      <gene_name>KERA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02247</protein_accession>
      <name>Neuroendocrine secretory protein 55</name>
      <uniprot_id>O18979</uniprot_id>
      <gene_name>GNAS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:54 UTC</creation_date>
  <update_date>2020-03-13 16:26:15 UTC</update_date>
  <accession>BMDB0001166</accession>
  <secondary_accessions>
    <accession>BMDB01166</accession>
  </secondary_accessions>
  <name>3-Hydroxybutyryl-CoA</name>
  <description/>
  <synonyms>
    <synonym>(3S)-3-Hydroxybutanoyl-CoA</synonym>
    <synonym>(S)-3-Hydroxybutyroyl-CoA</synonym>
    <synonym>(S)-3-Hydroxybutyryl-CoA</synonym>
    <synonym>L(+)-3-Hydroxybutyroyl-CoA</synonym>
    <synonym>L(+)-beta-Hydroxybutyroyl-CoA</synonym>
    <synonym>L-3-Hydroxybutanoyl-CoA</synonym>
    <synonym>L(+)-b-Hydroxybutyroyl-CoA</synonym>
    <synonym>L(+)-Β-hydroxybutyroyl-CoA</synonym>
  </synonyms>
  <chemical_formula>C25H42N7O18P3S</chemical_formula>
  <average_molecular_weight>853.623</average_molecular_weight>
  <monisotopic_moleculate_weight>853.151987801</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxybutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>(S)-3-hydroxybutanoyl-coa</traditional_iupac>
  <cas_registry_number/>
  <smiles>C[C@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14+,18+,19+,20-,24+/m0/s1</inchi>
  <inchikey>QHHKKMYHDBRONY-VKBDFPRVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (s)-3-hydroxyacyl coas. These are organic compounds containing a (S)-3-hydroxyl acylated coenzyme A derivative.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>(S)-3-hydroxyacyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hydroxybutanoyl-CoA</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-({2-[(2-{[(3S)-3-hydroxybutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>853.623</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>853.151987801</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H42N7O18P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14+,18+,19+,20-,24+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QHHKKMYHDBRONY-VKBDFPRVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>383.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>183.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>77.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Butyrate Metabolism</name>
      <smpdb_id>SMP0087185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087265</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32866</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01144</kegg_id>
  <foodb_id>FDB030161</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>9543037</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15453</chebi_id>
  <drugbank_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:55 UTC</creation_date>
  <update_date>2020-04-16 17:50:48 UTC</update_date>
  <accession>BMDB0001167</accession>
  <secondary_accessions>
    <accession>BMDB01167</accession>
  </secondary_accessions>
  <name>Pyruvaldehyde</name>
  <description/>
  <synonyms>
    <synonym>1,2-Propanedione</synonym>
    <synonym>2-Ketopropionaldehyde</synonym>
    <synonym>2-Oxopropanal</synonym>
    <synonym>2-Oxopropionaldehyde</synonym>
    <synonym>Acetylformaldehyde</synonym>
    <synonym>Acetylformyl</synonym>
    <synonym>alpha-Ketopropionaldehyde</synonym>
    <synonym>CH3COCHO</synonym>
    <synonym>Pyruvic aldehyde</synonym>
    <synonym>a-Ketopropionaldehyde</synonym>
    <synonym>Α-ketopropionaldehyde</synonym>
    <synonym>1-Ketopropionaldehyde</synonym>
    <synonym>2-Keto propionaldehyde</synonym>
    <synonym>2-oxo-Propionaldehyde</synonym>
    <synonym>Ketopropionaldehyde</synonym>
    <synonym>Methylglyoxal</synonym>
    <synonym>Propanedione</synonym>
    <synonym>Propanolone</synonym>
    <synonym>Pyroracemic aldehyde</synonym>
    <synonym>Aldehyde, pyruvic</synonym>
    <synonym>Oxopropanal</synonym>
  </synonyms>
  <chemical_formula>C3H4O2</chemical_formula>
  <average_molecular_weight>72.0627</average_molecular_weight>
  <monisotopic_moleculate_weight>72.021129372</monisotopic_moleculate_weight>
  <iupac_name>2-oxopropanal</iupac_name>
  <traditional_iupac>methylglyoxal</traditional_iupac>
  <cas_registry_number>78-98-8</cas_registry_number>
  <smiles>CC(=O)C=O</smiles>
  <inchi>InChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3</inchi>
  <inchikey>AIJULSRZWUXGPQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha ketoaldehydes. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Alpha ketoaldehydes</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Short-chain aldehydes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-ketoaldehyde</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Short-chain aldehyde</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo aldehyde</external_descriptor>
      <external_descriptor>a ketoaldehyde</external_descriptor>
      <external_descriptor>propanals</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>&lt; 25 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>16.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-oxopropanal</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>72.0627</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>72.021129372</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)C=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H4O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H4O2/c1-3(5)2-4/h2H,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AIJULSRZWUXGPQ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>34.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>17.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>6.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvaldehyde Degradation</name>
      <smpdb_id>SMP0087210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22405</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00546</kegg_id>
  <chemspider_id>857</chemspider_id>
  <foodb_id>FDB031000</foodb_id>
  <drugbank_id>DB03587</drugbank_id>
  <pubchem_compound_id>880</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17158</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007562</knapsack_id>
  <meta_cyc_id/>
  <bigg_id>35307</bigg_id>
  <wikipedia_id>Methylglyoxal</wikipedia_id>
  <metlin_id>6049</metlin_id>
  <synthesis_reference>Zhang, Jing-An; Chen, Yu-Ping.  Synthesis of pyruvaldehyde.    Jingxi Huagong  (2000),  17(9),  507-510.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:56 UTC</creation_date>
  <update_date>2020-03-13 16:26:16 UTC</update_date>
  <accession>BMDB0001168</accession>
  <secondary_accessions>
    <accession>BMDB01168</accession>
  </secondary_accessions>
  <name>2,4-Decadienoyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>(e,Z)-17-Hydroxy-1-methyl-17-propyl-CoA</synonym>
    <synonym>(e,Z)-17-Hydroxy-1-methyl-17-propyl-coenzyme A</synonym>
    <synonym>2,4-Decadienoyl-coenzyme A</synonym>
    <synonym>2-trans,4-cis-Decadienoyl-CoA</synonym>
    <synonym>2-trans,4-cis-Decadienoyl-coenzyme A</synonym>
    <synonym>4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-[2-({2-[(2E,4E)-deca-2,4-dienoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidate</synonym>
    <synonym>4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-[2-({2-[(2E,4E)-deca-2,4-dienoylsulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidate</synonym>
    <synonym>4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-[2-({2-[(2E,4E)-deca-2,4-dienoylsulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidic acid</synonym>
    <synonym>2,4-Decadienoyl-CoA</synonym>
  </synonyms>
  <chemical_formula>C31H50N7O17P3S</chemical_formula>
  <average_molecular_weight>917.752</average_molecular_weight>
  <monisotopic_moleculate_weight>917.219673435</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-{[({[(3-{[2-({2-[(2E,4E)-deca-2,4-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-({[(3-{[2-({2-[(2E,4E)-deca-2,4-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>79315-17-6</cas_registry_number>
  <smiles>CCCCC\C=C\C=C\C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(=O)O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C31H50N7O17P3S/c1-4-5-6-7-8-9-10-11-22(40)59-15-14-33-21(39)12-13-34-29(43)26(42)31(2,3)17-52-58(49,50)55-57(47,48)51-16-20-25(54-56(44,45)46)24(41)30(53-20)38-19-37-23-27(32)35-18-36-28(23)38/h8-11,18-20,24-26,30,41-42H,4-7,12-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46)/b9-8+,11-10+/t20-,24-,25-,26?,30-/m1/s1</inchi>
  <inchikey>FASAKYLWSRDQOH-IKZSJNQUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Medium-chain 2-enoyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>2-enoyl CoAs</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Acyl CoAs</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-{[({[(3-{[2-({2-[(2E,4E)-deca-2,4-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>917.752</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>917.219673435</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC\C=C\C=C\C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(=O)O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C31H50N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C31H50N7O17P3S/c1-4-5-6-7-8-9-10-11-22(40)59-15-14-33-21(39)12-13-34-29(43)26(42)31(2,3)17-52-58(49,50)55-57(47,48)51-16-20-25(54-56(44,45)46)24(41)30(53-20)38-19-37-23-27(32)35-18-36-28(23)38/h8-11,18-20,24-26,30,41-42H,4-7,12-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46)/b9-8+,11-10+/t20-,24-,25-,26?,30-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FASAKYLWSRDQOH-IKZSJNQUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>211.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>86.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367740</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022461</foodb_id>
  <kegg_id/>
  <chemspider_id>17216075</chemspider_id>
  <pubchem_compound_id>22833562</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6050</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:57 UTC</creation_date>
  <update_date>2020-04-15 22:32:51 UTC</update_date>
  <accession>BMDB0001169</accession>
  <secondary_accessions>
    <accession>BMDB01169</accession>
  </secondary_accessions>
  <name>4-Aminophenol</name>
  <description>4-Aminophenol, also known as 4-aminobenzenol or 4-hydroxyaniline, belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety. 4-Aminophenol exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 4-Aminophenol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>4-Aminobenzenol</synonym>
    <synonym>4-Hydroxyaniline</synonym>
    <synonym>p-Aminophenol</synonym>
    <synonym>p-Hydroxyaniline</synonym>
    <synonym>1-Amino-4-hydroxybenzene</synonym>
    <synonym>4-Amino-1-hydroxybenzene</synonym>
    <synonym>Activol</synonym>
    <synonym>Aminophenol</synonym>
    <synonym>Energol</synonym>
    <synonym>Fouramine p</synonym>
    <synonym>p-Hydroxyphenylamine</synonym>
    <synonym>Paramidophenol</synonym>
    <synonym>Paranol</synonym>
    <synonym>4-Aminophenol hydrochloride</synonym>
    <synonym>p-Aminophenol phosphate</synonym>
    <synonym>4-Aminophenol monosodium salt</synonym>
    <synonym>4-Aminophenol, 3H-labeled</synonym>
    <synonym>4-Aminophenol, ion(1+)</synonym>
    <synonym>4-Aminophenol conjugate monoacid</synonym>
    <synonym>4-Aminophenol monopotassium salt</synonym>
    <synonym>4-Aminophenol, 18O-labeled</synonym>
    <synonym>Para-aminophenol</synonym>
    <synonym>4-Aminophenol sulfate</synonym>
    <synonym>4-Aminophenol sulfate (2:1)</synonym>
    <synonym>4-Aminophenol</synonym>
  </synonyms>
  <chemical_formula>C6H7NO</chemical_formula>
  <average_molecular_weight>109.1259</average_molecular_weight>
  <monisotopic_moleculate_weight>109.052763851</monisotopic_moleculate_weight>
  <iupac_name>4-aminophenol</iupac_name>
  <traditional_iupac>aminophenol</traditional_iupac>
  <cas_registry_number>123-30-8</cas_registry_number>
  <smiles>NC1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2</inchi>
  <inchikey>PLIKAWJENQZMHA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Aniline and substituted anilines</sub_class>
    <direct_parent>Aniline and substituted anilines</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>p-Aminophenols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminophenol</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>P-aminophenol</substituent>
      <substituent>Phenol</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a phenol</external_descriptor>
      <external_descriptor>aminophenol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>boiling_point</kind>
      <value>187.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>16.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.04</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-aminophenol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>109.1259</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>109.052763851</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=CC=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H7NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PLIKAWJENQZMHA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>46.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99665</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022462</foodb_id>
  <chemspider_id>392</chemspider_id>
  <pubchem_compound_id>403</pubchem_compound_id>
  <kegg_id>C02372</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>17602</chebi_id>
  <wikipedia_id>4-Aminophenol</wikipedia_id>
  <meta_cyc_id>CPD-259</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>6051</metlin_id>
  <synthesis_reference>Zhu, Jianliang; Yang, Ying; Xu, Jinlai; Gu, Zhiqiang; Zhang, Xiaowei; Zheng, Zhigang; Li, Jianlin; Hao, Xiangyang.  Method for preparation of p-aminophenol.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2005),     6 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:41:59 UTC</creation_date>
  <update_date>2020-04-16 20:40:48 UTC</update_date>
  <accession>BMDB0001170</accession>
  <secondary_accessions>
    <accession>BMDB01170</accession>
  </secondary_accessions>
  <name>Lathosterol</name>
  <description/>
  <synonyms>
    <synonym>gamma-Cholesterol</synonym>
    <synonym>5alpha-Cholest-7-en-3beta-ol</synonym>
    <synonym>g-Cholesterol</synonym>
    <synonym>Γ-cholesterol</synonym>
    <synonym>5a-Cholest-7-en-3b-ol</synonym>
    <synonym>5Α-cholest-7-en-3β-ol</synonym>
    <synonym>(3beta)-Cholest-7-en-3-ol</synonym>
    <synonym>(3beta,5alpha)-Cholest-7-en-3-ol</synonym>
    <synonym>(3beta,alpha)-Cholest-7-en-3-ol</synonym>
    <synonym>(7)-Cholestenol</synonym>
    <synonym>3b-Hydroxy-5-cholestene</synonym>
    <synonym>3beta-Hydroxy-5alpha-cholest-7-ene</synonym>
    <synonym>5-a-Cholest-7-en-3-beta-ol</synonym>
    <synonym>5-alpha-Cholest-7-en-3-beta-ol</synonym>
    <synonym>7-Cholesten-3-beta-ol</synonym>
    <synonym>7-Cholestenol</synonym>
    <synonym>7-Cholesterol</synonym>
    <synonym>Cholest-7-en-3-ol</synonym>
    <synonym>Cholest-7-en-3beta-ol</synonym>
    <synonym>Cholest-7-en-ol</synonym>
    <synonym>Cholesterol - synthetic</synonym>
    <synonym>Cholesterol extra pure</synonym>
    <synonym>Cholesterol GR</synonym>
    <synonym>Cholesterol pharma</synonym>
    <synonym>Cholesterol,NF grade</synonym>
    <synonym>delta(7)-Cholestenol</synonym>
    <synonym>DELTA7-Cholesten-3beta-ol</synonym>
    <synonym>DELTA7-Cholestenol</synonym>
    <synonym>gamma-Cholestenol</synonym>
    <synonym>Lathosterol</synonym>
  </synonyms>
  <chemical_formula>C27H46O</chemical_formula>
  <average_molecular_weight>386.6535</average_molecular_weight>
  <monisotopic_moleculate_weight>386.354866094</monisotopic_moleculate_weight>
  <iupac_name>(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol</iupac_name>
  <traditional_iupac>(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol</traditional_iupac>
  <cas_registry_number>80-99-9</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</smiles>
  <inchi>InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h10,18-21,23-25,28H,6-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>IZVFFXVYBHFIHY-SKCNUYALSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>3-hydroxy delta-7-steroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-7-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-7-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-7-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3beta-sterol</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>cholestanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>122.0 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>386.6535</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>386.354866094</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H46O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h10,18-21,23-25,28H,6-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IZVFFXVYBHFIHY-SKCNUYALSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>120.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>50.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>80142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>80143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>80144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>140925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>140926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>140927</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022463</foodb_id>
  <chemspider_id>59151</chemspider_id>
  <pubchem_compound_id>65728</pubchem_compound_id>
  <kegg_id>C01189</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>17168</chebi_id>
  <wikipedia_id>Lathosterol</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00023744</knapsack_id>
  <bigg_id>37036</bigg_id>
  <metlin_id>6052</metlin_id>
  <synthesis_reference>Fieser, Louis F.  Cholesterol and companions. III. Cholestanol, lathosterol, and ketone 104.    Journal of the American Chemical Society  (1953),  75  4395-403.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:00 UTC</creation_date>
  <update_date>2020-03-13 16:26:17 UTC</update_date>
  <accession>BMDB0001172</accession>
  <secondary_accessions>
    <accession>BMDB01172</accession>
  </secondary_accessions>
  <name>2-Methyl-3-oxopropanoic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Methyl-3-oxopropanoate</synonym>
    <synonym>3-oxo-2-Methylpropanoate</synonym>
    <synonym>Methylmalonate semialdehyde</synonym>
    <synonym>3-oxo-2-Methylpropanoic acid</synonym>
    <synonym>Methylmalonic acid semialdehyde</synonym>
    <synonym>CH3-Malonate-semialdehyde</synonym>
    <synonym>Methylmalonate-semialdehyde</synonym>
    <synonym>2-Methyl-3-oxo-propanoate</synonym>
    <synonym>2-Methyl-3-oxopropanoic acid</synonym>
  </synonyms>
  <chemical_formula>C4H6O3</chemical_formula>
  <average_molecular_weight>102.0886</average_molecular_weight>
  <monisotopic_moleculate_weight>102.031694058</monisotopic_moleculate_weight>
  <iupac_name>2-methyl-3-oxopropanoic acid</iupac_name>
  <traditional_iupac>methylmalonate semialdehyde</traditional_iupac>
  <cas_registry_number>6236-08-4</cas_registry_number>
  <smiles>CC(C=O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7)</inchi>
  <inchikey>VOKUMXABRRXHAR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>1,3-dicarbonyl compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Short-chain aldehydes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Short-chain aldehyde</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>Oxo fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.053</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-methyl-3-oxopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>102.0886</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>102.031694058</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H6O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VOKUMXABRRXHAR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>22.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29869</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022464</foodb_id>
  <chemspider_id>290</chemspider_id>
  <pubchem_compound_id>296</pubchem_compound_id>
  <kegg_id>C00349</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>16256</chebi_id>
  <wikipedia_id>2-Methyl-3-oxopropanoic acid</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>34698</bigg_id>
  <metlin_id>6053</metlin_id>
  <synthesis_reference>Robinson, Wm. G.; Coon, Minor J.  Purification and properties of b-hydroxyisobutyric dehydrogenase.   Journal of Biological Chemistry  (1957),  225  511-21.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00260</protein_accession>
      <name>Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial</name>
      <uniprot_id>Q07536</uniprot_id>
      <gene_name>ALDH6A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00596</protein_accession>
      <name>4-aminobutyrate aminotransferase, mitochondrial</name>
      <uniprot_id>Q9BGI0</uniprot_id>
      <gene_name>ABAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:01 UTC</creation_date>
  <update_date>2020-04-15 22:28:13 UTC</update_date>
  <accession>BMDB0001173</accession>
  <secondary_accessions>
    <accession>BMDB01173</accession>
  </secondary_accessions>
  <name>5'-Methylthioadenosine</name>
  <description>5'-Methylthioadenosine, also known as MTA or thiomethyladenosine, belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. 5'-Methylthioadenosine is possibly soluble (in water) and a strong basic compound (based on its pKa). 5'-Methylthioadenosine exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>5'-Deoxy-5'-(methylthio)adenosine</synonym>
    <synonym>5-Methylthioadenosine</synonym>
    <synonym>9-(5-S-Methyl-5-thio-beta-D-ribofuranosyl)-9H-purin-6-amine</synonym>
    <synonym>Methylthioadenosine</synonym>
    <synonym>MTA</synonym>
    <synonym>S-Methyl-5'-thioadenosine</synonym>
    <synonym>Thiomethyladenosine</synonym>
    <synonym>9-(5-S-Methyl-5-thio-b-D-ribofuranosyl)-9H-purin-6-amine</synonym>
    <synonym>9-(5-S-Methyl-5-thio-β-D-ribofuranosyl)-9H-purin-6-amine</synonym>
    <synonym>1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-D-ribofuranose</synonym>
    <synonym>1-(6-Amino-9H-purin-9-yl)-1-deoxy-5-S-methyl-5-thio-beta-delta-ribofuranose</synonym>
    <synonym>5'-(Methylthio)-5'-deoxyadenosine</synonym>
    <synonym>5'-(Methylthio)adenosine</synonym>
    <synonym>5'-S-Methyl-5'-thio-adenosine</synonym>
    <synonym>5'-S-Methyl-5'-thioadenosine</synonym>
    <synonym>S-Methyl-5-thioadenosine</synonym>
    <synonym>Adenine(5'-deoxy-5'-methylthio)9-beta-D-furanoriboside</synonym>
    <synonym>5-MTDA</synonym>
    <synonym>5'-Methylthio-5'-deoxyadenosine</synonym>
    <synonym>5'-Deoxy-5'-methylthioadenosine</synonym>
    <synonym>5'-Methylthioadenosine, methyl-(14)C-labeled</synonym>
    <synonym>5'-Methylthioadenosine</synonym>
  </synonyms>
  <chemical_formula>C11H15N5O3S</chemical_formula>
  <average_molecular_weight>297.334</average_molecular_weight>
  <monisotopic_moleculate_weight>297.089560061</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol</iupac_name>
  <traditional_iupac>methylthioadenosine</traditional_iupac>
  <cas_registry_number>2457-80-9</cas_registry_number>
  <smiles>CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1</inchi>
  <inchikey>WUUGFSXJNOTRMR-IOSLPCCCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides  in which the ribose is thio-substituted at the 5'position by a S-alkyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>5'-deoxyribonucleosides</class>
    <sub_class>5'-deoxy-5'-thionucleosides</sub_class>
    <direct_parent>5'-deoxy-5'-thionucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Dialkylthioethers</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>5'-deoxy-5'-thionucleoside</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thioether</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>thioadenosine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>297.334</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>297.089560061</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H15N5O3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WUUGFSXJNOTRMR-IOSLPCCCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>119.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>74.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447222</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB031156</foodb_id>
  <chemspider_id>388321</chemspider_id>
  <pubchem_compound_id>439176</pubchem_compound_id>
  <kegg_id>C00170</kegg_id>
  <drugbank_id>DB02282</drugbank_id>
  <pdbe_id/>
  <chebi_id>17509</chebi_id>
  <wikipedia_id/>
  <meta_cyc_id>5-METHYLTHIOADENOSINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>34127</bigg_id>
  <metlin_id>3425</metlin_id>
  <synthesis_reference>Sufrin, Janice R.; Spiess, Arthur J.; Kramer, Debora L.; Libby, Paul R.; Porter, Carl W. Synthesis and antiproliferative effects of novel 5'-fluorinated analogs of 5'-deoxy-5'-(methylthio)adenosine. Journal of Medicinal Chemistry (1989), 32(5), 997-1001.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00126</protein_accession>
      <name>Spermine synthase</name>
      <uniprot_id>Q3SZA5</uniprot_id>
      <gene_name>SMS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:02 UTC</creation_date>
  <update_date>2020-04-16 20:38:37 UTC</update_date>
  <accession>BMDB0001175</accession>
  <secondary_accessions>
    <accession>BMDB01175</accession>
  </secondary_accessions>
  <name>Malonyl-CoA</name>
  <description>Malonyl-CoA, also known as malonyl CoA or CoA, malonyl, belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. Malonyl-CoA is possibly soluble (in water) and a strong basic compound (based on its pKa). Malonyl-CoA participates in a number of enzymatic reactions, within cattle. In particular, Malonyl-CoA can be biosynthesized from acetyl-CoA through its interaction with the enzyme acetyl-CoA carboxylase 1. In addition, Malonyl-CoA can be converted into malonic acid and coenzyme A through the action of the enzyme fatty acid synthase. malonyl/acetyl transferase domain. In cattle, malonyl-CoA is involved in the metabolic pathway called fatty acid biosynthesis pathway. Malonyl-CoA is a potentially toxic compound.</description>
  <synonyms>
    <synonym>Malonyl CoA</synonym>
    <synonym>Malonyl coenzyme A</synonym>
    <synonym>Malonyl-coenzyme A</synonym>
    <synonym>Omega-carboxyacyl-CoA</synonym>
    <synonym>Omega-carboxyacyl-coenzyme A</synonym>
    <synonym>S-(Hydrogen malonyl)coenzyme A</synonym>
    <synonym>S-(Hydrogen propanedioate</synonym>
    <synonym>S-(Hydrogen propanedioate) CoA</synonym>
    <synonym>S-(Hydrogen propanedioate) coenzyme A</synonym>
    <synonym>S-(Hydrogen propanedioic acid</synonym>
    <synonym>a, Malonyl coenzyme</synonym>
    <synonym>CoA, Malonyl</synonym>
    <synonym>coenzyme A, Malonyl</synonym>
  </synonyms>
  <chemical_formula>C24H38N7O19P3S</chemical_formula>
  <average_molecular_weight>853.58</average_molecular_weight>
  <monisotopic_moleculate_weight>853.115602295</monisotopic_moleculate_weight>
  <iupac_name>3-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-3-oxopropanoic acid</iupac_name>
  <traditional_iupac>3-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-3-oxopropanoic acid</traditional_iupac>
  <cas_registry_number>524-14-1</cas_registry_number>
  <smiles>CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C24H38N7O19P3S/c1-24(2,19(37)22(38)27-4-3-13(32)26-5-6-54-15(35)7-14(33)34)9-47-53(44,45)50-52(42,43)46-8-12-18(49-51(39,40)41)17(36)23(48-12)31-11-30-16-20(25)28-10-29-21(16)31/h10-12,17-19,23,36-37H,3-9H2,1-2H3,(H,26,32)(H,27,38)(H,33,34)(H,42,43)(H,44,45)(H2,25,28,29)(H2,39,40,41)/t12-,17-,18-,19?,23-/m1/s1</inchi>
  <inchikey>LTYOQGRJFJAKNA-VFLPNFFSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>1,3-dicarbonyl compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Short-chain aldehydes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Short-chain aldehyde</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>Oxo fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-3-oxopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>853.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>853.115602295</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H38N7O19P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H38N7O19P3S/c1-24(2,19(37)22(38)27-4-3-13(32)26-5-6-54-15(35)7-14(33)34)9-47-53(44,45)50-52(42,43)46-8-12-18(49-51(39,40)41)17(36)23(48-12)31-11-30-16-20(25)28-10-29-21(16)31/h10-12,17-19,23,36-37H,3-9H2,1-2H3,(H,26,32)(H,27,38)(H,33,34)(H,42,43)(H,44,45)(H2,25,28,29)(H2,39,40,41)/t12-,17-,18-,19?,23-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LTYOQGRJFJAKNA-VFLPNFFSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>400.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>178.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>74.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>LPS and Citrate Signaling and Inflammation</name>
      <smpdb_id>SMP0120946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>156275</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB001606</foodb_id>
  <chemspider_id>10213</chemspider_id>
  <pubchem_compound_id>10663</pubchem_compound_id>
  <kegg_id>C00083</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>15531</chebi_id>
  <wikipedia_id>Malonyl-CoA</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007260</knapsack_id>
  <bigg_id>33789</bigg_id>
  <metlin_id>6056</metlin_id>
  <synthesis_reference>Hulsmann, W. C.  Synthesis of malonyl coenzyme A from acetyl coenzyme A and oxalosuccinate in mitochondria.    Biochimica et Biophysica Acta  (1963),  77(3),  502-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00204</protein_accession>
      <name>Acetyl-CoA carboxylase 1</name>
      <uniprot_id>Q9TTS3</uniprot_id>
      <gene_name>ACACA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00368</protein_accession>
      <name>Fatty acid synthase</name>
      <uniprot_id>Q71SP7</uniprot_id>
      <gene_name>FASN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:03 UTC</creation_date>
  <update_date>2020-04-14 22:48:56 UTC</update_date>
  <accession>BMDB0001176</accession>
  <secondary_accessions>
    <accession>BMDB01176</accession>
  </secondary_accessions>
  <name>Cytidine monophosphate N-acetylneuraminic acid</name>
  <description>Cytidine monophosphate N-acetylneuraminic acid, also known as CMP acetylneuraminic acid or CMP-nana, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Cytidine monophosphate N-acetylneuraminic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cytidine monophosphate N-acetylneuraminic acid exists in all living organisms, ranging from bacteria to humans. In cattle, cytidine monophosphate N-acetylneuraminic acid is involved in the metabolic pathway called the amino sugar metabolism pathway.</description>
  <synonyms>
    <synonym>CMP Acetylneuraminic acid</synonym>
    <synonym>CMP-beta-Neu5ac</synonym>
    <synonym>CMP-N-Acetylneuraminate</synonym>
    <synonym>CMP-Nana</synonym>
    <synonym>CMP-Neu5ac</synonym>
    <synonym>CMP-NeuNAc</synonym>
    <synonym>CMP-Sialic acid</synonym>
    <synonym>Cytidine monophosphate N-acetylneuraminic acid</synonym>
    <synonym>CYTIDINE-5'-monophosphATE-5-N-acetylneuraminIC ACID</synonym>
    <synonym>Cytidine-5'-monophospho-N-acetylneuraminic acid</synonym>
    <synonym>Cytidine-5'-monophosphono-N-acetylneuraminic acid</synonym>
    <synonym>CMP-N-Acetyl-beta-neuraminate</synonym>
    <synonym>CMP Acetylneuraminate</synonym>
    <synonym>CMP-b-Neu5ac</synonym>
    <synonym>CMP-Β-neu5ac</synonym>
    <synonym>CMP-N-Acetylneuraminic acid</synonym>
    <synonym>CMP-Sialate</synonym>
    <synonym>Cytidine monophosphate N-acetylneuraminate</synonym>
    <synonym>Cytidine monophosphoric acid N-acetylneuraminic acid</synonym>
    <synonym>CYTIDINE-5'-monophosphate-5-N-acetylneuraminate</synonym>
    <synonym>CYTIDINE-5'-monophosphoric acid-5-N-acetylneuraminic acid</synonym>
    <synonym>Cytidine-5'-monophospho-N-acetylneuraminate</synonym>
    <synonym>Cytidine-5'-monophosphono-N-acetylneuraminate</synonym>
    <synonym>CMP-N-Acetyl-b-neuraminate</synonym>
    <synonym>CMP-N-Acetyl-b-neuraminic acid</synonym>
    <synonym>CMP-N-Acetyl-beta-neuraminic acid</synonym>
    <synonym>CMP-N-Acetyl-β-neuraminate</synonym>
    <synonym>CMP-N-Acetyl-β-neuraminic acid</synonym>
    <synonym>Cytidine 5'-monophosphate-N-acetylneuraminate</synonym>
    <synonym>Cytidine 5'-monophosphoric acid-N-acetylneuraminic acid</synonym>
    <synonym>CMP-N-Acylneuraminate</synonym>
    <synonym>Cytidine 5'-monophosphate N-acetylneuraminic acid</synonym>
    <synonym>Acetylneuraminic acid, CMP</synonym>
    <synonym>Acid, CMP acetylneuraminic</synonym>
    <synonym>Acid, CMP-sialic</synonym>
    <synonym>CMP Sialic acid</synonym>
    <synonym>Cytidine monophosphate N acetylneuraminic acid</synonym>
    <synonym>CMP-NeuAc</synonym>
    <synonym>Cytidine 5'-monophosphic acid-N-acetylneuraminic acid</synonym>
    <synonym>Cytidine 5'-monophospho-N-acetylneuraminate</synonym>
    <synonym>Cytidine 5'-monophospho-N-acetylneuraminic acid</synonym>
    <synonym>Cytidine 5’-monophosphate-N-acetylneuraminate</synonym>
    <synonym>Cytidine 5’-monophosphate-N-acetylneuraminic acid</synonym>
    <synonym>Cytidine 5’-monophosphic acid-N-acetylneuraminic acid</synonym>
    <synonym>Cytidine 5’-monophospho-N-acetylneuraminate</synonym>
    <synonym>Cytidine 5’-monophospho-N-acetylneuraminic acid</synonym>
    <synonym>Cytidine monophosphic acid N-acetylneuraminic acid</synonym>
    <synonym>Cytidine 5'-monophosphate-N-acetylneuraminic acid</synonym>
  </synonyms>
  <chemical_formula>C20H31N4O16P</chemical_formula>
  <average_molecular_weight>614.4511</average_molecular_weight>
  <monisotopic_moleculate_weight>614.147267476</monisotopic_moleculate_weight>
  <iupac_name>(2R,4S,5R,6R)-2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>cmp-sialic acid</traditional_iupac>
  <cas_registry_number>3063-71-6</cas_registry_number>
  <smiles>[H][C@]1(O[C@](C[C@H](O)[C@H]1NC(C)=O)(OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)C(O)=O)[C@H](O)[C@H](O)CO</smiles>
  <inchi>InChI=1S/C20H31N4O16P/c1-7(26)22-12-8(27)4-20(18(32)33,39-16(12)13(29)9(28)5-25)40-41(35,36)37-6-10-14(30)15(31)17(38-10)24-3-2-11(21)23-19(24)34/h2-3,8-10,12-17,25,27-31H,4-6H2,1H3,(H,22,26)(H,32,33)(H,35,36)(H2,21,23,34)/t8-,9+,10+,12+,13+,14+,15+,16+,17+,20+/m0/s1</inchi>
  <inchikey>TXCIAUNLDRJGJZ-BILDWYJOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine nucleotide sugars</sub_class>
    <direct_parent>Pyrimidine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>C-glucuronides</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkyl phosphates</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acylneuraminic acids</alternative_parent>
      <alternative_parent>Neuraminic acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Pyrimidine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>C-glucuronide</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkyl phosphate</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acylneuraminic acid</substituent>
      <substituent>N-acylneuraminic acid or derivatives</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Neuraminic acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyran</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine nucleotide sugar</substituent>
      <substituent>Pyrimidine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>CMP-N-acyl-beta-neuraminic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,4S,5R,6R)-2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>614.4511</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>614.147267476</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(O[C@](C[C@H](O)[C@H]1NC(C)=O)(OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)C(O)=O)[C@H](O)[C@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H31N4O16P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H31N4O16P/c1-7(26)22-12-8(27)4-20(18(32)33,39-16(12)13(29)9(28)5-25)40-41(35,36)37-6-10-14(30)15(31)17(38-10)24-3-2-11(21)23-19(24)34/h2-3,8-10,12-17,25,27-31H,4-6H2,1H3,(H,22,26)(H,32,33)(H,35,36)(H2,21,23,34)/t8-,9+,10+,12+,13+,14+,15+,16+,17+,20+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>TXCIAUNLDRJGJZ-BILDWYJOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>320.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>125.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>53.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>253178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>273119</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022466</foodb_id>
  <chemspider_id>395082</chemspider_id>
  <pubchem_compound_id>448209</pubchem_compound_id>
  <kegg_id>C00128</kegg_id>
  <drugbank_id>DB02485</drugbank_id>
  <pdbe_id/>
  <chebi_id>16556</chebi_id>
  <wikipedia_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>33954</bigg_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00789</protein_accession>
      <name>N-acylneuraminate cytidylyltransferase</name>
      <uniprot_id>Q3SZM5</uniprot_id>
      <gene_name>CMAS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00790</protein_accession>
      <name>Beta-galactoside alpha-2,6-sialyltransferase 2</name>
      <uniprot_id>A5D7T4</uniprot_id>
      <gene_name>ST6GAL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00791</protein_accession>
      <name>Alpha-N-acetylneuraminide alpha-2,8-sialyltransferase</name>
      <uniprot_id>Q6ZXD2</uniprot_id>
      <gene_name>ST8SIA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00792</protein_accession>
      <name>Lactosylceramide alpha-2,3-sialyltransferase</name>
      <uniprot_id>Q70D51</uniprot_id>
      <gene_name>ST3GAL5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:04 UTC</creation_date>
  <update_date>2020-03-13 16:26:19 UTC</update_date>
  <accession>BMDB0001177</accession>
  <secondary_accessions>
    <accession>BMDB01177</accession>
  </secondary_accessions>
  <name>(S)-Succinyldihydrolipoamide</name>
  <description/>
  <synonyms>
    <synonym>S-Succinyl-dihydrolipoamide</synonym>
    <synonym>S-Succinyldihydrolipoamide</synonym>
  </synonyms>
  <chemical_formula>C12H21NO4S2</chemical_formula>
  <average_molecular_weight>307.429</average_molecular_weight>
  <monisotopic_moleculate_weight>307.091199545</monisotopic_moleculate_weight>
  <iupac_name>4-{[(3R)-7-carbamoyl-1-sulfanylheptan-3-yl]sulfanyl}-4-oxobutanoic acid</iupac_name>
  <traditional_iupac>4-{[(3R)-7-carbamoyl-1-sulfanylheptan-3-yl]sulfanyl}-4-oxobutanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>NC(=O)CCCC[C@H](CCS)SC(=O)CCC(O)=O</smiles>
  <inchi>InChI=1S/C12H21NO4S2/c13-10(14)4-2-1-3-9(7-8-18)19-12(17)6-5-11(15)16/h9,18H,1-8H2,(H2,13,14)(H,15,16)/t9-/m1/s1</inchi>
  <inchikey>RJCJWONCSKSHES-SECBINFHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Thia fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acyl thioesters</alternative_parent>
      <alternative_parent>Fatty amides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl thioester</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thia fatty acid</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-{[(3R)-7-carbamoyl-1-sulfanylheptan-3-yl]sulfanyl}-4-oxobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>307.429</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>307.091199545</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)CCCC[C@H](CCS)SC(=O)CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H21NO4S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H21NO4S2/c13-10(14)4-2-1-3-9(7-8-18)19-12(17)6-5-11(15)16/h9,18H,1-8H2,(H2,13,14)(H,15,16)/t9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RJCJWONCSKSHES-SECBINFHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>78.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30640</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022467</foodb_id>
  <chemspider_id>388536</chemspider_id>
  <pubchem_compound_id>439425</pubchem_compound_id>
  <kegg_id>C01169</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>17432</chebi_id>
  <wikipedia_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>6058</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:06 UTC</creation_date>
  <update_date>2020-04-15 22:29:58 UTC</update_date>
  <accession>BMDB0001178</accession>
  <secondary_accessions>
    <accession>BMDB01178</accession>
  </secondary_accessions>
  <name>Adenosine diphosphate ribose</name>
  <description/>
  <synonyms>
    <synonym>Adenosine diphosphoric acid ribose</synonym>
    <synonym>(Rib5)ppa</synonym>
    <synonym>5-(Adenosine 5'-pyrophosphoryl)-D-ribose</synonym>
    <synonym>a5'pp5RIb</synonym>
    <synonym>Adenosine 5'-diphosphoribose</synonym>
    <synonym>AdoPPRib</synonym>
    <synonym>ADP Ribose</synonym>
    <synonym>ADP-D-Ribose</synonym>
    <synonym>ADP-Rib</synonym>
    <synonym>ADP-Ribose</synonym>
    <synonym>ADPribose</synonym>
    <synonym>D-Ribofuranos-5-yl-ADP</synonym>
    <synonym>Ribose adenosine diphosphate</synonym>
    <synonym>[5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [hydroxy-[(3,4,5-trihydroxyoxolan-2-yl)methoxy]phosphoryl] hydrogen phosphate</synonym>
    <synonym>Diphosphate ribose, adenosine</synonym>
    <synonym>5'-Diphosphoribose, adenosine</synonym>
    <synonym>Adenosine diphosphoribose</synonym>
    <synonym>Diphosphoribose, adenosine</synonym>
    <synonym>Adenosine 5' diphosphoribose</synonym>
    <synonym>Ribose, ADP</synonym>
    <synonym>Ribose, adenosine diphosphate</synonym>
  </synonyms>
  <chemical_formula>C15H23N5O14P2</chemical_formula>
  <average_molecular_weight>559.3157</average_molecular_weight>
  <monisotopic_moleculate_weight>559.071673493</monisotopic_moleculate_weight>
  <iupac_name>{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(3,4,5-trihydroxyoxolan-2-yl)methoxy]phosphoryl}oxy)phosphinic acid</iupac_name>
  <traditional_iupac>adp ribose</traditional_iupac>
  <cas_registry_number>20762-30-5</cas_registry_number>
  <smiles>NC1=C2N=CN(C3OC(COP(O)(=O)OP(O)(=O)OCC4OC(O)C(O)C4O)C(O)C3O)C2=NC=N1</smiles>
  <inchi>InChI=1S/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(23)8(21)5(32-14)1-30-35(26,27)34-36(28,29)31-2-6-9(22)11(24)15(25)33-6/h3-6,8-11,14-15,21-25H,1-2H2,(H,26,27)(H,28,29)(H2,16,17,18)</inchi>
  <inchikey>SRNWOUGRCWSEMX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine nucleotide sugars</sub_class>
    <direct_parent>Purine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(3,4,5-trihydroxyoxolan-2-yl)methoxy]phosphoryl}oxy)phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>559.3157</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>559.071673493</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=C2N=CN(C3OC(COP(O)(=O)OP(O)(=O)OCC4OC(O)C(O)C4O)C(O)C3O)C2=NC=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H23N5O14P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(23)8(21)5(32-14)1-30-35(26,27)34-36(28,29)31-2-6-9(22)11(24)15(25)33-6/h3-6,8-11,14-15,21-25H,1-2H2,(H,26,27)(H,28,29)(H2,16,17,18)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SRNWOUGRCWSEMX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>291.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>111.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180791</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022468</foodb_id>
  <chemspider_id>187</chemspider_id>
  <pubchem_compound_id>192</pubchem_compound_id>
  <kegg_id>C00301</kegg_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>16960</chebi_id>
  <wikipedia_id>Adenosine diphosphate ribose</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>34547</bigg_id>
  <metlin_id>6059</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00132</protein_accession>
      <name>Poly(ADP-ribose) glycohydrolase ARH3</name>
      <uniprot_id>Q3SYV9</uniprot_id>
      <gene_name>ADPRHL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00133</protein_accession>
      <name>Manganese-dependent ADP-ribose/CDP-alcohol diphosphatase</name>
      <uniprot_id>A7YY53</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00134</protein_accession>
      <name>[Protein ADP-ribosylarginine] hydrolase</name>
      <uniprot_id>Q32KR8</uniprot_id>
      <gene_name>ADPRH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00135</protein_accession>
      <name>Poly(ADP-ribose) glycohydrolase</name>
      <uniprot_id>O02776</uniprot_id>
      <gene_name>PARG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00136</protein_accession>
      <name>tRNA 2'-phosphotransferase 1</name>
      <uniprot_id>Q3ZBM7</uniprot_id>
      <gene_name>TRPT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:07 UTC</creation_date>
  <update_date>2020-03-13 16:26:20 UTC</update_date>
  <accession>BMDB0001179</accession>
  <secondary_accessions>
    <accession>BMDB01179</accession>
  </secondary_accessions>
  <name>Nicotinic acid adenine dinucleotide</name>
  <description/>
  <synonyms>
    <synonym>Deamido-NAD</synonym>
    <synonym>Deamido-nad+</synonym>
    <synonym>Deamino-nad+</synonym>
    <synonym>Nicotinate adenine dinucleotide</synonym>
    <synonym>Deamidonicotinamide adenine dinucleoetide</synonym>
    <synonym>NAAD</synonym>
    <synonym>NaADN</synonym>
  </synonyms>
  <chemical_formula>C21H27N6O15P2</chemical_formula>
  <average_molecular_weight>665.4178</average_molecular_weight>
  <monisotopic_moleculate_weight>665.100962248</monisotopic_moleculate_weight>
  <iupac_name>1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carboxy-1λ⁵-pyridin-1-ylium</iupac_name>
  <traditional_iupac>deamido-NAD(+)</traditional_iupac>
  <cas_registry_number>6450-77-7</cas_registry_number>
  <smiles>NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)[N+]4=CC=CC(=C4)C(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1</smiles>
  <inchi>InChI=1S/C21H26N6O15P2/c22-17-12-18(24-7-23-17)27(8-25-12)20-16(31)14(29)11(41-20)6-39-44(36,37)42-43(34,35)38-5-10-13(28)15(30)19(40-10)26-3-1-2-9(4-26)21(32)33/h1-4,7-8,10-11,13-16,19-20,28-31H,5-6H2,(H4-,22,23,24,32,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,19-,20-/m1/s1</inchi>
  <inchikey>SENPVEZBRZQVST-HISDBWNOSA-O</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Nicotinic acid nucleotides</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Pyridinecarboxylic acids</alternative_parent>
      <alternative_parent>Pyridinium derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Nicotinic-acid-nucleotide</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyridine carboxylic acid</substituent>
      <substituent>Pyridine carboxylic acid or derivatives</substituent>
      <substituent>Pyridine nucleotide</substituent>
      <substituent>Pyridinium</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>nicotinic acid dinucleotide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-9.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carboxy-1λ⁵-pyridin-1-ylium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>665.4178</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>665.100962248</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)[N+]4=CC=CC(=C4)C(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H27N6O15P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H26N6O15P2/c22-17-12-18(24-7-23-17)27(8-25-12)20-16(31)14(29)11(41-20)6-39-44(36,37)42-43(34,35)38-5-10-13(28)15(30)19(40-10)26-3-1-2-9(4-26)21(32)33/h1-4,7-8,10-11,13-16,19-20,28-31H,5-6H2,(H4-,22,23,24,32,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,19-,20-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SENPVEZBRZQVST-HISDBWNOSA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>312.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>140.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>58.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33544</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB031057</foodb_id>
  <drugbank_id>DB04099</drugbank_id>
  <chemspider_id>145043</chemspider_id>
  <pdbe_id/>
  <kegg_id>C00857</kegg_id>
  <chebi_id>18304</chebi_id>
  <pubchem_compound_id>165491</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>36219</bigg_id>
  <wikipedia_id/>
  <metlin_id>4234</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:08 UTC</creation_date>
  <update_date>2020-03-13 16:26:21 UTC</update_date>
  <accession>BMDB0001180</accession>
  <secondary_accessions>
    <accession>BMDB01180</accession>
  </secondary_accessions>
  <name>N2-Succinyl-L-glutamic acid 5-semialdehyde</name>
  <description/>
  <synonyms>
    <synonym>(2S)-2-(3-Carboxypropanoylamino)-5-oxopentanoic acid</synonym>
    <synonym>N-(3-Carboxypropanoyl)-5-oxo-L-norvaline</synonym>
    <synonym>N-Succinyl-L-glutamate 5-semialdehyde</synonym>
    <synonym>(2S)-2-(3-Carboxypropanoylamino)-5-oxopentanoate</synonym>
    <synonym>N-Succinyl-L-glutamic acid 5-semialdehyde</synonym>
    <synonym>N2-Succinyl-L-glutamate 5-semialdehyde</synonym>
  </synonyms>
  <chemical_formula>C9H13NO6</chemical_formula>
  <average_molecular_weight>231.2026</average_molecular_weight>
  <monisotopic_moleculate_weight>231.074287153</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-(3-carboxypropanamido)-5-oxopentanoic acid</iupac_name>
  <traditional_iupac>(2S)-2-(3-carboxypropanamido)-5-oxopentanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>OC(=O)CCC(=O)N[C@@H](CCC=O)C(O)=O</smiles>
  <inchi>InChI=1S/C9H13NO6/c11-5-1-2-6(9(15)16)10-7(12)3-4-8(13)14/h5-6H,1-4H2,(H,10,12)(H,13,14)(H,15,16)/t6-/m0/s1</inchi>
  <inchikey>XTOKIEIBKARFSZ-LURJTMIESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydrogen aldehydes</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydrogen aldehyde</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dicarboxylic acid monoamide</external_descriptor>
      <external_descriptor>glutamic semialdehyde</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-(3-carboxypropanamido)-5-oxopentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>231.2026</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>231.074287153</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC(=O)N[C@@H](CCC=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13NO6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13NO6/c11-5-1-2-6(9(15)16)10-7(12)3-4-8(13)14/h5-6H,1-4H2,(H,10,12)(H,13,14)(H,15,16)/t6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XTOKIEIBKARFSZ-LURJTMIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>120.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37961</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33892</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022470</foodb_id>
  <drugbank_id/>
  <chemspider_id>389690</chemspider_id>
  <pdbe_id/>
  <kegg_id>C05932</kegg_id>
  <chebi_id>27657</chebi_id>
  <pubchem_compound_id>440848</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id>CPD-822</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6061</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:09 UTC</creation_date>
  <update_date>2020-03-13 16:26:21 UTC</update_date>
  <accession>BMDB0001181</accession>
  <secondary_accessions>
    <accession>BMDB01181</accession>
  </secondary_accessions>
  <name>4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol</name>
  <description/>
  <synonyms>
    <synonym>4alpha-Carboxy-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol</synonym>
    <synonym>4Α-carboxy-4β-methyl-5α-cholesta-8,24-dien-3β-ol</synonym>
    <synonym>4a-Methylzymosterol-4-carboxylate</synonym>
    <synonym>4a-Methylzymosterol-4-carboxylic acid</synonym>
    <synonym>4alpha-Methylzymosterol-4-carboxylic acid</synonym>
    <synonym>4Α-methylzymosterol-4-carboxylate</synonym>
    <synonym>4Α-methylzymosterol-4-carboxylic acid</synonym>
    <synonym>4a-Carboxy-4b-methyl-5a-cholesta-8,24-dien-3b-ol</synonym>
  </synonyms>
  <chemical_formula>C29H46O3</chemical_formula>
  <average_molecular_weight>442.6737</average_molecular_weight>
  <monisotopic_moleculate_weight>442.344695338</monisotopic_moleculate_weight>
  <iupac_name>(2S,5S,6S,7R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid</iupac_name>
  <traditional_iupac>(2S,5S,6S,7R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)([C@@H]1CC3)C(O)=O</smiles>
  <inchi>InChI=1S/C29H46O3/c1-18(2)8-7-9-19(3)21-11-12-22-20-10-13-24-28(5,23(20)14-16-27(21,22)4)17-15-25(30)29(24,6)26(31)32/h8,19,21-22,24-25,30H,7,9-17H2,1-6H3,(H,31,32)/t19-,21?,22?,24-,25+,27-,28-,29+/m1/s1</inchi>
  <inchikey>MYWAIWDQTCHPTH-YCIQJMEESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Triterpenoids</sub_class>
    <direct_parent>Triterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>4-carboxy steroids</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cholesterols and derivatives</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>15-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>4-carboxy steroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cholestane-skeleton</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Steroid</substituent>
      <substituent>Steroid acid</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,5S,6S,7R,15R)-5-hydroxy-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-6-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>442.6737</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>442.344695338</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)([C@@H]1CC3)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C29H46O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C29H46O3/c1-18(2)8-7-9-19(3)21-11-12-22-20-10-13-24-28(5,23(20)14-16-27(21,22)4)17-15-25(30)29(24,6)26(31)32/h8,19,21-22,24-25,30H,7,9-17H2,1-6H3,(H,31,32)/t19-,21?,22?,24-,25+,27-,28-,29+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MYWAIWDQTCHPTH-YCIQJMEESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>131.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>53.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372258</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022471</foodb_id>
  <drugbank_id/>
  <chemspider_id/>
  <pdbe_id/>
  <kegg_id>C15808</kegg_id>
  <chebi_id/>
  <pubchem_compound_id>23724596</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6062</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:10 UTC</creation_date>
  <update_date>2020-03-13 16:26:22 UTC</update_date>
  <accession>BMDB0001182</accession>
  <secondary_accessions>
    <accession>BMDB01182</accession>
  </secondary_accessions>
  <name>6,8-Dihydroxypurine</name>
  <description/>
  <synonyms>
    <synonym>6,8-Purinediol</synonym>
    <synonym>7,9-Dihydro-1H-purine-6,8-dione</synonym>
    <synonym>7,9-Dihydro-8H-purin-8-one</synonym>
    <synonym>8-Oxohypoxanthine</synonym>
    <synonym>Purine-6,8(1H,9H)-dione</synonym>
    <synonym>Purine-6,8-diol</synonym>
    <synonym>Purine-6,8-dione</synonym>
  </synonyms>
  <chemical_formula>C5H4N4O2</chemical_formula>
  <average_molecular_weight>152.1109</average_molecular_weight>
  <monisotopic_moleculate_weight>152.033425392</monisotopic_moleculate_weight>
  <iupac_name>6,7,8,9-tetrahydro-3H-purine-6,8-dione</iupac_name>
  <traditional_iupac>7,9-dihydro-3H-purine-6,8-dione</traditional_iupac>
  <cas_registry_number>13231-00-0</cas_registry_number>
  <smiles>O=C1NC2=C(N1)C(=O)N=CN2</smiles>
  <inchi>InChI=1S/C5H4N4O2/c10-4-2-3(6-1-7-4)9-5(11)8-2/h1H,(H3,6,7,8,9,10,11)</inchi>
  <inchikey>BYUOBSUZYQAFJM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Hypoxanthines</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>0.167 mg/mL at 20 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.246</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6,7,8,9-tetrahydro-3H-purine-6,8-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>152.1109</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>152.033425392</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O=C1NC2=C(N1)C(=O)N=CN2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H4N4O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H4N4O2/c10-4-2-3(6-1-7-4)9-5(11)8-2/h1H,(H3,6,7,8,9,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BYUOBSUZYQAFJM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>82.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>44.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16675</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB019885</foodb_id>
  <drugbank_id/>
  <chemspider_id>75117</chemspider_id>
  <pdbe_id/>
  <kegg_id/>
  <chebi_id/>
  <pubchem_compound_id>83252</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Ohtsuka, Yozo; Sugimoto, Kikuo.  Oxazolopyrimidines.  III.  Formation of 6,8-dihydroxypurine by the oxidation of 7-aminooxazolo[5,4-d]pyrimidine with hydrogen peroxide-acetic acid.    Bulletin of the Chemical Society of Japan  (1970),  43(7),  2281.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:11 UTC</creation_date>
  <update_date>2020-04-16 20:39:23 UTC</update_date>
  <accession>BMDB0001183</accession>
  <secondary_accessions>
    <accession>BMDB01183</accession>
  </secondary_accessions>
  <name>Octanol</name>
  <description/>
  <synonyms>
    <synonym>1-Hydroxyoctane</synonym>
    <synonym>1-Octanol</synonym>
    <synonym>1-Oktanol</synonym>
    <synonym>Capryl alcohol</synonym>
    <synonym>Caprylic alcohol</synonym>
    <synonym>N-Heptyl carbinol</synonym>
    <synonym>N-Octan-1-ol</synonym>
    <synonym>Primary octyl alcohol</synonym>
    <synonym>2-Capryl alcohol</synonym>
    <synonym>2-Octanol</synonym>
    <synonym>2-Octanol ~99%</synonym>
    <synonym>Alcohol C-8</synonym>
    <synonym>Alfol 8</synonym>
    <synonym>DL-2-Octanol</synonym>
    <synonym>Dytol m-83</synonym>
    <synonym>Emery 3322</synonym>
    <synonym>Emery 3324</synonym>
    <synonym>Epal 8</synonym>
    <synonym>Heptyl carbinol</synonym>
    <synonym>Hexyl methyl carbinol</synonym>
    <synonym>Lorol 20</synonym>
    <synonym>Lorol C8</synonym>
    <synonym>N-Octanol</synonym>
    <synonym>N-Octyl alcohol</synonym>
    <synonym>N-Octyl-alcohol</synonym>
    <synonym>Octan-1-ol</synonym>
    <synonym>Octan-2-ol</synonym>
    <synonym>Octan-2-ol 98+ %</synonym>
    <synonym>Octilin</synonym>
    <synonym>Octyl alcohol</synonym>
    <synonym>Octyl alcohol normal-primary</synonym>
    <synonym>Octyl-alcohol</synonym>
    <synonym>Prim-N-octyl alcohol</synonym>
    <synonym>Sipol L8</synonym>
    <synonym>1 Octanol</synonym>
    <synonym>N Octanol</synonym>
    <synonym>Alcohol, N-octyl</synonym>
    <synonym>N Octyl alcohol</synonym>
  </synonyms>
  <chemical_formula>C8H18O</chemical_formula>
  <average_molecular_weight>130.2279</average_molecular_weight>
  <monisotopic_moleculate_weight>130.135765198</monisotopic_moleculate_weight>
  <iupac_name>octan-1-ol</iupac_name>
  <traditional_iupac>octanol</traditional_iupac>
  <cas_registry_number>111-87-5</cas_registry_number>
  <smiles>CCCCCCCCO</smiles>
  <inchi>InChI=1S/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3</inchi>
  <inchikey>KBPLFHHGFOOTCA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty alcohols</sub_class>
    <direct_parent>Fatty alcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Fatty alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fatty alcohols</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>octanol</external_descriptor>
      <external_descriptor>primary alcohol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-15.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.54 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.0</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>16.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>octan-1-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>130.2279</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>130.135765198</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H18O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KBPLFHHGFOOTCA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180871</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180872</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB012583</foodb_id>
  <drugbank_id>DB12452</drugbank_id>
  <chemspider_id>932</chemspider_id>
  <pdbe_id/>
  <kegg_id>C00756</kegg_id>
  <chebi_id>16188</chebi_id>
  <pubchem_compound_id>957</pubchem_compound_id>
  <knapsack_id>C00001264</knapsack_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Octanol</wikipedia_id>
  <metlin_id>6063</metlin_id>
  <synthesis_reference>Hagiwara, Nobue; Takahashi, Shigetoshi; Shibano, Toshishige.  n-Octanol.    Jpn. Tokkyo Koho  (1977),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:12 UTC</creation_date>
  <update_date>2020-03-13 16:26:23 UTC</update_date>
  <accession>BMDB0001184</accession>
  <secondary_accessions>
    <accession>BMDB01184</accession>
  </secondary_accessions>
  <name>Methyl propenyl ketone</name>
  <description/>
  <synonyms>
    <synonym>(3E)-Penten-2-one</synonym>
    <synonym>(e)-3-Penten-2-one</synonym>
    <synonym>(e)-Pent-3-en-2-one</synonym>
    <synonym>2-oxo-(3E)-Pentene</synonym>
    <synonym>trans-3-Penten-2-one</synonym>
    <synonym>(3E)-3-Penten-2-one</synonym>
    <synonym>(3E)-Pent-3-en-2-one</synonym>
    <synonym>2-oxo-3-Pentene</synonym>
    <synonym>3-Penten-2-one</synonym>
    <synonym>3-Penten-2-one (methyl vinyl ketone)</synonym>
    <synonym>Ethylidene acetone</synonym>
    <synonym>FEMA no. 3417</synonym>
    <synonym>Methyl 1-propenyl ketone</synonym>
    <synonym>Pent-3-en-2-one</synonym>
  </synonyms>
  <chemical_formula>C5H8O</chemical_formula>
  <average_molecular_weight>84.1164</average_molecular_weight>
  <monisotopic_moleculate_weight>84.057514878</monisotopic_moleculate_weight>
  <iupac_name>(3E)-pent-3-en-2-one</iupac_name>
  <traditional_iupac>(E)-3-penten-2-one</traditional_iupac>
  <cas_registry_number>625-33-2</cas_registry_number>
  <smiles>C\C=C\C(C)=O</smiles>
  <inchi>InChI=1S/C5H8O/c1-3-4-5(2)6/h3-4H,1-2H3/b4-3+</inchi>
  <inchikey>LABTWGUMFABVFG-ONEGZZNKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Enones</direct_parent>
    <alternative_parents>
      <alternative_parent>Acryloyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acryloyl-group</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Enone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Oxygenated hydrocarbons</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>boiling_point</kind>
      <value>122.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.52</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3E)-pent-3-en-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>84.1164</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>84.057514878</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C\C=C\C(C)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O/c1-3-4-5(2)6/h3-4H,1-2H3/b4-3+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LABTWGUMFABVFG-ONEGZZNKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>26.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1988</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>296205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>337446</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB008241</foodb_id>
  <drugbank_id/>
  <chemspider_id>553493</chemspider_id>
  <pdbe_id/>
  <kegg_id/>
  <chebi_id>89540</chebi_id>
  <pubchem_compound_id>637920</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:14 UTC</creation_date>
  <update_date>2020-04-16 20:38:37 UTC</update_date>
  <accession>BMDB0001185</accession>
  <secondary_accessions>
    <accession>BMDB01185</accession>
  </secondary_accessions>
  <name>S-Adenosylmethionine</name>
  <description/>
  <synonyms>
    <synonym>(3S)-5'-[(3-Amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner salt</synonym>
    <synonym>[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfonium</synonym>
    <synonym>Acylcarnitine</synonym>
    <synonym>AdoMet</synonym>
    <synonym>S-(5'-Deoxyadenosin-5'-yl)-L-methionine</synonym>
    <synonym>SAM</synonym>
    <synonym>SAMe</synonym>
    <synonym>(3S)-5'-[(3-Amino-3-carboxypropyl)methylsulphonio]-5'-deoxyadenosine, inner salt</synonym>
    <synonym>[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfonium</synonym>
    <synonym>[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulphonium</synonym>
    <synonym>[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulphonium</synonym>
    <synonym>[1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfonium</synonym>
    <synonym>[1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulphonium</synonym>
    <synonym>(3S)-5'-[(3-Amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine</synonym>
    <synonym>2-S-Adenosyl-L-methionine</synonym>
    <synonym>5'-Deoxyadenosine-5'-L-methionine disulfate ditosylate</synonym>
    <synonym>5'-Deoxyadenosine-5'-L-methionine disulphate ditosylate</synonym>
    <synonym>Active methionine</synonym>
    <synonym>Ademetionine</synonym>
    <synonym>Adenosylmethionine</synonym>
    <synonym>Donamet</synonym>
    <synonym>L-S-Adenosylmethionine</synonym>
    <synonym>S-(5'-Adenosyl)-L-methionine</synonym>
    <synonym>S-Adenosyl methionine</synonym>
    <synonym>S-Adenosyl-L-methionine</synonym>
    <synonym>S-Adenosyl-L-methionine disulfate tosylate</synonym>
    <synonym>S-Adenosyl-L-methionine disulphate tosylate</synonym>
    <synonym>S-Adenosyl-methionine</synonym>
    <synonym>ASTA medica brand OF ademetionine tosilate disulfate</synonym>
    <synonym>S Adenosylmethionine sulfate tosylate</synonym>
    <synonym>S-Adenosylmethionine sulfate tosylate</synonym>
    <synonym>Sulfate tosylate, S-adenosylmethionine</synonym>
    <synonym>Ademetionine europharma brand</synonym>
    <synonym>Amet, S</synonym>
    <synonym>Europharma brand OF ademetionine</synonym>
    <synonym>Gumbaral</synonym>
    <synonym>Knoll brand OF brand OF ademetionine tosilate disulfate</synonym>
    <synonym>S Adenosylmethionine</synonym>
    <synonym>S Amet</synonym>
    <synonym>Samyr</synonym>
    <synonym>Tosylate, S-adenosylmethionine sulfate</synonym>
    <synonym>S Adenosyl L methionine</synonym>
    <synonym>SAM-e</synonym>
  </synonyms>
  <chemical_formula>C15H23N6O5S</chemical_formula>
  <average_molecular_weight>399.445</average_molecular_weight>
  <monisotopic_moleculate_weight>399.145063566</monisotopic_moleculate_weight>
  <iupac_name>[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium</iupac_name>
  <traditional_iupac>SAMe</traditional_iupac>
  <cas_registry_number>485-80-3</cas_registry_number>
  <smiles>C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1</inchi>
  <inchikey>MEFKEPWMEQBLKI-AIRLBKTGSA-O</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides  in which the ribose is thio-substituted at the 5'position by a S-alkyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>5'-deoxyribonucleosides</class>
    <sub_class>5'-deoxy-5'-thionucleosides</sub_class>
    <direct_parent>5'-deoxy-5'-thionucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Methionine and derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfur compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>5'-deoxy-5'-thionucleoside</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Methionine or derivatives</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thia fatty acid</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>organic cation</external_descriptor>
      <external_descriptor>sulfonium compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>399.445</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>399.145063566</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H23N6O5S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MEFKEPWMEQBLKI-AIRLBKTGSA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>182.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>96.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447191</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB031152</foodb_id>
  <drugbank_id/>
  <chemspider_id>21169292</chemspider_id>
  <pdbe_id/>
  <kegg_id>C00019</kegg_id>
  <chebi_id>15414</chebi_id>
  <pubchem_compound_id>34756</pubchem_compound_id>
  <knapsack_id>C00007347</knapsack_id>
  <meta_cyc_id>S-ADENOSYLMETHIONINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33530</bigg_id>
  <wikipedia_id>S-Adenosyl_methionine</wikipedia_id>
  <metlin_id>6064</metlin_id>
  <synthesis_reference>Lin, Jian-Ping; Tian, Jun; You, Jian-Feng; Jin, Zhi-Hua; Xu, Zhi-Nan; Cen, Pei-Lin. An effective strategy for the co-production of S-adenosyl-L-methionine and glutathione by fed-batch fermentation. Biochemical Engineering Journal (2004), 21(1), 19-25.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00100</protein_accession>
      <name>Phenylethanolamine N-methyltransferase</name>
      <uniprot_id>P10938</uniprot_id>
      <gene_name>PNMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00122</protein_accession>
      <name>Histamine N-methyltransferase</name>
      <uniprot_id>Q58DV7</uniprot_id>
      <gene_name>HNMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00174</protein_accession>
      <name>S-adenosylmethionine synthetase</name>
      <uniprot_id>A7E3T7</uniprot_id>
      <gene_name>MAT2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00361</protein_accession>
      <name>Elongator complex protein 3</name>
      <uniprot_id>Q2KJ61</uniprot_id>
      <gene_name>ELP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00394</protein_accession>
      <name>tRNA (adenine-N(1)-)-methyltransferase catalytic subunit TRMT61A</name>
      <uniprot_id>A6H791</uniprot_id>
      <gene_name>TRMT61A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00395</protein_accession>
      <name>Histone-lysine N-methyltransferase SUV39H2</name>
      <uniprot_id>Q32PH7</uniprot_id>
      <gene_name>SUV39H2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00396</protein_accession>
      <name>Lipoyl synthase, mitochondrial</name>
      <uniprot_id>Q5BIP7</uniprot_id>
      <gene_name>LIAS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00397</protein_accession>
      <name>Protein-L-isoaspartate(D-aspartate) O-methyltransferase</name>
      <uniprot_id>P15246</uniprot_id>
      <gene_name>PCMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00398</protein_accession>
      <name>Histone-lysine N-methyltransferase SETD8</name>
      <uniprot_id>Q2YDJ8</uniprot_id>
      <gene_name>SETD8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00399</protein_accession>
      <name>Diphthine synthase</name>
      <uniprot_id>Q5E982</uniprot_id>
      <gene_name>DPH5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00400</protein_accession>
      <name>Putative histone-lysine N-methyltransferase PRDM6</name>
      <uniprot_id>A6QPM3</uniprot_id>
      <gene_name>PRDM6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00401</protein_accession>
      <name>tRNA (cytosine-5-)-methyltransferase</name>
      <uniprot_id>Q7YS61</uniprot_id>
      <gene_name>TRDMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00402</protein_accession>
      <name>EHMT1 protein</name>
      <uniprot_id>A5PK11</uniprot_id>
      <gene_name>EHMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00403</protein_accession>
      <name>S-adenosylmethionine synthetase isoform type-1</name>
      <uniprot_id>Q2KJC6</uniprot_id>
      <gene_name>MAT1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00404</protein_accession>
      <name>tRNA (guanine-N(1)-)-methyltransferase</name>
      <uniprot_id>Q3MHN8</uniprot_id>
      <gene_name>TRMT5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00405</protein_accession>
      <name>Ubiquinone biosynthesis methyltransferase COQ5, mitochondrial</name>
      <uniprot_id>Q0P5A2</uniprot_id>
      <gene_name>COQ5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00406</protein_accession>
      <name>Protein arginine N-methyltransferase 7</name>
      <uniprot_id>A6QQV6</uniprot_id>
      <gene_name>PRMT7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00407</protein_accession>
      <name>DNA (cytosine-5)-methyltransferase 1</name>
      <uniprot_id>Q24K09</uniprot_id>
      <gene_name>DNMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00408</protein_accession>
      <name>Cytosine-specific methyltransferase</name>
      <uniprot_id>B1P383</uniprot_id>
      <gene_name>Dnmt1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00409</protein_accession>
      <name>Thiopurine S-methyltransferase</name>
      <uniprot_id>Q17QQ2</uniprot_id>
      <gene_name>TPMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00410</protein_accession>
      <name>Hydroxyindole O-methyltransferase</name>
      <uniprot_id>P10950</uniprot_id>
      <gene_name>ASMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00411</protein_accession>
      <name>Protein arginine N-methyltransferase 5</name>
      <uniprot_id>A7YW45</uniprot_id>
      <gene_name>PRMT5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00412</protein_accession>
      <name>Guanidinoacetate N-methyltransferase</name>
      <uniprot_id>Q2TBQ3</uniprot_id>
      <gene_name>GAMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00413</protein_accession>
      <name>Hexaprenyldihydroxybenzoate methyltransferase, mitochondrial</name>
      <uniprot_id>Q3T131</uniprot_id>
      <gene_name>COQ3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00414</protein_accession>
      <name>Methionine synthase</name>
      <uniprot_id>Q4JIJ3</uniprot_id>
      <gene_name>MTR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00415</protein_accession>
      <name>S-adenosylmethionine decarboxylase proenzyme</name>
      <uniprot_id>P50243</uniprot_id>
      <gene_name>AMD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00416</protein_accession>
      <name>Protein arginine N-methyltransferase 6</name>
      <uniprot_id>Q5E9L5</uniprot_id>
      <gene_name>PRMT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00417</protein_accession>
      <name>Histone-lysine N-methyltransferase SUV39H1</name>
      <uniprot_id>Q2NL30</uniprot_id>
      <gene_name>SUV39H1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00418</protein_accession>
      <name>Histone-lysine N-methyltransferase EZH1</name>
      <uniprot_id>A7E2Z2</uniprot_id>
      <gene_name>EZH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00419</protein_accession>
      <name>Histone-lysine N-methyltransferase SUV420H1</name>
      <uniprot_id>Q29RP8</uniprot_id>
      <gene_name>SUV420H1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00420</protein_accession>
      <name>Phosphatidylethanolamine N-methyltransferase</name>
      <uniprot_id>Q7YRH6</uniprot_id>
      <gene_name>PEMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00421</protein_accession>
      <name>Catechol O-methyltransferase</name>
      <uniprot_id>A7MBI7</uniprot_id>
      <gene_name>COMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00422</protein_accession>
      <name>Histone-lysine N-methyltransferase SETMAR</name>
      <uniprot_id>Q0VD24</uniprot_id>
      <gene_name>SETMAR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00423</protein_accession>
      <name>tRNA (guanine-N(7)-)-methyltransferase</name>
      <uniprot_id>Q2YDF1</uniprot_id>
      <gene_name>METTL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01582</protein_accession>
      <name>Radical S-adenosyl methionine domain-containing protein 2</name>
      <uniprot_id>Q2HJF9</uniprot_id>
      <gene_name>RSAD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01583</protein_accession>
      <name>Molybdenum cofactor biosynthesis protein 1</name>
      <uniprot_id>Q1JQD7</uniprot_id>
      <gene_name>MOCS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01584</protein_accession>
      <name>Radical S-adenosyl methionine domain-containing protein 1, mitochondrial</name>
      <uniprot_id>A5D7B1</uniprot_id>
      <gene_name>RSAD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01585</protein_accession>
      <name>S-adenosylmethionine mitochondrial carrier protein</name>
      <uniprot_id>A6QR09</uniprot_id>
      <gene_name>SLC25A26</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:15 UTC</creation_date>
  <update_date>2020-04-14 22:48:57 UTC</update_date>
  <accession>BMDB0001186</accession>
  <secondary_accessions>
    <accession>BMDB01186</accession>
  </secondary_accessions>
  <name>N1-Acetylspermine</name>
  <description/>
  <synonyms>
    <synonym>N'-acetylspermine</synonym>
    <synonym>N'-monoacetylspermine</synonym>
    <synonym>N(1)-Acetylspermine</synonym>
    <synonym>N-(3-((4-((3-Aminopropyl)amino)butyl)amino)propyl)-acetamide</synonym>
    <synonym>N-Acetylspermine</synonym>
    <synonym>Monoacetylspermine</synonym>
    <synonym>N1-Monoacetylspermine</synonym>
    <synonym>N1-Acetylspermine</synonym>
  </synonyms>
  <chemical_formula>C12H28N4O</chemical_formula>
  <average_molecular_weight>244.3769</average_molecular_weight>
  <monisotopic_moleculate_weight>244.226311538</monisotopic_moleculate_weight>
  <iupac_name>N-[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl]acetamide</iupac_name>
  <traditional_iupac>N(1)-acetylspermine</traditional_iupac>
  <cas_registry_number>25593-72-0</cas_registry_number>
  <smiles>CC(=O)NCCCNCCCCNCCCN</smiles>
  <inchi>InChI=1S/C12H28N4O/c1-12(17)16-11-5-10-15-8-3-2-7-14-9-4-6-13/h14-15H,2-11,13H2,1H3,(H,16,17)</inchi>
  <inchikey>GUNURVWAJRRUAV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Carboxylic acid derivatives</sub_class>
    <direct_parent>Acetamides</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>acetamides</external_descriptor>
      <external_descriptor>acetylspermine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>16.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl]acetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>244.3769</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>244.226311538</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)NCCCNCCCCNCCCN</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H28N4O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H28N4O/c1-12(17)16-11-5-10-15-8-3-2-7-14-9-4-6-13/h14-15H,2-11,13H2,1H3,(H,16,17)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GUNURVWAJRRUAV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>79.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>30.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179799</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022474</foodb_id>
  <drugbank_id/>
  <chemspider_id>892</chemspider_id>
  <pdbe_id/>
  <kegg_id>C02567</kegg_id>
  <chebi_id>17312</chebi_id>
  <pubchem_compound_id>916</pubchem_compound_id>
  <knapsack_id/>
  <meta_cyc_id>N1-ACETYLSPERMINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>3369</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00128</protein_accession>
      <name>Peroxisomal N(1)-acetyl-spermine/spermidine oxidase</name>
      <uniprot_id>Q865R1</uniprot_id>
      <gene_name>PAOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:16 UTC</creation_date>
  <update_date>2020-03-13 16:26:25 UTC</update_date>
  <accession>BMDB0001187</accession>
  <secondary_accessions>
    <accession>BMDB01187</accession>
  </secondary_accessions>
  <name>1D-Myo-inositol 1,3,4,6-tetrakisphosphate</name>
  <description>1D-Myo-1d-myo-inositol 1,3,4,6-tetrakisphosphate, also known as 1d-myo-inositol 1,3,4,6-tetrakisphosphate, belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety. 1D-Myo-1d-myo-inositol 1,3,4,6-tetrakisphosphate is possibly soluble (in water) and an extremely strong acidic compound (based on its pKa). 1D-Myo-1d-myo-inositol 1,3,4,6-tetrakisphosphate exists in all eukaryotes, ranging from yeast to humans. 1D-Myo-1d-myo-inositol 1,3,4,6-tetrakisphosphate participates in a number of enzymatic reactions, within cattle. In particular, 1D-Myo-1d-myo-inositol 1,3,4,6-tetrakisphosphate can be biosynthesized from inositol 1,3,4-trisphosphate; which is catalyzed by the enzyme inositol-tetrakisphosphate 1-kinase. In addition, 1D-Myo-1d-myo-inositol 1,3,4,6-tetrakisphosphate can be converted into 1D-myo-inositol 3,4-bisphosphate through the action of the enzyme inositol polyphosphate 1-phosphatase. In cattle, 111d-myo-1d-myo-inositol 1,3,4,6-tetrakisphosphate is involved in the metabolic pathway called the inositol metabolism pathway.</description>
  <synonyms>
    <synonym>1D-Myo-inositol 1,3,4,6-tetrakisphosphate</synonym>
    <synonym>Inositol 1,3,4,6-tetrakisphosphate</synonym>
    <synonym>Inositol-1,3,4,6-tetrakisphosphate</synonym>
    <synonym>Inositol-1,3,4,6-tetraphosphate</synonym>
    <synonym>Ins-1,3,4,6-P4</synonym>
    <synonym>Myo-inositol-1,3,4,6-tetrakisphosphate</synonym>
    <synonym>1D-Myo-inositol 1,3,4,6-tetrakisphosphoric acid</synonym>
    <synonym>Inositol 1,3,4,6-tetrakisphosphoric acid</synonym>
    <synonym>Inositol-1,3,4,6-tetrakisphosphoric acid</synonym>
    <synonym>Inositol-1,3,4,6-tetraphosphoric acid</synonym>
    <synonym>Myo-inositol-1,3,4,6-tetrakisphosphoric acid</synonym>
    <synonym>D-Myo-inositol 1,3,4,6-tetrakisphosphoric acid</synonym>
    <synonym>D-Myo-inositol 1,3,4,5-tetrakis-*phosphate potass</synonym>
    <synonym>D-Myo-inositol-1,3,4,5-tetrakisphosphate octapotassium salt</synonym>
    <synonym>Inositol 1,3,4,6-tetrakis(phosphate)</synonym>
    <synonym>Inositol 1,3,4,6-tetraphosphate</synonym>
    <synonym>Ins(1,3,4,6)P4</synonym>
    <synonym>D-Myo-inositol 1,3,4,6-tetraphosphate</synonym>
    <synonym>D-myo-Inositol 1,3,4,6-tetrakisphosphate</synonym>
  </synonyms>
  <chemical_formula>C6H16O18P4</chemical_formula>
  <average_molecular_weight>500.0755</average_molecular_weight>
  <monisotopic_moleculate_weight>499.928709756</monisotopic_moleculate_weight>
  <iupac_name>{[(1R,2s,3S,4S,5r,6R)-2,5-dihydroxy-3,4,6-tris(phosphonooxy)cyclohexyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(1R,2s,3S,4S,5r,6R)-2,5-dihydroxy-3,4,6-tris(phosphonooxy)cyclohexyl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>110298-84-5</cas_registry_number>
  <smiles>O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@@H](O)[C@@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C6H16O18P4/c7-1-3(21-25(9,10)11)5(23-27(15,16)17)2(8)6(24-28(18,19)20)4(1)22-26(12,13)14/h1-8H,(H2,9,10,11)(H2,12,13,14)(H2,15,16,17)(H2,18,19,20)/t1-,2+,3-,4+,5-,6+</inchi>
  <inchikey>ZAWIXNGTTZTBKV-JMVOWJSSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Inositol phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclohexanols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Cyclohexanol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Inositol phosphate</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>myo-inositol tetrakisphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(1R,2s,3S,4S,5r,6R)-2,5-dihydroxy-3,4,6-tris(phosphonooxy)cyclohexyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>500.0755</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>499.928709756</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@@H](O)[C@@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H16O18P4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H16O18P4/c7-1-3(21-25(9,10)11)5(23-27(15,16)17)2(8)6(24-28(18,19)20)4(1)22-26(12,13)14/h1-8H,(H2,9,10,11)(H2,12,13,14)(H2,15,16,17)(H2,18,19,20)/t1-,2+,3-,4+,5-,6+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZAWIXNGTTZTBKV-JMVOWJSSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>307.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087256</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183020</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04477</kegg_id>
  <chemspider_id>17216082</chemspider_id>
  <foodb_id>FDB022475</foodb_id>
  <chebi_id>16155</chebi_id>
  <pubchem_compound_id/>
  <drugbank_id>DB04300</drugbank_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>43890</bigg_id>
  <wikipedia_id/>
  <metlin_id>6066</metlin_id>
  <synthesis_reference>Watanabe, Yutaka; Mitani, Motohiro; Morita, Takao; Ozaki, Shoichiro. Highly efficient protection by the tetraisopropyldisiloxane-1,3-diyl group in the synthesis of myo-inositol phosphates as inositol 1,3,4,6-tetrakisphosphate. Journal of the Chemical Society Chemical Communications. 1989, Issue 8, p.482-483. DOI: 10.1039/C39890000482</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00089</protein_accession>
      <name>Inositol-tetrakisphosphate 1-kinase</name>
      <uniprot_id>P0C0T1</uniprot_id>
      <gene_name>ITPK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:17 UTC</creation_date>
  <update_date>2020-03-13 16:26:25 UTC</update_date>
  <accession>BMDB0001188</accession>
  <secondary_accessions>
    <accession>BMDB01188</accession>
  </secondary_accessions>
  <name>(S)-2,3-Epoxysqualene</name>
  <description/>
  <synonyms>
    <synonym>(S)-Squalene-2,3-epoxide</synonym>
    <synonym>Squalene 2,3-epoxide</synonym>
    <synonym>Squalene 2,3-oxide</synonym>
  </synonyms>
  <chemical_formula>C30H50O</chemical_formula>
  <average_molecular_weight>426.7174</average_molecular_weight>
  <monisotopic_moleculate_weight>426.386166222</monisotopic_moleculate_weight>
  <iupac_name>(3S)-2,2-dimethyl-3-[(3Z,7E,11Z,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane</iupac_name>
  <traditional_iupac>(3S)-2,2-dimethyl-3-[(3Z,7E,11Z,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(C)=CCC\C(C)=C\CC\C(C)=C/CC\C=C(/C)CC\C=C(\C)CC[C@]1([H])OC1(C)C</smiles>
  <inchi>InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15-,26-16+,27-20+,28-21-/t29-/m0/s1</inchi>
  <inchikey>QYIMSPSDBYKPPY-CBMIWKPVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Triterpenoids</sub_class>
    <direct_parent>Triterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Epoxides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxirane</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>8.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>9.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3S)-2,2-dimethyl-3-[(3Z,7E,11Z,15E)-3,7,12,16,20-pentamethylhenicosa-3,7,11,15,19-pentaen-1-yl]oxirane</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>426.7174</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>426.386166222</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)=CCC\C(C)=C\CC\C(C)=C/CC\C=C(/C)CC\C=C(\C)CC[C@]1([H])OC1(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C30H50O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15-,26-16+,27-20+,28-21-/t29-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QYIMSPSDBYKPPY-CBMIWKPVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>12.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>143.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>55.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372210</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01054</kegg_id>
  <foodb_id>FDB022476</foodb_id>
  <pubchem_compound_id>53477723</pubchem_compound_id>
  <chemspider_id/>
  <drugbank_id/>
  <chebi_id>15441</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>EPOXYSQUALENE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>36708</bigg_id>
  <wikipedia_id/>
  <metlin_id>3530</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00804</protein_accession>
      <name>Lanosterol synthase</name>
      <uniprot_id>P84466</uniprot_id>
      <gene_name>LSS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:18 UTC</creation_date>
  <update_date>2020-03-13 16:26:26 UTC</update_date>
  <accession>BMDB0001189</accession>
  <secondary_accessions>
    <accession>BMDB01189</accession>
  </secondary_accessions>
  <name>2(N)-Methyl-norsalsolinol</name>
  <description/>
  <synonyms>
    <synonym>1,2,3,4-Tetrahydro-2-methyl-6,7-isoquinolinediol</synonym>
    <synonym>2-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline</synonym>
    <synonym>2-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide</synonym>
    <synonym>NMNSAL</synonym>
    <synonym>2-MDTIQ</synonym>
    <synonym>2-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride</synonym>
    <synonym>N-Methylnorsalsolinol</synonym>
  </synonyms>
  <chemical_formula>C10H13NO2</chemical_formula>
  <average_molecular_weight>179.2157</average_molecular_weight>
  <monisotopic_moleculate_weight>179.094628665</monisotopic_moleculate_weight>
  <iupac_name>2-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol</iupac_name>
  <traditional_iupac>2(N)-methyl-norsalsolinol</traditional_iupac>
  <cas_registry_number>63937-92-8</cas_registry_number>
  <smiles>CN1CCC2=CC(O)=C(O)C=C2C1</smiles>
  <inchi>InChI=1S/C10H13NO2/c1-11-3-2-7-4-9(12)10(13)5-8(7)6-11/h4-5,12-13H,2-3,6H2,1H3</inchi>
  <inchikey>WETXYFNVBDLWIW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrahydroisoquinolines</class>
    <sub_class/>
    <direct_parent>Tetrahydroisoquinolines</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
      <substituent>Tetrahydroisoquinoline</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>7.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>179.2157</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>179.094628665</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1CCC2=CC(O)=C(O)C=C2C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H13NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H13NO2/c1-11-3-2-7-4-9(12)10(13)5-8(7)6-11/h4-5,12-13H,2-3,6H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WETXYFNVBDLWIW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>43.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354426</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id>34632</chemspider_id>
  <foodb_id>FDB022477</foodb_id>
  <chebi_id>767276</chebi_id>
  <pubchem_compound_id>37764</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:19 UTC</creation_date>
  <update_date>2020-03-13 16:26:26 UTC</update_date>
  <accession>BMDB0001190</accession>
  <secondary_accessions>
    <accession>BMDB01190</accession>
  </secondary_accessions>
  <name>Indoleacetaldehyde</name>
  <description>Indoleacetaldehyde belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Indoleacetaldehyde is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Indoleacetaldehyde exists in all living species, ranging from bacteria to humans. Indoleacetaldehyde participates in a number of enzymatic reactions, within cattle. In particular, Indoleacetaldehyde can be biosynthesized from tryptamine through the action of the enzyme kynurenine 3-monooxygenase. In addition, Indoleacetaldehyde can be converted into indoleacetic acid; which is catalyzed by the enzyme aldehyde dehydrogenase, mitochondrial. In cattle, indoleacetaldehyde is involved in the metabolic pathway called the tryptophan metabolism pathway.</description>
  <synonyms>
    <synonym>1H-Indole-3-acetaldehyde</synonym>
    <synonym>2-(indol-3-yl)Acetaldehyde</synonym>
    <synonym>Indole-3-acetaldehyde</synonym>
    <synonym>1H-indol-3-Ylacetaldehyde</synonym>
    <synonym>2-(3-Indolyl)acetaldehyde</synonym>
    <synonym>indol-3-Ylacetaldehyde</synonym>
    <synonym>Tryptaldehyde</synonym>
  </synonyms>
  <chemical_formula>C10H9NO</chemical_formula>
  <average_molecular_weight>159.1846</average_molecular_weight>
  <monisotopic_moleculate_weight>159.068413915</monisotopic_moleculate_weight>
  <iupac_name>2-(1H-indol-3-yl)acetaldehyde</iupac_name>
  <traditional_iupac>indole-3-acetaldehyde</traditional_iupac>
  <cas_registry_number>2591-98-2</cas_registry_number>
  <smiles>O=CCC1=CNC2=C1C=CC=C2</smiles>
  <inchi>InChI=1S/C10H9NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,6-7,11H,5H2</inchi>
  <inchikey>WHOOUMGHGSPMGR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Indoles</sub_class>
    <direct_parent>3-alkylindoles</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydrogen aldehydes</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alkylindole</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Alpha-hydrogen aldehyde</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>indoleacetaldehyde</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(1H-indol-3-yl)acetaldehyde</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>159.1846</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>159.068413915</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O=CCC1=CNC2=C1C=CC=C2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H9NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H9NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,6-7,11H,5H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WHOOUMGHGSPMGR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>32.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9929</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31291</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00637</kegg_id>
  <chemspider_id>778</chemspider_id>
  <foodb_id>FDB013950</foodb_id>
  <chebi_id>18086</chebi_id>
  <pubchem_compound_id>800</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id>INDOLE_ACETALDEHYDE</meta_cyc_id>
  <knapsack_id>C00000109</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35561</bigg_id>
  <wikipedia_id/>
  <metlin_id>6068</metlin_id>
  <synthesis_reference>Gray, Reed A.  Preparation and properties of 3-indoleacetaldehyde.    Archives of Biochemistry and Biophysics  (1959),  81  480-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:21 UTC</creation_date>
  <update_date>2020-04-16 17:51:33 UTC</update_date>
  <accession>BMDB0001191</accession>
  <secondary_accessions>
    <accession>BMDB01191</accession>
  </secondary_accessions>
  <name>Deoxyuridine triphosphate</name>
  <description/>
  <synonyms>
    <synonym>2'-Deoxyuridine 5'-triphosphate</synonym>
    <synonym>2'-Deoxyuridine 5'-triphosphoric acid</synonym>
    <synonym>Deoxyuridine triphosphoric acid</synonym>
    <synonym>2'-Deoxyuridine-5'-triphosphorate</synonym>
    <synonym>2'-Deoxyuridine-5'-triphosphoric acid</synonym>
    <synonym>2'-Deoxyuridine-5'-triphosphoric acid = dUTP</synonym>
    <synonym>Deoxy-UTP</synonym>
    <synonym>Deoxyuridine-5'-triphosphate</synonym>
    <synonym>dUTP</synonym>
  </synonyms>
  <chemical_formula>C9H15N2O14P3</chemical_formula>
  <average_molecular_weight>468.1417</average_molecular_weight>
  <monisotopic_moleculate_weight>467.973612734</monisotopic_moleculate_weight>
  <iupac_name>({[({[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</iupac_name>
  <traditional_iupac>dUTP</traditional_iupac>
  <cas_registry_number>1173-82-6</cas_registry_number>
  <smiles>O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C9H15N2O14P3/c12-5-3-8(11-2-1-7(13)10-9(11)14)23-6(5)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,18,19)(H,20,21)(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1</inchi>
  <inchikey>AHCYMLUZIRLXAA-SHYZEUOFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside triphosphates. These are pyrimidine nucleotides with a triphosphate group  linked to the ribose moiety lacking a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine deoxyribonucleotides</sub_class>
    <direct_parent>Pyrimidine 2'-deoxyribonucleoside triphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside triphosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxyribonucleotides</external_descriptor>
      <external_descriptor>deoxyuridine phosphate</external_descriptor>
      <external_descriptor>pyrimidine 2'-deoxyribonucleoside 5'-triphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>({[({[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>468.1417</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>467.973612734</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H15N2O14P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H15N2O14P3/c12-5-3-8(11-2-1-7(13)10-9(11)14)23-6(5)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,18,19)(H,20,21)(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AHCYMLUZIRLXAA-SHYZEUOFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>238.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>83.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35188</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00460</kegg_id>
  <chemspider_id>58580</chemspider_id>
  <foodb_id>FDB030842</foodb_id>
  <chebi_id>17625</chebi_id>
  <pubchem_compound_id>65070</pubchem_compound_id>
  <drugbank_id>DB02333</drugbank_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id>C00019636</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35037</bigg_id>
  <wikipedia_id/>
  <metlin_id>6069</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:22 UTC</creation_date>
  <update_date>2020-03-13 16:26:27 UTC</update_date>
  <accession>BMDB0001192</accession>
  <secondary_accessions>
    <accession>BMDB01192</accession>
  </secondary_accessions>
  <name>Diadenosine pentaphosphate</name>
  <description/>
  <synonyms>
    <synonym>({[({[(2R,3S,4R,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)({[({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinate</synonym>
    <synonym>Diadenosine pentaphosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C20H29N10O22P5</chemical_formula>
  <average_molecular_weight>916.369</average_molecular_weight>
  <monisotopic_moleculate_weight>916.014597604</monisotopic_moleculate_weight>
  <iupac_name>({[({[(2R,3S,4R,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)({[({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid</iupac_name>
  <traditional_iupac>diadenosine pentaphosphate</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@]2([H])O[C@@]([H])(N3C=NC4=C(N)N=CN=C34)[C@]([H])(O)[C@]2([H])O)O[C@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O</smiles>
  <inchi>InChI=1S/C20H29N10O22P5/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(47-19)1-45-53(35,36)49-55(39,40)51-57(43,44)52-56(41,42)50-54(37,38)46-2-8-12(32)14(34)20(48-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H2,21,23,25)(H2,22,24,26)/t7-,8+,11-,12-,13-,14-,19+,20-/m1/s1</inchi>
  <inchikey>OIMACDRJUANHTJ-MRVWQQQFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside polyphosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside polyphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>({[({[(2R,3S,4R,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)({[({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>916.369</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>916.014597604</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@]2([H])O[C@@]([H])(N3C=NC4=C(N)N=CN=C34)[C@]([H])(O)[C@]2([H])O)O[C@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H29N10O22P5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H29N10O22P5/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(47-19)1-45-53(35,36)49-55(39,40)51-57(43,44)52-56(41,42)50-54(37,38)46-2-8-12(32)14(34)20(48-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H2,21,23,25)(H2,22,24,26)/t7-,8+,11-,12-,13-,14-,19+,20-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OIMACDRJUANHTJ-MRVWQQQFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>480.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>176.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>72.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1247527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1247528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1247529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1362856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1362857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1362858</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id/>
  <pubchem_compound_id/>
  <chemspider_id/>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:23 UTC</creation_date>
  <update_date>2020-03-13 16:26:28 UTC</update_date>
  <accession>BMDB0001193</accession>
  <secondary_accessions>
    <accession>BMDB01193</accession>
  </secondary_accessions>
  <name>5(S)-Hydroperoxyeicosatetraenoic acid</name>
  <description/>
  <synonyms>
    <synonym>(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoic acid</synonym>
    <synonym>(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoate</synonym>
    <synonym>(6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoate</synonym>
    <synonym>(6E,8Z,11Z,14Z)-(5S)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoic acid</synonym>
    <synonym>(S)-5-HPETE</synonym>
    <synonym>5(S)-Hydroperoxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoic acid</synonym>
    <synonym>5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid</synonym>
    <synonym>5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-eicosatetraenoic acid</synonym>
    <synonym>5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-icosatetraenoic acid</synonym>
    <synonym>5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate</synonym>
    <synonym>5S-HpETE</synonym>
    <synonym>(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyeicosa-6,8,11,14-tetraenoate</synonym>
    <synonym>(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-tetraenoic acid</synonym>
    <synonym>5(S)-Hydroperoxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoate</synonym>
    <synonym>5(S)-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoate</synonym>
    <synonym>5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-eicosatetraenoate</synonym>
    <synonym>5(S)-Hydroxyperoxy-6E,8Z,11Z,14Z-icosatetraenoate</synonym>
    <synonym>5-Hydroperoxy-6-trans-8,11,14-cis-eicosatetraenoic acid</synonym>
    <synonym>5(S)-Hydroperoxyeicosatetraenoate</synonym>
    <synonym>5-HPETE</synonym>
    <synonym>5-Hydroperoxy-6,8,11,14-eicosatetraenoic acid</synonym>
    <synonym>6,8,11,14-Eicosatetraenoic acid 5-hydroperoxide</synonym>
    <synonym>Arachidonic acid 5-hydroperoxide</synonym>
    <synonym>cis,trans-5-Hydroperoxy-6,8,11,14-eicosatetraenoic acid</synonym>
  </synonyms>
  <chemical_formula>C20H32O4</chemical_formula>
  <average_molecular_weight>336.4657</average_molecular_weight>
  <monisotopic_moleculate_weight>336.230059512</monisotopic_moleculate_weight>
  <iupac_name>(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid</iupac_name>
  <traditional_iupac>5-HpETE</traditional_iupac>
  <cas_registry_number>71774-08-8</cas_registry_number>
  <smiles>CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OO</smiles>
  <inchi>InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1</inchi>
  <inchikey>JNUUNUQHXIOFDA-JGKLHWIESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Hydroperoxyeicosatetraenoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl hydroperoxides</alternative_parent>
      <alternative_parent>Allylic hydroperoxides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroperoxy fatty acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Peroxols</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl hydroperoxide</substituent>
      <substituent>Allylic hydroperoxide</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroperoxide</substituent>
      <substituent>Hydroperoxy fatty acid</substituent>
      <substituent>Hydroperoxyeicosatetraenoic acid</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Peroxol</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>HPETE</external_descriptor>
      <external_descriptor>Hydroperoxy fatty acids</external_descriptor>
      <external_descriptor>Hydroxy/hydroperoxyeicosatetraenoic acids</external_descriptor>
      <external_descriptor>Hydroxy/hydroperoxyeicosatetraenoic acids</external_descriptor>
      <external_descriptor>Leukotrienes</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>336.4657</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>336.230059512</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](CCCC(O)=O)OO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H32O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JNUUNUQHXIOFDA-JGKLHWIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>102.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31513</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05356</kegg_id>
  <chemspider_id>4444340</chemspider_id>
  <foodb_id>FDB022480</foodb_id>
  <chebi_id>15632</chebi_id>
  <pubchem_compound_id>5280778</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>45650</bigg_id>
  <wikipedia_id/>
  <metlin_id>6070</metlin_id>
  <synthesis_reference>Dussault, Patrick; Lee, In Quen.  A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE.    Journal of Organic Chemistry  (1995),  60(1),  218-26.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:24 UTC</creation_date>
  <update_date>2020-04-15 22:26:11 UTC</update_date>
  <accession>BMDB0001195</accession>
  <secondary_accessions>
    <accession>BMDB01195</accession>
  </secondary_accessions>
  <name>Dyspropterin</name>
  <description/>
  <synonyms>
    <synonym>6-(1,2-Dioxopropyl)-5,6,7,8-tetrahydropterin</synonym>
    <synonym>6-Pyruvoyl-5,6,7,8-tetrahydropterin</synonym>
    <synonym>6-Pyruvoyltetrahydropterin</synonym>
    <synonym>6-Pyruvoyl-tetrahydropterin</synonym>
    <synonym>6-Pyruvoyl tetrahydropteridine</synonym>
    <synonym>Pyruvoyl-H4-pterin</synonym>
  </synonyms>
  <chemical_formula>C9H11N5O3</chemical_formula>
  <average_molecular_weight>237.2153</average_molecular_weight>
  <monisotopic_moleculate_weight>237.086189243</monisotopic_moleculate_weight>
  <iupac_name>1-(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)propane-1,2-dione</iupac_name>
  <traditional_iupac>1-(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)propane-1,2-dione</traditional_iupac>
  <cas_registry_number>89687-39-8</cas_registry_number>
  <smiles>CC(=O)C(=O)C1CNC2=C(N1)C(=O)NC(N)=N2</smiles>
  <inchi>InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h4,12H,2H2,1H3,(H4,10,11,13,14,17)</inchi>
  <inchikey>WBJZXBUVECZHCE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Pterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-amino ketones</alternative_parent>
      <alternative_parent>Alpha-diketones</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta-amino ketones</alternative_parent>
      <alternative_parent>Gamma-amino ketones</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-aminoketone</substituent>
      <substituent>Alpha-diketone</substituent>
      <substituent>Amine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Beta-aminoketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Gamma-aminoketone</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pterin</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>biopterins</external_descriptor>
      <external_descriptor>tetrahydropterin</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-(2-amino-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)propane-1,2-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>237.2153</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>237.086189243</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)C(=O)C1CNC2=C(N1)C(=O)NC(N)=N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H11N5O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h4,12H,2H2,1H3,(H4,10,11,13,14,17)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WBJZXBUVECZHCE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>125.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>67.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pterine Biosynthesis</name>
      <smpdb_id>SMP0087250</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34249</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03684</kegg_id>
  <chemspider_id>114280</chemspider_id>
  <foodb_id>FDB022481</foodb_id>
  <chebi_id>17804</chebi_id>
  <pubchem_compound_id>128973</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <meta_cyc_id>6-PYRUVOYL-5678-TETRAHYDROPTERIN</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>42328</bigg_id>
  <wikipedia_id>Dyspropterin</wikipedia_id>
  <metlin_id>6071</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:26 UTC</creation_date>
  <update_date>2020-03-13 16:26:29 UTC</update_date>
  <accession>BMDB0001196</accession>
  <secondary_accessions>
    <accession>BMDB01196</accession>
  </secondary_accessions>
  <name>N,N'-Diacetylchitobiosyldiphosphodolichol</name>
  <description/>
  <synonyms>
    <synonym>Chitobiosyldiphosphodolichol</synonym>
    <synonym>[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-(carboxyamino)-4-hydroxy-6-{[hydroxy({[hydroxy({[(6E)-3,7,10-trimethylundeca-6,9-dien-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]carbamate</synonym>
  </synonyms>
  <chemical_formula>C28H50N2O19P2</chemical_formula>
  <average_molecular_weight>780.6461</average_molecular_weight>
  <monisotopic_moleculate_weight>780.248300452</monisotopic_moleculate_weight>
  <iupac_name>[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-(carboxyamino)-4-hydroxy-6-{[hydroxy({[hydroxy({[(6E)-3,7,10-trimethylundeca-6,9-dien-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]carbamic acid</iupac_name>
  <traditional_iupac>(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-(carboxyamino)-4-hydroxy-6-{[hydroxy({hydroxy[(6E)-3,7,10-trimethylundeca-6,9-dien-1-yl]oxyphosphoryl}oxy)phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-ylcarbamic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(O)=O)[C@@H](O[C@@H]2CO)OP(=O)(O)OP(O)(=O)OCCC(C)CC\C=C(/C)CC=C(C)C)[C@H](NC(O)=O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C28H50N2O19P2/c1-14(2)8-9-15(3)6-5-7-16(4)10-11-44-50(40,41)49-51(42,43)48-26-20(30-28(38)39)23(35)24(18(13-32)46-26)47-25-19(29-27(36)37)22(34)21(33)17(12-31)45-25/h6,8,16-26,29-35H,5,7,9-13H2,1-4H3,(H,36,37)(H,38,39)(H,40,41)(H,42,43)/b15-6+/t16?,17-,18-,19-,20-,21-,22-,23-,24-,25+,26+/m1/s1</inchi>
  <inchikey>YBYNXPYEWMVKMB-HNLAPQKRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as disaccharide phosphates. These are disaccharides carrying  one or more phosphate group on a sugar unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Disaccharide phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Carbamic acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocyclic monoterpenoids</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic carbonic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Carbamic acid</substituent>
      <substituent>Carbamic acid derivative</substituent>
      <substituent>Carbonic acid derivative</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Disaccharide phosphate</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocyclic monoterpenoid</substituent>
      <substituent>Monoterpenoid</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.014</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-(carboxyamino)-4-hydroxy-6-{[hydroxy({[hydroxy({[(6E)-3,7,10-trimethylundeca-6,9-dien-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]carbamic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>780.6461</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>780.248300452</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(O)=O)[C@@H](O[C@@H]2CO)OP(=O)(O)OP(O)(=O)OCCC(C)CC\C=C(/C)CC=C(C)C)[C@H](NC(O)=O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C28H50N2O19P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C28H50N2O19P2/c1-14(2)8-9-15(3)6-5-7-16(4)10-11-44-50(40,41)49-51(42,43)48-26-20(30-28(38)39)23(35)24(18(13-32)46-26)47-25-19(29-27(36)37)22(34)21(33)17(12-31)45-25/h6,8,16-26,29-35H,5,7,9-13H2,1-4H3,(H,36,37)(H,38,39)(H,40,41)(H,42,43)/b15-6+/t16?,17-,18-,19-,20-,21-,22-,23-,24-,25+,26+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YBYNXPYEWMVKMB-HNLAPQKRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>329.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>171.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>74.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>63031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>320999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368511</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04537</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022482</foodb_id>
  <chemspider_id>17216085</chemspider_id>
  <pubchem_compound_id>22833564</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>1809476</bigg_id>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:27 UTC</creation_date>
  <update_date>2020-03-13 16:26:29 UTC</update_date>
  <accession>BMDB0001197</accession>
  <secondary_accessions>
    <accession>BMDB01197</accession>
  </secondary_accessions>
  <name>FADH</name>
  <description>Fadh, also known as Fadh or fadh, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. Fadh is possibly soluble (in water) and a strong basic compound (based on its pKa). Fadh exists in all living species, ranging from bacteria to humans. In cattle, fadh is involved in the metabolic pathway called the LPS and citrate signaling and inflammation pathway.</description>
  <synonyms>
    <synonym>1,5-Dihydro-fad</synonym>
    <synonym>DIHYDROFLAVINE-adenine dinucleotide</synonym>
    <synonym>Flavin adenine dinucleotide (reduced)</synonym>
    <synonym>1,5-Dihydro-p-5-ester with adenosine</synonym>
    <synonym>1,5-Dihydro-riboflavin 5'-(trihydrogen diphosphate) p'-&gt;5'-ester with adenosine</synonym>
    <synonym>Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine</synonym>
    <synonym>Adenosine 5'-(trihydrogen pyrophosphate), 5'-&gt;5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine</synonym>
    <synonym>Adenosine 5'-{3-[D-ribo-5-(7,8-dimethyl-2,4-dioxo-1,2,3,4,5,10-tetrahydrobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] dihydrogen diphosphate}</synonym>
    <synonym>Adenosine 5-(trihydrogen pyrophosphate)</synonym>
    <synonym>Adenosine pyrophosphate 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine</synonym>
    <synonym>Adenosine pyrophosphate, 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine</synonym>
    <synonym>Adenosine pyrophosphate, 5'-&gt;5'-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine</synonym>
    <synonym>Benzo[GR]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv</synonym>
    <synonym>Benzo[g]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv</synonym>
    <synonym>Dihydro-fad</synonym>
    <synonym>FADH2</synonym>
    <synonym>FDA</synonym>
    <synonym>Flavin adenine dinucleotide reduced</synonym>
    <synonym>Reduced flavine adenine dinucleotide</synonym>
  </synonyms>
  <chemical_formula>C27H35N9O15P2</chemical_formula>
  <average_molecular_weight>787.5656</average_molecular_weight>
  <monisotopic_moleculate_weight>787.172784519</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid</iupac_name>
  <traditional_iupac>fadh(.)</traditional_iupac>
  <cas_registry_number>1910-41-4</cas_registry_number>
  <smiles>CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=C(N2)C(=O)NC(=O)N1</smiles>
  <inchi>InChI=1S/C27H35N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,32,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H2,33,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1</inchi>
  <inchikey>YPZRHBJKEMOYQH-UYBVJOGSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Flavin nucleotides</class>
    <sub_class/>
    <direct_parent>Flavin nucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Alkyldiarylamines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Flavins</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary amines</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alkyldiarylamine</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Flavin</substituent>
      <substituent>Flavin nucleotide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pteridine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>flavin adenine dinucleotide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>787.5656</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>787.172784519</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=C(N2)C(=O)NC(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H35N9O15P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H35N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,32,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H2,33,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YPZRHBJKEMOYQH-UYBVJOGSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>355.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>188.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>69.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>LPS and Citrate Signaling and Inflammation</name>
      <smpdb_id>SMP0120946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>65421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179279</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181604</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01352</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB030853</foodb_id>
  <chemspider_id>393487</chemspider_id>
  <pubchem_compound_id>446013</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17877</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>132077</bigg_id>
  <wikipedia_id>Flavin adenine dinucleotide</wikipedia_id>
  <metlin_id>6073</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Kavakli I Halil; Sancar Aziz  Analysis of the role of intraprotein electron transfer in photoreactivation by DNA photolyase in vivo.    Biochemistry  (2004),  43(48),  15103-10.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:28 UTC</creation_date>
  <update_date>2020-04-16 17:54:11 UTC</update_date>
  <accession>BMDB0001198</accession>
  <secondary_accessions>
    <accession>BMDB01198</accession>
  </secondary_accessions>
  <name>Leukotriene C4</name>
  <description/>
  <synonyms>
    <synonym>(R-(R*,s*-(e,e,Z,Z)))-N-(S-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-N-L-gamma-glutamyl-L-cysteinyl)glycine</synonym>
    <synonym>5S,6R-LTC(Sub 4)</synonym>
    <synonym>5S-Hydroxy,6R-(S-glutathionyl),7E,9E,11Z,14Z-eicosatetraenoic acid</synonym>
    <synonym>LTC (Sub 4)</synonym>
    <synonym>LTC4</synonym>
    <synonym>(R-(R*,s*-(e,e,Z,Z)))-N-(S-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-N-L-g-glutamyl-L-cysteinyl)glycine</synonym>
    <synonym>(R-(R*,s*-(e,e,Z,Z)))-N-(S-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-N-L-γ-glutamyl-L-cysteinyl)glycine</synonym>
    <synonym>5S-Hydroxy,6R-(S-glutathionyl),7E,9E,11Z,14Z-eicosatetraenoate</synonym>
    <synonym>Leukotriene C-1</synonym>
    <synonym>Leukotriene C-4</synonym>
    <synonym>Leukotrienes C</synonym>
    <synonym>Leukotriene C</synonym>
    <synonym>Leukotriene C 1</synonym>
    <synonym>Leukotriene C 4</synonym>
    <synonym>Leukotriene C1</synonym>
    <synonym>(R-(R*,s*-(e,e,Z,Z)))-N-(S-(1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-N-L-gamma-glutamyl-L-cysteinyl)-glycine</synonym>
    <synonym>5S,6R-LTC</synonym>
    <synonym>L-gamma-Glutamyl-S-[(1R,2E,4E,6Z,9Z)-1-[(1S)-4-carboxy-1-hydroxybutyl]-2,4,6,9-pentadecatetraenyl]-L-cysteinyl-glycine</synonym>
    <synonym>Leucotriene C4</synonym>
    <synonym>LTC</synonym>
    <synonym>[R-[R*,s*-(e,e,Z,Z)]]-N-[S-[1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl]-N-L-gamma-glutamyl-L-cysteinyl]-glycine 5S,6R-LTC4</synonym>
    <synonym>5S,6R-LTC4</synonym>
    <synonym>Leukotriene C4</synonym>
  </synonyms>
  <chemical_formula>C30H47N3O9S</chemical_formula>
  <average_molecular_weight>625.774</average_molecular_weight>
  <monisotopic_moleculate_weight>625.303300807</monisotopic_moleculate_weight>
  <iupac_name>(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid</iupac_name>
  <traditional_iupac>leukotriene C4</traditional_iupac>
  <cas_registry_number>72025-60-6</cas_registry_number>
  <smiles>CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)[C@@H](O)CCCC(O)=O</smiles>
  <inchi>InChI=1S/C30H47N3O9S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-25(24(34)15-14-17-27(36)37)43-21-23(29(40)32-20-28(38)39)33-26(35)19-18-22(31)30(41)42/h6-7,9-13,16,22-25,34H,2-5,8,14-15,17-21,31H2,1H3,(H,32,40)(H,33,35)(H,36,37)(H,38,39)(H,41,42)/b7-6-,10-9-,12-11+,16-13+/t22-,23-,24-,25+/m0/s1</inchi>
  <inchikey>GWNVDXQDILPJIG-NXOLIXFESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Oligopeptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cysteine and derivatives</alternative_parent>
      <alternative_parent>Dialkylthioethers</alternative_parent>
      <alternative_parent>Gamma-glutamyl peptides</alternative_parent>
      <alternative_parent>Glutamine and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Hydroxyeicosatetraenoic acids</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Leukotrienes</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
      <alternative_parent>Tricarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-oligopeptide</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Cysteine or derivatives</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Eicosanoid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Gamma-glutamyl alpha peptide</substituent>
      <substituent>Glutamine or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Hydroxyeicosatetraenoic acid</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Leukotriene</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-substituted-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thia fatty acid</substituent>
      <substituent>Thioether</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Leukotrienes</external_descriptor>
      <external_descriptor>Leukotrienes</external_descriptor>
      <external_descriptor>leukotriene</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.015</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>625.774</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>625.303300807</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)[C@@H](O)CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C30H47N3O9S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C30H47N3O9S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-25(24(34)15-14-17-27(36)37)43-21-23(29(40)32-20-28(38)39)33-26(35)19-18-22(31)30(41)42/h6-7,9-13,16,22-25,34H,2-5,8,14-15,17-21,31H2,1H3,(H,32,40)(H,33,35)(H,36,37)(H,38,39)(H,41,42)/b7-6-,10-9-,12-11+,16-13+/t22-,23-,24-,25+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GWNVDXQDILPJIG-NXOLIXFESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>216.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>168.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>68.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>245436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>245437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>245438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>265383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>265384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>265385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435529</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02166</kegg_id>
  <drugbank_id>DB08855</drugbank_id>
  <foodb_id>FDB030979</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>5280493</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16978</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Leukotriene_C4</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id>LEUKOTRIENE-C4</meta_cyc_id>
  <synthesis_reference>Rokach, Joshua; Young, Robert N.; Kakushima, Masatoshi; Lau, Cheuk-Kun; Seguin, Rick; Frenette, Richard; Guindon, Yvan.  Synthesis of leukotrienes.  New synthesis of natural leukotriene A4.    Tetrahedron Letters  (1981),  22(11),  979-82.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01078</protein_accession>
      <name>Leukotriene C4 synthase</name>
      <uniprot_id>Q2NKS0</uniprot_id>
      <gene_name>LTC4S</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02087</protein_accession>
      <name>Multidrug resistance-associated protein 1</name>
      <uniprot_id>Q8HXQ5</uniprot_id>
      <gene_name>ABCC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:29 UTC</creation_date>
  <update_date>2020-03-13 16:26:31 UTC</update_date>
  <accession>BMDB0001199</accession>
  <secondary_accessions>
    <accession>BMDB01199</accession>
  </secondary_accessions>
  <name>N2-Succinyl-L-ornithine</name>
  <description/>
  <synonyms>
    <synonym>(2S)-5-Amino-2-(3-carboxypropanoylamino)pentanoic acid</synonym>
    <synonym>(2S)-5-Amino-2-(3-carboxypropanoylamino)pentanoate</synonym>
    <synonym>N(2)-Succinylornithine</synonym>
  </synonyms>
  <chemical_formula>C9H16N2O5</chemical_formula>
  <average_molecular_weight>232.2337</average_molecular_weight>
  <monisotopic_moleculate_weight>232.105921632</monisotopic_moleculate_weight>
  <iupac_name>(2S)-5-amino-2-(3-carboxypropanamido)pentanoic acid</iupac_name>
  <traditional_iupac>N(2)-succinyl-L-ornithine</traditional_iupac>
  <cas_registry_number>899816-95-6</cas_registry_number>
  <smiles>NCCC[C@H](NC(=O)CCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C9H16N2O5/c10-5-1-2-6(9(15)16)11-7(12)3-4-8(13)14/h6H,1-5,10H2,(H,11,12)(H,13,14)(H,15,16)/t6-/m0/s1</inchi>
  <inchikey>VWXQFHJBQHTHMK-LURJTMIESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N2-acyl-L-ornithine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-5-amino-2-(3-carboxypropanamido)pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>232.2337</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>232.105921632</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCC[C@H](NC(=O)CCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H16N2O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H16N2O5/c10-5-1-2-6(9(15)16)11-7(12)3-4-8(13)14/h6H,1-5,10H2,(H,11,12)(H,13,14)(H,15,16)/t6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VWXQFHJBQHTHMK-LURJTMIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>129.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>53.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24881</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24882</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31441</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03415</kegg_id>
  <drugbank_id>DB03582</drugbank_id>
  <foodb_id>FDB022485</foodb_id>
  <chemspider_id>113025</chemspider_id>
  <pubchem_compound_id>127370</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>27574</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6075</metlin_id>
  <meta_cyc_id>N2-SUCCINYLORNITHINE</meta_cyc_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:30 UTC</creation_date>
  <update_date>2020-03-13 16:26:31 UTC</update_date>
  <accession>BMDB0001200</accession>
  <secondary_accessions>
    <accession>BMDB01200</accession>
  </secondary_accessions>
  <name>N'-Formylkynurenine</name>
  <description>N'-n'-formylkynurenine belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. N'-n'-formylkynurenine is possibly soluble (in water) and a very strong basic compound (based on its pKa). N'-n'-formylkynurenine exists in all eukaryotes, ranging from yeast to humans. N'-n'-formylkynurenine participates in a number of enzymatic reactions, within cattle. In particular, N'-n'-formylkynurenine can be biosynthesized from L-tryptophan; which is mediated by the enzyme tryptophan 2,3-dioxygenase. In addition, N'-n'-formylkynurenine can be converted into formylanthranilic acid and L-alanine; which is catalyzed by the enzyme kynureninase. In cattle, n'-n'-formylkynurenine is involved in the metabolic pathway called the tryptophan metabolism pathway.</description>
  <synonyms>
    <synonym>3-(2-Formamidobenzoyl)alanine</synonym>
    <synonym>Formylkynurenine</synonym>
    <synonym>3-(N-Formylanthraniloyl)-alanine</synonym>
    <synonym>alpha-Amino-2-(formylamino)-gamma-oxo-benzenebutanoate</synonym>
    <synonym>alpha-Amino-2-(formylamino)-gamma-oxo-benzenebutanoic acid</synonym>
    <synonym>N'-formyl-kynurenine</synonym>
    <synonym>N-Formyl-D-kynurenine</synonym>
    <synonym>N-Formyl-delta-kynurenine</synonym>
    <synonym>N-Formyl-L-kynurenine</synonym>
    <synonym>N'-formylkynurenine, (R)-isomer</synonym>
    <synonym>N'-formylkynurenine, (S)-isomer</synonym>
    <synonym>N-Formylkynurenine</synonym>
  </synonyms>
  <chemical_formula>C11H12N2O4</chemical_formula>
  <average_molecular_weight>236.224</average_molecular_weight>
  <monisotopic_moleculate_weight>236.079706882</monisotopic_moleculate_weight>
  <iupac_name>2-amino-4-(2-formamidophenyl)-4-oxobutanoic acid</iupac_name>
  <traditional_iupac>N-formylkynurenine</traditional_iupac>
  <cas_registry_number>1022-31-7</cas_registry_number>
  <smiles>NC(CC(=O)C1=CC=CC=C1NC=O)C(O)=O</smiles>
  <inchi>InChI=1S/C11H12N2O4/c12-8(11(16)17)5-10(15)7-3-1-2-4-9(7)13-6-14/h1-4,6,8H,5,12H2,(H,13,14)(H,16,17)</inchi>
  <inchikey>BYHJHXPTQMMKCA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Alkyl-phenylketones</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha amino acids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Anilides</alternative_parent>
      <alternative_parent>Aryl alkyl ketones</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Beta-amino ketones</alternative_parent>
      <alternative_parent>Butyrophenones</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Gamma-keto acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-arylamides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkyl-phenylketone</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Anilide</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl alkyl ketone</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Beta-aminoketone</substituent>
      <substituent>Butyrophenone</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Gamma-keto acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Keto acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-arylamide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>non-proteinogenic alpha-amino acid</external_descriptor>
      <external_descriptor>non-proteinogenic amino acid derivative</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-4-(2-formamidophenyl)-4-oxobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>236.224</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>236.079706882</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CC(=O)C1=CC=CC=C1NC=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H12N2O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H12N2O4/c12-8(11(16)17)5-10(15)7-3-1-2-4-9(7)13-6-14/h1-4,6,8H,5,12H2,(H,13,14)(H,16,17)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BYHJHXPTQMMKCA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>109.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180401</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02406</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022486</foodb_id>
  <chemspider_id>886</chemspider_id>
  <pubchem_compound_id>910</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18377</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>1445551</bigg_id>
  <wikipedia_id>N'-Formylkynurenine</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Jayson, G. G.; Scholes, G.; Weiss, J.  Formation of formylkynurenine by the action of x-rays on tryptophan in aqueous solution.    Biochemical Journal  (1954),  57  386-90.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00012</protein_accession>
      <name>Tryptophan 2,3-dioxygenase</name>
      <uniprot_id>Q2KIQ5</uniprot_id>
      <gene_name>TDO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:31 UTC</creation_date>
  <update_date>2020-03-13 16:26:32 UTC</update_date>
  <accession>BMDB0001201</accession>
  <secondary_accessions>
    <accession>BMDB01201</accession>
  </secondary_accessions>
  <name>Guanosine diphosphate</name>
  <description>Guanosine diphosphate, also known as Guanosine diphosphate or GDP, belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. Guanosine diphosphate is possibly soluble (in water) and a moderately basic compound (based on its pKa). Guanosine diphosphate exists in all living species, ranging from bacteria to humans. In cattle, guanosine diphosphate is involved in a couple of metabolic pathways, which include the intracellular signalling through adenosine receptor A2A and adenosine pathway and the intracellular signalling through adenosine receptor A2B and adenosine pathway.</description>
  <synonyms>
    <synonym>Guanosine 5'-diphosphate</synonym>
    <synonym>Guanosine 5'-diphosphoric acid</synonym>
    <synonym>Guanosine diphosphoric acid</synonym>
    <synonym>5'-GDP</synonym>
    <synonym>GDP</synonym>
    <synonym>Guanosine 5'-(trihydrogen pyrophosphate)</synonym>
    <synonym>Guanosine 5'-pyrophosphate</synonym>
    <synonym>Guanosine mono(trihydrogen diphosphate)</synonym>
    <synonym>Guanosine pyrophosphate</synonym>
    <synonym>Guanosine-5'-diphosphate</synonym>
    <synonym>Guanosine-diphosphate</synonym>
    <synonym>PpG</synonym>
    <synonym>5'-Diphosphate, guanosine</synonym>
    <synonym>Diphosphate, guanosine 5'-trihydrogen</synonym>
    <synonym>Guanosine 5' diphosphate</synonym>
    <synonym>Guanosine 5' trihydrogen diphosphate</synonym>
    <synonym>5'-Trihydrogen diphosphate, guanosine</synonym>
    <synonym>Diphosphate, guanosine</synonym>
    <synonym>Guanosine 5'-trihydrogen diphosphate</synonym>
  </synonyms>
  <chemical_formula>C10H15N5O11P2</chemical_formula>
  <average_molecular_weight>443.2005</average_molecular_weight>
  <monisotopic_moleculate_weight>443.024329371</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>146-91-8</cas_registry_number>
  <smiles>NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C10H15N5O11P2/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(25-9)1-24-28(22,23)26-27(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1</inchi>
  <inchikey>QGWNDRXFNXRZMB-UUOKFMHZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside diphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ribonucleotides</external_descriptor>
      <external_descriptor>guanosine 5'-phosphate</external_descriptor>
      <external_descriptor>purine ribonucleoside 5'-diphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>443.2005</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>443.024329371</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H15N5O11P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H15N5O11P2/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(25-9)1-24-28(22,23)26-27(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QGWNDRXFNXRZMB-UUOKFMHZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>248.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>85.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Activation of cAMP-dependent protein kinase, PKA</name>
      <smpdb_id>SMP0108201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Activation of PKC Through G Protein-Coupled Receptor</name>
      <smpdb_id>SMP0108001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>BCR Signaling Pathway</name>
      <smpdb_id>SMP0120940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cadmium Induces DNA Synthesis and Proliferation in Macrophages </name>
      <smpdb_id>SMP0108212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Corticotropin Activation of Cortisol Production</name>
      <smpdb_id>SMP0108167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dopamine Activation of Neurological Reward System</name>
      <smpdb_id>SMP0107994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>EGF Signalling Pathway</name>
      <smpdb_id>SMP0120924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>EPO Signaling Pathway</name>
      <smpdb_id>SMP0120938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 4 and Serotonin</name>
      <smpdb_id>SMP0108169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 6 and Serotonin</name>
      <smpdb_id>SMP0108172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 7 and Serotonin</name>
      <smpdb_id>SMP0108170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histamine H1 Receptor Activation</name>
      <smpdb_id>SMP0108002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Insulin Signalling</name>
      <smpdb_id>SMP0108189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2a and Adenosine</name>
      <smpdb_id>SMP0108174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2b and Adenosine</name>
      <smpdb_id>SMP0108178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through FSH Receptor and Follicle Stimulating Hormone</name>
      <smpdb_id>SMP0108183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Histamine H2 Receptor and Histamine</name>
      <smpdb_id>SMP0107995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through LHCGR Receptor and Luteinizing Hormone/Choriogonadotropin</name>
      <smpdb_id>SMP0108184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through PGD2 receptor and Prostaglandin D2</name>
      <smpdb_id>SMP0107997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Prostacyclin Receptor and Prostacyclin</name>
      <smpdb_id>SMP0107998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA1 Signalling</name>
      <smpdb_id>SMP0108191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA2 Signalling</name>
      <smpdb_id>SMP0108193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA3 Signalling</name>
      <smpdb_id>SMP0108194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA4 Signalling</name>
      <smpdb_id>SMP0108196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA5 Signalling</name>
      <smpdb_id>SMP0108198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA6 Signalling</name>
      <smpdb_id>SMP0108199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Rac 1 cell motility signaling pathway </name>
      <smpdb_id>SMP0100484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Rac 1 Cell Motility Signaling Pathway</name>
      <smpdb_id>SMP0120885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vasopressin Regulation of Water Homeostasis</name>
      <smpdb_id>SMP0108181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451931</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00035</kegg_id>
  <drugbank_id>DB04315</drugbank_id>
  <foodb_id>FDB030875</foodb_id>
  <chemspider_id>8630</chemspider_id>
  <pubchem_compound_id>8977</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17552</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>33599</bigg_id>
  <wikipedia_id>Guanosine diphosphate</wikipedia_id>
  <metlin_id>6077</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Edlin, Gordon; Donini, P.  Synthesis of guanosine 5'-diphosphate, 2'-(or 3'-) diphosphate, and related nucleotides in a variety of physiological conditions.    Journal of Biological Chemistry  (1971),  246(13),  4371-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:33 UTC</creation_date>
  <update_date>2020-03-13 16:26:32 UTC</update_date>
  <accession>BMDB0001202</accession>
  <secondary_accessions>
    <accession>BMDB01202</accession>
  </secondary_accessions>
  <name>dCMP</name>
  <description/>
  <synonyms>
    <synonym>2'-Deoxycytidine 5'-monophosphate</synonym>
    <synonym>2'-DEOXYCYTIDINE-5'-monophosphATE</synonym>
    <synonym>Deoxycytidine monophosphate</synonym>
    <synonym>Deoxycytidylate</synonym>
    <synonym>Deoxycytidylic acid</synonym>
    <synonym>2'-Deoxycytidine 5'-monophosphoric acid</synonym>
    <synonym>2'-DEOXYCYTIDINE-5'-monophosphoric acid</synonym>
    <synonym>Deoxycytidine monophosphoric acid</synonym>
    <synonym>2'-Deoxycytosine 5'-monophosphate</synonym>
    <synonym>2'-Deoxycytosine 5'-monophosphoric acid</synonym>
    <synonym>2'-Deoxycytidine-3'-monophosphate</synonym>
    <synonym>2'-Deoxycytidine-5'-monophosphorate</synonym>
    <synonym>2'-Deoxycytidine-5'-phosphate</synonym>
    <synonym>Deoxycytidine-phosphate</synonym>
    <synonym>Acid, deoxycytidylic</synonym>
    <synonym>Deoxycytidylic acids</synonym>
    <synonym>Acids, deoxycytidylic</synonym>
    <synonym>monoPhosphate, deoxycytidine</synonym>
  </synonyms>
  <chemical_formula>C9H14N3O7P</chemical_formula>
  <average_molecular_weight>307.1971</average_molecular_weight>
  <monisotopic_moleculate_weight>307.056936329</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>dCMP</traditional_iupac>
  <cas_registry_number>1032-65-1</cas_registry_number>
  <smiles>NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1</smiles>
  <inchi>InChI=1S/C9H14N3O7P/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(19-8)4-18-20(15,16)17/h1-2,5-6,8,13H,3-4H2,(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1</inchi>
  <inchikey>NCMVOABPESMRCP-SHYZEUOFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside monophosphates. These are pyrimidine nucleotides with a monophosphate group  linked to the ribose moiety lacking a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine deoxyribonucleotides</sub_class>
    <direct_parent>Pyrimidine 2'-deoxyribonucleoside monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside monophosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2'-deoxycytidine phosphate</external_descriptor>
      <external_descriptor>Deoxyribonucleotides</external_descriptor>
      <external_descriptor>pyrimidine 2'-deoxyribonucleoside 5'-monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>307.1971</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>307.056936329</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H14N3O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H14N3O7P/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(19-8)4-18-20(15,16)17/h1-2,5-6,8,13H,3-4H2,(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NCMVOABPESMRCP-SHYZEUOFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>154.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>63.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178792</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181112</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00239</kegg_id>
  <drugbank_id>DB03798</drugbank_id>
  <foodb_id>FDB022488</foodb_id>
  <chemspider_id>13343</chemspider_id>
  <pubchem_compound_id>13945</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15918</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>34352</bigg_id>
  <wikipedia_id>DCMP</wikipedia_id>
  <metlin_id>6078</metlin_id>
  <meta_cyc_id>DCMP</meta_cyc_id>
  <synthesis_reference>Tanaka, Toshiki; Yamada, Yasuki; Ikehara, Morio. Chemical synthesis of deoxyribonucleotide with a 5'-phosphoryl group on a polystyrene polymer support by the phosphotriester method. Chemical &amp; Pharmaceutical Bulletin (1987), 35(7), 2726-33.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00613</protein_accession>
      <name>dCTP pyrophosphatase 1</name>
      <uniprot_id>Q32KY6</uniprot_id>
      <gene_name>DCTPP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00863</protein_accession>
      <name>Deoxycytidine kinase</name>
      <uniprot_id>Q3MHR2</uniprot_id>
      <gene_name>DCK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:34 UTC</creation_date>
  <update_date>2020-03-13 16:26:33 UTC</update_date>
  <accession>BMDB0001203</accession>
  <secondary_accessions>
    <accession>BMDB01203</accession>
  </secondary_accessions>
  <name>4a-Formyl-5a-cholesta-8,24-dien-3b-ol</name>
  <description/>
  <synonyms>
    <synonym>4alpha-Formyl-5alpha-cholesta-8,24-dien-3beta -ol</synonym>
  </synonyms>
  <chemical_formula>C28H44O2</chemical_formula>
  <average_molecular_weight>412.6478</average_molecular_weight>
  <monisotopic_moleculate_weight>412.334130652</monisotopic_moleculate_weight>
  <iupac_name>5-hydroxy-2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carbaldehyde</iupac_name>
  <traditional_iupac>5-hydroxy-2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carbaldehyde</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(CCC=C(C)C)C1CCC2C3=C(CCC12C)C1(C)CCC(O)C(C=O)C1CC3</smiles>
  <inchi>InChI=1S/C28H44O2/c1-18(2)7-6-8-19(3)22-11-12-23-20-9-10-24-21(17-29)26(30)14-16-28(24,5)25(20)13-15-27(22,23)4/h7,17,19,21-24,26,30H,6,8-16H2,1-5H3</inchi>
  <inchikey>ZLQSSFNCEUGGJF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Aldehydes</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a 3-&amp;beta;-hydroxysterol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-hydroxy-2,15-dimethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-6-carbaldehyde</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>412.6478</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>412.334130652</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(CCC=C(C)C)C1CCC2C3=C(CCC12C)C1(C)CCC(O)C(C=O)C1CC3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C28H44O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C28H44O2/c1-18(2)7-6-8-19(3)22-11-12-23-20-9-10-24-21(17-29)26(30)14-16-28(24,5)25(20)13-15-27(22,23)4/h7,17,19,21-24,26,30H,6,8-16H2,1-5H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZLQSSFNCEUGGJF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>126.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336246</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022489</foodb_id>
  <pubchem_compound_id>656456</pubchem_compound_id>
  <chemspider_id>570845</chemspider_id>
  <kegg_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6079</metlin_id>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:35 UTC</creation_date>
  <update_date>2020-04-15 22:15:00 UTC</update_date>
  <accession>BMDB0001204</accession>
  <secondary_accessions>
    <accession>BMDB01204</accession>
  </secondary_accessions>
  <name>trans-3-Hydroxycotinine glucuronide</name>
  <description/>
  <synonyms>
    <synonym>(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-{[(3R,5R)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylate</synonym>
  </synonyms>
  <chemical_formula>C16H20N2O8</chemical_formula>
  <average_molecular_weight>368.342</average_molecular_weight>
  <monisotopic_moleculate_weight>368.121965612</monisotopic_moleculate_weight>
  <iupac_name>(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R,5R)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>3HC-gluc</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@]1(C[C@@]([H])(N(C)C1=O)C1=CN=CC=C1)O[C@]1([H])O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O</smiles>
  <inchi>InChI=1S/C16H20N2O8/c1-18-8(7-3-2-4-17-6-7)5-9(14(18)22)25-16-12(21)10(19)11(20)13(26-16)15(23)24/h2-4,6,8-13,16,19-21H,5H2,1H3,(H,23,24)/t8-,9-,10+,11+,12-,13+,16-/m1/s1</inchi>
  <inchikey>WALNNKZUGHYSCT-YNESOLSOSA-N</inchikey>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(3R,5R)-1-methyl-2-oxo-5-(pyridin-3-yl)pyrrolidin-3-yl]oxy}oxane-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>368.342</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>368.121965612</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(C[C@@]([H])(N(C)C1=O)C1=CN=CC=C1)O[C@]1([H])O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H20N2O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H20N2O8/c1-18-8(7-3-2-4-17-6-7)5-9(14(18)22)25-16-12(21)10(19)11(20)13(26-16)15(23)24/h2-4,6,8-13,16,19-21H,5H2,1H3,(H,23,24)/t8-,9-,10+,11+,12-,13+,16-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WALNNKZUGHYSCT-YNESOLSOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>149.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>83.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1273585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1273586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1273587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1388566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1388567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1388568</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id/>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:36 UTC</creation_date>
  <update_date>2020-04-16 20:38:37 UTC</update_date>
  <accession>BMDB0001206</accession>
  <secondary_accessions>
    <accession>BMDB01206</accession>
  </secondary_accessions>
  <name>Acetyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>AcCoA</synonym>
    <synonym>Acetyl coenzyme A</synonym>
    <synonym>S-Acetyl-CoA</synonym>
    <synonym>S-Acetyl-coenzyme A</synonym>
    <synonym>Ac-CoA</synonym>
    <synonym>Ac-coenzyme A</synonym>
    <synonym>Ac-S-CoA</synonym>
    <synonym>Ac-S-coenzyme A</synonym>
    <synonym>Acetyl-coenzyme A</synonym>
    <synonym>Acetyl-S-CoA</synonym>
    <synonym>Acetyl-S-coenzyme A</synonym>
    <synonym>Acetylcoenzyme A</synonym>
    <synonym>S-Acetate CoA</synonym>
    <synonym>S-Acetate coenzyme A</synonym>
    <synonym>S-Acetyl coenzyme A</synonym>
    <synonym>coenzyme A, Acetyl</synonym>
    <synonym>Acetyl CoA</synonym>
    <synonym>CoA, Acetyl</synonym>
  </synonyms>
  <chemical_formula>C23H38N7O17P3S</chemical_formula>
  <average_molecular_weight>809.571</average_molecular_weight>
  <monisotopic_moleculate_weight>809.125773051</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-2-({[({[(3R)-3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>acetyl-CoA</traditional_iupac>
  <cas_registry_number>72-89-9</cas_registry_number>
  <smiles>CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1</inchi>
  <inchikey>ZSLZBFCDCINBPY-ZSJPKINUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>O-glucuronides</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>N-alkylpyrrolidines</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Pyrrolidine-2-ones</alternative_parent>
      <alternative_parent>Pyrrolidinylpyridines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-o-glucuronide</substituent>
      <substituent>2-pyrrolidone</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-alkylpyrrolidine</substituent>
      <substituent>O-glucuronide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidinylpyridine</substituent>
      <substituent>Pyrrolidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-2-({[({[(3R)-3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>809.571</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>809.125773051</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C23H38N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZSLZBFCDCINBPY-ZSJPKINUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>172.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>70.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Beta Oxidation of Very Long Chain Fatty Acids</name>
      <smpdb_id>SMP0087259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Butyrate Metabolism</name>
      <smpdb_id>SMP0087185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Caffeine Metabolism</name>
      <smpdb_id>SMP0087186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ethanol Degradation</name>
      <smpdb_id>SMP0087192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Elongation in Mitochondria</name>
      <smpdb_id>SMP0087194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ketone Body Metabolism</name>
      <smpdb_id>SMP0087202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>LPS and Citrate Signaling and Inflammation</name>
      <smpdb_id>SMP0120946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Retinol Metabolism</name>
      <smpdb_id>SMP0087260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36256</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00024</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022491</foodb_id>
  <chemspider_id>392413</chemspider_id>
  <pubchem_compound_id>444493</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15351</chebi_id>
  <knapsack_id>C00007259</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Acetyl-CoA</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33558</bigg_id>
  <metlin_id>6082</metlin_id>
  <synthesis_reference>Tucek, S.  The synthesis of acetyl coenzyme A and acetylcholine from citrate and acetate in the nerve endings of mammalian brain.    Biochimica et Biophysica Acta, General Subjects  (1966),  117(1),  278-80.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00175</protein_accession>
      <name>ATP-citrate synthase</name>
      <uniprot_id>Q32PF2</uniprot_id>
      <gene_name>ACLY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00204</protein_accession>
      <name>Acetyl-CoA carboxylase 1</name>
      <uniprot_id>Q9TTS3</uniprot_id>
      <gene_name>ACACA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00260</protein_accession>
      <name>Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial</name>
      <uniprot_id>Q07536</uniprot_id>
      <gene_name>ALDH6A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00358</protein_accession>
      <name>Serotonin N-acetyltransferase</name>
      <uniprot_id>O02785</uniprot_id>
      <gene_name>AANAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00359</protein_accession>
      <name>Hydroxymethylglutaryl-CoA synthase, mitochondrial</name>
      <uniprot_id>Q2KIE6</uniprot_id>
      <gene_name>HMGCS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00360</protein_accession>
      <name>Arylamine N-acetyltransferase 1</name>
      <uniprot_id>Q1JPA6</uniprot_id>
      <gene_name>NAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00361</protein_accession>
      <name>Elongator complex protein 3</name>
      <uniprot_id>Q2KJ61</uniprot_id>
      <gene_name>ELP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00362</protein_accession>
      <name>Citrate synthase, mitochondrial</name>
      <uniprot_id>Q29RK1</uniprot_id>
      <gene_name>CS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00363</protein_accession>
      <name>Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex</name>
      <uniprot_id>P11180</uniprot_id>
      <gene_name>DLAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00364</protein_accession>
      <name>N-terminal acetyltransferase complex ARD1 subunit homolog A</name>
      <uniprot_id>Q2KI14</uniprot_id>
      <gene_name>ARD1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00365</protein_accession>
      <name>Trifunctional enzyme subunit beta, mitochondrial</name>
      <uniprot_id>O46629</uniprot_id>
      <gene_name>HADHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00366</protein_accession>
      <name>2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial</name>
      <uniprot_id>Q0P5L8</uniprot_id>
      <gene_name>GCAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00367</protein_accession>
      <name>Acyl-CoA synthetase short-chain family member 3, mitochondrial</name>
      <uniprot_id>A7MB45</uniprot_id>
      <gene_name>ACSS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00368</protein_accession>
      <name>Fatty acid synthase</name>
      <uniprot_id>Q71SP7</uniprot_id>
      <gene_name>FASN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00369</protein_accession>
      <name>3-ketoacyl-CoA thiolase, mitochondrial</name>
      <uniprot_id>Q3T0R7</uniprot_id>
      <gene_name>ACAA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00370</protein_accession>
      <name>Diamine acetyltransferase 2</name>
      <uniprot_id>Q7PCJ8</uniprot_id>
      <gene_name>SAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00371</protein_accession>
      <name>Acetyl-CoA acetyltransferase, mitochondrial</name>
      <uniprot_id>Q29RZ0</uniprot_id>
      <gene_name>ACAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00372</protein_accession>
      <name>Diamine acetyltransferase 1</name>
      <uniprot_id>Q3T0Q0</uniprot_id>
      <gene_name>SAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:38 UTC</creation_date>
  <update_date>2020-03-13 16:26:34 UTC</update_date>
  <accession>BMDB0001209</accession>
  <secondary_accessions>
    <accession>BMDB01209</accession>
  </secondary_accessions>
  <name>Allantoic acid</name>
  <description/>
  <synonyms>
    <synonym>Bis[(aminocarbonyl)amino]acetic acid</synonym>
    <synonym>Diureidoacetic acid</synonym>
    <synonym>Bis[(aminocarbonyl)amino]acetate</synonym>
    <synonym>Diureidoacetate</synonym>
    <synonym>Allantoate</synonym>
    <synonym>Allantoic acid, monosodium salt</synonym>
  </synonyms>
  <chemical_formula>C4H8N4O4</chemical_formula>
  <average_molecular_weight>176.1307</average_molecular_weight>
  <monisotopic_moleculate_weight>176.054554764</monisotopic_moleculate_weight>
  <iupac_name>2,2-bis(carbamoylamino)acetic acid</iupac_name>
  <traditional_iupac>allantoic acid</traditional_iupac>
  <cas_registry_number>99-16-1</cas_registry_number>
  <smiles>NC(=O)NC(NC(N)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C4H8N4O4/c5-3(11)7-1(2(9)10)8-4(6)12/h1H,(H,9,10)(H3,5,7,11)(H3,6,8,12)</inchi>
  <inchikey>NUCLJNSWZCHRKL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-carbamoyl-alpha amino acids. N-carbamoyl-alpha amino acids are compounds containing an alpha amino acid which bears an carbamoyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-carbamoyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonic acid derivative</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-carbamoyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Urea</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>ureas</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>180 - 181 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,2-bis(carbamoylamino)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>176.1307</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>176.054554764</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)NC(NC(N)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8N4O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8N4O4/c5-3(11)7-1(2(9)10)8-4(6)12/h1H,(H,9,10)(H3,5,7,11)(H3,6,8,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NUCLJNSWZCHRKL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>147.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437253</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00499</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB012646</foodb_id>
  <chemspider_id>198</chemspider_id>
  <pubchem_compound_id>203</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30837</chebi_id>
  <knapsack_id>C00007470</knapsack_id>
  <meta_cyc_id>ALLANTOATE</meta_cyc_id>
  <wikipedia_id>Allantoic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>343</metlin_id>
  <synthesis_reference>Hermanowicz, Witold.  Allantoic acid. Formation of allantoic acid from allantoin.    Roczniki Chemii  (1948),  22  159-80.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00801</protein_accession>
      <name>Probable allantoicase</name>
      <uniprot_id>Q2KIG4</uniprot_id>
      <gene_name>ALLC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:39 UTC</creation_date>
  <update_date>2020-03-13 16:26:35 UTC</update_date>
  <accession>BMDB0001212</accession>
  <secondary_accessions>
    <accession>BMDB01212</accession>
  </secondary_accessions>
  <name>Hydantoin-5-propionic acid</name>
  <description/>
  <synonyms>
    <synonym>Hydantoin-propionate</synonym>
    <synonym>Hydantoin-propionic acid</synonym>
    <synonym>Hydantoin-5-propionate</synonym>
    <synonym>1-(2,4-(3H,5H)Imidazoledione)propionic acid</synonym>
    <synonym>Hydantoin-5-propionic acid</synonym>
  </synonyms>
  <chemical_formula>C6H8N2O4</chemical_formula>
  <average_molecular_weight>172.1387</average_molecular_weight>
  <monisotopic_moleculate_weight>172.048406754</monisotopic_moleculate_weight>
  <iupac_name>3-(2,5-dioxoimidazolidin-4-yl)propanoic acid</iupac_name>
  <traditional_iupac>hydantoin-5-propionic acid</traditional_iupac>
  <cas_registry_number>5624-26-0</cas_registry_number>
  <smiles>OC(=O)CCC1NC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C6H8N2O4/c9-4(10)2-1-3-5(11)8-6(12)7-3/h3H,1-2H2,(H,9,10)(H2,7,8,11,12)</inchi>
  <inchikey>VWFWNXQAMGDPGG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine  substituted by ketone group at positions 2 and 4.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Azolidines</class>
    <sub_class>Imidazolidines</sub_class>
    <direct_parent>Hydantoins</direct_parent>
    <alternative_parents>
      <alternative_parent>5-monosubstituted hydantoins</alternative_parent>
      <alternative_parent>Alpha amino acids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboximides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl ureas</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>5-monosubstituted hydantoin</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonic acid derivative</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboximide</substituent>
      <substituent>Hydantoin</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl urea</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Urea</substituent>
      <substituent>Ureide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>imidazolidine-2,4-dione</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-8.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(2,5-dioxoimidazolidin-4-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>172.1387</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>172.048406754</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC1NC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H8N2O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H8N2O4/c9-4(10)2-1-3-5(11)8-6(12)7-3/h3H,1-2H2,(H,9,10)(H2,7,8,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VWFWNXQAMGDPGG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>95.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>36.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362682</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05565</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022493</foodb_id>
  <chemspider_id>761</chemspider_id>
  <pubchem_compound_id>782</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28297</chebi_id>
  <knapsack_id/>
  <meta_cyc_id>HYDANTOIN-5-PROPIONATE</meta_cyc_id>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6084</metlin_id>
  <synthesis_reference>Hassall, H.; Greenberg, D. M.  Preparation of carbamylglutamic acid and hydantoin-5-propionic acid.    Methods Enzymol.  (1971),  17(Pt. B),  95-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:40 UTC</creation_date>
  <update_date>2020-03-13 16:26:35 UTC</update_date>
  <accession>BMDB0001213</accession>
  <secondary_accessions>
    <accession>BMDB01213</accession>
  </secondary_accessions>
  <name>1-Deoxy-D-xylulose 5-phosphate</name>
  <description/>
  <synonyms>
    <synonym>1-Deoxy-D-xylulose 5-phosphoric acid</synonym>
    <synonym>1-Deoxy-D-threo-pentulose 5-phosphate</synonym>
    <synonym>D-1-Deoxyxylulose-5-p</synonym>
    <synonym>Deoxyxylulose-5-phosphate</synonym>
    <synonym>DOXP</synonym>
    <synonym>DXP</synonym>
    <synonym>1-Deoxylulose 5-phosphate</synonym>
  </synonyms>
  <chemical_formula>C5H11O7P</chemical_formula>
  <average_molecular_weight>214.1104</average_molecular_weight>
  <monisotopic_moleculate_weight>214.024239218</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S)-2,3-dihydroxy-4-oxopentyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>1-deoxy-D-xylulose-5-phosphate</traditional_iupac>
  <cas_registry_number>190079-18-6</cas_registry_number>
  <smiles>CC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C5H11O7P/c1-3(6)5(8)4(7)2-12-13(9,10)11/h4-5,7-8H,2H2,1H3,(H2,9,10,11)/t4-,5-/m1/s1</inchi>
  <inchikey>AJPADPZSRRUGHI-RFZPGFLSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Acyloins</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Acyloin</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>xylulose phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S)-2,3-dihydroxy-4-oxopentyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>214.1104</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>214.024239218</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H11O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H11O7P/c1-3(6)5(8)4(7)2-12-13(9,10)11/h4-5,7-8H,2H2,1H3,(H2,9,10,11)/t4-,5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AJPADPZSRRUGHI-RFZPGFLSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>124.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30019</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C11437</kegg_id>
  <drugbank_id>DB02496</drugbank_id>
  <foodb_id>FDB022494</foodb_id>
  <chemspider_id>391473</chemspider_id>
  <pubchem_compound_id>443201</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16493</chebi_id>
  <knapsack_id>C00007292</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>1-Deoxy-D-xylulose 5-phosphate</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6085</metlin_id>
  <synthesis_reference>Blagg, Brian S. J.; Poulter, C. Dale.  Synthesis of 1-Deoxy-D-xylulose and 1-Deoxy-D-xylulose-5-phosphate.    Journal of Organic Chemistry  (1999),  64(5),  1508-1511.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:41 UTC</creation_date>
  <update_date>2020-03-13 16:26:36 UTC</update_date>
  <accession>BMDB0001216</accession>
  <secondary_accessions>
    <accession>BMDB01216</accession>
  </secondary_accessions>
  <name>Tetrahydropteridine</name>
  <description/>
  <synonyms>
    <synonym>5,6,7,8-Tetrahydropteridine</synonym>
    <synonym>5,6,7,8-Tetrahydro-pteridine</synonym>
    <synonym>H4-Biopterin</synonym>
    <synonym>THP</synonym>
    <synonym>Tetrahydropteridine</synonym>
  </synonyms>
  <chemical_formula>C6H8N4</chemical_formula>
  <average_molecular_weight>136.1545</average_molecular_weight>
  <monisotopic_moleculate_weight>136.074896276</monisotopic_moleculate_weight>
  <iupac_name>5,6,7,8-tetrahydropteridine</iupac_name>
  <traditional_iupac>5,6,7,8-tetrahydropteridine</traditional_iupac>
  <cas_registry_number>10593-78-9</cas_registry_number>
  <smiles>C1CNC2=C(N1)C=NC=N2</smiles>
  <inchi>InChI=1S/C6H8N4/c1-2-9-6-5(8-1)3-7-4-10-6/h3-4,8H,1-2H2,(H,7,9,10)</inchi>
  <inchikey>IDAICLIJTRXNER-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form  pyrimido(4,5-b)pyrazine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class/>
    <direct_parent>Pteridines and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidines and pyrimidine derivatives</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pteridine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>pteridines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5,6,7,8-tetrahydropteridine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>136.1545</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>136.074896276</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C1CNC2=C(N1)C=NC=N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H8N4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H8N4/c1-2-9-6-5(8-1)3-7-4-10-6/h3-4,8H,1-2H2,(H,7,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IDAICLIJTRXNER-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>49.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16404</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05650</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022495</foodb_id>
  <chemspider_id>151</chemspider_id>
  <pubchem_compound_id>156</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28889</chebi_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6086</metlin_id>
  <synthesis_reference>Taylor, E. C., Jr.; Carbon, John A.; Garland, Robert B.; Hoff, Dale R.; Howell, Charles F.; Sherman, Wm. R.  Recent developments in pteridine synthesis.    Ciba Foundation Symposium, Chem. and Biol. Pteridines  (1954),     104-20.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00597</protein_accession>
      <name>Dihydropteridine reductase</name>
      <uniprot_id>Q3T0Z7</uniprot_id>
      <gene_name>QDPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:42 UTC</creation_date>
  <update_date>2020-03-13 16:26:36 UTC</update_date>
  <accession>BMDB0001217</accession>
  <secondary_accessions>
    <accession>BMDB01217</accession>
  </secondary_accessions>
  <name>4a-Methylzymosterol</name>
  <description/>
  <synonyms>
    <synonym>(15S)-Prostaglandin e2</synonym>
    <synonym>(5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid</synonym>
    <synonym>(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate</synonym>
    <synonym>(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoate</synonym>
    <synonym>(e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid</synonym>
    <synonym>(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acid</synonym>
    <synonym>Dinoproston</synonym>
    <synonym>Dinoprostona</synonym>
    <synonym>Dinoprostone</synonym>
    <synonym>Dinoprostonum</synonym>
    <synonym>PGE2</synonym>
    <synonym>Prepidil</synonym>
    <synonym>Propess</synonym>
    <synonym>Prostin e2</synonym>
    <synonym>Cervidil</synonym>
    <synonym>(5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid</synonym>
    <synonym>(5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,11Α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,11Α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid</synonym>
    <synonym>(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoate</synonym>
    <synonym>(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoate</synonym>
    <synonym>(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>(e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoate</synonym>
    <synonym>(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoate</synonym>
    <synonym>(-)-Prostaglandin e2</synonym>
    <synonym>(5Z,13E,15S)-11-alpha,15-Dihydroxy-9-oxoprost-5,13-dienoate</synonym>
    <synonym>(5Z,13E,15S)-11-alpha,15-Dihydroxy-9-oxoprost-5,13-dienoic acid</synonym>
    <synonym>5-trans-PGE2</synonym>
    <synonym>Glandin</synonym>
    <synonym>L-Prostaglandin e2</synonym>
    <synonym>Minprositin e2</synonym>
    <synonym>Minprostin e2</synonym>
    <synonym>Prostaglandin e</synonym>
    <synonym>Prostaglandin e2alpha</synonym>
    <synonym>Prostarmon e</synonym>
    <synonym>Prostin</synonym>
    <synonym>e2, Prostaglandin</synonym>
    <synonym>Prepidil gel</synonym>
    <synonym>alpha, Prostaglandin e2</synonym>
    <synonym>e2 alpha, Prostaglandin</synonym>
    <synonym>e2alpha, Prostaglandin</synonym>
    <synonym>alpha, PGE2</synonym>
    <synonym>Prostenon</synonym>
    <synonym>Gel, prepidil</synonym>
    <synonym>PGE2 alpha</synonym>
    <synonym>PGE2alpha</synonym>
    <synonym>Prostaglandin e2 alpha</synonym>
    <synonym>(3beta,4alpha,5alpha)-4-Methylcholesta-8,24-dien-3-ol</synonym>
    <synonym>4alpha-Methyl-5alpha-cholesta-8,24-dien-3beta-ol</synonym>
    <synonym>(3b,4a,5a)-4-Methylcholesta-8,24-dien-3-ol</synonym>
    <synonym>(3β,4α,5α)-4-methylcholesta-8,24-dien-3-ol</synonym>
    <synonym>4a-Methyl-5a-cholesta-8,24-dien-3b-ol</synonym>
    <synonym>4α-methyl-5α-cholesta-8,24-dien-3β-ol</synonym>
    <synonym>(4S,5S)-4,10,13-Trimethyl-17-(6-methylhept-5-en-2-yl)-2,3,4,5,6,7,11,12,14, 15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol</synonym>
    <synonym>4alpha-Methylzymosterol</synonym>
  </synonyms>
  <chemical_formula>C28H46O</chemical_formula>
  <average_molecular_weight>398.6642</average_molecular_weight>
  <monisotopic_moleculate_weight>398.354866094</monisotopic_moleculate_weight>
  <iupac_name>(2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol</iupac_name>
  <traditional_iupac>4α-methylzymosterol</traditional_iupac>
  <cas_registry_number>363-24-6</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C</smiles>
  <inchi>InChI=1S/C28H46O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h8,19-20,22-24,26,29H,7,9-17H2,1-6H3/t19-,20+,22-,23+,24+,26+,27-,28+/m1/s1</inchi>
  <inchikey>FOUJWBXBKVVHCJ-YIJYGBTNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Prostaglandins and related compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Cyclopentanols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclopentanol</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Prostaglandin skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>prostaglandins E</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>398.6642</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>398.354866094</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C28H46O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C28H46O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h8,19-20,22-24,26,29H,7,9-17H2,1-6H3/t19-,20+,22-,23+,24+,26+,27-,28+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FOUJWBXBKVVHCJ-YIJYGBTNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>125.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182474</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <phenol_explorer_compound_id/>
  <drugbank_id>DB00917</drugbank_id>
  <foodb_id>FDB022498</foodb_id>
  <kegg_id>C00584</kegg_id>
  <chemspider_id>4444059</chemspider_id>
  <pubchem_compound_id>5280360</pubchem_compound_id>
  <chebi_id>15551</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id>5Z13E-15S-1115-DIHYDROXY-9-OXOPROS</meta_cyc_id>
  <bigg_id>35424</bigg_id>
  <wikipedia_id>Prostaglandin_E2</wikipedia_id>
  <metlin_id>6089</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:43 UTC</creation_date>
  <update_date>2020-03-13 16:26:37 UTC</update_date>
  <accession>BMDB0001219</accession>
  <secondary_accessions>
    <accession>BMDB01219</accession>
  </secondary_accessions>
  <name>Chlordecone alcohol</name>
  <description/>
  <synonyms>
    <synonym>1,2,3,4,6,7,8,9,10,10-Decachloropentacyclo[5.3.0.0(2,6).0(3,9).0(4,8)]decan-5-ol</synonym>
    <synonym>Reduced kepone</synonym>
    <synonym>Kepol</synonym>
  </synonyms>
  <chemical_formula>C10H2Cl10O</chemical_formula>
  <average_molecular_weight>492.652</average_molecular_weight>
  <monisotopic_moleculate_weight>487.699091756</monisotopic_moleculate_weight>
  <iupac_name>1,2,3,4,6,7,8,9,10,10-decachloropentacyclo[5.3.0.0²,⁶.0³,⁹.0⁴,⁸]decan-5-ol</iupac_name>
  <traditional_iupac>kepol</traditional_iupac>
  <cas_registry_number>1034-41-9</cas_registry_number>
  <smiles>OC1C2(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C41Cl</smiles>
  <inchi>InChI=1S/C10H2Cl10O/c11-2-1(21)3(12)6(15)4(2,13)8(17)5(2,14)7(3,16)9(6,18)10(8,19)20/h1,21H</inchi>
  <inchikey>MBEIHNKADVMCJM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Monoterpenoids</sub_class>
    <direct_parent>Monoterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl chlorides</alternative_parent>
      <alternative_parent>Chlorohydrins</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alkyl chloride</substituent>
      <substituent>Alkyl halide</substituent>
      <substituent>Chlorohydrin</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Halohydrin</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoterpenoid</substituent>
      <substituent>Norbornane monoterpenoid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>organochlorine compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1,2,3,4,6,7,8,9,10,10-decachloropentacyclo[5.3.0.0²,⁶.0³,⁹.0⁴,⁸]decan-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>492.652</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>487.699091756</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC1C2(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C(Cl)(Cl)C41Cl</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H2Cl10O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H2Cl10O/c11-2-1(21)3(12)6(15)4(2,13)8(17)5(2,14)7(3,16)9(6,18)10(8,19)20/h1,21H</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MBEIHNKADVMCJM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>83.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358257</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02817</kegg_id>
  <drugbank_id/>
  <chemspider_id>13344</chemspider_id>
  <foodb_id>FDB022497</foodb_id>
  <pdbe_id/>
  <chebi_id>17184</chebi_id>
  <pubchem_compound_id>13946</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id>6088</metlin_id>
  <synthesis_reference>Fariss, Marc W.; Smith, J. Doyle; Blanke, Robert V.; Guzelian, Philip S.  Convenient preparation of chlordecone alcohol (kepone alcohol) and its deuterated, tritiated and dechlorinated derivatives.    Journal of Agricultural and Food Chemistry  (1982),  30(1),  185-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:44 UTC</creation_date>
  <update_date>2020-04-16 20:37:57 UTC</update_date>
  <accession>BMDB0001220</accession>
  <secondary_accessions>
    <accession>BMDB01220</accession>
  </secondary_accessions>
  <name>Prostaglandin E2</name>
  <description>Prostaglandin e2, also known as dinoprostone or PGE2, belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Thus, prostaglandin E2 is considered to be an eicosanoid lipid molecule. Prostaglandin e2 is a drug which is used for the termination of pregnancy during the second trimester (from the 12th through the 20th gestational week as calculated from the first day of the last normal menstrual period), as well as for evacuation of the uterine contents in the management of missed abortion or intrauterine fetal death up to 28 weeks of gestational age as calculated from the first day of the last normal menstrual period. also used in the management of nonmetastatic gestational trophoblastic disease (benign hydatidiform mole). other indications include improving the cervical inducibility (cervical "ripening") in pregnant women at or near term with a medical or obstetrical need for labor induction, and the management of postpartum hemorrhage. Prostaglandin e2 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Prostaglandin e2 exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>(15S)-Prostaglandin e2</synonym>
    <synonym>(5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid</synonym>
    <synonym>(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate</synonym>
    <synonym>(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoate</synonym>
    <synonym>(e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid</synonym>
    <synonym>(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acid</synonym>
    <synonym>Dinoproston</synonym>
    <synonym>Dinoprostona</synonym>
    <synonym>Dinoprostone</synonym>
    <synonym>Dinoprostonum</synonym>
    <synonym>PGE2</synonym>
    <synonym>Prepidil</synonym>
    <synonym>Propess</synonym>
    <synonym>Prostin e2</synonym>
    <synonym>Cervidil</synonym>
    <synonym>(5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid</synonym>
    <synonym>(5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,11Α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,11Α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid</synonym>
    <synonym>(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoate</synonym>
    <synonym>(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoate</synonym>
    <synonym>(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>(e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoate</synonym>
    <synonym>(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoate</synonym>
    <synonym>(-)-Prostaglandin e2</synonym>
    <synonym>(5Z,13E,15S)-11-alpha,15-Dihydroxy-9-oxoprost-5,13-dienoate</synonym>
    <synonym>(5Z,13E,15S)-11-alpha,15-Dihydroxy-9-oxoprost-5,13-dienoic acid</synonym>
    <synonym>5-trans-PGE2</synonym>
    <synonym>Glandin</synonym>
    <synonym>L-Prostaglandin e2</synonym>
    <synonym>Minprositin e2</synonym>
    <synonym>Minprostin e2</synonym>
    <synonym>Prostaglandin e</synonym>
    <synonym>Prostaglandin e2alpha</synonym>
    <synonym>Prostarmon e</synonym>
    <synonym>Prostin</synonym>
    <synonym>e2, Prostaglandin</synonym>
    <synonym>Prepidil gel</synonym>
    <synonym>alpha, Prostaglandin e2</synonym>
    <synonym>e2 alpha, Prostaglandin</synonym>
    <synonym>e2alpha, Prostaglandin</synonym>
    <synonym>alpha, PGE2</synonym>
    <synonym>Prostenon</synonym>
    <synonym>Gel, prepidil</synonym>
    <synonym>PGE2 alpha</synonym>
    <synonym>PGE2alpha</synonym>
    <synonym>Prostaglandin e2 alpha</synonym>
  </synonyms>
  <chemical_formula>C20H32O5</chemical_formula>
  <average_molecular_weight>352.4651</average_molecular_weight>
  <monisotopic_moleculate_weight>352.224974134</monisotopic_moleculate_weight>
  <iupac_name>(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid</iupac_name>
  <traditional_iupac>dinoprostone</traditional_iupac>
  <cas_registry_number>363-24-6</cas_registry_number>
  <smiles>CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1</inchi>
  <inchikey>XEYBRNLFEZDVAW-ARSRFYASSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Prostaglandins and related compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Cyclopentanols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclopentanol</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Prostaglandin skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>prostaglandins E</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>67 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.82</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>352.4651</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>352.224974134</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H32O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XEYBRNLFEZDVAW-ARSRFYASSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>99.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Succinate Signalling During Inflammation</name>
      <smpdb_id>SMP0120886</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440666</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by GC-TOF/MS</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
          <pubmed_id>29197344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00584</kegg_id>
  <drugbank_id>DB00917</drugbank_id>
  <chemspider_id>4444059</chemspider_id>
  <foodb_id>FDB022498</foodb_id>
  <pdbe_id/>
  <chebi_id>15551</chebi_id>
  <pubchem_compound_id>5280360</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>5Z13E-15S-1115-DIHYDROXY-9-OXOPROS</meta_cyc_id>
  <wikipedia_id>Prostaglandin_E2</wikipedia_id>
  <knapsack_id/>
  <bigg_id>35424</bigg_id>
  <metlin_id>6089</metlin_id>
  <synthesis_reference>Corey, Elias J.; Weinshenker, Ned M.; Schaaf, Thomas K.; Huber, Willy. Stereo-controlled synthesis of dl-prostaglandins F2a and E2. Journal of the American Chemical Society (1969), 91(20), 5675-7.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
      <pubmed_id>29197344</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00528</protein_accession>
      <name>NAD+ dependent 15-hydroxyprostaglandin dehydrogenase</name>
      <uniprot_id>Q309F3</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01608</protein_accession>
      <name>Prostaglandin E2 receptor EP4 subtype</name>
      <uniprot_id>Q8MJ08</uniprot_id>
      <gene_name>PTGER4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01609</protein_accession>
      <name>Prostaglandin E receptor 4, subtype EP4</name>
      <uniprot_id>Q1JPJ5</uniprot_id>
      <gene_name>PTGER4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01610</protein_accession>
      <name>Prostaglandin E2 receptor EP3 subtype</name>
      <uniprot_id>P34979</uniprot_id>
      <gene_name>PTGER3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01611</protein_accession>
      <name>EP2 receptor</name>
      <uniprot_id>Q8MJ09</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01612</protein_accession>
      <name>Prostaglandin E2 receptor EP1</name>
      <uniprot_id>Q95M52</uniprot_id>
      <gene_name>ep1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01613</protein_accession>
      <name>Prostaglandin E2 receptor EP4</name>
      <uniprot_id>Q95M50</uniprot_id>
      <gene_name>ep4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01614</protein_accession>
      <name>Prostaglandin E2 receptor EP2</name>
      <uniprot_id>Q95M51</uniprot_id>
      <gene_name>ep2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:45 UTC</creation_date>
  <update_date>2020-04-15 22:00:21 UTC</update_date>
  <accession>BMDB0001227</accession>
  <secondary_accessions>
    <accession>BMDB01227</accession>
  </secondary_accessions>
  <name>5-Thymidylic acid</name>
  <description/>
  <synonyms>
    <synonym>(DT)1</synonym>
    <synonym>5'-Thymidylic acid</synonym>
    <synonym>5'-TMP</synonym>
    <synonym>5-Methyl-dUMP</synonym>
    <synonym>Deoxyribosylthymine monophosphate</synonym>
    <synonym>Ribothymidine 5'-monophosphate</synonym>
    <synonym>Thymidine 5'-(dihydrogen phosphate)</synonym>
    <synonym>Thymidine 5'-phosphate</synonym>
    <synonym>Thymidine 5'-phosphoric acid</synonym>
    <synonym>Thymidine monophosphate</synonym>
    <synonym>Thymidine-5'-monophosphoric acid</synonym>
    <synonym>THYMIDINE-5'-phosphATE</synonym>
    <synonym>Thymidylate</synonym>
    <synonym>Thymidylic acid</synonym>
    <synonym>TMP</synonym>
    <synonym>Deoxythymidine 5'-phosphate</synonym>
    <synonym>Deoxythymidylic acid</synonym>
    <synonym>5'-Thymidylate</synonym>
    <synonym>Deoxyribosylthymine monophosphoric acid</synonym>
    <synonym>Ribothymidine 5'-monophosphoric acid</synonym>
    <synonym>Thymidine 5'-(dihydrogen phosphoric acid)</synonym>
    <synonym>Thymidine monophosphoric acid</synonym>
    <synonym>Thymidine-5'-monophosphate</synonym>
    <synonym>THYMIDINE-5'-phosphoric acid</synonym>
    <synonym>Deoxythymidine 5'-phosphoric acid</synonym>
    <synonym>Deoxythymidylate</synonym>
    <synonym>5-Thymidylate</synonym>
    <synonym>2'-Deoxythymidine 5'-monophosphate</synonym>
    <synonym>5'-dTMP</synonym>
    <synonym>Deoxy TMP</synonym>
    <synonym>Deoxythymidine 5'-monophosphate</synonym>
    <synonym>Deoxythymidine monophosphate</synonym>
    <synonym>Deoxythymydilate</synonym>
    <synonym>Deoxythymydilic acid</synonym>
    <synonym>dTMP</synonym>
    <synonym>Thymidine 5'-monophosphate</synonym>
    <synonym>Thymidine 5'-phosphorate</synonym>
    <synonym>Thymidine 5'MP</synonym>
    <synonym>Thymidine mononucleotide</synonym>
    <synonym>Thymidine phosphate</synonym>
    <synonym>Thymidine-5'-monophosphorate</synonym>
    <synonym>Thymidylic acids</synonym>
    <synonym>Acids, thymidylic</synonym>
    <synonym>Acid, thymidylic</synonym>
    <synonym>monoPhosphate, thymidine</synonym>
  </synonyms>
  <chemical_formula>C10H15N2O8P</chemical_formula>
  <average_molecular_weight>322.2085</average_molecular_weight>
  <monisotopic_moleculate_weight>322.056601978</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>thymidylate</traditional_iupac>
  <cas_registry_number>365-07-1</cas_registry_number>
  <smiles>CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O</smiles>
  <inchi>InChI=1S/C10H15N2O8P/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(20-8)4-19-21(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1</inchi>
  <inchikey>GYOZYWVXFNDGLU-XLPZGREQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside monophosphates. These are pyrimidine nucleotides with a monophosphate group  linked to the ribose moiety lacking a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine deoxyribonucleotides</sub_class>
    <direct_parent>Pyrimidine 2'-deoxyribonucleoside monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside monophosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxyribonucleotides</external_descriptor>
      <external_descriptor>thymidine 5'-monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>322.2085</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>322.056601978</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(O)=O)O2)C(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H15N2O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H15N2O8P/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(20-8)4-19-21(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GYOZYWVXFNDGLU-XLPZGREQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>145.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>66.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>27.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439111</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00364</kegg_id>
  <drugbank_id>DB01643</drugbank_id>
  <chemspider_id>9319</chemspider_id>
  <foodb_id>FDB030840</foodb_id>
  <pdbe_id/>
  <chebi_id>17013</chebi_id>
  <pubchem_compound_id>9700</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <wikipedia_id>Thymidine_monophosphate</wikipedia_id>
  <knapsack_id>C00019637</knapsack_id>
  <bigg_id>34753</bigg_id>
  <metlin_id>6092</metlin_id>
  <synthesis_reference>Scarano, E.  Enzymic formation of thymidylic acid from 5-methyl-5'-deoxycytidylic acid.    Bollettino - Societa Italiana di Biologia Sperimentale  (1958),  34  945.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00536</protein_accession>
      <name>Thymidylate synthase</name>
      <uniprot_id>Q2TA32</uniprot_id>
      <gene_name>TYMS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:47 UTC</creation_date>
  <update_date>2020-03-13 16:26:39 UTC</update_date>
  <accession>BMDB0001228</accession>
  <secondary_accessions>
    <accession>BMDB01228</accession>
  </secondary_accessions>
  <name>L-Glutamic acid 5-phosphate</name>
  <description/>
  <synonyms>
    <synonym>(2S)-2-Amino-5-oxo-5-(phosphonooxy)pentanoic acid</synonym>
    <synonym>5-oxo-5-(Phosphonooxy)-L-norvaline</synonym>
    <synonym>L-Glutam-5-yl phosphate</synonym>
    <synonym>L-Glutamate 5-phosphate</synonym>
    <synonym>L-Glutamyl 5-phosphate</synonym>
    <synonym>(2S)-2-Amino-5-oxo-5-(phosphonooxy)pentanoate</synonym>
    <synonym>L-Glutam-5-yl phosphoric acid</synonym>
    <synonym>L-Glutamic acid 5-phosphoric acid</synonym>
    <synonym>L-Glutamyl 5-phosphoric acid</synonym>
    <synonym>L-gamma-Glutamyl-5-p</synonym>
    <synonym>L-gamma-Glutamyl-5-phosphate</synonym>
    <synonym>L-Glutamate-5-phosphate</synonym>
    <synonym>L-Glutamyl-5-p</synonym>
    <synonym>gamma-Glutamyl phosphate</synonym>
  </synonyms>
  <chemical_formula>C5H10NO7P</chemical_formula>
  <average_molecular_weight>227.1092</average_molecular_weight>
  <monisotopic_moleculate_weight>227.019488191</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-5-oxo-5-(phosphonooxy)pentanoic acid</iupac_name>
  <traditional_iupac>L-gamma-glutamyl phosphate</traditional_iupac>
  <cas_registry_number>13254-53-0</cas_registry_number>
  <smiles>N[C@@H](CCC(=O)OP(O)(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H10NO7P/c6-3(5(8)9)1-2-4(7)13-14(10,11)12/h3H,1-2,6H2,(H,8,9)(H2,10,11,12)/t3-/m0/s1</inchi>
  <inchikey>PJRXVIJAERNUIP-VKHMYHEASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Glutamic acid and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Acyl monophosphates</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl monophosphate</substituent>
      <substituent>Acyl phosphate</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>gamma-glutamyl phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-5-oxo-5-(phosphonooxy)pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>227.1092</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>227.019488191</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCC(=O)OP(O)(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10NO7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10NO7P/c6-3(5(8)9)1-2-4(7)13-14(10,11)12/h3H,1-2,6H2,(H,8,9)(H2,10,11,12)/t3-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PJRXVIJAERNUIP-VKHMYHEASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>147.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36001</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03287</kegg_id>
  <drugbank_id/>
  <chemspider_id>167893</chemspider_id>
  <foodb_id>FDB022500</foodb_id>
  <pdbe_id/>
  <chebi_id>17798</chebi_id>
  <pubchem_compound_id>193475</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <knapsack_id/>
  <bigg_id>41564</bigg_id>
  <metlin_id>6093</metlin_id>
  <synthesis_reference>Journal of Heterocyclic Chemistry  (1987),  24(1),  279-82.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:48 UTC</creation_date>
  <update_date>2020-03-13 16:26:39 UTC</update_date>
  <accession>BMDB0001229</accession>
  <secondary_accessions>
    <accession>BMDB01229</accession>
  </secondary_accessions>
  <name>Dopaquinone</name>
  <description>Dopaquinone belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Dopaquinone is possibly soluble (in water) and a very strong basic compound (based on its pKa). Dopaquinone exists in all living organisms, ranging from bacteria to humans. Dopaquinone can be biosynthesized from L-dopa through the action of the enzyme tyrosinase. In cattle, dopaquinone is involved in the metabolic pathway called the tyrosine metabolism pathway.</description>
  <synonyms>
    <synonym>(S)-2-Amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoate</synonym>
    <synonym>(S)-2-Amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid</synonym>
    <synonym>O-Dopaquinone</synonym>
    <synonym>4-(2-Carboxy-2-aminoethyl)-1,2-benzoquinone</synonym>
    <synonym>Dopaquinone, (S)-isomer</synonym>
    <synonym>L-Dopaquinone</synonym>
  </synonyms>
  <chemical_formula>C9H9NO4</chemical_formula>
  <average_molecular_weight>195.1721</average_molecular_weight>
  <monisotopic_moleculate_weight>195.053157781</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid</iupac_name>
  <traditional_iupac>dopaquinone</traditional_iupac>
  <cas_registry_number>4430-97-1</cas_registry_number>
  <smiles>N[C@@H](CC1=CC(=O)C(=O)C=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C9H9NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6H,3,10H2,(H,13,14)/t6-/m0/s1</inchi>
  <inchikey>AHMIDUVKSGCHAU-LURJTMIESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>O-benzoquinones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>O-benzoquinone</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Quinone</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>amino acid zwitterion</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>195.1721</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>195.053157781</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CC1=CC(=O)C(=O)C=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H9NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H9NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6H,3,10H2,(H,13,14)/t6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AHMIDUVKSGCHAU-LURJTMIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>49.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326835</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00822</kegg_id>
  <drugbank_id/>
  <chemspider_id>388447</chemspider_id>
  <foodb_id>FDB022501</foodb_id>
  <pdbe_id/>
  <chebi_id>16852</chebi_id>
  <pubchem_compound_id>439316</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>DOPAQUINONE</meta_cyc_id>
  <wikipedia_id>L-Dopaquinone</wikipedia_id>
  <knapsack_id/>
  <bigg_id>36114</bigg_id>
  <metlin_id>354</metlin_id>
  <synthesis_reference>Land E J; Riley P A  Spontaneous redox reactions of dopaquinone and the balance between the eumelanic and phaeomelanic pathways.    Pigment cell research / sponsored by the European Society for Pigment Cell Research and the International Pigment Cell Society  (2000),  13(4),  273-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00662</protein_accession>
      <name>Tyrosinase</name>
      <uniprot_id>Q8MIU0</uniprot_id>
      <gene_name>TYR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:49 UTC</creation_date>
  <update_date>2020-03-13 16:26:40 UTC</update_date>
  <accession>BMDB0001231</accession>
  <secondary_accessions>
    <accession>BMDB01231</accession>
  </secondary_accessions>
  <name>27-Deoxy-5b-cyprinol</name>
  <description/>
  <synonyms>
    <synonym>(3alpha,5beta,7alpha,12alpha)-Cholestane-3,7,12,26-tetrol</synonym>
    <synonym>3alpha,7alpha,12alpha,26-Tetrahydroxy-5beta-cholestane</synonym>
    <synonym>5beta-Cholestane 3alpha,7alpha,12alpha,27-tetrol</synonym>
    <synonym>5beta-Cholestane-3alpha,7alpha,12alpha,26-tetraol</synonym>
    <synonym>Cholestane-3,7,12,26(27)-tetrol</synonym>
    <synonym>Cholestane-3,7,12,26-tetrol</synonym>
    <synonym>Cholestane-3,7,12,27-tetrol</synonym>
    <synonym>5beta-Cholestane-3alpha,7alpha,12alpha,26-tetrol</synonym>
    <synonym>(3a,5b,7a,12a)-Cholestane-3,7,12,26-tetrol</synonym>
    <synonym>(3Α,5β,7α,12α)-cholestane-3,7,12,26-tetrol</synonym>
    <synonym>3a,7a,12a,26-Tetrahydroxy-5b-cholestane</synonym>
    <synonym>3Α,7α,12α,26-tetrahydroxy-5β-cholestane</synonym>
    <synonym>5b-Cholestane 3a,7a,12a,27-tetrol</synonym>
    <synonym>5Β-cholestane 3α,7α,12α,27-tetrol</synonym>
    <synonym>5b-Cholestane-3a,7a,12a,26-tetraol</synonym>
    <synonym>5Β-cholestane-3α,7α,12α,26-tetraol</synonym>
    <synonym>5b-Cholestane-3a,7a,12a,26-tetrol</synonym>
    <synonym>5Β-cholestane-3α,7α,12α,26-tetrol</synonym>
    <synonym>(25R)-5-beta-Cholestane-3-alpha,7-alpha,12-alpha,26-tetraol</synonym>
    <synonym>5-b-Cholestane-3a-7-tetraol</synonym>
    <synonym>5-beta-Cholestane-3-alpha-7-alpha-12-alpha-26-tetraol</synonym>
    <synonym>5-beta-Cholestane-3a-7-tetraol</synonym>
    <synonym>5beta-Cholestane-3alpha,7alpha,12alpha,27-tetraol</synonym>
    <synonym>5beta-Cholestane-3alpha,7alpha,12alpha,27-tetrol</synonym>
    <synonym>5beta-Cholestane-3alpha,7alpha,12alpha,27alpha-tetrol</synonym>
    <synonym>5 beta-Cholestane-3alpha,7alpha,12alpha,26-tetrol</synonym>
    <synonym>5-CTTL</synonym>
    <synonym>Cholestane-3,7,12,26-tetrol, (3alpha,5alpha,7alpha,12alpha)-isomer</synonym>
  </synonyms>
  <chemical_formula>C27H48O4</chemical_formula>
  <average_molecular_weight>436.6676</average_molecular_weight>
  <monisotopic_moleculate_weight>436.355260024</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol</iupac_name>
  <traditional_iupac>5-cttl</traditional_iupac>
  <cas_registry_number>862-53-3</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)CO</smiles>
  <inchi>InChI=1S/C27H48O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h16-25,28-31H,5-15H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>XJZGNVBLVFOSKJ-XZULNKEGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Tetrahydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Fatty alcohols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>26-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydroxy bile acid, alcohol, or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>12alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>26-hydroxy steroid</external_descriptor>
      <external_descriptor>3alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>7alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>C27 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>C27 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>17.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>436.6676</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>436.355260024</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H48O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H48O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h16-25,28-31H,5-15H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XJZGNVBLVFOSKJ-XZULNKEGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>124.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>53.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334101</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05446</kegg_id>
  <drugbank_id/>
  <chemspider_id>167758</chemspider_id>
  <foodb_id>FDB022502</foodb_id>
  <pdbe_id/>
  <chebi_id>17278</chebi_id>
  <pubchem_compound_id>193321</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <knapsack_id/>
  <bigg_id>45828</bigg_id>
  <metlin_id>6095</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:50 UTC</creation_date>
  <update_date>2020-04-15 22:28:15 UTC</update_date>
  <accession>BMDB0001232</accession>
  <secondary_accessions>
    <accession>BMDB01232</accession>
  </secondary_accessions>
  <name>4-Nitrophenol</name>
  <description>4-Nitrophenol, also known as niphen or PNP, belongs to the class of organic compounds known as nitrophenols. Nitrophenols are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms. 4-Nitrophenol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 4-Nitrophenol exists in all living species, ranging from bacteria to humans. 4-Nitrophenol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>4-Hydroxynitrobenzene</synonym>
    <synonym>Niphen</synonym>
    <synonym>p-Hydroxynitrobenzene</synonym>
    <synonym>p-Nitrophenol</synonym>
    <synonym>Paranitrophenol</synonym>
    <synonym>PNP</synonym>
    <synonym>Mononitrophenol</synonym>
    <synonym>1-Hydroxy-4-nitrobenzene</synonym>
    <synonym>4-Nitrophenol, (18)O-labeled CPD</synonym>
    <synonym>4-Nitrophenol, 1-(13)C-labeled CPD</synonym>
    <synonym>4-Nitrophenol, manganese (2+) salt</synonym>
    <synonym>4-Nitrophenol, silver(2+) salt</synonym>
    <synonym>4-Nitrophenol, sodium salt, (2:1), dihydrate</synonym>
    <synonym>4-Nitrophenol, tin (4+) salt</synonym>
    <synonym>4-Nitrophenol, 2,6-(13)C2-labeled CPD</synonym>
    <synonym>4-Nitrophenol, 2-(14)C-labeled CPD</synonym>
    <synonym>4-Nitrophenol, copper(1+) salt</synonym>
    <synonym>4-Nitrophenol, potassium salt</synonym>
    <synonym>4-Nitrophenol, tin (2+) salt</synonym>
    <synonym>4-Nitrophenol, 14C-labeled CPD</synonym>
    <synonym>4-Nitrophenol, ammonium salt</synonym>
    <synonym>4-Nitrophenol, ion(1-)</synonym>
    <synonym>4-Nitrophenol, ion(1-) hydride</synonym>
    <synonym>4-Nitrophenol, sodium salt</synonym>
    <synonym>4-Nitrophenol, 2,6-(14)C2-labeled CPD</synonym>
    <synonym>4-Nitrophenol, aluminum salt</synonym>
    <synonym>4-Nitrophenol, cesium salt</synonym>
    <synonym>4-Nitrophenol, iron(3+) salt</synonym>
    <synonym>4-Nitrophenol, lithium salt</synonym>
    <synonym>4-Nitrophenol, manganese salt</synonym>
    <synonym>4-Nitrophenol, zinc salt</synonym>
    <synonym>4-Hydroxy-1-nitrobenzene</synonym>
    <synonym>4-Nitrophenolate</synonym>
    <synonym>4-Nitrophenol</synonym>
  </synonyms>
  <chemical_formula>C6H5NO3</chemical_formula>
  <average_molecular_weight>139.1088</average_molecular_weight>
  <monisotopic_moleculate_weight>139.026943031</monisotopic_moleculate_weight>
  <iupac_name>4-nitrophenol</iupac_name>
  <traditional_iupac>P-nitrophenol</traditional_iupac>
  <cas_registry_number>100-02-7</cas_registry_number>
  <smiles>OC1=CC=C(C=C1)[N+]([O-])=O</smiles>
  <inchi>InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H</inchi>
  <inchikey>BTJIUGUIPKRLHP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as nitrophenols. Nitrophenols are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Nitrophenols</sub_class>
    <direct_parent>Nitrophenols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Nitroaromatic compounds</alternative_parent>
      <alternative_parent>Nitrobenzenes</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic oxoazanium compounds</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Allyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>C-nitro compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Nitroaromatic compound</substituent>
      <substituent>Nitrobenzene</substituent>
      <substituent>Nitrophenol</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitro compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxoazanium</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>mononitrophenol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>113.8 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>11.6 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.91</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-nitrophenol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>139.1088</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>139.026943031</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC1=CC=C(C=C1)[N+]([O-])=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H5NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BTJIUGUIPKRLHP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>98</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4839</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00870</kegg_id>
  <drugbank_id>DB04417</drugbank_id>
  <chemspider_id>955</chemspider_id>
  <foodb_id>FDB022503</foodb_id>
  <pdbe_id/>
  <chebi_id>16836</chebi_id>
  <pubchem_compound_id>980</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>P-NITROPHENOL</meta_cyc_id>
  <wikipedia_id>4-Nitrophenol</wikipedia_id>
  <knapsack_id/>
  <bigg_id>36247</bigg_id>
  <metlin_id>4100</metlin_id>
  <synthesis_reference>Fache, Eric; Righini, Sebastien.  Preparation of a nitrophenol.    Fr. Demande  (2004),     35 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00062</protein_accession>
      <name>Cytochrome P450 2E1</name>
      <uniprot_id>O18963</uniprot_id>
      <gene_name>CYP2E1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:51 UTC</creation_date>
  <update_date>2020-03-13 16:26:41 UTC</update_date>
  <accession>BMDB0001235</accession>
  <secondary_accessions>
    <accession>BMDB01235</accession>
  </secondary_accessions>
  <name>5-Aminoimidazole ribonucleotide</name>
  <description/>
  <synonyms>
    <synonym>1-(5'-Phosphoribosyl)-5-aminoimidazole</synonym>
    <synonym>1-(5-Phospho-D-ribosyl)-5-aminoimidazole</synonym>
    <synonym>5'-Phosphoribosyl-5-aminoimidazole</synonym>
    <synonym>5-Amino-1-beta-D-ribofuranosyl-5'-(dihydrogen phosphate)-imidazole</synonym>
    <synonym>5-Amino-1-ribofuranosylimidazole 5'-phosphate</synonym>
    <synonym>AIR</synonym>
    <synonym>Aminoimidazole ribonucleotide</synonym>
    <synonym>Aminoimidazole ribotide</synonym>
    <synonym>Phosphoribosylaminoimidazole</synonym>
    <synonym>5-Amino-1-(5-phospho-D-ribosyl)imidazole</synonym>
    <synonym>5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole</synonym>
    <synonym>5-Amino-1-b-D-ribofuranosyl-5'-(dihydrogen phosphate)-imidazole</synonym>
    <synonym>5-Amino-1-b-D-ribofuranosyl-5'-(dihydrogen phosphoric acid)-imidazole</synonym>
    <synonym>5-Amino-1-beta-D-ribofuranosyl-5'-(dihydrogen phosphoric acid)-imidazole</synonym>
    <synonym>5-Amino-1-β-D-ribofuranosyl-5'-(dihydrogen phosphate)-imidazole</synonym>
    <synonym>5-Amino-1-β-D-ribofuranosyl-5'-(dihydrogen phosphoric acid)-imidazole</synonym>
    <synonym>5-Amino-1-ribofuranosylimidazole 5'-phosphoric acid</synonym>
    <synonym>5-Amino-1-(5-phospho-b-D-ribosyl)imidazole</synonym>
    <synonym>5-Amino-1-(5-phospho-β-D-ribosyl)imidazole</synonym>
    <synonym>5-Aminoimidazole ribotide</synonym>
    <synonym>Aminoimidazole ribotide, (beta-D-ribofuranosyl)-isomer</synonym>
    <synonym>Aminoimidazole ribotide, (alpha-D-ribofuranosyl)-isomer</synonym>
    <synonym>Aminoimidazole ribotide, phosphonoribofuranosyl-isomer</synonym>
  </synonyms>
  <chemical_formula>C8H14N3O7P</chemical_formula>
  <average_molecular_weight>295.1864</average_molecular_weight>
  <monisotopic_moleculate_weight>295.056936329</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(5-amino-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>5-aminoimidazole ribotide</traditional_iupac>
  <cas_registry_number>25635-88-5</cas_registry_number>
  <smiles>NC1=CN=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C8H14N3O7P/c9-5-1-10-3-11(5)8-7(13)6(12)4(18-8)2-17-19(14,15)16/h1,3-4,6-8,12-13H,2,9H2,(H2,14,15,16)/t4-,6-,7-,8-/m1/s1</inchi>
  <inchikey>PDACUKOKVHBVHJ-XVFCMESISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Aminoimidazoles</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazole ribonucleosides and ribonucleotides</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminoimidazole</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazole ribonucleoside</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>7.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(5-amino-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>295.1864</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>295.056936329</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=CN=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H14N3O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H14N3O7P/c9-5-1-10-3-11(5)8-7(13)6(12)4(18-8)2-17-19(14,15)16/h1,3-4,6-8,12-13H,2,9H2,(H2,14,15,16)/t4-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PDACUKOKVHBVHJ-XVFCMESISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>160.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30100</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03373</kegg_id>
  <foodb_id>FDB022504</foodb_id>
  <pubchem_compound_id>161500</pubchem_compound_id>
  <chemspider_id>141854</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>138560</chebi_id>
  <meta_cyc_id>5-PHOSPHORIBOSYL-5-AMINOIMIDAZOLE</meta_cyc_id>
  <knapsack_id>C00019655</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>41727</bigg_id>
  <wikipedia_id>5-Aminoimidazole_ribotide</wikipedia_id>
  <metlin_id>6097</metlin_id>
  <synthesis_reference>Groziak M P; Bhat B; Leonard N J  Nonenzymatic synthesis of 5-aminoimidazole ribonucleoside and recognition of its facile rearrangement.    Proceedings of the National Academy of Sciences of the United States of America  (1988),  85(19),  7174-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00600</protein_accession>
      <name>Trifunctional purine biosynthetic protein adenosine-3</name>
      <uniprot_id>Q59A32</uniprot_id>
      <gene_name>GART</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00935</protein_accession>
      <name>Adenylosuccinate lyase</name>
      <uniprot_id>A3KN12</uniprot_id>
      <gene_name>ADSL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:52 UTC</creation_date>
  <update_date>2020-04-14 22:48:59 UTC</update_date>
  <accession>BMDB0001238</accession>
  <secondary_accessions>
    <accession>BMDB01238</accession>
  </secondary_accessions>
  <name>N-Acetylserotonin</name>
  <description>N-Acetylserotonin, also known as 5-hydroxymelatonin or ASE, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. N-Acetylserotonin is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetylserotonin exists in all living organisms, ranging from bacteria to humans. N-Acetylserotonin participates in a number of enzymatic reactions, within cattle. In particular, N-Acetylserotonin can be biosynthesized from serotonin and acetyl-CoA; which is mediated by the enzyme serotonin N-acetyltransferase. In addition, N-Acetylserotonin and S-adenosylmethionine can be converted into melatonin and S-adenosylhomocysteine; which is catalyzed by the enzyme acetylserotonin O-methyltransferase. In cattle, N-acetylserotonin is involved in the metabolic pathway called the tryptophan metabolism pathway.</description>
  <synonyms>
    <synonym>N-(2-(5-Hydroxy-1H-indol-3-yl)ethyl)acetamide</synonym>
    <synonym>N-Acetyl-5-hydroxytryptamine</synonym>
    <synonym>5-Hydroxy-N-acetyltryptamine</synonym>
    <synonym>5-Hydroxymelatonin</synonym>
    <synonym>ASE</synonym>
    <synonym>Desmethylmelatonin</synonym>
    <synonym>O-Demethylmelatonin</synonym>
    <synonym>N-Acetylhydroxytryptamine</synonym>
  </synonyms>
  <chemical_formula>C12H14N2O2</chemical_formula>
  <average_molecular_weight>218.2518</average_molecular_weight>
  <monisotopic_moleculate_weight>218.105527702</monisotopic_moleculate_weight>
  <iupac_name>N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]acetamide</iupac_name>
  <traditional_iupac>N-acetylserotonin</traditional_iupac>
  <cas_registry_number>1210-83-9</cas_registry_number>
  <smiles>CC(=O)NCCC1=CNC2=C1C=C(O)C=C2</smiles>
  <inchi>InChI=1S/C12H14N2O2/c1-8(15)13-5-4-9-7-14-12-3-2-10(16)6-11(9)12/h2-3,6-7,14,16H,4-5H2,1H3,(H,13,15)</inchi>
  <inchikey>MVAWJSIDNICKHF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Hydroxyindoles</sub_class>
    <direct_parent>Hydroxyindoles</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>3-alkylindoles</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-alkylindole</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyindole</substituent>
      <substituent>Indole</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>acetamides</external_descriptor>
      <external_descriptor>hydroxyindoles</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]acetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>218.2518</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>218.105527702</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)NCCC1=CNC2=C1C=C(O)C=C2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H14N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H14N2O2/c1-8(15)13-5-4-9-7-14-12-3-2-10(16)6-11(9)12/h2-3,6-7,14,16H,4-5H2,1H3,(H,13,15)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MVAWJSIDNICKHF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>65.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>61.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37988</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451986</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00978</kegg_id>
  <foodb_id>FDB031021</foodb_id>
  <pubchem_compound_id>903</pubchem_compound_id>
  <chemspider_id>879</chemspider_id>
  <drugbank_id>DB04275</drugbank_id>
  <pdbe_id/>
  <chebi_id>17697</chebi_id>
  <meta_cyc_id>N-ACETYL-SEROTONIN</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>36527</bigg_id>
  <wikipedia_id>N-acetyl-serotonin</wikipedia_id>
  <metlin_id>366</metlin_id>
  <synthesis_reference>Balemans M G; Mans D; Smith I; Van Benthem J  The influence of GABA on the synthesis of N-acetylserotonin, melatonin, O-acetyl-5-hydroxytryptophol and O-acetyl-5-methoxytryptophol in the pineal gland of the male Wistar rat.    Reproduction, nutrition, development  (1983),  23(1),  151-60.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00410</protein_accession>
      <name>Hydroxyindole O-methyltransferase</name>
      <uniprot_id>P10950</uniprot_id>
      <gene_name>ASMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:54 UTC</creation_date>
  <update_date>2020-03-13 16:26:42 UTC</update_date>
  <accession>BMDB0001240</accession>
  <secondary_accessions>
    <accession>BMDB01240</accession>
  </secondary_accessions>
  <name>Pseudooxynicotine</name>
  <description/>
  <synonyms>
    <synonym>4-(Methylamino)-1-(3-pyridinyl)-1-butanone</synonym>
    <synonym>4-(Methylamino)-1-(3-pyridyl)-1-butanone</synonym>
    <synonym>4-(Methylamino)-1-(pyridin-3-yl)butan-1-one</synonym>
  </synonyms>
  <chemical_formula>C10H14N2O</chemical_formula>
  <average_molecular_weight>178.231</average_molecular_weight>
  <monisotopic_moleculate_weight>178.11061308</monisotopic_moleculate_weight>
  <iupac_name>4-(methylamino)-1-(pyridin-3-yl)butan-1-one</iupac_name>
  <traditional_iupac>pseudooxynicotine</traditional_iupac>
  <cas_registry_number>2055-23-4</cas_registry_number>
  <smiles>CNCCCC(=O)C1=CC=CN=C1</smiles>
  <inchi>InChI=1S/C10H14N2O/c1-11-6-3-5-10(13)9-4-2-7-12-8-9/h2,4,7-8,11H,3,5-6H2,1H3</inchi>
  <inchikey>SGDIDUFQYHRMPR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Aryl alkyl ketones</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Gamma-amino ketones</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridines and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Aryl alkyl ketone</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Gamma-aminoketone</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aminoacylpyridine</external_descriptor>
      <external_descriptor>pyridine alkaloid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-(methylamino)-1-(pyridin-3-yl)butan-1-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>178.231</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>178.11061308</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CNCCCC(=O)C1=CC=CN=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H14N2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H14N2O/c1-11-6-3-5-10(13)9-4-2-7-12-8-9/h2,4,7-8,11H,3,5-6H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SGDIDUFQYHRMPR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>41.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345615</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C20361</kegg_id>
  <foodb_id>FDB022506</foodb_id>
  <pubchem_compound_id>434</pubchem_compound_id>
  <chemspider_id>421</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>37753</chebi_id>
  <meta_cyc_id>CPD-14092</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6100</metlin_id>
  <synthesis_reference>Kisaki, Takuro; Maeda, Susumu; Sasaki, So; Mikami, Yoichi; Uchida, Setsuko.  Pseudooxynicotine.    Jpn. Kokai Tokkyo Koho  (1977),     6 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:55 UTC</creation_date>
  <update_date>2020-03-13 16:26:42 UTC</update_date>
  <accession>BMDB0001241</accession>
  <secondary_accessions>
    <accession>BMDB01241</accession>
  </secondary_accessions>
  <name>2-Aminomuconic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Aminomuconate</synonym>
    <synonym>2-Aminohexa-2,4-dienedioate</synonym>
    <synonym>2-Aminohexa-2,4-dienedioic acid</synonym>
    <synonym>O-Aminomuconate</synonym>
    <synonym>2-Amino-muconate</synonym>
  </synonyms>
  <chemical_formula>C6H7NO4</chemical_formula>
  <average_molecular_weight>157.1241</average_molecular_weight>
  <monisotopic_moleculate_weight>157.037507717</monisotopic_moleculate_weight>
  <iupac_name>(2Z,4E)-5-aminohexa-2,4-dienedioic acid</iupac_name>
  <traditional_iupac>2-aminomuconate semialdehyde</traditional_iupac>
  <cas_registry_number>4548-99-6</cas_registry_number>
  <smiles>N\C(=C\C=C/C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H7NO4/c7-4(6(10)11)2-1-3-5(8)9/h1-3H,7H2,(H,8,9)(H,10,11)/b3-1-,4-2+</inchi>
  <inchikey>ZRHONLCTYUYMIQ-HSFFGMMNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Enamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Enamine</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2Z,4E)-5-aminohexa-2,4-dienedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>157.1241</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>157.037507717</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N\C(=C\C=C/C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H7NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H7NO4/c7-4(6(10)11)2-1-3-5(8)9/h1-3H,7H2,(H,8,9)(H,10,11)/b3-1-,4-2+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZRHONLCTYUYMIQ-HSFFGMMNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>100.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335865</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02220</kegg_id>
  <pubchem_compound_id>5280499</pubchem_compound_id>
  <chemspider_id>4444139</chemspider_id>
  <foodb_id>FDB022507</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>15745</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>2-Aminomuconic acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>1445654</bigg_id>
  <metlin_id>321</metlin_id>
  <synthesis_reference>He, Z.; Spain, J. C. Preparation of 2-aminomuconate from 2-aminophenol by coupled enzymatic dioxygenation and dehydrogenation reactions. Journal of Industrial Microbiology &amp; Biotechnology (1999), 23(2), 138-142.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:56 UTC</creation_date>
  <update_date>2020-03-13 16:26:43 UTC</update_date>
  <accession>BMDB0001242</accession>
  <secondary_accessions>
    <accession>BMDB01242</accession>
  </secondary_accessions>
  <name>Obtusifoliol</name>
  <description/>
  <synonyms>
    <synonym>4,4-Dimethyl-14a-hydroxymethyl-5a-cholesta-8,24-dien-3b-ol</synonym>
    <synonym>4,4-Dimethyl-14alpha-hydroxymethyl-5alpha-cholesta-8,24-dien-3beta-ol</synonym>
  </synonyms>
  <chemical_formula>C30H50O2</chemical_formula>
  <average_molecular_weight>442.7168</average_molecular_weight>
  <monisotopic_moleculate_weight>442.381080844</monisotopic_moleculate_weight>
  <iupac_name>11-(hydroxymethyl)-2,6,6,15-tetramethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol</iupac_name>
  <traditional_iupac>obtusifoliol</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(CCC=C(C)C)C1CCC2(CO)C3=C(CCC12C)C1(C)CCC(O)C(C)(C)C1CC3</smiles>
  <inchi>InChI=1S/C30H50O2/c1-20(2)9-8-10-21(3)22-14-18-30(19-31)24-11-12-25-27(4,5)26(32)15-16-28(25,6)23(24)13-17-29(22,30)7/h9,21-22,25-26,31-32H,8,10-19H2,1-7H3</inchi>
  <inchikey>DWVYYKFZEDMMPU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Triterpenoids</sub_class>
    <direct_parent>Triterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>3-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Steroid</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a 3-&amp;beta;-hydroxysterol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>11-(hydroxymethyl)-2,6,6,15-tetramethyl-14-(6-methylhept-5-en-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>442.7168</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>442.381080844</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(CCC=C(C)C)C1CCC2(CO)C3=C(CCC12C)C1(C)CCC(O)C(C)(C)C1CC3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C30H50O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C30H50O2/c1-20(2)9-8-10-21(3)22-14-18-30(19-31)24-11-12-25-27(4,5)26(32)15-16-28(25,6)23(24)13-17-29(22,30)7/h9,21-22,25-26,31-32H,8,10-19H2,1-7H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DWVYYKFZEDMMPU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>136.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>55.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180515</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01943</kegg_id>
  <foodb_id>FDB030262</foodb_id>
  <pubchem_compound_id>656449</pubchem_compound_id>
  <chemspider_id>570838</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <knapsack_id>C00007368</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6102</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00014</protein_accession>
      <name>Lanosterol 14-alpha demethylase</name>
      <uniprot_id>Q4PJW3</uniprot_id>
      <gene_name>CYP51A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:57 UTC</creation_date>
  <update_date>2020-03-13 16:26:43 UTC</update_date>
  <accession>BMDB0001243</accession>
  <secondary_accessions>
    <accession>BMDB01243</accession>
  </secondary_accessions>
  <name>Isobutyryl-CoA</name>
  <description/>
  <synonyms>
    <synonym>2-Methylpropanoyl-CoA</synonym>
    <synonym>2-Methylpropionyl-CoA</synonym>
    <synonym>Isobutanoyl-CoA</synonym>
    <synonym>2-Methylpropanoyl-coenzyme A</synonym>
    <synonym>2-Methylpropionyl-coenzyme A</synonym>
    <synonym>alpha-Methylpropionyl-CoA</synonym>
    <synonym>alpha-Methylpropionyl-coenzyme A</synonym>
    <synonym>Isobutyryl- CoA</synonym>
    <synonym>Isobutyryl- coenzyme A</synonym>
    <synonym>S-(2-Methylpropanoate</synonym>
    <synonym>S-(2-Methylpropanoate)CoA</synonym>
    <synonym>S-(2-Methylpropanoate)coenzyme A</synonym>
    <synonym>S-(2-Methylpropanoic acid</synonym>
    <synonym>S-(2-Methylpropanoyl)-CoA</synonym>
    <synonym>S-(2-Methylpropanoyl)-coenzyme A</synonym>
    <synonym>Isobutyryl-coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C25H42N7O17P3S</chemical_formula>
  <average_molecular_weight>837.624</average_molecular_weight>
  <monisotopic_moleculate_weight>837.157073179</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>isobutyryl- coa</traditional_iupac>
  <cas_registry_number>15621-60-0</cas_registry_number>
  <smiles>CC(C)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C25H42N7O17P3S/c1-13(2)24(37)53-8-7-27-15(33)5-6-28-22(36)19(35)25(3,4)10-46-52(43,44)49-51(41,42)45-9-14-18(48-50(38,39)40)17(34)23(47-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-14,17-19,23,34-35H,5-10H2,1-4H3,(H,27,33)(H,28,36)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,17-,18-,19+,23-/m1/s1</inchi>
  <inchikey>AEWHYWSPVRZHCT-NDZSKPAWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>methyl-branched fatty acyl-CoA</external_descriptor>
      <external_descriptor>short-chain fatty acyl-CoA</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>837.624</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>837.157073179</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H42N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C25H42N7O17P3S/c1-13(2)24(37)53-8-7-27-15(33)5-6-28-22(36)19(35)25(3,4)10-46-52(43,44)49-51(41,42)45-9-14-18(48-50(38,39)40)17(34)23(47-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-14,17-19,23,34-35H,5-10H2,1-4H3,(H,27,33)(H,28,36)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,17-,18-,19+,23-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AEWHYWSPVRZHCT-NDZSKPAWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>181.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>75.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34627</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00630</kegg_id>
  <foodb_id>FDB022508</foodb_id>
  <pubchem_compound_id>3036931</pubchem_compound_id>
  <chemspider_id>2300823</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>15479</chebi_id>
  <meta_cyc_id>ISOBUTYRYL-COA</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>35538</bigg_id>
  <wikipedia_id>Isobutyryl-CoA</wikipedia_id>
  <metlin_id>6103</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00894</protein_accession>
      <name>Isobutyryl-CoA dehydrogenase, mitochondrial</name>
      <uniprot_id>Q0NXR6</uniprot_id>
      <gene_name>ACAD8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:42:58 UTC</creation_date>
  <update_date>2020-03-13 16:26:44 UTC</update_date>
  <accession>BMDB0001244</accession>
  <secondary_accessions>
    <accession>BMDB01244</accession>
  </secondary_accessions>
  <name>15-Keto-13,14-dihydroprostaglandin A2</name>
  <description/>
  <synonyms>
    <synonym>(5Z)-9,15-Dioxo-prosta-5,10-dien-1-Oate</synonym>
    <synonym>(5Z)-9,15-Dioxo-prosta-5,10-dien-1-Oic acid</synonym>
    <synonym>15-Keto-13,14-dihydro-pga2</synonym>
    <synonym>9,15-Dioxo-5Z,10-prostadienoate</synonym>
    <synonym>9,15-Dioxo-5Z,10-prostadienoic acid</synonym>
    <synonym>DHK-PGA2</synonym>
    <synonym>15-Keto-13,14-dihydroprostaglandin a2</synonym>
  </synonyms>
  <chemical_formula>C20H30O4</chemical_formula>
  <average_molecular_weight>334.4498</average_molecular_weight>
  <monisotopic_moleculate_weight>334.214409448</monisotopic_moleculate_weight>
  <iupac_name>(5Z)-7-[(1R,5S)-2-oxo-5-(3-oxooctyl)cyclopent-3-en-1-yl]hept-5-enoic acid</iupac_name>
  <traditional_iupac>13,14-dihydro-15-keto-PGA2</traditional_iupac>
  <cas_registry_number>74872-89-2</cas_registry_number>
  <smiles>CCCCCC(=O)CC[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,13,15-16,18H,2-3,5-6,8-12,14H2,1H3,(H,23,24)/b7-4-/t16-,18+/m0/s1</inchi>
  <inchikey>FMKLAIBZMCURLI-BFVRRIQPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Prostaglandins and related compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Prostaglandin skeleton</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Prostaglandins</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5Z)-7-[(1R,5S)-2-oxo-5-(3-oxooctyl)cyclopent-3-en-1-yl]hept-5-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>334.4498</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>334.214409448</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCC(=O)CC[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H30O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,13,15-16,18H,2-3,5-6,8-12,14H2,1H3,(H,23,24)/b7-4-/t16-,18+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FMKLAIBZMCURLI-BFVRRIQPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>71.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>97.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343842</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022509</foodb_id>
  <pubchem_compound_id>5283042</pubchem_compound_id>
  <chemspider_id>4446169</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>89315</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:00 UTC</creation_date>
  <update_date>2020-03-13 16:26:44 UTC</update_date>
  <accession>BMDB0001245</accession>
  <secondary_accessions>
    <accession>BMDB01245</accession>
  </secondary_accessions>
  <name>dCDP</name>
  <description/>
  <synonyms>
    <synonym>2'-Deoxycytidine 5'-diphosphate</synonym>
    <synonym>2'-Deoxycytidine diphosphate</synonym>
    <synonym>D-1beta-Ribofuranosylcytosine diphosphate</synonym>
    <synonym>Deoxycytidine diphosphate</synonym>
    <synonym>2'-Deoxycytidine 5'-diphosphoric acid</synonym>
    <synonym>2'-Deoxycytidine diphosphoric acid</synonym>
    <synonym>D-1b-Ribofuranosylcytosine diphosphate</synonym>
    <synonym>D-1b-Ribofuranosylcytosine diphosphoric acid</synonym>
    <synonym>D-1beta-Ribofuranosylcytosine diphosphoric acid</synonym>
    <synonym>D-1Β-ribofuranosylcytosine diphosphate</synonym>
    <synonym>D-1Β-ribofuranosylcytosine diphosphoric acid</synonym>
    <synonym>Deoxycytidine diphosphoric acid</synonym>
    <synonym>2'-Deoxy-cytidine 5'-pyrophosphate</synonym>
    <synonym>2'-Deoxy-cytidine pyrophosphate</synonym>
    <synonym>2'-Deoxycytidine-5'-diphosphate</synonym>
    <synonym>4-Amino-1-[2-deoxy-5-O-[hydroxy(phosphonooxy)phosphinyl]-beta-D-erythro-pentofuranosyl]-2(1H)-pyrimidinone</synonym>
    <synonym>4-Amino-1-[2-deoxy-5-O-[hydroxy(phosphonooxy)phosphinyl]-beta-delta-erythro-pentofuranosyl]-2(1H)-pyrimidinone</synonym>
    <synonym>delta-1beta-Ribofuranosylcytosine diphosphate</synonym>
    <synonym>Deoxy-CDP</synonym>
    <synonym>Deoxycytidine 5'-diphosphate</synonym>
  </synonyms>
  <chemical_formula>C9H15N3O10P2</chemical_formula>
  <average_molecular_weight>387.177</average_molecular_weight>
  <monisotopic_moleculate_weight>387.023266739</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>dCDP</traditional_iupac>
  <cas_registry_number>800-73-7</cas_registry_number>
  <smiles>NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O1</smiles>
  <inchi>InChI=1S/C9H15N3O10P2/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(21-8)4-20-24(18,19)22-23(15,16)17/h1-2,5-6,8,13H,3-4H2,(H,18,19)(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1</inchi>
  <inchikey>FTDHDKPUHBLBTL-SHYZEUOFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organic oxoanionic compounds</class>
    <sub_class>Organic pyrophosphates</sub_class>
    <direct_parent>Organic pyrophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2'-deoxycytidine phosphate</external_descriptor>
      <external_descriptor>Deoxyribonucleotides</external_descriptor>
      <external_descriptor>pyrimidine 2'-deoxyribonucleoside 5'-diphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.005</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>387.177</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>387.023266739</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)N(C=C1)[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H15N3O10P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H15N3O10P2/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(21-8)4-20-24(18,19)22-23(15,16)17/h1-2,5-6,8,13H,3-4H2,(H,18,19)(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FTDHDKPUHBLBTL-SHYZEUOFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>201.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>74.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>30.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447974</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447975</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00705</kegg_id>
  <foodb_id>FDB022510</foodb_id>
  <pubchem_compound_id>150855</pubchem_compound_id>
  <chemspider_id>132961</chemspider_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>28846</chebi_id>
  <meta_cyc_id>DCDP</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>50858</bigg_id>
  <wikipedia_id>Deoxycytidine_diphosphate</wikipedia_id>
  <metlin_id>6105</metlin_id>
  <synthesis_reference>Nara, Takashi; Misawa, Masanaru.  Bacterial phosphorylation of 5'-deoxycytidine monophosphate to di-or triphosphate.    Jpn. Tokkyo Koho  (1971),     2 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:01 UTC</creation_date>
  <update_date>2020-03-13 16:26:45 UTC</update_date>
  <accession>BMDB0001247</accession>
  <secondary_accessions>
    <accession>BMDB01247</accession>
  </secondary_accessions>
  <name>Aluminum</name>
  <description>Aluminum, also known as aluminium ion or al(3+), belongs to the class of inorganic compounds known as homogeneous post-transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a post-transition metal atom. Aluminum is possibly soluble (in water) and possibly neutral.</description>
  <synonyms>
    <synonym>Al(3+)</synonym>
    <synonym>Aluminium ion</synonym>
    <synonym>ALUMINUM ion</synonym>
    <synonym>Al</synonym>
    <synonym>Alloy</synonym>
    <synonym>ALN</synonym>
    <synonym>Alugel</synonym>
    <synonym>Alum</synonym>
    <synonym>Alumen</synonym>
    <synonym>Alumina</synonym>
    <synonym>Alloys</synonym>
  </synonyms>
  <chemical_formula>Al</chemical_formula>
  <average_molecular_weight>26.9815</average_molecular_weight>
  <monisotopic_moleculate_weight>26.981538441</monisotopic_moleculate_weight>
  <iupac_name>aluminium(3+) ion</iupac_name>
  <traditional_iupac>aluminium(3+) ion</traditional_iupac>
  <cas_registry_number/>
  <smiles>[Al+3]</smiles>
  <inchi>InChI=1S/Al/q+3</inchi>
  <inchikey>REDXJYDRNCIFBQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous post-transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a post-transition metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous post-transition metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous post-transition metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous post-transition metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a cation</external_descriptor>
      <external_descriptor>aluminium cation</external_descriptor>
      <external_descriptor>monoatomic aluminium</external_descriptor>
      <external_descriptor>monoatomic trication</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>aluminium(3+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>26.9815</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>26.981538441</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Al+3]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Al</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Al/q+3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>REDXJYDRNCIFBQ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>43 - 166</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.889 - 1.000</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized 2% fat (market)</comment>
      <references>
        <reference>
          <reference_text>Koo WW, Kaplan LA, Krug-Wispe SK: Aluminum contamination of infant formulas. JPEN J Parenter Enteral Nutr. 1988 Mar-Apr;12(2):170-3. doi: 10.1177/0148607188012002170.</reference_text>
          <pubmed_id>3361685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.889 - 1.482</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized. skim milk (market)</comment>
      <references>
        <reference>
          <reference_text>Koo WW, Kaplan LA, Krug-Wispe SK: Aluminum contamination of infant formulas. JPEN J Parenter Enteral Nutr. 1988 Mar-Apr;12(2):170-3. doi: 10.1177/0148607188012002170.</reference_text>
          <pubmed_id>3361685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.889 - 1.0748</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized. whole milk (market)</comment>
      <references>
        <reference>
          <reference_text>Koo WW, Kaplan LA, Krug-Wispe SK: Aluminum contamination of infant formulas. JPEN J Parenter Enteral Nutr. 1988 Mar-Apr;12(2):170-3. doi: 10.1177/0148607188012002170.</reference_text>
          <pubmed_id>3361685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>135 +/- 23</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>148 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>155 +/- 14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>147 +/- 7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.563 +/- 0.0296</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.341 +/- 0.0111</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.889 +/- 0.0371</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS.  Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.282 +/- 0.0185</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.667 +/- 0.0371</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.245 +/- 0.0222</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>43.734 - 154.180</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.413 - 11.971</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>157.0 +/- 5.0</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by ICP-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id/>
  <pubchem_compound_id>104727</pubchem_compound_id>
  <drugbank_id/>
  <foodb_id/>
  <chemspider_id/>
  <chebi_id>49470</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Aluminium</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Kang, B. S.; Kim, W. B.; Park, Y. S.; Yoo, Y. H.  Recovery of aluminum from anthracite ash.    Konghak Nonjip  (1989),  30  57-70. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Koo WW, Kaplan LA, Krug-Wispe SK: Aluminum contamination of infant formulas. JPEN J Parenter Enteral Nutr. 1988 Mar-Apr;12(2):170-3. doi: 10.1177/0148607188012002170.</reference_text>
      <pubmed_id>3361685</pubmed_id>
    </reference>
    <reference>
      <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
    </reference>
    <reference>
      <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:02 UTC</creation_date>
  <update_date>2020-04-16 17:51:34 UTC</update_date>
  <accession>BMDB0001248</accession>
  <secondary_accessions>
    <accession>BMDB01248</accession>
  </secondary_accessions>
  <name>FAD</name>
  <description/>
  <synonyms>
    <synonym>Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with riboflavine</synonym>
    <synonym>Adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diphosphate]</synonym>
    <synonym>Flavin adenine dinucleotide</synonym>
    <synonym>FLAVIN-adenine dinucleotide</synonym>
    <synonym>Riboflavin 5'-(trihydrogen diphosphate), 5'-5'-ester with adenosine</synonym>
    <synonym>Riboflavin 5'-adenosine diphosphate</synonym>
    <synonym>Adeflavin</synonym>
    <synonym>Adenosine 5'-(trihydrogen pyrophosphoric acid), 5'-5'-ester with riboflavine</synonym>
    <synonym>Adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diphosphoric acid]</synonym>
    <synonym>Riboflavin 5'-(trihydrogen diphosphoric acid), 5'-5'-ester with adenosine</synonym>
    <synonym>Riboflavin 5'-adenosine diphosphoric acid</synonym>
    <synonym>1H-Purin-6-amine flavin dinucleotide</synonym>
    <synonym>1H-Purin-6-amine flavine dinucleotide</synonym>
    <synonym>Adenine-flavin dinucleotide</synonym>
    <synonym>Adenine-flavine dinucleotide</synonym>
    <synonym>Adenine-riboflavin dinuceotide</synonym>
    <synonym>Adenine-riboflavin dinucleotide</synonym>
    <synonym>Adenine-riboflavine dinucleotide</synonym>
    <synonym>Flamitajin b</synonym>
    <synonym>Flanin F</synonym>
    <synonym>Flavin adenine dinucleotide oxidized</synonym>
    <synonym>Flavine adenosine diphosphate</synonym>
    <synonym>Flavine-adenine dinucleotide</synonym>
    <synonym>Flavitan</synonym>
    <synonym>Flaziren</synonym>
    <synonym>Isoalloxazine-adenine dinucleotide</synonym>
    <synonym>Riboflavin-adenine dinucleotide</synonym>
    <synonym>Riboflavine-adenine dinucleotide</synonym>
    <synonym>Dinucleotide, flavin-adenine</synonym>
  </synonyms>
  <chemical_formula>C27H33N9O15P2</chemical_formula>
  <average_molecular_weight>785.5497</average_molecular_weight>
  <monisotopic_moleculate_weight>785.157134455</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid</iupac_name>
  <traditional_iupac>flavine-adenine dinucleotide</traditional_iupac>
  <cas_registry_number>146-14-5</cas_registry_number>
  <smiles>CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2</smiles>
  <inchi>InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1</inchi>
  <inchikey>VWWQXMAJTJZDQX-UYBVJOGSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Flavin nucleotides</class>
    <sub_class/>
    <direct_parent>Flavin nucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>(3'-&gt;5')-dinucleotides</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Flavins</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Pyrazines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Quinoxalines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(3'-&gt;5')-dinucleotide</substituent>
      <substituent>(3'-&gt;5')-dinucleotide or analogue</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Diazanaphthalene</substituent>
      <substituent>Flavin</substituent>
      <substituent>Flavin nucleotide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Isoalloxazine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pteridine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrazine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Quinoxaline</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>flavin adenine dinucleotide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>5 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>785.5497</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>785.157134455</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H33N9O15P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VWWQXMAJTJZDQX-UYBVJOGSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>356.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>177.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>70.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Butyrate Metabolism</name>
      <smpdb_id>SMP0087185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Caffeine Metabolism</name>
      <smpdb_id>SMP0087186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>D-Arginine and D-Ornithine Metabolism</name>
      <smpdb_id>SMP0087190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutathione Metabolism</name>
      <smpdb_id>SMP0087167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerol Phosphate Shuttle</name>
      <smpdb_id>SMP0087199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ion Channels and Their Functional Role in Vascular Endothelium</name>
      <smpdb_id>SMP0108207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>LPS and Citrate Signaling and Inflammation</name>
      <smpdb_id>SMP0120946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Electron Transport Chain</name>
      <smpdb_id>SMP0087261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Plasmalogen Synthesis</name>
      <smpdb_id>SMP0087264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvaldehyde Degradation</name>
      <smpdb_id>SMP0087210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Riboflavin Metabolism</name>
      <smpdb_id>SMP0087211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Threonine and 2-Oxobutanoate Degradation</name>
      <smpdb_id>SMP0087262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Thyroid Hormone Synthesis</name>
      <smpdb_id>SMP0087269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin B6 Metabolism</name>
      <smpdb_id>SMP0087240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin K Metabolism</name>
      <smpdb_id>SMP0087227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>71096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181703</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00016</kegg_id>
  <drugbank_id>DB03147</drugbank_id>
  <foodb_id>FDB022511</foodb_id>
  <chemspider_id>559059</chemspider_id>
  <pubchem_compound_id>643975</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16238</chebi_id>
  <meta_cyc_id>FAD</meta_cyc_id>
  <knapsack_id>C00001500</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33521</bigg_id>
  <wikipedia_id>Fad</wikipedia_id>
  <metlin_id>6106</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00022</protein_accession>
      <name>Nitric oxide synthase, endothelial</name>
      <uniprot_id>P29473</uniprot_id>
      <gene_name>NOS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00066</protein_accession>
      <name>Cytochrome b5 reductase 4</name>
      <uniprot_id>Q32LH7</uniprot_id>
      <gene_name>CYB5R4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00069</protein_accession>
      <name>Nitric oxide synthase, inducible</name>
      <uniprot_id>Q27995</uniprot_id>
      <gene_name>NOS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00092</protein_accession>
      <name>Glycerol-3-phosphate dehydrogenase, mitochondrial</name>
      <uniprot_id>A6QLU1</uniprot_id>
      <gene_name>GPD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00119</protein_accession>
      <name>Dimethylaniline monooxygenase [N-oxide-forming] 3</name>
      <uniprot_id>Q8HYJ9</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00121</protein_accession>
      <name>Glutaryl-CoA dehydrogenase, mitochondrial</name>
      <uniprot_id>Q2KHZ9</uniprot_id>
      <gene_name>GCDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00128</protein_accession>
      <name>Peroxisomal N(1)-acetyl-spermine/spermidine oxidase</name>
      <uniprot_id>Q865R1</uniprot_id>
      <gene_name>PAOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00339</protein_accession>
      <name>Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial</name>
      <uniprot_id>P31039</uniprot_id>
      <gene_name>SDHA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00344</protein_accession>
      <name>Electron transfer flavoprotein-ubiquinone oxidoreductase, mitochondrial</name>
      <uniprot_id>Q2KIG0</uniprot_id>
      <gene_name>ETFDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00357</protein_accession>
      <name>L-2-hydroxyglutarate dehydrogenase, mitochondrial</name>
      <uniprot_id>A7MBI3</uniprot_id>
      <gene_name>L2HGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00387</protein_accession>
      <name>Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)</name>
      <uniprot_id>Q58DK4</uniprot_id>
      <gene_name>DAK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00428</protein_accession>
      <name>Isovaleryl-CoA dehydrogenase, mitochondrial</name>
      <uniprot_id>Q3SZI8</uniprot_id>
      <gene_name>IVD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00501</protein_accession>
      <name>Thioredoxin reductase 2, mitochondrial</name>
      <uniprot_id>Q9N2I8</uniprot_id>
      <gene_name>TXNRD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00527</protein_accession>
      <name>Protoporphyrinogen oxidase</name>
      <uniprot_id>P56602</uniprot_id>
      <gene_name>PPOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00540</protein_accession>
      <name>Thioredoxin reductase 1, cytoplasmic</name>
      <uniprot_id>O62768</uniprot_id>
      <gene_name>TXNRD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00603</protein_accession>
      <name>Xanthine dehydrogenase/oxidase</name>
      <uniprot_id>P80457</uniprot_id>
      <gene_name>XDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00618</protein_accession>
      <name>D-aspartate oxidase</name>
      <uniprot_id>P31228</uniprot_id>
      <gene_name>DDO</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00677</protein_accession>
      <name>Aldehyde oxidase</name>
      <uniprot_id>P48034</uniprot_id>
      <gene_name>AOX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00689</protein_accession>
      <name>Dihydropyrimidine dehydrogenase [NADP+]</name>
      <uniprot_id>Q28007</uniprot_id>
      <gene_name>DPYD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00788</protein_accession>
      <name>Short-chain specific acyl-CoA dehydrogenase, mitochondrial</name>
      <uniprot_id>Q3ZBF6</uniprot_id>
      <gene_name>ACADS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00800</protein_accession>
      <name>D-2-hydroxyglutarate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q1JPD3</uniprot_id>
      <gene_name>D2HGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00866</protein_accession>
      <name>NADH-cytochrome b5 reductase 1</name>
      <uniprot_id>Q3MHW9</uniprot_id>
      <gene_name>CYB5R1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00867</protein_accession>
      <name>Pyridine nucleotide-disulfide oxidoreductase domain-containing protein 2</name>
      <uniprot_id>Q3MHH6</uniprot_id>
      <gene_name>PYROXD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00868</protein_accession>
      <name>Flavin containing monooxygenase 2 (Non-functional)</name>
      <uniprot_id>Q0P566</uniprot_id>
      <gene_name>FMO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00869</protein_accession>
      <name>Truncated flavin-containing monooxygenase 3</name>
      <uniprot_id>Q8HYK2</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00870</protein_accession>
      <name>Very long-chain specific acyl-CoA dehydrogenase, mitochondrial</name>
      <uniprot_id>P48818</uniprot_id>
      <gene_name>ACADVL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00871</protein_accession>
      <name>Medium-chain specific acyl-CoA dehydrogenase, mitochondrial</name>
      <uniprot_id>Q3SZB4</uniprot_id>
      <gene_name>ACADM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00872</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 10, mitochondrial</name>
      <uniprot_id>P34942</uniprot_id>
      <gene_name>NDUFA10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00873</protein_accession>
      <name>Probable proline dehydrogenase 2</name>
      <uniprot_id>A6QQ74</uniprot_id>
      <gene_name>PRODH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00874</protein_accession>
      <name>NADPH oxidase 4</name>
      <uniprot_id>Q6V1P7</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00875</protein_accession>
      <name>Lactate dehydrogenase D</name>
      <uniprot_id>Q148K4</uniprot_id>
      <gene_name>LDHD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00876</protein_accession>
      <name>Dihydrouridine synthase 1-like (S. cerevisiae)</name>
      <uniprot_id>A0JNQ2</uniprot_id>
      <gene_name>DUS1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00877</protein_accession>
      <name>Ubiquinone biosynthesis monooxygenase COQ6</name>
      <uniprot_id>Q2KIL4</uniprot_id>
      <gene_name>COQ6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00878</protein_accession>
      <name>NADPH:adrenodoxin oxidoreductase, mitochondrial</name>
      <uniprot_id>P08165</uniprot_id>
      <gene_name>FDXR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00879</protein_accession>
      <name>Succinate dehydrogenase complex, subunit A, flavoprotein</name>
      <uniprot_id>A7E3V1</uniprot_id>
      <gene_name>SDHA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00880</protein_accession>
      <name>Flavin-containing monooxygenase 3</name>
      <uniprot_id>Q8HYK1</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00881</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 9, mitochondrial</name>
      <uniprot_id>P34943</uniprot_id>
      <gene_name>NDUFA9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00882</protein_accession>
      <name>Flavin-containing monooxygenase 3</name>
      <uniprot_id>Q8HYK4</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00883</protein_accession>
      <name>L-gulonolactone oxidase</name>
      <uniprot_id>Q3ZC33</uniprot_id>
      <gene_name>GULO</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00884</protein_accession>
      <name>FAD-dependent oxidoreductase domain-containing protein 1</name>
      <uniprot_id>Q5EA45</uniprot_id>
      <gene_name>FOXRED1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00885</protein_accession>
      <name>Amine oxidase [flavin-containing] B</name>
      <uniprot_id>P56560</uniprot_id>
      <gene_name>MAOB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00886</protein_accession>
      <name>Oxidoreductase NAD-binding domain-containing protein 1</name>
      <uniprot_id>Q58DM7</uniprot_id>
      <gene_name>OXNAD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00887</protein_accession>
      <name>Acyl-Coenzyme A dehydrogenase family, member 9</name>
      <uniprot_id>A5D974</uniprot_id>
      <gene_name>ACAD9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00888</protein_accession>
      <name>Short/branched chain specific acyl-CoA dehydrogenase, mitochondrial</name>
      <uniprot_id>Q5EAD4</uniprot_id>
      <gene_name>ACADSB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00889</protein_accession>
      <name>Apoptosis-inducing factor 2</name>
      <uniprot_id>A5PJM4</uniprot_id>
      <gene_name>AIFM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00890</protein_accession>
      <name>Amine oxidase [flavin-containing] A</name>
      <uniprot_id>P21398</uniprot_id>
      <gene_name>MAOA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00891</protein_accession>
      <name>Flavin-containing monooxygenase 3</name>
      <uniprot_id>Q8HYK3</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00892</protein_accession>
      <name>Acyl-Coenzyme A dehydrogenase family, member 11</name>
      <uniprot_id>Q0P5G8</uniprot_id>
      <gene_name>ACAD11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00893</protein_accession>
      <name>NADPH--cytochrome P450 reductase</name>
      <uniprot_id>Q3SYT8</uniprot_id>
      <gene_name>POR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00894</protein_accession>
      <name>Isobutyryl-CoA dehydrogenase, mitochondrial</name>
      <uniprot_id>Q0NXR6</uniprot_id>
      <gene_name>ACAD8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00895</protein_accession>
      <name>Peroxisomal sarcosine oxidase</name>
      <uniprot_id>Q29RU9</uniprot_id>
      <gene_name>PIPOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00896</protein_accession>
      <name>Flavin-containing monooxygenase 3</name>
      <uniprot_id>Q8HYK0</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00897</protein_accession>
      <name>Squalene monooxygenase</name>
      <uniprot_id>A5D9A8</uniprot_id>
      <gene_name>SQLE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00898</protein_accession>
      <name>Thioredoxin reductase 3</name>
      <uniprot_id>Q9GKW9</uniprot_id>
      <gene_name>trxr3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00899</protein_accession>
      <name>NADH-cytochrome b5 reductase 3</name>
      <uniprot_id>P07514</uniprot_id>
      <gene_name>CYB5R3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00900</protein_accession>
      <name>Dihydrouridine synthase 2-like, SMM1 homolog (S. cerevisiae)</name>
      <uniprot_id>Q0VC60</uniprot_id>
      <gene_name>DUS2L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00901</protein_accession>
      <name>Pyridine nucleotide-disulfide oxidoreductase domain-containing protein 1</name>
      <uniprot_id>A7YVH9</uniprot_id>
      <gene_name>PYROXD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00902</protein_accession>
      <name>Acyl-Coenzyme A dehydrogenase family, member 9</name>
      <uniprot_id>Q3MHJ6</uniprot_id>
      <gene_name>ACAD9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00903</protein_accession>
      <name>Putative acyl-CoA dehydrogenase</name>
      <uniprot_id>Q1JPD5</uniprot_id>
      <gene_name>ACAD11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00904</protein_accession>
      <name>ERO1-like protein alpha</name>
      <uniprot_id>A5PJN2</uniprot_id>
      <gene_name>ERO1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00905</protein_accession>
      <name>Prenylcysteine oxidase-like</name>
      <uniprot_id>Q0P5H1</uniprot_id>
      <gene_name>PCYOX1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00906</protein_accession>
      <name>Methylenetetrahydrofolate reductase</name>
      <uniprot_id>Q5I598</uniprot_id>
      <gene_name>MTHFR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00907</protein_accession>
      <name>Peroxisomal acyl-coenzyme A oxidase 1</name>
      <uniprot_id>Q3SZP5</uniprot_id>
      <gene_name>ACOX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00908</protein_accession>
      <name>Succinate dehydrogenase complex subunit A</name>
      <uniprot_id>Q0QF04</uniprot_id>
      <gene_name>SDHA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00909</protein_accession>
      <name>NADPH-dependent diflavin oxidoreductase 1</name>
      <uniprot_id>Q1JPJ0</uniprot_id>
      <gene_name>NDOR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01428</protein_accession>
      <name>Cytochrome b-245 heavy chain</name>
      <uniprot_id>O46522</uniprot_id>
      <gene_name>CYBB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02108</protein_accession>
      <name>DUS4L protein</name>
      <uniprot_id>A6QPA8</uniprot_id>
      <gene_name>DUS4L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02109</protein_accession>
      <name>SDHA protein</name>
      <uniprot_id>Q2HJI1</uniprot_id>
      <gene_name>SDHA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02110</protein_accession>
      <name>DHCR24 protein</name>
      <uniprot_id>A6QR14</uniprot_id>
      <gene_name>DHCR24</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02111</protein_accession>
      <name>Mitochondrial translation optimization 1 homolog (S. cerevisiae)</name>
      <uniprot_id>Q1JQB6</uniprot_id>
      <gene_name>MTO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02112</protein_accession>
      <name>Apoptosis-inducing factor, mitochondrion-associated, 3</name>
      <uniprot_id>Q2KJ59</uniprot_id>
      <gene_name>AIFM3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02113</protein_accession>
      <name>ACOX3 protein</name>
      <uniprot_id>A4IFA4</uniprot_id>
      <gene_name>ACOX3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02114</protein_accession>
      <name>FMO5 protein</name>
      <uniprot_id>A6QLN7</uniprot_id>
      <gene_name>FMO5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02115</protein_accession>
      <name>Six transmembrane epithelial antigen of the prostate 2</name>
      <uniprot_id>A0JNK9</uniprot_id>
      <gene_name>STEAP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02116</protein_accession>
      <name>Electron transfer flavoprotein subunit alpha, mitochondrial</name>
      <uniprot_id>Q2KJE4</uniprot_id>
      <gene_name>ETFA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02117</protein_accession>
      <name>Predicted NADPH oxidase-5</name>
      <uniprot_id>A7E3L4</uniprot_id>
      <gene_name>Nox5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02118</protein_accession>
      <name>Acyl-Coenzyme A dehydrogenase, long chain</name>
      <uniprot_id>Q08D92</uniprot_id>
      <gene_name>ACADL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02119</protein_accession>
      <name>FMO3 protein</name>
      <uniprot_id>Q3SZW0</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02120</protein_accession>
      <name>CYB5RL protein</name>
      <uniprot_id>A6QP65</uniprot_id>
      <gene_name>CYB5RL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02121</protein_accession>
      <name>Apoptosis-inducing factor (AIF)-like mitchondrion-associated inducer of death</name>
      <uniprot_id>Q5BIR2</uniprot_id>
      <gene_name>AMID</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02122</protein_accession>
      <name>Electron transfer flavoprotein subunit beta</name>
      <uniprot_id>Q2TBV3</uniprot_id>
      <gene_name>ETFB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02123</protein_accession>
      <name>ACOX2 protein</name>
      <uniprot_id>A6QPZ7</uniprot_id>
      <gene_name>ACOX2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02124</protein_accession>
      <name>CYB5R3 protein</name>
      <uniprot_id>A6H7G0</uniprot_id>
      <gene_name>CYB5R3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:03 UTC</creation_date>
  <update_date>2020-03-13 16:26:46 UTC</update_date>
  <accession>BMDB0001250</accession>
  <secondary_accessions>
    <accession>BMDB01250</accession>
  </secondary_accessions>
  <name>N-Acetylarylamine</name>
  <description/>
  <synonyms>
    <synonym>Acetamidobenzene</synonym>
    <synonym>Acetanil</synonym>
    <synonym>Acetanilid</synonym>
    <synonym>Acetanilide</synonym>
    <synonym>Acetic acid anilide</synonym>
    <synonym>N-Acetylaminobenzene</synonym>
    <synonym>N-Phenylacetamide</synonym>
    <synonym>Acetate anilide</synonym>
    <synonym>Antifebrin</synonym>
    <synonym>N-Acetylarylamine</synonym>
  </synonyms>
  <chemical_formula>C8H9NO</chemical_formula>
  <average_molecular_weight>135.1632</average_molecular_weight>
  <monisotopic_moleculate_weight>135.068413915</monisotopic_moleculate_weight>
  <iupac_name>N-phenylacetamide</iupac_name>
  <traditional_iupac>acetanilide</traditional_iupac>
  <cas_registry_number>55576-55-1</cas_registry_number>
  <smiles>CC(=O)NC1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)</inchi>
  <inchikey>FZERHIULMFGESH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class/>
    <direct_parent>Benzene and substituted derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>acetamides</external_descriptor>
      <external_descriptor>anilide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>6.39 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.16</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-phenylacetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>135.1632</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>135.068413915</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)NC1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H9NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FZERHIULMFGESH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>29.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>77049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>77050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>77051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>137055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>137056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>137057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99678</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C07565</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022512</foodb_id>
  <chemspider_id>880</chemspider_id>
  <pubchem_compound_id>904</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28884</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>N-Phenylacetamide</wikipedia_id>
  <metlin_id>6107</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:04 UTC</creation_date>
  <update_date>2020-03-13 16:26:47 UTC</update_date>
  <accession>BMDB0001251</accession>
  <secondary_accessions>
    <accession>BMDB01251</accession>
  </secondary_accessions>
  <name>Lanosterin</name>
  <description/>
  <synonyms>
    <synonym>(3beta)-Lanosta-8,24-dien-3-ol</synonym>
    <synonym>(3beta,5alpha)-4,4,14-Trimethylcholesta-8,24-dien-3-ol</synonym>
    <synonym>4,4',14alpha-Trimethyl-5alpha-cholesta-8,24-dien-3beta-ol</synonym>
    <synonym>(3b)-Lanosta-8,24-dien-3-ol</synonym>
    <synonym>(3β)-Lanosta-8,24-dien-3-ol</synonym>
    <synonym>(3b,5a)-4,4,14-Trimethylcholesta-8,24-dien-3-ol</synonym>
    <synonym>(3β,5α)-4,4,14-Trimethylcholesta-8,24-dien-3-ol</synonym>
    <synonym>4,4',14a-Trimethyl-5a-cholesta-8,24-dien-3b-ol</synonym>
    <synonym>4,4',14α-Trimethyl-5α-cholesta-8,24-dien-3β-ol</synonym>
    <synonym>(3 beta)-Lanosta-8,24-dien-3-ol</synonym>
    <synonym>(3alpha)-4,4,14-Trimethyl-cholesta-8,24-dien-3-ol</synonym>
    <synonym>(3beta,5alpha)-4,4,14-Trimethyl-cholesta-8,24-dien-3-ol</synonym>
    <synonym>Botalan base 138</synonym>
    <synonym>Lanosta-8,24-dien-3-ol</synonym>
    <synonym>Lanosta-8,24-dien-3beta-ol</synonym>
    <synonym>Lanosta-8,24-dienol</synonym>
    <synonym>Lanosterol</synonym>
    <synonym>Lanster</synonym>
    <synonym>4,4,14 alpha-Trimethyl-5 alpha-cholesta-8,24-dien-3 beta-ol</synonym>
    <synonym>Kryptosterol</synonym>
    <synonym>Lanosterin</synonym>
    <synonym>3beta-Hydroxy-lansota-8,24-dien-21-oic acid</synonym>
    <synonym>3beta-Hydroxylanosta-8,24-diene</synonym>
    <synonym>3β-Hydroxy-lansota-8,24-dien-21-oic acid</synonym>
    <synonym>3β-Hydroxylanosta-8,24-diene</synonym>
    <synonym>4,4,14alpha-Trimethylcholesta-8,24-dien-3beta-ol</synonym>
    <synonym>4,4,14α-Trimethylcholesta-8,24-dien-3β-ol</synonym>
    <synonym>5alpha-Lanosta-8,24-dien-3beta-ol</synonym>
    <synonym>5α-Lanosta-8,24-dien-3β-ol</synonym>
    <synonym>Lanosta-8,24-dien-3β-ol</synonym>
    <synonym>Lanostadien-3beta-ol</synonym>
    <synonym>Lanostadien-3β-ol</synonym>
  </synonyms>
  <chemical_formula>C30H50O</chemical_formula>
  <average_molecular_weight>426.7174</average_molecular_weight>
  <monisotopic_moleculate_weight>426.386166222</monisotopic_moleculate_weight>
  <iupac_name>(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol</iupac_name>
  <traditional_iupac>(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol</traditional_iupac>
  <cas_registry_number>79-63-0</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C</smiles>
  <inchi>InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1</inchi>
  <inchikey>CAHGCLMLTWQZNJ-BQNIITSRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Triterpenoids</sub_class>
    <direct_parent>Triterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>14-alpha-methylsteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>14-alpha-methylsteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Steroid</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3beta-sterol</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>tetracyclic triterpenoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>140.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,5S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>426.7174</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>426.386166222</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C30H50O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CAHGCLMLTWQZNJ-BQNIITSRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>134.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>55.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>128906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1568</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01724</kegg_id>
  <pubchem_compound_id>246983</pubchem_compound_id>
  <drugbank_id>DB03696</drugbank_id>
  <foodb_id>FDB013802</foodb_id>
  <chemspider_id>216175</chemspider_id>
  <chebi_id>16521</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>LANOSTEROL</meta_cyc_id>
  <knapsack_id>C00003657</knapsack_id>
  <wikipedia_id>Lanosterol</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>38253</bigg_id>
  <metlin_id>6108</metlin_id>
  <synthesis_reference>Maienthal, Millard; Franklin, Philip J. Preparation of lanosterol from bromolanosterol. Journal of Organic Chemistry (1955), 20 1627-30.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00804</protein_accession>
      <name>Lanosterol synthase</name>
      <uniprot_id>P84466</uniprot_id>
      <gene_name>LSS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:05 UTC</creation_date>
  <update_date>2020-04-15 22:34:15 UTC</update_date>
  <accession>BMDB0001252</accession>
  <secondary_accessions>
    <accession>BMDB01252</accession>
  </secondary_accessions>
  <name>Betaine aldehyde</name>
  <description/>
  <synonyms>
    <synonym>Glycine betaine aldehyde</synonym>
    <synonym>(Formylmethyl)trimethyl-ammonium</synonym>
    <synonym>(Formylmethyl)trimethylammonium</synonym>
    <synonym>BTL</synonym>
    <synonym>N,N,N-Trimethyl-2-oxo ethanaminium</synonym>
    <synonym>N,N,N-Trimethyl-2-oxo-ethanaminium</synonym>
    <synonym>Trimethyl(formylmethyl)ammonium</synonym>
  </synonyms>
  <chemical_formula>C5H12NO</chemical_formula>
  <average_molecular_weight>102.1549</average_molecular_weight>
  <monisotopic_moleculate_weight>102.091889011</monisotopic_moleculate_weight>
  <iupac_name>trimethyl(2-oxoethyl)azanium</iupac_name>
  <traditional_iupac>betaine aldehyde</traditional_iupac>
  <cas_registry_number>7418-61-3</cas_registry_number>
  <smiles>C[N+](C)(C)CC=O</smiles>
  <inchi>InChI=1S/C5H12NO/c1-6(2,3)4-5-7/h5H,4H2,1-3H3/q+1</inchi>
  <inchikey>SXKNCCSPZDCRFD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Quaternary ammonium salts</sub_class>
    <direct_parent>Tetraalkylammonium salts</direct_parent>
    <alternative_parents>
      <alternative_parent>Aldehydes</alternative_parent>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>quaternary ammonium ion</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-8.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>trimethyl(2-oxoethyl)azanium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>102.1549</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>102.091889011</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)CC=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H12NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H12NO/c1-6(2,3)4-5-7/h5H,4H2,1-3H3/q+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SXKNCCSPZDCRFD-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445829</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00576</kegg_id>
  <pubchem_compound_id>249</pubchem_compound_id>
  <drugbank_id>DB04401</drugbank_id>
  <foodb_id>FDB022513</foodb_id>
  <chemspider_id>244</chemspider_id>
  <chebi_id>15710</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Betaine_aldehyde</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35400</bigg_id>
  <metlin_id>278</metlin_id>
  <synthesis_reference>Cromwell, B. T.; Rennie, S. D.  Biosynthesis and metabolism of betaines in plants. II. Biosynthesis of glycinebetaine(betaine) in higher plants.    Biochemical Journal  (1954),  58  318-22.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:06 UTC</creation_date>
  <update_date>2020-03-13 16:26:48 UTC</update_date>
  <accession>BMDB0001253</accession>
  <secondary_accessions>
    <accession>BMDB01253</accession>
  </secondary_accessions>
  <name>5,6-Dihydroxyindole-2-carboxylic acid</name>
  <description>5,6-Dihydroxyindole-2-carboxylic acid, also known as 5,6-dihydroxyindole-2-carboxylic acid or 5,6-dihydroxyindole-2-carboxylic acid, belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. 5,6-Dihydroxyindole-2-carboxylic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 5,6-Dihydroxyindole-2-carboxylic acid participates in a number of enzymatic reactions, within cattle. In particular, 5,6-Dihydroxyindole-2-carboxylic acid can be biosynthesized from L-dopachrome; which is mediated by the enzyme L-dopachrome tautomerase. In addition, 5,6-Dihydroxyindole-2-carboxylic acid can be converted into melanin through its interaction with the enzyme tyrosinase. In cattle, 5,6-dihydroxyindole-2-carboxylic acid is involved in the metabolic pathway called the tyrosine metabolism pathway.</description>
  <synonyms>
    <synonym>5,6-DHICA</synonym>
    <synonym>5,6-Dihydroxy-2-indolecarboxylic acid</synonym>
    <synonym>5,6-Dihydroxy-2-indolylcarboxylic acid</synonym>
    <synonym>5,6-Dihydroxyindole-2-carboxylate</synonym>
    <synonym>DHI2c</synonym>
    <synonym>DHICA</synonym>
    <synonym>5,6-Dihydroxy-2-indolecarboxylate</synonym>
    <synonym>5,6-Dihydroxy-2-indolylcarboxylate</synonym>
    <synonym>5,6-Dihydroxy-1H-indole-2-carboxylate</synonym>
    <synonym>5,6-Dihydroxy-1H-indole-2-carboxylic acid</synonym>
  </synonyms>
  <chemical_formula>C9H7NO4</chemical_formula>
  <average_molecular_weight>193.1562</average_molecular_weight>
  <monisotopic_moleculate_weight>193.037507717</monisotopic_moleculate_weight>
  <iupac_name>5,6-dihydroxy-1H-indole-2-carboxylic acid</iupac_name>
  <traditional_iupac>dhica</traditional_iupac>
  <cas_registry_number>4790-08-3</cas_registry_number>
  <smiles>OC(=O)C1=CC2=C(N1)C=C(O)C(O)=C2</smiles>
  <inchi>InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1-3,10-12H,(H,13,14)</inchi>
  <inchikey>YFTGOBNOJKXZJC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Indolecarboxylic acids and derivatives</sub_class>
    <direct_parent>Indolecarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxyindoles</alternative_parent>
      <alternative_parent>Indoles</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrrole 2-carboxylic acids</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyindole</substituent>
      <substituent>Indole</substituent>
      <substituent>Indolecarboxylic acid derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Pyrrole-2-carboxylic acid</substituent>
      <substituent>Pyrrole-2-carboxylic acid or derivatives</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dihydroxyindole</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5,6-dihydroxy-1H-indole-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>193.1562</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>193.037507717</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1=CC2=C(N1)C=C(O)C(O)=C2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H7NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1-3,10-12H,(H,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YFTGOBNOJKXZJC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>93.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>48.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352110</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04185</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022514</foodb_id>
  <chemspider_id>106648</chemspider_id>
  <pubchem_compound_id>119405</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>2003</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>1444022</bigg_id>
  <wikipedia_id/>
  <metlin_id>6110</metlin_id>
  <synthesis_reference>Chioccara, Francesco; Novellino, Ettore. Biomimetic synthesis of 5,6-dihydroxyindole-2-carboxylic acid and of its benzyl ester. Synthetic Communications (1987), 17(15), 1815-21.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:08 UTC</creation_date>
  <update_date>2020-04-16 17:50:35 UTC</update_date>
  <accession>BMDB0001254</accession>
  <secondary_accessions>
    <accession>BMDB01254</accession>
  </secondary_accessions>
  <name>Glucosamine 6-phosphate</name>
  <description>Glucosamine 6-phosphate, also known as GLCN-6-p or glucose-6-phosphoric acid, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Glucosamine 6-phosphate is possibly soluble (in water) and a very strong basic compound (based on its pKa). Glucosamine 6-phosphate exists in all living species, ranging from bacteria to humans. Glucosamine 6-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Glucosamine 6-phosphate and acetic acid can be biosynthesized from N-acetyl-D-glucosamine 6-phosphate; which is mediated by the enzyme putative N-acetylglucosamine-6-phosphate deacetylase. In addition, Glucosamine 6-phosphate can be converted into N-acetyl-D-glucosamine 6-phosphate; which is catalyzed by the enzyme glucosamine 6-phosphate N-acetyltransferase. In cattle, glucosamine 6-phosphate is involved in the metabolic pathway called the amino sugar metabolism pathway.</description>
  <synonyms>
    <synonym>2-Amino-2-deoxy-6-O-phosphono-alpha-D-glucopyranose</synonym>
    <synonym>alpha-D-Glucosamine 6-(dihydrogen phosphate)</synonym>
    <synonym>2-Amino-2-deoxy-6-O-phosphono-a-D-glucopyranose</synonym>
    <synonym>2-Amino-2-deoxy-6-O-phosphono-α-D-glucopyranose</synonym>
    <synonym>a-D-Glucosamine 6-(dihydrogen phosphate)</synonym>
    <synonym>a-D-Glucosamine 6-(dihydrogen phosphoric acid)</synonym>
    <synonym>alpha-D-Glucosamine 6-(dihydrogen phosphoric acid)</synonym>
    <synonym>Α-D-glucosamine 6-(dihydrogen phosphate)</synonym>
    <synonym>Α-D-glucosamine 6-(dihydrogen phosphoric acid)</synonym>
    <synonym>Glucosamine 6-phosphoric acid</synonym>
    <synonym>2-Amino-2-deoxy-D-glucose 6-phosphate</synonym>
    <synonym>2-Amino-2-deoxyglucose 6-phosphate</synonym>
    <synonym>2-Amino-D-glucose-6-phosphate</synonym>
    <synonym>D-Glucosamine 6-phosphate</synonym>
    <synonym>D-Glucosamine phosphate</synonym>
    <synonym>D-Glucosamine-6-phosphate</synonym>
    <synonym>Glucosamine 6 -phosphate</synonym>
    <synonym>Glucosamine-6-p</synonym>
    <synonym>Glucosamine-6-phosphate</synonym>
    <synonym>Glucose-6-phosphorate</synonym>
    <synonym>Glucose-6-phosphoric acid</synonym>
    <synonym>Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester</synonym>
    <synonym>GLCN-6-p</synonym>
    <synonym>Glucosamine 6-phosphate, disodium salt</synonym>
    <synonym>Glucosamine 6-phosphate, monosodium salt</synonym>
  </synonyms>
  <chemical_formula>C6H14NO8P</chemical_formula>
  <average_molecular_weight>259.151</average_molecular_weight>
  <monisotopic_moleculate_weight>259.045702941</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>α-D-glucosamine 6-phosphate</traditional_iupac>
  <cas_registry_number>3616-42-0</cas_registry_number>
  <smiles>N[C@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1</inchi>
  <inchikey>XHMJOUIAFHJHBW-UKFBFLRUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Aminosaccharides</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino saccharide</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-amino-2-deoxy-D-glucopyranose 6-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>259.151</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>259.045702941</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H14NO8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XHMJOUIAFHJHBW-UKFBFLRUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>162.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>48.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447961</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00352</kegg_id>
  <drugbank_id>DB02657</drugbank_id>
  <foodb_id>FDB022515</foodb_id>
  <chemspider_id>388356</chemspider_id>
  <pubchem_compound_id>439217</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15873</chebi_id>
  <meta_cyc_id>CPD-13469</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>34709</bigg_id>
  <wikipedia_id/>
  <metlin_id>6111</metlin_id>
  <synthesis_reference>Cacioppo, F.; Pandolfo, L.; Arena, E.  Synthesis of glucosamine 6-phosphate in tissues of rachitic rats.    Giorn. Biochim.  (1964),  13(4),  249-55.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00827</protein_accession>
      <name>Glucosamine--fructose-6-phosphate aminotransferase [isomerizing] 2</name>
      <uniprot_id>Q08DQ2</uniprot_id>
      <gene_name>GFPT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00937</protein_accession>
      <name>Glucosamine-6-phosphate isomerase 2</name>
      <uniprot_id>Q17QL1</uniprot_id>
      <gene_name>GNPDA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00938</protein_accession>
      <name>Putative N-acetylglucosamine-6-phosphate deacetylase</name>
      <uniprot_id>A7MBC0</uniprot_id>
      <gene_name>AMDHD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:09 UTC</creation_date>
  <update_date>2020-04-16 20:38:38 UTC</update_date>
  <accession>BMDB0001256</accession>
  <secondary_accessions>
    <accession>BMDB01256</accession>
  </secondary_accessions>
  <name>Spermine</name>
  <description>Spermine, also known as gerontine or musculamine, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Spermine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Spermine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Spermine exists in all living species, ranging from bacteria to humans. 5'-Methylthioadenosine and spermine can be biosynthesized from S-adenosylmethioninamine and spermidine through the action of the enzyme spermine synthase. In cattle, spermine is involved in the metabolic pathway called spermidine and spermine biosynthesis pathway. Spermine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>4,9-Diaza-1,12-dodecanediamine</synonym>
    <synonym>4,9-Diazadodecane-1,12-diamine</synonym>
    <synonym>N,N'-bis(3-aminopropyl)-1,4-butanediamine</synonym>
    <synonym>1,5,10,14-Tetraazatetradecane</synonym>
    <synonym>4,9-Diazadodecamethylenediamine</synonym>
    <synonym>Diaminopropyl-tetramethylenediamine</synonym>
    <synonym>Diaminopropyltetramethylenediamine</synonym>
    <synonym>Gerontine</synonym>
    <synonym>Musculamine</synonym>
    <synonym>N,N'-bis(3-aminopropyl)-1,4-tetramethylenediamine</synonym>
    <synonym>N,N'-bis(3-aminopropyl)butane-1,4-diamine</synonym>
    <synonym>N1,N4-Bis(3-aminopropyl)-1,4-butanediamine</synonym>
    <synonym>Neuridine</synonym>
    <synonym>Spermin</synonym>
    <synonym>Spermine dihydrate</synonym>
    <synonym>Spermine puriss</synonym>
    <synonym>SPM</synonym>
  </synonyms>
  <chemical_formula>C10H26N4</chemical_formula>
  <average_molecular_weight>202.3402</average_molecular_weight>
  <monisotopic_moleculate_weight>202.215746852</monisotopic_moleculate_weight>
  <iupac_name>(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine</iupac_name>
  <traditional_iupac>spermine</traditional_iupac>
  <cas_registry_number>71-44-3</cas_registry_number>
  <smiles>NCCCNCCCCNCCCN</smiles>
  <inchi>InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2</inchi>
  <inchikey>PFNFFQXMRSDOHW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>Dialkylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary aliphatic amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>polyazaalkane</external_descriptor>
      <external_descriptor>tetraamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>29 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>202.3402</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>202.215746852</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCNCCCCNCCCN</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H26N4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PFNFFQXMRSDOHW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>76.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>62.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31892</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.2+/-0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>0.2+/-0.1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0700 - 7.560</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>colostrum</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Ploszaj T, Wojtasik A, Kukulska W, Podgurniak M: Polyamines in cow's and sow's milk. Comp Biochem Physiol B Biochem Mol Biol. 1995 Jul;111(3):427-33.</reference_text>
          <pubmed_id>7613766</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Ploszaj T, Wojtasik A, Kukulska W, Podgurniak M: Polyamines in cow's and sow's milk. Comp Biochem Physiol B Biochem Mol Biol. 1995 Jul;111(3):427-33.</reference_text>
          <pubmed_id>7613766</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>3+/-3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>0.11+/-0.03</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00750</kegg_id>
  <drugbank_id>DB00127</drugbank_id>
  <foodb_id>FDB003225</foodb_id>
  <chemspider_id>1072</chemspider_id>
  <pubchem_compound_id>1103</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15746</chebi_id>
  <meta_cyc_id>SPERMINE</meta_cyc_id>
  <knapsack_id>C00001432</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35875</bigg_id>
  <wikipedia_id>Spermine</wikipedia_id>
  <metlin_id>255</metlin_id>
  <synthesis_reference>Wrede, Fritz; Strack, Erich; Hettche, Otto.  Spermine. VII.    Z. physiol. Chem.  (1928),  173  61-8.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Motyl T, Ploszaj T, Wojtasik A, Kukulska W, Podgurniak M: Polyamines in cow's and sow's milk. Comp Biochem Physiol B Biochem Mol Biol. 1995 Jul;111(3):427-33.</reference_text>
      <pubmed_id>7613766</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00126</protein_accession>
      <name>Spermine synthase</name>
      <uniprot_id>Q3SZA5</uniprot_id>
      <gene_name>SMS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01355</protein_accession>
      <name>Solute carrier family 22 member 1</name>
      <uniprot_id>A7MBE0</uniprot_id>
      <gene_name>SLC22A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:10 UTC</creation_date>
  <update_date>2020-04-16 20:37:58 UTC</update_date>
  <accession>BMDB0001257</accession>
  <secondary_accessions>
    <accession>BMDB01257</accession>
  </secondary_accessions>
  <name>Spermidine</name>
  <description>Spermidine, also known as SPD, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Spermidine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Spermidine exists in all living species, ranging from bacteria to humans. Spermidine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1,5,10-Triazadecane</synonym>
    <synonym>4-Azaoctamethylenediamine</synonym>
    <synonym>4-Azaoctane-1,8-diamine</synonym>
    <synonym>N-(3-Aminopropyl)-1,4-butane-diamine</synonym>
    <synonym>Spermidin</synonym>
    <synonym>1,8-Diamino-4-azaoctane</synonym>
    <synonym>Aminopropylbutandiamine</synonym>
    <synonym>N-(3-Aminopropyl)-1,4-butanediamine</synonym>
    <synonym>N-(3-Aminopropyl)-1,4-diamino-butane</synonym>
    <synonym>N-(3-Aminopropyl)-1,4-diaminobutane</synonym>
    <synonym>N-(3-Aminopropyl)-4-aminobutylamine</synonym>
    <synonym>N-(4-Aminobutyl)-1,3-diaminopropane</synonym>
    <synonym>N-(gamma-Aminopropyl)tetramethylenediamine</synonym>
    <synonym>SPD</synonym>
  </synonyms>
  <chemical_formula>C7H19N3</chemical_formula>
  <average_molecular_weight>145.2459</average_molecular_weight>
  <monisotopic_moleculate_weight>145.157897623</monisotopic_moleculate_weight>
  <iupac_name>(4-aminobutyl)(3-aminopropyl)amine</iupac_name>
  <traditional_iupac>spermidine</traditional_iupac>
  <cas_registry_number>124-20-9</cas_registry_number>
  <smiles>NCCCCNCCCN</smiles>
  <inchi>InChI=1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2</inchi>
  <inchikey>ATHGHQPFGPMSJY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>Dialkylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary aliphatic amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>polyazaalkane</external_descriptor>
      <external_descriptor>triamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>&lt; 25 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4-aminobutyl)(3-aminopropyl)amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>145.2459</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>145.157897623</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCCNCCCN</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H19N3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ATHGHQPFGPMSJY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>64.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>44.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445246</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.2+/-0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>0.09+/-0.03</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>colostrum</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Ploszaj T, Wojtasik A, Kukulska W, Podgurniak M: Polyamines in cow's and sow's milk. Comp Biochem Physiol B Biochem Mol Biol. 1995 Jul;111(3):427-33.</reference_text>
          <pubmed_id>7613766</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.200 - 4.400</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Motyl T, Ploszaj T, Wojtasik A, Kukulska W, Podgurniak M: Polyamines in cow's and sow's milk. Comp Biochem Physiol B Biochem Mol Biol. 1995 Jul;111(3):427-33.</reference_text>
          <pubmed_id>7613766</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.88 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.89 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.84 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.70 +/- 0.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>37+/-22</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>0.11+/-0.04</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>0.4+/-0.2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>1071</chemspider_id>
  <kegg_id>C00315</kegg_id>
  <pubchem_compound_id>1102</pubchem_compound_id>
  <foodb_id>FDB012039</foodb_id>
  <drugbank_id>DB03566</drugbank_id>
  <pdbe_id/>
  <chebi_id>16610</chebi_id>
  <knapsack_id>C00001431</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34593</bigg_id>
  <wikipedia_id>Spermidine</wikipedia_id>
  <metlin_id>254</metlin_id>
  <meta_cyc_id>SPERMIDINE</meta_cyc_id>
  <synthesis_reference>Bergeron, Raymond J., Jr.  Preparation and formulation spermidine analogues for pharmaceutical use as tumor growth inhibitors.    U.S.  (2001),     31 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Motyl T, Ploszaj T, Wojtasik A, Kukulska W, Podgurniak M: Polyamines in cow's and sow's milk. Comp Biochem Physiol B Biochem Mol Biol. 1995 Jul;111(3):427-33.</reference_text>
      <pubmed_id>7613766</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00126</protein_accession>
      <name>Spermine synthase</name>
      <uniprot_id>Q3SZA5</uniprot_id>
      <gene_name>SMS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00127</protein_accession>
      <name>Deoxyhypusine synthase</name>
      <uniprot_id>Q6EWQ6</uniprot_id>
      <gene_name>DHPS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00128</protein_accession>
      <name>Peroxisomal N(1)-acetyl-spermine/spermidine oxidase</name>
      <uniprot_id>Q865R1</uniprot_id>
      <gene_name>PAOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01355</protein_accession>
      <name>Solute carrier family 22 member 1</name>
      <uniprot_id>A7MBE0</uniprot_id>
      <gene_name>SLC22A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:11 UTC</creation_date>
  <update_date>2020-04-15 22:35:46 UTC</update_date>
  <accession>BMDB0001259</accession>
  <secondary_accessions>
    <accession>BMDB01259</accession>
  </secondary_accessions>
  <name>Succinic acid semialdehyde</name>
  <description>Succinic acid semialdehyde, also known as Succinic acid semialdehyde or Succinic acid semialdehyde, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Succinic acid semialdehyde is a drug. Succinic acid semialdehyde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Succinic acid semialdehyde exists in all living species, ranging from bacteria to humans. Succinic acid semialdehyde participates in a number of enzymatic reactions, within cattle. In particular, Succinic acid semialdehyde and L-glutamic acid can be biosynthesized from gamma-aminobutyric acid and oxoglutaric acid through its interaction with the enzyme 4-aminobutyrate aminotransferase, mitochondrial. In addition, Succinic acid semialdehyde can be converted into succinic acid; which is mediated by the enzyme succinate-semialdehyde dehydrogenase, mitochondrial. In cattle, succinic acid semialdehyde is involved in the metabolic pathway called the glutamate metabolism pathway. Succinic acid semialdehyde is a potentially toxic compound.</description>
  <synonyms>
    <synonym>3-Formylpropanoic acid</synonym>
    <synonym>3-Formylpropionic acid</synonym>
    <synonym>4-Oxobutanoate</synonym>
    <synonym>beta-Formylpropionic acid</synonym>
    <synonym>Semialdehyde succinique</synonym>
    <synonym>Succinaldehydic acid</synonym>
    <synonym>Succinate semialdehyde</synonym>
    <synonym>Succinic semialdehyde</synonym>
    <synonym>3-Formylpropanoate</synonym>
    <synonym>3-Formylpropionate</synonym>
    <synonym>4-Oxobutanoic acid</synonym>
    <synonym>b-Formylpropionate</synonym>
    <synonym>b-Formylpropionic acid</synonym>
    <synonym>beta-Formylpropionate</synonym>
    <synonym>Β-formylpropionate</synonym>
    <synonym>Β-formylpropionic acid</synonym>
    <synonym>Succinaldehydate</synonym>
    <synonym>2-Formylpropionic acid ethyl ester</synonym>
    <synonym>Butryaldehydate</synonym>
    <synonym>Butryaldehydic acid</synonym>
    <synonym>gamma-Oxybutyrate</synonym>
    <synonym>gamma-Oxybutyric acid</synonym>
    <synonym>Succinic semialdehyde, calcium salt</synonym>
    <synonym>Succinic acid semialdehyde</synonym>
  </synonyms>
  <chemical_formula>C4H6O3</chemical_formula>
  <average_molecular_weight>102.0886</average_molecular_weight>
  <monisotopic_moleculate_weight>102.031694058</monisotopic_moleculate_weight>
  <iupac_name>4-oxobutanoic acid</iupac_name>
  <traditional_iupac>succinic semialdehyde</traditional_iupac>
  <cas_registry_number>692-29-5</cas_registry_number>
  <smiles>OC(=O)CCC=O</smiles>
  <inchi>InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7)</inchi>
  <inchikey>UIUJIQZEACWQSV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Straight chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydrogen aldehydes</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydrogen aldehyde</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fatty aldehydes</external_descriptor>
      <external_descriptor>aldehydic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-oxobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>102.0886</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>102.031694058</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H6O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UIUJIQZEACWQSV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>22.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22303</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>1080</chemspider_id>
  <kegg_id>C00232</kegg_id>
  <pubchem_compound_id>1112</pubchem_compound_id>
  <foodb_id>FDB022516</foodb_id>
  <drugbank_id>DBMET01476</drugbank_id>
  <pdbe_id/>
  <chebi_id>16265</chebi_id>
  <knapsack_id>C00019682</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34331</bigg_id>
  <wikipedia_id>Succinic semialdehyde</wikipedia_id>
  <metlin_id>6114</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Bruce, R.; Sims, K.; Pitts, F. N., Jr.  Synthesis and purification of succinic semialdehyde.    Analytical Biochemistry  (1971),  41(1),  271-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00595</protein_accession>
      <name>Hydroxyacid-oxoacid transhydrogenase, mitochondrial</name>
      <uniprot_id>A6QP15</uniprot_id>
      <gene_name>ADHFE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00596</protein_accession>
      <name>4-aminobutyrate aminotransferase, mitochondrial</name>
      <uniprot_id>Q9BGI0</uniprot_id>
      <gene_name>ABAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:12 UTC</creation_date>
  <update_date>2020-03-13 16:26:50 UTC</update_date>
  <accession>BMDB0001260</accession>
  <secondary_accessions>
    <accession>BMDB01260</accession>
  </secondary_accessions>
  <name>ADP-Ribosyl-L-arginine</name>
  <description/>
  <synonyms>
    <synonym>N(Omega)-(ADP-D-ribosyl)-arginine</synonym>
    <synonym>N(Omega)-(ADP-D-ribosyl)-L-arginine</synonym>
    <synonym>N(Omega)-(ADP-delta-ribosyl)-arginine</synonym>
    <synonym>N(Omega)-(ADP-delta-ribosyl)-L-arginine</synonym>
    <synonym>N(W)-(ADP-D-Ribosyl)-arginine</synonym>
    <synonym>N(W)-(ADP-D-Ribosyl)-L-arginine</synonym>
    <synonym>N(W)-(ADP-delta-Ribosyl)-arginine</synonym>
    <synonym>N(W)-(ADP-delta-Ribosyl)-L-arginine</synonym>
    <synonym>N2-(ADP-D-Ribosyl)-L-arginine</synonym>
    <synonym>N2-(ADP-delta-Ribosyl)-L-arginine</synonym>
    <synonym>2-Amino-5-(n'-{5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}carbamimidamido)pentanoate</synonym>
  </synonyms>
  <chemical_formula>C21H35N9O15P2</chemical_formula>
  <average_molecular_weight>715.5014</average_molecular_weight>
  <monisotopic_moleculate_weight>715.172784519</monisotopic_moleculate_weight>
  <iupac_name>2-amino-5-[(E)-[amino({5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}amino)methylidene]amino]pentanoic acid</iupac_name>
  <traditional_iupac>2-amino-5-[(E)-{amino[(5-{[({[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl)amino]methylidene}amino]pentanoic acid</traditional_iupac>
  <cas_registry_number>103960-56-1</cas_registry_number>
  <smiles>NC(CCC\N=C(/N)NC1OC(COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C(N)N=CN=C23)C(O)C1O)C(O)=O</smiles>
  <inchi>InChI=1S/C21H35N9O15P2/c22-8(20(35)36)2-1-3-25-21(24)29-18-14(33)12(31)9(43-18)4-41-46(37,38)45-47(39,40)42-5-10-13(32)15(34)19(44-10)30-7-28-11-16(23)26-6-27-17(11)30/h6-10,12-15,18-19,31-34H,1-5,22H2,(H,35,36)(H,37,38)(H,39,40)(H2,23,26,27)(H3,24,25,29)</inchi>
  <inchikey>IWVSYNGKNZFSSA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine nucleotide sugars</sub_class>
    <direct_parent>Purine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Alpha amino acids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Guanidines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-9.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-5-[(E)-[amino({5-[({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl}amino)methylidene]amino]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>715.5014</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>715.172784519</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CCC\N=C(/N)NC1OC(COP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=NC3=C(N)N=CN=C23)C(O)C1O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H35N9O15P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H35N9O15P2/c22-8(20(35)36)2-1-3-25-21(24)29-18-14(33)12(31)9(43-18)4-41-46(37,38)45-47(39,40)42-5-10-13(32)15(34)19(44-10)30-7-28-11-16(23)26-6-27-17(11)30/h6-10,12-15,18-19,31-34H,1-5,22H2,(H,35,36)(H,37,38)(H,39,40)(H2,23,26,27)(H3,24,25,29)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IWVSYNGKNZFSSA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>385.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>151.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>65.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>65891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369210</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>479</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>493</pubchem_compound_id>
  <foodb_id>FDB022517</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6115</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:13 UTC</creation_date>
  <update_date>2020-03-13 16:26:51 UTC</update_date>
  <accession>BMDB0001261</accession>
  <secondary_accessions>
    <accession>BMDB01261</accession>
  </secondary_accessions>
  <name>Coproporphyrinogen III</name>
  <description>Coproporphyrinogen iii III, also known as coproporphyrinogen III III, belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure. Coproporphyrinogen iii III is possibly soluble (in water) and a weakly acidic compound (based on its pKa). Coproporphyrinogen iii III exists in all living species, ranging from bacteria to humans. In cattle, coproporphyrinogen III iii is involved in the metabolic pathway called the porphyrin metabolism pathway. Coproporphyrinogen iii III is a potentially toxic compound.</description>
  <synonyms>
    <synonym>3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropionic acid</synonym>
    <synonym>5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-21H,23H-porphine-2,7,12,18-tetrapropanoic acid</synonym>
    <synonym>COPROPORPHYRIN III</synonym>
    <synonym>3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropionate</synonym>
    <synonym>5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-21H,23H-porphine-2,7,12,18-tetrapropanoate</synonym>
    <synonym>3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoate</synonym>
    <synonym>3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoic acid</synonym>
    <synonym>5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-2,7,12,18-porphinetetrapropionate</synonym>
    <synonym>5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-2,7,12,18-porphinetetrapropionic acid</synonym>
    <synonym>Coproporphyrinogen</synonym>
    <synonym>Coproporphyrinogen-III</synonym>
  </synonyms>
  <chemical_formula>C36H44N4O8</chemical_formula>
  <average_molecular_weight>660.7566</average_molecular_weight>
  <monisotopic_moleculate_weight>660.315914404</monisotopic_moleculate_weight>
  <iupac_name>3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number>2624-63-7</cas_registry_number>
  <smiles>CC1=C2CC3=C(C)C(CCC(O)=O)=C(CC4=C(CCC(O)=O)C(C)=C(CC5=C(CCC(O)=O)C(C)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3</smiles>
  <inchi>InChI=1S/C36H44N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)</inchi>
  <inchikey>NIUVHXTXUXOFEB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
      <alternative_parent>Tetracarboxylic acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Porphyrin</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
      <substituent>Tetracarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>coproporphyrinogen</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>660.7566</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>660.315914404</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C2CC3=C(C)C(CCC(O)=O)=C(CC4=C(CCC(O)=O)C(C)=C(CC5=C(CCC(O)=O)C(C)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C36H44N4O8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C36H44N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NIUVHXTXUXOFEB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>212.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>181.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>72.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22465</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>315</chemspider_id>
  <kegg_id>C03263</kegg_id>
  <pubchem_compound_id>321</pubchem_compound_id>
  <foodb_id>FDB022518</foodb_id>
  <drugbank_id>DB04461</drugbank_id>
  <pdbe_id/>
  <chebi_id>15439</chebi_id>
  <knapsack_id>C00007284</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>41515</bigg_id>
  <wikipedia_id>Coproporphyrinogen III</wikipedia_id>
  <metlin_id>6116</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Shoolingin-Jordan, Peter M.  The biosynthesis of coproporphyrinogen III.    Porphyrin Handbook  (2003),  12  33-74.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01255</protein_accession>
      <name>N-acetyltransferase 14</name>
      <uniprot_id>Q3MHZ1</uniprot_id>
      <gene_name>NAT14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:14 UTC</creation_date>
  <update_date>2020-04-14 22:49:02 UTC</update_date>
  <accession>BMDB0001262</accession>
  <secondary_accessions>
    <accession>BMDB01262</accession>
  </secondary_accessions>
  <name>Maltotriose</name>
  <description>Maltotriose belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Maltotriose is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Maltotriose exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>alpha-D-GLC-(1-&gt;4)-alpha-D-GLC-(1-&gt;4)-D-GLC</synonym>
    <synonym>alpha-D-Glucosyl-(1-&gt;4)-alpha-D-glucosyl-(1-&gt;4)-D-glucoose</synonym>
    <synonym>D-Maltotriose</synonym>
    <synonym>Glcalpha1-4glcalpha1-4GLC</synonym>
    <synonym>Amylotriose</synonym>
    <synonym>a-D-GLC-(1-&gt;4)-a-D-GLC-(1-&gt;4)-D-GLC</synonym>
    <synonym>Α-D-GLC-(1-&gt;4)-α-D-GLC-(1-&gt;4)-D-GLC</synonym>
    <synonym>a-D-Glucosyl-(1-&gt;4)-a-D-glucosyl-(1-&gt;4)-D-glucoose</synonym>
    <synonym>Α-D-glucosyl-(1-&gt;4)-α-D-glucosyl-(1-&gt;4)-D-glucoose</synonym>
    <synonym>4-O-(4-O-Hexopyranosylhexopyranosyl)hexose</synonym>
    <synonym>D-(+)-Maltotriose</synonym>
    <synonym>delta-(+)-Maltotriose</synonym>
    <synonym>O-alpha-D-Glucopyranosyl-(1beta94)-O-alpha-D-glucopyranosyl-(1beta94)-O-alpha-D-glucose</synonym>
    <synonym>O-alpha-delta-Glucopyranosyl-(1beta94)-O-alpha-delta-glucopyranosyl-(1beta94)-O-alpha-delta-glucose</synonym>
  </synonyms>
  <chemical_formula>C18H32O16</chemical_formula>
  <average_molecular_weight>504.4371</average_molecular_weight>
  <monisotopic_moleculate_weight>504.169034976</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>maltotriose</traditional_iupac>
  <cas_registry_number>1109-28-0</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C18H32O16/c19-1-4-7(22)8(23)12(27)17(31-4)34-15-6(3-21)32-18(13(28)10(15)25)33-14-5(2-20)30-16(29)11(26)9(14)24/h4-29H,1-3H2/t4-,5-,6-,7-,8+,9-,10-,11-,12-,13-,14-,15-,16?,17-,18-/m1/s1</inchi>
  <inchikey>FYGDTMLNYKFZSV-DZOUCCHMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Oligosaccharides</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Oligosaccharide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>504.4371</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>504.169034976</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)C(O)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H32O16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H32O16/c19-1-4-7(22)8(23)12(27)17(31-4)34-15-6(3-21)32-18(13(28)10(15)25)33-14-5(2-20)30-16(29)11(26)9(14)24/h4-29H,1-3H2/t4-,5-,6-,7-,8+,9-,10-,11-,12-,13-,14-,15-,16?,17-,18-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FYGDTMLNYKFZSV-DZOUCCHMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>268.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>100.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334236</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>388669</chemspider_id>
  <kegg_id>C01835</kegg_id>
  <pubchem_compound_id>439586</pubchem_compound_id>
  <foodb_id>FDB001196</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>140999</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>38512</bigg_id>
  <wikipedia_id>Maltotriose</wikipedia_id>
  <metlin_id>3585</metlin_id>
  <meta_cyc_id>MALTOTRIOSE</meta_cyc_id>
  <synthesis_reference>Wallenfels, Kurt; Bender, Hans.  Maltotriose.    (1965),     2 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:16 UTC</creation_date>
  <update_date>2020-03-13 16:26:52 UTC</update_date>
  <accession>BMDB0001263</accession>
  <secondary_accessions>
    <accession>BMDB01263</accession>
  </secondary_accessions>
  <name>Allysine</name>
  <description>Allysine, also known as 6-oxonorleucine or alpha-aasa, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Allysine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Allysine exists in all eukaryotes, ranging from yeast to humans. Allysine participates in a number of enzymatic reactions, within cattle. In particular, Allysine and L-glutamic acid can be biosynthesized from saccharopine through the action of the enzyme Alpha-aminoadipic semialdehyde synthase, mitochondrial. In addition, Allysine can be converted into aminoadipic acid; which is catalyzed by the enzyme Alpha-aminoadipic semialdehyde dehydrogenase. In cattle, allysine is involved in the metabolic pathway called the lysine degradation pathway. Allysine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2-Amino-5-formylvaleric acid</synonym>
    <synonym>2-Aminoadipate 6-semialdehyde</synonym>
    <synonym>6-Oxonorleucine</synonym>
    <synonym>alpha-Aminoadipic acid delta-semialdehyde</synonym>
    <synonym>alpha-Aminoadipic delta-semialdehyde</synonym>
    <synonym>HCO-[CH2]3-CH(NH2)-COOH</synonym>
    <synonym>2-Amino-5-formylvalerate</synonym>
    <synonym>2-Aminoadipic acid 6-semialdehyde</synonym>
    <synonym>a-Aminoadipate delta-semialdehyde</synonym>
    <synonym>a-Aminoadipic acid delta-semialdehyde</synonym>
    <synonym>alpha-Aminoadipate delta-semialdehyde</synonym>
    <synonym>Α-aminoadipate δ-semialdehyde</synonym>
    <synonym>Α-aminoadipic acid δ-semialdehyde</synonym>
    <synonym>a-Aminoadipic delta-semialdehyde</synonym>
    <synonym>Α-aminoadipic δ-semialdehyde</synonym>
    <synonym>a-Aminoadipate δ-semialdehyde</synonym>
    <synonym>a-Aminoadipic acid δ-semialdehyde</synonym>
    <synonym>a-Aminoadipic δ-semialdehyde</synonym>
    <synonym>(2S)-2-Amino-6-oxohexanoate</synonym>
    <synonym>(2S)-2-Amino-6-oxohexanoic acid</synonym>
    <synonym>2-Amino-hexanedioate</synonym>
    <synonym>2-Amino-hexanedioic acid</synonym>
    <synonym>2-Amino-hexanedioic acid semialdhyde</synonym>
    <synonym>2-Aminoadipate semialdehyde</synonym>
    <synonym>2-Aminoadipate-6-semialdehyde</synonym>
    <synonym>5-Formyl-norvaline</synonym>
    <synonym>6-oxo-L-Norleucine</synonym>
    <synonym>6-oxo-Norleucine</synonym>
    <synonym>alpha-Aminoadipic semialdehyde</synonym>
    <synonym>L-2-Aminoadipate 6-semialdehyde</synonym>
    <synonym>L-6-Oxonorleucine</synonym>
    <synonym>L-Allysine</synonym>
    <synonym>2-Aminoadipic semialdehyde</synonym>
    <synonym>alpha-AASA</synonym>
    <synonym>alpha-Aminoadipate semialdehyde</synonym>
  </synonyms>
  <chemical_formula>C6H11NO3</chemical_formula>
  <average_molecular_weight>145.1564</average_molecular_weight>
  <monisotopic_moleculate_weight>145.073893223</monisotopic_moleculate_weight>
  <iupac_name>2-amino-6-oxohexanoic acid</iupac_name>
  <traditional_iupac>allysine</traditional_iupac>
  <cas_registry_number>1962-83-0</cas_registry_number>
  <smiles>NC(CCCC=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)</inchi>
  <inchikey>GFXYTQPNNXGICT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydrogen aldehydes</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-hydrogen aldehyde</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>non-proteinogenic alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-6-oxohexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>145.1564</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>145.073893223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CCCC=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H11NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GFXYTQPNNXGICT-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>90462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>90463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>90464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>153621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>153622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>153623</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>202</chemspider_id>
  <kegg_id>C01475</kegg_id>
  <pubchem_compound_id>207</pubchem_compound_id>
  <foodb_id>FDB010644</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>17027</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>1445244</bigg_id>
  <wikipedia_id>Allysine</wikipedia_id>
  <metlin_id>6118</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00631</protein_accession>
      <name>Alpha-aminoadipic semialdehyde synthase, mitochondrial</name>
      <uniprot_id>A8E657</uniprot_id>
      <gene_name>AASS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00632</protein_accession>
      <name>Probable saccharopine dehydrogenase</name>
      <uniprot_id>Q3T067</uniprot_id>
      <gene_name>SCCPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00954</protein_accession>
      <name>Alpha-aminoadipic semialdehyde dehydrogenase</name>
      <uniprot_id>Q2KJC9</uniprot_id>
      <gene_name>ALDH7A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:17 UTC</creation_date>
  <update_date>2020-04-15 22:28:17 UTC</update_date>
  <accession>BMDB0001264</accession>
  <secondary_accessions>
    <accession>BMDB01264</accession>
  </secondary_accessions>
  <name>Dehydroascorbic acid</name>
  <description>Dehydroascorbic acid, also known as dehydroascorbate or dhaa, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Dehydroascorbic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dehydroascorbic acid exists in all living organisms, ranging from bacteria to humans. Norepinephrine and dehydroascorbic acid can be biosynthesized from dopamine and ascorbic acid through its interaction with the enzyme dopamine beta-hydroxylase. In cattle, dehydroascorbic acid is involved in the metabolic pathway called the tyrosine metabolism pathway.</description>
  <synonyms>
    <synonym>Dehydroascorbate</synonym>
    <synonym>1-Dehydroascorbate</synonym>
    <synonym>1-Dehydroascorbic acid</synonym>
    <synonym>Dehydro-L-ascorbate</synonym>
    <synonym>Dehydro-L-ascorbic acid</synonym>
    <synonym>DHAA</synonym>
    <synonym>L-Dehydroascorbate</synonym>
    <synonym>L-Dehydroascorbic acid</synonym>
    <synonym>L-Threo-2,3-hexodiulosonic acid gamma-lactone</synonym>
    <synonym>L-Threo-hexo-2,3-diulosono-1,4-lactone</synonym>
    <synonym>Oxidized ascorbate</synonym>
    <synonym>Oxidized ascorbic acid</synonym>
    <synonym>Oxidized vitamin C</synonym>
    <synonym>Dehydroerythorbic acid</synonym>
  </synonyms>
  <chemical_formula>C6H6O6</chemical_formula>
  <average_molecular_weight>174.1082</average_molecular_weight>
  <monisotopic_moleculate_weight>174.016437924</monisotopic_moleculate_weight>
  <iupac_name>(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione</iupac_name>
  <traditional_iupac>(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione</traditional_iupac>
  <cas_registry_number>490-83-5</cas_registry_number>
  <smiles>[H][C@@]1(OC(=O)C(=O)C1=O)[C@H](O)CO</smiles>
  <inchi>InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5-/m1/s1</inchi>
  <inchikey>SBJKKFFYIZUCET-DUZGATOHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Lactones</class>
    <sub_class>Gamma butyrolactones</sub_class>
    <direct_parent>Gamma butyrolactones</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Furanones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>3-furanone</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Gamma butyrolactone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5R)-5-[(1R)-1,2-dihydroxyethyl]oxolane-2,3,4-trione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>174.1082</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>174.016437924</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(OC(=O)C(=O)C1=O)[C@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H6O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SBJKKFFYIZUCET-DUZGATOHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>100.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>33.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335262</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.240 +/- 0.172</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized whole milk</comment>
      <references>
        <reference>
          <reference_text>Bilic N: Assay for both ascorbic and dehydroascorbic acid in dairy foods by high-performance liquid chromatography using precolumn derivatization with methoxy- and ethoxy-1,2-phenylenediamine. J Chromatogr. 1991 May 10;543(2):367-74.</reference_text>
          <pubmed_id>1880195</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.730 +/- 1.149</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Bilic N: Assay for both ascorbic and dehydroascorbic acid in dairy foods by high-performance liquid chromatography using precolumn derivatization with methoxy- and ethoxy-1,2-phenylenediamine. J Chromatogr. 1991 May 10;543(2):367-74.</reference_text>
          <pubmed_id>1880195</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>182283</chemspider_id>
  <kegg_id>C00425</kegg_id>
  <pubchem_compound_id>210328</pubchem_compound_id>
  <foodb_id>FDB021459</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>17242</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>34945</bigg_id>
  <wikipedia_id>Dehydroascorbic acid</wikipedia_id>
  <metlin_id>342</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Utsumi, Isamu; Harada, Kiyoshi; Miura, Hiroshi.  Dehydroascorbic acid.    Jpn. Tokkyo Koho  (1972),     2 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Bilic N: Assay for both ascorbic and dehydroascorbic acid in dairy foods by high-performance liquid chromatography using precolumn derivatization with methoxy- and ethoxy-1,2-phenylenediamine. J Chromatogr. 1991 May 10;543(2):367-74.</reference_text>
      <pubmed_id>1880195</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00655</protein_accession>
      <name>Dopamine beta-hydroxylase</name>
      <uniprot_id>P15101</uniprot_id>
      <gene_name>DBH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00665</protein_accession>
      <name>Peptidyl-glycine alpha-amidating monooxygenase</name>
      <uniprot_id>P10731</uniprot_id>
      <gene_name>PAM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:18 UTC</creation_date>
  <update_date>2020-03-13 16:26:53 UTC</update_date>
  <accession>BMDB0001265</accession>
  <secondary_accessions>
    <accession>BMDB01265</accession>
  </secondary_accessions>
  <name>Fucose 1-phosphate</name>
  <description>Fucose 1-phosphate belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Fucose 1-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Fucose 1-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Fucose 1-phosphate can be converted into GDP-L-fucose; which is catalyzed by the enzyme fucose-1-phosphate guanylyltransferase. In addition, Fucose 1-phosphate can be biosynthesized from L-fucose through its interaction with the enzyme L-fucose kinase. In cattle, fucose 1-phosphate is involved in the metabolic pathway called the fructose and mannose degradation pathway.</description>
  <synonyms>
    <synonym>6-Deoxy-1-O-phosphono-L-galactopyranose</synonym>
    <synonym>6-Deoxy-L-galactose 1-phosphate</synonym>
    <synonym>L-Fucose 1-phosphate</synonym>
    <synonym>6-Deoxy-L-galactose 1-phosphoric acid</synonym>
    <synonym>L-Fucose 1-phosphoric acid</synonym>
    <synonym>Fucose 1-phosphoric acid</synonym>
    <synonym>(3,4,5-Trihydroxy-6-methyl-tetrahydropyran-2-yl)oxyphosphonate</synonym>
    <synonym>(3,4,5-Trihydroxy-6-methyl-tetrahydropyran-2-yl)oxyphosphonic acid</synonym>
    <synonym>6-Deoxy-L-galactopyranose 1-(dihydrogen phosphate)</synonym>
    <synonym>Fuculose 1-phosphate</synonym>
    <synonym>L-Fucose-1P</synonym>
  </synonyms>
  <chemical_formula>C6H13O8P</chemical_formula>
  <average_molecular_weight>244.1364</average_molecular_weight>
  <monisotopic_moleculate_weight>244.034803904</monisotopic_moleculate_weight>
  <iupac_name>{[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>fuculose 1-phosphate</traditional_iupac>
  <cas_registry_number>16562-58-6</cas_registry_number>
  <smiles>C[C@@H]1OC(OP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H13O8P/c1-2-3(7)4(8)5(9)6(13-2)14-15(10,11)12/h2-9H,1H3,(H2,10,11,12)/t2-,3+,4+,5-,6?/m0/s1</inchi>
  <inchikey>PTVXQARCLQPGIR-DHVFOXMCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharide phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>deoxyaldohexose phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>244.1364</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>244.034803904</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H]1OC(OP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O8P/c1-2-3(7)4(8)5(9)6(13-2)14-15(10,11)12/h2-9H,1H3,(H2,10,11,12)/t2-,3+,4+,5-,6?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PTVXQARCLQPGIR-DHVFOXMCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>136.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355803</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>388911</chemspider_id>
  <kegg_id>C02985</kegg_id>
  <pubchem_compound_id>439871</pubchem_compound_id>
  <foodb_id>FDB022520</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>28319</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>40955</bigg_id>
  <wikipedia_id/>
  <metlin_id>6120</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:19 UTC</creation_date>
  <update_date>2020-04-16 17:51:35 UTC</update_date>
  <accession>BMDB0001266</accession>
  <secondary_accessions>
    <accession>BMDB01266</accession>
  </secondary_accessions>
  <name>L-Sorbose</name>
  <description>D-Fructose, also known as D-tagatose or D-lyxo-2-hexulose, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. D-Fructose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Fructose exists in all living species, ranging from bacteria to humans. D-Fructose participates in a number of enzymatic reactions, within cattle. In particular, D-Fructose can be biosynthesized from sorbitol through its interaction with the enzyme sorbitol dehydrogenase. In addition, D-Fructose can be biosynthesized from Beta-D-fructose 2-phosphate through the action of the enzyme 14 kda phosphohistidine phosphatase. In cattle, D-fructose is involved in the metabolic pathway called the fructose and mannose degradation pathway. D-Fructose is a potentially toxic compound.</description>
  <synonyms>
    <synonym>alpha-L-Sorbopyranose</synonym>
    <synonym>Hex-2-ulose</synonym>
    <synonym>L(-) Sorbose for biochemistry</synonym>
    <synonym>L(-)-Sorbose</synonym>
    <synonym>L-(-)-Sorbose</synonym>
    <synonym>L-(-)-Sorbose 99%</synonym>
    <synonym>L-1,3,4,5,6-Pentahydroxyhexan-2-one</synonym>
    <synonym>L-Sorbinose</synonym>
    <synonym>L-Xylo-2-hexulose</synonym>
    <synonym>L-Xylo-hexulose</synonym>
    <synonym>Sorbin</synonym>
    <synonym>Sorbinose</synonym>
    <synonym>Sorbose</synonym>
    <synonym>Xylo-hexulose</synonym>
    <synonym>alpha-L-Xylo-hexopyranos-2-ulose</synonym>
    <synonym>Α-L-xylo-hexopyranos-2-ulose</synonym>
    <synonym>Α-L-sorbopyranose</synonym>
    <synonym>a-L-Sorbopyranose</synonym>
  </synonyms>
  <chemical_formula>C6H12O6</chemical_formula>
  <average_molecular_weight>180.1559</average_molecular_weight>
  <monisotopic_moleculate_weight>180.063388116</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>α-L-sorbopyranose</traditional_iupac>
  <cas_registry_number>470-15-5</cas_registry_number>
  <smiles>OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4+,5-,6+/m0/s1</inchi>
  <inchikey>LKDRXBCSQODPBY-BGPJRJDNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharides</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-sorbopyranose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>165 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>360.0 mg/mL at 17 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>180.1559</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>180.063388116</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4+,5-,6+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LKDRXBCSQODPBY-BGPJRJDNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>110.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>36.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181748</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>763.813 +/- 751.731</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>763.813 +/- 751.731</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C08356</kegg_id>
  <foodb_id>FDB001126</foodb_id>
  <chemspider_id>390208</chemspider_id>
  <pubchem_compound_id>441484</pubchem_compound_id>
  <pdbe_id>SOE</pdbe_id>
  <chebi_id>10295</chebi_id>
  <drugbank_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>SORBOSE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Sorbose</wikipedia_id>
  <metlin_id>6121</metlin_id>
  <synthesis_reference>Banjopnoppakun, Tanaphat; Moonmangmee, Somporn; Moonmangmee, Duangtip.  Production of L-sorbose by thermotolerant acetic acid bacteria.    Proceeding of the Kasetsart University Annual Conference, 44th, Bangkok, Thailand, Jan. 30-Feb. 2, 2006  (2006),     117-123.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00784</protein_accession>
      <name>Sorbitol dehydrogenase</name>
      <uniprot_id>Q58D31</uniprot_id>
      <gene_name>SORD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:20 UTC</creation_date>
  <update_date>2020-03-13 16:26:54 UTC</update_date>
  <accession>BMDB0001267</accession>
  <secondary_accessions>
    <accession>BMDB01267</accession>
  </secondary_accessions>
  <name>4-Oxo-4-(3-pyridyl)-butanamide</name>
  <description/>
  <synonyms>
    <synonym>4-(3-Pyridyl)-4-oxobutyramide</synonym>
    <synonym>POBAM</synonym>
    <synonym>4-oxo-4-(Pyridin-3-yl)butanimidate</synonym>
  </synonyms>
  <chemical_formula>C9H10N2O2</chemical_formula>
  <average_molecular_weight>178.1879</average_molecular_weight>
  <monisotopic_moleculate_weight>178.074227574</monisotopic_moleculate_weight>
  <iupac_name>4-oxo-4-(pyridin-3-yl)butanamide</iupac_name>
  <traditional_iupac>4-oxo-4-(3-pyridyl)-butanamide</traditional_iupac>
  <cas_registry_number/>
  <smiles>NC(=O)CCC(=O)C1=CN=CC=C1</smiles>
  <inchi>InChI=1S/C9H10N2O2/c10-9(13)4-3-8(12)7-2-1-5-11-6-7/h1-2,5-6H,3-4H2,(H2,10,13)</inchi>
  <inchikey>DJEKVKGYYASXCW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Aryl alkyl ketones</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Fatty amides</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Pyridines and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Aryl alkyl ketone</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Pyridine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-oxo-4-(pyridin-3-yl)butanamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>178.1879</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>178.074227574</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)CCC(=O)C1=CN=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10N2O2/c10-9(13)4-3-8(12)7-2-1-5-11-6-7/h1-2,5-6H,3-4H2,(H2,10,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DJEKVKGYYASXCW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>73.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359973</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022521</foodb_id>
  <chemspider_id>422</chemspider_id>
  <pubchem_compound_id>435</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6122</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:21 UTC</creation_date>
  <update_date>2020-03-13 16:26:55 UTC</update_date>
  <accession>BMDB0001268</accession>
  <secondary_accessions>
    <accession>BMDB01268</accession>
  </secondary_accessions>
  <name>4-Fumarylacetoacetic acid</name>
  <description/>
  <synonyms>
    <synonym>Fumarylacetoacetone</synonym>
    <synonym>Fumarylacetoacetate</synonym>
    <synonym>Fumarylacetoacetic acid</synonym>
    <synonym>4-Fumarylacetoacetate</synonym>
    <synonym>4-Fumaryl-acetoacetate</synonym>
    <synonym>(2E)-4,6-Dioxo-2-octenedioic acid</synonym>
    <synonym>4-Fumarylacetoacetic acid</synonym>
  </synonyms>
  <chemical_formula>C8H8O6</chemical_formula>
  <average_molecular_weight>200.1455</average_molecular_weight>
  <monisotopic_moleculate_weight>200.032087988</monisotopic_moleculate_weight>
  <iupac_name>(2E)-4,6-dioxooct-2-enedioic acid</iupac_name>
  <traditional_iupac>4-fumarylacetoacetic acid</traditional_iupac>
  <cas_registry_number>28613-33-4</cas_registry_number>
  <smiles>OC(=O)CC(=O)CC(=O)\C=C\C(O)=O</smiles>
  <inchi>InChI=1S/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1+</inchi>
  <inchikey>GACSIVHAIFQKTC-OWOJBTEDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12  carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Medium-chain keto acids and derivatives</sub_class>
    <direct_parent>Medium-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Acryloyl compounds</alternative_parent>
      <alternative_parent>Beta-diketones</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Beta-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Enones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>1,3-diketone</substituent>
      <substituent>Acryloyl-group</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha,beta-unsaturated ketone</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Beta-keto acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Enone</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Medium-chain keto acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
      <external_descriptor>beta-diketone</external_descriptor>
      <external_descriptor>oxo dicarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-4,6-dioxooct-2-enedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>200.1455</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>200.032087988</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC(=O)CC(=O)\C=C\C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H8O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GACSIVHAIFQKTC-OWOJBTEDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>108.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>44.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38002</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>61898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>118520</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01061</kegg_id>
  <foodb_id>FDB022522</foodb_id>
  <chemspider_id>4444081</chemspider_id>
  <pubchem_compound_id>5280398</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30907</chebi_id>
  <drugbank_id/>
  <knapsack_id>C00007599</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>4-FUMARYL-ACETOACETATE</meta_cyc_id>
  <bigg_id>1485275</bigg_id>
  <wikipedia_id>Fumarylacetoacetic_acid</wikipedia_id>
  <metlin_id>6123</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00427</protein_accession>
      <name>Fumarylacetoacetase</name>
      <uniprot_id>A5PKH3</uniprot_id>
      <gene_name>FAH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:22 UTC</creation_date>
  <update_date>2020-03-13 16:26:55 UTC</update_date>
  <accession>BMDB0001269</accession>
  <secondary_accessions>
    <accession>BMDB01269</accession>
  </secondary_accessions>
  <name>Methylmalonyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>(R)-Methylmalonyl-CoA</synonym>
    <synonym>(R)-Methylmalonyl-coenzyme A</synonym>
    <synonym>(S)-2-Methyl-3-oxopropanoyl-CoA</synonym>
    <synonym>(S)-Methyl-malonyl-CoA</synonym>
    <synonym>(S)-Methyl-malonyl-coenzyme A</synonym>
    <synonym>CH3-Malonyl-CoA</synonym>
    <synonym>CH3-Malonyl-coenzyme A</synonym>
    <synonym>D-Methylmalonyl-CoA</synonym>
    <synonym>D-Methylmalonyl-coenzyme A</synonym>
    <synonym>L-Methylmalonyl-CoA</synonym>
    <synonym>L-Methylmalonyl-coenzyme A</synonym>
    <synonym>Methyl-malonyl-coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C25H40N7O19P3S</chemical_formula>
  <average_molecular_weight>867.607</average_molecular_weight>
  <monisotopic_moleculate_weight>867.131252359</monisotopic_moleculate_weight>
  <iupac_name>(2S)-3-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-2-methyl-3-oxopropanoic acid</iupac_name>
  <traditional_iupac>(2S)-3-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-2-methyl-3-oxopropanoic acid</traditional_iupac>
  <cas_registry_number>104809-02-1</cas_registry_number>
  <smiles>C[C@@H](C(O)=O)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C25H40N7O19P3S/c1-12(23(37)38)24(39)55-7-6-27-14(33)4-5-28-21(36)18(35)25(2,3)9-48-54(45,46)51-53(43,44)47-8-13-17(50-52(40,41)42)16(34)22(49-13)32-11-31-15-19(26)29-10-30-20(15)32/h10-13,16-18,22,34-35H,4-9H2,1-3H3,(H,27,33)(H,28,36)(H,37,38)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t12-,13+,16+,17+,18?,22+/m0/s1</inchi>
  <inchikey>MZFOKIKEPGUZEN-PNEPRAIJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-dicarbonyl compounds</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,3-dicarbonyl compound</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-3-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-2-methyl-3-oxopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>867.607</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>867.131252359</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](C(O)=O)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H40N7O19P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C25H40N7O19P3S/c1-12(23(37)38)24(39)55-7-6-27-14(33)4-5-28-21(36)18(35)25(2,3)9-48-54(45,46)51-53(43,44)47-8-13-17(50-52(40,41)42)16(34)22(49-13)32-11-31-15-19(26)29-10-30-20(15)32/h10-13,16-18,22,34-35H,4-9H2,1-3H3,(H,27,33)(H,28,36)(H,37,38)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t12-,13+,16+,17+,18?,22+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MZFOKIKEPGUZEN-PNEPRAIJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>400.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>183.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>75.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35830</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022523</foodb_id>
  <chemspider_id>388424</chemspider_id>
  <kegg_id>C00683</kegg_id>
  <pubchem_compound_id>439291</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15466</chebi_id>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>37090</bigg_id>
  <wikipedia_id>Methylmalonyl-CoA</wikipedia_id>
  <metlin_id>462</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00254</protein_accession>
      <name>Methylmalonyl-CoA epimerase, mitochondrial</name>
      <uniprot_id>Q2KIZ3</uniprot_id>
      <gene_name>MCEE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00623</protein_accession>
      <name>Methylmalonyl-CoA mutase, mitochondrial</name>
      <uniprot_id>Q9GK13</uniprot_id>
      <gene_name>MUT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:24 UTC</creation_date>
  <update_date>2020-03-13 16:26:56 UTC</update_date>
  <accession>BMDB0001270</accession>
  <secondary_accessions>
    <accession>BMDB01270</accession>
  </secondary_accessions>
  <name>Glyceric acid 1,3-biphosphate</name>
  <description/>
  <synonyms>
    <synonym>(R)-2-Hydroxy-3-(phosphonooxy)-1-monoanhydride with phosphoric propanoic acid</synonym>
    <synonym>1,3-Bisphospho-D-glycerate</synonym>
    <synonym>3-Phospho-D-glyceroyl phosphate</synonym>
    <synonym>D-Glycerate 1,3-diphosphate</synonym>
    <synonym>(R)-2-Hydroxy-3-(phosphonooxy)-1-monoanhydride with phosphoric propanoate</synonym>
    <synonym>1,3-Bisphospho-D-glyceric acid</synonym>
    <synonym>3-Phospho-D-glyceroyl phosphoric acid</synonym>
    <synonym>D-Glyceric acid 1,3-diphosphoric acid</synonym>
    <synonym>Glycerate 1,3-biphosphate</synonym>
    <synonym>Glyceric acid 1,3-biphosphoric acid</synonym>
    <synonym>3-Phospho-D-glyceroyl dihydrogen phosphoric acid</synonym>
    <synonym>1,3-Biphosphoglycerate</synonym>
    <synonym>1,3-Bisphosphoglycerate</synonym>
    <synonym>1,3-Bisphosphoglyceric acid</synonym>
    <synonym>1,3-Diphosphoglycerate</synonym>
    <synonym>1,3-Diphosphoglyceric acid</synonym>
    <synonym>3-Phospho-D-glyceroyl-phosphate</synonym>
    <synonym>3-Phosphoglyceroyl phosphate</synonym>
    <synonym>3-Phosphoglyceroyl-p</synonym>
    <synonym>3-Phosphoglyceroyl-phosphate</synonym>
    <synonym>3-Phosphonato-D-glyceroyl phosphate</synonym>
    <synonym>3-Phosphonatoglyceroyl phosphate</synonym>
    <synonym>3-p-Glyceroyl-p</synonym>
    <synonym>D-Glycerate 1,3-biphosphate</synonym>
    <synonym>D-Glycerate 1,3-bisphosphate</synonym>
    <synonym>D-Glyceric acid 1,3-biphosphate</synonym>
    <synonym>D-Glyceric acid 1,3-bisphosphate</synonym>
    <synonym>D-Glyceric acid 1,3-diphosphate</synonym>
    <synonym>DPG</synonym>
    <synonym>Glycerate 1,3-bisphosphate</synonym>
    <synonym>Glycerate 1,3-diphosphate</synonym>
    <synonym>Glyceric acid 1,3-bisphosphate</synonym>
    <synonym>Glyceric acid 1,3-diphosphate</synonym>
    <synonym>Phosphoglyceroyl-p</synonym>
    <synonym>p-Glyceroyl-p</synonym>
    <synonym>Glyceric acid 1,3-biphosphate</synonym>
  </synonyms>
  <chemical_formula>C3H8O10P2</chemical_formula>
  <average_molecular_weight>266.0371</average_molecular_weight>
  <monisotopic_moleculate_weight>265.9592695</monisotopic_moleculate_weight>
  <iupac_name>{[(2R)-2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>1,3-bisphospho-D-glycerate</traditional_iupac>
  <cas_registry_number>38168-82-0</cas_registry_number>
  <smiles>O[C@H](COP(O)(O)=O)C(=O)OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)/t2-/m1/s1</inchi>
  <inchikey>LJQLQCAXBUHEAZ-UWTATZPHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure  R-CO-P(O)(O)OH, R=H or organyl.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic phosphoric acids and derivatives</class>
    <sub_class>Phosphate esters</sub_class>
    <direct_parent>Acyl monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sugar acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyl monophosphate</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Glyceric_acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2,3-bisphosphoglyceric acid</external_descriptor>
      <external_descriptor>acyl monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R)-2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>266.0371</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>265.9592695</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H](COP(O)(O)=O)C(=O)OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H8O10P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)/t2-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LJQLQCAXBUHEAZ-UWTATZPHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>170.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerol Phosphate Shuttle</name>
      <smpdb_id>SMP0087199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Electron Transport Chain</name>
      <smpdb_id>SMP0087261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2796</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31687</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00236</kegg_id>
  <foodb_id>FDB030188</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>439191</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16001</chebi_id>
  <drugbank_id/>
  <knapsack_id>C00019552</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>1,3-Bisphosphoglyceric acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00154</protein_accession>
      <name>Glyceraldehyde-3-phosphate dehydrogenase</name>
      <uniprot_id>P10096</uniprot_id>
      <gene_name>GAPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00209</protein_accession>
      <name>Glyceraldehyde-3-phosphate dehydrogenase, testis-specific</name>
      <uniprot_id>Q2KJE5</uniprot_id>
      <gene_name>GAPDHS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00692</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q9XSN4</uniprot_id>
      <gene_name>GAPDL17</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00693</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q862K5</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00694</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q0QES8</uniprot_id>
      <gene_name>GAPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00695</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q4H0Z3</uniprot_id>
      <gene_name>gapdh</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00697</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q712W6</uniprot_id>
      <gene_name>GAPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00919</protein_accession>
      <name>Phosphoglycerate mutase 2</name>
      <uniprot_id>Q32KV0</uniprot_id>
      <gene_name>PGAM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00920</protein_accession>
      <name>Bisphosphoglycerate mutase</name>
      <uniprot_id>Q3T014</uniprot_id>
      <gene_name>BPGM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00921</protein_accession>
      <name>Phosphoglycerate mutase 1</name>
      <uniprot_id>Q3SZ62</uniprot_id>
      <gene_name>PGAM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:25 UTC</creation_date>
  <update_date>2020-03-13 16:26:56 UTC</update_date>
  <accession>BMDB0001271</accession>
  <secondary_accessions>
    <accession>BMDB01271</accession>
  </secondary_accessions>
  <name>Pseudouridine 5'-phosphate</name>
  <description/>
  <synonyms>
    <synonym>(1S)-1,4-Anhydro-1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-5-O-phosphono-D-ribitol</synonym>
    <synonym>5-(5-O-Phosphono-beta-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione</synonym>
    <synonym>5-(5-O-Phosphono-b-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione</synonym>
    <synonym>5-(5-O-Phosphono-β-D-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione</synonym>
    <synonym>Pseudouridine 5'-phosphoric acid</synonym>
    <synonym>Pseudouridylic acid</synonym>
  </synonyms>
  <chemical_formula>C9H13N2O9P</chemical_formula>
  <average_molecular_weight>324.1813</average_molecular_weight>
  <monisotopic_moleculate_weight>324.035866536</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5S)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>pseudouridine 5'-phosphate</traditional_iupac>
  <cas_registry_number>1157-60-4</cas_registry_number>
  <smiles>O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)C1=CNC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C9H13N2O9P/c12-5-4(2-19-21(16,17)18)20-7(6(5)13)3-1-10-9(15)11-8(3)14/h1,4-7,12-13H,2H2,(H2,16,17,18)(H2,10,11,14,15)/t4-,5-,6-,7+/m1/s1</inchi>
  <inchikey>MOBMOJGXNHLLIR-GBNDHIKLSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Nucleoside and nucleotide analogues</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C-nucleoside phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5S)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>324.1813</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>324.035866536</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)C1=CNC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13N2O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13N2O9P/c12-5-4(2-19-21(16,17)18)20-7(6(5)13)3-1-10-9(15)11-8(3)14/h1,4-7,12-13H,2H2,(H2,16,17,18)(H2,10,11,14,15)/t4-,5-,6-,7+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MOBMOJGXNHLLIR-GBNDHIKLSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>174.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>63.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30661</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01168</kegg_id>
  <foodb_id>FDB022525</foodb_id>
  <chemspider_id>388535</chemspider_id>
  <pubchem_compound_id>439424</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18116</chebi_id>
  <drugbank_id>DB03829</drugbank_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:26 UTC</creation_date>
  <update_date>2020-04-14 22:49:03 UTC</update_date>
  <accession>BMDB0001272</accession>
  <secondary_accessions>
    <accession>BMDB01272</accession>
  </secondary_accessions>
  <name>Nicotine glucuronide</name>
  <description/>
  <synonyms>
    <synonym>(S)-1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt</synonym>
    <synonym>3,4,5-Trihydroxy-6-[5-(1-methylpyrrolidin-2-yl)pyridin-1-yl]-oxane-2-carboxylate</synonym>
    <synonym>Nicotine N-glucuronide</synonym>
    <synonym>(S)-1-a-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt</synonym>
    <synonym>(S)-1-Α-D-glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt</synonym>
    <synonym>3,4,5-Trihydroxy-6-[5-(1-methylpyrrolidin-2-yl)pyridin-1-yl]-oxane-2-carboxylic acid</synonym>
    <synonym>(S)-1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-pyridinium inner salt</synonym>
    <synonym>(S)-1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-pyridinium inner salt</synonym>
    <synonym>(S)-1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)pyridinium inner salt</synonym>
    <synonym>1-alpha-D-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-(S)-pyridinium</synonym>
    <synonym>1-alpha-D-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridinium</synonym>
    <synonym>1-alpha-delta-Glucopyranuronosyl-3-(1-methyl-2-pyrrolidinyl)-(S)-pyridinium</synonym>
    <synonym>1-alpha-delta-Glucopyranuronosyl-3-[(2S)-1-methyl-2-pyrrolidinyl]-pyridinium</synonym>
    <synonym>Nicotine-glucuronide</synonym>
  </synonyms>
  <chemical_formula>C16H22N2O6</chemical_formula>
  <average_molecular_weight>338.3557</average_molecular_weight>
  <monisotopic_moleculate_weight>338.147786446</monisotopic_moleculate_weight>
  <iupac_name>1-[(2S,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]-1λ⁵-pyridin-1-ylium</iupac_name>
  <traditional_iupac>nicotine glucuronide</traditional_iupac>
  <cas_registry_number>152306-59-7</cas_registry_number>
  <smiles>CN1CCC[C@H]1C1=C[N+](=CC=C1)[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C([O-])=O</smiles>
  <inchi>InChI=1S/C16H22N2O6/c1-17-6-3-5-10(17)9-4-2-7-18(8-9)15-13(21)11(19)12(20)14(24-15)16(22)23/h2,4,7-8,10-15,19-21H,3,5-6H2,1H3/t10-,11-,12-,13+,14-,15-/m0/s1</inchi>
  <inchikey>SAWAIULJDYFLPD-SOAFEQHCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group  linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside triphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purines and purine derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside triphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ribonucleotides</external_descriptor>
      <external_descriptor>guanosine 5'-phosphate</external_descriptor>
      <external_descriptor>purine ribonucleoside 5'-triphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>7.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(2S,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]-1λ⁵-pyridin-1-ylium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>338.3557</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>338.147786446</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1CCC[C@H]1C1=C[N+](=CC=C1)[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C([O-])=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H22N2O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H22N2O6/c1-17-6-3-5-10(17)9-4-2-7-18(8-9)15-13(21)11(19)12(20)14(24-15)16(22)23/h2,4,7-8,10-15,19-21H,3,5-6H2,1H3/t10-,11-,12-,13+,14-,15-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SAWAIULJDYFLPD-SOAFEQHCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>117.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>94.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>70718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>129261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>129262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>129263</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022526</foodb_id>
  <chemspider_id>2299987</chemspider_id>
  <pubchem_compound_id>3035848</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>63860</chebi_id>
  <drugbank_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6127</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:27 UTC</creation_date>
  <update_date>2020-04-15 22:35:47 UTC</update_date>
  <accession>BMDB0001273</accession>
  <secondary_accessions>
    <accession>BMDB01273</accession>
  </secondary_accessions>
  <name>Guanosine triphosphate</name>
  <description>Guanosine triphosphate, also known as 5'-GTP or guanosine triphosphate, belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety. Guanosine triphosphate is possibly soluble (in water) and a moderately basic compound (based on its pKa). Guanosine triphosphate exists in all living species, ranging from bacteria to humans. In cattle, guanosine triphosphate is involved in a couple of metabolic pathways, which include the intracellular signalling through adenosine receptor A2A and adenosine pathway and the intracellular signalling through adenosine receptor A2B and adenosine pathway.</description>
  <synonyms>
    <synonym>5'-GTP</synonym>
    <synonym>Guanosine 5'-triphosphate</synonym>
    <synonym>Guanosine 5'-triphosphoric acid</synonym>
    <synonym>GUANOSINE-5'-triphosphATE</synonym>
    <synonym>H4GTP</synonym>
    <synonym>GUANOSINE-5'-triphosphoric acid</synonym>
    <synonym>Guanosine triphosphoric acid</synonym>
    <synonym>GTG</synonym>
    <synonym>GTP</synonym>
    <synonym>Guanosine 5'-(tetrahydrogen triphosphate)</synonym>
    <synonym>Guanosine 5'-triphosphorate</synonym>
    <synonym>Guanosine mono(tetrahydrogen triphosphate) (ester)</synonym>
    <synonym>Triphosphate, guanosine</synonym>
  </synonyms>
  <chemical_formula>C10H16N5O14P3</chemical_formula>
  <average_molecular_weight>523.1804</average_molecular_weight>
  <monisotopic_moleculate_weight>522.990659781</monisotopic_moleculate_weight>
  <iupac_name>({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</iupac_name>
  <traditional_iupac>triphosphate, guanosine</traditional_iupac>
  <cas_registry_number>86-01-1</cas_registry_number>
  <smiles>NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1</smiles>
  <inchi>InChI=1S/C10H16N5O14P3/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1</inchi>
  <inchikey>XKMLYUALXHKNFT-UUOKFMHZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group  linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside triphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purines and purine derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside triphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ribonucleotides</external_descriptor>
      <external_descriptor>guanosine 5'-phosphate</external_descriptor>
      <external_descriptor>purine ribonucleoside 5'-triphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>523.1804</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>522.990659781</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H16N5O14P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H16N5O14P3/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XKMLYUALXHKNFT-UUOKFMHZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>294.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>97.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Activation of cAMP-dependent protein kinase, PKA</name>
      <smpdb_id>SMP0108201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Activation of PKC Through G Protein-Coupled Receptor</name>
      <smpdb_id>SMP0108001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>BCR Signaling Pathway</name>
      <smpdb_id>SMP0120940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cadmium Induces DNA Synthesis and Proliferation in Macrophages </name>
      <smpdb_id>SMP0108212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Corticotropin Activation of Cortisol Production</name>
      <smpdb_id>SMP0108167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Dopamine Activation of Neurological Reward System</name>
      <smpdb_id>SMP0107994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>EGF Signalling Pathway</name>
      <smpdb_id>SMP0120924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>EPO Signaling Pathway</name>
      <smpdb_id>SMP0120938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 4 and Serotonin</name>
      <smpdb_id>SMP0108169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 6 and Serotonin</name>
      <smpdb_id>SMP0108172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 7 and Serotonin</name>
      <smpdb_id>SMP0108170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histamine H1 Receptor Activation</name>
      <smpdb_id>SMP0108002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Insulin Signalling</name>
      <smpdb_id>SMP0108189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2a and Adenosine</name>
      <smpdb_id>SMP0108174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2b and Adenosine</name>
      <smpdb_id>SMP0108178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through FSH Receptor and Follicle Stimulating Hormone</name>
      <smpdb_id>SMP0108183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Histamine H2 Receptor and Histamine</name>
      <smpdb_id>SMP0107995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through LHCGR Receptor and Luteinizing Hormone/Choriogonadotropin</name>
      <smpdb_id>SMP0108184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through PGD2 receptor and Prostaglandin D2</name>
      <smpdb_id>SMP0107997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Prostacyclin Receptor and Prostacyclin</name>
      <smpdb_id>SMP0107998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ion Channels and Their Functional Role in Vascular Endothelium</name>
      <smpdb_id>SMP0108207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA1 Signalling</name>
      <smpdb_id>SMP0108191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA2 Signalling</name>
      <smpdb_id>SMP0108193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA3 Signalling</name>
      <smpdb_id>SMP0108194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA4 Signalling</name>
      <smpdb_id>SMP0108196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA5 Signalling</name>
      <smpdb_id>SMP0108198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA6 Signalling</name>
      <smpdb_id>SMP0108199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pterine Biosynthesis</name>
      <smpdb_id>SMP0087250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Rac 1 cell motility signaling pathway </name>
      <smpdb_id>SMP0100484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Rac 1 Cell Motility Signaling Pathway</name>
      <smpdb_id>SMP0120885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>T Cell Receptor Signaling Pathway </name>
      <smpdb_id>SMP0120935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vasopressin Regulation of Water Homeostasis</name>
      <smpdb_id>SMP0108181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178132</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180449</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00044</kegg_id>
  <foodb_id>FDB022527</foodb_id>
  <chemspider_id>6569</chemspider_id>
  <pubchem_compound_id>6830</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15996</chebi_id>
  <drugbank_id>DB04137</drugbank_id>
  <knapsack_id>C00007223</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>33641</bigg_id>
  <wikipedia_id>Guanosine triphosphate</wikipedia_id>
  <metlin_id>6128</metlin_id>
  <synthesis_reference>Stiller, Regine; Thiem, Joachim.  Preparative enzymatic conversion of guanosine-5'-monophosphate to guanosine-5'-triphosphate.    Synlett  (1990),   (11),  709-10.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:28 UTC</creation_date>
  <update_date>2020-03-13 16:26:58 UTC</update_date>
  <accession>BMDB0001274</accession>
  <secondary_accessions>
    <accession>BMDB01274</accession>
  </secondary_accessions>
  <name>dTDP</name>
  <description/>
  <synonyms>
    <synonym>2'-Deoxyribosylthymine 5'-(trihydrogen diphosphate)</synonym>
    <synonym>Deoxy-TDP</synonym>
    <synonym>Deoxythymidine 5'-diphosphate</synonym>
    <synonym>Thymidine 5'-diphosphate</synonym>
    <synonym>Thymidine 5'-pyrophosphate</synonym>
    <synonym>THYMIDINE-5'- diphosphATE</synonym>
    <synonym>2'-Deoxyribosylthymine 5'-(trihydrogen diphosphoric acid)</synonym>
    <synonym>Deoxythymidine 5'-diphosphoric acid</synonym>
    <synonym>Thymidine 5'-diphosphoric acid</synonym>
    <synonym>Thymidine 5'-pyrophosphoric acid</synonym>
    <synonym>THYMIDINE-5'- diphosphoric acid</synonym>
    <synonym>TDP</synonym>
  </synonyms>
  <chemical_formula>C10H16N2O11P2</chemical_formula>
  <average_molecular_weight>402.1884</average_molecular_weight>
  <monisotopic_moleculate_weight>402.022932388</monisotopic_moleculate_weight>
  <iupac_name>{[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>dTDP</traditional_iupac>
  <cas_registry_number>491-97-4</cas_registry_number>
  <smiles>CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O2)C(=O)NC1=O</smiles>
  <inchi>InChI=1S/C10H16N2O11P2/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(22-8)4-21-25(19,20)23-24(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,19,20)(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1</inchi>
  <inchikey>UJLXYODCHAELLY-XLPZGREQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside diphosphates. These are pyrimidine nucleotides with a diphosphate group  linked to the ribose moiety lacking a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine deoxyribonucleotides</sub_class>
    <direct_parent>Pyrimidine 2'-deoxyribonucleoside diphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside diphosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxyribonucleotides</external_descriptor>
      <external_descriptor>pyrimidine 2'-deoxyribonucleoside 5'-diphosphate</external_descriptor>
      <external_descriptor>thymidine phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>402.1884</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>402.022932388</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O2)C(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H16N2O11P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H16N2O11P2/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(22-8)4-21-25(19,20)23-24(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,19,20)(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UJLXYODCHAELLY-XLPZGREQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>192.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>77.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439110</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00363</kegg_id>
  <foodb_id>FDB022528</foodb_id>
  <chemspider_id>144320</chemspider_id>
  <pubchem_compound_id>164628</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18075</chebi_id>
  <drugbank_id>DB03103</drugbank_id>
  <knapsack_id>C00019696</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34750</bigg_id>
  <wikipedia_id>Thymidine_diphosphate</wikipedia_id>
  <metlin_id>6129</metlin_id>
  <meta_cyc_id>TDP</meta_cyc_id>
  <synthesis_reference>Rupprath, Carsten; Kopp, Maren; Hirtz, Dennis; Mueller, Rolf; Elling, Lothar.  An enzyme module system for in situ regeneration of deoxythymidine 5'-diphosphate (dTDP)-activated deoxy sugars.    Advanced Synthesis &amp; Catalysis  (2007),  349(8+9),  1489-1496.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00437</protein_accession>
      <name>dTDP-D-glucose 4,6-dehydratase</name>
      <uniprot_id>A6QLW2</uniprot_id>
      <gene_name>TGDS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:29 UTC</creation_date>
  <update_date>2020-03-13 16:26:58 UTC</update_date>
  <accession>BMDB0001275</accession>
  <secondary_accessions>
    <accession>BMDB01275</accession>
  </secondary_accessions>
  <name>Propionyl-CoA</name>
  <description>Propionyl-CoA, also known as propionyl-coa, belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. Propionyl-CoA is possibly soluble (in water) and a strong basic compound (based on its pKa). Propionyl-CoA participates in a number of enzymatic reactions, within cattle. In particular, Propionyl-CoA and L-carnitine can be converted into propionylcarnitine through the action of the enzyme carnitine O-acetyltransferase. In addition, Propionyl-CoA and L-carnitine can be converted into propionylcarnitine through the action of the enzyme carnitine O-acetyltransferase. In cattle, propionyl-CoA is involved in the metabolic pathway called the oxidation OF branched-chain fatty acids pathway. Propionyl-CoA is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2-Methylacetyl-CoA</synonym>
    <synonym>2-Methylacetyl-coenzyme A</synonym>
    <synonym>alpha-Methylacetyl-CoA</synonym>
    <synonym>alpha-Methylacetyl-coenzyme A</synonym>
    <synonym>Propanoyl-CoA</synonym>
    <synonym>Propanoyl-coenzyme A</synonym>
    <synonym>Propionyl-coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C24H40N7O17P3S</chemical_formula>
  <average_molecular_weight>823.597</average_molecular_weight>
  <monisotopic_moleculate_weight>823.141423115</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-(propanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-(propanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>317-66-8</cas_registry_number>
  <smiles>CCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C24H40N7O17P3S/c1-4-15(33)52-8-7-26-14(32)5-6-27-22(36)19(35)24(2,3)10-45-51(42,43)48-50(40,41)44-9-13-18(47-49(37,38)39)17(34)23(46-13)31-12-30-16-20(25)28-11-29-21(16)31/h11-13,17-19,23,34-35H,4-10H2,1-3H3,(H,26,32)(H,27,36)(H,40,41)(H,42,43)(H2,25,28,29)(H2,37,38,39)/t13-,17-,18-,19?,23-/m1/s1</inchi>
  <inchikey>QAQREVBBADEHPA-UXYNFSPESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-(propanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>823.597</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>823.141423115</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H40N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H40N7O17P3S/c1-4-15(33)52-8-7-26-14(32)5-6-27-22(36)19(35)24(2,3)10-45-51(42,43)48-50(40,41)44-9-13-18(47-49(37,38)39)17(34)23(46-13)31-12-30-16-20(25)28-11-29-21(16)31/h11-13,17-19,23,34-35H,4-10H2,1-3H3,(H,26,32)(H,27,36)(H,40,41)(H,42,43)(H2,25,28,29)(H2,37,38,39)/t13-,17-,18-,19?,23-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QAQREVBBADEHPA-UXYNFSPESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>176.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>72.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Threonine and 2-Oxobutanoate Degradation</name>
      <smpdb_id>SMP0087262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171449</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00100</kegg_id>
  <foodb_id>FDB022529</foodb_id>
  <chemspider_id>388310</chemspider_id>
  <pubchem_compound_id>439164</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15539</chebi_id>
  <drugbank_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>33852</bigg_id>
  <wikipedia_id>Propionyl-CoA</wikipedia_id>
  <metlin_id>6130</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Sokatch, John R.; Sanders, Lois E.; Marshall, Vincent P.  Oxidation of methylmalonate semialdehyde to propionyl coenzyme A in Pseudomonas aeruginosa grown on valine.    Journal of Biological Chemistry  (1968),  243(10),  2500-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00253</protein_accession>
      <name>Propionyl-CoA carboxylase beta chain, mitochondrial</name>
      <uniprot_id>Q2TBR0</uniprot_id>
      <gene_name>PCCB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00260</protein_accession>
      <name>Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial</name>
      <uniprot_id>Q07536</uniprot_id>
      <gene_name>ALDH6A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00530</protein_accession>
      <name>Non-specific lipid-transfer protein</name>
      <uniprot_id>P07857</uniprot_id>
      <gene_name>SCP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:31 UTC</creation_date>
  <update_date>2020-03-13 16:26:59 UTC</update_date>
  <accession>BMDB0001276</accession>
  <secondary_accessions>
    <accession>BMDB01276</accession>
  </secondary_accessions>
  <name>N1-Acetylspermidine</name>
  <description/>
  <synonyms>
    <synonym>1-N-Acetylspermidine</synonym>
    <synonym>An N-acetylspermidine</synonym>
    <synonym>N(1)-Acetylspermidine</synonym>
    <synonym>N-(3-((4-Aminobutyl)amino)propyl)-acetamide</synonym>
    <synonym>N-(3-((4-Aminobutyl)amino)propyl)acetamide</synonym>
    <synonym>N-Acetylspermidine</synonym>
    <synonym>N1-Acetylspermidine</synonym>
  </synonyms>
  <chemical_formula>C9H21N3O</chemical_formula>
  <average_molecular_weight>187.2825</average_molecular_weight>
  <monisotopic_moleculate_weight>187.168462309</monisotopic_moleculate_weight>
  <iupac_name>N-{3-[(4-aminobutyl)amino]propyl}acetamide</iupac_name>
  <traditional_iupac>N1-acetylspermidine</traditional_iupac>
  <cas_registry_number>14278-49-0</cas_registry_number>
  <smiles>CC(=O)NCCCNCCCCN</smiles>
  <inchi>InChI=1S/C9H21N3O/c1-9(13)12-8-4-7-11-6-3-2-5-10/h11H,2-8,10H2,1H3,(H,12,13)</inchi>
  <inchikey>MQTAVJHICJWXBR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboximidic acids and derivatives</class>
    <sub_class>Carboximidic acids</sub_class>
    <direct_parent>Carboximidic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>acetylspermidine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>16.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-{3-[(4-aminobutyl)amino]propyl}acetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>187.2825</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>187.168462309</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)NCCCNCCCCN</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H21N3O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H21N3O/c1-9(13)12-8-4-7-11-6-3-2-5-10/h11H,2-8,10H2,1H3,(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MQTAVJHICJWXBR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>67.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33856</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00612</kegg_id>
  <foodb_id>FDB022530</foodb_id>
  <chemspider_id>482</chemspider_id>
  <pubchem_compound_id>496</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17927</chebi_id>
  <drugbank_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>3323</metlin_id>
  <meta_cyc_id>CPD-568</meta_cyc_id>
  <synthesis_reference>Lurdes M; Almeida S; Grehn L; Ragnarsson U  Facile synthesis of monoacetylated spermidines, illustrating selective deacetylation and application of a common precursor.    Acta chemica Scandinavica (Copenhagen, Denmark : 1989)  (1989),  43(10),  990-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00128</protein_accession>
      <name>Peroxisomal N(1)-acetyl-spermine/spermidine oxidase</name>
      <uniprot_id>Q865R1</uniprot_id>
      <gene_name>PAOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:32 UTC</creation_date>
  <update_date>2020-03-13 16:26:59 UTC</update_date>
  <accession>BMDB0001278</accession>
  <secondary_accessions>
    <accession>BMDB01278</accession>
  </secondary_accessions>
  <name>Presqualene diphosphate</name>
  <description/>
  <synonyms>
    <synonym>[(1S,2S,3S)-2-[(e)-4,8-Dimethylnona-3,7-dienyl]-2-methyl-3-[(2E,6E)-2,6,10-trimethylundeca-1,5,9-trienyl]cyclopropan-1-yl]methyl diphosphate</synonym>
    <synonym>[(1S,2S,3S)-2-[(e)-4,8-Dimethylnona-3,7-dienyl]-2-methyl-3-[(2E,6E)-2,6,10-trimethylundeca-1,5,9-trienyl]cyclopropan-1-yl]methyl diphosphoric acid</synonym>
    <synonym>Presqualene diphosphoric acid</synonym>
    <synonym>[(1R,2R,3R)-2-[(e)-4,8-Dimethylnona-3,7-dienyl]-2-methyl-3-[(2E,6E)-2,6,10-trimethylundeca-1,5,9-trienyl]cyclopropan-1-yl]methyl diphosphate</synonym>
    <synonym>[(1R,2R,3R)-2-[(e)-4,8-Dimethylnona-3,7-dienyl]-2-methyl-3-[(2E,6E)-2,6,10-trimethylundeca-1,5,9-trienyl]cyclopropan-1-yl]methyl diphosphoric acid</synonym>
    <synonym>(1alpha,2beta(e),3beta(1E,5E))-Diphosphoric acid mono((2-(4,8-dimethyl-3,7-nonadienyl)-2-methyl-3-(2,6,10-trimethyl-1,5,9-undecatrienyl)cyclopropyl)methyl) ester</synonym>
    <synonym>Presqualene pyrophosphate</synonym>
  </synonyms>
  <chemical_formula>C30H52O7P2</chemical_formula>
  <average_molecular_weight>586.6772</average_molecular_weight>
  <monisotopic_moleculate_weight>586.318827042</monisotopic_moleculate_weight>
  <iupac_name>[({[(1S,2S,3S)-2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-2-methyl-3-[(1E,5E)-2,6,10-trimethylundeca-1,5,9-trien-1-yl]cyclopropyl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>presqualene diphosphate</traditional_iupac>
  <cas_registry_number>29849-75-0</cas_registry_number>
  <smiles>CC(C)=CCC\C(C)=C\CC\C(C)=C\[C@@]1([H])[C@]([H])(COP(O)(=O)OP(O)(O)=O)[C@@]1(C)CC\C=C(/C)CCC=C(C)C</smiles>
  <inchi>InChI=1S/C30H52O7P2/c1-23(2)13-9-15-25(5)17-11-18-27(7)21-28-29(22-36-39(34,35)37-38(31,32)33)30(28,8)20-12-19-26(6)16-10-14-24(3)4/h13-14,17,19,21,28-29H,9-12,15-16,18,20,22H2,1-8H3,(H,34,35)(H2,31,32,33)/b25-17+,26-19+,27-21+/t28-,29-,30-/m0/s1</inchi>
  <inchikey>ATZKAUGGNMSCCY-VYCBRMPGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Triterpenoids</sub_class>
    <direct_parent>Triterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>triterpenoid</external_descriptor>
      <external_descriptor>triterpenyl phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(1S,2S,3S)-2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-2-methyl-3-[(1E,5E)-2,6,10-trimethylundeca-1,5,9-trien-1-yl]cyclopropyl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>586.6772</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>586.318827042</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)=CCC\C(C)=C\CC\C(C)=C\[C@@]1([H])[C@]([H])(COP(O)(=O)OP(O)(O)=O)[C@@]1(C)CC\C=C(/C)CCC=C(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C30H52O7P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C30H52O7P2/c1-23(2)13-9-15-25(5)17-11-18-27(7)21-28-29(22-36-39(34,35)37-38(31,32)33)30(28,8)20-12-19-26(6)16-10-14-24(3)4/h13-14,17,19,21,28-29H,9-12,15-16,18,20,22H2,1-8H3,(H,34,35)(H2,31,32,33)/b25-17+,26-19+,27-21+/t28-,29-,30-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ATZKAUGGNMSCCY-VYCBRMPGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>165.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>66.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181709</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03428</kegg_id>
  <foodb_id>FDB022531</foodb_id>
  <chemspider_id>4444207</chemspider_id>
  <pubchem_compound_id>5280592</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15442</chebi_id>
  <drugbank_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6132</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Rogers, Daniel H.; Yi, Eugene C.; Poulter, C. Dale.  Enantioselective Synthesis of (+)-Presqualene Diphosphate.    Journal of Organic Chemistry  (1995),  60(4),  941-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00261</protein_accession>
      <name>Squalene synthetase</name>
      <uniprot_id>Q32KR6</uniprot_id>
      <gene_name>FDFT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:34 UTC</creation_date>
  <update_date>2020-03-13 16:27:00 UTC</update_date>
  <accession>BMDB0001280</accession>
  <secondary_accessions>
    <accession>BMDB01280</accession>
  </secondary_accessions>
  <name>2-Aminomuconic acid semialdehyde</name>
  <description>2-Aminomuconic acid semialdehyde belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 2-Aminomuconic acid semialdehyde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Aminomuconic acid semialdehyde exists in all living organisms, ranging from bacteria to humans. 2-Aminomuconic acid semialdehyde can be biosynthesized from 2-amino-3-carboxymuconic acid semialdehyde; which is catalyzed by the enzyme 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase. In cattle, 2-aminomuconic acid semialdehyde is involved in the metabolic pathway called the tryptophan metabolism pathway.</description>
  <synonyms>
    <synonym>2-Aminomuconate 6-semialdehyde</synonym>
    <synonym>2-Aminomuconate semialdehyde</synonym>
    <synonym>2-Aminomuconic semialdehyde</synonym>
    <synonym>2-Aminomuconic acid 6-semialdehyde</synonym>
  </synonyms>
  <chemical_formula>C6H7NO3</chemical_formula>
  <average_molecular_weight>141.1247</average_molecular_weight>
  <monisotopic_moleculate_weight>141.042593095</monisotopic_moleculate_weight>
  <iupac_name>(2E,4Z)-2-amino-6-oxohexa-2,4-dienoic acid</iupac_name>
  <traditional_iupac>2-aminomuconic semialdehyde</traditional_iupac>
  <cas_registry_number>245128-91-0</cas_registry_number>
  <smiles>N\C(=C\C=C/C=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H7NO3/c7-5(6(9)10)3-1-2-4-8/h1-4H,7H2,(H,9,10)/b2-1-,5-3+</inchi>
  <inchikey>QCGTZPZKJPTAEP-REDYYMJGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Aldehydes</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Enals</alternative_parent>
      <alternative_parent>Enamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha,beta-unsaturated aldehyde</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Enal</substituent>
      <substituent>Enamine</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Oxo fatty acids</external_descriptor>
      <external_descriptor>alpha,beta-unsaturated monocarboxylic acid</external_descriptor>
      <external_descriptor>muconic semialdehyde</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>7.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E,4Z)-2-amino-6-oxohexa-2,4-dienoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>141.1247</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>141.042593095</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N\C(=C\C=C/C=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H7NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H7NO3/c7-5(6(9)10)3-1-2-4-8/h1-4H,7H2,(H,9,10)/b2-1-,5-3+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QCGTZPZKJPTAEP-REDYYMJGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364242</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03824</kegg_id>
  <foodb_id>FDB022532</foodb_id>
  <chemspider_id>4444230</chemspider_id>
  <pubchem_compound_id>5280625</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15745</chebi_id>
  <drugbank_id/>
  <knapsack_id>C00007492</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>1445635</bigg_id>
  <wikipedia_id/>
  <metlin_id>6133</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00639</protein_accession>
      <name>2-amino-3-carboxymuconate-6-semialdehyde decarboxylase</name>
      <uniprot_id>Q0II68</uniprot_id>
      <gene_name>ACMSD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:35 UTC</creation_date>
  <update_date>2020-03-13 16:27:00 UTC</update_date>
  <accession>BMDB0001282</accession>
  <secondary_accessions>
    <accession>BMDB01282</accession>
  </secondary_accessions>
  <name>Diadenosine hexaphosphate</name>
  <description/>
  <synonyms>
    <synonym>Adenosine 5'-hexaphosphate 5'-ester with adenosine</synonym>
    <synonym>Adenosine-(5')-hexaphospho-(5')-adenosine</synonym>
    <synonym>Ap(6)a</synonym>
    <synonym>AP6a</synonym>
    <synonym>AppppppA</synonym>
    <synonym>Diadenosine 5',5''''-P1,P6-hexaphosphate</synonym>
    <synonym>P1,P6-Di(adenosine-5')hexaphosphate</synonym>
    <synonym>Adenosine 5'-hexaphosphoric acid 5'-ester with adenosine</synonym>
    <synonym>Diadenosine 5',5''''-P1,P6-hexaphosphoric acid</synonym>
    <synonym>P1,P6-Di(adenosine-5')hexaphosphoric acid</synonym>
    <synonym>Diadenosine hexaphosphoric acid</synonym>
    <synonym>Adenosine 5'-(heptahydrogen hexaphosphate) p-&gt;5'-ester with adenosine</synonym>
    <synonym>Adenosine 5'-(heptahydrogen hexaphosphate)5'-5'-ester with adenosine</synonym>
    <synonym>P1,P6-Bis(5'-adenosyl)hexaphosphoric acid</synonym>
    <synonym>p(1),p(6)-Bis(5'-adenosyl)hexaphosphoric acid</synonym>
    <synonym>Diadenosine hexaphosphate</synonym>
  </synonyms>
  <chemical_formula>C20H30N10O25P6</chemical_formula>
  <average_molecular_weight>996.3468</average_molecular_weight>
  <monisotopic_moleculate_weight>995.980925632</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid</iupac_name>
  <traditional_iupac>AppppppA</traditional_iupac>
  <cas_registry_number>56983-23-4</cas_registry_number>
  <smiles>NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@@H](O)[C@H]3O)C2=NC=N1</smiles>
  <inchi>InChI=1S/C20H30N10O25P6/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(49-19)1-47-56(35,36)51-58(39,40)53-60(43,44)55-61(45,46)54-59(41,42)52-57(37,38)48-2-8-12(32)14(34)20(50-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1</inchi>
  <inchikey>PZCFFCOJNXGTIM-XPWFQUROSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside polyphosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside polyphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>diadenosyl hexaphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>996.3468</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>995.980925632</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@@H](O)[C@H]3O)C2=NC=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H30N10O25P6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H30N10O25P6/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(49-19)1-47-56(35,36)51-58(39,40)53-60(43,44)55-61(45,46)54-59(41,42)52-57(37,38)48-2-8-12(32)14(34)20(50-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PZCFFCOJNXGTIM-XPWFQUROSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>527.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>187.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>76.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31881</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31882</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C20190</kegg_id>
  <foodb_id>FDB022533</foodb_id>
  <chemspider_id>110267</chemspider_id>
  <pubchem_compound_id>123694</pubchem_compound_id>
  <pdbe_id>B6P</pdbe_id>
  <chebi_id>63689</chebi_id>
  <drugbank_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Sawai, Hiroaki; Inaba, Toshiko; Hirano, Atsushi; Wakai, Hiromichi; Shimazu, Masamitsu.  Magnesium(II) ion-mediated conversion of mono- and oligonucleotides to 5'-polyphosphates in aqueous solution.    Tetrahedron Letters  (1993),  34(30),  4801-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:36 UTC</creation_date>
  <update_date>2020-03-13 16:27:01 UTC</update_date>
  <accession>BMDB0001285</accession>
  <secondary_accessions>
    <accession>BMDB01285</accession>
  </secondary_accessions>
  <name>Geranyl-PP</name>
  <description/>
  <synonyms>
    <synonym>Geranyl pyrophosphate</synonym>
    <synonym>Polyisopentenylpyrophosphate</synonym>
    <synonym>Polyisopentenyldiphosphate</synonym>
    <synonym>trans-Polyisopentenyldiphosphate</synonym>
    <synonym>Polyprenyl diphosphate</synonym>
    <synonym>Geranyl pyrophosphoric acid</synonym>
    <synonym>Polyisopentenylpyrophosphoric acid</synonym>
    <synonym>Polyisopentenyldiphosphoric acid</synonym>
    <synonym>trans-Polyisopentenyldiphosphoric acid</synonym>
    <synonym>Polyprenyl diphosphoric acid</synonym>
    <synonym>(2E)-3,7-Dimethylocta-2,6-dien-1-yl trihydrogen diphosphate</synonym>
    <synonym>Geranyl diphosphate</synonym>
    <synonym>Geranyl-diphosphate</synonym>
    <synonym>Geranyl-pyrophosphate</synonym>
    <synonym>Monoterpenyl diphosphate</synonym>
    <synonym>Neryl diphosphate</synonym>
    <synonym>trans-Geranyl pyrophosphate</synonym>
  </synonyms>
  <chemical_formula>C10H20O7P2</chemical_formula>
  <average_molecular_weight>314.2091</average_molecular_weight>
  <monisotopic_moleculate_weight>314.068426018</monisotopic_moleculate_weight>
  <iupac_name>[({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>geranyl diphosphate</traditional_iupac>
  <cas_registry_number>763-10-0</cas_registry_number>
  <smiles>CC(C)=CCC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)O</smiles>
  <inchi>InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+</inchi>
  <inchikey>GVVPGTZRZFNKDS-JXMROGBWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Isoprenoid phosphates</sub_class>
    <direct_parent>Isoprenoid phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Acyclic monoterpenoids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyclic monoterpenoid</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isoprenoid phosphate</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monoterpenoid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Acyclic monoterpenoids</external_descriptor>
      <external_descriptor>Acyclic monoterpenoids</external_descriptor>
      <external_descriptor>Linear monoterpenes</external_descriptor>
      <external_descriptor>polyprenol diphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>314.2091</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>314.068426018</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)=CCC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H20O7P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GVVPGTZRZFNKDS-JXMROGBWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29815</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05847</kegg_id>
  <foodb_id>FDB001463</foodb_id>
  <chemspider_id>393471</chemspider_id>
  <pubchem_compound_id>445995</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17211</chebi_id>
  <drugbank_id>DB02552</drugbank_id>
  <knapsack_id>C00000846</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34712</bigg_id>
  <wikipedia_id/>
  <metlin_id>6134</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Runquist M; Ericsson J; Thelin A; Chojnacki T; Dallner G  Biosynthesis of trans,trans,trans-geranylgeranyl diphosphate by the cytosolic fraction from rat tissues.    Biochemical and biophysical research communications  (1992),  186(1),  157-65.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00864</protein_accession>
      <name>Farnesyl pyrophosphate synthetase</name>
      <uniprot_id>Q8WMY2</uniprot_id>
      <gene_name>FDPS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00865</protein_accession>
      <name>Geranylgeranyl pyrophosphate synthetase</name>
      <uniprot_id>P56966</uniprot_id>
      <gene_name>GGPS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:37 UTC</creation_date>
  <update_date>2020-03-13 16:27:02 UTC</update_date>
  <accession>BMDB0001286</accession>
  <secondary_accessions>
    <accession>BMDB01286</accession>
  </secondary_accessions>
  <name>4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol</name>
  <description/>
  <synonyms>
    <synonym>(3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol</synonym>
    <synonym>14-Demethyllanosterol</synonym>
    <synonym>4,4-Dimethyl-5 alpha -cholesta-8,24-dien-3 beta -ol</synonym>
    <synonym>4,4-Dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol</synonym>
    <synonym>4,4-Dimethyl-5-alpha-cholesta-8,24-dien-3-beta-ol</synonym>
    <synonym>4,4-Dimethyl-5a-cholesta-8,24-dien-3b-ol</synonym>
    <synonym>4,4-Dimethyl-5alpha -cholesta-8,24-dien-3-beta -ol</synonym>
    <synonym>4,4-Dimethyl-5alpha-cholest-7-en-3beta-ol</synonym>
    <synonym>4,4-Dimethyl-5alpha-cholesta-8,24-dien-3beta-ol</synonym>
    <synonym>4,4-Dimethyl-8,24-cholestadienol</synonym>
    <synonym>4,4-Dimethylzymosterol</synonym>
    <synonym>4,4-Dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol, (3beta)-isomer</synonym>
  </synonyms>
  <chemical_formula>C29H48O</chemical_formula>
  <average_molecular_weight>412.6908</average_molecular_weight>
  <monisotopic_moleculate_weight>412.370516158</monisotopic_moleculate_weight>
  <iupac_name>(2S,5S,7R,11R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol</iupac_name>
  <traditional_iupac>(2S,5S,7R,11R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol</traditional_iupac>
  <cas_registry_number>7448-02-4</cas_registry_number>
  <smiles>[H][C@@]12CCC([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CC[C@@]2([H])C(C)(C)[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C29H48O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,20,22-23,25-26,30H,8,10-18H2,1-7H3/t20-,22?,23+,25+,26+,28-,29-/m1/s1</inchi>
  <inchikey>CHGIKSSZNBCNDW-GKBRUXRCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Triterpenoids</sub_class>
    <direct_parent>Triterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cholesterols and derivatives</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholestane-skeleton</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Steroid</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,5S,7R,11R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>412.6908</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>412.370516158</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CCC([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CC[C@@]2([H])C(C)(C)[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C29H48O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C29H48O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,20,22-23,25-26,30H,8,10-18H2,1-7H3/t20-,22?,23+,25+,26+,28-,29-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CHGIKSSZNBCNDW-GKBRUXRCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>130.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>53.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178921</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178922</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181247</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022534</foodb_id>
  <chemspider_id>25994967</chemspider_id>
  <pubchem_compound_id>50990081</pubchem_compound_id>
  <chebi_id>18364</chebi_id>
  <kegg_id>C05108</kegg_id>
  <pdbe_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>45128</bigg_id>
  <wikipedia_id/>
  <metlin_id>6135</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:38 UTC</creation_date>
  <update_date>2020-03-13 16:27:02 UTC</update_date>
  <accession>BMDB0001290</accession>
  <secondary_accessions>
    <accession>BMDB01290</accession>
  </secondary_accessions>
  <name>Glutaconyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>Glutaconyl-1-CoA</synonym>
    <synonym>Glutaconyl-1-coenzyme A</synonym>
    <synonym>Glutaconyl-coenzyme A</synonym>
    <synonym>Pent-2-enoyl-CoA</synonym>
    <synonym>Pent-2-enoyl-coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C26H40N7O19P3S</chemical_formula>
  <average_molecular_weight>879.618</average_molecular_weight>
  <monisotopic_moleculate_weight>879.131252359</monisotopic_moleculate_weight>
  <iupac_name>5-{[2-(3-{3-[({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-5-oxopent-3-enoic acid</iupac_name>
  <traditional_iupac>glutaconyl-coa</traditional_iupac>
  <cas_registry_number>6712-05-6</cas_registry_number>
  <smiles>CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)C=CCC(O)=O</smiles>
  <inchi>InChI=1S/C26H40N7O19P3S/c1-26(2,21(39)24(40)29-7-6-15(34)28-8-9-56-17(37)5-3-4-16(35)36)11-49-55(46,47)52-54(44,45)48-10-14-20(51-53(41,42)43)19(38)25(50-14)33-13-32-18-22(27)30-12-31-23(18)33/h3,5,12-14,19-21,25,38-39H,4,6-11H2,1-2H3,(H,28,34)(H,29,40)(H,35,36)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)</inchi>
  <inchikey>URTLOTISFJPPOU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>2-enoyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Acyl CoAs</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-{[2-(3-{3-[({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-5-oxopent-3-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>879.618</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>879.131252359</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)C=CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H40N7O19P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H40N7O19P3S/c1-26(2,21(39)24(40)29-7-6-15(34)28-8-9-56-17(37)5-3-4-16(35)36)11-49-55(46,47)52-54(44,45)48-10-14-20(51-53(41,42)43)19(38)25(50-14)33-13-32-18-22(27)30-12-31-23(18)33/h3,5,12-14,19-21,25,38-39H,4,6-11H2,1-2H3,(H,28,34)(H,29,40)(H,35,36)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>URTLOTISFJPPOU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>400.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>188.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>78.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>291357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>331245</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022535</foodb_id>
  <chemspider_id>10739300</chemspider_id>
  <pubchem_compound_id>741</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Glutaconyl-CoA</wikipedia_id>
  <metlin_id>6136</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:39 UTC</creation_date>
  <update_date>2020-03-13 16:27:03 UTC</update_date>
  <accession>BMDB0001291</accession>
  <secondary_accessions>
    <accession>BMDB01291</accession>
  </secondary_accessions>
  <name>trans-D-Decenoyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>T2-Decenoyl-CoA</synonym>
    <synonym>T2-Decenoyl-coenzyme A</synonym>
    <synonym>trans-2,3-Dehydrodecanoyl-CoA</synonym>
    <synonym>trans-2,3-Dehydrodecanoyl-coenzyme A</synonym>
    <synonym>trans-delta-Decenoyl-CoA</synonym>
    <synonym>trans-delta-Decenoyl-coenzyme A</synonym>
    <synonym>4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-[2-({2-[(2E)-dec-2-enoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidate</synonym>
    <synonym>4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-[2-({2-[(2E)-dec-2-enoylsulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidate</synonym>
    <synonym>4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-[2-({2-[(2E)-dec-2-enoylsulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidic acid</synonym>
  </synonyms>
  <chemical_formula>C31H52N7O17P3S</chemical_formula>
  <average_molecular_weight>919.768</average_molecular_weight>
  <monisotopic_moleculate_weight>919.235323499</monisotopic_moleculate_weight>
  <iupac_name>{[5-(6-amino-9H-purin-9-yl)-2-{[({[(3-{[2-({2-[(2E)-dec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[5-(6-aminopurin-9-yl)-2-({[(3-{[2-({2-[(2E)-dec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>37325-74-9</cas_registry_number>
  <smiles>CCCCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12</smiles>
  <inchi>InChI=1S/C31H52N7O17P3S/c1-4-5-6-7-8-9-10-11-22(40)59-15-14-33-21(39)12-13-34-29(43)26(42)31(2,3)17-52-58(49,50)55-57(47,48)51-16-20-25(54-56(44,45)46)24(41)30(53-20)38-19-37-23-27(32)35-18-36-28(23)38/h10-11,18-20,24-26,30,41-42H,4-9,12-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46)/b11-10+</inchi>
  <inchikey>MGNBGCRQQFMNBM-ZHACJKMWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Medium-chain 2-enoyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>2-enoyl CoAs</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Acyl CoAs</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[5-(6-amino-9H-purin-9-yl)-2-{[({[(3-{[2-({2-[(2E)-dec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>919.768</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>919.235323499</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C31H52N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C31H52N7O17P3S/c1-4-5-6-7-8-9-10-11-22(40)59-15-14-33-21(39)12-13-34-29(43)26(42)31(2,3)17-52-58(49,50)55-57(47,48)51-16-20-25(54-56(44,45)46)24(41)30(53-20)38-19-37-23-27(32)35-18-36-28(23)38/h10-11,18-20,24-26,30,41-42H,4-9,12-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46)/b11-10+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MGNBGCRQQFMNBM-ZHACJKMWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>210.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>86.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370917</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022536</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>5462212</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6137</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:41 UTC</creation_date>
  <update_date>2020-03-13 16:27:03 UTC</update_date>
  <accession>BMDB0001292</accession>
  <secondary_accessions>
    <accession>BMDB01292</accession>
  </secondary_accessions>
  <name>1-Deoxy-D-xylulose</name>
  <description/>
  <synonyms>
    <synonym>1-Deoxy-xylulose</synonym>
  </synonyms>
  <chemical_formula>C5H10O4</chemical_formula>
  <average_molecular_weight>134.1305</average_molecular_weight>
  <monisotopic_moleculate_weight>134.057908808</monisotopic_moleculate_weight>
  <iupac_name>(2S,3S,4R)-2-(hydroxymethyl)oxolane-3,4-diol</iupac_name>
  <traditional_iupac>1-deoxy-xylulose</traditional_iupac>
  <cas_registry_number/>
  <smiles>OC[C@@H]1OC[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C5H10O4/c6-1-4-5(8)3(7)2-9-4/h3-8H,1-2H2/t3-,4+,5+/m1/s1</inchi>
  <inchikey>KZVAAIRBJJYZOW-WISUUJSJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3S,4R)-2-(hydroxymethyl)oxolane-3,4-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>134.1305</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>134.057908808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H]1OC[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O4/c6-1-4-5(8)3(7)2-9-4/h3-8H,1-2H2/t3-,4+,5+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KZVAAIRBJJYZOW-WISUUJSJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>69.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34280</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34282</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C06257</kegg_id>
  <chemspider_id>17216098</chemspider_id>
  <foodb_id>FDB022537</foodb_id>
  <pubchem_compound_id>12444984</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6138</metlin_id>
  <synthesis_reference>Backstrom, Allyson D.; Austin, R.; McMordie Austin S.; Begley, Tadhg P. A new synthesis of 1-deoxy-D-threo-2-pentulose, a biosynthetic precursor to the thiazole moiety of thiamin. Journal of Carbohydrate Chemistry (1995), 14(1), 171-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:42 UTC</creation_date>
  <update_date>2020-04-16 22:58:49 UTC</update_date>
  <accession>BMDB0001294</accession>
  <secondary_accessions>
    <accession>BMDB01294</accession>
  </secondary_accessions>
  <name>2,3-Diphosphoglyceric acid</name>
  <description/>
  <synonyms>
    <synonym>2,3-Bisphospho-D-glycerate</synonym>
    <synonym>2,3-Bisphosphoglyceric acid</synonym>
    <synonym>2,3-BPG</synonym>
    <synonym>2,3-Disphospho-D-glycerate</synonym>
    <synonym>D-Greenwald ester</synonym>
    <synonym>DPG</synonym>
    <synonym>Glyceric acid bis(dihydrogen phosphate)</synonym>
    <synonym>Glyceric acid diphosphate</synonym>
    <synonym>2,3-Bisphospho-D-glyceric acid</synonym>
    <synonym>2,3-Bisphosphoglycerate</synonym>
    <synonym>2,3-Disphospho-D-glyceric acid</synonym>
    <synonym>Glycerate bis(dihydrogen phosphate)</synonym>
    <synonym>Glyceric acid bis(dihydrogen phosphoric acid)</synonym>
    <synonym>Glycerate diphosphate</synonym>
    <synonym>Glyceric acid diphosphoric acid</synonym>
    <synonym>2,3-Diphosphoglycerate</synonym>
    <synonym>(2R)-2,3-Bis(phosphonooxy)-propanoate</synonym>
    <synonym>(2R)-2,3-Bis(phosphonooxy)-propanoic acid</synonym>
    <synonym>(R)-2,3-Bis(phosphonooxy)-propanoate</synonym>
    <synonym>(R)-2,3-Bis(phosphonooxy)-propanoic acid</synonym>
    <synonym>2,3-Bis(phosphonooxy)-propanoate</synonym>
    <synonym>2,3-Bis(phosphonooxy)-propanoic acid</synonym>
    <synonym>2,3-Diphospho-D-glycerate</synonym>
    <synonym>2,3-Diphospho-D-glyceric acid</synonym>
    <synonym>2,3-Diphospho-D-glyceric acid pentasodium salt</synonym>
    <synonym>D-Glyceric acid bis</synonym>
    <synonym>D-Glyceric acid bis(dihydrogen phosphate)</synonym>
    <synonym>Diphosphoglycerate</synonym>
    <synonym>Diphosphoglyceric acid</synonym>
    <synonym>Glycerate 2,3-diphosphate</synonym>
    <synonym>2,3 Diphosphoglyceric acid</synonym>
    <synonym>2,3 Bisphosphoglycerate</synonym>
    <synonym>2,3 Diphosphoglycerate</synonym>
    <synonym>2,3-DPG</synonym>
    <synonym>2,3-Diphosphoglycerate, (D)-isomer</synonym>
    <synonym>Glycerate 2,3-bisphosphate</synonym>
    <synonym>2,3-Bisphosphate, glycerate</synonym>
    <synonym>(2R)-2,3-Bis(phosphonooxy)propanoic acid</synonym>
    <synonym>(2R)-2,3-Bis(phosphonooxy)propionic acid</synonym>
    <synonym>2,3-Bis(phosphonooxy)propanoic acid</synonym>
    <synonym>2,3-Bis(phosphonooxy)propionic acid</synonym>
    <synonym>2,3-Diphosphoglyceric acid</synonym>
    <synonym>2,3-Diphosphonooxypropanoic acid</synonym>
    <synonym>2,3-Diphosphonooxypropionic acid</synonym>
  </synonyms>
  <chemical_formula>C3H8O10P2</chemical_formula>
  <average_molecular_weight>266.0371</average_molecular_weight>
  <monisotopic_moleculate_weight>265.9592695</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2,3-bis(phosphonooxy)propanoic acid</iupac_name>
  <traditional_iupac>diphosphoglycerate</traditional_iupac>
  <cas_registry_number>138-81-8</cas_registry_number>
  <smiles>OC(=O)[C@@H](COP(O)(O)=O)OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C3H8O10P2/c4-3(5)2(13-15(9,10)11)1-12-14(6,7)8/h2H,1H2,(H,4,5)(H2,6,7,8)(H2,9,10,11)/t2-/m1/s1</inchi>
  <inchikey>XOHUEYCVLUUEJJ-UWTATZPHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glyceric_acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2,3-bisphosphoglyceric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2,3-bis(phosphonooxy)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>266.0371</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>265.9592695</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)[C@@H](COP(O)(O)=O)OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H8O10P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H8O10P2/c4-3(5)2(13-15(9,10)11)1-12-14(6,7)8/h2H,1H2,(H,4,5)(H2,6,7,8)(H2,9,10,11)/t2-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XOHUEYCVLUUEJJ-UWTATZPHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>170.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177963</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445960</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01159</kegg_id>
  <foodb_id>FDB022538</foodb_id>
  <chemspider_id>161681</chemspider_id>
  <pubchem_compound_id>186004</pubchem_compound_id>
  <chebi_id>17720</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>23-DIPHOSPHOGLYCERATE</meta_cyc_id>
  <bigg_id>1315507</bigg_id>
  <wikipedia_id>2,3-Bisphosphoglyceric acid</wikipedia_id>
  <metlin_id>153</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00919</protein_accession>
      <name>Phosphoglycerate mutase 2</name>
      <uniprot_id>Q32KV0</uniprot_id>
      <gene_name>PGAM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00920</protein_accession>
      <name>Bisphosphoglycerate mutase</name>
      <uniprot_id>Q3T014</uniprot_id>
      <gene_name>BPGM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00921</protein_accession>
      <name>Phosphoglycerate mutase 1</name>
      <uniprot_id>Q3SZ62</uniprot_id>
      <gene_name>PGAM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:43 UTC</creation_date>
  <update_date>2020-04-15 22:00:24 UTC</update_date>
  <accession>BMDB0001295</accession>
  <secondary_accessions>
    <accession>BMDB01295</accession>
  </secondary_accessions>
  <name>2-Hydroxyphytanoyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>(3S)-2-Hydroxyphytanoyl-CoA</synonym>
    <synonym>(3S)-2-Hydroxyphytanoyl-coenzyme A</synonym>
    <synonym>(3S,7R,11R)-2-Hydroxy-3,7,11,15-tetramethylhexadecanoyl-CoA</synonym>
    <synonym>(3S,7R,11R)-2-Hydroxy-3,7,11,15-tetramethylhexadecanoyl-coenzyme A</synonym>
    <synonym>2-Hydroxyphytanoyl-coenzyme A</synonym>
    <synonym>3(S)-2-Hydroxyphytanoyl-CoA</synonym>
    <synonym>3(S)-2-Hydroxyphytanoyl-coenzyme A</synonym>
    <synonym>3S2hPhy-CoA</synonym>
    <synonym>3S2hPhy-coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C41H74N7O18P3S</chemical_formula>
  <average_molecular_weight>1078.049</average_molecular_weight>
  <monisotopic_moleculate_weight>1077.402388825</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(3S,7R,11R)-2-hydroxy-3,7,11,15-tetramethylhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-3-({2-[(2-{[(3S,7R,11R)-2-hydroxy-3,7,11,15-tetramethylhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>172787-73-4</cas_registry_number>
  <smiles>CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](C)C(O)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C41H74N7O18P3S/c1-25(2)11-8-12-26(3)13-9-14-27(4)15-10-16-28(5)32(50)40(54)70-20-19-43-30(49)17-18-44-38(53)35(52)41(6,7)22-63-69(60,61)66-68(58,59)62-21-29-34(65-67(55,56)57)33(51)39(64-29)48-24-47-31-36(42)45-23-46-37(31)48/h23-29,32-35,39,50-52H,8-22H2,1-7H3,(H,43,49)(H,44,53)(H,58,59)(H,60,61)(H2,42,45,46)(H2,55,56,57)/t26-,27-,28+,29-,32?,33-,34-,35?,39-/m1/s1</inchi>
  <inchikey>WNVFJMYPVBOLKV-PJDIVXIPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(3S,7R,11R)-2-hydroxy-3,7,11,15-tetramethylhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1078.049</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1077.402388825</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](C)C(O)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C41H74N7O18P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C41H74N7O18P3S/c1-25(2)11-8-12-26(3)13-9-14-27(4)15-10-16-28(5)32(50)40(54)70-20-19-43-30(49)17-18-44-38(53)35(52)41(6,7)22-63-69(60,61)66-68(58,59)62-21-29-34(65-67(55,56)57)33(51)39(64-29)48-24-47-31-36(42)45-23-46-37(31)48/h23-29,32-35,39,50-52H,8-22H2,1-7H3,(H,43,49)(H,44,53)(H,58,59)(H,60,61)(H2,42,45,46)(H2,55,56,57)/t26-,27-,28+,29-,32?,33-,34-,35?,39-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WNVFJMYPVBOLKV-PJDIVXIPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>383.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>256.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>108.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350601</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C07343</kegg_id>
  <foodb_id>FDB022539</foodb_id>
  <chemspider_id>390032</chemspider_id>
  <pubchem_compound_id>441263</pubchem_compound_id>
  <chebi_id>15475</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>2364545</bigg_id>
  <wikipedia_id/>
  <metlin_id>6140</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00688</protein_accession>
      <name>Phytanoyl-CoA dioxygenase, peroxisomal</name>
      <uniprot_id>O18778</uniprot_id>
      <gene_name>PHYH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:44 UTC</creation_date>
  <update_date>2020-04-14 22:49:05 UTC</update_date>
  <accession>BMDB0001296</accession>
  <secondary_accessions>
    <accession>BMDB01296</accession>
  </secondary_accessions>
  <name>Maltotetraose</name>
  <description>Maltotetraose belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Maltotetraose is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Maltotetraose exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>alpha-1,4-Tetraglucose</synonym>
    <synonym>Amylotetraose</synonym>
    <synonym>O-alpha-D-Glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-O-alpha-D-glucopyranosyl-(1-4)-D-glucose</synonym>
    <synonym>O-alpha-D-Glucopyranosyl-(1-&gt;4)-O(4xi)-alpha-D-xylo-hexopyranosyl-(1-&gt;4)-O-alpha-D-glucopyranosyl-(1-&gt;4)-D-glucose</synonym>
    <synonym>O-alpha-D-Glucopyranosyl-(1.4)-O-alpha-D-glucopyranosyl-(1.4)-O-alpha-D-glucopyranosyl-(1.4)-D-glucose</synonym>
    <synonym>O-alpha-delta-Glucopyranosyl-(1-4)-O-alpha-delta-glucopyranosyl-(1-4)-O-alpha-delta-glucopyranosyl-(1-4)-delta-glucose</synonym>
    <synonym>O-alpha-delta-Glucopyranosyl-(1-&gt;4)-O(4xi)-alpha-delta-xylo-hexopyranosyl-(1-&gt;4)-O-alpha-delta-glucopyranosyl-(1-&gt;4)-delta-glucose</synonym>
    <synonym>O-alpha-delta-Glucopyranosyl-(1.4)-O-alpha-delta-glucopyranosyl-(1.4)-O-alpha-delta-glucopyranosyl-(1.4)-delta-glucose</synonym>
  </synonyms>
  <chemical_formula>C24H42O21</chemical_formula>
  <average_molecular_weight>666.5777</average_molecular_weight>
  <monisotopic_moleculate_weight>666.221858406</monisotopic_moleculate_weight>
  <iupac_name>(3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol</iupac_name>
  <traditional_iupac>(3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol</traditional_iupac>
  <cas_registry_number>34612-38-9</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)C(O)O[C@@H]4CO)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C24H42O21/c25-1-5-9(29)10(30)15(35)22(40-5)44-19-7(3-27)42-24(17(37)12(19)32)45-20-8(4-28)41-23(16(36)13(20)33)43-18-6(2-26)39-21(38)14(34)11(18)31/h5-38H,1-4H2/t5-,6-,7-,8-,9-,10+,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21?,22-,23-,24-/m1/s1</inchi>
  <inchikey>LUEWUZLMQUOBSB-AYQJAVFRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Oligosaccharides</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Oligosaccharide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-8.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-5-{[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-(hydroxymethyl)oxane-2,3,4-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>666.5777</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>666.221858406</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)C(O)O[C@@H]4CO)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C24H42O21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C24H42O21/c25-1-5-9(29)10(30)15(35)22(40-5)44-19-7(3-27)42-24(17(37)12(19)32)45-20-8(4-28)41-23(16(36)13(20)33)43-18-6(2-26)39-21(38)14(34)11(18)31/h5-38H,1-4H2/t5-,6-,7-,8-,9-,10+,11-,12-,13-,14-,15-,16-,17-,18-,19-,20-,21?,22-,23-,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LUEWUZLMQUOBSB-AYQJAVFRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>347.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>133.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>62.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>368760</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02052</kegg_id>
  <foodb_id>FDB001195</foodb_id>
  <chemspider_id>388711</chemspider_id>
  <pubchem_compound_id>439639</pubchem_compound_id>
  <chebi_id>143180</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00018031</knapsack_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Maltodextrin</wikipedia_id>
  <metlin_id>4199</metlin_id>
  <synthesis_reference>Zhu, Ming.  Production of maltotetraose.    Wuxi Qinggong Daxue Xuebao  (1999),  18(2),  7-12.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:45 UTC</creation_date>
  <update_date>2020-04-14 22:49:06 UTC</update_date>
  <accession>BMDB0001297</accession>
  <secondary_accessions>
    <accession>BMDB01297</accession>
  </secondary_accessions>
  <name>Norcotinine</name>
  <description/>
  <synonyms>
    <synonym>(RS)-Norcotinine</synonym>
    <synonym>5-(3-Pyridinyl)-2-pyrrolidinone</synonym>
    <synonym>Demethylcotinine</synonym>
    <synonym>Norcotinine, (+-)-isomer</synonym>
    <synonym>Norcotinine, (R)-isomer</synonym>
    <synonym>Norcotinine, (S)-isomer</synonym>
  </synonyms>
  <chemical_formula>C9H10N2O</chemical_formula>
  <average_molecular_weight>162.1885</average_molecular_weight>
  <monisotopic_moleculate_weight>162.079312952</monisotopic_moleculate_weight>
  <iupac_name>5-(pyridin-3-yl)pyrrolidin-2-one</iupac_name>
  <traditional_iupac>5-pyridin-3-ylpyrrolidin-2-one</traditional_iupac>
  <cas_registry_number>17114-40-8</cas_registry_number>
  <smiles>O=C1CCC(N1)C1=CN=CC=C1</smiles>
  <inchi>InChI=1S/C9H10N2O/c12-9-4-3-8(11-9)7-2-1-5-10-6-7/h1-2,5-6,8H,3-4H2,(H,11,12)</inchi>
  <inchikey>FXFANIORDKRCCA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class/>
    <direct_parent>Pyridines and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Cyclic carboximidic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactims</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrrolines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Cyclic carboximidic acid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactim</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Pyrroline</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a secondary metabolite</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.013</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-(pyridin-3-yl)pyrrolidin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>162.1885</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>162.079312952</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O=C1CCC(N1)C1=CN=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10N2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10N2O/c12-9-4-3-8(11-9)7-2-1-5-10-6-7/h1-2,5-6,8H,3-4H2,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FXFANIORDKRCCA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>41.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>44.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>84209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145994</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022540</foodb_id>
  <chemspider_id>400</chemspider_id>
  <pubchem_compound_id>413</pubchem_compound_id>
  <chebi_id>89406</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6142</metlin_id>
  <synthesis_reference>Dewey, Lovell J.  Metabolites of nicotine and a synthesis of nornicotine.    Journal of the American Chemical Society  (1958),  80  1634-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:46 UTC</creation_date>
  <update_date>2020-03-13 16:27:06 UTC</update_date>
  <accession>BMDB0001299</accession>
  <secondary_accessions>
    <accession>BMDB01299</accession>
  </secondary_accessions>
  <name>5-Methylthioribulose 1-phosphate</name>
  <description/>
  <synonyms>
    <synonym>5-S-Methyl-1-O-phosphono-5-thio-D-ribulose</synonym>
    <synonym>5-(Methylsulfanyl)-D-ribulose 1-phosphate</synonym>
    <synonym>5-(Methylsulfanyl)-D-ribulose 1-phosphoric acid</synonym>
    <synonym>5-(Methylsulphanyl)-D-ribulose 1-phosphate</synonym>
    <synonym>5-(Methylsulphanyl)-D-ribulose 1-phosphoric acid</synonym>
    <synonym>5-Methylthioribulose 1-phosphoric acid</synonym>
    <synonym>1-Phospho-5-S-methylthioribulose</synonym>
    <synonym>1-Phosphomethylthioribulose</synonym>
    <synonym>1PMT-Ribulose</synonym>
    <synonym>5-Methylthio-2-ribulose-1-phosphate</synonym>
    <synonym>5-Methylthio-5-deoxy-D-ribulose 1-phosphate</synonym>
    <synonym>5-Methylthio-5-deoxy-D-ribulose-1-phosphate</synonym>
    <synonym>5-Methylthioribulose-1-phosphate</synonym>
    <synonym>5-S-Methyl-5-thio-D-erythro-pent-2-ulose 1-(dihydrogen phosphate)</synonym>
    <synonym>5-S-Methyl-5-thio-D-ribulose 1-(dihydrogen phosphate)</synonym>
    <synonym>Methylthioribulose-1-phosphate</synonym>
    <synonym>MTRu-1-p</synonym>
    <synonym>S-Methyl-5-thio-D-ribulose 1-phosphate</synonym>
    <synonym>1-PMT-Ribulose</synonym>
    <synonym>Methylthioribulose 1-phosphate</synonym>
  </synonyms>
  <chemical_formula>C6H13O7PS</chemical_formula>
  <average_molecular_weight>260.202</average_molecular_weight>
  <monisotopic_moleculate_weight>260.011959972</monisotopic_moleculate_weight>
  <iupac_name>{[(3R,4S)-3,4-dihydroxy-5-(methylsulfanyl)-2-oxopentyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>methylthioribulose-1-phosphate</traditional_iupac>
  <cas_registry_number>86316-83-8</cas_registry_number>
  <smiles>CSC[C@@H](O)[C@@H](O)C(=O)COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C6H13O7PS/c1-15-3-5(8)6(9)4(7)2-13-14(10,11)12/h5-6,8-9H,2-3H2,1H3,(H2,10,11,12)/t5-,6+/m1/s1</inchi>
  <inchikey>CNSJRYUMVMWNMC-RITPCOANSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Glycerone phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Acyloins</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Dialkylthioethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Acyloin</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Glycerone phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thioether</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>deoxyribulose phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(3R,4S)-3,4-dihydroxy-5-(methylsulfanyl)-2-oxopentyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>260.202</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>260.011959972</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CSC[C@@H](O)[C@@H](O)C(=O)COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O7PS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O7PS/c1-15-3-5(8)6(9)4(7)2-13-14(10,11)12/h5-6,8-9H,2-3H2,1H3,(H2,10,11,12)/t5-,6+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CNSJRYUMVMWNMC-RITPCOANSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>124.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>53.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182051</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04582</kegg_id>
  <foodb_id>FDB022541</foodb_id>
  <chemspider_id>152225</chemspider_id>
  <pubchem_compound_id>174549</pubchem_compound_id>
  <chebi_id>28096</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>44103</bigg_id>
  <wikipedia_id/>
  <metlin_id>6143</metlin_id>
  <synthesis_reference>Imker, Heidi J.; Fedorov, Alexander A.; Fedorov, Elena V.; Almo, Steven C.; Gerlt, John A.  Mechanistic Diversity in the RuBisCO Superfamily: The "Enolase" in the Methionine Salvage Pathway in Geobacillus kaustophilus.    Biochemistry  (2007),  46(13),  4077-4089.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01077</protein_accession>
      <name>Methylthioribose-1-phosphate isomerase</name>
      <uniprot_id>Q2NL31</uniprot_id>
      <gene_name>MRI1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:48 UTC</creation_date>
  <update_date>2020-03-13 16:27:06 UTC</update_date>
  <accession>BMDB0001300</accession>
  <secondary_accessions>
    <accession>BMDB01300</accession>
  </secondary_accessions>
  <name>Nitrophenylphosphate</name>
  <description/>
  <synonyms>
    <synonym>Nitrophenylphosphoric acid</synonym>
    <synonym>4-Nitrophenyl hydrogen phosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C6H5NO6P</chemical_formula>
  <average_molecular_weight>218.0808</average_molecular_weight>
  <monisotopic_moleculate_weight>217.985448409</monisotopic_moleculate_weight>
  <iupac_name>4-nitrophenyl hydrogen phosphate</iupac_name>
  <traditional_iupac>4-nitrophenyl hydrogen phosphate</traditional_iupac>
  <cas_registry_number/>
  <smiles>OP([O-])(=O)OC1=CC=C(C=C1)N(=O)=O</smiles>
  <inchi>InChI=1S/C6H6NO6P/c8-7(9)5-1-3-6(4-2-5)13-14(10,11)12/h1-4H,(H2,10,11,12)/p-1</inchi>
  <inchikey>XZKIHKMTEMTJQX-UHFFFAOYSA-M</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenyl phosphates. These are aromatic organooxygen compounds containing a phosphate group, which is O-esterified with a phenyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic phosphoric acids and derivatives</class>
    <sub_class>Phosphate esters</sub_class>
    <direct_parent>Phenyl phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Nitroaromatic compounds</alternative_parent>
      <alternative_parent>Nitrobenzenes</alternative_parent>
      <alternative_parent>Organic anions</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic oxoazanium compounds</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>C-nitro compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Nitroaromatic compound</substituent>
      <substituent>Nitrobenzene</substituent>
      <substituent>Organic anion</substituent>
      <substituent>Organic nitro compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxoazanium</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenyl phosphate</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-nitrophenyl hydrogen phosphate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>218.0808</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>217.985448409</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OP([O-])(=O)OC1=CC=C(C=C1)N(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H5NO6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H6NO6P/c8-7(9)5-1-3-6(4-2-5)13-14(10,11)12/h1-4H,(H2,10,11,12)/p-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XZKIHKMTEMTJQX-UHFFFAOYSA-M</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>115.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1350763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1350764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1350765</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id/>
  <foodb_id/>
  <kegg_id/>
  <chebi_id/>
  <pubchem_compound_id>3313668</pubchem_compound_id>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <wikipedia_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference>Kirchberger J; Kopperschlager G  Purification of impure 4-nitrophenylphosphate preparations.    Zeitschrift fur medizinische Laboratoriumsdiagnostik  (1985),  26(3),  176-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:49 UTC</creation_date>
  <update_date>2020-04-15 22:07:25 UTC</update_date>
  <accession>BMDB0001301</accession>
  <secondary_accessions>
    <accession>BMDB01301</accession>
  </secondary_accessions>
  <name>1-Pyrroline-5-carboxylic acid</name>
  <description/>
  <synonyms>
    <synonym>3,4-Dihydro-2H-pyrrole-2-carboxylate</synonym>
    <synonym>Delta(1)-Pyrroline-5-carboxylic acid</synonym>
    <synonym>3,4-Dihydro-2H-pyrrole-2-carboxylic acid</synonym>
    <synonym>delta(1)-Pyrroline-5-carboxylate</synonym>
    <synonym>Δ(1)-pyrroline-5-carboxylate</synonym>
    <synonym>Δ(1)-pyrroline-5-carboxylic acid</synonym>
    <synonym>1-Pyrroline-5-carboxylate</synonym>
    <synonym>delta(1)Pyrroline-5-carboxylate</synonym>
    <synonym>delta-1-Pyrroline-5-carboxylate, 14C-labeled, (+-)-isomer</synonym>
    <synonym>Pyrroline-5-carboxylate</synonym>
    <synonym>delta-1-Pyrroline-5-carboxylate</synonym>
    <synonym>delta-1-Pyrroline-5-carboxylate, (+-)-isomer</synonym>
    <synonym>delta-1-Pyrroline-5-carboxylic acid</synonym>
    <synonym>(S)-1-Pyrroline-5-carboxylate</synonym>
    <synonym>D1-Pyrroline-5-carboxylate</synonym>
    <synonym>D1-Pyrroline-5-carboxylic acid</synonym>
    <synonym>DL-1-Pyrroline-5-carboxylate</synonym>
    <synonym>DL-1-Pyrroline-5-carboxylic acid</synonym>
    <synonym>L-1-Pyrroline-5-carboxylate</synonym>
    <synonym>L-delta 1-Pyrroline-5-carboxylate</synonym>
    <synonym>Pyrroline 5-carboxylate</synonym>
  </synonyms>
  <chemical_formula>C5H7NO2</chemical_formula>
  <average_molecular_weight>113.1146</average_molecular_weight>
  <monisotopic_moleculate_weight>113.047678473</monisotopic_moleculate_weight>
  <iupac_name>3,4-dihydro-2H-pyrrole-2-carboxylic acid</iupac_name>
  <traditional_iupac>1-pyrroline-5-carboxylic acid</traditional_iupac>
  <cas_registry_number>2906-39-0</cas_registry_number>
  <smiles>OC(=O)C1CCC=N1</smiles>
  <inchi>InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)</inchi>
  <inchikey>DWAKNKKXGALPNW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrroline carboxylic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyrroline</substituent>
      <substituent>Pyrroline carboxylic acid</substituent>
      <substituent>Pyrroline carboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>1-pyrrolinecarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3,4-dihydro-2H-pyrrole-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>113.1146</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>113.047678473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1CCC=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H7NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DWAKNKKXGALPNW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>49.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>27.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34876</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022542</foodb_id>
  <kegg_id>C04322</kegg_id>
  <chemspider_id>1159</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>1196</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>1372</chebi_id>
  <knapsack_id>C00007606</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>l-delta(1)-pyrroline_5-carboxylate</meta_cyc_id>
  <bigg_id>42766</bigg_id>
  <wikipedia_id>1-Pyrroline-5-carboxylic acid</wikipedia_id>
  <metlin_id>6145</metlin_id>
  <synthesis_reference>Vogel, Henry J.; Davis, Bernard D. Glutamic g-semialdehyde and D1-pyrroline-5-carboxylic acid, intermediates in the biosynthesis of proline. Journal of the American Chemical Society (1952), 74 109-12.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00860</protein_accession>
      <name>Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial</name>
      <uniprot_id>A7YWE4</uniprot_id>
      <gene_name>ALDH4A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00873</protein_accession>
      <name>Probable proline dehydrogenase 2</name>
      <uniprot_id>A6QQ74</uniprot_id>
      <gene_name>PRODH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01016</protein_accession>
      <name>Pyrroline-5-carboxylate reductase 3</name>
      <uniprot_id>Q58D08</uniprot_id>
      <gene_name>PYCRL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01018</protein_accession>
      <name>Pyrroline-5-carboxylate reductase 2</name>
      <uniprot_id>Q17QJ7</uniprot_id>
      <gene_name>PYCR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01024</protein_accession>
      <name>Pyrroline-5-carboxylate reductase 1, mitochondrial</name>
      <uniprot_id>Q58DT4</uniprot_id>
      <gene_name>PYCR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:50 UTC</creation_date>
  <update_date>2020-04-15 21:35:51 UTC</update_date>
  <accession>BMDB0001302</accession>
  <secondary_accessions>
    <accession>BMDB01302</accession>
  </secondary_accessions>
  <name>Molybdenum</name>
  <description>Molybdenum, also known as Mo, belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Molybdenum exists as a solid, possibly soluble (in water), and possibly neutral molecule. Molybdenum exists in all living organisms, ranging from bacteria to humans. In cattle, molybdenum is involved in the metabolic pathway called the caffeine metabolism pathway. Molybdenum is a potentially toxic compound.</description>
  <synonyms>
    <synonym>Mo</synonym>
    <synonym>Molybdaen</synonym>
    <synonym>Molybdene</synonym>
    <synonym>Molybdenum atom</synonym>
    <synonym>Molybdenum elemental</synonym>
    <synonym>Molybdenum insoluble compounds</synonym>
    <synonym>Molybdenum metallic</synonym>
  </synonyms>
  <chemical_formula>Mo</chemical_formula>
  <average_molecular_weight>95.94</average_molecular_weight>
  <monisotopic_moleculate_weight>97.905407846</monisotopic_moleculate_weight>
  <iupac_name>molybdenum(2+) ion</iupac_name>
  <traditional_iupac>molybdenum(2+) ion</traditional_iupac>
  <cas_registry_number>7439-98-7</cas_registry_number>
  <smiles>[Mo++]</smiles>
  <inchi>InChI=1S/Mo/q+2</inchi>
  <inchikey>MMVYPOCJESWGTC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous transition metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous transition metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous transition metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a cation</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>2622 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>molybdenum(2+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>95.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>97.905407846</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Mo++]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Mo</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Mo/q+2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MMVYPOCJESWGTC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Sulfate/Sulfite Metabolism</name>
      <smpdb_id>SMP0087216</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29995</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>3+/-1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.41</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.26 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.25 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.25 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.154 +/- 0.00208</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized non-fat milk</comment>
      <references>
        <reference>
          <reference_text>Lopez-Garcia I, Vinas P, Romero-Romero R, Hernandez-Cordoba M: Liquid chromatography-electrothermal atomic absorption spectrometry for the separation and preconcentration of molybdenum in milk and infant formulas. Anal Chim Acta. 2007 Aug 6;597(2):187-94. doi: 10.1016/j.aca.2007.07.003. Epub 2007 Jul 5.</reference_text>
          <pubmed_id>17683729</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.29 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.163 +/- 0.00104</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized skim milk</comment>
      <references>
        <reference>
          <reference_text>Lopez-Garcia I, Vinas P, Romero-Romero R, Hernandez-Cordoba M: Liquid chromatography-electrothermal atomic absorption spectrometry for the separation and preconcentration of molybdenum in milk and infant formulas. Anal Chim Acta. 2007 Aug 6;597(2):187-94. doi: 10.1016/j.aca.2007.07.003. Epub 2007 Jul 5.</reference_text>
          <pubmed_id>17683729</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.180 +/- 0.00208</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Pasteurized whole milk</comment>
      <references>
        <reference>
          <reference_text>Lopez-Garcia I, Vinas P, Romero-Romero R, Hernandez-Cordoba M: Liquid chromatography-electrothermal atomic absorption spectrometry for the separation and preconcentration of molybdenum in milk and infant formulas. Anal Chim Acta. 2007 Aug 6;597(2):187-94. doi: 10.1016/j.aca.2007.07.003. Epub 2007 Jul 5.</reference_text>
          <pubmed_id>17683729</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.216 +/- 0.00938</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.170 +/- 0.00417</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.229 +/- 0.0104</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS.  Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.161 +/- 0.00417</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.146 +/- 0.0208</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.106 +/- 0.00730</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.417 - 1.876</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.108 - 0.111</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.0187 +/- 0.008</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by ICP-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>0.06+/-0.01</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00150</kegg_id>
  <foodb_id>FDB003653</foodb_id>
  <chemspider_id>161267</chemspider_id>
  <pubchem_compound_id>185498</pubchem_compound_id>
  <pdbe_id/>
  <drugbank_id/>
  <chebi_id>28685</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Molybdenum</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Lopez-Garcia I, Vinas P, Romero-Romero R, Hernandez-Cordoba M: Liquid chromatography-electrothermal atomic absorption spectrometry for the separation and preconcentration of molybdenum in milk and infant formulas. Anal Chim Acta. 2007 Aug 6;597(2):187-94. doi: 10.1016/j.aca.2007.07.003. Epub 2007 Jul 5.</reference_text>
      <pubmed_id>17683729</pubmed_id>
    </reference>
    <reference>
      <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
    </reference>
    <reference>
      <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00221</protein_accession>
      <name>MOSC domain-containing protein 2, mitochondrial</name>
      <uniprot_id>Q1LZH1</uniprot_id>
      <gene_name>MOSC2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00603</protein_accession>
      <name>Xanthine dehydrogenase/oxidase</name>
      <uniprot_id>P80457</uniprot_id>
      <gene_name>XDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00677</protein_accession>
      <name>Aldehyde oxidase</name>
      <uniprot_id>P48034</uniprot_id>
      <gene_name>AOX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:51 UTC</creation_date>
  <update_date>2020-04-14 21:29:10 UTC</update_date>
  <accession>BMDB0001303</accession>
  <secondary_accessions>
    <accession>BMDB01303</accession>
  </secondary_accessions>
  <name>Zinc</name>
  <description>Zinc, also known as ZN2+ or zinc ion, belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Zinc is possibly soluble (in water) and possibly neutral. Zinc exists in all living species, ranging from bacteria to humans. Zinc is a potentially toxic compound.</description>
  <synonyms>
    <synonym>Dietary zinc</synonym>
    <synonym>Zinc cation</synonym>
    <synonym>ZINC ion</synonym>
    <synonym>Zinc, ion (ZN2+)</synonym>
    <synonym>ZN(II)</synonym>
    <synonym>ZN(2+)</synonym>
    <synonym>ZN2+</synonym>
    <synonym>Mannosidase b, alpha</synonym>
    <synonym>alpha Mannosidase b</synonym>
    <synonym>alpha-D-Mannoside mannohydrolase</synonym>
    <synonym>Neutral alpha-mannosidase</synonym>
    <synonym>alpha D Mannosidase</synonym>
    <synonym>alpha-D-Mannosidase</synonym>
    <synonym>Lysosomal alpha-mannosidase</synonym>
    <synonym>Mannohydrolase, alpha-D-mannoside</synonym>
    <synonym>alpha Mannosidase</synonym>
    <synonym>alpha-Mannosidase</synonym>
    <synonym>LAMAN</synonym>
    <synonym>Lysosomal alpha mannosidase</synonym>
    <synonym>Neutral alpha mannosidase</synonym>
    <synonym>alpha D Mannoside mannohydrolase</synonym>
    <synonym>alpha-Mannosidase, lysosomal</synonym>
    <synonym>alpha-Mannosidase, neutral</synonym>
    <synonym>Topostin b</synonym>
  </synonyms>
  <chemical_formula>Zn</chemical_formula>
  <average_molecular_weight>65.409</average_molecular_weight>
  <monisotopic_moleculate_weight>63.929146578</monisotopic_moleculate_weight>
  <iupac_name>zinc(2+) ion</iupac_name>
  <traditional_iupac>zinc(2+) ion</traditional_iupac>
  <cas_registry_number>23713-49-7</cas_registry_number>
  <smiles>[Zn++]</smiles>
  <inchi>InChI=1S/Zn/q+2</inchi>
  <inchikey>PTFCDOFLOPIGGS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous transition metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous transition metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous transition metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a cation</external_descriptor>
      <external_descriptor>divalent metal cation</external_descriptor>
      <external_descriptor>monoatomic dication</external_descriptor>
      <external_descriptor>zinc cation</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>zinc(2+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>65.409</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>63.929146578</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Zn++]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Zn</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Zn/q+2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PTFCDOFLOPIGGS-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Angiotensin Metabolism</name>
      <smpdb_id>SMP0119379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Degradation of Superoxides</name>
      <smpdb_id>SMP0087191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ethanol Degradation</name>
      <smpdb_id>SMP0087192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gastric Acid Production</name>
      <smpdb_id>SMP0119381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutathione Metabolism</name>
      <smpdb_id>SMP0087167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Alanine</name>
      <smpdb_id>SMP0119369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Protein Synthesis: Cysteine</name>
      <smpdb_id>SMP0119388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvaldehyde Degradation</name>
      <smpdb_id>SMP0087210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34447</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>12+/-2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>39+/-60</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>81.0286</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>70 +/- 16</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw whole milk</comment>
      <references>
        <reference>
          <reference_text>Zhang P, Allen JC: A novel dialysis procedure measuring free Zn2+ in bovine milk and plasma. J Nutr. 1995 Jul;125(7):1904-10. doi: 10.1093/jn/125.7.1904.</reference_text>
          <pubmed_id>7616307</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>55.0383</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>55.0383</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>64.211</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>61.154</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>58.096</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>68.798</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>61.154</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>64.211</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>68.798</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>62.683</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>44.306 +/- 1.911</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>64.211</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20.578 +/- 1.468</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>64.211</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>49.733 +/- 3.134</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS.  Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>63.294</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18.713 +/- 1.162</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>63.294</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20.945 +/- 1.177</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>58.096</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15.518 +/- 2.920</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>68.798</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>61.154</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>62.683</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>73.384</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>73.384</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>62.683</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>62.683</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>61.154</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>62.683</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>45.865 - 61.154</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>56.567</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>56.567</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>71.856</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>64.0585</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>64.0585</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>54 +/- 8 </concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>65 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>69 +/- 6 </concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>65 +/- 3 </concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.338 - 49.534</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>45.865 +/- 3.0577</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Campillo N, Vinas P, Lopez-Garcia I, Hernandez-Cordoba M: Direct determination of copper and zinc in cow milk, human milk and infant formula samples using electrothermal atomization atomic absorption spectrometry. Talanta. 1998 Aug;46(4):615-22.</reference_text>
          <pubmed_id>18967184</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>47.165 - 48.357</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2.39 +/- 0.51</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by ICP-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>10+/-3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>4+/-1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00038</kegg_id>
  <foodb_id>FDB031256</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>32051</pubchem_compound_id>
  <pdbe_id/>
  <drugbank_id/>
  <chebi_id>29105</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Zhang P, Allen JC: A novel dialysis procedure measuring free Zn2+ in bovine milk and plasma. J Nutr. 1995 Jul;125(7):1904-10. doi: 10.1093/jn/125.7.1904.</reference_text>
      <pubmed_id>7616307</pubmed_id>
    </reference>
    <reference>
      <reference_text>Campillo N, Vinas P, Lopez-Garcia I, Hernandez-Cordoba M: Direct determination of copper and zinc in cow milk, human milk and infant formula samples using electrothermal atomization atomic absorption spectrometry. Talanta. 1998 Aug;46(4):615-22.</reference_text>
      <pubmed_id>18967184</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
      <pubmed_id>22081685</pubmed_id>
    </reference>
    <reference>
      <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
    </reference>
    <reference>
      <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00133</protein_accession>
      <name>Manganese-dependent ADP-ribose/CDP-alcohol diphosphatase</name>
      <uniprot_id>A7YY53</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00159</protein_accession>
      <name>5'-nucleotidase</name>
      <uniprot_id>Q05927</uniprot_id>
      <gene_name>NT5E</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00198</protein_accession>
      <name>Alkaline phosphatase</name>
      <uniprot_id>A6QQR9</uniprot_id>
      <gene_name>LOC100125266</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00233</protein_accession>
      <name>Disintegrin and metalloproteinase domain-containing protein 10</name>
      <uniprot_id>Q10741</uniprot_id>
      <gene_name>ADAM10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00402</protein_accession>
      <name>EHMT1 protein</name>
      <uniprot_id>A5PK11</uniprot_id>
      <gene_name>EHMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00408</protein_accession>
      <name>Cytosine-specific methyltransferase</name>
      <uniprot_id>B1P383</uniprot_id>
      <gene_name>Dnmt1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00499</protein_accession>
      <name>Cytosol aminopeptidase</name>
      <uniprot_id>P00727</uniprot_id>
      <gene_name>LAP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00552</protein_accession>
      <name>Carboxypeptidase E</name>
      <uniprot_id>P04836</uniprot_id>
      <gene_name>CPE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00554</protein_accession>
      <name>Carboxypeptidase B</name>
      <uniprot_id>P00732</uniprot_id>
      <gene_name>CPB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00562</protein_accession>
      <name>Aspartoacylase</name>
      <uniprot_id>P46446</uniprot_id>
      <gene_name>ASPA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00572</protein_accession>
      <name>Glutamyl aminopeptidase</name>
      <uniprot_id>Q32LQ0</uniprot_id>
      <gene_name>ENPEP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00580</protein_accession>
      <name>Activation-induced cytidine deaminase</name>
      <uniprot_id>Q2PT36</uniprot_id>
      <gene_name>AICDA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00587</protein_accession>
      <name>Superoxide dismutase [Cu-Zn]</name>
      <uniprot_id>A4URH1</uniprot_id>
      <gene_name>SOD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00589</protein_accession>
      <name>Superoxide dismutase [Cu-Zn]</name>
      <uniprot_id>A3KLR9</uniprot_id>
      <gene_name>ECSOD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00612</protein_accession>
      <name>N(G),N(G)-dimethylarginine dimethylaminohydrolase 1</name>
      <uniprot_id>P56965</uniprot_id>
      <gene_name>DDAH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00650</protein_accession>
      <name>Cytosolic non-specific dipeptidase</name>
      <uniprot_id>Q3ZC84</uniprot_id>
      <gene_name>CNDP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00665</protein_accession>
      <name>Peptidyl-glycine alpha-amidating monooxygenase</name>
      <uniprot_id>P10731</uniprot_id>
      <gene_name>PAM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00784</protein_accession>
      <name>Sorbitol dehydrogenase</name>
      <uniprot_id>Q58D31</uniprot_id>
      <gene_name>SORD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00795</protein_accession>
      <name>Methionine aminopeptidase 1</name>
      <uniprot_id>A6QLA4</uniprot_id>
      <gene_name>METAP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00797</protein_accession>
      <name>Methionine aminopeptidase 2</name>
      <uniprot_id>Q3ZC89</uniprot_id>
      <gene_name>METAP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00820</protein_accession>
      <name>A disintegrin and metalloproteinase with thrombospondin motifs 4</name>
      <uniprot_id>Q9TT93</uniprot_id>
      <gene_name>ADAMTS4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00825</protein_accession>
      <name>Aprataxin and PNK-like factor</name>
      <uniprot_id>A0JNH9</uniprot_id>
      <gene_name>APLF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00828</protein_accession>
      <name>DNA-(apurinic or apyrimidinic site) lyase 2</name>
      <uniprot_id>Q5E9N9</uniprot_id>
      <gene_name>APEX2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00974</protein_accession>
      <name>Carboxypeptidase N catalytic chain</name>
      <uniprot_id>Q2KJ83</uniprot_id>
      <gene_name>CPN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00991</protein_accession>
      <name>Alcohol dehydrogenase class-3</name>
      <uniprot_id>Q3ZC42</uniprot_id>
      <gene_name>ADH5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01005</protein_accession>
      <name>Angiotensin-converting enzyme</name>
      <uniprot_id>P12820</uniprot_id>
      <gene_name>ACE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01034</protein_accession>
      <name>Carbonic anhydrase 1</name>
      <uniprot_id>Q1LZA1</uniprot_id>
      <gene_name>CA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01035</protein_accession>
      <name>Protein kinase C, zeta</name>
      <uniprot_id>A0JNH7</uniprot_id>
      <gene_name>PRKCZ</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01036</protein_accession>
      <name>Aminopeptidase B</name>
      <uniprot_id>A2T1U6</uniprot_id>
      <gene_name>AP-B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01037</protein_accession>
      <name>A disintegrin and metalloproteinase with thrombospondin motifs 5</name>
      <uniprot_id>Q9TT92</uniprot_id>
      <gene_name>ADAMTS5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01038</protein_accession>
      <name>Protein kinase C, alpha</name>
      <uniprot_id>B0JYP1</uniprot_id>
      <gene_name>PRKCA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01039</protein_accession>
      <name>Angiotensin-converting enzyme 2</name>
      <uniprot_id>Q58DD0</uniprot_id>
      <gene_name>ACE2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01040</protein_accession>
      <name>Lys-63-specific deubiquitinase BRCC36</name>
      <uniprot_id>A5PJP6</uniprot_id>
      <gene_name>BRCC3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01041</protein_accession>
      <name>Breast cancer type 1 susceptibility protein homolog</name>
      <uniprot_id>Q864U1</uniprot_id>
      <gene_name>BRCA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01042</protein_accession>
      <name>Carboxypeptidase A1 (Pancreatic)</name>
      <uniprot_id>A6H6Y4</uniprot_id>
      <gene_name>CPA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01043</protein_accession>
      <name>Disintegrin and metalloproteinase domain-containing protein 2</name>
      <uniprot_id>O77780</uniprot_id>
      <gene_name>ADAM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01044</protein_accession>
      <name>Carbonic anhydrase 6</name>
      <uniprot_id>P18915</uniprot_id>
      <gene_name>CA6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01045</protein_accession>
      <name>Translocase of inner mitochondrial membrane 13</name>
      <uniprot_id>A1A4M0</uniprot_id>
      <gene_name>TIMM13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01046</protein_accession>
      <name>Matrix metallopeptidase 2 (Gelatinase A, 72kDa gelatinase, 72kDa type IV collagenase)</name>
      <uniprot_id>A6QPN5</uniprot_id>
      <gene_name>MMP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01047</protein_accession>
      <name>Pancreatic carboxypeptidase B</name>
      <uniprot_id>B1PZ69</uniprot_id>
      <gene_name>pCPB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01048</protein_accession>
      <name>Ubiquitin carboxyl-terminal hydrolase</name>
      <uniprot_id>A7Z056</uniprot_id>
      <gene_name>USP20</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01049</protein_accession>
      <name>A disintegrin and metalloproteinase with thrombospondin motifs 2</name>
      <uniprot_id>P79331</uniprot_id>
      <gene_name>ADAMTS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01050</protein_accession>
      <name>AFG3-like protein 2</name>
      <uniprot_id>Q2KJI7</uniprot_id>
      <gene_name>AFG3L2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01051</protein_accession>
      <name>DNA topoisomerase</name>
      <uniprot_id>A0JN73</uniprot_id>
      <gene_name>TOP3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01052</protein_accession>
      <name>Ubiquitin isopeptidase T</name>
      <uniprot_id>A1L548</uniprot_id>
      <gene_name>USP5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01053</protein_accession>
      <name>Cytochrome c oxidase subunit 5B, mitochondrial</name>
      <uniprot_id>P00428</uniprot_id>
      <gene_name>COX5B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01054</protein_accession>
      <name>Cleavage and polyadenylation specificity factor subunit 3</name>
      <uniprot_id>P79101</uniprot_id>
      <gene_name>CPSF3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01055</protein_accession>
      <name>Carboxypeptidase B2</name>
      <uniprot_id>Q2KIG3</uniprot_id>
      <gene_name>CPB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01056</protein_accession>
      <name>Probable C-&gt;U-editing enzyme APOBEC-2</name>
      <uniprot_id>Q3SYR3</uniprot_id>
      <gene_name>APOBEC2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01057</protein_accession>
      <name>Betaine--homocysteine S-methyltransferase 1</name>
      <uniprot_id>Q5I597</uniprot_id>
      <gene_name>BHMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01058</protein_accession>
      <name>Aminopeptidase N</name>
      <uniprot_id>P79098</uniprot_id>
      <gene_name>ANPEP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01059</protein_accession>
      <name>Aprataxin</name>
      <uniprot_id>Q7YRZ2</uniprot_id>
      <gene_name>APTX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01060</protein_accession>
      <name>Carbonic anhydrase 2</name>
      <uniprot_id>P00921</uniprot_id>
      <gene_name>CA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01061</protein_accession>
      <name>tRNA-specific adenosine deaminase 2</name>
      <uniprot_id>Q5E9J7</uniprot_id>
      <gene_name>DEADC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01062</protein_accession>
      <name>Carbonic anhydrase 3</name>
      <uniprot_id>Q3SZX4</uniprot_id>
      <gene_name>CA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01063</protein_accession>
      <name>Protein kinase C, delta</name>
      <uniprot_id>A0JN97</uniprot_id>
      <gene_name>PRKCD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01064</protein_accession>
      <name>Diacylglycerol kinase alpha</name>
      <uniprot_id>A0JN54</uniprot_id>
      <gene_name>DGKA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01065</protein_accession>
      <name>Ubiquitin carboxyl-terminal hydrolase</name>
      <uniprot_id>A6QNM7</uniprot_id>
      <gene_name>USP33</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01066</protein_accession>
      <name>Carbonic anhydrase 4</name>
      <uniprot_id>Q95323</uniprot_id>
      <gene_name>CA4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01067</protein_accession>
      <name>Ester hydrolase C11orf54 homolog</name>
      <uniprot_id>Q2HJH3</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01068</protein_accession>
      <name>Carboxypeptidase A1</name>
      <uniprot_id>P00730</uniprot_id>
      <gene_name>CPA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01069</protein_accession>
      <name>Carboxypeptidase A5</name>
      <uniprot_id>A0JNG8</uniprot_id>
      <gene_name>CPA5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01070</protein_accession>
      <name>Carboxypeptidase O</name>
      <uniprot_id>Q0II73</uniprot_id>
      <gene_name>CPO</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01071</protein_accession>
      <name>E3 ubiquitin-protein ligase BRE1A</name>
      <uniprot_id>A2VDP1</uniprot_id>
      <gene_name>RNF20</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01202</protein_accession>
      <name>CDC42BPG protein</name>
      <uniprot_id>A6QP95</uniprot_id>
      <gene_name>CDC42BPG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01211</protein_accession>
      <name>PRKCB protein</name>
      <uniprot_id>A5D7N0</uniprot_id>
      <gene_name>PRKCB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01331</protein_accession>
      <name>Arf-GAP with coiled-coil, ANK repeat and PH domain-containing protein 1</name>
      <uniprot_id>A5PK26</uniprot_id>
      <gene_name>ACAP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01332</protein_accession>
      <name>Arf-GAP with SH3 domain, ANK repeat and PH domain-containing protein 1</name>
      <uniprot_id>O97902</uniprot_id>
      <gene_name>ASAP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01345</protein_accession>
      <name>Cartilage oligomeric matrix protein</name>
      <uniprot_id>P35445</uniprot_id>
      <gene_name>COMP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01398</protein_accession>
      <name>ADAMTS1 protein</name>
      <uniprot_id>A7MB07</uniprot_id>
      <gene_name>ADAMTS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01640</protein_accession>
      <name>Zinc finger protein 775</name>
      <uniprot_id>A0JNI3</uniprot_id>
      <gene_name>ZNF775</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01641</protein_accession>
      <name>ZNF404 protein</name>
      <uniprot_id>A6QQ61</uniprot_id>
      <gene_name>ZNF404</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01647</protein_accession>
      <name>ZNF14 protein</name>
      <uniprot_id>A2VE73</uniprot_id>
      <gene_name>ZNF14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01648</protein_accession>
      <name>LOC100124511 protein</name>
      <uniprot_id>A1A4K0</uniprot_id>
      <gene_name>LOC100124511</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01651</protein_accession>
      <name>ZNF773 protein</name>
      <uniprot_id>A6QPU7</uniprot_id>
      <gene_name>ZNF773</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01652</protein_accession>
      <name>LOC516156 protein</name>
      <uniprot_id>A6QNX0</uniprot_id>
      <gene_name>LOC516156</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01654</protein_accession>
      <name>ZBTB44 protein</name>
      <uniprot_id>A6QNQ1</uniprot_id>
      <gene_name>ZBTB44</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01656</protein_accession>
      <name>MATR3 protein</name>
      <uniprot_id>A4IF82</uniprot_id>
      <gene_name>MATR3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01658</protein_accession>
      <name>ZFP3 protein</name>
      <uniprot_id>A5PJK9</uniprot_id>
      <gene_name>ZFP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01663</protein_accession>
      <name>FIZ1 protein</name>
      <uniprot_id>A6QNZ1</uniprot_id>
      <gene_name>FIZ1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01665</protein_accession>
      <name>DDX41 protein</name>
      <uniprot_id>A3KN07</uniprot_id>
      <gene_name>DDX41</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01667</protein_accession>
      <name>LOC100125388 protein</name>
      <uniprot_id>A6QQC1</uniprot_id>
      <gene_name>LOC100125388</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01670</protein_accession>
      <name>IKAROS family zinc finger 2 (Helios)</name>
      <uniprot_id>A0JNA9</uniprot_id>
      <gene_name>IKZF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01676</protein_accession>
      <name>Zinc finger protein LOC509810</name>
      <uniprot_id>A0JN57</uniprot_id>
      <gene_name>LOC509810</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01682</protein_accession>
      <name>ZNF583 protein</name>
      <uniprot_id>A3KN44</uniprot_id>
      <gene_name>ZNF583</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01684</protein_accession>
      <name>ZCCHC9 protein</name>
      <uniprot_id>A6H756</uniprot_id>
      <gene_name>ZCCHC9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01685</protein_accession>
      <name>ZNF565 protein</name>
      <uniprot_id>A6QNV5</uniprot_id>
      <gene_name>ZNF565</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01686</protein_accession>
      <name>ZNF774 protein</name>
      <uniprot_id>A6QNQ4</uniprot_id>
      <gene_name>ZNF774</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01687</protein_accession>
      <name>Zinc finger protein 688</name>
      <uniprot_id>A2VDY1</uniprot_id>
      <gene_name>ZNF688</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01689</protein_accession>
      <name>MGC155143 protein</name>
      <uniprot_id>A5D7M1</uniprot_id>
      <gene_name>MGC155143</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01692</protein_accession>
      <name>ZC3H10 protein</name>
      <uniprot_id>A5D7H8</uniprot_id>
      <gene_name>ZC3H10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01696</protein_accession>
      <name>PLAGL1 protein</name>
      <uniprot_id>A6QQH3</uniprot_id>
      <gene_name>PLAGL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01701</protein_accession>
      <name>ZNF226 protein</name>
      <uniprot_id>A7E325</uniprot_id>
      <gene_name>ZNF226</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01703</protein_accession>
      <name>Zinc finger protein 238</name>
      <uniprot_id>A0JN76</uniprot_id>
      <gene_name>ZNF238</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01704</protein_accession>
      <name>Y-linked zinc finger protein</name>
      <uniprot_id>A1XCL6</uniprot_id>
      <gene_name>ZFY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01705</protein_accession>
      <name>ZNF771 protein</name>
      <uniprot_id>A7E347</uniprot_id>
      <gene_name>ZNF771</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01706</protein_accession>
      <name>ZNF667 protein</name>
      <uniprot_id>A6QNL4</uniprot_id>
      <gene_name>ZNF667</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01712</protein_accession>
      <name>PRDM9 protein</name>
      <uniprot_id>A6QNW2</uniprot_id>
      <gene_name>PRDM9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01714</protein_accession>
      <name>Muscleblind-like 2</name>
      <uniprot_id>A1L584</uniprot_id>
      <gene_name>MBNL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01715</protein_accession>
      <name>LOC407241 protein</name>
      <uniprot_id>A6QL89</uniprot_id>
      <gene_name>LOC407241</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01718</protein_accession>
      <name>MGC139239 protein</name>
      <uniprot_id>A4FUW9</uniprot_id>
      <gene_name>MGC139239</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01720</protein_accession>
      <name>MGC157163 protein</name>
      <uniprot_id>A7MBK4</uniprot_id>
      <gene_name>MGC157163</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01725</protein_accession>
      <name>ZNF423 protein</name>
      <uniprot_id>A6QNQ0</uniprot_id>
      <gene_name>ZNF423</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01729</protein_accession>
      <name>ZNF674 protein</name>
      <uniprot_id>A6QP08</uniprot_id>
      <gene_name>ZNF674</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01730</protein_accession>
      <name>ZNF383 protein</name>
      <uniprot_id>A6QQH4</uniprot_id>
      <gene_name>ZNF383</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01731</protein_accession>
      <name>Kruppel-like factor 15</name>
      <uniprot_id>A2VE49</uniprot_id>
      <gene_name>LOC407241</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01736</protein_accession>
      <name>LOC100125413 protein</name>
      <uniprot_id>A6QQI0</uniprot_id>
      <gene_name>LOC100125413</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01737</protein_accession>
      <name>ZNF48 protein</name>
      <uniprot_id>A6QQT2</uniprot_id>
      <gene_name>ZNF48</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01740</protein_accession>
      <name>ZC3H11A protein</name>
      <uniprot_id>A5PKI2</uniprot_id>
      <gene_name>ZC3H11A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01743</protein_accession>
      <name>MGC157324 protein</name>
      <uniprot_id>A4IFV3</uniprot_id>
      <gene_name>MGC157324</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01746</protein_accession>
      <name>Zinc finger and BTB domain containing 5</name>
      <uniprot_id>A0JN94</uniprot_id>
      <gene_name>ZBTB5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01747</protein_accession>
      <name>Zinc finger, CCHC domain containing 10</name>
      <uniprot_id>A7E3S6</uniprot_id>
      <gene_name>ZCCHC10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01750</protein_accession>
      <name>VEZF1 protein</name>
      <uniprot_id>A6QQ84</uniprot_id>
      <gene_name>VEZF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01751</protein_accession>
      <name>ZNF131 protein</name>
      <uniprot_id>A6QR64</uniprot_id>
      <gene_name>ZNF131</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01753</protein_accession>
      <name>MBNL2 protein</name>
      <uniprot_id>A5PKK4</uniprot_id>
      <gene_name>MBNL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01756</protein_accession>
      <name>MKRN1 protein</name>
      <uniprot_id>A2VDX6</uniprot_id>
      <gene_name>MKRN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01757</protein_accession>
      <name>ZNF304 protein</name>
      <uniprot_id>A6QLF1</uniprot_id>
      <gene_name>ZNF304</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01758</protein_accession>
      <name>LOC100125304 protein</name>
      <uniprot_id>A4IFL9</uniprot_id>
      <gene_name>LOC100125304</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01759</protein_accession>
      <name>LOC100124429 protein</name>
      <uniprot_id>A7MB20</uniprot_id>
      <gene_name>LOC100124429</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01761</protein_accession>
      <name>ZNF784 protein</name>
      <uniprot_id>A5PJI8</uniprot_id>
      <gene_name>ZNF784</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01762</protein_accession>
      <name>ZFP36L1 protein</name>
      <uniprot_id>A7MB98</uniprot_id>
      <gene_name>ZFP36L1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01765</protein_accession>
      <name>RP9 protein</name>
      <uniprot_id>A7E3C9</uniprot_id>
      <gene_name>RP9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01766</protein_accession>
      <name>MBNL1 protein</name>
      <uniprot_id>A5PJM0</uniprot_id>
      <gene_name>MBNL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01767</protein_accession>
      <name>ZNF346 protein</name>
      <uniprot_id>A7YWD0</uniprot_id>
      <gene_name>ZNF346</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01771</protein_accession>
      <name>PHF1 protein</name>
      <uniprot_id>A6H7D5</uniprot_id>
      <gene_name>PHF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01773</protein_accession>
      <name>ZNF777 protein</name>
      <uniprot_id>A6QPN3</uniprot_id>
      <gene_name>ZNF777</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01776</protein_accession>
      <name>ZFP64 protein</name>
      <uniprot_id>A5PKJ0</uniprot_id>
      <gene_name>ZFP64</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01777</protein_accession>
      <name>ZFP2 protein</name>
      <uniprot_id>A5D7K3</uniprot_id>
      <gene_name>ZFP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01778</protein_accession>
      <name>KLF10 protein</name>
      <uniprot_id>A6QQG6</uniprot_id>
      <gene_name>KLF10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01780</protein_accession>
      <name>Unkempt homolog (Drosophila)</name>
      <uniprot_id>A1A4K6</uniprot_id>
      <gene_name>UNK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01781</protein_accession>
      <name>PIAS3 protein</name>
      <uniprot_id>A6QQU9</uniprot_id>
      <gene_name>PIAS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01784</protein_accession>
      <name>Zinc finger, CCHC domain containing 3</name>
      <uniprot_id>A1A4J3</uniprot_id>
      <gene_name>ZCCHC3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01788</protein_accession>
      <name>ZNF180 protein</name>
      <uniprot_id>A6QP07</uniprot_id>
      <gene_name>ZNF180</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01792</protein_accession>
      <name>ZNF200 protein</name>
      <uniprot_id>A4IF67</uniprot_id>
      <gene_name>ZNF200</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01793</protein_accession>
      <name>ZNF582 protein</name>
      <uniprot_id>A6QLH7</uniprot_id>
      <gene_name>ZNF582</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01794</protein_accession>
      <name>ZNF391 protein</name>
      <uniprot_id>A6QPV7</uniprot_id>
      <gene_name>ZNF391</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01796</protein_accession>
      <name>Putative uncharacterized protein</name>
      <uniprot_id>A6QNZ9</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01798</protein_accession>
      <name>ZNF689 protein</name>
      <uniprot_id>A4IFR4</uniprot_id>
      <gene_name>ZNF689</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01802</protein_accession>
      <name>ZNF502 protein</name>
      <uniprot_id>A6QR50</uniprot_id>
      <gene_name>ZNF502</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01803</protein_accession>
      <name>LOC100124497 protein</name>
      <uniprot_id>A6QPF7</uniprot_id>
      <gene_name>LOC100124497</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01805</protein_accession>
      <name>MGC152083 protein</name>
      <uniprot_id>A6QNU7</uniprot_id>
      <gene_name>MGC152083</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01806</protein_accession>
      <name>ZNF189 protein</name>
      <uniprot_id>A5PJY6</uniprot_id>
      <gene_name>ZNF189</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01808</protein_accession>
      <name>ZNF554 protein</name>
      <uniprot_id>A6QNX1</uniprot_id>
      <gene_name>ZNF554</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01809</protein_accession>
      <name>Zinc finger protein 264</name>
      <uniprot_id>A6MHW2</uniprot_id>
      <gene_name>Zfp264</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01886</protein_accession>
      <name>LOC100138545 protein</name>
      <uniprot_id>A6QQE3</uniprot_id>
      <gene_name>LOC100138545</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02020</protein_accession>
      <name>Calreticulin</name>
      <uniprot_id>P52193</uniprot_id>
      <gene_name>CALR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02046</protein_accession>
      <name>Calreticulin-3</name>
      <uniprot_id>Q2TBR8</uniprot_id>
      <gene_name>CALR3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02254</protein_accession>
      <name>SIRT6 protein</name>
      <uniprot_id>A5D7K6</uniprot_id>
      <gene_name>SIRT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02258</protein_accession>
      <name>Sirtuin-like protein 2</name>
      <uniprot_id>B2CZT3</uniprot_id>
      <gene_name>SIRT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02259</protein_accession>
      <name>SIRT2 protein</name>
      <uniprot_id>A6QP26</uniprot_id>
      <gene_name>SIRT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02298</protein_accession>
      <name>Zinc-finger protein X-linked</name>
      <uniprot_id>B5TQW5</uniprot_id>
      <gene_name>Zfx</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02299</protein_accession>
      <name>Sequestosome 1</name>
      <uniprot_id>A7E3V0</uniprot_id>
      <gene_name>SQSTM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02300</protein_accession>
      <name>ZNF514 protein</name>
      <uniprot_id>A8QQJ5</uniprot_id>
      <gene_name>ZNF514</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02301</protein_accession>
      <name>ZC3H7A protein</name>
      <uniprot_id>A7Z062</uniprot_id>
      <gene_name>ZC3H7A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02302</protein_accession>
      <name>ZFAND3 protein</name>
      <uniprot_id>A6QLV5</uniprot_id>
      <gene_name>ZFAND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02303</protein_accession>
      <name>ADP-ribosylation factor GTPase-activating protein 3</name>
      <uniprot_id>Q17R07</uniprot_id>
      <gene_name>ARFGAP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02304</protein_accession>
      <name>ZNF75A protein</name>
      <uniprot_id>A8E4M3</uniprot_id>
      <gene_name>ZNF75A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02305</protein_accession>
      <name>MMP27 protein</name>
      <uniprot_id>A5PJJ3</uniprot_id>
      <gene_name>MMP27</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02306</protein_accession>
      <name>ACAP1 protein</name>
      <uniprot_id>A6QQE2</uniprot_id>
      <gene_name>ACAP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02307</protein_accession>
      <name>Differentially expressed in FDCP 8 homolog</name>
      <uniprot_id>A5PJM7</uniprot_id>
      <gene_name>DEF8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02308</protein_accession>
      <name>Putative uncharacterized protein</name>
      <uniprot_id>A6QQC5</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02309</protein_accession>
      <name>TRAF4 protein</name>
      <uniprot_id>A7MBK6</uniprot_id>
      <gene_name>TRAF4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02310</protein_accession>
      <name>MDM2 protein</name>
      <uniprot_id>A5PJW5</uniprot_id>
      <gene_name>MDM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02311</protein_accession>
      <name>APOBEC3Z2</name>
      <uniprot_id>B7T154</uniprot_id>
      <gene_name>APOBEC3Z2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02312</protein_accession>
      <name>N-chimaerin</name>
      <uniprot_id>Q17QN0</uniprot_id>
      <gene_name>CHN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02313</protein_accession>
      <name>SH3RF2 protein</name>
      <uniprot_id>A4IFR5</uniprot_id>
      <gene_name>SH3RF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02314</protein_accession>
      <name>TRIM3 protein</name>
      <uniprot_id>A7MB36</uniprot_id>
      <gene_name>TRIM3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02315</protein_accession>
      <name>DMD protein</name>
      <uniprot_id>A8WFL6</uniprot_id>
      <gene_name>DMD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02316</protein_accession>
      <name>Tripartite motif-containing 37</name>
      <uniprot_id>A8WFQ1</uniprot_id>
      <gene_name>TRIM37</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02317</protein_accession>
      <name>ADAM3A protein</name>
      <uniprot_id>A5D7M5</uniprot_id>
      <gene_name>ADAM3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02318</protein_accession>
      <name>NR1I2 protein</name>
      <uniprot_id>A2VDU4</uniprot_id>
      <gene_name>NR1I2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02319</protein_accession>
      <name>BFAR protein</name>
      <uniprot_id>A5PJN7</uniprot_id>
      <gene_name>BFAR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02320</protein_accession>
      <name>Polycomb complex protein BMI-1</name>
      <uniprot_id>Q32KX7</uniprot_id>
      <gene_name>BMI1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02321</protein_accession>
      <name>Cysteine and histidine-rich protein 1</name>
      <uniprot_id>Q7YR89</uniprot_id>
      <gene_name>CYHR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02322</protein_accession>
      <name>ZBTB25 protein</name>
      <uniprot_id>B0JYK0</uniprot_id>
      <gene_name>ZBTB25</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02323</protein_accession>
      <name>ACAP3 protein</name>
      <uniprot_id>A4IFL7</uniprot_id>
      <gene_name>ACAP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02324</protein_accession>
      <name>100125581 protein</name>
      <uniprot_id>A6QQ06</uniprot_id>
      <gene_name>100125581</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02325</protein_accession>
      <name>RNF219 protein</name>
      <uniprot_id>A7Z060</uniprot_id>
      <gene_name>RNF219</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02326</protein_accession>
      <name>ZNF592 protein</name>
      <uniprot_id>A7MAY9</uniprot_id>
      <gene_name>ZNF592</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02327</protein_accession>
      <name>ZMYM2 protein</name>
      <uniprot_id>A6QLH9</uniprot_id>
      <gene_name>ZMYM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02328</protein_accession>
      <name>PRMT3 protein</name>
      <uniprot_id>A6QL80</uniprot_id>
      <gene_name>PRMT3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02329</protein_accession>
      <name>RNF2 protein</name>
      <uniprot_id>A6QLQ0</uniprot_id>
      <gene_name>RNF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02330</protein_accession>
      <name>HDAC6 protein</name>
      <uniprot_id>A5PJZ7</uniprot_id>
      <gene_name>HDAC6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02331</protein_accession>
      <name>CHN1 protein</name>
      <uniprot_id>A7Z037</uniprot_id>
      <gene_name>CHN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02332</protein_accession>
      <name>ZNF274 protein</name>
      <uniprot_id>A6QPT6</uniprot_id>
      <gene_name>ZNF274</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02333</protein_accession>
      <name>CpG-binding protein</name>
      <uniprot_id>Q5EA28</uniprot_id>
      <gene_name>CXXC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02334</protein_accession>
      <name>RNF145 protein</name>
      <uniprot_id>A6QQC8</uniprot_id>
      <gene_name>RNF145</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02335</protein_accession>
      <name>LOC525062 protein</name>
      <uniprot_id>A5D7I2</uniprot_id>
      <gene_name>LOC525062</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02336</protein_accession>
      <name>ZNF286A protein</name>
      <uniprot_id>A8WFL9</uniprot_id>
      <gene_name>ZNF286A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02337</protein_accession>
      <name>LHX1 protein</name>
      <uniprot_id>A7Z015</uniprot_id>
      <gene_name>LHX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02338</protein_accession>
      <name>RNF122 protein</name>
      <uniprot_id>A7MB42</uniprot_id>
      <gene_name>RNF122</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02339</protein_accession>
      <name>RNF220 protein</name>
      <uniprot_id>A6QP97</uniprot_id>
      <gene_name>RNF220</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02340</protein_accession>
      <name>PLEKHF2 protein</name>
      <uniprot_id>A4IFN8</uniprot_id>
      <gene_name>PLEKHF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02341</protein_accession>
      <name>FYVE, RhoGEF and PH domain containing 5</name>
      <uniprot_id>A1L566</uniprot_id>
      <gene_name>FGD5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02342</protein_accession>
      <name>ZBTB1 protein</name>
      <uniprot_id>A7E356</uniprot_id>
      <gene_name>ZBTB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02343</protein_accession>
      <name>Myelin transcription factor 1-like</name>
      <uniprot_id>A0JN68</uniprot_id>
      <gene_name>MYT1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02344</protein_accession>
      <name>ZFAND5 protein</name>
      <uniprot_id>A7MBA8</uniprot_id>
      <gene_name>ZFAND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02345</protein_accession>
      <name>D4, zinc and double PHD fingers family 2</name>
      <uniprot_id>A6QQS0</uniprot_id>
      <gene_name>DPF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02346</protein_accession>
      <name>MORC3 protein</name>
      <uniprot_id>A7E3B0</uniprot_id>
      <gene_name>MORC3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02347</protein_accession>
      <name>Zinc finger imprinted 3</name>
      <uniprot_id>A9P499</uniprot_id>
      <gene_name>Zim3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02348</protein_accession>
      <name>ZNF277 protein</name>
      <uniprot_id>A3KN09</uniprot_id>
      <gene_name>ZNF277</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02349</protein_accession>
      <name>CA13 protein</name>
      <uniprot_id>A7E338</uniprot_id>
      <gene_name>CA13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02350</protein_accession>
      <name>SMYD1 protein</name>
      <uniprot_id>A3KMV0</uniprot_id>
      <gene_name>SMYD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02351</protein_accession>
      <name>TRIM2 protein</name>
      <uniprot_id>A4IF63</uniprot_id>
      <gene_name>TRIM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02352</protein_accession>
      <name>CPZ protein</name>
      <uniprot_id>A3KN58</uniprot_id>
      <gene_name>CPZ</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02353</protein_accession>
      <name>USP3 protein</name>
      <uniprot_id>A6QNU1</uniprot_id>
      <gene_name>USP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02354</protein_accession>
      <name>NEIL1 protein</name>
      <uniprot_id>A6QQJ6</uniprot_id>
      <gene_name>NEIL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02355</protein_accession>
      <name>MLL5 protein</name>
      <uniprot_id>A2VE12</uniprot_id>
      <gene_name>MLL5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02356</protein_accession>
      <name>LOC616969 protein</name>
      <uniprot_id>A6QP67</uniprot_id>
      <gene_name>LOC616969</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02357</protein_accession>
      <name>VPS41 protein</name>
      <uniprot_id>A3KN15</uniprot_id>
      <gene_name>VPS41</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02358</protein_accession>
      <name>Cleavage and polyadenylation specificity factor subunit 4</name>
      <uniprot_id>O19137</uniprot_id>
      <gene_name>CPSF4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02359</protein_accession>
      <name>Sp1 transcription factor</name>
      <uniprot_id>A0JNC9</uniprot_id>
      <gene_name>SP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02360</protein_accession>
      <name>BLVRA protein</name>
      <uniprot_id>A5D7K0</uniprot_id>
      <gene_name>BLVRA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02361</protein_accession>
      <name>SP7 protein</name>
      <uniprot_id>A7MB06</uniprot_id>
      <gene_name>SP7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02362</protein_accession>
      <name>ZNF521 protein</name>
      <uniprot_id>A7Z030</uniprot_id>
      <gene_name>ZNF521</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02363</protein_accession>
      <name>LOC100137827 protein</name>
      <uniprot_id>A7E391</uniprot_id>
      <gene_name>LOC100137827</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02364</protein_accession>
      <name>ISL1 protein</name>
      <uniprot_id>A6H796</uniprot_id>
      <gene_name>ISL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02365</protein_accession>
      <name>GMIP protein</name>
      <uniprot_id>A4FV18</uniprot_id>
      <gene_name>GMIP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02366</protein_accession>
      <name>ZSWIM1 protein</name>
      <uniprot_id>A6QNK2</uniprot_id>
      <gene_name>ZSWIM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02367</protein_accession>
      <name>Transcription factor IIIB 50 kDa subunit</name>
      <uniprot_id>Q29S07</uniprot_id>
      <gene_name>BRF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02368</protein_accession>
      <name>ADH4 protein</name>
      <uniprot_id>A6QPF3</uniprot_id>
      <gene_name>ADH4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02369</protein_accession>
      <name>PXMP3 protein</name>
      <uniprot_id>A6QLK9</uniprot_id>
      <gene_name>PXMP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02370</protein_accession>
      <name>Enigma protein</name>
      <uniprot_id>A1L5A7</uniprot_id>
      <gene_name>PDLIM7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02371</protein_accession>
      <name>TRAIP protein</name>
      <uniprot_id>A6QQB7</uniprot_id>
      <gene_name>TRAIP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02372</protein_accession>
      <name>ZNF644 protein</name>
      <uniprot_id>A3KMW9</uniprot_id>
      <gene_name>ZNF644</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02373</protein_accession>
      <name>DNAJA4 protein</name>
      <uniprot_id>A7E312</uniprot_id>
      <gene_name>DNAJA4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02374</protein_accession>
      <name>ARFGAP2 protein</name>
      <uniprot_id>A6QR32</uniprot_id>
      <gene_name>ARFGAP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02375</protein_accession>
      <name>ERAP1 protein</name>
      <uniprot_id>A7MB81</uniprot_id>
      <gene_name>ERAP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02376</protein_accession>
      <name>TCF19 protein</name>
      <uniprot_id>A4IFF7</uniprot_id>
      <gene_name>TCF19</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02377</protein_accession>
      <name>KLF13 protein</name>
      <uniprot_id>A3KN57</uniprot_id>
      <gene_name>KLF13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02378</protein_accession>
      <name>DTX3 protein</name>
      <uniprot_id>A7Z074</uniprot_id>
      <gene_name>DTX3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02379</protein_accession>
      <name>APOBEC3Z3</name>
      <uniprot_id>B7T155</uniprot_id>
      <gene_name>APOBEC3Z3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02380</protein_accession>
      <name>GATAD2A protein</name>
      <uniprot_id>A7YY50</uniprot_id>
      <gene_name>GATAD2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02381</protein_accession>
      <name>COUP transcription factor 1</name>
      <uniprot_id>Q9TTR8</uniprot_id>
      <gene_name>NR2F1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02382</protein_accession>
      <name>ZNF133 protein</name>
      <uniprot_id>A8WFL5</uniprot_id>
      <gene_name>ZNF133</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02383</protein_accession>
      <name>RNF121 protein</name>
      <uniprot_id>A6QPD7</uniprot_id>
      <gene_name>RNF121</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02384</protein_accession>
      <name>MYLIP protein</name>
      <uniprot_id>A6QQD1</uniprot_id>
      <gene_name>MYLIP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02385</protein_accession>
      <name>KLF5 protein</name>
      <uniprot_id>A4IFB2</uniprot_id>
      <gene_name>KLF5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02386</protein_accession>
      <name>Zinc-finger protein Y-linked</name>
      <uniprot_id>B5TQY4</uniprot_id>
      <gene_name>Zfy</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02387</protein_accession>
      <name>PJA2 protein</name>
      <uniprot_id>A6QR43</uniprot_id>
      <gene_name>PJA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02388</protein_accession>
      <name>Activating transcription factor 2</name>
      <uniprot_id>A2VDL1</uniprot_id>
      <gene_name>ATF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02389</protein_accession>
      <name>MICALL2 protein</name>
      <uniprot_id>A6H735</uniprot_id>
      <gene_name>MICALL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02390</protein_accession>
      <name>Cysteine and histidine-rich domain-containing protein 1</name>
      <uniprot_id>Q29RL2</uniprot_id>
      <gene_name>CHORDC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02391</protein_accession>
      <name>Protein BUD31 homolog</name>
      <uniprot_id>Q2NKU3</uniprot_id>
      <gene_name>BUD31</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02392</protein_accession>
      <name>Transcription factor COE2</name>
      <uniprot_id>Q08DL5</uniprot_id>
      <gene_name>EBF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02393</protein_accession>
      <name>TRMT1 protein</name>
      <uniprot_id>A6QP09</uniprot_id>
      <gene_name>TRMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02394</protein_accession>
      <name>CPB1 protein</name>
      <uniprot_id>A7YWU8</uniprot_id>
      <gene_name>CPB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02395</protein_accession>
      <name>BARD1 protein</name>
      <uniprot_id>A5PJF0</uniprot_id>
      <gene_name>BARD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02396</protein_accession>
      <name>Doublesex- and mab-3-related transcription factor A2</name>
      <uniprot_id>A6QQ94</uniprot_id>
      <gene_name>DMRTA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02397</protein_accession>
      <name>FGD1 protein</name>
      <uniprot_id>A5D7I5</uniprot_id>
      <gene_name>FGD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02398</protein_accession>
      <name>LHX3</name>
      <uniprot_id>B8Q0B9</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02399</protein_accession>
      <name>DnaJ homolog subfamily A member 1</name>
      <uniprot_id>Q5E954</uniprot_id>
      <gene_name>DNAJA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02400</protein_accession>
      <name>ZFAND1 protein</name>
      <uniprot_id>A6QP88</uniprot_id>
      <gene_name>ZFAND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02401</protein_accession>
      <name>UHRF1 protein</name>
      <uniprot_id>A7E320</uniprot_id>
      <gene_name>UHRF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02402</protein_accession>
      <name>Cellular nucleic acid-binding protein</name>
      <uniprot_id>Q3T0Q6</uniprot_id>
      <gene_name>CNBP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02403</protein_accession>
      <name>Cytosolic carboxypeptidase-like protein 5</name>
      <uniprot_id>Q58CX9</uniprot_id>
      <gene_name>AGBL5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02404</protein_accession>
      <name>Zinc finger protein AEBP2</name>
      <uniprot_id>A4FV57</uniprot_id>
      <gene_name>AEBP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02405</protein_accession>
      <name>COUP transcription factor 2</name>
      <uniprot_id>Q9TTR7</uniprot_id>
      <gene_name>NR2F2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02406</protein_accession>
      <name>DNAJA4 protein</name>
      <uniprot_id>A8NJX6</uniprot_id>
      <gene_name>DNAJA4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02407</protein_accession>
      <name>ABLIM3 protein</name>
      <uniprot_id>A5PKK3</uniprot_id>
      <gene_name>ABLIM3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02408</protein_accession>
      <name>PYGO2 protein</name>
      <uniprot_id>A7E348</uniprot_id>
      <gene_name>PYGO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02409</protein_accession>
      <name>AKAP8 protein</name>
      <uniprot_id>A7MB37</uniprot_id>
      <gene_name>AKAP8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02410</protein_accession>
      <name>RNF130 protein</name>
      <uniprot_id>A5PJQ3</uniprot_id>
      <gene_name>RNF130</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02411</protein_accession>
      <name>LOC516032 protein</name>
      <uniprot_id>A0JNP8</uniprot_id>
      <gene_name>LOC516032</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02412</protein_accession>
      <name>RNF185 protein</name>
      <uniprot_id>A4IFC2</uniprot_id>
      <gene_name>RNF185</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02413</protein_accession>
      <name>UBR7 protein</name>
      <uniprot_id>A3KMX6</uniprot_id>
      <gene_name>UBR7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02414</protein_accession>
      <name>LOC514433 protein</name>
      <uniprot_id>A8KC74</uniprot_id>
      <gene_name>LOC514433</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02415</protein_accession>
      <name>ZNF34 protein</name>
      <uniprot_id>A8E4K3</uniprot_id>
      <gene_name>ZNF34</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02416</protein_accession>
      <name>TRMU protein</name>
      <uniprot_id>A3KN16</uniprot_id>
      <gene_name>TRMU</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02417</protein_accession>
      <name>ZZZ3 protein</name>
      <uniprot_id>A6QLC9</uniprot_id>
      <gene_name>ZZZ3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02418</protein_accession>
      <name>DZIP1 protein</name>
      <uniprot_id>A8QW11</uniprot_id>
      <gene_name>DZIP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02419</protein_accession>
      <name>RNF6 protein</name>
      <uniprot_id>A5D7H4</uniprot_id>
      <gene_name>RNF6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02420</protein_accession>
      <name>CPM protein</name>
      <uniprot_id>A7MBD9</uniprot_id>
      <gene_name>CPM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02421</protein_accession>
      <name>CHD4 protein</name>
      <uniprot_id>A8KC83</uniprot_id>
      <gene_name>CHD4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02422</protein_accession>
      <name>Zinc finger protein 12</name>
      <uniprot_id>A8KC86</uniprot_id>
      <gene_name>ZNF12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02423</protein_accession>
      <name>Retinoid X receptor, beta</name>
      <uniprot_id>A6H7I6</uniprot_id>
      <gene_name>RXRB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02424</protein_accession>
      <name>DPF1 protein</name>
      <uniprot_id>A2VEA5</uniprot_id>
      <gene_name>DPF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02425</protein_accession>
      <name>DCTD protein</name>
      <uniprot_id>A6QQC3</uniprot_id>
      <gene_name>DCTD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02426</protein_accession>
      <name>Zinc fingers and homeoboxes 1</name>
      <uniprot_id>A8KC64</uniprot_id>
      <gene_name>ZHX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02427</protein_accession>
      <name>Protein Churchill</name>
      <uniprot_id>Q2HJG7</uniprot_id>
      <gene_name>CHURC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02428</protein_accession>
      <name>RNF166 protein</name>
      <uniprot_id>A6H736</uniprot_id>
      <gene_name>RNF166</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02429</protein_accession>
      <name>ZNRF2 protein</name>
      <uniprot_id>A5PKM1</uniprot_id>
      <gene_name>ZNRF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02430</protein_accession>
      <name>Brother of regulator of imprinted sites</name>
      <uniprot_id>B2CML0</uniprot_id>
      <gene_name>BORIS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02431</protein_accession>
      <name>RNF111 protein</name>
      <uniprot_id>A6QLE0</uniprot_id>
      <gene_name>RNF111</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02432</protein_accession>
      <name>Pol protein</name>
      <uniprot_id>A8BDN6</uniprot_id>
      <gene_name>pol</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02433</protein_accession>
      <name>Melanophilin</name>
      <uniprot_id>A2VDU9</uniprot_id>
      <gene_name>MLPH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02434</protein_accession>
      <name>BRAP protein</name>
      <uniprot_id>A6H716</uniprot_id>
      <gene_name>BRAP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02435</protein_accession>
      <name>Gag protein</name>
      <uniprot_id>A8BDN3</uniprot_id>
      <gene_name>gag</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02436</protein_accession>
      <name>RNF5 protein</name>
      <uniprot_id>A4FUF7</uniprot_id>
      <gene_name>RNF5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02437</protein_accession>
      <name>LOC789074 protein</name>
      <uniprot_id>A8E4R0</uniprot_id>
      <gene_name>LOC789074</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02438</protein_accession>
      <name>SPG7 protein</name>
      <uniprot_id>A7E2Z6</uniprot_id>
      <gene_name>SPG7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02439</protein_accession>
      <name>ZFAND2A protein</name>
      <uniprot_id>A4IFV6</uniprot_id>
      <gene_name>ZFAND2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02440</protein_accession>
      <name>CIT protein</name>
      <uniprot_id>A7YVE7</uniprot_id>
      <gene_name>CIT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02441</protein_accession>
      <name>APOBEC3F</name>
      <uniprot_id>A0FDH2</uniprot_id>
      <gene_name>APOBEC3F</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02442</protein_accession>
      <name>UHRF2 protein</name>
      <uniprot_id>A6QNQ3</uniprot_id>
      <gene_name>UHRF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02443</protein_accession>
      <name>DNAJA1 protein</name>
      <uniprot_id>A6QM13</uniprot_id>
      <gene_name>DNAJA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02444</protein_accession>
      <name>CXXC-type zinc finger protein 5</name>
      <uniprot_id>Q32LB3</uniprot_id>
      <gene_name>CXXC5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02445</protein_accession>
      <name>Ankyrin repeat and MYND domain-containing protein 2</name>
      <uniprot_id>Q0VCS9</uniprot_id>
      <gene_name>ANKMY2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02446</protein_accession>
      <name>ZMYM6 protein</name>
      <uniprot_id>A6QP33</uniprot_id>
      <gene_name>ZMYM6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02447</protein_accession>
      <name>ZNF444 protein</name>
      <uniprot_id>A7Z091</uniprot_id>
      <gene_name>ZNF444</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02448</protein_accession>
      <name>Tripartite motif-containing 11</name>
      <uniprot_id>A0JN74</uniprot_id>
      <gene_name>TRIM11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02449</protein_accession>
      <name>TRIM40 protein</name>
      <uniprot_id>A6QLL6</uniprot_id>
      <gene_name>TRIM40</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02450</protein_accession>
      <name>MAN2C1 protein</name>
      <uniprot_id>A8YXY9</uniprot_id>
      <gene_name>MAN2C1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02451</protein_accession>
      <name>ABLIM1 protein</name>
      <uniprot_id>A6QR39</uniprot_id>
      <gene_name>ABLIM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02452</protein_accession>
      <name>ADAM33 protein</name>
      <uniprot_id>A6QPR2</uniprot_id>
      <gene_name>ADAM33</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02453</protein_accession>
      <name>APOBEC3Z1</name>
      <uniprot_id>B7T153</uniprot_id>
      <gene_name>APOBEC3Z1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02454</protein_accession>
      <name>Protein ariadne-1 homolog</name>
      <uniprot_id>A2VEA3</uniprot_id>
      <gene_name>ARIH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02455</protein_accession>
      <name>RNPEP protein</name>
      <uniprot_id>A4FV56</uniprot_id>
      <gene_name>RNPEP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02456</protein_accession>
      <name>EWSR1 protein</name>
      <uniprot_id>A8E651</uniprot_id>
      <gene_name>EWSR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02457</protein_accession>
      <name>LMO7 protein</name>
      <uniprot_id>A8E4L8</uniprot_id>
      <gene_name>LMO7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02458</protein_accession>
      <name>MARCH7 protein</name>
      <uniprot_id>A6QR47</uniprot_id>
      <gene_name>07-Mar</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02459</protein_accession>
      <name>Ring finger protein 18</name>
      <uniprot_id>A9Q1J6</uniprot_id>
      <gene_name>RNF18</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02460</protein_accession>
      <name>Zinc finger, C3HC type 1</name>
      <uniprot_id>A5D9C3</uniprot_id>
      <gene_name>ZC3HC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02461</protein_accession>
      <name>ZNF740 protein</name>
      <uniprot_id>A7YY68</uniprot_id>
      <gene_name>ZNF740</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02462</protein_accession>
      <name>RING1 protein</name>
      <uniprot_id>A8E4N5</uniprot_id>
      <gene_name>RING1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02463</protein_accession>
      <name>RNF12 protein</name>
      <uniprot_id>A5PKC6</uniprot_id>
      <gene_name>RNF12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02464</protein_accession>
      <name>PIAS4 protein</name>
      <uniprot_id>A4FV15</uniprot_id>
      <gene_name>PIAS4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02465</protein_accession>
      <name>RNF145 protein</name>
      <uniprot_id>A6QLT6</uniprot_id>
      <gene_name>RNF145</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02466</protein_accession>
      <name>Cysteine and glycine-rich protein 3</name>
      <uniprot_id>Q4U0T9</uniprot_id>
      <gene_name>CSRP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02467</protein_accession>
      <name>Ring finger protein 14</name>
      <uniprot_id>A2VDU5</uniprot_id>
      <gene_name>RNF14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02468</protein_accession>
      <name>Y-linked zinc finger protein</name>
      <uniprot_id>A1XCK6</uniprot_id>
      <gene_name>ZFY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02469</protein_accession>
      <name>RAR-related orphan receptor C</name>
      <uniprot_id>A3QU33</uniprot_id>
      <gene_name>RORC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02470</protein_accession>
      <name>PR domain zinc finger protein 9</name>
      <uniprot_id>A3RLY6</uniprot_id>
      <gene_name>PRDM9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02471</protein_accession>
      <name>Cysteine and glycine-rich protein 2</name>
      <uniprot_id>Q32LE9</uniprot_id>
      <gene_name>CSRP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02472</protein_accession>
      <name>ZNF547 protein</name>
      <uniprot_id>A7YY23</uniprot_id>
      <gene_name>ZNF547</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02473</protein_accession>
      <name>IARS protein</name>
      <uniprot_id>A7MBC5</uniprot_id>
      <gene_name>IARS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02474</protein_accession>
      <name>CPXM1 protein</name>
      <uniprot_id>A3KN30</uniprot_id>
      <gene_name>CPXM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02475</protein_accession>
      <name>PLEKHF1 protein</name>
      <uniprot_id>A2VE19</uniprot_id>
      <gene_name>PLEKHF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02476</protein_accession>
      <name>LOC514433 protein</name>
      <uniprot_id>A5PKL0</uniprot_id>
      <gene_name>LOC514433</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02477</protein_accession>
      <name>ZFAND2B protein</name>
      <uniprot_id>A6H743</uniprot_id>
      <gene_name>ZFAND2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02478</protein_accession>
      <name>RAR-related orphan receptor C</name>
      <uniprot_id>A3QU31</uniprot_id>
      <gene_name>RORC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02479</protein_accession>
      <name>FBXO5 protein</name>
      <uniprot_id>A2VEA6</uniprot_id>
      <gene_name>FBXO5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02480</protein_accession>
      <name>Sec23 (S. cerevisiae) homolog B</name>
      <uniprot_id>A5D958</uniprot_id>
      <gene_name>SEC23B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02481</protein_accession>
      <name>PDZ and LIM domain 1</name>
      <uniprot_id>A6H7E3</uniprot_id>
      <gene_name>PDLIM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02482</protein_accession>
      <name>Zinc binding alcohol dehydrogenase, domain containing 1</name>
      <uniprot_id>A7E3P5</uniprot_id>
      <gene_name>ZADH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02483</protein_accession>
      <name>Cysteine-rich protein 1</name>
      <uniprot_id>Q56K04</uniprot_id>
      <gene_name>CRIP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02484</protein_accession>
      <name>ZNF295 protein</name>
      <uniprot_id>A2VDQ3</uniprot_id>
      <gene_name>ZNF295</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02485</protein_accession>
      <name>USP39 protein</name>
      <uniprot_id>A6QQX8</uniprot_id>
      <gene_name>USP39</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02486</protein_accession>
      <name>CA8 protein</name>
      <uniprot_id>A4IFV2</uniprot_id>
      <gene_name>CA8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02487</protein_accession>
      <name>ARHGEF2 protein</name>
      <uniprot_id>A6H6Z8</uniprot_id>
      <gene_name>ARHGEF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02488</protein_accession>
      <name>Anaphase-promoting complex subunit 11</name>
      <uniprot_id>Q3ZCF6</uniprot_id>
      <gene_name>ANAPC11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02489</protein_accession>
      <name>TRAF5 protein</name>
      <uniprot_id>A7YWC7</uniprot_id>
      <gene_name>TRAF5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02490</protein_accession>
      <name>SYVN1 protein</name>
      <uniprot_id>A6QQN0</uniprot_id>
      <gene_name>SYVN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02491</protein_accession>
      <name>Zinc-finger protein Y-linked</name>
      <uniprot_id>B5TQX8</uniprot_id>
      <gene_name>Zfy</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02492</protein_accession>
      <name>ADP-ribosylation factor GTPase-activating protein 2</name>
      <uniprot_id>A1L520</uniprot_id>
      <gene_name>ARFGAP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02493</protein_accession>
      <name>KLF4 protein</name>
      <uniprot_id>A7YWE2</uniprot_id>
      <gene_name>KLF4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02494</protein_accession>
      <name>Arf-GAP domain and FG repeats-containing protein 1</name>
      <uniprot_id>Q2TA45</uniprot_id>
      <gene_name>AGFG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02495</protein_accession>
      <name>HNF4G protein</name>
      <uniprot_id>A7E311</uniprot_id>
      <gene_name>HNF4G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02496</protein_accession>
      <name>RSPRY1 protein</name>
      <uniprot_id>A4IFG8</uniprot_id>
      <gene_name>RSPRY1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02497</protein_accession>
      <name>ZSCAN2 protein</name>
      <uniprot_id>A6QPD1</uniprot_id>
      <gene_name>ZSCAN2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02498</protein_accession>
      <name>RFWD2 protein</name>
      <uniprot_id>A2VE77</uniprot_id>
      <gene_name>RFWD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02499</protein_accession>
      <name>Baculoviral IAP repeat-containing protein 5</name>
      <uniprot_id>Q6J1J1</uniprot_id>
      <gene_name>BIRC5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02500</protein_accession>
      <name>TRIM25 protein</name>
      <uniprot_id>A6QLA8</uniprot_id>
      <gene_name>TRIM25</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02501</protein_accession>
      <name>DnaJ homolog subfamily A member 2</name>
      <uniprot_id>Q2HJ94</uniprot_id>
      <gene_name>DNAJA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02502</protein_accession>
      <name>Ankyrin repeat and zinc finger domain-containing protein 1</name>
      <uniprot_id>Q58CQ5</uniprot_id>
      <gene_name>ANKZF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02503</protein_accession>
      <name>ZRANB2 protein</name>
      <uniprot_id>A7YWH2</uniprot_id>
      <gene_name>ZRANB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02504</protein_accession>
      <name>GLI1 protein</name>
      <uniprot_id>A6H727</uniprot_id>
      <gene_name>GLI1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02505</protein_accession>
      <name>Doublesex- and mab-3-related transcription factor C2</name>
      <uniprot_id>Q32LE6</uniprot_id>
      <gene_name>DMRTC2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02506</protein_accession>
      <name>NRAP protein</name>
      <uniprot_id>A5D7L9</uniprot_id>
      <gene_name>NRAP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02507</protein_accession>
      <name>CBLC protein</name>
      <uniprot_id>A6QPZ5</uniprot_id>
      <gene_name>CBLC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02508</protein_accession>
      <name>LNX1 protein</name>
      <uniprot_id>A4IFA2</uniprot_id>
      <gene_name>LNX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02509</protein_accession>
      <name>SCEL protein</name>
      <uniprot_id>A6QLJ6</uniprot_id>
      <gene_name>SCEL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02510</protein_accession>
      <name>ZNF713 protein</name>
      <uniprot_id>A8SM77</uniprot_id>
      <gene_name>ZNF713</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02511</protein_accession>
      <name>PRICKLE1 protein</name>
      <uniprot_id>A5D7T1</uniprot_id>
      <gene_name>PRICKLE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02512</protein_accession>
      <name>ADAM23 protein</name>
      <uniprot_id>A4FUX7</uniprot_id>
      <gene_name>ADAM23</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02513</protein_accession>
      <name>PPARD protein</name>
      <uniprot_id>A4IFL4</uniprot_id>
      <gene_name>PPARD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02514</protein_accession>
      <name>Cysteine-rich protein 2</name>
      <uniprot_id>Q0VFX8</uniprot_id>
      <gene_name>CRIP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02515</protein_accession>
      <name>Cysteine and glycine-rich protein 1</name>
      <uniprot_id>Q3MHY1</uniprot_id>
      <gene_name>CSRP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02516</protein_accession>
      <name>NBR1 protein</name>
      <uniprot_id>A6QQS9</uniprot_id>
      <gene_name>NBR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02517</protein_accession>
      <name>YY1 protein</name>
      <uniprot_id>A5D7T6</uniprot_id>
      <gene_name>YY1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02518</protein_accession>
      <name>Hmm291030</name>
      <uniprot_id>A0A2V3</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02519</protein_accession>
      <name>DnaJ homolog subfamily C member 24</name>
      <uniprot_id>Q0VBY7</uniprot_id>
      <gene_name>DNAJC24</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02520</protein_accession>
      <name>ZDHHC13 protein</name>
      <uniprot_id>A6QNQ5</uniprot_id>
      <gene_name>ZDHHC13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02521</protein_accession>
      <name>Microtubule associated monoxygenase, calponin and LIM domain containing 1</name>
      <uniprot_id>A2VDL7</uniprot_id>
      <gene_name>MICAL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02522</protein_accession>
      <name>RNF31 protein</name>
      <uniprot_id>A6QNU0</uniprot_id>
      <gene_name>RNF31</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02523</protein_accession>
      <name>RNF135 protein</name>
      <uniprot_id>A6H717</uniprot_id>
      <gene_name>RNF135</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02524</protein_accession>
      <name>DnaJ (Hsp40) homolog, subfamily A, member 3</name>
      <uniprot_id>A1A4J9</uniprot_id>
      <gene_name>DNAJA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02525</protein_accession>
      <name>RCHY1 protein</name>
      <uniprot_id>A4IFE2</uniprot_id>
      <gene_name>RCHY1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02526</protein_accession>
      <name>Zinc finger RAD18 domain-containing protein C1orf124 homolog</name>
      <uniprot_id>A5D979</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02527</protein_accession>
      <name>CDC42BPA protein</name>
      <uniprot_id>A5PKC1</uniprot_id>
      <gene_name>CDC42BPA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02528</protein_accession>
      <name>ADNP2 protein</name>
      <uniprot_id>A6QLD7</uniprot_id>
      <gene_name>ADNP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02529</protein_accession>
      <name>ZNF192 protein</name>
      <uniprot_id>A6QQG2</uniprot_id>
      <gene_name>ZNF192</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02530</protein_accession>
      <name>MYST4 protein</name>
      <uniprot_id>A7E390</uniprot_id>
      <gene_name>MYST4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02531</protein_accession>
      <name>APOBEC3B protein</name>
      <uniprot_id>A8QIC6</uniprot_id>
      <gene_name>APOBEC3B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02532</protein_accession>
      <name>Splicing factor 1</name>
      <uniprot_id>A2VDM7</uniprot_id>
      <gene_name>SF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02533</protein_accession>
      <name>CHD4 protein</name>
      <uniprot_id>A7E3C8</uniprot_id>
      <gene_name>CHD4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02534</protein_accession>
      <name>Rabphilin 3A homolog (Mouse)</name>
      <uniprot_id>A6QR65</uniprot_id>
      <gene_name>RPH3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02535</protein_accession>
      <name>MGC142792 protein</name>
      <uniprot_id>A4FV50</uniprot_id>
      <gene_name>MGC142792</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02536</protein_accession>
      <name>Nuclear transition protein 2</name>
      <uniprot_id>B3LF31</uniprot_id>
      <gene_name>Tnp2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02537</protein_accession>
      <name>LHX5 protein</name>
      <uniprot_id>A6QQY6</uniprot_id>
      <gene_name>LHX5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02538</protein_accession>
      <name>ASAP3 protein</name>
      <uniprot_id>A3KMY6</uniprot_id>
      <gene_name>ASAP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:52 UTC</creation_date>
  <update_date>2020-04-16 20:38:38 UTC</update_date>
  <accession>BMDB0001304</accession>
  <secondary_accessions>
    <accession>BMDB01304</accession>
  </secondary_accessions>
  <name>QH2</name>
  <description/>
  <synonyms>
    <synonym>CoQH2</synonym>
    <synonym>Coenzymes QH2</synonym>
    <synonym>Reduced ubiquinone</synonym>
    <synonym>Ubiquinol</synonym>
    <synonym>Ubiquinone-1</synonym>
    <synonym>Coenzyme Q10, reduced</synonym>
    <synonym>Ubiquinol-10</synonym>
  </synonyms>
  <chemical_formula>(C5H8)nC14H20O4</chemical_formula>
  <average_molecular_weight/>
  <monisotopic_moleculate_weight/>
  <iupac_name/>
  <traditional_iupac/>
  <cas_registry_number>56275-39-9</cas_registry_number>
  <smiles>COC1=C(O)C(C)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1OC</smiles>
  <inchi>InChI=1S/C19H28O4/c1-12(2)8-7-9-13(3)10-11-15-14(4)16(20)18(22-5)19(23-6)17(15)21/h8,10,20-21H,7,9,11H2,1-6H3/b13-10+</inchi>
  <inchikey>RNUCUWWMTTWKAH-JLHYYAGUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as ubiquinols. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methylbenzene-1,4-diol moiety to which an isoprenyl group is attached at ring position 2(or 6).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Quinone and hydroquinone lipids</sub_class>
    <direct_parent>Ubiquinols</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aromatic monoterpenoids</alternative_parent>
      <alternative_parent>Dimethoxybenzenes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroquinones</alternative_parent>
      <alternative_parent>Meta cresols</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>Monocyclic monoterpenoids</alternative_parent>
      <alternative_parent>Ortho cresols</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Toluenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aromatic monoterpenoid</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Dimethoxybenzene</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroquinone</substituent>
      <substituent>M-cresol</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Monocyclic monoterpenoid</substituent>
      <substituent>Monoterpenoid</substituent>
      <substituent>O-cresol</substituent>
      <substituent>O-dimethoxybenzene</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Toluene</substituent>
      <substituent>Ubiquinol skeleton</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=C(O)C(C)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1OC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>(C5H8)nC14H20O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O4/c1-12(2)8-7-9-13(3)10-11-15-14(4)16(20)18(22-5)19(23-6)17(15)21/h8,10,20-21H,7,9,11H2,1-6H3/b13-10+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RNUCUWWMTTWKAH-JLHYYAGUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>63141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1307410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1307411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1307412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1421920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1421921</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1421922</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022543</foodb_id>
  <kegg_id>C00390</kegg_id>
  <chemspider_id>4444052</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>5280344</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Coenzyme Q10</wikipedia_id>
  <metlin_id>6146</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00097</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial</name>
      <uniprot_id>P42026</uniprot_id>
      <gene_name>NDUFS7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00099</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial</name>
      <uniprot_id>P17694</uniprot_id>
      <gene_name>NDUFS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00262</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IX89</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00263</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>P03887</uniprot_id>
      <gene_name>MT-ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00264</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q45LU7</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00265</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q6JTG2</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00266</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IXE1</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00267</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>B1NZU0</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00268</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45M50</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00269</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MI0</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00270</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q3L5H4</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00271</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45LG6</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00272</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1NZ26</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00273</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] flavoprotein 2, mitochondrial</name>
      <uniprot_id>P04394</uniprot_id>
      <gene_name>NDUFV2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00274</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q8HBP4</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00275</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0B8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00276</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>B1P0I6</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00277</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q6JTH0</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00278</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q45MJ0</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00279</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q85EA2</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00280</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q7JAL5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00281</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q8HC63</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00282</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q6QTH1</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00283</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q45MC5</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00284</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>Q7JAS5</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00285</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q8HC24</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00286</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0J6</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00287</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4L</name>
      <uniprot_id>Q3L5T0</uniprot_id>
      <gene_name>ND4L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00288</protein_accession>
      <name>NADH dehydrogenase subunit 4</name>
      <uniprot_id>C5IX88</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00289</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q3L5J7</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00290</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>Q85UJ0</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00291</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>B1P078</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00292</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>B1P0N6</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00293</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>Q7JAS9</uniprot_id>
      <gene_name>ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00294</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P092</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00295</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q45MX4</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00296</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>P03924</uniprot_id>
      <gene_name>MT-ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00297</protein_accession>
      <name>Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial</name>
      <uniprot_id>Q3T189</uniprot_id>
      <gene_name>SDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00298</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0N5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00299</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q6JTD6</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00300</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45LK5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00301</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>B1NZ92</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00302</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>A4ZI01</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00303</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>P03920</uniprot_id>
      <gene_name>MT-ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00304</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q85E90</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00305</protein_accession>
      <name>NADH-ubiquinone oxidoreductase 75 kDa subunit, mitochondrial</name>
      <uniprot_id>P15690</uniprot_id>
      <gene_name>NDUFS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00306</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q45M46</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00307</protein_accession>
      <name>NADH dehydrogenase subunit 4</name>
      <uniprot_id>C5IX62</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00308</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q45MC9</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00309</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45LU6</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00310</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>B1P044</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00311</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q45LV6</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00312</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>B1P0M6</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00313</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0M2</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00314</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q6QTH0</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00315</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q85BD6</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00316</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q6JTD5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00317</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4L</name>
      <uniprot_id>Q7JAS8</uniprot_id>
      <gene_name>ND4L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00318</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IX37</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00319</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>P03910</uniprot_id>
      <gene_name>MT-ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00320</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q45M85</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00321</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P027</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00322</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q8HAW7</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00323</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q6JTE4</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00324</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>Q45LU9</uniprot_id>
      <gene_name>ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00325</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MC8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00326</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4L</name>
      <uniprot_id>P03902</uniprot_id>
      <gene_name>MT-ND4L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00327</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45LV9</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00328</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q85BS9</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00329</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial</name>
      <uniprot_id>P23709</uniprot_id>
      <gene_name>NDUFS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00330</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q7JAT5</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00331</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>B1NZ38</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00332</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MW0</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00333</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q8HQD4</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00334</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q7JAS7</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00335</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MP5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00336</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>P03898</uniprot_id>
      <gene_name>MT-ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00337</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>P03892</uniprot_id>
      <gene_name>MT-ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00338</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q8HBM0</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00339</protein_accession>
      <name>Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial</name>
      <uniprot_id>P31039</uniprot_id>
      <gene_name>SDHA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00340</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>B1P0L9</uniprot_id>
      <gene_name>ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00341</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q7JAT6</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00342</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MA2</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00343</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1NZY8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00344</protein_accession>
      <name>Electron transfer flavoprotein-ubiquinone oxidoreductase, mitochondrial</name>
      <uniprot_id>Q2KIG0</uniprot_id>
      <gene_name>ETFDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00345</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 8, mitochondrial</name>
      <uniprot_id>P42028</uniprot_id>
      <gene_name>NDUFS8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00346</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q45MY2</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00347</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IXC8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00348</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial</name>
      <uniprot_id>P25708</uniprot_id>
      <gene_name>NDUFV1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00349</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1NZB7</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00350</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>Q85UI9</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00351</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>Q6QTG4</uniprot_id>
      <gene_name>ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00352</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q45LS1</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:53 UTC</creation_date>
  <update_date>2020-03-13 16:27:09 UTC</update_date>
  <accession>BMDB0001308</accession>
  <secondary_accessions>
    <accession>BMDB01308</accession>
  </secondary_accessions>
  <name>5'-Phosphoribosyl-N-formylglycinamide</name>
  <description/>
  <synonyms>
    <synonym>N-Formyl-gar</synonym>
    <synonym>N-Formylglycinamide ribonucleotide</synonym>
    <synonym>N2-Formyl-N1-(5-phospho-D-ribosyl)glycinamide</synonym>
    <synonym>5'-p-Ribosyl-N-formylglycineamide</synonym>
    <synonym>5'-Phosphoribosyl-formylglycinamide</synonym>
    <synonym>5'-Phosphoribosyl-N-formylglycineamide</synonym>
    <synonym>5-Phosphoribosyl-N-formalglycineamide</synonym>
    <synonym>FGAR</synonym>
    <synonym>N(2)-Formyl-N(1)-(5-phospho-D-ribosyl)glycinamide</synonym>
    <synonym>Formylglycinamide ribonucleotide</synonym>
    <synonym>Formylglycineamideribotide</synonym>
    <synonym>Phosphoribosyl-N-formylglycineamide</synonym>
    <synonym>2-(Formylamino)-N-(5-O-phosphono-beta-D-ribofuranosyl)acetamide</synonym>
    <synonym>2-(Formylamino)-N-(5-O-phosphono-β-D-ribofuranosyl)acetamide</synonym>
    <synonym>5'-Phosphoribosyl-N-formylglycinamide</synonym>
    <synonym>5’-Phosphoribosyl-N-formylglycinamide</synonym>
    <synonym>Formylglycinamide ribotide</synonym>
    <synonym>Phosphoribosylformylglycinamide</synonym>
    <synonym>alpha-N-Formylglycinamide ribonucleotide</synonym>
    <synonym>α-N-Formylglycinamide ribonucleotide</synonym>
  </synonyms>
  <chemical_formula>C8H15N2O9P</chemical_formula>
  <average_molecular_weight>314.1865</average_molecular_weight>
  <monisotopic_moleculate_weight>314.0515166</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoacetamido)oxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoacetamido)oxolan-2-yl]methoxyphosphonic acid</traditional_iupac>
  <cas_registry_number>349-34-8</cas_registry_number>
  <smiles>O[C@H]1[C@@H](O)[C@H](NC(=O)CNC=O)O[C@@H]1COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C8H15N2O9P/c11-3-9-1-5(12)10-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H,9,11)(H,10,12)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1</inchi>
  <inchikey>VDXLUNDMVKSKHO-XVFCMESISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glycinamide ribonucleotides. Glycinamide ribonucleotides are compounds in which the amide N atom of glycineamide is linked to the C-1 of a ribosyl (or deoxyribosyl) moiety. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Glycinamide ribonucleotides</class>
    <sub_class/>
    <direct_parent>Glycinamide ribonucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-formyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycinamide-ribonucleotide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-formyl-alpha amino acid or derivatives</substituent>
      <substituent>N-formyl-alpha-amino acid</substituent>
      <substituent>N-substituted-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-glycosyl compound</external_descriptor>
      <external_descriptor>amido monocarboxylic acid amide</external_descriptor>
      <external_descriptor>ribose monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-formamidoacetamido)oxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>314.1865</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>314.0515166</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1[C@@H](O)[C@H](NC(=O)CNC=O)O[C@@H]1COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H15N2O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H15N2O9P/c11-3-9-1-5(12)10-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H,9,11)(H,10,12)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VDXLUNDMVKSKHO-XVFCMESISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>174.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35344</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB030552</foodb_id>
  <kegg_id>C04376</kegg_id>
  <chemspider_id>115687</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>130805</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <knapsack_id>C00019642</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>43690</bigg_id>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:55 UTC</creation_date>
  <update_date>2020-03-13 16:27:10 UTC</update_date>
  <accession>BMDB0001309</accession>
  <secondary_accessions>
    <accession>BMDB01309</accession>
  </secondary_accessions>
  <name>m-Chlorohippuric acid</name>
  <description/>
  <synonyms>
    <synonym>m-Chlorohippate</synonym>
    <synonym>m-Chlorohippic acid</synonym>
    <synonym>3-Chlorohippuric acid</synonym>
    <synonym>3-Chlorohippate</synonym>
    <synonym>3-Chlorohippic acid</synonym>
    <synonym>(3-Chloro-benzoylamino)-acetic acid</synonym>
    <synonym>(3-Chlorobenzoylamino)acetic acid</synonym>
    <synonym>m-Chlorohippurate</synonym>
    <synonym>N-(3-Chlorobenzoyl)glycine</synonym>
    <synonym>2-{[(3-chlorophenyl)(hydroxy)methylidene]amino}acetate</synonym>
  </synonyms>
  <chemical_formula>C9H8ClNO3</chemical_formula>
  <average_molecular_weight>213.618</average_molecular_weight>
  <monisotopic_moleculate_weight>213.019270834</monisotopic_moleculate_weight>
  <iupac_name>2-[(3-chlorophenyl)formamido]acetic acid</iupac_name>
  <traditional_iupac>m-chlorohippuric acid</traditional_iupac>
  <cas_registry_number>57728-59-3</cas_registry_number>
  <smiles>OC(=O)CNC(=O)C1=CC(Cl)=CC=C1</smiles>
  <inchi>InChI=1S/C9H8ClNO3/c10-7-3-1-2-6(4-7)9(14)11-5-8(12)13/h1-4H,5H2,(H,11,14)(H,12,13)</inchi>
  <inchikey>ICYUIIJXZHPESK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>Hippuric acids</direct_parent>
    <alternative_parents>
      <alternative_parent>3-halobenzoic acids and derivatives</alternative_parent>
      <alternative_parent>Aryl chlorides</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Chlorobenzenes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-halobenzoic acid or derivatives</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl chloride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Chlorobenzene</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Halobenzoic acid or derivatives</substituent>
      <substituent>Hippuric acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(3-chlorophenyl)formamido]acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>213.618</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>213.019270834</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CNC(=O)C1=CC(Cl)=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H8ClNO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H8ClNO3/c10-7-3-1-2-6(4-7)9(14)11-5-8(12)13/h1-4H,5H2,(H,11,14)(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ICYUIIJXZHPESK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>362331</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022545</foodb_id>
  <kegg_id/>
  <chemspider_id>435</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>448</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>613377</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6149</metlin_id>
  <synthesis_reference>Taboada, J.; Pavon, A.; Cetina, R.  Synthesis of substituted hippuric acids and ir spectra of the intermediate amidoalcohols.    Revista de la Sociedad Quimica de Mexico  (1975),  19(1),  10-12.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:56 UTC</creation_date>
  <update_date>2020-03-13 16:27:10 UTC</update_date>
  <accession>BMDB0001310</accession>
  <secondary_accessions>
    <accession>BMDB01310</accession>
  </secondary_accessions>
  <name>D-Alanine</name>
  <description/>
  <synonyms>
    <synonym>(2R)-2-Aminopropanoic acid</synonym>
    <synonym>(R)-2-Aminopropanoic acid</synonym>
    <synonym>(R)-Alanine</synonym>
    <synonym>D-2-Aminopropionic acid</synonym>
    <synonym>D-Ala</synonym>
    <synonym>D-Alanin</synonym>
    <synonym>D-alpha-Alanine</synonym>
    <synonym>D-alpha-Aminopropionic acid</synonym>
    <synonym>DAL</synonym>
    <synonym>(2R)-2-Aminopropanoate</synonym>
    <synonym>(R)-2-Aminopropanoate</synonym>
    <synonym>D-2-Aminopropionate</synonym>
    <synonym>D-a-Alanine</synonym>
    <synonym>D-Α-alanine</synonym>
    <synonym>D-a-Aminopropionate</synonym>
    <synonym>D-a-Aminopropionic acid</synonym>
    <synonym>D-alpha-Aminopropionate</synonym>
    <synonym>D-Α-aminopropionate</synonym>
    <synonym>D-Α-aminopropionic acid</synonym>
    <synonym>Alanine</synonym>
    <synonym>D(-)-a -Alanine</synonym>
    <synonym>D(-)-alpha-Alanine</synonym>
    <synonym>D-(-)-Alanine</synonym>
    <synonym>(2R)-2-Aminopropionic acid</synonym>
    <synonym>(R)-2-Aminopropionic acid</synonym>
    <synonym>D(-)-Α-alanine</synonym>
  </synonyms>
  <chemical_formula>C3H7NO2</chemical_formula>
  <average_molecular_weight>89.0932</average_molecular_weight>
  <monisotopic_moleculate_weight>89.047678473</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-aminopropanoic acid</iupac_name>
  <traditional_iupac>D-alanine</traditional_iupac>
  <cas_registry_number>338-69-2</cas_registry_number>
  <smiles>C[C@@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1</inchi>
  <inchikey>QNAYBMKLOCPYGJ-UWTATZPHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alanine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>D-alpha-amino acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alanine or derivatives</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>D-alpha-amino acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D-alpha-amino acid</external_descriptor>
      <external_descriptor>Other amino acids</external_descriptor>
      <external_descriptor>alanine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>292 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>165.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.912</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-aminopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>89.0932</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>89.047678473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QNAYBMKLOCPYGJ-UWTATZPHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>20.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1620</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445525</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022546</foodb_id>
  <kegg_id>C00133</kegg_id>
  <chemspider_id>64234</chemspider_id>
  <drugbank_id>DB01786</drugbank_id>
  <pubchem_compound_id>71080</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15570</chebi_id>
  <knapsack_id>C00019654</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>D-ALANINE</meta_cyc_id>
  <bigg_id>33977</bigg_id>
  <wikipedia_id>Alanine</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:57 UTC</creation_date>
  <update_date>2020-04-16 20:40:49 UTC</update_date>
  <accession>BMDB0001311</accession>
  <secondary_accessions>
    <accession>BMDB01311</accession>
  </secondary_accessions>
  <name>D-Lactic acid</name>
  <description>L-Lactic acid, also known as D-lactate or D-milchsaeure, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. L-Lactic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. L-Lactic acid exists in all living species, ranging from bacteria to humans. L-Lactic acid participates in a number of enzymatic reactions, within cattle. In particular, L-Lactic acid can be converted into pyruvic acid; which is catalyzed by the enzyme L-lactate dehydrogenase. In addition, L-Lactic acid can be converted into L-lactic acid through the action of the enzyme monocarboxylate transporter. In cattle, L-lactic acid is involved in the metabolic pathway called cancer (via the Warburg effect). L-Lactic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(-)-Lactic acid</synonym>
    <synonym>(R)-(-)-Lactic acid</synonym>
    <synonym>D-2-Hydroxypropanoic acid</synonym>
    <synonym>D-2-Hydroxypropionic acid</synonym>
    <synonym>D-Milchsaeure</synonym>
    <synonym>LACTIC ACID</synonym>
    <synonym>D-Lactate</synonym>
    <synonym>(-)-Lactate</synonym>
    <synonym>(R)-(-)-Lactate</synonym>
    <synonym>D-2-Hydroxypropanoate</synonym>
    <synonym>D-2-Hydroxypropionate</synonym>
    <synonym>LACTate</synonym>
    <synonym>L-Lactate</synonym>
    <synonym>(R)-2-Hydroxypropanoate</synonym>
    <synonym>(R)-2-Hydroxypropanoic acid</synonym>
    <synonym>(R)-2-Hydroxypropionate</synonym>
    <synonym>(R)-2-Hydroxypropionic acid</synonym>
    <synonym>(R)-a-Hydroxypropionate</synonym>
    <synonym>(R)-a-Hydroxypropionic acid</synonym>
    <synonym>(R)-alpha-Hydroxypropionate</synonym>
    <synonym>(R)-alpha-Hydroxypropionic acid</synonym>
    <synonym>(R)-Lactate</synonym>
    <synonym>(R)-Lactic acid</synonym>
    <synonym>D-(-)-Lactate</synonym>
    <synonym>D-(-)-Lactic acid</synonym>
    <synonym>delta-(-)-Lactate</synonym>
    <synonym>delta-(-)-Lactic acid</synonym>
    <synonym>delta-2-Hydroxypropanoate</synonym>
    <synonym>delta-2-Hydroxypropanoic acid</synonym>
    <synonym>delta-2-Hydroxypropionate</synonym>
    <synonym>delta-2-Hydroxypropionic acid</synonym>
    <synonym>delta-Lactate</synonym>
    <synonym>delta-Lactic acid</synonym>
    <synonym>DLA</synonym>
    <synonym>L-(+)-Lactate</synonym>
    <synonym>Propel</synonym>
    <synonym>Tisulac</synonym>
    <synonym>2 Hydroxypropanoic acid</synonym>
    <synonym>2 Hydroxypropionic acid</synonym>
    <synonym>2-Hydroxypropanoic acid</synonym>
    <synonym>Ammonium lactate</synonym>
    <synonym>L Lactic acid</synonym>
    <synonym>2-Hydroxypropionic acid</synonym>
    <synonym>Sarcolactic acid</synonym>
    <synonym>D Lactic acid</synonym>
    <synonym>Lactate, ammonium</synonym>
    <synonym>L-Lactic acid</synonym>
    <synonym>D-Lactic acid</synonym>
  </synonyms>
  <chemical_formula>C3H6O3</chemical_formula>
  <average_molecular_weight>90.0779</average_molecular_weight>
  <monisotopic_moleculate_weight>90.031694058</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-hydroxypropanoic acid</iupac_name>
  <traditional_iupac>D-lactic acid</traditional_iupac>
  <cas_registry_number>10326-41-7</cas_registry_number>
  <smiles>C[C@@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1</inchi>
  <inchikey>JVTAAEKCZFNVCJ-UWTATZPHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Alpha hydroxy acids and derivatives</sub_class>
    <direct_parent>Alpha hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxypropanoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>52.8 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-hydroxypropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>90.0779</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>90.031694058</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H6O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JVTAAEKCZFNVCJ-UWTATZPHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>18.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvaldehyde Degradation</name>
      <smpdb_id>SMP0087210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438632</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>3560 +/- 270</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Ewaschuk JB, Naylor JM, Barabash WA, Zello GA: High-performance liquid chromatographic assay of lactic, pyruvic and acetic acids and lactic acid stereoisomers in calf feces, rumen fluid and urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Jun 15;805(2):347-51. doi: 10.1016/j.jchromb.2004.03.004.</reference_text>
          <pubmed_id>15135111</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB030146</foodb_id>
  <kegg_id>C00256</kegg_id>
  <chemspider_id>55423</chemspider_id>
  <drugbank_id>DB03066</drugbank_id>
  <pubchem_compound_id>61503</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>42111</chebi_id>
  <knapsack_id>C00019549</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>34414</bigg_id>
  <wikipedia_id>Lactic_acid</wikipedia_id>
  <metlin_id>6150</metlin_id>
  <synthesis_reference>Hsieh, Chun Lung; Houng, Jer Yiing.  Preparation of D-lactic acid from D,L-lactic acid ester using wheat germ or pancreatic lipase.    U.S.  (1997),     5 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:58 UTC</creation_date>
  <update_date>2020-03-13 16:27:11 UTC</update_date>
  <accession>BMDB0001312</accession>
  <secondary_accessions>
    <accession>BMDB01312</accession>
  </secondary_accessions>
  <name>Diadenosine diphosphate</name>
  <description/>
  <synonyms>
    <synonym>Diadenosine diphosphoric acid</synonym>
    <synonym>Diadenosine pyrophosphate</synonym>
    <synonym>Diadenosine-5',5'-pyrophosphate</synonym>
    <synonym>p(1),p(2)-Di(adenosine 5'-)diphosphate</synonym>
    <synonym>p(1),p(2)-Diadenosine-5'-pyrophosphate</synonym>
    <synonym>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4R,5S)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinate</synonym>
    <synonym>AppA</synonym>
    <synonym>p(1),p(2)- Di(adenosine 5'-)diphosphate</synonym>
  </synonyms>
  <chemical_formula>C20H26N10O13P2</chemical_formula>
  <average_molecular_weight>676.4272</average_molecular_weight>
  <monisotopic_moleculate_weight>676.115603992</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4R,5S)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(2R,3S,4R,5S)-5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid</traditional_iupac>
  <cas_registry_number>14938-28-4</cas_registry_number>
  <smiles>NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)O[C@@H]4[C@@H](CO)O[C@@H]([C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@@H](O)[C@H]3O)C2=NC=N1</smiles>
  <inchi>InChI=1S/C20H26N10O13P2/c21-15-9-17(25-3-23-15)29(5-27-9)19-12(33)11(32)8(41-19)2-39-44(35,36)43-45(37,38)42-14-7(1-31)40-20(13(14)34)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20+/m1/s1</inchi>
  <inchikey>FHISWBUCBBVWGG-SNESVTBZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (3'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (3'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(3'-&gt;5')-dinucleotides and analogues</class>
    <sub_class>(3'-&gt;5')-dinucleotides</sub_class>
    <direct_parent>(3'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(3'-&gt;5')-dinucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4R,5S)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>676.4272</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>676.115603992</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)O[C@@H]4[C@@H](CO)O[C@@H]([C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@@H](O)[C@H]3O)C2=NC=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H26N10O13P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H26N10O13P2/c21-15-9-17(25-3-23-15)29(5-27-9)19-12(33)11(32)8(41-19)2-39-44(35,36)43-45(37,38)42-14-7(1-31)40-20(13(14)34)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FHISWBUCBBVWGG-SNESVTBZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>340.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>144.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>58.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364818</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022547</foodb_id>
  <kegg_id/>
  <chemspider_id>163689</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>188326</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:43:59 UTC</creation_date>
  <update_date>2020-03-13 16:27:12 UTC</update_date>
  <accession>BMDB0001313</accession>
  <secondary_accessions>
    <accession>BMDB01313</accession>
  </secondary_accessions>
  <name>D-Myo-inositol 4-phosphate</name>
  <description/>
  <synonyms>
    <synonym>D-Myo-inositol 4-phosphoric acid</synonym>
    <synonym>Myoinositol 4-phosphate</synonym>
    <synonym>Inositol 4-monophosphate</synonym>
    <synonym>Inositol 4-phosphate</synonym>
  </synonyms>
  <chemical_formula>C6H13O9P</chemical_formula>
  <average_molecular_weight>260.1358</average_molecular_weight>
  <monisotopic_moleculate_weight>260.029718526</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H]C1(O)[C@]([H])(O)[C@]([H])(O)C([H])(OP(O)(O)=O)[C@]([H])(O)[C@@]1([H])O</smiles>
  <inchi>InChI=1S/C6H13O9P/c7-1-2(8)4(10)6(5(11)3(1)9)15-16(12,13)14/h1-11H,(H2,12,13,14)/t1?,2-,3-,4-,5+,6?/m0/s1</inchi>
  <inchikey>INAPMGSXUVUWAF-GFWFORPUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Inositol phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclohexanols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Cyclohexanol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Inositol phosphate</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>260.1358</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>260.029718526</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]C1(O)[C@]([H])(O)[C@]([H])(O)C([H])(OP(O)(O)=O)[C@]([H])(O)[C@@]1([H])O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O9P/c7-1-2(8)4(10)6(5(11)3(1)9)15-16(12,13)14/h1-11H,(H2,12,13,14)/t1?,2-,3-,4-,5+,6?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>INAPMGSXUVUWAF-GFWFORPUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>167.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34567</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id>440043</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Billington, David C.; Baker, Raymond; Kulagowski, Janusz J.; Mawer, Ian M.  Synthesis of myo-inositol 1-phosphate and 4-phosphate, and of their individual enantiomers.    Journal of the Chemical Society, Chemical Communications  (1987),   (4),  314-16.  </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00461</protein_accession>
      <name>Inositol polyphosphate 1-phosphatase</name>
      <uniprot_id>P21327</uniprot_id>
      <gene_name>INPP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:00 UTC</creation_date>
  <update_date>2020-04-16 20:36:46 UTC</update_date>
  <accession>BMDB0001314</accession>
  <secondary_accessions>
    <accession>BMDB01314</accession>
  </secondary_accessions>
  <name>Cyclic GMP</name>
  <description>Cyclic GMP, also known as CGMP or GMP, cyclic, belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group. Cyclic GMP is possibly soluble (in water) and a moderately basic compound (based on its pKa). Cyclic GMP exists in all living species, ranging from bacteria to humans. In cattle, cyclic GMP is involved in the metabolic pathway called ion channels and their functional role in vascular endothelium pathway.</description>
  <synonyms>
    <synonym>CGMP</synonym>
    <synonym>Guanosine 3',5'-cyclic monophosphate</synonym>
    <synonym>Guanosine 3',5'-cyclic phosphate</synonym>
    <synonym>Guanosine cyclic monophosphate</synonym>
    <synonym>Guanosine 3',5'-cyclic monophosphoric acid</synonym>
    <synonym>Guanosine 3',5'-cyclic phosphoric acid</synonym>
    <synonym>Guanosine cyclic monophosphoric acid</synonym>
    <synonym>3',5'-Cyclic GMP</synonym>
    <synonym>3',5'-Guanosine</synonym>
    <synonym>3',5'-Guanosine monophosphate</synonym>
    <synonym>Cyclic 3',5'-guanosine monophosphate</synonym>
    <synonym>Cyclic guanosine 3',5'-monophosphate</synonym>
    <synonym>Cyclic-GMP</synonym>
    <synonym>Guanosine 3',5'-cyclic-monophosphate</synonym>
    <synonym>Guanosine 3',5'-monophosphate</synonym>
    <synonym>Guanosine cyclic-monophosphate</synonym>
    <synonym>Guanosine-cyclic-phosphoric-acid</synonym>
    <synonym>Cyclic 3',5'-monophosphate, guanosine</synonym>
    <synonym>GMP, Cyclic</synonym>
    <synonym>Guanosine cyclic-3',5'-monophosphate</synonym>
    <synonym>monoPhosphate, guanosine cyclic</synonym>
    <synonym>3',5'-monoPhosphate, guanosine cyclic</synonym>
    <synonym>Cyclic-3',5'-monophosphate, guanosine</synonym>
    <synonym>Guanosine cyclic 3',5'-monophosphate</synonym>
    <synonym>Guanosine cyclic 3,5 monophosphate</synonym>
    <synonym>Cyclic monophosphate, guanosine</synonym>
    <synonym>Guanosine cyclic 3',5' monophosphate</synonym>
  </synonyms>
  <chemical_formula>C10H12N5O7P</chemical_formula>
  <average_molecular_weight>345.2053</average_molecular_weight>
  <monisotopic_moleculate_weight>345.047434275</monisotopic_moleculate_weight>
  <iupac_name>9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one</iupac_name>
  <traditional_iupac>cyclic-GMP</traditional_iupac>
  <cas_registry_number>7665-99-8</cas_registry_number>
  <smiles>NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1</smiles>
  <inchi>InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1</inchi>
  <inchikey>ZOOGRGPOEVQQDX-UUOKFMHZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Cyclic purine nucleotides</sub_class>
    <direct_parent>3',5'-cyclic purine nucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic phosphoric acids and derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3',5'-cyclic purine ribonucleotide</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3',5'-Cyclic nuclcleotides</external_descriptor>
      <external_descriptor>3',5'-cyclic purine nucleotide</external_descriptor>
      <external_descriptor>guanyl ribonucleotide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>345.2053</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>345.047434275</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N5O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZOOGRGPOEVQQDX-UUOKFMHZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>170.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>71.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ion Channels and Their Functional Role in Vascular Endothelium</name>
      <smpdb_id>SMP0108207</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449670</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00942</kegg_id>
  <chemspider_id>22734</chemspider_id>
  <pubchem_compound_id>24316</pubchem_compound_id>
  <drugbank_id>DB02315</drugbank_id>
  <foodb_id>FDB030764</foodb_id>
  <pdbe_id/>
  <chebi_id>16356</chebi_id>
  <knapsack_id>C00019673</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>1485267</bigg_id>
  <wikipedia_id>Cyclic guanosine monophosphate</wikipedia_id>
  <metlin_id>6152</metlin_id>
  <synthesis_reference>Sekhar, Konjeti R.; Grondin, Pascal; Francis, Sharron H.; Corbin, Jackie D.  Design and synthesis of xanthines and cyclic GMP analogs as potent inhibitors of PDE5.    Phosphodiesterase Inhibitors  (1996),     135-146.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00029</protein_accession>
      <name>Guanylate cyclase soluble subunit beta-1</name>
      <uniprot_id>P16068</uniprot_id>
      <gene_name>GUCY1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00429</protein_accession>
      <name>Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'</name>
      <uniprot_id>P16586</uniprot_id>
      <gene_name>PDE6C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00430</protein_accession>
      <name>Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha</name>
      <uniprot_id>P11541</uniprot_id>
      <gene_name>PDE6A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00431</protein_accession>
      <name>Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit beta</name>
      <uniprot_id>P23439</uniprot_id>
      <gene_name>PDE6B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00433</protein_accession>
      <name>Retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma</name>
      <uniprot_id>P22571</uniprot_id>
      <gene_name>PDE6H</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00434</protein_accession>
      <name>cGMP-specific 3',5'-cyclic phosphodiesterase</name>
      <uniprot_id>Q28156</uniprot_id>
      <gene_name>PDE5A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00435</protein_accession>
      <name>Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma</name>
      <uniprot_id>P04972</uniprot_id>
      <gene_name>PDE6G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00436</protein_accession>
      <name>Atrial natriuretic peptide receptor B</name>
      <uniprot_id>P46197</uniprot_id>
      <gene_name>NPR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01109</protein_accession>
      <name>Retinal guanylyl cyclase 2</name>
      <uniprot_id>O02740</uniprot_id>
      <gene_name>GUCY2F</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01117</protein_accession>
      <name>Guanylate cyclase soluble subunit alpha-1</name>
      <uniprot_id>P19687</uniprot_id>
      <gene_name>GUCY1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01122</protein_accession>
      <name>Guanylate cyclase</name>
      <uniprot_id>O77690</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01125</protein_accession>
      <name>Retinal guanylyl cyclase 1</name>
      <uniprot_id>P55203</uniprot_id>
      <gene_name>GUCY2D</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01179</protein_accession>
      <name>cGMP-dependent protein kinase 1, alpha isozyme</name>
      <uniprot_id>P00516</uniprot_id>
      <gene_name>PRKG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01196</protein_accession>
      <name>cGMP-dependent protein kinase 1, beta isozyme</name>
      <uniprot_id>P21136</uniprot_id>
      <gene_name>PRKG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01256</protein_accession>
      <name>cGMP-dependent 3',5'-cyclic phosphodiesterase</name>
      <uniprot_id>P14099</uniprot_id>
      <gene_name>PDE2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01337</protein_accession>
      <name>Inositol 1,4,5-trisphosphate receptor type 1</name>
      <uniprot_id>Q9TU34</uniprot_id>
      <gene_name>ITPR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02679</protein_accession>
      <name>cGMP-gated cation channel alpha-1</name>
      <uniprot_id>Q00194</uniprot_id>
      <gene_name>CNGA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02680</protein_accession>
      <name>Cyclic nucleotide-gated cation channel alpha-3</name>
      <uniprot_id>Q29441</uniprot_id>
      <gene_name>CNGA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:01 UTC</creation_date>
  <update_date>2020-04-15 22:10:05 UTC</update_date>
  <accession>BMDB0001315</accession>
  <secondary_accessions>
    <accession>BMDB01315</accession>
  </secondary_accessions>
  <name>Phosphorus</name>
  <description>Phosphine, also known as phosphor or 15P, belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'. Phosphine exists as a solid, possibly soluble (in water), and possibly neutral molecule. Phosphine exists in all eukaryotes, ranging from yeast to humans. Phosphine is a potentially toxic compound. Phosphine has been found to be associated with several diseases known as cerebrotendinous xanthomatosis and fructose intolerance, hereditary; also phosphine has been linked to the inborn metabolic disorders including glycerol intolerance syndrome.</description>
  <synonyms>
    <synonym>15P</synonym>
    <synonym>Fosforo</synonym>
    <synonym>P</synonym>
    <synonym>Phosphor</synonym>
    <synonym>Phosphore</synonym>
    <synonym>Hittorf'S phosphorus</synonym>
    <synonym>Phosphorous</synonym>
    <synonym>Phosphorus-30</synonym>
    <synonym>Red phosphorus</synonym>
    <synonym>Violet phosphorus</synonym>
    <synonym>White phosphorus</synonym>
    <synonym>Phosphorus 31</synonym>
    <synonym>Phosphorus, red</synonym>
    <synonym>Phosphorus-31</synonym>
    <synonym>Phosphorus, white</synonym>
    <synonym>Phosphorus, black</synonym>
    <synonym>Yellow phosphorus</synonym>
    <synonym>Phosphorus, yellow</synonym>
    <synonym>Black phosphorus</synonym>
    <synonym>Phosphorus</synonym>
  </synonyms>
  <chemical_formula>P</chemical_formula>
  <average_molecular_weight>30.9738</average_molecular_weight>
  <monisotopic_moleculate_weight>30.973761512</monisotopic_moleculate_weight>
  <iupac_name>phosphanylidyne</iupac_name>
  <traditional_iupac>phosphanylidyne</traditional_iupac>
  <cas_registry_number>7723-14-0</cas_registry_number>
  <smiles>[P]</smiles>
  <inchi>InChI=1S/P</inchi>
  <inchikey>OAICVXFJPJFONN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Homogeneous other non-metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous other non-metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous other non metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>monoatomic phosphorus</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>phosphanylidyne</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>30.9738</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>30.973761512</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[P]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OAICVXFJPJFONN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>5.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181085</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>2760</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Dacos Chemistry Analyzer in Hereford cows</comment>
      <references>
        <reference>
          <reference_text>Early RJ, McBride BW, Ball RO: Growth and metabolism in somatotropin-treated steers: I. Growth, serum chemistry and carcass weights. J Anim Sci. 1990 Dec;68(12):4134-43. doi: 10.2527/1990.68124134x.</reference_text>
          <pubmed_id>2286555</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1480 +/- 20 </concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>McAdam PA, O'Dell GD: Mineral profile of blood plasma of lactating dairy cows. J Dairy Sci. 1982 Jul;65(7):1219-26. doi: 10.3168/jds.S0022-0302(82)82333-3.</reference_text>
          <pubmed_id>7108016</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1129.989-1992.00859</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Briggs modification of the Bell-Doisy method (1922)</comment>
      <references>
        <reference>
          <reference_text>Arthur K. Anderson, Howard E. Gayley, Avery D. Pratt. Studies on the Chemical Composition of Bovine Blood. J. Dairy Science (1930) 13(4):336-348   doi: 10.3168/jds.S0022-0302(30)93530-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1298+/-164</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>32820+/-6825</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>21915+/-3094</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>34994.82 +/- 530.33</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Total phosphorus in Jersey cows milk with 6.05% fat</comment>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27139.27 +/- 1425.10</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Total phosphorus in Holstein-Friesian cows milk with 3.51% fat</comment>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35190.13 +/- 550.92</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Total phosphorus in Jersey cows milk with 5.93% fat</comment>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19000 - 23000</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: The minerals of milk. Reprod Nutr Dev. 2005 Jul-Aug;45(4):473-83. doi: 10.1051/rnd:2005030.</reference_text>
          <pubmed_id>16045895</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29.414 +/- 530.332</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29.414 +/- 550.921</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12725.0159 +/- 450.0318</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12915.0293 +/- 1008.0123</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12965.327 +/- 374.438</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13535.955 +/- 582.0999</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14223.945 +/- 779.761</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14473.669 +/- 352.378</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15495.506 +/- 484.152</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16420.571 +/- 366.202</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18769.560 +/- 476.210</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20521.154 +/- 458.268</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>26260.971 +/- 822.705</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27139.269 +/- 1425.101</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28460.538 +/- 684.460</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
          <pubmed_id>23040012</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>19781 +/- 478</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25132 +/- 1669</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>22155 +/- 2514</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>21317 +/- 549</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27354.872 - 29707.979</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23000 - 52800</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk, range over first 90 day in lactation</comment>
      <references>
        <reference>
          <reference_text>Tsioulpas A, Grandison AS, Lewis MJ: Changes in physical properties of bovine milk from the colostrum period to early lactation. J Dairy Sci. 2007 Nov;90(11):5012-7. doi: 10.3168/jds.2007-0192.</reference_text>
          <pubmed_id>17954740</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27943.149</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28531.426</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28531.426</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27943.149</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29707.979</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>25295.903</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32649.363</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>35002.471</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29413.841</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27943.149</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32943.502</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30590.395</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29707.979</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29707.979</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28237.287</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28237.287</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27354.872</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32943.502</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29413.841</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32943.502</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27060.734</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27060.734</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28531.426</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28472.598</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28531.426</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>24707.626</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>24707.626</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>26178.318</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27354.872</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27354.872</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>26884.251 - 115684.637</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>9202 +/- 64</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by ICP-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>12395+/-1908</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>21818+/-2594</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>15602+/-2618</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C06262</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB013348</foodb_id>
  <chemspider_id>4575369</chemspider_id>
  <pubchem_compound_id>5462309</pubchem_compound_id>
  <chebi_id>28659</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Phosphorus</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Gaucheron F: The minerals of milk. Reprod Nutr Dev. 2005 Jul-Aug;45(4):473-83. doi: 10.1051/rnd:2005030.</reference_text>
      <pubmed_id>16045895</pubmed_id>
    </reference>
    <reference>
      <reference_text>Tsioulpas A, Grandison AS, Lewis MJ: Changes in physical properties of bovine milk from the colostrum period to early lactation. J Dairy Sci. 2007 Nov;90(11):5012-7. doi: 10.3168/jds.2007-0192.</reference_text>
      <pubmed_id>17954740</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen HB, Poulsen NA, Andersen KK, Hammershoj M, Poulsen HD, Larsen LB: Distinct composition of bovine milk from Jersey and Holstein-Friesian cows with good, poor, or noncoagulation properties as reflected in protein genetic variants and isoforms. J Dairy Sci. 2012 Dec;95(12):6905-17. doi: 10.3168/jds.2012-5675. Epub 2012 Oct 3.</reference_text>
      <pubmed_id>23040012</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
      <pubmed_id>22081685</pubmed_id>
    </reference>
    <reference>
      <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:02 UTC</creation_date>
  <update_date>2020-04-15 22:00:25 UTC</update_date>
  <accession>BMDB0001316</accession>
  <secondary_accessions>
    <accession>BMDB01316</accession>
  </secondary_accessions>
  <name>6-Phosphogluconic acid</name>
  <description>6-Phosphogluconic acid, also known as 6-phospho-D-gluconate or gluconate 6-phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. 6-Phosphogluconic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Phosphogluconic acid exists in all living species, ranging from bacteria to humans. 6-Phosphogluconic acid can be biosynthesized from gluconolactone and water; which is catalyzed by the enzyme 6-phosphogluconolactonase. In cattle, 6-phosphogluconic acid is involved in the metabolic pathway called the pentose phosphate pathway.</description>
  <synonyms>
    <synonym>6-Phospho-D-gluconate</synonym>
    <synonym>6-Phospho-D-gluconic acid</synonym>
    <synonym>6-Phosphogluconate</synonym>
    <synonym>6-O-Phosphono-D-gluconic acid</synonym>
    <synonym>6-p-Gluconate</synonym>
    <synonym>D-Gluconic acid 6-(dihydrogen phosphate)</synonym>
    <synonym>D-Gluconic acid 6-phosphate</synonym>
    <synonym>Gluconic acid-6-phosphate</synonym>
    <synonym>Gluconate 6-phosphate</synonym>
  </synonyms>
  <chemical_formula>C6H13O10P</chemical_formula>
  <average_molecular_weight>276.1352</average_molecular_weight>
  <monisotopic_moleculate_weight>276.024633148</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)hexanoic acid</iupac_name>
  <traditional_iupac>6-phosphogluconic acid</traditional_iupac>
  <cas_registry_number>921-62-0</cas_registry_number>
  <smiles>O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H13O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-5,7-10H,1H2,(H,11,12)(H2,13,14,15)/t2-,3-,4+,5-/m1/s1</inchi>
  <inchikey>BIRSGZKFKXLSJQ-SQOUGZDYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharide phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Medium-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sugar acids and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Gluconic_acid</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>gluconic acid phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)hexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>276.1352</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>276.024633148</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O10P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-5,7-10H,1H2,(H,11,12)(H2,13,14,15)/t2-,3-,4+,5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BIRSGZKFKXLSJQ-SQOUGZDYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>184.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>49.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1921</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438875</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438876</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00345</kegg_id>
  <chemspider_id>82615</chemspider_id>
  <pubchem_compound_id>91493</pubchem_compound_id>
  <drugbank_id>DB02076</drugbank_id>
  <foodb_id>FDB030611</foodb_id>
  <pdbe_id/>
  <chebi_id>48928</chebi_id>
  <knapsack_id>C00007481</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD-2961</meta_cyc_id>
  <bigg_id>34686</bigg_id>
  <wikipedia_id>6-Phosphogluconic_acid</wikipedia_id>
  <metlin_id>367</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00356</protein_accession>
      <name>6-phosphogluconate dehydrogenase, decarboxylating</name>
      <uniprot_id>Q3ZCI4</uniprot_id>
      <gene_name>PGD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:04 UTC</creation_date>
  <update_date>2020-03-13 16:27:14 UTC</update_date>
  <accession>BMDB0001318</accession>
  <secondary_accessions>
    <accession>BMDB01318</accession>
  </secondary_accessions>
  <name>4-Methylpentanal</name>
  <description>4-Methylpentanal, also known as isohexanal or isocaproaldehyde, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. 4-Methylpentanal is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Methylpentanal participates in a number of enzymatic reactions, within cattle. In particular, Pregnenolone and 4-methylpentanal can be biosynthesized from 20a,22b-dihydroxycholesterol; which is catalyzed by the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In addition, 17a-Hydroxypregnenolone and 4-methylpentanal can be biosynthesized from 17a,20a-dihydroxycholesterol through the action of the enzyme cholesterol side-chain cleavage enzyme, mitochondrial. In cattle, 4-methylpentanal is involved in the metabolic pathway called the steroidogenesis pathway.</description>
  <synonyms>
    <synonym>4-Methyl valeraldehyde</synonym>
    <synonym>Isocaproaldehyde</synonym>
    <synonym>Isohexanal</synonym>
    <synonym>4-Methyl-valeraldehyde</synonym>
    <synonym>4-Methylvaleraldehyde</synonym>
    <synonym>Isocaproaldehyde: 4-methyl-pentanal</synonym>
    <synonym>Isohexana</synonym>
  </synonyms>
  <chemical_formula>C6H12O</chemical_formula>
  <average_molecular_weight>100.1589</average_molecular_weight>
  <monisotopic_moleculate_weight>100.088815006</monisotopic_moleculate_weight>
  <iupac_name>4-methylpentanal</iupac_name>
  <traditional_iupac>isocaproaldehyde</traditional_iupac>
  <cas_registry_number>1119-16-0</cas_registry_number>
  <smiles>CC(C)CCC=O</smiles>
  <inchi>InChI=1S/C6H12O/c1-6(2)4-3-5-7/h5-6H,3-4H2,1-2H3</inchi>
  <inchikey>JGEGJYXHCFUMJF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Alpha-hydrogen aldehydes</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydrogen aldehyde</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>alpha-CH2-containing aldehyde</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-methylpentanal</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>100.1589</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>100.088815006</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CCC=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O/c1-6(2)4-3-5-7/h5-6H,3-4H2,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JGEGJYXHCFUMJF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroidogenesis</name>
      <smpdb_id>SMP0087238</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353814</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02373</kegg_id>
  <chemspider_id>126</chemspider_id>
  <pubchem_compound_id>129</pubchem_compound_id>
  <drugbank_id/>
  <foodb_id>FDB022551</foodb_id>
  <pdbe_id/>
  <chebi_id>17998</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>39716</bigg_id>
  <wikipedia_id/>
  <metlin_id>6155</metlin_id>
  <synthesis_reference>Matsuura K; Deyashiki Y; Bunai Y; Ohya I; Hara A  Aldose reductase is a major reductase for isocaproaldehyde, a product of side-chain cleavage of cholesterol, in human and animal adrenal glands.    Archives of biochemistry and biophysics  (1996),  328(2),  265-71.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00053</protein_accession>
      <name>Cholesterol side-chain cleavage enzyme, mitochondrial</name>
      <uniprot_id>P00189</uniprot_id>
      <gene_name>CYP11A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:05 UTC</creation_date>
  <update_date>2020-03-13 16:27:14 UTC</update_date>
  <accession>BMDB0001319</accession>
  <secondary_accessions>
    <accession>BMDB01319</accession>
  </secondary_accessions>
  <name>Pyridoxine 5'-phosphate</name>
  <description>Pyridoxine 5'-phosphate, also known as pyridoxine 5'-phosphate or Pyridoxine 5'-phosphate, belongs to the class of organic compounds known as pyridoxine 5'-phosphates. These are pyridoxines that carry a phosphate group at the 5-position. Pyridoxine 5'-phosphate is possibly soluble (in water) and a very strong basic compound (based on its pKa). Pyridoxine 5'-phosphate exists in all living species, ranging from bacteria to humans. Pyridoxine 5'-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Pyridoxine 5'-phosphate can be biosynthesized from pyridoxine; which is mediated by the enzyme pyridoxal kinase. In addition, Pyridoxine 5'-phosphate can be converted into pyridoxal 5'-phosphate; which is catalyzed by the enzyme pyridoxine 5'-phosphate oxidase. In cattle, pyridoxine 5'-phosphate is involved in the metabolic pathway called the vitamin B6 metabolism pathway.</description>
  <synonyms>
    <synonym>Pyridoxine 5'-(dihydrogen phosphate)</synonym>
    <synonym>Pyridoxine 5-phosphate</synonym>
    <synonym>Pyridoxine phosphate</synonym>
    <synonym>PYRIDOXINE-5'-phosphATE</synonym>
    <synonym>Pyridoxol 5'-phosphate</synonym>
    <synonym>Pyridoxol 5-phosphate</synonym>
    <synonym>Pyridoxyl-5-phosphate</synonym>
    <synonym>Pyridoxine 5'-(dihydrogen phosphoric acid)</synonym>
    <synonym>Pyridoxine 5-phosphoric acid</synonym>
    <synonym>Pyridoxine phosphoric acid</synonym>
    <synonym>PYRIDOXINE-5'-phosphoric acid</synonym>
    <synonym>Pyridoxol 5'-phosphoric acid</synonym>
    <synonym>Pyridoxol 5-phosphoric acid</synonym>
    <synonym>Pyridoxyl-5-phosphoric acid</synonym>
    <synonym>Pyridoxine 5'-phosphoric acid</synonym>
    <synonym>5-Hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridylmethyl dihydrogen phosphate</synonym>
    <synonym>5-Hydroxy-6-methyl-3,4-pyridinedimethanol alpha( 3)-(dihydrogen phosphate)</synonym>
    <synonym>Pyridoxine-5P</synonym>
    <synonym>Pyridoxine-p</synonym>
    <synonym>Pyridoxine-phosphate</synonym>
    <synonym>Pyridoxine 5-phosphate hydrochloride</synonym>
    <synonym>5-Phosphopyridoxine</synonym>
  </synonyms>
  <chemical_formula>C8H12NO6P</chemical_formula>
  <average_molecular_weight>249.1577</average_molecular_weight>
  <monisotopic_moleculate_weight>249.040223633</monisotopic_moleculate_weight>
  <iupac_name>{[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>pyridoxine-5'-phosphate</traditional_iupac>
  <cas_registry_number>447-05-2</cas_registry_number>
  <smiles>CC1=NC=C(COP(O)(O)=O)C(CO)=C1O</smiles>
  <inchi>InChI=1S/C8H12NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2,10-11H,3-4H2,1H3,(H2,12,13,14)</inchi>
  <inchikey>WHOMFKWHIQZTHY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridoxine-5'-phosphates. These are pyridoxines that carry a phosphate group at the 5-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyridoxines</sub_class>
    <direct_parent>Pyridoxine-5'-phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyridines</alternative_parent>
      <alternative_parent>Methylpyridines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyridine</substituent>
      <substituent>Methylpyridine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyridoxine-5'-phosphate</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>vitamin B6 phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>249.1577</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>249.040223633</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=NC=C(COP(O)(O)=O)C(CO)=C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H12NO6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H12NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2,10-11H,3-4H2,1H3,(H2,12,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WHOMFKWHIQZTHY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>120.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Vitamin B6 Metabolism</name>
      <smpdb_id>SMP0087240</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31015</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00627</kegg_id>
  <chemspider_id>1026</chemspider_id>
  <pubchem_compound_id>1055</pubchem_compound_id>
  <drugbank_id>DB02209</drugbank_id>
  <foodb_id>FDB031140</foodb_id>
  <pdbe_id/>
  <chebi_id>28803</chebi_id>
  <knapsack_id>C00007505</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>35527</bigg_id>
  <wikipedia_id/>
  <metlin_id>6156</metlin_id>
  <synthesis_reference>Argoudelis, Chris J. Preparation of crystalline pyridoxine 5'-phosphate and some of its properties. Journal of Agricultural and Food Chemistry (1986), 34(6), 995-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00214</protein_accession>
      <name>Pyridoxine-5'-phosphate oxidase</name>
      <uniprot_id>Q5E9K3</uniprot_id>
      <gene_name>PNPO</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:06 UTC</creation_date>
  <update_date>2020-03-13 16:27:15 UTC</update_date>
  <accession>BMDB0001320</accession>
  <secondary_accessions>
    <accession>BMDB01320</accession>
  </secondary_accessions>
  <name>(13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid</name>
  <description/>
  <synonyms>
    <synonym>(13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoate</synonym>
    <synonym>(13E)-11a-Hydroxy-9,15-dioxoprost-13-enoate</synonym>
    <synonym>(13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoic acid</synonym>
    <synonym>(13E)-11Α-hydroxy-9,15-dioxoprost-13-enoate</synonym>
    <synonym>(13E)-11Α-hydroxy-9,15-dioxoprost-13-enoic acid</synonym>
    <synonym>(13E)-11alpha-Hydroxy-9,15-dioxoprost-13-en-1-Oic acid</synonym>
    <synonym>(13E)-11a-Hydroxy-9,15-dioxoprost-13-en-1-Oate</synonym>
    <synonym>(13E)-11a-Hydroxy-9,15-dioxoprost-13-en-1-Oic acid</synonym>
    <synonym>(13E)-11alpha-Hydroxy-9,15-dioxoprost-13-en-1-Oate</synonym>
    <synonym>(13E)-11Α-hydroxy-9,15-dioxoprost-13-en-1-Oate</synonym>
    <synonym>(13E)-11Α-hydroxy-9,15-dioxoprost-13-en-1-Oic acid</synonym>
    <synonym>(11a,13E)-11-Hydroxy-9,15-dioxoprost-13-en-1-Oate</synonym>
    <synonym>(11a,13E)-11-Hydroxy-9,15-dioxoprost-13-en-1-Oic acid</synonym>
    <synonym>(11alpha,13E)-11-Hydroxy-9,15-dioxoprost-13-en-1-Oate</synonym>
    <synonym>(11alpha,13E)-11-Hydroxy-9,15-dioxoprost-13-en-1-Oic acid</synonym>
    <synonym>(13E)-11-alpha-Hydroxy-9,15-dioxoprost-13-enoate</synonym>
    <synonym>(13E)-11-alpha-Hydroxy-9,15-dioxoprost-13-enoic acid</synonym>
    <synonym>1-Hydroxy-9,15-dioxo-(11a,13E)-prost-13-en-1-Oate</synonym>
    <synonym>1-Hydroxy-9,15-dioxo-(11a,13E)-prost-13-en-1-Oic acid</synonym>
    <synonym>15-Keto pge1</synonym>
    <synonym>15-Keto-pge</synonym>
    <synonym>15-Keto-pge1</synonym>
    <synonym>15-Keto-pge1-alpha</synonym>
    <synonym>15-Keto-prostaglandin e1</synonym>
    <synonym>15-Ketoprostaglandin e</synonym>
    <synonym>15-Ketoprostaglandin e1</synonym>
    <synonym>15-oxo-PGE1</synonym>
    <synonym>15-Oxoprostaglandin e1</synonym>
    <synonym>3-Hydroxy-5-oxo-2-(3-oxo-1-octenyl)-cyclopentaneheptanoate</synonym>
    <synonym>3-Hydroxy-5-oxo-2-(3-oxo-1-octenyl)-cyclopentaneheptanoic acid</synonym>
    <synonym>9,15-Dioxo-11R-hydroxy-13E-prostaenoate</synonym>
    <synonym>9,15-Dioxo-11R-hydroxy-13E-prostaenoic acid</synonym>
    <synonym>15-Ketoprostaglandin e, (11alpha,13E)-(+-)-isomer</synonym>
    <synonym>15-Ketoprostaglandin e, (5Z,11alpha)-isomer, 2H-labeled</synonym>
    <synonym>(13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid</synonym>
  </synonyms>
  <chemical_formula>C20H32O5</chemical_formula>
  <average_molecular_weight>352.4651</average_molecular_weight>
  <monisotopic_moleculate_weight>352.224974134</monisotopic_moleculate_weight>
  <iupac_name>7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]heptanoic acid</iupac_name>
  <traditional_iupac>15-keto-PGE1</traditional_iupac>
  <cas_registry_number>22973-19-9</cas_registry_number>
  <smiles>CCCCCC(=O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,16-17,19,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t16-,17-,19-/m1/s1</inchi>
  <inchikey>VXPBDCBTMSKCKZ-XQHNHVHJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Prostaglandins and related compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Acryloyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Cyclopentanols</alternative_parent>
      <alternative_parent>Enones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acryloyl-group</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Alpha,beta-unsaturated ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclopentanol</substituent>
      <substituent>Enone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Prostaglandin skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>prostaglandins E</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]heptanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>352.4651</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>352.224974134</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCC(=O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H32O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,16-17,19,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t16-,17-,19-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VXPBDCBTMSKCKZ-XQHNHVHJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>91.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>97.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357666</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04654</kegg_id>
  <chemspider_id>4444295</chemspider_id>
  <pubchem_compound_id>5280710</pubchem_compound_id>
  <drugbank_id/>
  <foodb_id>FDB022553</foodb_id>
  <pdbe_id/>
  <chebi_id>15548</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>44269</bigg_id>
  <wikipedia_id/>
  <metlin_id>6157</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:07 UTC</creation_date>
  <update_date>2020-03-13 16:27:15 UTC</update_date>
  <accession>BMDB0001321</accession>
  <secondary_accessions>
    <accession>BMDB01321</accession>
  </secondary_accessions>
  <name>D-Erythrose 4-phosphate</name>
  <description/>
  <synonyms>
    <synonym>4-O-Phosphono-D-erythrose</synonym>
    <synonym>ERYTHOSE-4-phosphATE</synonym>
    <synonym>ERYTHOSE-4-phosphoric acid</synonym>
    <synonym>D-Erythrose 4-phosphoric acid</synonym>
    <synonym>D-Erythrose 4-PO4</synonym>
    <synonym>D-Erythrose-4-p</synonym>
    <synonym>D-Erythrose-4-phosphate</synonym>
    <synonym>Erythrose 4-phosphate</synonym>
    <synonym>Erythrose 4-PO4</synonym>
    <synonym>Erythrose-4-p</synonym>
    <synonym>Erythrose-4-phosphate</synonym>
    <synonym>Erythrose-4P</synonym>
    <synonym>Threose 4-phosphate</synonym>
    <synonym>Erythrose 4-phosphate, (r*,r*)-isomer</synonym>
    <synonym>Erythrose 4-phosphate, ((r*,r*)-(+-))-isomer</synonym>
    <synonym>Erythrose 4-phosphate, 14c4-labeled, (r*,r*)-isomer</synonym>
    <synonym>Erythrose 4-phosphate, ((r*,s*)-(+-))-isomer</synonym>
  </synonyms>
  <chemical_formula>C4H9O7P</chemical_formula>
  <average_molecular_weight>200.0838</average_molecular_weight>
  <monisotopic_moleculate_weight>200.008589154</monisotopic_moleculate_weight>
  <iupac_name>[(2R,3R)-2,3-dihydroxy-4-oxobutoxy]phosphonic acid</iupac_name>
  <traditional_iupac>4-O-phosphono-D-erythrose</traditional_iupac>
  <cas_registry_number>585-18-2</cas_registry_number>
  <smiles>O[C@H](COP(O)(O)=O)[C@@H](O)C=O</smiles>
  <inchi>InChI=1S/C4H9O7P/c5-1-3(6)4(7)2-11-12(8,9)10/h1,3-4,6-7H,2H2,(H2,8,9,10)/t3-,4+/m0/s1</inchi>
  <inchikey>NGHMDNPXVRFFGS-IUYQGCFVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharide phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Alpha-hydroxyaldehydes</alternative_parent>
      <alternative_parent>Beta-hydroxy aldehydes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-hydroxyaldehyde</substituent>
      <substituent>Beta-hydroxy aldehyde</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>erythrose phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(2R,3R)-2,3-dihydroxy-4-oxobutoxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>200.0838</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>200.008589154</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H](COP(O)(O)=O)[C@@H](O)C=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H9O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H9O7P/c5-1-3(6)4(7)2-11-12(8,9)10/h1,3-4,6-7H,2H2,(H2,8,9,10)/t3-,4+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NGHMDNPXVRFFGS-IUYQGCFVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>124.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>36.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33971</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33972</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38023</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00279</kegg_id>
  <chemspider_id>109096</chemspider_id>
  <pubchem_compound_id>122357</pubchem_compound_id>
  <drugbank_id>DB03937</drugbank_id>
  <foodb_id>FDB001614</foodb_id>
  <pdbe_id/>
  <chebi_id>48153</chebi_id>
  <knapsack_id>C00007472</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>34479</bigg_id>
  <wikipedia_id>Erythrose_4-phosphate</wikipedia_id>
  <metlin_id>6158</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00103</protein_accession>
      <name>Transaldolase</name>
      <uniprot_id>Q2TBL6</uniprot_id>
      <gene_name>TALDO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00104</protein_accession>
      <name>Transaldolase</name>
      <uniprot_id>Q58DR3</uniprot_id>
      <gene_name>TALDO1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:08 UTC</creation_date>
  <update_date>2020-04-15 22:07:26 UTC</update_date>
  <accession>BMDB0001322</accession>
  <secondary_accessions>
    <accession>BMDB01322</accession>
  </secondary_accessions>
  <name>Oleoyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>Octadecenoyl-CoA (N-C18:1CoA)</synonym>
    <synonym>4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(9Z)-octadec-9-enoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidate</synonym>
    <synonym>4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(9Z)-octadec-9-enoylsulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidate</synonym>
    <synonym>4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(9Z)-octadec-9-enoylsulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid</synonym>
  </synonyms>
  <chemical_formula>C39H68N7O17P3S</chemical_formula>
  <average_molecular_weight>1031.98</average_molecular_weight>
  <monisotopic_moleculate_weight>1031.360524011</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z)-octadec-9-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z)-octadec-9-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>1716-06-9</cas_registry_number>
  <smiles>CCCCCCCC\C=C/CCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C39H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h11-12,26-28,32-34,38,49-50H,4-10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b12-11-/t28-,32-,33-,34?,38-/m1/s1</inchi>
  <inchikey>XDUHQPOXLUAVEE-ZXQNDDKTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z)-octadec-9-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1031.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1031.360524011</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCC\C=C/CCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C39H68N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C39H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h11-12,26-28,32-34,38,49-50H,4-10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b12-11-/t28-,32-,33-,34?,38-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XDUHQPOXLUAVEE-ZXQNDDKTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>246.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>103.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>321639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369309</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>4444057</chemspider_id>
  <pubchem_compound_id>5280355</pubchem_compound_id>
  <foodb_id>FDB022554</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <kegg_id>C00510</kegg_id>
  <chebi_id>15534</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6159</metlin_id>
  <synthesis_reference>noue, Satoshi; Oba, Yuichi; Oga, Hajime.  Manufacture of fatty acyl-coenzyme A using luciferase.    Jpn. Kokai Tokkyo Koho  (2004),     15 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00670</protein_accession>
      <name>Acyl-CoA desaturase</name>
      <uniprot_id>Q9TT94</uniprot_id>
      <gene_name>SCD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00829</protein_accession>
      <name>Stearoyl-CoA desaturase 5</name>
      <uniprot_id>Q2KIA4</uniprot_id>
      <gene_name>SCD5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:09 UTC</creation_date>
  <update_date>2020-04-15 22:15:05 UTC</update_date>
  <accession>BMDB0001324</accession>
  <secondary_accessions>
    <accession>BMDB01324</accession>
  </secondary_accessions>
  <name>N'-Hydroxymethylnorcotinine</name>
  <description/>
  <synonyms>
    <synonym>(5S)-1-(Hydroxymethyl)-5-(3-pyridinyl)-2-pyrrolidinone</synonym>
    <synonym>(S)-1-(Hydroxymethyl)-5-(3-pyridinyl)-2-pyrrolidinone</synonym>
    <synonym>N'-hydroxymethyl-norcotinine</synonym>
    <synonym>N-(Hydroxymethyl)-norcotinine</synonym>
    <synonym>N-Hydroxymethylnorcotinine</synonym>
    <synonym>5-(3'-Pyridyl)-1-hydroxymethyl-2-pyrrolidone</synonym>
    <synonym>N-(Hydroxymethyl)norcotinine</synonym>
  </synonyms>
  <chemical_formula>C10H12N2O2</chemical_formula>
  <average_molecular_weight>192.2145</average_molecular_weight>
  <monisotopic_moleculate_weight>192.089877638</monisotopic_moleculate_weight>
  <iupac_name>(5S)-1-(hydroxymethyl)-5-(pyridin-3-yl)pyrrolidin-2-one</iupac_name>
  <traditional_iupac>(5S)-1-(hydroxymethyl)-5-(pyridin-3-yl)pyrrolidin-2-one</traditional_iupac>
  <cas_registry_number>157129-55-0</cas_registry_number>
  <smiles>OCN1[C@@H](CCC1=O)C1=CN=CC=C1</smiles>
  <inchi>InChI=1S/C10H12N2O2/c13-7-12-9(3-4-10(12)14)8-2-1-5-11-6-8/h1-2,5-6,9,13H,3-4,7H2/t9-/m0/s1</inchi>
  <inchikey>GQUFOBHEPVFQMD-VIFPVBQESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyrrolidinylpyridines</sub_class>
    <direct_parent>Pyrrolidinylpyridines</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Alkanolamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>N-alkylpyrrolidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrrolidine-2-ones</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-pyrrolidone</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Alkanolamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>N-alkylpyrrolidine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidinylpyridine</substituent>
      <substituent>Pyrrolidone</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5S)-1-(hydroxymethyl)-5-(pyridin-3-yl)pyrrolidin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>192.2145</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>192.089877638</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCN1[C@@H](CCC1=O)C1=CN=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N2O2/c13-7-12-9(3-4-10(12)14)8-2-1-5-11-6-8/h1-2,5-6,9,13H,3-4,7H2/t9-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GQUFOBHEPVFQMD-VIFPVBQESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>53.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344184</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id/>
  <pubchem_compound_id>25201488</pubchem_compound_id>
  <foodb_id>FDB031011</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <kegg_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:10 UTC</creation_date>
  <update_date>2020-04-15 22:35:50 UTC</update_date>
  <accession>BMDB0001325</accession>
  <secondary_accessions>
    <accession>BMDB01325</accession>
  </secondary_accessions>
  <name>N6,N6,N6-Trimethyl-L-lysine</name>
  <description>N6,N6,N6-Trimethyl-L-lysine, also known as epsilon-N-trimethyl-L-lysine or n6,n6,n6-trimethyl-l-lysine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. N6,N6,N6-Trimethyl-L-lysine is possibly soluble (in water) and a very strong basic compound (based on its pKa). N6,N6,N6-Trimethyl-L-lysine exists in all living organisms, ranging from bacteria to humans. N6,N6,N6-Trimethyl-L-lysine participates in a number of enzymatic reactions, within cattle. In particular, N6,N6,N6-Trimethyl-L-lysine and S-adenosylhomocysteine can be biosynthesized from L-lysine and S-adenosylmethionine; which is catalyzed by the enzyme histone-lysine N-methyltransferase SETD7. In addition, N6,N6,N6-Trimethyl-L-lysine and oxoglutaric acid can be converted into 3-hydroxy-N6,N6,N6-trimethyl-L-lysine and succinic acid; which is mediated by the enzyme n6,n6,n6-trimethyl-l-lysine dioxygenase, mitochondrial. In cattle, N6,N6,N6-trimethyl-L-lysine is involved in the metabolic pathway called carnitine synthesis pathway.</description>
  <synonyms>
    <synonym>(S)-2-Amino-6-(trimethylammonio)hexanoate</synonym>
    <synonym>(S)-2-Amino-6-(trimethylammonio)hexanoic acid</synonym>
    <synonym>delta-Trimethyllysine</synonym>
    <synonym>epsilon-N-Trimethyl-L-lysine</synonym>
    <synonym>epsilon-Trimethyl-L-lysine</synonym>
    <synonym>N(6),N(6),N(6)-Trimethyl-L-lysine</synonym>
    <synonym>S)-5-Amino-5-carboxy-N,N,N-trimethyl-1-pentanaminium</synonym>
    <synonym>Trimethyllysine</synonym>
    <synonym>6-N-L-Trimethyl-L-lysine</synonym>
    <synonym>epsilon-N-Trimethyl-lysine</synonym>
    <synonym>TRIMETHYLLLYSINE</synonym>
    <synonym>Trimethyllysine hydroxide, inner salt, (S)-isomer</synonym>
    <synonym>Trimethyllysine, (+-)-isomer</synonym>
    <synonym>Trimethyllysine hydroxide,inner salt, (+-)-isomer</synonym>
    <synonym>Trimethyllysine chloride, (S)-isomer</synonym>
    <synonym>(2S)-2-Amino-6-(trimethylazaniumyl)hexanoic acid</synonym>
  </synonyms>
  <chemical_formula>C9H20N2O2</chemical_formula>
  <average_molecular_weight>188.2673</average_molecular_weight>
  <monisotopic_moleculate_weight>188.152477894</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-6-(trimethylazaniumyl)hexanoate</iupac_name>
  <traditional_iupac>n-trimethyllysine</traditional_iupac>
  <cas_registry_number>19253-88-4</cas_registry_number>
  <smiles>C[N+](C)(C)CCCC[C@H](N)C([O-])=O</smiles>
  <inchi>InChI=1S/C9H20N2O2/c1-11(2,3)7-5-4-6-8(10)9(12)13/h8H,4-7,10H2,1-3H3/t8-/m0/s1</inchi>
  <inchikey>MXNRLFUSFKVQSK-QMMMGPOBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-6-(trimethylazaniumyl)hexanoate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>188.2673</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>188.152477894</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)CCCC[C@H](N)C([O-])=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H20N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H20N2O2/c1-11(2,3)7-5-4-6-8(10)9(12)13/h8H,4-7,10H2,1-3H3/t8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MXNRLFUSFKVQSK-QMMMGPOBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>74.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18619</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351240</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>389120</chemspider_id>
  <pubchem_compound_id>440120</pubchem_compound_id>
  <foodb_id>FDB022556</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <kegg_id>C03793</kegg_id>
  <chebi_id>17311</chebi_id>
  <meta_cyc_id>N6N6N6-TRIMETHYL-L-LYSINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>42542</bigg_id>
  <wikipedia_id/>
  <metlin_id>6161</metlin_id>
  <synthesis_reference>Chen F M; Benoiton N L  A synthesis of N6,N6,N6-trimethyl-L-lysine dioxalate in gram amounts.    Biochemistry and cell biology = Biochimie et biologie cellulaire  (1986),  64(3),  182-3.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00622</protein_accession>
      <name>Trimethyllysine dioxygenase, mitochondrial</name>
      <uniprot_id>Q0VC74</uniprot_id>
      <gene_name>TMLHE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:12 UTC</creation_date>
  <update_date>2020-04-14 21:15:19 UTC</update_date>
  <accession>BMDB0001327</accession>
  <secondary_accessions>
    <accession>BMDB01327</accession>
  </secondary_accessions>
  <name>Rubidium</name>
  <description>Rubidium, also known as Rb+ or rubidium ion, belongs to the class of inorganic compounds known as homogeneous alkali metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a alkali metal atom. Rubidium exists as a solid, possibly soluble (in water), and possibly neutral molecule.</description>
  <synonyms>
    <synonym>RB(+)</synonym>
    <synonym>Rb+</synonym>
    <synonym>RUBIDIUM ion</synonym>
    <synonym>Rubidium(1+)</synonym>
    <synonym>Rubidium +</synonym>
    <synonym>Rubidium</synonym>
  </synonyms>
  <chemical_formula>Rb</chemical_formula>
  <average_molecular_weight>85.4678</average_molecular_weight>
  <monisotopic_moleculate_weight>84.911789341</monisotopic_moleculate_weight>
  <iupac_name>rubidium(1+) ion</iupac_name>
  <traditional_iupac>rubidium(1+) ion</traditional_iupac>
  <cas_registry_number>7440-17-7</cas_registry_number>
  <smiles>[Rb+]</smiles>
  <inchi>InChI=1S/Rb/q+1</inchi>
  <inchikey>NCCSSGKUIKYAJD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous alkali metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a alkali metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous alkali metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous alkali metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous alkali metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a cation</external_descriptor>
      <external_descriptor>alkali metal cation</external_descriptor>
      <external_descriptor>monoatomic monocation</external_descriptor>
      <external_descriptor>monovalent inorganic cation</external_descriptor>
      <external_descriptor>rubidium molecular entity</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>39 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>rubidium(1+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>85.4678</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>84.911789341</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Rb+]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Rb</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Rb/q+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NCCSSGKUIKYAJD-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300081</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1.8+/-0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>80+/-16</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>37+/-7</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.7 - 39</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>G.K. Murthy, U. Rhea, J.T.Peeler. Rubidium and Lead Content of Market Milk. Journal of Dairy Science. 50(5), May 1967, p. 651-654</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9.419 +/- 0.948</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.289 +/- 0.234</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.962 +/- 0.737</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS.  Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.781 +/- 0.211</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.833 +/- 1.404</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.277 +/- 0.351</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.405 - 9.817</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>25+/-5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>5.82 +/- 0.08</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by ICP-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>40+/-7</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>49+/-9</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>94865</chemspider_id>
  <pubchem_compound_id>105153</pubchem_compound_id>
  <foodb_id>FDB003783</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <kegg_id>C17061</kegg_id>
  <chebi_id>49847</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Rubidium</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>G.K. Murthy, U. Rhea, J.T.Peeler. Rubidium and Lead Content of Market Milk. Journal of Dairy Science. 50(5), May 1967, p. 651-654</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
    </reference>
    <reference>
      <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:13 UTC</creation_date>
  <update_date>2020-03-13 16:27:18 UTC</update_date>
  <accession>BMDB0001328</accession>
  <secondary_accessions>
    <accession>BMDB01328</accession>
  </secondary_accessions>
  <name>dTDP-D-glucose</name>
  <description>dTDP-D-Glucose belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. dTDP-D-Glucose is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). dTDP-D-Glucose exists in all living organisms, ranging from bacteria to humans. In cattle, dTDP-D-glucose is involved in a couple of metabolic pathways, which include the nucleotide sugars metabolism pathway and the fructose and mannose degradation pathway.</description>
  <synonyms>
    <synonym>dTDP-delta-Glucose</synonym>
    <synonym>dTDP-Glucose</synonym>
    <synonym>DTDPglucose</synonym>
    <synonym>mono-a-D-Glucopyranosyl ester</synonym>
    <synonym>mono-alpha-D-Glucopyranosyl ester</synonym>
    <synonym>mono-alpha-delta-Glucopyranosyl ester</synonym>
    <synonym>TDP-D-Glucose</synonym>
    <synonym>TDP-delta-Glucose</synonym>
    <synonym>TDP-GLC</synonym>
    <synonym>TDPG</synonym>
    <synonym>Thymidine 5-diphosphate-D-glucose</synonym>
    <synonym>Thymidine 5-diphosphate-delta-glucose</synonym>
  </synonyms>
  <chemical_formula>C16H26N2O16P2</chemical_formula>
  <average_molecular_weight>564.329</average_molecular_weight>
  <monisotopic_moleculate_weight>564.075755818</monisotopic_moleculate_weight>
  <iupac_name>{[hydroxy({[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy}({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid</iupac_name>
  <traditional_iupac>dtdp-D-glucose</traditional_iupac>
  <cas_registry_number>2196-62-5</cas_registry_number>
  <smiles>CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)O2)C(=O)NC1=O</smiles>
  <inchi>InChI=1S/C16H26N2O16P2/c1-6-3-18(16(25)17-14(6)24)10-2-7(20)9(31-10)5-30-35(26,27)34-36(28,29)33-15-13(23)12(22)11(21)8(4-19)32-15/h3,7-13,15,19-23H,2,4-5H2,1H3,(H,26,27)(H,28,29)(H,17,24,25)/t7-,8+,9+,10+,11+,12-,13+,15?/m0/s1</inchi>
  <inchikey>YSYKRGRSMLTJNL-KFQCIAAJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine nucleotide sugars</sub_class>
    <direct_parent>Pyrimidine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidine 2'-deoxyribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine nucleotide sugar</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dTDP-alpha-D-glucose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[hydroxy({[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy}({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>564.329</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>564.075755818</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)O2)C(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H26N2O16P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H26N2O16P2/c1-6-3-18(16(25)17-14(6)24)10-2-7(20)9(31-10)5-30-35(26,27)34-36(28,29)33-15-13(23)12(22)11(21)8(4-19)32-15/h3,7-13,15,19-23H,2,4-5H2,1H3,(H,26,27)(H,28,29)(H,17,24,25)/t7-,8+,9+,10+,11+,12-,13+,15?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YSYKRGRSMLTJNL-KFQCIAAJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>271.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>109.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38025</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31912</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>388455</chemspider_id>
  <pubchem_compound_id>439324</pubchem_compound_id>
  <foodb_id>FDB022557</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <kegg_id>C00842</kegg_id>
  <chebi_id>35248</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>36175</bigg_id>
  <wikipedia_id/>
  <metlin_id>6163</metlin_id>
  <synthesis_reference>Goncalves, Ruth J.  Thymidine diphosphate glucose and biosynthesis of glucosides in wheat germ. I.    Enzymologia  (1963),  26(5),  287-93.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00437</protein_accession>
      <name>dTDP-D-glucose 4,6-dehydratase</name>
      <uniprot_id>A6QLW2</uniprot_id>
      <gene_name>TGDS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:14 UTC</creation_date>
  <update_date>2020-04-15 22:15:05 UTC</update_date>
  <accession>BMDB0001329</accession>
  <secondary_accessions>
    <accession>BMDB01329</accession>
  </secondary_accessions>
  <name>2'-Hydroxynicotine</name>
  <description/>
  <synonyms>
    <synonym>2-Hydroxynicotine</synonym>
  </synonyms>
  <chemical_formula>C10H14N2O</chemical_formula>
  <average_molecular_weight>178.235</average_molecular_weight>
  <monisotopic_moleculate_weight>178.110613079</monisotopic_moleculate_weight>
  <iupac_name>(2R)-1-methyl-2-(pyridin-3-yl)pyrrolidin-2-ol</iupac_name>
  <traditional_iupac>(2R)-1-methyl-2-(pyridin-3-yl)pyrrolidin-2-ol</traditional_iupac>
  <cas_registry_number>1824020-12-3</cas_registry_number>
  <smiles>CN1CCC[C@@]1(O)C1=CC=CN=C1</smiles>
  <inchi>InChI=1S/C10H14N2O/c1-12-7-3-5-10(12,13)9-4-2-6-11-8-9/h2,4,6,8,13H,3,5,7H2,1H3/t10-/m1/s1</inchi>
  <inchikey>BOQRPPFUUSHFGW-SNVBAGLBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyrrolidinylpyridines</sub_class>
    <direct_parent>Pyrrolidinylpyridines</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Alkanolamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-alkylpyrrolidines</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Alkanolamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-alkylpyrrolidine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidinylpyridine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>7.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-1-methyl-2-(pyridin-3-yl)pyrrolidin-2-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>178.235</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>178.110613079</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1CCC[C@@]1(O)C1=CC=CN=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H14N2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H14N2O/c1-12-7-3-5-10(12,13)9-4-2-6-11-8-9/h2,4,6,8,13H,3,5,7H2,1H3/t10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BOQRPPFUUSHFGW-SNVBAGLBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>36.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1319482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1319483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1319484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1433917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1433918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1433919</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>19951246</chemspider_id>
  <pubchem_compound_id>23615292</pubchem_compound_id>
  <foodb_id>FDB022558</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <kegg_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6164</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:15 UTC</creation_date>
  <update_date>2020-04-15 22:15:06 UTC</update_date>
  <accession>BMDB0001330</accession>
  <secondary_accessions>
    <accession>BMDB01330</accession>
  </secondary_accessions>
  <name>2-Amino-3-carboxymuconic acid semialdehyde</name>
  <description>2-Amino-3-carboxymuconic acid semialdehyde, also known as 2-amino-3-carboxymuconic acid semialdehyde or ACS, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 2-Amino-3-carboxymuconic acid semialdehyde is possibly soluble (in water) and a very strong basic compound (based on its pKa). 2-Amino-3-carboxymuconic acid semialdehyde exists in all living species, ranging from bacteria to humans. 2-Amino-3-carboxymuconic acid semialdehyde participates in a number of enzymatic reactions, within cattle. In particular, 2-Amino-3-carboxymuconic acid semialdehyde can be biosynthesized from 3-hydroxyanthranilic acid; which is mediated by the enzyme 3,4-dihydroxyphenylacetaldehyde. In addition, 2-Amino-3-carboxymuconic acid semialdehyde can be converted into 2-aminomuconic acid semialdehyde through the action of the enzyme 2-amino-3-carboxymuconic acid semialdehyde decarboxylase. In cattle, 2-amino-3-carboxymuconic acid semialdehyde is involved in the metabolic pathway called the tryptophan metabolism pathway.</description>
  <synonyms>
    <synonym>2-Amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioate</synonym>
    <synonym>2-Amino-3-(3-oxoprop-1-enyl)-but-2-enedioate</synonym>
    <synonym>2-Amino-3-carboxymuconate semialdehyde</synonym>
    <synonym>2-Amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acid</synonym>
    <synonym>2-Amino-3-(3-oxoprop-1-enyl)-but-2-enedioic acid</synonym>
    <synonym>2-Amino-3-carboxymuconate-6-semialdehyde</synonym>
    <synonym>ACS</synonym>
    <synonym>Amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioate</synonym>
    <synonym>Amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acid</synonym>
  </synonyms>
  <chemical_formula>C7H7NO5</chemical_formula>
  <average_molecular_weight>185.1342</average_molecular_weight>
  <monisotopic_moleculate_weight>185.032422339</monisotopic_moleculate_weight>
  <iupac_name>(2Z)-2-amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid</iupac_name>
  <traditional_iupac>(2Z)-2-amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid</traditional_iupac>
  <cas_registry_number>16597-19-6</cas_registry_number>
  <smiles>N\C(C(O)=O)=C(\C=C/C=O)/C(O)=O</smiles>
  <inchi>InChI=1S/C7H7NO5/c8-5(7(12)13)4(6(10)11)2-1-3-9/h1-3H,8H2,(H,10,11)(H,12,13)/b2-1-,5-4-</inchi>
  <inchikey>KACPVQQHDVBVFC-OIFXTYEKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Aldehydes</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Branched fatty acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Enals</alternative_parent>
      <alternative_parent>Enamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha,beta-unsaturated aldehyde</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Enal</substituent>
      <substituent>Enamine</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Unsaturated fatty acid</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-amino-3-(3-oxoprop-1-enyl)but-2-enedioic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2Z)-2-amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>185.1342</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>185.032422339</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N\C(C(O)=O)=C(\C=C/C=O)/C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H7NO5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H7NO5/c8-5(7(12)13)4(6(10)11)2-1-3-9/h1-3H,8H2,(H,10,11)(H,12,13)/b2-1-,5-4-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KACPVQQHDVBVFC-OIFXTYEKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>117.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356463</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>4444266</chemspider_id>
  <pubchem_compound_id>5280673</pubchem_compound_id>
  <foodb_id>FDB022559</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <kegg_id>C04409</kegg_id>
  <chebi_id>995</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>1445617</bigg_id>
  <wikipedia_id/>
  <metlin_id>6165</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00639</protein_accession>
      <name>2-amino-3-carboxymuconate-6-semialdehyde decarboxylase</name>
      <uniprot_id>Q0II68</uniprot_id>
      <gene_name>ACMSD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00666</protein_accession>
      <name>3-hydroxyanthranilate 3,4-dioxygenase</name>
      <uniprot_id>Q0VCA8</uniprot_id>
      <gene_name>HAAO</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:16 UTC</creation_date>
  <update_date>2020-04-16 20:36:52 UTC</update_date>
  <accession>BMDB0001333</accession>
  <secondary_accessions>
    <accession>BMDB01333</accession>
  </secondary_accessions>
  <name>Manganese</name>
  <description>Manganese, also known as MN(ii) or MN2+, belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Manganese exists as a solid, possibly soluble (in water), and possibly neutral molecule. Manganese exists in all living species, ranging from bacteria to humans. Manganese is a potentially toxic compound.</description>
  <synonyms>
    <synonym>MANGANESE (II) ion</synonym>
    <synonym>Manganese(II)</synonym>
    <synonym>Manganese, ion (MN2+)</synonym>
    <synonym>Manganous ion</synonym>
    <synonym>MN(II)</synonym>
    <synonym>MN(2+)</synonym>
    <synonym>MN2+</synonym>
  </synonyms>
  <chemical_formula>Mn</chemical_formula>
  <average_molecular_weight>54.938</average_molecular_weight>
  <monisotopic_moleculate_weight>54.938049636</monisotopic_moleculate_weight>
  <iupac_name>manganese(2+) ion</iupac_name>
  <traditional_iupac>manganese(2+) ion</traditional_iupac>
  <cas_registry_number>7439-96-5</cas_registry_number>
  <smiles>[Mn++]</smiles>
  <inchi>InChI=1S/Mn/q+2</inchi>
  <inchikey>WAEMQWOKJMHJLA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous transition metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous transition metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous transition metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a cation</external_descriptor>
      <external_descriptor>divalent metal cation</external_descriptor>
      <external_descriptor>manganese cation</external_descriptor>
      <external_descriptor>monoatomic dication</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>1244 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>manganese(2+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>54.938</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>54.938049636</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Mn++]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Mn</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Mn/q+2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WAEMQWOKJMHJLA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Degradation of Superoxides</name>
      <smpdb_id>SMP0087191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fc Epsilon Receptor I Signaling in Mast Cells</name>
      <smpdb_id>SMP0108186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>LPS and Citrate Signaling and Inflammation</name>
      <smpdb_id>SMP0120946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylinositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30259</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>0.12+/-0.02</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.6 - 1.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.546</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Whole Milk</comment>
      <references>
        <reference>
          <reference_text>Raghib MH, Chan WY, Rennert OM: Comparative biological availability of manganese from extrinsically labelled milk diets using sucking rats as a model. Br J Nutr. 1986 Jan;55(1):49-58.</reference_text>
          <pubmed_id>3663578</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.64</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.37 +/- 0.15</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>A. PECHOVÁ et al. Contents of Zn, Cu, Mn and Se in Milk in Relation to their Concentrations in Blood, Milk Yield and Stage of Lactation in Dairy Cattle. Acta Vet. Brno 2008, 77: 523-531</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.5 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.45 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.50 +/- 0.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.6 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.749 +/- 0.109</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.713 +/- 0.218</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.511 +/- 0.0910</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS.  Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.495 +/- 0.728</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.165 +/- 0.0728</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.149 +/- 2.0751</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.82</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.82</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.728 - 5.279</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.456</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.638</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.456</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.82</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.82</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.82</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.928 - 1.838</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>59+/-62</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2.5 +/- 0.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by ICP-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>&lt;LOQ</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>25916</chemspider_id>
  <pubchem_compound_id>27854</pubchem_compound_id>
  <foodb_id>FDB031005</foodb_id>
  <drugbank_id>DB06757</drugbank_id>
  <pdbe_id/>
  <kegg_id>C19610</kegg_id>
  <chebi_id>29035</chebi_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Manganese</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Raghib MH, Chan WY, Rennert OM: Comparative biological availability of manganese from extrinsically labelled milk diets using sucking rats as a model. Br J Nutr. 1986 Jan;55(1):49-58.</reference_text>
      <pubmed_id>3663578</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. PECHOVÁ et al. Contents of Zn, Cu, Mn and Se in Milk in Relation to their Concentrations in Blood, Milk Yield and Stage of Lactation in Dairy Cattle. Acta Vet. Brno 2008, 77: 523-531</reference_text>
    </reference>
    <reference>
      <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
    </reference>
    <reference>
      <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00141</protein_accession>
      <name>Proto-oncogene tyrosine-protein kinase Fyn</name>
      <uniprot_id>A0JNB0</uniprot_id>
      <gene_name>FYN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00146</protein_accession>
      <name>Activin receptor type-2A</name>
      <uniprot_id>Q28043</uniprot_id>
      <gene_name>ACVR2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00152</protein_accession>
      <name>Activin receptor type-2B</name>
      <uniprot_id>Q95126</uniprot_id>
      <gene_name>ACVR2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00177</protein_accession>
      <name>Ectonucleotide pyrophosphatase/phosphodiesterase family member 2</name>
      <uniprot_id>A1A4K5</uniprot_id>
      <gene_name>ENPP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00204</protein_accession>
      <name>Acetyl-CoA carboxylase 1</name>
      <uniprot_id>Q9TTS3</uniprot_id>
      <gene_name>ACACA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00205</protein_accession>
      <name>Activin receptor type-1</name>
      <uniprot_id>Q28041</uniprot_id>
      <gene_name>ACVR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00381</protein_accession>
      <name>Polypeptide N-acetylgalactosaminyltransferase 6</name>
      <uniprot_id>Q5EA41</uniprot_id>
      <gene_name>GALNT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00382</protein_accession>
      <name>Polypeptide N-acetylgalactosaminyltransferase 1</name>
      <uniprot_id>Q07537</uniprot_id>
      <gene_name>GALNT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00387</protein_accession>
      <name>Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)</name>
      <uniprot_id>Q58DK4</uniprot_id>
      <gene_name>DAK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00390</protein_accession>
      <name>Cholinephosphotransferase 1</name>
      <uniprot_id>Q1LZE6</uniprot_id>
      <gene_name>CHPT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00391</protein_accession>
      <name>Ethanolaminephosphotransferase 1</name>
      <uniprot_id>Q17QM4</uniprot_id>
      <gene_name>SELI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00434</protein_accession>
      <name>cGMP-specific 3',5'-cyclic phosphodiesterase</name>
      <uniprot_id>Q28156</uniprot_id>
      <gene_name>PDE5A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00444</protein_accession>
      <name>U8 snoRNA-decapping enzyme</name>
      <uniprot_id>A1A4Q9</uniprot_id>
      <gene_name>NUDT16</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00445</protein_accession>
      <name>Diphosphoinositol polyphosphate phosphohydrolase 3-beta</name>
      <uniprot_id>Q58CW0</uniprot_id>
      <gene_name>NUDT11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00448</protein_accession>
      <name>Isocitrate dehydrogenase [NADP], mitochondrial</name>
      <uniprot_id>Q04467</uniprot_id>
      <gene_name>IDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00450</protein_accession>
      <name>Endonuclease G, mitochondrial</name>
      <uniprot_id>P38447</uniprot_id>
      <gene_name>ENDOG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00454</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit gamma, mitochondrial</name>
      <uniprot_id>Q58CP0</uniprot_id>
      <gene_name>IDH3G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00460</protein_accession>
      <name>Polyribonucleotide 5'-hydroxyl-kinase Clp1</name>
      <uniprot_id>A2VE01</uniprot_id>
      <gene_name>CLP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00468</protein_accession>
      <name>Protein phosphatase 1B</name>
      <uniprot_id>O62830</uniprot_id>
      <gene_name>PPM1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00470</protein_accession>
      <name>Integrin-linked kinase-associated serine/threonine phosphatase 2C</name>
      <uniprot_id>Q0IIF0</uniprot_id>
      <gene_name>ILKAP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00471</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial</name>
      <uniprot_id>O77784</uniprot_id>
      <gene_name>IDH3B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00477</protein_accession>
      <name>Bis(5'-adenosyl)-triphosphatase</name>
      <uniprot_id>Q1KZG4</uniprot_id>
      <gene_name>FHIT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00484</protein_accession>
      <name>Endoribonuclease Dicer</name>
      <uniprot_id>Q6TUI4</uniprot_id>
      <gene_name>DICER1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00489</protein_accession>
      <name>Nucleoside diphosphate-linked moiety X motif 17</name>
      <uniprot_id>A4FUG7</uniprot_id>
      <gene_name>NUDT17</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00494</protein_accession>
      <name>Protein phosphatase 1K, mitochondrial</name>
      <uniprot_id>Q2PC20</uniprot_id>
      <gene_name>PPM1K</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00499</protein_accession>
      <name>Cytosol aminopeptidase</name>
      <uniprot_id>P00727</uniprot_id>
      <gene_name>LAP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00502</protein_accession>
      <name>TGF-beta receptor type-1</name>
      <uniprot_id>O46680</uniprot_id>
      <gene_name>TGFBR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00504</protein_accession>
      <name>Protein phosphatase 1G</name>
      <uniprot_id>P79126</uniprot_id>
      <gene_name>PPM1G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00511</protein_accession>
      <name>Protein phosphatase 1L</name>
      <uniprot_id>A5PJZ2</uniprot_id>
      <gene_name>PPM1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00512</protein_accession>
      <name>Peroxisomal NADH pyrophosphatase NUDT12</name>
      <uniprot_id>Q29RH3</uniprot_id>
      <gene_name>NUDT12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00516</protein_accession>
      <name>Isocitrate dehydrogenase [NADP] cytoplasmic</name>
      <uniprot_id>Q9XSG3</uniprot_id>
      <gene_name>IDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00521</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit alpha, mitochondrial</name>
      <uniprot_id>P41563</uniprot_id>
      <gene_name>IDH3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00524</protein_accession>
      <name>Protein phosphatase 1A</name>
      <uniprot_id>O62829</uniprot_id>
      <gene_name>PPM1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00553</protein_accession>
      <name>Arginase-1</name>
      <uniprot_id>Q2KJ64</uniprot_id>
      <gene_name>ARG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00558</protein_accession>
      <name>Arginase-2, mitochondrial</name>
      <uniprot_id>Q58DL1</uniprot_id>
      <gene_name>ARG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00586</protein_accession>
      <name>Superoxide dismutase [Mn], mitochondrial</name>
      <uniprot_id>P41976</uniprot_id>
      <gene_name>SOD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00600</protein_accession>
      <name>Trifunctional purine biosynthetic protein adenosine-3</name>
      <uniprot_id>Q59A32</uniprot_id>
      <gene_name>GART</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00604</protein_accession>
      <name>Beta-1,4-galactosyltransferase 1</name>
      <uniprot_id>P08037</uniprot_id>
      <gene_name>B4GALT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00615</protein_accession>
      <name>Pyruvate carboxylase, mitochondrial</name>
      <uniprot_id>Q29RK2</uniprot_id>
      <gene_name>PC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00617</protein_accession>
      <name>Phosphoenolpyruvate carboxykinase, cytosolic [GTP]</name>
      <uniprot_id>Q8HYZ4</uniprot_id>
      <gene_name>PPCK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00640</protein_accession>
      <name>Beta-1,4-galactosyltransferase 3</name>
      <uniprot_id>Q5EA87</uniprot_id>
      <gene_name>B4GALT3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00641</protein_accession>
      <name>Xaa-Pro aminopeptidase 1</name>
      <uniprot_id>Q1JPJ2</uniprot_id>
      <gene_name>XPNPEP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00642</protein_accession>
      <name>Serine/threonine-protein phosphatase 2A catalytic subunit alpha isoform</name>
      <uniprot_id>P67774</uniprot_id>
      <gene_name>PPP2CA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00643</protein_accession>
      <name>Serine/threonine-protein phosphatase PP1-alpha catalytic subunit</name>
      <uniprot_id>Q3T0E7</uniprot_id>
      <gene_name>PPP1CA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00644</protein_accession>
      <name>UDP-N-acetyl-alpha-D-galactosamine:polypeptide N-acetylgalactosaminyltransferase 6 (GalNAc-T6)</name>
      <uniprot_id>A6H6Z5</uniprot_id>
      <gene_name>GALNT6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00645</protein_accession>
      <name>UDP-N-acetyl-alpha-D-galactosamine:polypeptide N-acetylgalactosaminyltransferase 13 (GalNAc-T13)</name>
      <uniprot_id>Q08DM9</uniprot_id>
      <gene_name>GALNT13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00646</protein_accession>
      <name>Serine/threonine-protein phosphatase PP1-beta catalytic subunit</name>
      <uniprot_id>Q3SWW9</uniprot_id>
      <gene_name>PPP1CB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00647</protein_accession>
      <name>Serine/threonine-protein phosphatase 4 catalytic subunit</name>
      <uniprot_id>A6H772</uniprot_id>
      <gene_name>PPP4C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00648</protein_accession>
      <name>Oligoribonuclease, mitochondrial</name>
      <uniprot_id>A2VE52</uniprot_id>
      <gene_name>REXO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00649</protein_accession>
      <name>Serine/threonine-protein phosphatase PP1-gamma catalytic subunit</name>
      <uniprot_id>P61287</uniprot_id>
      <gene_name>PPP1CC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00650</protein_accession>
      <name>Cytosolic non-specific dipeptidase</name>
      <uniprot_id>Q3ZC84</uniprot_id>
      <gene_name>CNDP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00651</protein_accession>
      <name>Protein O-linked-mannose beta-1,2-N-acetylglucosaminyltransferase 1</name>
      <uniprot_id>Q5EAB6</uniprot_id>
      <gene_name>POMGNT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00652</protein_accession>
      <name>Protein prune homolog</name>
      <uniprot_id>Q5E9Y6</uniprot_id>
      <gene_name>PRUNE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00653</protein_accession>
      <name>N-acetyllactosaminide alpha-1,3-galactosyltransferase</name>
      <uniprot_id>P14769</uniprot_id>
      <gene_name>GGTA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00654</protein_accession>
      <name>Serine/threonine-protein phosphatase 2A catalytic subunit beta isoform</name>
      <uniprot_id>Q0P594</uniprot_id>
      <gene_name>PPP2CB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00795</protein_accession>
      <name>Methionine aminopeptidase 1</name>
      <uniprot_id>A6QLA4</uniprot_id>
      <gene_name>METAP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00797</protein_accession>
      <name>Methionine aminopeptidase 2</name>
      <uniprot_id>Q3ZC89</uniprot_id>
      <gene_name>METAP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01592</protein_accession>
      <name>LYR motif-containing protein 4</name>
      <uniprot_id>Q0VCG0</uniprot_id>
      <gene_name>LYRM4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01595</protein_accession>
      <name>Ribonuclease H2 subunit A</name>
      <uniprot_id>Q2TBT5</uniprot_id>
      <gene_name>RNASEH2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01917</protein_accession>
      <name>Ribosomal protein S6 modification-like protein B</name>
      <uniprot_id>Q0VCE9</uniprot_id>
      <gene_name>RIMKLB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01918</protein_accession>
      <name>GALNTL1 protein</name>
      <uniprot_id>A6QLD9</uniprot_id>
      <gene_name>GALNTL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01919</protein_accession>
      <name>Galactose-3-O-sulfotransferase 4</name>
      <uniprot_id>Q5E9W5</uniprot_id>
      <gene_name>GAL3ST4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01920</protein_accession>
      <name>GALNT4 protein</name>
      <uniprot_id>A7YY74</uniprot_id>
      <gene_name>GALNT4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01921</protein_accession>
      <name>GALNT12 protein</name>
      <uniprot_id>A6QLX6</uniprot_id>
      <gene_name>GALNT12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01922</protein_accession>
      <name>UDP-N-acetyl-alpha-D-galactosamine:polypeptide N-acetylgalactosaminyltransferase-like 4</name>
      <uniprot_id>Q0IIK7</uniprot_id>
      <gene_name>GALNTL4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:17 UTC</creation_date>
  <update_date>2020-04-15 22:28:21 UTC</update_date>
  <accession>BMDB0001335</accession>
  <secondary_accessions>
    <accession>BMDB01335</accession>
  </secondary_accessions>
  <name>Prostaglandin I2</name>
  <description>Prostaglandin i2, also known as prostaglandin I2 or prostaglandin I2, belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Thus, prostaglandin I2 is considered to be an eicosanoid lipid molecule. Prostaglandin i2 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Prostaglandin i2 exists in all living organisms, ranging from bacteria to humans. Prostaglandin i2 participates in a number of enzymatic reactions, within cattle. In particular, Prostaglandin I2 can be converted into prostaglandin I2 through the action of the enzyme prostaglandin I2 receptor. In addition, Prostaglandin I2 can be converted into prostaglandin I2 through the action of the enzyme prostaglandin I2 receptor. In cattle, prostaglandin I2 is involved in the metabolic pathway called the intracellular signalling through prostaglandin I2 receptor and prostaglandin I2 pathway.</description>
  <synonyms>
    <synonym>(5Z,13E)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,9alpha,11alpha,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oic acid</synonym>
    <synonym>Epoprostenol</synonym>
    <synonym>Flolan</synonym>
    <synonym>PGI2</synonym>
    <synonym>PGX</synonym>
    <synonym>Prostacyclin</synonym>
    <synonym>Prostaglandin X</synonym>
    <synonym>Vasocyclin</synonym>
    <synonym>(5Z,13E)-(15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-6,9Α-epoxy-11α,15-dihydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-6,9Α-epoxy-11α,15-dihydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,9a,11a,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,9a,11a,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oic acid</synonym>
    <synonym>(5Z,9alpha,11alpha,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,9Α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,9Α,11α,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-Oic acid</synonym>
    <synonym>(5Z,13E)-(15S)-6,9-alpha-Epoxy-11-alpha,15-dihydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-6,9-alpha-Epoxy-11-alpha,15-dihydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E,15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E,15S)-6,9a-Epoxy-11a,15-dihydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>Prostacycline</synonym>
    <synonym>Epoprostanol</synonym>
    <synonym>Epoprostenol sodium</synonym>
    <synonym>Epoprostenol sodium salt, (5Z,9alpha,11alpha,13E,15S)-isomer</synonym>
    <synonym>Prostaglandin I(2)</synonym>
    <synonym>Veletri</synonym>
  </synonyms>
  <chemical_formula>C20H32O5</chemical_formula>
  <average_molecular_weight>352.4651</average_molecular_weight>
  <monisotopic_moleculate_weight>352.224974134</monisotopic_moleculate_weight>
  <iupac_name>5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid</iupac_name>
  <traditional_iupac>epoprostenol</traditional_iupac>
  <cas_registry_number>35121-78-9</cas_registry_number>
  <smiles>CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2OC(C[C@H]12)=CCCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17+,18+,19-/m0/s1</inchi>
  <inchikey>KAQKFAOMNZTLHT-OZUDYXHBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Prostaglandins and related compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Fatty alcohols</alternative_parent>
      <alternative_parent>Heterocyclic fatty acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Medium-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Fatty alcohol</substituent>
      <substituent>Heterocyclic fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Prostaglandin skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>prostaglandins I</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2-ylidene]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>352.4651</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>352.224974134</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2OC(C[C@H]12)=CCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H32O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17+,18+,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KAQKFAOMNZTLHT-OZUDYXHBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>86.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>99.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>41.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Prostacyclin Receptor and Prostacyclin</name>
      <smpdb_id>SMP0107998</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310924</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355796</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355797</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01312</kegg_id>
  <chemspider_id>4445566</chemspider_id>
  <foodb_id>FDB022560</foodb_id>
  <drugbank_id/>
  <chebi_id>15552</chebi_id>
  <pubchem_compound_id>5282411</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <wikipedia_id>Prostacyclin</wikipedia_id>
  <bigg_id>37333</bigg_id>
  <metlin_id>778</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00024</protein_accession>
      <name>Prostacyclin synthase</name>
      <uniprot_id>Q29626</uniprot_id>
      <gene_name>PTGIS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01340</protein_accession>
      <name>Prostacyclin receptor</name>
      <uniprot_id>P79393</uniprot_id>
      <gene_name>PTGIR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:19 UTC</creation_date>
  <update_date>2020-04-16 20:40:41 UTC</update_date>
  <accession>BMDB0001336</accession>
  <secondary_accessions>
    <accession>BMDB01336</accession>
  </secondary_accessions>
  <name>3,4-Dihydroxybenzeneacetic acid</name>
  <description>3,4-Dihydroxybenzeneacetic acid, also known as 3,4-dihydroxybenzeneacetic acid or 3,4-dihydroxybenzeneacetic acid, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-Dihydroxybenzeneacetic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 3,4-Dihydroxybenzeneacetic acid exists in all living organisms, ranging from bacteria to humans. 3,4-Dihydroxybenzeneacetic acid participates in a number of enzymatic reactions, within cattle. In particular, 3,4-Dihydroxybenzeneacetic acid can be biosynthesized from 3,4-dihydroxyphenylacetaldehyde; which is catalyzed by the enzyme 3,4-dihydroxyphenylacetaldehyde. In addition, 3,4-Dihydroxybenzeneacetic acid and guaiacol can be converted into homovanillic acid and pyrocatechol; which is mediated by the enzyme catechol O-methyltransferase. In cattle, 3,4-dihydroxybenzeneacetic acid is involved in the metabolic pathway called the tyrosine metabolism pathway.</description>
  <synonyms>
    <synonym>2-(3,4-DIHYDROXYPHENYL)acetIC ACID</synonym>
    <synonym>3,4-Dihydroxyphenyl acetic acid</synonym>
    <synonym>3,4-Dihydroxyphenylacetic acid</synonym>
    <synonym>Dopacetic acid</synonym>
    <synonym>Homoprotocatechuic acid</synonym>
    <synonym>Homoprotocatechuate</synonym>
    <synonym>2-(3,4-DIHYDROXYPHENYL)acetate</synonym>
    <synonym>3,4-Dihydroxyphenyl acetate</synonym>
    <synonym>3,4-Dihydroxyphenylacetate</synonym>
    <synonym>Dopacetate</synonym>
    <synonym>3,4-Dihydroxybenzeneacetate</synonym>
    <synonym>DOPAC</synonym>
    <synonym>3,4 Dihydroxyphenylacetic acid</synonym>
    <synonym>3,4-Dihydroxyphenylacetic acid, monosodium salt</synonym>
    <synonym>(3,4-Dihydroxyphenyl)-acetic acid</synonym>
    <synonym>(3,4-Dihydroxyphenyl)acetate</synonym>
    <synonym>(3,4-Dihydroxyphenyl)acetic acid</synonym>
    <synonym>3,4-DHPOP</synonym>
    <synonym>3,4-Dihydroxy-benzeneacetic acid</synonym>
    <synonym>3,4-Dihydroxy-phenylacetic acid</synonym>
    <synonym>DHY</synonym>
    <synonym>Dihydroxyphenylacetate</synonym>
    <synonym>Dihydroxyphenylacetic acid</synonym>
    <synonym>HAA</synonym>
    <synonym>Homogentisic acid</synonym>
  </synonyms>
  <chemical_formula>C8H8O4</chemical_formula>
  <average_molecular_weight>168.1467</average_molecular_weight>
  <monisotopic_moleculate_weight>168.042258744</monisotopic_moleculate_weight>
  <iupac_name>2-(3,4-dihydroxyphenyl)acetic acid</iupac_name>
  <traditional_iupac>3,4 dihydroxyphenylacetic acid</traditional_iupac>
  <cas_registry_number>102-32-9</cas_registry_number>
  <smiles>OC(=O)CC1=CC(O)=C(O)C=C1</smiles>
  <inchi>InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)</inchi>
  <inchikey>CFFZDZCDUFSOFZ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Benzenediols</sub_class>
    <direct_parent>Catechols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Catechol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>catechols</external_descriptor>
      <external_descriptor>dihydroxyphenylacetic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>168 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>4 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.98</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(3,4-dihydroxyphenyl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>168.1467</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>168.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC1=CC(O)=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CFFZDZCDUFSOFZ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38029</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01161</kegg_id>
  <chemspider_id>532</chemspider_id>
  <foodb_id>FDB000316</foodb_id>
  <drugbank_id>DB01702</drugbank_id>
  <chebi_id>41941</chebi_id>
  <pubchem_compound_id>547</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id>572</phenol_explorer_compound_id>
  <knapsack_id>C00040996</knapsack_id>
  <wikipedia_id>DOPAC</wikipedia_id>
  <bigg_id>36946</bigg_id>
  <metlin_id>6170</metlin_id>
  <meta_cyc_id>CPD-782</meta_cyc_id>
  <synthesis_reference>Joray, Marcel; Breuninger, Manfred.  Process for the preparation of phenolic compounds.    PCT Int. Appl.  (2007),     15pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:20 UTC</creation_date>
  <update_date>2020-04-15 21:57:06 UTC</update_date>
  <accession>BMDB0001337</accession>
  <secondary_accessions>
    <accession>BMDB01337</accession>
  </secondary_accessions>
  <name>Leukotriene A4</name>
  <description/>
  <synonyms>
    <synonym>(5S,6S,7E,9E,11Z,14Z)-5,6-Epoxyicosa-7,9,11,14-tetraenoate</synonym>
    <synonym>(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyeicosa-7,9,11,14-tetraenoate</synonym>
    <synonym>(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyeicosa-7,9,11,14-tetraenoic acid</synonym>
    <synonym>(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetraenoate</synonym>
    <synonym>5(S)-5,6-Oxido-7,9-trans-11,14-cis-eicosatetraenoic acid</synonym>
    <synonym>5S,6S-Epoxy-7E,9E,11Z,14Z-eicosatetraenoic acid</synonym>
    <synonym>5S,6S-Leukotriene a4</synonym>
    <synonym>LTA4</synonym>
    <synonym>(5S,6S,7E,9E,11Z,14Z)-5,6-Epoxyicosa-7,9,11,14-tetraenoic acid</synonym>
    <synonym>(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetraenoic acid</synonym>
    <synonym>5(S)-5,6-Oxido-7,9-trans-11,14-cis-eicosatetraenoate</synonym>
    <synonym>5S,6S-Epoxy-7E,9E,11Z,14Z-eicosatetraenoate</synonym>
    <synonym>(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa- 7,9,11,14-tetraenoate</synonym>
    <synonym>(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa- 7,9,11,14-tetraenoic acid</synonym>
    <synonym>(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetrenoioc acid</synonym>
    <synonym>Leukotriene a</synonym>
    <synonym>Leukotriene a 4</synonym>
    <synonym>Leukotrienes a</synonym>
    <synonym>Leukotriene a-4</synonym>
  </synonyms>
  <chemical_formula>C20H30O3</chemical_formula>
  <average_molecular_weight>318.4504</average_molecular_weight>
  <monisotopic_moleculate_weight>318.219494826</monisotopic_moleculate_weight>
  <iupac_name>4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraen-1-yl]oxiran-2-yl]butanoic acid</iupac_name>
  <traditional_iupac>leukotriene A4</traditional_iupac>
  <cas_registry_number>72059-45-1</cas_registry_number>
  <smiles>CCCCC\C=C/C\C=C/C=C/C=C/[C@@H]1O[C@H]1CCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1</inchi>
  <inchikey>UFPQIRYSPUYQHK-WAQVJNLQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as epoxy fatty acids. These are fatty acids containing an oxirane ring as part of the aliphatic chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Epoxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Epoxides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Epoxy fatty acid</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxirane</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Epoxy fatty acids</external_descriptor>
      <external_descriptor>Leukotrienes</external_descriptor>
      <external_descriptor>Leukotrienes</external_descriptor>
      <external_descriptor>epoxy fatty acid</external_descriptor>
      <external_descriptor>leukotriene</external_descriptor>
      <external_descriptor>long-chain fatty acid</external_descriptor>
      <external_descriptor>oxylipin</external_descriptor>
      <external_descriptor>polyunsaturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraen-1-yl]oxiran-2-yl]butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>318.4504</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>318.219494826</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC\C=C/C\C=C/C=C/C=C/[C@@H]1O[C@H]1CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H30O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UFPQIRYSPUYQHK-WAQVJNLQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>49.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>99.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180998</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00909</kegg_id>
  <chemspider_id>4444074</chemspider_id>
  <foodb_id>FDB022561</foodb_id>
  <drugbank_id/>
  <chebi_id>15651</chebi_id>
  <pubchem_compound_id>5280383</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <wikipedia_id>Leukotriene</wikipedia_id>
  <bigg_id>36355</bigg_id>
  <metlin_id>3449</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:21 UTC</creation_date>
  <update_date>2020-04-16 20:38:39 UTC</update_date>
  <accession>BMDB0001338</accession>
  <secondary_accessions>
    <accession>BMDB01338</accession>
  </secondary_accessions>
  <name>Palmityl-CoA</name>
  <description>Palmityl-CoA, also known as palmitoyl CoA or CoA, palmitoyl, belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. Palmityl-CoA is possibly soluble (in water) and a strong basic compound (based on its pKa). Palmityl-CoA exists in all living species, ranging from bacteria to humans. Palmityl-CoA participates in a number of enzymatic reactions, within cattle. In particular, Palmityl-CoA and glycerol 3-phosphate can be converted into lpa(16:0/0:0); which is mediated by the enzyme glycerol-3-phosphate acyltransferase. In addition, Lpa(16:0/0:0) and palmityl-CoA can be converted into PA(16:0/16:0); which is catalyzed by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. In cattle, palmityl-CoA is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(16:0/16:0/16:0) pathway and the glycerolipid metabolism pathway.</description>
  <synonyms>
    <synonym>coenzyme A, S-Hexadecanoate</synonym>
    <synonym>Palmitoyl coenzyme A</synonym>
    <synonym>S-Palmitoylcoenzyme A</synonym>
    <synonym>coenzyme A, S-Hexadecanoic acid</synonym>
    <synonym>Hexadecanoyl-CoA</synonym>
    <synonym>CoA, Hexadecanoyl</synonym>
    <synonym>CoA, Palmityl</synonym>
    <synonym>Hexadecanoyl CoA</synonym>
    <synonym>coenzyme A, Palmitoyl</synonym>
    <synonym>Palmityl CoA</synonym>
    <synonym>CoA, Palmitoyl</synonym>
    <synonym>Palmitoyl CoA</synonym>
  </synonyms>
  <chemical_formula>C37H66N7O17P3S</chemical_formula>
  <average_molecular_weight>1005.943</average_molecular_weight>
  <monisotopic_moleculate_weight>1005.344873947</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(hexadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>palmitoyl-coa</traditional_iupac>
  <cas_registry_number>1763-10-6</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C37H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h24-26,30-32,36,47-48H,4-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/t26-,30-,31-,32+,36-/m1/s1</inchi>
  <inchikey>MNBKLUUYKPBKDU-BBECNAHFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-fucopyranose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(hexadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1005.943</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1005.344873947</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C37H66N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C37H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h24-26,30-32,36,47-48H,4-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/t26-,30-,31-,32+,36-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MNBKLUUYKPBKDU-BBECNAHFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>236.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>102.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:0)</name>
      <smpdb_id>SMP0077151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:0)</name>
      <smpdb_id>SMP0077153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:0)</name>
      <smpdb_id>SMP0077171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:0)</name>
      <smpdb_id>SMP0077173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077235</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077237</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077238</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077239</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077240</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077241</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077242</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077243</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077244</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077245</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077246</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077247</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077248</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077249</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077250</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077251</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077252</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077253</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077254</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077255</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077256</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077257</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077258</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077259</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077260</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077261</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077262</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077263</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077264</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077265</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077266</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077267</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077268</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077269</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077270</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077271</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077272</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077273</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077274</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077275</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077276</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077277</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077278</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077279</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077280</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077281</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077282</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077283</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077284</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077285</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077286</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077287</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077288</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077289</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077290</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077291</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077292</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077293</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077294</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077295</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077296</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077297</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077298</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:0)</name>
      <smpdb_id>SMP0077299</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077300</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077301</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077302</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077303</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077304</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077305</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077306</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077307</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077308</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077309</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:0)</name>
      <smpdb_id>SMP0077310</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077311</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:0)</name>
      <smpdb_id>SMP0077312</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077313</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077314</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077315</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077316</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077317</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077318</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077319</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077320</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077330</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077331</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077332</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077334</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077335</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077336</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077337</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077339</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077341</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077342</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077348</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077349</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077350</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077351</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077357</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077365</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077366</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077367</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077368</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077369</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077371</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077372</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077374</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077375</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077376</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077377</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077378</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077379</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077380</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077381</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077382</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077383</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077384</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077385</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077386</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077387</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077388</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077389</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077390</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077391</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077392</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077393</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077394</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077395</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077396</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077397</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077398</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077399</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077400</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077401</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077404</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077406</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077415</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077416</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077419</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077420</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077421</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077422</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077423</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077424</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077425</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077427</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077428</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077431</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077432</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077433</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077434</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077435</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077437</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077438</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077439</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077440</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077441</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077442</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077443</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077444</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077445</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077446</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077447</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077448</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077449</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077450</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077451</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077452</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077453</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077454</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077455</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077456</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077457</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077458</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077459</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077460</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077461</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077462</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077463</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077464</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077465</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077466</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077467</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077468</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077469</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077470</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077471</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077472</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077473</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077474</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077475</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077476</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077477</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077478</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077479</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077480</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077481</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077482</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077483</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077484</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077485</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077486</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077487</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077488</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077489</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077490</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077491</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077492</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077493</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077494</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077495</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077496</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077497</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077498</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077499</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077500</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077501</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077502</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077503</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077504</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077505</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077506</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077507</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077508</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077509</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077510</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077511</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077512</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077513</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077514</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077515</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077516</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077517</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077518</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077519</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077520</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077521</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077522</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077523</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077524</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077525</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077526</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077527</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077528</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077529</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077530</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077531</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077532</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077533</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077534</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077535</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077536</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077537</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077538</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077539</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077540</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077541</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077542</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077543</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077544</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077545</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077546</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077547</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077548</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077549</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077550</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077551</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077552</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077553</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077554</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077555</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077556</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077557</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077558</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077559</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077560</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077561</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077562</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077563</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077564</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077565</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077566</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <smpdb_id>SMP0077640</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077701</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:0)</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077704</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077715</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077716</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077717</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077718</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077719</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077720</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077721</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077722</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078127</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078128</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:0)</name>
      <smpdb_id>SMP0078132</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078133</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078134</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078135</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078136</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078137</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078138</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078139</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078140</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078141</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078142</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078143</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078144</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078145</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078146</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078147</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078148</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078149</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078150</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078151</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078152</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078153</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078154</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078155</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078158</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078159</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078163</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078614</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078615</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078616</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078617</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078618</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078619</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078623</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078624</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078625</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078626</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078627</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078628</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078629</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078630</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078634</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078635</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078636</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078637</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078638</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078639</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078640</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078641</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078642</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078643</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078644</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078646</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078647</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078648</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078649</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078650</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078651</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078652</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0079091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079095</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079096</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079097</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079098</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079100</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079101</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079104</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079105</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079106</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079107</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079108</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079109</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079110</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079111</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079112</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079113</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079114</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079115</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079116</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079117</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079118</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079119</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079120</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079464</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079465</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079466</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079467</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079468</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079469</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079470</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079471</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079472</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079473</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079474</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079475</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079476</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079477</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079478</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079479</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079480</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079481</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079482</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079483</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079484</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079485</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079486</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079487</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079774</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079775</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079776</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079777</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079778</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079779</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079780</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079781</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079782</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079783</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079784</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079785</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079786</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079787</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079788</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079789</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079790</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0080019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0080021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080022</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080023</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080024</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080025</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080026</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080027</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080028</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080029</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080030</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080031</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080032</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080033</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080034</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080035</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080036</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080038</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080040</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080041</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080042</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080237</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080245</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/16:0)</name>
      <smpdb_id>SMP0108480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/16:0)</name>
      <smpdb_id>SMP0108463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/12:0)</name>
      <smpdb_id>SMP0108479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/14:0)</name>
      <smpdb_id>SMP0108468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/15:0)</name>
      <smpdb_id>SMP0108507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/16:0)</name>
      <smpdb_id>SMP0108467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/17:0)</name>
      <smpdb_id>SMP0108458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/18:0)</name>
      <smpdb_id>SMP0108518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/8:0)</name>
      <smpdb_id>SMP0108504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0108626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0108627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0108628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0108629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0108630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0108631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0108632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0108633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0108634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0108635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0108636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0108637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0108638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0108639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0108640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0108641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0108642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/16:0)</name>
      <smpdb_id>SMP0108496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/16:0)</name>
      <smpdb_id>SMP0072655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0072683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/16:0)</name>
      <smpdb_id>SMP0072710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/16:0)</name>
      <smpdb_id>SMP0072736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0072737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:0)</name>
      <smpdb_id>SMP0072738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0072739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0072740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:0)</name>
      <smpdb_id>SMP0072745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0072746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:0)</name>
      <smpdb_id>SMP0072753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0072754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/24:0)</name>
      <smpdb_id>SMP0072760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0072761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0073089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/16:0)</name>
      <smpdb_id>SMP0073116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/16:0)</name>
      <smpdb_id>SMP0073142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:0)</name>
      <smpdb_id>SMP0073144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:0)</name>
      <smpdb_id>SMP0073151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:0)</name>
      <smpdb_id>SMP0073159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/24:0)</name>
      <smpdb_id>SMP0073166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/16:0)</name>
      <smpdb_id>SMP0073494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/16:0)</name>
      <smpdb_id>SMP0073520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:0)</name>
      <smpdb_id>SMP0073522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:0)</name>
      <smpdb_id>SMP0073529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:0)</name>
      <smpdb_id>SMP0073537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/24:0)</name>
      <smpdb_id>SMP0073544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:0)</name>
      <smpdb_id>SMP0073871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:0)</name>
      <smpdb_id>SMP0073873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:0)</name>
      <smpdb_id>SMP0073880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:0)</name>
      <smpdb_id>SMP0073888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/24:0)</name>
      <smpdb_id>SMP0073895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:0)</name>
      <smpdb_id>SMP0073922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0073923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0073924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:0)</name>
      <smpdb_id>SMP0073929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0073930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:0)</name>
      <smpdb_id>SMP0073937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0073938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/24:0)</name>
      <smpdb_id>SMP0073944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0073945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0073952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:0)</name>
      <smpdb_id>SMP0074069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:0)</name>
      <smpdb_id>SMP0074077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/24:0)</name>
      <smpdb_id>SMP0074084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0074122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0074129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:0)</name>
      <smpdb_id>SMP0074177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0074178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/24:0)</name>
      <smpdb_id>SMP0074184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0074185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0074192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:0/24:0)</name>
      <smpdb_id>SMP0074219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0074220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/16:0)</name>
      <smpdb_id>SMP0108332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/16:0)</name>
      <smpdb_id>SMP0108299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/16:0)</name>
      <smpdb_id>SMP0108972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/16:0)</name>
      <smpdb_id>SMP0108997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0109025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0109047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0109068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/16:0)</name>
      <smpdb_id>SMP0108293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/16:0)</name>
      <smpdb_id>SMP0108247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/10:0)</name>
      <smpdb_id>SMP0108274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/19:0)</name>
      <smpdb_id>SMP0108269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/21:0)</name>
      <smpdb_id>SMP0108251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/16:0)</name>
      <smpdb_id>SMP0108302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/16:0)</name>
      <smpdb_id>SMP0108280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/16:0)</name>
      <smpdb_id>SMP0108383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/16:0)</name>
      <smpdb_id>SMP0108380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/16:0)</name>
      <smpdb_id>SMP0108346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/10:0)</name>
      <smpdb_id>SMP0108350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/15:0)</name>
      <smpdb_id>SMP0108355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/16:0)</name>
      <smpdb_id>SMP0108381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/17:0)</name>
      <smpdb_id>SMP0108364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/18:0)</name>
      <smpdb_id>SMP0108356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/22:0)</name>
      <smpdb_id>SMP0108385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/16:0)</name>
      <smpdb_id>SMP0108391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/16:0)</name>
      <smpdb_id>SMP0108359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/16:0)</name>
      <smpdb_id>SMP0108430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/10:0)</name>
      <smpdb_id>SMP0108404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/12:0)</name>
      <smpdb_id>SMP0108406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/16:0)</name>
      <smpdb_id>SMP0108412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/16:0)</name>
      <smpdb_id>SMP0108427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/16:0)</name>
      <smpdb_id>SMP0108450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/13:0)</name>
      <smpdb_id>SMP0108513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/14:0)</name>
      <smpdb_id>SMP0108449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/15:0)</name>
      <smpdb_id>SMP0108493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/16:0)</name>
      <smpdb_id>SMP0108500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/18:0)</name>
      <smpdb_id>SMP0108474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/19:0)</name>
      <smpdb_id>SMP0108446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0110137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0110138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/16:0)</name>
      <smpdb_id>SMP0108530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/16:0)</name>
      <smpdb_id>SMP0108490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/16:0)</name>
      <smpdb_id>SMP0110371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/16:0)</name>
      <smpdb_id>SMP0110393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/16:0)</name>
      <smpdb_id>SMP0110414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/16:0)</name>
      <smpdb_id>SMP0110434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/16:0)</name>
      <smpdb_id>SMP0110453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/17:0)</name>
      <smpdb_id>SMP0110454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/18:0)</name>
      <smpdb_id>SMP0110455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0110459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/16:0)</name>
      <smpdb_id>SMP0110555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/16:0)</name>
      <smpdb_id>SMP0110671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/16:0)</name>
      <smpdb_id>SMP0110692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/16:0)</name>
      <smpdb_id>SMP0110712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/16:0)</name>
      <smpdb_id>SMP0110731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/16:0)</name>
      <smpdb_id>SMP0110749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/17:0)</name>
      <smpdb_id>SMP0110750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/18:0)</name>
      <smpdb_id>SMP0110751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/16:0)</name>
      <smpdb_id>SMP0110847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0110956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0110976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0110995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/16:0)</name>
      <smpdb_id>SMP0111013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/16:0)</name>
      <smpdb_id>SMP0111034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/16:0)</name>
      <smpdb_id>SMP0111054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/16:0)</name>
      <smpdb_id>SMP0111073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/16:0)</name>
      <smpdb_id>SMP0111091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/17:0)</name>
      <smpdb_id>SMP0111092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/18:0)</name>
      <smpdb_id>SMP0111093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/19:0)</name>
      <smpdb_id>SMP0111094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0111105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0111106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0111107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/16:0)</name>
      <smpdb_id>SMP0111253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/16:0)</name>
      <smpdb_id>SMP0111280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/16:0)</name>
      <smpdb_id>SMP0111298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/16:0)</name>
      <smpdb_id>SMP0111315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/16:0)</name>
      <smpdb_id>SMP0111331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/16:0)</name>
      <smpdb_id>SMP0111346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/17:0)</name>
      <smpdb_id>SMP0111347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/18:0)</name>
      <smpdb_id>SMP0111348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0111359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0111467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/16:0)</name>
      <smpdb_id>SMP0111490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/16:0)</name>
      <smpdb_id>SMP0111507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/16:0)</name>
      <smpdb_id>SMP0111523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/16:0)</name>
      <smpdb_id>SMP0111538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/16:0)</name>
      <smpdb_id>SMP0111552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/17:0)</name>
      <smpdb_id>SMP0111553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/18:0)</name>
      <smpdb_id>SMP0111554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0111660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/16:0)</name>
      <smpdb_id>SMP0111680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/16:0)</name>
      <smpdb_id>SMP0111696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/16:0)</name>
      <smpdb_id>SMP0111711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/16:0)</name>
      <smpdb_id>SMP0111725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/16:0)</name>
      <smpdb_id>SMP0111738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/17:0)</name>
      <smpdb_id>SMP0111739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/18:0)</name>
      <smpdb_id>SMP0111740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0111833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Elongation in Mitochondria</name>
      <smpdb_id>SMP0087194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181385</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00154</kegg_id>
  <chemspider_id>559149</chemspider_id>
  <pubchem_compound_id>644109</pubchem_compound_id>
  <foodb_id>FDB031086</foodb_id>
  <pdbe_id/>
  <chebi_id>15525</chebi_id>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id>C00007462</knapsack_id>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00085</protein_accession>
      <name>Serine palmitoyltransferase 1</name>
      <uniprot_id>Q3MHG1</uniprot_id>
      <gene_name>SPTLC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00245</protein_accession>
      <name>Carnitine O-palmitoyltransferase 1, muscle isoform</name>
      <uniprot_id>Q58DK1</uniprot_id>
      <gene_name>CPT1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00246</protein_accession>
      <name>Carnitine O-palmitoyltransferase 2, mitochondrial</name>
      <uniprot_id>Q2KJB7</uniprot_id>
      <gene_name>CPT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00247</protein_accession>
      <name>Probable palmitoyltransferase ZDHHC6</name>
      <uniprot_id>Q2HJ95</uniprot_id>
      <gene_name>ZDHHC6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00248</protein_accession>
      <name>Palmitoyltransferase ZDHHC9</name>
      <uniprot_id>Q58DA8</uniprot_id>
      <gene_name>ZDHHC9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00249</protein_accession>
      <name>Probable palmitoyltransferase ZDHHC21</name>
      <uniprot_id>A2VDT6</uniprot_id>
      <gene_name>ZDHHC21</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00250</protein_accession>
      <name>Probable palmitoyltransferase ZDHHC20</name>
      <uniprot_id>Q0VC89</uniprot_id>
      <gene_name>ZDHHC20</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00251</protein_accession>
      <name>Probable palmitoyltransferase ZDHHC16</name>
      <uniprot_id>Q58CU4</uniprot_id>
      <gene_name>ZDHHC16</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00252</protein_accession>
      <name>Probable palmitoyltransferase ZDHHC4</name>
      <uniprot_id>Q58DT3</uniprot_id>
      <gene_name>ZDHHC4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:22 UTC</creation_date>
  <update_date>2020-04-15 22:15:09 UTC</update_date>
  <accession>BMDB0001339</accession>
  <secondary_accessions>
    <accession>BMDB01339</accession>
  </secondary_accessions>
  <name>Glutaryl-CoA</name>
  <description/>
  <synonyms>
    <synonym>Glutaryl-coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C26H42N7O19P3S</chemical_formula>
  <average_molecular_weight>881.633</average_molecular_weight>
  <monisotopic_moleculate_weight>881.146902423</monisotopic_moleculate_weight>
  <iupac_name>5-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-5-oxopentanoic acid</iupac_name>
  <traditional_iupac>5-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-5-oxopentanoic acid</traditional_iupac>
  <cas_registry_number>103192-48-9</cas_registry_number>
  <smiles>CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCCC(O)=O</smiles>
  <inchi>InChI=1S/C26H42N7O19P3S/c1-26(2,21(39)24(40)29-7-6-15(34)28-8-9-56-17(37)5-3-4-16(35)36)11-49-55(46,47)52-54(44,45)48-10-14-20(51-53(41,42)43)19(38)25(50-14)33-13-32-18-22(27)30-12-31-23(18)33/h12-14,19-21,25,38-39H,3-11H2,1-2H3,(H,28,34)(H,29,40)(H,35,36)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)/t14-,19-,20-,21?,25-/m1/s1</inchi>
  <inchikey>SYKWLIJQEHRDNH-KRPIADGTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Long-chain fatty acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>2,3,4-saturated fatty acyl CoAs</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fatty acyl CoAs</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-5-oxopentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>881.633</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>881.146902423</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H42N7O19P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H42N7O19P3S/c1-26(2,21(39)24(40)29-7-6-15(34)28-8-9-56-17(37)5-3-4-16(35)36)11-49-55(46,47)52-54(44,45)48-10-14-20(51-53(41,42)43)19(38)25(50-14)33-13-32-18-22(27)30-12-31-23(18)33/h12-14,19-21,25,38-39H,3-11H2,1-2H3,(H,28,34)(H,29,40)(H,35,36)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)/t14-,19-,20-,21?,25-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SYKWLIJQEHRDNH-KRPIADGTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>400.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>187.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>78.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33907</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00527</kegg_id>
  <chemspider_id>388388</chemspider_id>
  <foodb_id>FDB022563</foodb_id>
  <drugbank_id/>
  <chebi_id>15524</chebi_id>
  <pubchem_compound_id>439252</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <wikipedia_id>Glutaryl-CoA</wikipedia_id>
  <bigg_id>35255</bigg_id>
  <metlin_id>6173</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00121</protein_accession>
      <name>Glutaryl-CoA dehydrogenase, mitochondrial</name>
      <uniprot_id>Q2KHZ9</uniprot_id>
      <gene_name>GCDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:23 UTC</creation_date>
  <update_date>2020-03-13 16:27:23 UTC</update_date>
  <accession>BMDB0001340</accession>
  <secondary_accessions>
    <accession>BMDB01340</accession>
  </secondary_accessions>
  <name>Diguanosine tetraphosphate</name>
  <description/>
  <synonyms>
    <synonym>(PPG)2</synonym>
    <synonym>Bis(5'-guanosyl) tetraphosphate</synonym>
    <synonym>Bis(guanylyl) diphosphate</synonym>
    <synonym>g(5')P4(5')g</synonym>
    <synonym>GP4g</synonym>
    <synonym>GPPPPG</synonym>
    <synonym>Guanosine(5')tetraphospho(5')guanosine</synonym>
    <synonym>P1,P4-Bis(5'-guanosyl) tetraphosphate</synonym>
    <synonym>Bis(5'-guanosyl) tetraphosphoric acid</synonym>
    <synonym>Bis(guanylyl) diphosphoric acid</synonym>
    <synonym>P1,P4-Bis(5'-guanosyl) tetraphosphoric acid</synonym>
    <synonym>Diguanosine tetraphosphoric acid</synonym>
    <synonym>[5-(2-Amino-6-hydroxy-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-[[[[5-(2-amino-6-hydroxy-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-phosphinic acid</synonym>
  </synonyms>
  <chemical_formula>C20H28N10O21P4</chemical_formula>
  <average_molecular_weight>868.3858</average_molecular_weight>
  <monisotopic_moleculate_weight>868.038094056</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>diguanosine tetraphosphate</traditional_iupac>
  <cas_registry_number>4130-19-2</cas_registry_number>
  <smiles>NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=C(N)NC4=O)[C@@H](O)[C@H]2O)C(=O)N1</smiles>
  <inchi>InChI=1S/C20H28N10O21P4/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(47-17)1-45-52(37,38)49-54(41,42)51-55(43,44)50-53(39,40)46-2-6-10(32)12(34)18(48-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1</inchi>
  <inchikey>OLGWXCQXRSSQPO-MHARETSRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside polyphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside polyphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>guanosine 5'-phosphate</external_descriptor>
      <external_descriptor>purine ribonucleoside 5'-tetraphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>868.3858</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>868.038094056</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=C(N)NC4=O)[C@@H](O)[C@H]2O)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H28N10O21P4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H28N10O21P4/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(47-17)1-45-52(37,38)49-54(41,42)51-55(43,44)50-53(39,40)46-2-6-10(32)12(34)18(48-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OLGWXCQXRSSQPO-MHARETSRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>465.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>168.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>68.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30187</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01261</kegg_id>
  <chemspider_id>144813</chemspider_id>
  <foodb_id>FDB031082</foodb_id>
  <drugbank_id/>
  <chebi_id>15883</chebi_id>
  <pubchem_compound_id>165186</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <bigg_id/>
  <metlin_id>4175</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:24 UTC</creation_date>
  <update_date>2020-04-16 17:52:23 UTC</update_date>
  <accession>BMDB0001341</accession>
  <secondary_accessions>
    <accession>BMDB01341</accession>
  </secondary_accessions>
  <name>ADP</name>
  <description>Adp, also known as H3ADP or magnesium ADP, belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. Adp is possibly soluble (in water) and a strong basic compound (based on its pKa). Adp exists in all living species, ranging from bacteria to humans. Adp is a potentially toxic compound.</description>
  <synonyms>
    <synonym>5'-Adenylphosphoric acid</synonym>
    <synonym>Adenosine 5'-diphosphate</synonym>
    <synonym>ADENOSINE-5'-diphosphATE</synonym>
    <synonym>H3ADP</synonym>
    <synonym>5'-Adenylphosphate</synonym>
    <synonym>Adenosine 5'-diphosphoric acid</synonym>
    <synonym>ADENOSINE-5'-diphosphoric acid</synonym>
    <synonym>Adenosindiphosphorsaeure</synonym>
    <synonym>Adenosine 5'-pyrophosphate</synonym>
    <synonym>Adenosine diphosphate</synonym>
    <synonym>Adenosine pyrophosphate</synonym>
    <synonym>Adenosine-5-diphosphate</synonym>
    <synonym>Adenosine-diphosphate</synonym>
    <synonym>5'-Pyrophosphate, adenosine</synonym>
    <synonym>Adenosine 5' pyrophosphate</synonym>
    <synonym>Diphosphate, adenosine</synonym>
    <synonym>Magnesium ADP</synonym>
    <synonym>MgADP</synonym>
    <synonym>Pyrophosphate, adenosine</synonym>
    <synonym>ADP, Magnesium</synonym>
    <synonym>Adenosine diphosphoric acid</synonym>
    <synonym>ADP</synonym>
  </synonyms>
  <chemical_formula>C10H15N5O10P2</chemical_formula>
  <average_molecular_weight>427.2011</average_molecular_weight>
  <monisotopic_moleculate_weight>427.029414749</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>adenosine-diphosphate</traditional_iupac>
  <cas_registry_number>58-64-0</cas_registry_number>
  <smiles>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>XTWYTFMLZFPYCI-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside diphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ribonucleotides</external_descriptor>
      <external_descriptor>adenosine 5'-phosphate</external_descriptor>
      <external_descriptor>purine ribonucleoside 5'-diphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>427.2011</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>427.029414749</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H15N5O10P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XTWYTFMLZFPYCI-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>232.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>84.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Beta Oxidation of Very Long Chain Fatty Acids</name>
      <smpdb_id>SMP0087259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gastric Acid Production</name>
      <smpdb_id>SMP0119381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutathione Metabolism</name>
      <smpdb_id>SMP0087167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Degradation</name>
      <smpdb_id>SMP0087253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Electron Transport Chain</name>
      <smpdb_id>SMP0087261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Muscle/Heart Contraction</name>
      <smpdb_id>SMP0119378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pantothenate and CoA Biosynthesis</name>
      <smpdb_id>SMP0087207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis</name>
      <smpdb_id>SMP0072037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:0)</name>
      <smpdb_id>SMP0080430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0080431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/15:0)</name>
      <smpdb_id>SMP0080432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:0)</name>
      <smpdb_id>SMP0080433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0080434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:0)</name>
      <smpdb_id>SMP0080435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0080436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0080437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:0)</name>
      <smpdb_id>SMP0080442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0080443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:0)</name>
      <smpdb_id>SMP0080450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0080451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:0)</name>
      <smpdb_id>SMP0080457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0080458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0080459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0080460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0080461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/15:0)</name>
      <smpdb_id>SMP0080487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:0)</name>
      <smpdb_id>SMP0080488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0080489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:0)</name>
      <smpdb_id>SMP0080490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0080491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0080492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:0)</name>
      <smpdb_id>SMP0080497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0080498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:0)</name>
      <smpdb_id>SMP0080505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0080506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:0)</name>
      <smpdb_id>SMP0080512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0080513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:0)</name>
      <smpdb_id>SMP0080514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0080515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:0)</name>
      <smpdb_id>SMP0080516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0080517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0080518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:0)</name>
      <smpdb_id>SMP0080523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0080524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:0)</name>
      <smpdb_id>SMP0080531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0080532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:0)</name>
      <smpdb_id>SMP0080538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0080539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:0)</name>
      <smpdb_id>SMP0080565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0080566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0080567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:0)</name>
      <smpdb_id>SMP0080572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0080573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:0)</name>
      <smpdb_id>SMP0080580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0080581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:0)</name>
      <smpdb_id>SMP0080587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0080588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0080595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:0)</name>
      <smpdb_id>SMP0080712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0080713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:0)</name>
      <smpdb_id>SMP0080720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0080721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:0)</name>
      <smpdb_id>SMP0080727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0080728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0080765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0080772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:0)</name>
      <smpdb_id>SMP0080820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0080821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:0)</name>
      <smpdb_id>SMP0080827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0080828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0080835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:0)</name>
      <smpdb_id>SMP0080864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0080865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis</name>
      <smpdb_id>SMP0072048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:0)</name>
      <smpdb_id>SMP0082233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0082234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/15:0)</name>
      <smpdb_id>SMP0082235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:0)</name>
      <smpdb_id>SMP0082236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0082237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:0)</name>
      <smpdb_id>SMP0082238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0082239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0082240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:0)</name>
      <smpdb_id>SMP0082245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0082246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:0)</name>
      <smpdb_id>SMP0082253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0082254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:0)</name>
      <smpdb_id>SMP0082260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0082261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0082262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0082263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0082264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/15:0)</name>
      <smpdb_id>SMP0082290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:0)</name>
      <smpdb_id>SMP0082291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0082292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:0)</name>
      <smpdb_id>SMP0082293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0082294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0082295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:0)</name>
      <smpdb_id>SMP0082300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0082301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:0)</name>
      <smpdb_id>SMP0082308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0082309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:0)</name>
      <smpdb_id>SMP0082315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0082316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:0)</name>
      <smpdb_id>SMP0082317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0082318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:0)</name>
      <smpdb_id>SMP0082319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0082320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0082321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:0)</name>
      <smpdb_id>SMP0082326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0082327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:0)</name>
      <smpdb_id>SMP0082334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0082335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:0)</name>
      <smpdb_id>SMP0082341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0082342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:0)</name>
      <smpdb_id>SMP0082368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0082369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0082370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:0)</name>
      <smpdb_id>SMP0082375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0082376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:0)</name>
      <smpdb_id>SMP0082383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0082384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:0)</name>
      <smpdb_id>SMP0082390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0082391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0082398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:0)</name>
      <smpdb_id>SMP0082520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0082521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:0)</name>
      <smpdb_id>SMP0082528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0082529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:0)</name>
      <smpdb_id>SMP0082535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0082536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0082574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0082581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:0)</name>
      <smpdb_id>SMP0082629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0082630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:0)</name>
      <smpdb_id>SMP0082636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0082637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0082644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:0)</name>
      <smpdb_id>SMP0082671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0082672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylinositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Riboflavin Metabolism</name>
      <smpdb_id>SMP0087211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Selenoamino Acid Metabolism</name>
      <smpdb_id>SMP0087161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sulfate/Sulfite Metabolism</name>
      <smpdb_id>SMP0087216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Thiamine Metabolism</name>
      <smpdb_id>SMP0087212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Threonine and 2-Oxobutanoate Degradation</name>
      <smpdb_id>SMP0087262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Trehalose Degradation</name>
      <smpdb_id>SMP0087263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ubiquitin–Proteasome Pathway</name>
      <smpdb_id>SMP0120929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38031</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1065</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1624</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>1522</spectrum_id>
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      <spectrum_id>1523</spectrum_id>
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      <spectrum_id>5202</spectrum_id>
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      <spectrum_id>180252</spectrum_id>
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      <spectrum_id>180253</spectrum_id>
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    <spectrum>
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      <spectrum_id>180254</spectrum_id>
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    <spectrum>
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      <spectrum_id>182586</spectrum_id>
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    <spectrum>
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      <spectrum_id>182587</spectrum_id>
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    <spectrum>
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      <spectrum_id>182588</spectrum_id>
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    <spectrum>
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      <spectrum_id>438912</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439037</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449629</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0 - 26.600</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44.</reference_text>
          <pubmed_id>7196410</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB021817</foodb_id>
  <chemspider_id>5800</chemspider_id>
  <pubchem_compound_id>6022</pubchem_compound_id>
  <kegg_id>C00008</kegg_id>
  <chebi_id>16761</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00019353</knapsack_id>
  <meta_cyc_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>33496</bigg_id>
  <wikipedia_id>ADP</wikipedia_id>
  <metlin_id>6175</metlin_id>
  <synthesis_reference>Yamagata, Yukio.  Prebiotic formation of ADP and ATP from AMP, calcium phosphates and cyanate in aqueous solution.    Origins of Life and Evolution of the Biosphere  (1999),  29(5),  511-520.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44.</reference_text>
      <pubmed_id>7196410</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00089</protein_accession>
      <name>Inositol-tetrakisphosphate 1-kinase</name>
      <uniprot_id>P0C0T1</uniprot_id>
      <gene_name>ITPK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00101</protein_accession>
      <name>Diphosphomevalonate decarboxylase</name>
      <uniprot_id>Q0P570</uniprot_id>
      <gene_name>MVD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00118</protein_accession>
      <name>Monofunctional C1-tetrahydrofolate synthase, mitochondrial</name>
      <uniprot_id>Q0VCR7</uniprot_id>
      <gene_name>MTHFD1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00132</protein_accession>
      <name>Poly(ADP-ribose) glycohydrolase ARH3</name>
      <uniprot_id>Q3SYV9</uniprot_id>
      <gene_name>ADPRHL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00133</protein_accession>
      <name>Manganese-dependent ADP-ribose/CDP-alcohol diphosphatase</name>
      <uniprot_id>A7YY53</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00134</protein_accession>
      <name>[Protein ADP-ribosylarginine] hydrolase</name>
      <uniprot_id>Q32KR8</uniprot_id>
      <gene_name>ADPRH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00135</protein_accession>
      <name>Poly(ADP-ribose) glycohydrolase</name>
      <uniprot_id>O02776</uniprot_id>
      <gene_name>PARG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00137</protein_accession>
      <name>G protein-coupled receptor kinase 7</name>
      <uniprot_id>Q8WMV0</uniprot_id>
      <gene_name>GRK7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00138</protein_accession>
      <name>Cystic fibrosis transmembrane conductance regulator</name>
      <uniprot_id>P35071</uniprot_id>
      <gene_name>CFTR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00140</protein_accession>
      <name>6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 1</name>
      <uniprot_id>P49872</uniprot_id>
      <gene_name>PFKFB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00141</protein_accession>
      <name>Proto-oncogene tyrosine-protein kinase Fyn</name>
      <uniprot_id>A0JNB0</uniprot_id>
      <gene_name>FYN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00142</protein_accession>
      <name>[3-methyl-2-oxobutanoate dehydrogenase [lipoamide]] kinase, mitochondrial</name>
      <uniprot_id>Q2KJG8</uniprot_id>
      <gene_name>BCKDK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00143</protein_accession>
      <name>Insulin-like growth factor 1 receptor</name>
      <uniprot_id>Q05688</uniprot_id>
      <gene_name>IGF1R</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00145</protein_accession>
      <name>Sodium/potassium-transporting ATPase subunit alpha-1</name>
      <uniprot_id>Q08DA1</uniprot_id>
      <gene_name>ATP1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00146</protein_accession>
      <name>Activin receptor type-2A</name>
      <uniprot_id>Q28043</uniprot_id>
      <gene_name>ACVR2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00147</protein_accession>
      <name>Arsenical pump-driving ATPase</name>
      <uniprot_id>A5PJI5</uniprot_id>
      <gene_name>ASNA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00148</protein_accession>
      <name>Glutamine synthetase</name>
      <uniprot_id>P15103</uniprot_id>
      <gene_name>GLUL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00152</protein_accession>
      <name>Activin receptor type-2B</name>
      <uniprot_id>Q95126</uniprot_id>
      <gene_name>ACVR2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00153</protein_accession>
      <name>Calcium-transporting ATPase type 2C member 1</name>
      <uniprot_id>P57709</uniprot_id>
      <gene_name>ATP2C1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00155</protein_accession>
      <name>6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 3</name>
      <uniprot_id>Q28901</uniprot_id>
      <gene_name>PFKFB3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00157</protein_accession>
      <name>Probable phospholipid-transporting ATPase IIB</name>
      <uniprot_id>A1A4J6</uniprot_id>
      <gene_name>ATP9B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00158</protein_accession>
      <name>Sodium/potassium-transporting ATPase subunit alpha-2</name>
      <uniprot_id>A2VDL6</uniprot_id>
      <gene_name>ATP1A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00162</protein_accession>
      <name>6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 2</name>
      <uniprot_id>P26285</uniprot_id>
      <gene_name>PFKFB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00166</protein_accession>
      <name>Beta-adrenergic receptor kinase 2</name>
      <uniprot_id>P26818</uniprot_id>
      <gene_name>ADRBK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00168</protein_accession>
      <name>Cell division control protein 2 homolog</name>
      <uniprot_id>P48734</uniprot_id>
      <gene_name>CDC2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00169</protein_accession>
      <name>Folylpolyglutamate synthase, mitochondrial</name>
      <uniprot_id>A6H751</uniprot_id>
      <gene_name>FPGS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00172</protein_accession>
      <name>ITK protein</name>
      <uniprot_id>A7Z039</uniprot_id>
      <gene_name>ITK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00175</protein_accession>
      <name>ATP-citrate synthase</name>
      <uniprot_id>Q32PF2</uniprot_id>
      <gene_name>ACLY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00178</protein_accession>
      <name>G protein-coupled receptor kinase 5</name>
      <uniprot_id>P43249</uniprot_id>
      <gene_name>GRK5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00179</protein_accession>
      <name>YES1 protein</name>
      <uniprot_id>A7MB57</uniprot_id>
      <gene_name>YES1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00180</protein_accession>
      <name>FGR protein</name>
      <uniprot_id>A5PKG9</uniprot_id>
      <gene_name>FGR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00183</protein_accession>
      <name>Tyrosine-protein kinase receptor</name>
      <uniprot_id>A8KC75</uniprot_id>
      <gene_name>NTRK3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00185</protein_accession>
      <name>Activated CDC42 kinase 1</name>
      <uniprot_id>Q17R13</uniprot_id>
      <gene_name>TNK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00186</protein_accession>
      <name>Integrin-linked protein kinase</name>
      <uniprot_id>Q3SWY2</uniprot_id>
      <gene_name>ILK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00189</protein_accession>
      <name>ATP synthase subunit beta, mitochondrial</name>
      <uniprot_id>P00829</uniprot_id>
      <gene_name>ATP5B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00191</protein_accession>
      <name>ATP10D protein</name>
      <uniprot_id>A7Z029</uniprot_id>
      <gene_name>ATP10D</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00196</protein_accession>
      <name>Probable phospholipid-transporting ATPase IA</name>
      <uniprot_id>Q29449</uniprot_id>
      <gene_name>ATP8A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00197</protein_accession>
      <name>Glutathione synthetase</name>
      <uniprot_id>Q5EAC2</uniprot_id>
      <gene_name>GSS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00199</protein_accession>
      <name>Cell division protein kinase 9</name>
      <uniprot_id>Q5EAB2</uniprot_id>
      <gene_name>CDK9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00200</protein_accession>
      <name>Tyrosine-protein kinase receptor</name>
      <uniprot_id>A7Z067</uniprot_id>
      <gene_name>CSF1R</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00202</protein_accession>
      <name>Beta-adrenergic receptor kinase 1</name>
      <uniprot_id>P21146</uniprot_id>
      <gene_name>ADRBK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00203</protein_accession>
      <name>Tyrosine-protein kinase CSK</name>
      <uniprot_id>Q0VBZ0</uniprot_id>
      <gene_name>CSK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00204</protein_accession>
      <name>Acetyl-CoA carboxylase 1</name>
      <uniprot_id>Q9TTS3</uniprot_id>
      <gene_name>ACACA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00205</protein_accession>
      <name>Activin receptor type-1</name>
      <uniprot_id>Q28041</uniprot_id>
      <gene_name>ACVR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00207</protein_accession>
      <name>Sarcoplasmic/endoplasmic reticulum calcium ATPase 1</name>
      <uniprot_id>Q0VCY0</uniprot_id>
      <gene_name>ATP2A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00211</protein_accession>
      <name>Tyrosine-protein kinase</name>
      <uniprot_id>A3KMY9</uniprot_id>
      <gene_name>JAK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00253</protein_accession>
      <name>Propionyl-CoA carboxylase beta chain, mitochondrial</name>
      <uniprot_id>Q2TBR0</uniprot_id>
      <gene_name>PCCB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00255</protein_accession>
      <name>Creatine kinase S-type, mitochondrial</name>
      <uniprot_id>Q3ZBP1</uniprot_id>
      <gene_name>CKMT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00256</protein_accession>
      <name>Creatine kinase B-type</name>
      <uniprot_id>Q5EA61</uniprot_id>
      <gene_name>CKB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00257</protein_accession>
      <name>Creatine kinase U-type, mitochondrial</name>
      <uniprot_id>Q9TTK8</uniprot_id>
      <gene_name>CKMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00258</protein_accession>
      <name>Creatine kinase M-type</name>
      <uniprot_id>Q9XSC6</uniprot_id>
      <gene_name>CKM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00387</protein_accession>
      <name>Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)</name>
      <uniprot_id>Q58DK4</uniprot_id>
      <gene_name>DAK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00449</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>B3IVN4</uniprot_id>
      <gene_name>PKM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00457</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>Q3ZC87</uniprot_id>
      <gene_name>PKM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00458</protein_accession>
      <name>Interleukin-1 receptor-associated kinase 1</name>
      <uniprot_id>Q2LGB3</uniprot_id>
      <gene_name>IRAK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00459</protein_accession>
      <name>Myosin light chain kinase, smooth muscle</name>
      <uniprot_id>Q28824</uniprot_id>
      <gene_name>MYLK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00460</protein_accession>
      <name>Polyribonucleotide 5'-hydroxyl-kinase Clp1</name>
      <uniprot_id>A2VE01</uniprot_id>
      <gene_name>CLP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00465</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>Q1JPG7</uniprot_id>
      <gene_name>PKLR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00474</protein_accession>
      <name>Mitogen-activated protein kinase kinase kinase 7</name>
      <uniprot_id>A2VDU3</uniprot_id>
      <gene_name>MAP3K7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00475</protein_accession>
      <name>Mitogen-activated protein kinase kinase kinase 13</name>
      <uniprot_id>A7MBB4</uniprot_id>
      <gene_name>MAP3K13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00477</protein_accession>
      <name>Bis(5'-adenosyl)-triphosphatase</name>
      <uniprot_id>Q1KZG4</uniprot_id>
      <gene_name>FHIT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00479</protein_accession>
      <name>6-phosphofructokinase, liver type</name>
      <uniprot_id>A1A4J1</uniprot_id>
      <gene_name>PFKL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00483</protein_accession>
      <name>Interleukin-1 receptor-associated kinase 4</name>
      <uniprot_id>Q1RMT8</uniprot_id>
      <gene_name>IRAK4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00486</protein_accession>
      <name>Nucleoside diphosphate kinase 7</name>
      <uniprot_id>Q5E9Y9</uniprot_id>
      <gene_name>NME7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00497</protein_accession>
      <name>Pyruvate kinase</name>
      <uniprot_id>A5D984</uniprot_id>
      <gene_name>PKM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00503</protein_accession>
      <name>Nucleoside diphosphate kinase A 1</name>
      <uniprot_id>P52174</uniprot_id>
      <gene_name>NME1-1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00507</protein_accession>
      <name>Nucleoside diphosphate kinase B</name>
      <uniprot_id>Q3T0Q4</uniprot_id>
      <gene_name>NME2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00513</protein_accession>
      <name>Serine/threonine-protein kinase 12</name>
      <uniprot_id>Q7YRC6</uniprot_id>
      <gene_name>AURKB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00518</protein_accession>
      <name>Nucleoside diphosphate kinase A 2</name>
      <uniprot_id>P52175</uniprot_id>
      <gene_name>NME1-2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00522</protein_accession>
      <name>ADP-dependent glucokinase</name>
      <uniprot_id>A2VE47</uniprot_id>
      <gene_name>ADPGK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00523</protein_accession>
      <name>6-phosphofructokinase, muscle type</name>
      <uniprot_id>Q0IIG5</uniprot_id>
      <gene_name>PFKM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00538</protein_accession>
      <name>Galactokinase</name>
      <uniprot_id>A6H768</uniprot_id>
      <gene_name>GALK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00584</protein_accession>
      <name>GTP:AMP phosphotransferase mitochondrial</name>
      <uniprot_id>P08760</uniprot_id>
      <gene_name>AK3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00600</protein_accession>
      <name>Trifunctional purine biosynthetic protein adenosine-3</name>
      <uniprot_id>Q59A32</uniprot_id>
      <gene_name>GART</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00615</protein_accession>
      <name>Pyruvate carboxylase, mitochondrial</name>
      <uniprot_id>Q29RK2</uniprot_id>
      <gene_name>PC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00703</protein_accession>
      <name>N-acetyl-D-glucosamine kinase</name>
      <uniprot_id>Q3SZM9</uniprot_id>
      <gene_name>NAGK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00762</protein_accession>
      <name>ATP synthase subunit beta</name>
      <uniprot_id>Q0QEM9</uniprot_id>
      <gene_name>ATP5B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00856</protein_accession>
      <name>Glutamate dehydrogenase 1, mitochondrial</name>
      <uniprot_id>P00366</uniprot_id>
      <gene_name>GLUD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00857</protein_accession>
      <name>5-oxoprolinase</name>
      <uniprot_id>Q75WB5</uniprot_id>
      <gene_name>OPLAH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00912</protein_accession>
      <name>Hexokinase-1</name>
      <uniprot_id>P27595</uniprot_id>
      <gene_name>HK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00917</protein_accession>
      <name>RAC-alpha serine/threonine-protein kinase</name>
      <uniprot_id>Q01314</uniprot_id>
      <gene_name>AKT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00930</protein_accession>
      <name>Glycerol kinase</name>
      <uniprot_id>Q0IID9</uniprot_id>
      <gene_name>GK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00933</protein_accession>
      <name>Putative glycerol kinase 5</name>
      <uniprot_id>Q08D86</uniprot_id>
      <gene_name>GK5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00949</protein_accession>
      <name>Phosphomevalonate kinase</name>
      <uniprot_id>Q2KIU2</uniprot_id>
      <gene_name>PMVK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01035</protein_accession>
      <name>Protein kinase C, zeta</name>
      <uniprot_id>A0JNH7</uniprot_id>
      <gene_name>PRKCZ</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01038</protein_accession>
      <name>Protein kinase C, alpha</name>
      <uniprot_id>B0JYP1</uniprot_id>
      <gene_name>PRKCA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01063</protein_accession>
      <name>Protein kinase C, delta</name>
      <uniprot_id>A0JN97</uniprot_id>
      <gene_name>PRKCD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01064</protein_accession>
      <name>Diacylglycerol kinase alpha</name>
      <uniprot_id>A0JN54</uniprot_id>
      <gene_name>DGKA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01116</protein_accession>
      <name>Nucleoside diphosphate kinase</name>
      <uniprot_id>A1A4N9</uniprot_id>
      <gene_name>NME1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01123</protein_accession>
      <name>Nucleoside diphosphate kinase</name>
      <uniprot_id>Q56JV4</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01127</protein_accession>
      <name>Nucleoside diphosphate kinase</name>
      <uniprot_id>A5PK70</uniprot_id>
      <gene_name>NME3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01141</protein_accession>
      <name>Glycerate kinase</name>
      <uniprot_id>Q2KJF7</uniprot_id>
      <gene_name>GLYCTK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01142</protein_accession>
      <name>Serine/threonine-protein kinase PAK 1</name>
      <uniprot_id>Q08E52</uniprot_id>
      <gene_name>PAK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01143</protein_accession>
      <name>Mitogen-activated protein kinase 7</name>
      <uniprot_id>A5PKJ4</uniprot_id>
      <gene_name>MAPK7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01144</protein_accession>
      <name>Dual specificity protein kinase CLK3</name>
      <uniprot_id>Q3SX21</uniprot_id>
      <gene_name>CLK3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01145</protein_accession>
      <name>MAP kinase-activated protein kinase 3</name>
      <uniprot_id>Q3SYZ2</uniprot_id>
      <gene_name>MAPKAPK3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01146</protein_accession>
      <name>Mitogen-activated protein kinase 11</name>
      <uniprot_id>A1A4H8</uniprot_id>
      <gene_name>MAPK11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01147</protein_accession>
      <name>Inhibitor of nuclear factor kappa-B kinase subunit beta</name>
      <uniprot_id>Q95KV0</uniprot_id>
      <gene_name>IKBKB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01148</protein_accession>
      <name>Adenylate kinase isoenzyme 4, mitochondrial</name>
      <uniprot_id>Q0VCP1</uniprot_id>
      <gene_name>AK3L1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01149</protein_accession>
      <name>Casein kinase I isoform gamma-3</name>
      <uniprot_id>P35509</uniprot_id>
      <gene_name>CSNK1G3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01150</protein_accession>
      <name>Phosphoglycerate kinase</name>
      <uniprot_id>Q58DJ6</uniprot_id>
      <gene_name>PGK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01151</protein_accession>
      <name>CTP synthase 2</name>
      <uniprot_id>Q1RMS2</uniprot_id>
      <gene_name>CTPS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01152</protein_accession>
      <name>Ribosomal protein S6 kinase beta-1</name>
      <uniprot_id>Q6TJY3</uniprot_id>
      <gene_name>RPS6KB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01153</protein_accession>
      <name>Casein kinase I isoform beta</name>
      <uniprot_id>P35507</uniprot_id>
      <gene_name>CSNK1B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01154</protein_accession>
      <name>MAPK12 protein</name>
      <uniprot_id>A5PJL3</uniprot_id>
      <gene_name>MAPK12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01155</protein_accession>
      <name>Adenylate kinase isoenzyme 5</name>
      <uniprot_id>A4IFD0</uniprot_id>
      <gene_name>Ak5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01156</protein_accession>
      <name>Adenylate kinase 2, mitochondrial</name>
      <uniprot_id>P08166</uniprot_id>
      <gene_name>AK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01157</protein_accession>
      <name>Serum/glucocorticoid regulated kinase 2</name>
      <uniprot_id>Q0VD39</uniprot_id>
      <gene_name>SGK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01158</protein_accession>
      <name>cAMP-dependent protein kinase catalytic subunit beta</name>
      <uniprot_id>P05131</uniprot_id>
      <gene_name>PRKACB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01159</protein_accession>
      <name>Dual serine/threonine and tyrosine protein kinase</name>
      <uniprot_id>Q4TVR5</uniprot_id>
      <gene_name>DSTYK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01160</protein_accession>
      <name>Phosphoglycerate kinase 1</name>
      <uniprot_id>Q3T0P6</uniprot_id>
      <gene_name>PGK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01161</protein_accession>
      <name>Protein kinase C beta type</name>
      <uniprot_id>P05126</uniprot_id>
      <gene_name>PRKCB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01162</protein_accession>
      <name>Hepatocyte growth factor receptor</name>
      <uniprot_id>Q769I5</uniprot_id>
      <gene_name>MET</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01163</protein_accession>
      <name>Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha isoform</name>
      <uniprot_id>P32871</uniprot_id>
      <gene_name>PIK3CA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01164</protein_accession>
      <name>Guanylate kinase</name>
      <uniprot_id>P46195</uniprot_id>
      <gene_name>GUK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01165</protein_accession>
      <name>Casein kinase I isoform delta</name>
      <uniprot_id>P35508</uniprot_id>
      <gene_name>CSNK1D</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01166</protein_accession>
      <name>Bruton agammaglobulinemia tyrosine kinase</name>
      <uniprot_id>Q3ZC95</uniprot_id>
      <gene_name>BTK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01167</protein_accession>
      <name>LIM domain kinase 2</name>
      <uniprot_id>Q32L23</uniprot_id>
      <gene_name>LIMK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01168</protein_accession>
      <name>Phosphoglycerate kinase</name>
      <uniprot_id>Q32KN6</uniprot_id>
      <gene_name>PGK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01169</protein_accession>
      <name>V-raf murine sarcoma 3611 viral oncogene homolog</name>
      <uniprot_id>Q5BIM4</uniprot_id>
      <gene_name>ARAF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01170</protein_accession>
      <name>Protein kinase C, eta</name>
      <uniprot_id>Q0P5H4</uniprot_id>
      <gene_name>PRKCH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01171</protein_accession>
      <name>Cell division protein kinase 4</name>
      <uniprot_id>Q32KY4</uniprot_id>
      <gene_name>CDK4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01172</protein_accession>
      <name>Glycogen phosphorylase, brain form</name>
      <uniprot_id>Q3B7M9</uniprot_id>
      <gene_name>PYGB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01173</protein_accession>
      <name>Mevalonate kinase</name>
      <uniprot_id>Q5E9T8</uniprot_id>
      <gene_name>MVK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01174</protein_accession>
      <name>Phosphorylase b kinase gamma catalytic chain, testis/liver isoform</name>
      <uniprot_id>Q2KJ16</uniprot_id>
      <gene_name>PHKG2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01175</protein_accession>
      <name>Lymphocyte-specific protein tyrosine kinase</name>
      <uniprot_id>Q3ZCM0</uniprot_id>
      <gene_name>LCK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01176</protein_accession>
      <name>Mast/stem cell growth factor receptor</name>
      <uniprot_id>P43481</uniprot_id>
      <gene_name>KIT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01177</protein_accession>
      <name>Phosphatidylinositol-5-phosphate 4-kinase type-2 gamma</name>
      <uniprot_id>Q0P5F7</uniprot_id>
      <gene_name>PIP4K2C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01178</protein_accession>
      <name>ARAF protein</name>
      <uniprot_id>Q2KJA0</uniprot_id>
      <gene_name>ARAF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01179</protein_accession>
      <name>cGMP-dependent protein kinase 1, alpha isozyme</name>
      <uniprot_id>P00516</uniprot_id>
      <gene_name>PRKG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01180</protein_accession>
      <name>Cell division protein kinase 10</name>
      <uniprot_id>Q2TBL8</uniprot_id>
      <gene_name>CDK10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01181</protein_accession>
      <name>p21 protein (Cdc42/Rac)-activated kinase 4</name>
      <uniprot_id>Q17QZ0</uniprot_id>
      <gene_name>PAK4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01182</protein_accession>
      <name>Serine/threonine-protein kinase PRP4 homolog</name>
      <uniprot_id>Q08DZ2</uniprot_id>
      <gene_name>PRPF4B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01183</protein_accession>
      <name>MAP kinase-interacting serine/threonine-protein kinase 1</name>
      <uniprot_id>Q58D94</uniprot_id>
      <gene_name>MKNK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01184</protein_accession>
      <name>Serine/threonine-protein kinase PLK4</name>
      <uniprot_id>A2VDZ4</uniprot_id>
      <gene_name>PLK4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01185</protein_accession>
      <name>Protein kinase N1</name>
      <uniprot_id>A1A4I4</uniprot_id>
      <gene_name>PKN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01186</protein_accession>
      <name>Phosphatidylinositol 4-kinase beta</name>
      <uniprot_id>O02810</uniprot_id>
      <gene_name>PI4KB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01187</protein_accession>
      <name>Casein kinase II subunit alpha'</name>
      <uniprot_id>P20427</uniprot_id>
      <gene_name>CSNK2A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01188</protein_accession>
      <name>MAPK14 protein</name>
      <uniprot_id>A6QLR9</uniprot_id>
      <gene_name>MAPK14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01189</protein_accession>
      <name>Obg-like ATPase 1</name>
      <uniprot_id>Q2HJ33</uniprot_id>
      <gene_name>OLA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01190</protein_accession>
      <name>STK38L protein</name>
      <uniprot_id>A7MB32</uniprot_id>
      <gene_name>STK38L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01191</protein_accession>
      <name>Mitogen-activated protein kinase 1</name>
      <uniprot_id>P46196</uniprot_id>
      <gene_name>MAPK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01192</protein_accession>
      <name>Phosphatidylinositol 4-kinase alpha</name>
      <uniprot_id>O02811</uniprot_id>
      <gene_name>PI4KA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01193</protein_accession>
      <name>Cell division protein kinase 5</name>
      <uniprot_id>Q02399</uniprot_id>
      <gene_name>CDK5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01194</protein_accession>
      <name>Phosphatidylinositol-4-phosphate 5-kinase-like protein 1</name>
      <uniprot_id>Q17QS4</uniprot_id>
      <gene_name>PIP5KL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01195</protein_accession>
      <name>Mitogen-activated protein kinase 13</name>
      <uniprot_id>Q5E9Q6</uniprot_id>
      <gene_name>MAPK13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01196</protein_accession>
      <name>cGMP-dependent protein kinase 1, beta isozyme</name>
      <uniprot_id>P21136</uniprot_id>
      <gene_name>PRKG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01197</protein_accession>
      <name>Casein kinase I isoform gamma-1</name>
      <uniprot_id>A7E3X2</uniprot_id>
      <gene_name>CSNK1G1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01198</protein_accession>
      <name>RPS6KA1 protein</name>
      <uniprot_id>A4IFF4</uniprot_id>
      <gene_name>RPS6KA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01199</protein_accession>
      <name>Serine/threonine-protein kinase PLK1</name>
      <uniprot_id>Q2TA25</uniprot_id>
      <gene_name>PLK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01200</protein_accession>
      <name>Pyridoxal kinase</name>
      <uniprot_id>Q0II59</uniprot_id>
      <gene_name>PDXK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01201</protein_accession>
      <name>Mitogen-activated protein kinase 13</name>
      <uniprot_id>Q3T0N5</uniprot_id>
      <gene_name>MAPK13</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01202</protein_accession>
      <name>CDC42BPG protein</name>
      <uniprot_id>A6QP95</uniprot_id>
      <gene_name>CDC42BPG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01203</protein_accession>
      <name>Protein kinase C gamma type</name>
      <uniprot_id>P05128</uniprot_id>
      <gene_name>PRKCG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01204</protein_accession>
      <name>Serine/threonine-protein kinase H1</name>
      <uniprot_id>Q0V7M1</uniprot_id>
      <gene_name>PSKH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01205</protein_accession>
      <name>Cell division protein kinase 2</name>
      <uniprot_id>Q5E9Y0</uniprot_id>
      <gene_name>CDK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01206</protein_accession>
      <name>Inhibitor of nuclear factor kappa-B kinase subunit alpha</name>
      <uniprot_id>Q95KV1</uniprot_id>
      <gene_name>CHUK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01207</protein_accession>
      <name>cAMP-dependent protein kinase catalytic subunit alpha</name>
      <uniprot_id>P00517</uniprot_id>
      <gene_name>PRKACA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01208</protein_accession>
      <name>Glycogen phosphorylase, liver form</name>
      <uniprot_id>Q0VCM4</uniprot_id>
      <gene_name>PYGL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01209</protein_accession>
      <name>Adenylate kinase isoenzyme 1</name>
      <uniprot_id>P00570</uniprot_id>
      <gene_name>AK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01210</protein_accession>
      <name>Myosin light chain kinase 2, skeletal/cardiac muscle</name>
      <uniprot_id>A4IFM7</uniprot_id>
      <gene_name>MYLK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01211</protein_accession>
      <name>PRKCB protein</name>
      <uniprot_id>A5D7N0</uniprot_id>
      <gene_name>PRKCB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01212</protein_accession>
      <name>Pantothenate kinase 3</name>
      <uniprot_id>Q08DA5</uniprot_id>
      <gene_name>PANK3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01213</protein_accession>
      <name>Calcium/calmodulin-dependent protein kinase type II beta chain</name>
      <uniprot_id>Q3MHJ9</uniprot_id>
      <gene_name>CAMK2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01214</protein_accession>
      <name>PRKACB protein</name>
      <uniprot_id>A6QNX4</uniprot_id>
      <gene_name>PRKACB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01215</protein_accession>
      <name>Protein kinase C alpha type</name>
      <uniprot_id>P04409</uniprot_id>
      <gene_name>PRKCA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01216</protein_accession>
      <name>Casein kinase I isoform alpha</name>
      <uniprot_id>P67827</uniprot_id>
      <gene_name>CSNK1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01217</protein_accession>
      <name>Glutamate-cysteine ligase catalytic subunit</name>
      <uniprot_id>Q32S38</uniprot_id>
      <gene_name>GCLC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01218</protein_accession>
      <name>Spleen tyrosine kinase</name>
      <uniprot_id>Q32PK0</uniprot_id>
      <gene_name>SYK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01219</protein_accession>
      <name>UMP-CMP kinase</name>
      <uniprot_id>Q2KIW9</uniprot_id>
      <gene_name>CMPK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01220</protein_accession>
      <name>Tyrosine-protein kinase receptor</name>
      <uniprot_id>Q0V7M6</uniprot_id>
      <gene_name>DDR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01221</protein_accession>
      <name>Casein kinase II subunit alpha</name>
      <uniprot_id>P68399</uniprot_id>
      <gene_name>CSNK2A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01222</protein_accession>
      <name>RPS6KA3 protein</name>
      <uniprot_id>A5PJL4</uniprot_id>
      <gene_name>RPS6KA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01223</protein_accession>
      <name>V-FES feline sarcoma viral/V-FPS fujinami avian sarcoma viral oncogene homolog</name>
      <uniprot_id>Q5E9H3</uniprot_id>
      <gene_name>FES</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01224</protein_accession>
      <name>Dual specificity mitogen-activated protein kinase kinase 6</name>
      <uniprot_id>Q5E9X2</uniprot_id>
      <gene_name>MAP2K6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01225</protein_accession>
      <name>Calcium/calmodulin-dependent protein kinase type II delta chain</name>
      <uniprot_id>Q2HJF7</uniprot_id>
      <gene_name>CAMK2D</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01226</protein_accession>
      <name>Proto-oncogene serine/threonine-protein kinase pim-1</name>
      <uniprot_id>Q9N0P9</uniprot_id>
      <gene_name>PIM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01227</protein_accession>
      <name>Adenylate kinase isoenzyme 6</name>
      <uniprot_id>A5PJA1</uniprot_id>
      <gene_name>AK6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01228</protein_accession>
      <name>Megakaryocyte-associated tyrosine kinase isoform a</name>
      <uniprot_id>Q58D16</uniprot_id>
      <gene_name>MATK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01891</protein_accession>
      <name>Leukotriene B4 receptor 1</name>
      <uniprot_id>Q3T181</uniprot_id>
      <gene_name>LTB4R</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02044</protein_accession>
      <name>P2Y purinoceptor 14</name>
      <uniprot_id>Q3SX17</uniprot_id>
      <gene_name>P2RY14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02583</protein_accession>
      <name>Purinergic receptor P2Y, G-protein coupled, 12</name>
      <uniprot_id>Q0IIL0</uniprot_id>
      <gene_name>P2RY12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:26 UTC</creation_date>
  <update_date>2020-03-13 16:27:24 UTC</update_date>
  <accession>BMDB0001342</accession>
  <secondary_accessions>
    <accession>BMDB01342</accession>
  </secondary_accessions>
  <name>Thymidine 5'-triphosphate</name>
  <description/>
  <synonyms>
    <synonym>2'-Deoxythymidine triphosphate</synonym>
    <synonym>5'-TTP</synonym>
    <synonym>Deoxy-TTP</synonym>
    <synonym>Deoxythymidine 5'-triphosphate</synonym>
    <synonym>Deoxythymidine triphosphate</synonym>
    <synonym>DTHD5'ppp</synonym>
    <synonym>PPPDT</synonym>
    <synonym>THYMIDINE-5'-triphosphATE</synonym>
    <synonym>TTP</synonym>
    <synonym>2'-Deoxythymidine triphosphoric acid</synonym>
    <synonym>Deoxythymidine 5'-triphosphoric acid</synonym>
    <synonym>Deoxythymidine triphosphoric acid</synonym>
    <synonym>THYMIDINE-5'-triphosphoric acid</synonym>
    <synonym>Thymidine 5'-triphosphoric acid</synonym>
    <synonym>2'-Deoxythymidine 5'-triphosphate</synonym>
    <synonym>5-Methyl-dUTP</synonym>
    <synonym>dTTP</synonym>
    <synonym>Thymidine mono(tetrahydrogen triphosphate)</synonym>
    <synonym>Thymidine triphosphate</synonym>
    <synonym>Thymidine 5'-triphosphate, magnesium salt</synonym>
    <synonym>Thymidine 5'-triphosphate, trisodium salt</synonym>
    <synonym>2'-Deoxythymidine-5'-triphosphate</synonym>
    <synonym>Thymidine 5'-triphosphate, p''-(32)p-labeled</synonym>
  </synonyms>
  <chemical_formula>C10H17N2O14P3</chemical_formula>
  <average_molecular_weight>482.1683</average_molecular_weight>
  <monisotopic_moleculate_weight>481.989262798</monisotopic_moleculate_weight>
  <iupac_name>{[hydroxy({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphoryl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>dTTP</traditional_iupac>
  <cas_registry_number>365-08-2</cas_registry_number>
  <smiles>CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)NC1=O</smiles>
  <inchi>InChI=1S/C10H17N2O14P3/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(24-8)4-23-28(19,20)26-29(21,22)25-27(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,19,20)(H,21,22)(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1</inchi>
  <inchikey>NHVNXKFIZYSCEB-XLPZGREQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside triphosphates. These are pyrimidine nucleotides with a triphosphate group  linked to the ribose moiety lacking a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine deoxyribonucleotides</sub_class>
    <direct_parent>Pyrimidine 2'-deoxyribonucleoside triphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside triphosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxyribonucleotides</external_descriptor>
      <external_descriptor>pyrimidine 2'-deoxyribonucleoside 5'-triphosphate</external_descriptor>
      <external_descriptor>thymidine phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[hydroxy({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphoryl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>482.1683</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>481.989262798</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H17N2O14P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H17N2O14P3/c1-5-3-12(10(15)11-9(5)14)8-2-6(13)7(24-8)4-23-28(19,20)26-29(21,22)25-27(16,17)18/h3,6-8,13H,2,4H2,1H3,(H,19,20)(H,21,22)(H,11,14,15)(H2,16,17,18)/t6-,7+,8+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NHVNXKFIZYSCEB-XLPZGREQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>238.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>88.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180398</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00459</kegg_id>
  <chemspider_id>58493</chemspider_id>
  <foodb_id>FDB030841</foodb_id>
  <drugbank_id>DB02452</drugbank_id>
  <chebi_id>18077</chebi_id>
  <pubchem_compound_id>64968</pubchem_compound_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00019695</knapsack_id>
  <wikipedia_id>Deoxythymidine_Triphosphate</wikipedia_id>
  <bigg_id>35032</bigg_id>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Ikehara, Morio; Ohtsuka, Eiko. Coenzyme analogs. XXI. A new synthesis of thymidine 5'-triphosphate and the use of P1,P2-bis(2-cyanoethyl) pyrophosphate in the nucleoside triphosphate synthesis. Chemical &amp; Pharmaceutical Bulletin (1963), 11(11), 1358-63.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:27 UTC</creation_date>
  <update_date>2020-04-15 22:31:13 UTC</update_date>
  <accession>BMDB0001343</accession>
  <secondary_accessions>
    <accession>BMDB01343</accession>
  </secondary_accessions>
  <name>Mevalonic acid-5P</name>
  <description/>
  <synonyms>
    <synonym>(R)-5-Phosphomevalonate</synonym>
    <synonym>(R)-5-Phosphomevaloonic acid</synonym>
    <synonym>(R)-Mevalonic acid 5-phosphate</synonym>
    <synonym>(R)-5-Phosphomevalonic acid</synonym>
    <synonym>(R)-5-Phosphomevaloonate</synonym>
    <synonym>(R)-Mevalonate 5-phosphate</synonym>
    <synonym>(R)-Mevalonic acid 5-phosphoric acid</synonym>
    <synonym>Mevalonate-5P</synonym>
    <synonym>5-Phosphomevalonate</synonym>
    <synonym>Mevalonate-5-p</synonym>
    <synonym>Mevalonate-5-phosphate</synonym>
    <synonym>Mevalonate-p</synonym>
    <synonym>p-Mevalonate</synonym>
    <synonym>5-Phosphomevalonic acid</synonym>
    <synonym>Mevalonate 5-phosphate</synonym>
    <synonym>Phosphomevalonate</synonym>
    <synonym>Phosphomevalonic acid</synonym>
    <synonym>Phosphomevalonic acid, (+-)-isomer</synonym>
  </synonyms>
  <chemical_formula>C6H13O7P</chemical_formula>
  <average_molecular_weight>228.137</average_molecular_weight>
  <monisotopic_moleculate_weight>228.039889282</monisotopic_moleculate_weight>
  <iupac_name>(3R)-3-hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid</iupac_name>
  <traditional_iupac>mevalonate-5-phosphate</traditional_iupac>
  <cas_registry_number>73566-35-5</cas_registry_number>
  <smiles>C[C@@](O)(CCOP(O)(O)=O)CC(O)=O</smiles>
  <inchi>InChI=1S/C6H13O7P/c1-6(9,4-5(7)8)2-3-13-14(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H2,10,11,12)/t6-/m1/s1</inchi>
  <inchikey>OKZYCXHTTZZYSK-ZCFIWIBFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic phosphoric acids and derivatives</class>
    <sub_class>Phosphate esters</sub_class>
    <direct_parent>Monoalkyl phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Short-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain hydroxy acid</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
      <external_descriptor>carboxyalkyl phosphate</external_descriptor>
      <external_descriptor>primary alcohol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R)-3-hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>228.137</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>228.039889282</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@](O)(CCOP(O)(O)=O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O7P/c1-6(9,4-5(7)8)2-3-13-14(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H2,10,11,12)/t6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OKZYCXHTTZZYSK-ZCFIWIBFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>124.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180629</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01107</kegg_id>
  <foodb_id>FDB031001</foodb_id>
  <chemspider_id>388517</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>439400</pubchem_compound_id>
  <chebi_id>17436</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00007304</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>36819</bigg_id>
  <wikipedia_id/>
  <metlin_id>6177</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00949</protein_accession>
      <name>Phosphomevalonate kinase</name>
      <uniprot_id>Q2KIU2</uniprot_id>
      <gene_name>PMVK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:28 UTC</creation_date>
  <update_date>2020-03-13 16:27:25 UTC</update_date>
  <accession>BMDB0001345</accession>
  <secondary_accessions>
    <accession>BMDB01345</accession>
  </secondary_accessions>
  <name>4-Trimethylammoniobutanal</name>
  <description>4-Trimethylammoniobutanal, also known as 4-trimethylammoniobutanal, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. 4-Trimethylammoniobutanal is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Trimethylammoniobutanal exists in all living organisms, ranging from bacteria to humans. 4-Trimethylammoniobutanal participates in a number of enzymatic reactions, within cattle. In particular, Glycine and 4-trimethylammoniobutanal can be biosynthesized from 3-hydroxy-N6,N6,N6-trimethyl-L-lysine through its interaction with the enzyme serine hydroxymethyltransferase, cytosolic. In addition, 4-Trimethylammoniobutanal can be converted into 4-trimethylammoniobutanoic acid through its interaction with the enzyme 4-4-trimethylammoniobutanal dehydrogenase. In cattle, 4-trimethylammoniobutanal is involved in the metabolic pathway called carnitine synthesis pathway.</description>
  <synonyms>
    <synonym>4-(Trimethylamino)butanal</synonym>
    <synonym>4-(Trimethylammonio)butanal</synonym>
    <synonym>gamma-Trimethylaminobutyraldehyde</synonym>
    <synonym>N,N,N-Trimethyl-4-oxo-1-butanaminium</synonym>
    <synonym>Trimethyl-(4-oxobutyl)ammonium</synonym>
    <synonym>Trimethylaminobutyraldehyde</synonym>
  </synonyms>
  <chemical_formula>C7H16NO</chemical_formula>
  <average_molecular_weight>130.208</average_molecular_weight>
  <monisotopic_moleculate_weight>130.123189139</monisotopic_moleculate_weight>
  <iupac_name>trimethyl(4-oxobutyl)azanium</iupac_name>
  <traditional_iupac>trimethylaminobutyraldehyde</traditional_iupac>
  <cas_registry_number>64595-66-0</cas_registry_number>
  <smiles>C[N+](C)(C)CCCC=O</smiles>
  <inchi>InChI=1S/C7H16NO/c1-8(2,3)6-4-5-7-9/h7H,4-6H2,1-3H3/q+1</inchi>
  <inchikey>OITBLCDWXSXNCN-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Alpha-hydrogen aldehydes</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydrogen aldehyde</substituent>
      <substituent>Amine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>butanals</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>trimethyl(4-oxobutyl)azanium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>130.208</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>130.123189139</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)CCCC=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H16NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H16NO/c1-8(2,3)6-4-5-7-9/h7H,4-6H2,1-3H3/q+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OITBLCDWXSXNCN-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289275</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01149</kegg_id>
  <foodb_id>FDB022567</foodb_id>
  <chemspider_id>130</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>133</pubchem_compound_id>
  <chebi_id>18020</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>36920</bigg_id>
  <wikipedia_id/>
  <metlin_id>6179</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00593</protein_accession>
      <name>4-trimethylaminobutyraldehyde dehydrogenase</name>
      <uniprot_id>Q2KJH9</uniprot_id>
      <gene_name>ALDH9A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:29 UTC</creation_date>
  <update_date>2020-03-13 16:27:26 UTC</update_date>
  <accession>BMDB0001346</accession>
  <secondary_accessions>
    <accession>BMDB01346</accession>
  </secondary_accessions>
  <name>GDP-4-Dehydro-6-deoxy-D-mannose</name>
  <description>GDP-4-Dehydro-6-deoxy-D-mannose, also known as GDP-4-dehydro-D-rhamnose or GDP-4-keto-6-deoxymannose, belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. GDP-4-Dehydro-6-deoxy-D-mannose is possibly soluble (in water) and a strong basic compound (based on its pKa). GDP-4-Dehydro-6-deoxy-D-mannose exists in all living organisms, ranging from bacteria to humans. GDP-4-Dehydro-6-deoxy-D-mannose participates in a number of enzymatic reactions, within cattle. In particular, GDP-4-Dehydro-6-deoxy-D-mannose can be biosynthesized from guanosine diphosphate mannose through its interaction with the enzyme GDP-mannose 4,6 dehydratase. In addition, GDP-4-Dehydro-6-deoxy-D-mannose can be biosynthesized from GDP-L-fucose; which is mediated by the enzyme GDP-L-fucose synthase. In cattle, GDP-4-dehydro-6-deoxy-D-mannose is involved in the metabolic pathway called the fructose and mannose degradation pathway.</description>
  <synonyms>
    <synonym>GDP-4-Dehydro-6-deoxy-D-talose</synonym>
    <synonym>GDP-4-Dehydro-D-rhamnose</synonym>
    <synonym>GDP-4-Keto-6-deoxy-D-mannose</synonym>
    <synonym>GDP-4-Keto-6-deoxymannose</synonym>
    <synonym>GDP-4-oxo-6-Deoxy-D-mannose</synonym>
    <synonym>Guanosine 5'-(trihydrogen diphosphate), p'-(6-deoxy-alpha-D-lyxo-hexopyranos-4-ulos-1-yl) ester</synonym>
    <synonym>Guanosine diphosphate-4-keto-6-deoxy-D-mannose</synonym>
    <synonym>GDP-4-Dehydro-alpha-D-rhamnose</synonym>
    <synonym>GDP-4-Dehydro-6-deoxy-alpha-D-mannose</synonym>
    <synonym>Guanosine 5'-(trihydrogen diphosphate), p'-(6-deoxy-a-D-lyxo-hexopyranos-4-ulos-1-yl) ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen diphosphate), p'-(6-deoxy-α-D-lyxo-hexopyranos-4-ulos-1-yl) ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-a-D-lyxo-hexopyranos-4-ulos-1-yl) ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-alpha-D-lyxo-hexopyranos-4-ulos-1-yl) ester</synonym>
    <synonym>Guanosine 5'-(trihydrogen diphosphoric acid), p'-(6-deoxy-α-D-lyxo-hexopyranos-4-ulos-1-yl) ester</synonym>
    <synonym>Guanosine diphosphoric acid-4-keto-6-deoxy-D-mannose</synonym>
    <synonym>GDP-4-Dehydro-a-D-rhamnose</synonym>
    <synonym>GDP-4-Dehydro-α-D-rhamnose</synonym>
    <synonym>GDP-4-Dehydro-6-deoxy-a-D-mannose</synonym>
    <synonym>GDP-4-Dehydro-6-deoxy-α-D-mannose</synonym>
    <synonym>GDP-4-Keto-6-D-deoxymannose</synonym>
    <synonym>GDP-4-oxo-6-Deoxymannose</synonym>
  </synonyms>
  <chemical_formula>C16H23N5O15P2</chemical_formula>
  <average_molecular_weight>587.3258</average_molecular_weight>
  <monisotopic_moleculate_weight>587.066588115</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>gdp-4-keto-6-deoxymannose</traditional_iupac>
  <cas_registry_number>18186-48-6</cas_registry_number>
  <smiles>C[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@@H](O)C1=O</smiles>
  <inchi>InChI=1S/C16H23N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5-,8-,9+,10-,11+,14-,15-/m1/s1</inchi>
  <inchikey>PNHLMHWWFOPQLK-BKUUWRAGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine nucleotide sugars</sub_class>
    <direct_parent>Purine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>GDP-sugar</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>587.3258</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>587.066588115</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@@H](O)C1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H23N5O15P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H23N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5-,8-,9+,10-,11+,14-,15-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PNHLMHWWFOPQLK-BKUUWRAGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>304.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>116.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32230</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01222</kegg_id>
  <foodb_id>FDB022568</foodb_id>
  <chemspider_id>388554</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>439446</pubchem_compound_id>
  <chebi_id>16955</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00007244</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>37116</bigg_id>
  <wikipedia_id/>
  <metlin_id>6180</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Oths, Philip J.; Mayer, Robert M.; Floss, Heinz G.  Stereochemistry and mechanism of the GDP-mannose dehydratase reaction.    Carbohydrate Research  (1990),  198(1),  91-100.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:30 UTC</creation_date>
  <update_date>2020-04-15 22:32:54 UTC</update_date>
  <accession>BMDB0001347</accession>
  <secondary_accessions>
    <accession>BMDB01347</accession>
  </secondary_accessions>
  <name>Isopentenyl pyrophosphate</name>
  <description/>
  <synonyms>
    <synonym>3-Methyl-3-butenyl pyrophosphate</synonym>
    <synonym>3-Methylbut-3-en-1-yl trihydrogen diphosphate</synonym>
    <synonym>3-Methylbut-3-enyl phosphono hydrogen phosphate</synonym>
    <synonym>delta-3-Isopentenyl pyrophosphate</synonym>
    <synonym>delta3-Isopentenyl diphosphate</synonym>
    <synonym>delta3-Methyl-3-butenyl diphosphate</synonym>
    <synonym>Diphosphoric acid mono(3-methyl-3-butenyl) ester</synonym>
    <synonym>IPP</synonym>
    <synonym>IPPP</synonym>
    <synonym>mono(3-Methyl-3-butenyl) diphosphate</synonym>
    <synonym>3-Methyl-3-butenyl pyrophosphoric acid</synonym>
    <synonym>3-Methylbut-3-en-1-yl trihydrogen diphosphoric acid</synonym>
    <synonym>3-Methylbut-3-enyl phosphono hydrogen phosphoric acid</synonym>
    <synonym>delta-3-Isopentenyl pyrophosphoric acid</synonym>
    <synonym>Δ-3-isopentenyl pyrophosphate</synonym>
    <synonym>Δ-3-isopentenyl pyrophosphoric acid</synonym>
    <synonym>delta3-Isopentenyl diphosphoric acid</synonym>
    <synonym>Δ3-isopentenyl diphosphate</synonym>
    <synonym>Δ3-isopentenyl diphosphoric acid</synonym>
    <synonym>delta3-Methyl-3-butenyl diphosphoric acid</synonym>
    <synonym>Δ3-methyl-3-butenyl diphosphate</synonym>
    <synonym>Δ3-methyl-3-butenyl diphosphoric acid</synonym>
    <synonym>Diphosphate mono(3-methyl-3-butenyl) ester</synonym>
    <synonym>mono(3-Methyl-3-butenyl) diphosphoric acid</synonym>
    <synonym>Isopentenyl pyrophosphoric acid</synonym>
    <synonym>delta(3)-Isopentenyl-PP</synonym>
    <synonym>delta-3-Isopentenyl pyrophosphat</synonym>
    <synonym>IPR</synonym>
    <synonym>Isopentenyl diphosphate</synonym>
    <synonym>Isopentenyl-PP</synonym>
    <synonym>Isopentenyl pyrophosphate, 4-(14)C-labeled</synonym>
  </synonyms>
  <chemical_formula>C5H12O7P2</chemical_formula>
  <average_molecular_weight>246.0921</average_molecular_weight>
  <monisotopic_moleculate_weight>246.005825762</monisotopic_moleculate_weight>
  <iupac_name>({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid</iupac_name>
  <traditional_iupac>isopentenyl-diphosphate</traditional_iupac>
  <cas_registry_number>358-71-4</cas_registry_number>
  <smiles>CC(=C)CCOP(O)(=O)OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)</inchi>
  <inchikey>NUHSROFQTUXZQQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Isoprenoid phosphates</sub_class>
    <direct_parent>Isoprenoid phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isoprenoid phosphate</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>C5 isoprenoids (hemiterpenes)</external_descriptor>
      <external_descriptor>C5 isoprenoids (hemiterpenes)</external_descriptor>
      <external_descriptor>prenol phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>246.0921</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>246.005825762</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=C)CCOP(O)(=O)OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H12O7P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NUHSROFQTUXZQQ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>48.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3259</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00129</kegg_id>
  <foodb_id>FDB030946</foodb_id>
  <chemspider_id>1158</chemspider_id>
  <drugbank_id>DB04714</drugbank_id>
  <pubchem_compound_id>1195</pubchem_compound_id>
  <chebi_id>16584</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00000848</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33956</bigg_id>
  <wikipedia_id>Isopentenyl pyrophosphate</wikipedia_id>
  <metlin_id>6181</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Kao, Chai-Lin; Kittleman, William; Zhang, Hua; Seto, Haruo; Liu, Hung-Wen. Stereochemical Analysis of Isopentenyl Diphosphate Isomerase Type II from Staphylococcus aureus Using Chemically Synthesized (S)- and (R)-[2-2H]Isopentenyl Diphosphates. Org Lett. 2005 Dec 8;7(25):5677-80.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00101</protein_accession>
      <name>Diphosphomevalonate decarboxylase</name>
      <uniprot_id>Q0P570</uniprot_id>
      <gene_name>MVD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00451</protein_accession>
      <name>Isopentenyl-diphosphate Delta-isomerase 1</name>
      <uniprot_id>Q1LZ95</uniprot_id>
      <gene_name>IDI1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00864</protein_accession>
      <name>Farnesyl pyrophosphate synthetase</name>
      <uniprot_id>Q8WMY2</uniprot_id>
      <gene_name>FDPS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00865</protein_accession>
      <name>Geranylgeranyl pyrophosphate synthetase</name>
      <uniprot_id>P56966</uniprot_id>
      <gene_name>GGPS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:32 UTC</creation_date>
  <update_date>2020-04-16 20:37:31 UTC</update_date>
  <accession>BMDB0001348</accession>
  <secondary_accessions>
    <accession>BMDB01348</accession>
  </secondary_accessions>
  <name>SM(d18:1/18:0)</name>
  <description/>
  <synonyms>
    <synonym>Sphingomyelin</synonym>
    <synonym>N-(Octadecanoyl)-1-phosphocholine-sphing-4-enine</synonym>
    <synonym>Sphingomyelin(D18:1/18:0)</synonym>
    <synonym>N-(Octadecanoyl)-1-phosphocholine-sphingosine</synonym>
    <synonym>N-(Octadecanoyl)-1-phosphocholine-D-erythro-sphingosine</synonym>
    <synonym>N-(Octadecanoyl)-1-phosphocholine-4-sphingenine</synonym>
    <synonym>N-(Octadecanoyl)-1-phosphocholine-D-sphingosine</synonym>
    <synonym>N-(Octadecanoyl)-1-phosphocholine-sphingenine</synonym>
    <synonym>N-(Octadecanoyl)-1-phosphocholine-erythro-4-sphingenine</synonym>
  </synonyms>
  <chemical_formula>C41H83N2O6P</chemical_formula>
  <average_molecular_weight>731.097</average_molecular_weight>
  <monisotopic_moleculate_weight>730.598875399</monisotopic_moleculate_weight>
  <iupac_name>(2-{[(2S,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium</iupac_name>
  <traditional_iupac>(2-{[(2S,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium</traditional_iupac>
  <cas_registry_number/>
  <smiles>CCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)C(O)\C=C\CCCCCCCCCCCCC</smiles>
  <inchi>InChI=1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b34-32+/t39-,40?/m0/s1</inchi>
  <inchikey>LKQLRGMMMAHREN-NWVYORHESA-N</inchikey>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2-{[(2S,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>731.097</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>730.598875399</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)C(O)\C=C\CCCCCCCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C41H83N2O6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b34-32+/t39-,40?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LKQLRGMMMAHREN-NWVYORHESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>107.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>223.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>92.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1243492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1243493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1243494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1358860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1358861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1358862</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>12+/-2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>6+/-2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>8+/-1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.19+/-0.13</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>8+/-2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>5+/-1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id/>
  <kegg_id/>
  <chemspider_id/>
  <pubchem_compound_id/>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:33 UTC</creation_date>
  <update_date>2020-04-16 17:51:37 UTC</update_date>
  <accession>BMDB0001349</accession>
  <secondary_accessions>
    <accession>BMDB01349</accession>
  </secondary_accessions>
  <name>Selenium</name>
  <description>Selenium, also known as se(2-), belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'. Selenium is possibly soluble (in water) and possibly neutral. In cattle, selenium is involved in the metabolic pathway called the selenoamino acid metabolism pathway.</description>
  <synonyms>
    <synonym>Se(2-)</synonym>
  </synonyms>
  <chemical_formula>Se</chemical_formula>
  <average_molecular_weight>78.96</average_molecular_weight>
  <monisotopic_moleculate_weight>79.916521828</monisotopic_moleculate_weight>
  <iupac_name>selandiide</iupac_name>
  <traditional_iupac>selandiide</traditional_iupac>
  <cas_registry_number>22541-48-6</cas_registry_number>
  <smiles>[Se--]</smiles>
  <inchi>InChI=1S/Se/q-2</inchi>
  <inchikey>HMUBNCUQSSTAIB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Homogeneous other non-metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous other non-metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous other non metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>an anion</external_descriptor>
      <external_descriptor>elemental selenium</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>selandiide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>78.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>79.916521828</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Se--]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Se</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Se/q-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HMUBNCUQSSTAIB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>13.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35917</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1.4+/-0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.279 - 0.494</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.195</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.177</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.21</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.208</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.177</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.204</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.204</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.204</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.122</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.36 +/- 0.09</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>A. PECHOVÁ et al. Contents of Zn, Cu, Mn and Se in Milk in Relation to their Concentrations in Blood, Milk Yield and Stage of Lactation in Dairy Cattle. Acta Vet. Brno 2008, 77: 523-531</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.3 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.35 +/- 0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.36 +/- 0.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.165 +/- 0.0127</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.33 +/- 0.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.147 +/- 0.00127</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.162 +/- 0.00507</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS.  Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.138 +/- 0.00253</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.114 +/- 0.0127</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0545 +/- 0.00253</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB031170</foodb_id>
  <kegg_id/>
  <chemspider_id/>
  <pubchem_compound_id>107674</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>15076</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Selenium</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Zhu, Shihui; Zhu, Liu; Kaisuya, Romeo; Shou, Jianchuan.  Apparatus and process for production of high purity selenium.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2007), 12pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>A. PECHOVÁ et al. Contents of Zn, Cu, Mn and Se in Milk in Relation to their Concentrations in Blood, Milk Yield and Stage of Lactation in Dairy Cattle. Acta Vet. Brno 2008, 77: 523-531</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
    </reference>
    <reference>
      <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00391</protein_accession>
      <name>Ethanolaminephosphotransferase 1</name>
      <uniprot_id>Q17QM4</uniprot_id>
      <gene_name>SELI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00501</protein_accession>
      <name>Thioredoxin reductase 2, mitochondrial</name>
      <uniprot_id>Q9N2I8</uniprot_id>
      <gene_name>TXNRD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00539</protein_accession>
      <name>Selenocysteine lyase</name>
      <uniprot_id>A2VDS1</uniprot_id>
      <gene_name>SCLY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00540</protein_accession>
      <name>Thioredoxin reductase 1, cytoplasmic</name>
      <uniprot_id>O62768</uniprot_id>
      <gene_name>TXNRD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00541</protein_accession>
      <name>Phospholipid hydroperoxide glutathione peroxidase, mitochondrial</name>
      <uniprot_id>Q9N2J2</uniprot_id>
      <gene_name>GPX4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00542</protein_accession>
      <name>Glutathione peroxidase 3</name>
      <uniprot_id>P37141</uniprot_id>
      <gene_name>GPX3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00543</protein_accession>
      <name>Iodothyronine deiodinase</name>
      <uniprot_id>Q5I3B0</uniprot_id>
      <gene_name>DIO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00544</protein_accession>
      <name>Glutathione peroxidase 1</name>
      <uniprot_id>P00435</uniprot_id>
      <gene_name>GPX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00545</protein_accession>
      <name>Iodothyronine deiodinase</name>
      <uniprot_id>Q9BDR5</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00546</protein_accession>
      <name>Type II iodothyronine deiodinase</name>
      <uniprot_id>Q5I3B2</uniprot_id>
      <gene_name>DIO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00547</protein_accession>
      <name>Methionine-R-sulfoxide reductase B1</name>
      <uniprot_id>Q3MHL9</uniprot_id>
      <gene_name>SEPX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00548</protein_accession>
      <name>Type III iodothyronine deiodinase</name>
      <uniprot_id>Q5I3B1</uniprot_id>
      <gene_name>DIO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00614</protein_accession>
      <name>Selenide, water dikinase 1</name>
      <uniprot_id>Q0VC82</uniprot_id>
      <gene_name>SEPHS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01619</protein_accession>
      <name>Selenoprotein T</name>
      <uniprot_id>A6QP01</uniprot_id>
      <gene_name>SELT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01620</protein_accession>
      <name>Selenoprotein S</name>
      <uniprot_id>Q2KI76</uniprot_id>
      <gene_name>SELS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01621</protein_accession>
      <name>Selenoprotein P</name>
      <uniprot_id>P49907</uniprot_id>
      <gene_name>SEPP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01622</protein_accession>
      <name>Selenoprotein K</name>
      <uniprot_id>Q32PE3</uniprot_id>
      <gene_name>SELK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01623</protein_accession>
      <name>15 kDa selenoprotein</name>
      <uniprot_id>A8YXY3</uniprot_id>
      <gene_name>15-Sep</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01893</protein_accession>
      <name>Uncharacterized protein C17orf37 homolog</name>
      <uniprot_id>Q148C8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01894</protein_accession>
      <name>Selenium-binding protein 1</name>
      <uniprot_id>Q2KJ32</uniprot_id>
      <gene_name>SELENBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:34 UTC</creation_date>
  <update_date>2020-03-13 16:27:28 UTC</update_date>
  <accession>BMDB0001351</accession>
  <secondary_accessions>
    <accession>BMDB01351</accession>
  </secondary_accessions>
  <name>Deoxyribose 1-phosphate</name>
  <description/>
  <synonyms>
    <synonym>2-Deoxy-1-O-phosphono-D-erythro-pentofuranose</synonym>
    <synonym>2-Deoxy-1-O-phosphono-D-ribofuranose</synonym>
    <synonym>2-Deoxy-D-ribose 1-phosphate</synonym>
    <synonym>2-Deoxy-D-ribose 1-phosphoric acid</synonym>
    <synonym>Deoxyribose 1-phosphoric acid</synonym>
    <synonym>2-Deoxy-alpha-D-ribose 1-phosphate</synonym>
    <synonym>2-Deoxy-alpha-delta-ribose 1-phosphate</synonym>
    <synonym>2-Deoxy-D-erythro-pentofuranose 1-phosphate</synonym>
    <synonym>2-Deoxy-D-ribose-1-phosphate</synonym>
    <synonym>2-Deoxy-delta-erythro-pentofuranose 1-phosphate</synonym>
    <synonym>2-Deoxy-delta-ribose 1-phosphate</synonym>
    <synonym>2-Deoxy-delta-ribose-1-phosphate</synonym>
    <synonym>2-Deoxyribofuranose 1-phosphate</synonym>
    <synonym>D-2-Deoxy-ribofuranose 1-phosphate</synonym>
    <synonym>delta-2-Deoxy-ribofuranose 1-phosphate</synonym>
    <synonym>Deoxyribose-1-phosphate</synonym>
    <synonym>2-Deoxyribose 1-phosphate</synonym>
    <synonym>2-Deoxyribose 1-phosphate, (alpha-D-erythro)-isomer</synonym>
    <synonym>2-Deoxyribose 1-phosphate, (beta-D-erythro)-isomer</synonym>
  </synonyms>
  <chemical_formula>C5H11O7P</chemical_formula>
  <average_molecular_weight>214.1104</average_molecular_weight>
  <monisotopic_moleculate_weight>214.024239218</monisotopic_moleculate_weight>
  <iupac_name>{[(4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>deoxyribose-1-phosphate</traditional_iupac>
  <cas_registry_number>17210-42-3</cas_registry_number>
  <smiles>OC[C@H]1OC(C[C@@H]1O)OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C5H11O7P/c6-2-4-3(7)1-5(11-4)12-13(8,9)10/h3-7H,1-2H2,(H2,8,9,10)/t3-,4+,5?/m0/s1</inchi>
  <inchikey>KBDKAJNTYKVSEK-PYHARJCCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-deoxyribose 1-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>214.1104</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>214.024239218</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1OC(C[C@@H]1O)OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H11O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H11O7P/c6-2-4-3(7)1-5(11-4)12-13(8,9)10/h3-7H,1-2H2,(H2,8,9,10)/t3-,4+,5?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KBDKAJNTYKVSEK-PYHARJCCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>116.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33853</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00672</kegg_id>
  <foodb_id>FDB022571</foodb_id>
  <chemspider_id>388420</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>439287</pubchem_compound_id>
  <chebi_id>28542</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>35664</bigg_id>
  <wikipedia_id/>
  <metlin_id>6182</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:35 UTC</creation_date>
  <update_date>2020-03-13 16:27:28 UTC</update_date>
  <accession>BMDB0001352</accession>
  <secondary_accessions>
    <accession>BMDB01352</accession>
  </secondary_accessions>
  <name>Hydroxypyruvic acid</name>
  <description>Hydroxypyruvic acid, also known as Hydroxypyruvic acid or OH-pyr, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Hydroxypyruvic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Hydroxypyruvic acid exists in all living organisms, ranging from bacteria to humans. Hydroxypyruvic acid and L-alanine can be biosynthesized from pyruvic acid and L-serine through its interaction with the enzyme serine--pyruvate aminotransferase. In cattle, hydroxypyruvic acid is involved in the metabolic pathway called the glycine and serine metabolism pathway.</description>
  <synonyms>
    <synonym>3-Hydroxypyruvate</synonym>
    <synonym>3-Hydroxypyruvic acid</synonym>
    <synonym>Hydroxypyruvate</synonym>
    <synonym>3-Hydroxy-2-oxopropanoate</synonym>
    <synonym>3-Hydroxy-2-oxopropanoic acid</synonym>
    <synonym>beta-Hydroxypyruvate</synonym>
    <synonym>OH-Pyr</synonym>
    <synonym>OH-Pyruvate</synonym>
    <synonym>Hydroxypyruvic acid, lithium salt</synonym>
  </synonyms>
  <chemical_formula>C3H4O4</chemical_formula>
  <average_molecular_weight>104.0615</average_molecular_weight>
  <monisotopic_moleculate_weight>104.010958616</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxy-2-oxopropanoic acid</iupac_name>
  <traditional_iupac>hydroxypyruvic acid</traditional_iupac>
  <cas_registry_number>1113-60-6</cas_registry_number>
  <smiles>OCC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h4H,1H2,(H,6,7)</inchi>
  <inchikey>HHDDCCUIIUWNGJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Beta hydroxy acids and derivatives</sub_class>
    <direct_parent>Beta hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Keto acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>3-hydroxy monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxy-2-oxopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>104.0615</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>104.010958616</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H4O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h4H,1H2,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HHDDCCUIIUWNGJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>19.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38036</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00168</kegg_id>
  <foodb_id>FDB030913</foodb_id>
  <chemspider_id>939</chemspider_id>
  <drugbank_id>DB02951</drugbank_id>
  <pubchem_compound_id>964</pubchem_compound_id>
  <chebi_id>30841</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00007563</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34120</bigg_id>
  <wikipedia_id>Hydroxypyruvic_acid</wikipedia_id>
  <metlin_id>482</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Behal, Francis J.  Hydroxypyruvic acid formation in Aspergillus niger.    Archives of Biochemistry and Biophysics  (1960),  88  110-12.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:36 UTC</creation_date>
  <update_date>2020-03-13 16:27:29 UTC</update_date>
  <accession>BMDB0001353</accession>
  <secondary_accessions>
    <accession>BMDB01353</accession>
  </secondary_accessions>
  <name>2-Keto-3-deoxy-D-gluconic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Dehydro-3-deoxy-D-gluconate</synonym>
    <synonym>2-Keto-3-deoxy-D-gluconate</synonym>
    <synonym>3-Deoxy-2-oxo-D-gluconate</synonym>
    <synonym>3-Deoxy-D-erythro-2-hexulosonic acid</synonym>
    <synonym>2-Dehydro-3-deoxy-D-gluconic acid</synonym>
    <synonym>3-Deoxy-2-oxo-D-gluconic acid</synonym>
    <synonym>3-Deoxy-D-erythro-2-hexulosonate</synonym>
    <synonym>2-keto-3-Deoxygluconate</synonym>
  </synonyms>
  <chemical_formula>C6H10O6</chemical_formula>
  <average_molecular_weight>178.14</average_molecular_weight>
  <monisotopic_moleculate_weight>178.047738052</monisotopic_moleculate_weight>
  <iupac_name>(4S,5R)-4,5,6-trihydroxy-2-oxohexanoic acid</iupac_name>
  <traditional_iupac>2-dehydro-3-deoxy-D-gluconate</traditional_iupac>
  <cas_registry_number>17510-99-5</cas_registry_number>
  <smiles>[H][C@@](O)(CO)[C@@]([H])(O)CC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H10O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3,5,7-8,10H,1-2H2,(H,11,12)/t3-,5+/m0/s1</inchi>
  <inchikey>WPAMZTWLKIDIOP-WVZVXSGGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12  carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Medium-chain keto acids and derivatives</sub_class>
    <direct_parent>Medium-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Medium-chain keto acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>hexonic acid</external_descriptor>
      <external_descriptor>ketoaldonic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4S,5R)-4,5,6-trihydroxy-2-oxohexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>178.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>178.047738052</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](O)(CO)[C@@]([H])(O)CC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O6/c7-2-5(10)3(8)1-4(9)6(11)12/h3,5,7-8,10H,1-2H2,(H,11,12)/t3-,5+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WPAMZTWLKIDIOP-WVZVXSGGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>115.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>36.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35599</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00204</kegg_id>
  <foodb_id/>
  <drugbank_id/>
  <chemspider_id/>
  <pdbe_id/>
  <chebi_id>17032</chebi_id>
  <pubchem_compound_id>161227</pubchem_compound_id>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Plantier-Royon, Richard; Anker, Daniel; Robert-Baudouy, , Janine. New synthesis of 3-deoxy-D-erythro-2-hexulosonic acid (KDG) from D-glucose. Journal of Carbohydrate Chemistry (1991), 10(2), 239-49.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:38 UTC</creation_date>
  <update_date>2020-03-13 16:27:29 UTC</update_date>
  <accession>BMDB0001354</accession>
  <secondary_accessions>
    <accession>BMDB01354</accession>
  </secondary_accessions>
  <name>5,10-Methenyltetrahydrofolic acid</name>
  <description>5,10-5,10-5,10-methenyltetrahydrofolic acid, also known as 5,10-5,10-methenyltetrahydrofolic acid or 5,10-methenyl-THF, belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. 5,10-5,10-5,10-methenyltetrahydrofolic acid is possibly soluble (in water) and a moderately basic compound (based on its pKa). 5,10-5,10-5,10-methenyltetrahydrofolic acid exists in all living species, ranging from bacteria to humans. 5,10-5,10-5,10-methenyltetrahydrofolic acid participates in a number of enzymatic reactions, within cattle. In particular, 5,10-5,10-5,10-methenyltetrahydrofolic acid can be biosynthesized from 10-formyltetrahydrofolate; which is catalyzed by the enzyme C-1-tetrahydrofolate synthase, cytoplasmic. In addition, 5,10-5,10-5,10-methenyltetrahydrofolic acid can be biosynthesized from N5-formyl-THF; which is mediated by the enzyme 5-formyltetrahydrofolate cyclo-ligase. In cattle, 5,10-5,10-methenyltetrahydrofolic acid is involved in the metabolic pathway called the folate metabolism pathway.</description>
  <synonyms>
    <synonym>5,10-Methenyltetrahydrofolate</synonym>
    <synonym>5,10-Methenyl-THF</synonym>
    <synonym>Anhydro-leucovorin</synonym>
    <synonym>Anhydro-leucovorin a</synonym>
    <synonym>Anhydroleucovorin</synonym>
    <synonym>Anhydroleucovorin a</synonym>
    <synonym>CH-THF</synonym>
    <synonym>Methenyl-tetrahydrofolate</synonym>
    <synonym>Methenyl-THF</synonym>
    <synonym>Methenyltetrahydrofolate</synonym>
    <synonym>Methenyltetrahydrofolic acid</synonym>
    <synonym>N5-N10-CH-THF</synonym>
    <synonym>N5-N10-Methenyltetrahydrofolate</synonym>
    <synonym>5,10-Methenyltetrahydropteroylglutamate</synonym>
    <synonym>N5,N10-Methenyl tetrahydrofolate</synonym>
  </synonyms>
  <chemical_formula>C20H21N7O6</chemical_formula>
  <average_molecular_weight>455.424</average_molecular_weight>
  <monisotopic_moleculate_weight>455.155331439</monisotopic_moleculate_weight>
  <iupac_name>(6aR)-3-amino-8-(4-{[(1S)-3-carboxy-1-carboxylatopropyl]carbamoyl}phenyl)-1-oxo-1H,4H,5H,6H,6aH,7H,8H-10λ⁵-imidazo[1,5-f]pteridin-10-ylium</iupac_name>
  <traditional_iupac>(6aR)-3-amino-8-(4-{[(1S)-3-carboxy-1-carboxylatopropyl]carbamoyl}phenyl)-1-oxo-4H,5H,6H,6aH,7H-10λ⁵-imidazo[1,5-f]pteridin-10-ylium</traditional_iupac>
  <cas_registry_number>7444-29-3</cas_registry_number>
  <smiles>[H][C@@]12CN(C=[N+]1C1=C(NC2)NC(N)=NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C([O-])=O</smiles>
  <inchi>InChI=1S/C20H21N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/t12-,13+/m1/s1</inchi>
  <inchikey>MEANFMOQMXYMCT-OLZOCXBDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Tetrahydrofolic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxamidines</alternative_parent>
      <alternative_parent>Carboxylic acid salts</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Glutamic acid and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hippuric acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-imidazoline</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amidine</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzamide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoic acid or derivatives</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid amidine</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hippuric acid</substituent>
      <substituent>Hippuric acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tetrahydrofolic acid</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(6aR)-3-amino-8-(4-{[(1S)-3-carboxy-1-carboxylatopropyl]carbamoyl}phenyl)-1-oxo-1H,4H,5H,6H,6aH,7H,8H-10λ⁵-imidazo[1,5-f]pteridin-10-ylium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>455.424</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>455.155331439</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CN(C=[N+]1C1=C(NC2)NC(N)=NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C([O-])=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H21N7O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H21N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/t12-,13+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MEANFMOQMXYMCT-OLZOCXBDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>192.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>145.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>43.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30970</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022573</foodb_id>
  <chemspider_id>559356</chemspider_id>
  <pubchem_compound_id>135450599</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id>C00445</kegg_id>
  <chebi_id>15636</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>34999</bigg_id>
  <wikipedia_id>5,10-Methenyltetrahydrofolate</wikipedia_id>
  <metlin_id>6185</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00374</protein_accession>
      <name>Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrial</name>
      <uniprot_id>Q0P5C2</uniprot_id>
      <gene_name>MTHFD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:39 UTC</creation_date>
  <update_date>2020-03-13 16:27:30 UTC</update_date>
  <accession>BMDB0001356</accession>
  <secondary_accessions>
    <accession>BMDB01356</accession>
  </secondary_accessions>
  <name>2-Methyl-3-hydroxybutyryl-CoA</name>
  <description/>
  <synonyms>
    <synonym>(2S,3S)-3-Hydroxy-2-methylbutanoyl-CoA</synonym>
    <synonym>(2S,3S)-3-Hydroxy-2-methylbutanoyl-coenzyme A</synonym>
    <synonym>(2S,3S)-3-Hydroxy-2-methylbutyryl-CoA</synonym>
    <synonym>(2S,3S)-3-Hydroxy-2-methylbutyryl-coenzyme A</synonym>
    <synonym>(S)-3-Hydroxy-2-methylbutyryl-CoA</synonym>
    <synonym>(S)-3-Hydroxy-2-methylbutyryl-coenzyme A</synonym>
    <synonym>2-Methyl-3-hydroxybutyryl-coenzyme A</synonym>
    <synonym>3-Hydroxy-2-methylbutyryl-CoA</synonym>
    <synonym>3-Hydroxy-2-methylbutyryl-coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C26H44N7O18P3S</chemical_formula>
  <average_molecular_weight>867.65</average_molecular_weight>
  <monisotopic_moleculate_weight>867.167637865</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(2S,3S)-3-hydroxy-2-methylbutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-3-({2-[(2-{[(2S,3S)-3-hydroxy-2-methylbutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>52227-66-4</cas_registry_number>
  <smiles>C[C@H](O)[C@H](C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C26H44N7O18P3S/c1-13(14(2)34)25(39)55-8-7-28-16(35)5-6-29-23(38)20(37)26(3,4)10-48-54(45,46)51-53(43,44)47-9-15-19(50-52(40,41)42)18(36)24(49-15)33-12-32-17-21(27)30-11-31-22(17)33/h11-15,18-20,24,34,36-37H,5-10H2,1-4H3,(H,28,35)(H,29,38)(H,43,44)(H,45,46)(H2,27,30,31)(H2,40,41,42)/t13-,14-,15+,18+,19+,20?,24+/m0/s1</inchi>
  <inchikey>PEKYNTFSOBAABV-SYASONGASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (s)-3-hydroxyacyl coas. These are organic compounds containing a (S)-3-hydroxyl acylated coenzyme A derivative.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>(S)-3-hydroxyacyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-3-({2-[(2-{[(2S,3S)-3-hydroxy-2-methylbutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>867.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>867.167637865</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](O)[C@H](C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H44N7O18P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H44N7O18P3S/c1-13(14(2)34)25(39)55-8-7-28-16(35)5-6-29-23(38)20(37)26(3,4)10-48-54(45,46)51-53(43,44)47-9-15-19(50-52(40,41)42)18(36)24(49-15)33-12-32-17-21(27)30-11-31-22(17)33/h11-15,18-20,24,34,36-37H,5-10H2,1-4H3,(H,28,35)(H,29,38)(H,43,44)(H,45,46)(H2,27,30,31)(H2,40,41,42)/t13-,14-,15+,18+,19+,20?,24+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PEKYNTFSOBAABV-SYASONGASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>383.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>187.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>77.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>59946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>59947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>59948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>116184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>116185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>116186</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04405</kegg_id>
  <foodb_id>FDB022575</foodb_id>
  <drugbank_id/>
  <chemspider_id>389295</chemspider_id>
  <pubchem_compound_id>440326</pubchem_compound_id>
  <chebi_id>15449</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>43751</bigg_id>
  <metlin_id>6186</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00961</protein_accession>
      <name>3-hydroxyacyl-CoA dehydrogenase type-2</name>
      <uniprot_id>O02691</uniprot_id>
      <gene_name>HSD17B10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:40 UTC</creation_date>
  <update_date>2020-04-16 20:40:05 UTC</update_date>
  <accession>BMDB0001358</accession>
  <secondary_accessions>
    <accession>BMDB01358</accession>
  </secondary_accessions>
  <name>Retinal</name>
  <description>13-cis-13-cis-13-cis-retinal, also known as 13Z-13-cis-retinal or 13-cis-retinal, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Thus, 13-cis-13-cis-retinal is considered to be an isoprenoid lipid molecule. 13-cis-13-cis-13-cis-retinal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 13-cis-13-cis-13-cis-retinal exists in all living organisms, ranging from bacteria to humans. In cattle, 13-cis-13-cis-retinal is involved in the metabolic pathway called the retinol metabolism pathway.</description>
  <synonyms>
    <synonym>all-trans-Retinaldehyde</synonym>
    <synonym>all-trans-Retinene</synonym>
    <synonym>all-trans-Vitamin a aldehyde</synonym>
    <synonym>Retinaldehyde</synonym>
    <synonym>Retinene</synonym>
    <synonym>Vitamin a aldehyde</synonym>
    <synonym>all-trans-Retinal</synonym>
    <synonym>Aldehyde, vitamin a</synonym>
    <synonym>Axerophthal</synonym>
    <synonym>11 cis Retinal</synonym>
    <synonym>11-cis-Retinal</synonym>
    <synonym>3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal</synonym>
    <synonym>all-e-Retinal</synonym>
    <synonym>all-epsilon-Retinal</synonym>
    <synonym>alpha-Retinene</synonym>
    <synonym>e-Retinal</synonym>
    <synonym>epsilon-Retinal</synonym>
    <synonym>Retinene 1</synonym>
    <synonym>trans-Retinal</synonym>
    <synonym>trans-Vitamin a aldehyde</synonym>
    <synonym>Vitamin a1 aldehyde</synonym>
  </synonyms>
  <chemical_formula>C20H28O</chemical_formula>
  <average_molecular_weight>284.4357</average_molecular_weight>
  <monisotopic_moleculate_weight>284.214015518</monisotopic_moleculate_weight>
  <iupac_name>(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal</iupac_name>
  <traditional_iupac>retinaldehyde</traditional_iupac>
  <cas_registry_number>116-31-4</cas_registry_number>
  <smiles>C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O</smiles>
  <inchi>InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+</inchi>
  <inchikey>NCYCYZXNIZJOKI-OVSJKPMPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Retinoids</sub_class>
    <direct_parent>Retinoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Aldehydes</alternative_parent>
      <alternative_parent>Diterpenoids</alternative_parent>
      <alternative_parent>Enals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Alpha,beta-unsaturated aldehyde</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Diterpenoid</substituent>
      <substituent>Enal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Retinoid skeleton</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Retinoids</external_descriptor>
      <external_descriptor>Retinoids</external_descriptor>
      <external_descriptor>retinal</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>63 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>284.4357</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>284.214015518</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H28O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NCYCYZXNIZJOKI-OVSJKPMPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>96.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Retinol Metabolism</name>
      <smpdb_id>SMP0087260</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30676</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00376</kegg_id>
  <foodb_id>FDB022576</foodb_id>
  <drugbank_id/>
  <chemspider_id/>
  <pubchem_compound_id>638015</pubchem_compound_id>
  <chebi_id>17898</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>RETINAL</meta_cyc_id>
  <wikipedia_id>Retinal</wikipedia_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Duhamel, Lucette; Duhamel, Pierre; Lecouve, Jean Pierre. A new synthesis of retinals. Journal of Chemical Research, Synopses (1986), (1), 34-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00102</protein_accession>
      <name>Prostaglandin-H2 D-isomerase</name>
      <uniprot_id>O02853</uniprot_id>
      <gene_name>PTGDS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00601</protein_accession>
      <name>Retinal dehydrogenase 1</name>
      <uniprot_id>P48644</uniprot_id>
      <gene_name>ALDH1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00606</protein_accession>
      <name>Hydroxysteroid 17-beta dehydrogenase 6</name>
      <uniprot_id>Q3T001</uniprot_id>
      <gene_name>HSD17B6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00713</protein_accession>
      <name>Retinol dehydrogenase 8</name>
      <uniprot_id>Q9N126</uniprot_id>
      <gene_name>RDH8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00715</protein_accession>
      <name>11-cis retinol dehydrogenase</name>
      <uniprot_id>Q27979</uniprot_id>
      <gene_name>RDH5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00716</protein_accession>
      <name>Retinol dehydrogenase 10</name>
      <uniprot_id>Q8HZT6</uniprot_id>
      <gene_name>RDH10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01869</protein_accession>
      <name>Gamma-aminobutyric acid receptor subunit rho-2</name>
      <uniprot_id>Q0II76</uniprot_id>
      <gene_name>GABRR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01885</protein_accession>
      <name>Cellular retinoic acid-binding protein 1</name>
      <uniprot_id>P62964</uniprot_id>
      <gene_name>CRABP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01888</protein_accession>
      <name>Cellular retinoic acid-binding protein 2</name>
      <uniprot_id>Q5PXY7</uniprot_id>
      <gene_name>CRABP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01964</protein_accession>
      <name>Retinol-binding protein 5</name>
      <uniprot_id>P82708</uniprot_id>
      <gene_name>RBP5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01965</protein_accession>
      <name>Retinol-binding protein 1</name>
      <uniprot_id>P02694</uniprot_id>
      <gene_name>RBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01966</protein_accession>
      <name>Retinol-binding protein 3</name>
      <uniprot_id>P12661</uniprot_id>
      <gene_name>RBP3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01968</protein_accession>
      <name>Retinol-binding protein 4</name>
      <uniprot_id>P18902</uniprot_id>
      <gene_name>RBP4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02678</protein_accession>
      <name>RPE-retinal G protein-coupled receptor</name>
      <uniprot_id>P47803</uniprot_id>
      <gene_name>RGR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:41 UTC</creation_date>
  <update_date>2020-03-13 16:27:31 UTC</update_date>
  <accession>BMDB0001359</accession>
  <secondary_accessions>
    <accession>BMDB01359</accession>
  </secondary_accessions>
  <name>Phytanoyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>3,7,11,15-Tetramethyl hexadecanoyl CoA</synonym>
    <synonym>3,7,11,15-Tetramethyl hexadecanoyl coenzyme A</synonym>
    <synonym>Phytanoyl CoA</synonym>
    <synonym>Phytanoyl coenzyme A</synonym>
    <synonym>Phytanoyl-coenzyme A</synonym>
    <synonym>Phytanyl CoA</synonym>
    <synonym>Phytanyl coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C41H74N7O17P3S</chemical_formula>
  <average_molecular_weight>1062.049</average_molecular_weight>
  <monisotopic_moleculate_weight>1061.407474203</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-2,2-dimethyl-3-({2-[(2-{[(3S,7R,11R)-3,7,11,15-tetramethylhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-({2-[(2-{[(3S,7R,11R)-3,7,11,15-tetramethylhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>146622-45-9</cas_registry_number>
  <smiles>CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](C)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C41H74N7O17P3S/c1-26(2)11-8-12-27(3)13-9-14-28(4)15-10-16-29(5)21-32(50)69-20-19-43-31(49)17-18-44-39(53)36(52)41(6,7)23-62-68(59,60)65-67(57,58)61-22-30-35(64-66(54,55)56)34(51)40(63-30)48-25-47-33-37(42)45-24-46-38(33)48/h24-30,34-36,40,51-52H,8-23H2,1-7H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/t27-,28-,29+,30-,34-,35-,36?,40-/m1/s1</inchi>
  <inchikey>NRJQGHHZMSOUEN-IYJVDCLDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Long-chain fatty acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>2,3,4-saturated fatty acyl CoAs</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Diterpenoids</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Diterpenoid</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-2,2-dimethyl-3-({2-[(2-{[(3S,7R,11R)-3,7,11,15-tetramethylhexadecanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1062.049</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1061.407474203</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@H](C)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C41H74N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C41H74N7O17P3S/c1-26(2)11-8-12-27(3)13-9-14-28(4)15-10-16-29(5)21-32(50)69-20-19-43-31(49)17-18-44-39(53)36(52)41(6,7)23-62-68(59,60)65-67(57,58)61-22-30-35(64-66(54,55)56)34(51)40(63-30)48-25-47-33-37(42)45-24-46-38(33)48/h24-30,34-36,40,51-52H,8-23H2,1-7H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/t27-,28-,29+,30-,34-,35-,36?,40-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NRJQGHHZMSOUEN-IYJVDCLDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>254.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>106.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>289986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329574</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02060</kegg_id>
  <foodb_id>FDB022577</foodb_id>
  <drugbank_id/>
  <chemspider_id>388712</chemspider_id>
  <pubchem_compound_id>439640</pubchem_compound_id>
  <chebi_id>15538</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <wikipedia_id>Phytanoyl-CoA</wikipedia_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>2364522</bigg_id>
  <metlin_id>6189</metlin_id>
  <synthesis_reference>Kershaw, N. J.; Mukherji, M.; MacKinnon, C. H.; Claridge, T. D. W.; Odell, B.; Wierzbicki, A. S.; Lloyd, M. D.; Schofield, C. J. Studies on phytanoyl-CoA 2-hydroxylase and synthesis of phytanoyl-Coenzyme A. Bioorganic &amp; Medicinal Chemistry Letters (2001) 11(18), 17 September 2001, p.2545-2548</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00688</protein_accession>
      <name>Phytanoyl-CoA dioxygenase, peroxisomal</name>
      <uniprot_id>O18778</uniprot_id>
      <gene_name>PHYH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:42 UTC</creation_date>
  <update_date>2020-03-13 16:27:31 UTC</update_date>
  <accession>BMDB0001361</accession>
  <secondary_accessions>
    <accession>BMDB01361</accession>
  </secondary_accessions>
  <name>Carbon monoxide</name>
  <description>Carbon monoxide, also known as Carbon monoxide or C#O, belongs to the class of inorganic carbon monoxidempounds known as homogeneous other non-metal carbon monoxidempounds. These are inorganic non-metallic carbon monoxidempounds in which the largest atom belongs to the class of 'other non-metals'. Carbon monoxide is a drug which is used as a marker of respiratory status in spirometry tests [l2557], [f4].</description>
  <synonyms>
    <synonym>[CO]</synonym>
    <synonym>C#O</synonym>
    <synonym>CO</synonym>
    <synonym>Monoxide, carbon</synonym>
  </synonyms>
  <chemical_formula>CO</chemical_formula>
  <average_molecular_weight>28.01</average_molecular_weight>
  <monisotopic_moleculate_weight>27.99491462</monisotopic_moleculate_weight>
  <iupac_name/>
  <traditional_iupac/>
  <cas_registry_number>630-08-0</cas_registry_number>
  <smiles>[C-]#[O+]</smiles>
  <inchi>InChI=1S/CO/c1-2</inchi>
  <inchikey>UGFAIRIUMAVXCW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Homogeneous other non-metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous other non-metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous other non metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>carbon oxide</external_descriptor>
      <external_descriptor>one-carbon compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>28.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>27.99491462</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[C-]#[O+]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/CO/c1-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UGFAIRIUMAVXCW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>26.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>99069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>99070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>99071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>164148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>164149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>164150</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00237</kegg_id>
  <foodb_id>FDB022578</foodb_id>
  <drugbank_id>DB11588</drugbank_id>
  <chemspider_id>275</chemspider_id>
  <pubchem_compound_id>281</pubchem_compound_id>
  <chebi_id>17245</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>CARBON-MONOXIDE</meta_cyc_id>
  <wikipedia_id>Carbon_monoxide</wikipedia_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>1749973</bigg_id>
  <metlin_id/>
  <synthesis_reference>Ivanova, Svetlana; Pitchon, Veronique; Petit, Corinne. Application of the direct exchange method in the preparation of gold catalysts supported on different oxide materials. Journal of Molecular Catalysis A: Chemical (2006), 256(1-2), 278-283.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01344</protein_accession>
      <name>Calcium-activated potassium channel subunit alpha-1</name>
      <uniprot_id>Q28204</uniprot_id>
      <gene_name>KCNMA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:43 UTC</creation_date>
  <update_date>2020-03-13 16:27:32 UTC</update_date>
  <accession>BMDB0001362</accession>
  <secondary_accessions>
    <accession>BMDB01362</accession>
  </secondary_accessions>
  <name>Hydrogen</name>
  <description/>
  <synonyms>
    <synonym>e 949</synonym>
    <synonym>e-949</synonym>
    <synonym>e949</synonym>
    <synonym>H2</synonym>
    <synonym>Molecular hydrogen</synonym>
    <synonym>Dihydrogen</synonym>
    <synonym>Hydrogen gas</synonym>
    <synonym>Hydrogen-1</synonym>
    <synonym>Hydrogen 1</synonym>
  </synonyms>
  <chemical_formula>H2</chemical_formula>
  <average_molecular_weight>2.0159</average_molecular_weight>
  <monisotopic_moleculate_weight>2.015650064</monisotopic_moleculate_weight>
  <iupac_name/>
  <traditional_iupac/>
  <cas_registry_number>1333-74-0</cas_registry_number>
  <smiles>[H][H]</smiles>
  <inchi>InChI=1S/H2/h1H</inchi>
  <inchikey>UFHFLCQGNIYNRP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as other non-metal hydrides. These are inorganic compounds in which the heaviest atom bonded to a hydrogen atom is belongs to the class of 'other non-metals'.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Other non-metal organides</class>
    <sub_class>Other non-metal hydrides</sub_class>
    <direct_parent>Other non-metal hydrides</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Other non-metal hydride</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>elemental hydrogen</external_descriptor>
      <external_descriptor>elemental molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-259.2 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.00162 mg/mL at 21 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>average_mass</kind>
      <value>2.0159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>2.015650064</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][H]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/H2/h1H</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UFHFLCQGNIYNRP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>0.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Apoptotic DNA Fragmentation and Tissue Homeostasis</name>
      <smpdb_id>SMP0108203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Threonine and 2-Oxobutanoate Degradation</name>
      <smpdb_id>SMP0087262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31189</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00282</kegg_id>
  <foodb_id>FDB016247</foodb_id>
  <drugbank_id/>
  <chemspider_id/>
  <pdbe_id/>
  <chebi_id>18276</chebi_id>
  <pubchem_compound_id>783</pubchem_compound_id>
  <meta_cyc_id>HYDROGEN-MOLECULE</meta_cyc_id>
  <wikipedia_id>Hydrogen</wikipedia_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Ait-Ichou, I.; Formenti, M.; Pommier, B.; Teichner, S. J. Photocatalytic dehydrogenation of isopropanol on platinum/titania catalysts. Journal of Catalysis (1985), 91(2), 293-307.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00189</protein_accession>
      <name>ATP synthase subunit beta, mitochondrial</name>
      <uniprot_id>P00829</uniprot_id>
      <gene_name>ATP5B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00595</protein_accession>
      <name>Hydroxyacid-oxoacid transhydrogenase, mitochondrial</name>
      <uniprot_id>A6QP15</uniprot_id>
      <gene_name>ADHFE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00717</protein_accession>
      <name>ATP synthase subunit f, mitochondrial</name>
      <uniprot_id>Q28851</uniprot_id>
      <gene_name>ATP5J2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00718</protein_accession>
      <name>ATP synthase lipid-binding protein, mitochondrial</name>
      <uniprot_id>P32876</uniprot_id>
      <gene_name>ATP5G1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00719</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>Q85CR8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00720</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>Q45MM4</uniprot_id>
      <gene_name>ATP6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00721</protein_accession>
      <name>Similar to ATP synthase A chain (Protein 6)</name>
      <uniprot_id>Q85E89</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00722</protein_accession>
      <name>H+-transporting lysosomal 21kDa ATPase V0 subunit c transcript variant 1</name>
      <uniprot_id>A1XE98</uniprot_id>
      <gene_name>ATP6V0B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00723</protein_accession>
      <name>ATP synthase protein 8</name>
      <uniprot_id>Q45MQ1</uniprot_id>
      <gene_name>ATP8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00724</protein_accession>
      <name>V-type proton ATPase subunit d 1</name>
      <uniprot_id>P61420</uniprot_id>
      <gene_name>ATP6V0D1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00725</protein_accession>
      <name>ATP synthase lipid-binding protein, mitochondrial</name>
      <uniprot_id>Q3ZC75</uniprot_id>
      <gene_name>ATP5G3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00726</protein_accession>
      <name>ATP synthase subunit d, mitochondrial</name>
      <uniprot_id>P13620</uniprot_id>
      <gene_name>ATP5H</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00727</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>P00847</uniprot_id>
      <gene_name>MT-ATP6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00728</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>Q7JAT1</uniprot_id>
      <gene_name>ATP6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00729</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>Q45LV1</uniprot_id>
      <gene_name>ATP6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00730</protein_accession>
      <name>ATP synthase subunit alpha, mitochondrial</name>
      <uniprot_id>P19483</uniprot_id>
      <gene_name>ATP5A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00731</protein_accession>
      <name>V-type proton ATPase subunit B, brain isoform</name>
      <uniprot_id>P31408</uniprot_id>
      <gene_name>ATP6V1B2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00732</protein_accession>
      <name>V-type proton ATPase subunit C 1</name>
      <uniprot_id>P21282</uniprot_id>
      <gene_name>ATP6V1C1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00733</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>Q85E91</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00734</protein_accession>
      <name>ATP synthase protein 8</name>
      <uniprot_id>Q7JAT2</uniprot_id>
      <gene_name>ATP8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00735</protein_accession>
      <name>ATP synthase</name>
      <uniprot_id>Q862C2</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00736</protein_accession>
      <name>ATP synthase subunit s, mitochondrial</name>
      <uniprot_id>P22027</uniprot_id>
      <gene_name>ATP5S</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00737</protein_accession>
      <name>V-type proton ATPase subunit d 2</name>
      <uniprot_id>Q2KJB6</uniprot_id>
      <gene_name>ATP6V0D2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00738</protein_accession>
      <name>ATP synthase subunit gamma, mitochondrial</name>
      <uniprot_id>P05631</uniprot_id>
      <gene_name>ATP5C1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00739</protein_accession>
      <name>V-type proton ATPase subunit F</name>
      <uniprot_id>Q28029</uniprot_id>
      <gene_name>ATP6V1F</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00740</protein_accession>
      <name>V-type proton ATPase 116 kDa subunit a isoform 2</name>
      <uniprot_id>O97681</uniprot_id>
      <gene_name>ATP6V0A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00741</protein_accession>
      <name>V-type proton ATPase 21 kDa proteolipid subunit</name>
      <uniprot_id>Q2TA24</uniprot_id>
      <gene_name>ATP6V0B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00742</protein_accession>
      <name>ATP synthase protein 8</name>
      <uniprot_id>P03929</uniprot_id>
      <gene_name>MT-ATP8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00743</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>Q85E93</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00744</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>B1NZT1</uniprot_id>
      <gene_name>ATP6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00745</protein_accession>
      <name>V-type proton ATPase subunit e 1</name>
      <uniprot_id>P81103</uniprot_id>
      <gene_name>ATP6V0E1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00746</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>Q85E97</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00747</protein_accession>
      <name>V-type proton ATPase subunit E 1</name>
      <uniprot_id>P11019</uniprot_id>
      <gene_name>ATP6V1E1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00748</protein_accession>
      <name>ATP synthase subunit g, mitochondrial</name>
      <uniprot_id>Q28852</uniprot_id>
      <gene_name>ATP5L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00749</protein_accession>
      <name>ATP synthase protein 8</name>
      <uniprot_id>Q45LL1</uniprot_id>
      <gene_name>ATP8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00750</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>B1P0J1</uniprot_id>
      <gene_name>ATP6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00751</protein_accession>
      <name>V-type proton ATPase subunit B, kidney isoform</name>
      <uniprot_id>P31407</uniprot_id>
      <gene_name>ATP6V1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00752</protein_accession>
      <name>V-type proton ATPase 116 kDa subunit a isoform 1</name>
      <uniprot_id>Q29466</uniprot_id>
      <gene_name>ATP6V0A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00753</protein_accession>
      <name>ATP synthase subunit e, mitochondrial</name>
      <uniprot_id>Q00361</uniprot_id>
      <gene_name>ATP5I</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00754</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>Q85E92</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00755</protein_accession>
      <name>ATP synthase</name>
      <uniprot_id>Q862U3</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00756</protein_accession>
      <name>ATP synthase subunit b, mitochondrial</name>
      <uniprot_id>P13619</uniprot_id>
      <gene_name>ATP5F1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00757</protein_accession>
      <name>ATP synthase protein 8</name>
      <uniprot_id>B1P0L6</uniprot_id>
      <gene_name>ATP8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00758</protein_accession>
      <name>V-type proton ATPase subunit G 1</name>
      <uniprot_id>P79251</uniprot_id>
      <gene_name>ATP6V1G1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00759</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>B1NZU4</uniprot_id>
      <gene_name>ATP6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00760</protein_accession>
      <name>ATP synthase subunit epsilon, mitochondrial</name>
      <uniprot_id>P05632</uniprot_id>
      <gene_name>ATP5E</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00761</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>Q3L5Q7</uniprot_id>
      <gene_name>ATP6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00762</protein_accession>
      <name>ATP synthase subunit beta</name>
      <uniprot_id>Q0QEM9</uniprot_id>
      <gene_name>ATP5B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00763</protein_accession>
      <name>ATP synthase subunit delta, mitochondrial</name>
      <uniprot_id>P05630</uniprot_id>
      <gene_name>ATP5D</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00764</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>A1XEE3</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00765</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>B1P0A0</uniprot_id>
      <gene_name>ATP6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00766</protein_accession>
      <name>ATP synthase subunit O, mitochondrial</name>
      <uniprot_id>P13621</uniprot_id>
      <gene_name>ATP5O</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00767</protein_accession>
      <name>V-type proton ATPase subunit E 2</name>
      <uniprot_id>Q32LB7</uniprot_id>
      <gene_name>ATP6V1E2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00768</protein_accession>
      <name>V-type proton ATPase subunit S1</name>
      <uniprot_id>P40682</uniprot_id>
      <gene_name>ATP6AP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00769</protein_accession>
      <name>ATP synthase protein 8</name>
      <uniprot_id>B1NZI9</uniprot_id>
      <gene_name>ATP8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00770</protein_accession>
      <name>ATP synthase-coupling factor 6, mitochondrial</name>
      <uniprot_id>P02721</uniprot_id>
      <gene_name>ATP5J</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00771</protein_accession>
      <name>V-type proton ATPase 16 kDa proteolipid subunit</name>
      <uniprot_id>P23956</uniprot_id>
      <gene_name>ATP6V0C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00772</protein_accession>
      <name>ATP synthase protein 8</name>
      <uniprot_id>Q45LM4</uniprot_id>
      <gene_name>ATP8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00773</protein_accession>
      <name>V-type proton ATPase catalytic subunit A</name>
      <uniprot_id>P31404</uniprot_id>
      <gene_name>ATP6V1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00774</protein_accession>
      <name>V-type proton ATPase subunit H</name>
      <uniprot_id>O46563</uniprot_id>
      <gene_name>ATP6V1H</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00775</protein_accession>
      <name>ATP synthase protein 8</name>
      <uniprot_id>Q45LV2</uniprot_id>
      <gene_name>ATP8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00776</protein_accession>
      <name>Similar to ATPase 6</name>
      <uniprot_id>Q85EA5</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00777</protein_accession>
      <name>ATP synthase lipid-binding protein, mitochondrial</name>
      <uniprot_id>P07926</uniprot_id>
      <gene_name>ATP5G2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00778</protein_accession>
      <name>V-type proton ATPase subunit D</name>
      <uniprot_id>P39942</uniprot_id>
      <gene_name>ATP6V1D</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00779</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>Q85E95</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00780</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>B1NZK3</uniprot_id>
      <gene_name>ATP6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00781</protein_accession>
      <name>ATP synthase subunit a</name>
      <uniprot_id>Q85AQ8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00782</protein_accession>
      <name>V-type proton ATPase subunit e 2</name>
      <uniprot_id>Q2KIB5</uniprot_id>
      <gene_name>ATP6V0E2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01970</protein_accession>
      <name>ATP6AP1 protein</name>
      <uniprot_id>Q3MHZ3</uniprot_id>
      <gene_name>ATP6AP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01971</protein_accession>
      <name>ATPase, H+ transporting, lysosomal 13kDa, V1 subunit G2</name>
      <uniprot_id>Q0VCV6</uniprot_id>
      <gene_name>ATP6V1G2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01972</protein_accession>
      <name>T-cell, immune regulator 1, ATPase, H+ transporting, lysosomal V0 subunit A3</name>
      <uniprot_id>Q1RMS1</uniprot_id>
      <gene_name>TCIRG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01973</protein_accession>
      <name>ATP6V1C2 protein</name>
      <uniprot_id>A4IFJ9</uniprot_id>
      <gene_name>ATP6V1C2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01974</protein_accession>
      <name>ATP6V1B1 protein</name>
      <uniprot_id>A6QP02</uniprot_id>
      <gene_name>ATP6V1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01975</protein_accession>
      <name>ATP6V0B</name>
      <uniprot_id>A1XEC7</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01976</protein_accession>
      <name>ATP6V1G2 protein</name>
      <uniprot_id>Q2NKS1</uniprot_id>
      <gene_name>ATP6V1G2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01977</protein_accession>
      <name>ATP6V0A1 protein</name>
      <uniprot_id>A7Z016</uniprot_id>
      <gene_name>ATP6V0A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01978</protein_accession>
      <name>ATP synthase, H+ transporting, mitochondrial F0 complex, subunit d isoform a</name>
      <uniprot_id>Q1JP98</uniprot_id>
      <gene_name>ATP5H</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01979</protein_accession>
      <name>ATPase, H+ transporting, lysosomal 31kD, V1 subunit E isoform 1</name>
      <uniprot_id>Q58DR7</uniprot_id>
      <gene_name>ATP6V1E1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:45 UTC</creation_date>
  <update_date>2020-04-15 22:32:56 UTC</update_date>
  <accession>BMDB0001364</accession>
  <secondary_accessions>
    <accession>BMDB01364</accession>
  </secondary_accessions>
  <name>Adenosine tetraphosphate</name>
  <description/>
  <synonyms>
    <synonym>Adenosine 5'-tetraphosphate</synonym>
    <synonym>Adenosine 5'-tetraphosphoric acid</synonym>
    <synonym>Adenosine tetraphosphoric acid</synonym>
    <synonym>Ap4</synonym>
    <synonym>ATPP</synonym>
    <synonym>P4A</synonym>
  </synonyms>
  <chemical_formula>C10H17N5O16P4</chemical_formula>
  <average_molecular_weight>587.1609</average_molecular_weight>
  <monisotopic_moleculate_weight>586.962075569</monisotopic_moleculate_weight>
  <iupac_name>{[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>adenosine tetraphosphic acid</traditional_iupac>
  <cas_registry_number>58337-43-2</cas_registry_number>
  <smiles>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C10H17N5O16P4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(28-10)1-27-33(21,22)30-35(25,26)31-34(23,24)29-32(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H,25,26)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>WWMWAMFHUSTZTA-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside polyphosphates. These are purine ribobucleotides with polyphosphate (with 4 or more phosphate) group linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside polyphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside polyphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>adenosine 5'-phosphate</external_descriptor>
      <external_descriptor>purine ribonucleoside 5'-tetraphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>587.1609</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>586.962075569</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H17N5O16P4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H17N5O16P4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(28-10)1-27-33(21,22)30-35(25,26)31-34(23,24)29-32(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H,25,26)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WWMWAMFHUSTZTA-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>325.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>106.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>42.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35644</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03483</kegg_id>
  <foodb_id>FDB022579</foodb_id>
  <chemspider_id>13390</chemspider_id>
  <pubchem_compound_id>14003</pubchem_compound_id>
  <chebi_id>18334</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Adenosine 5'-tetraphosphate</wikipedia_id>
  <metlin_id>6191</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:46 UTC</creation_date>
  <update_date>2020-04-15 22:15:11 UTC</update_date>
  <accession>BMDB0001365</accession>
  <secondary_accessions>
    <accession>BMDB01365</accession>
  </secondary_accessions>
  <name>Cotinine methonium ion</name>
  <description/>
  <synonyms>
    <synonym>N-Methylcotininium ion</synonym>
  </synonyms>
  <chemical_formula>C11H15N2O</chemical_formula>
  <average_molecular_weight>191.2496</average_molecular_weight>
  <monisotopic_moleculate_weight>191.118438112</monisotopic_moleculate_weight>
  <iupac_name>1-methyl-3-(1-methyl-5-oxopyrrolidin-2-yl)pyridin-1-ium</iupac_name>
  <traditional_iupac>cotinine methonium ion</traditional_iupac>
  <cas_registry_number>89932-52-5</cas_registry_number>
  <smiles>CN1C(CCC1=O)C1=C[N+](C)=CC=C1</smiles>
  <inchi>InChI=1S/C11H15N2O/c1-12-7-3-4-9(8-12)10-5-6-11(14)13(10)2/h3-4,7-8,10H,5-6H2,1-2H3/q+1</inchi>
  <inchikey>VHRXFWHPQMABEK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyrrolidinylpyridines</sub_class>
    <direct_parent>Pyrrolidinylpyridines</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>N-alkylpyrrolidines</alternative_parent>
      <alternative_parent>N-methylpyridinium compounds</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridinium derivatives</alternative_parent>
      <alternative_parent>Pyrrolidine-2-ones</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-pyrrolidone</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>N-alkylpyrrolidine</substituent>
      <substituent>N-methylpyridinium</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridinium</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidinylpyridine</substituent>
      <substituent>Pyrrolidone</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-methyl-3-(1-methyl-5-oxopyrrolidin-2-yl)pyridin-1-ium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>191.2496</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>191.118438112</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C(CCC1=O)C1=C[N+](C)=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H15N2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H15N2O/c1-12-7-3-4-9(8-12)10-5-6-11(14)13(10)2/h3-4,7-8,10H,5-6H2,1-2H3/q+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VHRXFWHPQMABEK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>24.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>55.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302895</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022580</foodb_id>
  <chemspider_id>563</chemspider_id>
  <pubchem_compound_id>583</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <drugbank_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6192</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:47 UTC</creation_date>
  <update_date>2020-04-16 20:40:06 UTC</update_date>
  <accession>BMDB0001366</accession>
  <secondary_accessions>
    <accession>BMDB01366</accession>
  </secondary_accessions>
  <name>Purine</name>
  <description>Purine, also known as purine base or 1H-purine, belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring. Purine exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Purine exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>Purine base</synonym>
    <synonym>1H-Purine</synonym>
    <synonym>6H-Imidazo[4,5-D]pyrimidine</synonym>
    <synonym>7-Methyltheophylline</synonym>
    <synonym>7H-Imidazo(4,5-D)pyrimidine</synonym>
    <synonym>7H-Purine</synonym>
    <synonym>9H-Purine</synonym>
    <synonym>beta-Purine</synonym>
    <synonym>Caffedrine</synonym>
    <synonym>Caffein</synonym>
    <synonym>Cafipel</synonym>
    <synonym>Coffeine</synonym>
    <synonym>Dasin</synonym>
    <synonym>Dexitac</synonym>
    <synonym>Diurex</synonym>
    <synonym>Durvitan</synonym>
    <synonym>Imidazo(4,5-D)pyrimidine</synonym>
    <synonym>Isopurine</synonym>
    <synonym>Koffein</synonym>
    <synonym>Mateina</synonym>
    <synonym>Methyltheobromine</synonym>
    <synonym>Phensal</synonym>
    <synonym>Propoxyphene compound 65</synonym>
    <synonym>{6h-imidazo[4,5-D]pyrimidine}</synonym>
    <synonym>{7h-imidazo[4,} 5-D]pyrimidine</synonym>
    <synonym>{Imidazo[4,5-D]pyrimidine}</synonym>
  </synonyms>
  <chemical_formula>C5H4N4</chemical_formula>
  <average_molecular_weight>120.1121</average_molecular_weight>
  <monisotopic_moleculate_weight>120.043596148</monisotopic_moleculate_weight>
  <iupac_name>7H-purine</iupac_name>
  <traditional_iupac>purine</traditional_iupac>
  <cas_registry_number>120-73-0</cas_registry_number>
  <smiles>N1C=NC2=C1C=NC=N2</smiles>
  <inchi>InChI=1S/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9)</inchi>
  <inchikey>KDCGOANMDULRCW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Purines and purine derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidines and pyrimidine derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Purine</substituent>
      <substituent>Pyrimidine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a ring</external_descriptor>
      <external_descriptor>purine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>214 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>500.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.37</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>7H-purine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>120.1121</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>120.043596148</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N1C=NC2=C1C=NC=N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H4N4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H4N4/c1-4-5(8-2-6-1)9-3-7-4/h1-3H,(H,6,7,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KDCGOANMDULRCW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>33.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451865</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB007311</foodb_id>
  <kegg_id>C15587</kegg_id>
  <chemspider_id>1015</chemspider_id>
  <pubchem_compound_id>1044</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17258</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Purine</wikipedia_id>
  <metlin_id>6193</metlin_id>
  <synthesis_reference>Beaman, Alden G. New synthesis of purine. Journal of the American Chemical Society (1954), 76 5633-6.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00698</protein_accession>
      <name>Purine nucleoside phosphorylase</name>
      <uniprot_id>P55859</uniprot_id>
      <gene_name>NP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:48 UTC</creation_date>
  <update_date>2020-04-14 22:49:08 UTC</update_date>
  <accession>BMDB0001367</accession>
  <secondary_accessions>
    <accession>BMDB01367</accession>
  </secondary_accessions>
  <name>N-Acetyl-glucosamine 1-phosphate</name>
  <description>N-Acetyl-glucosamine 1-phosphate, also known as n-acetyl-glucosamine 1-phosphate, belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group. N-Acetyl-glucosamine 1-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-glucosamine 1-phosphate exists in all eukaryotes, ranging from yeast to humans. N-Acetyl-glucosamine 1-phosphate participates in a number of enzymatic reactions, within cattle. In particular, N-Acetyl-glucosamine 1-phosphate can be biosynthesized from N-acetyl-D-glucosamine 6-phosphate; which is catalyzed by the enzyme phosphoacetylglucosamine mutase. In addition, N-Acetyl-glucosamine 1-phosphate and uridine triphosphate can be converted into uridine diphosphate-N-acetylglucosamine through its interaction with the enzyme UDP-N-acetylhexosamine pyrophosphorylase. In cattle, N-acetyl-glucosamine 1-phosphate is involved in the metabolic pathway called the amino sugar metabolism pathway.</description>
  <synonyms>
    <synonym>2-(Acetylamino)-2-deoxy-D-glucopyranose 1-(dihydrogen phosphate)</synonym>
    <synonym>2-Acetamido-2-deoxy-1-O-phosphono-D-glucopyranose</synonym>
    <synonym>N-Acetyl-D-glucosamine 1-phosphate</synonym>
    <synonym>N-Acetylglucosamine-1-phosphate</synonym>
    <synonym>2-(Acetylamino)-2-deoxy-D-glucopyranose 1-(dihydrogen phosphoric acid)</synonym>
    <synonym>N-Acetyl-D-glucosamine 1-phosphoric acid</synonym>
    <synonym>N-Acetylglucosamine-1-phosphoric acid</synonym>
    <synonym>N-Acetyl-glucosamine 1-phosphoric acid</synonym>
    <synonym>D-Glucosamine 1-phosphate</synonym>
    <synonym>delta-Glucosamine 1-phosphate</synonym>
    <synonym>N-Acetyl-alpha-D-glucosamine 1-phosphate</synonym>
    <synonym>N-Acetyl-alpha-delta-glucosamine 1-phosphate</synonym>
    <synonym>N-Acetyl-delta-glucosamine 1-phosphate</synonym>
    <synonym>N-Acetyl-glucosamine-1-phosphate</synonym>
    <synonym>GlcNAc-1-phosphate</synonym>
  </synonyms>
  <chemical_formula>C8H16NO9P</chemical_formula>
  <average_molecular_weight>301.1877</average_molecular_weight>
  <monisotopic_moleculate_weight>301.056267627</monisotopic_moleculate_weight>
  <iupac_name>{[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>6866-69-9</cas_registry_number>
  <smiles>CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C8H16NO9P/c1-3(11)9-5-7(13)6(12)4(2-10)17-8(5)18-19(14,15)16/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H2,14,15,16)/t4-,5-,6-,7-,8?/m1/s1</inchi>
  <inchikey>FZLJPEPAYPUMMR-RTRLPJTCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>N-acyl-alpha-hexosamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acetyl-D-glucosamine 1-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>301.1877</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>301.056267627</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16NO9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16NO9P/c1-3(11)9-5-7(13)6(12)4(2-10)17-8(5)18-19(14,15)16/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H2,14,15,16)/t4-,5-,6-,7-,8?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FZLJPEPAYPUMMR-RTRLPJTCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>165.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>57.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180356</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04256</kegg_id>
  <foodb_id>FDB022581</foodb_id>
  <chemspider_id>389248</chemspider_id>
  <pubchem_compound_id>440272</pubchem_compound_id>
  <chebi_id>7125</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <knapsack_id>C00019581</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>43457</bigg_id>
  <wikipedia_id/>
  <metlin_id>6194</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:49 UTC</creation_date>
  <update_date>2020-03-13 16:27:35 UTC</update_date>
  <accession>BMDB0001368</accession>
  <secondary_accessions>
    <accession>BMDB01368</accession>
  </secondary_accessions>
  <name>3-Mercaptopyruvic acid</name>
  <description>3-3-3-mercaptopyruvic acid, also known as 3-mercaptopyruvic acid or 3-3-mercaptopyruvic acid, belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. 3-3-3-mercaptopyruvic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3-3-3-mercaptopyruvic acid exists in all living organisms, ranging from bacteria to humans. 3-3-3-mercaptopyruvic acid participates in a number of enzymatic reactions, within cattle. In particular, 3-3-3-mercaptopyruvic acid and cyanide can be converted into pyruvic acid and thiocyanate through its interaction with the enzyme 3-3-mercaptopyruvic acid sulfurtransferase. In addition, 3-3-3-mercaptopyruvic acid can be biosynthesized from 3-mercaptolactic acid; which is catalyzed by the enzyme L-lactate dehydrogenase. In cattle, 3-3-mercaptopyruvic acid is involved in the metabolic pathway called the cysteine metabolism pathway.</description>
  <synonyms>
    <synonym>3-Mercapto-2-oxopropanoic acid</synonym>
    <synonym>3-Mercaptopyruvate</synonym>
    <synonym>Mercaptopyruvate</synonym>
    <synonym>3-Mercapto-2-oxopropanoate</synonym>
    <synonym>Mercaptopyruvic acid</synonym>
    <synonym>3-Mercapto-pyruvate</synonym>
    <synonym>3-Mercapto-pyruvic acid</synonym>
    <synonym>beta-3-Mercapto-2-oxo-propanoate</synonym>
    <synonym>beta-3-Mercapto-2-oxo-propanoic acid</synonym>
    <synonym>beta-Mercaptopyruvate</synonym>
    <synonym>beta-Mercaptopyruvic acid</synonym>
    <synonym>beta-Thiopyruvate</synonym>
    <synonym>beta-Thiopyruvic acid</synonym>
    <synonym>Thiopyruvate</synonym>
    <synonym>3-Mercaptopyruvate monosodium salt</synonym>
  </synonyms>
  <chemical_formula>C3H4O3S</chemical_formula>
  <average_molecular_weight>120.127</average_molecular_weight>
  <monisotopic_moleculate_weight>119.988114684</monisotopic_moleculate_weight>
  <iupac_name>2-oxo-3-sulfanylpropanoic acid</iupac_name>
  <traditional_iupac>β-mercaptopyruvic acid</traditional_iupac>
  <cas_registry_number>2464-23-5</cas_registry_number>
  <smiles>OC(=O)C(=O)CS</smiles>
  <inchi>InChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6)</inchi>
  <inchikey>OJOLFAIGOXZBCI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Alpha-keto acids and derivatives</sub_class>
    <direct_parent>Alpha-keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organosulfur compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>thiol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-oxo-3-sulfanylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>120.127</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>119.988114684</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C(=O)CS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H4O3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OJOLFAIGOXZBCI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334734</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00957</kegg_id>
  <foodb_id>FDB030434</foodb_id>
  <chemspider_id>96</chemspider_id>
  <pubchem_compound_id>98</pubchem_compound_id>
  <chebi_id>16208</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <knapsack_id>C00007464</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>36476</bigg_id>
  <wikipedia_id>3-Mercaptopyruvic_acid</wikipedia_id>
  <metlin_id>6195</metlin_id>
  <meta_cyc_id>3-MERCAPTO-PYRUVATE</meta_cyc_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:50 UTC</creation_date>
  <update_date>2020-03-13 16:27:35 UTC</update_date>
  <accession>BMDB0001369</accession>
  <secondary_accessions>
    <accession>BMDB01369</accession>
  </secondary_accessions>
  <name>Pyrroline hydroxycarboxylic acid</name>
  <description/>
  <synonyms>
    <synonym>Pyrroline hydroxycarboxylate</synonym>
    <synonym>3-Hydroxy-L-1-pyrroline-5-carboxylate</synonym>
    <synonym>L-1-Pyrroline 3-hydroxy-5-carboxylate</synonym>
    <synonym>L-1-Pyrroline-3-hydroxy-5-carboxylate</synonym>
    <synonym>L-Delta1-Pyrroline 3-hydroxy-5-carboxylate</synonym>
    <synonym>Pyrroline-hydroxy-carboxylate</synonym>
    <synonym>3,4-Dihydro-3-hydroxy-2H-pyrrole-5-carboxylic acid</synonym>
    <synonym>3-Hydroxy delta 1-pyrroline-5-carboxylic acid</synonym>
    <synonym>3-Hydroxy delta 1-pyrroline-5-carboxylic acid, anion</synonym>
  </synonyms>
  <chemical_formula>C5H7NO3</chemical_formula>
  <average_molecular_weight>129.114</average_molecular_weight>
  <monisotopic_moleculate_weight>129.042593095</monisotopic_moleculate_weight>
  <iupac_name>4-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid</iupac_name>
  <traditional_iupac>pyrroline-hydroxy-carboxylate</traditional_iupac>
  <cas_registry_number>22573-88-2</cas_registry_number>
  <smiles>OC1CC(N=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h2-4,7H,1H2,(H,8,9)</inchi>
  <inchikey>WFOFKRKDDKGRIK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrroline carboxylic acids</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyrroline</substituent>
      <substituent>Pyrroline carboxylic acid</substituent>
      <substituent>Pyrroline carboxylic acid or derivatives</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>1-pyrrolinecarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>129.114</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>129.042593095</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC1CC(N=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H7NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h2-4,7H,1H2,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WFOFKRKDDKGRIK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>69.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181038</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181039</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181040</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04281</kegg_id>
  <foodb_id>FDB022582</foodb_id>
  <chemspider_id>1030</chemspider_id>
  <pubchem_compound_id>1059</pubchem_compound_id>
  <chebi_id>27391</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>43511</bigg_id>
  <wikipedia_id/>
  <metlin_id>6196</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:52 UTC</creation_date>
  <update_date>2020-03-13 16:27:36 UTC</update_date>
  <accession>BMDB0001370</accession>
  <secondary_accessions>
    <accession>BMDB01370</accession>
  </secondary_accessions>
  <name>Diaminopimelic acid</name>
  <description>Diaminopimelic acid, also known as LL-2,6-diaminopimelate or acid, diaminopimelic, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Diaminopimelic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Diaminopimelic acid exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>(S,S)-2,6-Diaminopimelic acid</synonym>
    <synonym>(S-(R*,r*))-2,6-diaminoheptanedioic acid</synonym>
    <synonym>L,L-2,6-Diaminopimelic acid</synonym>
    <synonym>LL-2,6-Diaminoheptanedioate</synonym>
    <synonym>LL-2,6-Diaminopimelate</synonym>
    <synonym>LL-2,6-Diaminopimelic acid</synonym>
    <synonym>(S,S)-2,6-Diaminopimelate</synonym>
    <synonym>(S-(R*,r*))-2,6-diaminoheptanedioate</synonym>
    <synonym>L,L-2,6-Diaminopimelate</synonym>
    <synonym>LL-2,6-Diaminoheptanedioic acid</synonym>
    <synonym>Diaminopimelate</synonym>
    <synonym>(   (R*,s*)-2,6-diamino-heptanedioate</synonym>
    <synonym>(   (R*,s*)-2,6-diamino-heptanedioic acid</synonym>
    <synonym>(2R,6S)-2,6-Diamino-heptanedioate</synonym>
    <synonym>(2R,6S)-2,6-Diamino-heptanedioic acid</synonym>
    <synonym>(R*,s*)-2,6-diamino-heptanedioate</synonym>
    <synonym>(R*,s*)-2,6-diamino-heptanedioic acid</synonym>
    <synonym>2,6-Diamino-heptanedioate</synonym>
    <synonym>2,6-Diamino-heptanedioic acid</synonym>
    <synonym>2,6-Diaminoheptanedioate</synonym>
    <synonym>2,6-Diaminoheptanedioic acid</synonym>
    <synonym>2,6-Diaminopimelate</synonym>
    <synonym>2,6-Diaminopimelic acid</synonym>
    <synonym>a,A'-diaminopimelate</synonym>
    <synonym>a,A'-diaminopimelic acid</synonym>
    <synonym>a,e-Diaminopimelate</synonym>
    <synonym>a,e-Diaminopimelic acid</synonym>
    <synonym>D,L-Diaminopimelate</synonym>
    <synonym>D,L-Meso-diaminoheptanedioate</synonym>
    <synonym>D,L-Meso-diaminoheptanedioic acid</synonym>
    <synonym>DAPA</synonym>
    <synonym>DL-2,6-Diaminoheptanedioate</synonym>
    <synonym>DL-2,6-Diaminoheptanedioic acid</synonym>
    <synonym>DL-2,6-Diaminopimelate</synonym>
    <synonym>DL-2,6-Diaminopimelic acid</synonym>
    <synonym>L,L-2,6-Diaminoheptanedioate</synonym>
    <synonym>L,L-2,6-Diaminoheptanedioic acid</synonym>
    <synonym>L,L-Diaminopimelate</synonym>
    <synonym>Meso-1-alpha,epsilon-diaminopimelate</synonym>
    <synonym>Meso-2,6-diamino-heptanedioate</synonym>
    <synonym>Meso-2,6-diamino-heptanedioic acid</synonym>
    <synonym>Meso-2,6-diaminoheptanedioate</synonym>
    <synonym>Meso-2,6-diaminoheptanedioic acid</synonym>
    <synonym>Meso-alpha,alpha'-diaminopimelate</synonym>
    <synonym>Meso-alpha,alpha'-diaminopimelic acid</synonym>
    <synonym>Meso-alpha,epsilon-diaminopimelate</synonym>
    <synonym>Meso-alpha,epsilon-diaminopimelic acid</synonym>
    <synonym>Meso-diaminoheptanedioate</synonym>
    <synonym>Meso-diaminoheptanedioic acid</synonym>
    <synonym>Meso-diaminopimelate</synonym>
    <synonym>Acid, diaminopimelic</synonym>
    <synonym>2,6 Diaminopimelic acid</synonym>
    <synonym>Acid, 2,6-diaminopimelic</synonym>
    <synonym>Diamino-pimelate</synonym>
    <synonym>Diaminopimelic acid</synonym>
  </synonyms>
  <chemical_formula>C7H14N2O4</chemical_formula>
  <average_molecular_weight>190.1971</average_molecular_weight>
  <monisotopic_moleculate_weight>190.095356946</monisotopic_moleculate_weight>
  <iupac_name>(2S,6S)-2,6-diaminoheptanedioic acid</iupac_name>
  <traditional_iupac>diamino-pimelic acid</traditional_iupac>
  <cas_registry_number>583-93-7</cas_registry_number>
  <smiles>N[C@@H](CCC[C@H](N)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C7H14N2O4/c8-4(6(10)11)2-1-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1</inchi>
  <inchikey>GMKMEZVLHJARHF-WHFBIAKZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2,6-diaminopimelic acid</external_descriptor>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>300 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-4.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,6S)-2,6-diaminoheptanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>190.1971</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>190.095356946</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCC[C@H](N)C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H14N2O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H14N2O4/c8-4(6(10)11)2-1-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GMKMEZVLHJARHF-WHFBIAKZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>126.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183047</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00666</kegg_id>
  <foodb_id>FDB030951</foodb_id>
  <chemspider_id>388416</chemspider_id>
  <pubchem_compound_id>439283</pubchem_compound_id>
  <chebi_id>16026</chebi_id>
  <pdbe_id/>
  <drugbank_id>DB03590</drugbank_id>
  <knapsack_id>C00007596</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Diaminopimelic acid</wikipedia_id>
  <metlin_id>352</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Gao, Yong.  Synthesis of diaminopimelic acid (DAP) and analogues: mechanistic studies on DAP aminotransferase, epimerase and dehydrogenase.    (1998),     166 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:53 UTC</creation_date>
  <update_date>2020-04-16 17:54:13 UTC</update_date>
  <accession>BMDB0001371</accession>
  <secondary_accessions>
    <accession>BMDB01371</accession>
  </secondary_accessions>
  <name>Nitrogen</name>
  <description>Nitrogen, also known as Nitrogen or N#N, belongs to the class of inorganic compounds known as other non-metal nitrides. These are inorganic compounds of nitrogen where nitrogen has a formal oxidation state of -3, and the heaviest atom bonded to it belongs to the class of 'other non-metals'. Nitrogen exists as a solid, possibly soluble (in water), and possibly neutral molecule. Nitrogen exists in all living organisms, ranging from bacteria to humans. In cattle, nitrogen is involved in the metabolic pathway called the nitric oxide signaling pathway.</description>
  <synonyms>
    <synonym>Molecular nitrogen</synonym>
    <synonym>N2</synonym>
    <synonym>N#N</synonym>
    <synonym>Nitrogen</synonym>
    <synonym>Dinitrogen</synonym>
    <synonym>Nitrogen gas</synonym>
  </synonyms>
  <chemical_formula>N2</chemical_formula>
  <average_molecular_weight>28.0134</average_molecular_weight>
  <monisotopic_moleculate_weight>28.00614801</monisotopic_moleculate_weight>
  <iupac_name>diazyne</iupac_name>
  <traditional_iupac>nitrogen</traditional_iupac>
  <cas_registry_number>7727-37-9</cas_registry_number>
  <smiles>N#N</smiles>
  <inchi>InChI=1S/N2/c1-2</inchi>
  <inchikey>IJGRMHOSHXDMSA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as other non-metal nitrides. These are inorganic compounds of nitrogen where nitrogen has a formal oxidation state of -3, and the heaviest atom bonded to it belongs to the class of 'other non-metals'.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Other non-metal organides</class>
    <sub_class>Other non-metal nitrides</sub_class>
    <direct_parent>Other non-metal nitrides</direct_parent>
    <alternative_parents>
      <alternative_parent>Inorganic nitrides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Inorganic nitride</substituent>
      <substituent>Other non-metal nitride</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a non-metabolic compound</external_descriptor>
      <external_descriptor>diatomic nitrogen</external_descriptor>
      <external_descriptor>elemental molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-210.01 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>18.1 mg/mL at 21 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.67</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>diazyne</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>28.0134</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>28.00614801</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N#N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/N2/c1-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IJGRMHOSHXDMSA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>47.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>26.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32716</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00697</kegg_id>
  <chemspider_id/>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>17997</chebi_id>
  <pubchem_compound_id>947</pubchem_compound_id>
  <meta_cyc_id>NITROGEN-MOLECULE</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Nitrogen</wikipedia_id>
  <foodb_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01814</protein_accession>
      <name>Mitochondrial 2-oxoglutarate/malate carrier protein</name>
      <uniprot_id>P22292</uniprot_id>
      <gene_name>SLC25A11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:54 UTC</creation_date>
  <update_date>2020-04-15 22:00:29 UTC</update_date>
  <accession>BMDB0001372</accession>
  <secondary_accessions>
    <accession>BMDB01372</accession>
  </secondary_accessions>
  <name>Thiamine pyrophosphate</name>
  <description>Thiamine pyrophosphate, also known as thiamine pyrophosphate or thiamine pyrophosphate, belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group. Thiamine pyrophosphate is possibly soluble (in water) and a very strong basic compound (based on its pKa). Thiamine pyrophosphate exists in all living species, ranging from bacteria to humans. Thiamine pyrophosphate participates in a number of enzymatic reactions, within cattle. In particular, S-(2-Methylbutanoyl)-dihydrolipoamide and thiamine pyrophosphate can be biosynthesized from lipoamide and 2-methyl-1-hydroxypropyl-THPP; which is mediated by the enzymes 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial and 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial. In addition, Ketoleucine and thiamine pyrophosphate can be converted into 3-methyl-1-hydroxybutyl-THPP; which is mediated by the enzyme 2-oxoisovalerate dehydrogenase. In cattle, thiamine pyrophosphate is involved in the metabolic pathway called the valine, leucine, and isoleucine degradation pathway.</description>
  <synonyms>
    <synonym>Thiamin diphosphate</synonym>
    <synonym>Thiamin pyrophosphate</synonym>
    <synonym>Thiamine diphosphate</synonym>
    <synonym>THPP</synonym>
    <synonym>TPP</synonym>
    <synonym>Thiamin diphosphoric acid</synonym>
    <synonym>Thiamin pyrophosphoric acid</synonym>
    <synonym>Thiamine diphosphoric acid</synonym>
    <synonym>Thiamine pyrophosphoric acid</synonym>
    <synonym>Thaimine pyrophosphate</synonym>
    <synonym>Thiamin-ppi</synonym>
    <synonym>Thiamine-ppi</synonym>
    <synonym>Thiamine-pyrophosphate</synonym>
    <synonym>Cocarboxylase</synonym>
    <synonym>Berolase</synonym>
    <synonym>Pyrophosphate, thiamine</synonym>
  </synonyms>
  <chemical_formula>C12H19N4O7P2S</chemical_formula>
  <average_molecular_weight>425.314</average_molecular_weight>
  <monisotopic_moleculate_weight>425.044967696</monisotopic_moleculate_weight>
  <iupac_name>3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium</iupac_name>
  <traditional_iupac>thiamin pyrophosphate</traditional_iupac>
  <cas_registry_number>154-87-0</cas_registry_number>
  <smiles>CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N</smiles>
  <inchi>InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)/p+1</inchi>
  <inchikey>AYEKOFBPNLCAJY-UHFFFAOYSA-O</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazines</class>
    <sub_class>Pyrimidines and pyrimidine derivatives</sub_class>
    <direct_parent>Thiamine phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>4,5-disubstituted thiazoles</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>4,5-disubstituted 1,3-thiazole</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Thiamine-phosphate</substituent>
      <substituent>Thiazole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>1,3-thiazolium cation</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>425.314</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>425.044967696</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H19N4O7P2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)/p+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AYEKOFBPNLCAJY-UHFFFAOYSA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>168.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>95.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Thiamine Metabolism</name>
      <smpdb_id>SMP0087212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Threonine and 2-Oxobutanoate Degradation</name>
      <smpdb_id>SMP0087262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5215</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445905</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00068</kegg_id>
  <foodb_id>FDB022584</foodb_id>
  <drugbank_id/>
  <chemspider_id>1100</chemspider_id>
  <pubchem_compound_id>1132</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>9532</chebi_id>
  <meta_cyc_id>THIAMINE-PYROPHOSPHATE</meta_cyc_id>
  <knapsack_id>C00019627</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33732</bigg_id>
  <wikipedia_id>Thiamine pyrophosphate</wikipedia_id>
  <metlin_id>2832</metlin_id>
  <synthesis_reference>Zabrodskaya, S. V.; Oparin, D. A.; Ostrovskii, Yu. M. Selective synthesis of thiamine diphosphate. Zhurnal Obshchei Khimii (1989), 59(1), 226-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00488</protein_accession>
      <name>Acetolactate synthase-like protein</name>
      <uniprot_id>A6QQT9</uniprot_id>
      <gene_name>ILVBL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00607</protein_accession>
      <name>Transketolase-like protein 1</name>
      <uniprot_id>Q2NL26</uniprot_id>
      <gene_name>TKTL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00608</protein_accession>
      <name>Transketolase-like protein 2</name>
      <uniprot_id>Q2NKZ4</uniprot_id>
      <gene_name>TKTL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00609</protein_accession>
      <name>Transketolase</name>
      <uniprot_id>Q6B855</uniprot_id>
      <gene_name>TKT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00637</protein_accession>
      <name>2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial</name>
      <uniprot_id>P11178</uniprot_id>
      <gene_name>BCKDHA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01073</protein_accession>
      <name>2-oxoglutarate dehydrogenase E1 component, mitochondrial</name>
      <uniprot_id>Q148N0</uniprot_id>
      <gene_name>OGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01074</protein_accession>
      <name>Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial</name>
      <uniprot_id>A7MB35</uniprot_id>
      <gene_name>PDHA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01075</protein_accession>
      <name>Thiamin pyrophosphokinase 1</name>
      <uniprot_id>Q5E9T4</uniprot_id>
      <gene_name>TPK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01076</protein_accession>
      <name>Pyruvate dehydrogenase E1 component subunit beta, mitochondrial</name>
      <uniprot_id>P11966</uniprot_id>
      <gene_name>PDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01985</protein_accession>
      <name>Mitochondrial thiamine pyrophosphate carrier</name>
      <uniprot_id>Q29RM1</uniprot_id>
      <gene_name>SLC25A19</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02542</protein_accession>
      <name>HACL1 protein</name>
      <uniprot_id>A5PJL6</uniprot_id>
      <gene_name>HACL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02543</protein_accession>
      <name>OGDH protein</name>
      <uniprot_id>A8KC82</uniprot_id>
      <gene_name>OGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02544</protein_accession>
      <name>ILVBL protein</name>
      <uniprot_id>B0JYQ9</uniprot_id>
      <gene_name>ILVBL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:55 UTC</creation_date>
  <update_date>2020-03-13 16:27:37 UTC</update_date>
  <accession>BMDB0001373</accession>
  <secondary_accessions>
    <accession>BMDB01373</accession>
  </secondary_accessions>
  <name>Dephospho-CoA</name>
  <description>Dephospho-CoA, also known as Dephospho-coa, belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. Thus, dephospho-CoA is considered to be a fatty ester lipid molecule. Dephospho-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dephospho-CoA exists in all living species, ranging from bacteria to humans. In cattle, dephospho-CoA is involved in the metabolic pathway called pantothenate and CoA biosynthesis pathway.</description>
  <synonyms>
    <synonym>3'-Dephospho-CoA</synonym>
    <synonym>3'-Dephospho-coenzyme A</synonym>
    <synonym>3'-O-Dephosphono-CoA</synonym>
    <synonym>3'-O-Dephosphono-coenzyme A</synonym>
    <synonym>Dephospho-coenzyme A</synonym>
    <synonym>Dephosphocoenzyme A</synonym>
    <synonym>DpCoA</synonym>
    <synonym>Dephospho CoA</synonym>
    <synonym>3'-Desphospho-coenzyme A</synonym>
    <synonym>2'-(5''-Triphosphoribosyl)-3'-dephospho-CoA</synonym>
    <synonym>Desphospho-CoA</synonym>
  </synonyms>
  <chemical_formula>C21H35N7O13P2S</chemical_formula>
  <average_molecular_weight>687.554</average_molecular_weight>
  <monisotopic_moleculate_weight>687.148877955</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphinic acid</iupac_name>
  <traditional_iupac>{[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy)phosphinic acid</traditional_iupac>
  <cas_registry_number>3633-59-8</cas_registry_number>
  <smiles>CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCS</smiles>
  <inchi>InChI=1S/C21H35N7O13P2S/c1-21(2,16(32)19(33)24-4-3-12(29)23-5-6-44)8-39-43(36,37)41-42(34,35)38-7-11-14(30)15(31)20(40-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-32,44H,3-8H2,1-2H3,(H,23,29)(H,24,33)(H,34,35)(H,36,37)(H2,22,25,26)/t11-,14-,15-,16?,20-/m1/s1</inchi>
  <inchikey>KDTSHFARGAKYJN-DRCCLKDXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside diphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>687.554</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>687.148877955</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H35N7O13P2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H35N7O13P2S/c1-21(2,16(32)19(33)24-4-3-12(29)23-5-6-44)8-39-43(36,37)41-42(34,35)38-7-11-14(30)15(31)20(40-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-32,44H,3-8H2,1-2H3,(H,23,29)(H,24,33)(H,34,35)(H,36,37)(H2,22,25,26)/t11-,14-,15-,16?,20-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KDTSHFARGAKYJN-DRCCLKDXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>300.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>151.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>62.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pantothenate and CoA Biosynthesis</name>
      <smpdb_id>SMP0087207</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30169</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00882</kegg_id>
  <foodb_id>FDB022585</foodb_id>
  <drugbank_id/>
  <chemspider_id>388463</chemspider_id>
  <pubchem_compound_id>439335</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15468</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>36283</bigg_id>
  <wikipedia_id/>
  <metlin_id>3689</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:57 UTC</creation_date>
  <update_date>2020-03-13 16:27:38 UTC</update_date>
  <accession>BMDB0001374</accession>
  <secondary_accessions>
    <accession>BMDB01374</accession>
  </secondary_accessions>
  <name>Choloyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-({4-[(1S,5R,9R,10R,11S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]pentanoyl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidate</synonym>
    <synonym>4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-({4-[(1S,5R,9R,10R,11S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]pentanoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidate</synonym>
    <synonym>4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-({4-[(1S,5R,9R,10R,11S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]pentanoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid</synonym>
  </synonyms>
  <chemical_formula>C45H74N7O20P3S</chemical_formula>
  <average_molecular_weight>1158.1</average_molecular_weight>
  <monisotopic_moleculate_weight>1157.392219979</monisotopic_moleculate_weight>
  <iupac_name>4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-({4-[(1S,5R,9R,10R,11S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoyl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid</iupac_name>
  <traditional_iupac>4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-(2-{[2-({4-[(1S,5R,9R,10R,11S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoyl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H]C(C)(CCC(=O)SCCN=C(O)CCN=C(O)C([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O)C1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)CC4([H])C[C@]([H])(O)CCC4(C)[C@@]3([H])C[C@]([H])(O)C12C</smiles>
  <inchi>InChI=1S/C45H74N7O20P3S/c1-23(26-7-8-27-34-28(18-31(55)45(26,27)5)44(4)12-10-25(53)16-24(44)17-29(34)54)6-9-33(57)76-15-14-47-32(56)11-13-48-41(60)38(59)43(2,3)20-69-75(66,67)72-74(64,65)68-19-30-37(71-73(61,62)63)36(58)42(70-30)52-22-51-35-39(46)49-21-50-40(35)52/h21-31,34,36-38,42,53-55,58-59H,6-20H2,1-5H3,(H,47,56)(H,48,60)(H,64,65)(H,66,67)(H2,46,49,50)(H2,61,62,63)/t23?,24?,25-,26?,27+,28+,29-,30-,31+,34+,36-,37-,38?,42-,44?,45?/m1/s1</inchi>
  <inchikey>ZKWNOTQHFKYUNU-OYVVZFPHSA-N</inchikey>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-({4-[(1S,5R,9R,10R,11S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoyl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1158.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1157.392219979</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]C(C)(CCC(=O)SCCN=C(O)CCN=C(O)C([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O)C1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)CC4([H])C[C@]([H])(O)CCC4(C)[C@@]3([H])C[C@]([H])(O)C12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C45H74N7O20P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C45H74N7O20P3S/c1-23(26-7-8-27-34-28(18-31(55)45(26,27)5)44(4)12-10-25(53)16-24(44)17-29(34)54)6-9-33(57)76-15-14-47-32(56)11-13-48-41(60)38(59)43(2,3)20-69-75(66,67)72-74(64,65)68-19-30-37(71-73(61,62)63)36(58)42(70-30)52-22-51-35-39(46)49-21-50-40(35)52/h21-31,34,36-38,42,53-55,58-59H,6-20H2,1-5H3,(H,47,56)(H,48,60)(H,64,65)(H,66,67)(H2,46,49,50)(H2,61,62,63)/t23?,24?,25-,26?,27+,28+,29-,30-,31+,34+,36-,37-,38?,42-,44?,45?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZKWNOTQHFKYUNU-OYVVZFPHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>431.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>271.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>114.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1223848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1223849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1223850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1339477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1339478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1339479</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id/>
  <pubchem_compound_id/>
  <foodb_id/>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:58 UTC</creation_date>
  <update_date>2020-04-15 22:07:28 UTC</update_date>
  <accession>BMDB0001375</accession>
  <secondary_accessions>
    <accession>BMDB01375</accession>
  </secondary_accessions>
  <name>3-Hydroxy-3-methylglutaryl-CoA</name>
  <description/>
  <synonyms>
    <synonym>(3S)-3-Hydroxy-3-methylglutaryl-coenzyme A</synonym>
    <synonym>(S)-3-Hydroxy-3-methylglutaryl-CoA</synonym>
    <synonym>(S)-3-Hydroxy-3-methylglutaryl-coenzyme A</synonym>
    <synonym>HMG-CoA</synonym>
    <synonym>HMG-coenzyme A</synonym>
    <synonym>Hydroxymethylglutaroyl coenzyme A</synonym>
    <synonym>Hydroxymethylglutaryl-CoA</synonym>
    <synonym>(3S)-3-Hydroxy-3-methylglutaryl-CoA</synonym>
    <synonym>(S)-3-Hydroxy-3-methylglutaryl coenzyme A</synonym>
    <synonym>3-Hydroxy-3-methylglutaryl CoA</synonym>
    <synonym>3-Hydroxy-3-methylglutaryl coenzyme A</synonym>
    <synonym>Hydroxymethylglutaryl CoA</synonym>
    <synonym>Hydroxymethylglutaryl coenzyme A</synonym>
    <synonym>beta-Hydroxy-beta-methylglutaryl CoA</synonym>
    <synonym>beta-Hydroxy-beta-methylglutaryl-CoA</synonym>
    <synonym>beta-Hydroxy-beta-methylglutaryl-coenzyme A</synonym>
    <synonym>Β-hydroxy-β-methylglutaryl CoA</synonym>
    <synonym>Β-hydroxy-β-methylglutaryl-CoA</synonym>
    <synonym>Β-hydroxy-β-methylglutaryl-coenzyme A</synonym>
    <synonym>3-Hydroxy-3-methylglutaryl-CoA</synonym>
  </synonyms>
  <chemical_formula>C27H44N7O20P3S</chemical_formula>
  <average_molecular_weight>911.659</average_molecular_weight>
  <monisotopic_moleculate_weight>911.157467109</monisotopic_moleculate_weight>
  <iupac_name>(3S)-5-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-3-hydroxy-3-methyl-5-oxopentanoic acid</iupac_name>
  <traditional_iupac>HMG-CoA</traditional_iupac>
  <cas_registry_number>26926-09-0</cas_registry_number>
  <smiles>C[C@](O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1</inchi>
  <inchikey>CABVTRNMFUVUDM-VRHQGPGLSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (s)-3-hydroxy-3-alkylglutaryl coas. These are 3-hydroxy-3-alkylglutaryl-CoAs where the 3-hydroxy-3-alkylglutaryl component has (S)-configuration.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>(S)-3-hydroxy-3-alkylglutaryl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>(R)-3-hydroxyacyl CoAs</alternative_parent>
      <alternative_parent>(S)-3-hydroxyacyl CoAs</alternative_parent>
      <alternative_parent>2,3,4-saturated fatty acyl CoAs</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hydroxy fatty acyl-CoA</external_descriptor>
      <external_descriptor>3-hydroxy-3-methylglutaryl-CoA</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3S)-5-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-3-hydroxy-3-methyl-5-oxopentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>911.659</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>911.157467109</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@](O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H44N7O20P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CABVTRNMFUVUDM-VRHQGPGLSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>421.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>193.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>82.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Butyrate Metabolism</name>
      <smpdb_id>SMP0087185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ketone Body Metabolism</name>
      <smpdb_id>SMP0087202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>177980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180293</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00356</kegg_id>
  <foodb_id>FDB030158</foodb_id>
  <drugbank_id/>
  <chemspider_id>392859</chemspider_id>
  <pubchem_compound_id>445127</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15467</chebi_id>
  <meta_cyc_id>3-HYDROXY-3-METHYL-GLUTARYL-COA</meta_cyc_id>
  <knapsack_id>C00007270</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Williamson I P; Rodwell V W  Isolation and purification of 3-hydroxy-3-methylglutaryl-coenzyme A by ion-exchange chromatography.    Journal of lipid research  (1981),  22(1),  184-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00359</protein_accession>
      <name>Hydroxymethylglutaryl-CoA synthase, mitochondrial</name>
      <uniprot_id>Q2KIE6</uniprot_id>
      <gene_name>HMGCS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01139</protein_accession>
      <name>Hydroxymethylglutaryl-CoA lyase, mitochondrial</name>
      <uniprot_id>Q29448</uniprot_id>
      <gene_name>HMGCL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:44:59 UTC</creation_date>
  <update_date>2020-03-13 16:27:39 UTC</update_date>
  <accession>BMDB0001376</accession>
  <secondary_accessions>
    <accession>BMDB01376</accession>
  </secondary_accessions>
  <name>2-Keto-3-deoxy-6-phosphogluconic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Dehydro-3-deoxy-6-phospho-D-gluconate</synonym>
    <synonym>2-Dehydro-3-deoxy-D-gluconate 6-phosphate</synonym>
    <synonym>2-Keto-3-deoxy-6-phosphogluconate</synonym>
    <synonym>3-Deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate</synonym>
    <synonym>6-Phospho-2-dehydro-3-deoxy-D-gluconate</synonym>
    <synonym>KDPG Intermediate</synonym>
    <synonym>2-Dehydro-3-deoxy-6-phospho-D-gluconic acid</synonym>
    <synonym>2-Dehydro-3-deoxy-D-gluconic acid 6-phosphoric acid</synonym>
    <synonym>3-Deoxy-D-erythro-hex-2-ulosonate 6-phosphate</synonym>
    <synonym>3-Deoxy-D-erythro-hex-2-ulosonic acid 6-phosphoric acid</synonym>
    <synonym>6-Phospho-2-dehydro-3-deoxy-D-gluconic acid</synonym>
    <synonym>KDPG Intermediic acid</synonym>
    <synonym>2-Dehydro-3-deoxy-D-gluconate-6-phosphate</synonym>
    <synonym>2-Keto-3-deoxy-6-p-gluconate</synonym>
    <synonym>2-Keto-3-deoxy-6-phospho-gluconate</synonym>
    <synonym>2-Keto-3-deoxygluconate-6-p</synonym>
    <synonym>6-p-2-K-3-Deo-gluconate</synonym>
    <synonym>6-Phospho-2-dehydro-3-deoxygluconate</synonym>
    <synonym>6-Phospho-2-keto-3-deoxygluconate</synonym>
  </synonyms>
  <chemical_formula>C6H11O9P</chemical_formula>
  <average_molecular_weight>258.1199</average_molecular_weight>
  <monisotopic_moleculate_weight>258.014068462</monisotopic_moleculate_weight>
  <iupac_name>(4S,5R)-4,5-dihydroxy-2-oxo-6-(phosphonooxy)hexanoic acid</iupac_name>
  <traditional_iupac>kdpg intermediate</traditional_iupac>
  <cas_registry_number>27244-54-8</cas_registry_number>
  <smiles>O[C@H](COP(O)(O)=O)[C@@H](O)CC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H11O9P/c7-3(1-4(8)6(10)11)5(9)2-15-16(12,13)14/h3,5,7,9H,1-2H2,(H,10,11)(H2,12,13,14)/t3-,5+/m0/s1</inchi>
  <inchikey>OVPRPPOVAXRCED-WVZVXSGGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12  carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Medium-chain keto acids and derivatives</sub_class>
    <direct_parent>Medium-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Medium-chain keto acid</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>ketoaldonic acid phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4S,5R)-4,5-dihydroxy-2-oxo-6-(phosphonooxy)hexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>258.1199</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>258.014068462</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H](COP(O)(O)=O)[C@@H](O)CC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H11O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H11O9P/c7-3(1-4(8)6(10)11)5(9)2-15-16(12,13)14/h3,5,7,9H,1-2H2,(H,10,11)(H2,12,13,14)/t3-,5+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OVPRPPOVAXRCED-WVZVXSGGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>161.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25796</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25704</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38044</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C04442</kegg_id>
  <foodb_id>FDB022588</foodb_id>
  <drugbank_id/>
  <chemspider_id>2338483</chemspider_id>
  <pubchem_compound_id>3080745</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15925</chebi_id>
  <meta_cyc_id>2-KETO-3-DEOXY-6-P-GLUCONATE</meta_cyc_id>
  <knapsack_id>C00019434</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6202</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:01 UTC</creation_date>
  <update_date>2020-04-15 20:48:03 UTC</update_date>
  <accession>BMDB0001377</accession>
  <secondary_accessions>
    <accession>BMDB01377</accession>
  </secondary_accessions>
  <name>Oxygen</name>
  <description/>
  <synonyms>
    <synonym>[OO]</synonym>
    <synonym>Dioxygene</synonym>
    <synonym>Disauerstoff</synonym>
    <synonym>e 948</synonym>
    <synonym>e-948</synonym>
    <synonym>e948</synonym>
    <synonym>Molecular oxygen</synonym>
    <synonym>O2</synonym>
    <synonym>OXYGEN molecule</synonym>
    <synonym>Dioxygen</synonym>
    <synonym>Oxygen-16</synonym>
    <synonym>Oxygen 16</synonym>
  </synonyms>
  <chemical_formula>O2</chemical_formula>
  <average_molecular_weight>31.9988</average_molecular_weight>
  <monisotopic_moleculate_weight>31.989829244</monisotopic_moleculate_weight>
  <iupac_name>oxidanone</iupac_name>
  <traditional_iupac>singlet oxygen</traditional_iupac>
  <cas_registry_number>7782-44-7</cas_registry_number>
  <smiles>O=O</smiles>
  <inchi>InChI=1S/O2/c1-2</inchi>
  <inchikey>MYMOFIZGZYHOMD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as other non-metal oxides. These are inorganic compounds containing an oxygen atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen belongs to the class of 'other non-metals'.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Other non-metal organides</class>
    <sub_class>Other non-metal oxides</sub_class>
    <direct_parent>Other non-metal oxides</direct_parent>
    <alternative_parents>
      <alternative_parent>Inorganic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Inorganic oxide</substituent>
      <substituent>Other non-metal oxide</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a non-metabolic compound</external_descriptor>
      <external_descriptor>diatomic oxygen</external_descriptor>
      <external_descriptor>elemental molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-218.4 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>37.5 mg/mL at 21 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.65</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>oxidanone</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>31.9988</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>31.989829244</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/O2/c1-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MYMOFIZGZYHOMD-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>34.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>2.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Androstenedione Metabolism</name>
      <smpdb_id>SMP0087271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Caffeine Metabolism</name>
      <smpdb_id>SMP0087186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>D-Arginine and D-Ornithine Metabolism</name>
      <smpdb_id>SMP0087190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Degradation of Superoxides</name>
      <smpdb_id>SMP0087191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ethanol Degradation</name>
      <smpdb_id>SMP0087192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Electron Transport Chain</name>
      <smpdb_id>SMP0087261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Retinol Metabolism</name>
      <smpdb_id>SMP0087260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Riboflavin Metabolism</name>
      <smpdb_id>SMP0087211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroidogenesis</name>
      <smpdb_id>SMP0087238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sulfate/Sulfite Metabolism</name>
      <smpdb_id>SMP0087216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Taurine and Hypotaurine Metabolism</name>
      <smpdb_id>SMP0087214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ubiquinone Biosynthesis</name>
      <smpdb_id>SMP0087215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin B6 Metabolism</name>
      <smpdb_id>SMP0087240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin K Metabolism</name>
      <smpdb_id>SMP0087227</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33832</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00007</kegg_id>
  <foodb_id>FDB022589</foodb_id>
  <drugbank_id>DB09140</drugbank_id>
  <chemspider_id>952</chemspider_id>
  <pubchem_compound_id>977</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15379</chebi_id>
  <meta_cyc_id>OXYGEN-MOLECULE</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>33493</bigg_id>
  <wikipedia_id>Oxygen</wikipedia_id>
  <metlin_id>3195</metlin_id>
  <synthesis_reference>Wynn, Richard L.  Production of hydrogen and oxygen by thermal disassociation of water.    U.S. Pat. Appl. Publ.  (2007),     26pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00114</protein_accession>
      <name>Thiosulfate sulfurtransferase</name>
      <uniprot_id>P00586</uniprot_id>
      <gene_name>TST</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01444</protein_accession>
      <name>Myoglobin</name>
      <uniprot_id>Q865L4</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01447</protein_accession>
      <name>Neuroglobin</name>
      <uniprot_id>Q6WZ19</uniprot_id>
      <gene_name>NGB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01492</protein_accession>
      <name>Hemoglobin subunit beta</name>
      <uniprot_id>P02070</uniprot_id>
      <gene_name>HBB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01498</protein_accession>
      <name>Hemoglobin subunit mu</name>
      <uniprot_id>A1A4Q3</uniprot_id>
      <gene_name>HBM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01506</protein_accession>
      <name>Hemoglobin subunit epsilon-2</name>
      <uniprot_id>P06642</uniprot_id>
      <gene_name>HBE2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01513</protein_accession>
      <name>Hemoglobin subunit epsilon-4</name>
      <uniprot_id>P06643</uniprot_id>
      <gene_name>HBE4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01523</protein_accession>
      <name>Hemoglobin, theta 1</name>
      <uniprot_id>A1A4Q7</uniprot_id>
      <gene_name>HBQ1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01554</protein_accession>
      <name>Myoglobin</name>
      <uniprot_id>P02192</uniprot_id>
      <gene_name>MB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01558</protein_accession>
      <name>Hemoglobin fetal subunit beta</name>
      <uniprot_id>P02081</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01569</protein_accession>
      <name>Hemoglobin subunit alpha</name>
      <uniprot_id>P01966</uniprot_id>
      <gene_name>HBA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:02 UTC</creation_date>
  <update_date>2020-03-13 16:27:40 UTC</update_date>
  <accession>BMDB0001379</accession>
  <secondary_accessions>
    <accession>BMDB01379</accession>
  </secondary_accessions>
  <name>Diguanosine triphosphate</name>
  <description/>
  <synonyms>
    <synonym>Diguanosine triphosphoric acid</synonym>
    <synonym>Diguanosine-5'-triphosphate</synonym>
    <synonym>GP3g</synonym>
    <synonym>Bis[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinate</synonym>
    <synonym>Diguanosine triphosphate</synonym>
    <synonym>Diguanosine-5'-triphosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C20H27N10O18P3</chemical_formula>
  <average_molecular_weight>788.4059</average_molecular_weight>
  <monisotopic_moleculate_weight>788.071763646</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphinic acid</traditional_iupac>
  <cas_registry_number>6674-45-9</cas_registry_number>
  <smiles>NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(N)=NC3=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C20H27N10O18P3/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(45-17)1-43-49(37,38)47-51(41,42)48-50(39,40)44-2-6-10(32)12(34)18(46-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H,41,42)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1</inchi>
  <inchikey>AAXYAFFKOSNMEB-MHARETSRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside triphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside triphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>788.4059</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>788.071763646</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(N)=NC3=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H27N10O18P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H27N10O18P3/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(45-17)1-43-49(37,38)47-51(41,42)48-50(39,40)44-2-6-10(32)12(34)18(46-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H,41,42)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AAXYAFFKOSNMEB-MHARETSRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>418.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>157.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>65.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>67541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281948</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022590</foodb_id>
  <drugbank_id>DB03931</drugbank_id>
  <chemspider_id>392652</chemspider_id>
  <pubchem_compound_id>444841</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:03 UTC</creation_date>
  <update_date>2020-03-13 16:27:41 UTC</update_date>
  <accession>BMDB0001380</accession>
  <secondary_accessions>
    <accession>BMDB01380</accession>
  </secondary_accessions>
  <name>Diguanosine pentaphosphate</name>
  <description/>
  <synonyms>
    <synonym>Diguanosine pentaphosphoric acid</synonym>
    <synonym>Diguanosine-pentaphosphate</synonym>
    <synonym>GPPPPPG</synonym>
    <synonym>({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)({[({[(2S,3R,4S,5S)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinate</synonym>
    <synonym>Diguanosine pentaphosphate</synonym>
  </synonyms>
  <chemical_formula>C20H29N10O24P5</chemical_formula>
  <average_molecular_weight>948.3657</average_molecular_weight>
  <monisotopic_moleculate_weight>948.004424466</monisotopic_moleculate_weight>
  <iupac_name>{[(2S,3R,4S,5S)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid</iupac_name>
  <traditional_iupac>[(2S,3R,4S,5S)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid</traditional_iupac>
  <cas_registry_number>78101-73-2</cas_registry_number>
  <smiles>NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1O[C@@H](CO[P@](O)(=O)O[P@](O)(=O)O[P@](O)(=O)O[P@@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(N)=NC3=O)[C@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C20H29N10O24P5/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(49-17)1-47-55(37,38)51-57(41,42)53-59(45,46)54-58(43,44)52-56(39,40)48-2-6-10(32)12(34)18(50-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6+,9-,10+,11-,12+,17-,18+</inchi>
  <inchikey>RELSGTOCAPVUGP-DTFXMBEISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside polyphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside polyphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2S,3R,4S,5S)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>948.3657</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>948.004424466</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1O[C@@H](CO[P@](O)(=O)O[P@](O)(=O)O[P@](O)(=O)O[P@@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(N)=NC3=O)[C@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H29N10O24P5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H29N10O24P5/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(49-17)1-47-55(37,38)51-57(41,42)53-59(45,46)54-58(43,44)52-56(39,40)48-2-6-10(32)12(34)18(50-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6+,9-,10+,11-,12+,17-,18+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RELSGTOCAPVUGP-DTFXMBEISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>511.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>178.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>71.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335241</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022591</foodb_id>
  <drugbank_id/>
  <chemspider_id>4484327</chemspider_id>
  <pubchem_compound_id>5327071</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:05 UTC</creation_date>
  <update_date>2020-04-15 22:28:23 UTC</update_date>
  <accession>BMDB0001381</accession>
  <secondary_accessions>
    <accession>BMDB01381</accession>
  </secondary_accessions>
  <name>Prostaglandin H2</name>
  <description/>
  <synonyms>
    <synonym>(5Z,13E)-(15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E,15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acid</synonym>
    <synonym>9,11-Epoxymethano-PGH2</synonym>
    <synonym>PGH2</synonym>
    <synonym>(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E,15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E,15S)-9a,11a-Epidioxy-15-hydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E,15S)-9alpha,11alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E,15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E,15S)-9Α,11α-epidioxy-15-hydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acid</synonym>
    <synonym>(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-Oic acid</synonym>
    <synonym>(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoate</synonym>
    <synonym>(5Z,9a,11a,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoate</synonym>
    <synonym>(5Z,9Α,11α,13E,15S)-9,11-epidioxy-15-hydroxy-prosta-5,13-dienoic acid</synonym>
    <synonym>(15S)Hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoate</synonym>
    <synonym>(15S)Hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoic acid</synonym>
    <synonym>(5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}hept-5-enoate</synonym>
    <synonym>(5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}hept-5-enoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-9,11-Epidioxy-15-hydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E,15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E,15S)-9-alpha,11-alpha-Epidioxy-15-hydroxyprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,9alpha,11alpha,13E,15S)-9,11-Epidioxy-15-hydroxy-prosta-5,13-dien-1-Oic acid</synonym>
    <synonym>15-Hydroxy-9alpha,11alpha-peroxidoprosta-5,13-dienoate</synonym>
    <synonym>15-Hydroxy-9alpha,11alpha-peroxidoprosta-5,13-dienoic acid</synonym>
    <synonym>9S,11R-Epidioxy-15S-hydroxy-5Z,13E-prostadienoate</synonym>
    <synonym>9S,11R-Epidioxy-15S-hydroxy-5Z,13E-prostadienoic acid</synonym>
    <synonym>Endoperoxide H2</synonym>
    <synonym>Prostaglandin R2</synonym>
    <synonym>Prostaglandin-H2</synonym>
    <synonym>PGH(2)</synonym>
  </synonyms>
  <chemical_formula>C20H32O5</chemical_formula>
  <average_molecular_weight>352.4651</average_molecular_weight>
  <monisotopic_moleculate_weight>352.224974134</monisotopic_moleculate_weight>
  <iupac_name>(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid</iupac_name>
  <traditional_iupac>prostaglandin H2</traditional_iupac>
  <cas_registry_number>42935-17-1</cas_registry_number>
  <smiles>CCCCC[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1</inchi>
  <inchikey>YIBNHAJFJUQSRA-YNNPMVKQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Prostaglandins and related compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-dioxanes</alternative_parent>
      <alternative_parent>1,2-dioxolanes</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkyl peroxides</alternative_parent>
      <alternative_parent>Heterocyclic fatty acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkyl peroxide</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Heterocyclic fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Ortho-dioxane</substituent>
      <substituent>Ortho-dioxolane</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Prostaglandin skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>oxylipin</external_descriptor>
      <external_descriptor>prostaglandins H</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>352.4651</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>352.224974134</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H32O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YIBNHAJFJUQSRA-YNNPMVKQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>75.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>98.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38045</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345174</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00427</kegg_id>
  <foodb_id>FDB031134</foodb_id>
  <chemspider_id>392800</chemspider_id>
  <pubchem_compound_id>445049</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>15554</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Prostaglandin H2</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34952</bigg_id>
  <metlin_id>3495</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00024</protein_accession>
      <name>Prostacyclin synthase</name>
      <uniprot_id>Q29626</uniprot_id>
      <gene_name>PTGIS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00102</protein_accession>
      <name>Prostaglandin-H2 D-isomerase</name>
      <uniprot_id>O02853</uniprot_id>
      <gene_name>PTGDS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00802</protein_accession>
      <name>Prostaglandin E synthase 2</name>
      <uniprot_id>Q66LN0</uniprot_id>
      <gene_name>PTGES2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:06 UTC</creation_date>
  <update_date>2020-03-13 16:27:42 UTC</update_date>
  <accession>BMDB0001383</accession>
  <secondary_accessions>
    <accession>BMDB01383</accession>
  </secondary_accessions>
  <name>Sphinganine 1-phosphate</name>
  <description/>
  <synonyms>
    <synonym>(2S,3R)-2-Amino-3-hydroxyoctadecyl dihydrogen phosphate</synonym>
    <synonym>Dihydrosphingosine 1-phosphate</synonym>
    <synonym>Dihydrosphingosine-1-phosphate</synonym>
    <synonym>(2S,3R)-2-Amino-3-hydroxyoctadecyl dihydrogen phosphoric acid</synonym>
    <synonym>Dihydrosphingosine 1-phosphoric acid</synonym>
    <synonym>Dihydrosphingosine-1-phosphoric acid</synonym>
    <synonym>Sphinganine 1-phosphoric acid</synonym>
    <synonym>2-Amino-3-hydroxyoctadecyl dihydrogen phosphate</synonym>
  </synonyms>
  <chemical_formula>C18H40NO5P</chemical_formula>
  <average_molecular_weight>381.4877</average_molecular_weight>
  <monisotopic_moleculate_weight>381.264409907</monisotopic_moleculate_weight>
  <iupac_name>{[(2S,3R)-2-amino-3-hydroxyoctadecyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>dihydrosphingosine 1-phosphate</traditional_iupac>
  <cas_registry_number>19794-97-9</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C18H40NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h17-18,20H,2-16,19H2,1H3,(H2,21,22,23)/t17-,18+/m0/s1</inchi>
  <inchikey>YHEDRJPUIRMZMP-ZWKOTPCHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Sphingolipids</class>
    <sub_class>Phosphosphingolipids</sub_class>
    <direct_parent>Phosphosphingolipids</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phosphoethanolamines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoethanolamine</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sphingoid-1-phosphate or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Sphingoid base 1-phosphates</external_descriptor>
      <external_descriptor>Sphingoid base 1-phosphates</external_descriptor>
      <external_descriptor>sphingoid 1-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2S,3R)-2-amino-3-hydroxyoctadecyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>381.4877</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>381.264409907</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H40NO5P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H40NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h17-18,20H,2-16,19H2,1H3,(H2,21,22,23)/t17-,18+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YHEDRJPUIRMZMP-ZWKOTPCHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>101.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>45.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38046</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180488</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01120</kegg_id>
  <foodb_id>FDB022594</foodb_id>
  <chemspider_id>559277</chemspider_id>
  <pubchem_compound_id>644260</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>16893</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id>C00007541</knapsack_id>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>1485322</bigg_id>
  <metlin_id>3512</metlin_id>
  <synthesis_reference>Schick, Andreas; Kolter, Thomas; Giannis, Athanassios; Sandhoff, Konrad.  Synthesis of phosphoramide analogs of sphinganine-1-phosphate.    Tetrahedron  (1996),  52(8),  2945-56.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:07 UTC</creation_date>
  <update_date>2020-03-13 16:27:42 UTC</update_date>
  <accession>BMDB0001385</accession>
  <secondary_accessions>
    <accession>BMDB01385</accession>
  </secondary_accessions>
  <name>3-Keto-b-D-galactose</name>
  <description/>
  <synonyms>
    <synonym>3-Dehydro-beta-D-galactose</synonym>
    <synonym>3-Dehydro-beta-delta-galactose</synonym>
    <synonym>3-Keto-beta-D-galactose</synonym>
    <synonym>3-Keto-beta-delta-galactose</synonym>
    <synonym>3-Keto-β-D-galactose</synonym>
    <synonym>3-Keto-b-D-galactose</synonym>
  </synonyms>
  <chemical_formula>C6H10O6</chemical_formula>
  <average_molecular_weight>178.14</average_molecular_weight>
  <monisotopic_moleculate_weight>178.047738052</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,5S,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-one</iupac_name>
  <traditional_iupac>3-keto-b-D-galactose</traditional_iupac>
  <cas_registry_number/>
  <smiles>OC[C@H]1O[C@@H](O)[C@H](O)C(=O)[C@H]1O</smiles>
  <inchi>InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-3,5-8,10-11H,1H2/t2-,3+,5-,6-/m1/s1</inchi>
  <inchikey>APIQNBNBIICCON-FKMSRSAHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>ketohexose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,5S,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)oxan-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>178.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>178.047738052</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@@H](O)[C@H](O)C(=O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-3,5-8,10-11H,1H2/t2-,3+,5-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>APIQNBNBIICCON-FKMSRSAHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>107.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357222</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05394</kegg_id>
  <foodb_id>FDB030433</foodb_id>
  <chemspider_id>389534</chemspider_id>
  <pubchem_compound_id>440653</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>27453</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6206</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:08 UTC</creation_date>
  <update_date>2020-03-13 16:27:43 UTC</update_date>
  <accession>BMDB0001387</accession>
  <secondary_accessions>
    <accession>BMDB01387</accession>
  </secondary_accessions>
  <name>N-Methylphenylethanolamine</name>
  <description/>
  <synonyms>
    <synonym>(+-)-alpha-((Methylamino)methyl)benzenemethanol</synonym>
    <synonym>(+-)-Halostachine</synonym>
    <synonym>alpha-[(Methylamino)methyl]-benzyl alcohol</synonym>
    <synonym>(+-)-a-((Methylamino)methyl)benzenemethanol</synonym>
    <synonym>(+-)-Α-((methylamino)methyl)benzenemethanol</synonym>
    <synonym>a-[(Methylamino)methyl]-benzyl alcohol</synonym>
    <synonym>Α-[(methylamino)methyl]-benzyl alcohol</synonym>
    <synonym>2-(Methylamino)-1-phenylethanol</synonym>
    <synonym>2-Methylamino-1-phenylethanol</synonym>
    <synonym>alpha-((Methylamino)methyl)-DL-benzyl alcohol</synonym>
    <synonym>alpha-(Methylaminomethyl)benzyl alcohol</synonym>
    <synonym>DL-alpha-(Methylaminomethyl)benzyl alcohol</synonym>
    <synonym>Halostachine</synonym>
    <synonym>MPEOA</synonym>
    <synonym>N-Methylphenylethanolamine hydrochloride</synonym>
    <synonym>N-Methylphenylethanolamine hydrochloride, (+-)-isomer</synonym>
    <synonym>N-Methylphenylethanolamine, (+-)-isomer</synonym>
    <synonym>N-Methylphenylethanolamine, (R)-isomer</synonym>
  </synonyms>
  <chemical_formula>C9H13NO</chemical_formula>
  <average_molecular_weight>151.2056</average_molecular_weight>
  <monisotopic_moleculate_weight>151.099714043</monisotopic_moleculate_weight>
  <iupac_name>2-(methylamino)-1-phenylethan-1-ol</iupac_name>
  <traditional_iupac>halostachine</traditional_iupac>
  <cas_registry_number>68579-60-2</cas_registry_number>
  <smiles>CNCC(O)C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C9H13NO/c1-10-7-9(11)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3</inchi>
  <inchikey>ZCTYHONEGJTYQV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>Aralkylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>alkaloid</external_descriptor>
      <external_descriptor>phenylethanolamines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>74 - 76 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(methylamino)-1-phenylethan-1-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>151.2056</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>151.099714043</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CNCC(O)C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13NO/c1-10-7-9(11)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZCTYHONEGJTYQV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>32.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38048</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32569</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C03711</kegg_id>
  <foodb_id>FDB022596</foodb_id>
  <chemspider_id>889</chemspider_id>
  <pubchem_compound_id>913</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>16913</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>N-METHYLPHENYLETHANOLAMINE</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Halostachine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6207</metlin_id>
  <synthesis_reference>Syrneva, Yu. I.  The pharmacology of the new alkaloid halostachine.    Farmakologiya i Toksikologiya (Moscow)  (1941),  4(No. 1),  45-51.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00100</protein_accession>
      <name>Phenylethanolamine N-methyltransferase</name>
      <uniprot_id>P10938</uniprot_id>
      <gene_name>PNMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:14 UTC</creation_date>
  <update_date>2020-04-16 20:37:31 UTC</update_date>
  <accession>BMDB0001388</accession>
  <secondary_accessions>
    <accession>BMDB01388</accession>
  </secondary_accessions>
  <name>Alpha-Linolenic acid</name>
  <description>Alpha-Linolenic acid, also known as A-linolenate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Alpha-Linolenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.</description>
  <synonyms>
    <synonym>a-Linolenate</synonym>
    <synonym>a-Linolenic acid</synonym>
    <synonym>alpha-Linolenate</synonym>
    <synonym>Α-linolenate</synonym>
    <synonym>Α-linolenic acid</synonym>
    <synonym>Elaidolinolenate</synonym>
  </synonyms>
  <chemical_formula>C18H30O2</chemical_formula>
  <average_molecular_weight>278.436</average_molecular_weight>
  <monisotopic_moleculate_weight>278.224580206</monisotopic_moleculate_weight>
  <iupac_name>(9E,12E,15E)-octadeca-9,12,15-trienoic acid</iupac_name>
  <traditional_iupac>elaidolinoleic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H]\C(CC)=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])CCCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3+,7-6+,10-9+</inchi>
  <inchikey>DTOSIQBPPRVQHS-IUQGRGSQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Lineolic acids and derivatives</sub_class>
    <direct_parent>Lineolic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Octadecanoid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(9E,12E,15E)-octadeca-9,12,15-trienoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>278.436</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>278.224580206</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]\C(CC)=C(\[H])C\C([H])=C(/[H])C\C([H])=C(/[H])CCCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H30O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3+,7-6+,10-9+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DTOSIQBPPRVQHS-IUQGRGSQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>89.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>92237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>155823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>155824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>155825</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>3763.2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>1338.33</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Intramuscular (IMF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>40120.75</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>0</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Perirenal (PF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>34354.61</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage with flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>16474.0192</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Subcutaneous (SF) fat of beef steers fed red clover silage without flaxseed.</comment>
      <references>
        <reference>
          <reference_text>C. Mapiye, T.D.Turner, D.C.Rolland, J.A.Basarab, V.S.Baron, T.A.McAllister, H.C. Block, B.Uttaro, J.L.Aalhus, M.E.R.Dugan. Adipose tissue and muscle fatty acid profiles of steers fed red clover silage with and without flaxseed. Livestock Science. 151(2013)11-20.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed grasshay with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>7434.38</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Calf-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>8404.09</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. With growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>8260.43</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Without growth promoting implants</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value>9018.23</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>Fatty acid of subcutaneous fat. Yearling-finished</comment>
      <references>
        <reference>
          <reference_text>Mapiye C, Turner TD, Basarab JA, Baron VS, Aalhus JL, Dugan ME: Subcutaneous fatty acid composition of steers finished as weanlings or yearlings with and without growth promotants. J Anim Sci Biotechnol. 2013 Nov 4;4(1):41. doi: 10.1186/2049-1891-4-41.</reference_text>
          <pubmed_id>24188642</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with flaxseed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed barley silage diet for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed barley silage diet with flaxseed for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed hay for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Cull beef cows fed hay with flaxseed for 12 weeks</comment>
      <references>
        <reference>
          <reference_text>He ML, McAllister TA, Kastelic JP, Mir PS, Aalhus JL, Dugan ME, Aldai N, McKinnon JJ: Feeding flaxseed in grass hay and barley silage diets to beef cows increases alpha-linolenic acid and its biohydrogenation intermediates in subcutaneous fat. J Anim Sci. 2012 Feb;90(2):592-604. doi: 10.2527/jas.2011-4281.</reference_text>
          <pubmed_id>22274861</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Adipose Tissue</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Fatty acid of subcutaneous fat from beef steers. Steers were fed red clove silage with sunflower seed for 205 days.</comment>
      <references>
        <reference>
          <reference_text>Petri RM, Mapiye C, Dugan ME, McAllister TA: Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed. PLoS One. 2014 Aug 5;9(8):e104167. doi: 10.1371/journal.pone.0104167. eCollection 2014.</reference_text>
          <pubmed_id>25093808</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3591.49</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3950.639</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4668.936</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.78 +/- 0.22</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC–MS/MS </comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>71.83</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>71.83</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>71.83</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>933.787</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.8 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.01 +/- 0.03</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.4 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC–MS/MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.44 +/- 0.53</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk from a Danish Holstein herd by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.52 +/- 0.53</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised whole milk (3.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.39 +/- 0.53</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in commercial Danish pasteurised semi skimmed milk (1.5% fat) by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.36 +/- 0.09</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Free fatty acid in raw milk by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Bashar Amer, Caroline Nebel, Hanne C. Bertram, Grith Mortensen, Kjeld Hermansen, Trine K. Dalsgaard. Novel method for quantification of individual free fatty acids in milk using an in-solution derivatisation approach and gas chromatography- mass spectrometry. International Dairy Journal 32 (2013) 199-203</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1077.470 +/- 359.157</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
          <pubmed_id>16899705</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1221.133 +/- 502.819</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>933.807 +/- 466.904</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the calibration set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1041.554 +/- 359.157</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>790.145 +/- 323.241</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>The samples were collected from crossbred Holstein × Normande dairy cows, Montbéliarde cattles and Prim'Holstein. The fat content was estimated by MIR spectrometry. This the validation set of samples</comment>
      <references>
        <reference>
          <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples have been collected from Heifer cows.</comment>
      <references>
        <reference>
          <reference_text>Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub  2013 Jun 5.</reference_text>
          <pubmed_id>23871026</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Oocyte</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by CP9010 autosampler onto a capillary column within a CP9001 gas chromatograph in slaughtered cow ovaries.</comment>
      <references>
        <reference>
          <reference_text>McEvoy TG, Coull GD, Broadbent PJ, Hutchinson JS, Speake BK: Fatty acid composition of lipids in immature cattle, pig and sheep oocytes with intact zona pellucida. J Reprod Fertil. 2000 Jan;118(1):163-70.</reference_text>
          <pubmed_id>10793638</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.5 +/- 0.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by FAMEs/GC–MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id/>
  <foodb_id/>
  <pubchem_compound_id>5282822</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Alpha-Linolenic acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Li, Guihua; Qian, Xiangming; Jiang, Yanchao; Ma, Shushi.  Preparation of a-linolenic acid from linseed oil.    Zhengzhou Gongcheng Xueyuan Xuebao  (2004),  25(3),  13-15. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2.</reference_text>
      <pubmed_id>16899705</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158.</reference_text>
      <pubmed_id>20855010</pubmed_id>
    </reference>
    <reference>
      <reference_text>Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026.</reference_text>
      <pubmed_id>29570652</pubmed_id>
    </reference>
    <reference>
      <reference_text>van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21.</reference_text>
      <pubmed_id>28219465</pubmed_id>
    </reference>
    <reference>
      <reference_text>Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.</reference_text>
      <pubmed_id>19038946</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189</reference_text>
    </reference>
    <reference>
      <reference_text>M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80   doi: 10.1016/j.livsci.2014.03.021</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:15 UTC</creation_date>
  <update_date>2020-04-16 20:40:49 UTC</update_date>
  <accession>BMDB0001389</accession>
  <secondary_accessions>
    <accession>BMDB01389</accession>
  </secondary_accessions>
  <name>Melatonin</name>
  <description>Melatonin, also known as circadin or melatol, belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Melatonin is a drug which is used orally for jet lag, insomnia, shift-work disorder, circadian rhythm disorders in the blind (evidence for efficacy), and benzodiazepine and nicotine withdrawal. evidence indicates that melatonin is likely effective for treating circadian rhythm sleep disorders in blind children and adults. it has received fda orphan drug status as an oral medication for this use. a number of studies have shown that melatonin may be effective for treating sleep-wake cycle disturbances in children and adolescents with mental retardation, autism, and other central nervous system disorders. it appears to decrease the time to fall asleep in children with developmental disabilities, such as cerebral palsy, autism, and mental retardation. it may also improve secondary insomnia associated with various sleep-wake cycle disturbances. other possible uses for which there is some evidence for include: benzodiazepine withdrawal, cluster headache, delayed sleep phase syndrome (dsps), primary insomnia, jet lag, nicotine withdrawal, preoperative anxiety and sedation, prostate cancer, solid tumors (when combined with il-2 therapy in certain cancers), sunburn prevention (topical use), tardive dyskinesia, thrombocytopenia associated with cancer, chemotherapy and other disorders. . Melatonin exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Melatonin exists in all living organisms, ranging from bacteria to humans. Melatonin participates in a number of enzymatic reactions, within cattle. In particular, Melatonin and S-adenosylhomocysteine can be biosynthesized from N-acetylserotonin and S-adenosylmethionine through the action of the enzyme acetylserotonin O-methyltransferase. In addition, Melatonin can be converted into 6-hydroxymelatonin; which is mediated by the enzyme cytochrome P450 1A1. In cattle, melatonin is involved in the metabolic pathway called the tryptophan metabolism pathway. Melatonin is a potentially toxic compound.</description>
  <synonyms>
    <synonym>5-Methoxy-N-acetyltryptamine</synonym>
    <synonym>Melatonine</synonym>
    <synonym>N-[2-(5-Methoxyindol-3-yl)ethyl]acetamide</synonym>
    <synonym>N-Acetyl-5-methoxytryptamine</synonym>
    <synonym>Melatonina</synonym>
    <synonym>Circadin</synonym>
    <synonym>Melatol</synonym>
    <synonym>Melatonin (synth.) standard-grade</synonym>
    <synonym>Melatonin (synth.) ultra-pure</synonym>
    <synonym>Melovine</synonym>
    <synonym>MT6</synonym>
    <synonym>N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide</synonym>
    <synonym>N-(2-(5-Methoxyindol-3-yl)ethyl)-acetamide</synonym>
    <synonym>N-(2-(5-Methoxyindol-3-yl)ethyl)acetamide</synonym>
    <synonym>N-Acetyl-5-methoxy-tryptamine</synonym>
    <synonym>N-Acetyl-5-methoxy-tryptamine melatonine</synonym>
    <synonym>N-[2-(5-Methoxy-1H-indol-3-yl)ethyl)acetamide</synonym>
    <synonym>N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]-acetamide</synonym>
    <synonym>N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide</synonym>
    <synonym>N-[2-(5-Methoxyindol-3-yl)ethyl]-acetamide</synonym>
    <synonym>Regulin</synonym>
    <synonym>{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-} acetamide</synonym>
    <synonym>{N-[2-(5-methoxyindol-3-yl)ethyl]-} acetamide</synonym>
    <synonym>3-(2-Acetamidoethyl)-5-methoxyindole</synonym>
    <synonym>Melatonin</synonym>
  </synonyms>
  <chemical_formula>C13H16N2O2</chemical_formula>
  <average_molecular_weight>232.2783</average_molecular_weight>
  <monisotopic_moleculate_weight>232.121177766</monisotopic_moleculate_weight>
  <iupac_name>N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide</iupac_name>
  <traditional_iupac>melatonin</traditional_iupac>
  <cas_registry_number>73-31-4</cas_registry_number>
  <smiles>COC1=CC2=C(NC=C2CCNC(C)=O)C=C1</smiles>
  <inchi>InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)</inchi>
  <inchikey>DRLFMBDRBRZALE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Indoles</sub_class>
    <direct_parent>3-alkylindoles</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alkylindole</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Indole alkaloids</external_descriptor>
      <external_descriptor>Melatonin</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>acetamides</external_descriptor>
      <external_descriptor>tryptamines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>232.2783</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>232.121177766</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC2=C(NC=C2CCNC(C)=O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H16N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DRLFMBDRBRZALE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>66.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1548</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5230</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438131</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00003 - 0.00006458</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from early lactation, diurnal range</comment>
      <references>
        <reference>
          <reference_text>Eriksson L, Valtonen M, Laitinen JT, Paananen M, Kaikkonen M: Diurnal rhythm of melatonin in bovine milk: pharmacokinetics of exogenous melatonin in lactating cows and goats. Acta Vet Scand. 1998;39(3):301-10.</reference_text>
          <pubmed_id>9787493</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01598</kegg_id>
  <foodb_id>FDB004234</foodb_id>
  <chemspider_id>872</chemspider_id>
  <pubchem_compound_id>896</pubchem_compound_id>
  <drugbank_id>DB01065</drugbank_id>
  <chebi_id>16796</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>N-ACETYL-5-METHOXY-TRYPTAMINE</meta_cyc_id>
  <knapsack_id/>
  <wikipedia_id>Melatonin</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>37965</bigg_id>
  <metlin_id>73</metlin_id>
  <synthesis_reference>Reddy, Gaddam Om; Sarma, Mamillapilli Ramabhadra; Prabhakar, Chebiyyam.  An improved process for the preparation of melatonin.    Indian  (2001),     30 pp.  </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Eriksson L, Valtonen M, Laitinen JT, Paananen M, Kaikkonen M: Diurnal rhythm of melatonin in bovine milk: pharmacokinetics of exogenous melatonin in lactating cows and goats. Acta Vet Scand. 1998;39(3):301-10.</reference_text>
      <pubmed_id>9787493</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00410</protein_accession>
      <name>Hydroxyindole O-methyltransferase</name>
      <uniprot_id>P10950</uniprot_id>
      <gene_name>ASMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01828</protein_accession>
      <name>Melatonin receptor type 1A</name>
      <uniprot_id>O02769</uniprot_id>
      <gene_name>MTNR1A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02000</protein_accession>
      <name>Melatonin receptor 1A</name>
      <uniprot_id>B5LED7</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02001</protein_accession>
      <name>Melatonin receptor 1A</name>
      <uniprot_id>B5LED8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:16 UTC</creation_date>
  <update_date>2020-04-15 22:15:13 UTC</update_date>
  <accession>BMDB0001390</accession>
  <secondary_accessions>
    <accession>BMDB01390</accession>
  </secondary_accessions>
  <name>Hydroxycotinine</name>
  <description/>
  <synonyms>
    <synonym>(3R-trans)-3-Hydroxy-1-methyl-5-(3-pyridinyl)-2-pyrrolidinone</synonym>
    <synonym>3-Hydroxy-1-methyl-5-(3-pyridinyl)-2-pyrrolidinone</synonym>
    <synonym>3-Hydroxycotinine</synonym>
    <synonym>trans-3'-Hydroxycotinine</synonym>
    <synonym>trans-3-Hydroxycotinine</synonym>
    <synonym>1-Methyl-3-hydroxy-5-(3-pyridyl)-2-pyrrolidinone</synonym>
    <synonym>3'-Hydroxycotinine</synonym>
  </synonyms>
  <chemical_formula>C10H12N2O2</chemical_formula>
  <average_molecular_weight>192.2145</average_molecular_weight>
  <monisotopic_moleculate_weight>192.089877638</monisotopic_moleculate_weight>
  <iupac_name>(5S)-3-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one</iupac_name>
  <traditional_iupac>hydroxycotinine</traditional_iupac>
  <cas_registry_number>34834-67-8</cas_registry_number>
  <smiles>CN1[C@@H](CC(O)C1=O)C1=CN=CC=C1</smiles>
  <inchi>InChI=1S/C10H12N2O2/c1-12-8(5-9(13)10(12)14)7-3-2-4-11-6-7/h2-4,6,8-9,13H,5H2,1H3/t8-,9?/m0/s1</inchi>
  <inchikey>XOKCJXZZNAUIQN-IENPIDJESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyrrolidinylpyridines</sub_class>
    <direct_parent>Pyrrolidinylpyridines</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>N-alkylpyrrolidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrrolidine-2-ones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-pyrrolidone</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>N-alkylpyrrolidine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidinylpyridine</substituent>
      <substituent>Pyrrolidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>logp</kind>
      <value>-1.45</value>
      <source>LI,NY &amp; GORROD,JW (1992)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5S)-3-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>192.2145</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>192.089877638</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1[C@@H](CC(O)C1=O)C1=CN=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N2O2/c1-12-8(5-9(13)10(12)14)7-3-2-4-11-6-7/h2-4,6,8-9,13H,5H2,1H3/t8-,9?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XOKCJXZZNAUIQN-IENPIDJESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>53.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347790</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022597</foodb_id>
  <chemspider_id>8395266</chemspider_id>
  <pubchem_compound_id>10219774</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6210</metlin_id>
  <synthesis_reference>Jacob, Peyton, III; Shulgin, Alexander T.; Benowitz, Neal L. Synthesis of (3'R,5'S)-trans-3'-hydroxycotinine, a major metabolite of nicotine. Metabolic formation of 3'-hydroxycotinine in humans is highly stereoselective. J. Med. Chem. (1990), 33 (7), pp 1888–1891</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:17 UTC</creation_date>
  <update_date>2020-03-13 16:27:45 UTC</update_date>
  <accession>BMDB0001391</accession>
  <secondary_accessions>
    <accession>BMDB01391</accession>
  </secondary_accessions>
  <name>GDP-4-Dehydro-6-L-deoxygalactose</name>
  <description/>
  <synonyms>
    <synonym>GDP-4-Dehydro-6-deoxy-D-talose</synonym>
    <synonym>GDP-4-Keto-6-deoxymannose</synonym>
    <synonym>GDP-4-Keto-6-L-deoxygalactose</synonym>
    <synonym>GDP-4-oxo-6-Deoxy-D-mannose</synonym>
    <synonym>GDP-4-oxo-6-Deoxymannose</synonym>
  </synonyms>
  <chemical_formula>C16H23N5O15P2</chemical_formula>
  <average_molecular_weight>587.3258</average_molecular_weight>
  <monisotopic_moleculate_weight>587.066588115</monisotopic_moleculate_weight>
  <iupac_name>[({[(3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3S,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>{[(3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(3S,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxyphosphinic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>C[C@@H]1OC(OP(O)(=O)OP(O)(=O)OCC2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@H](O)C1=O</smiles>
  <inchi>InChI=1S/C16H23N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5?,8+,9+,10+,11-,14+,15?/m0/s1</inchi>
  <inchikey>PNHLMHWWFOPQLK-GTXIGXBOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine nucleotide sugars</sub_class>
    <direct_parent>Pyrimidine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Pyrimidine 2'-deoxyribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Ketone</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine nucleotide sugar</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>TDP-sugar</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3S,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>587.3258</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>587.066588115</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H]1OC(OP(O)(=O)OP(O)(=O)OCC2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@H](O)C1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H23N5O15P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H23N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5?,8+,9+,10+,11-,14+,15?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PNHLMHWWFOPQLK-GTXIGXBOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>304.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>116.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>49.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359079</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id/>
  <foodb_id>FDB022598</foodb_id>
  <pubchem_compound_id>136948341</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <kegg_id>C14830  </kegg_id>
  <drugbank_id/>
  <chebi_id>16955</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:19 UTC</creation_date>
  <update_date>2020-04-16 17:54:14 UTC</update_date>
  <accession>BMDB0001392</accession>
  <secondary_accessions>
    <accession>BMDB01392</accession>
  </secondary_accessions>
  <name>p-Aminobenzoic acid</name>
  <description>4-Aminobenzoic acid, also known as paba or p-aminobenzoate, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. 4-Aminobenzoic acid exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. 4-Aminobenzoic acid exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>1-Amino-4-carboxybenzene</synonym>
    <synonym>4-Amino-benzoic acid</synonym>
    <synonym>4-Aminobenzoesaeure</synonym>
    <synonym>4-Carboxyaniline</synonym>
    <synonym>4-Carboxyphenylamine</synonym>
    <synonym>ABEE</synonym>
    <synonym>gamma-Aminobenzoic acid</synonym>
    <synonym>p-Aminobenzoesaeure</synonym>
    <synonym>p-Carboxyaniline</synonym>
    <synonym>p-Carboxyphenylamine</synonym>
    <synonym>PABA</synonym>
    <synonym>Para-aminobenzoic acid</synonym>
    <synonym>4-Aminobenzoic acid</synonym>
    <synonym>p-Aminobenzoate</synonym>
    <synonym>RVPaba lipstick</synonym>
    <synonym>4-Amino-benzoate</synonym>
    <synonym>g-Aminobenzoate</synonym>
    <synonym>g-Aminobenzoic acid</synonym>
    <synonym>gamma-Aminobenzoate</synonym>
    <synonym>Γ-aminobenzoate</synonym>
    <synonym>Γ-aminobenzoic acid</synonym>
    <synonym>Para-aminobenzoate</synonym>
    <synonym>4-Aminobenzoate</synonym>
    <synonym>Acido p-aminobenzoico</synonym>
    <synonym>Acidum paraminobenzoicum</synonym>
    <synonym>Actipol</synonym>
    <synonym>Amben</synonym>
    <synonym>Aminobenzoate</synonym>
    <synonym>Aminobenzoic acid</synonym>
    <synonym>Aniline-4-carboxylate</synonym>
    <synonym>Aniline-4-carboxylic acid</synonym>
    <synonym>Anti-chromotrichia factor</synonym>
    <synonym>Anticanitic vitamin</synonym>
    <synonym>Anticantic vitamin</synonym>
    <synonym>Antichromotrichia factor</synonym>
    <synonym>Bacterial vitamin H1</synonym>
    <synonym>Chromotrichia factor</synonym>
    <synonym>Hachemina</synonym>
    <synonym>Kyselina p-aminobenzoova</synonym>
    <synonym>p-Amino-benzoate</synonym>
    <synonym>p-Amino-benzoic acid</synonym>
    <synonym>PAB</synonym>
    <synonym>Pabacyd</synonym>
    <synonym>Pabafilm</synonym>
    <synonym>Pabagel</synonym>
    <synonym>Pabamine</synonym>
    <synonym>Pabanol</synonym>
    <synonym>Papacidum</synonym>
    <synonym>Paraminol</synonym>
    <synonym>Paranate</synonym>
    <synonym>Potaba</synonym>
    <synonym>Romavit</synonym>
    <synonym>Rvpaba</synonym>
    <synonym>Sunbrella</synonym>
    <synonym>Super shade by coppertone</synonym>
    <synonym>Trichochromogenic factor</synonym>
    <synonym>Trochromogenic factor</synonym>
    <synonym>Vitamin BX</synonym>
    <synonym>Vitamin h'</synonym>
    <synonym>4 Aminobenzoic acid</synonym>
    <synonym>4 Aminobenzoic acid, potassium salt</synonym>
    <synonym>Epitelplast</synonym>
    <synonym>Jumer brand OF aminobenzoic acid</synonym>
    <synonym>Medea brand OF aminobenzoic acid</synonym>
    <synonym>Paraminan</synonym>
    <synonym>4-Aminobenzoate, potassium</synonym>
    <synonym>Epit vit</synonym>
    <synonym>Llorens brand OF aminobenzoic acid</synonym>
    <synonym>Pabasan</synonym>
    <synonym>Potassium aminobenzoate</synonym>
    <synonym>4-Aminobenzoic acid, potassium salt</synonym>
    <synonym>Aminobenzoate, potassium</synonym>
    <synonym>Glenwood brand OF potassium aminobezoate</synonym>
    <synonym>Llorens brand OF aminobenzoic acid sodium salt</synonym>
    <synonym>Magnesium para-aminobenzoate</synonym>
    <synonym>Potassium 4 aminobenzoate</synonym>
    <synonym>Potassium 4-aminobenzoate</synonym>
    <synonym>p Aminobenzoic acid</synonym>
    <synonym>Para aminobenzoic acid</synonym>
    <synonym>Para-aminobenzoate, magnesium</synonym>
    <synonym>p-Aminobenzoic acid</synonym>
  </synonyms>
  <chemical_formula>C7H7NO2</chemical_formula>
  <average_molecular_weight>137.136</average_molecular_weight>
  <monisotopic_moleculate_weight>137.047678473</monisotopic_moleculate_weight>
  <iupac_name>4-aminobenzoic acid</iupac_name>
  <traditional_iupac>sunbrella</traditional_iupac>
  <cas_registry_number>150-13-0</cas_registry_number>
  <smiles>NC1=CC=C(C=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)</inchi>
  <inchikey>ALYNCZNDIQEVRV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>Aminobenzoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminobenzoic acid</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aminobenzoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>188.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>6.11 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.83</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-aminobenzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>137.136</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>137.047678473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=CC=C(C=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H7NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ALYNCZNDIQEVRV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181792</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437153</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>953</chemspider_id>
  <foodb_id>FDB001037</foodb_id>
  <pubchem_compound_id>978</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <kegg_id>C00568</kegg_id>
  <drugbank_id>DB02362</drugbank_id>
  <chebi_id>30753</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id>C00001401</knapsack_id>
  <wikipedia_id>4-Aminobenzoic_Acid</wikipedia_id>
  <bigg_id/>
  <metlin_id>3261</metlin_id>
  <synthesis_reference>Sato, Ryu; Kimura, Koichi; Takahashi, Akira.  Preparation of p-aminobenzoic acid from styrene polymers.    Jpn. Kokai Tokkyo Koho  (2007),     13pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:20 UTC</creation_date>
  <update_date>2020-04-16 20:39:24 UTC</update_date>
  <accession>BMDB0001394</accession>
  <secondary_accessions>
    <accession>BMDB01394</accession>
  </secondary_accessions>
  <name>Heparin</name>
  <description>Heparin, also known as heparin or heparin, belongs to the class of organic compounds known as disaccharide sulfates. These are disaccharides carrying one or more sulfate group on a sugar unit. Heparin is possibly soluble (in water) and possibly neutral. In cattle, heparin is involved in the metabolic pathway called the FC Epsilon receptor i signaling in mast cells pathway. Heparin is a potentially toxic compound.</description>
  <synonyms>
    <synonym>alpha-Heparin</synonym>
    <synonym>Clivarine</synonym>
    <synonym>Heparin sodium</synonym>
    <synonym>Arteven</synonym>
    <synonym>Bemiparin</synonym>
    <synonym>Certoparin</synonym>
    <synonym>Clexane</synonym>
    <synonym>Dalteparin</synonym>
    <synonym>Enoxaparin</synonym>
    <synonym>Eparina</synonym>
    <synonym>Fraxiparin</synonym>
    <synonym>Heparin sulfate</synonym>
    <synonym>Heparin sulphate</synonym>
    <synonym>Heparinate</synonym>
    <synonym>Heparinic acid</synonym>
    <synonym>Heparinsodiumsalt</synonym>
    <synonym>Thromboliquine</synonym>
  </synonyms>
  <chemical_formula>(C12H19NO19S3)nH2O</chemical_formula>
  <average_molecular_weight/>
  <monisotopic_moleculate_weight/>
  <iupac_name/>
  <traditional_iupac/>
  <cas_registry_number>9005-49-6</cas_registry_number>
  <smiles>[H]O[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](O[C@@H]2O[C@H]([C@@H](O)[C@H](O)[C@H]2OS(O)(=O)=O)C(O)=O)[C@H](O)[C@H]1NS(O)(=O)=O</smiles>
  <inchi>InChI=1S/C12H21NO20S3/c14-4-3(13-34(20,21)22)11(19)30-2(1-29-35(23,24)25)7(4)31-12-9(33-36(26,27)28)6(16)5(15)8(32-12)10(17)18/h2-9,11-16,19H,1H2,(H,17,18)(H,20,21,22)(H,23,24,25)(H,26,27,28)/t2-,3-,4-,5+,6+,7-,8-,9-,11+,12-/m1/s1</inchi>
  <inchikey>OHJKXVLJWUPWQG-PNRHKHKDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as disaccharide sulfates. These are disaccharides carrying  one or more sulfate group on a sugar unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Disaccharide sulfates</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>O-glucuronides</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sulfuric acid monoamides</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-o-glucuronide</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Disaccharide sulfate</substituent>
      <substituent>Glucuronic acid or derivatives</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>O-glucuronide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoamide</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]O[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](O[C@@H]2O[C@H]([C@@H](O)[C@H](O)[C@H]2OS(O)(=O)=O)C(O)=O)[C@H](O)[C@H]1NS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>(C12H19NO19S3)nH2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H21NO20S3/c14-4-3(13-34(20,21)22)11(19)30-2(1-29-35(23,24)25)7(4)31-12-9(33-36(26,27)28)6(16)5(15)8(32-12)10(17)18/h2-9,11-16,19H,1H2,(H,17,18)(H,20,21,22)(H,23,24,25)(H,26,27,28)/t2-,3-,4-,5+,6+,7-,8-,9-,11+,12-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OHJKXVLJWUPWQG-PNRHKHKDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1316716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1316717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1316718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1431166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1431167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1431168</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>7988167</chemspider_id>
  <foodb_id>FDB022599</foodb_id>
  <pubchem_compound_id>9812414</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <kegg_id>C00374</kegg_id>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Heparin</wikipedia_id>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Kuberan, Balagurunathan; Beeler, David L.; Lawrence, Roger; Lech, Miroslaw; Rosenberg, Robert D. Rapid Two-Step Synthesis of Mitrin from Heparosan: A Replacement for Heparin. Journal of the American Chemical Society (2003), 125(41), 12424-12425.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00115</protein_accession>
      <name>Heparanase</name>
      <uniprot_id>Q9MYY0</uniprot_id>
      <gene_name>HPSE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00230</protein_accession>
      <name>Angiogenin-1</name>
      <uniprot_id>P10152</uniprot_id>
      <gene_name>ANG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00231</protein_accession>
      <name>Platelet-activating factor acetylhydrolase IB subunit alpha</name>
      <uniprot_id>P43033</uniprot_id>
      <gene_name>PAFAH1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00232</protein_accession>
      <name>Coagulation factor XI</name>
      <uniprot_id>Q5NTB3</uniprot_id>
      <gene_name>F11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00233</protein_accession>
      <name>Disintegrin and metalloproteinase domain-containing protein 10</name>
      <uniprot_id>Q10741</uniprot_id>
      <gene_name>ADAM10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00234</protein_accession>
      <name>Tissue-type plasminogen activator</name>
      <uniprot_id>Q28198</uniprot_id>
      <gene_name>PLAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00235</protein_accession>
      <name>Hepatic triacylglycerol lipase</name>
      <uniprot_id>Q3SZ79</uniprot_id>
      <gene_name>LIPC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00236</protein_accession>
      <name>Lipoprotein lipase</name>
      <uniprot_id>P11151</uniprot_id>
      <gene_name>LPL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01345</protein_accession>
      <name>Cartilage oligomeric matrix protein</name>
      <uniprot_id>P35445</uniprot_id>
      <gene_name>COMP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01349</protein_accession>
      <name>Vascular endothelial growth factor A</name>
      <uniprot_id>P15691</uniprot_id>
      <gene_name>VEGFA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01351</protein_accession>
      <name>Prolargin</name>
      <uniprot_id>Q9GKN8</uniprot_id>
      <gene_name>PRELP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01377</protein_accession>
      <name>Fibronectin</name>
      <uniprot_id>P07589</uniprot_id>
      <gene_name>FN1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01378</protein_accession>
      <name>Periostin, osteoblast specific factor</name>
      <uniprot_id>Q2KJC7</uniprot_id>
      <gene_name>POSTN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01379</protein_accession>
      <name>Beta-2-glycoprotein 1</name>
      <uniprot_id>P17690</uniprot_id>
      <gene_name>APOH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01380</protein_accession>
      <name>Histidine-rich glycoprotein</name>
      <uniprot_id>P33433</uniprot_id>
      <gene_name>HRG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01381</protein_accession>
      <name>Glycoprotein (Transmembrane) nmb</name>
      <uniprot_id>Q2TA04</uniprot_id>
      <gene_name>GPNMB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01382</protein_accession>
      <name>Connective tissue growth factor</name>
      <uniprot_id>O18739</uniprot_id>
      <gene_name>CTGF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01383</protein_accession>
      <name>Osteoblast-specific factor 2</name>
      <uniprot_id>Q8HZM3</uniprot_id>
      <gene_name>OSF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01384</protein_accession>
      <name>Heparin-binding growth factor 1</name>
      <uniprot_id>P03968</uniprot_id>
      <gene_name>FGF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01385</protein_accession>
      <name>Fibroblast growth factor 18</name>
      <uniprot_id>Q0VCA0</uniprot_id>
      <gene_name>FGF18</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01386</protein_accession>
      <name>Bone morphogenetic protein 4</name>
      <uniprot_id>Q5I4I9</uniprot_id>
      <gene_name>BMP4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01387</protein_accession>
      <name>Monocyte chemotactic protein 1B</name>
      <uniprot_id>P80343</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01388</protein_accession>
      <name>Fibroblast growth factor 4</name>
      <uniprot_id>P48803</uniprot_id>
      <gene_name>FGF4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01389</protein_accession>
      <name>CCDC80 protein</name>
      <uniprot_id>A5PKA3</uniprot_id>
      <gene_name>CCDC80</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01390</protein_accession>
      <name>LOC789567 protein</name>
      <uniprot_id>A6H7H3</uniprot_id>
      <gene_name>LOC789567</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01391</protein_accession>
      <name>Heparin-binding growth factor 2</name>
      <uniprot_id>P03969</uniprot_id>
      <gene_name>FGF2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01392</protein_accession>
      <name>C6H4ORF31 protein</name>
      <uniprot_id>A6QPN7</uniprot_id>
      <gene_name>C6H4ORF31</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01393</protein_accession>
      <name>Bone morphogenetic protein 4</name>
      <uniprot_id>Q6RXL5</uniprot_id>
      <gene_name>BMP4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01394</protein_accession>
      <name>Thrombospondin-2</name>
      <uniprot_id>Q95116</uniprot_id>
      <gene_name>THBS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01395</protein_accession>
      <name>BMP4</name>
      <uniprot_id>Q4VS18</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01396</protein_accession>
      <name>Secreted frizzled-related protein 1</name>
      <uniprot_id>O19116</uniprot_id>
      <gene_name>SFRP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01397</protein_accession>
      <name>Follistatin-related protein 1</name>
      <uniprot_id>Q58D84</uniprot_id>
      <gene_name>FSTL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01398</protein_accession>
      <name>ADAMTS1 protein</name>
      <uniprot_id>A7MB07</uniprot_id>
      <gene_name>ADAMTS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01399</protein_accession>
      <name>R-spondin-3</name>
      <uniprot_id>Q1RMU1</uniprot_id>
      <gene_name>RSPO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01400</protein_accession>
      <name>Regakine-1</name>
      <uniprot_id>P82943</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01401</protein_accession>
      <name>COL5A3 protein</name>
      <uniprot_id>A7E3A1</uniprot_id>
      <gene_name>COL5A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01402</protein_accession>
      <name>Antithrombin-III</name>
      <uniprot_id>P41361</uniprot_id>
      <gene_name>SERPINC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01403</protein_accession>
      <name>C-X-C motif chemokine 6</name>
      <uniprot_id>P80221</uniprot_id>
      <gene_name>CXCL6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01404</protein_accession>
      <name>Tenascin-X</name>
      <uniprot_id>O18977</uniprot_id>
      <gene_name>TN-X</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01405</protein_accession>
      <name>Apolipoprotein E</name>
      <uniprot_id>Q03247</uniprot_id>
      <gene_name>APOE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01406</protein_accession>
      <name>Thrombospondin-1</name>
      <uniprot_id>Q28178</uniprot_id>
      <gene_name>THBS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01407</protein_accession>
      <name>Fibroblast growth factor 5</name>
      <uniprot_id>A0MTF4</uniprot_id>
      <gene_name>FGF5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01408</protein_accession>
      <name>Platelet factor 4</name>
      <uniprot_id>P02777</uniprot_id>
      <gene_name>PF4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01409</protein_accession>
      <name>Low density lipoprotein receptor-related protein associated protein 1</name>
      <uniprot_id>Q148K7</uniprot_id>
      <gene_name>LRPAP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01410</protein_accession>
      <name>C-C motif chemokine 8</name>
      <uniprot_id>Q09141</uniprot_id>
      <gene_name>CCL8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01411</protein_accession>
      <name>Hepatoma-derived growth factor</name>
      <uniprot_id>Q9XSK7</uniprot_id>
      <gene_name>HDGF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01412</protein_accession>
      <name>Pleiotrophin</name>
      <uniprot_id>P21782</uniprot_id>
      <gene_name>PTN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01413</protein_accession>
      <name>ABI family, member 3 (NESH) binding protein</name>
      <uniprot_id>A1L573</uniprot_id>
      <gene_name>ABI3BP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01414</protein_accession>
      <name>Seminal plasma protein BSP-30 kDa</name>
      <uniprot_id>P81019</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01415</protein_accession>
      <name>Patched homolog</name>
      <uniprot_id>Q1MW23</uniprot_id>
      <gene_name>PTCH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01416</protein_accession>
      <name>Vascular endothelial growth factor B</name>
      <uniprot_id>Q9XS49</uniprot_id>
      <gene_name>VEGFB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01417</protein_accession>
      <name>Similar to connective tissue growth factor</name>
      <uniprot_id>Q862T0</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01418</protein_accession>
      <name>Bone morphogenetic protein-4</name>
      <uniprot_id>Q4LEV0</uniprot_id>
      <gene_name>BMP-4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:21 UTC</creation_date>
  <update_date>2020-04-15 22:26:23 UTC</update_date>
  <accession>BMDB0001396</accession>
  <secondary_accessions>
    <accession>BMDB01396</accession>
  </secondary_accessions>
  <name>5-Methyltetrahydrofolic acid</name>
  <description>5-Methyltetrahydrofolic acid, also known as 5-methyltetrahydrofolic acid or 5-methyltetrahydrofolic acid, belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. 5-Methyltetrahydrofolic acid is possibly soluble (in water) and a strong basic compound (based on its pKa). 5-Methyltetrahydrofolic acid exists in all eukaryotes, ranging from yeast to humans. 5-Methyltetrahydrofolic acid participates in a number of enzymatic reactions, within cattle. In particular, Homocysteine and 5-methyltetrahydrofolic acid can be converted into L-methionine and tetrahydrofolic acid through its interaction with the enzyme methionine synthase. In addition, 5-Methyltetrahydrofolic acid can be biosynthesized from 5,10-methylene-THF; which is catalyzed by the enzyme methylenetetrahydrofolate reductase. In cattle, 5-methyltetrahydrofolic acid is involved in a couple of metabolic pathways, which include the betaine metabolism pathway and the folate metabolism pathway.</description>
  <synonyms>
    <synonym>5-Methyltetrahydrofolate</synonym>
    <synonym>5-Methyl tetrahydrofolate</synonym>
    <synonym>5-Methyl-5,6,7,8-tetrahydrofolate</synonym>
    <synonym>5-Methyl-tetrahydrofolate</synonym>
    <synonym>5-Methyltetrahydropteroylglutamate</synonym>
    <synonym>Methyl folate</synonym>
    <synonym>Methyl-tetrahydrofolate</synonym>
    <synonym>N( 5)-Methyltetrahydrofolate</synonym>
    <synonym>N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamate</synonym>
    <synonym>N-(4-(((2-Amino-1,4,5,6,7,8-hexahydro-5-methyl-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid</synonym>
    <synonym>N-(5-Methyl-5,6,7,8-tetrahydropteroyl)-L-glutamate</synonym>
    <synonym>N-(5-Methyl-5,6,7,8-tetrahydropteroyl)-L-glutamic acid</synonym>
    <synonym>N5-Methyl-tetrahydrofolate</synonym>
    <synonym>N5-Methyl-tetrahydrofolic acid</synonym>
    <synonym>N5-Methyltetrahydrofolate</synonym>
    <synonym>N5-Methyltetrahydropteroyl mono-L-glutamate</synonym>
    <synonym>[(6S)-5-Methyl-5,6,7,8-tetrahydropteroyl]glutamate</synonym>
    <synonym>5-Methyltetrahydrofolate, (DL-glu)-isomer</synonym>
    <synonym>5-Methyltetrahydrofolate, (L-glu)-(R)-isomer</synonym>
    <synonym>5-Methyltetrahydrofolate, (L-glu)-(S)-isomer</synonym>
    <synonym>5-Methyltetrahydrofolate, calcium salt (1:1), (L-glu)-isomer</synonym>
    <synonym>5-Methyltetrahydrofolate, methyl-(14)C-labeled, (DL-glu)-isomer</synonym>
    <synonym>5-Methyltetrahydrofolate, methyl-(14)C-labeled, (L-glu)-isomer</synonym>
    <synonym>CH3-FH4</synonym>
    <synonym>L-Methyl folate</synonym>
    <synonym>N(5)-Methyltetrahydrofolic acid</synonym>
    <synonym>Prefolic a</synonym>
    <synonym>Mefolinate</synonym>
    <synonym>Levomefolic acid</synonym>
    <synonym>L-Methylfolate</synonym>
    <synonym>Deplin</synonym>
  </synonyms>
  <chemical_formula>C20H25N7O6</chemical_formula>
  <average_molecular_weight>459.4558</average_molecular_weight>
  <monisotopic_moleculate_weight>459.186631567</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</iupac_name>
  <traditional_iupac>(2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</traditional_iupac>
  <cas_registry_number>134-35-0</cas_registry_number>
  <smiles>CN1C(CNC2=CC=C(C=C2)C(=O)N[C@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)NC(N)=N2</smiles>
  <inchi>InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12?,13-/m1/s1</inchi>
  <inchikey>ZNOVTXRBGFNYRX-ZGTCLIOFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Tetrahydrofolic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminobenzamides</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylarylamines</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Glutamic acid and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hippuric acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalkylamines</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminobenzamide</substituent>
      <substituent>Aminobenzoic acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzamide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoic acid or derivatives</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkylarylamine</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hippuric acid</substituent>
      <substituent>Hippuric acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylalkylamine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tertiary aliphatic/aromatic amine</substituent>
      <substituent>Tertiary amine</substituent>
      <substituent>Tetrahydrofolic acid</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-[(4-{[(2-amino-5-methyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>459.4558</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>459.186631567</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C(CNC2=CC=C(C=C2)C(=O)N[C@H](CCC(O)=O)C(O)=O)CNC2=C1C(=O)NC(N)=N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H25N7O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H25N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,12-13,22H,6-9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t12?,13-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZNOVTXRBGFNYRX-ZGTCLIOFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>198.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>126.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>98049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>98050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>98051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>162879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>162880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>162881</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>388371</chemspider_id>
  <foodb_id>FDB022600</foodb_id>
  <pubchem_compound_id>439234</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <kegg_id>C00440</kegg_id>
  <drugbank_id/>
  <chebi_id>15641</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id>Levomefolic acid</wikipedia_id>
  <bigg_id>34988</bigg_id>
  <metlin_id>6215</metlin_id>
  <synthesis_reference>Gennari, Federico.  Process for producing 5-methyltetrahydrofolic acid and its salts.    U.S.  (1992),     6 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:22 UTC</creation_date>
  <update_date>2020-04-15 23:55:50 UTC</update_date>
  <accession>BMDB0001397</accession>
  <secondary_accessions>
    <accession>BMDB01397</accession>
  </secondary_accessions>
  <name>Guanosine monophosphate</name>
  <description>Guanosine monophosphate, also known as guanylic acid or 5'-GMP, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Guanosine monophosphate is possibly soluble (in water) and a moderately basic compound (based on its pKa). Guanosine monophosphate exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>5'-GMP</synonym>
    <synonym>GMP</synonym>
    <synonym>Guanosine 5'-phosphate</synonym>
    <synonym>Guanosine-5'-monophosphate</synonym>
    <synonym>Guanylic acid</synonym>
    <synonym>pG</synonym>
    <synonym>Guanosine 5'-monophosphate</synonym>
    <synonym>Guanosine 5'-phosphoric acid</synonym>
    <synonym>Guanosine-5'-monophosphoric acid</synonym>
    <synonym>Guanylate</synonym>
    <synonym>Guanosine 5'-monophosphoric acid</synonym>
    <synonym>Guanosine monophosphoric acid</synonym>
    <synonym>e 626</synonym>
    <synonym>Guanidine monophosphate</synonym>
    <synonym>Guanosine 5'-phosphorate</synonym>
    <synonym>Guanosine-5'-phosphate</synonym>
    <synonym>Guanosine-phosphate</synonym>
    <synonym>5' Guanylic acid</synonym>
    <synonym>Acid, 5'-guanylic</synonym>
    <synonym>Acid, guanylic</synonym>
    <synonym>Guanosine 5' monophosphate</synonym>
    <synonym>5'-monoPhosphate, guanosine</synonym>
    <synonym>monoPhosphate, guanosine</synonym>
    <synonym>5'-Guanylic acid</synonym>
  </synonyms>
  <chemical_formula>C10H14N5O8P</chemical_formula>
  <average_molecular_weight>363.2206</average_molecular_weight>
  <monisotopic_moleculate_weight>363.057998961</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>guanylate</traditional_iupac>
  <cas_registry_number>85-32-5</cas_registry_number>
  <smiles>NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1</smiles>
  <inchi>InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1</inchi>
  <inchikey>RQFCJASXJCIDSX-UUOKFMHZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ribonucleotides</external_descriptor>
      <external_descriptor>guanosine 5'-phosphate</external_descriptor>
      <external_descriptor>purine ribonucleoside 5'-monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>369 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>363.2206</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>363.057998961</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H14N5O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RQFCJASXJCIDSX-UUOKFMHZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>201.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>75.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>30.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448138</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw whole milk</comment>
      <references>
        <reference>
          <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
          <pubmed_id>6539345</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44.</reference_text>
          <pubmed_id>7196410</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>6545</chemspider_id>
  <foodb_id>FDB030896</foodb_id>
  <pubchem_compound_id>6804</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <kegg_id>C00144</kegg_id>
  <drugbank_id>DB01972</drugbank_id>
  <chebi_id>17345</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>GMP</meta_cyc_id>
  <knapsack_id>C00019635</knapsack_id>
  <wikipedia_id>Guanosine_monophosphate</wikipedia_id>
  <bigg_id>34024</bigg_id>
  <metlin_id>6216</metlin_id>
  <synthesis_reference>Sato, Katsuaki; Matsui, Hiroshi; Ei, Hitoshi; Takinami, Koichi.  Guanosine-5'-monophosphate.    Jpn. Kokai Tokkyo Koho  (1979),     3 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.</reference_text>
      <pubmed_id>6539345</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gil A, Sanchez-Medina F: Acid-soluble nucleotides of cow's, goat's and sheep's milks, at different stages of lactation. J Dairy Res. 1981 Feb;48(1):35-44.</reference_text>
      <pubmed_id>7196410</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00429</protein_accession>
      <name>Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'</name>
      <uniprot_id>P16586</uniprot_id>
      <gene_name>PDE6C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00430</protein_accession>
      <name>Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha</name>
      <uniprot_id>P11541</uniprot_id>
      <gene_name>PDE6A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00431</protein_accession>
      <name>Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit beta</name>
      <uniprot_id>P23439</uniprot_id>
      <gene_name>PDE6B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00432</protein_accession>
      <name>GMP reductase 2</name>
      <uniprot_id>Q32L93</uniprot_id>
      <gene_name>GMPR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00433</protein_accession>
      <name>Retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma</name>
      <uniprot_id>P22571</uniprot_id>
      <gene_name>PDE6H</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00434</protein_accession>
      <name>cGMP-specific 3',5'-cyclic phosphodiesterase</name>
      <uniprot_id>Q28156</uniprot_id>
      <gene_name>PDE5A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00435</protein_accession>
      <name>Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma</name>
      <uniprot_id>P04972</uniprot_id>
      <gene_name>PDE6G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00436</protein_accession>
      <name>Atrial natriuretic peptide receptor B</name>
      <uniprot_id>P46197</uniprot_id>
      <gene_name>NPR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01587</protein_accession>
      <name>Guanylate binding protein family, member 6</name>
      <uniprot_id>Q0V7P3</uniprot_id>
      <gene_name>GBP6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01588</protein_accession>
      <name>Guanylate binding protein 1, interferon-inducible</name>
      <uniprot_id>A5D955</uniprot_id>
      <gene_name>GBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:23 UTC</creation_date>
  <update_date>2020-03-13 16:27:48 UTC</update_date>
  <accession>BMDB0001398</accession>
  <secondary_accessions>
    <accession>BMDB01398</accession>
  </secondary_accessions>
  <name>Guaiacol</name>
  <description>Guaiacol, also known as Guaiacol or Guaiacol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Guaiacol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Guaiacol exists in all living species, ranging from bacteria to humans. Guaiacol participates in a number of enzymatic reactions, within cattle. In particular, Norepinephrine and guaiacol can be converted into normetanephrine and pyrocatechol; which is mediated by the enzyme catechol O-methyltransferase. In addition, Epinephrine and guaiacol can be converted into metanephrine and pyrocatechol; which is mediated by the enzyme catechol O-methyltransferase. In cattle, guaiacol is involved in the metabolic pathway called the tyrosine metabolism pathway. Guaiacol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Hydroxy-2-methoxybenzene</synonym>
    <synonym>2-Hydroxyanisole</synonym>
    <synonym>Catechol monomethyl ether</synonym>
    <synonym>O-Methoxyphenol</synonym>
    <synonym>Creodon</synonym>
    <synonym>2-Methoxyphenol</synonym>
    <synonym>2-Methoxy-phenol</synonym>
    <synonym>Anastil</synonym>
    <synonym>Guaiacol (liquid) extra pure</synonym>
    <synonym>Guaiastil</synonym>
    <synonym>Guaicol</synonym>
    <synonym>Guaicolina</synonym>
    <synonym>Guajakol</synonym>
    <synonym>Guajol</synonym>
    <synonym>Guasol</synonym>
    <synonym>Guiacol</synonym>
    <synonym>Methoxyphenol</synonym>
    <synonym>Methylcatachol</synonym>
    <synonym>Methylcatechol</synonym>
    <synonym>O-Guaiacol</synonym>
    <synonym>O-Hydroxyanisole</synonym>
    <synonym>O-Methoxy-phenol</synonym>
    <synonym>O-Methyl catechol</synonym>
    <synonym>Pyrocatechol monomethyl ether</synonym>
    <synonym>Pyroguaiac acid</synonym>
    <synonym>2-Hydroxy-anisole</synonym>
    <synonym>Catechol, methyl</synonym>
    <synonym>Methyl catechol</synonym>
    <synonym>2-Methoxyl-4-vinylphenol</synonym>
    <synonym>Guaiacol</synonym>
  </synonyms>
  <chemical_formula>C7H8O2</chemical_formula>
  <average_molecular_weight>124.139</average_molecular_weight>
  <monisotopic_moleculate_weight>124.052429498</monisotopic_moleculate_weight>
  <iupac_name>2-methoxyphenol</iupac_name>
  <traditional_iupac>guaiacol</traditional_iupac>
  <cas_registry_number>90-05-1</cas_registry_number>
  <smiles>COC1=C(O)C=CC=C1</smiles>
  <inchi>InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3</inchi>
  <inchikey>LHGVFZTZFXWLCP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Methoxyphenols</sub_class>
    <direct_parent>Methoxyphenols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a guaiacol</external_descriptor>
      <external_descriptor>monomethoxybenzene</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>28 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>18.7 mg/mL at 15 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.32</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-methoxyphenol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>124.139</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>124.052429498</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=C(O)C=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H8O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LHGVFZTZFXWLCP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>29.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>7243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>13915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4283</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>447</chemspider_id>
  <foodb_id>FDB011885</foodb_id>
  <pubchem_compound_id>460</pubchem_compound_id>
  <phenol_explorer_compound_id>650</phenol_explorer_compound_id>
  <kegg_id>C15572</kegg_id>
  <drugbank_id>DB11359</drugbank_id>
  <chebi_id>28591</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>CPD-400</meta_cyc_id>
  <knapsack_id>C00029459</knapsack_id>
  <wikipedia_id>Guaiacol</wikipedia_id>
  <bigg_id/>
  <metlin_id>6217</metlin_id>
  <synthesis_reference>Chen, Jiehua; Xu, Baocai; Zhang, Hong; Ye, Jianfeng.  Method for preparing guaiacol from catechol and dimethyl carbonate.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2007),     6pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00421</protein_accession>
      <name>Catechol O-methyltransferase</name>
      <uniprot_id>A7MBI7</uniprot_id>
      <gene_name>COMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:24 UTC</creation_date>
  <update_date>2020-03-13 16:27:48 UTC</update_date>
  <accession>BMDB0001399</accession>
  <secondary_accessions>
    <accession>BMDB01399</accession>
  </secondary_accessions>
  <name>4,6-Dideoxy-4-oxo-dTDP-D-glucose</name>
  <description/>
  <synonyms>
    <synonym>dTDP-4-Dehydro-6-deoxy-D-glucose</synonym>
    <synonym>dTDP-4-Dehydro-6-deoxy-L-mannose</synonym>
    <synonym>dTDP-4-Dehydro-L-rhamnose</synonym>
    <synonym>dTDP-4-oxo-6-Deoxy-D-glucose</synonym>
    <synonym>dTDP-4-oxo-6-Deoxy-L-mannose</synonym>
    <synonym>dTDP-4-oxo-L-Rhamnose</synonym>
    <synonym>TDP-4-Keto-6-deoxy-D-glucose</synonym>
    <synonym>TDP-4-oxo-6-Deoxy-D-glucose</synonym>
    <synonym>dTDP-6-Deoxy-4-ketoglucose</synonym>
    <synonym>dTDP-KDG</synonym>
    <synonym>dTDP-6-Deoxy-D-xylo-4-hexulose</synonym>
    <synonym>Thymidine diphosphate-6-deoxy-xylo-4-hexulose, alpha-isomer</synonym>
    <synonym>Thymidine diphosphate-6-deoxy-xylo-4-hexulose</synonym>
    <synonym>dTDP-DXH</synonym>
    <synonym>Thymidine diphosphate-6-deoxy-D-xylo-4-hexulose</synonym>
  </synonyms>
  <chemical_formula>C16H24N2O15P2</chemical_formula>
  <average_molecular_weight>546.3137</average_molecular_weight>
  <monisotopic_moleculate_weight>546.065191132</monisotopic_moleculate_weight>
  <iupac_name>{[(3R,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy}({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>[(3R,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy({hydroxy[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methoxyphosphoryl}oxy)phosphinic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>C[C@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H](C[C@@H]2O)N2C=C(C)C(=O)NC2=O)[C@H](O)[C@@H](O)C1=O</smiles>
  <inchi>InChI=1S/C16H24N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-10,12-13,15,19,21-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/t7-,8+,9-,10-,12+,13-,15?/m1/s1</inchi>
  <inchikey>PSXWNITXWWECNY-SRPWTXKTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine nucleotide sugars</sub_class>
    <direct_parent>Pyrimidine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Pyrimidine 2'-deoxyribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Ketone</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine nucleotide sugar</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>TDP-sugar</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(3R,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy}({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>546.3137</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>546.065191132</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H]1OC(OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H](C[C@@H]2O)N2C=C(C)C(=O)NC2=O)[C@H](O)[C@@H](O)C1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H24N2O15P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H24N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-10,12-13,15,19,21-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/t7-,8+,9-,10-,12+,13-,15?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PSXWNITXWWECNY-SRPWTXKTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>247.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>106.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>45.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38056</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34138</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>391705</chemspider_id>
  <foodb_id>FDB022601</foodb_id>
  <pubchem_compound_id>443496</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <kegg_id>C11907</kegg_id>
  <drugbank_id/>
  <chebi_id>16620</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <bigg_id>35701</bigg_id>
  <metlin_id>6218</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:26 UTC</creation_date>
  <update_date>2020-04-16 20:38:41 UTC</update_date>
  <accession>BMDB0001401</accession>
  <secondary_accessions>
    <accession>BMDB01401</accession>
  </secondary_accessions>
  <name>Glucose 6-phosphate</name>
  <description>Glucose 6-phosphate, also known as robison ester or GLC6P, belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Glucose 6-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Glucose 6-phosphate exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>6-O-Phosphono-D-glucopyranose</synonym>
    <synonym>D-Glucose 6-phosphate</synonym>
    <synonym>GLC6p</synonym>
    <synonym>Robison ester</synonym>
    <synonym>D-Glucose 6-phosphoric acid</synonym>
    <synonym>Glucose 6-phosphoric acid</synonym>
    <synonym>a-D-Glucose 6- phosphate</synonym>
    <synonym>alpha-D-Glucose 6- phosphate</synonym>
    <synonym>alpha-D-Glucose 6-phosphate</synonym>
    <synonym>alpha-D-Hexose 6-phosphate</synonym>
    <synonym>D(+)-Glucopyranose 6-phosphate</synonym>
    <synonym>D-Glucose-6-dihydrogen phosphate</synonym>
    <synonym>D-Hexose 6-phosphate</synonym>
    <synonym>Glucose-6-phosphate</synonym>
    <synonym>Glucose 6-phosphate</synonym>
    <synonym>D-Glucopyranose 6-phosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C6H13O9P</chemical_formula>
  <average_molecular_weight>260.1358</average_molecular_weight>
  <monisotopic_moleculate_weight>260.029718526</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>glucose 6-phosphate</traditional_iupac>
  <cas_registry_number>56-73-5</cas_registry_number>
  <smiles>OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1</inchi>
  <inchikey>NBSCHQHZLSJFNQ-GASJEMHNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D-glucose 6-phosphate</external_descriptor>
      <external_descriptor>D-hexopyranose 6-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>260.1358</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>260.029718526</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NBSCHQHZLSJFNQ-GASJEMHNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>156.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1558</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5259</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5261</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5262</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1930</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1948</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38057</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>46.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
          <pubmed_id>2760296</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>83</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Rulquin H, Verite R: Effects of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 1. Diets based on corn silage. J Dairy Sci. 1998 Dec;81(12):3239-47. doi: 10.3168/jds.S0022-0302(98)75888-6.</reference_text>
          <pubmed_id>9891269</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>41</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>62</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
          <pubmed_id>11132867</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>5743</chemspider_id>
  <foodb_id>FDB021818</foodb_id>
  <pubchem_compound_id>5958</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <kegg_id>C00092</kegg_id>
  <drugbank_id/>
  <chebi_id>4170</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>D-glucose-6-phosphate</meta_cyc_id>
  <knapsack_id>C00007306</knapsack_id>
  <wikipedia_id>Glucose_6-phosphate</wikipedia_id>
  <bigg_id>36977</bigg_id>
  <metlin_id>145</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83.</reference_text>
      <pubmed_id>2760296</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hurtaud C, Rulquin H, Verite R: Effects of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 1. Diets based on corn silage. J Dairy Sci. 1998 Dec;81(12):3239-47. doi: 10.3168/jds.S0022-0302(98)75888-6.</reference_text>
      <pubmed_id>9891269</pubmed_id>
    </reference>
    <reference>
      <reference_text>Hurtaud C, Lemosquet S, Rulquin H: Effect of graded duodenal infusions of glucose on yield and composition of milk from dairy cows. 2. Diets based on grass silage. J Dairy Sci. 2000 Dec;83(12):2952-62. doi: 10.3168/jds.S0022-0302(00)75195-2.</reference_text>
      <pubmed_id>11132867</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00165</protein_accession>
      <name>Glucose-6-phosphatase</name>
      <uniprot_id>Q29RU6</uniprot_id>
      <gene_name>G6PC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00173</protein_accession>
      <name>Glucose-6-phosphatase 3</name>
      <uniprot_id>Q148G2</uniprot_id>
      <gene_name>G6PC3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00522</protein_accession>
      <name>ADP-dependent glucokinase</name>
      <uniprot_id>A2VE47</uniprot_id>
      <gene_name>ADPGK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00912</protein_accession>
      <name>Hexokinase-1</name>
      <uniprot_id>P27595</uniprot_id>
      <gene_name>HK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00992</protein_accession>
      <name>Glucose-6-phosphate 1-dehydrogenase</name>
      <uniprot_id>Q0P587</uniprot_id>
      <gene_name>H6PD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00997</protein_accession>
      <name>Glucose-6-phosphate 1-dehydrogenase</name>
      <uniprot_id>Q5EM56</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01026</protein_accession>
      <name>Inositol-3-phosphate synthase 1</name>
      <uniprot_id>Q2NL29</uniprot_id>
      <gene_name>ISYNA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01172</protein_accession>
      <name>Glycogen phosphorylase, brain form</name>
      <uniprot_id>Q3B7M9</uniprot_id>
      <gene_name>PYGB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01208</protein_accession>
      <name>Glycogen phosphorylase, liver form</name>
      <uniprot_id>Q0VCM4</uniprot_id>
      <gene_name>PYGL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01246</protein_accession>
      <name>Glucose-6-phosphate isomerase</name>
      <uniprot_id>Q3ZBD7</uniprot_id>
      <gene_name>GPI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:27 UTC</creation_date>
  <update_date>2020-04-16 17:54:14 UTC</update_date>
  <accession>BMDB0001403</accession>
  <secondary_accessions>
    <accession>BMDB01403</accession>
  </secondary_accessions>
  <name>Prostaglandin D2</name>
  <description>Prostaglandin D2, also known as prostaglandin D2 or Prostaglandin d2, belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Thus, prostaglandin D2 is considered to be an eicosanoid lipid molecule. Prostaglandin D2 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Prostaglandin D2 exists in all living organisms, ranging from bacteria to humans. Prostaglandin D2 participates in a number of enzymatic reactions, within cattle. In particular, Prostaglandin D2 can be converted into prostaglandin D2 through its interaction with the enzyme prostaglandin D2 receptor. In addition, Prostaglandin D2 can be converted into prostaglandin D2; which is mediated by the enzyme prostaglandin D2 receptor. In cattle, prostaglandin D2 is involved in the metabolic pathway called the intracellular signalling through prostaglandin D2 receptor and prostaglandin D2 pathway.</description>
  <synonyms>
    <synonym>(5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E,15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate</synonym>
    <synonym>11-Dehydroprostaglandin F2-alpha</synonym>
    <synonym>PGD2</synonym>
    <synonym>(5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-9Α,15-dihydroxy-11-oxoprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-9Α,15-dihydroxy-11-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E,15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E,15S)-9Α,15-dihydroxy-11-oxoprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E,15S)-9Α,15-dihydroxy-11-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>11-Dehydroprostaglandin F2-a</synonym>
    <synonym>11-Dehydroprostaglandin F2-α</synonym>
    <synonym>(5Z,13E)-(15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-9,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E,15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate</synonym>
    <synonym>(5Z,13E,15S)-9-alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,13E,15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dien-1-Oic acid</synonym>
    <synonym>(5Z,9-alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,9-alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oic acid</synonym>
    <synonym>(5Z,9alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,9alpha,13E,15S)-9,15-Dihydroxy-11-oxo-prosta-5,13-dien-1-Oic acid</synonym>
    <synonym>11-Dehydroprostaglandin F2alpha</synonym>
    <synonym>9S,15S-Dihydroxy-11-oxo-5Z,13E-prostadienoate</synonym>
    <synonym>9S,15S-Dihydroxy-11-oxo-5Z,13E-prostadienoic acid</synonym>
    <synonym>F2alpha, 11-Dehydroprostaglandin</synonym>
    <synonym>11 Dehydroprostaglandin F2alpha</synonym>
    <synonym>11 Dehydroprostaglandin F2 alpha</synonym>
    <synonym>D2, Prostaglandin</synonym>
    <synonym>F2 alpha, 11-Dehydroprostaglandin</synonym>
    <synonym>alpha, 11-Dehydroprostaglandin F2</synonym>
    <synonym>11-Dehydroprostaglandin F2 alpha</synonym>
  </synonyms>
  <chemical_formula>C20H32O5</chemical_formula>
  <average_molecular_weight>352.4651</average_molecular_weight>
  <monisotopic_moleculate_weight>352.224974134</monisotopic_moleculate_weight>
  <iupac_name>(5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid</iupac_name>
  <traditional_iupac>prostaglandin D2</traditional_iupac>
  <cas_registry_number>41598-07-6</cas_registry_number>
  <smiles>[H][C@](O)(CCCCC)\C=C\[C@@]1([H])C(=O)C[C@]([H])(O)[C@]1([H])C\C=C/CCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1</inchi>
  <inchikey>BHMBVRSPMRCCGG-OUTUXVNYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Prostaglandins and related compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Cyclopentanols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclopentanol</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Prostaglandin skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>prostaglandins D</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>56 - 57 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>352.4651</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>352.224974134</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@](O)(CCCCC)\C=C\[C@@]1([H])C(=O)C[C@]([H])(O)[C@]1([H])C\C=C/CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H32O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BHMBVRSPMRCCGG-OUTUXVNYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>99.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fc Epsilon Receptor I Signaling in Mast Cells</name>
      <smpdb_id>SMP0108186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through PGD2 receptor and Prostaglandin D2</name>
      <smpdb_id>SMP0107997</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>256182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>256183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>256184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>276123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>276124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>276125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440660</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00696</kegg_id>
  <foodb_id>FDB022602</foodb_id>
  <drugbank_id>DB02056</drugbank_id>
  <chemspider_id>395250</chemspider_id>
  <pubchem_compound_id>448457</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15555</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id>35725</bigg_id>
  <wikipedia_id>Prostaglandin_D2</wikipedia_id>
  <metlin_id>6221</metlin_id>
  <synthesis_reference>Ogawa, Yuji; Nunomoto, Makoto; Shibasaki, Masakatsu. A novel synthesis of prostaglandin D2. Journal of Organic Chemistry (1986), 51(9), 1625-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00102</protein_accession>
      <name>Prostaglandin-H2 D-isomerase</name>
      <uniprot_id>O02853</uniprot_id>
      <gene_name>PTGDS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01335</protein_accession>
      <name>Prostaglandin D2 receptor</name>
      <uniprot_id>A5D7K8</uniprot_id>
      <gene_name>PTGDR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:28 UTC</creation_date>
  <update_date>2020-03-20 00:57:43 UTC</update_date>
  <accession>BMDB0001405</accession>
  <secondary_accessions>
    <accession>BMDB0002332</accession>
    <accession>BMDB01405</accession>
    <accession>BMDB02332</accession>
  </secondary_accessions>
  <name>3-Sulfinylpyruvic acid</name>
  <description>3-Sulfinylpyruvic acid, also known as 3-sulfinylpyruvic acid or 3-sulfinylpyruvic acid, belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. 3-Sulfinylpyruvic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Sulfinylpyruvic acid exists in all living organisms, ranging from bacteria to humans. 3-Sulfinylpyruvic acid and L-glutamic acid can be biosynthesized from 3-sulfinoalanine and oxoglutaric acid; which is catalyzed by the enzyme aspartate aminotransferase, cytoplasmic. In cattle, 3-sulfinylpyruvic acid is involved in the metabolic pathway called the cysteine metabolism pathway.</description>
  <synonyms>
    <synonym>3-Sulfinopyruvate</synonym>
    <synonym>3-Sulfinylpyruvate</synonym>
    <synonym>3-Sulfinopyruvic acid</synonym>
    <synonym>3-Sulphinopyruvate</synonym>
    <synonym>3-Sulphinopyruvic acid</synonym>
    <synonym>3-Sulphinylpyruvate</synonym>
    <synonym>3-Sulphinylpyruvic acid</synonym>
    <synonym>beta-Sulfinyl pyruvate</synonym>
    <synonym>beta-Sulfinyl pyruvic acid</synonym>
    <synonym>2-oxo-3-Sulfinopropanoic acid</synonym>
    <synonym>beta-Sulfinyl-pyruvate</synonym>
    <synonym>beta-Sulfinyl-pyruvic acid</synonym>
    <synonym>Β-sulfinyl pyruvate</synonym>
    <synonym>Β-sulfinyl pyruvic acid</synonym>
    <synonym>Β-sulfinyl-pyruvate</synonym>
    <synonym>Β-sulfinyl-pyruvic acid</synonym>
    <synonym>3-Sulfinylpyruvic acid</synonym>
  </synonyms>
  <chemical_formula>C3H4O5S</chemical_formula>
  <average_molecular_weight>152.126</average_molecular_weight>
  <monisotopic_moleculate_weight>151.977943928</monisotopic_moleculate_weight>
  <iupac_name>2-oxo-3-sulfinopropanoic acid</iupac_name>
  <traditional_iupac>3-sulfinylpyruvate</traditional_iupac>
  <cas_registry_number>88947-38-0</cas_registry_number>
  <smiles>OC(=O)C(=O)CS(O)=O</smiles>
  <inchi>InChI=1S/C3H4O5S/c4-2(3(5)6)1-9(7)8/h1H2,(H,5,6)(H,7,8)</inchi>
  <inchikey>JXYLQEMXCAAMOL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Alpha-keto acids and derivatives</sub_class>
    <direct_parent>Alpha-keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkanesulfinic acids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organosulfur compounds</alternative_parent>
      <alternative_parent>Sulfinic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkanesulfinic acid</substituent>
      <substituent>Alkanesulfinic acid or derivatives</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Sulfinic acid</substituent>
      <substituent>Sulfinic acid derivative</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>organosulfinic acid</external_descriptor>
      <external_descriptor>sulfur-containing carboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-oxo-3-sulfinopropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>152.126</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>151.977943928</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C(=O)CS(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H4O5S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H4O5S/c4-2(3(5)6)1-9(7)8/h1H2,(H,5,6)(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JXYLQEMXCAAMOL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>91.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>26.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>353772</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05527</kegg_id>
  <foodb_id>FDB022965</foodb_id>
  <drugbank_id/>
  <chemspider_id>108</chemspider_id>
  <pubchem_compound_id>110</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>1665</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6627</metlin_id>
  <synthesis_reference>Chatagner, Fernande; Bergeret, Bernadette; Fromageot, Claude.  Transaminations taking part in the metabolism of cysteinesulfinic acid in mammals.    Ann. Acad. Sci. Fennicae  (1955),  II;No.60(Ser. A),  393-400.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:29 UTC</creation_date>
  <update_date>2020-04-16 20:37:59 UTC</update_date>
  <accession>BMDB0001406</accession>
  <secondary_accessions>
    <accession>BMDB01406</accession>
  </secondary_accessions>
  <name>Niacinamide</name>
  <description>Niacinamide, also known as nicotinamid or vitamin B3, belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group. Niacinamide exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Niacinamide exists in all living species, ranging from bacteria to humans. Niacinamide participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylmethionine and niacinamide can be converted into S-adenosylhomocysteine and 1-methylnicotinamide through the action of the enzyme nicotinamide N-methyltransferase. In addition, Niacinamide and ribose-1-arsenate can be converted into nicotinamide riboside and phosphoric acid through its interaction with the enzyme purine nucleoside phosphorylase. In cattle, niacinamide is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway. Niacinamide is a potentially toxic compound.</description>
  <synonyms>
    <synonym>3-Pyridinecarboxamide</synonym>
    <synonym>beta-Pyridinecarboxamide</synonym>
    <synonym>Niacin</synonym>
    <synonym>Nicotinamid</synonym>
    <synonym>Nicotinic acid amide</synonym>
    <synonym>Nicotinsaeureamid</synonym>
    <synonym>Nikotinamid</synonym>
    <synonym>Nikotinsaeureamid</synonym>
    <synonym>Vitamin b3</synonym>
    <synonym>Vitamin PP</synonym>
    <synonym>Nicotinamide</synonym>
    <synonym>b-Pyridinecarboxamide</synonym>
    <synonym>Β-pyridinecarboxamide</synonym>
    <synonym>Nicotinate amide</synonym>
    <synonym>3-Carbamoylpyridine</synonym>
    <synonym>3-Pyridinecarboxylic acid amide</synonym>
    <synonym>Acid amide</synonym>
    <synonym>Amid kyseliny nikotinove</synonym>
    <synonym>Amide PP</synonym>
    <synonym>Aminicotin</synonym>
    <synonym>Amixicotyn</synonym>
    <synonym>Amnicotin</synonym>
    <synonym>Austrovit PP</synonym>
    <synonym>Benicot</synonym>
    <synonym>Delonin amide</synonym>
    <synonym>Dipegyl</synonym>
    <synonym>Dipigyl</synonym>
    <synonym>Endobion</synonym>
    <synonym>Factor PP</synonym>
    <synonym>Hansamid</synonym>
    <synonym>Inovitan PP</synonym>
    <synonym>m-(Aminocarbonyl)pyridine</synonym>
    <synonym>Mediatric</synonym>
    <synonym>NAM</synonym>
    <synonym>Nandervit-N</synonym>
    <synonym>Niacevit</synonym>
    <synonym>Niamide</synonym>
    <synonym>Niavit PP</synonym>
    <synonym>Nicamide</synonym>
    <synonym>Nicamina</synonym>
    <synonym>Nicamindon</synonym>
    <synonym>Nicasir</synonym>
    <synonym>Nicobion</synonym>
    <synonym>Nicofort</synonym>
    <synonym>Nicogen</synonym>
    <synonym>Nicomidol</synonym>
    <synonym>Nicosan 2</synonym>
    <synonym>Nicosylamide</synonym>
    <synonym>Nicota</synonym>
    <synonym>Nicotamide</synonym>
    <synonym>Nicotilamide</synonym>
    <synonym>Nicotililamido</synonym>
    <synonym>Nicotinamida</synonym>
    <synonym>Nicotinamidum</synonym>
    <synonym>Nicotine acid amide</synonym>
    <synonym>Nicotine amide</synonym>
    <synonym>Nicotinic amide</synonym>
    <synonym>Nicotinsaureamid</synonym>
    <synonym>Nicotol</synonym>
    <synonym>Nicotylamide</synonym>
    <synonym>Nicotylamidum</synonym>
    <synonym>Nicovel</synonym>
    <synonym>Nicovit</synonym>
    <synonym>Nicovitina</synonym>
    <synonym>Nicovitol</synonym>
    <synonym>Nicozymin</synonym>
    <synonym>Nictoamide</synonym>
    <synonym>Niko-tamin</synonym>
    <synonym>Niocinamide</synonym>
    <synonym>Niozymin</synonym>
    <synonym>Papulex</synonym>
    <synonym>Pelmin</synonym>
    <synonym>Pelmine</synonym>
    <synonym>Pelonin amide</synonym>
    <synonym>PP-Faktor</synonym>
    <synonym>Propamine a</synonym>
    <synonym>Pyridine-3-carboxylic acid amide</synonym>
    <synonym>Savacotyl</synonym>
    <synonym>Vi-nicotyl</synonym>
    <synonym>Vi-noctyl</synonym>
    <synonym>Witamina PP</synonym>
    <synonym>3 Pyridinecarboxamide</synonym>
    <synonym>Astra brand OF niacinamide</synonym>
    <synonym>b 3, Vitamin</synonym>
    <synonym>Niacinamide merck brand</synonym>
    <synonym>Pharmagenix brand OF niacinamide</synonym>
    <synonym>b3, Vitamin</synonym>
    <synonym>Enduramide</synonym>
    <synonym>Jenapharm, nicotinsäureamid</synonym>
    <synonym>Niacinamide jenapharm brand</synonym>
    <synonym>Niacinamide pharmagenix brand</synonym>
    <synonym>Jenapharm brand OF niacinamide</synonym>
    <synonym>Nicotinsäureamid jenapharm</synonym>
    <synonym>Vitamin b 3</synonym>
    <synonym>Merck brand OF niacinamide</synonym>
    <synonym>Niacinamide astra brand</synonym>
    <synonym>Niacinamide</synonym>
  </synonyms>
  <chemical_formula>C6H6N2O</chemical_formula>
  <average_molecular_weight>122.1246</average_molecular_weight>
  <monisotopic_moleculate_weight>122.048012824</monisotopic_moleculate_weight>
  <iupac_name>pyridine-3-carboxamide</iupac_name>
  <traditional_iupac>nicotinamide</traditional_iupac>
  <cas_registry_number>98-92-0</cas_registry_number>
  <smiles>NC(=O)C1=CC=CN=C1</smiles>
  <inchi>InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)</inchi>
  <inchikey>DFPAKSUCGFBDDF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyridinecarboxylic acids and derivatives</sub_class>
    <direct_parent>Nicotinamides</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Nicotinamide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Pyridine alkaloids</external_descriptor>
      <external_descriptor>Water-soluble vitamins</external_descriptor>
      <external_descriptor>a vitamin</external_descriptor>
      <external_descriptor>an aliphatic amide</external_descriptor>
      <external_descriptor>pyridine alkaloid</external_descriptor>
      <external_descriptor>pyridinecarboxamide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>130 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>500 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.37</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.39</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>pyridine-3-carboxamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>122.1246</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>122.048012824</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)C1=CC=CN=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H6N2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DFPAKSUCGFBDDF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>55.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1068</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1559</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1561</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5281</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31946</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.6 +/- 2.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Organic milk</comment>
      <references>
        <reference>
          <reference_text>Superfoodly: https://www.superfoodly.com/nicotinamide-riboside-food-sources/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.2 +/- 3.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Conventional milk</comment>
      <references>
        <reference>
          <reference_text>Superfoodly: https://www.superfoodly.com/nicotinamide-riboside-food-sources/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.3 +/- 1.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk (n=18)</comment>
      <references>
        <reference>
          <reference_text>Trammell SA, Yu L, Redpath P, Migaud ME, Brenner C: Nicotinamide Riboside Is a Major NAD+ Precursor Vitamin in Cow Milk. J Nutr. 2016 May;146(5):957-63. doi: 10.3945/jn.116.230078. Epub 2016 Apr 6.</reference_text>
          <pubmed_id>27052539</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.6 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.4 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11.3 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>10.3 +/- 0.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.7 +/- 0.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.4 +/- 0.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 1035 Friesian Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>135.28 +/- 8.64</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Korean commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>141.86 +/- 6.17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in New Zealand commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>90.35 +/- 6.44</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in Australian commercial beef sirloin.</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>96.76 +/- 6.23</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by NMR in US commercial beef sirloin</comment>
      <references>
        <reference>
          <reference_text>Jung Y, Lee J, Kwon J, Lee KS, Ryu DH, Hwang GS: Discrimination of the geographical origin of beef by (1)H NMR-based metabolomics. J Agric Food Chem. 2010 Oct 13;58(19):10458-66. doi: 10.1021/jf102194t.</reference_text>
          <pubmed_id>20831251</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00153</kegg_id>
  <foodb_id>FDB012485</foodb_id>
  <drugbank_id>DB02701</drugbank_id>
  <chemspider_id>911</chemspider_id>
  <pubchem_compound_id>936</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17154</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00000209</knapsack_id>
  <meta_cyc_id>NIACINAMIDE</meta_cyc_id>
  <bigg_id>34058</bigg_id>
  <wikipedia_id>Nicotinamide</wikipedia_id>
  <metlin_id>1497</metlin_id>
  <synthesis_reference>Galat, Alexander. Nicotinamide from nicotinonitrile by catalytic hydration. Journal of the American Chemical Society (1948), 70 3945.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309.</reference_text>
      <pubmed_id>17558655</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Trammell SA, Yu L, Redpath P, Migaud ME, Brenner C: Nicotinamide Riboside Is a Major NAD+ Precursor Vitamin in Cow Milk. J Nutr. 2016 May;146(5):957-63. doi: 10.3945/jn.116.230078. Epub 2016 Apr 6.</reference_text>
      <pubmed_id>27052539</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Superfoodly: https://www.superfoodly.com/nicotinamide-riboside-food-sources/</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00136</protein_accession>
      <name>tRNA 2'-phosphotransferase 1</name>
      <uniprot_id>Q3ZBM7</uniprot_id>
      <gene_name>TRPT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00830</protein_accession>
      <name>Ecto-ADP-ribosyltransferase 5</name>
      <uniprot_id>Q0VC22</uniprot_id>
      <gene_name>ART5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00831</protein_accession>
      <name>NAD-dependent deacetylase sirtuin-7</name>
      <uniprot_id>Q0P595</uniprot_id>
      <gene_name>SIRT7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00832</protein_accession>
      <name>Poly [ADP-ribose] polymerase 1</name>
      <uniprot_id>P18493</uniprot_id>
      <gene_name>PARP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00833</protein_accession>
      <name>NAD-dependent deacetylase sirtuin-5</name>
      <uniprot_id>Q3ZBQ0</uniprot_id>
      <gene_name>SIRT5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:31 UTC</creation_date>
  <update_date>2020-03-13 16:27:51 UTC</update_date>
  <accession>BMDB0001409</accession>
  <secondary_accessions>
    <accession>BMDB01409</accession>
  </secondary_accessions>
  <name>dUMP</name>
  <description/>
  <synonyms>
    <synonym>2'-Deoxyuridine 5'-monophosphate</synonym>
    <synonym>2'-Deoxyuridine 5'-phosphate</synonym>
    <synonym>Deoxyuridine 5'-phosphate</synonym>
    <synonym>Deoxyuridine monophosphate</synonym>
    <synonym>Deoxyuridylate</synonym>
    <synonym>Deoxyuridylic acid</synonym>
    <synonym>2'-Deoxyuridine 5'-monophosphoric acid</synonym>
    <synonym>2'-Deoxyuridine 5'-phosphoric acid</synonym>
    <synonym>Deoxyuridine 5'-phosphoric acid</synonym>
    <synonym>Deoxyuridine monophosphoric acid</synonym>
    <synonym>2'-Deoxy-5'-uridylate</synonym>
    <synonym>2'-Deoxy-5'-uridylic acid</synonym>
    <synonym>2'-Deoxyuridylate</synonym>
    <synonym>2'-Deoxyuridylic acid</synonym>
    <synonym>Deoxy-UMP</synonym>
    <synonym>Deoxyuridine 5'-monophosphate</synonym>
    <synonym>2'-Deoxyuridine-5'-monophosphate</synonym>
    <synonym>2'-Deoxyuridylic acid, disodium salt</synonym>
  </synonyms>
  <chemical_formula>C9H13N2O8P</chemical_formula>
  <average_molecular_weight>308.1819</average_molecular_weight>
  <monisotopic_moleculate_weight>308.040951914</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>2'-deoxyuridylic acid</traditional_iupac>
  <cas_registry_number>964-26-1</cas_registry_number>
  <smiles>O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O</smiles>
  <inchi>InChI=1S/C9H13N2O8P/c12-5-3-8(11-2-1-7(13)10-9(11)14)19-6(5)4-18-20(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1</inchi>
  <inchikey>JSRLJPSBLDHEIO-SHYZEUOFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside monophosphates. These are pyrimidine nucleotides with a monophosphate group  linked to the ribose moiety lacking a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine deoxyribonucleotides</sub_class>
    <direct_parent>Pyrimidine 2'-deoxyribonucleoside monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine 2'-deoxyribonucleoside monophosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxyribonucleotides</external_descriptor>
      <external_descriptor>deoxyuridine phosphate</external_descriptor>
      <external_descriptor>pyrimidine 2'-deoxyribonucleoside 5'-monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>308.1819</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>308.040951914</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13N2O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13N2O8P/c12-5-3-8(11-2-1-7(13)10-9(11)14)19-6(5)4-18-20(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JSRLJPSBLDHEIO-SHYZEUOFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>145.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>61.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439046</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00365</kegg_id>
  <foodb_id>FDB022604</foodb_id>
  <drugbank_id>DB03800</drugbank_id>
  <chemspider_id>58574</chemspider_id>
  <pubchem_compound_id>65063</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17622</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00019282</knapsack_id>
  <meta_cyc_id>DUMP</meta_cyc_id>
  <bigg_id>34762</bigg_id>
  <wikipedia_id>Deoxyuridine_monophosphate</wikipedia_id>
  <metlin_id>6225</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00536</protein_accession>
      <name>Thymidylate synthase</name>
      <uniprot_id>Q2TA32</uniprot_id>
      <gene_name>TYMS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:32 UTC</creation_date>
  <update_date>2020-03-13 16:27:51 UTC</update_date>
  <accession>BMDB0001410</accession>
  <secondary_accessions>
    <accession>BMDB01410</accession>
  </secondary_accessions>
  <name>2-Amino-4-oxo-6-(1',2'-dioxoprolyl)-7,8-dihydroxypteridine</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C9H9N5O5</chemical_formula>
  <average_molecular_weight>267.1983</average_molecular_weight>
  <monisotopic_moleculate_weight>267.060368423</monisotopic_moleculate_weight>
  <iupac_name>1-(2-amino-7,8-dihydroxy-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)propane-1,2-dione</iupac_name>
  <traditional_iupac>1-(2-amino-7,8-dihydroxy-4-oxo-3,7-dihydropteridin-6-yl)propane-1,2-dione</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(=O)C(=O)C1=NC2=C(N=C(N)NC2=O)N(O)C1O</smiles>
  <inchi>InChI=1S/C9H9N5O5/c1-2(15)5(16)3-8(18)14(19)6-4(11-3)7(17)13-9(10)12-6/h8,18-19H,1H3,(H3,10,12,13,17)</inchi>
  <inchikey>QBHQZPRDJMYEDG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Pterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkanolamines</alternative_parent>
      <alternative_parent>Alpha-diketones</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketimines</alternative_parent>
      <alternative_parent>N-organohydroxylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkanolamine</substituent>
      <substituent>Alpha-diketone</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Ketimine</substituent>
      <substituent>Ketone</substituent>
      <substituent>N-organohydroxylamine</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pterin</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-(2-amino-7,8-dihydroxy-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)propane-1,2-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>267.1983</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>267.060368423</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)C(=O)C1=NC2=C(N=C(N)NC2=O)N(O)C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H9N5O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H9N5O5/c1-2(15)5(16)3-8(18)14(19)6-4(11-3)7(17)13-9(10)12-6/h8,18-19H,1H3,(H3,10,12,13,17)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QBHQZPRDJMYEDG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>157.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>69.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312871</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358231</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358232</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358233</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05255</kegg_id>
  <foodb_id>FDB022605</foodb_id>
  <drugbank_id/>
  <chemspider_id>389496</chemspider_id>
  <pubchem_compound_id>135532281</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:33 UTC</creation_date>
  <update_date>2020-04-15 22:15:16 UTC</update_date>
  <accession>BMDB0001411</accession>
  <secondary_accessions>
    <accession>BMDB01411</accession>
  </secondary_accessions>
  <name>Cotinine N-oxide</name>
  <description/>
  <synonyms>
    <synonym>(-)-Cotinine N-oxide</synonym>
    <synonym>(5S)-1-Methyl-5-(1-oxido-3-pyridinyl)-2-pyrrolidinone</synonym>
    <synonym>(S)-1-Methyl-5-(1-oxido-3-pyridinyl)-2-pyrrolidinone</synonym>
    <synonym>(S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone N-oxide</synonym>
    <synonym>3-[(2S)-1-Methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate</synonym>
    <synonym>Cotinine-N-oxide</synonym>
    <synonym>3-[(2S)-1-Methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olic acid</synonym>
    <synonym>Cotinine-1-N-oxide</synonym>
  </synonyms>
  <chemical_formula>C10H12N2O2</chemical_formula>
  <average_molecular_weight>192.2145</average_molecular_weight>
  <monisotopic_moleculate_weight>192.089877638</monisotopic_moleculate_weight>
  <iupac_name>3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate</iupac_name>
  <traditional_iupac>3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate</traditional_iupac>
  <cas_registry_number>36508-80-2</cas_registry_number>
  <smiles>CN1[C@@H](CCC1=O)C1=C[N+]([O-])=CC=C1</smiles>
  <inchi>InChI=1S/C10H12N2O2/c1-11-9(4-5-10(11)13)8-3-2-6-12(14)7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1</inchi>
  <inchikey>CIPULDKLIIVIER-VIFPVBQESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyrrolidinylpyridines</sub_class>
    <direct_parent>Pyrrolidinylpyridines</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>N-alkylpyrrolidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridinium derivatives</alternative_parent>
      <alternative_parent>Pyrrolidine-2-ones</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-pyrrolidone</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>N-alkylpyrrolidine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridinium</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidinylpyridine</substituent>
      <substituent>Pyrrolidone</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>192.2145</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>192.089877638</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1[C@@H](CCC1=O)C1=C[N+]([O-])=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N2O2/c1-11-9(4-5-10(11)13)8-3-2-6-12(14)7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CIPULDKLIIVIER-VIFPVBQESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>45.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>52.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>103863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>103864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>103865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>170016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>170017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>170018</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022606</foodb_id>
  <drugbank_id/>
  <chemspider_id>7991264</chemspider_id>
  <pubchem_compound_id>9815514</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>89087</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-3185</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6227</metlin_id>
  <synthesis_reference>Riah, Omar; Dousset, Jean Claude; Courriere, Philippe; Baziard-Mouysset, Genevieve; Ecalle, Rene.  Synthesis of cotinine and cotinine N-oxide. Evaluation of their interaction with nicotine in the insecticidal activity.    Natural Product Letters  (1997),  11(1),  37-45.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:34 UTC</creation_date>
  <update_date>2020-03-13 16:27:52 UTC</update_date>
  <accession>BMDB0001412</accession>
  <secondary_accessions>
    <accession>BMDB01412</accession>
  </secondary_accessions>
  <name>7,8-Dihydropteroic acid</name>
  <description/>
  <synonyms>
    <synonym>4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoic acid</synonym>
    <synonym>7,8-Dihydropteroate</synonym>
    <synonym>Dihydropteroate</synonym>
    <synonym>Dihydropteroinsaeure</synonym>
    <synonym>4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoate</synonym>
    <synonym>Dihydropteroic acid</synonym>
    <synonym>4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoate</synonym>
    <synonym>4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoic acid</synonym>
    <synonym>4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoate</synonym>
    <synonym>4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]-benzoic acid</synonym>
    <synonym>Dihydropterate</synonym>
    <synonym>H2Pte</synonym>
    <synonym>p-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]-benzoate</synonym>
    <synonym>p-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]-benzoic acid</synonym>
  </synonyms>
  <chemical_formula>C14H14N6O3</chemical_formula>
  <average_molecular_weight>314.2994</average_molecular_weight>
  <monisotopic_moleculate_weight>314.112738344</monisotopic_moleculate_weight>
  <iupac_name>4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid</iupac_name>
  <traditional_iupac>7,8-dihydropteroic acid</traditional_iupac>
  <cas_registry_number>2134-76-1</cas_registry_number>
  <smiles>NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(O)=O)CN2)C(=O)N1</smiles>
  <inchi>InChI=1S/C14H14N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,16H,5-6H2,(H,22,23)(H4,15,17,19,20,21)</inchi>
  <inchikey>WBFYVDCHGVNRBH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Pterins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminobenzoic acids</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Ketimines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalkylamines</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminobenzoic acid</substituent>
      <substituent>Aminobenzoic acid or derivatives</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoic acid or derivatives</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imine</substituent>
      <substituent>Ketimine</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylalkylamine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pterin</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>pteroic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>314.2994</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>314.112738344</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(O)=O)CN2)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H14N6O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H14N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,16H,5-6H2,(H,22,23)(H4,15,17,19,20,21)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WBFYVDCHGVNRBH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>141.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>93.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32290</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00921</kegg_id>
  <foodb_id>FDB030621</foodb_id>
  <drugbank_id/>
  <chemspider_id>165</chemspider_id>
  <pubchem_compound_id>170</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>4581</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007228</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6228</metlin_id>
  <synthesis_reference>Bartels, Rainer; Bock, Lothar. Determination of pteroic acid by high-performance thin-layer chromatography. Contribution to the investigation of 7,8-dihydropteroate synthase. Journal of Chromatography (1994), 659(1), 185-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:35 UTC</creation_date>
  <update_date>2020-04-15 22:07:32 UTC</update_date>
  <accession>BMDB0001413</accession>
  <secondary_accessions>
    <accession>BMDB01413</accession>
  </secondary_accessions>
  <name>Citicoline</name>
  <description/>
  <synonyms>
    <synonym>[2-CYTIDYLATE-o'-phosphonyloxyl]-ethyl-trimethyl-ammonium</synonym>
    <synonym>CDP-Colina</synonym>
    <synonym>Citicolina</synonym>
    <synonym>Citicolinum</synonym>
    <synonym>Citidin difosfato de colina</synonym>
    <synonym>Cyticholine</synonym>
    <synonym>Cytidindiphosphocholin</synonym>
    <synonym>Cytidine 5'-(choline diphosphate)</synonym>
    <synonym>Cytidine 5'-(cholinyl pyrophosphate)</synonym>
    <synonym>Cytidine 5'-diphosphocholine</synonym>
    <synonym>Cytidine 5'-diphosphoric choline</synonym>
    <synonym>Nicholin</synonym>
    <synonym>[2-CYTIDYLic acid-o'-phosphonyloxyl]-ethyl-trimethyl-ammonium</synonym>
    <synonym>Cytidine 5'-(choline diphosphoric acid)</synonym>
    <synonym>Cytidine 5'-(cholinyl pyrophosphoric acid)</synonym>
    <synonym>Audes</synonym>
    <synonym>CDP-Choline</synonym>
    <synonym>Cereb</synonym>
    <synonym>Choline 5'-cytidine diphosphate</synonym>
    <synonym>Choline cytidine diphosphate</synonym>
    <synonym>Citicholine</synonym>
    <synonym>Citidoline</synonym>
    <synonym>Citifar</synonym>
    <synonym>Colite</synonym>
    <synonym>Corenalin</synonym>
    <synonym>Cyscholin</synonym>
    <synonym>Cytidine 5'-diphosphate choline</synonym>
    <synonym>Cytidine 5-diphosphate-trihydrogen</synonym>
    <synonym>Cytidine choline diphosphate</synonym>
    <synonym>Cytidine diphosphate choline</synonym>
    <synonym>Cytidine diphosphate choline ester</synonym>
    <synonym>Cytidine diphosphocholine</synonym>
    <synonym>Cytidine diphosphorylcholine</synonym>
    <synonym>Cytidine-5' diphosphocholine</synonym>
    <synonym>Cytidine-5'-pyrophosphate-hydroxycholine</synonym>
    <synonym>Cytidoline</synonym>
    <synonym>Difosfocin</synonym>
    <synonym>Emicholine F</synonym>
    <synonym>Ensign</synonym>
    <synonym>Haocolin</synonym>
    <synonym>Hornbest</synonym>
    <synonym>Neucolis</synonym>
    <synonym>Nicolin</synonym>
    <synonym>Niticolin</synonym>
    <synonym>p-Hydroxide[2-(trimethylammonio)ethyl] ester</synonym>
    <synonym>Reagin</synonym>
    <synonym>Recofnan</synonym>
    <synonym>Recognan</synonym>
    <synonym>Rexort</synonym>
    <synonym>Sintoclar</synonym>
    <synonym>Somazina</synonym>
    <synonym>Somazine</synonym>
    <synonym>Suncholin</synonym>
    <synonym>Cidifos</synonym>
    <synonym>Diphosphate choline, cytidine</synonym>
    <synonym>Choline, CDP</synonym>
    <synonym>CDP Choline</synonym>
    <synonym>5'-Diphosphocholine, cytidine</synonym>
    <synonym>Cytidine 5' diphosphocholine</synonym>
    <synonym>Choline, cytidine diphosphate</synonym>
  </synonyms>
  <chemical_formula>C14H26N4O11P2</chemical_formula>
  <average_molecular_weight>488.324</average_molecular_weight>
  <monisotopic_moleculate_weight>488.107330718</monisotopic_moleculate_weight>
  <iupac_name>{2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]ethyl}trimethylazanium</iupac_name>
  <traditional_iupac>[2-({[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)ethyl]trimethylazanium</traditional_iupac>
  <cas_registry_number>987-78-0</cas_registry_number>
  <smiles>C[N+](C)(C)CCOP([O-])(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O</smiles>
  <inchi>InChI=1S/C14H26N4O11P2/c1-18(2,3)6-7-26-30(22,23)29-31(24,25)27-8-9-11(19)12(20)13(28-9)17-5-4-10(15)16-14(17)21/h4-5,9,11-13,19-20H,6-8H2,1-3H3,(H3-,15,16,21,22,23,24,25)/t9-,11-,12-,13-/m1/s1</inchi>
  <inchikey>RZZPDXZPRHQOCG-OJAKKHQRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group  linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine ribonucleotides</sub_class>
    <direct_parent>Pyrimidine ribonucleoside diphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Phosphocholines</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphocholine</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>nucleotide-(amino alcohol)s</external_descriptor>
      <external_descriptor>phosphocholines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.032</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]ethyl}trimethylazanium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>488.324</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>488.107330718</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)CCOP([O-])(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H26N4O11P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H26N4O11P2/c1-18(2,3)6-7-26-30(22,23)29-31(24,25)27-8-9-11(19)12(20)13(28-9)17-5-4-10(15)16-14(17)21/h4-5,9,11-13,19-20H,6-8H2,1-3H3,(H3-,15,16,21,22,23,24,25)/t9-,11-,12-,13-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RZZPDXZPRHQOCG-OJAKKHQRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>213.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>113.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>42.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>295104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>336036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439055</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448136</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00307</kegg_id>
  <foodb_id>FDB022608</foodb_id>
  <chemspider_id>13207</chemspider_id>
  <pubchem_compound_id>13804</pubchem_compound_id>
  <drugbank_id>DB04290</drugbank_id>
  <chebi_id>16436</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007231</knapsack_id>
  <meta_cyc_id/>
  <bigg_id>1485298</bigg_id>
  <wikipedia_id>Citicoline</wikipedia_id>
  <metlin_id>6229</metlin_id>
  <synthesis_reference>Fujio, Tatsuro.  New production method of useful substances using ATP regeneration system.    Kiraru Tekunoroji no Shintenkai  (2001),     187-198.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00133</protein_accession>
      <name>Manganese-dependent ADP-ribose/CDP-alcohol diphosphatase</name>
      <uniprot_id>A7YY53</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00390</protein_accession>
      <name>Cholinephosphotransferase 1</name>
      <uniprot_id>Q1LZE6</uniprot_id>
      <gene_name>CHPT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:36 UTC</creation_date>
  <update_date>2020-04-16 20:38:41 UTC</update_date>
  <accession>BMDB0001414</accession>
  <secondary_accessions>
    <accession>BMDB01414</accession>
  </secondary_accessions>
  <name>Putrescine</name>
  <description>Putrescine, also known as 1,4-butanediamine or 1,4-diaminobutane, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Putrescine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Putrescine exists in all living species, ranging from bacteria to humans. Putrescine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1,4-Butanediamine</synonym>
    <synonym>1,4-Butylenediamine</synonym>
    <synonym>1,4-DIAMINOBUTANE</synonym>
    <synonym>1,4-Tetramethylenediamine</synonym>
    <synonym>Butane-1,4-diamine</synonym>
    <synonym>Butylenediamine</synonym>
    <synonym>H2N(CH2)4nh2</synonym>
    <synonym>Putrescin</synonym>
    <synonym>Putrescina</synonym>
    <synonym>Putreszin</synonym>
    <synonym>Tetramethylendiamin</synonym>
    <synonym>Tetramethylenediamine</synonym>
    <synonym>1,4-Butanediammonium</synonym>
    <synonym>Tetramethyldiamine</synonym>
    <synonym>1,4 Diaminobutane</synonym>
    <synonym>1,4 Butanediamine</synonym>
  </synonyms>
  <chemical_formula>C4H12N2</chemical_formula>
  <average_molecular_weight>88.1515</average_molecular_weight>
  <monisotopic_moleculate_weight>88.100048394</monisotopic_moleculate_weight>
  <iupac_name>butane-1,4-diamine</iupac_name>
  <traditional_iupac>putrescine</traditional_iupac>
  <cas_registry_number>110-60-1</cas_registry_number>
  <smiles>NCCCCN</smiles>
  <inchi>InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2</inchi>
  <inchikey>KIDHWZJUCRJVML-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>Monoalkylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Biogenic amines</external_descriptor>
      <external_descriptor>alkane-alpha,omega-diamine</external_descriptor>
      <external_descriptor>an aliphatic &amp;alpha;,&amp;omega;-diamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>27.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.7</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>butane-1,4-diamine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>88.1515</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>88.100048394</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCCN</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H12N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KIDHWZJUCRJVML-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>52.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>27.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5292</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5296</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1047</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32315</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.04+/-0.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>0.2+/-0.1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>1.3+/-0.4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by GC-TOF/MS</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>9-22</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>103+/-58</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS &amp; NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>26.31 +/- 12.21</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>52.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>122.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>314.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>26.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>29-111</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>52 +/- 17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>122 +/- 29</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>214 +/- 89</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>28 +/- 12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>28.0 +/- 12.0</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by GC-MS</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>2+/-1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>11+/-3</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB001494</foodb_id>
  <kegg_id>C00134</kegg_id>
  <chemspider_id>13837702</chemspider_id>
  <drugbank_id>DB01917</drugbank_id>
  <pubchem_compound_id>1045</pubchem_compound_id>
  <chebi_id>17148</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00001428</knapsack_id>
  <bigg_id>33980</bigg_id>
  <wikipedia_id>Putrescine</wikipedia_id>
  <metlin_id>3226</metlin_id>
  <meta_cyc_id>PUTRESCINE</meta_cyc_id>
  <synthesis_reference>Dudley, H. W.; Thorpe, W. V. Synthesis of N-methylputrescine and of putrescine. Biochemical Journal (1925), 19 845-9.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
      <pubmed_id>25599412</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00128</protein_accession>
      <name>Peroxisomal N(1)-acetyl-spermine/spermidine oxidase</name>
      <uniprot_id>Q865R1</uniprot_id>
      <gene_name>PAOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00922</protein_accession>
      <name>Ornithine decarboxylase</name>
      <uniprot_id>P27117</uniprot_id>
      <gene_name>ODC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00923</protein_accession>
      <name>Ornithine decarboxylase</name>
      <uniprot_id>Q2TBX3</uniprot_id>
      <gene_name>ADC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:37 UTC</creation_date>
  <update_date>2020-03-13 16:27:54 UTC</update_date>
  <accession>BMDB0001416</accession>
  <secondary_accessions>
    <accession>BMDB01416</accession>
  </secondary_accessions>
  <name>Pantetheine 4'-phosphate</name>
  <description>Pantetheine 4'-phosphate, also known as Pantetheine 4'-phosphate or PSH-4'-p, belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Pantetheine 4'-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Pantetheine 4'-phosphate exists in all living species, ranging from bacteria to humans. Pantetheine 4'-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Pantetheine 4'-phosphate can be biosynthesized from pantetheine through the action of the enzyme pantothenate kinase 1. In addition, Pantetheine 4'-phosphate can be biosynthesized from 4'-phosphopantothenoylcysteine through its interaction with the enzyme phosphopantothenoylcysteine decarboxylase. In cattle, pantetheine 4'-phosphate is involved in the metabolic pathway called pantothenate and CoA biosynthesis pathway.</description>
  <synonyms>
    <synonym>4'-Phosphopantetheine</synonym>
    <synonym>Pantotheine-4'-phosphate</synonym>
    <synonym>Phosphopantetheine</synonym>
    <synonym>PSH-4'-p</synonym>
    <synonym>Pantotheine-4'-phosphoric acid</synonym>
    <synonym>Pantetheine 4'-phosphoric acid</synonym>
    <synonym>4'-Phosphopantotheine</synonym>
    <synonym>D-Pantetheine 4'-phosphate</synonym>
    <synonym>Phospho-pantotheine</synonym>
    <synonym>Pantetheine-4'-phosphate</synonym>
  </synonyms>
  <chemical_formula>C11H23N2O7PS</chemical_formula>
  <average_molecular_weight>358.348</average_molecular_weight>
  <monisotopic_moleculate_weight>358.096358302</monisotopic_moleculate_weight>
  <iupac_name>[3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphonic acid</iupac_name>
  <traditional_iupac>pantetheine 4'-phosphate</traditional_iupac>
  <cas_registry_number>2226-71-3</cas_registry_number>
  <smiles>CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)NCCS</smiles>
  <inchi>InChI=1S/C11H23N2O7PS/c1-11(2,7-20-21(17,18)19)9(15)10(16)13-4-3-8(14)12-5-6-22/h9,15,22H,3-7H2,1-2H3,(H,12,14)(H,13,16)(H2,17,18,19)</inchi>
  <inchikey>JDMUPRLRUUMCTL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic phosphoric acids and derivatives</class>
    <sub_class>Phosphate esters</sub_class>
    <direct_parent>Monoalkyl phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>phosphopantetheine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>358.348</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>358.096358302</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)(COP(O)(O)=O)C(O)C(=O)NCCC(=O)NCCS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H23N2O7PS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H23N2O7PS/c1-11(2,7-20-21(17,18)19)9(15)10(16)13-4-3-8(14)12-5-6-22/h9,15,22H,3-7H2,1-2H3,(H,12,14)(H,13,16)(H2,17,18,19)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JDMUPRLRUUMCTL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>145.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>81.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pantothenate and CoA Biosynthesis</name>
      <smpdb_id>SMP0087207</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33673</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022609</foodb_id>
  <kegg_id>C01134</kegg_id>
  <chemspider_id>962</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>987</pubchem_compound_id>
  <chebi_id>16858</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>36886</bigg_id>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Masuda, Toru; Fujii, Shoichiro; Takanohashi, Kunio.  Pantetheine 4'-phosphate.    Jpn. Tokkyo Koho  (1971),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00368</protein_accession>
      <name>Fatty acid synthase</name>
      <uniprot_id>Q71SP7</uniprot_id>
      <gene_name>FASN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01088</protein_accession>
      <name>Acyl carrier protein, mitochondrial</name>
      <uniprot_id>P52505</uniprot_id>
      <gene_name>NDUFAB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:39 UTC</creation_date>
  <update_date>2020-03-13 16:27:55 UTC</update_date>
  <accession>BMDB0001417</accession>
  <secondary_accessions>
    <accession>BMDB01417</accession>
  </secondary_accessions>
  <name>Permanganate</name>
  <description/>
  <synonyms>
    <synonym>[MnO3(OH)]</synonym>
    <synonym>HMnO4</synonym>
    <synonym>Mangan(VII)-saeure</synonym>
    <synonym>Manganic(VII) acid</synonym>
    <synonym>Permangansaeure</synonym>
    <synonym>Uebermangansaeure</synonym>
    <synonym>Permanganic acid</synonym>
    <synonym>MnO4(1-)</synonym>
    <synonym>Permanganate</synonym>
  </synonyms>
  <chemical_formula>HMnO4</chemical_formula>
  <average_molecular_weight>119.942</average_molecular_weight>
  <monisotopic_moleculate_weight>119.925528</monisotopic_moleculate_weight>
  <iupac_name>manganesoylol</iupac_name>
  <traditional_iupac>permanganic acid</traditional_iupac>
  <cas_registry_number>14333-13-2</cas_registry_number>
  <smiles>O[Mn](=O)(=O)=O</smiles>
  <inchi>InChI=1S/Mn.H2O.3O/h;1H2;;;/q+1;;;;/p-1</inchi>
  <inchikey>ZJBYBXHCMWGGRR-UHFFFAOYSA-M</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as inorganic oxides. These are inorganic chemical compounds with one or more oxygen atoms combined with another element.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Miscellaneous inorganic compounds</super_class>
    <class>Inorganic oxides</class>
    <sub_class/>
    <direct_parent>Inorganic oxides</direct_parent>
    <alternative_parents>
      <alternative_parent>Inorganic salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Inorganic oxide</substituent>
      <substituent>Inorganic salt</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>manganese oxoacid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>manganesoylol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>119.942</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>119.925528</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[Mn](=O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>HMnO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Mn.H2O.3O/h;1H2;;;/q+1;;;;/p-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZJBYBXHCMWGGRR-UHFFFAOYSA-M</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>71.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>6.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>6.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1273999</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1274000</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1274001</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1388983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1388984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1388985</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022610</foodb_id>
  <kegg_id/>
  <chemspider_id>374116</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>422689</pubchem_compound_id>
  <chebi_id>35124</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Permanganate</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Atanasiu, Ion A.; Lazar, Lya B.; Constantinescu, Maria.  Preparation of permanganate by both direct current and alternating current anodic dissolution of manganese and its alloys.    Buletinul Institutului Politehnic Gheorghe Gheorghiu-Dej Bucuresti  (1967),  29(1),  49-57.  </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:40 UTC</creation_date>
  <update_date>2020-03-13 16:27:55 UTC</update_date>
  <accession>BMDB0001419</accession>
  <secondary_accessions>
    <accession>BMDB01419</accession>
  </secondary_accessions>
  <name>24-Hydroxycholesterol</name>
  <description/>
  <synonyms>
    <synonym>(24S)-Hydroxycholesterol</synonym>
    <synonym>24S-Hydroxy-cholesterol</synonym>
    <synonym>Cerebrosterol</synonym>
    <synonym>Cholest-5-en-3beta,24S-diol</synonym>
    <synonym>Cholest-5-ene-3,24-diol</synonym>
    <synonym>(24S)-24-Hydroxycholesterol</synonym>
    <synonym>(24S)-Cholest-5-ene-3beta,24-diol</synonym>
    <synonym>Cholest-5-en-3b,24S-diol</synonym>
    <synonym>Cholest-5-en-3β,24S-diol</synonym>
    <synonym>(24S)-Cholest-5-ene-3b,24-diol</synonym>
    <synonym>(24S)-Cholest-5-ene-3β,24-diol</synonym>
    <synonym>24(S)-Hydroxycholesterol</synonym>
    <synonym>24S-Cholest-5-ene-3b,24-diol</synonym>
    <synonym>24S-Hydroxycholesterol</synonym>
    <synonym>Cerebrosterin</synonym>
    <synonym>Cholest-5-ene-3b,24b-diol</synonym>
  </synonyms>
  <chemical_formula>C27H46O2</chemical_formula>
  <average_molecular_weight>402.6529</average_molecular_weight>
  <monisotopic_moleculate_weight>402.349780716</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol</iupac_name>
  <traditional_iupac>24(S)-hydroxycholesterol</traditional_iupac>
  <cas_registry_number>474-73-7</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@H](O)C(C)C</smiles>
  <inchi>InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>IOWMKBFJCNLRTC-XWXSNNQWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Bile acids, alcohols and derivatives</sub_class>
    <direct_parent>Dihydroxy bile acids, alcohols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>24-hydroxysteroid</substituent>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Dihydroxy bile acid, alcohol, or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>24-hydroxycholesterol</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
      <external_descriptor>oxysterol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>402.6529</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>402.349780716</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@H](O)C(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H46O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IOWMKBFJCNLRTC-XWXSNNQWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>122.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342441</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022611</foodb_id>
  <kegg_id>C13550</kegg_id>
  <chemspider_id>108790</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>121948</pubchem_compound_id>
  <chebi_id>34310</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>2197434</bigg_id>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Prasad V V; Ponticorvo L; Lieberman S  Identification of 24-hydroxycholesterol in bovine adrenals in both free and esterified forms and in bovine brains as its sulfate ester.    Journal of steroid biochemistry  (1984),  21(6),  733-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:41 UTC</creation_date>
  <update_date>2020-03-13 16:27:56 UTC</update_date>
  <accession>BMDB0001420</accession>
  <secondary_accessions>
    <accession>BMDB01420</accession>
  </secondary_accessions>
  <name>25,26-dihydroxyvitamin D</name>
  <description/>
  <synonyms>
    <synonym>25,26-Dihydroxycholecalciferol</synonym>
    <synonym>25,26-Dihydroxyvitamin D3</synonym>
    <synonym>9,10-Secocholesta-5,7,10(19)-triene-3b,25,26-triol</synonym>
  </synonyms>
  <chemical_formula>C27H44O3</chemical_formula>
  <average_molecular_weight>416.6365</average_molecular_weight>
  <monisotopic_moleculate_weight>416.329045274</monisotopic_moleculate_weight>
  <iupac_name>(6R)-6-[(1R,3aS,5Z,7aS)-5-{2-[(1Z,5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-1,2-diol</iupac_name>
  <traditional_iupac>25,26-dihydroxyvitamin D</traditional_iupac>
  <cas_registry_number>29261-12-9</cas_registry_number>
  <smiles>[H][C@@]12CC[C@]([H])([C@H](C)CCCC(C)(O)CO)[C@@]1(C)CC\C(C2)=C\C=C1\C[C@@H](O)CCC1=C</smiles>
  <inchi>InChI=1S/C27H44O3/c1-19-7-11-24(29)17-22(19)9-8-21-13-15-27(4)23(16-21)10-12-25(27)20(2)6-5-14-26(3,30)18-28/h8-9,20,23-25,28-30H,1,5-7,10-18H2,2-4H3/b21-8-,22-9-/t20-,23+,24+,25-,26?,27+/m1/s1</inchi>
  <inchikey>WWGCQHXFACVYPT-JKVVTCAUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Sesquiterpenoids</sub_class>
    <direct_parent>Sesquiterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Fatty alcohols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sesquiterpenoid</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.14</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(6R)-6-[(1R,3aS,5Z,7aS)-5-{2-[(1Z,5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-1,2-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>416.6365</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>416.329045274</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@]([H])([C@H](C)CCCC(C)(O)CO)[C@@]1(C)CC\C(C2)=C\C=C1\C[C@@H](O)CCC1=C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H44O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H44O3/c1-19-7-11-24(29)17-22(19)9-8-21-13-15-27(4)23(16-21)10-12-25(27)20(2)6-5-14-26(3,30)18-28/h8-9,20,23-25,28-30H,1,5-7,10-18H2,2-4H3/b21-8-,22-9-/t20-,23+,24+,25-,26?,27+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WWGCQHXFACVYPT-JKVVTCAUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>126.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>52.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327180</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021794</foodb_id>
  <kegg_id/>
  <chemspider_id/>
  <drugbank_id/>
  <pubchem_compound_id>53477727</pubchem_compound_id>
  <chebi_id>89079</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:42 UTC</creation_date>
  <update_date>2020-03-13 16:27:56 UTC</update_date>
  <accession>BMDB0001421</accession>
  <secondary_accessions>
    <accession>BMDB01421</accession>
  </secondary_accessions>
  <name>4,4-Dimethyl-14a-formyl-5a-cholesta-8,24-dien-3b-ol</name>
  <description/>
  <synonyms>
    <synonym>4,4-Dimethyl-14-alpha-formyl-5-alpha-cholesta-8,24-dien-3-beta-ol</synonym>
    <synonym>32-Ketolanosterol</synonym>
    <synonym>32-Oxolanosterol</synonym>
  </synonyms>
  <chemical_formula>C30H48O2</chemical_formula>
  <average_molecular_weight>440.7009</average_molecular_weight>
  <monisotopic_moleculate_weight>440.36543078</monisotopic_moleculate_weight>
  <iupac_name>(2S,5S,11S,14R,15R)-5-hydroxy-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-11-carbaldehyde</iupac_name>
  <traditional_iupac>(2S,5S,11S,14R,15R)-5-hydroxy-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-11-carbaldehyde</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@]1(CC[C@@]2(C=O)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)C1CC3)[C@H](C)CCC=C(C)C</smiles>
  <inchi>InChI=1S/C30H48O2/c1-20(2)9-8-10-21(3)22-14-18-30(19-31)24-11-12-25-27(4,5)26(32)15-16-28(25,6)23(24)13-17-29(22,30)7/h9,19,21-22,25-26,32H,8,10-18H2,1-7H3/t21-,22-,25?,26+,28-,29-,30-/m1/s1</inchi>
  <inchikey>PGGIMLIQOHYFIS-DHVLVQQASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Triterpenoids</sub_class>
    <direct_parent>Triterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Aldehydes</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Steroid</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,5S,11S,14R,15R)-5-hydroxy-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-ene-11-carbaldehyde</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>440.7009</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>440.36543078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2(C=O)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)C1CC3)[C@H](C)CCC=C(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C30H48O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C30H48O2/c1-20(2)9-8-10-21(3)22-14-18-30(19-31)24-11-12-25-27(4,5)26(32)15-16-28(25,6)23(24)13-17-29(22,30)7/h9,19,21-22,25-26,32H,8,10-18H2,1-7H3/t21-,22-,25?,26+,28-,29-,30-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PGGIMLIQOHYFIS-DHVLVQQASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>135.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>55.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>330513</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022612</foodb_id>
  <pubchem_compound_id>133187</pubchem_compound_id>
  <chemspider_id>117524</chemspider_id>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6233</metlin_id>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:43 UTC</creation_date>
  <update_date>2020-03-13 16:27:57 UTC</update_date>
  <accession>BMDB0001422</accession>
  <secondary_accessions>
    <accession>BMDB01422</accession>
  </secondary_accessions>
  <name>3-Hydroxy-N6,N6,N6-trimethyl-L-lysine</name>
  <description>3-Hydroxy-N6,N6,N6-trimethyl-L-lysine belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine exists in all living organisms, ranging from bacteria to humans. 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine participates in a number of enzymatic reactions, within cattle. In particular, 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine and succinic acid can be biosynthesized from N6,N6,N6-trimethyl-L-lysine and oxoglutaric acid through its interaction with the enzyme trimethyllysine dioxygenase, mitochondrial. In addition, 3-Hydroxy-N6,N6,N6-trimethyl-L-lysine can be converted into glycine and 4-trimethylammoniobutanal; which is mediated by the enzyme serine hydroxymethyltransferase, cytosolic. In cattle, 3-hydroxy-N6,N6,N6-trimethyl-L-lysine is involved in the metabolic pathway called carnitine synthesis pathway.</description>
  <synonyms>
    <synonym>3-Hydroxy-N(6),N(6),N(6)-trimethyl-L-lysine</synonym>
    <synonym>3-Hydroxy-N(6),N(6),N(6)-trimethyllysine</synonym>
    <synonym>3-Hydroxy-N6,N6,N6-trimethyl-L-lysin-N6-ium</synonym>
  </synonyms>
  <chemical_formula>C9H21N2O3</chemical_formula>
  <average_molecular_weight>205.2746</average_molecular_weight>
  <monisotopic_moleculate_weight>205.155217548</monisotopic_moleculate_weight>
  <iupac_name>[(5S)-5-amino-5-carboxy-4-hydroxypentyl]trimethylazanium</iupac_name>
  <traditional_iupac>[(5S)-5-amino-5-carboxy-4-hydroxypentyl]trimethylazanium</traditional_iupac>
  <cas_registry_number/>
  <smiles>C[N+](C)(C)CCCC(O)[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C9H20N2O3/c1-11(2,3)6-4-5-7(12)8(10)9(13)14/h7-8,12H,4-6,10H2,1-3H3/p+1/t7?,8-/m0/s1</inchi>
  <inchikey>ZRJHLGYVUCPZNH-MQWKRIRWSA-O</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Medium-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>alpha-amino-acid cation</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(5S)-5-amino-5-carboxy-4-hydroxypentyl]trimethylazanium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>205.2746</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>205.155217548</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)CCCC(O)[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H21N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H20N2O3/c1-11(2,3)6-4-5-7(12)8(10)9(13)14/h7-8,12H,4-6,10H2,1-3H3/p+1/t7?,8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZRJHLGYVUCPZNH-MQWKRIRWSA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>83.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>65.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319062</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022613</foodb_id>
  <kegg_id>C01259</kegg_id>
  <chemspider_id>388565</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>439460</pubchem_compound_id>
  <chebi_id>15786</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>37211</bigg_id>
  <wikipedia_id/>
  <metlin_id>6234</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:44 UTC</creation_date>
  <update_date>2020-04-15 22:31:16 UTC</update_date>
  <accession>BMDB0001423</accession>
  <secondary_accessions>
    <accession>BMDB01423</accession>
  </secondary_accessions>
  <name>Coenzyme A</name>
  <description/>
  <synonyms>
    <synonym>3'-Phosphoadenosine-(5')diphospho(4')pantatheine</synonym>
    <synonym>[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (3R)-3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate</synonym>
    <synonym>CoA</synonym>
    <synonym>CoA-SH</synonym>
    <synonym>CoASH</synonym>
    <synonym>Coenzym a</synonym>
    <synonym>HSCoA</synonym>
    <synonym>Koenzym a</synonym>
    <synonym>[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (3R)-3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphoric acid</synonym>
    <synonym>[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (3R)-3-hydroxy-4-({3-oxo-3-[(2-sulphanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate</synonym>
    <synonym>[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (3R)-3-hydroxy-4-({3-oxo-3-[(2-sulphanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphoric acid</synonym>
    <synonym>a, Coenzyme</synonym>
    <synonym>18-CoA-18-oxo-Dinor-LTB4</synonym>
    <synonym>Acetoacetyl coenzyme A sodium salt</synonym>
    <synonym>CoA Hydrate</synonym>
    <synonym>coenzyme A Hydrate</synonym>
    <synonym>coenzyme A-SH</synonym>
    <synonym>coenzyme ASH</synonym>
    <synonym>Depot-zeel</synonym>
    <synonym>Propionyl CoA</synonym>
    <synonym>Propionyl coenzyme A</synonym>
    <synonym>S-Propanoate</synonym>
    <synonym>S-Propanoate CoA</synonym>
    <synonym>S-Propanoate coenzyme A</synonym>
    <synonym>S-Propanoic acid</synonym>
    <synonym>S-Propionate CoA</synonym>
    <synonym>S-Propionate coenzyme A</synonym>
    <synonym>Zeel</synonym>
    <synonym>Coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C21H36N7O16P3S</chemical_formula>
  <average_molecular_weight>767.534</average_molecular_weight>
  <monisotopic_moleculate_weight>767.115208365</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>coenzyme A</traditional_iupac>
  <cas_registry_number>85-61-0</cas_registry_number>
  <smiles>CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS</smiles>
  <inchi>InChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1</inchi>
  <inchikey>RGJOEKWQDUBAIZ-IBOSZNHHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as coenzyme a and derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Coenzyme A and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>adenosine 3',5'-bisphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>767.534</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>767.115208365</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H36N7O16P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RGJOEKWQDUBAIZ-IBOSZNHHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>346.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>162.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>65.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>72687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218126</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022614</foodb_id>
  <kegg_id>C00010</kegg_id>
  <chemspider_id/>
  <drugbank_id>DB01992</drugbank_id>
  <pubchem_compound_id>87642</pubchem_compound_id>
  <chebi_id>15346</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007258</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Coenzyme_A</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:45 UTC</creation_date>
  <update_date>2020-03-13 16:27:58 UTC</update_date>
  <accession>BMDB0001424</accession>
  <secondary_accessions>
    <accession>BMDB01424</accession>
  </secondary_accessions>
  <name>4-(3-Pyridyl)-3-butenoic acid</name>
  <description/>
  <synonyms>
    <synonym>4-(3-Pyridyl)-3-butenoate</synonym>
    <synonym>(3E)-4-(Pyridin-3-yl)but-3-enoate</synonym>
  </synonyms>
  <chemical_formula>C9H9NO2</chemical_formula>
  <average_molecular_weight>163.1733</average_molecular_weight>
  <monisotopic_moleculate_weight>163.063328537</monisotopic_moleculate_weight>
  <iupac_name>(3E)-4-(pyridin-3-yl)but-3-enoic acid</iupac_name>
  <traditional_iupac>4-(3-pyridyl)-3-butenoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>OC(=O)C\C=C\C1=CN=CC=C1</smiles>
  <inchi>InChI=1S/C9H9NO2/c11-9(12)5-1-3-8-4-2-6-10-7-8/h1-4,6-7H,5H2,(H,11,12)/b3-1+</inchi>
  <inchikey>MHVJWSPYMHAALE-HNQUOIGGSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class/>
    <direct_parent>Pyridines and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3E)-4-(pyridin-3-yl)but-3-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>163.1733</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>163.063328537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C\C=C\C1=CN=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H9NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H9NO2/c11-9(12)5-1-3-8-4-2-6-10-7-8/h1-4,6-7H,5H2,(H,11,12)/b3-1+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MHVJWSPYMHAALE-HNQUOIGGSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>50.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>355341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38068</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB022615</foodb_id>
  <pubchem_compound_id>5478892</pubchem_compound_id>
  <chemspider_id>17216119</chemspider_id>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6236</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:47 UTC</creation_date>
  <update_date>2020-04-16 20:38:00 UTC</update_date>
  <accession>BMDB0001425</accession>
  <secondary_accessions>
    <accession>BMDB01425</accession>
  </secondary_accessions>
  <name>Estrone sulfate</name>
  <description>Estrone sulfate, also known as evex or conestoral, belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. Estrone sulfate exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Estrone sulfate exists in all living organisms, ranging from bacteria to humans. Estrone sulfate and adenosine 3',5'-diphosphate can be biosynthesized from estrone and phosphoadenosine phosphosulfate through its interaction with the enzyme estrogen sulfotransferase. In cattle, estrone sulfate is involved in the metabolic pathway called the estrone metabolism pathway.</description>
  <synonyms>
    <synonym>3-Hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulphate</synonym>
    <synonym>Estrone hydrogen sulfate</synonym>
    <synonym>Estrone sulphate</synonym>
    <synonym>3-Hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulfate</synonym>
    <synonym>3-Hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulfuric acid</synonym>
    <synonym>3-Hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulphuric acid</synonym>
    <synonym>Estrone hydrogen sulfuric acid</synonym>
    <synonym>Estrone hydrogen sulphate</synonym>
    <synonym>Estrone hydrogen sulphuric acid</synonym>
    <synonym>Estrone sulfuric acid</synonym>
    <synonym>Estrone sulphuric acid</synonym>
    <synonym>Conestoral</synonym>
    <synonym>Estrogenic substances</synonym>
    <synonym>Estrone</synonym>
    <synonym>Estrone  hydrogen sulfate</synonym>
    <synonym>Estrone  hydrogen sulphate</synonym>
    <synonym>Estrone 3-sulfate</synonym>
    <synonym>Estrone 3-sulphate</synonym>
    <synonym>Estrone sulfate sodium</synonym>
    <synonym>Estrone sulphate sodium</synonym>
    <synonym>Estrone-3-sulfate</synonym>
    <synonym>Estrone-3-sulphate</synonym>
    <synonym>Premarin</synonym>
    <synonym>Sodium estrone 3-monosulfate</synonym>
    <synonym>Sodium estrone 3-monosulphate</synonym>
    <synonym>Sodium estrone 3-sulfate</synonym>
    <synonym>Sodium estrone 3-sulphate</synonym>
    <synonym>Estrone sulfate, sodium salt</synonym>
    <synonym>Potassium estrone sulfate</synonym>
    <synonym>Sodium estrone sulfate</synonym>
    <synonym>Estrone sulfate, ammonium salt</synonym>
    <synonym>Oestrone sulphate</synonym>
    <synonym>Evex</synonym>
    <synonym>Estrone sulfate, 16-(14)C-labeled</synonym>
    <synonym>Estrone sulfate, 14C-labeled</synonym>
    <synonym>Estrone sulfate, potassium salt</synonym>
  </synonyms>
  <chemical_formula>C18H22O5S</chemical_formula>
  <average_molecular_weight>350.429</average_molecular_weight>
  <monisotopic_moleculate_weight>350.118794504</monisotopic_moleculate_weight>
  <iupac_name>[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl]oxidanesulfonic acid</iupac_name>
  <traditional_iupac>Ogen</traditional_iupac>
  <cas_registry_number>481-97-0</cas_registry_number>
  <smiles>C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(OS(O)(=O)=O)=C4)[C@@H]1CCC2=O</smiles>
  <inchi>InChI=1S/C18H22O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,18+/m1/s1</inchi>
  <inchikey>JKKFKPJIXZFSSB-CBZIJGRNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Sulfated steroids</sub_class>
    <direct_parent>Sulfated steroids</direct_parent>
    <alternative_parents>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>Arylsulfates</alternative_parent>
      <alternative_parent>Estrane steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenanthrenes and derivatives</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
      <alternative_parent>Tetralins</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>17-oxosteroid</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Arylsulfate</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Estrane-skeleton</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Phenanthrene</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfated steroid skeleton</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
      <substituent>Tetralin</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>17-oxo steroid</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>C18 steroids (estrogens) and derivatives</external_descriptor>
      <external_descriptor>Estrogens</external_descriptor>
      <external_descriptor>steroid sulfate</external_descriptor>
      <external_descriptor>sulfates</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>254.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl]oxidanesulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>350.429</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>350.118794504</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(OS(O)(=O)=O)=C4)[C@@H]1CCC2=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H22O5S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H22O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,18+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JKKFKPJIXZFSSB-CBZIJGRNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>89.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Androgen and Estrogen Metabolism</name>
      <smpdb_id>SMP0087251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Estrone Metabolism</name>
      <smpdb_id>SMP0087272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sulfate/Sulfite Metabolism</name>
      <smpdb_id>SMP0087216</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>159834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>159835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>159836</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000582 +/- 0.000002854</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk with 0% fat</comment>
      <references>
        <reference>
          <reference_text>Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024.  Epub 2010 May 25.</reference_text>
          <pubmed_id>20541211</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000588 +/- 0.00003995</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk with 0% fat</comment>
      <references>
        <reference>
          <reference_text>Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024.  Epub 2010 May 25.</reference_text>
          <pubmed_id>20541211</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000574 +/- 0.00005137</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial whole milk with 3.3.% fat</comment>
      <references>
        <reference>
          <reference_text>Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024.  Epub 2010 May 25.</reference_text>
          <pubmed_id>20541211</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000665 +/- 0.0000371</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial whole milk with 3.3.% fat</comment>
      <references>
        <reference>
          <reference_text>Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024.  Epub 2010 May 25.</reference_text>
          <pubmed_id>20541211</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000648 +/- 0.000005707</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Organic, Commercial, whole 3.3% fat</comment>
      <references>
        <reference>
          <reference_text>Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024.  Epub 2010 May 25.</reference_text>
          <pubmed_id>20541211</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.000685 +/- 0.00003139</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Organic, Commercial, whole 3.3% fat</comment>
      <references>
        <reference>
          <reference_text>Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024.  Epub 2010 May 25.</reference_text>
          <pubmed_id>20541211</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C02538</kegg_id>
  <drugbank_id>DB04574</drugbank_id>
  <foodb_id>FDB021804</foodb_id>
  <pubchem_compound_id>3001028</pubchem_compound_id>
  <chemspider_id>2272513</chemspider_id>
  <chebi_id>17474</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Estrone sulfate</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>40054</bigg_id>
  <metlin_id>3556</metlin_id>
  <synthesis_reference>Price, Wm. H. Process for the production of alkali metal estrone sulfate salts. (1959), US Patent 2917522 19591215</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024.  Epub 2010 May 25.</reference_text>
      <pubmed_id>20541211</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00378</protein_accession>
      <name>Estrogen sulfotransferase</name>
      <uniprot_id>P19217</uniprot_id>
      <gene_name>SULT1E1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00606</protein_accession>
      <name>Hydroxysteroid 17-beta dehydrogenase 6</name>
      <uniprot_id>Q3T001</uniprot_id>
      <gene_name>HSD17B6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00927</protein_accession>
      <name>Estradiol 17-beta-dehydrogenase 12</name>
      <uniprot_id>Q5E9H7</uniprot_id>
      <gene_name>HSD17B12</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:48 UTC</creation_date>
  <update_date>2020-04-16 20:40:06 UTC</update_date>
  <accession>BMDB0001426</accession>
  <secondary_accessions>
    <accession>BMDB01426</accession>
  </secondary_accessions>
  <name>Formaldehyde</name>
  <description>Formaldehydee, also known as formaldehyde or formaldehyde, belongs to the class of organic compounds known as carbonyl compounds. These are organic compounds containing a carbonyl group, with the general structure RC(=O)R', where R=organyl, R'=H, N, O, organyl group or halide group. Formaldehydee exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Formaldehydee exists in all living species, ranging from bacteria to humans. Formaldehydee participates in a number of enzymatic reactions, within cattle. In particular, Paraxanthine and formaldehydee can be biosynthesized from caffeine through its interaction with the enzyme cytochrome P450 1A2. In addition, Theobromine and formaldehydee can be biosynthesized from caffeine; which is catalyzed by the enzymes cytochrome P450 1A2 and cytochrome P450 2E1. In cattle, formaldehydee is involved in the metabolic pathway called the caffeine metabolism pathway. Formaldehydee is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound.</description>
  <synonyms>
    <synonym>Formaldehyd</synonym>
    <synonym>FORMALIN</synonym>
    <synonym>Methanal</synonym>
    <synonym>Methylene oxide</synonym>
    <synonym>Oxomethane</synonym>
    <synonym>Oxomethylene</synonym>
    <synonym>Hyperband</synonym>
    <synonym>Methaldehyde</synonym>
    <synonym>Methylene glycol</synonym>
    <synonym>Aldeide formica</synonym>
    <synonym>Fannoform</synonym>
    <synonym>Formalina</synonym>
    <synonym>Formaline</synonym>
    <synonym>Formalith</synonym>
    <synonym>Formic aldehyde</synonym>
    <synonym>Formol</synonym>
    <synonym>Paraform</synonym>
  </synonyms>
  <chemical_formula>CH2O</chemical_formula>
  <average_molecular_weight>30.026</average_molecular_weight>
  <monisotopic_moleculate_weight>30.010564686</monisotopic_moleculate_weight>
  <iupac_name>formaldehyde</iupac_name>
  <traditional_iupac>formaldehyde</traditional_iupac>
  <cas_registry_number>50-00-0</cas_registry_number>
  <smiles>C=O</smiles>
  <inchi>InChI=1S/CH2O/c1-2/h1H2</inchi>
  <inchikey>WSFSSNUMVMOOMR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as carbonyl compounds. These are organic compounds containing a carbonyl group, with the general structure RC(=O)R', where R=organyl, R'=H, N, O, organyl group or halide group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Carbonyl compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aldehyde</external_descriptor>
      <external_descriptor>an &lt;i&gt;n&lt;/i&gt;-alkanal</external_descriptor>
      <external_descriptor>one-carbon compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-92 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>400 mg/mL at 20 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.35</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-8.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>formaldehyde</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>30.026</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>30.010564686</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>CH2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/CH2O/c1-2/h1H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WSFSSNUMVMOOMR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>6.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>2.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Caffeine Metabolism</name>
      <smpdb_id>SMP0087186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4842</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00067</kegg_id>
  <drugbank_id>DB03843</drugbank_id>
  <foodb_id>FDB009445</foodb_id>
  <pubchem_compound_id>712</pubchem_compound_id>
  <chemspider_id>692</chemspider_id>
  <chebi_id>16842</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id>FORMALDEHYDE</meta_cyc_id>
  <wikipedia_id>Formaldehyde</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33726</bigg_id>
  <metlin_id>3198</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00895</protein_accession>
      <name>Peroxisomal sarcosine oxidase</name>
      <uniprot_id>Q29RU9</uniprot_id>
      <gene_name>PIPOX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:49 UTC</creation_date>
  <update_date>2020-04-15 22:15:18 UTC</update_date>
  <accession>BMDB0001427</accession>
  <secondary_accessions>
    <accession>BMDB01427</accession>
  </secondary_accessions>
  <name>5'-Hydroxycotinine</name>
  <description/>
  <synonyms>
    <synonym>5-Hydroxycotinine</synonym>
    <synonym>Allohydroxycotinine</synonym>
  </synonyms>
  <chemical_formula>C10H12N2O2</chemical_formula>
  <average_molecular_weight>192.2145</average_molecular_weight>
  <monisotopic_moleculate_weight>192.089877638</monisotopic_moleculate_weight>
  <iupac_name>(5R)-5-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one</iupac_name>
  <traditional_iupac>5-hydroxycotinine</traditional_iupac>
  <cas_registry_number>61192-50-5</cas_registry_number>
  <smiles>CN1C(=O)CC[C@@]1(O)C1=CN=CC=C1</smiles>
  <inchi>InChI=1S/C10H12N2O2/c1-12-9(13)4-5-10(12,14)8-3-2-6-11-7-8/h2-3,6-7,14H,4-5H2,1H3/t10-/m1/s1</inchi>
  <inchikey>BBNHNZGTKSWIHD-SNVBAGLBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyrrolidinylpyridines</sub_class>
    <direct_parent>Pyrrolidinylpyridines</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Alkanolamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>N-alkylpyrrolidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrrolidine-2-ones</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-pyrrolidone</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Alkanolamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>N-alkylpyrrolidine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidinylpyridine</substituent>
      <substituent>Pyrrolidone</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5R)-5-hydroxy-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>192.2145</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>192.089877638</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C(=O)CC[C@@]1(O)C1=CN=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12N2O2/c1-12-9(13)4-5-10(12,14)8-3-2-6-11-7-8/h2-3,6-7,14H,4-5H2,1H3/t10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BBNHNZGTKSWIHD-SNVBAGLBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>53.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17990</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349353</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB022616</foodb_id>
  <pubchem_compound_id>9815515</pubchem_compound_id>
  <chemspider_id>7991265</chemspider_id>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6239</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:50 UTC</creation_date>
  <update_date>2020-04-14 22:49:13 UTC</update_date>
  <accession>BMDB0001429</accession>
  <secondary_accessions>
    <accession>BMDB01429</accession>
  </secondary_accessions>
  <name>Phosphate</name>
  <description>Phosphoric acid, also known as phosphate or [po(OH)3], belongs to the class of inorganic compounds known as non-metal phosphates. These are inorganic non-metallic compounds containing a phosphate as its largest oxoanion. Phosphoric acid exists as a solid, possibly soluble (in water), and a moderately acidic compound (based on its pKa) molecule. Phosphoric acid exists in all living species, ranging from bacteria to humans. Phosphoric acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>[PO(OH)3]</synonym>
    <synonym>Acide phosphorique</synonym>
    <synonym>Acidum phosphoricum</synonym>
    <synonym>H3PO4</synonym>
    <synonym>Orthophosphoric acid</synonym>
    <synonym>Phosphorsaeureloesungen</synonym>
    <synonym>Phosphorsaeure</synonym>
    <synonym>Phosphoric acid</synonym>
    <synonym>Orthophosphate</synonym>
    <synonym>Phosphate</synonym>
    <synonym>Diphosphate tetrasodium</synonym>
    <synonym>Marphos</synonym>
    <synonym>NFB</synonym>
    <synonym>ortho- Phosphoric acid</synonym>
    <synonym>Phosphoric acid (acd/name 4.0)</synonym>
    <synonym>Sodium pyrophosphate</synonym>
    <synonym>Sodium pyrophosphate decahydrate</synonym>
    <synonym>Sodium pyrophosphate decahydrate biochemica</synonym>
    <synonym>Sonac</synonym>
    <synonym>Tetra-sodium pyrophosphate</synonym>
    <synonym>Tetrasodium pyrophosphate 10-hydrate</synonym>
    <synonym>Tetrasodium pyrophosphate decahydrate</synonym>
    <synonym>White phosphoric acid</synonym>
    <synonym>K-Etchant</synonym>
    <synonym>Uni-etch</synonym>
    <synonym>Concise etchant</synonym>
    <synonym>Condact</synonym>
    <synonym>Hydrogen phosphoric acid</synonym>
    <synonym>Dihydrogen phosphate</synonym>
    <synonym>Hydrogen phosphate</synonym>
  </synonyms>
  <chemical_formula>H3O4P</chemical_formula>
  <average_molecular_weight>97.9952</average_molecular_weight>
  <monisotopic_moleculate_weight>97.976895096</monisotopic_moleculate_weight>
  <iupac_name>phosphoric acid</iupac_name>
  <traditional_iupac>phosphoric acid</traditional_iupac>
  <cas_registry_number>7664-38-2</cas_registry_number>
  <smiles>OP(O)(O)=O</smiles>
  <inchi>InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)</inchi>
  <inchikey>NBIIXXVUZAFLBC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as non-metal phosphates. These are inorganic non-metallic compounds containing a phosphate as its largest oxoanion.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Non-metal oxoanionic compounds</class>
    <sub_class>Non-metal phosphates</sub_class>
    <direct_parent>Non-metal phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Inorganic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Inorganic oxide</substituent>
      <substituent>Non-metal phosphate</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>phosphoric acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>phosphoric acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>97.9952</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>97.976895096</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>H3O4P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NBIIXXVUZAFLBC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>14.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>5.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Activation of cAMP-dependent protein kinase, PKA</name>
      <smpdb_id>SMP0108201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Amino Sugar Metabolism</name>
      <smpdb_id>SMP0087175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>BCR Signaling Pathway</name>
      <smpdb_id>SMP0120940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Betaine Metabolism</name>
      <smpdb_id>SMP0087182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>BTG Family Proteins and Cell Cycle Regulation</name>
      <smpdb_id>SMP0108205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cadmium Induces DNA Synthesis and Proliferation in Macrophages </name>
      <smpdb_id>SMP0108212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis</name>
      <smpdb_id>SMP0072032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:0)</name>
      <smpdb_id>SMP0077151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:0)</name>
      <smpdb_id>SMP0077153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:0)</name>
      <smpdb_id>SMP0077171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:0)</name>
      <smpdb_id>SMP0077173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077198</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077199</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077200</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077201</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077205</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077206</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077207</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077208</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077209</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077210</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077211</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077212</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077213</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077214</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077215</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077216</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077217</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077218</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077219</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077220</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077221</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077222</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077223</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077224</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077225</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077226</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077227</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077228</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077229</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077230</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077231</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077232</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077233</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077234</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077235</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077237</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077238</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077239</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077240</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077241</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077242</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077243</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077244</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077245</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077246</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077247</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077248</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077249</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077250</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077251</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077253</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077254</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077255</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077256</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077257</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077258</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077259</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077260</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077265</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077266</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077267</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077268</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077269</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077279</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077281</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077282</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077283</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077284</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077285</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077286</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077287</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077288</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077289</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077290</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077291</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077292</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077293</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077294</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077295</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077296</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077297</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077298</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:0)</name>
      <smpdb_id>SMP0077299</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077300</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077301</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077302</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077303</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077304</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077305</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077306</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077307</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077308</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077309</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:0)</name>
      <smpdb_id>SMP0077310</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077311</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:0)</name>
      <smpdb_id>SMP0077312</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077313</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077314</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077315</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077316</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077317</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077318</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077319</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077320</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077321</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077322</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077323</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077324</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077325</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077326</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077327</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077328</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077329</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077330</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077331</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077332</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077333</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077334</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077335</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077336</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077337</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077338</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077339</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077340</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077341</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077342</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077343</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077344</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077345</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077346</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077347</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077348</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077349</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077350</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077351</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077352</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077353</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077354</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077355</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077356</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077357</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077358</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077359</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077360</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077361</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077363</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077364</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077365</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077366</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077367</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077368</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077369</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077370</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077371</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077372</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077373</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077374</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077375</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077376</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077377</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077378</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077379</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077380</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077381</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077382</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077383</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077384</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077385</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077386</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077387</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077388</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077389</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077390</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077391</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077392</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077393</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077394</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077395</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077396</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077397</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077398</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077399</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077400</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077402</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077403</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077404</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077405</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077406</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077407</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077408</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077409</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077410</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077411</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077412</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077413</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077414</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077415</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077416</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077417</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077418</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077419</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077420</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077421</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077422</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077423</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077424</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077425</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077426</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077427</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077428</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077429</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077430</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077431</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077432</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077433</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077434</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077435</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077436</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077437</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077438</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077439</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077440</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077441</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077442</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077443</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077444</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077445</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077446</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077447</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077448</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077449</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077450</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077451</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077452</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077453</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077454</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077455</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077456</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077457</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077459</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077460</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077461</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077462</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077463</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077464</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077465</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077466</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077470</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077471</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077472</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077474</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077475</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077476</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077477</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077478</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077479</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077480</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077481</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077482</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077483</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077484</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077485</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077486</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077487</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077488</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077489</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077490</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077491</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077492</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077493</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077494</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077495</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077496</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077497</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077498</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077499</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077500</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077501</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077502</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077503</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077504</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077505</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077506</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077507</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077508</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077509</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077510</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077511</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077512</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077513</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077514</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077515</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077516</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077517</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077518</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077519</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077520</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077521</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077522</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077523</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077524</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077525</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077526</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077527</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077528</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077529</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077530</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077531</smpdb_id>
      <kegg_map_id/>
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    <pathway>
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      <smpdb_id>SMP0077532</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077603</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077604</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077606</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077608</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077609</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077679</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077680</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077681</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077682</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077688</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077689</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077690</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077691</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077692</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077693</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077694</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077695</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077696</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077697</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077698</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077699</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077700</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077701</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077702</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077703</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077704</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077705</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077706</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077707</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077708</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077709</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077710</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077723</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077724</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077725</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077726</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077730</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077731</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077732</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077733</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077734</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077735</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077736</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077741</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077742</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077743</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077744</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077745</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077746</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077747</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077749</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077750</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077751</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077752</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077753</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077754</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077755</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077756</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077757</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077758</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077760</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077761</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077762</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077763</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077766</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077802</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077835</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077836</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077837</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077838</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077839</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077840</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077841</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077842</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077844</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077845</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077846</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077847</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077848</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077849</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077850</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077851</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077853</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077854</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077855</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077856</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077857</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077858</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077859</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077860</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077861</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077862</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077863</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077864</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077865</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077866</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077867</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077868</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077869</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077870</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077871</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077872</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077873</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077874</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077875</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077876</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077877</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077878</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077879</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077880</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077881</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077882</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077883</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077884</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077885</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077886</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077887</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077888</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077889</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077890</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077891</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077892</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077893</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077894</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077895</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077896</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077897</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077898</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077899</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077900</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077901</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077902</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077903</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077904</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077905</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077906</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077907</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077908</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077909</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077910</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077911</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077912</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077913</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077914</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077915</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077916</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077917</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077918</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077920</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077921</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077922</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077925</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077926</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077929</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077930</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077932</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077933</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077934</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077935</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077936</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077937</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077938</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077939</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077940</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077941</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077942</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077943</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077944</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077945</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077947</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077948</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077950</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077951</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077953</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:0)</name>
      <smpdb_id>SMP0078219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078284</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078285</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078287</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078304</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078305</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078306</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078307</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078308</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078309</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078310</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078311</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078312</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078313</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078314</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078315</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078316</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078317</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078318</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078319</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078320</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078321</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078322</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078323</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078324</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078325</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078326</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078327</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078328</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078329</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078330</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078331</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078332</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078333</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078334</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078335</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078350</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078351</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078352</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078353</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078354</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078355</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078356</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078357</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078358</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078359</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078360</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078361</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078362</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078363</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078364</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078365</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078366</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078370</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078371</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078372</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078373</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078374</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078375</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078376</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078377</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078378</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078379</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078380</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078381</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078382</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078383</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078384</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078385</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078386</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078387</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078388</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078389</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078390</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078391</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078394</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078395</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078396</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078398</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078399</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078400</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078401</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078404</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078407</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078408</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078423</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078424</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078425</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078426</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078427</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078428</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078429</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078430</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078431</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078432</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078433</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078434</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078435</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078436</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078437</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078438</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078439</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078440</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078441</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078443</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078444</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078445</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078446</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078447</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078448</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078449</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078450</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078451</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078452</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078453</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078454</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078457</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078458</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078460</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078461</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078462</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078463</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078464</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078465</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078466</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078467</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078468</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078475</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078493</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078542</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078611</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078612</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078613</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078614</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078615</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078616</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078617</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078618</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078619</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078620</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078621</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078622</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078623</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078624</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078625</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078626</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078627</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078628</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078629</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078630</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078631</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078632</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078633</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078634</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078635</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078636</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078637</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078638</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078639</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078640</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078641</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078642</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078643</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078644</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078645</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078646</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078647</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078648</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078649</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078650</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078652</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078654</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078655</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078656</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078657</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078658</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078659</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078660</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078661</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078662</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078663</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078664</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078665</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078666</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078667</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078668</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078669</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078670</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078671</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078672</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078673</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078674</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078675</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078676</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078677</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078678</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078679</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078680</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078681</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078682</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078683</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078684</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078685</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078686</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078687</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078688</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078689</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078690</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078692</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078693</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078694</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078696</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078697</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078698</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078699</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078700</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078701</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078702</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078703</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078704</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078705</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078706</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078707</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078708</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078709</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078710</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078711</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078712</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078713</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078714</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078715</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078717</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078718</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078719</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078723</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078738</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078744</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078745</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078746</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078747</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078748</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078749</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078754</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078755</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078756</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078757</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078758</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078774</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078775</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078776</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078777</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078778</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078779</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078780</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078781</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078782</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078783</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078784</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078785</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078786</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078787</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078788</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078789</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078790</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078791</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078792</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078793</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078794</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078795</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078796</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078797</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078798</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078799</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078800</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078801</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078802</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078803</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078804</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078805</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078806</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078807</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078808</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078809</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078810</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078811</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078812</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078813</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078814</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078815</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078816</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078817</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078818</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078819</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078820</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078821</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078822</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078823</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078824</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078825</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078826</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078827</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078828</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078829</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078830</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078831</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078832</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078833</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078834</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078835</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078837</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078838</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078840</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078841</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078842</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078843</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078844</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078845</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078846</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078847</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078848</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078849</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078850</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078851</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078852</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078853</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078854</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078855</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078856</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078857</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078858</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078859</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078861</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078862</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078864</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078870</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078871</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078872</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078873</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078875</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078876</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078877</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078878</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078879</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078880</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078887</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:0)</name>
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    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0079152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079222</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079223</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079224</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079225</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079226</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079227</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079228</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079229</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079230</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079231</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079232</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079233</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079234</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079235</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079237</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079238</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079240</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079241</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079242</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079243</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079249</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079251</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079252</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079254</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079255</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079258</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079260</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079261</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079262</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079263</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079264</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079265</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079267</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079268</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079269</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079270</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079271</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079272</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079273</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079274</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079275</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079276</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079277</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079278</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079279</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079280</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079281</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079282</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079283</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079284</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079285</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079286</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079287</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079288</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079289</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079290</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079291</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079292</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079293</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079294</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079295</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079297</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079298</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079299</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079300</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079301</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079302</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079303</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079304</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079305</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079306</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079307</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079308</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079309</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079310</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079311</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079312</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079313</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079314</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079315</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079316</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079317</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079318</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079321</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <smpdb_id>SMP0079438</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079440</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079441</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079443</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079444</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079445</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079449</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079450</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079451</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079454</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079464</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079465</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079466</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079467</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079468</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079481</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079485</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079488</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079489</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079490</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079491</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079492</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079500</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079505</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079506</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079507</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079508</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0079603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0079604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079623</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079626</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079627</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079657</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079658</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079659</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079664</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079707</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079709</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079715</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079716</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079717</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079720</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079722</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079723</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079725</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079727</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079729</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079739</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079760</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079761</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079762</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079763</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079768</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079773</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079791</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079792</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079793</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079795</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079796</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079797</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079798</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079799</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079800</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079801</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079802</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079803</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079804</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079805</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079806</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079807</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079808</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079809</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079810</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079811</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079814</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079815</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079817</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079818</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079819</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079820</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079821</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079822</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079823</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079824</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079828</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079830</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079831</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079835</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079836</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079837</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079841</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079842</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079846</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079847</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079851</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079852</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079855</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079856</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079857</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079858</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079988</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080004</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0080018</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080029</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080030</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080032</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080033</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080034</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080039</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080044</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080045</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080046</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080050</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080051</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080052</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080053</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080184</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080228</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080229</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080230</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080234</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080235</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080236</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080237</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080238</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080239</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080240</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080241</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080242</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080243</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080244</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080245</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080246</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080247</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080248</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080249</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080250</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080251</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080252</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080253</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080258</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080262</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080263</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080264</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080265</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080266</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080271</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080275</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080276</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080277</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080288</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080297</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080298</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080299</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080300</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080308</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080309</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>CD40L Signalling Pathway</name>
      <smpdb_id>SMP0120942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Circadian Rhythms</name>
      <smpdb_id>SMP0119382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>CXCR4 Signaling Pathway</name>
      <smpdb_id>SMP0120933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis</name>
      <smpdb_id>SMP0071338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/10:0)</name>
      <smpdb_id>SMP0108241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/12:0)</name>
      <smpdb_id>SMP0108483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/13:0)</name>
      <smpdb_id>SMP0108481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/14:0)</name>
      <smpdb_id>SMP0108477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/15:0)</name>
      <smpdb_id>SMP0108517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/16:0)</name>
      <smpdb_id>SMP0108480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/17:0)</name>
      <smpdb_id>SMP0108472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/18:0)</name>
      <smpdb_id>SMP0108485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/19:0)</name>
      <smpdb_id>SMP0108526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/8:0)</name>
      <smpdb_id>SMP0108478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-13:0)</name>
      <smpdb_id>SMP0108541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-15:0)</name>
      <smpdb_id>SMP0108542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-17:0)</name>
      <smpdb_id>SMP0108543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-21:0)</name>
      <smpdb_id>SMP0108544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-25:0)</name>
      <smpdb_id>SMP0108545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-12:0)</name>
      <smpdb_id>SMP0108546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-13:0)</name>
      <smpdb_id>SMP0108547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-14:0)</name>
      <smpdb_id>SMP0108548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-15:0)</name>
      <smpdb_id>SMP0108549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-16:0)</name>
      <smpdb_id>SMP0108550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-17:0)</name>
      <smpdb_id>SMP0108551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-18:0)</name>
      <smpdb_id>SMP0108552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-19:0)</name>
      <smpdb_id>SMP0108553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-20:0)</name>
      <smpdb_id>SMP0108554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-21:0)</name>
      <smpdb_id>SMP0108555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-22:0)</name>
      <smpdb_id>SMP0108556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-24:0)</name>
      <smpdb_id>SMP0108557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/12:0)</name>
      <smpdb_id>SMP0108470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/13:0)</name>
      <smpdb_id>SMP0108512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/14:0)</name>
      <smpdb_id>SMP0108445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/15:0)</name>
      <smpdb_id>SMP0108471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0108558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0108559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0108560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0108561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0108562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0108563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0108564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0108565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0108566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0108567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0108568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0108569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0108570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0108571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0108572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0108573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0108574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/13:0)</name>
      <smpdb_id>SMP0108460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/15:0)</name>
      <smpdb_id>SMP0108469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/16:0)</name>
      <smpdb_id>SMP0108463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/8:0)</name>
      <smpdb_id>SMP0108451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0108575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0108576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0108577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0108578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0108579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0108580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0108581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0108582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0108583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0108584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0108585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0108586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0108587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0108588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0108589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0108590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0108591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/13:0)</name>
      <smpdb_id>SMP0108534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/14:0)</name>
      <smpdb_id>SMP0108525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/15:0)</name>
      <smpdb_id>SMP0108522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/17:0)</name>
      <smpdb_id>SMP0108488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/18:0)</name>
      <smpdb_id>SMP0108489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/19:0)</name>
      <smpdb_id>SMP0108447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0108592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0108593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0108594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0108595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0108596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0108597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0108598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0108599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0108600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0108601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0108602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0108603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0108604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0108605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0108606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0108607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0108608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/15:0)</name>
      <smpdb_id>SMP0108476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/17:0)</name>
      <smpdb_id>SMP0108461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/18:0)</name>
      <smpdb_id>SMP0108523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/8:0)</name>
      <smpdb_id>SMP0108494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0108609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0108610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0108611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0108612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0108613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0108614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0108615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0108616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0108617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0108618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0108619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0108620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0108621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0108622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0108623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0108624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0108625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/12:0)</name>
      <smpdb_id>SMP0108479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/14:0)</name>
      <smpdb_id>SMP0108468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/15:0)</name>
      <smpdb_id>SMP0108507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/16:0)</name>
      <smpdb_id>SMP0108467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/17:0)</name>
      <smpdb_id>SMP0108458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/18:0)</name>
      <smpdb_id>SMP0108518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/8:0)</name>
      <smpdb_id>SMP0108504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0108626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0108627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0108628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0108629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0108630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0108631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0108632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0108633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0108634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0108635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0108636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0108637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0108638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0108639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0108640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0108641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0108642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/12:0)</name>
      <smpdb_id>SMP0108465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/13:0)</name>
      <smpdb_id>SMP0108456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/17:0)</name>
      <smpdb_id>SMP0108506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0108643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0108644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0108645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0108646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0108647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0108648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0108649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0108650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0108651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0108652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0108653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0108654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0108655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0108656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0108657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0108658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0108659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/12:0)</name>
      <smpdb_id>SMP0108495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/13:0)</name>
      <smpdb_id>SMP0108492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/17:0)</name>
      <smpdb_id>SMP0108452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/18:0)</name>
      <smpdb_id>SMP0108448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/19:0)</name>
      <smpdb_id>SMP0108503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/8:0)</name>
      <smpdb_id>SMP0108466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0108660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0108661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0108662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0108663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0108664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0108665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0108666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0108667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0108668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0108669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0108670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0108671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0108672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0108673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0108674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0108675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0108676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/12:0)</name>
      <smpdb_id>SMP0108511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/13:0)</name>
      <smpdb_id>SMP0108473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/15:0)</name>
      <smpdb_id>SMP0108533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/16:0)</name>
      <smpdb_id>SMP0108496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/17:0)</name>
      <smpdb_id>SMP0108521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/19:0)</name>
      <smpdb_id>SMP0108514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0108677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0108678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0108679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-21:0)</name>
      <smpdb_id>SMP0108680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-25:0)</name>
      <smpdb_id>SMP0108681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0108682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0108683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0108684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0108685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0108686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0108687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0108688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0108689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-20:0)</name>
      <smpdb_id>SMP0108690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-21:0)</name>
      <smpdb_id>SMP0108691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-22:0)</name>
      <smpdb_id>SMP0108692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-24:0)</name>
      <smpdb_id>SMP0108693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-13:0)</name>
      <smpdb_id>SMP0108694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-15:0)</name>
      <smpdb_id>SMP0108695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-17:0)</name>
      <smpdb_id>SMP0108696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0108697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0108698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-12:0)</name>
      <smpdb_id>SMP0108699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-13:0)</name>
      <smpdb_id>SMP0108700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-14:0)</name>
      <smpdb_id>SMP0108701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-15:0)</name>
      <smpdb_id>SMP0108702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-16:0)</name>
      <smpdb_id>SMP0108703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-17:0)</name>
      <smpdb_id>SMP0108704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-18:0)</name>
      <smpdb_id>SMP0108705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0108706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0108707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0108708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0108709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0108710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0108711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0108712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0108713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0108714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0108715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0108716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0108717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0108718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0108719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0108720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0108721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0108722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0108723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0108724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0108725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0108726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0108727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0108728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0108729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0108730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0108731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0108732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0108733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0108734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0108735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0108736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0108737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0108738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0108739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0108740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0108741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0108742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0108743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0108744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/17:0)</name>
      <smpdb_id>SMP0108457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/8:0)</name>
      <smpdb_id>SMP0108519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0108745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0108746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0108747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0108748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0108749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0108750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0108751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0108752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0108753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0108754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0108755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0108756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0108757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0108759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0111848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0108761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0108763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0108765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0108767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0108768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0108770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0108772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0108774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0108775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0108777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0108778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0108779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0108780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0108781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0108782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0108783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0108784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0108785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0108786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0108787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0108788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0108789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0108790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0108791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0108792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0108793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0108794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0108795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0108796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0108797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0108798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0108799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0108800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0108801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0108802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0108803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0108804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0108805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0108806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0108807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0108808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0108809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0108810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0108811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0108812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0108813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0108814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0108815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0108816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0108817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0108818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0108819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0108820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0108821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0108822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0108823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0108824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0108825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0108826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0108827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0108828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0108829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0108830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0108831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0108832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0108833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0108834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0108835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0108836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0108837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0108838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0108839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0108840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0108841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0108842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0108843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0108844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0108845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0108846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0108847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0108848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0108849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0108850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0108851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0108852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0108853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0108854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0108855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0108856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0108857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0108858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0108859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0108860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0108861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0108862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0108863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0108864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0108865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0108866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0108867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0108868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0108869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0108870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0108871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0108872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0108873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0108874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0108875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0108876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0108877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0108878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0108879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0108880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0108881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0108882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0108883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0108884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0108885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0108886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0108887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0108888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0108889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0108890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0108891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0108892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0108893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0108894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0108895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0108896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0108897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0108898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0108899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0108900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0108901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0108902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0108903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0108904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0108905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0108906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0108907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0108908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0108909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0108910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0108911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0108912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/a-25:0)</name>
      <smpdb_id>SMP0108913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0108914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0108915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0108916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/a-25:0)</name>
      <smpdb_id>SMP0108917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0108918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0108919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-24:0/a-25:0)</name>
      <smpdb_id>SMP0108920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0108921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(12:0/12:0/12:0)</name>
      <smpdb_id>SMP0108243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/14:0)</name>
      <smpdb_id>SMP0072652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/14:1(9Z))</name>
      <smpdb_id>SMP0072653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/15:0)</name>
      <smpdb_id>SMP0072654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/16:0)</name>
      <smpdb_id>SMP0072655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/16:1(9Z))</name>
      <smpdb_id>SMP0072656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:0)</name>
      <smpdb_id>SMP0072657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:1(11Z))</name>
      <smpdb_id>SMP0072658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:1(9Z))</name>
      <smpdb_id>SMP0072659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:0)</name>
      <smpdb_id>SMP0072664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:1(11Z))</name>
      <smpdb_id>SMP0072665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:0)</name>
      <smpdb_id>SMP0072672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:1(13Z))</name>
      <smpdb_id>SMP0072673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/24:0)</name>
      <smpdb_id>SMP0072679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/24:1(15Z))</name>
      <smpdb_id>SMP0072680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0072681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0072682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0072683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0072684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0072685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/15:0)</name>
      <smpdb_id>SMP0072709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/16:0)</name>
      <smpdb_id>SMP0072710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/16:1(9Z))</name>
      <smpdb_id>SMP0072711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:0)</name>
      <smpdb_id>SMP0072712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:1(11Z))</name>
      <smpdb_id>SMP0072713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:1(9Z))</name>
      <smpdb_id>SMP0072714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:0)</name>
      <smpdb_id>SMP0072719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:1(11Z))</name>
      <smpdb_id>SMP0072720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:0)</name>
      <smpdb_id>SMP0072727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:1(13Z))</name>
      <smpdb_id>SMP0072728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/24:0)</name>
      <smpdb_id>SMP0072734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/24:1(15Z))</name>
      <smpdb_id>SMP0072735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/16:0)</name>
      <smpdb_id>SMP0072736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0072737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:0)</name>
      <smpdb_id>SMP0072738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0072739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0072740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:0)</name>
      <smpdb_id>SMP0072745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0072746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:0)</name>
      <smpdb_id>SMP0072753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0072754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/24:0)</name>
      <smpdb_id>SMP0072760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0072761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0072762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0072763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:0)</name>
      <smpdb_id>SMP0072787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0072788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0072789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:0)</name>
      <smpdb_id>SMP0072794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0072795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:0)</name>
      <smpdb_id>SMP0072802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0072803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/24:0)</name>
      <smpdb_id>SMP0072809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0072810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0072817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0072825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0072832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0072860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0072868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0072875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0072880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0072888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0072895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0072899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0072907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0072914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0072917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0072925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0072932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:0)</name>
      <smpdb_id>SMP0072934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0072935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:0)</name>
      <smpdb_id>SMP0072942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0072943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/24:0)</name>
      <smpdb_id>SMP0072949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0072950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0072958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0072965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0072973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0072980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0072987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0072994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:0)</name>
      <smpdb_id>SMP0073042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0073043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/24:0)</name>
      <smpdb_id>SMP0073049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0073050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0073057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:0/24:0)</name>
      <smpdb_id>SMP0073084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0073085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0073087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0073088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0073089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/15:0)</name>
      <smpdb_id>SMP0073115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/16:0)</name>
      <smpdb_id>SMP0073116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/16:1(9Z))</name>
      <smpdb_id>SMP0073117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:0)</name>
      <smpdb_id>SMP0073118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:1(11Z))</name>
      <smpdb_id>SMP0073119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:1(9Z))</name>
      <smpdb_id>SMP0073120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:0)</name>
      <smpdb_id>SMP0073125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:1(11Z))</name>
      <smpdb_id>SMP0073126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:0)</name>
      <smpdb_id>SMP0073133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:1(13Z))</name>
      <smpdb_id>SMP0073134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/24:0)</name>
      <smpdb_id>SMP0073140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/24:1(15Z))</name>
      <smpdb_id>SMP0073141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/16:0)</name>
      <smpdb_id>SMP0073142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:0)</name>
      <smpdb_id>SMP0073144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:0)</name>
      <smpdb_id>SMP0073151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:0)</name>
      <smpdb_id>SMP0073159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/24:0)</name>
      <smpdb_id>SMP0073166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0073193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0073194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0073195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:0)</name>
      <smpdb_id>SMP0073200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0073201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:0)</name>
      <smpdb_id>SMP0073208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0073209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/24:0)</name>
      <smpdb_id>SMP0073215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0073216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0073223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:0)</name>
      <smpdb_id>SMP0073340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0073341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:0)</name>
      <smpdb_id>SMP0073348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0073349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/24:0)</name>
      <smpdb_id>SMP0073355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0073356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0073393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0073400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:0)</name>
      <smpdb_id>SMP0073448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0073449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/24:0)</name>
      <smpdb_id>SMP0073455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0073456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0073463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/24:0/24:0)</name>
      <smpdb_id>SMP0073490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0073491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/15:0)</name>
      <smpdb_id>SMP0073493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/16:0)</name>
      <smpdb_id>SMP0073494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/16:1(9Z))</name>
      <smpdb_id>SMP0073495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:0)</name>
      <smpdb_id>SMP0073496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:1(11Z))</name>
      <smpdb_id>SMP0073497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:1(9Z))</name>
      <smpdb_id>SMP0073498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:0)</name>
      <smpdb_id>SMP0073503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:1(11Z))</name>
      <smpdb_id>SMP0073504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:0)</name>
      <smpdb_id>SMP0073511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:1(13Z))</name>
      <smpdb_id>SMP0073512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/24:0)</name>
      <smpdb_id>SMP0073518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/24:1(15Z))</name>
      <smpdb_id>SMP0073519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/16:0)</name>
      <smpdb_id>SMP0073520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:0)</name>
      <smpdb_id>SMP0073522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:0)</name>
      <smpdb_id>SMP0073529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:0)</name>
      <smpdb_id>SMP0073537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/24:0)</name>
      <smpdb_id>SMP0073544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:0)</name>
      <smpdb_id>SMP0073571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0073572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0073573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:0)</name>
      <smpdb_id>SMP0073578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0073579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:0)</name>
      <smpdb_id>SMP0073586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0073587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/24:0)</name>
      <smpdb_id>SMP0073593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0073594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0073601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:0)</name>
      <smpdb_id>SMP0073718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0073719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:0)</name>
      <smpdb_id>SMP0073726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0073727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/24:0)</name>
      <smpdb_id>SMP0073733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0073734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0073771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0073778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:0)</name>
      <smpdb_id>SMP0073826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0073827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/24:0)</name>
      <smpdb_id>SMP0073833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0073834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0073841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/24:0/24:0)</name>
      <smpdb_id>SMP0073868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0073869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:0)</name>
      <smpdb_id>SMP0073871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:0)</name>
      <smpdb_id>SMP0073873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:0)</name>
      <smpdb_id>SMP0073880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:0)</name>
      <smpdb_id>SMP0073888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/24:0)</name>
      <smpdb_id>SMP0073895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:0)</name>
      <smpdb_id>SMP0073922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0073923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0073924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:0)</name>
      <smpdb_id>SMP0073929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0073930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:0)</name>
      <smpdb_id>SMP0073937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0073938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/24:0)</name>
      <smpdb_id>SMP0073944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0073945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0073952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:0)</name>
      <smpdb_id>SMP0074069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:0)</name>
      <smpdb_id>SMP0074077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/24:0)</name>
      <smpdb_id>SMP0074084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0074122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0074129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:0)</name>
      <smpdb_id>SMP0074177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0074178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/24:0)</name>
      <smpdb_id>SMP0074184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0074185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0074192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:0/24:0)</name>
      <smpdb_id>SMP0074219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0074220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0074222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0074223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0074247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0074248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0074249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:0)</name>
      <smpdb_id>SMP0074254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0074255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:0)</name>
      <smpdb_id>SMP0074262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0074263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/24:0)</name>
      <smpdb_id>SMP0074269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0074270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0074277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:0)</name>
      <smpdb_id>SMP0074394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:0)</name>
      <smpdb_id>SMP0074402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/24:0)</name>
      <smpdb_id>SMP0074409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0074447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0074454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:0)</name>
      <smpdb_id>SMP0074502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0074503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/24:0)</name>
      <smpdb_id>SMP0074509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0074510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0074517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/24:0/24:0)</name>
      <smpdb_id>SMP0074544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0074545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:0)</name>
      <smpdb_id>SMP0074547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0074548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0074549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:0)</name>
      <smpdb_id>SMP0074554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0074555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:0)</name>
      <smpdb_id>SMP0074562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0074563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/24:0)</name>
      <smpdb_id>SMP0074569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0074570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0074577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:0)</name>
      <smpdb_id>SMP0074695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:0)</name>
      <smpdb_id>SMP0074703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/24:0)</name>
      <smpdb_id>SMP0074710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0074748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0074756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:0)</name>
      <smpdb_id>SMP0074804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0074805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/24:0)</name>
      <smpdb_id>SMP0074811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0074812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0074819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/24:0/24:0)</name>
      <smpdb_id>SMP0074846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0074847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0074855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:0)</name>
      <smpdb_id>SMP0074972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:0)</name>
      <smpdb_id>SMP0074980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/24:0)</name>
      <smpdb_id>SMP0074988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0075126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0075127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0075131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0075139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0075146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0075148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0075380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0076011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0076012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0076020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0076027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:0)</name>
      <smpdb_id>SMP0076029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0076030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:0)</name>
      <smpdb_id>SMP0076037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0076038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/24:0)</name>
      <smpdb_id>SMP0076044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0076045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0076053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0076060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/20:0)</name>
      <smpdb_id>SMP0108262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/21:0)</name>
      <smpdb_id>SMP0108257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/22:0)</name>
      <smpdb_id>SMP0108278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/a-21:0)</name>
      <smpdb_id>SMP0108922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/a-25:0)</name>
      <smpdb_id>SMP0108923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-21:0)</name>
      <smpdb_id>SMP0108924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-22:0)</name>
      <smpdb_id>SMP0108925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-24:0)</name>
      <smpdb_id>SMP0108926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/21:0)</name>
      <smpdb_id>SMP0108277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/22:0)</name>
      <smpdb_id>SMP0108311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0108927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0108928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0108929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0108930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0108931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0108932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0108933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/10:0)</name>
      <smpdb_id>SMP0108328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/12:0)</name>
      <smpdb_id>SMP0108244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/13:0)</name>
      <smpdb_id>SMP0108317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/14:0)</name>
      <smpdb_id>SMP0108266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/15:0)</name>
      <smpdb_id>SMP0108275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/16:0)</name>
      <smpdb_id>SMP0108332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/17:0)</name>
      <smpdb_id>SMP0108292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/18:0)</name>
      <smpdb_id>SMP0108327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/21:0)</name>
      <smpdb_id>SMP0108305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/22:0)</name>
      <smpdb_id>SMP0108316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/8:0)</name>
      <smpdb_id>SMP0108301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0108934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0108935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0108936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0108937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0108938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0108939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0108940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0108941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0108942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0108943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0108944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0108945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0108946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0108947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0108948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0108949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0108950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/10:0)</name>
      <smpdb_id>SMP0108279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/12:0)</name>
      <smpdb_id>SMP0108261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/13:0)</name>
      <smpdb_id>SMP0108286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/14:0)</name>
      <smpdb_id>SMP0108255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/15:0)</name>
      <smpdb_id>SMP0108252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/16:0)</name>
      <smpdb_id>SMP0108299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/17:0)</name>
      <smpdb_id>SMP0108308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/18:0)</name>
      <smpdb_id>SMP0108282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/22:0)</name>
      <smpdb_id>SMP0108265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/8:0)</name>
      <smpdb_id>SMP0108319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0108951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0108952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0108953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0108954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0108955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0108956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0108957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0108958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0108959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0108960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0108961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0108962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0108963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0108964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0108965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0108966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0108967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0108968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/13:0)</name>
      <smpdb_id>SMP0108969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/14:0)</name>
      <smpdb_id>SMP0108970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/15:0)</name>
      <smpdb_id>SMP0108971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/16:0)</name>
      <smpdb_id>SMP0108972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/17:0)</name>
      <smpdb_id>SMP0108973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/18:0)</name>
      <smpdb_id>SMP0108974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/8:0)</name>
      <smpdb_id>SMP0108975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-13:0)</name>
      <smpdb_id>SMP0108976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-15:0)</name>
      <smpdb_id>SMP0108977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-17:0)</name>
      <smpdb_id>SMP0108978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0108979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0108980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0108981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0108982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0108983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0108984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0108985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0108986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0108987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0108988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0108989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0108990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0108991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0108992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/12:0)</name>
      <smpdb_id>SMP0108993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/13:0)</name>
      <smpdb_id>SMP0108994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/14:0)</name>
      <smpdb_id>SMP0108995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/15:0)</name>
      <smpdb_id>SMP0108996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/16:0)</name>
      <smpdb_id>SMP0108997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/17:0)</name>
      <smpdb_id>SMP0108998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/18:0)</name>
      <smpdb_id>SMP0108999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/8:0)</name>
      <smpdb_id>SMP0109000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-13:0)</name>
      <smpdb_id>SMP0109001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-15:0)</name>
      <smpdb_id>SMP0109002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-17:0)</name>
      <smpdb_id>SMP0109003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0109021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0109022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0109023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0109024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0109025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0109026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0109027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/8:0)</name>
      <smpdb_id>SMP0109028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0109029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0109030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0109031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0109032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0109033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0109034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0109035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0109036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0109037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0109038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-19:0)</name>
      <smpdb_id>SMP0109039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0109043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0109044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0109045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0109046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0109047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0109048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0109049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/8:0)</name>
      <smpdb_id>SMP0109050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0109051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0109052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0109053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0109054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0109055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0109056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0109057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0109058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0109059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0109060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-19:0)</name>
      <smpdb_id>SMP0109061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0109064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0109065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0109066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0109067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0109068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0109069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0109070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/8:0)</name>
      <smpdb_id>SMP0109071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0109072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0109073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0109074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0109075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0109076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0109078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0109079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0109080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0109081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0109082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-19:0)</name>
      <smpdb_id>SMP0109083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/10:0)</name>
      <smpdb_id>SMP0108330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/14:0)</name>
      <smpdb_id>SMP0108290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/17:0)</name>
      <smpdb_id>SMP0108312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/19:0)</name>
      <smpdb_id>SMP0108270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/21:0)</name>
      <smpdb_id>SMP0108300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/22:0)</name>
      <smpdb_id>SMP0108259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/10:0)</name>
      <smpdb_id>SMP0108320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/12:0)</name>
      <smpdb_id>SMP0108331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/13:0)</name>
      <smpdb_id>SMP0108318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/16:0)</name>
      <smpdb_id>SMP0108293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/17:0)</name>
      <smpdb_id>SMP0108304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/18:0)</name>
      <smpdb_id>SMP0108297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/19:0)</name>
      <smpdb_id>SMP0108288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/21:0)</name>
      <smpdb_id>SMP0108322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/22:0)</name>
      <smpdb_id>SMP0108314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/8:0)</name>
      <smpdb_id>SMP0108263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/10:0)</name>
      <smpdb_id>SMP0108256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/13:0)</name>
      <smpdb_id>SMP0108326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/15:0)</name>
      <smpdb_id>SMP0108250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/16:0)</name>
      <smpdb_id>SMP0108247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/21:0)</name>
      <smpdb_id>SMP0108313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/22:0)</name>
      <smpdb_id>SMP0108283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/8:0)</name>
      <smpdb_id>SMP0108276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/12:0)</name>
      <smpdb_id>SMP0108248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/13:0)</name>
      <smpdb_id>SMP0108295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/19:0)</name>
      <smpdb_id>SMP0108249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/21:0)</name>
      <smpdb_id>SMP0108271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/10:0)</name>
      <smpdb_id>SMP0108267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/12:0)</name>
      <smpdb_id>SMP0108324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/17:0)</name>
      <smpdb_id>SMP0108284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/21:0)</name>
      <smpdb_id>SMP0108306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/10:0)</name>
      <smpdb_id>SMP0108274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/19:0)</name>
      <smpdb_id>SMP0108269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/21:0)</name>
      <smpdb_id>SMP0108251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/13:0)</name>
      <smpdb_id>SMP0108289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/14:0)</name>
      <smpdb_id>SMP0108253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/16:0)</name>
      <smpdb_id>SMP0108302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/17:0)</name>
      <smpdb_id>SMP0108254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/19:0)</name>
      <smpdb_id>SMP0108264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/21:0)</name>
      <smpdb_id>SMP0108281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/22:0)</name>
      <smpdb_id>SMP0108294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/8:0)</name>
      <smpdb_id>SMP0108296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/10:0)</name>
      <smpdb_id>SMP0108315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/13:0)</name>
      <smpdb_id>SMP0108307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/17:0)</name>
      <smpdb_id>SMP0108273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/21:0)</name>
      <smpdb_id>SMP0108323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/8:0)</name>
      <smpdb_id>SMP0108287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/13:0)</name>
      <smpdb_id>SMP0108291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/15:0)</name>
      <smpdb_id>SMP0108272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/18:0)</name>
      <smpdb_id>SMP0108258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0109204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0109205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0109206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0109207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0109208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0109209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0109210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0109211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0109212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0109213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/10:0)</name>
      <smpdb_id>SMP0108309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/12:0)</name>
      <smpdb_id>SMP0108333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/13:0)</name>
      <smpdb_id>SMP0108329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/17:0)</name>
      <smpdb_id>SMP0108303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/19:0)</name>
      <smpdb_id>SMP0108321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:0)</name>
      <smpdb_id>SMP0076182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0076183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/21:0)</name>
      <smpdb_id>SMP0108390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:0)</name>
      <smpdb_id>SMP0076190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0076191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/24:0)</name>
      <smpdb_id>SMP0076197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0076198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/8:0)</name>
      <smpdb_id>SMP0108268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-13:0)</name>
      <smpdb_id>SMP0109214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-15:0)</name>
      <smpdb_id>SMP0109215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-17:0)</name>
      <smpdb_id>SMP0109216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0109217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0109218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-12:0)</name>
      <smpdb_id>SMP0109219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-13:0)</name>
      <smpdb_id>SMP0109220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-14:0)</name>
      <smpdb_id>SMP0109221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-15:0)</name>
      <smpdb_id>SMP0109222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-16:0)</name>
      <smpdb_id>SMP0109223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-17:0)</name>
      <smpdb_id>SMP0109224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-18:0)</name>
      <smpdb_id>SMP0109225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0109226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0109227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0109228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0109229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0109230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0076206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0076213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/21:0)</name>
      <smpdb_id>SMP0108389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/22:0)</name>
      <smpdb_id>SMP0108370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0109231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0109232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0109233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0109234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0109235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0109236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0109237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0109238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0109239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0109240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0109241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0109242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0109243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0109244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0109245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0109246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0109247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:0)</name>
      <smpdb_id>SMP0076290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/24:0)</name>
      <smpdb_id>SMP0076297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/24:0/24:0)</name>
      <smpdb_id>SMP0076332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/10:0)</name>
      <smpdb_id>SMP0108298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/14:0)</name>
      <smpdb_id>SMP0108246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/15:0)</name>
      <smpdb_id>SMP0108285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/16:0)</name>
      <smpdb_id>SMP0108280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/19:0)</name>
      <smpdb_id>SMP0108310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/21:0)</name>
      <smpdb_id>SMP0108245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/22:0)</name>
      <smpdb_id>SMP0108260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/8:0)</name>
      <smpdb_id>SMP0108325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0109330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0109370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0109371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0109372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0109373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0109374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0109375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0109376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0109377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0109378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0109379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0109380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0109381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0109382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0109383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0109384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0109385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0109386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0109387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0109388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0109389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0109390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0109391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0109392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0109393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0109394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0109395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0109396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0109397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0109398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0109400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0109401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0109402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0109403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0109404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0109405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0109406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0109407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0109408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0109409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0109410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0109411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0109412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0109413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0109414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0109415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0109416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0109417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0109418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0109419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0109420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0109421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0109422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0109423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0109424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0109425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0109426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0076342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0076349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/10:0)</name>
      <smpdb_id>SMP0108335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/12:0)</name>
      <smpdb_id>SMP0108363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/13:0)</name>
      <smpdb_id>SMP0108339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/17:0)</name>
      <smpdb_id>SMP0108349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/18:0)</name>
      <smpdb_id>SMP0108337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/22:0)</name>
      <smpdb_id>SMP0108367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/12:0)</name>
      <smpdb_id>SMP0108361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/13:0)</name>
      <smpdb_id>SMP0108351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/14:0)</name>
      <smpdb_id>SMP0108344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/15:0)</name>
      <smpdb_id>SMP0108371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/16:0)</name>
      <smpdb_id>SMP0108383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/18:0)</name>
      <smpdb_id>SMP0108387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/22:0)</name>
      <smpdb_id>SMP0108366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0109440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/13:0)</name>
      <smpdb_id>SMP0108368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/16:0)</name>
      <smpdb_id>SMP0108380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/17:0)</name>
      <smpdb_id>SMP0108345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/18:0)</name>
      <smpdb_id>SMP0108341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/22:0)</name>
      <smpdb_id>SMP0108388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/10:0)</name>
      <smpdb_id>SMP0108347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/13:0)</name>
      <smpdb_id>SMP0108342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/14:0)</name>
      <smpdb_id>SMP0108338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/16:0)</name>
      <smpdb_id>SMP0108346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/17:0)</name>
      <smpdb_id>SMP0108352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/18:0)</name>
      <smpdb_id>SMP0108386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/22:0)</name>
      <smpdb_id>SMP0108334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/8:0)</name>
      <smpdb_id>SMP0108365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/10:0)</name>
      <smpdb_id>SMP0108372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/13:0)</name>
      <smpdb_id>SMP0108358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/14:0)</name>
      <smpdb_id>SMP0108375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/15:0)</name>
      <smpdb_id>SMP0108348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/17:0)</name>
      <smpdb_id>SMP0108384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/18:0)</name>
      <smpdb_id>SMP0108369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/22:0)</name>
      <smpdb_id>SMP0108392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/8:0)</name>
      <smpdb_id>SMP0108354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/10:0)</name>
      <smpdb_id>SMP0108350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/15:0)</name>
      <smpdb_id>SMP0108355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/16:0)</name>
      <smpdb_id>SMP0108381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/17:0)</name>
      <smpdb_id>SMP0108364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/18:0)</name>
      <smpdb_id>SMP0108356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/22:0)</name>
      <smpdb_id>SMP0108385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/12:0)</name>
      <smpdb_id>SMP0108376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/17:0)</name>
      <smpdb_id>SMP0108393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/8:0)</name>
      <smpdb_id>SMP0108377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/17:0)</name>
      <smpdb_id>SMP0108396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/18:0)</name>
      <smpdb_id>SMP0108399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/10:0)</name>
      <smpdb_id>SMP0108340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/12:0)</name>
      <smpdb_id>SMP0108374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/13:0)</name>
      <smpdb_id>SMP0108336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/14:0)</name>
      <smpdb_id>SMP0108373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/15:0)</name>
      <smpdb_id>SMP0108382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/16:0)</name>
      <smpdb_id>SMP0108391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/17:0)</name>
      <smpdb_id>SMP0108397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/18:0)</name>
      <smpdb_id>SMP0108398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/22:0)</name>
      <smpdb_id>SMP0108400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/8:0)</name>
      <smpdb_id>SMP0108343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0109556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0109557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0109558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0109559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0109560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0109561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0109562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0109563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0109564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0109565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0109566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0109567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0109568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0109569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0109570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0109571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0109572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/17:0)</name>
      <smpdb_id>SMP0108395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/18:0)</name>
      <smpdb_id>SMP0108394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/22:0)</name>
      <smpdb_id>SMP0108401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/10:0)</name>
      <smpdb_id>SMP0108360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/12:0)</name>
      <smpdb_id>SMP0108357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/13:0)</name>
      <smpdb_id>SMP0108353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/16:0)</name>
      <smpdb_id>SMP0108359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/18:0)</name>
      <smpdb_id>SMP0108378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/22:0)</name>
      <smpdb_id>SMP0108362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/8:0)</name>
      <smpdb_id>SMP0108379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0109694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0109695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0109696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0109697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0109698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0109699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0109700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0109701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0109702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0109703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0109704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0109705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0109706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0109707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0109708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0109709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0109710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0109711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0109712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0109713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0109714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0109715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0109716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0109717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0109718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0109719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0109720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0109721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0109722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0109723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0109724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0109725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0109726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0109727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0109728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0109729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0109730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0109731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0109732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0109733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0109734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0109735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0109736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0109737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0109738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0109739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0109740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0109741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0109742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0109743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0109744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0109745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0109746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0109747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0109748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0109749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/10:0)</name>
      <smpdb_id>SMP0108437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/12:0)</name>
      <smpdb_id>SMP0108408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/13:0)</name>
      <smpdb_id>SMP0108423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/12:0)</name>
      <smpdb_id>SMP0108405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/13:0)</name>
      <smpdb_id>SMP0108403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/14:0)</name>
      <smpdb_id>SMP0108414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/15:0)</name>
      <smpdb_id>SMP0108426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/18:0)</name>
      <smpdb_id>SMP0108407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/8:0)</name>
      <smpdb_id>SMP0108420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0109763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/13:0)</name>
      <smpdb_id>SMP0108436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/15:0)</name>
      <smpdb_id>SMP0108428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/16:0)</name>
      <smpdb_id>SMP0108430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/17:0)</name>
      <smpdb_id>SMP0108419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/18:0)</name>
      <smpdb_id>SMP0108413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/8:0)</name>
      <smpdb_id>SMP0108411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/10:0)</name>
      <smpdb_id>SMP0108440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/13:0)</name>
      <smpdb_id>SMP0108422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/10:0)</name>
      <smpdb_id>SMP0108425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/8:0)</name>
      <smpdb_id>SMP0108410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/10:0)</name>
      <smpdb_id>SMP0108404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/12:0)</name>
      <smpdb_id>SMP0108406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/10:0)</name>
      <smpdb_id>SMP0108439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/12:0)</name>
      <smpdb_id>SMP0108402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/14:0)</name>
      <smpdb_id>SMP0108415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/15:0)</name>
      <smpdb_id>SMP0108434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/16:0)</name>
      <smpdb_id>SMP0108412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/17:0)</name>
      <smpdb_id>SMP0108431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/8:0)</name>
      <smpdb_id>SMP0108409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/10:0)</name>
      <smpdb_id>SMP0108421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/17:0)</name>
      <smpdb_id>SMP0108417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/8:0)</name>
      <smpdb_id>SMP0108432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/10:0)</name>
      <smpdb_id>SMP0108424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/12:0)</name>
      <smpdb_id>SMP0108435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/13:0)</name>
      <smpdb_id>SMP0108433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/17:0)</name>
      <smpdb_id>SMP0108438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:0)</name>
      <smpdb_id>SMP0076986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/24:0)</name>
      <smpdb_id>SMP0076993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/8:0)</name>
      <smpdb_id>SMP0108441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0077001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/24:0/24:0)</name>
      <smpdb_id>SMP0077028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/10:0)</name>
      <smpdb_id>SMP0108416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/14:0)</name>
      <smpdb_id>SMP0108418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/16:0)</name>
      <smpdb_id>SMP0108427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/8:0)</name>
      <smpdb_id>SMP0108429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0108540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0077031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0077037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:0/24:0/24:0)</name>
      <smpdb_id>SMP0077147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:1(15Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/10:0)</name>
      <smpdb_id>SMP0108443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/12:0)</name>
      <smpdb_id>SMP0108502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/16:0)</name>
      <smpdb_id>SMP0108450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/18:0)</name>
      <smpdb_id>SMP0108535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0110069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0110070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/12:0)</name>
      <smpdb_id>SMP0108459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/13:0)</name>
      <smpdb_id>SMP0108498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/14:0)</name>
      <smpdb_id>SMP0108462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/15:0)</name>
      <smpdb_id>SMP0108442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/17:0)</name>
      <smpdb_id>SMP0108464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/19:0)</name>
      <smpdb_id>SMP0108499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0110086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0110087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/10:0)</name>
      <smpdb_id>SMP0108455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/12:0)</name>
      <smpdb_id>SMP0108475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/14:0)</name>
      <smpdb_id>SMP0108532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/15:0)</name>
      <smpdb_id>SMP0108529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/17:0)</name>
      <smpdb_id>SMP0108491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/18:0)</name>
      <smpdb_id>SMP0108510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0110103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0110104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/12:0)</name>
      <smpdb_id>SMP0108486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/15:0)</name>
      <smpdb_id>SMP0108528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/17:0)</name>
      <smpdb_id>SMP0108505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0110120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0110121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/13:0)</name>
      <smpdb_id>SMP0108513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/14:0)</name>
      <smpdb_id>SMP0108449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/15:0)</name>
      <smpdb_id>SMP0108493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/16:0)</name>
      <smpdb_id>SMP0108500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/18:0)</name>
      <smpdb_id>SMP0108474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/19:0)</name>
      <smpdb_id>SMP0108446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0110137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0110138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/12:0)</name>
      <smpdb_id>SMP0108516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/16:0)</name>
      <smpdb_id>SMP0108530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/17:0)</name>
      <smpdb_id>SMP0108509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0110154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0110155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/13:0)</name>
      <smpdb_id>SMP0108524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/15:0)</name>
      <smpdb_id>SMP0108501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/17:0)</name>
      <smpdb_id>SMP0108453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/18:0)</name>
      <smpdb_id>SMP0108520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0110171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0110172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/10:0)</name>
      <smpdb_id>SMP0108482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/12:0)</name>
      <smpdb_id>SMP0108444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/14:0)</name>
      <smpdb_id>SMP0108497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/15:0)</name>
      <smpdb_id>SMP0108487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/17:0)</name>
      <smpdb_id>SMP0108484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/18:0)</name>
      <smpdb_id>SMP0108531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/19:0)</name>
      <smpdb_id>SMP0108538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0110185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0110186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0110187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0110188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0110189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0110190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0110191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0110192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0110193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0110194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0110195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-20:0)</name>
      <smpdb_id>SMP0110196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/12:0)</name>
      <smpdb_id>SMP0108508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/13:0)</name>
      <smpdb_id>SMP0108539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/14:0)</name>
      <smpdb_id>SMP0108515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/15:0)</name>
      <smpdb_id>SMP0108454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/16:0)</name>
      <smpdb_id>SMP0108490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/17:0)</name>
      <smpdb_id>SMP0108527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/18:0)</name>
      <smpdb_id>SMP0108537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/19:0)</name>
      <smpdb_id>SMP0108536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/8:0)</name>
      <smpdb_id>SMP0108242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0110197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0110198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0110199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0110200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0110201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0110202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0110203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0110204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0110205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0110206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0110207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0110208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0110209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0110210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0110211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0110212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0110213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0110217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0110218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0110223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0110233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0110234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0110248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0110249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0110262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0110263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0110264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0110265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0110266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0110267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0110268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0110269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0110270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0110271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0110272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0110273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0110274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0110275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/12:0)</name>
      <smpdb_id>SMP0110367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/13:0)</name>
      <smpdb_id>SMP0110368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/14:0)</name>
      <smpdb_id>SMP0110369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/15:0)</name>
      <smpdb_id>SMP0110370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/16:0)</name>
      <smpdb_id>SMP0110371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/17:0)</name>
      <smpdb_id>SMP0110372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/18:0)</name>
      <smpdb_id>SMP0110373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0110377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/13:0)</name>
      <smpdb_id>SMP0110390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/14:0)</name>
      <smpdb_id>SMP0110391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/15:0)</name>
      <smpdb_id>SMP0110392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/16:0)</name>
      <smpdb_id>SMP0110393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/17:0)</name>
      <smpdb_id>SMP0110394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/18:0)</name>
      <smpdb_id>SMP0110395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0110399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/14:0)</name>
      <smpdb_id>SMP0110412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/15:0)</name>
      <smpdb_id>SMP0110413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/16:0)</name>
      <smpdb_id>SMP0110414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/17:0)</name>
      <smpdb_id>SMP0110415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/18:0)</name>
      <smpdb_id>SMP0110416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0110420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/15:0)</name>
      <smpdb_id>SMP0110433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/16:0)</name>
      <smpdb_id>SMP0110434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/17:0)</name>
      <smpdb_id>SMP0110435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/18:0)</name>
      <smpdb_id>SMP0110436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0110440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/16:0)</name>
      <smpdb_id>SMP0110453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/17:0)</name>
      <smpdb_id>SMP0110454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/18:0)</name>
      <smpdb_id>SMP0110455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0110459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/17:0)</name>
      <smpdb_id>SMP0110472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/18:0)</name>
      <smpdb_id>SMP0110473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0110477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/18:0)</name>
      <smpdb_id>SMP0110490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0110494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0110510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0110524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0110538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0110551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/13:0)</name>
      <smpdb_id>SMP0110552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/14:0)</name>
      <smpdb_id>SMP0110553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/15:0)</name>
      <smpdb_id>SMP0110554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/16:0)</name>
      <smpdb_id>SMP0110555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/17:0)</name>
      <smpdb_id>SMP0110556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/18:0)</name>
      <smpdb_id>SMP0110557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-13:0)</name>
      <smpdb_id>SMP0110558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-15:0)</name>
      <smpdb_id>SMP0110559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-17:0)</name>
      <smpdb_id>SMP0110560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0110561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0110562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0110563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0110564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0110565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0110566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0110567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0110568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0110569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0110570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0110571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0110572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0110573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0110574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/a-13:0)</name>
      <smpdb_id>SMP0110630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/12:0)</name>
      <smpdb_id>SMP0110667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/13:0)</name>
      <smpdb_id>SMP0110668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/14:0)</name>
      <smpdb_id>SMP0110669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/15:0)</name>
      <smpdb_id>SMP0110670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/16:0)</name>
      <smpdb_id>SMP0110671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/17:0)</name>
      <smpdb_id>SMP0110672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/18:0)</name>
      <smpdb_id>SMP0110673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/13:0)</name>
      <smpdb_id>SMP0110689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/14:0)</name>
      <smpdb_id>SMP0110690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/15:0)</name>
      <smpdb_id>SMP0110691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/16:0)</name>
      <smpdb_id>SMP0110692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/17:0)</name>
      <smpdb_id>SMP0110693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/18:0)</name>
      <smpdb_id>SMP0110694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/14:0)</name>
      <smpdb_id>SMP0110710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/15:0)</name>
      <smpdb_id>SMP0110711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/16:0)</name>
      <smpdb_id>SMP0110712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/17:0)</name>
      <smpdb_id>SMP0110713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/18:0)</name>
      <smpdb_id>SMP0110714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/15:0)</name>
      <smpdb_id>SMP0110730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/16:0)</name>
      <smpdb_id>SMP0110731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/17:0)</name>
      <smpdb_id>SMP0110732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/18:0)</name>
      <smpdb_id>SMP0110733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/16:0)</name>
      <smpdb_id>SMP0110749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/17:0)</name>
      <smpdb_id>SMP0110750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/18:0)</name>
      <smpdb_id>SMP0110751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/17:0)</name>
      <smpdb_id>SMP0110767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/18:0)</name>
      <smpdb_id>SMP0110768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/18:0)</name>
      <smpdb_id>SMP0110784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0110807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/10:0)</name>
      <smpdb_id>SMP0110842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/12:0)</name>
      <smpdb_id>SMP0110843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/13:0)</name>
      <smpdb_id>SMP0110844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/14:0)</name>
      <smpdb_id>SMP0110845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/15:0)</name>
      <smpdb_id>SMP0110846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/16:0)</name>
      <smpdb_id>SMP0110847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/17:0)</name>
      <smpdb_id>SMP0110848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/18:0)</name>
      <smpdb_id>SMP0110849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-13:0)</name>
      <smpdb_id>SMP0110850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-15:0)</name>
      <smpdb_id>SMP0110851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-17:0)</name>
      <smpdb_id>SMP0110852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0110952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0110953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0110954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0110955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0110956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0110957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0110958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0110959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0110960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0110961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0110962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0110963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0110964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0110965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0110966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0110967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0110968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0110972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0110973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0110974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0110975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0110976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0110977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0110978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0110979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0110980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0110981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0110982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0110983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0110984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0110985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0110986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0110987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0110988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0110991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0110992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0110993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0110994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0110995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0110996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0110997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0110998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0110999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0111000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0111001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0111002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0111003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0111004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0111005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0111006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0111007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/12:0)</name>
      <smpdb_id>SMP0111009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/13:0)</name>
      <smpdb_id>SMP0111010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/14:0)</name>
      <smpdb_id>SMP0111011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/15:0)</name>
      <smpdb_id>SMP0111012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/16:0)</name>
      <smpdb_id>SMP0111013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/17:0)</name>
      <smpdb_id>SMP0111014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/18:0)</name>
      <smpdb_id>SMP0111015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/19:0)</name>
      <smpdb_id>SMP0111016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0111027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0111028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0111029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/13:0)</name>
      <smpdb_id>SMP0111031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/14:0)</name>
      <smpdb_id>SMP0111032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/15:0)</name>
      <smpdb_id>SMP0111033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/16:0)</name>
      <smpdb_id>SMP0111034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/17:0)</name>
      <smpdb_id>SMP0111035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/18:0)</name>
      <smpdb_id>SMP0111036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/19:0)</name>
      <smpdb_id>SMP0111037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0111048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0111049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0111050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/14:0)</name>
      <smpdb_id>SMP0111052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/15:0)</name>
      <smpdb_id>SMP0111053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/16:0)</name>
      <smpdb_id>SMP0111054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/17:0)</name>
      <smpdb_id>SMP0111055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/18:0)</name>
      <smpdb_id>SMP0111056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/19:0)</name>
      <smpdb_id>SMP0111057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0111068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0111069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0111070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/15:0)</name>
      <smpdb_id>SMP0111072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/16:0)</name>
      <smpdb_id>SMP0111073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/17:0)</name>
      <smpdb_id>SMP0111074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/18:0)</name>
      <smpdb_id>SMP0111075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/19:0)</name>
      <smpdb_id>SMP0111076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0111087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0111088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0111089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/16:0)</name>
      <smpdb_id>SMP0111091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/17:0)</name>
      <smpdb_id>SMP0111092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/18:0)</name>
      <smpdb_id>SMP0111093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/19:0)</name>
      <smpdb_id>SMP0111094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0111105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0111106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0111107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/17:0)</name>
      <smpdb_id>SMP0111109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/18:0)</name>
      <smpdb_id>SMP0111110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/19:0)</name>
      <smpdb_id>SMP0111111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0111122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0111123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0111124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/18:0)</name>
      <smpdb_id>SMP0111126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/19:0)</name>
      <smpdb_id>SMP0111127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0111138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0111139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0111140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/19:0)</name>
      <smpdb_id>SMP0111142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0111143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0111144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0111145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0111146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0111147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0111148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0111149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0111150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0111151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0111152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0111153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0111164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0111165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0111166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0111177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0111178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0111179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0111189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0111190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0111191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0111200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0111201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0111202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0111210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0111211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0111212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0111219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0111220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0111221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0111227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0111228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0111229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0111234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0111235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0111236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0111240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0111241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0111242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0111245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0111246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0111247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/12:0)</name>
      <smpdb_id>SMP0111249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/13:0)</name>
      <smpdb_id>SMP0111250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/14:0)</name>
      <smpdb_id>SMP0111251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/15:0)</name>
      <smpdb_id>SMP0111252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/16:0)</name>
      <smpdb_id>SMP0111253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/17:0)</name>
      <smpdb_id>SMP0111254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/18:0)</name>
      <smpdb_id>SMP0111255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-13:0)</name>
      <smpdb_id>SMP0111256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-15:0)</name>
      <smpdb_id>SMP0111257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-17:0)</name>
      <smpdb_id>SMP0111258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-12:0)</name>
      <smpdb_id>SMP0111259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-13:0)</name>
      <smpdb_id>SMP0111260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-14:0)</name>
      <smpdb_id>SMP0111261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-15:0)</name>
      <smpdb_id>SMP0111262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-16:0)</name>
      <smpdb_id>SMP0111263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-17:0)</name>
      <smpdb_id>SMP0111264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-18:0)</name>
      <smpdb_id>SMP0111265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0111266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0111267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0111268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0111269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0111270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0111271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0111272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/12:0)</name>
      <smpdb_id>SMP0111276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/13:0)</name>
      <smpdb_id>SMP0111277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/14:0)</name>
      <smpdb_id>SMP0111278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/15:0)</name>
      <smpdb_id>SMP0111279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/16:0)</name>
      <smpdb_id>SMP0111280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/17:0)</name>
      <smpdb_id>SMP0111281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/18:0)</name>
      <smpdb_id>SMP0111282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0111293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/13:0)</name>
      <smpdb_id>SMP0111295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/14:0)</name>
      <smpdb_id>SMP0111296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/15:0)</name>
      <smpdb_id>SMP0111297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/16:0)</name>
      <smpdb_id>SMP0111298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/17:0)</name>
      <smpdb_id>SMP0111299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/18:0)</name>
      <smpdb_id>SMP0111300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0111311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/14:0)</name>
      <smpdb_id>SMP0111313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/15:0)</name>
      <smpdb_id>SMP0111314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/16:0)</name>
      <smpdb_id>SMP0111315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/17:0)</name>
      <smpdb_id>SMP0111316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/18:0)</name>
      <smpdb_id>SMP0111317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0111328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/15:0)</name>
      <smpdb_id>SMP0111330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/16:0)</name>
      <smpdb_id>SMP0111331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/17:0)</name>
      <smpdb_id>SMP0111332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/18:0)</name>
      <smpdb_id>SMP0111333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0111344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/16:0)</name>
      <smpdb_id>SMP0111346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/17:0)</name>
      <smpdb_id>SMP0111347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/18:0)</name>
      <smpdb_id>SMP0111348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0111359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/17:0)</name>
      <smpdb_id>SMP0111361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/18:0)</name>
      <smpdb_id>SMP0111362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0111373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/18:0)</name>
      <smpdb_id>SMP0111375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0111386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0111398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0111409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0111419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0111428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0111436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0111443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0111449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0111454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0111458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0111461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0111463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0111464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0111465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0111466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0111467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0111468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0111469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0111470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0111471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0111472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0111473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0111474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0111475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0111476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0111477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0111478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0111479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0111480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0111481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0111482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/12:0)</name>
      <smpdb_id>SMP0111486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/13:0)</name>
      <smpdb_id>SMP0111487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/14:0)</name>
      <smpdb_id>SMP0111488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/15:0)</name>
      <smpdb_id>SMP0111489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/16:0)</name>
      <smpdb_id>SMP0111490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/17:0)</name>
      <smpdb_id>SMP0111491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/18:0)</name>
      <smpdb_id>SMP0111492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/13:0)</name>
      <smpdb_id>SMP0111504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/14:0)</name>
      <smpdb_id>SMP0111505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/15:0)</name>
      <smpdb_id>SMP0111506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/16:0)</name>
      <smpdb_id>SMP0111507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/17:0)</name>
      <smpdb_id>SMP0111508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/18:0)</name>
      <smpdb_id>SMP0111509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/14:0)</name>
      <smpdb_id>SMP0111521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/15:0)</name>
      <smpdb_id>SMP0111522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/16:0)</name>
      <smpdb_id>SMP0111523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/17:0)</name>
      <smpdb_id>SMP0111524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/18:0)</name>
      <smpdb_id>SMP0111525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/15:0)</name>
      <smpdb_id>SMP0111537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/16:0)</name>
      <smpdb_id>SMP0111538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/17:0)</name>
      <smpdb_id>SMP0111539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/18:0)</name>
      <smpdb_id>SMP0111540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/16:0)</name>
      <smpdb_id>SMP0111552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/17:0)</name>
      <smpdb_id>SMP0111553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/18:0)</name>
      <smpdb_id>SMP0111554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/17:0)</name>
      <smpdb_id>SMP0111566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/18:0)</name>
      <smpdb_id>SMP0111567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/18:0)</name>
      <smpdb_id>SMP0111579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0111656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0111657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0111658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0111659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0111660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0111661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0111662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0111663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0111664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0111665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0111666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0111667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0111668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0111669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0111670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0111671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0111672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/12:0)</name>
      <smpdb_id>SMP0111676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/13:0)</name>
      <smpdb_id>SMP0111677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/14:0)</name>
      <smpdb_id>SMP0111678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/15:0)</name>
      <smpdb_id>SMP0111679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/16:0)</name>
      <smpdb_id>SMP0111680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/17:0)</name>
      <smpdb_id>SMP0111681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/18:0)</name>
      <smpdb_id>SMP0111682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/13:0)</name>
      <smpdb_id>SMP0111693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/14:0)</name>
      <smpdb_id>SMP0111694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/15:0)</name>
      <smpdb_id>SMP0111695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/16:0)</name>
      <smpdb_id>SMP0111696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/17:0)</name>
      <smpdb_id>SMP0111697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/18:0)</name>
      <smpdb_id>SMP0111698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/14:0)</name>
      <smpdb_id>SMP0111709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/15:0)</name>
      <smpdb_id>SMP0111710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/16:0)</name>
      <smpdb_id>SMP0111711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/17:0)</name>
      <smpdb_id>SMP0111712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/18:0)</name>
      <smpdb_id>SMP0111713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/15:0)</name>
      <smpdb_id>SMP0111724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/16:0)</name>
      <smpdb_id>SMP0111725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/17:0)</name>
      <smpdb_id>SMP0111726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/18:0)</name>
      <smpdb_id>SMP0111727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/16:0)</name>
      <smpdb_id>SMP0111738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/17:0)</name>
      <smpdb_id>SMP0111739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/18:0)</name>
      <smpdb_id>SMP0111740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/17:0)</name>
      <smpdb_id>SMP0111751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/18:0)</name>
      <smpdb_id>SMP0111752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/18:0)</name>
      <smpdb_id>SMP0111763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0111829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0111830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0111831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0111832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0111833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0111834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0111835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0111836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0111837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0111838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0111839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0111840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0111841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0111842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0111843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0111844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0111845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>EGF Signalling Pathway</name>
      <smpdb_id>SMP0120924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>EPO Signaling Pathway</name>
      <smpdb_id>SMP0120938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 4 and Serotonin</name>
      <smpdb_id>SMP0108169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 6 and Serotonin</name>
      <smpdb_id>SMP0108172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Excitatory Neural Signalling Through 5-HTR 7 and Serotonin</name>
      <smpdb_id>SMP0108170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>FAS signaling pathway ( CD95 )</name>
      <smpdb_id>SMP0120939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gastric Acid Production</name>
      <smpdb_id>SMP0119381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>GnRH Signaling Pathway</name>
      <smpdb_id>SMP0120925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Growth Hormone Signaling Pathway </name>
      <smpdb_id>SMP0120923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Insulin Signalling</name>
      <smpdb_id>SMP0108189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2a and Adenosine</name>
      <smpdb_id>SMP0108174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Adenosine Receptor A2b and Adenosine</name>
      <smpdb_id>SMP0108178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through FSH Receptor and Follicle Stimulating Hormone</name>
      <smpdb_id>SMP0108183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Histamine H2 Receptor and Histamine</name>
      <smpdb_id>SMP0107995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through LHCGR Receptor and Luteinizing Hormone/Choriogonadotropin</name>
      <smpdb_id>SMP0108184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Intracellular Signalling Through Prostacyclin Receptor and Prostacyclin</name>
      <smpdb_id>SMP0107998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Leucine Stimulation on Insulin Signaling</name>
      <smpdb_id>SMP0108000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>LPS and Citrate Signaling and Inflammation</name>
      <smpdb_id>SMP0120946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Electron Transport Chain</name>
      <smpdb_id>SMP0087261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Muscle/Heart Contraction</name>
      <smpdb_id>SMP0119378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>NF-kB Signaling Pathway</name>
      <smpdb_id>SMP0120926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nitric Oxide Signaling Pathway</name>
      <smpdb_id>SMP0108206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>P53 Signaling Pathway</name>
      <smpdb_id>SMP0100482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylinositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Plasmalogen Synthesis</name>
      <smpdb_id>SMP0087264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Rac 1 cell motility signaling pathway </name>
      <smpdb_id>SMP0100484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Rac 1 Cell Motility Signaling Pathway</name>
      <smpdb_id>SMP0120885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ras Signaling Pathway </name>
      <smpdb_id>SMP0108210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Riboflavin Metabolism</name>
      <smpdb_id>SMP0087211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Stat3 Signaling Pathway</name>
      <smpdb_id>SMP0120936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sulfate/Sulfite Metabolism</name>
      <smpdb_id>SMP0087216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>T Cell Receptor Signaling Pathway </name>
      <smpdb_id>SMP0120935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Thiamine Metabolism</name>
      <smpdb_id>SMP0087212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>TNF/Stress Related Signaling</name>
      <smpdb_id>SMP0100483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Toll-Like Receptor Pathway 1</name>
      <smpdb_id>SMP0120931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Toll-Like Receptor Pathway 2</name>
      <smpdb_id>SMP0120937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Trehalose Degradation</name>
      <smpdb_id>SMP0087263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183023</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>513.839 +/- 87.395</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by Fiske &amp; Subbarow (1925) method. Samples have been collected from White Shorthorn x Galloway (Blue-grey).</comment>
      <references>
        <reference>
          <reference_text>C. R. E. Cogginsa and A. C. Field. Diurnal variation in the chemical composition of plasma from lactating beef cows on three dietary energy intakes. J. agric. Sri., Camb. (1976), 86, 595-602</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12530.088</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1000 - 4000</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>An increase in the acidity of the ruminal fluid also increased the absorption of phosphate, as did an increase in the ruminal Ca2&amp;#135; concentration over the range (1-4)mmol per litre</comment>
      <references>
        <reference>
          <reference_text>Wadhwa DR, Care AD: The absorption of phosphate ions from the ovine reticulorumen. Vet J. 2002 Mar;163(2):182-6.</reference_text>
          <pubmed_id>12093193</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00009</kegg_id>
  <drugbank_id>DB09394</drugbank_id>
  <foodb_id>FDB013380</foodb_id>
  <pubchem_compound_id>1004</pubchem_compound_id>
  <chemspider_id/>
  <chebi_id>26078</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00007408</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Phosphoric_Acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Cremer, Josef; Hartmann, Fridolin; Rodis, Franz; Hinz, Arnulf.  Preparation of alkali or alkaline earth phosphates with simultaneous recovery of volatile mineral acids.    Ger.  (1966),     2 pp.  CODEN: GWXXAW  DE  1227435  19661027  CAN 66:12584  AN 1967:12584   </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
      <pubmed_id>29197344</pubmed_id>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00101</protein_accession>
      <name>Diphosphomevalonate decarboxylase</name>
      <uniprot_id>Q0P570</uniprot_id>
      <gene_name>MVD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00118</protein_accession>
      <name>Monofunctional C1-tetrahydrofolate synthase, mitochondrial</name>
      <uniprot_id>Q0VCR7</uniprot_id>
      <gene_name>MTHFD1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00137</protein_accession>
      <name>G protein-coupled receptor kinase 7</name>
      <uniprot_id>Q8WMV0</uniprot_id>
      <gene_name>GRK7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00138</protein_accession>
      <name>Cystic fibrosis transmembrane conductance regulator</name>
      <uniprot_id>P35071</uniprot_id>
      <gene_name>CFTR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00139</protein_accession>
      <name>Serine/threonine-protein phosphatase dullard</name>
      <uniprot_id>Q1RMV9</uniprot_id>
      <gene_name>DULLARD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00140</protein_accession>
      <name>6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 1</name>
      <uniprot_id>P49872</uniprot_id>
      <gene_name>PFKFB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00141</protein_accession>
      <name>Proto-oncogene tyrosine-protein kinase Fyn</name>
      <uniprot_id>A0JNB0</uniprot_id>
      <gene_name>FYN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00142</protein_accession>
      <name>[3-methyl-2-oxobutanoate dehydrogenase [lipoamide]] kinase, mitochondrial</name>
      <uniprot_id>Q2KJG8</uniprot_id>
      <gene_name>BCKDK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00143</protein_accession>
      <name>Insulin-like growth factor 1 receptor</name>
      <uniprot_id>Q05688</uniprot_id>
      <gene_name>IGF1R</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00144</protein_accession>
      <name>Dual specificity protein phosphatase 14</name>
      <uniprot_id>Q17QM8</uniprot_id>
      <gene_name>DUSP14</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00145</protein_accession>
      <name>Sodium/potassium-transporting ATPase subunit alpha-1</name>
      <uniprot_id>Q08DA1</uniprot_id>
      <gene_name>ATP1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00146</protein_accession>
      <name>Activin receptor type-2A</name>
      <uniprot_id>Q28043</uniprot_id>
      <gene_name>ACVR2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00147</protein_accession>
      <name>Arsenical pump-driving ATPase</name>
      <uniprot_id>A5PJI5</uniprot_id>
      <gene_name>ASNA1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00148</protein_accession>
      <name>Glutamine synthetase</name>
      <uniprot_id>P15103</uniprot_id>
      <gene_name>GLUL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00149</protein_accession>
      <name>Cytosolic purine 5'-nucleotidase</name>
      <uniprot_id>O46411</uniprot_id>
      <gene_name>NT5C2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00150</protein_accession>
      <name>Fructose-1,6-bisphosphatase isozyme 2</name>
      <uniprot_id>Q2KJJ9</uniprot_id>
      <gene_name>FBP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00151</protein_accession>
      <name>Acylphosphatase-1</name>
      <uniprot_id>P41500</uniprot_id>
      <gene_name>ACYP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00152</protein_accession>
      <name>Activin receptor type-2B</name>
      <uniprot_id>Q95126</uniprot_id>
      <gene_name>ACVR2B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00153</protein_accession>
      <name>Calcium-transporting ATPase type 2C member 1</name>
      <uniprot_id>P57709</uniprot_id>
      <gene_name>ATP2C1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00154</protein_accession>
      <name>Glyceraldehyde-3-phosphate dehydrogenase</name>
      <uniprot_id>P10096</uniprot_id>
      <gene_name>GAPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00155</protein_accession>
      <name>6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 3</name>
      <uniprot_id>Q28901</uniprot_id>
      <gene_name>PFKFB3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00156</protein_accession>
      <name>Ectonucleoside triphosphate diphosphohydrolase 8</name>
      <uniprot_id>A0JND9</uniprot_id>
      <gene_name>ENTPD8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00157</protein_accession>
      <name>Probable phospholipid-transporting ATPase IIB</name>
      <uniprot_id>A1A4J6</uniprot_id>
      <gene_name>ATP9B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00158</protein_accession>
      <name>Sodium/potassium-transporting ATPase subunit alpha-2</name>
      <uniprot_id>A2VDL6</uniprot_id>
      <gene_name>ATP1A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00159</protein_accession>
      <name>5'-nucleotidase</name>
      <uniprot_id>Q05927</uniprot_id>
      <gene_name>NT5E</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00160</protein_accession>
      <name>Dual specificity protein phosphatase 26</name>
      <uniprot_id>Q17QJ3</uniprot_id>
      <gene_name>DUSP26</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00161</protein_accession>
      <name>Phosphorylase</name>
      <uniprot_id>B0JYK6</uniprot_id>
      <gene_name>PYGM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00162</protein_accession>
      <name>6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 2</name>
      <uniprot_id>P26285</uniprot_id>
      <gene_name>PFKFB2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00163</protein_accession>
      <name>Ectonucleoside triphosphate diphosphohydrolase 1</name>
      <uniprot_id>O18956</uniprot_id>
      <gene_name>ENTPD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00164</protein_accession>
      <name>Dynamin-1</name>
      <uniprot_id>Q08DF4</uniprot_id>
      <gene_name>DNM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00165</protein_accession>
      <name>Glucose-6-phosphatase</name>
      <uniprot_id>Q29RU6</uniprot_id>
      <gene_name>G6PC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00166</protein_accession>
      <name>Beta-adrenergic receptor kinase 2</name>
      <uniprot_id>P26818</uniprot_id>
      <gene_name>ADRBK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00167</protein_accession>
      <name>Dual specificity phosphatase DUPD1</name>
      <uniprot_id>P0C591</uniprot_id>
      <gene_name>DUPD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00168</protein_accession>
      <name>Cell division control protein 2 homolog</name>
      <uniprot_id>P48734</uniprot_id>
      <gene_name>CDC2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00169</protein_accession>
      <name>Folylpolyglutamate synthase, mitochondrial</name>
      <uniprot_id>A6H751</uniprot_id>
      <gene_name>FPGS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00170</protein_accession>
      <name>Dynamin-2</name>
      <uniprot_id>A6H7I5</uniprot_id>
      <gene_name>DNM2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00171</protein_accession>
      <name>Interferon-inducible GTPase 5</name>
      <uniprot_id>Q32KW9</uniprot_id>
      <gene_name>IRGC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00172</protein_accession>
      <name>ITK protein</name>
      <uniprot_id>A7Z039</uniprot_id>
      <gene_name>ITK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00173</protein_accession>
      <name>Glucose-6-phosphatase 3</name>
      <uniprot_id>Q148G2</uniprot_id>
      <gene_name>G6PC3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00174</protein_accession>
      <name>S-adenosylmethionine synthetase</name>
      <uniprot_id>A7E3T7</uniprot_id>
      <gene_name>MAT2A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00175</protein_accession>
      <name>ATP-citrate synthase</name>
      <uniprot_id>Q32PF2</uniprot_id>
      <gene_name>ACLY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00176</protein_accession>
      <name>Fructose-1,6-bisphosphatase 1</name>
      <uniprot_id>Q3SZB7</uniprot_id>
      <gene_name>FBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00177</protein_accession>
      <name>Ectonucleotide pyrophosphatase/phosphodiesterase family member 2</name>
      <uniprot_id>A1A4K5</uniprot_id>
      <gene_name>ENPP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00178</protein_accession>
      <name>G protein-coupled receptor kinase 5</name>
      <uniprot_id>P43249</uniprot_id>
      <gene_name>GRK5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00179</protein_accession>
      <name>YES1 protein</name>
      <uniprot_id>A7MB57</uniprot_id>
      <gene_name>YES1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00180</protein_accession>
      <name>FGR protein</name>
      <uniprot_id>A5PKG9</uniprot_id>
      <gene_name>FGR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00181</protein_accession>
      <name>Dual specificity protein phosphatase 10</name>
      <uniprot_id>Q0IID7</uniprot_id>
      <gene_name>DUSP10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00182</protein_accession>
      <name>Dynamin-1-like protein</name>
      <uniprot_id>Q2KIA5</uniprot_id>
      <gene_name>DNM1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00183</protein_accession>
      <name>Tyrosine-protein kinase receptor</name>
      <uniprot_id>A8KC75</uniprot_id>
      <gene_name>NTRK3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00184</protein_accession>
      <name>Serine/threonine protein phosphatase</name>
      <uniprot_id>A9ZTK8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00185</protein_accession>
      <name>Activated CDC42 kinase 1</name>
      <uniprot_id>Q17R13</uniprot_id>
      <gene_name>TNK2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00186</protein_accession>
      <name>Integrin-linked protein kinase</name>
      <uniprot_id>Q3SWY2</uniprot_id>
      <gene_name>ILK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00187</protein_accession>
      <name>Dual specificity protein phosphatase 18</name>
      <uniprot_id>Q5BIP9</uniprot_id>
      <gene_name>DUSP18</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00188</protein_accession>
      <name>Serine/threonine protein phosphatase</name>
      <uniprot_id>A5D7T5</uniprot_id>
      <gene_name>PPP3CC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00189</protein_accession>
      <name>ATP synthase subunit beta, mitochondrial</name>
      <uniprot_id>P00829</uniprot_id>
      <gene_name>ATP5B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00190</protein_accession>
      <name>Putative tyrosine-protein phosphatase auxilin</name>
      <uniprot_id>Q27974</uniprot_id>
      <gene_name>DNAJC6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00191</protein_accession>
      <name>ATP10D protein</name>
      <uniprot_id>A7Z029</uniprot_id>
      <gene_name>ATP10D</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00192</protein_accession>
      <name>Acylphosphatase-2</name>
      <uniprot_id>P07033</uniprot_id>
      <gene_name>ACYP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00193</protein_accession>
      <name>2',3'-cyclic-nucleotide 3'-phosphodiesterase</name>
      <uniprot_id>P06623</uniprot_id>
      <gene_name>CNP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00194</protein_accession>
      <name>Eyes absent homolog 2</name>
      <uniprot_id>Q58DB6</uniprot_id>
      <gene_name>EYA2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00195</protein_accession>
      <name>3'(2'),5'-bisphosphate nucleotidase 1</name>
      <uniprot_id>Q3ZCK3</uniprot_id>
      <gene_name>BPNT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00196</protein_accession>
      <name>Probable phospholipid-transporting ATPase IA</name>
      <uniprot_id>Q29449</uniprot_id>
      <gene_name>ATP8A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00197</protein_accession>
      <name>Glutathione synthetase</name>
      <uniprot_id>Q5EAC2</uniprot_id>
      <gene_name>GSS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00198</protein_accession>
      <name>Alkaline phosphatase</name>
      <uniprot_id>A6QQR9</uniprot_id>
      <gene_name>LOC100125266</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00199</protein_accession>
      <name>Cell division protein kinase 9</name>
      <uniprot_id>Q5EAB2</uniprot_id>
      <gene_name>CDK9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00200</protein_accession>
      <name>Tyrosine-protein kinase receptor</name>
      <uniprot_id>A7Z067</uniprot_id>
      <gene_name>CSF1R</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00201</protein_accession>
      <name>Nucleoside-triphosphatase C1orf57 homolog</name>
      <uniprot_id>Q1LZ78</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00202</protein_accession>
      <name>Beta-adrenergic receptor kinase 1</name>
      <uniprot_id>P21146</uniprot_id>
      <gene_name>ADRBK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00203</protein_accession>
      <name>Tyrosine-protein kinase CSK</name>
      <uniprot_id>Q0VBZ0</uniprot_id>
      <gene_name>CSK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00204</protein_accession>
      <name>Acetyl-CoA carboxylase 1</name>
      <uniprot_id>Q9TTS3</uniprot_id>
      <gene_name>ACACA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00205</protein_accession>
      <name>Activin receptor type-1</name>
      <uniprot_id>Q28041</uniprot_id>
      <gene_name>ACVR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00206</protein_accession>
      <name>Dual specificity protein phosphatase 6</name>
      <uniprot_id>Q2KJ36</uniprot_id>
      <gene_name>DUSP6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00207</protein_accession>
      <name>Sarcoplasmic/endoplasmic reticulum calcium ATPase 1</name>
      <uniprot_id>Q0VCY0</uniprot_id>
      <gene_name>ATP2A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00208</protein_accession>
      <name>Serine/threonine protein phosphatase</name>
      <uniprot_id>A6H703</uniprot_id>
      <gene_name>PPP3CB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00209</protein_accession>
      <name>Glyceraldehyde-3-phosphate dehydrogenase, testis-specific</name>
      <uniprot_id>Q2KJE5</uniprot_id>
      <gene_name>GAPDHS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00210</protein_accession>
      <name>Enolase-phosphatase E1</name>
      <uniprot_id>Q0VD27</uniprot_id>
      <gene_name>ENOPH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00211</protein_accession>
      <name>Tyrosine-protein kinase</name>
      <uniprot_id>A3KMY9</uniprot_id>
      <gene_name>JAK1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01357</protein_accession>
      <name>SLC34A1 protein</name>
      <uniprot_id>A7YY70</uniprot_id>
      <gene_name>SLC34A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01358</protein_accession>
      <name>Growth hormone receptor</name>
      <uniprot_id>B3VHT8</uniprot_id>
      <gene_name>ghr</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01359</protein_accession>
      <name>Annexin A3</name>
      <uniprot_id>Q3SWX7</uniprot_id>
      <gene_name>ANXA3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01360</protein_accession>
      <name>ANKH protein</name>
      <uniprot_id>A8E659</uniprot_id>
      <gene_name>ANKH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:51 UTC</creation_date>
  <update_date>2020-03-13 16:28:00 UTC</update_date>
  <accession>BMDB0001430</accession>
  <secondary_accessions>
    <accession>BMDB01430</accession>
  </secondary_accessions>
  <name>L-Dopachrome</name>
  <description/>
  <synonyms>
    <synonym>2-L-Carboxy-2,3-dihydroindole-5,6-quinone</synonym>
  </synonyms>
  <chemical_formula>C9H7NO4</chemical_formula>
  <average_molecular_weight>193.158</average_molecular_weight>
  <monisotopic_moleculate_weight>193.037507709</monisotopic_moleculate_weight>
  <iupac_name>(2S)-5,6-dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acid</iupac_name>
  <traditional_iupac>L-dopachrome</traditional_iupac>
  <cas_registry_number>89762-39-0</cas_registry_number>
  <smiles>OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1</smiles>
  <inchi>InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10H,1H2,(H,13,14)/t6-/m0/s1</inchi>
  <inchikey>VJNCICVKUHKIIV-LURJTMIESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Enamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Indolines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrrolidine carboxylic acids</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Dihydroindole</substituent>
      <substituent>Enamine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indole or derivatives</substituent>
      <substituent>Ketone</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidine carboxylic acid</substituent>
      <substituent>Pyrrolidine carboxylic acid or derivatives</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>dopachrome</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.087</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-8.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-5,6-dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>193.158</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>193.037507709</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)[C@@H]1CC2=CC(=O)C(=O)C=C2N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H7NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10H,1H2,(H,13,14)/t6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VJNCICVKUHKIIV-LURJTMIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>83.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1298716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1298717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1298718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1413322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1413323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1413324</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01693</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022618</foodb_id>
  <pubchem_compound_id>5459802</pubchem_compound_id>
  <chemspider_id>4573572</chemspider_id>
  <chebi_id>15772</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id>Dopachrome</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00123</protein_accession>
      <name>Macrophage migration inhibitory factor</name>
      <uniprot_id>P80177</uniprot_id>
      <gene_name>MIF</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00125</protein_accession>
      <name>L-dopachrome tautomerase</name>
      <uniprot_id>Q95119</uniprot_id>
      <gene_name>DCT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:52 UTC</creation_date>
  <update_date>2020-04-14 22:49:14 UTC</update_date>
  <accession>BMDB0001431</accession>
  <secondary_accessions>
    <accession>BMDB01431</accession>
  </secondary_accessions>
  <name>Pyridoxamine</name>
  <description>Pyridoxamine, also known as PM, belongs to the class of organic compounds known as pyridoxamine 5'-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5'-position. Pyridoxamine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Pyridoxamine exists in all living species, ranging from bacteria to humans. Pyridoxamine participates in a number of enzymatic reactions, within cattle. In particular, Pyridoxamine can be converted into pyridoxal; which is catalyzed by the enzyme pyridoxine-5'-phosphate oxidase. In addition, Pyridoxamine can be converted into pyridoxamine 5'-phosphate through its interaction with the enzyme pyridoxal kinase. In cattle, pyridoxamine is involved in the metabolic pathway called the vitamin B6 metabolism pathway.</description>
  <synonyms>
    <synonym>4-(AMINOMETHYL)-5-(hydroxymethyl)-2-methylpyridin-3-ol</synonym>
    <synonym>PM</synonym>
    <synonym>2-Methyl-4-aminomethyl-5-hydroxymethyl-3-pyridinol</synonym>
    <synonym>4-(Aminomethyl)-5-(hydroxymethyl)-2-methyl-3-pyridinol</synonym>
    <synonym>4-(Aminomethyl)-5-hydroxy-6-methyl-3-pyridinemethanol</synonym>
    <synonym>Pyridoxylamine</synonym>
  </synonyms>
  <chemical_formula>C8H12N2O2</chemical_formula>
  <average_molecular_weight>168.1931</average_molecular_weight>
  <monisotopic_moleculate_weight>168.089877638</monisotopic_moleculate_weight>
  <iupac_name>4-(aminomethyl)-5-(hydroxymethyl)-2-methylpyridin-3-ol</iupac_name>
  <traditional_iupac>pyridoxamine</traditional_iupac>
  <cas_registry_number>85-87-0</cas_registry_number>
  <smiles>CC1=C(O)C(CN)=C(CO)C=N1</smiles>
  <inchi>InChI=1S/C8H12N2O2/c1-5-8(12)7(2-9)6(4-11)3-10-5/h3,11-12H,2,4,9H2,1H3</inchi>
  <inchikey>NHZMQXZHNVQTQA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridoxamine 5'-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5'-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyridoxamines</sub_class>
    <direct_parent>Pyridoxamine 5'-phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyridines</alternative_parent>
      <alternative_parent>Methylpyridines</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyridine</substituent>
      <substituent>Methylpyridine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyridoxamine 5'-phosphate</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Water-soluble vitamins</external_descriptor>
      <external_descriptor>aminoalkylpyridine</external_descriptor>
      <external_descriptor>hydroxymethylpyridine</external_descriptor>
      <external_descriptor>monohydroxypyridine</external_descriptor>
      <external_descriptor>vitamin B6</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>815 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-(aminomethyl)-5-(hydroxymethyl)-2-methylpyridin-3-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>168.1931</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>168.089877638</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(O)C(CN)=C(CO)C=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H12N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H12N2O2/c1-5-8(12)7(2-9)6(4-11)3-10-5/h3,11-12H,2,4,9H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NHZMQXZHNVQTQA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>79.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Vitamin B6 Metabolism</name>
      <smpdb_id>SMP0087240</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4991</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447950</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.099 +/- 0.038</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Coburn SP, Mahuren JD, Pauly TA, Ericson KL, Townsend DW: Alkaline phosphatase activity and pyridoxal phosphate concentrations in the milk of various species. J Nutr. 1992 Dec;122(12):2348-53. doi: 10.1093/jn/122.12.2348.</reference_text>
          <pubmed_id>1453218</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00534</kegg_id>
  <drugbank_id>DB11673</drugbank_id>
  <foodb_id>FDB021819</foodb_id>
  <pubchem_compound_id>1052</pubchem_compound_id>
  <chemspider_id>1023</chemspider_id>
  <chebi_id>16410</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00007504</knapsack_id>
  <meta_cyc_id>PYRIDOXAMINE</meta_cyc_id>
  <wikipedia_id>Pyridoxamine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35277</bigg_id>
  <metlin_id>238</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Coburn SP, Mahuren JD, Pauly TA, Ericson KL, Townsend DW: Alkaline phosphatase activity and pyridoxal phosphate concentrations in the milk of various species. J Nutr. 1992 Dec;122(12):2348-53. doi: 10.1093/jn/122.12.2348.</reference_text>
      <pubmed_id>1453218</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:53 UTC</creation_date>
  <update_date>2020-04-15 21:36:02 UTC</update_date>
  <accession>BMDB0001432</accession>
  <secondary_accessions>
    <accession>BMDB01432</accession>
  </secondary_accessions>
  <name>Agmatine</name>
  <description/>
  <synonyms>
    <synonym>(4-Aminobutyl) guanidine</synonym>
    <synonym>(4-Aminobutyl)guanidine</synonym>
    <synonym>N-(4-Aminobutyl)guanidine</synonym>
    <synonym>(4-Aminobutyl)-guanidine</synonym>
    <synonym>1-(4-Aminobutyl)guanidine</synonym>
    <synonym>1-Amino-4-guanidinobutane</synonym>
    <synonym>1-Amino-4-guanidobutane</synonym>
    <synonym>4-Guanidino-1-butanamine</synonym>
    <synonym>Agmatinium</synonym>
    <synonym>Argmatine</synonym>
    <synonym>N-(Aminoiminomethyl)-1,4-butanediamine</synonym>
    <synonym>N-4-Aminobutylguanidine</synonym>
    <synonym>1 Amino 4 guanidinobutane</synonym>
    <synonym>4-(Aminobutyl)guanidine</synonym>
  </synonyms>
  <chemical_formula>C5H14N4</chemical_formula>
  <average_molecular_weight>130.1915</average_molecular_weight>
  <monisotopic_moleculate_weight>130.121846468</monisotopic_moleculate_weight>
  <iupac_name>N-(4-aminobutyl)guanidine</iupac_name>
  <traditional_iupac>agmatine</traditional_iupac>
  <cas_registry_number>306-60-5</cas_registry_number>
  <smiles>NCCCCNC(N)=N</smiles>
  <inchi>InChI=1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9)</inchi>
  <inchikey>QYPPJABKJHAVHS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Guanidines</sub_class>
    <direct_parent>Guanidines</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Amines</external_descriptor>
      <external_descriptor>guanidines</external_descriptor>
      <external_descriptor>primary amino compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>12.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-(4-aminobutyl)guanidine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>130.1915</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>130.121846468</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCCNC(N)=N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H14N4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QYPPJABKJHAVHS-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>87.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>48.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5316</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5320</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22887</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22888</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451914</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00179</kegg_id>
  <drugbank_id>DB08838</drugbank_id>
  <foodb_id>FDB008310</foodb_id>
  <pubchem_compound_id>199</pubchem_compound_id>
  <chemspider_id>194</chemspider_id>
  <chebi_id>17431</chebi_id>
  <pdbe_id/>
  <knapsack_id>C00001400</knapsack_id>
  <meta_cyc_id/>
  <wikipedia_id>Agmatine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34153</bigg_id>
  <metlin_id>3523</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:54 UTC</creation_date>
  <update_date>2020-03-13 16:28:02 UTC</update_date>
  <accession>BMDB0001433</accession>
  <secondary_accessions>
    <accession>BMDB01433</accession>
  </secondary_accessions>
  <name>Diadenosine heptaphosphate</name>
  <description/>
  <synonyms>
    <synonym>Diadenosine heptaphosphoric acid</synonym>
    <synonym>Adenosine 5'-(octahydrogen heptaphosphate)</synonym>
    <synonym>Ap7a</synonym>
    <synonym>Bis({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinate</synonym>
  </synonyms>
  <chemical_formula>C20H31N10O28P7</chemical_formula>
  <average_molecular_weight>1076.3267</average_molecular_weight>
  <monisotopic_moleculate_weight>1075.947256042</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>Ap7A</traditional_iupac>
  <cas_registry_number>106597-55-1</cas_registry_number>
  <smiles>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C20H31N10O28P7/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(51-19)1-49-59(35,36)53-61(39,40)55-63(43,44)57-65(47,48)58-64(45,46)56-62(41,42)54-60(37,38)50-2-8-12(32)14(34)20(52-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H,47,48)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1</inchi>
  <inchikey>IBORMIZOWBHWTG-XPWFQUROSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside polyphosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside polyphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-8.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1076.3267</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1075.947256042</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H31N10O28P7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H31N10O28P7/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(51-19)1-49-59(35,36)53-61(39,40)55-63(43,44)57-65(47,48)58-64(45,46)56-62(41,42)54-60(37,38)50-2-8-12(32)14(34)20(52-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H,47,48)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IBORMIZOWBHWTG-XPWFQUROSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>573.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>198.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>80.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>298833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>340710</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id/>
  <foodb_id>FDB022619</foodb_id>
  <pubchem_compound_id>53477728</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:56 UTC</creation_date>
  <update_date>2020-03-13 16:28:03 UTC</update_date>
  <accession>BMDB0001434</accession>
  <secondary_accessions>
    <accession>BMDB01434</accession>
  </secondary_accessions>
  <name>3-Methoxytyrosine</name>
  <description/>
  <synonyms>
    <synonym>3-Methoxy-tyrosine</synonym>
    <synonym>3-O-Methyldopa</synonym>
    <synonym>L-3-Methoxy tyrosine</synonym>
    <synonym>L-3-Methoxytyrosine</synonym>
    <synonym>L-4-Hydroxy-3-methoxyphenylalanine</synonym>
    <synonym>Vanilalanine</synonym>
    <synonym>3-Methoxytyrosine, (L-tyr)-isomer</synonym>
    <synonym>3-Methoxytyrosine, (D-tyr)-isomer</synonym>
    <synonym>3-Methoxytyrosine, (L-tyr)-isomer, alpha-(14)C-labeled</synonym>
    <synonym>3-Methoxytyrosine, (DL-tyr)-isomer</synonym>
    <synonym>3-O-Methyl-dopa</synonym>
    <synonym>3-OMD CPD</synonym>
    <synonym>3-Methoxydopa</synonym>
    <synonym>2-Amino-3-(4-hydroxy-3-methoxyphenyl)propanoate</synonym>
    <synonym>3-Methoxytyrosine</synonym>
  </synonyms>
  <chemical_formula>C10H13NO4</chemical_formula>
  <average_molecular_weight>211.2145</average_molecular_weight>
  <monisotopic_moleculate_weight>211.084457909</monisotopic_moleculate_weight>
  <iupac_name>2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acid</iupac_name>
  <traditional_iupac>3-O-methyldopa</traditional_iupac>
  <cas_registry_number>7636-26-2</cas_registry_number>
  <smiles>COC1=C(O)C=CC(CC(N)C(O)=O)=C1</smiles>
  <inchi>InChI=1S/C10H13NO4/c1-15-9-5-6(2-3-8(9)12)4-7(11)10(13)14/h2-3,5,7,12H,4,11H2,1H3,(H,13,14)</inchi>
  <inchikey>PFDUUKDQEHURQC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Tyrosine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Alpha amino acids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Phenylalanine and derivatives</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Tyrosine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a guaiacol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>211.2145</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>211.084457909</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=C(O)C=CC(CC(N)C(O)=O)=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H13NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H13NO4/c1-15-9-5-6(2-3-8(9)12)4-7(11)10(13)14/h2-3,5,7,12H,4,11H2,1H3,(H,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PFDUUKDQEHURQC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>53.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>49803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>49804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>49805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122729</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>1607</chemspider_id>
  <foodb_id>FDB022620</foodb_id>
  <pubchem_compound_id>1670</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Zampella Angela; D'Orsi Rosa; Sepe Valentina; Casapullo Agostino; Monti Maria Chiara; D'Auria Maria Valeria  Concise synthesis of all stereoisomers of beta-methoxytyrosine and determination of the absolute configuration of the residue in callipeltin A.    Organic letters  (2005),  7(16),  3585-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:57 UTC</creation_date>
  <update_date>2020-03-13 16:28:03 UTC</update_date>
  <accession>BMDB0001438</accession>
  <secondary_accessions>
    <accession>BMDB01438</accession>
  </secondary_accessions>
  <name>25-Hydroxyvitamin D2</name>
  <description/>
  <synonyms>
    <synonym>25-Hydroxycalciferol</synonym>
    <synonym>25-Hydroxyergocalciferol</synonym>
    <synonym>25-Hydroxyvitamin D</synonym>
    <synonym>9,10-Secoergosta-5,7,10(19),22-tetraene-3b,25-diol</synonym>
    <synonym>Ercalcidiol</synonym>
    <synonym>25 Hydroxycalciferol</synonym>
    <synonym>9,10-Secoergosta-5,7,10(19),22-tetraene-3 beta,25-diol</synonym>
    <synonym>25 Hydroxyvitamin D2</synonym>
    <synonym>25-Hydroxyvitamin D 2</synonym>
    <synonym>25 Hydroxyvitamin D 2</synonym>
    <synonym>25 Hydroxyergocalciferol</synonym>
    <synonym>25-Hydroxyvitamin D2</synonym>
  </synonyms>
  <chemical_formula>C28H44O2</chemical_formula>
  <average_molecular_weight>412.6478</average_molecular_weight>
  <monisotopic_moleculate_weight>412.334130652</monisotopic_moleculate_weight>
  <iupac_name>(1S,3Z)-3-{2-[(3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol</iupac_name>
  <traditional_iupac>25-hydroxyvitamin D</traditional_iupac>
  <cas_registry_number>21343-40-8</cas_registry_number>
  <smiles>C[C@H](\C=C\[C@H](C)C(O)(C)C)C1CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C</smiles>
  <inchi>InChI=1S/C28H44O2/c1-19-10-14-24(29)18-23(19)13-12-22-8-7-17-28(6)25(15-16-26(22)28)20(2)9-11-21(3)27(4,5)30/h9,11-13,20-21,24-26,29-30H,1,7-8,10,14-18H2,2-6H3/b11-9+,22-12+,23-13-/t20-,21+,24+,25?,26+,28-/m1/s1</inchi>
  <inchikey>KJKIIUAXZGLUND-BJWBXCNSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Vitamin D and derivatives</sub_class>
    <direct_parent>Vitamin D and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Triterpenoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,3Z)-3-{2-[(3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>412.6478</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>412.334130652</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](\C=C\[C@H](C)C(O)(C)C)C1CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C28H44O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C28H44O2/c1-19-10-14-24(29)18-23(19)13-12-22-8-7-17-28(6)25(15-16-26(22)28)20(2)9-11-21(3)27(4,5)30/h9,11-13,20-21,24-26,29-30H,1,7-8,10,14-18H2,2-6H3/b11-9+,22-12+,23-13-/t20-,21+,24+,25?,26+,28-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KJKIIUAXZGLUND-BJWBXCNSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>130.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>67227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>67228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>67229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>124983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>124984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>124985</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>17216121</chemspider_id>
  <foodb_id>FDB022621</foodb_id>
  <pubchem_compound_id>22833566</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>2289188</bigg_id>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Sardina, F. Javier; Mourino, Antonio; Castedo, Luis. Studies on the synthesis of side-chain hydroxylated metabolites of vitamin D. 2. Stereocontrolled synthesis of 25-hydroxyvitamin D2. Journal of Organic Chemistry (1986), 51(8), 1264-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:58 UTC</creation_date>
  <update_date>2020-03-13 16:28:04 UTC</update_date>
  <accession>BMDB0001439</accession>
  <secondary_accessions>
    <accession>BMDB01439</accession>
  </secondary_accessions>
  <name>Phosphoribosyl formamidocarboxamide</name>
  <description/>
  <synonyms>
    <synonym>1-(5'-Phosphoribosyl)-5-formamido-4-imidazolecarboxamide</synonym>
    <synonym>5'-Phosphoribosyl-5-formamido-4-imidazolecarboxamide</synonym>
    <synonym>5-Formamido-1-(5-phosphoribosyl)imidazole-4-carboxamide</synonym>
    <synonym>FAICAR</synonym>
    <synonym>5-Formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide</synonym>
    <synonym>5'-p-Ribosyl-5-formamido-4-imidazole carboxamide</synonym>
    <synonym>5'-Phosphoribosyl-5-formamido-4-imidazole carboxamide</synonym>
    <synonym>5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide</synonym>
    <synonym>5-Formamido-1-(5-phosphoribosyl)-imidazole-4-carboxamide</synonym>
    <synonym>5-Phosphoribosyl-5-formamido-4-imid-carboxamide</synonym>
    <synonym>Phosphoribosyl-formamido-carboxamide</synonym>
    <synonym>5-Formamidoimidazole-4-carboxamide ribotide</synonym>
  </synonyms>
  <chemical_formula>C10H15N4O9P</chemical_formula>
  <average_molecular_weight>366.2213</average_molecular_weight>
  <monisotopic_moleculate_weight>366.05766461</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(4-carbamoyl-5-formamido-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(4-carbamoyl-5-formamidoimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>NC(=O)C1=C(NC=O)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C10H15N4O9P/c11-8(18)5-9(13-3-15)14(2-12-5)10-7(17)6(16)4(23-10)1-22-24(19,20)21/h2-4,6-7,10,16-17H,1H2,(H2,11,18)(H,13,15)(H2,19,20,21)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>ABCOOORLYAOBOZ-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Imidazole ribonucleosides and ribonucleotides</class>
    <sub_class>1-ribosyl-imidazolecarboxamides</sub_class>
    <direct_parent>1-ribosyl-imidazolecarboxamides</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>2-heteroaryl carboxamides</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbonylimidazoles</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-arylamides</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>1-ribosyl-imidazolecarboxamide</substituent>
      <substituent>2-heteroaryl carboxamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazole-4-carbonyl group</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-arylamide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>1-(phosphoribosyl)imidazolecarboxamide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(4-carbamoyl-5-formamido-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>366.2213</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>366.05766461</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)C1=C(NC=O)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H15N4O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H15N4O9P/c11-8(18)5-9(13-3-15)14(2-12-5)10-7(17)6(16)4(23-10)1-22-24(19,20)21/h2-4,6-7,10,16-17H,1H2,(H2,11,18)(H,13,15)(H2,19,20,21)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ABCOOORLYAOBOZ-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>206.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>74.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>30.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34399</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>145893</chemspider_id>
  <foodb_id>FDB031113</foodb_id>
  <pubchem_compound_id>166760</pubchem_compound_id>
  <kegg_id>C04734</kegg_id>
  <pdbe_id/>
  <chebi_id>18381</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>44434</bigg_id>
  <wikipedia_id/>
  <metlin_id>6247</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00598</protein_accession>
      <name>Bifunctional purine biosynthesis protein PURH</name>
      <uniprot_id>Q0VCK0</uniprot_id>
      <gene_name>ATIC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00935</protein_accession>
      <name>Adenylosuccinate lyase</name>
      <uniprot_id>A3KN12</uniprot_id>
      <gene_name>ADSL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:45:59 UTC</creation_date>
  <update_date>2020-03-13 16:28:04 UTC</update_date>
  <accession>BMDB0001440</accession>
  <secondary_accessions>
    <accession>BMDB01440</accession>
  </secondary_accessions>
  <name>dGTP</name>
  <description/>
  <synonyms>
    <synonym>2'-Deoxyguanosine 5'-triphosphate</synonym>
    <synonym>Deoxyguanosine 5'-triphosphate</synonym>
    <synonym>Deoxyguanosine triphosphate</synonym>
    <synonym>2'-Deoxyguanosine 5'-triphosphoric acid</synonym>
    <synonym>Deoxyguanosine 5'-triphosphoric acid</synonym>
    <synonym>Deoxyguanosine triphosphoric acid</synonym>
    <synonym>2'-Deoxyguanosine triphosphate</synonym>
    <synonym>Deoxy-GTP</synonym>
    <synonym>Deoxyguanosine triphosphate, 3H-labeled</synonym>
  </synonyms>
  <chemical_formula>C10H16N5O13P3</chemical_formula>
  <average_molecular_weight>507.181</average_molecular_weight>
  <monisotopic_moleculate_weight>506.995745159</monisotopic_moleculate_weight>
  <iupac_name>({[({[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</iupac_name>
  <traditional_iupac>dGTP</traditional_iupac>
  <cas_registry_number>2564-35-4</cas_registry_number>
  <smiles>NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)N1</smiles>
  <inchi>InChI=1S/C10H16N5O13P3/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(26-6)2-25-30(21,22)28-31(23,24)27-29(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1</inchi>
  <inchikey>HAAZLUGHYHWQIW-KVQBGUIXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate group  linked to the ribose moiety lacking a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine deoxyribonucleotides</sub_class>
    <direct_parent>Purine 2'-deoxyribonucleoside triphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Purines and purine derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine 2'-deoxyribonucleoside triphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Deoxyribonucleotides</external_descriptor>
      <external_descriptor>deoxyguanosine phosphate</external_descriptor>
      <external_descriptor>guanyl deoxyribonucleotide</external_descriptor>
      <external_descriptor>purine 2'-deoxyribonucleoside 5'-triphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>({[({[(2R,3S,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>507.181</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>506.995745159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O2)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H16N5O13P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H16N5O13P3/c11-10-13-8-7(9(17)14-10)12-3-15(8)6-1-4(16)5(26-6)2-25-30(21,22)28-31(23,24)27-29(18,19)20/h3-6,16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,11,13,14,17)/t4-,5+,6+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HAAZLUGHYHWQIW-KVQBGUIXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>274.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>95.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4957</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>58613</chemspider_id>
  <foodb_id>FDB022623</foodb_id>
  <pubchem_compound_id>65103</pubchem_compound_id>
  <kegg_id>C00286</kegg_id>
  <pdbe_id/>
  <chebi_id>16497</chebi_id>
  <drugbank_id>DB02181</drugbank_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00019346</knapsack_id>
  <bigg_id>34502</bigg_id>
  <wikipedia_id>Deoxyguanosine triphosphate</wikipedia_id>
  <metlin_id>6248</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:01 UTC</creation_date>
  <update_date>2020-03-13 16:28:05 UTC</update_date>
  <accession>BMDB0001441</accession>
  <secondary_accessions>
    <accession>BMDB01441</accession>
  </secondary_accessions>
  <name>Dihydropteridine</name>
  <description/>
  <synonyms>
    <synonym>6,7-Dihydropteridine</synonym>
    <synonym>Dihydropteridine</synonym>
  </synonyms>
  <chemical_formula>C6H6N4</chemical_formula>
  <average_molecular_weight>134.1386</average_molecular_weight>
  <monisotopic_moleculate_weight>134.059246212</monisotopic_moleculate_weight>
  <iupac_name>6,7-dihydropteridine</iupac_name>
  <traditional_iupac>dihydropteridine</traditional_iupac>
  <cas_registry_number/>
  <smiles>C1CN=C2N=CN=CC2=N1</smiles>
  <inchi>InChI=1S/C6H6N4/c1-2-9-6-5(8-1)3-7-4-10-6/h3-4H,1-2H2</inchi>
  <inchikey>KVDQMARGGBLIJM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form  pyrimido(4,5-b)pyrazine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class/>
    <direct_parent>Pteridines and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidines and pyrimidine derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pteridine</substituent>
      <substituent>Pyrimidine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>6,7-dihydropteridines</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6,7-dihydropteridine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>134.1386</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>134.059246212</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C1CN=C2N=CN=CC2=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H6N4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H6N4/c1-2-9-6-5(8-1)3-7-4-10-6/h3-4H,1-2H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KVDQMARGGBLIJM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>49.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>36.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30253</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>162</chemspider_id>
  <foodb_id>FDB022624</foodb_id>
  <kegg_id>C05649</kegg_id>
  <chebi_id>30156</chebi_id>
  <pubchem_compound_id>167</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6249</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00597</protein_accession>
      <name>Dihydropteridine reductase</name>
      <uniprot_id>Q3T0Z7</uniprot_id>
      <gene_name>QDPR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:02 UTC</creation_date>
  <update_date>2020-04-16 20:38:01 UTC</update_date>
  <accession>BMDB0001442</accession>
  <secondary_accessions>
    <accession>BMDB01442</accession>
  </secondary_accessions>
  <name>Prostaglandin E1</name>
  <description/>
  <synonyms>
    <synonym>(11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid</synonym>
    <synonym>(13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate</synonym>
    <synonym>11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acid</synonym>
    <synonym>Alprostadil</synonym>
    <synonym>Alprostadilum</synonym>
    <synonym>Befar</synonym>
    <synonym>Caverject</synonym>
    <synonym>Edex</synonym>
    <synonym>Muse</synonym>
    <synonym>PGE-1</synonym>
    <synonym>PGE1</synonym>
    <synonym>Prostin VR</synonym>
    <synonym>Prostin VR pediatric</synonym>
    <synonym>(11a,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oate</synonym>
    <synonym>(11a,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid</synonym>
    <synonym>(11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oate</synonym>
    <synonym>(11Α,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oate</synonym>
    <synonym>(11Α,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oic acid</synonym>
    <synonym>(13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoate</synonym>
    <synonym>(13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acid</synonym>
    <synonym>(13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acid</synonym>
    <synonym>(13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoate</synonym>
    <synonym>(13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoic acid</synonym>
    <synonym>11a,15a-Dihydroxy-9-oxo-13-trans-prostenoate</synonym>
    <synonym>11a,15a-Dihydroxy-9-oxo-13-trans-prostenoic acid</synonym>
    <synonym>11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoate</synonym>
    <synonym>11Α,15α-dihydroxy-9-oxo-13-trans-prostenoate</synonym>
    <synonym>11Α,15α-dihydroxy-9-oxo-13-trans-prostenoic acid</synonym>
    <synonym>Prink</synonym>
    <synonym>Vitaros</synonym>
    <synonym>Caverject impulse</synonym>
    <synonym>U-10136prostin</synonym>
    <synonym>U-10136alprostadil</synonym>
    <synonym>(+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate</synonym>
    <synonym>(+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid</synonym>
    <synonym>(-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate</synonym>
    <synonym>(-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid</synonym>
    <synonym>(-)-Prostaglandin e1</synonym>
    <synonym>(13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoate</synonym>
    <synonym>(13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid</synonym>
    <synonym>(13E)-(15S)-11-alpha,15-Dihydroxy-9-oxoprost-13-enoate</synonym>
    <synonym>(13E)-(15S)-11-alpha,15-Dihydroxy-9-oxoprost-13-enoic acid</synonym>
    <synonym>11,15-Dihydroxy-9-oxoprost-13-en-1-Oate</synonym>
    <synonym>11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid</synonym>
    <synonym>11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid (acd/name 4.0)</synonym>
    <synonym>3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate</synonym>
    <synonym>3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid</synonym>
    <synonym>Alprostadil prostoglandin e1</synonym>
    <synonym>Alprostadil(usan)</synonym>
    <synonym>L-Prostaglandin e1</synonym>
    <synonym>Lipo pge1</synonym>
    <synonym>Lipo-pge1</synonym>
    <synonym>Viridal</synonym>
    <synonym>Prostaglandin e1alpha</synonym>
    <synonym>Sugiran</synonym>
    <synonym>Vasaprostan</synonym>
    <synonym>Minprog</synonym>
    <synonym>PGE1alpha</synonym>
    <synonym>Prostavasin</synonym>
    <synonym>Prostine VR</synonym>
    <synonym>Abbott brand OF alprostadil</synonym>
    <synonym>Paladin brand OF alprostadil</synonym>
    <synonym>Schwarz pharma brand OF alprostadil</synonym>
    <synonym>Astra brand OF alprostadil</synonym>
    <synonym>Hoyer brand OF alprostadil</synonym>
    <synonym>Allphar brand OF alprostadil</synonym>
    <synonym>AstraZeneca brand OF alprostadil</synonym>
    <synonym>Janssen brand OF alprostadil</synonym>
    <synonym>Pharmacia brand 1 OF alprostadil</synonym>
    <synonym>Pharmacia brand 2 OF alprostadil</synonym>
    <synonym>Schwarz brand OF alprostadil</synonym>
    <synonym>Vivus brand OF alprostadil</synonym>
    <synonym>Prostaglandin e1</synonym>
  </synonyms>
  <chemical_formula>C20H34O5</chemical_formula>
  <average_molecular_weight>354.487</average_molecular_weight>
  <monisotopic_moleculate_weight>354.240624195</monisotopic_moleculate_weight>
  <iupac_name>7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid</iupac_name>
  <traditional_iupac>alprostadil</traditional_iupac>
  <cas_registry_number>745-65-3</cas_registry_number>
  <smiles>CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1</inchi>
  <inchikey>GMVPRGQOIOIIMI-DWKJAMRDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Prostaglandins and related compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Cyclopentanols</alternative_parent>
      <alternative_parent>Fatty alcohols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclopentanol</substituent>
      <substituent>Fatty alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Prostaglandin skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>prostaglandins E</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>354.487</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>354.240624195</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H34O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GMVPRGQOIOIIMI-DWKJAMRDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>94.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>98.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>42.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>50532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>50533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>50534</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>4444306</chemspider_id>
  <foodb_id>FDB022625</foodb_id>
  <pubchem_compound_id>5280723</pubchem_compound_id>
  <kegg_id>C04741</kegg_id>
  <pdbe_id/>
  <chebi_id>15544</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>44455</bigg_id>
  <wikipedia_id>Prostaglandin_E1</wikipedia_id>
  <metlin_id>416</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Liang, Yong-tao; Wei, Feng-ping; Li, Gui-ying; Wang, En-si.  Chemoenzymic synthesis of prostaglandin E1.    Jilin Daxue Ziran Kexue Xuebao  (2001),   (2),  77-80.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:03 UTC</creation_date>
  <update_date>2020-03-13 16:28:06 UTC</update_date>
  <accession>BMDB0001443</accession>
  <secondary_accessions>
    <accession>BMDB01443</accession>
  </secondary_accessions>
  <name>Phosphite</name>
  <description/>
  <synonyms>
    <synonym>[p(OH)3]</synonym>
    <synonym>H3PO3</synonym>
    <synonym>p(OH)3</synonym>
    <synonym>Phosphorige saeure</synonym>
    <synonym>Phosphorus trihydroxide</synonym>
    <synonym>Phosphonic acid</synonym>
    <synonym>Dihydroxyphosphine oxide</synonym>
    <synonym>Phosphite</synonym>
  </synonyms>
  <chemical_formula>H3O3P</chemical_formula>
  <average_molecular_weight>81.995</average_molecular_weight>
  <monisotopic_moleculate_weight>81.981980955</monisotopic_moleculate_weight>
  <iupac_name>phosphorous acid</iupac_name>
  <traditional_iupac>phosphorous acid</traditional_iupac>
  <cas_registry_number>14901-63-4</cas_registry_number>
  <smiles>OP(O)O</smiles>
  <inchi>InChI=1S/H3O3P/c1-4(2)3/h1-3H</inchi>
  <inchikey>OJMIONKXNSYLSR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as non-metal phosphites. These are inorganic non-metallic compounds containing a phosphite as its largest oxoanion.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Non-metal oxoanionic compounds</class>
    <sub_class>Non-metal phosphites</sub_class>
    <direct_parent>Non-metal phosphites</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Non-metal phosphite</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>phosphorus oxoacid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>17.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>phosphorous acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>81.995</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>81.981980955</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OP(O)O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>H3O3P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/H3O3P/c1-4(2)3/h1-3H</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OJMIONKXNSYLSR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>14.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>5.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>71484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>71485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>71486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>130167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>130168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>130169</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>97036</chemspider_id>
  <foodb_id>FDB022626</foodb_id>
  <pubchem_compound_id>107909</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id>36361</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Phosphorous acid</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:04 UTC</creation_date>
  <update_date>2020-03-13 16:28:06 UTC</update_date>
  <accession>BMDB0001444</accession>
  <secondary_accessions>
    <accession>BMDB01444</accession>
  </secondary_accessions>
  <name>Adenosine octaphosphate</name>
  <description/>
  <synonyms>
    <synonym>Adenosine octaphosphoric acid</synonym>
    <synonym>{[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}[({[({[({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinate</synonym>
  </synonyms>
  <chemical_formula>C20H32N10O31P8</chemical_formula>
  <average_molecular_weight>1156.305</average_molecular_weight>
  <monisotopic_moleculate_weight>1155.913590274</monisotopic_moleculate_weight>
  <iupac_name>{[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}[({[({[({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid</iupac_name>
  <traditional_iupac>Ap8A</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@]2([H])O[C@@]([H])(N3C=NC4=C(N)N=CN=C34)[C@]([H])(O)[C@]2([H])O)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O</smiles>
  <inchi>InChI=1S/C20H32N10O31P8/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(53-19)1-51-62(35,36)55-64(39,40)57-66(43,44)59-68(47,48)61-69(49,50)60-67(45,46)58-65(41,42)56-63(37,38)52-2-8-12(32)14(34)20(54-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H,47,48)(H,49,50)(H2,21,23,25)(H2,22,24,26)/t7-,8+,11-,12-,13-,14-,19-,20-/m1/s1</inchi>
  <inchikey>KNWWPGOAVAWQPI-LSZNOLIESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside polyphosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside polyphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}[({[({[({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1156.305</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1155.913590274</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@]2([H])O[C@@]([H])(N3C=NC4=C(N)N=CN=C34)[C@]([H])(O)[C@]2([H])O)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H32N10O31P8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H32N10O31P8/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(53-19)1-51-62(35,36)55-64(39,40)57-66(43,44)59-68(47,48)61-69(49,50)60-67(45,46)58-65(41,42)56-63(37,38)52-2-8-12(32)14(34)20(54-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H,47,48)(H,49,50)(H2,21,23,25)(H2,22,24,26)/t7-,8+,11-,12-,13-,14-,19-,20-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KNWWPGOAVAWQPI-LSZNOLIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>620.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>209.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>85.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>30</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1311073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1311074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1311075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1425556</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1425557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1425558</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id/>
  <foodb_id/>
  <kegg_id/>
  <chebi_id/>
  <pubchem_compound_id/>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:06 UTC</creation_date>
  <update_date>2020-03-13 16:28:07 UTC</update_date>
  <accession>BMDB0001445</accession>
  <secondary_accessions>
    <accession>BMDB01445</accession>
  </secondary_accessions>
  <name>N-Acetyl-D-glucosaminyldiphosphodolichol</name>
  <description/>
  <synonyms>
    <synonym>N-Acetyl-D-glucosaminyl-diphosphodolichol</synonym>
    <synonym>N-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-2-{[hydroxy({[hydroxy({[(6E)-3,7,11-trimethyldodeca-6,10-dien-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-6-(hydroxymethyl)oxan-3-yl]ethanimidate</synonym>
  </synonyms>
  <chemical_formula>C23H43NO12P2</chemical_formula>
  <average_molecular_weight>587.5345</average_molecular_weight>
  <monisotopic_moleculate_weight>587.226048869</monisotopic_moleculate_weight>
  <iupac_name>{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}({[hydroxy({[(6E)-3,7,11-trimethyldodeca-6,10-dien-1-yl]oxy})phosphoryl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy({hydroxy[(6E)-3,7,11-trimethyldodeca-6,10-dien-1-yl]oxyphosphoryl}oxy)phosphinic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>OC[C@H]1O[C@@H](OP(O)(=O)OP(O)(=O)OCCC(C)CC\C=C(/C)CCC=C(C)C)[C@H](NC(=O)C)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C23H43NO12P2/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-33-37(29,30)36-38(31,32)35-23-20(24-18(5)26)22(28)21(27)19(14-25)34-23/h8,10,17,19-23,25,27-28H,6-7,9,11-14H2,1-5H3,(H,24,26)(H,29,30)(H,31,32)/b16-10+/t17?,19-,20-,21-,22-,23+/m1/s1</inchi>
  <inchikey>OZGJPDIBINDRGZ-GKXPKBPWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>N-acyl-alpha-hexosamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sesquiterpenoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Farsesane sesquiterpenoid</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sesquiterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}({[hydroxy({[(6E)-3,7,11-trimethyldodeca-6,10-dien-1-yl]oxy})phosphoryl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>587.5345</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>587.226048869</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@@H](OP(O)(=O)OP(O)(=O)OCCC(C)CC\C=C(/C)CCC=C(C)C)[C@H](NC(=O)C)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C23H43NO12P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C23H43NO12P2/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-33-37(29,30)36-38(31,32)35-23-20(24-18(5)26)22(28)21(27)19(14-25)34-23/h8,10,17,19-23,25,27-28H,6-7,9,11-14H2,1-5H3,(H,24,26)(H,29,30)(H,31,32)/b16-10+/t17?,19-,20-,21-,22-,23+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OZGJPDIBINDRGZ-GKXPKBPWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>201.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>139.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>58.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>323172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>371263</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>371264</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>371265</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022628</foodb_id>
  <chemspider_id>10128137</chemspider_id>
  <pubchem_compound_id>11953837</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <kegg_id>C04500</kegg_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>1809448</bigg_id>
  <wikipedia_id/>
  <metlin_id>6251</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00805</protein_accession>
      <name>UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase</name>
      <uniprot_id>Q5EA65</uniprot_id>
      <gene_name>DPAGT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:07 UTC</creation_date>
  <update_date>2020-04-14 22:49:14 UTC</update_date>
  <accession>BMDB0001448</accession>
  <secondary_accessions>
    <accession>BMDB01448</accession>
  </secondary_accessions>
  <name>Sulfate</name>
  <description/>
  <synonyms>
    <synonym>[S(OH)2O2]</synonym>
    <synonym>[SO2(OH)2]</synonym>
    <synonym>Acide sulfurique</synonym>
    <synonym>Acido sulfurico</synonym>
    <synonym>Acidum sulfuricum</synonym>
    <synonym>H2SO4</synonym>
    <synonym>Schwefelsaeureloesungen</synonym>
    <synonym>Sulphuric acid</synonym>
    <synonym>Sulfuric acid</synonym>
    <synonym>Acide sulphurique</synonym>
    <synonym>Acido sulphurico</synonym>
    <synonym>Acidum sulphuricum</synonym>
    <synonym>Sulphate</synonym>
    <synonym>Sulfate</synonym>
  </synonyms>
  <chemical_formula>H2O4S</chemical_formula>
  <average_molecular_weight>98.078</average_molecular_weight>
  <monisotopic_moleculate_weight>97.967379242</monisotopic_moleculate_weight>
  <iupac_name>sulfuric acid</iupac_name>
  <traditional_iupac>sulfuric acid</traditional_iupac>
  <cas_registry_number>14808-79-8</cas_registry_number>
  <smiles>OS(O)(=O)=O</smiles>
  <inchi>InChI=1S/H2O4S/c1-5(2,3)4/h(H2,1,2,3,4)</inchi>
  <inchikey>QAOWNCQODCNURD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as non-metal sulfates. These are inorganic non-metallic compounds containing a sulfate as its largest oxoanion.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Non-metal oxoanionic compounds</class>
    <sub_class>Non-metal sulfates</sub_class>
    <direct_parent>Non-metal sulfates</direct_parent>
    <alternative_parents>
      <alternative_parent>Inorganic oxides</alternative_parent>
      <alternative_parent>Organic sulfuric acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Inorganic oxide</substituent>
      <substituent>Non-metal sulfate</substituent>
      <substituent>Sulfuric acid</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>sulfur oxoacid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>sulfuric acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>98.078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>97.967379242</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OS(O)(=O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>H2O4S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/H2O4S/c1-5(2,3)4/h(H2,1,2,3,4)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QAOWNCQODCNURD-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>13.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>6.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>935</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>449919</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450031</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB11309</drugbank_id>
  <foodb_id>FDB013392</foodb_id>
  <chemspider_id>1086</chemspider_id>
  <pubchem_compound_id>1117</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>26836</chebi_id>
  <kegg_id>C00059</kegg_id>
  <knapsack_id>C00007530</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>NH42SO4</meta_cyc_id>
  <bigg_id>33697</bigg_id>
  <wikipedia_id>Sulfuric_acid</wikipedia_id>
  <metlin_id>3233</metlin_id>
  <synthesis_reference>Zhang, Qiu-Ju; Wang, Xiao; Chen, Jian-Min; Zhuang, Guo-Shun.  Formation of Fe(II) (aq) and sulfate via heterogeneous reaction of SO2 with Fe2O3.    Gaodeng Xuexiao Huaxue Xuebao  (2006),  27(7),  1347-1350.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00081</protein_accession>
      <name>Arylsulfatase A</name>
      <uniprot_id>Q08DD1</uniprot_id>
      <gene_name>ARSA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00113</protein_accession>
      <name>Mercaptopyruvate sulfurtransferase</name>
      <uniprot_id>Q3MHG3</uniprot_id>
      <gene_name>MPST</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00114</protein_accession>
      <name>Thiosulfate sulfurtransferase</name>
      <uniprot_id>P00586</uniprot_id>
      <gene_name>TST</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00115</protein_accession>
      <name>Heparanase</name>
      <uniprot_id>Q9MYY0</uniprot_id>
      <gene_name>HPSE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01345</protein_accession>
      <name>Cartilage oligomeric matrix protein</name>
      <uniprot_id>P35445</uniprot_id>
      <gene_name>COMP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01346</protein_accession>
      <name>LOC782657 protein</name>
      <uniprot_id>A8R4B3</uniprot_id>
      <gene_name>LOC782657</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01347</protein_accession>
      <name>Solute carrier family 26, member 6</name>
      <uniprot_id>Q08DQ8</uniprot_id>
      <gene_name>SLC26A6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01348</protein_accession>
      <name>Testis anion transporter 1</name>
      <uniprot_id>A6QNW6</uniprot_id>
      <gene_name>SLC26A8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01349</protein_accession>
      <name>Vascular endothelial growth factor A</name>
      <uniprot_id>P15691</uniprot_id>
      <gene_name>VEGFA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01350</protein_accession>
      <name>Sodium-independent sulfate anion transporter</name>
      <uniprot_id>Q58DD2</uniprot_id>
      <gene_name>SLC26A11</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01351</protein_accession>
      <name>Prolargin</name>
      <uniprot_id>Q9GKN8</uniprot_id>
      <gene_name>PRELP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01352</protein_accession>
      <name>Sulfate transporter</name>
      <uniprot_id>Q9BEG8</uniprot_id>
      <gene_name>SLC26A2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01353</protein_accession>
      <name>CD97 antigen</name>
      <uniprot_id>Q8SQA4</uniprot_id>
      <gene_name>CD97</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01354</protein_accession>
      <name>SLC26A3 protein</name>
      <uniprot_id>A4IFH8</uniprot_id>
      <gene_name>SLC26A3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:08 UTC</creation_date>
  <update_date>2020-03-13 16:28:08 UTC</update_date>
  <accession>BMDB0001449</accession>
  <secondary_accessions>
    <accession>BMDB01449</accession>
  </secondary_accessions>
  <name>Allopregnanolone</name>
  <description/>
  <synonyms>
    <synonym>(3alpha,5alpha)-3-Hydroxypregnan-20-one</synonym>
    <synonym>3alpha,5alpha-Tetrahydroprogesterone</synonym>
    <synonym>3alpha,5alpha-THP</synonym>
    <synonym>3alpha-Hydroxy-5alpha-dihydroprogesterone</synonym>
    <synonym>3alpha-Hydroxy-5alpha-pregnan-20-one</synonym>
    <synonym>3alpha-OH DHP</synonym>
    <synonym>5alpha-Pregnan-3alpha-ol-20-one</synonym>
    <synonym>Allopregnan-3alpha-ol-20-one</synonym>
    <synonym>Allotetrahydroprogesterone</synonym>
    <synonym>Brexanolona</synonym>
    <synonym>Brexanolonum</synonym>
    <synonym>SAGE-547</synonym>
    <synonym>SGE-102</synonym>
    <synonym>Zulresso</synonym>
    <synonym>(3a,5a)-3-Hydroxypregnan-20-one</synonym>
    <synonym>(3Α,5α)-3-hydroxypregnan-20-one</synonym>
    <synonym>3a,5a-Tetrahydroprogesterone</synonym>
    <synonym>3Α,5α-tetrahydroprogesterone</synonym>
    <synonym>3a,5a-THP</synonym>
    <synonym>3Α,5α-THP</synonym>
    <synonym>3a-Hydroxy-5a-dihydroprogesterone</synonym>
    <synonym>3Α-hydroxy-5α-dihydroprogesterone</synonym>
    <synonym>3a-Hydroxy-5a-pregnan-20-one</synonym>
    <synonym>3Α-hydroxy-5α-pregnan-20-one</synonym>
    <synonym>3a-OH DHP</synonym>
    <synonym>3Α-OH DHP</synonym>
    <synonym>5a-Pregnan-3a-ol-20-one</synonym>
    <synonym>5Α-pregnan-3α-ol-20-one</synonym>
    <synonym>Allopregnan-3a-ol-20-one</synonym>
    <synonym>Allopregnan-3α-ol-20-one</synonym>
    <synonym>(+)-3a-Hydroxy-5a-pregnan-20-one</synonym>
    <synonym>(3a)-Allopregnanolone</synonym>
    <synonym>3-a-Tetrahydroprogesterone</synonym>
    <synonym>3-alpha-Tetrahydroprogesterone</synonym>
    <synonym>3a,5a-Pregnanolone</synonym>
    <synonym>3a-Hydroxy-5a-pregnane-20-one</synonym>
    <synonym>5a-Pregnane-3a-ol-20-one</synonym>
    <synonym>3-Hydroxypregnan-20-one</synonym>
    <synonym>alpha-Hydroxy-5 alpha-pregnan-20-one, 3</synonym>
    <synonym>Pregnan-3alpha-ol-20-one</synonym>
    <synonym>Pregnanolone, (3alpha)-isomer</synonym>
    <synonym>3 Hydroxypregnan 20 one</synonym>
    <synonym>3 alpha Hydroxy 5 alpha pregnan 20 one</synonym>
    <synonym>3 alpha-Hydroxy-5 alpha-pregnan-20-one</synonym>
    <synonym>Pregnan 3alpha ol 20 one</synonym>
    <synonym>alpha-Pregnan-20-one, 3 alpha-hydroxy-5</synonym>
    <synonym>(+)-3alpha-Hydroxy-5alpha-pregnan-20-one</synonym>
    <synonym>(+)-3Α-hydroxy-5α-pregnan-20-one</synonym>
    <synonym>(3alpha)-Allopregnanolone</synonym>
    <synonym>(3Α)-allopregnanolone</synonym>
    <synonym>3alpha,5alpha-Pregnanolone</synonym>
    <synonym>3alpha-Hydroxy-5alpha-pregnane-20-one</synonym>
    <synonym>3Α,5α-pregnanolone</synonym>
    <synonym>3Α-hydroxy-5α-pregnane-20-one</synonym>
    <synonym>5alpha-Pregnane-3alpha-ol-20-one</synonym>
    <synonym>5Α-pregnane-3α-ol-20-one</synonym>
    <synonym>Allopregnanolone</synonym>
  </synonyms>
  <chemical_formula>C21H34O2</chemical_formula>
  <average_molecular_weight>318.4935</average_molecular_weight>
  <monisotopic_moleculate_weight>318.255880332</monisotopic_moleculate_weight>
  <iupac_name>1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one</iupac_name>
  <traditional_iupac>1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone</traditional_iupac>
  <cas_registry_number>516-54-1</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O</smiles>
  <inchi>InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16-,17+,18-,19-,20-,21+/m0/s1</inchi>
  <inchikey>AURFZBICLPNKBZ-SYBPFIFISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Pregnane steroids</sub_class>
    <direct_parent>Gluco/mineralocorticoids, progestogins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>20-oxosteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hydroxy-5alpha-pregnan-20-one</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>177 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>318.4935</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>318.255880332</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H34O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16-,17+,18-,19-,20-,21+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AURFZBICLPNKBZ-SYBPFIFISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>92.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>105371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171847</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>171848</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB11859</drugbank_id>
  <foodb_id>FDB022630</foodb_id>
  <chemspider_id>83760</chemspider_id>
  <pubchem_compound_id>92786</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>50169</chebi_id>
  <kegg_id>C13712</kegg_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Allopregnanolone</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Wiebe, J. P.; Deline, C.; Buckingham, K. D.; Dave, Vinod; Stothers, J. B. Synthesis of the allylic gonadal steroids, 3a-hydroxy-4-pregnen-20-one and 3a-hydroxy-4-androsten-17-one, and of 3a-hydroxy-5a-pregnan-20-one. Steroids (1985), 45(1), 39-51.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:09 UTC</creation_date>
  <update_date>2020-04-16 20:38:42 UTC</update_date>
  <accession>BMDB0001451</accession>
  <secondary_accessions>
    <accession>BMDB01451</accession>
  </secondary_accessions>
  <name>Lipoic acid</name>
  <description>Lipoic acid, also known as RLA or a-lipoate, belongs to the class of organic compounds known as lipoic acids and derivatives. Lipoic acids and derivatives are compounds containing a lipoic acid moiety (or a derivative thereof), which consists of a pentanoic acid (or derivative) attached to the C3 carbon atom of a 1,2-dithiolane ring. Lipoic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Lipoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Lipoic acid exists in all living species, ranging from bacteria to humans. In cattle, lipoic acid is involved in the metabolic pathway called the glycine and serine metabolism pathway.</description>
  <synonyms>
    <synonym>(+)-alpha-Lipoic acid</synonym>
    <synonym>(R)-(+)-Lipoate</synonym>
    <synonym>(R)-(+)-Lipoic acid</synonym>
    <synonym>(R)-1,2-Dithiolane-3-pentanoic acid</synonym>
    <synonym>(R)-1,2-Dithiolane-3-valeric acid</synonym>
    <synonym>(R)-6,8-Thioctic acid</synonym>
    <synonym>alpha-Lipoic acid</synonym>
    <synonym>Lipoic acid</synonym>
    <synonym>R-(+)-Lipoic acid</synonym>
    <synonym>R-LA</synonym>
    <synonym>RLA</synonym>
    <synonym>Thioctic acid</synonym>
    <synonym>Thioctic acid D-form</synonym>
    <synonym>1,2-Dithiolane-3R-pentanoic acid</synonym>
    <synonym>(+)-a-Lipoate</synonym>
    <synonym>(+)-a-Lipoic acid</synonym>
    <synonym>(+)-alpha-Lipoate</synonym>
    <synonym>(+)-Α-lipoate</synonym>
    <synonym>(+)-Α-lipoic acid</synonym>
    <synonym>(R)-1,2-Dithiolane-3-pentanoate</synonym>
    <synonym>(R)-1,2-Dithiolane-3-valerate</synonym>
    <synonym>(R)-6,8-Thioctate</synonym>
    <synonym>a-Lipoate</synonym>
    <synonym>a-Lipoic acid</synonym>
    <synonym>alpha-Lipoate</synonym>
    <synonym>Α-lipoate</synonym>
    <synonym>Α-lipoic acid</synonym>
    <synonym>Lipoate</synonym>
    <synonym>R-(+)-Lipoate</synonym>
    <synonym>Thioctate</synonym>
    <synonym>Thioctate D-form</synonym>
    <synonym>1,2-Dithiolane-3R-pentanoate</synonym>
    <synonym>(R)-Lipoate</synonym>
    <synonym>Alpha Lippon al</synonym>
    <synonym>Alpha-Lippon al</synonym>
    <synonym>AlphaLippon al</synonym>
    <synonym>Alphaflam</synonym>
    <synonym>Hexal brand OF thioctic acid</synonym>
    <synonym>Injekt, thiogamma</synonym>
    <synonym>Liponsaure ratiopharm</synonym>
    <synonym>Liponsaure-ratiopharm</synonym>
    <synonym>Stadapharm brand OF thioctic acid</synonym>
    <synonym>Thioctacide T</synonym>
    <synonym>Verla lipon</synonym>
    <synonym>Viatris brand OF thioctic acid</synonym>
    <synonym>alpha Liponaure heumann</synonym>
    <synonym>alpha Liponsaure von CT</synonym>
    <synonym>AlphaLiponsaure von CT</synonym>
    <synonym>Duralipon</synonym>
    <synonym>Ratiopharm brand OF thioctic acid</synonym>
    <synonym>Aliud brand OF thioctic acid</synonym>
    <synonym>Alpha-Liponsaure sofotec</synonym>
    <synonym>AlphaLipon stada</synonym>
    <synonym>Azulipont</synonym>
    <synonym>Heumann brand OF thioctic acid</synonym>
    <synonym>Illa brand OF thioctic acid</synonym>
    <synonym>Illa brand OF thioctic acid tromethamine</synonym>
    <synonym>Juta brand OF thioctic acid</synonym>
    <synonym>MTW Alphaliponsaure</synonym>
    <synonym>Pleomix Alpha</synonym>
    <synonym>PleomixAlpha</synonym>
    <synonym>PleomixAlpha N</synonym>
    <synonym>Q Pharm brand OF thioctic acid</synonym>
    <synonym>Q-Pharm brand OF thioctic acid</synonym>
    <synonym>Thiogamma injekt</synonym>
    <synonym>alpha Vibolex</synonym>
    <synonym>AlphaVibolex</synonym>
    <synonym>Biomo brand OF thioctic acid</synonym>
    <synonym>Biomo-lipon</synonym>
    <synonym>Biomolipon</synonym>
    <synonym>CT-Arzneimittel brand OF thioctic acid</synonym>
    <synonym>Acid, alpha-lipoic</synonym>
    <synonym>Alpha Lipogamma</synonym>
    <synonym>Alpha Lipon stada</synonym>
    <synonym>Alpha-Lipogamma</synonym>
    <synonym>Alpha-Lipon stada</synonym>
    <synonym>AlphaLipogamma</synonym>
    <synonym>AlphaLiponsaure sofotec</synonym>
    <synonym>Fenint</synonym>
    <synonym>Juthiac</synonym>
    <synonym>Merck dura brand OF thioctic acid</synonym>
    <synonym>Pleomix Alpha N</synonym>
    <synonym>Rosen brand OF thioctic acid</synonym>
    <synonym>Thiogamma oral</synonym>
    <synonym>Tromlipon</synonym>
    <synonym>Trommsdorgg brand OF thioctic acid</synonym>
    <synonym>Viatris brand OF thioctic acid tromethamine</synonym>
    <synonym>Worwag brand OF thioctic acid</synonym>
    <synonym>Worwag brand OF thioctic acid meglumine</synonym>
    <synonym>alpha Lipoic acid</synonym>
    <synonym>alpha-Liponsaure von CT</synonym>
    <synonym>alpha-Vibolex</synonym>
    <synonym>AlphaLiponaure heumann</synonym>
    <synonym>Biomo lipon</synonym>
    <synonym>CT Arzneimittel brand OF thioctic acid</synonym>
    <synonym>Esparma brand OF thioctic acid</synonym>
    <synonym>Alpha Liponsaure sofotec</synonym>
    <synonym>Azupharma brand OF thioctic acid</synonym>
    <synonym>Generosan brand OF thioctic acid</synonym>
    <synonym>Lichtenstein brand OF thioctic acid</synonym>
    <synonym>Liponsaureratiopharm</synonym>
    <synonym>MTW Brand OF thioctic acid</synonym>
    <synonym>MTW-Alphaliponsaure</synonym>
    <synonym>MTWAlphaliponsaure</synonym>
    <synonym>Neurium</synonym>
    <synonym>Pharmacia brand OF thioctic acid</synonym>
    <synonym>Pleomix-Alpha</synonym>
    <synonym>Pleomix-Alpha N</synonym>
    <synonym>Sofotec brand OF thioctic acid</synonym>
    <synonym>Thioctacid</synonym>
    <synonym>Verla brand OF thioctic acid</synonym>
    <synonym>Verla-lipon</synonym>
    <synonym>VerlaLipon</synonym>
    <synonym>alpha-Liponaure heumann</synonym>
    <synonym>Espa lipon</synonym>
    <synonym>Espa-lipon</synonym>
    <synonym>Espalipon</synonym>
    <synonym>(R)-Lipoic acid</synonym>
  </synonyms>
  <chemical_formula>C8H14O2S2</chemical_formula>
  <average_molecular_weight>206.326</average_molecular_weight>
  <monisotopic_moleculate_weight>206.043521072</monisotopic_moleculate_weight>
  <iupac_name>5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid</iupac_name>
  <traditional_iupac>lipoic acid</traditional_iupac>
  <cas_registry_number>1200-22-2</cas_registry_number>
  <smiles>OC(=O)CCCC[C@@H]1CCSS1</smiles>
  <inchi>InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1</inchi>
  <inchikey>AGBQKNBQESQNJD-SSDOTTSWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as lipoic acids and derivatives. Lipoic acids and derivatives are compounds containing a lipoic acid moiety (or a derivative thereof), which consists of a pentanoic acid (or derivative) attached to the C3 carbon atom of a 1,2-dithiolane ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Dithiolanes</class>
    <sub_class>Lipoic acids and derivatives</sub_class>
    <direct_parent>Lipoic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-dithiolanes</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heterocyclic fatty acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic disulfides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Thia fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-dithiolane</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Heterocyclic fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lipoic_acid_derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic disulfide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Thia fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Thia fatty acids</external_descriptor>
      <external_descriptor>Thia fatty acids</external_descriptor>
      <external_descriptor>dithiolanes</external_descriptor>
      <external_descriptor>heterocyclic fatty acid</external_descriptor>
      <external_descriptor>lipoic acid</external_descriptor>
      <external_descriptor>thia fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>206.326</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>206.043521072</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCCC[C@@H]1CCSS1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H14O2S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AGBQKNBQESQNJD-SSDOTTSWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>100076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>100077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179471</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By GC-TOFMS and UPLC-QTOFMS</comment>
      <references>
        <reference>
          <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
          <pubmed_id>27999311</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB00166</drugbank_id>
  <foodb_id>FDB022631</foodb_id>
  <chemspider_id>5886</chemspider_id>
  <pubchem_compound_id>6112</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>30314</chebi_id>
  <kegg_id>C16241</kegg_id>
  <knapsack_id>C00000754</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>LIPOIC-ACID</meta_cyc_id>
  <bigg_id>35801</bigg_id>
  <wikipedia_id>Lipoic_acid</wikipedia_id>
  <metlin_id>126</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
      <pubmed_id>27999311</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00363</protein_accession>
      <name>Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex</name>
      <uniprot_id>P11180</uniprot_id>
      <gene_name>DLAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00509</protein_accession>
      <name>Acyl-coenzyme A synthetase ACSM1, mitochondrial</name>
      <uniprot_id>Q9BEA2</uniprot_id>
      <gene_name>ACSM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00628</protein_accession>
      <name>Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial</name>
      <uniprot_id>P11179</uniprot_id>
      <gene_name>DLST</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00785</protein_accession>
      <name>Pyruvate dehydrogenase protein X component</name>
      <uniprot_id>P22439</uniprot_id>
      <gene_name>PDHX</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00786</protein_accession>
      <name>Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial</name>
      <uniprot_id>P11181</uniprot_id>
      <gene_name>DBT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00787</protein_accession>
      <name>Aminomethyltransferase, mitochondrial</name>
      <uniprot_id>P25285</uniprot_id>
      <gene_name>AMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01981</protein_accession>
      <name>Glycine cleavage system H protein, mitochondrial</name>
      <uniprot_id>P20821</uniprot_id>
      <gene_name>GCSH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:10 UTC</creation_date>
  <update_date>2020-04-15 22:31:55 UTC</update_date>
  <accession>BMDB0001452</accession>
  <secondary_accessions>
    <accession>BMDB01452</accession>
  </secondary_accessions>
  <name>Thromboxane A2</name>
  <description/>
  <synonyms>
    <synonym>(5Z,13E)-(15S)-9alpha,11alpha-Epoxy-15-hydroxythromboxa-5,13-dienoate</synonym>
    <synonym>(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-Oic acid</synonym>
    <synonym>9S,11S-Epoxy,15S-hydroxy-thromboxa-5Z,13E-dien-1-Oic acid</synonym>
    <synonym>TXA-2</synonym>
    <synonym>TXA2</synonym>
    <synonym>(5Z,13E)-(15S)-9a,11a-Epoxy-15-hydroxythromboxa-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-9a,11a-Epoxy-15-hydroxythromboxa-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-9alpha,11alpha-Epoxy-15-hydroxythromboxa-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-9Α,11α-epoxy-15-hydroxythromboxa-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-9Α,11α-epoxy-15-hydroxythromboxa-5,13-dienoic acid</synonym>
    <synonym>(5Z,9a,11a,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,9a,11a,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-Oic acid</synonym>
    <synonym>(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxythromboxa-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,9Α,11α,13E,15S)-9,11-epoxy-15-hydroxythromboxa-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,9Α,11α,13E,15S)-9,11-epoxy-15-hydroxythromboxa-5,13-dien-1-Oic acid</synonym>
    <synonym>9S,11S-Epoxy,15S-hydroxy-thromboxa-5Z,13E-dien-1-Oate</synonym>
    <synonym>(1S-(1alpha,3alpha,3R*),4beta(Z),5alpha)-7-(3-(3-hydroxy-1-octenyl)-2,6-dioxabicyclo(3.1.1)hept-4-yl)-5-heptenoate</synonym>
    <synonym>(1S-(1alpha,3alpha,3R*),4beta(Z),5alpha)-7-(3-(3-hydroxy-1-octenyl)-2,6-dioxabicyclo(3.1.1)hept-4-yl)-5-heptenoic acid</synonym>
    <synonym>(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-Hydroxy-1-octenyl]-2,6-dioxabicyclo[3.1.1]hept-4-yl]-5-heptenoate</synonym>
    <synonym>(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-Hydroxy-1-octenyl]-2,6-dioxabicyclo[3.1.1]hept-4-yl]-5-heptenoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-9,11-Epoxy-15-hydroxythromba-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-9,11-Epoxy-15-hydroxythromba-5,13-dienoic acid</synonym>
    <synonym>(5Z,13E)-(15S)-9-alpha,11-alpha-Epoxy-15-hydroxythromboxa-5,13-dienoate</synonym>
    <synonym>(5Z,13E)-(15S)-9-alpha,11-alpha-Epoxy-15-hydroxythromboxa-5,13-dienoic acid</synonym>
    <synonym>(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxy-thromboxa-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,9alpha,11alpha,13E,15S)-9,11-Epoxy-15-hydroxy-thromboxa-5,13-dien-1-Oic acid</synonym>
    <synonym>7-[3-(3-Hydroxy-1-octenyl)-2,6-dioxabicyclo[3.1.1]hept-4-yl]-[1S-[1alpha,3alpha(1E,3R*),4beta(Z),5alpha]]-5-heptenoate</synonym>
    <synonym>7-[3-(3-Hydroxy-1-octenyl)-2,6-dioxabicyclo[3.1.1]hept-4-yl]-[1S-[1alpha,3alpha(1E,3R*),4beta(Z),5alpha]]-5-heptenoic acid</synonym>
    <synonym>Cid</synonym>
    <synonym>Rabbit aorta contracting substance</synonym>
    <synonym>RCS</synonym>
    <synonym>a2, Thromboxane</synonym>
  </synonyms>
  <chemical_formula>C20H32O5</chemical_formula>
  <average_molecular_weight>352.4651</average_molecular_weight>
  <monisotopic_moleculate_weight>352.224974134</monisotopic_moleculate_weight>
  <iupac_name>(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,6-dioxabicyclo[3.1.1]heptan-4-yl]hept-5-enoic acid</iupac_name>
  <traditional_iupac>thromboxane</traditional_iupac>
  <cas_registry_number>57576-52-0</cas_registry_number>
  <smiles>CCCCC[C@H](O)\C=C\[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C\C=C/CCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-20(24-17)25-18)10-7-4-5-8-11-19(22)23/h4,7,12-13,15-18,20-21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,20+/m0/s1</inchi>
  <inchikey>DSNBHJFQCNUKMA-SCKDECHMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as thromboxanes. These are eicosanoids structurally characterized by the presence of a 6-member ether containing ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Thromboxanes</direct_parent>
    <alternative_parents>
      <alternative_parent>1,3-dioxanes</alternative_parent>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heterocyclic fatty acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Oxetanes</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Heterocyclic fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Meta-dioxane</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Oxetane</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Thromboxane</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Thromboxanes</external_descriptor>
      <external_descriptor>Thromboxanes</external_descriptor>
      <external_descriptor>epoxy monocarboxylic acid</external_descriptor>
      <external_descriptor>thromboxane</external_descriptor>
      <external_descriptor>thromboxanes A</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5Z)-7-[(1S,3R,4S,5S)-3-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-2,6-dioxabicyclo[3.1.1]heptan-4-yl]hept-5-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>352.4651</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>352.224974134</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC[C@H](O)\C=C\[C@H]1O[C@H]2C[C@H](O2)[C@@H]1C\C=C/CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H32O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-20(24-17)25-18)10-7-4-5-8-11-19(22)23/h4,7,12-13,15-18,20-21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,20+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DSNBHJFQCNUKMA-SCKDECHMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>75.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>97.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>86178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>86179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>86180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>148431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>148432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>148433</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022632</foodb_id>
  <chemspider_id>4444137</chemspider_id>
  <pubchem_compound_id>5280497</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15627</chebi_id>
  <kegg_id>C02198</kegg_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>39305</bigg_id>
  <wikipedia_id>Thromboxane A2</wikipedia_id>
  <metlin_id>6253</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01892</protein_accession>
      <name>Thromboxane A2 receptor</name>
      <uniprot_id>Q95125</uniprot_id>
      <gene_name>TBXA2R</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:11 UTC</creation_date>
  <update_date>2020-03-13 16:28:09 UTC</update_date>
  <accession>BMDB0001453</accession>
  <secondary_accessions>
    <accession>BMDB01453</accession>
  </secondary_accessions>
  <name>Thiocyanate</name>
  <description/>
  <synonyms>
    <synonym>[S-C#N](-)</synonym>
    <synonym>N#C-S(-)</synonym>
    <synonym>Rhodanid</synonym>
    <synonym>Rhodanide</synonym>
    <synonym>SCN(-)</synonym>
    <synonym>THIOCYANATE ion</synonym>
    <synonym>Thiocyanate ion (1-)</synonym>
    <synonym>Thiozyanat</synonym>
    <synonym>THIOCYANic acid ion</synonym>
    <synonym>Thiocyanic acid ion (1-)</synonym>
    <synonym>Thiocyanic acid</synonym>
    <synonym>SCN</synonym>
    <synonym>Ammonium sulfocyanate</synonym>
    <synonym>HSCN</synonym>
    <synonym>Hydrogen thiocyanate</synonym>
    <synonym>Nitridosulfanidocarbon</synonym>
    <synonym>Silver thiocyanate agscn</synonym>
    <synonym>Thallium thiocyanate</synonym>
    <synonym>Thiocyanid</synonym>
    <synonym>Weedazol TL</synonym>
    <synonym>Thiocyanogen ((SCN)2(1-))</synonym>
    <synonym>Thiocyanate ion (2-)</synonym>
  </synonyms>
  <chemical_formula>CNS</chemical_formula>
  <average_molecular_weight>58.082</average_molecular_weight>
  <monisotopic_moleculate_weight>57.975144695</monisotopic_moleculate_weight>
  <iupac_name>cyanosulfanide</iupac_name>
  <traditional_iupac>thiocyanate</traditional_iupac>
  <cas_registry_number>302-04-5</cas_registry_number>
  <smiles>[S-]C#N</smiles>
  <inchi>InChI=1S/CHNS/c2-1-3/h3H/p-1</inchi>
  <inchikey>ZMZDMBWJUHKJPS-UHFFFAOYSA-M</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as thiocyanates. These are salts or esters of thiocyanic acid, with the general formula RSC#N (R=alkyl, aryl).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organosulfur compounds</super_class>
    <class>Thiocyanates</class>
    <sub_class/>
    <direct_parent>Thiocyanates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic anions</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic anion</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Thiocyanate</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a perthiol</external_descriptor>
      <external_descriptor>pseudohalide anion</external_descriptor>
      <external_descriptor>sulfur molecular entity</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>cyanosulfanide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>58.082</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>57.975144695</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[S-]C#N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>CNS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/CHNS/c2-1-3/h3H/p-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZMZDMBWJUHKJPS-UHFFFAOYSA-M</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>23.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>16.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>4.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179265</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181592</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB013883</foodb_id>
  <chemspider_id>8961</chemspider_id>
  <pubchem_compound_id>9322</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18022</chebi_id>
  <kegg_id>C01755</kegg_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>38336</bigg_id>
  <wikipedia_id>Thiocyanate</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Lang, Konrad.  Thiocyanate formation in the animal body. II.    Biochemische Zeitschrift  (1933),  263  262-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00114</protein_accession>
      <name>Thiosulfate sulfurtransferase</name>
      <uniprot_id>P00586</uniprot_id>
      <gene_name>TST</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:13 UTC</creation_date>
  <update_date>2020-03-13 16:28:10 UTC</update_date>
  <accession>BMDB0001454</accession>
  <secondary_accessions>
    <accession>BMDB01454</accession>
  </secondary_accessions>
  <name>Guanosine tetraphosphate adenosine</name>
  <description/>
  <synonyms>
    <synonym>a(5')P4(5')g</synonym>
    <synonym>Guanosine tetraphosphoric acid adenosine</synonym>
    <synonym>Guanosine 5'-(pentahydrogen tetraphosphate), 5'-&gt;3'-ester with adenosine</synonym>
    <synonym>AP4g</synonym>
    <synonym>Adenosine 5'-p(1)-tetraphosphate-p(4)-5'''-guanosine</synonym>
    <synonym>p(1)-(5'-Adenosyl),p(4)-(5'-guanosyl) tetraphosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C20H28N10O20P4</chemical_formula>
  <average_molecular_weight>852.3864</average_molecular_weight>
  <monisotopic_moleculate_weight>852.043179434</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxyphosphinic acid</traditional_iupac>
  <cas_registry_number>100849-67-0</cas_registry_number>
  <smiles>NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C20H28N10O20P4/c21-14-8-15(24-3-23-14)29(4-25-8)18-12(33)10(31)6(46-18)1-44-51(36,37)48-53(40,41)50-54(42,43)49-52(38,39)45-2-7-11(32)13(34)19(47-7)30-5-26-9-16(30)27-20(22)28-17(9)35/h3-7,10-13,18-19,31-34H,1-2H2,(H,36,37)(H,38,39)(H,40,41)(H,42,43)(H2,21,23,24)(H3,22,27,28,35)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1</inchi>
  <inchikey>SJXJAXXRDJWRCR-INFSMZHSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside polyphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside polyphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>adenosine 5'-phosphate</external_descriptor>
      <external_descriptor>guanosine 5'-phosphate</external_descriptor>
      <external_descriptor>purine ribonucleoside 5'-tetraphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-8.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>852.3864</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>852.043179434</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H28N10O20P4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H28N10O20P4/c21-14-8-15(24-3-23-14)29(4-25-8)18-12(33)10(31)6(46-18)1-44-51(36,37)48-53(40,41)50-54(42,43)49-52(38,39)45-2-7-11(32)13(34)19(47-7)30-5-26-9-16(30)27-20(22)28-17(9)35/h3-7,10-13,18-19,31-34H,1-2H2,(H,36,37)(H,38,39)(H,40,41)(H,42,43)(H2,21,23,24)(H3,22,27,28,35)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SJXJAXXRDJWRCR-INFSMZHSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>449.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>167.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>68.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180425</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022633</foodb_id>
  <chemspider_id>8947177</chemspider_id>
  <pubchem_compound_id>10771862</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>52968</chebi_id>
  <kegg_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:14 UTC</creation_date>
  <update_date>2020-03-13 16:28:11 UTC</update_date>
  <accession>BMDB0001455</accession>
  <secondary_accessions>
    <accession>BMDB01455</accession>
  </secondary_accessions>
  <name>Alloepipregnanolone</name>
  <description/>
  <synonyms>
    <synonym>(3beta,5alpha)-3-Hydroxypregnan-20-one</synonym>
    <synonym>3beta-Hydroxy-5alpha-pregnane-20-one</synonym>
    <synonym>5alpha-Pregnan-3beta-ol-20-one</synonym>
    <synonym>Allopregnan-3beta-ol-20-one</synonym>
    <synonym>Epiallopregnanolone</synonym>
    <synonym>3beta-Hydroxy-5alpha-pregnan-20-one</synonym>
    <synonym>(3b,5a)-3-Hydroxypregnan-20-one</synonym>
    <synonym>(3Β,5α)-3-hydroxypregnan-20-one</synonym>
    <synonym>3b-Hydroxy-5a-pregnane-20-one</synonym>
    <synonym>3Β-hydroxy-5α-pregnane-20-one</synonym>
    <synonym>5a-Pregnan-3b-ol-20-one</synonym>
    <synonym>5Α-pregnan-3β-ol-20-one</synonym>
    <synonym>Allopregnan-3b-ol-20-one</synonym>
    <synonym>Allopregnan-3β-ol-20-one</synonym>
    <synonym>3b-Hydroxy-5a-pregnan-20-one</synonym>
    <synonym>3Β-hydroxy-5α-pregnan-20-one</synonym>
    <synonym>3-Deoxo-3b-hydroxy-5a-dihydroprogesterone</synonym>
    <synonym>3b-Allopregnanolone</synonym>
    <synonym>3b-Hydroxy-5a,17b-pregnan-20-one</synonym>
    <synonym>3b-Hydroxy-5a-tetrahydroprogesterone</synonym>
    <synonym>5a-Dihydropregnenolone</synonym>
    <synonym>5a-Pregnane-3b-ol-20-one</synonym>
    <synonym>Allopregnanolone</synonym>
    <synonym>Isopregnanolone</synonym>
    <synonym>3 alpha, 5 beta Tetrahydroprogesterone</synonym>
    <synonym>Allopregnan 3 beta ol 20 one</synonym>
    <synonym>Allopregnan-3 beta-ol-20-one</synonym>
    <synonym>Pregnanolone, (3beta)-isomer</synonym>
    <synonym>Pregnanolone, (3beta, 5alpha)-isomer</synonym>
    <synonym>Pregnanolone, (3beta, 5beta,14beta)-isomer</synonym>
    <synonym>beta-Ol-20-one, allopregnan-3</synonym>
    <synonym>beta-Pregnan-20-one, 3 alpha-hydroxy-5</synonym>
    <synonym>3 alpha Hydroxy 5 beta pregnan 20 one</synonym>
    <synonym>3-Hydroxypregnan-20-one</synonym>
    <synonym>3beta Hydroxy 5alpha pregnan 20 one</synonym>
    <synonym>Eltanolone</synonym>
    <synonym>Epipregnanolone</synonym>
    <synonym>Pregnanolone</synonym>
    <synonym>Pregnanolone, (3alpha)-isomer</synonym>
    <synonym>Pregnanolone, (3alpha,5alpha)-isomer</synonym>
    <synonym>Pregnanolone, (3beta, 5alpha, 8alpha, 17beta)-isomer</synonym>
    <synonym>alpha-Hydroxy-5 alpha-pregnan-20-one, 3</synonym>
    <synonym>3 Hydroxypregnan 20 one</synonym>
    <synonym>3 alpha Hydroxy 5 alpha pregnan 20 one</synonym>
    <synonym>3 alpha, 5 beta-Tetrahydroprogesterone</synonym>
    <synonym>3 alpha-Hydroxy-5 alpha-pregnan-20-one</synonym>
    <synonym>3 alpha-Hydroxy-5 beta-pregnan-20-one</synonym>
    <synonym>Pregnan 3alpha ol 20 one</synonym>
    <synonym>Pregnanolone, (3alpha, 5beta, 17-alpha)-isomer</synonym>
    <synonym>Pregnanolone, (3alpha,5beta)-isomer</synonym>
    <synonym>Pregnanolone, (3beta, 5alpha, 17alpha)-isomer</synonym>
    <synonym>alpha-Hydroxy-5 beta-pregnan-20-one, 3</synonym>
    <synonym>alpha-Pregnan-20-one, 3 alpha-hydroxy-5</synonym>
    <synonym>Pregnan-3alpha-ol-20-one</synonym>
    <synonym>Pregnanolone, (3beta, 5beta)-isomer</synonym>
    <synonym>Pregnanolone, (3beta, 5beta, 17alpha)-isomer</synonym>
    <synonym>Pregnanolone, (5alpha)-isomer</synonym>
    <synonym>Sepranolone</synonym>
  </synonyms>
  <chemical_formula>C21H34O2</chemical_formula>
  <average_molecular_weight>318.4935</average_molecular_weight>
  <monisotopic_moleculate_weight>318.255880332</monisotopic_moleculate_weight>
  <iupac_name>1-[(1S,2S,5S,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one</iupac_name>
  <traditional_iupac>isopregnanolone</traditional_iupac>
  <cas_registry_number>516-55-2</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15-,16-,17+,18-,19-,20-,21+/m0/s1</inchi>
  <inchikey>AURFZBICLPNKBZ-FZCSVUEKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Pregnane steroids</sub_class>
    <direct_parent>Gluco/mineralocorticoids, progestogins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>20-oxosteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hydroxy-5alpha-pregnan-20-one</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>194.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(1S,2S,5S,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethan-1-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>318.4935</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>318.255880332</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H34O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15-,16-,17+,18-,19-,20-,21+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AURFZBICLPNKBZ-FZCSVUEKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>92.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280997</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022634</foodb_id>
  <drugbank_id>DB12972</drugbank_id>
  <chemspider_id>83761</chemspider_id>
  <pubchem_compound_id>92787</pubchem_compound_id>
  <kegg_id>C15484</kegg_id>
  <chebi_id>11909</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Kametani, Tetsuji; Suzuki, Koji; Nemoto, Hideo. Efficient synthesis of a pregnane-type steroid. Total synthesis of (+)-5a-dihydropregnenolone [(+)-3b-hydroxy-5a-pregnan-20-one]. Journal of the Chemical Society, Perkin Transactions 1.  1980, p.2805-2807</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:15 UTC</creation_date>
  <update_date>2020-03-13 16:28:11 UTC</update_date>
  <accession>BMDB0001457</accession>
  <secondary_accessions>
    <accession>BMDB01457</accession>
  </secondary_accessions>
  <name>5-b-Cholestane-3a ,7a ,12a-triol</name>
  <description/>
  <synonyms>
    <synonym>3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestane</synonym>
    <synonym>3alpha,7alpha,12alpha-Trihydroxycoprostane</synonym>
    <synonym>3a,7a,12a-Trihydroxy-5b-cholestane</synonym>
    <synonym>3Α,7α,12α-trihydroxy-5β-cholestane</synonym>
    <synonym>3a,7a,12a-Trihydroxycoprostane</synonym>
    <synonym>3Α,7α,12α-trihydroxycoprostane</synonym>
    <synonym>5b-Cholestane-3a,7a,12a-triol</synonym>
    <synonym>5Β-cholestane-3α,7α,12α-triol</synonym>
    <synonym>5-beta-Cholestane-3-alpha,7-alpha,12-alpha-triol</synonym>
    <synonym>3,7,12-Trihydroxycholestane</synonym>
    <synonym>3,7,12-Trihydroxycoprostane</synonym>
    <synonym>3,7,12-Trihydroxycoprostane, (3alpha,5alpha,7alpha,12alpha)-isomer</synonym>
    <synonym>3,7,12-Trihydroxycoprostane, (3beta,5alpha,7alpha,12alpha)-isomer</synonym>
    <synonym>3,7,12-Trihydroxycoprostane, (3beta,5beta,7alpha,12alpha)-isomer</synonym>
    <synonym>3alpha, 7alpha,12alpha-Trihydroxy-5beta-cholestane</synonym>
    <synonym>5 beta-Cholestane-3 alpha,7 alpha,12 alpha-triol</synonym>
    <synonym>Chtriol</synonym>
    <synonym>Trihydroxycoprostane</synonym>
    <synonym>(3alpha,5beta,7alpha,12alpha)-Cholestane-3,7,12-triol</synonym>
    <synonym>(3Α,5β,7α,12α)-cholestane-3,7,12-triol</synonym>
    <synonym>5beta-Cholestan-3alpha,7alpha,12alpha-triol</synonym>
    <synonym>5Β-cholestan-3α,7α,12α-triol</synonym>
    <synonym>5beta-Cholestane-3alpha,7alpha,12alpha-triol</synonym>
  </synonyms>
  <chemical_formula>C27H48O3</chemical_formula>
  <average_molecular_weight>420.6682</average_molecular_weight>
  <monisotopic_moleculate_weight>420.360345402</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</iupac_name>
  <traditional_iupac>(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</traditional_iupac>
  <cas_registry_number>547-96-6</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C</smiles>
  <inchi>InChI=1S/C27H48O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h16-25,28-30H,6-15H2,1-5H3/t17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>RIVQQZVHIVNQFH-XJZYBRFWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>7-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>7-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>12alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>3alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>7alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>C27 bile acids, alcohols, and derivatives</external_descriptor>
      <external_descriptor>C27 bile acids, alcohols, and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,9,16-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>420.6682</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>420.360345402</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H48O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H48O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h16-25,28-30H,6-15H2,1-5H3/t17-,18+,19-,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RIVQQZVHIVNQFH-XJZYBRFWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>122.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>52.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Bile Acid Biosynthesis</name>
      <smpdb_id>SMP0087236</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>67488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>67489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>67490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>125328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>125329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>125330</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022635</foodb_id>
  <drugbank_id/>
  <chemspider_id>141053</chemspider_id>
  <pubchem_compound_id>160520</pubchem_compound_id>
  <kegg_id>C05454</kegg_id>
  <chebi_id>16496</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>45846</bigg_id>
  <wikipedia_id/>
  <metlin_id>6254</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:16 UTC</creation_date>
  <update_date>2020-03-13 16:28:12 UTC</update_date>
  <accession>BMDB0001458</accession>
  <secondary_accessions>
    <accession>BMDB01458</accession>
  </secondary_accessions>
  <name>Biotin amide</name>
  <description/>
  <synonyms>
    <synonym>5-[(3AS,6R,6ar)-2-hydroxy-1H,3ah,4H,6H,6ah-thieno[3,4-D]imidazol-6-yl]pentanimidate</synonym>
  </synonyms>
  <chemical_formula>C10H17N3O2S</chemical_formula>
  <average_molecular_weight>243.326</average_molecular_weight>
  <monisotopic_moleculate_weight>243.104147493</monisotopic_moleculate_weight>
  <iupac_name>5-[(3aR,4R,6aS)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamide</iupac_name>
  <traditional_iupac>5-[(3aR,4R,6aS)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamide</traditional_iupac>
  <cas_registry_number>6929-42-6</cas_registry_number>
  <smiles>[H][C@@]12CS[C@H](CCCCC(N)=O)[C@]1([H])NC(=O)N2</smiles>
  <inchi>InChI=1S/C10H17N3O2S/c11-8(14)4-2-1-3-7-9-6(5-16-7)12-10(15)13-9/h6-7,9H,1-5H2,(H2,11,14)(H2,12,13,15)/t6-,7-,9-/m1/s1</inchi>
  <inchikey>XFLVBMBRLSCJAI-ZXFLCMHBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as biotin and derivatives. These are organic compounds containing a ureido (tetrahydroimidizalone) ring fused with a tetrahydrothiophene ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Biotin and derivatives</class>
    <sub_class/>
    <direct_parent>Biotin and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Dialkylthioethers</alternative_parent>
      <alternative_parent>Fatty amides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolidinones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Thienoimidazolidines</alternative_parent>
      <alternative_parent>Thiolanes</alternative_parent>
      <alternative_parent>Thiophenes</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Biotin_derivative</substituent>
      <substituent>Carbonic acid derivative</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazolidine</substituent>
      <substituent>Imidazolidinone</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Thienoimidazolidine</substituent>
      <substituent>Thioether</substituent>
      <substituent>Thiolane</substituent>
      <substituent>Thiophene</substituent>
      <substituent>Urea</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-[(3aR,4R,6aS)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>243.326</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>243.104147493</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CS[C@H](CCCCC(N)=O)[C@]1([H])NC(=O)N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H17N3O2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H17N3O2S/c11-8(14)4-2-1-3-7-9-6(5-16-7)12-10(15)13-9/h6-7,9H,1-5H2,(H2,11,14)(H2,12,13,15)/t6-,7-,9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XFLVBMBRLSCJAI-ZXFLCMHBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>84.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>61.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334845</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022636</foodb_id>
  <drugbank_id/>
  <chemspider_id>388677</chemspider_id>
  <pubchem_compound_id>439597</pubchem_compound_id>
  <kegg_id>C01893</kegg_id>
  <chebi_id>16615</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6255</metlin_id>
  <synthesis_reference>Tsuboi, Toshinori; Akagi, Chihiro; Yoshimura, Yoshio; Shoji, Osamu.  Microbial preparation of biotinamide.    Jpn. Tokkyo Koho  (1971),     4 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01240</protein_accession>
      <name>Biotinidase</name>
      <uniprot_id>A6QQ07</uniprot_id>
      <gene_name>BTD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:18 UTC</creation_date>
  <update_date>2020-03-13 16:28:12 UTC</update_date>
  <accession>BMDB0001459</accession>
  <secondary_accessions>
    <accession>BMDB01459</accession>
  </secondary_accessions>
  <name>Guanosine triphosphate adenosine</name>
  <description/>
  <synonyms>
    <synonym>Guanosine triphosphoric acid adenosine</synonym>
    <synonym>[({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][({[(2R,3R,4S,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinate</synonym>
  </synonyms>
  <chemical_formula>C20H27N10O17P3</chemical_formula>
  <average_molecular_weight>772.41</average_molecular_weight>
  <monisotopic_moleculate_weight>772.076850443</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][({[(2R,3R,4S,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid</iupac_name>
  <traditional_iupac>{[(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy({[(2R,3R,4S,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=NC4=C(N)N=CN=C34)[C@@]([H])(O)[C@@]2([H])O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@@]([H])(O)[C@@]1([H])O</smiles>
  <inchi>InChI=1S/C20H27N10O17P3/c21-14-8-15(24-3-23-14)29(4-25-8)18-12(33)10(31)6(44-18)1-42-48(36,37)46-50(40,41)47-49(38,39)43-2-7-11(32)13(34)19(45-7)30-5-26-9-16(30)27-20(22)28-17(9)35/h3-7,10-13,18-19,31-34H,1-2H2,(H,36,37)(H,38,39)(H,40,41)(H2,21,23,24)(H3,22,27,28,35)/t6-,7-,10+,11+,12+,13+,18-,19-/m1/s1</inchi>
  <inchikey>PMJUJCUPNRCBNP-BXGBUAHJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside triphosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside triphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][({[(2R,3R,4S,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>772.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>772.076850443</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=NC4=C(N)N=CN=C34)[C@@]([H])(O)[C@@]2([H])O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@@]([H])(O)[C@@]1([H])O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H27N10O17P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H27N10O17P3/c21-14-8-15(24-3-23-14)29(4-25-8)18-12(33)10(31)6(44-18)1-42-48(36,37)46-50(40,41)47-49(38,39)43-2-7-11(32)13(34)19(45-7)30-5-26-9-16(30)27-20(22)28-17(9)35/h3-7,10-13,18-19,31-34H,1-2H2,(H,36,37)(H,38,39)(H,40,41)(H2,21,23,24)(H3,22,27,28,35)/t6-,7-,10+,11+,12+,13+,18-,19-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PMJUJCUPNRCBNP-BXGBUAHJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>404.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>167.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>63.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1243171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1243172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1243173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1358554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1358555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1358556</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id/>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:19 UTC</creation_date>
  <update_date>2020-03-13 16:28:13 UTC</update_date>
  <accession>BMDB0001460</accession>
  <secondary_accessions>
    <accession>BMDB01460</accession>
  </secondary_accessions>
  <name>Diethylthiophosphate</name>
  <description/>
  <synonyms>
    <synonym>DETP</synonym>
    <synonym>Diethylthiophosphoric acid</synonym>
    <synonym>Diethylthiophosphorate</synonym>
    <synonym>O,O-Diethyl phosphorothionate</synonym>
    <synonym>O,O-Diethyl phosphorothionate, ammonium salt</synonym>
    <synonym>O,O-Diethyl phosphorothionate, sodium salt</synonym>
    <synonym>O,O-Diethyl phosphorothioate</synonym>
    <synonym>O,O-Diethyl phosphorothionate, potassium salt</synonym>
    <synonym>O,O-Diethyl hydrogen thiophosphoric acid</synonym>
    <synonym>Diethylthiophosphate</synonym>
  </synonyms>
  <chemical_formula>C4H11O3PS</chemical_formula>
  <average_molecular_weight>170.167</average_molecular_weight>
  <monisotopic_moleculate_weight>170.01665142</monisotopic_moleculate_weight>
  <iupac_name>diethoxy(sulfanylidene)phosphinous acid</iupac_name>
  <traditional_iupac>DETP</traditional_iupac>
  <cas_registry_number>5871-17-0</cas_registry_number>
  <smiles>CCOP(O)(=S)OCC</smiles>
  <inchi>InChI=1S/C4H11O3PS/c1-3-6-8(5,9)7-4-2/h3-4H2,1-2H3,(H,5,9)</inchi>
  <inchikey>PKUWKAXTAVNIJR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as thiophosphate diesters. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where exactly two R-groups are organyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic thiophosphoric acids and derivatives</class>
    <sub_class>Thiophosphoric acid esters</sub_class>
    <direct_parent>Thiophosphate diesters</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Thiophosphate diester</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>organic thiophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>diethoxy(sulfanylidene)phosphinous acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>170.167</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>170.01665142</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCOP(O)(=S)OCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H11O3PS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H11O3PS/c1-3-6-8(5,9)7-4-2/h3-4H2,1-2H3,(H,5,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PKUWKAXTAVNIJR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>38.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5322</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5323</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437588</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022638</foodb_id>
  <drugbank_id>DB07674</drugbank_id>
  <chemspider_id>635</chemspider_id>
  <pubchem_compound_id>655</pubchem_compound_id>
  <kegg_id>C06607</kegg_id>
  <chebi_id>28006</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6256</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:20 UTC</creation_date>
  <update_date>2020-03-13 16:28:13 UTC</update_date>
  <accession>BMDB0001464</accession>
  <secondary_accessions>
    <accession>BMDB01464</accession>
  </secondary_accessions>
  <name>1-Methylnicotinamide iodide</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C7H9IN2O</chemical_formula>
  <average_molecular_weight>264.0636</average_molecular_weight>
  <monisotopic_moleculate_weight>263.97595634</monisotopic_moleculate_weight>
  <iupac_name>3-carbamoyl-1-methylpyridin-1-ium iodide</iupac_name>
  <traditional_iupac>1-methylnicotinamide iodide</traditional_iupac>
  <cas_registry_number/>
  <smiles>[I-].C[N+]1=CC=CC(=C1)C(N)=O</smiles>
  <inchi>InChI=1S/C7H8N2O.HI/c1-9-4-2-3-6(5-9)7(8)10;/h2-5H,1H3,(H-,8,10);1H</inchi>
  <inchikey>IWEIZMCTGMHCRE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyridinecarboxylic acids and derivatives</sub_class>
    <direct_parent>Nicotinamides</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-methylpyridinium compounds</alternative_parent>
      <alternative_parent>Organic iodide salts</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Pyridinium derivatives</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-methylpyridinium</substituent>
      <substituent>Nicotinamide</substituent>
      <substituent>Organic iodide salt</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Pyridinium</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-carbamoyl-1-methylpyridin-1-ium iodide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>264.0636</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>263.97595634</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[I-].C[N+]1=CC=CC(=C1)C(N)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H9IN2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H8N2O.HI/c1-9-4-2-3-6(5-9)7(8)10;/h2-5H,1H3,(H-,8,10);1H</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IWEIZMCTGMHCRE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>46.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>39.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1287943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1287944</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1287945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1402717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1402718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1402719</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022639</foodb_id>
  <kegg_id/>
  <chemspider_id/>
  <pubchem_compound_id>72660</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Karrer, P.; Benz, F.  Reduction product of nicotinic amide methiodide. II.    Helvetica Chimica Acta  (1936),  19  1028-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:21 UTC</creation_date>
  <update_date>2020-03-13 16:28:14 UTC</update_date>
  <accession>BMDB0001466</accession>
  <secondary_accessions>
    <accession>BMDB01466</accession>
  </secondary_accessions>
  <name>Dimethylaniline-N-oxide</name>
  <description/>
  <synonyms>
    <synonym>Dimethyl(phenyl)amine oxide</synonym>
    <synonym>Dimethylaniline N-oxide</synonym>
    <synonym>N,N-Dimethylaniline N-oxide</synonym>
    <synonym>NN-Dimethylaniline-N-oxide</synonym>
    <synonym>Dimethylaniline N-oxide hydrochloride</synonym>
  </synonyms>
  <chemical_formula>C8H11NO</chemical_formula>
  <average_molecular_weight>137.179</average_molecular_weight>
  <monisotopic_moleculate_weight>137.084063979</monisotopic_moleculate_weight>
  <iupac_name>N-methyl-N-phenylmethanamine oxide</iupac_name>
  <traditional_iupac>dimethylaniline N-oxide</traditional_iupac>
  <cas_registry_number>874-52-2</cas_registry_number>
  <smiles>C[N+](C)([O-])C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C8H11NO/c1-9(2,10)8-6-4-3-5-7-8/h3-7H,1-2H3</inchi>
  <inchikey>LKQUDAOAMBKKQW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class/>
    <direct_parent>Benzene and substituted derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Trisubstituted amine oxides and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-oxide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Trisubstituted n-oxide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N,N-dimethylaniline</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.59</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-methyl-N-phenylmethanamine oxide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>137.179</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>137.084063979</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)([O-])C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H11NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H11NO/c1-9(2,10)8-6-4-3-5-7-8/h3-7H,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LKQUDAOAMBKKQW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>26.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366255</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022640</foodb_id>
  <drugbank_id/>
  <chemspider_id>925</chemspider_id>
  <pubchem_compound_id>950</pubchem_compound_id>
  <kegg_id>C01183</kegg_id>
  <chebi_id>17735</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6259</metlin_id>
  <synthesis_reference>Ziegler, Daniel M.; Pettit, Flora H.  Formation of an intermediate N-oxide in the oxidative demethylation of N,N-dimethylaniline catalyzed by liver microsomes.    Biochemical and Biophysical Research Communications  (1964),  15(2),  188-93.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00119</protein_accession>
      <name>Dimethylaniline monooxygenase [N-oxide-forming] 3</name>
      <uniprot_id>Q8HYJ9</uniprot_id>
      <gene_name>FMO3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:22 UTC</creation_date>
  <update_date>2020-03-13 16:28:14 UTC</update_date>
  <accession>BMDB0001469</accession>
  <secondary_accessions>
    <accession>BMDB01469</accession>
  </secondary_accessions>
  <name>Undecaprenyl diphosphate</name>
  <description/>
  <synonyms>
    <synonym>Diphosphoric acid, mono(3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaenyl) ester</synonym>
    <synonym>Undecaprenyl pyrophosphate</synonym>
    <synonym>UndPP</synonym>
    <synonym>Diphosphate, mono(3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaenyl) ester</synonym>
    <synonym>Undecaprenyl pyrophosphoric acid</synonym>
    <synonym>Undecaprenyl diphosphoric acid</synonym>
    <synonym>Bactoprenyl pyrophosphate</synonym>
    <synonym>Diphosphoric acid mono(3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaenyl) ester</synonym>
    <synonym>Undecaprenyl-PP</synonym>
    <synonym>UPP</synonym>
  </synonyms>
  <chemical_formula>C55H92O7P2</chemical_formula>
  <average_molecular_weight>927.2623</average_molecular_weight>
  <monisotopic_moleculate_weight>926.631828322</monisotopic_moleculate_weight>
  <iupac_name>{[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>undecaprenyl pyrophosphate</traditional_iupac>
  <cas_registry_number>23-13-2</cas_registry_number>
  <smiles>CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C55H92O7P2/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-61-64(59,60)62-63(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3,(H,59,60)(H2,56,57,58)/b46-25+,47-27+,48-29+,49-31+,50-33+,51-35+,52-37+,53-39+,54-41+,55-43+</inchi>
  <inchikey>NTXGVHCCXVHYCL-RDQGWRCRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Polyprenols</sub_class>
    <direct_parent>Bactoprenol diphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Isoprenoid phosphates</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Polyprenyl diphosphates</alternative_parent>
      <alternative_parent>Polyprenyl monophosphates</alternative_parent>
      <alternative_parent>Polyterpenoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Bactoprenol diphosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isoprenoid phosphate</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyprenyl diphosphate</substituent>
      <substituent>Polyprenyl monophosphate</substituent>
      <substituent>Polyterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Bactoprenol diphosphates</external_descriptor>
      <external_descriptor>all-trans-polyprenyl diphosphate</external_descriptor>
      <external_descriptor>undecaprenyl diphosphate</external_descriptor>
      <external_descriptor>undecaprenyl phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>9.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>16.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>927.2623</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>926.631828322</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C55H92O7P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C55H92O7P2/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-61-64(59,60)62-63(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3,(H,59,60)(H2,56,57,58)/b46-25+,47-27+,48-29+,49-31+,50-33+,51-35+,52-37+,53-39+,54-41+,55-43+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NTXGVHCCXVHYCL-RDQGWRCRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>287.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>114.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34966</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022641</foodb_id>
  <drugbank_id/>
  <chemspider_id>4444213</chemspider_id>
  <pubchem_compound_id>5280604</pubchem_compound_id>
  <kegg_id>C03543</kegg_id>
  <chebi_id>17047</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>C55-isoprenyl pyrophosphate</wikipedia_id>
  <metlin_id>3706</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:23 UTC</creation_date>
  <update_date>2020-03-13 16:28:15 UTC</update_date>
  <accession>BMDB0001470</accession>
  <secondary_accessions>
    <accession>BMDB01470</accession>
  </secondary_accessions>
  <name>Tiglic acid</name>
  <description/>
  <synonyms>
    <synonym>(e)-2,3-Dimethylacrylic acid</synonym>
    <synonym>(e)-2-Methylbut-2-enoic acid</synonym>
    <synonym>(e)-2-Methylcrotonic acid</synonym>
    <synonym>Methyl methacrylic acid</synonym>
    <synonym>Tiglinsaeure</synonym>
    <synonym>trans-2,3-Dimethylacrylic acid</synonym>
    <synonym>trans-2-Methyl-2-butenoic acid</synonym>
    <synonym>trans-2-Methylcrotonic acid</synonym>
    <synonym>trans-alpha,beta-Dimethylacrylic acid</synonym>
    <synonym>(e)-2,3-Dimethylacrylate</synonym>
    <synonym>(e)-2-Methylbut-2-enoate</synonym>
    <synonym>(e)-2-Methylcrotonate</synonym>
    <synonym>Methyl methacrylate</synonym>
    <synonym>trans-2,3-Dimethylacrylate</synonym>
    <synonym>trans-2-Methyl-2-butenoate</synonym>
    <synonym>trans-2-Methylcrotonate</synonym>
    <synonym>trans-a,b-Dimethylacrylate</synonym>
    <synonym>trans-a,b-Dimethylacrylic acid</synonym>
    <synonym>trans-alpha,beta-Dimethylacrylate</synonym>
    <synonym>trans-Α,β-dimethylacrylate</synonym>
    <synonym>trans-Α,β-dimethylacrylic acid</synonym>
    <synonym>Tiglate</synonym>
    <synonym>(2E)-2-Methyl-2-butenoate</synonym>
    <synonym>(2E)-2-Methyl-2-butenoic acid</synonym>
    <synonym>(e)-2-Methyl-2-butenoate</synonym>
    <synonym>(e)-2-Methyl-2-butenoic acid</synonym>
    <synonym>(e)-2-Methyl-crotonate</synonym>
    <synonym>(e)-2-Methyl-crotonic acid</synonym>
    <synonym>2,3-Dimethylacrylate</synonym>
    <synonym>2,3-Dimethylacrylic acid</synonym>
    <synonym>2-Methyl-(e)-2-butenoate</synonym>
    <synonym>2-Methyl-(e)-2-butenoic acid</synonym>
    <synonym>2-Methyl-2-butenoate</synonym>
    <synonym>2-Methyl-2-butenoic acid</synonym>
    <synonym>2-Methyl-crotonate</synonym>
    <synonym>2-Methyl-crotonic acid</synonym>
    <synonym>2-Methylbut-2-enoate</synonym>
    <synonym>2-Methylbut-2-enoic acid</synonym>
    <synonym>Cevadate</synonym>
    <synonym>Cevadic acid</synonym>
    <synonym>e-Tiglate</synonym>
    <synonym>e-Tiglic acid</synonym>
    <synonym>epsilon-Tiglate</synonym>
    <synonym>epsilon-Tiglic acid</synonym>
    <synonym>Methylbutenoicacid</synonym>
    <synonym>Tiglinate</synonym>
    <synonym>Tiglinic acid</synonym>
    <synonym>trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoate</synonym>
    <synonym>trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acid</synonym>
    <synonym>trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acid = tiglinate</synonym>
    <synonym>trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acid = tiglinic acid</synonym>
    <synonym>Tiglic acid, (Z)-isomer</synonym>
    <synonym>Tiglic acid, (e)-isomer</synonym>
  </synonyms>
  <chemical_formula>C5H8O2</chemical_formula>
  <average_molecular_weight>100.1158</average_molecular_weight>
  <monisotopic_moleculate_weight>100.0524295</monisotopic_moleculate_weight>
  <iupac_name>(2E)-2-methylbut-2-enoic acid</iupac_name>
  <traditional_iupac>tiglic acid</traditional_iupac>
  <cas_registry_number>80-59-1</cas_registry_number>
  <smiles>C\C=C(/C)C(O)=O</smiles>
  <inchi>InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3+</inchi>
  <inchikey>UIERETOOQGIECD-ONEGZZNKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Methyl-branched fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-methylbut-2-enoic acid</external_descriptor>
      <external_descriptor>Branched fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>61 - 65 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-2-methylbut-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>100.1158</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>100.0524295</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C\C=C(/C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UIERETOOQGIECD-ONEGZZNKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>27.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3988</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438508</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB000774</foodb_id>
  <drugbank_id/>
  <chemspider_id>111629</chemspider_id>
  <pubchem_compound_id>125468</pubchem_compound_id>
  <kegg_id>C08279</kegg_id>
  <chebi_id>9592</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>CPD-7077</meta_cyc_id>
  <knapsack_id>C00001207</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Tiglic_acid</wikipedia_id>
  <metlin_id>6261</metlin_id>
  <synthesis_reference>Jacob, Carl; Hafner, Walter; Wick, Manfred.  Tiglic acid.    Ger. Offen.  (1976),     6 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:25 UTC</creation_date>
  <update_date>2020-03-13 16:28:15 UTC</update_date>
  <accession>BMDB0001471</accession>
  <secondary_accessions>
    <accession>BMDB01471</accession>
  </secondary_accessions>
  <name>Epipregnanolone</name>
  <description/>
  <synonyms>
    <synonym>(3beta,5beta)-3-Hydroxypregnan-20-one</synonym>
    <synonym>3beta-Hydroxy-5beta-pregnane-20-one</synonym>
    <synonym>3beta-Hydroxy-5beta-tetrahydroprogesterone</synonym>
    <synonym>(3b,5b)-3-Hydroxypregnan-20-one</synonym>
    <synonym>(3Β,5β)-3-hydroxypregnan-20-one</synonym>
    <synonym>3b-Hydroxy-5b-pregnane-20-one</synonym>
    <synonym>3Β-hydroxy-5β-pregnane-20-one</synonym>
    <synonym>3b-Hydroxy-5b-tetrahydroprogesterone</synonym>
    <synonym>3Β-hydroxy-5β-tetrahydroprogesterone</synonym>
    <synonym>3-Deoxo-3b-hydroxy-5b-dihydroprogesterone</synonym>
    <synonym>3b,5b-Pregnanolone</synonym>
    <synonym>3b-Hydroxy-5b-pregnan-20-one</synonym>
    <synonym>5b-Pregnan-3b-ol-20-one</synonym>
    <synonym>5b-Pregnane-3b-hydroxy-20-one</synonym>
    <synonym>5b-Pregnane-3b-ol-20-one</synonym>
    <synonym>Pregnanolone I</synonym>
    <synonym>3-Hydroxypregnan-20-one</synonym>
    <synonym>Pregnanolone, (3beta)-isomer</synonym>
    <synonym>3 Hydroxypregnan 20 one</synonym>
    <synonym>3Β-hydroxy-5β-pregnan-20-one</synonym>
    <synonym>3-Deoxo-3beta-hydroxy-5beta-dihydroprogesterone</synonym>
    <synonym>3-Deoxo-3β-hydroxy-5β-dihydroprogesterone</synonym>
    <synonym>3beta,5beta-Pregnanolone</synonym>
    <synonym>3beta-Hydroxy-5beta-pregnan-20-one</synonym>
    <synonym>3Β,5β-pregnanolone</synonym>
    <synonym>5beta-Pregnan-3beta-ol-20-one</synonym>
    <synonym>5beta-Pregnane-3beta-hydroxy-20-one</synonym>
    <synonym>5beta-Pregnane-3beta-ol-20-one</synonym>
    <synonym>5Β-pregnan-3β-ol-20-one</synonym>
    <synonym>5Β-pregnane-3β-hydroxy-20-one</synonym>
    <synonym>5Β-pregnane-3β-ol-20-one</synonym>
    <synonym>Epipregnanolone</synonym>
  </synonyms>
  <chemical_formula>C21H34O2</chemical_formula>
  <average_molecular_weight>318.4935</average_molecular_weight>
  <monisotopic_moleculate_weight>318.255880332</monisotopic_moleculate_weight>
  <iupac_name>1-[(1S,2S,5S,7R,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one</iupac_name>
  <traditional_iupac>1-[(1S,2S,5S,7R,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone</traditional_iupac>
  <cas_registry_number>128-21-2</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O</smiles>
  <inchi>InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16+,17-,18+,19+,20+,21-/m1/s1</inchi>
  <inchikey>AURFZBICLPNKBZ-GRWISUQFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Pregnane steroids</sub_class>
    <direct_parent>Gluco/mineralocorticoids, progestogins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>20-oxosteroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hydroxy-5beta-pregnan-20-one</external_descriptor>
      <external_descriptor>3beta-hydroxy steroid</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(1S,2S,5S,7R,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>318.4935</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>318.255880332</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H34O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16+,17-,18+,19+,20+,21-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AURFZBICLPNKBZ-GRWISUQFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>92.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99687</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C11825</kegg_id>
  <foodb_id>FDB022642</foodb_id>
  <chemspider_id>198867</chemspider_id>
  <pubchem_compound_id>228491</pubchem_compound_id>
  <chebi_id>16229</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Epipregnanolone</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Halpern, Otto.  Pregnenolones and androstenolones.    U.S.  (1969),     6 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:26 UTC</creation_date>
  <update_date>2020-03-13 16:28:16 UTC</update_date>
  <accession>BMDB0001472</accession>
  <secondary_accessions>
    <accession>BMDB01472</accession>
  </secondary_accessions>
  <name>Guanosine pentaphosphate adenosine</name>
  <description/>
  <synonyms>
    <synonym>Guanosine pentaphosphoric acid adenosine</synonym>
    <synonym>P1-(5'-Adenosyl)-P5-(5'-guanosyl) pentaphosphate</synonym>
    <synonym>({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinate</synonym>
  </synonyms>
  <chemical_formula>C20H29N10O23P5</chemical_formula>
  <average_molecular_weight>932.3663</average_molecular_weight>
  <monisotopic_moleculate_weight>932.009509844</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid</traditional_iupac>
  <cas_registry_number>56983-24-5</cas_registry_number>
  <smiles>NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)O[P@](O)(=O)O[P@@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C20H29N10O23P5/c21-14-8-15(24-3-23-14)29(4-25-8)18-12(33)10(31)6(48-18)1-46-54(36,37)50-56(40,41)52-58(44,45)53-57(42,43)51-55(38,39)47-2-7-11(32)13(34)19(49-7)30-5-26-9-16(30)27-20(22)28-17(9)35/h3-7,10-13,18-19,31-34H,1-2H2,(H,36,37)(H,38,39)(H,40,41)(H,42,43)(H,44,45)(H2,21,23,24)(H3,22,27,28,35)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1</inchi>
  <inchikey>CNMILLPGDWDFCZ-INFSMZHSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside polyphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside polyphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-9.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>932.3663</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>932.009509844</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)O[P@](O)(=O)O[P@@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H29N10O23P5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H29N10O23P5/c21-14-8-15(24-3-23-14)29(4-25-8)18-12(33)10(31)6(48-18)1-46-54(36,37)50-56(40,41)52-58(44,45)53-57(42,43)51-55(38,39)47-2-7-11(32)13(34)19(49-7)30-5-26-9-16(30)27-20(22)28-17(9)35/h3-7,10-13,18-19,31-34H,1-2H2,(H,36,37)(H,38,39)(H,40,41)(H,42,43)(H,44,45)(H2,21,23,24)(H3,22,27,28,35)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CNMILLPGDWDFCZ-INFSMZHSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>496.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>177.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>72.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334202</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334203</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022643</foodb_id>
  <chemspider_id>5254634</chemspider_id>
  <pubchem_compound_id>6852180</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:27 UTC</creation_date>
  <update_date>2020-04-14 22:49:15 UTC</update_date>
  <accession>BMDB0001473</accession>
  <secondary_accessions>
    <accession>BMDB01473</accession>
  </secondary_accessions>
  <name>Dihydroxyacetone phosphate</name>
  <description>Dihydroxyacetone phosphate, also known as Dihydroxyacetone phosphate or Dihydroxyacetone phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Dihydroxyacetone phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydroxyacetone phosphate exists in all living species, ranging from bacteria to humans. Dihydroxyacetone phosphate participates in a number of enzymatic reactions, within cattle. In particular, Ubiquinol 8 and dihydroxyacetone phosphate can be biosynthesized from coenzyme Q10 and glycerol 3-phosphate through the action of the enzyme glycerol-3-phosphate dehydrogenase, mitochondrial. In addition, Dihydroxyacetone phosphate can be converted into glycerol 3-phosphate through its interaction with the enzyme glycerol-3-phosphate dehydrogenase [nad(+)], cytoplasmic. In cattle, dihydroxyacetone phosphate is involved in the metabolic pathway called the mitochondrial electron transport chain pathway. Dihydroxyacetone phosphate is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1,3-Dihydroxy-2-propanone monodihydrogen phosphate</synonym>
    <synonym>1,3-Dihydroxy-2-propanone phosphate</synonym>
    <synonym>1,3-Dihydroxyacetone 1-phosphate</synonym>
    <synonym>1-Hydroxy-3-(phosphonooxy)-2-propanone</synonym>
    <synonym>1-Hydroxy-3-(phosphonooxy)acetone</synonym>
    <synonym>3-Hydroxy-2-oxopropyl phosphate</synonym>
    <synonym>DHAP</synonym>
    <synonym>Dihydroxyacetone monophosphate</synonym>
    <synonym>Glycerone monophosphate</synonym>
    <synonym>Glycerone phosphate</synonym>
    <synonym>1,3-Dihydroxy-2-propanone monodihydrogen phosphoric acid</synonym>
    <synonym>1,3-Dihydroxy-2-propanone phosphoric acid</synonym>
    <synonym>1,3-Dihydroxyacetone 1-phosphoric acid</synonym>
    <synonym>3-Hydroxy-2-oxopropyl phosphoric acid</synonym>
    <synonym>Dihydroxyacetone monophosphoric acid</synonym>
    <synonym>Glycerone monophosphoric acid</synonym>
    <synonym>Glycerone phosphoric acid</synonym>
    <synonym>Dihydroxyacetone phosphoric acid</synonym>
    <synonym>1,3-Dihydroxy-2-propanone mono(dihydrogen phosphate)</synonym>
    <synonym>Di-OH-acetone-p</synonym>
    <synonym>Dihydroxy-acetone-p</synonym>
    <synonym>Dihydroxy-acetone-phosphate</synonym>
    <synonym>Dihydroxyacetone 3-phosphate</synonym>
    <synonym>Dihydroxyacetone-p</synonym>
    <synonym>Dihydroxyacetone-phosphate</synonym>
    <synonym>Glycerone-phosphate</synonym>
    <synonym>Phosphoric acid ester with 1,3-dihydroxy-2-propanone</synonym>
    <synonym>3-Phosphate, dihydroxyacetone</synonym>
    <synonym>Phosphate, dihydroxyacetone</synonym>
    <synonym>Dihydroxyacetone 3 phosphate</synonym>
  </synonyms>
  <chemical_formula>C3H7O6P</chemical_formula>
  <average_molecular_weight>170.0578</average_molecular_weight>
  <monisotopic_moleculate_weight>169.998024468</monisotopic_moleculate_weight>
  <iupac_name>(3-hydroxy-2-oxopropoxy)phosphonic acid</iupac_name>
  <traditional_iupac>dihydroxyacetone-phosphate</traditional_iupac>
  <cas_registry_number>57-04-5</cas_registry_number>
  <smiles>OCC(=O)COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)</inchi>
  <inchikey>GNGACRATGGDKBX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharide phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Glycerone phosphates</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Glycerone or derivatives</substituent>
      <substituent>Glycerone phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>glycerone phosphates</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3-hydroxy-2-oxopropoxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>170.0578</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>169.998024468</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(=O)COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7O6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GNGACRATGGDKBX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>104.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Cardiolipin Biosynthesis</name>
      <smpdb_id>SMP0072032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:0)</name>
      <smpdb_id>SMP0077151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:0)</name>
      <smpdb_id>SMP0077153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:0)</name>
      <smpdb_id>SMP0077171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:0)</name>
      <smpdb_id>SMP0077173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077217</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077218</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077219</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077220</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077221</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077222</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077223</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077224</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077225</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077226</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077227</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077228</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077229</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077230</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077231</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077232</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077233</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077234</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077235</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077237</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077238</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077239</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077240</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077241</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077242</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077243</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077244</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077245</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077246</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077247</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077248</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077249</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077250</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077251</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077252</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077253</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077254</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077255</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077256</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077257</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077258</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077259</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077260</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077261</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077262</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077263</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077264</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077265</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077266</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077267</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077268</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077269</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077270</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077271</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077272</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077273</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077274</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077275</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077276</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077277</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077278</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077279</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077280</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077281</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077282</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077283</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077284</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077285</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077286</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077287</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077288</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077289</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077290</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077291</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077292</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077293</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077294</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077295</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077296</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077297</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0077298</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:0)</name>
      <smpdb_id>SMP0077299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:0)</name>
      <smpdb_id>SMP0077310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0077311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:0)</name>
      <smpdb_id>SMP0077312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077318</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077330</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077332</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077334</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077336</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077339</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077340</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077341</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077343</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0077345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077350</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077351</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077365</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077366</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077367</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077368</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077369</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077375</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077377</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077378</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077379</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077381</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077386</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077388</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077389</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077390</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077391</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077392</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077393</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077394</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077395</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077396</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077397</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077398</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077399</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077400</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077401</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0077402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077404</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077405</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077406</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077407</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077411</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077412</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077413</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0077414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0077415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077421</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077422</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077423</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077424</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077425</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077430</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077431</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077432</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077433</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077434</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077435</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077437</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077438</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077439</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077440</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077441</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077442</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077443</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077444</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077445</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077446</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077447</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077448</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077449</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077450</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077451</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077452</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077453</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077454</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077455</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077456</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077457</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077458</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077459</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077460</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077461</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077462</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077463</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077464</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077465</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077481</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077482</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077483</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077484</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077485</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077486</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077487</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077488</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077489</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077490</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077491</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077492</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077493</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077494</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077495</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077496</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077497</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077498</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077499</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077500</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077501</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077502</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077503</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077505</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077507</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077509</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077510</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077511</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077514</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077515</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077516</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077519</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077520</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077522</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077523</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077524</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077525</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077526</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077527</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077528</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077529</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077530</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077531</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077532</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077533</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077534</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077536</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077537</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077538</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077541</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077542</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077549</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077550</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077551</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077552</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077553</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077554</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077555</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077556</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077557</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077558</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077559</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077560</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077561</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077562</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077563</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077564</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077565</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077566</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077567</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077569</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077599</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077600</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077601</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077602</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/16:0)</name>
      <smpdb_id>SMP0077603</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/18:0)</name>
      <smpdb_id>SMP0077604</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077605</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077607</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077608</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077609</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077612</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077613</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077621</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077622</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077695</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077696</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077697</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077699</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077700</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077701</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077702</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077703</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077704</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077705</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077706</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077707</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077708</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077709</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077710</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077711</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077712</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077713</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077714</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077715</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077716</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077717</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077718</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077719</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077720</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077722</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077723</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077724</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077725</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077726</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077727</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077728</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077729</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077730</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077731</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077732</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077733</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077734</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077735</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077736</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077737</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077740</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077741</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077742</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077743</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077744</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077745</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077746</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077747</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077748</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077749</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077750</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0077751</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077752</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077753</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077754</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077755</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077756</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077760</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0077761</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077762</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0077763</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077765</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077766</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077767</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077768</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077769</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0077771</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077772</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077773</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077774</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077775</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077776</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077777</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077778</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077780</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077781</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077783</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077784</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077785</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077786</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077787</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077790</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0077791</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077792</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077793</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077794</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077795</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077796</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077797</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077798</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077801</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077802</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077803</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077804</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077805</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077806</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077808</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077809</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077810</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077811</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077812</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077813</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077814</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077815</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077816</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077817</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0077825</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0077829</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077835</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077836</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077837</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077841</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077842</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077843</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077844</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077845</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077846</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077847</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077850</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077851</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077852</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077853</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077854</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077855</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077856</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077857</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077858</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077859</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077860</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077861</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077862</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077863</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077864</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077865</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077866</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077867</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077868</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077869</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077870</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077871</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077872</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077873</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077874</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077875</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077876</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077877</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077878</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077879</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077880</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077881</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077882</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077883</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077884</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077885</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077886</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077887</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077888</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077889</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0077890</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077891</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0077892</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077893</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077894</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077895</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077897</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0077900</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077901</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0077902</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077903</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077904</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077905</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077906</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077908</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077909</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077910</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077911</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077912</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077916</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077924</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077932</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077933</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077934</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077935</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077936</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077937</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077938</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077939</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077940</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0077941</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077942</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0077943</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077944</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0077947</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0077948</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0077950</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0077951</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077952</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078155</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078156</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078157</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078158</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078159</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078160</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078161</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078162</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078163</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078164</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078165</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078166</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078167</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078168</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078169</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078170</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078171</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078172</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078173</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078174</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078177</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078178</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078179</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078180</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078181</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078182</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078191</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078193</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078194</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078195</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078196</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078197</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078198</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078199</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078200</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078201</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078202</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078203</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078204</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078205</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078206</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078207</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078208</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078209</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078210</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078211</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078212</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078213</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078214</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078215</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078216</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078217</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/16:1(9Z))</name>
      <smpdb_id>SMP0078218</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:0)</name>
      <smpdb_id>SMP0078219</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078220</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078221</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078222</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078223</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078224</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078225</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078226</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078227</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078228</smpdb_id>
      <kegg_map_id/>
    </pathway>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078229</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078231</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078233</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078234</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078235</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078236</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078242</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078243</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078244</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078245</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078246</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078247</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078248</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078249</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078250</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078251</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078252</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078253</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078254</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078255</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078256</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078257</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078258</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078259</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078260</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078261</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078262</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078263</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078264</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078265</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078266</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078267</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078268</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078269</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078270</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078271</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078272</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078273</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078274</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078275</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078276</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078277</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078278</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078279</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078280</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078281</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078282</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078283</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078284</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078285</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078286</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078287</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078288</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078289</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078290</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078291</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078292</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078293</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078294</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078295</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078296</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078297</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078298</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078299</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078300</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0078301</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078302</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078303</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078304</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078305</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078306</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078307</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078308</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078309</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078310</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078311</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078312</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078313</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078314</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078315</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078316</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078317</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078319</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078323</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078324</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078325</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078326</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078327</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078328</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078329</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078330</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078331</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078332</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078333</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078334</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078335</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078336</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078337</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078338</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078339</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078340</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078341</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078342</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078343</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078344</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078345</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078346</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078347</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078348</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078349</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078350</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078351</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078352</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078353</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0078354</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078355</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078356</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078357</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078358</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078359</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0078360</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078361</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078362</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078363</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078364</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078365</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078366</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078367</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078368</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078369</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078370</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078371</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078372</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078373</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078374</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078375</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078376</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078377</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078378</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078379</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078380</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078381</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078382</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078383</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078384</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078385</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078386</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078387</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078388</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078389</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078392</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078393</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078394</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078395</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078397</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078398</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078399</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078400</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078401</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078402</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078403</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078404</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078405</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078406</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078407</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078408</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078409</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078410</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078411</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078412</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078413</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078414</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078415</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078416</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078417</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078418</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078419</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078420</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078421</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078422</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078423</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078424</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078425</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078426</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078427</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078428</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078429</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078430</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078431</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078432</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078433</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078434</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078435</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078436</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078437</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078438</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078439</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078440</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078441</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078442</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078443</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078444</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078445</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078446</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078447</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078448</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078449</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078450</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078451</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078452</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078453</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078454</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078455</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078456</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078457</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078458</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078459</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078460</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078461</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078462</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078463</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078464</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078465</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078466</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078467</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078468</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078469</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078470</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078471</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078473</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078474</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078475</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078478</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078480</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078481</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078482</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078483</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078484</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078485</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078486</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078487</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078488</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078489</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078490</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078491</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078492</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078493</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078494</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078495</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078496</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078497</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078498</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078499</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078500</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078501</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078502</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078503</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078504</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078505</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078506</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078507</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078508</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078509</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078530</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078531</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078535</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:0)</name>
      <smpdb_id>SMP0078536</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078537</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078538</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078541</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078628</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(11Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078713</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078714</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078715</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078716</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078717</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078718</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078719</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078720</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078721</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078722</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078723</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078724</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078725</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078726</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078727</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078728</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078729</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078730</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078731</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078732</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078733</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078734</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078735</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078736</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078737</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078738</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078739</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078740</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078741</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078742</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078743</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078744</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078745</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078746</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078747</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078748</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078749</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078750</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078751</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078752</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078753</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078754</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078755</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078756</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078757</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078758</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078759</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078760</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078761</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078762</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078763</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078764</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078765</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078766</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078768</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078769</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078772</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078774</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078777</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078778</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078779</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078787</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078788</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078789</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078790</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078792</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078793</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078794</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078795</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078796</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078797</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078798</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078799</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078800</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078801</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078802</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078803</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078804</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078805</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078806</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078807</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078808</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078809</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078810</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078811</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078812</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078813</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078814</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078815</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078816</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078817</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078818</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078819</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078820</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078821</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078822</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078823</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078824</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078825</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078826</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0078830</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0078832</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078834</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0078840</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0078842</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078844</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078852</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078853</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078854</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078855</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078859</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0078860</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078861</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0078862</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078863</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078864</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078865</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078866</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078869</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078870</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078872</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078873</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078874</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078875</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0078876</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0078877</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078878</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078879</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078880</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078881</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078882</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078883</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0078884</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0078885</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0078887</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0078888</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0078889</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0078890</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0078891</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0078892</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0078917</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079082</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079085</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079090</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0079091</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079092</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079093</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079094</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079095</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079096</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079097</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079098</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079099</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079100</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079101</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079102</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079103</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079104</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079106</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079113</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079121</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079122</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079123</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079124</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079126</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079130</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079131</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079132</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079134</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079142</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079143</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079144</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079147</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079148</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079149</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079151</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:0)</name>
      <smpdb_id>SMP0079152</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079153</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079154</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079155</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079156</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079157</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079158</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079159</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079160</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079173</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079176</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079180</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079216</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079217</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079218</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079219</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079220</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079221</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079225</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079226</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079231</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079315</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079316</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079453</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079454</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079455</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079456</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079457</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079458</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079459</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079460</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079461</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079462</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079463</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079464</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079465</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079466</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079467</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079468</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079469</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079470</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079471</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079472</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079473</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079474</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079475</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079476</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079477</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079478</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079479</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079480</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079481</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079482</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079483</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079484</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079485</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079486</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079487</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079488</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079489</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079490</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079491</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079492</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079493</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079494</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079495</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079496</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079497</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079498</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079499</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079500</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079501</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079502</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079503</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079504</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079505</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079506</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079507</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079508</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079509</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079510</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:0)</name>
      <smpdb_id>SMP0079511</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079512</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079513</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079514</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079515</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079516</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079517</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079518</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079519</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079520</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079521</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079522</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079523</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079524</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079525</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079526</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079527</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079528</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079529</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079530</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079531</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079532</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079533</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079534</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079535</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079536</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079537</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079538</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079539</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079540</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079541</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079542</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079543</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079544</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079545</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079546</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079547</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079548</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079549</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079550</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079551</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079552</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079553</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079554</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079555</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079556</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079557</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079558</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079559</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079560</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079562</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079563</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079564</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079565</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079566</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079567</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079568</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079569</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079570</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079571</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079572</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079573</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079574</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079575</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079576</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079577</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079578</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079579</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079580</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079581</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079582</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079583</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079584</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079585</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079586</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079588</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/16:0)</name>
      <smpdb_id>SMP0079590</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079591</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079592</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079593</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/16:0)</name>
      <smpdb_id>SMP0079594</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079595</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079596</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079597</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0079598</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079599</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079600</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079601</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079602</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0079603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0079604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0079622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
      <smpdb_id>SMP0079654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
      <smpdb_id>SMP0079656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079673</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079679</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079739</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079743</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079744</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079748</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0079749</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079750</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0079751</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079754</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079755</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079756</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079757</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0079758</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079759</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079760</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079761</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079762</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079763</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079764</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0079765</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079766</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079767</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079771</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079772</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079773</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079779</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0079784</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z))</name>
      <smpdb_id>SMP0079797</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0079798</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0079800</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079803</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0079804</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0079807</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080003</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080004</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080005</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080006</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080007</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080008</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080009</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080010</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080011</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080012</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080013</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080014</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0080015</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080016</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080017</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/18:2(9Z,12Z)/16:0)</name>
      <smpdb_id>SMP0080018</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0)</name>
      <smpdb_id>SMP0080019</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080020</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0080021</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080022</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080023</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080024</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080025</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080026</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080029</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080030</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080031</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080032</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080033</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080034</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080039</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080043</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080044</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080045</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080046</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080051</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080052</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080053</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080054</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080055</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080056</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080060</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080061</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080065</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0)</name>
      <smpdb_id>SMP0080066</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080067</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080068</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080069</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080199</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080200</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080201</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080202</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080203</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080204</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080205</smpdb_id>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080206</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080210</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080236</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080237</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
      <smpdb_id>SMP0080238</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080239</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080240</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080241</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080242</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
      <smpdb_id>SMP0080246</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080247</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080248</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080249</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080250</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080251</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080252</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080253</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080258</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080259</smpdb_id>
      <kegg_map_id/>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080260</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080261</smpdb_id>
      <kegg_map_id/>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080262</smpdb_id>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0)</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
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      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z))</name>
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    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(6Z,9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(8Z,11Z,14Z,17Z)/18:3(9Z,12Z,15Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cardiolipin Biosynthesis CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis</name>
      <smpdb_id>SMP0071338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/10:0)</name>
      <smpdb_id>SMP0108241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/12:0)</name>
      <smpdb_id>SMP0108483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/13:0)</name>
      <smpdb_id>SMP0108481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/14:0)</name>
      <smpdb_id>SMP0108477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/15:0)</name>
      <smpdb_id>SMP0108517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/16:0)</name>
      <smpdb_id>SMP0108480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/17:0)</name>
      <smpdb_id>SMP0108472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/18:0)</name>
      <smpdb_id>SMP0108485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/19:0)</name>
      <smpdb_id>SMP0108526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/8:0)</name>
      <smpdb_id>SMP0108478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-13:0)</name>
      <smpdb_id>SMP0108541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-15:0)</name>
      <smpdb_id>SMP0108542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-17:0)</name>
      <smpdb_id>SMP0108543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-21:0)</name>
      <smpdb_id>SMP0108544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/a-25:0)</name>
      <smpdb_id>SMP0108545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-12:0)</name>
      <smpdb_id>SMP0108546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-13:0)</name>
      <smpdb_id>SMP0108547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-14:0)</name>
      <smpdb_id>SMP0108548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-15:0)</name>
      <smpdb_id>SMP0108549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-16:0)</name>
      <smpdb_id>SMP0108550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-17:0)</name>
      <smpdb_id>SMP0108551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-18:0)</name>
      <smpdb_id>SMP0108552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-19:0)</name>
      <smpdb_id>SMP0108553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-20:0)</name>
      <smpdb_id>SMP0108554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-21:0)</name>
      <smpdb_id>SMP0108555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-22:0)</name>
      <smpdb_id>SMP0108556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/i-24:0)</name>
      <smpdb_id>SMP0108557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/12:0)</name>
      <smpdb_id>SMP0108470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/13:0)</name>
      <smpdb_id>SMP0108512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/14:0)</name>
      <smpdb_id>SMP0108445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/15:0)</name>
      <smpdb_id>SMP0108471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0108558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0108559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0108560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0108561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0108562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0108563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0108564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0108565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0108566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0108567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0108568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0108569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0108570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0108571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0108572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0108573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0108574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/13:0)</name>
      <smpdb_id>SMP0108460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/15:0)</name>
      <smpdb_id>SMP0108469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/16:0)</name>
      <smpdb_id>SMP0108463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/8:0)</name>
      <smpdb_id>SMP0108451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0108575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0108576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0108577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0108578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0108579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0108580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0108581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0108582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0108583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0108584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0108585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0108586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0108587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0108588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0108589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0108590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0108591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/13:0)</name>
      <smpdb_id>SMP0108534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/14:0)</name>
      <smpdb_id>SMP0108525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/15:0)</name>
      <smpdb_id>SMP0108522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/17:0)</name>
      <smpdb_id>SMP0108488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/18:0)</name>
      <smpdb_id>SMP0108489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/19:0)</name>
      <smpdb_id>SMP0108447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0108592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0108593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0108594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0108595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0108596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0108597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0108598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0108599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0108600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0108601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0108602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0108603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0108604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0108605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0108606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0108607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0108608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/15:0)</name>
      <smpdb_id>SMP0108476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/17:0)</name>
      <smpdb_id>SMP0108461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/18:0)</name>
      <smpdb_id>SMP0108523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/8:0)</name>
      <smpdb_id>SMP0108494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0108609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0108610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0108611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0108612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0108613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0108614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0108615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0108616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0108617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0108618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0108619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0108620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0108621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0108622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0108623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0108624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0108625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/12:0)</name>
      <smpdb_id>SMP0108479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/14:0)</name>
      <smpdb_id>SMP0108468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/15:0)</name>
      <smpdb_id>SMP0108507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/16:0)</name>
      <smpdb_id>SMP0108467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/17:0)</name>
      <smpdb_id>SMP0108458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/18:0)</name>
      <smpdb_id>SMP0108518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/8:0)</name>
      <smpdb_id>SMP0108504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0108626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0108627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0108628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0108629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0108630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0108631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0108632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0108633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0108634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0108635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0108636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0108637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0108638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0108639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0108640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0108641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0108642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/12:0)</name>
      <smpdb_id>SMP0108465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/13:0)</name>
      <smpdb_id>SMP0108456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/17:0)</name>
      <smpdb_id>SMP0108506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0108643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0108644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0108645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0108646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0108647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0108648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0108649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0108650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0108651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0108652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0108653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0108654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0108655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0108656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0108657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0108658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0108659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/12:0)</name>
      <smpdb_id>SMP0108495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/13:0)</name>
      <smpdb_id>SMP0108492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/17:0)</name>
      <smpdb_id>SMP0108452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/18:0)</name>
      <smpdb_id>SMP0108448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/19:0)</name>
      <smpdb_id>SMP0108503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/8:0)</name>
      <smpdb_id>SMP0108466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0108660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0108661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0108662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0108663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0108664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0108665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0108666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0108667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0108668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0108669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0108670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0108671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0108672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0108673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0108674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0108675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0108676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/12:0)</name>
      <smpdb_id>SMP0108511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/13:0)</name>
      <smpdb_id>SMP0108473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/15:0)</name>
      <smpdb_id>SMP0108533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/16:0)</name>
      <smpdb_id>SMP0108496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/17:0)</name>
      <smpdb_id>SMP0108521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/19:0)</name>
      <smpdb_id>SMP0108514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0108677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0108678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0108679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-21:0)</name>
      <smpdb_id>SMP0108680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/a-25:0)</name>
      <smpdb_id>SMP0108681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0108682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0108683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0108684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0108685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0108686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0108687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0108688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0108689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-20:0)</name>
      <smpdb_id>SMP0108690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-21:0)</name>
      <smpdb_id>SMP0108691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-22:0)</name>
      <smpdb_id>SMP0108692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/19:0/i-24:0)</name>
      <smpdb_id>SMP0108693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-13:0)</name>
      <smpdb_id>SMP0108694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-15:0)</name>
      <smpdb_id>SMP0108695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-17:0)</name>
      <smpdb_id>SMP0108696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0108697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0108698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-12:0)</name>
      <smpdb_id>SMP0108699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-13:0)</name>
      <smpdb_id>SMP0108700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-14:0)</name>
      <smpdb_id>SMP0108701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-15:0)</name>
      <smpdb_id>SMP0108702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-16:0)</name>
      <smpdb_id>SMP0108703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-17:0)</name>
      <smpdb_id>SMP0108704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-18:0)</name>
      <smpdb_id>SMP0108705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0108706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0108707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0108708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0108709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0108710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0108711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0108712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0108713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0108714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0108715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0108716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0108717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0108718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0108719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0108720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0108721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0108722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0108723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0108724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0108725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0108726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0108727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0108728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0108729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0108730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0108731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0108732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0108733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0108734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0108735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0108736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0108737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0108738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0108739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0108740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0108741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0108742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0108743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0108744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/17:0)</name>
      <smpdb_id>SMP0108457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/8:0)</name>
      <smpdb_id>SMP0108519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0108745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0108746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0108747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0108748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0108749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0108750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0108751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0108752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0108753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0108754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0108755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0108756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0108757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0108759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0111848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0108761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0108763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0108765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0108767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0108768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0108770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0108772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0108774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0108775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0108777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0108778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0108779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0108780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0108781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0108782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0108783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0108784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0108785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0108786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0108787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0108788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0108789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0108790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0108791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0108792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0108793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0108794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0108795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0108796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0108797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0108798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0108799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0108800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0108801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0108802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0108803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0108804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0108805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0108806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0108807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0108808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0108809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0108810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0108811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0108812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0108813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0108814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0108815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0108816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0108817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0108818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0108819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0108820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0108821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0108822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0108823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0108824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0108825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0108826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0108827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0108828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0108829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0108830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0108831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0108832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0108833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0108834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0108835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0108836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0108837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0108838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0108839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0108840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0108841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0108842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0108843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0108844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0108845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0108846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0108847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0108848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0108849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0108850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0108851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0108852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0108853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0108854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0108855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0108856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0108857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0108858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0108859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0108860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0108861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0108862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0108863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0108864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0108865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0108866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0108867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0108868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0108869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0108870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0108871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0108872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0108873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0108874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0108875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0108876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0108877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0108878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0108879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0108880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0108881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0108882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0108883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0108884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0108885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0108886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0108887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0108888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0108889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0108890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0108891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0108892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0108893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0108894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0108895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0108896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0108897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0108898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0108899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0108900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0108901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0108902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0108903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0108904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0108905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0108906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0108907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0108908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0108909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0108910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0108911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0108912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/a-25:0)</name>
      <smpdb_id>SMP0108913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0108914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0108915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0108916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/a-25:0)</name>
      <smpdb_id>SMP0108917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0108918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0108919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-24:0/a-25:0)</name>
      <smpdb_id>SMP0108920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0108921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(12:0/12:0/12:0)</name>
      <smpdb_id>SMP0108243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/14:0)</name>
      <smpdb_id>SMP0072652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/14:1(9Z))</name>
      <smpdb_id>SMP0072653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/15:0)</name>
      <smpdb_id>SMP0072654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/16:0)</name>
      <smpdb_id>SMP0072655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/16:1(9Z))</name>
      <smpdb_id>SMP0072656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:0)</name>
      <smpdb_id>SMP0072657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:1(11Z))</name>
      <smpdb_id>SMP0072658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:1(9Z))</name>
      <smpdb_id>SMP0072659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:0)</name>
      <smpdb_id>SMP0072664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:1(11Z))</name>
      <smpdb_id>SMP0072665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:0)</name>
      <smpdb_id>SMP0072672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:1(13Z))</name>
      <smpdb_id>SMP0072673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/24:0)</name>
      <smpdb_id>SMP0072679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/24:1(15Z))</name>
      <smpdb_id>SMP0072680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0072681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0072682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0072683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0072684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0072685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/15:0)</name>
      <smpdb_id>SMP0072709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/16:0)</name>
      <smpdb_id>SMP0072710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/16:1(9Z))</name>
      <smpdb_id>SMP0072711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:0)</name>
      <smpdb_id>SMP0072712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:1(11Z))</name>
      <smpdb_id>SMP0072713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:1(9Z))</name>
      <smpdb_id>SMP0072714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:0)</name>
      <smpdb_id>SMP0072719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:1(11Z))</name>
      <smpdb_id>SMP0072720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:0)</name>
      <smpdb_id>SMP0072727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:1(13Z))</name>
      <smpdb_id>SMP0072728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/24:0)</name>
      <smpdb_id>SMP0072734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/24:1(15Z))</name>
      <smpdb_id>SMP0072735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/16:0)</name>
      <smpdb_id>SMP0072736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0072737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:0)</name>
      <smpdb_id>SMP0072738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0072739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0072740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:0)</name>
      <smpdb_id>SMP0072745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0072746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:0)</name>
      <smpdb_id>SMP0072753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0072754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/24:0)</name>
      <smpdb_id>SMP0072760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0072761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0072762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0072763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:0)</name>
      <smpdb_id>SMP0072787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0072788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0072789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:0)</name>
      <smpdb_id>SMP0072794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0072795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:0)</name>
      <smpdb_id>SMP0072802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0072803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/24:0)</name>
      <smpdb_id>SMP0072809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0072810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0072817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0072825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0072832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0072860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0072868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0072875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0072880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0072888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0072895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0072899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0072907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0072914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0072917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0072925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0072932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:0)</name>
      <smpdb_id>SMP0072934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0072935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:0)</name>
      <smpdb_id>SMP0072942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0072943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/24:0)</name>
      <smpdb_id>SMP0072949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0072950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0072958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0072965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0072973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0072980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0072987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0072994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:0)</name>
      <smpdb_id>SMP0073042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0073043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/24:0)</name>
      <smpdb_id>SMP0073049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0073050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0073057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:0/24:0)</name>
      <smpdb_id>SMP0073084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0073085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0073087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0073088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0073089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/15:0)</name>
      <smpdb_id>SMP0073115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/16:0)</name>
      <smpdb_id>SMP0073116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/16:1(9Z))</name>
      <smpdb_id>SMP0073117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:0)</name>
      <smpdb_id>SMP0073118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:1(11Z))</name>
      <smpdb_id>SMP0073119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:1(9Z))</name>
      <smpdb_id>SMP0073120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:0)</name>
      <smpdb_id>SMP0073125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:1(11Z))</name>
      <smpdb_id>SMP0073126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:0)</name>
      <smpdb_id>SMP0073133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:1(13Z))</name>
      <smpdb_id>SMP0073134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/24:0)</name>
      <smpdb_id>SMP0073140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/15:0/24:1(15Z))</name>
      <smpdb_id>SMP0073141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/16:0)</name>
      <smpdb_id>SMP0073142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:0)</name>
      <smpdb_id>SMP0073144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:0)</name>
      <smpdb_id>SMP0073151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:0)</name>
      <smpdb_id>SMP0073159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/24:0)</name>
      <smpdb_id>SMP0073166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0073193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0073194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0073195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:0)</name>
      <smpdb_id>SMP0073200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0073201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:0)</name>
      <smpdb_id>SMP0073208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0073209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/24:0)</name>
      <smpdb_id>SMP0073215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0073216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0073223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:0)</name>
      <smpdb_id>SMP0073340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0073341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:0)</name>
      <smpdb_id>SMP0073348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0073349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/24:0)</name>
      <smpdb_id>SMP0073355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0073356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0073393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0073400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:0)</name>
      <smpdb_id>SMP0073448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0073449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/24:0)</name>
      <smpdb_id>SMP0073455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0073456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0073463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/24:0/24:0)</name>
      <smpdb_id>SMP0073490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0073491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/15:0)</name>
      <smpdb_id>SMP0073493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/16:0)</name>
      <smpdb_id>SMP0073494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/16:1(9Z))</name>
      <smpdb_id>SMP0073495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:0)</name>
      <smpdb_id>SMP0073496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:1(11Z))</name>
      <smpdb_id>SMP0073497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:1(9Z))</name>
      <smpdb_id>SMP0073498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:0)</name>
      <smpdb_id>SMP0073503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:1(11Z))</name>
      <smpdb_id>SMP0073504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:0)</name>
      <smpdb_id>SMP0073511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:1(13Z))</name>
      <smpdb_id>SMP0073512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/24:0)</name>
      <smpdb_id>SMP0073518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/15:0/24:1(15Z))</name>
      <smpdb_id>SMP0073519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/16:0)</name>
      <smpdb_id>SMP0073520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:0)</name>
      <smpdb_id>SMP0073522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:0)</name>
      <smpdb_id>SMP0073529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:0)</name>
      <smpdb_id>SMP0073537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/24:0)</name>
      <smpdb_id>SMP0073544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:0)</name>
      <smpdb_id>SMP0073571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0073572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0073573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:0)</name>
      <smpdb_id>SMP0073578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0073579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:0)</name>
      <smpdb_id>SMP0073586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0073587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/24:0)</name>
      <smpdb_id>SMP0073593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0073594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0073601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0073672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0073679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0073701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0073709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0073716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:0)</name>
      <smpdb_id>SMP0073718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0073719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:0)</name>
      <smpdb_id>SMP0073726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0073727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/24:0)</name>
      <smpdb_id>SMP0073733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0073734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0073771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0073778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:0)</name>
      <smpdb_id>SMP0073826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0073827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/24:0)</name>
      <smpdb_id>SMP0073833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0073834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0073841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/24:0/24:0)</name>
      <smpdb_id>SMP0073868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0073869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(15:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:0)</name>
      <smpdb_id>SMP0073871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0073872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:0)</name>
      <smpdb_id>SMP0073873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0073874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0073875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:0)</name>
      <smpdb_id>SMP0073880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0073881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:0)</name>
      <smpdb_id>SMP0073888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0073889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/24:0)</name>
      <smpdb_id>SMP0073895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0073896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0073897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0073898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:0)</name>
      <smpdb_id>SMP0073922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0073923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0073924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:0)</name>
      <smpdb_id>SMP0073929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0073930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:0)</name>
      <smpdb_id>SMP0073937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0073938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/24:0)</name>
      <smpdb_id>SMP0073944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0073945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0073946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0073952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0073960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0073967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0073969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0073974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0073982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0073989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0073991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0073992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0073994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0073995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0073996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0073997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0073998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:0)</name>
      <smpdb_id>SMP0074069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:0)</name>
      <smpdb_id>SMP0074077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/24:0)</name>
      <smpdb_id>SMP0074084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0074122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0074129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:0)</name>
      <smpdb_id>SMP0074177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0074178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/24:0)</name>
      <smpdb_id>SMP0074184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0074185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0074192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:0/24:0)</name>
      <smpdb_id>SMP0074219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0074220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0074222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0074223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:0)</name>
      <smpdb_id>SMP0074247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0074248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0074249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:0)</name>
      <smpdb_id>SMP0074254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0074255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:0)</name>
      <smpdb_id>SMP0074262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0074263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/24:0)</name>
      <smpdb_id>SMP0074269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0074270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0074277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:0)</name>
      <smpdb_id>SMP0074394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:0)</name>
      <smpdb_id>SMP0074402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/24:0)</name>
      <smpdb_id>SMP0074409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0074447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0074454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:0)</name>
      <smpdb_id>SMP0074502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0074503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/24:0)</name>
      <smpdb_id>SMP0074509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0074510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0074517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/24:0/24:0)</name>
      <smpdb_id>SMP0074544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0074545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:0)</name>
      <smpdb_id>SMP0074547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0074548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0074549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:0)</name>
      <smpdb_id>SMP0074554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0074555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:0)</name>
      <smpdb_id>SMP0074562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0074563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/24:0)</name>
      <smpdb_id>SMP0074569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0074570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0074577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:0)</name>
      <smpdb_id>SMP0074695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:0)</name>
      <smpdb_id>SMP0074703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/24:0)</name>
      <smpdb_id>SMP0074710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0074748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0074756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0074774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0074781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0074795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0074802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:0)</name>
      <smpdb_id>SMP0074804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0074805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/24:0)</name>
      <smpdb_id>SMP0074811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0074812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0074819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0074837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0074844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/24:0/24:0)</name>
      <smpdb_id>SMP0074846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0074847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0074849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0074855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0074870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0074872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0074877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0074885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0074892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0074894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0074915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0074918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0074926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0074933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0074954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0074955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0074963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0074970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0074971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:0)</name>
      <smpdb_id>SMP0074972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0074973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:0)</name>
      <smpdb_id>SMP0074980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0074981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0074984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0074987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/24:0)</name>
      <smpdb_id>SMP0074988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0074989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0074990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0074991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0074992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0074994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0074996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0074997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0074998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0074999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0075126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0075127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0075131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0075139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0075146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0075148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0075380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0075611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0075614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0075622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0075629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0075816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/24:0/24:0)</name>
      <smpdb_id>SMP0075818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0075819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(6Z,9Z,12Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0075840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0075841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0075849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0075856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:0)</name>
      <smpdb_id>SMP0075858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0075859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:0)</name>
      <smpdb_id>SMP0075866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0075867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/24:0)</name>
      <smpdb_id>SMP0075873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0075874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0075875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0075882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0075889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0075891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0075906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0075911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0075918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0075933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0075936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0075943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0075956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0075957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0075964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:0)</name>
      <smpdb_id>SMP0075966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0075967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/24:0)</name>
      <smpdb_id>SMP0075973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0075974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0075975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0075981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0075983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0075995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0075996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0075998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0075999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:3(9Z,12Z,15Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0076011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0076012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0076020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0076027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:0)</name>
      <smpdb_id>SMP0076029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0076030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:0)</name>
      <smpdb_id>SMP0076037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0076038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/24:0)</name>
      <smpdb_id>SMP0076044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0076045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0076053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0076060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/20:0)</name>
      <smpdb_id>SMP0108262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/21:0)</name>
      <smpdb_id>SMP0108257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/22:0)</name>
      <smpdb_id>SMP0108278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/a-21:0)</name>
      <smpdb_id>SMP0108922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/a-25:0)</name>
      <smpdb_id>SMP0108923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-21:0)</name>
      <smpdb_id>SMP0108924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-22:0)</name>
      <smpdb_id>SMP0108925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/19:0/i-24:0)</name>
      <smpdb_id>SMP0108926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/21:0)</name>
      <smpdb_id>SMP0108277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/22:0)</name>
      <smpdb_id>SMP0108311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0108927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0108928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0108929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0108930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0108931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0108932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0108933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/10:0)</name>
      <smpdb_id>SMP0108328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/12:0)</name>
      <smpdb_id>SMP0108244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/13:0)</name>
      <smpdb_id>SMP0108317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/14:0)</name>
      <smpdb_id>SMP0108266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/15:0)</name>
      <smpdb_id>SMP0108275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/16:0)</name>
      <smpdb_id>SMP0108332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/17:0)</name>
      <smpdb_id>SMP0108292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/18:0)</name>
      <smpdb_id>SMP0108327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/21:0)</name>
      <smpdb_id>SMP0108305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/22:0)</name>
      <smpdb_id>SMP0108316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/8:0)</name>
      <smpdb_id>SMP0108301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0108934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0108935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0108936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0108937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0108938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0108939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0108940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0108941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0108942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0108943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0108944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0108945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0108946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0108947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0108948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0108949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0108950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/10:0)</name>
      <smpdb_id>SMP0108279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/12:0)</name>
      <smpdb_id>SMP0108261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/13:0)</name>
      <smpdb_id>SMP0108286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/14:0)</name>
      <smpdb_id>SMP0108255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/15:0)</name>
      <smpdb_id>SMP0108252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/16:0)</name>
      <smpdb_id>SMP0108299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/17:0)</name>
      <smpdb_id>SMP0108308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/18:0)</name>
      <smpdb_id>SMP0108282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/22:0)</name>
      <smpdb_id>SMP0108265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/8:0)</name>
      <smpdb_id>SMP0108319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0108951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0108952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0108953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0108954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0108955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0108956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0108957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0108958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0108959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0108960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0108961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0108962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0108963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0108964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0108965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0108966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0108967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0108968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/13:0)</name>
      <smpdb_id>SMP0108969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/14:0)</name>
      <smpdb_id>SMP0108970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/15:0)</name>
      <smpdb_id>SMP0108971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/16:0)</name>
      <smpdb_id>SMP0108972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/17:0)</name>
      <smpdb_id>SMP0108973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/18:0)</name>
      <smpdb_id>SMP0108974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/8:0)</name>
      <smpdb_id>SMP0108975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-13:0)</name>
      <smpdb_id>SMP0108976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-15:0)</name>
      <smpdb_id>SMP0108977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-17:0)</name>
      <smpdb_id>SMP0108978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0108979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0108980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0108981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0108982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0108983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0108984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0108985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0108986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0108987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0108988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0108989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0108990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0108991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0108992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/12:0)</name>
      <smpdb_id>SMP0108993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/13:0)</name>
      <smpdb_id>SMP0108994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/14:0)</name>
      <smpdb_id>SMP0108995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/15:0)</name>
      <smpdb_id>SMP0108996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/16:0)</name>
      <smpdb_id>SMP0108997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/17:0)</name>
      <smpdb_id>SMP0108998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/18:0)</name>
      <smpdb_id>SMP0108999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/8:0)</name>
      <smpdb_id>SMP0109000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-13:0)</name>
      <smpdb_id>SMP0109001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-15:0)</name>
      <smpdb_id>SMP0109002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-17:0)</name>
      <smpdb_id>SMP0109003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0109021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0109022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0109023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0109024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0109025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0109026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0109027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/8:0)</name>
      <smpdb_id>SMP0109028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0109029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0109030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0109031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0109032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0109033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0109034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0109035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0109036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0109037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0109038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-19:0)</name>
      <smpdb_id>SMP0109039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0109043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0109044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0109045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0109046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0109047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0109048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0109049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/8:0)</name>
      <smpdb_id>SMP0109050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0109051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0109052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0109053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0109054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0109055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0109056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0109057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0109058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0109059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0109060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-19:0)</name>
      <smpdb_id>SMP0109061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0109064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0109065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0109066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0109067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0109068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0109069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0109070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/8:0)</name>
      <smpdb_id>SMP0109071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0109072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0109073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0109074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0109075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0109076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0109078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0109079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0109080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0109081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0109082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-19:0)</name>
      <smpdb_id>SMP0109083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/10:0)</name>
      <smpdb_id>SMP0108330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/14:0)</name>
      <smpdb_id>SMP0108290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/17:0)</name>
      <smpdb_id>SMP0108312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/19:0)</name>
      <smpdb_id>SMP0108270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/21:0)</name>
      <smpdb_id>SMP0108300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/22:0)</name>
      <smpdb_id>SMP0108259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/10:0)</name>
      <smpdb_id>SMP0108320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/12:0)</name>
      <smpdb_id>SMP0108331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/13:0)</name>
      <smpdb_id>SMP0108318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/16:0)</name>
      <smpdb_id>SMP0108293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/17:0)</name>
      <smpdb_id>SMP0108304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/18:0)</name>
      <smpdb_id>SMP0108297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/19:0)</name>
      <smpdb_id>SMP0108288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/21:0)</name>
      <smpdb_id>SMP0108322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/22:0)</name>
      <smpdb_id>SMP0108314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/8:0)</name>
      <smpdb_id>SMP0108263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/10:0)</name>
      <smpdb_id>SMP0108256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/13:0)</name>
      <smpdb_id>SMP0108326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/15:0)</name>
      <smpdb_id>SMP0108250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/16:0)</name>
      <smpdb_id>SMP0108247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/21:0)</name>
      <smpdb_id>SMP0108313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/22:0)</name>
      <smpdb_id>SMP0108283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/8:0)</name>
      <smpdb_id>SMP0108276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/12:0)</name>
      <smpdb_id>SMP0108248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/13:0)</name>
      <smpdb_id>SMP0108295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/19:0)</name>
      <smpdb_id>SMP0108249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/21:0)</name>
      <smpdb_id>SMP0108271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/10:0)</name>
      <smpdb_id>SMP0108267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/12:0)</name>
      <smpdb_id>SMP0108324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/17:0)</name>
      <smpdb_id>SMP0108284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/21:0)</name>
      <smpdb_id>SMP0108306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/10:0)</name>
      <smpdb_id>SMP0108274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/19:0)</name>
      <smpdb_id>SMP0108269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/21:0)</name>
      <smpdb_id>SMP0108251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/13:0)</name>
      <smpdb_id>SMP0108289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/14:0)</name>
      <smpdb_id>SMP0108253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/16:0)</name>
      <smpdb_id>SMP0108302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/17:0)</name>
      <smpdb_id>SMP0108254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/19:0)</name>
      <smpdb_id>SMP0108264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/21:0)</name>
      <smpdb_id>SMP0108281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/22:0)</name>
      <smpdb_id>SMP0108294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/8:0)</name>
      <smpdb_id>SMP0108296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/10:0)</name>
      <smpdb_id>SMP0108315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/13:0)</name>
      <smpdb_id>SMP0108307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/17:0)</name>
      <smpdb_id>SMP0108273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/21:0)</name>
      <smpdb_id>SMP0108323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/8:0)</name>
      <smpdb_id>SMP0108287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/13:0)</name>
      <smpdb_id>SMP0108291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/15:0)</name>
      <smpdb_id>SMP0108272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/18:0)</name>
      <smpdb_id>SMP0108258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0109204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0109205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0109206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0109207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0109208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0109209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0109210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0109211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0109212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0109213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/10:0)</name>
      <smpdb_id>SMP0108309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/12:0)</name>
      <smpdb_id>SMP0108333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/13:0)</name>
      <smpdb_id>SMP0108329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/17:0)</name>
      <smpdb_id>SMP0108303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/19:0)</name>
      <smpdb_id>SMP0108321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:0)</name>
      <smpdb_id>SMP0076182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0076183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/21:0)</name>
      <smpdb_id>SMP0108390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:0)</name>
      <smpdb_id>SMP0076190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0076191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/24:0)</name>
      <smpdb_id>SMP0076197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0076198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/8:0)</name>
      <smpdb_id>SMP0108268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-13:0)</name>
      <smpdb_id>SMP0109214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-15:0)</name>
      <smpdb_id>SMP0109215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-17:0)</name>
      <smpdb_id>SMP0109216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-21:0)</name>
      <smpdb_id>SMP0109217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/a-25:0)</name>
      <smpdb_id>SMP0109218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-12:0)</name>
      <smpdb_id>SMP0109219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-13:0)</name>
      <smpdb_id>SMP0109220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-14:0)</name>
      <smpdb_id>SMP0109221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-15:0)</name>
      <smpdb_id>SMP0109222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-16:0)</name>
      <smpdb_id>SMP0109223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-17:0)</name>
      <smpdb_id>SMP0109224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-18:0)</name>
      <smpdb_id>SMP0109225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-19:0)</name>
      <smpdb_id>SMP0109226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-20:0)</name>
      <smpdb_id>SMP0109227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-21:0)</name>
      <smpdb_id>SMP0109228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-22:0)</name>
      <smpdb_id>SMP0109229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:0/i-24:0)</name>
      <smpdb_id>SMP0109230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0076206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0076213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/21:0)</name>
      <smpdb_id>SMP0108389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/22:0)</name>
      <smpdb_id>SMP0108370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0109231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0109232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0109233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0109234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0109235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0109236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0109237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0109238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0109239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0109240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0109241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0109242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0109243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0109244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0109245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0109246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0109247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:0)</name>
      <smpdb_id>SMP0076290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/24:0)</name>
      <smpdb_id>SMP0076297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/24:0/24:0)</name>
      <smpdb_id>SMP0076332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/10:0)</name>
      <smpdb_id>SMP0108298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/14:0)</name>
      <smpdb_id>SMP0108246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/15:0)</name>
      <smpdb_id>SMP0108285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/16:0)</name>
      <smpdb_id>SMP0108280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/19:0)</name>
      <smpdb_id>SMP0108310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/21:0)</name>
      <smpdb_id>SMP0108245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/22:0)</name>
      <smpdb_id>SMP0108260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/8:0)</name>
      <smpdb_id>SMP0108325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0109330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0109370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0109371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0109372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0109373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0109374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0109375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0109376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0109377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0109378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0109379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0109380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0109381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0109382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0109383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0109384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0109385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0109386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0109387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0109388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0109389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0109390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0109391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0109392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0109393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0109394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0109395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0109396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0109397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0109398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0109400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0109401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0109402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0109403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0109404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0109405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0109406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0109407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0109408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0109409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0109410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0109411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0109412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0109413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0109414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0109415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0109416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0109417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0109418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0109419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0109420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0109421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0109422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0109423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0109424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0109425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0109426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0076335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0076342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0076349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:1(11Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0076471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:2(11Z,14Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0076591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0076596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0076603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(5Z,8Z,11Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:3(8Z,11Z,14Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0076787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0076790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0076797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(5Z,8Z,11Z,14Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:4(8Z,11Z,14Z,17Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0076931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0076932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0076939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:0)</name>
      <smpdb_id>SMP0076941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/24:0)</name>
      <smpdb_id>SMP0076948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0076956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0076974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0076981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/24:0)</name>
      <smpdb_id>SMP0076983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0076984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0076985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/10:0)</name>
      <smpdb_id>SMP0108335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/12:0)</name>
      <smpdb_id>SMP0108363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/13:0)</name>
      <smpdb_id>SMP0108339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/17:0)</name>
      <smpdb_id>SMP0108349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/18:0)</name>
      <smpdb_id>SMP0108337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/10:0/22:0)</name>
      <smpdb_id>SMP0108367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/12:0)</name>
      <smpdb_id>SMP0108361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/13:0)</name>
      <smpdb_id>SMP0108351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/14:0)</name>
      <smpdb_id>SMP0108344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/15:0)</name>
      <smpdb_id>SMP0108371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/16:0)</name>
      <smpdb_id>SMP0108383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/18:0)</name>
      <smpdb_id>SMP0108387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/22:0)</name>
      <smpdb_id>SMP0108366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0109440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/13:0)</name>
      <smpdb_id>SMP0108368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/16:0)</name>
      <smpdb_id>SMP0108380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/17:0)</name>
      <smpdb_id>SMP0108345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/18:0)</name>
      <smpdb_id>SMP0108341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/22:0)</name>
      <smpdb_id>SMP0108388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/10:0)</name>
      <smpdb_id>SMP0108347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/13:0)</name>
      <smpdb_id>SMP0108342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/14:0)</name>
      <smpdb_id>SMP0108338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/16:0)</name>
      <smpdb_id>SMP0108346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/17:0)</name>
      <smpdb_id>SMP0108352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/18:0)</name>
      <smpdb_id>SMP0108386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/22:0)</name>
      <smpdb_id>SMP0108334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/8:0)</name>
      <smpdb_id>SMP0108365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/10:0)</name>
      <smpdb_id>SMP0108372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/13:0)</name>
      <smpdb_id>SMP0108358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/14:0)</name>
      <smpdb_id>SMP0108375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/15:0)</name>
      <smpdb_id>SMP0108348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/17:0)</name>
      <smpdb_id>SMP0108384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/18:0)</name>
      <smpdb_id>SMP0108369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/22:0)</name>
      <smpdb_id>SMP0108392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/8:0)</name>
      <smpdb_id>SMP0108354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/10:0)</name>
      <smpdb_id>SMP0108350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/15:0)</name>
      <smpdb_id>SMP0108355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/16:0)</name>
      <smpdb_id>SMP0108381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/17:0)</name>
      <smpdb_id>SMP0108364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/18:0)</name>
      <smpdb_id>SMP0108356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/22:0)</name>
      <smpdb_id>SMP0108385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/12:0)</name>
      <smpdb_id>SMP0108376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/17:0)</name>
      <smpdb_id>SMP0108393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/8:0)</name>
      <smpdb_id>SMP0108377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/17:0)</name>
      <smpdb_id>SMP0108396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/18:0)</name>
      <smpdb_id>SMP0108399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/10:0)</name>
      <smpdb_id>SMP0108340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/12:0)</name>
      <smpdb_id>SMP0108374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/13:0)</name>
      <smpdb_id>SMP0108336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/14:0)</name>
      <smpdb_id>SMP0108373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/15:0)</name>
      <smpdb_id>SMP0108382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/16:0)</name>
      <smpdb_id>SMP0108391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/17:0)</name>
      <smpdb_id>SMP0108397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/18:0)</name>
      <smpdb_id>SMP0108398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/22:0)</name>
      <smpdb_id>SMP0108400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/8:0)</name>
      <smpdb_id>SMP0108343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-13:0)</name>
      <smpdb_id>SMP0109556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-15:0)</name>
      <smpdb_id>SMP0109557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-17:0)</name>
      <smpdb_id>SMP0109558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-21:0)</name>
      <smpdb_id>SMP0109559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/a-25:0)</name>
      <smpdb_id>SMP0109560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-12:0)</name>
      <smpdb_id>SMP0109561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-13:0)</name>
      <smpdb_id>SMP0109562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-14:0)</name>
      <smpdb_id>SMP0109563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-15:0)</name>
      <smpdb_id>SMP0109564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-16:0)</name>
      <smpdb_id>SMP0109565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-17:0)</name>
      <smpdb_id>SMP0109566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-18:0)</name>
      <smpdb_id>SMP0109567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-19:0)</name>
      <smpdb_id>SMP0109568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-20:0)</name>
      <smpdb_id>SMP0109569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-21:0)</name>
      <smpdb_id>SMP0109570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-22:0)</name>
      <smpdb_id>SMP0109571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/i-24:0)</name>
      <smpdb_id>SMP0109572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/17:0)</name>
      <smpdb_id>SMP0108395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/18:0)</name>
      <smpdb_id>SMP0108394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/22:0)</name>
      <smpdb_id>SMP0108401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/10:0)</name>
      <smpdb_id>SMP0108360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/12:0)</name>
      <smpdb_id>SMP0108357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/13:0)</name>
      <smpdb_id>SMP0108353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/16:0)</name>
      <smpdb_id>SMP0108359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/18:0)</name>
      <smpdb_id>SMP0108378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/22:0)</name>
      <smpdb_id>SMP0108362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/8:0)</name>
      <smpdb_id>SMP0108379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0109694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0109695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0109696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0109697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0109698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0109699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0109700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0109701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0109702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0109703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0109704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0109705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0109706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0109707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0109708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0109709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0109710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0109711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0109712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0109713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0109714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0109715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0109716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0109717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0109718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0109719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0109720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0109721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0109722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0109723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0109724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0109725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0109726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0109727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0109728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0109729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0109730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0109731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0109732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0109733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0109734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0109735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0109736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0109737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0109738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0109739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0109740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0109741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0109742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0109743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0109744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0109745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0109746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0109747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0109748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0109749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0109750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0109751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0109752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0109753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0109754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0109755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0109756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0109757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0109758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0109759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/10:0)</name>
      <smpdb_id>SMP0108437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/12:0)</name>
      <smpdb_id>SMP0108408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/10:0/13:0)</name>
      <smpdb_id>SMP0108423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/12:0)</name>
      <smpdb_id>SMP0108405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/13:0)</name>
      <smpdb_id>SMP0108403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/14:0)</name>
      <smpdb_id>SMP0108414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/15:0)</name>
      <smpdb_id>SMP0108426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/18:0)</name>
      <smpdb_id>SMP0108407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/8:0)</name>
      <smpdb_id>SMP0108420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0109760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0109761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0109762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0109763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0109764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0109765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0109766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0109767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0109768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0109769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0109770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0109771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0109772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0109773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0109774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0109775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0109776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/13:0)</name>
      <smpdb_id>SMP0108436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/15:0)</name>
      <smpdb_id>SMP0108428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/16:0)</name>
      <smpdb_id>SMP0108430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/17:0)</name>
      <smpdb_id>SMP0108419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/18:0)</name>
      <smpdb_id>SMP0108413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/8:0)</name>
      <smpdb_id>SMP0108411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0109777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0109778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0109779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0109780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0109781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0109782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0109783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0109784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0109785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0109786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0109787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0109788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0109789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0109790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0109791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0109792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0109793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/10:0)</name>
      <smpdb_id>SMP0108440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/13:0)</name>
      <smpdb_id>SMP0108422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/10:0)</name>
      <smpdb_id>SMP0108425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/8:0)</name>
      <smpdb_id>SMP0108410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0109811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0109812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0109813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0109814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0109815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0109816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0109817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0109818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0109819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0109820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0109821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0109822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0109823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0109824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0109825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0109826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0109827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/10:0)</name>
      <smpdb_id>SMP0108404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/12:0)</name>
      <smpdb_id>SMP0108406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0109828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0109829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0109830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0109831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0109832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0109833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0109834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0109835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0109836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0109837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0109838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0109839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0109840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0109841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0109842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0109843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0109844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/10:0)</name>
      <smpdb_id>SMP0108439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/12:0)</name>
      <smpdb_id>SMP0108402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/14:0)</name>
      <smpdb_id>SMP0108415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/15:0)</name>
      <smpdb_id>SMP0108434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/16:0)</name>
      <smpdb_id>SMP0108412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/17:0)</name>
      <smpdb_id>SMP0108431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/8:0)</name>
      <smpdb_id>SMP0108409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0109845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0109846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0109847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0109848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0109849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0109850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0109851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0109852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0109853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0109854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0109855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0109856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0109857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0109858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0109859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0109860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0109861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/10:0)</name>
      <smpdb_id>SMP0108421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/17:0)</name>
      <smpdb_id>SMP0108417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/8:0)</name>
      <smpdb_id>SMP0108432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0109862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0109863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0109864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0109865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0109866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0109867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0109868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0109869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0109870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0109871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0109872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0109873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0109874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0109875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0109876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0109877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0109878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/10:0)</name>
      <smpdb_id>SMP0108424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/12:0)</name>
      <smpdb_id>SMP0108435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/13:0)</name>
      <smpdb_id>SMP0108433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/17:0)</name>
      <smpdb_id>SMP0108438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:0)</name>
      <smpdb_id>SMP0076986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0076987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/24:0)</name>
      <smpdb_id>SMP0076993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0076994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/8:0)</name>
      <smpdb_id>SMP0108441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-13:0)</name>
      <smpdb_id>SMP0109879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-15:0)</name>
      <smpdb_id>SMP0109880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-17:0)</name>
      <smpdb_id>SMP0109881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-21:0)</name>
      <smpdb_id>SMP0109882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/a-25:0)</name>
      <smpdb_id>SMP0109883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-12:0)</name>
      <smpdb_id>SMP0109884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-13:0)</name>
      <smpdb_id>SMP0109885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-14:0)</name>
      <smpdb_id>SMP0109886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-15:0)</name>
      <smpdb_id>SMP0109887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-16:0)</name>
      <smpdb_id>SMP0109888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-17:0)</name>
      <smpdb_id>SMP0109889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-18:0)</name>
      <smpdb_id>SMP0109890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-19:0)</name>
      <smpdb_id>SMP0109891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-20:0)</name>
      <smpdb_id>SMP0109892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-21:0)</name>
      <smpdb_id>SMP0109893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-22:0)</name>
      <smpdb_id>SMP0109894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:0/i-24:0)</name>
      <smpdb_id>SMP0109895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0076995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0076996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0076998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0076999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0077001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/24:0/24:0)</name>
      <smpdb_id>SMP0077028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/10:0)</name>
      <smpdb_id>SMP0108416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/14:0)</name>
      <smpdb_id>SMP0108418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/16:0)</name>
      <smpdb_id>SMP0108427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/8:0)</name>
      <smpdb_id>SMP0108429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0109896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0109897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0109898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0109899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0109900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0109901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0109902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0109903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0109904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0109905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0109906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0109907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0109908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0109909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0109910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0109911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0109912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0109913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0109914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0109915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0109916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0109917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0109918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0109919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0109920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0109921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0109922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0109923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0109924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0109925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0109926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0109927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0109928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0109929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0109930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0109931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0109932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0109933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0109934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0109935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0109936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0109937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0109938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0109939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0109940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0109941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0109942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0109943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0109944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0109945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0109946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0109947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0109948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0109949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0109950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0109951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0109952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0109953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0109954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0109955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0109956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0109957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0109958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0109959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0109960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0109961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0109962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0109963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0109964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0109965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0109966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0109967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0109968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0109969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0109970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0109971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0109972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0109973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0109974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0109975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0109976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0109977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0109978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0109979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0109980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0109981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0109982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0109983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0109984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0109985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0109986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0109987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0109988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0109989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0109990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0109991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0109992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0109993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0109994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0109995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0109996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0109997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0109998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0109999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/19:2(10Z,13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0108540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0077031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0077037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0077067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:2(13Z,16Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:4(7Z,10Z,13Z,16Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0077116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0077119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0077141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0077142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0/24:0)</name>
      <smpdb_id>SMP0077144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:0/24:0/24:0)</name>
      <smpdb_id>SMP0077147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0077148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(24:1(15Z)/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0077150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/10:0)</name>
      <smpdb_id>SMP0108443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/12:0)</name>
      <smpdb_id>SMP0108502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/16:0)</name>
      <smpdb_id>SMP0108450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/18:0)</name>
      <smpdb_id>SMP0108535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-21:0)</name>
      <smpdb_id>SMP0110069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0110070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/12:0)</name>
      <smpdb_id>SMP0108459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/13:0)</name>
      <smpdb_id>SMP0108498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/14:0)</name>
      <smpdb_id>SMP0108462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/15:0)</name>
      <smpdb_id>SMP0108442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/17:0)</name>
      <smpdb_id>SMP0108464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/19:0)</name>
      <smpdb_id>SMP0108499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-21:0)</name>
      <smpdb_id>SMP0110086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0110087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/10:0)</name>
      <smpdb_id>SMP0108455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/12:0)</name>
      <smpdb_id>SMP0108475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/14:0)</name>
      <smpdb_id>SMP0108532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/15:0)</name>
      <smpdb_id>SMP0108529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/17:0)</name>
      <smpdb_id>SMP0108491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/18:0)</name>
      <smpdb_id>SMP0108510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0110103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0110104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/12:0)</name>
      <smpdb_id>SMP0108486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/15:0)</name>
      <smpdb_id>SMP0108528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/17:0)</name>
      <smpdb_id>SMP0108505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-21:0)</name>
      <smpdb_id>SMP0110120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0110121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/13:0)</name>
      <smpdb_id>SMP0108513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/14:0)</name>
      <smpdb_id>SMP0108449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/15:0)</name>
      <smpdb_id>SMP0108493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/16:0)</name>
      <smpdb_id>SMP0108500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/18:0)</name>
      <smpdb_id>SMP0108474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/19:0)</name>
      <smpdb_id>SMP0108446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-21:0)</name>
      <smpdb_id>SMP0110137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0110138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/12:0)</name>
      <smpdb_id>SMP0108516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/16:0)</name>
      <smpdb_id>SMP0108530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/17:0)</name>
      <smpdb_id>SMP0108509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-21:0)</name>
      <smpdb_id>SMP0110154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0110155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/13:0)</name>
      <smpdb_id>SMP0108524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/15:0)</name>
      <smpdb_id>SMP0108501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/17:0)</name>
      <smpdb_id>SMP0108453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/18:0)</name>
      <smpdb_id>SMP0108520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-21:0)</name>
      <smpdb_id>SMP0110171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0110172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/10:0)</name>
      <smpdb_id>SMP0108482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/12:0)</name>
      <smpdb_id>SMP0108444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/14:0)</name>
      <smpdb_id>SMP0108497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/15:0)</name>
      <smpdb_id>SMP0108487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/17:0)</name>
      <smpdb_id>SMP0108484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/18:0)</name>
      <smpdb_id>SMP0108531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/19:0)</name>
      <smpdb_id>SMP0108538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0110185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0110186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0110187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0110188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0110189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0110190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0110191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0110192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0110193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0110194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0110195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/i-20:0)</name>
      <smpdb_id>SMP0110196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/12:0)</name>
      <smpdb_id>SMP0108508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/13:0)</name>
      <smpdb_id>SMP0108539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/14:0)</name>
      <smpdb_id>SMP0108515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/15:0)</name>
      <smpdb_id>SMP0108454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/16:0)</name>
      <smpdb_id>SMP0108490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/17:0)</name>
      <smpdb_id>SMP0108527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/18:0)</name>
      <smpdb_id>SMP0108537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/19:0)</name>
      <smpdb_id>SMP0108536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/8:0)</name>
      <smpdb_id>SMP0108242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-13:0)</name>
      <smpdb_id>SMP0110197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-15:0)</name>
      <smpdb_id>SMP0110198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-17:0)</name>
      <smpdb_id>SMP0110199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-21:0)</name>
      <smpdb_id>SMP0110200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/a-25:0)</name>
      <smpdb_id>SMP0110201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-12:0)</name>
      <smpdb_id>SMP0110202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-13:0)</name>
      <smpdb_id>SMP0110203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-14:0)</name>
      <smpdb_id>SMP0110204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-15:0)</name>
      <smpdb_id>SMP0110205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-16:0)</name>
      <smpdb_id>SMP0110206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-17:0)</name>
      <smpdb_id>SMP0110207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-18:0)</name>
      <smpdb_id>SMP0110208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-19:0)</name>
      <smpdb_id>SMP0110209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-20:0)</name>
      <smpdb_id>SMP0110210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-21:0)</name>
      <smpdb_id>SMP0110211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-22:0)</name>
      <smpdb_id>SMP0110212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/i-24:0)</name>
      <smpdb_id>SMP0110213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-21:0)</name>
      <smpdb_id>SMP0110217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0110218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0110223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-21:0)</name>
      <smpdb_id>SMP0110233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0110234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-21:0)</name>
      <smpdb_id>SMP0110248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0110249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0110262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0110263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0110264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0110265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0110266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0110267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0110268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0110269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0110270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0110271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0110272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0110273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0110274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0110275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/12:0)</name>
      <smpdb_id>SMP0110367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/13:0)</name>
      <smpdb_id>SMP0110368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/14:0)</name>
      <smpdb_id>SMP0110369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/15:0)</name>
      <smpdb_id>SMP0110370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/16:0)</name>
      <smpdb_id>SMP0110371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/17:0)</name>
      <smpdb_id>SMP0110372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/18:0)</name>
      <smpdb_id>SMP0110373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/a-25:0)</name>
      <smpdb_id>SMP0110377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/13:0)</name>
      <smpdb_id>SMP0110390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/14:0)</name>
      <smpdb_id>SMP0110391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/15:0)</name>
      <smpdb_id>SMP0110392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/16:0)</name>
      <smpdb_id>SMP0110393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/17:0)</name>
      <smpdb_id>SMP0110394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/18:0)</name>
      <smpdb_id>SMP0110395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/a-25:0)</name>
      <smpdb_id>SMP0110399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/14:0)</name>
      <smpdb_id>SMP0110412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/15:0)</name>
      <smpdb_id>SMP0110413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/16:0)</name>
      <smpdb_id>SMP0110414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/17:0)</name>
      <smpdb_id>SMP0110415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/18:0)</name>
      <smpdb_id>SMP0110416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0110420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/15:0)</name>
      <smpdb_id>SMP0110433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/16:0)</name>
      <smpdb_id>SMP0110434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/17:0)</name>
      <smpdb_id>SMP0110435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/18:0)</name>
      <smpdb_id>SMP0110436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/a-25:0)</name>
      <smpdb_id>SMP0110440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/16:0)</name>
      <smpdb_id>SMP0110453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/17:0)</name>
      <smpdb_id>SMP0110454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/18:0)</name>
      <smpdb_id>SMP0110455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/a-25:0)</name>
      <smpdb_id>SMP0110459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/17:0)</name>
      <smpdb_id>SMP0110472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/18:0)</name>
      <smpdb_id>SMP0110473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/a-25:0)</name>
      <smpdb_id>SMP0110477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/18:0)</name>
      <smpdb_id>SMP0110490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/a-25:0)</name>
      <smpdb_id>SMP0110494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/a-25:0)</name>
      <smpdb_id>SMP0110510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/a-25:0)</name>
      <smpdb_id>SMP0110524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/a-25:0)</name>
      <smpdb_id>SMP0110538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/12:0)</name>
      <smpdb_id>SMP0110551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/13:0)</name>
      <smpdb_id>SMP0110552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/14:0)</name>
      <smpdb_id>SMP0110553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/15:0)</name>
      <smpdb_id>SMP0110554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/16:0)</name>
      <smpdb_id>SMP0110555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/17:0)</name>
      <smpdb_id>SMP0110556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/18:0)</name>
      <smpdb_id>SMP0110557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-13:0)</name>
      <smpdb_id>SMP0110558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-15:0)</name>
      <smpdb_id>SMP0110559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-17:0)</name>
      <smpdb_id>SMP0110560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-21:0)</name>
      <smpdb_id>SMP0110561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/a-25:0)</name>
      <smpdb_id>SMP0110562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-12:0)</name>
      <smpdb_id>SMP0110563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-13:0)</name>
      <smpdb_id>SMP0110564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-14:0)</name>
      <smpdb_id>SMP0110565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-15:0)</name>
      <smpdb_id>SMP0110566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-16:0)</name>
      <smpdb_id>SMP0110567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-17:0)</name>
      <smpdb_id>SMP0110568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-18:0)</name>
      <smpdb_id>SMP0110569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-19:0)</name>
      <smpdb_id>SMP0110570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-20:0)</name>
      <smpdb_id>SMP0110571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-21:0)</name>
      <smpdb_id>SMP0110572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-22:0)</name>
      <smpdb_id>SMP0110573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/i-24:0)</name>
      <smpdb_id>SMP0110574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/a-13:0)</name>
      <smpdb_id>SMP0110630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/12:0)</name>
      <smpdb_id>SMP0110667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/13:0)</name>
      <smpdb_id>SMP0110668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/14:0)</name>
      <smpdb_id>SMP0110669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/15:0)</name>
      <smpdb_id>SMP0110670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/16:0)</name>
      <smpdb_id>SMP0110671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/17:0)</name>
      <smpdb_id>SMP0110672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/18:0)</name>
      <smpdb_id>SMP0110673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0110674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0110675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0110676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0110677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0110678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0110679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0110680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0110681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0110682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0110683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0110684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-20:0)</name>
      <smpdb_id>SMP0110685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0110686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0110687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0110688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/13:0)</name>
      <smpdb_id>SMP0110689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/14:0)</name>
      <smpdb_id>SMP0110690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/15:0)</name>
      <smpdb_id>SMP0110691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/16:0)</name>
      <smpdb_id>SMP0110692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/17:0)</name>
      <smpdb_id>SMP0110693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/18:0)</name>
      <smpdb_id>SMP0110694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0110695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0110696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0110697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0110698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0110699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0110700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0110701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0110702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0110703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0110704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0110705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-20:0)</name>
      <smpdb_id>SMP0110706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0110707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0110708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0110709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/14:0)</name>
      <smpdb_id>SMP0110710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/15:0)</name>
      <smpdb_id>SMP0110711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/16:0)</name>
      <smpdb_id>SMP0110712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/17:0)</name>
      <smpdb_id>SMP0110713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/18:0)</name>
      <smpdb_id>SMP0110714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/15:0)</name>
      <smpdb_id>SMP0110730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/16:0)</name>
      <smpdb_id>SMP0110731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/17:0)</name>
      <smpdb_id>SMP0110732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/18:0)</name>
      <smpdb_id>SMP0110733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0110734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0110735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0110736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0110737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0110738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0110739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0110740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0110741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0110742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0110743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0110744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-20:0)</name>
      <smpdb_id>SMP0110745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0110746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0110747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0110748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/16:0)</name>
      <smpdb_id>SMP0110749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/17:0)</name>
      <smpdb_id>SMP0110750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/18:0)</name>
      <smpdb_id>SMP0110751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0110752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0110753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0110754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0110755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0110756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0110757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0110758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0110759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0110760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0110761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0110762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-20:0)</name>
      <smpdb_id>SMP0110763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0110764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0110765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0110766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/17:0)</name>
      <smpdb_id>SMP0110767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/18:0)</name>
      <smpdb_id>SMP0110768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0110769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0110770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0110771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0110772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0110773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0110774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0110775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0110776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0110777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0110778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0110779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-20:0)</name>
      <smpdb_id>SMP0110780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0110781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0110782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0110783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/18:0)</name>
      <smpdb_id>SMP0110784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0110785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0110786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0110787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0110788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0110789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0110790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0110791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0110792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0110793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0110794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0110795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-20:0)</name>
      <smpdb_id>SMP0110796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0110797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0110798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0110799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0110800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0110801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0110802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0110803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0110804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0110805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0110806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0110807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0110808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0110809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0110810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-20:0)</name>
      <smpdb_id>SMP0110811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0110812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0110813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0110814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0110815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0110816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0110817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0110818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0110819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0110820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0110821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0110822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0110823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0110824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-20:0)</name>
      <smpdb_id>SMP0110825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0110826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0110827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0110828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0110829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0110830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0110831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0110832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0110833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0110834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0110835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0110836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0110837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-20:0)</name>
      <smpdb_id>SMP0110838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0110839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0110840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0110841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/10:0)</name>
      <smpdb_id>SMP0110842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/12:0)</name>
      <smpdb_id>SMP0110843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/13:0)</name>
      <smpdb_id>SMP0110844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/14:0)</name>
      <smpdb_id>SMP0110845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/15:0)</name>
      <smpdb_id>SMP0110846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/16:0)</name>
      <smpdb_id>SMP0110847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/17:0)</name>
      <smpdb_id>SMP0110848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/18:0)</name>
      <smpdb_id>SMP0110849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-13:0)</name>
      <smpdb_id>SMP0110850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-15:0)</name>
      <smpdb_id>SMP0110851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-17:0)</name>
      <smpdb_id>SMP0110852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/a-25:0)</name>
      <smpdb_id>SMP0110853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-12:0)</name>
      <smpdb_id>SMP0110854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-13:0)</name>
      <smpdb_id>SMP0110855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-14:0)</name>
      <smpdb_id>SMP0110856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-15:0)</name>
      <smpdb_id>SMP0110857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-16:0)</name>
      <smpdb_id>SMP0110858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-17:0)</name>
      <smpdb_id>SMP0110859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-18:0)</name>
      <smpdb_id>SMP0110860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-19:0)</name>
      <smpdb_id>SMP0110861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-20:0)</name>
      <smpdb_id>SMP0110862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-21:0)</name>
      <smpdb_id>SMP0110863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-22:0)</name>
      <smpdb_id>SMP0110864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/i-24:0)</name>
      <smpdb_id>SMP0110865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0110866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0110867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0110868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0110869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0110870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0110871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0110872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0110873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-20:0)</name>
      <smpdb_id>SMP0110874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0110875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0110876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0110877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0110878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0110879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0110880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0110881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0110882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0110883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0110884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-20:0)</name>
      <smpdb_id>SMP0110885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0110886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0110887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0110888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0110889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0110890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0110891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0110892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0110893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0110894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-20:0)</name>
      <smpdb_id>SMP0110895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0110896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0110897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0110898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0110899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0110900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0110901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0110902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0110903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-20:0)</name>
      <smpdb_id>SMP0110904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0110905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0110906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0110907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0110908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0110909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0110910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0110911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-20:0)</name>
      <smpdb_id>SMP0110912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0110913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0110914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0110915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0110916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0110917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0110918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-20:0)</name>
      <smpdb_id>SMP0110919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0110920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0110921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0110922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0110923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0110924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-20:0)</name>
      <smpdb_id>SMP0110925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0110926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0110927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0110928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-19:0)</name>
      <smpdb_id>SMP0110929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0110943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-20:0)</name>
      <smpdb_id>SMP0110944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-21:0)</name>
      <smpdb_id>SMP0110945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-22:0)</name>
      <smpdb_id>SMP0110946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-19:0/i-24:0)</name>
      <smpdb_id>SMP0110947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0110948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0110949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0110950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0110951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0110952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0110953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0110954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0110955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0110956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0110957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0110958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0110959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0110960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0110961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0110962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0110963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0110964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0110965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0110966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0110967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0110968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0110969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0110970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0110971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0110972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0110973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0110974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0110975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0110976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0110977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0110978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0110979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0110980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0110981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0110982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0110983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0110984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0110985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0110986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0110987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0110988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0110989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0110990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0110991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0110992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0110993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0110994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0110995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0110996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0110997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0110998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0110999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0111000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0111001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0111002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0111003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0111004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0111005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0111006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0111007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/12:0)</name>
      <smpdb_id>SMP0111009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/13:0)</name>
      <smpdb_id>SMP0111010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/14:0)</name>
      <smpdb_id>SMP0111011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/15:0)</name>
      <smpdb_id>SMP0111012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/16:0)</name>
      <smpdb_id>SMP0111013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/17:0)</name>
      <smpdb_id>SMP0111014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/18:0)</name>
      <smpdb_id>SMP0111015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/19:0)</name>
      <smpdb_id>SMP0111016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-19:0)</name>
      <smpdb_id>SMP0111027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-21:0)</name>
      <smpdb_id>SMP0111028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0111029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/13:0)</name>
      <smpdb_id>SMP0111031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/14:0)</name>
      <smpdb_id>SMP0111032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/15:0)</name>
      <smpdb_id>SMP0111033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/16:0)</name>
      <smpdb_id>SMP0111034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/17:0)</name>
      <smpdb_id>SMP0111035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/18:0)</name>
      <smpdb_id>SMP0111036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/19:0)</name>
      <smpdb_id>SMP0111037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-19:0)</name>
      <smpdb_id>SMP0111048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-21:0)</name>
      <smpdb_id>SMP0111049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0111050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/14:0)</name>
      <smpdb_id>SMP0111052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/15:0)</name>
      <smpdb_id>SMP0111053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/16:0)</name>
      <smpdb_id>SMP0111054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/17:0)</name>
      <smpdb_id>SMP0111055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/18:0)</name>
      <smpdb_id>SMP0111056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/19:0)</name>
      <smpdb_id>SMP0111057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0111068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0111069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0111070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/15:0)</name>
      <smpdb_id>SMP0111072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/16:0)</name>
      <smpdb_id>SMP0111073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/17:0)</name>
      <smpdb_id>SMP0111074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/18:0)</name>
      <smpdb_id>SMP0111075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/19:0)</name>
      <smpdb_id>SMP0111076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-19:0)</name>
      <smpdb_id>SMP0111087</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-21:0)</name>
      <smpdb_id>SMP0111088</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0111089</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111090</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/16:0)</name>
      <smpdb_id>SMP0111091</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/17:0)</name>
      <smpdb_id>SMP0111092</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/18:0)</name>
      <smpdb_id>SMP0111093</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/19:0)</name>
      <smpdb_id>SMP0111094</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111095</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111096</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111097</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111098</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111099</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-19:0)</name>
      <smpdb_id>SMP0111105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-21:0)</name>
      <smpdb_id>SMP0111106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0111107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/17:0)</name>
      <smpdb_id>SMP0111109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/18:0)</name>
      <smpdb_id>SMP0111110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/19:0)</name>
      <smpdb_id>SMP0111111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111117</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111118</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-19:0)</name>
      <smpdb_id>SMP0111122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-21:0)</name>
      <smpdb_id>SMP0111123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0111124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/18:0)</name>
      <smpdb_id>SMP0111126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/19:0)</name>
      <smpdb_id>SMP0111127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111136</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111137</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-19:0)</name>
      <smpdb_id>SMP0111138</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-21:0)</name>
      <smpdb_id>SMP0111139</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0111140</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111141</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/19:0)</name>
      <smpdb_id>SMP0111142</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-13:0)</name>
      <smpdb_id>SMP0111143</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-15:0)</name>
      <smpdb_id>SMP0111144</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/a-17:0)</name>
      <smpdb_id>SMP0111145</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-12:0)</name>
      <smpdb_id>SMP0111146</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-13:0)</name>
      <smpdb_id>SMP0111147</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-14:0)</name>
      <smpdb_id>SMP0111148</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-15:0)</name>
      <smpdb_id>SMP0111149</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-16:0)</name>
      <smpdb_id>SMP0111150</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-17:0)</name>
      <smpdb_id>SMP0111151</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-18:0)</name>
      <smpdb_id>SMP0111152</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/19:0/i-19:0)</name>
      <smpdb_id>SMP0111153</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111154</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111155</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111156</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111157</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111158</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111159</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111160</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111162</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-19:0)</name>
      <smpdb_id>SMP0111164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-21:0)</name>
      <smpdb_id>SMP0111165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0111166</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111167</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111168</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111170</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111171</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111173</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111174</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111175</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111176</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-19:0)</name>
      <smpdb_id>SMP0111177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-21:0)</name>
      <smpdb_id>SMP0111178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0111179</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111181</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111182</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111183</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111184</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111188</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-19:0)</name>
      <smpdb_id>SMP0111189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-21:0)</name>
      <smpdb_id>SMP0111190</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0111191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111192</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111195</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-19:0)</name>
      <smpdb_id>SMP0111200</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-21:0)</name>
      <smpdb_id>SMP0111201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0111202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111206</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111208</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111209</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-19:0)</name>
      <smpdb_id>SMP0111210</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-21:0)</name>
      <smpdb_id>SMP0111211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0111212</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111215</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111216</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-19:0)</name>
      <smpdb_id>SMP0111219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-21:0)</name>
      <smpdb_id>SMP0111220</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0111221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111226</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-19:0)</name>
      <smpdb_id>SMP0111227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-21:0)</name>
      <smpdb_id>SMP0111228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0111229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111232</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-19:0)</name>
      <smpdb_id>SMP0111234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-21:0)</name>
      <smpdb_id>SMP0111235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0111236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-19:0)</name>
      <smpdb_id>SMP0111240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-21:0)</name>
      <smpdb_id>SMP0111241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0111242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-19:0)</name>
      <smpdb_id>SMP0111245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-21:0)</name>
      <smpdb_id>SMP0111246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0111247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/12:0)</name>
      <smpdb_id>SMP0111249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/13:0)</name>
      <smpdb_id>SMP0111250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/14:0)</name>
      <smpdb_id>SMP0111251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/15:0)</name>
      <smpdb_id>SMP0111252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/16:0)</name>
      <smpdb_id>SMP0111253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/17:0)</name>
      <smpdb_id>SMP0111254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/18:0)</name>
      <smpdb_id>SMP0111255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-13:0)</name>
      <smpdb_id>SMP0111256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-15:0)</name>
      <smpdb_id>SMP0111257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/a-17:0)</name>
      <smpdb_id>SMP0111258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-12:0)</name>
      <smpdb_id>SMP0111259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-13:0)</name>
      <smpdb_id>SMP0111260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-14:0)</name>
      <smpdb_id>SMP0111261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-15:0)</name>
      <smpdb_id>SMP0111262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-16:0)</name>
      <smpdb_id>SMP0111263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-17:0)</name>
      <smpdb_id>SMP0111264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-18:0)</name>
      <smpdb_id>SMP0111265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-20:0)</name>
      <smpdb_id>SMP0111266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-21:0)</name>
      <smpdb_id>SMP0111267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-22:0)</name>
      <smpdb_id>SMP0111268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/i-24:0)</name>
      <smpdb_id>SMP0111269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0111270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0111271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0111272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/12:0)</name>
      <smpdb_id>SMP0111276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/13:0)</name>
      <smpdb_id>SMP0111277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/14:0)</name>
      <smpdb_id>SMP0111278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/15:0)</name>
      <smpdb_id>SMP0111279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/16:0)</name>
      <smpdb_id>SMP0111280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/17:0)</name>
      <smpdb_id>SMP0111281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/18:0)</name>
      <smpdb_id>SMP0111282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-22:0)</name>
      <smpdb_id>SMP0111293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/13:0)</name>
      <smpdb_id>SMP0111295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/14:0)</name>
      <smpdb_id>SMP0111296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/15:0)</name>
      <smpdb_id>SMP0111297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/16:0)</name>
      <smpdb_id>SMP0111298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/17:0)</name>
      <smpdb_id>SMP0111299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/18:0)</name>
      <smpdb_id>SMP0111300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-22:0)</name>
      <smpdb_id>SMP0111311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/14:0)</name>
      <smpdb_id>SMP0111313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/15:0)</name>
      <smpdb_id>SMP0111314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/16:0)</name>
      <smpdb_id>SMP0111315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/17:0)</name>
      <smpdb_id>SMP0111316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/18:0)</name>
      <smpdb_id>SMP0111317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0111328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/15:0)</name>
      <smpdb_id>SMP0111330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/16:0)</name>
      <smpdb_id>SMP0111331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/17:0)</name>
      <smpdb_id>SMP0111332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/18:0)</name>
      <smpdb_id>SMP0111333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-22:0)</name>
      <smpdb_id>SMP0111344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/16:0)</name>
      <smpdb_id>SMP0111346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/17:0)</name>
      <smpdb_id>SMP0111347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/18:0)</name>
      <smpdb_id>SMP0111348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-22:0)</name>
      <smpdb_id>SMP0111359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/17:0)</name>
      <smpdb_id>SMP0111361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/18:0)</name>
      <smpdb_id>SMP0111362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-22:0)</name>
      <smpdb_id>SMP0111373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/18:0)</name>
      <smpdb_id>SMP0111375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-22:0)</name>
      <smpdb_id>SMP0111386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-22:0)</name>
      <smpdb_id>SMP0111398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111407</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-22:0)</name>
      <smpdb_id>SMP0111409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-22:0)</name>
      <smpdb_id>SMP0111419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-22:0)</name>
      <smpdb_id>SMP0111428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-22:0)</name>
      <smpdb_id>SMP0111436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-22:0)</name>
      <smpdb_id>SMP0111443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-22:0)</name>
      <smpdb_id>SMP0111449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-22:0)</name>
      <smpdb_id>SMP0111454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-22:0)</name>
      <smpdb_id>SMP0111458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-22:0)</name>
      <smpdb_id>SMP0111461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/12:0)</name>
      <smpdb_id>SMP0111463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/13:0)</name>
      <smpdb_id>SMP0111464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0111465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/15:0)</name>
      <smpdb_id>SMP0111466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/16:0)</name>
      <smpdb_id>SMP0111467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/17:0)</name>
      <smpdb_id>SMP0111468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/18:0)</name>
      <smpdb_id>SMP0111469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-13:0)</name>
      <smpdb_id>SMP0111470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-15:0)</name>
      <smpdb_id>SMP0111471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/a-17:0)</name>
      <smpdb_id>SMP0111472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-12:0)</name>
      <smpdb_id>SMP0111473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-13:0)</name>
      <smpdb_id>SMP0111474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-14:0)</name>
      <smpdb_id>SMP0111475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-15:0)</name>
      <smpdb_id>SMP0111476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-16:0)</name>
      <smpdb_id>SMP0111477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-17:0)</name>
      <smpdb_id>SMP0111478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-18:0)</name>
      <smpdb_id>SMP0111479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-21:0)</name>
      <smpdb_id>SMP0111480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-22:0)</name>
      <smpdb_id>SMP0111481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/i-24:0)</name>
      <smpdb_id>SMP0111482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/12:0)</name>
      <smpdb_id>SMP0111486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/13:0)</name>
      <smpdb_id>SMP0111487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/14:0)</name>
      <smpdb_id>SMP0111488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/15:0)</name>
      <smpdb_id>SMP0111489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/16:0)</name>
      <smpdb_id>SMP0111490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/17:0)</name>
      <smpdb_id>SMP0111491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/18:0)</name>
      <smpdb_id>SMP0111492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/i-24:0)</name>
      <smpdb_id>SMP0111503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/13:0)</name>
      <smpdb_id>SMP0111504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/14:0)</name>
      <smpdb_id>SMP0111505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/15:0)</name>
      <smpdb_id>SMP0111506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/16:0)</name>
      <smpdb_id>SMP0111507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/17:0)</name>
      <smpdb_id>SMP0111508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/18:0)</name>
      <smpdb_id>SMP0111509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/i-24:0)</name>
      <smpdb_id>SMP0111520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/14:0)</name>
      <smpdb_id>SMP0111521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/15:0)</name>
      <smpdb_id>SMP0111522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/16:0)</name>
      <smpdb_id>SMP0111523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/17:0)</name>
      <smpdb_id>SMP0111524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/18:0)</name>
      <smpdb_id>SMP0111525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/15:0)</name>
      <smpdb_id>SMP0111537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/16:0)</name>
      <smpdb_id>SMP0111538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/17:0)</name>
      <smpdb_id>SMP0111539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/18:0)</name>
      <smpdb_id>SMP0111540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/15:0/i-24:0)</name>
      <smpdb_id>SMP0111551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/16:0)</name>
      <smpdb_id>SMP0111552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/17:0)</name>
      <smpdb_id>SMP0111553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/18:0)</name>
      <smpdb_id>SMP0111554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/16:0/i-24:0)</name>
      <smpdb_id>SMP0111565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/17:0)</name>
      <smpdb_id>SMP0111566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/18:0)</name>
      <smpdb_id>SMP0111567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/17:0/i-24:0)</name>
      <smpdb_id>SMP0111578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/18:0)</name>
      <smpdb_id>SMP0111579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/18:0/i-24:0)</name>
      <smpdb_id>SMP0111590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-13:0/i-24:0)</name>
      <smpdb_id>SMP0111601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-15:0/i-24:0)</name>
      <smpdb_id>SMP0111611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/a-17:0/i-24:0)</name>
      <smpdb_id>SMP0111620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-12:0/i-24:0)</name>
      <smpdb_id>SMP0111628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-13:0/i-24:0)</name>
      <smpdb_id>SMP0111635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-14:0/i-24:0)</name>
      <smpdb_id>SMP0111641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-15:0/i-24:0)</name>
      <smpdb_id>SMP0111646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-16:0/i-24:0)</name>
      <smpdb_id>SMP0111650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-17:0/i-24:0)</name>
      <smpdb_id>SMP0111653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-18:0/i-24:0)</name>
      <smpdb_id>SMP0111655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/12:0)</name>
      <smpdb_id>SMP0111656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/13:0)</name>
      <smpdb_id>SMP0111657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0111658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/15:0)</name>
      <smpdb_id>SMP0111659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/16:0)</name>
      <smpdb_id>SMP0111660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/17:0)</name>
      <smpdb_id>SMP0111661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/18:0)</name>
      <smpdb_id>SMP0111662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-13:0)</name>
      <smpdb_id>SMP0111663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-15:0)</name>
      <smpdb_id>SMP0111664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/a-17:0)</name>
      <smpdb_id>SMP0111665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-12:0)</name>
      <smpdb_id>SMP0111666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-13:0)</name>
      <smpdb_id>SMP0111667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-14:0)</name>
      <smpdb_id>SMP0111668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-15:0)</name>
      <smpdb_id>SMP0111669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-16:0)</name>
      <smpdb_id>SMP0111670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-17:0)</name>
      <smpdb_id>SMP0111671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-18:0)</name>
      <smpdb_id>SMP0111672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-22:0)</name>
      <smpdb_id>SMP0111673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/i-24:0)</name>
      <smpdb_id>SMP0111674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/12:0)</name>
      <smpdb_id>SMP0111676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/13:0)</name>
      <smpdb_id>SMP0111677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/14:0)</name>
      <smpdb_id>SMP0111678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/15:0)</name>
      <smpdb_id>SMP0111679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/16:0)</name>
      <smpdb_id>SMP0111680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/17:0)</name>
      <smpdb_id>SMP0111681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/18:0)</name>
      <smpdb_id>SMP0111682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-13:0)</name>
      <smpdb_id>SMP0111683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-15:0)</name>
      <smpdb_id>SMP0111684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/a-17:0)</name>
      <smpdb_id>SMP0111685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-12:0)</name>
      <smpdb_id>SMP0111686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-13:0)</name>
      <smpdb_id>SMP0111687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-14:0)</name>
      <smpdb_id>SMP0111688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-15:0)</name>
      <smpdb_id>SMP0111689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-16:0)</name>
      <smpdb_id>SMP0111690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-17:0)</name>
      <smpdb_id>SMP0111691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/i-18:0)</name>
      <smpdb_id>SMP0111692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/13:0)</name>
      <smpdb_id>SMP0111693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/14:0)</name>
      <smpdb_id>SMP0111694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/15:0)</name>
      <smpdb_id>SMP0111695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/16:0)</name>
      <smpdb_id>SMP0111696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/17:0)</name>
      <smpdb_id>SMP0111697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/18:0)</name>
      <smpdb_id>SMP0111698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-13:0)</name>
      <smpdb_id>SMP0111699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-15:0)</name>
      <smpdb_id>SMP0111700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/a-17:0)</name>
      <smpdb_id>SMP0111701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-12:0)</name>
      <smpdb_id>SMP0111702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-13:0)</name>
      <smpdb_id>SMP0111703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-14:0)</name>
      <smpdb_id>SMP0111704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-15:0)</name>
      <smpdb_id>SMP0111705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-16:0)</name>
      <smpdb_id>SMP0111706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-17:0)</name>
      <smpdb_id>SMP0111707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/i-18:0)</name>
      <smpdb_id>SMP0111708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/14:0)</name>
      <smpdb_id>SMP0111709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/15:0)</name>
      <smpdb_id>SMP0111710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/16:0)</name>
      <smpdb_id>SMP0111711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/17:0)</name>
      <smpdb_id>SMP0111712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/18:0)</name>
      <smpdb_id>SMP0111713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/15:0)</name>
      <smpdb_id>SMP0111724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/16:0)</name>
      <smpdb_id>SMP0111725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/17:0)</name>
      <smpdb_id>SMP0111726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/18:0)</name>
      <smpdb_id>SMP0111727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-13:0)</name>
      <smpdb_id>SMP0111728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-15:0)</name>
      <smpdb_id>SMP0111729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/a-17:0)</name>
      <smpdb_id>SMP0111730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-12:0)</name>
      <smpdb_id>SMP0111731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-13:0)</name>
      <smpdb_id>SMP0111732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-14:0)</name>
      <smpdb_id>SMP0111733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-15:0)</name>
      <smpdb_id>SMP0111734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-16:0)</name>
      <smpdb_id>SMP0111735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-17:0)</name>
      <smpdb_id>SMP0111736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/15:0/i-18:0)</name>
      <smpdb_id>SMP0111737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/16:0)</name>
      <smpdb_id>SMP0111738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/17:0)</name>
      <smpdb_id>SMP0111739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/18:0)</name>
      <smpdb_id>SMP0111740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-13:0)</name>
      <smpdb_id>SMP0111741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-15:0)</name>
      <smpdb_id>SMP0111742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/a-17:0)</name>
      <smpdb_id>SMP0111743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-12:0)</name>
      <smpdb_id>SMP0111744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-13:0)</name>
      <smpdb_id>SMP0111745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-14:0)</name>
      <smpdb_id>SMP0111746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-15:0)</name>
      <smpdb_id>SMP0111747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-16:0)</name>
      <smpdb_id>SMP0111748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-17:0)</name>
      <smpdb_id>SMP0111749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/16:0/i-18:0)</name>
      <smpdb_id>SMP0111750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/17:0)</name>
      <smpdb_id>SMP0111751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/18:0)</name>
      <smpdb_id>SMP0111752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-13:0)</name>
      <smpdb_id>SMP0111753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-15:0)</name>
      <smpdb_id>SMP0111754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/a-17:0)</name>
      <smpdb_id>SMP0111755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-12:0)</name>
      <smpdb_id>SMP0111756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-13:0)</name>
      <smpdb_id>SMP0111757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-14:0)</name>
      <smpdb_id>SMP0111758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-15:0)</name>
      <smpdb_id>SMP0111759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-16:0)</name>
      <smpdb_id>SMP0111760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-17:0)</name>
      <smpdb_id>SMP0111761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/17:0/i-18:0)</name>
      <smpdb_id>SMP0111762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/18:0)</name>
      <smpdb_id>SMP0111763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-13:0)</name>
      <smpdb_id>SMP0111764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-15:0)</name>
      <smpdb_id>SMP0111765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/a-17:0)</name>
      <smpdb_id>SMP0111766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-12:0)</name>
      <smpdb_id>SMP0111767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-13:0)</name>
      <smpdb_id>SMP0111768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-14:0)</name>
      <smpdb_id>SMP0111769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-15:0)</name>
      <smpdb_id>SMP0111770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-16:0)</name>
      <smpdb_id>SMP0111771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-17:0)</name>
      <smpdb_id>SMP0111772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/18:0/i-18:0)</name>
      <smpdb_id>SMP0111773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-13:0)</name>
      <smpdb_id>SMP0111774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-15:0)</name>
      <smpdb_id>SMP0111775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/a-17:0)</name>
      <smpdb_id>SMP0111776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-12:0)</name>
      <smpdb_id>SMP0111777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-13:0)</name>
      <smpdb_id>SMP0111778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-14:0)</name>
      <smpdb_id>SMP0111779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-15:0)</name>
      <smpdb_id>SMP0111780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-16:0)</name>
      <smpdb_id>SMP0111781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-17:0)</name>
      <smpdb_id>SMP0111782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-13:0/i-18:0)</name>
      <smpdb_id>SMP0111783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/a-15:0)</name>
      <smpdb_id>SMP0111784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/a-17:0)</name>
      <smpdb_id>SMP0111785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-12:0)</name>
      <smpdb_id>SMP0111786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-13:0)</name>
      <smpdb_id>SMP0111787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-14:0)</name>
      <smpdb_id>SMP0111788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-15:0)</name>
      <smpdb_id>SMP0111789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-16:0)</name>
      <smpdb_id>SMP0111790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-17:0)</name>
      <smpdb_id>SMP0111791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-15:0/i-18:0)</name>
      <smpdb_id>SMP0111792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/a-17:0)</name>
      <smpdb_id>SMP0111793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-12:0)</name>
      <smpdb_id>SMP0111794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-13:0)</name>
      <smpdb_id>SMP0111795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-14:0)</name>
      <smpdb_id>SMP0111796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-15:0)</name>
      <smpdb_id>SMP0111797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-16:0)</name>
      <smpdb_id>SMP0111798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-17:0)</name>
      <smpdb_id>SMP0111799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/a-17:0/i-18:0)</name>
      <smpdb_id>SMP0111800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-12:0)</name>
      <smpdb_id>SMP0111801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-13:0)</name>
      <smpdb_id>SMP0111802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-14:0)</name>
      <smpdb_id>SMP0111803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-15:0)</name>
      <smpdb_id>SMP0111804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-16:0)</name>
      <smpdb_id>SMP0111805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-17:0)</name>
      <smpdb_id>SMP0111806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-12:0/i-18:0)</name>
      <smpdb_id>SMP0111807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-13:0)</name>
      <smpdb_id>SMP0111808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-14:0)</name>
      <smpdb_id>SMP0111809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-15:0)</name>
      <smpdb_id>SMP0111810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-16:0)</name>
      <smpdb_id>SMP0111811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-17:0)</name>
      <smpdb_id>SMP0111812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-13:0/i-18:0)</name>
      <smpdb_id>SMP0111813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-14:0)</name>
      <smpdb_id>SMP0111814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-15:0)</name>
      <smpdb_id>SMP0111815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-16:0)</name>
      <smpdb_id>SMP0111816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-17:0)</name>
      <smpdb_id>SMP0111817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-14:0/i-18:0)</name>
      <smpdb_id>SMP0111818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-15:0)</name>
      <smpdb_id>SMP0111819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-16:0)</name>
      <smpdb_id>SMP0111820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-17:0)</name>
      <smpdb_id>SMP0111821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-15:0/i-18:0)</name>
      <smpdb_id>SMP0111822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-16:0)</name>
      <smpdb_id>SMP0111823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-17:0)</name>
      <smpdb_id>SMP0111824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-16:0/i-18:0)</name>
      <smpdb_id>SMP0111825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-17:0/i-17:0)</name>
      <smpdb_id>SMP0111826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-17:0/i-18:0)</name>
      <smpdb_id>SMP0111827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-18:0/i-18:0)</name>
      <smpdb_id>SMP0111828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/12:0)</name>
      <smpdb_id>SMP0111829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/13:0)</name>
      <smpdb_id>SMP0111830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0111831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/15:0)</name>
      <smpdb_id>SMP0111832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/16:0)</name>
      <smpdb_id>SMP0111833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/17:0)</name>
      <smpdb_id>SMP0111834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/18:0)</name>
      <smpdb_id>SMP0111835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-13:0)</name>
      <smpdb_id>SMP0111836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-15:0)</name>
      <smpdb_id>SMP0111837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/a-17:0)</name>
      <smpdb_id>SMP0111838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-12:0)</name>
      <smpdb_id>SMP0111839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-13:0)</name>
      <smpdb_id>SMP0111840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-14:0)</name>
      <smpdb_id>SMP0111841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-15:0)</name>
      <smpdb_id>SMP0111842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-16:0)</name>
      <smpdb_id>SMP0111843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-17:0)</name>
      <smpdb_id>SMP0111844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-18:0)</name>
      <smpdb_id>SMP0111845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/i-24:0)</name>
      <smpdb_id>SMP0111846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fructose and Mannose Degradation</name>
      <smpdb_id>SMP0087197</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerol Phosphate Shuttle</name>
      <smpdb_id>SMP0087199</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycerolipid Metabolism</name>
      <smpdb_id>SMP0087230</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Electron Transport Chain</name>
      <smpdb_id>SMP0087261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Plasmalogen Synthesis</name>
      <smpdb_id>SMP0087264</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>9073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>15745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20985</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438882</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00111</kegg_id>
  <foodb_id>FDB001618</foodb_id>
  <chemspider_id>648</chemspider_id>
  <pubchem_compound_id>668</pubchem_compound_id>
  <chebi_id>16108</chebi_id>
  <pdbe_id/>
  <drugbank_id>DB04326</drugbank_id>
  <meta_cyc_id>DIHYDROXY-ACETONE-PHOSPHATE</meta_cyc_id>
  <knapsack_id>C00007560</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33898</bigg_id>
  <wikipedia_id>Dihydroxyacetone_phosphate</wikipedia_id>
  <metlin_id>6262</metlin_id>
  <synthesis_reference>Ballou, Clinton E.; Fischer, Hermann O. L. The synthesis of dihydroxyacetone phosphate. Journal of the American Chemical Society (1956), 78 1659-61.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00092</protein_accession>
      <name>Glycerol-3-phosphate dehydrogenase, mitochondrial</name>
      <uniprot_id>A6QLU1</uniprot_id>
      <gene_name>GPD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00212</protein_accession>
      <name>Dihydroxyacetone phosphate acyltransferase</name>
      <uniprot_id>A4IF87</uniprot_id>
      <gene_name>GNPAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00387</protein_accession>
      <name>Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)</name>
      <uniprot_id>Q58DK4</uniprot_id>
      <gene_name>DAK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00531</protein_accession>
      <name>Fructose-bisphosphate aldolase</name>
      <uniprot_id>A6QLL8</uniprot_id>
      <gene_name>ALDOA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00532</protein_accession>
      <name>Fructose-bisphosphate aldolase</name>
      <uniprot_id>Q3ZBY4</uniprot_id>
      <gene_name>ALDOC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00533</protein_accession>
      <name>Fructose-bisphosphate aldolase</name>
      <uniprot_id>A5PK73</uniprot_id>
      <gene_name>ALDOB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00534</protein_accession>
      <name>Fructose-bisphosphate aldolase B</name>
      <uniprot_id>Q3T0S5</uniprot_id>
      <gene_name>ALDOB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00696</protein_accession>
      <name>Triosephosphate isomerase</name>
      <uniprot_id>Q5E956</uniprot_id>
      <gene_name>TPI1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:28 UTC</creation_date>
  <update_date>2020-03-13 16:28:17 UTC</update_date>
  <accession>BMDB0001474</accession>
  <secondary_accessions>
    <accession>BMDB01474</accession>
  </secondary_accessions>
  <name>3,4-Dihydroxyphenylglycol O-sulfate</name>
  <description/>
  <synonyms>
    <synonym>3,4-Dihydroxyphenylglycol O-sulfuric acid</synonym>
    <synonym>3,4-Dihydroxyphenylglycol O-sulphate</synonym>
    <synonym>3,4-Dihydroxyphenylglycol O-sulphuric acid</synonym>
    <synonym>3,4-Dihydroxyphenylethylene glycol sulfate</synonym>
    <synonym>3,4-Dihydroxyphenylethylene glycol sulphate</synonym>
    <synonym>[4-(1,2-Dihydroxyethyl)-2-hydroxyphenyl]oxidanesulfonate</synonym>
    <synonym>[4-(1,2-Dihydroxyethyl)-2-hydroxyphenyl]oxidanesulphonate</synonym>
    <synonym>[4-(1,2-Dihydroxyethyl)-2-hydroxyphenyl]oxidanesulphonic acid</synonym>
  </synonyms>
  <chemical_formula>C8H10O7S</chemical_formula>
  <average_molecular_weight>250.226</average_molecular_weight>
  <monisotopic_moleculate_weight>250.014723364</monisotopic_moleculate_weight>
  <iupac_name>[4-(1,2-dihydroxyethyl)-2-hydroxyphenyl]oxidanesulfonic acid</iupac_name>
  <traditional_iupac>[4-(1,2-dihydroxyethyl)-2-hydroxyphenyl]oxidanesulfonic acid</traditional_iupac>
  <cas_registry_number>3415-68-7</cas_registry_number>
  <smiles>OCC(O)C1=CC(O)=C(OS(O)(=O)=O)C=C1</smiles>
  <inchi>InChI=1S/C8H10O7S/c9-4-7(11)5-1-2-8(6(10)3-5)15-16(12,13)14/h1-3,7,9-11H,4H2,(H,12,13,14)</inchi>
  <inchikey>MFYFKAXYRXODPL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic sulfuric acids and derivatives</class>
    <sub_class>Arylsulfates</sub_class>
    <direct_parent>Phenylsulfates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenylsulfate</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[4-(1,2-dihydroxyethyl)-2-hydroxyphenyl]oxidanesulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>250.226</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>250.014723364</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(O)C1=CC(O)=C(OS(O)(=O)=O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H10O7S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H10O7S/c9-4-7(11)5-1-2-8(6(10)3-5)15-16(12,13)14/h1-3,7,9-11H,4H2,(H,12,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MFYFKAXYRXODPL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>124.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>52.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359010</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022644</foodb_id>
  <chemspider_id>17216128</chemspider_id>
  <pubchem_compound_id>22833570</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:29 UTC</creation_date>
  <update_date>2020-03-13 16:28:17 UTC</update_date>
  <accession>BMDB0001475</accession>
  <secondary_accessions>
    <accession>BMDB01475</accession>
  </secondary_accessions>
  <name>Zirconium</name>
  <description>Zirconium, also known as circonio or zircat, belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Zirconium exists as a solid, possibly soluble (in water), and possibly neutral molecule.</description>
  <synonyms>
    <synonym>Circonio</synonym>
    <synonym>Zircat</synonym>
    <synonym>Zirconio</synonym>
    <synonym>Zirkonium</synonym>
    <synonym>Zr</synonym>
  </synonyms>
  <chemical_formula>Zr</chemical_formula>
  <average_molecular_weight>91.224</average_molecular_weight>
  <monisotopic_moleculate_weight>89.904703679</monisotopic_moleculate_weight>
  <iupac_name>zirconium(4+) ion</iupac_name>
  <traditional_iupac>zirconium(4+) ion</traditional_iupac>
  <cas_registry_number>7440-67-7</cas_registry_number>
  <smiles>[Zr+4]</smiles>
  <inchi>InChI=1S/Zr/q+4</inchi>
  <inchikey>GBNDTYKAOXLLID-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous transition metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous transition metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous transition metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>1857 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>zirconium(4+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>91.224</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>89.904703679</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Zr+4]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Zr</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Zr/q+4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GBNDTYKAOXLLID-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>43746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>43747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>43748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>143550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>143551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>143552</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00153 - 0.0469</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Hermansen JE, Badsberg JH, Kristensen T, Gundersen V: Major and trace elements in organically or conventionally produced milk. J Dairy Res. 2005 Aug;72(3):362-8. doi: 10.1017/S0022029905000968.</reference_text>
          <pubmed_id>16174368</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.020 +/- 0.003</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.010 +/- 0.004</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.010 +/- 0.002</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.3 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.050 +/- 0.012</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured by ICP-MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB004189</foodb_id>
  <chemspider_id>103026</chemspider_id>
  <pubchem_compound_id>115139</pubchem_compound_id>
  <chebi_id>33342</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Zirconium</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Hermansen JE, Badsberg JH, Kristensen T, Gundersen V: Major and trace elements in organically or conventionally produced milk. J Dairy Res. 2005 Aug;72(3):362-8. doi: 10.1017/S0022029905000968.</reference_text>
      <pubmed_id>16174368</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:30 UTC</creation_date>
  <update_date>2020-04-15 22:18:23 UTC</update_date>
  <accession>BMDB0001476</accession>
  <secondary_accessions>
    <accession>BMDB01476</accession>
  </secondary_accessions>
  <name>3-Hydroxyanthranilic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Amino-3-hydroxy-benzoic acid</synonym>
    <synonym>2-Amino-3-hydroxybenzoic acid</synonym>
    <synonym>3-Ohaa</synonym>
    <synonym>3-Oxyanthranilic acid</synonym>
    <synonym>2-Amino-3-hydroxy-benzoate</synonym>
    <synonym>2-Amino-3-hydroxybenzoate</synonym>
    <synonym>3-Oxyanthranilate</synonym>
    <synonym>3-Hydroxyanthranilate</synonym>
    <synonym>3-Hydroxanthranilate</synonym>
    <synonym>3-Hydroxy-2-aminobenzoate</synonym>
    <synonym>3-Hydroxy-2-aminobenzoic acid</synonym>
    <synonym>3-Hydroxy-anthranilate</synonym>
    <synonym>3-Hydroxy-anthranilic acid</synonym>
    <synonym>3-Hydroxy-anthranilsaeure</synonym>
    <synonym>3-Hydroxyantranilic acid</synonym>
    <synonym>3-OH-Anthranilic acid</synonym>
    <synonym>3 Hydroxyanthranilic acid</synonym>
    <synonym>Acid, 3-hydroxyanthranilic</synonym>
  </synonyms>
  <chemical_formula>C7H7NO3</chemical_formula>
  <average_molecular_weight>153.1354</average_molecular_weight>
  <monisotopic_moleculate_weight>153.042593095</monisotopic_moleculate_weight>
  <iupac_name>2-amino-3-hydroxybenzoic acid</iupac_name>
  <traditional_iupac>3-hydroxyanthranilic acid</traditional_iupac>
  <cas_registry_number>548-93-6</cas_registry_number>
  <smiles>NC1=C(O)C=CC=C1C(O)=O</smiles>
  <inchi>InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)</inchi>
  <inchikey>WJXSWCUQABXPFS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>Hydroxybenzoic acid derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminobenzoic acids</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
      <alternative_parent>o-Aminophenols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminobenzoic acid</substituent>
      <substituent>Aminobenzoic acid or derivatives</substituent>
      <substituent>Aminophenol</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxybenzoic acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>O-aminophenol</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aminobenzoic acid</external_descriptor>
      <external_descriptor>monohydroxybenzoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-3-hydroxybenzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>153.1354</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>153.042593095</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=C(O)C=CC=C1C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H7NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WJXSWCUQABXPFS-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>83.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1560</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4811</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178992</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178993</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178994</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181319</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451633</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00632</kegg_id>
  <foodb_id>FDB010582</foodb_id>
  <chemspider_id>84</chemspider_id>
  <pubchem_compound_id>86</pubchem_compound_id>
  <chebi_id>15793</chebi_id>
  <pdbe_id/>
  <drugbank_id>DB03644</drugbank_id>
  <meta_cyc_id>3-HYDROXY-ANTHRANILATE</meta_cyc_id>
  <knapsack_id>C00007568</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>1485273</bigg_id>
  <wikipedia_id>3-hydroxyanthranilic_acid</wikipedia_id>
  <metlin_id>3275</metlin_id>
  <synthesis_reference>Warnell, J. L. 3-Hydroxyanthranilic acid. Biochemical Preparations (1958), 6 20-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00666</protein_accession>
      <name>3-hydroxyanthranilate 3,4-dioxygenase</name>
      <uniprot_id>Q0VCA8</uniprot_id>
      <gene_name>HAAO</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:31 UTC</creation_date>
  <update_date>2020-03-13 16:28:19 UTC</update_date>
  <accession>BMDB0001480</accession>
  <secondary_accessions>
    <accession>BMDB01480</accession>
  </secondary_accessions>
  <name>3-Dehydrosphinganine</name>
  <description/>
  <synonyms>
    <synonym>3-Dehydro-D-sphinganine</synonym>
    <synonym>3-Ketodihydrosphingosine</synonym>
    <synonym>3-Ketosphinganine</synonym>
    <synonym>(2S)-2-Amino-1-hydroxyoctadecan-3-one</synonym>
    <synonym>1-Hydroxy-2-amino-3-oxo-octadecane</synonym>
    <synonym>2-Amino-1-hydroxy-3-octadecanone</synonym>
    <synonym>KDHS</synonym>
    <synonym>Ketodihydrosphingosine</synonym>
    <synonym>(+-)-Isomer OF ketodihydrosphingosine</synonym>
    <synonym>(S)-Isomer OF ketodihydrosphingosine</synonym>
  </synonyms>
  <chemical_formula>C18H37NO2</chemical_formula>
  <average_molecular_weight>299.4919</average_molecular_weight>
  <monisotopic_moleculate_weight>299.282429433</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-1-hydroxyoctadecan-3-one</iupac_name>
  <traditional_iupac>3-ketosphinganine</traditional_iupac>
  <cas_registry_number>16105-69-4</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCC(=O)[C@@H](N)CO</smiles>
  <inchi>InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17,20H,2-16,19H2,1H3/t17-/m0/s1</inchi>
  <inchikey>KBUNOSOGGAARKZ-KRWDZBQOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as beta-hydroxy ketones. These are ketones containing a hydroxyl group attached to the beta-carbon atom, relative to the C=O group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Beta-hydroxy ketones</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-amino ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-aminoketone</substituent>
      <substituent>Amine</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-amino-1-hydroxyoctadecan-3-one</external_descriptor>
      <external_descriptor>Sphing-4-enines (Sphingosines)</external_descriptor>
      <external_descriptor>Sphinganines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>7.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-1-hydroxyoctadecan-3-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>299.4919</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>299.282429433</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCC(=O)[C@@H](N)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H37NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17,20H,2-16,19H2,1H3/t17-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KBUNOSOGGAARKZ-KRWDZBQOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>90.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>39.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181379</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02934</kegg_id>
  <foodb_id>FDB022645</foodb_id>
  <chemspider_id>388895</chemspider_id>
  <pubchem_compound_id>439853</pubchem_compound_id>
  <chebi_id>17862</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id>DEHYDROSPHINGANINE</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>1453300</bigg_id>
  <wikipedia_id/>
  <metlin_id>3428</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00071</protein_accession>
      <name>3-ketodihydrosphingosine reductase</name>
      <uniprot_id>Q2KIJ5</uniprot_id>
      <gene_name>KDSR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:33 UTC</creation_date>
  <update_date>2020-03-13 16:28:19 UTC</update_date>
  <accession>BMDB0001481</accession>
  <secondary_accessions>
    <accession>BMDB01481</accession>
  </secondary_accessions>
  <name>N-Sulfo-D-glucosamine</name>
  <description/>
  <synonyms>
    <synonym>N-SulphO-D-glucosamine</synonym>
    <synonym>N-[(2R,3R,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)oxan-3-yl]sulfamate</synonym>
    <synonym>N-[(2R,3R,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)oxan-3-yl]sulphamate</synonym>
    <synonym>N-[(2R,3R,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)oxan-3-yl]sulphamic acid</synonym>
  </synonyms>
  <chemical_formula>C6H13NO8S</chemical_formula>
  <average_molecular_weight>259.234</average_molecular_weight>
  <monisotopic_moleculate_weight>259.036187087</monisotopic_moleculate_weight>
  <iupac_name>N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]sulfamic acid</iupac_name>
  <traditional_iupac>N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]sulfamic acid</traditional_iupac>
  <cas_registry_number>909257-48-3</cas_registry_number>
  <smiles>OC[C@H]1O[C@@H](O)[C@H](NS(O)(=O)=O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H13NO8S/c8-1-2-4(9)5(10)3(6(11)15-2)7-16(12,13)14/h2-11H,1H2,(H,12,13,14)/t2-,3-,4-,5-,6-/m1/s1</inchi>
  <inchikey>PRDZVHCOEWJPOB-QZABAPFNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sulfuric acid monoamides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sulfuric acid monoamide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]sulfamic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>259.234</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>259.036187087</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@@H](O)[C@H](NS(O)(=O)=O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13NO8S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13NO8S/c8-1-2-4(9)5(10)3(6(11)15-2)7-16(12,13)14/h2-11H,1H2,(H,12,13,14)/t2-,3-,4-,5-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PRDZVHCOEWJPOB-QZABAPFNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>156.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350307</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01075</kegg_id>
  <foodb_id>FDB022646</foodb_id>
  <chemspider_id>388505</chemspider_id>
  <pubchem_compound_id>439388</pubchem_compound_id>
  <chebi_id>16702</chebi_id>
  <pdbe_id/>
  <drugbank_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6267</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:34 UTC</creation_date>
  <update_date>2020-03-13 16:28:20 UTC</update_date>
  <accession>BMDB0001483</accession>
  <secondary_accessions>
    <accession>BMDB01483</accession>
  </secondary_accessions>
  <name>Prostaglandin F2b</name>
  <description/>
  <synonyms>
    <synonym>5-Heptenoic acid, 7-[3,5-dihydroxy-2(3-hydroxy-1-octenyl)cyclopentyl]-, stereoisomer</synonym>
    <synonym>9beta,11alpha-PGF2a</synonym>
    <synonym>9beta,11alpha-PGF2alpha</synonym>
    <synonym>PGF2b</synonym>
    <synonym>PGF2beta</synonym>
    <synonym>Prostaglandin F2-beta</synonym>
    <synonym>5-Heptenoate, 7-[3,5-dihydroxy-2(3-hydroxy-1-octenyl)cyclopentyl]-, stereoisomer</synonym>
    <synonym>9b,11a-PGF2a</synonym>
    <synonym>9Β,11α-PGF2a</synonym>
    <synonym>9Β,11α-PGF2α</synonym>
    <synonym>PGF2Β</synonym>
    <synonym>Prostaglandin F2-b</synonym>
    <synonym>Prostaglandin F2-β</synonym>
    <synonym>(5Z,13E)-9,11,15-Trihydroxy-prosta-5,13-dien-1-Oate</synonym>
    <synonym>(5Z,13E)-9,11,15-Trihydroxy-prosta-5,13-dien-1-Oic acid</synonym>
    <synonym>7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoate</synonym>
    <synonym>7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid</synonym>
    <synonym>7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid stereoisomer</synonym>
    <synonym>7-[3a,5b-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoate</synonym>
    <synonym>7-[3a,5b-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid</synonym>
    <synonym>9b,11a-PGF2</synonym>
    <synonym>Prostaglandin F2beta</synonym>
    <synonym>Prostaglandin F2beta, (5Z,8beta,9beta,11alpha,12alpha,13E,15S)-isomer</synonym>
    <synonym>Prostaglandin F2beta, (5Z,9beta,11beta,13E,15S)-isomer</synonym>
    <synonym>Prostaglandin F2beta, (5Z,9beta,11beta,13E,15R)-isomer</synonym>
    <synonym>Prostaglandin F2b</synonym>
    <synonym>Prostaglandin F2β</synonym>
  </synonyms>
  <chemical_formula>C20H34O5</chemical_formula>
  <average_molecular_weight>354.481</average_molecular_weight>
  <monisotopic_moleculate_weight>354.240624198</monisotopic_moleculate_weight>
  <iupac_name>(5Z)-7-[(1R,2R,3R,5R)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid</iupac_name>
  <traditional_iupac>pgf(sub 2-β)</traditional_iupac>
  <cas_registry_number>4510-16-1</cas_registry_number>
  <smiles>CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H](O)[C@@H]1C\C=C/CCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18+,19+/m0/s1</inchi>
  <inchikey>PXGPLTODNUVGFL-JZFBHDEDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Prostaglandins and related compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclopentanols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclopentanol</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Prostaglandin skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>prostaglandins Fbeta</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>logp</kind>
      <value>4.39</value>
      <source>BODOR,H &amp; HUANG,M (1992)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5Z)-7-[(1R,2R,3R,5R)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>354.481</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>354.240624198</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H](O)[C@@H]1C\C=C/CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H34O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18+,19+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PXGPLTODNUVGFL-JZFBHDEDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>100.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>333840</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02314</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022647</foodb_id>
  <chemspider_id>4444144</chemspider_id>
  <pubchem_compound_id>5280506</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28922</chebi_id>
  <knapsack_id/>
  <wikipedia_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:35 UTC</creation_date>
  <update_date>2020-04-15 22:00:39 UTC</update_date>
  <accession>BMDB0001484</accession>
  <secondary_accessions>
    <accession>BMDB01484</accession>
  </secondary_accessions>
  <name>Acetoacetyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>3-Acetoacetyl-CoA</synonym>
    <synonym>Acetoacetyl coenzyme A</synonym>
    <synonym>S-Acetoacetyl-CoA</synonym>
    <synonym>S-Acetoacetyl-coenzym a</synonym>
    <synonym>S-Acetoacetyl-coenzyme A</synonym>
    <synonym>Acetoacetyl CoA</synonym>
  </synonyms>
  <chemical_formula>C25H40N7O18P3S</chemical_formula>
  <average_molecular_weight>851.607</average_molecular_weight>
  <monisotopic_moleculate_weight>851.136337737</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>acetoacetyl-coa</traditional_iupac>
  <cas_registry_number>1420-36-6</cas_registry_number>
  <smiles>CC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C25H40N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-12,14,18-20,24,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18-,19-,20+,24-/m1/s1</inchi>
  <inchikey>OJFDKHTZOUZBOS-CITAKDKDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aminopiperidines. Aminopiperidines are compounds containing a piperidine that carries an amino group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Piperidines</class>
    <sub_class>Aminopiperidines</sub_class>
    <direct_parent>Aminopiperidines</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>4-aminopiperidine</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>bipiperidine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>851.607</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>851.136337737</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H40N7O18P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C25H40N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-12,14,18-20,24,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18-,19-,20+,24-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OJFDKHTZOUZBOS-CITAKDKDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>380.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>182.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>76.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Butyrate Metabolism</name>
      <smpdb_id>SMP0087185</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ketone Body Metabolism</name>
      <smpdb_id>SMP0087202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33301</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00332</kegg_id>
  <chemspider_id/>
  <drugbank_id>DB03059</drugbank_id>
  <foodb_id/>
  <pubchem_compound_id>92153</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15345</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007269</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Acetoacetyl-CoA</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00359</protein_accession>
      <name>Hydroxymethylglutaryl-CoA synthase, mitochondrial</name>
      <uniprot_id>Q2KIE6</uniprot_id>
      <gene_name>HMGCS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00371</protein_accession>
      <name>Acetyl-CoA acetyltransferase, mitochondrial</name>
      <uniprot_id>Q29RZ0</uniprot_id>
      <gene_name>ACAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:36 UTC</creation_date>
  <update_date>2020-04-16 17:52:25 UTC</update_date>
  <accession>BMDB0001485</accession>
  <secondary_accessions>
    <accession>BMDB01485</accession>
  </secondary_accessions>
  <name>Octane</name>
  <description/>
  <synonyms>
    <synonym>CH3-[CH2]6-CH3</synonym>
    <synonym>N-Octane</synonym>
    <synonym>N-Oktan</synonym>
    <synonym>Oktan</synonym>
  </synonyms>
  <chemical_formula>C8H18</chemical_formula>
  <average_molecular_weight>114.2285</average_molecular_weight>
  <monisotopic_moleculate_weight>114.140850576</monisotopic_moleculate_weight>
  <iupac_name>octane</iupac_name>
  <traditional_iupac>octane</traditional_iupac>
  <cas_registry_number>111-65-9</cas_registry_number>
  <smiles>CCCCCCCC</smiles>
  <inchi>InChI=1S/C8H18/c1-3-5-7-8-6-4-2/h3-8H2,1-2H3</inchi>
  <inchikey>TVMXDCGIABBOFY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Hydrocarbons</super_class>
    <class>Saturated hydrocarbons</class>
    <sub_class>Alkanes</sub_class>
    <direct_parent>Alkanes</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Acyclic alkane</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkane</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydrocarbons</external_descriptor>
      <external_descriptor>Hydrocarbons</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>alkane</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-56.8 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.00066 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.18</value>
      <source>MILLER,MM ET AL. (1985)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>octane</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>114.2285</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>114.140850576</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H18/c1-3-5-7-8-6-4-2/h3-8H2,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>TVMXDCGIABBOFY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18557</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5332</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5333</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351018</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples have been collected from Heifer cows.</comment>
      <references>
        <reference>
          <reference_text>Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub  2013 Jun 5.</reference_text>
          <pubmed_id>23871026</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01387</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB000758</foodb_id>
  <chemspider_id>349</chemspider_id>
  <pubchem_compound_id>356</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17590</chebi_id>
  <knapsack_id>C00035857</knapsack_id>
  <wikipedia_id>Octane</wikipedia_id>
  <meta_cyc_id>CPD-148</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6270</metlin_id>
  <synthesis_reference>Lewis, H. F.; Yohe, G. R.  The preparation of pure octane.    Proceedings of the Iowa Academy of Science  (1925),  32  327-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:37 UTC</creation_date>
  <update_date>2020-04-16 20:38:42 UTC</update_date>
  <accession>BMDB0001487</accession>
  <secondary_accessions>
    <accession>BMDB01487</accession>
  </secondary_accessions>
  <name>NADH</name>
  <description>Nadhh, also known as NAD or DPNH, belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage. Nadhh exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Nadhh exists in all living species, ranging from bacteria to humans. In cattle, nadhh is involved in the metabolic pathway called cancer (via the Warburg effect).</description>
  <synonyms>
    <synonym>1,4-DIHYDRONICOTINAMIDE adenine dinucleotide</synonym>
    <synonym>DPNH</synonym>
    <synonym>Nicotinamide adenine dinucleotide (reduced)</synonym>
    <synonym>Reduced nicotinamide adenine dinucleotide</synonym>
    <synonym>b-DPNH</synonym>
    <synonym>b-NADH</synonym>
    <synonym>beta-DPNH</synonym>
    <synonym>beta-NADH</synonym>
    <synonym>Dihydrocodehydrogenase I</synonym>
    <synonym>Dihydrocozymase</synonym>
    <synonym>Dihydronicotinamide adenine dinucleotide</synonym>
    <synonym>Dihydronicotinamide mononucleotide</synonym>
    <synonym>ENADA</synonym>
    <synonym>NADH2</synonym>
    <synonym>Reduced codehydrogenase I</synonym>
    <synonym>Reduced diphosphopyridine nucleotide</synonym>
    <synonym>Reduced nicotinamide adenine diphosphate</synonym>
    <synonym>Reduced nicotinamide-adenine dinucleotide</synonym>
    <synonym>Nadide</synonym>
    <synonym>Coenzyme I</synonym>
    <synonym>DPN</synonym>
    <synonym>Diphosphopyridine nucleotide</synonym>
    <synonym>Nicotinamide adenine dinucleotide</synonym>
    <synonym>Nicotinamide-adenine dinucleotide</synonym>
    <synonym>NAD</synonym>
    <synonym>Nucleotide, diphosphopyridine</synonym>
    <synonym>Adenine dinucleotide, dihydronicotinamide</synonym>
    <synonym>Dinucleotide, dihydronicotinamide adenine</synonym>
    <synonym>Dinucleotide, nicotinamide-adenine</synonym>
  </synonyms>
  <chemical_formula>C21H29N7O14P2</chemical_formula>
  <average_molecular_weight>665.441</average_molecular_weight>
  <monisotopic_moleculate_weight>665.124771695</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid</iupac_name>
  <traditional_iupac>NADH</traditional_iupac>
  <cas_registry_number>58-68-4</cas_registry_number>
  <smiles>NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1</inchi>
  <inchikey>BOPGDPNILDQYTO-NNYOXOHSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Amino acids and derivatives</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Dihydropyridines</alternative_parent>
      <alternative_parent>Enamines</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>N-substituted nicotinamides</alternative_parent>
      <alternative_parent>Nicotinamide nucleotides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dihydropyridine</substituent>
      <substituent>Enamine</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyridine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>N-substituted nicotinamide</substituent>
      <substituent>Nicotinamide-nucleotide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>NAD</external_descriptor>
      <external_descriptor>NAD(P)H</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>665.441</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>665.124771695</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H29N7O14P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BOPGDPNILDQYTO-NNYOXOHSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>317.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>143</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>57.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26882</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218129</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>48+/-26</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>94+/-75</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>101+/-45</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>21+/-8</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00004</kegg_id>
  <drugbank_id>DB00157</drugbank_id>
  <foodb_id>FDB022649</foodb_id>
  <chemspider_id>903</chemspider_id>
  <pubchem_compound_id>439153</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16908</chebi_id>
  <knapsack_id>C00019343</knapsack_id>
  <wikipedia_id>Nicotinamide_adenine_dinucleotide</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>33484</bigg_id>
  <metlin_id>3687</metlin_id>
  <synthesis_reference>Marek, Miroslav; Vrbova, Eva; Horakova, Irena; Musil, Petr; Kefurt, Karel.  NADH manufacture with immobilized Candida formate dehydrogenase.    Czech.  (1992),     4 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00066</protein_accession>
      <name>Cytochrome b5 reductase 4</name>
      <uniprot_id>Q32LH7</uniprot_id>
      <gene_name>CYB5R4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00097</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 7, mitochondrial</name>
      <uniprot_id>P42026</uniprot_id>
      <gene_name>NDUFS7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00099</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 2, mitochondrial</name>
      <uniprot_id>P17694</uniprot_id>
      <gene_name>NDUFS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00154</protein_accession>
      <name>Glyceraldehyde-3-phosphate dehydrogenase</name>
      <uniprot_id>P10096</uniprot_id>
      <gene_name>GAPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00209</protein_accession>
      <name>Glyceraldehyde-3-phosphate dehydrogenase, testis-specific</name>
      <uniprot_id>Q2KJE5</uniprot_id>
      <gene_name>GAPDHS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00259</protein_accession>
      <name>Lambda-crystallin homolog</name>
      <uniprot_id>Q8SPX7</uniprot_id>
      <gene_name>CRYL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00260</protein_accession>
      <name>Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial</name>
      <uniprot_id>Q07536</uniprot_id>
      <gene_name>ALDH6A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00262</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IX89</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00263</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>P03887</uniprot_id>
      <gene_name>MT-ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00264</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q45LU7</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00265</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q6JTG2</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00266</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IXE1</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00267</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>B1NZU0</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00268</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45M50</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00269</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MI0</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00270</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q3L5H4</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00271</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45LG6</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00272</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1NZ26</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00273</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] flavoprotein 2, mitochondrial</name>
      <uniprot_id>P04394</uniprot_id>
      <gene_name>NDUFV2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00274</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q8HBP4</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00275</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0B8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00276</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>B1P0I6</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00277</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q6JTH0</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00278</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q45MJ0</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00279</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q85EA2</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00280</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q7JAL5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00281</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q8HC63</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00282</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q6QTH1</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00283</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q45MC5</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00284</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>Q7JAS5</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00285</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q8HC24</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00286</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0J6</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00287</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4L</name>
      <uniprot_id>Q3L5T0</uniprot_id>
      <gene_name>ND4L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00288</protein_accession>
      <name>NADH dehydrogenase subunit 4</name>
      <uniprot_id>C5IX88</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00289</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q3L5J7</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00290</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>Q85UJ0</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00291</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>B1P078</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00292</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>B1P0N6</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00293</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>Q7JAS9</uniprot_id>
      <gene_name>ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00294</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P092</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00295</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q45MX4</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00296</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>P03924</uniprot_id>
      <gene_name>MT-ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00298</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0N5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00299</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q6JTD6</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00300</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45LK5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00301</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>B1NZ92</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00302</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>A4ZI01</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00303</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>P03920</uniprot_id>
      <gene_name>MT-ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00304</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q85E90</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00305</protein_accession>
      <name>NADH-ubiquinone oxidoreductase 75 kDa subunit, mitochondrial</name>
      <uniprot_id>P15690</uniprot_id>
      <gene_name>NDUFS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00306</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q45M46</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00307</protein_accession>
      <name>NADH dehydrogenase subunit 4</name>
      <uniprot_id>C5IX62</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00308</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q45MC9</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00309</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45LU6</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00310</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>B1P044</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00311</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q45LV6</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00312</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>B1P0M6</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00313</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P0M2</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00314</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q6QTH0</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00315</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q85BD6</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00316</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q6JTD5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00317</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4L</name>
      <uniprot_id>Q7JAS8</uniprot_id>
      <gene_name>ND4L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00318</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IX37</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00319</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>P03910</uniprot_id>
      <gene_name>MT-ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00320</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q45M85</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00321</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1P027</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00322</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q8HAW7</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00323</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q6JTE4</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00324</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>Q45LU9</uniprot_id>
      <gene_name>ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00325</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MC8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00326</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4L</name>
      <uniprot_id>P03902</uniprot_id>
      <gene_name>MT-ND4L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00327</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45LV9</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00328</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q85BS9</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00329</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 3, mitochondrial</name>
      <uniprot_id>P23709</uniprot_id>
      <gene_name>NDUFS3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00330</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q7JAT5</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00331</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>B1NZ38</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00332</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MW0</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00333</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q8HQD4</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00334</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q7JAS7</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00335</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MP5</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00336</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>P03898</uniprot_id>
      <gene_name>MT-ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00337</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>P03892</uniprot_id>
      <gene_name>MT-ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00338</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q8HBM0</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00340</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>B1P0L9</uniprot_id>
      <gene_name>ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00341</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 1</name>
      <uniprot_id>Q7JAT6</uniprot_id>
      <gene_name>ND1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00342</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>Q45MA2</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00343</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1NZY8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00345</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] iron-sulfur protein 8, mitochondrial</name>
      <uniprot_id>P42028</uniprot_id>
      <gene_name>NDUFS8</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00346</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 2</name>
      <uniprot_id>Q45MY2</uniprot_id>
      <gene_name>ND2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00347</protein_accession>
      <name>NADH dehydrogenase subunit 5</name>
      <uniprot_id>C5IXC8</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00348</protein_accession>
      <name>NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial</name>
      <uniprot_id>P25708</uniprot_id>
      <gene_name>NDUFV1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00349</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 5</name>
      <uniprot_id>B1NZB7</uniprot_id>
      <gene_name>ND5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00350</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 6</name>
      <uniprot_id>Q85UI9</uniprot_id>
      <gene_name>ND6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00351</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 3</name>
      <uniprot_id>Q6QTG4</uniprot_id>
      <gene_name>ND3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00352</protein_accession>
      <name>NADH-ubiquinone oxidoreductase chain 4</name>
      <uniprot_id>Q45LS1</uniprot_id>
      <gene_name>ND4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00374</protein_accession>
      <name>Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrial</name>
      <uniprot_id>Q0P5C2</uniprot_id>
      <gene_name>MTHFD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00385</protein_accession>
      <name>L-threonine 3-dehydrogenase, mitochondrial</name>
      <uniprot_id>Q2KIR8</uniprot_id>
      <gene_name>TDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00448</protein_accession>
      <name>Isocitrate dehydrogenase [NADP], mitochondrial</name>
      <uniprot_id>Q04467</uniprot_id>
      <gene_name>IDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00454</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit gamma, mitochondrial</name>
      <uniprot_id>Q58CP0</uniprot_id>
      <gene_name>IDH3G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00471</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial</name>
      <uniprot_id>O77784</uniprot_id>
      <gene_name>IDH3B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00516</protein_accession>
      <name>Isocitrate dehydrogenase [NADP] cytoplasmic</name>
      <uniprot_id>Q9XSG3</uniprot_id>
      <gene_name>IDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00521</protein_accession>
      <name>Isocitrate dehydrogenase [NAD] subunit alpha, mitochondrial</name>
      <uniprot_id>P41563</uniprot_id>
      <gene_name>IDH3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00528</protein_accession>
      <name>NAD+ dependent 15-hydroxyprostaglandin dehydrogenase</name>
      <uniprot_id>Q309F3</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00550</protein_accession>
      <name>3-hydroxyisobutyrate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q2HJD7</uniprot_id>
      <gene_name>HIBADH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00573</protein_accession>
      <name>L-lactate dehydrogenase A-like 6B</name>
      <uniprot_id>Q3T056</uniprot_id>
      <gene_name>LDHAL6B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00574</protein_accession>
      <name>L-lactate dehydrogenase B chain</name>
      <uniprot_id>Q5E9B1</uniprot_id>
      <gene_name>LDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00575</protein_accession>
      <name>L-lactate dehydrogenase A chain</name>
      <uniprot_id>P19858</uniprot_id>
      <gene_name>LDHA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00576</protein_accession>
      <name>L-lactate dehydrogenase</name>
      <uniprot_id>B0JYN3</uniprot_id>
      <gene_name>LDHB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00577</protein_accession>
      <name>L-lactate dehydrogenase</name>
      <uniprot_id>Q2KJG0</uniprot_id>
      <gene_name>LDHC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00593</protein_accession>
      <name>4-trimethylaminobutyraldehyde dehydrogenase</name>
      <uniprot_id>Q2KJH9</uniprot_id>
      <gene_name>ALDH9A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00601</protein_accession>
      <name>Retinal dehydrogenase 1</name>
      <uniprot_id>P48644</uniprot_id>
      <gene_name>ALDH1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00603</protein_accession>
      <name>Xanthine dehydrogenase/oxidase</name>
      <uniprot_id>P80457</uniprot_id>
      <gene_name>XDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00606</protein_accession>
      <name>Hydroxysteroid 17-beta dehydrogenase 6</name>
      <uniprot_id>Q3T001</uniprot_id>
      <gene_name>HSD17B6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00616</protein_accession>
      <name>Malate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q32LG3</uniprot_id>
      <gene_name>MDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00619</protein_accession>
      <name>Malate dehydrogenase</name>
      <uniprot_id>Q58DR9</uniprot_id>
      <gene_name>MDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00620</protein_accession>
      <name>Malate dehydrogenase, cytoplasmic</name>
      <uniprot_id>Q3T145</uniprot_id>
      <gene_name>MDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00621</protein_accession>
      <name>Malate dehydrogenase</name>
      <uniprot_id>Q0QF29</uniprot_id>
      <gene_name>MDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00630</protein_accession>
      <name>Corticosteroid 11-beta-dehydrogenase isozyme 2</name>
      <uniprot_id>O77667</uniprot_id>
      <gene_name>HSD11B2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00631</protein_accession>
      <name>Alpha-aminoadipic semialdehyde synthase, mitochondrial</name>
      <uniprot_id>A8E657</uniprot_id>
      <gene_name>AASS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00632</protein_accession>
      <name>Probable saccharopine dehydrogenase</name>
      <uniprot_id>Q3T067</uniprot_id>
      <gene_name>SCCPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00677</protein_accession>
      <name>Aldehyde oxidase</name>
      <uniprot_id>P48034</uniprot_id>
      <gene_name>AOX1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00692</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q9XSN4</uniprot_id>
      <gene_name>GAPDL17</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00693</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q862K5</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00694</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q0QES8</uniprot_id>
      <gene_name>GAPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00695</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q4H0Z3</uniprot_id>
      <gene_name>gapdh</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00697</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q712W6</uniprot_id>
      <gene_name>GAPDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00715</protein_accession>
      <name>11-cis retinol dehydrogenase</name>
      <uniprot_id>Q27979</uniprot_id>
      <gene_name>RDH5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00784</protein_accession>
      <name>Sorbitol dehydrogenase</name>
      <uniprot_id>Q58D31</uniprot_id>
      <gene_name>SORD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00832</protein_accession>
      <name>Poly [ADP-ribose] polymerase 1</name>
      <uniprot_id>P18493</uniprot_id>
      <gene_name>PARP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00848</protein_accession>
      <name>UDP-glucose 6-dehydrogenase</name>
      <uniprot_id>P12378</uniprot_id>
      <gene_name>UGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00856</protein_accession>
      <name>Glutamate dehydrogenase 1, mitochondrial</name>
      <uniprot_id>P00366</uniprot_id>
      <gene_name>GLUD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00866</protein_accession>
      <name>NADH-cytochrome b5 reductase 1</name>
      <uniprot_id>Q3MHW9</uniprot_id>
      <gene_name>CYB5R1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00899</protein_accession>
      <name>NADH-cytochrome b5 reductase 3</name>
      <uniprot_id>P07514</uniprot_id>
      <gene_name>CYB5R3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00931</protein_accession>
      <name>Glycerol-3-phosphate dehydrogenase [NAD+], cytoplasmic</name>
      <uniprot_id>Q5EA88</uniprot_id>
      <gene_name>GPD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00961</protein_accession>
      <name>3-hydroxyacyl-CoA dehydrogenase type-2</name>
      <uniprot_id>O02691</uniprot_id>
      <gene_name>HSD17B10</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00988</protein_accession>
      <name>Aldehyde dehydrogenase X, mitochondrial</name>
      <uniprot_id>P52476</uniprot_id>
      <gene_name>ALDH1B1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00990</protein_accession>
      <name>Aldehyde dehydrogenase, mitochondrial</name>
      <uniprot_id>P20000</uniprot_id>
      <gene_name>ALDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00991</protein_accession>
      <name>Alcohol dehydrogenase class-3</name>
      <uniprot_id>Q3ZC42</uniprot_id>
      <gene_name>ADH5</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01001</protein_accession>
      <name>NAD(P) transhydrogenase, mitochondrial</name>
      <uniprot_id>P11024</uniprot_id>
      <gene_name>NNT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01002</protein_accession>
      <name>Inosine-5'-monophosphate dehydrogenase 2</name>
      <uniprot_id>Q3SWY3</uniprot_id>
      <gene_name>IMPDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01003</protein_accession>
      <name>Inosine-5'-monophosphate dehydrogenase</name>
      <uniprot_id>A0JNA3</uniprot_id>
      <gene_name>IMPDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01009</protein_accession>
      <name>3-hydroxybutyrate dehydrogenase type 2</name>
      <uniprot_id>Q3T046</uniprot_id>
      <gene_name>BDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01010</protein_accession>
      <name>D-beta-hydroxybutyrate dehydrogenase, mitochondrial</name>
      <uniprot_id>Q02337</uniprot_id>
      <gene_name>BDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01017</protein_accession>
      <name>15-hydroxyprostaglandin dehydrogenase [NAD+]</name>
      <uniprot_id>Q3T0C2</uniprot_id>
      <gene_name>HPGD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01022</protein_accession>
      <name>3 beta-hydroxysteroid dehydrogenase/Delta 5--&gt;4-isomerase</name>
      <uniprot_id>P14893</uniprot_id>
      <gene_name>HSD3B</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01072</protein_accession>
      <name>D-3-phosphoglycerate dehydrogenase</name>
      <uniprot_id>Q5EAD2</uniprot_id>
      <gene_name>PHGDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01093</protein_accession>
      <name>Isocitrate dehydrogenase 3 (NAD+) gamma isoform a</name>
      <uniprot_id>Q58D96</uniprot_id>
      <gene_name>IDH3G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01094</protein_accession>
      <name>Glyceraldehyde phosphate dehydrogenase</name>
      <uniprot_id>Q865L2</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01095</protein_accession>
      <name>Glyceraldehyde-3-phosphate dehydrogenase</name>
      <uniprot_id>Q2QJG6</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01096</protein_accession>
      <name>NAD(+)-dependent isocitrate dehydrogenase subunit 3</name>
      <uniprot_id>Q9BGH9</uniprot_id>
      <gene_name>IDH3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01097</protein_accession>
      <name>Similar to glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q862P5</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01098</protein_accession>
      <name>Similar to glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q862K1</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01099</protein_accession>
      <name>Isocitrate dehydrogenase 1</name>
      <uniprot_id>Q0QEQ4</uniprot_id>
      <gene_name>IDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01100</protein_accession>
      <name>Isocitrate dehydrogenase 3 (NAD+) alpha</name>
      <uniprot_id>Q148J8</uniprot_id>
      <gene_name>IDH3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01101</protein_accession>
      <name>NAD(+)-isocitrate dehydrogenase subunit 1 IDH1-C</name>
      <uniprot_id>Q9TVD2</uniprot_id>
      <gene_name>IDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01102</protein_accession>
      <name>Similar to glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>Q862S2</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01103</protein_accession>
      <name>Isocitrate dehydrogenase 3 (NAD+) gamma isoform a</name>
      <uniprot_id>Q58D82</uniprot_id>
      <gene_name>IDH3G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01104</protein_accession>
      <name>Isocitrate dehydrogenase 3 (NAD+) gamma isoform a</name>
      <uniprot_id>Q58DM0</uniprot_id>
      <gene_name>IDH3G</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01105</protein_accession>
      <name>Glyceraldehyde 3-phosphate dehydrogenase</name>
      <uniprot_id>O77679</uniprot_id>
      <gene_name>G3PDH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02255</protein_accession>
      <name>GPD1L protein</name>
      <uniprot_id>A6QQR7</uniprot_id>
      <gene_name>GPD1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02260</protein_accession>
      <name>C-terminal-binding protein 2</name>
      <uniprot_id>Q0VCQ1</uniprot_id>
      <gene_name>CTBP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02562</protein_accession>
      <name>Malic enzyme</name>
      <uniprot_id>Q0VCX7</uniprot_id>
      <gene_name>ME3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02563</protein_accession>
      <name>Malic enzyme</name>
      <uniprot_id>Q08DM3</uniprot_id>
      <gene_name>ME2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02564</protein_accession>
      <name>Malic enzyme</name>
      <uniprot_id>Q5MAA9</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02565</protein_accession>
      <name>C-terminal binding protein 2</name>
      <uniprot_id>A5D9E5</uniprot_id>
      <gene_name>CTBP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02566</protein_accession>
      <name>Malic enzyme</name>
      <uniprot_id>B8YB77</uniprot_id>
      <gene_name>ME1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02567</protein_accession>
      <name>C-terminal binding protein 1</name>
      <uniprot_id>A5D9F1</uniprot_id>
      <gene_name>CTBP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02568</protein_accession>
      <name>Malic enzyme</name>
      <uniprot_id>B8Y898</uniprot_id>
      <gene_name>ME1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02569</protein_accession>
      <name>Similar to C-terminal binding protein 1</name>
      <uniprot_id>Q2HJ80</uniprot_id>
      <gene_name>LOC515578</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:38 UTC</creation_date>
  <update_date>2020-04-16 20:39:25 UTC</update_date>
  <accession>BMDB0001488</accession>
  <secondary_accessions>
    <accession>BMDB01488</accession>
  </secondary_accessions>
  <name>Nicotinic acid</name>
  <description>Nicotinic acid, also known as niacin or nicotinate, belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group. Nicotinic acid is a drug which is used for the treatment of type iv and v hyperlipidemia. it is indicated as ajunctive therapy. Nicotinic acid exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Nicotinic acid exists in all living species, ranging from bacteria to humans. Nicotinic acid and ribose 1-phosphate can be biosynthesized from nicotinate D-ribonucleoside through the action of the enzyme purine nucleoside phosphorylase. In cattle, nicotinic acid is involved in the metabolic pathway called the nicotinate and nicotinamide metabolism pathway. Nicotinic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>3-Carboxypyridine</synonym>
    <synonym>3-Pyridinecarboxylic acid</synonym>
    <synonym>3-Pyridylcarboxylic acid</synonym>
    <synonym>Acide nicotinique</synonym>
    <synonym>Acido nicotinico</synonym>
    <synonym>Acidum nicotinicum</synonym>
    <synonym>Anti-pellagra vitamin</synonym>
    <synonym>beta-Pyridinecarboxylic acid</synonym>
    <synonym>m-Pyridinecarboxylic acid</synonym>
    <synonym>Niacin</synonym>
    <synonym>Nikotinsaeure</synonym>
    <synonym>P.P. factor</synonym>
    <synonym>Pellagra preventive factor</synonym>
    <synonym>PP Factor</synonym>
    <synonym>Pyridine-beta-carboxylic acid</synonym>
    <synonym>Vitamin b3</synonym>
    <synonym>Niacor</synonym>
    <synonym>Niaspan</synonym>
    <synonym>3-Pyridinecarboxylate</synonym>
    <synonym>3-Pyridylcarboxylate</synonym>
    <synonym>b-Pyridinecarboxylate</synonym>
    <synonym>b-Pyridinecarboxylic acid</synonym>
    <synonym>beta-Pyridinecarboxylate</synonym>
    <synonym>Β-pyridinecarboxylate</synonym>
    <synonym>Β-pyridinecarboxylic acid</synonym>
    <synonym>m-Pyridinecarboxylate</synonym>
    <synonym>Pyridine-b-carboxylate</synonym>
    <synonym>Pyridine-b-carboxylic acid</synonym>
    <synonym>Pyridine-beta-carboxylate</synonym>
    <synonym>Pyridine-β-carboxylate</synonym>
    <synonym>Pyridine-β-carboxylic acid</synonym>
    <synonym>Nicotinate</synonym>
    <synonym>3-Carboxylpyridine</synonym>
    <synonym>Akotin</synonym>
    <synonym>Apelagrin</synonym>
    <synonym>Daskil</synonym>
    <synonym>Efacin</synonym>
    <synonym>Enduracin</synonym>
    <synonym>Linic</synonym>
    <synonym>Niac</synonym>
    <synonym>Niacine</synonym>
    <synonym>Nicacid</synonym>
    <synonym>Nicamin</synonym>
    <synonym>Nicangin</synonym>
    <synonym>Nico-span</synonym>
    <synonym>Nicobid</synonym>
    <synonym>Nicocap</synonym>
    <synonym>Nicodelmine</synonym>
    <synonym>Nicolar</synonym>
    <synonym>Niconacid</synonym>
    <synonym>Nicosan 3</synonym>
    <synonym>Nicotinipca</synonym>
    <synonym>Nicyl</synonym>
    <synonym>Nyclin</synonym>
    <synonym>Pellagrin</synonym>
    <synonym>Pelonin</synonym>
    <synonym>Slo-niacin</synonym>
    <synonym>Wampocap</synonym>
    <synonym>Aluminum salt, niacin</synonym>
    <synonym>Induracin</synonym>
    <synonym>Niacin cobalt (2+) salt</synonym>
    <synonym>Niacin iron (2+) salt</synonym>
    <synonym>Niacin lithium salt</synonym>
    <synonym>Niacin magnesium salt</synonym>
    <synonym>Niacin sodium salt</synonym>
    <synonym>Nico-400</synonym>
    <synonym>Potassium salt, niacin</synonym>
    <synonym>Sodium salt, niacin</synonym>
    <synonym>Tosylate, niacin</synonym>
    <synonym>Nicotinate, lithium</synonym>
    <synonym>Hydrochloride, niacin</synonym>
    <synonym>Niacin aluminum salt</synonym>
    <synonym>Niacin calcium salt</synonym>
    <synonym>Niacin copper (2+) salt</synonym>
    <synonym>Niacin hydrochloride</synonym>
    <synonym>Niacin lithium salt, hemihydrate</synonym>
    <synonym>Nico400</synonym>
    <synonym>Tartrate, niacin</synonym>
    <synonym>3 Pyridinecarboxylic acid</synonym>
    <synonym>Lithium nicotinate</synonym>
    <synonym>Niacin ammonium salt</synonym>
    <synonym>Niacin manganese (2+) salt</synonym>
    <synonym>Niacin potassium salt</synonym>
    <synonym>Niacin tartrate</synonym>
    <synonym>Niacin tosylate</synonym>
    <synonym>Niacin zinc salt</synonym>
    <synonym>Nico 400</synonym>
  </synonyms>
  <chemical_formula>C6H5NO2</chemical_formula>
  <average_molecular_weight>123.1094</average_molecular_weight>
  <monisotopic_moleculate_weight>123.032028409</monisotopic_moleculate_weight>
  <iupac_name>pyridine-3-carboxylic acid</iupac_name>
  <traditional_iupac>niacin</traditional_iupac>
  <cas_registry_number>59-67-6</cas_registry_number>
  <smiles>OC(=O)C1=CN=CC=C1</smiles>
  <inchi>InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)</inchi>
  <inchikey>PVNIIMVLHYAWGP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyridinecarboxylic acids and derivatives</sub_class>
    <direct_parent>Pyridinecarboxylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine carboxylic acid</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Pyridine alkaloids</external_descriptor>
      <external_descriptor>Water-soluble vitamins</external_descriptor>
      <external_descriptor>pyridine alkaloid</external_descriptor>
      <external_descriptor>pyridinemonocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>236.6 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>18.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.36</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>pyridine-3-carboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>123.1094</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>123.032028409</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C1=CN=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H5NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PVNIIMVLHYAWGP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>50.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1037</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2756</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27987</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1604</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5336</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5337</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5338</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5339</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181120</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438192</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Colostrum</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.0669</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with blend of hydrogenated vegetable oils</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.0669</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.554</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.148</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.493</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.123</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.311</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added nonfat milk solids, vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.554</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.204</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, protein fortified, with added vitamin A and vitamin D (fat free and skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.392</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.635</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.635</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.529</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.311</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.823</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, producer, fluid, 3.7% milkfat</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.204</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.311</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids and vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.204</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added nonfat milk solids, without added vitamin A</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.473</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.473</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.311</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.392</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.311</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.498</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.229</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.229</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.473</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>7.0669</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>8.935</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32.492</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Enriched, sterilized, whole commercial milk</comment>
      <references>
        <reference>
          <reference_text>Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309.</reference_text>
          <pubmed_id>17558655</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>6.823 - 7.148</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>Zanardi E, Caligiani A, Palla L, Mariani M, Ghidini S, Di Ciccio PA, Palla G, Ianieri A: Metabolic profiling by (1)H NMR of ground beef irradiated at different irradiation doses. Meat Sci. 2015 May;103:83-9. doi: 10.1016/j.meatsci.2015.01.005. Epub 2015 Jan 15.</reference_text>
          <pubmed_id>25637742</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>43</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>62.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>41.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>37.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>60+/-10</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>37.45 +/- 7.48</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>18-46</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>24.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>35.7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>32.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>21.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>43 +/- 11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>62 +/- 17</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>41 +/- 12</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>37 +/- 8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00253</kegg_id>
  <drugbank_id>DB00627</drugbank_id>
  <foodb_id>FDB001014</foodb_id>
  <chemspider_id>913</chemspider_id>
  <pubchem_compound_id>938</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15940</chebi_id>
  <knapsack_id>C00000208</knapsack_id>
  <wikipedia_id>Niacin</wikipedia_id>
  <meta_cyc_id>NIACINE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34401</bigg_id>
  <metlin_id>6272</metlin_id>
  <synthesis_reference>McElvain, S. M.; Goese, M. A. Preparation of nicotinic acid from pyridine. Journal of the American Chemical Society (1941), 63 2283-4.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309.</reference_text>
      <pubmed_id>17558655</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
      <pubmed_id>22081685</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00535</protein_accession>
      <name>Diacylglycerol O-acyltransferase 2</name>
      <uniprot_id>Q70VZ8</uniprot_id>
      <gene_name>DGAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:40 UTC</creation_date>
  <update_date>2020-03-13 16:28:22 UTC</update_date>
  <accession>BMDB0001489</accession>
  <secondary_accessions>
    <accession>BMDB01489</accession>
  </secondary_accessions>
  <name>Ribose 1-phosphate</name>
  <description/>
  <synonyms>
    <synonym>1-O-Phosphono-alpha-D-ribofuranose</synonym>
    <synonym>1-Phospho-alpha-D-ribofuranose</synonym>
    <synonym>D-Ribose 1-phosphate</synonym>
    <synonym>1-O-Phosphono-a-D-ribofuranose</synonym>
    <synonym>1-O-Phosphono-α-D-ribofuranose</synonym>
    <synonym>1-Phospho-a-D-ribofuranose</synonym>
    <synonym>1-Phospho-α-D-ribofuranose</synonym>
    <synonym>D-Ribose 1-phosphoric acid</synonym>
    <synonym>Ribose 1-phosphoric acid</synonym>
    <synonym>1-O-Phosphono-D-ribofuranose</synonym>
    <synonym>a-D-Ribofuranose 1-(dihydrogen phosphate)</synonym>
    <synonym>a-D-Ribose 1-phosphate</synonym>
    <synonym>alpha-D-Ribofuranose 1-(dihydrogen phosphate)</synonym>
    <synonym>alpha-D-Ribofuranose 1-phosphate</synonym>
    <synonym>alpha-D-Ribose 1-phosphate</synonym>
    <synonym>D-Ribofuranose 1-(dihydrogen phosphate)</synonym>
    <synonym>D-Ribofuranose 1-phosphate</synonym>
    <synonym>D-Ribose-1-phosphate</synonym>
    <synonym>D-Ribose-1P</synonym>
    <synonym>Ribofuranose 1-phosphate</synonym>
    <synonym>Ribose 1-phosphate, (beta-D)-isomer</synonym>
    <synonym>Ribose 1-phosphate, (alpha-D)-isomer</synonym>
  </synonyms>
  <chemical_formula>C5H11O8P</chemical_formula>
  <average_molecular_weight>230.1098</average_molecular_weight>
  <monisotopic_moleculate_weight>230.01915384</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>ribose 1-phosphate</traditional_iupac>
  <cas_registry_number>14075-00-4</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C5H11O8P/c6-1-2-3(7)4(8)5(12-2)13-14(9,10)11/h2-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5-/m1/s1</inchi>
  <inchikey>YXJDFQJKERBOBM-TXICZTDVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D-ribose 1-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>230.1098</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>230.01915384</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H11O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H11O8P/c6-1-2-3(7)4(8)5(12-2)13-14(9,10)11/h2-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YXJDFQJKERBOBM-TXICZTDVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>136.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438398</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00620</kegg_id>
  <drugbank_id>DB03101</drugbank_id>
  <foodb_id>FDB031271</foodb_id>
  <chemspider_id>388373</chemspider_id>
  <pubchem_compound_id>439236</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16300</chebi_id>
  <knapsack_id/>
  <wikipedia_id/>
  <meta_cyc_id>RIBOSE-1P</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34994</bigg_id>
  <metlin_id>6273</metlin_id>
  <synthesis_reference>Tochikura, Tatsurokuro; Sakai, Takuo; Ogata, Koichi.  Ribose 1-phosphate production by fermentation.    Jpn. Tokkyo Koho  (1969),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00698</protein_accession>
      <name>Purine nucleoside phosphorylase</name>
      <uniprot_id>P55859</uniprot_id>
      <gene_name>NP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:41 UTC</creation_date>
  <update_date>2020-04-16 20:40:42 UTC</update_date>
  <accession>BMDB0001490</accession>
  <secondary_accessions>
    <accession>BMDB01490</accession>
  </secondary_accessions>
  <name>Vanylglycol</name>
  <description>Vanylglycol, also known as MHPG or vanylglycol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Vanylglycol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Vanylglycol and pyrocatechol can be biosynthesized from 3,4-dihydroxyphenylglycol and guaiacol through its interaction with the enzyme catechol O-methyltransferase. In cattle, vanylglycol is involved in the metabolic pathway called the tyrosine metabolism pathway.</description>
  <synonyms>
    <synonym>1-(4-Hydroxy-3-methoxyphenyl)-1,2-ethanediol</synonym>
    <synonym>3-Methoxy-4-hydroxyphenethylene glycol</synonym>
    <synonym>3-Methoxy-4-hydroxyphenyl glycol</synonym>
    <synonym>4-Hydroxy-3-methoxy-b-phenylglycol</synonym>
    <synonym>4-Hydroxy-3-methoxy-beta-phenylglycol</synonym>
    <synonym>4-Hydroxy-3-methoxyphenyl glycol</synonym>
    <synonym>HMPG</synonym>
    <synonym>Hydroxymethoxyphenylglycol</synonym>
    <synonym>Methoxyhydroxyphenylglycol</synonym>
    <synonym>MHPG</synonym>
    <synonym>MOPEG</synonym>
    <synonym>4 Hydroxy 3 methoxyphenylethyleneglycol</synonym>
    <synonym>4 Hydroxy 3 methoxyphenylglycol</synonym>
    <synonym>4-Hydroxy-3-methoxyphenylethyleneglycol</synonym>
    <synonym>Methoxyhydroxyphenylglycol, (-)-isomer</synonym>
    <synonym>4 Hydroxy 3 methoxyphenylethylene glycol</synonym>
    <synonym>4-Hydroxy-3-methoxyphenylglycol</synonym>
    <synonym>Methoxyhydroxyphenylglycol, (+)-isomer</synonym>
    <synonym>4-Hydroxy-3-methoxyphenylethylene glycol</synonym>
    <synonym>Methoxyhydroxyphenylglycol, (+-)-isomer</synonym>
  </synonyms>
  <chemical_formula>C9H12O4</chemical_formula>
  <average_molecular_weight>184.1892</average_molecular_weight>
  <monisotopic_moleculate_weight>184.073558872</monisotopic_moleculate_weight>
  <iupac_name>1-(4-hydroxy-3-methoxyphenyl)ethane-1,2-diol</iupac_name>
  <traditional_iupac>methoxyhydroxyphenylglycol</traditional_iupac>
  <cas_registry_number>534-82-7</cas_registry_number>
  <smiles>COC1=CC(=CC=C1O)C(O)CO</smiles>
  <inchi>InChI=1S/C9H12O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,10-12H,5H2,1H3</inchi>
  <inchikey>FBWPWWWZWKPJFL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Methoxyphenols</sub_class>
    <direct_parent>Methoxyphenols</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a guaiacol</external_descriptor>
      <external_descriptor>methoxybenzene</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-(4-hydroxy-3-methoxyphenyl)ethane-1,2-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>184.1892</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>184.073558872</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC(=CC=C1O)C(O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H12O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H12O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,10-12H,5H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FBWPWWWZWKPJFL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>69.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22915</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05594</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB030440</foodb_id>
  <chemspider_id>10348</chemspider_id>
  <pubchem_compound_id>10805</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>846276</chebi_id>
  <knapsack_id/>
  <wikipedia_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6274</metlin_id>
  <synthesis_reference>Kessler J A; Gordon E K; Reid J L; Kopin I J  Homovanillic acid and 3-methoxy-4-hydroxyphenylethyleneglycol production by the monkey spinal cord.    Journal of neurochemistry  (1976),  26(6),  1057-61.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:42 UTC</creation_date>
  <update_date>2020-04-16 17:51:41 UTC</update_date>
  <accession>BMDB0001491</accession>
  <secondary_accessions>
    <accession>BMDB01491</accession>
  </secondary_accessions>
  <name>Pyridoxal 5'-phosphate</name>
  <description>Pyridoxal 5'-phosphate, also known as phosphopyridoxal or PLP, belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively. Pyridoxal 5'-phosphate is a drug which is used for nutritional supplementation and for treating dietary shortage or imbalance. Pyridoxal 5'-phosphate exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Pyridoxal 5'-phosphate exists in all living species, ranging from bacteria to humans. In cattle, pyridoxal 5'-phosphate is involved in the metabolic pathway called the glycine and serine metabolism pathway. Pyridoxal 5'-phosphate is a potentially toxic compound. Pyridoxal 5'-phosphate has been found to be associated with several diseases known as rheumatoid arthritis, epilepsy, early-onset, vitamin b6-dependent, odontohypophosphatasia, and pyridoxamine 5-prime-phosphate oxidase deficiency; also pyridoxal 5'-phosphate has been linked to the inborn metabolic disorders including celiac disease.</description>
  <synonyms>
    <synonym>3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde</synonym>
    <synonym>3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate</synonym>
    <synonym>Codecarboxylase</synonym>
    <synonym>Phosphoric acid mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester</synonym>
    <synonym>PLP</synonym>
    <synonym>Pyridoxal 5'-(dihydrogen phosphate)</synonym>
    <synonym>Pyridoxal 5-monophosphoric acid ester</synonym>
    <synonym>Pyridoxal 5-phosphate</synonym>
    <synonym>Pyridoxal phosphate</synonym>
    <synonym>PYRIDOXAL-5'-phosphATE</synonym>
    <synonym>3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphoric acid</synonym>
    <synonym>Phosphate mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester</synonym>
    <synonym>Pyridoxal 5'-(dihydrogen phosphoric acid)</synonym>
    <synonym>Pyridoxal 5-monophosphate ester</synonym>
    <synonym>Pyridoxal 5-phosphoric acid</synonym>
    <synonym>Pyridoxal phosphoric acid</synonym>
    <synonym>PYRIDOXAL-5'-phosphoric acid</synonym>
    <synonym>Pyridoxal 5'-phosphoric acid</synonym>
    <synonym>Apolon b6</synonym>
    <synonym>Biosechs</synonym>
    <synonym>Coenzyme b6</synonym>
    <synonym>Hairoxal</synonym>
    <synonym>Hexermin-p</synonym>
    <synonym>Hi-pyridoxin</synonym>
    <synonym>Hiadelon</synonym>
    <synonym>Himitan</synonym>
    <synonym>PAL-p</synonym>
    <synonym>Phosphopyridoxal</synonym>
    <synonym>Phosphopyridoxal coenzyme</synonym>
    <synonym>Pidopidon</synonym>
    <synonym>Piodel</synonym>
    <synonym>Pydoxal</synonym>
    <synonym>Pyridoxal p</synonym>
    <synonym>Pyridoxal-p</synonym>
    <synonym>Pyridoxyl phosphate</synonym>
    <synonym>Pyromijin</synonym>
    <synonym>Sechvitan</synonym>
    <synonym>Vitahexin-p</synonym>
    <synonym>Vitazechs</synonym>
    <synonym>Phosphate, pyridoxal</synonym>
    <synonym>Pyridoxal 5 phosphate</synonym>
  </synonyms>
  <chemical_formula>C8H10NO6P</chemical_formula>
  <average_molecular_weight>247.1419</average_molecular_weight>
  <monisotopic_moleculate_weight>247.024573569</monisotopic_moleculate_weight>
  <iupac_name>[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid</iupac_name>
  <traditional_iupac>pyridoxal phosphate</traditional_iupac>
  <cas_registry_number>54-47-7</cas_registry_number>
  <smiles>CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O</smiles>
  <inchi>InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)</inchi>
  <inchikey>NGVDGCNFYWLIFO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyridine carboxaldehydes</sub_class>
    <direct_parent>Pyridoxals and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Aryl-aldehydes</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyridines</alternative_parent>
      <alternative_parent>Methylpyridines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aldehyde</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Aryl-aldehyde</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyridine</substituent>
      <substituent>Methylpyridine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Pyridoxal</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>methylpyridines</external_descriptor>
      <external_descriptor>monohydroxypyridine</external_descriptor>
      <external_descriptor>pyridinecarbaldehyde</external_descriptor>
      <external_descriptor>vitamin B6 phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>255 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>28 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>247.1419</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>247.024573569</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H10NO6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NGVDGCNFYWLIFO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>116.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Alanine Metabolism</name>
      <smpdb_id>SMP0087164</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Cysteine Metabolism</name>
      <smpdb_id>SMP0087189</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glucose-Alanine Cycle</name>
      <smpdb_id>SMP0087221</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Homocysteine Degradation</name>
      <smpdb_id>SMP0087201</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Malate-Aspartate Shuttle</name>
      <smpdb_id>SMP0087204</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Selenoamino Acid Metabolism</name>
      <smpdb_id>SMP0087161</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Sphingolipid Metabolism</name>
      <smpdb_id>SMP0087244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Taurine and Hypotaurine Metabolism</name>
      <smpdb_id>SMP0087214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Threonine and 2-Oxobutanoate Degradation</name>
      <smpdb_id>SMP0087262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin B6 Metabolism</name>
      <smpdb_id>SMP0087240</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438275</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438277</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438278</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439170</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.557 +/- 0.522</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Coburn SP, Mahuren JD, Pauly TA, Ericson KL, Townsend DW: Alkaline phosphatase activity and pyridoxal phosphate concentrations in the milk of various species. J Nutr. 1992 Dec;122(12):2348-53. doi: 10.1093/jn/122.12.2348.</reference_text>
          <pubmed_id>1453218</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00018</kegg_id>
  <drugbank_id>DB00114</drugbank_id>
  <foodb_id>FDB021820</foodb_id>
  <chemspider_id>1022</chemspider_id>
  <pubchem_compound_id>1051</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18405</chebi_id>
  <knapsack_id>C00007503</knapsack_id>
  <wikipedia_id>Pyridoxal_phosphate</wikipedia_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>33526</bigg_id>
  <metlin_id>6275</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Coburn SP, Mahuren JD, Pauly TA, Ericson KL, Townsend DW: Alkaline phosphatase activity and pyridoxal phosphate concentrations in the milk of various species. J Nutr. 1992 Dec;122(12):2348-53. doi: 10.1093/jn/122.12.2348.</reference_text>
      <pubmed_id>1453218</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00082</protein_accession>
      <name>Serine racemase</name>
      <uniprot_id>A0JNI4</uniprot_id>
      <gene_name>SRR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00083</protein_accession>
      <name>Serine hydroxymethyltransferase, mitochondrial</name>
      <uniprot_id>Q3SZ20</uniprot_id>
      <gene_name>SHMT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00085</protein_accession>
      <name>Serine palmitoyltransferase 1</name>
      <uniprot_id>Q3MHG1</uniprot_id>
      <gene_name>SPTLC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00087</protein_accession>
      <name>Serine hydroxymethyltransferase, cytosolic</name>
      <uniprot_id>Q5E9P9</uniprot_id>
      <gene_name>SHMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00088</protein_accession>
      <name>L-serine dehydratase</name>
      <uniprot_id>Q0VCW4</uniprot_id>
      <gene_name>SDS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00161</protein_accession>
      <name>Phosphorylase</name>
      <uniprot_id>B0JYK6</uniprot_id>
      <gene_name>PYGM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00214</protein_accession>
      <name>Pyridoxine-5'-phosphate oxidase</name>
      <uniprot_id>Q5E9K3</uniprot_id>
      <gene_name>PNPO</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00215</protein_accession>
      <name>Cysteine conjugate-beta lyase</name>
      <uniprot_id>A0JN49</uniprot_id>
      <gene_name>CCBL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00216</protein_accession>
      <name>Pyridoxal phosphate phosphatase</name>
      <uniprot_id>Q3ZBF9</uniprot_id>
      <gene_name>PDXP</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00217</protein_accession>
      <name>Similar to aspartate aminotransferase</name>
      <uniprot_id>Q862R2</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00218</protein_accession>
      <name>Similar to aspartate aminotransferase</name>
      <uniprot_id>Q862Q8</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00219</protein_accession>
      <name>Cytoplasmic cysteine conjugate-beta lyase</name>
      <uniprot_id>A5D991</uniprot_id>
      <gene_name>CCBL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00220</protein_accession>
      <name>Glutamate decarboxylase</name>
      <uniprot_id>B6A7R2</uniprot_id>
      <gene_name>GAD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00221</protein_accession>
      <name>MOSC domain-containing protein 2, mitochondrial</name>
      <uniprot_id>Q1LZH1</uniprot_id>
      <gene_name>MOSC2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00222</protein_accession>
      <name>4-aminobutyrate aminotransferase</name>
      <uniprot_id>A2VDK2</uniprot_id>
      <gene_name>ABAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00223</protein_accession>
      <name>Pyridoxal phosphate phosphatase PHOSPHO2</name>
      <uniprot_id>Q2KI06</uniprot_id>
      <gene_name>PHOSPHO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00224</protein_accession>
      <name>Glutamic-pyruvate transaminase</name>
      <uniprot_id>Q7YRA0</uniprot_id>
      <gene_name>GPT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00225</protein_accession>
      <name>1-aminocyclopropane-1-carboxylate synthase</name>
      <uniprot_id>Q0V8M2</uniprot_id>
      <gene_name>ACS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00226</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>A4IFQ7</uniprot_id>
      <gene_name>BCAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00227</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase, mitochondrial</name>
      <uniprot_id>Q5EA40</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00228</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>Q0V8J6</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00229</protein_accession>
      <name>Branched-chain-amino-acid aminotransferase</name>
      <uniprot_id>Q5E9U7</uniprot_id>
      <gene_name>BCAT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00239</protein_accession>
      <name>Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial</name>
      <uniprot_id>Q5E9N4</uniprot_id>
      <gene_name>AADAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00366</protein_accession>
      <name>2-amino-3-ketobutyrate coenzyme A ligase, mitochondrial</name>
      <uniprot_id>Q0P5L8</uniprot_id>
      <gene_name>GCAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00539</protein_accession>
      <name>Selenocysteine lyase</name>
      <uniprot_id>A2VDS1</uniprot_id>
      <gene_name>SCLY</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00561</protein_accession>
      <name>Histidine decarboxylase</name>
      <uniprot_id>Q5EA83</uniprot_id>
      <gene_name>HDC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00567</protein_accession>
      <name>Aspartate aminotransferase, cytoplasmic</name>
      <uniprot_id>P33097</uniprot_id>
      <gene_name>GOT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00569</protein_accession>
      <name>Aspartate aminotransferase, mitochondrial</name>
      <uniprot_id>P12344</uniprot_id>
      <gene_name>GOT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00571</protein_accession>
      <name>Putative aspartate aminotransferase, cytoplasmic 2</name>
      <uniprot_id>Q2T9S8</uniprot_id>
      <gene_name>GOT1L1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00596</protein_accession>
      <name>4-aminobutyrate aminotransferase, mitochondrial</name>
      <uniprot_id>Q9BGI0</uniprot_id>
      <gene_name>ABAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00624</protein_accession>
      <name>5-aminolevulinate synthase, nonspecific, mitochondrial</name>
      <uniprot_id>A6QLI6</uniprot_id>
      <gene_name>ALAS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00629</protein_accession>
      <name>5-aminolevulinate synthase, erythroid-specific, mitochondrial</name>
      <uniprot_id>Q3ZC31</uniprot_id>
      <gene_name>ALAS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00793</protein_accession>
      <name>Alanine--glyoxylate aminotransferase 2, mitochondrial</name>
      <uniprot_id>Q17QF0</uniprot_id>
      <gene_name>AGXT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00818</protein_accession>
      <name>Cystathionine gamma-lyase</name>
      <uniprot_id>Q58DW2</uniprot_id>
      <gene_name>CTH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00855</protein_accession>
      <name>Phosphoserine aminotransferase</name>
      <uniprot_id>A6QR28</uniprot_id>
      <gene_name>PSAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00858</protein_accession>
      <name>Alanine aminotransferase 1</name>
      <uniprot_id>A4IFH5</uniprot_id>
      <gene_name>GPT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00859</protein_accession>
      <name>Tyrosine aminotransferase</name>
      <uniprot_id>Q58CZ9</uniprot_id>
      <gene_name>TAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00861</protein_accession>
      <name>Kynurenine--oxoglutarate transaminase 3</name>
      <uniprot_id>Q0P5G4</uniprot_id>
      <gene_name>CCBL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00862</protein_accession>
      <name>Glutamate decarboxylase 1</name>
      <uniprot_id>Q0VCA1</uniprot_id>
      <gene_name>GAD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00922</protein_accession>
      <name>Ornithine decarboxylase</name>
      <uniprot_id>P27117</uniprot_id>
      <gene_name>ODC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00923</protein_accession>
      <name>Ornithine decarboxylase</name>
      <uniprot_id>Q2TBX3</uniprot_id>
      <gene_name>ADC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00936</protein_accession>
      <name>Aromatic-L-amino-acid decarboxylase</name>
      <uniprot_id>P27718</uniprot_id>
      <gene_name>DDC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01172</protein_accession>
      <name>Glycogen phosphorylase, brain form</name>
      <uniprot_id>Q3B7M9</uniprot_id>
      <gene_name>PYGB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01208</protein_accession>
      <name>Glycogen phosphorylase, liver form</name>
      <uniprot_id>Q0VCM4</uniprot_id>
      <gene_name>PYGL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01247</protein_accession>
      <name>Glycogen phosphorylase, muscle form</name>
      <uniprot_id>P79334</uniprot_id>
      <gene_name>PYGM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01327</protein_accession>
      <name>Ornithine aminotransferase, mitochondrial</name>
      <uniprot_id>Q3ZCF5</uniprot_id>
      <gene_name>OAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01361</protein_accession>
      <name>TAT protein</name>
      <uniprot_id>A6H7B2</uniprot_id>
      <gene_name>TAT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01362</protein_accession>
      <name>SPTLC2 protein</name>
      <uniprot_id>A5PKM3</uniprot_id>
      <gene_name>SPTLC2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01363</protein_accession>
      <name>Molybdenum cofactor sulfurase</name>
      <uniprot_id>Q9N0E7</uniprot_id>
      <gene_name>MOCOS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01364</protein_accession>
      <name>Pyridoxal-dependent decarboxylase domain-containing protein 1</name>
      <uniprot_id>A7MBC2</uniprot_id>
      <gene_name>PDXDC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01365</protein_accession>
      <name>CBS protein</name>
      <uniprot_id>A7MBF8</uniprot_id>
      <gene_name>CBS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01366</protein_accession>
      <name>Alanine--glyoxylate aminotransferase 2-like 1</name>
      <uniprot_id>Q5E9S4</uniprot_id>
      <gene_name>AGXT2L1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01367</protein_accession>
      <name>AGXT protein</name>
      <uniprot_id>A7MBF1</uniprot_id>
      <gene_name>AGXT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01368</protein_accession>
      <name>NFS1 protein</name>
      <uniprot_id>A5PKG4</uniprot_id>
      <gene_name>NFS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01369</protein_accession>
      <name>1-aminocyclopropane-1-carboxylate synthase-like protein 1</name>
      <uniprot_id>Q5E9H2</uniprot_id>
      <gene_name>ACCS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01370</protein_accession>
      <name>Serum albumin</name>
      <uniprot_id>P02769</uniprot_id>
      <gene_name>ALB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01371</protein_accession>
      <name>SDSL protein</name>
      <uniprot_id>A5PKH5</uniprot_id>
      <gene_name>SDSL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01372</protein_accession>
      <name>Proline synthetase co-transcribed bacterial homolog protein</name>
      <uniprot_id>Q3T0G5</uniprot_id>
      <gene_name>PROSC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01373</protein_accession>
      <name>CTH protein</name>
      <uniprot_id>B0JYP8</uniprot_id>
      <gene_name>CTH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01374</protein_accession>
      <name>DDC protein</name>
      <uniprot_id>A5PJV5</uniprot_id>
      <gene_name>DDC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01375</protein_accession>
      <name>SGPL1 protein</name>
      <uniprot_id>A5D788</uniprot_id>
      <gene_name>SGPL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01376</protein_accession>
      <name>Glutamate decarboxylase-like protein 1</name>
      <uniprot_id>A6QM00</uniprot_id>
      <gene_name>GADL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:43 UTC</creation_date>
  <update_date>2020-04-16 20:39:25 UTC</update_date>
  <accession>BMDB0001492</accession>
  <secondary_accessions>
    <accession>BMDB01492</accession>
  </secondary_accessions>
  <name>Gamma-Tocopherol</name>
  <description>Gamma-Tocopherol, also known as vitaplus e or DL-alpha-tocopherol, belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. Gamma-Tocopherol exists as a liquid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule.</description>
  <synonyms>
    <synonym>DL-alpha-Tocopherol</synonym>
    <synonym>DL-a-Tocopherol</synonym>
    <synonym>DL-Α-tocopherol</synonym>
    <synonym>g-Tocopherol</synonym>
    <synonym>Γ-tocopherol</synonym>
    <synonym>3,4-Dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol</synonym>
    <synonym>7,8-Dimethyltocol</synonym>
    <synonym>7,8-Dimethyltocolo-xylotocopherol</synonym>
    <synonym>Methyltocols</synonym>
    <synonym>O-Xylotocopherol</synonym>
    <synonym>Tocopherol</synonym>
    <synonym>Tocopherols</synonym>
    <synonym>Vitamin e gamma</synonym>
    <synonym>Bioweyxin</synonym>
    <synonym>e-Mulsin</synonym>
    <synonym>Embial</synonym>
    <synonym>GNR-Pharma brand OF tocopherol actetate</synonym>
    <synonym>Organon brand OF tocopherol acetate</synonym>
    <synonym>Schwarzhaupt brand OF tocopherol acetate</synonym>
    <synonym>Snow-e muscle, energy and feritility</synonym>
    <synonym>Spondyvit</synonym>
    <synonym>Tocolion</synonym>
    <synonym>Tocopherol rodisma-med brand</synonym>
    <synonym>Tocopherol worwag brand</synonym>
    <synonym>Togasan vitamin e</synonym>
    <synonym>Unique e</synonym>
    <synonym>Vibolex</synonym>
    <synonym>Vita-e</synonym>
    <synonym>Vitamin e dragees</synonym>
    <synonym>Atarost brand OF tocopherol acetate</synonym>
    <synonym>Biocur brand OF tocopherol acetate</synonym>
    <synonym>Cambridge laboratories brand OF tocopherol actetate</synonym>
    <synonym>Dal e</synonym>
    <synonym>Detulin</synonym>
    <synonym>e Vitamin e</synonym>
    <synonym>EVI-mirale, vitamin-e</synonym>
    <synonym>Elex verla</synonym>
    <synonym>Eplonat</synonym>
    <synonym>Richelet brand OF tocopherol acetate</synonym>
    <synonym>Roche nicholas brand OF tocopherol acetate</synonym>
    <synonym>Rodisma med brand OF tocopherol</synonym>
    <synonym>Sciencex brand OF tocopherol acetate</synonym>
    <synonym>Steigerwald brand OF tocopherol acetate</synonym>
    <synonym>Strathmann brand OF tocopherol</synonym>
    <synonym>Tocopherol grunwalder brand</synonym>
    <synonym>Tocopherol stadapharm brand</synonym>
    <synonym>Verla brand OF tocopherol</synonym>
    <synonym>Vit. e stada</synonym>
    <synonym>VitaPlus e</synonym>
    <synonym>Vitamin-e evi-mirale</synonym>
    <synonym>Vitamine e GNR</synonym>
    <synonym>Vitazell</synonym>
    <synonym>Worwag brand OF tocopherol</synonym>
    <synonym>Alcala brand OF tocopherol acetate</synonym>
    <synonym>Bio e</synonym>
    <synonym>Biopto-e</synonym>
    <synonym>e Vicotrat</synonym>
    <synonym>e-Ferol</synonym>
    <synonym>EUNOVA vitamin e</synonym>
    <synonym>Equivit e</synonym>
    <synonym>Evion</synonym>
    <synonym>Internation animal health brand OF tocopherol acetate</synonym>
    <synonym>MIP brand OF tocopherol acetate</synonym>
    <synonym>Sanum-kehlbeck brand OF tocopherol actetate</synonym>
    <synonym>Tocopherol infirmarius-rovit brand</synonym>
    <synonym>Tocopherol twardy brand</synonym>
    <synonym>Tocovital</synonym>
    <synonym>Vitamin-e dragees</synonym>
    <synonym>Wiedemann brand OF tocopherol</synonym>
    <synonym>Abortosan</synonym>
    <synonym>Arkopharma brand OF tocopherol acetate</synonym>
    <synonym>Dal vita brand OF vitamin e succinate</synonym>
    <synonym>Eu rho brand OF tocopherol</synonym>
    <synonym>Eusovit</synonym>
    <synonym>Infirmarius-rovit brand OF tocopherol</synonym>
    <synonym>Richtavit e</synonym>
    <synonym>Riemser brand OF tocopherol</synonym>
    <synonym>Tocopherol ausrichter brand</synonym>
    <synonym>Tocopherol balkanpharma brand</synonym>
    <synonym>Vitagutt vitamin e</synonym>
    <synonym>Vitamin e natur</synonym>
    <synonym>Vitamin e, togasan</synonym>
    <synonym>Ratiopharm brand OF tocopherol</synonym>
    <synonym>Aliud brand OF tocopherol</synonym>
    <synonym>Bottger brand OF tocopherol acetate</synonym>
    <synonym>Dermorelle</synonym>
    <synonym>e Ferol</synonym>
    <synonym>e-Vitamin-ratiopharm</synonym>
    <synonym>Heyl brand OF tocopherol acetate</synonym>
    <synonym>Kohler brand OF tocopherol</synonym>
    <synonym>Lasar</synonym>
    <synonym>Puncto e</synonym>
    <synonym>Rodisma-med brand OF tocopherol</synonym>
    <synonym>Sanum kehlbeck brand OF tocopherol actetate</synonym>
    <synonym>Scot tussin brand OF tocopherol acetate</synonym>
    <synonym>Stadapharm brand OF tocopherol</synonym>
    <synonym>Tocopa</synonym>
    <synonym>Tocopherol bayer</synonym>
    <synonym>Tocopherol grace brand</synonym>
    <synonym>Tocopherol ratiopharm brand</synonym>
    <synonym>Twardy brand OF tocopherol</synonym>
    <synonym>Uno vit</synonym>
    <synonym>Uno-vit</synonym>
    <synonym>Veyx brand OF tocopherol</synonym>
    <synonym>Vit e hydrosol</synonym>
    <synonym>Vita e</synonym>
    <synonym>Vitamin e al</synonym>
    <synonym>Wiedemann brand OF vitamin e succinate</synonym>
    <synonym>Ausrichter brand OF tocopherol</synonym>
    <synonym>Auxina e</synonym>
    <synonym>Balkanpharma brand OF tocopherol</synonym>
    <synonym>Blackmores brand OF tocopherol</synonym>
    <synonym>Dal-e</synonym>
    <synonym>Davitamon</synonym>
    <synonym>e-Vicotrat</synonym>
    <synonym>Ecoro</synonym>
    <synonym>Ephynal</synonym>
    <synonym>Grunwalder brand OF tocopherol</synonym>
    <synonym>ICN brand OF tocopherol acetate</synonym>
    <synonym>Mucos brand OF tocopherol acetate</synonym>
    <synonym>Tocopherol togal brand</synonym>
    <synonym>Tocopherol verla brand</synonym>
    <synonym>Togal brand OF tocopherol</synonym>
    <synonym>Troyapharm brand OF tocopherol acetate</synonym>
    <synonym>Vita-plus e</synonym>
    <synonym>Vitamin e sanum</synonym>
    <synonym>Vitamin e MP</synonym>
    <synonym>Vitamin emp</synonym>
    <synonym>Woelm brand OF tocopherol acetate</synonym>
    <synonym>Bayer brand OF tocopherol acetate</synonym>
    <synonym>GNR Pharma brand OF tocopherol actetate</synonym>
    <synonym>Grace brand OF tocopherol</synonym>
    <synonym>Malton e</synonym>
    <synonym>Merck brand OF tocopherol acetate</synonym>
    <synonym>Mowivit vitamin e</synonym>
    <synonym>Tocopherol wiedemann brand</synonym>
    <synonym>UnoVit</synonym>
    <synonym>Vitamin e evi mirale</synonym>
    <synonym>Vitamin e suspension</synonym>
    <synonym>Vitamin e, mowivit</synonym>
    <synonym>Vitamin e, vitagutt</synonym>
    <synonym>Vitamin e-MP</synonym>
    <synonym>Adisseo brand OF tocopherol</synonym>
    <synonym>Antioxidans e-hevert</synonym>
    <synonym>Aquasol e</synonym>
    <synonym>AstraZeneca brand OF tocopherol acetate</synonym>
    <synonym>Biosan</synonym>
    <synonym>Dal-vita brand OF vitamin e succinate</synonym>
    <synonym>Dragees, vitamin-e</synonym>
    <synonym>e Mulsin</synonym>
    <synonym>Hervert brand OF tocopherol acetate</synonym>
    <synonym>Hydrovit e</synonym>
    <synonym>Infirmarius rovit brand OF tocopherol</synonym>
    <synonym>Jenapharm brand OF tocopherol</synonym>
    <synonym>Kentucky brand OF tocopherol</synonym>
    <synonym>Micorvit e</synonym>
    <synonym>Sanavitan S</synonym>
    <synonym>Scot-tussin brand OF tocopherol acetate</synonym>
    <synonym>Tocopharm</synonym>
    <synonym>Tocopherol kentucky brand</synonym>
    <synonym>Vita plus e</synonym>
    <synonym>VitaE</synonym>
    <synonym>Medphano brand OF tocopherol acetate</synonym>
    <synonym>VitaminE evimirale</synonym>
  </synonyms>
  <chemical_formula>C28H48O2</chemical_formula>
  <average_molecular_weight>416.6795</average_molecular_weight>
  <monisotopic_moleculate_weight>416.36543078</monisotopic_moleculate_weight>
  <iupac_name>2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol</iupac_name>
  <traditional_iupac>2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-1-benzopyran-6-ol</traditional_iupac>
  <cas_registry_number>10191-41-0</cas_registry_number>
  <smiles>CC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=CC(O)=C(C)C(C)=C2O1</smiles>
  <inchi>InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3</inchi>
  <inchikey>QUEDXNHFTDJVIY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Quinone and hydroquinone lipids</sub_class>
    <direct_parent>Tocopherols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-benzopyrans</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Diterpenoids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-benzopyran</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzopyran</substituent>
      <substituent>Chromane</substituent>
      <substituent>Diterpenoid</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Tocopherol</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>vitamin E</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>128 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>8.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>9.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>416.6795</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>416.36543078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CCCC(C)CCCC(C)CCCC1(C)CCC2=CC(O)=C(C)C(C)=C2O1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C28H48O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QUEDXNHFTDJVIY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>29.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>130.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>54.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>81432</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>81433</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>81434</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142541</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0264 +/- 0.00720</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Holstein. corn silage with concentrates</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0744 +/- 0.00960</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Holstein. Diet: grass silage with concentates</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB002431</foodb_id>
  <chemspider_id>14266</chemspider_id>
  <pubchem_compound_id>14986</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>298402</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007365</knapsack_id>
  <bigg_id>2296479</bigg_id>
  <wikipedia_id>Gamma-Tocopherol</wikipedia_id>
  <metlin_id>6276</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
      <pubmed_id>27999311</pubmed_id>
    </reference>
    <reference>
      <reference_text>International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP02253</protein_accession>
      <name>SEC14-like protein 2</name>
      <uniprot_id>P58875</uniprot_id>
      <gene_name>SEC14L2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:44 UTC</creation_date>
  <update_date>2020-03-13 16:28:24 UTC</update_date>
  <accession>BMDB0001493</accession>
  <secondary_accessions>
    <accession>BMDB01493</accession>
  </secondary_accessions>
  <name>3-Methylcrotonyl-CoA</name>
  <description/>
  <synonyms>
    <synonym>3-Methylbut-2-enoyl-CoA</synonym>
    <synonym>3-Methylbut-2-enoyl-coenzyme A</synonym>
    <synonym>3-Methylcrotonoyl-CoA</synonym>
    <synonym>3-Methylcrotonoyl-coenzyme A</synonym>
    <synonym>3-Methylcrotonyl-coenzyme A</synonym>
    <synonym>b-Methylcrotonyl-CoA (HMDB01493</synonym>
    <synonym>b-Methylcrotonyl-coenzyme A (HMDB01493</synonym>
    <synonym>beta-Methylcrotonoyl-CoA</synonym>
    <synonym>beta-Methylcrotonoyl-coenzyme A</synonym>
    <synonym>beta-Methylcrotonyl-CoA (HMDB01493</synonym>
    <synonym>beta-Methylcrotonyl-coenzyme A (HMDB01493</synonym>
    <synonym>Dimethylacryloyl-CoA</synonym>
    <synonym>Dimethylacryloyl-coenzyme A</synonym>
  </synonyms>
  <chemical_formula>C26H42N7O17P3S</chemical_formula>
  <average_molecular_weight>849.635</average_molecular_weight>
  <monisotopic_moleculate_weight>849.157073179</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-methylbut-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-methylbut-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>793193-48-3</cas_registry_number>
  <smiles>CC(C)=CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C26H42N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h9,12-13,15,19-21,25,36-37H,5-8,10-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21?,25-/m1/s1</inchi>
  <inchikey>BXIPALATIYNHJN-TVCSPYKZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-methylbut-2-enoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>849.635</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>849.157073179</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)=CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C26H42N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C26H42N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h9,12-13,15,19-21,25,36-37H,5-8,10-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21?,25-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BXIPALATIYNHJN-TVCSPYKZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>186.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>75.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25224</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31783</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>388909</chemspider_id>
  <foodb_id>FDB022652</foodb_id>
  <drugbank_id/>
  <kegg_id>C03069</kegg_id>
  <chebi_id>15486</chebi_id>
  <pubchem_compound_id>439869</pubchem_compound_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>41135</bigg_id>
  <wikipedia_id>Methylcrotonyl-CoA</wikipedia_id>
  <metlin_id>6277</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:46 UTC</creation_date>
  <update_date>2020-04-14 22:49:16 UTC</update_date>
  <accession>BMDB0001494</accession>
  <secondary_accessions>
    <accession>BMDB01494</accession>
  </secondary_accessions>
  <name>Acetylphosphate</name>
  <description/>
  <synonyms>
    <synonym>Acetic acid, monoanhydride with phosphoric acid</synonym>
    <synonym>Acetyl phosphate</synonym>
    <synonym>Acetylphosphoric acid</synonym>
    <synonym>Monoacetyl phosphate</synonym>
    <synonym>Acetate, monoanhydride with phosphate</synonym>
    <synonym>Acetyl phosphoric acid</synonym>
    <synonym>Monoacetyl phosphoric acid</synonym>
    <synonym>Acetyl-p</synonym>
  </synonyms>
  <chemical_formula>C2H5O5P</chemical_formula>
  <average_molecular_weight>140.0319</average_molecular_weight>
  <monisotopic_moleculate_weight>139.987459782</monisotopic_moleculate_weight>
  <iupac_name>(acetyloxy)phosphonic acid</iupac_name>
  <traditional_iupac>acetylphosphate</traditional_iupac>
  <cas_registry_number>590-54-5</cas_registry_number>
  <smiles>CC(=O)OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C2H5O5P/c1-2(3)7-8(4,5)6/h1H3,(H2,4,5,6)</inchi>
  <inchikey>LIPOUNRJVLNBCD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure  R-CO-P(O)(O)OH, R=H or organyl.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic phosphoric acids and derivatives</class>
    <sub_class>Phosphate esters</sub_class>
    <direct_parent>Acyl monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetate salts</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetate salt</substituent>
      <substituent>Acyl monophosphate</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid salt</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>acyl monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(acetyloxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>140.0319</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>139.987459782</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H5O5P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H5O5P/c1-2(3)7-8(4,5)6/h1H3,(H2,4,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LIPOUNRJVLNBCD-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>83.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>23.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277244</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>181</chemspider_id>
  <foodb_id>FDB022653</foodb_id>
  <drugbank_id>DB02897</drugbank_id>
  <kegg_id>C00227</kegg_id>
  <chebi_id>15350</chebi_id>
  <pubchem_compound_id>186</pubchem_compound_id>
  <pdbe_id/>
  <knapsack_id>C00019559</knapsack_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6278</metlin_id>
  <synthesis_reference>Costakel, O.; Kitzoulesco, I.  The possibility of acetylphosphate synthesis in cancerous and noncancerous human serum at pH 4.    Rev. sci. Med., Acad. rep. populaire Roumaine  (1960),  5  7-10.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:47 UTC</creation_date>
  <update_date>2020-04-15 22:26:28 UTC</update_date>
  <accession>BMDB0001495</accession>
  <secondary_accessions>
    <accession>BMDB01495</accession>
  </secondary_accessions>
  <name>Queuine</name>
  <description/>
  <synonyms>
    <synonym>2-Amino-5-((((1S,4S,5R)-4,5-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-1,7-dihydro-4H-pyrrolo(2,3-D)pyrimidin-4-one</synonym>
    <synonym>7-(3,4-trans-4,5-cis-Dihydroxy-1-cyclopenten-3-ylaminomethyl)-7-deazaguanine</synonym>
    <synonym>Base Q</synonym>
  </synonyms>
  <chemical_formula>C12H15N5O3</chemical_formula>
  <average_molecular_weight>277.2792</average_molecular_weight>
  <monisotopic_moleculate_weight>277.117489371</monisotopic_moleculate_weight>
  <iupac_name>5-({[(1R,4R,5S)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-2-imino-1H,2H,3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one</iupac_name>
  <traditional_iupac>5-({[(1R,4R,5S)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-2-imino-1H,3H,7H-pyrrolo[2,3-d]pyrimidin-4-one</traditional_iupac>
  <cas_registry_number>72496-59-4</cas_registry_number>
  <smiles>O[C@@H]1C=C[C@@H](NCC2=CNC3=C2C(=O)NC(=N)N3)[C@@H]1O</smiles>
  <inchi>InChI=1S/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)/t6-,7-,9+/m1/s1</inchi>
  <inchikey>WYROLENTHWJFLR-BHNWBGBOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrrolo[2,3-d]pyrimidines. These are aromatic heteropolycyclic compounds containing a pyrrolo[2,3-d]pyrimidine ring system, which is an pyrrolopyrimidine isomers having the 3 ring nitrogen atoms at the 1-, 5-, and 7-positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyrrolopyrimidines</class>
    <sub_class>Pyrrolo[2,3-d]pyrimidines</sub_class>
    <direct_parent>Pyrrolo[2,3-d]pyrimidines</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Pyrrolo[2,3-d]pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Substituted pyrrole</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>7.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-({[(1R,4R,5S)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-2-imino-1H,2H,3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>277.2792</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>277.117489371</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]1C=C[C@@H](NCC2=CNC3=C2C(=O)NC(=N)N3)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H15N5O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H15N5O3/c13-12-16-10-8(11(20)17-12)5(4-15-10)3-14-6-1-2-7(18)9(6)19/h1-2,4,6-7,9,14,18-19H,3H2,(H4,13,15,16,17,20)/t6-,7-,9+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WYROLENTHWJFLR-BHNWBGBOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>133.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>83.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>27.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>310035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354607</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354609</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id/>
  <foodb_id>FDB022654</foodb_id>
  <drugbank_id/>
  <kegg_id>C01449</kegg_id>
  <chebi_id>17433</chebi_id>
  <pubchem_compound_id>53477731</pubchem_compound_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Queuine</wikipedia_id>
  <metlin_id>6279</metlin_id>
  <synthesis_reference>Akimoto, Hiroshi; Imamiya, Eiko; Hitaka, Takenori; Nomura, Hiroaki; Nishimura, Susumu. Synthesis of queuine, the base of naturally occurring hypermodified nucleoside (queuosine), and its analogs. Journal of the Chemical Society, Perkin Transactions 1: Org</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:48 UTC</creation_date>
  <update_date>2020-03-13 16:28:26 UTC</update_date>
  <accession>BMDB0001496</accession>
  <secondary_accessions>
    <accession>BMDB01496</accession>
  </secondary_accessions>
  <name>7a-Hydroxycholesterol</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C27H46O2</chemical_formula>
  <average_molecular_weight>402.663</average_molecular_weight>
  <monisotopic_moleculate_weight>402.349780721</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,9S,10R,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol</iupac_name>
  <traditional_iupac>(1S,2R,5S,9S,10R,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@]2([H])[C@@]3([H])[C@]([H])(O)C=C4C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C</smiles>
  <inchi>InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22-,23+,24-,25-,26+,27-/m1/s1</inchi>
  <inchikey>OYXZMSRRJOYLLO-WIFYNPISSA-N</inchikey>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,9S,10R,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>402.663</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>402.349780721</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@]2([H])[C@@]3([H])[C@]([H])(O)C=C4C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H46O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22-,23+,24-,25-,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OYXZMSRRJOYLLO-WIFYNPISSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>122.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>50.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1296139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1296140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1296141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1410787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1410788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1410789</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id/>
  <pdbe_id/>
  <kegg_id/>
  <chebi_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:49 UTC</creation_date>
  <update_date>2020-04-16 20:39:26 UTC</update_date>
  <accession>BMDB0001497</accession>
  <secondary_accessions>
    <accession>BMDB01497</accession>
  </secondary_accessions>
  <name>Nicotine-1'-N-oxide</name>
  <description/>
  <synonyms>
    <synonym>1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olate</synonym>
    <synonym>3-(1-Methyl-1-oxidopyrrolidin-2-yl)pyridine</synonym>
    <synonym>Nicotine 1-N-oxide</synonym>
    <synonym>1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olic acid</synonym>
    <synonym>(1's,2's)-Nicotine-n'-oxide</synonym>
    <synonym>(2S)-N-Oxide 3-(1-methyl-2-pyrrolidinyl)-pyridine</synonym>
    <synonym>1'-Oxide nicotine</synonym>
    <synonym>1-Methyl-2-(3-pyridyl)pyrrolidine 1-oxide</synonym>
    <synonym>3-(1-Methyl-1-oxido-2-pyrrolidinyl)pyridine</synonym>
    <synonym>N-Oxide 3-(1-methyl-2-pyrrolidinyl)pyridine</synonym>
    <synonym>N-Oxide-(1-methyl-2-pyrrolidinyl)pyridine</synonym>
    <synonym>Nicotine 1'-oxide</synonym>
    <synonym>Nicotine n'-oxide</synonym>
    <synonym>Nicotine N(1')-oxide</synonym>
    <synonym>Nicotine-1'-oxide</synonym>
    <synonym>Nicotine 1-N-oxide, (R)-isomer</synonym>
    <synonym>Nicotine 1-N-oxide, dihydrochloride, (S)-isomer</synonym>
    <synonym>Nicotine 1-N-oxide, (1S-cis)-isomer</synonym>
    <synonym>Nicotine 1-N-oxide, (1S-trans)-isomer</synonym>
    <synonym>Nicotine 1-N-oxide, (2S)-isomer</synonym>
    <synonym>Nicotine 1-N-oxide, 14C-labeled CPD</synonym>
    <synonym>Nicotine 1-N-oxide, dihydrochloride, (1S-trans)-isomer</synonym>
    <synonym>Nicotine 1-N-oxide, (1R-cis)-isomer</synonym>
    <synonym>Nicotine 1-N-oxide, (1R-trans)-isomer</synonym>
    <synonym>Nicotine 1-N-oxide, (S)-isomer</synonym>
    <synonym>Nicotine 1-N-oxide, dihydrochloride, (1R-trans)-isomer</synonym>
  </synonyms>
  <chemical_formula>C10H14N2O</chemical_formula>
  <average_molecular_weight>178.231</average_molecular_weight>
  <monisotopic_moleculate_weight>178.11061308</monisotopic_moleculate_weight>
  <iupac_name>1-methyl-2-(pyridin-3-yl)pyrrolidin-1-ium-1-olate</iupac_name>
  <traditional_iupac>nicotine 1-N-oxide</traditional_iupac>
  <cas_registry_number>63551-14-4</cas_registry_number>
  <smiles>C[N+]1([O-])CCCC1C1=CN=CC=C1</smiles>
  <inchi>InChI=1S/C10H14N2O/c1-12(13)7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3</inchi>
  <inchikey>RWFBQHICRCUQJJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyrrolidinylpyridines</sub_class>
    <direct_parent>Pyrrolidinylpyridines</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-alkylpyrrolidines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Trialkyl amine oxides</alternative_parent>
      <alternative_parent>Trisubstituted amine oxides and derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-alkylpyrrolidine</substituent>
      <substituent>N-oxide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidinylpyridine</substituent>
      <substituent>Trialkyl amine oxide</substituent>
      <substituent>Trisubstituted n-oxide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>pyrrolidine N-oxide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-79 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.17</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.038</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-methyl-2-(pyridin-3-yl)pyrrolidin-1-ium-1-olate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>178.231</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>178.11061308</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+]1([O-])CCCC1C1=CN=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H14N2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H14N2O/c1-12(13)7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RWFBQHICRCUQJJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>39.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314005</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>314007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>359640</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>396</chemspider_id>
  <foodb_id>FDB022656</foodb_id>
  <drugbank_id/>
  <kegg_id/>
  <chebi_id>30734</chebi_id>
  <pubchem_compound_id>409</pubchem_compound_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:51 UTC</creation_date>
  <update_date>2020-04-15 22:32:59 UTC</update_date>
  <accession>BMDB0001498</accession>
  <secondary_accessions>
    <accession>BMDB01498</accession>
  </secondary_accessions>
  <name>Inositol 1,4,5-trisphosphate</name>
  <description/>
  <synonyms>
    <synonym>1,4,5-Insp3</synonym>
    <synonym>D-Myo-inositol 1,4,5-trisphosphate</synonym>
    <synonym>D-MYO-inositol-1,4,5-triphosphATE</synonym>
    <synonym>Ins(1,4,5)P3</synonym>
    <synonym>InsP3</synonym>
    <synonym>IP3</synonym>
    <synonym>1D-Myo-inositol 1,4,5-trisphosphate</synonym>
    <synonym>D-Myo-inositol 1,4,5-trisphosphoric acid</synonym>
    <synonym>D-MYO-inositol-1,4,5-triphosphoric acid</synonym>
    <synonym>1D-Myo-inositol 1,4,5-trisphosphoric acid</synonym>
    <synonym>Inositol 1,4,5-trisphosphoric acid</synonym>
    <synonym>Myo-inositol 1,4,5-trisphosphate</synonym>
    <synonym>1,4,5-IP3</synonym>
    <synonym>Inositol 1,4,5-triphosphate</synonym>
    <synonym>Myoinositol 1,4,5-triphosphate</synonym>
  </synonyms>
  <chemical_formula>C6H15O15P3</chemical_formula>
  <average_molecular_weight>420.0956</average_molecular_weight>
  <monisotopic_moleculate_weight>419.962379346</monisotopic_moleculate_weight>
  <iupac_name>{[(1R,2S,3R,4R,5S,6R)-2,3,5-trihydroxy-4,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>InsP3</traditional_iupac>
  <cas_registry_number>88269-39-0</cas_registry_number>
  <smiles>O[C@@H]1[C@H](O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H](O)[C@@H]1OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C6H15O15P3/c7-1-2(8)5(20-23(13,14)15)6(21-24(16,17)18)3(9)4(1)19-22(10,11)12/h1-9H,(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)/t1-,2+,3+,4-,5-,6-/m1/s1</inchi>
  <inchikey>MMWCIQZXVOZEGG-XJTPDSDZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as inositol phosphates. Inositol phosphates are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Inositol phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclohexanols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Cyclohexanol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Inositol phosphate</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>myo-inositol trisphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(1R,2S,3R,4R,5S,6R)-2,3,5-trihydroxy-4,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>420.0956</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>419.962379346</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]1[C@H](O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H](O)[C@@H]1OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H15O15P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H15O15P3/c7-1-2(8)5(20-23(13,14)15)6(21-24(16,17)18)3(9)4(1)19-22(10,11)12/h1-9H,(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)/t1-,2+,3+,4-,5-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MMWCIQZXVOZEGG-XJTPDSDZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>260.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Activation of PKC Through G Protein-Coupled Receptor</name>
      <smpdb_id>SMP0108001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>BCR Signaling Pathway</name>
      <smpdb_id>SMP0120940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>EGF Signalling Pathway</name>
      <smpdb_id>SMP0120924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fc Epsilon Receptor I Signaling in Mast Cells</name>
      <smpdb_id>SMP0108186</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>G-Protein Signaling Through Tubby Proteins</name>
      <smpdb_id>SMP0120943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histamine H1 Receptor Activation</name>
      <smpdb_id>SMP0108002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Metabolism</name>
      <smpdb_id>SMP0087242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Inositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ion Channel and Phorbal Esters Signaling Pathway</name>
      <smpdb_id>SMP0120945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA1 Signalling</name>
      <smpdb_id>SMP0108191</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA2 Signalling</name>
      <smpdb_id>SMP0108193</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA3 Signalling</name>
      <smpdb_id>SMP0108194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA4 Signalling</name>
      <smpdb_id>SMP0108196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysophosphatidic Acid LPA5 Signalling</name>
      <smpdb_id>SMP0108198</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Muscle/Heart Contraction</name>
      <smpdb_id>SMP0119378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylinositol Phosphate Metabolism</name>
      <smpdb_id>SMP0087258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>T Cell Receptor Signaling Pathway </name>
      <smpdb_id>SMP0120935</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180623</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>388562</chemspider_id>
  <foodb_id>FDB022657</foodb_id>
  <drugbank_id>DB03401</drugbank_id>
  <kegg_id>C01245</kegg_id>
  <chebi_id>16595</chebi_id>
  <pubchem_compound_id>439456</pubchem_compound_id>
  <pdbe_id/>
  <knapsack_id>C00007460</knapsack_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>1485108</bigg_id>
  <wikipedia_id>Inositol trisphosphate</wikipedia_id>
  <metlin_id>6282</metlin_id>
  <synthesis_reference>Cooke, Allan M.; Potter, Barry V. L.; Gigg, Roy. Synthesis of DL-myo-inositol 1,4,5-trisphosphate. Tetrahedron Letters (1987), 28(20), 2305-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00072</protein_accession>
      <name>1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase beta-1</name>
      <uniprot_id>P10894</uniprot_id>
      <gene_name>PLCB1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00073</protein_accession>
      <name>1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase delta-4</name>
      <uniprot_id>P21671</uniprot_id>
      <gene_name>PLCD4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00074</protein_accession>
      <name>1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase zeta-1</name>
      <uniprot_id>Q1RML2</uniprot_id>
      <gene_name>PLCZ1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00075</protein_accession>
      <name>1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase delta-1</name>
      <uniprot_id>P10895</uniprot_id>
      <gene_name>PLCD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00076</protein_accession>
      <name>1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase gamma-1</name>
      <uniprot_id>P08487</uniprot_id>
      <gene_name>PLCG1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00077</protein_accession>
      <name>1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase beta-4</name>
      <uniprot_id>Q07722</uniprot_id>
      <gene_name>PLCB4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01330</protein_accession>
      <name>Myosin-Ic</name>
      <uniprot_id>Q27966</uniprot_id>
      <gene_name>MYO1C</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01334</protein_accession>
      <name>Inositol 1,4,5-trisphosphate receptor type 2</name>
      <uniprot_id>Q8WN96</uniprot_id>
      <gene_name>ITPR2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01335</protein_accession>
      <name>Prostaglandin D2 receptor</name>
      <uniprot_id>A5D7K8</uniprot_id>
      <gene_name>PTGDR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01336</protein_accession>
      <name>Erlin-2</name>
      <uniprot_id>Q1RMU4</uniprot_id>
      <gene_name>ERLIN2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01337</protein_accession>
      <name>Inositol 1,4,5-trisphosphate receptor type 1</name>
      <uniprot_id>Q9TU34</uniprot_id>
      <gene_name>ITPR1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01338</protein_accession>
      <name>Inositol 1,4,5-trisphosphate receptor type 3</name>
      <uniprot_id>Q8WN95</uniprot_id>
      <gene_name>ITPR3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:52 UTC</creation_date>
  <update_date>2020-03-13 16:28:27 UTC</update_date>
  <accession>BMDB0001499</accession>
  <secondary_accessions>
    <accession>BMDB01499</accession>
  </secondary_accessions>
  <name>GDP-D-Rhamnose</name>
  <description/>
  <synonyms>
    <synonym>GDP-6-Deoxy-D-mannose</synonym>
    <synonym>GDP-6-Deoxy-alpha-D-mannose</synonym>
    <synonym>GDP-alpha-D-Rhamnose</synonym>
    <synonym>GDP-6-Deoxy-a-D-mannose</synonym>
    <synonym>GDP-6-Deoxy-α-D-mannose</synonym>
    <synonym>GDP-a-D-Rhamnose</synonym>
    <synonym>GDP-Α-D-rhamnose</synonym>
    <synonym>GDP-6-Deoxy-alpha-delta-mannose</synonym>
    <synonym>GDP-6-Deoxy-delta-mannose</synonym>
    <synonym>GDP-delta-Rhamnose</synonym>
    <synonym>Guanosine-5-diphosphate-rhamnose</synonym>
    <synonym>GDP-Rhamnose</synonym>
    <synonym>Guanosine diphosphate rhamnose</synonym>
    <synonym>Guanosine-5'-diphosphoric acid-rhamnose</synonym>
    <synonym>GDP-D-Rhamnose</synonym>
  </synonyms>
  <chemical_formula>C16H25N5O15P2</chemical_formula>
  <average_molecular_weight>589.3417</average_molecular_weight>
  <monisotopic_moleculate_weight>589.082238179</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphinic acid</traditional_iupac>
  <cas_registry_number>15839-74-4</cas_registry_number>
  <smiles>C[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(N)=NC3=O)[C@@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1</inchi>
  <inchikey>LQEBEXMHBLQMDB-GDJBGNAASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine nucleotide sugars</sub_class>
    <direct_parent>Purine nucleotide sugars</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>GDP-sugar</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>589.3417</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>589.082238179</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(N)=NC3=O)[C@@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H25N5O15P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LQEBEXMHBLQMDB-GDJBGNAASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>307.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>116.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>49.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271469</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>388945</chemspider_id>
  <foodb_id>FDB022658</foodb_id>
  <drugbank_id>DB02547</drugbank_id>
  <kegg_id>C03117</kegg_id>
  <chebi_id>17661</chebi_id>
  <pubchem_compound_id>439912</pubchem_compound_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6283</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:53 UTC</creation_date>
  <update_date>2020-03-13 16:28:28 UTC</update_date>
  <accession>BMDB0001501</accession>
  <secondary_accessions>
    <accession>BMDB01501</accession>
  </secondary_accessions>
  <name>Guanosine diphosphate adenosine</name>
  <description/>
  <synonyms>
    <synonym>Guanosine diphosphoric acid adenosine</synonym>
    <synonym>{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonate</synonym>
  </synonyms>
  <chemical_formula>C20H26N10O14P2</chemical_formula>
  <average_molecular_weight>692.4266</average_molecular_weight>
  <monisotopic_moleculate_weight>692.110518614</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3R,4R,5R)-4-[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3R,4R,5R)-4-({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>65331-78-4</cas_registry_number>
  <smiles>NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)O[C@@H]2[C@@H](CO)O[C@H]([C@@H]2OP(O)(O)=O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C20H26N10O14P2/c21-14-8-15(24-3-23-14)29(4-25-8)19-13(43-45(35,36)37)12(6(1-31)41-19)44-46(38,39)40-2-7-10(32)11(33)18(42-7)30-5-26-9-16(30)27-20(22)28-17(9)34/h3-7,10-13,18-19,31-33H,1-2H2,(H,38,39)(H2,21,23,24)(H2,35,36,37)(H3,22,27,28,34)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1</inchi>
  <inchikey>LHSVDZHIRYSVJP-INFSMZHSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (3'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (3'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(3'-&gt;5')-dinucleotides and analogues</class>
    <sub_class>(3'-&gt;5')-dinucleotides</sub_class>
    <direct_parent>(3'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Dialkyl phosphates</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(3'-&gt;5')-dinucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Dialkyl phosphate</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3R,4R,5R)-4-[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>692.4266</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>692.110518614</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)O[C@@H]2[C@@H](CO)O[C@H]([C@@H]2OP(O)(O)=O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H26N10O14P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H26N10O14P2/c21-14-8-15(24-3-23-14)29(4-25-8)19-13(43-45(35,36)37)12(6(1-31)41-19)44-46(38,39)40-2-7-10(32)11(33)18(42-7)30-5-26-9-16(30)27-20(22)28-17(9)34/h3-7,10-13,18-19,31-33H,1-2H2,(H,38,39)(H2,21,23,24)(H2,35,36,37)(H3,22,27,28,34)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LHSVDZHIRYSVJP-INFSMZHSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>356.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>145.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>58.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>328161</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022659</foodb_id>
  <chemspider_id>8637730</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>10462318</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:54 UTC</creation_date>
  <update_date>2020-03-13 16:28:29 UTC</update_date>
  <accession>BMDB0001504</accession>
  <secondary_accessions>
    <accession>BMDB01504</accession>
  </secondary_accessions>
  <name>Aminoparathion</name>
  <description/>
  <synonyms>
    <synonym>Amino-parathion</synonym>
    <synonym>AP</synonym>
  </synonyms>
  <chemical_formula>C10H16NO3PS</chemical_formula>
  <average_molecular_weight>261.278</average_molecular_weight>
  <monisotopic_moleculate_weight>261.058850585</monisotopic_moleculate_weight>
  <iupac_name>O-4-aminophenyl O,O-diethyl phosphorothioate</iupac_name>
  <traditional_iupac>O-4-aminophenyl O,O-diethyl phosphorothioate</traditional_iupac>
  <cas_registry_number>3735-01-1</cas_registry_number>
  <smiles>CCOP(=S)(OCC)OC1=CC=C(N)C=C1</smiles>
  <inchi>InChI=1S/C10H16NO3PS/c1-3-12-15(16,13-4-2)14-10-7-5-9(11)6-8-10/h5-8H,3-4,11H2,1-2H3</inchi>
  <inchikey>XIZOTXGJXSTQDI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic thiophosphoric acids and derivatives</class>
    <sub_class>Thiophosphoric acid esters</sub_class>
    <direct_parent>Phenyl thiophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Thiophosphate triesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenyl thiophosphate</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Thiophosphate triester</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>organothiophosphate insecticide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>0.39 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.6</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>O-4-aminophenyl O,O-diethyl phosphorothioate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>261.278</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>261.058850585</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCOP(=S)(OCC)OC1=CC=C(N)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H16NO3PS</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H16NO3PS/c1-3-12-15(16,13-4-2)14-10-7-5-9(11)6-8-10/h5-8H,3-4,11H2,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XIZOTXGJXSTQDI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>53.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>70.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370071</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022660</foodb_id>
  <chemspider_id>215</chemspider_id>
  <kegg_id>C06605</kegg_id>
  <pubchem_compound_id>220</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>2657</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6284</metlin_id>
  <synthesis_reference>Rung, Bruno; Schwack, Wolfgang.  Aminoparathion: A highly reactive metabolite of parathion. 1. Reactions with polyphenols and polyphenol oxidase.    Journal of Agricultural and Food Chemistry  (2005),  53(23),  9140-9145.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:55 UTC</creation_date>
  <update_date>2020-03-13 16:28:29 UTC</update_date>
  <accession>BMDB0001507</accession>
  <secondary_accessions>
    <accession>BMDB01507</accession>
  </secondary_accessions>
  <name>Diguanosine diphosphate</name>
  <description/>
  <synonyms>
    <synonym>Diguanosine diphosphoric acid</synonym>
    <synonym>Guanosine 5'-diphospho-5'-guanosine</synonym>
    <synonym>{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinate</synonym>
  </synonyms>
  <chemical_formula>C20H26N10O15P2</chemical_formula>
  <average_molecular_weight>708.426</average_molecular_weight>
  <monisotopic_moleculate_weight>708.105433236</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic acid</traditional_iupac>
  <cas_registry_number>34692-44-9</cas_registry_number>
  <smiles>NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(N)=NC3=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C20H26N10O15P2/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(43-17)1-41-46(37,38)45-47(39,40)42-2-6-10(32)12(34)18(44-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1</inchi>
  <inchikey>LFEYGVXBDRXHGF-MHARETSRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside diphosphates. These are purine nucleotides with diphosphate group  linked to the ribose moiety lacking a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine deoxyribonucleotides</sub_class>
    <direct_parent>Purine 2'-deoxyribonucleoside diphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine 2'-deoxyribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>708.426</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>708.105433236</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(N)=NC3=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H26N10O15P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H26N10O15P2/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(43-17)1-41-46(37,38)45-47(39,40)42-2-6-10(32)12(34)18(44-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LFEYGVXBDRXHGF-MHARETSRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>372.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>146.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>61.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>64921</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304057</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304058</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347166</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022661</foodb_id>
  <chemspider_id>167649</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>193190</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id>86S</pdbe_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:57 UTC</creation_date>
  <update_date>2020-04-15 22:33:00 UTC</update_date>
  <accession>BMDB0001508</accession>
  <secondary_accessions>
    <accession>BMDB01508</accession>
  </secondary_accessions>
  <name>dADP</name>
  <description/>
  <synonyms>
    <synonym>[({[(2R,3S,5S)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonate</synonym>
  </synonyms>
  <chemical_formula>C10H15N5O9P2</chemical_formula>
  <average_molecular_weight>411.204</average_molecular_weight>
  <monisotopic_moleculate_weight>411.034501079</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,5S)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>{[(2R,3S,5S)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@]1(O)C[C@]([H])(O[C@]1([H])COP(O)(=O)OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12</smiles>
  <inchi>InChI=1S/C10H15N5O9P2/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(23-7)2-22-26(20,21)24-25(17,18)19/h3-7,16H,1-2H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)/t5-,6+,7-/m0/s1</inchi>
  <inchikey>DAEAPNUQQAICNR-XVMARJQXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside diphosphates. These are purine nucleotides with diphosphate group  linked to the ribose moiety lacking a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine deoxyribonucleotides</sub_class>
    <direct_parent>Purine 2'-deoxyribonucleoside diphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxolanes</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxolane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine 2'-deoxyribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,5S)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>411.204</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>411.034501079</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@]1(O)C[C@]([H])(O[C@]1([H])COP(O)(=O)OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H15N5O9P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H15N5O9P2/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(23-7)2-22-26(20,21)24-25(17,18)19/h3-7,16H,1-2H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)/t5-,6+,7-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DAEAPNUQQAICNR-XVMARJQXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>212.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>83.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1315204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1315205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1315206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1429678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1429679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1429680</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <drugbank_id/>
  <pubchem_compound_id>92436381</pubchem_compound_id>
  <kegg_id/>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Deoxyadenosine diphosphate</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Nara, Takashi; Misawa, Masanaru.  Bacterial phosphorylation of 5'-deoxyadenosine monophosphate to di- or triphosphate.    Jpn. Tokkyo Koho  (1971),     2 pp. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:58 UTC</creation_date>
  <update_date>2020-03-13 16:28:30 UTC</update_date>
  <accession>BMDB0001509</accession>
  <secondary_accessions>
    <accession>BMDB01509</accession>
  </secondary_accessions>
  <name>20-Hydroxy-leukotriene B4</name>
  <description/>
  <synonyms>
    <synonym>(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyeicosa-6,8,10,14-tetraenoate</synonym>
    <synonym>(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoate</synonym>
    <synonym>20-Hydroxy-LTB4</synonym>
    <synonym>20-OH-Leukotriene b4</synonym>
    <synonym>20-OH-LTB4</synonym>
    <synonym>(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyeicosa-6,8,10,14-tetraenoic acid</synonym>
    <synonym>(6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoic acid</synonym>
    <synonym>(5S,12R)-5,12,20-Trihydroxy-(6Z,8E,10E,14Z)-eicosatetraenoate</synonym>
    <synonym>(5S,12R)-5,12,20-Trihydroxy-(6Z,8E,10E,14Z)-eicosatetraenoic acid</synonym>
    <synonym>(5S,6Z,8E,10E,12R,14Z)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoate</synonym>
    <synonym>(5S,6Z,8E,10E,12R,14Z)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoic acid</synonym>
    <synonym>20-Hydroxy LTB4</synonym>
    <synonym>20-Hydroxyleukotriene b4</synonym>
    <synonym>20-OH-5S,12S-Dihydroxy-6,10-trans-8,14-cis-eicosatetraenoate</synonym>
    <synonym>20-OH-5S,12S-Dihydroxy-6,10-trans-8,14-cis-eicosatetraenoic acid</synonym>
    <synonym>5,12,20-THETE</synonym>
    <synonym>5,12,20-TriHETE</synonym>
    <synonym>5S,12R,20-Trihydroxy-6Z,8E,10E,14Z-eicosatetraenoate</synonym>
    <synonym>5S,12R,20-Trihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid</synonym>
    <synonym>Omega-hydroxy-LTB4</synonym>
    <synonym>W-Hydroxy-LTB4</synonym>
    <synonym>[S-[R*,s*-(e,Z,e,Z)]]-5,12,20-trihydroxy-6,8,10,14-eicosatetraenoate</synonym>
    <synonym>[S-[R*,s*-(e,Z,e,Z)]]-5,12,20-trihydroxy-6,8,10,14-eicosatetraenoic acid</synonym>
    <synonym>20-Hydroxy-leukotriene b</synonym>
    <synonym>5,12,20-Trihydroxy-6,8,10,14-eicosatetraenoic acid</synonym>
    <synonym>5,12,20-Trihydroxy-6,8,10,14-eicosatetraenoic acid, (S-(r*,s*-(e,Z,e,Z)))-isomer</synonym>
  </synonyms>
  <chemical_formula>C20H32O5</chemical_formula>
  <average_molecular_weight>352.4651</average_molecular_weight>
  <monisotopic_moleculate_weight>352.224974134</monisotopic_moleculate_weight>
  <iupac_name>(5S,6Z,8E,10E,12R,14Z)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid</iupac_name>
  <traditional_iupac>20-hydroxy-LTB4</traditional_iupac>
  <cas_registry_number>79516-82-8</cas_registry_number>
  <smiles>OCCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H32O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1</inchi>
  <inchikey>PTJFJXLGRSTECQ-PSPARDEHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Leukotrienes</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Hydroxyeicosatetraenoic acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Hydroxyeicosatetraenoic acid</substituent>
      <substituent>Leukotriene</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Leukotrienes</external_descriptor>
      <external_descriptor>Leukotrienes</external_descriptor>
      <external_descriptor>hydroxy monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5S,6Z,8E,10E,12R,14Z)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>352.4651</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>352.224974134</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H32O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H32O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PTJFJXLGRSTECQ-PSPARDEHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>104.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arachidonic Acid Metabolism</name>
      <smpdb_id>SMP0087220</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>60174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>60175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>60176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>116469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>116470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>116471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435511</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022663</foodb_id>
  <chemspider_id>4444320</chemspider_id>
  <kegg_id>C04853</kegg_id>
  <pubchem_compound_id>5280745</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>15646</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6287</metlin_id>
  <synthesis_reference>Zamboni, Robert; Rokach, Joshua.  Stereospecific synthesis of two metabolites of LTB4.    Tetrahedron Letters  (1982),  23(46),  4751-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:46:59 UTC</creation_date>
  <update_date>2020-04-15 22:15:23 UTC</update_date>
  <accession>BMDB0001510</accession>
  <secondary_accessions>
    <accession>BMDB01510</accession>
  </secondary_accessions>
  <name>Bupropion</name>
  <description/>
  <synonyms>
    <synonym>(+-)-Bupropion</synonym>
    <synonym>Amfebutamona</synonym>
    <synonym>Amfebutamone</synonym>
    <synonym>Amfebutamonum</synonym>
    <synonym>Wellbatrin</synonym>
    <synonym>Wellbutrin</synonym>
    <synonym>Zyban</synonym>
    <synonym>Bupropion hydrochloride</synonym>
    <synonym>Bupropion, (+-)-isomer</synonym>
    <synonym>Glaxo wellcome brand 1 OF bupropion hydrochloride</synonym>
    <synonym>Glaxo wellcome brand 3 OF bupropion hydrochloride</synonym>
    <synonym>Zyban (anti-smoking)</synonym>
    <synonym>GlaxoSmithKline brand 2 OF bupropion hydrochloride</synonym>
    <synonym>(+-)-1-(3-Chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone</synonym>
    <synonym>Esteve brand OF bupropion hydrochloride</synonym>
    <synonym>Glaxo wellcome brand 2 OF bupropion hydrochloride</synonym>
    <synonym>Bupropion hydrochloride, (+-)-isomer</synonym>
    <synonym>GlaxoSmithKline brand 1 OF bupropion hydrochloride</synonym>
    <synonym>Quomen</synonym>
    <synonym>Zyntabac</synonym>
    <synonym>Zyban (bupropion)</synonym>
  </synonyms>
  <chemical_formula>C13H18ClNO</chemical_formula>
  <average_molecular_weight>239.741</average_molecular_weight>
  <monisotopic_moleculate_weight>239.10769191</monisotopic_moleculate_weight>
  <iupac_name>2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one</iupac_name>
  <traditional_iupac>bupropion</traditional_iupac>
  <cas_registry_number>34841-39-9</cas_registry_number>
  <smiles>CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1</smiles>
  <inchi>InChI=1S/C13H18ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,15H,1-4H3</inchi>
  <inchikey>SNPPWIUOZRMYNY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Alkyl-phenylketones</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-amino ketones</alternative_parent>
      <alternative_parent>Aryl alkyl ketones</alternative_parent>
      <alternative_parent>Aryl chlorides</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Chlorobenzenes</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylpropanes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkyl-phenylketone</substituent>
      <substituent>Alpha-aminoketone</substituent>
      <substituent>Amine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl alkyl ketone</substituent>
      <substituent>Aryl chloride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Chlorobenzene</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylpropane</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aromatic ketone</external_descriptor>
      <external_descriptor>monochlorobenzenes</external_descriptor>
      <external_descriptor>propanone</external_descriptor>
      <external_descriptor>secondary amino compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>239.741</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>239.10769191</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H18ClNO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H18ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,15H,1-4H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SNPPWIUOZRMYNY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>29.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>67.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>65016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>65017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>65018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122327</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442893</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442894</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442904</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442906</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452393</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022664</foodb_id>
  <chemspider_id>431</chemspider_id>
  <kegg_id>C06860</kegg_id>
  <pubchem_compound_id>444</pubchem_compound_id>
  <drugbank_id>DB01156</drugbank_id>
  <chebi_id>3219</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>CPD-3481</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Bupropion</wikipedia_id>
  <metlin_id>1435</metlin_id>
  <synthesis_reference>Xia, Min; Xu, Bao-feng. Study on synthesis of the amfebutamone hydrochloride. Shandong Huagong (2003), 32(3), 3-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:00 UTC</creation_date>
  <update_date>2020-04-16 20:40:39 UTC</update_date>
  <accession>BMDB0001511</accession>
  <secondary_accessions>
    <accession>BMDB01511</accession>
  </secondary_accessions>
  <name>Phosphocreatine</name>
  <description>Phosphocreatine, also known as creatine-p or neo-ton, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Phosphocreatine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Phosphocreatine exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>Creatine phosphate</synonym>
    <synonym>Creatine phosphic acid</synonym>
    <synonym>N-(N-Phosphonoamido)sarcosine</synonym>
    <synonym>N-(Phosphonoamidino)sarcosine</synonym>
    <synonym>N-Phosphorylcreatine</synonym>
    <synonym>N(Omega)-phosphonocreatine</synonym>
    <synonym>Phosphorylcreatine</synonym>
    <synonym>{[imino(phosphonoamino)methyl](methyl)amino}acetic acid</synonym>
    <synonym>N-Phosphocreatine</synonym>
    <synonym>Creatine phosphoric acid</synonym>
    <synonym>{[imino(phosphonoamino)methyl](methyl)amino}acetate</synonym>
    <synonym>Creatine-p</synonym>
    <synonym>Creatine-phosphate</synonym>
    <synonym>Creatinephosphoric acid</synonym>
    <synonym>N-(Phosphonoamidino)-sarcosine</synonym>
    <synonym>N-Phosphorocreatine</synonym>
    <synonym>N-[Imino(phosphonoamino)methyl]-N-methyl-glycine</synonym>
    <synonym>Neo-ton</synonym>
    <synonym>p-Creatine</synonym>
  </synonyms>
  <chemical_formula>C4H10N3O5P</chemical_formula>
  <average_molecular_weight>211.1131</average_molecular_weight>
  <monisotopic_moleculate_weight>211.035806957</monisotopic_moleculate_weight>
  <iupac_name>2-(N-methyl-N'-phosphonocarbamimidamido)acetic acid</iupac_name>
  <traditional_iupac>creatine-phosphate</traditional_iupac>
  <cas_registry_number>67-07-2</cas_registry_number>
  <smiles>CN(CC(O)=O)C(=N)NP(O)(O)=O</smiles>
  <inchi>InChI=1S/C4H10N3O5P/c1-7(2-3(8)9)4(5)6-13(10,11)12/h2H2,1H3,(H,8,9)(H4,5,6,10,11,12)</inchi>
  <inchikey>DRBBFCLWYRJSJZ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Guanidines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic phosphoric acids and derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>phosphagen</external_descriptor>
      <external_descriptor>phosphoamino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>13.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(N-methyl-N'-phosphonocarbamimidamido)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>211.1131</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>211.035806957</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN(CC(O)=O)C(=N)NP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H10N3O5P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H10N3O5P/c1-7(2-3(8)9)4(5)6-13(10,11)12/h2H2,1H3,(H,8,9)(H4,5,6,10,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DRBBFCLWYRJSJZ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>133.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>53.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5368</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>250532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451958</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>60.35 +/- 28.96</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>50 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>46 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>59 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>49.33 +/- 52.66</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>38.24 +/- 39.15</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from 20 healthy Holstein Friesian dairy cows </comment>
      <references>
        <reference>
          <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
          <pubmed_id>23738862</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022665</foodb_id>
  <chemspider_id>567</chemspider_id>
  <kegg_id>C02305</kegg_id>
  <pubchem_compound_id>587</pubchem_compound_id>
  <drugbank_id>DB13191</drugbank_id>
  <chebi_id>17287</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>CREATINE-P</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>1594794</bigg_id>
  <wikipedia_id>Phosphocreatine</wikipedia_id>
  <metlin_id>6288</metlin_id>
  <synthesis_reference>Hou, Lixiang.  Method for producing creatine phosphate.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2004),     7 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
      <pubmed_id>23738862</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00255</protein_accession>
      <name>Creatine kinase S-type, mitochondrial</name>
      <uniprot_id>Q3ZBP1</uniprot_id>
      <gene_name>CKMT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00256</protein_accession>
      <name>Creatine kinase B-type</name>
      <uniprot_id>Q5EA61</uniprot_id>
      <gene_name>CKB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00257</protein_accession>
      <name>Creatine kinase U-type, mitochondrial</name>
      <uniprot_id>Q9TTK8</uniprot_id>
      <gene_name>CKMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00258</protein_accession>
      <name>Creatine kinase M-type</name>
      <uniprot_id>Q9XSC6</uniprot_id>
      <gene_name>CKM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:01 UTC</creation_date>
  <update_date>2020-03-13 16:28:32 UTC</update_date>
  <accession>BMDB0001512</accession>
  <secondary_accessions>
    <accession>BMDB01512</accession>
  </secondary_accessions>
  <name>Thiamin triphosphate</name>
  <description>Thiamine triphosphate, also known as thiamine triphosphate or THTP, belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group. Thiamine triphosphate is possibly soluble (in water) and a very strong basic compound (based on its pKa). Thiamine triphosphate exists in all living species, ranging from bacteria to humans. Thiamine triphosphate participates in a number of enzymatic reactions, within cattle. In particular, Thiamine triphosphate can be biosynthesized from thiamine pyrophosphate through its interaction with the enzyme thiamin pyrophosphokinase. In addition, Thiamine triphosphate can be converted into thiamine pyrophosphate through the action of the enzyme thiamine-triphosphatase. In cattle, thiamine triphosphate is involved in the metabolic pathway called the thiamine metabolism pathway.</description>
  <synonyms>
    <synonym>Thiamin triphosphate</synonym>
    <synonym>Thiamin triphosphoric acid</synonym>
    <synonym>Thiamine triphosphoric acid</synonym>
    <synonym>THTP</synonym>
    <synonym>Triphosphate, thiamin</synonym>
    <synonym>Triphosphate, thiamine</synonym>
  </synonyms>
  <chemical_formula>C12H20N4O10P3S</chemical_formula>
  <average_molecular_weight>505.294</average_molecular_weight>
  <monisotopic_moleculate_weight>505.011298106</monisotopic_moleculate_weight>
  <iupac_name>3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium</iupac_name>
  <traditional_iupac>thiamin triphosphate</traditional_iupac>
  <cas_registry_number>3475-65-8</cas_registry_number>
  <smiles>CC1=C(CCOP(O)(=O)OP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=C(N)N=C(C)N=C1</smiles>
  <inchi>InChI=1S/C12H19N4O10P3S/c1-8-11(30-7-16(8)6-10-5-14-9(2)15-12(10)13)3-4-24-28(20,21)26-29(22,23)25-27(17,18)19/h5,7H,3-4,6H2,1-2H3,(H5-,13,14,15,17,18,19,20,21,22,23)/p+1</inchi>
  <inchikey>IWLROWZYZPNOFC-UHFFFAOYSA-O</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazines</class>
    <sub_class>Pyrimidines and pyrimidine derivatives</sub_class>
    <direct_parent>Thiamine phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>4,5-disubstituted thiazoles</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>4,5-disubstituted 1,3-thiazole</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Thiamine-phosphate</substituent>
      <substituent>Thiazole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>1,3-thiazolium cation</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>505.294</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>505.011298106</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCOP(O)(=O)OP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=C(N)N=C(C)N=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H20N4O10P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H19N4O10P3S/c1-8-11(30-7-16(8)6-10-5-14-9(2)15-12(10)13)3-4-24-28(20,21)26-29(22,23)25-27(17,18)19/h5,7H,3-4,6H2,1-2H3,(H5-,13,14,15,17,18,19,20,21,22,23)/p+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IWLROWZYZPNOFC-UHFFFAOYSA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>215.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>106.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>41.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Thiamine Metabolism</name>
      <smpdb_id>SMP0087212</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181544</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03028</kegg_id>
  <foodb_id>FDB022666</foodb_id>
  <drugbank_id/>
  <chemspider_id>496</chemspider_id>
  <pdbe_id/>
  <chebi_id>9534</chebi_id>
  <pubchem_compound_id>511</pubchem_compound_id>
  <meta_cyc_id/>
  <wikipedia_id>Thiamine triphosphate</wikipedia_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>41046</bigg_id>
  <metlin_id>3586</metlin_id>
  <synthesis_reference>Grandfils C; Bettendorff L; de Rycker C; Schoffeniels E  Synthesis of [gamma-32P]thiamine triphosphate.    Analytical biochemistry  (1988),  169(2),  274-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01243</protein_accession>
      <name>Thiamine-triphosphatase</name>
      <uniprot_id>Q8MKF1</uniprot_id>
      <gene_name>THTPA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:02 UTC</creation_date>
  <update_date>2020-03-13 16:28:32 UTC</update_date>
  <accession>BMDB0001513</accession>
  <secondary_accessions>
    <accession>BMDB01513</accession>
  </secondary_accessions>
  <name>Dolichyl diphosphate</name>
  <description/>
  <synonyms>
    <synonym>Dolichyl diphosphoric acid</synonym>
    <synonym>[({[(7E)-3,8-dimethyldec-7-en-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonate</synonym>
  </synonyms>
  <chemical_formula>C12H26O7P2</chemical_formula>
  <average_molecular_weight>344.2782</average_molecular_weight>
  <monisotopic_moleculate_weight>344.11537621</monisotopic_moleculate_weight>
  <iupac_name>[({[(7E)-3,8-dimethyldec-7-en-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>{[(7E)-3,8-dimethyldec-7-en-1-yl]oxy(hydroxy)phosphoryl}oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>37247-98-6</cas_registry_number>
  <smiles>CC\C(C)=C\CCCC(C)CCOP(O)(=O)OP(O)(O)=O</smiles>
  <inchi>InChI=1S/C12H26O7P2/c1-4-11(2)7-5-6-8-12(3)9-10-18-21(16,17)19-20(13,14)15/h7,12H,4-6,8-10H2,1-3H3,(H,16,17)(H2,13,14,15)/b11-7+</inchi>
  <inchikey>FFBTVOMODCZDNV-YRNVUSSQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organic oxoanionic compounds</class>
    <sub_class>Organic pyrophosphates</sub_class>
    <direct_parent>Organic pyrophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(7E)-3,8-dimethyldec-7-en-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>344.2782</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>344.11537621</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC\C(C)=C\CCCC(C)CCOP(O)(=O)OP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H26O7P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H26O7P2/c1-4-11(2)7-5-6-8-12(3)9-10-18-21(16,17)19-20(13,14)15/h7,12H,4-6,8-10H2,1-3H3,(H,16,17)(H2,13,14,15)/b11-7+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FFBTVOMODCZDNV-YRNVUSSQSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>113.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>81.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307508</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>307509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>351474</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022667</foodb_id>
  <chemspider_id>13748633</chemspider_id>
  <drugbank_id/>
  <pubchem_compound_id>5462166</pubchem_compound_id>
  <kegg_id>C00621</kegg_id>
  <pdbe_id/>
  <chebi_id>15750</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6290</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00841</protein_accession>
      <name>Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit DAD1</name>
      <uniprot_id>Q5E9C2</uniprot_id>
      <gene_name>DAD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00842</protein_accession>
      <name>Dolichyl-diphosphooligosaccharide--protein glycosyltransferase 48 kDa subunit</name>
      <uniprot_id>A6QPY0</uniprot_id>
      <gene_name>DDOST</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00843</protein_accession>
      <name>Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit 2</name>
      <uniprot_id>Q3SZI6</uniprot_id>
      <gene_name>RPN2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00844</protein_accession>
      <name>Dolichyl-diphosphooligosaccharide--protein glycosyltransferase subunit STT3A</name>
      <uniprot_id>Q2KJI2</uniprot_id>
      <gene_name>STT3A</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:03 UTC</creation_date>
  <update_date>2020-04-15 22:28:34 UTC</update_date>
  <accession>BMDB0001514</accession>
  <secondary_accessions>
    <accession>BMDB01514</accession>
  </secondary_accessions>
  <name>Glucosamine</name>
  <description>Glucosamine, also known as dona or chitosamine, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Glucosamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Glucosamine exists in all living organisms, ranging from bacteria to humans. Glucosamine can be converted into glucosamine 6-phosphate; which is mediated by the enzyme hexokinase-1. In cattle, glucosamine is involved in the metabolic pathway called the amino sugar metabolism pathway.</description>
  <synonyms>
    <synonym>2-Amino-2-deoxy-D-glucose</synonym>
    <synonym>Chitosamine</synonym>
    <synonym>D-Glucosamine</synonym>
    <synonym>(+)-2-Amino-2-deoxy-D-glucopyranose</synonym>
    <synonym>(3R,4R,5S,6R)-3-Amino-6-(hydroxymethyl)oxane-2,4,5-triol</synonym>
    <synonym>2-Amino-2-deoxy-D-glucopyranose</synonym>
    <synonym>2-Amino-2-deoxyglucose</synonym>
    <synonym>2-Aminoglucose</synonym>
    <synonym>2-Deoxy-2-amino-D-glucose</synonym>
    <synonym>2-Deoxy-2-aminoglucose</synonym>
    <synonym>Cosamin</synonym>
    <synonym>D-(+)-Glucosamine</synonym>
    <synonym>Dona</synonym>
    <synonym>Fides ecopharma brand OF glucosamine sulfate</synonym>
    <synonym>Rottapharm brand OF glucosamine sulfate</synonym>
    <synonym>Xicil</synonym>
    <synonym>2 Amino 2 deoxyglucose</synonym>
    <synonym>Glucosamine sulfate</synonym>
    <synonym>Sulfate, glucosamine</synonym>
    <synonym>Dona S</synonym>
    <synonym>Opfermann brand OF glucosamine sulfate</synonym>
    <synonym>Hespercorbin</synonym>
  </synonyms>
  <chemical_formula>C6H13NO5</chemical_formula>
  <average_molecular_weight>179.1711</average_molecular_weight>
  <monisotopic_moleculate_weight>179.079372531</monisotopic_moleculate_weight>
  <iupac_name>(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol</iupac_name>
  <traditional_iupac>glucosamine</traditional_iupac>
  <cas_registry_number>3416-24-8</cas_registry_number>
  <smiles>N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1</inchi>
  <inchikey>MSWZFWKMSRAUBD-IVMDWMLBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Hexoses</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Aminosaccharides</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino saccharide</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Amino sugars</external_descriptor>
      <external_descriptor>D-glucosamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.73</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.49</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>179.1711</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>179.079372531</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13NO5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MSWZFWKMSRAUBD-IVMDWMLBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>116.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>75216</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>75217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>75218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>134817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>134818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>134819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218132</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By GC-TOFMS and UPLC-QTOFMS</comment>
      <references>
        <reference>
          <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
          <pubmed_id>27999311</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>388352</chemspider_id>
  <foodb_id>FDB022668</foodb_id>
  <kegg_id>C00329</kegg_id>
  <pubchem_compound_id>439213</pubchem_compound_id>
  <drugbank_id>DB01296</drugbank_id>
  <chebi_id>47977</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>34633</bigg_id>
  <wikipedia_id>Glucosamine</wikipedia_id>
  <metlin_id>266</metlin_id>
  <synthesis_reference>Li, Nan; Li, Jiheng.  Preparation of D-glucosamine hydrochloride.    Zhongguo Yaoke Daxue Xuebao  (1997),  28(1),  56-58.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
      <pubmed_id>27999311</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:05 UTC</creation_date>
  <update_date>2020-04-15 22:31:21 UTC</update_date>
  <accession>BMDB0001517</accession>
  <secondary_accessions>
    <accession>BMDB01517</accession>
  </secondary_accessions>
  <name>AICAR</name>
  <description/>
  <synonyms>
    <synonym>1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide</synonym>
    <synonym>5'-Phospho-ribosyl-5-amino-4-imidazole carboxamide</synonym>
    <synonym>5'-Phosphoribosyl-5-amino-4-imidazolecarboxamide</synonym>
    <synonym>5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide</synonym>
    <synonym>5-Aminoimidazole-4-carboxamide ribotide</synonym>
    <synonym>5-Phosphoribosyl-4-carbamoyl-5-aminoimidazole</synonym>
    <synonym>Acadesine 5'-monophosphate</synonym>
    <synonym>AICA-Ribonucleotide</synonym>
    <synonym>5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide</synonym>
    <synonym>Acadesine 5'-monophosphoric acid</synonym>
    <synonym>5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamide</synonym>
    <synonym>5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamide</synonym>
    <synonym>5'-p-Ribosyl-5-amino-4-imidazole carboxamide</synonym>
    <synonym>5'-Phosphoribosyl-5-amino-4-imidazole carboxamide</synonym>
    <synonym>5-Amino-4-imidazolecarboxamide ribotide</synonym>
    <synonym>AICA Ribonucleotide</synonym>
    <synonym>Aminoimidazole carboxamide ribonucleotide</synonym>
    <synonym>Z-Nucleotide</synonym>
    <synonym>4-Carboxy-5-aminoimidazole ribotide</synonym>
    <synonym>5-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide monophosphate</synonym>
    <synonym>5-Amino-4-imidazolecarboxamide ribofuranoside 5'-monophosphate</synonym>
    <synonym>AICA Ribonucleotide, (D-ribofuranosyl)-isomer</synonym>
    <synonym>AICAriboside 5'-monophosphate</synonym>
    <synonym>CAIR</synonym>
    <synonym>ZMP</synonym>
  </synonyms>
  <chemical_formula>C9H15N4O8P</chemical_formula>
  <average_molecular_weight>338.2112</average_molecular_weight>
  <monisotopic_moleculate_weight>338.062749988</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>aica ribonucleotide</traditional_iupac>
  <cas_registry_number>3031-94-5</cas_registry_number>
  <smiles>NC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1</inchi>
  <inchikey>NOTGFIUVDGNKRI-UUOKFMHZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Imidazole ribonucleosides and ribonucleotides</class>
    <sub_class>1-ribosyl-imidazolecarboxamides</sub_class>
    <direct_parent>1-ribosyl-imidazolecarboxamides</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>2-heteroaryl carboxamides</alternative_parent>
      <alternative_parent>Amino acids and derivatives</alternative_parent>
      <alternative_parent>Aminoimidazoles</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonylimidazoles</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>1-ribosyl-imidazolecarboxamide</substituent>
      <substituent>2-heteroaryl carboxamide</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminoimidazole</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazole-4-carbonyl group</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>1-(phosphoribosyl)imidazolecarboxamide</external_descriptor>
      <external_descriptor>aminoimidazole</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.08</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>338.2112</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>338.062749988</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H15N4O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NOTGFIUVDGNKRI-UUOKFMHZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>203.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>69.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>24637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>31195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437236</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448130</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>58620</chemspider_id>
  <pubchem_compound_id>65110</pubchem_compound_id>
  <chebi_id>18406</chebi_id>
  <drugbank_id>DB01700</drugbank_id>
  <pdbe_id/>
  <kegg_id>C04677</kegg_id>
  <foodb_id>FDB030675</foodb_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007383</knapsack_id>
  <bigg_id>44312</bigg_id>
  <wikipedia_id>AICA_ribonucleotide</wikipedia_id>
  <metlin_id>6294</metlin_id>
  <synthesis_reference>Schmitt, Laurent; Caperelli, Carol A.  Enantiospecific synthesis of carbocyclic aminoimidazole carboxamide ribonucleotide (C-AICAR), succinoaminoimidazole carboxamide ribonucleotide (C-SAICAR), and a new intermediate for SAICAR analogs.    Nucleosides &amp; Nucleotides  (1995),  14(9 &amp; 10),  1929-45.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:06 UTC</creation_date>
  <update_date>2020-03-13 16:28:34 UTC</update_date>
  <accession>BMDB0001518</accession>
  <secondary_accessions>
    <accession>BMDB01518</accession>
  </secondary_accessions>
  <name>Alpha-CEHC</name>
  <description>Alpha-Cehc, also known as Α-cehc, belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. Alpha-Cehc is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Alpha-Cehc exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>a-CEHC</synonym>
    <synonym>Α-cehc</synonym>
    <synonym>3-(6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoate</synonym>
    <synonym>α-Carboxyethyl hydrochroman</synonym>
    <synonym>alpha-Carboxyethyl hydrochroman</synonym>
    <synonym>2,5,7,8-Tetramethyl-2(2'-carboxyethyl)-6-hydroxychroman</synonym>
    <synonym>2,5,7,8-Tetramethyl-2-(β-carboxyethyl)-6-hydroxychroman</synonym>
    <synonym>2,5,7,8-Tetramethyl-2-(beta-carboxyethyl)-6-hydroxychroman</synonym>
    <synonym>6-Hydroxy-2-(2-carboxylethyl)-2,5,7,8-tetramethylchroman</synonym>
    <synonym>6-Hydroxy-2-carboxylethyl-2,5,7,8-tetramethylchroman</synonym>
    <synonym>alpha-CEHC</synonym>
  </synonyms>
  <chemical_formula>C16H22O4</chemical_formula>
  <average_molecular_weight>278.3435</average_molecular_weight>
  <monisotopic_moleculate_weight>278.151809192</monisotopic_moleculate_weight>
  <iupac_name>3-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoic acid</iupac_name>
  <traditional_iupac>α-cehc</traditional_iupac>
  <cas_registry_number>4072-32-6</cas_registry_number>
  <smiles>CC1=C(O)C(C)=C2CCC(C)(CCC(O)=O)OC2=C1C</smiles>
  <inchi>InChI=1S/C16H22O4/c1-9-10(2)15-12(11(3)14(9)19)5-7-16(4,20-15)8-6-13(17)18/h19H,5-8H2,1-4H3,(H,17,18)</inchi>
  <inchikey>AXODOWFEFKOVSH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Benzopyrans</class>
    <sub_class>1-benzopyrans</sub_class>
    <direct_parent>1-benzopyrans</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-benzopyran</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.88</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>278.3435</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>278.151809192</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(O)C(C)=C2CCC(C)(CCC(O)=O)OC2=C1C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H22O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H22O4/c1-9-10(2)15-12(11(3)14(9)19)5-7-16(4,20-15)8-6-13(17)18/h19H,5-8H2,1-4H3,(H,17,18)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AXODOWFEFKOVSH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>77.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>30.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38105</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29966</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29967</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450245</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by UPLC-Q-TOF MS E</comment>
      <references>
        <reference>
          <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
          <pubmed_id>28342601</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022669</foodb_id>
  <drugbank_id/>
  <chemspider_id>8119154</chemspider_id>
  <pdbe_id/>
  <chebi_id>626842</chebi_id>
  <pubchem_compound_id>9943542</pubchem_compound_id>
  <meta_cyc_id/>
  <wikipedia_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference>Pope, Simon A. S.; Burtin, Guillaume E.; Clayton, Peter T.; Madge, David J.; Muller, David P. R.  Synthesis and analysis of conjugates of the major vitamin E metabolite, a-CEHC.    Free Radical Biology &amp; Medicine  (2002),  33(6),  807-817. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.</reference_text>
      <pubmed_id>28342601</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:07 UTC</creation_date>
  <update_date>2020-04-16 17:51:42 UTC</update_date>
  <accession>BMDB0001520</accession>
  <secondary_accessions>
    <accession>BMDB01520</accession>
  </secondary_accessions>
  <name>Flavin Mononucleotide</name>
  <description/>
  <synonyms>
    <synonym>Riboflavin 5'-(dihydrogen phosphate)</synonym>
    <synonym>Riboflavin 5'-monophosphate</synonym>
    <synonym>Riboflavin 5'-phosphate</synonym>
    <synonym>Riboflavin monophosphate</synonym>
    <synonym>Riboflavin-5-phosphate</synonym>
    <synonym>Riboflavine dihydrogen phosphate</synonym>
    <synonym>Riboflavin 5'-(dihydrogen phosphoric acid)</synonym>
    <synonym>Riboflavin 5'-monophosphoric acid</synonym>
    <synonym>Riboflavin 5'-phosphoric acid</synonym>
    <synonym>Riboflavin monophosphoric acid</synonym>
    <synonym>Riboflavin-5-phosphoric acid</synonym>
    <synonym>Riboflavine dihydrogen phosphoric acid</synonym>
    <synonym>Flanin</synonym>
    <synonym>Flavine mononucleotide</synonym>
    <synonym>Flavol</synonym>
    <synonym>FMN</synonym>
    <synonym>Riboflavin</synonym>
    <synonym>Riboflavin mononucleotide</synonym>
    <synonym>Riboflavin phosphate</synonym>
    <synonym>Riboflavin-5'-phosphate na</synonym>
    <synonym>Riboflavine 5'-monophosphate</synonym>
    <synonym>Riboflavine 5'-phosphate</synonym>
    <synonym>Riboflavine monophosphate</synonym>
    <synonym>Riboflavine phosphate</synonym>
    <synonym>Riboflavine-5'-phosphate</synonym>
    <synonym>Vitamin b2 phosphate</synonym>
    <synonym>5'-monoPhosphate, riboflavin</synonym>
    <synonym>5'-Phosphate, riboflavin</synonym>
    <synonym>Flavin mononucleotide sodium salt</synonym>
    <synonym>Mononucleotide, riboflavin</synonym>
    <synonym>Flavin mononucleotide monosodium salt</synonym>
    <synonym>Flavin mononucleotide monosodium salt, dihydrate</synonym>
    <synonym>Phosphate, sodium riboflavin</synonym>
    <synonym>Riboflavin 5' phosphate</synonym>
    <synonym>Riboflavin phosphate, sodium</synonym>
    <synonym>Mononucleotide, flavin</synonym>
    <synonym>Riboflavin 5' monophosphate</synonym>
    <synonym>Flavin mononucleotide disodium salt</synonym>
    <synonym>Sodium riboflavin phosphate</synonym>
  </synonyms>
  <chemical_formula>C17H21N4O9P</chemical_formula>
  <average_molecular_weight>456.3438</average_molecular_weight>
  <monisotopic_moleculate_weight>456.104614802</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>riboflavin 5'-phosphate</traditional_iupac>
  <cas_registry_number>146-17-8</cas_registry_number>
  <smiles>CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=NC(=O)NC(=O)C1=N2</smiles>
  <inchi>InChI=1S/C17H21N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29)/t11-,12+,14-/m0/s1</inchi>
  <inchikey>FVTCRASFADXXNN-SCRDCRAPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Flavin nucleotides</class>
    <sub_class/>
    <direct_parent>Flavin nucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Flavins</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Pyrazines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Quinoxalines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Diazanaphthalene</substituent>
      <substituent>Flavin</substituent>
      <substituent>Flavin nucleotide</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isoalloxazine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Pteridine</substituent>
      <substituent>Pyrazine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Quinoxaline</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>flavin mononucleotide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>290 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>92 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>456.3438</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>456.104614802</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=NC(=O)NC(=O)C1=N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C17H21N4O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C17H21N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29)/t11-,12+,14-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FVTCRASFADXXNN-SCRDCRAPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>201.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>107.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>42.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ion Channels and Their Functional Role in Vascular Endothelium</name>
      <smpdb_id>SMP0108207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pantothenate and CoA Biosynthesis</name>
      <smpdb_id>SMP0087207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Riboflavin Metabolism</name>
      <smpdb_id>SMP0087211</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin B6 Metabolism</name>
      <smpdb_id>SMP0087240</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38106</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1080</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439065</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00061</kegg_id>
  <foodb_id>FDB030862</foodb_id>
  <drugbank_id>DB03247</drugbank_id>
  <chemspider_id>559060</chemspider_id>
  <pdbe_id/>
  <chebi_id>17621</chebi_id>
  <pubchem_compound_id>643976</pubchem_compound_id>
  <meta_cyc_id>FMN</meta_cyc_id>
  <wikipedia_id>Flavin_mononucleotide</wikipedia_id>
  <knapsack_id>C00019686</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>33703</bigg_id>
  <metlin_id>6295</metlin_id>
  <synthesis_reference>Ono, Shigeru; Hirano, Hiroko; Sato, Yoshiyuki.  Formation of flavin adenine dinucleotide and flavin mononucleotide by lens homogenate.    Experimental Eye Research  (1982),  34(2),  297-301.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00387</protein_accession>
      <name>Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)</name>
      <uniprot_id>Q58DK4</uniprot_id>
      <gene_name>DAK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:08 UTC</creation_date>
  <update_date>2020-04-15 22:00:44 UTC</update_date>
  <accession>BMDB0001521</accession>
  <secondary_accessions>
    <accession>BMDB01521</accession>
  </secondary_accessions>
  <name>Tetradecanoyl-CoA</name>
  <description>Tetradecanoyl-CoA , also known as myristoyl-CoA or N-C14:0CoA, belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. Tetradecanoyl-CoA is possibly soluble (in water) and a strong basic compound (based on its pKa). Tetradecanoyl-CoA exists in all living species, ranging from bacteria to humans. Tetradecanoyl-CoA participates in a number of enzymatic reactions, within cattle. In particular, Tetradecanoyl-CoA and glycerol 3-phosphate can be converted into lpa(14:0/0:0) through the action of the enzyme glycerol-3-phosphate acyltransferase. In addition, Lpa(14:0/0:0) and tetradecanoyl-CoA can be converted into PA(14:0/14:0) through its interaction with the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. In cattle, tetradecanoyl-CoA is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(14:0/14:0/14:0) pathway.</description>
  <synonyms>
    <synonym>Myristoyl-CoA</synonym>
    <synonym>Myristoyl-coenzyme A</synonym>
    <synonym>N-C14:0CoA</synonym>
    <synonym>N-C14:0coenzyme A</synonym>
    <synonym>S-Tetradecanoyl-coenzyme A</synonym>
    <synonym>Tetradecanoyl CoA</synonym>
    <synonym>Tetradecanoyl coenzyme A</synonym>
    <synonym>Tetradecanoyl-coenzyme A</synonym>
    <synonym>Tetradecanoyl-CoA</synonym>
  </synonyms>
  <chemical_formula>C35H62N7O17P3S</chemical_formula>
  <average_molecular_weight>977.89</average_molecular_weight>
  <monisotopic_moleculate_weight>977.313573819</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-(tetradecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-(tetradecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid</traditional_iupac>
  <cas_registry_number>3130-72-1</cas_registry_number>
  <smiles>CCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</smiles>
  <inchi>InChI=1S/C35H62N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-26(44)63-19-18-37-25(43)16-17-38-33(47)30(46)35(2,3)21-56-62(53,54)59-61(51,52)55-20-24-29(58-60(48,49)50)28(45)34(57-24)42-23-41-27-31(36)39-22-40-32(27)42/h22-24,28-30,34,45-46H,4-21H2,1-3H3,(H,37,43)(H,38,47)(H,51,52)(H,53,54)(H2,36,39,40)(H2,48,49,50)/t24-,28-,29-,30?,34-/m1/s1</inchi>
  <inchikey>DUAFKXOFBZQTQE-XVDJLSDJSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acyl thioesters</sub_class>
    <direct_parent>Long-chain fatty acyl CoAs</direct_parent>
    <alternative_parents>
      <alternative_parent>2,3,4-saturated fatty acyl CoAs</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Coenzyme A and derivatives</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine ribonucleoside diphosphates</alternative_parent>
      <alternative_parent>Ribonucleoside 3'-phosphates</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Coenzyme a or derivatives</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside 3',5'-bisphosphate</substituent>
      <substituent>Purine ribonucleoside bisphosphate</substituent>
      <substituent>Purine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Ribonucleoside 3'-phosphate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fatty acyl CoAs</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-(tetradecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>977.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>977.313573819</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C35H62N7O17P3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C35H62N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-26(44)63-19-18-37-25(43)16-17-38-33(47)30(46)35(2,3)21-56-62(53,54)59-61(51,52)55-20-24-29(58-60(48,49)50)28(45)34(57-24)42-23-41-27-31(36)39-22-40-32(27)42/h22-24,28-30,34,45-46H,4-21H2,1-3H3,(H,37,43)(H,38,47)(H,51,52)(H,53,54)(H2,36,39,40)(H2,48,49,50)/t24-,28-,29-,30?,34-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DUAFKXOFBZQTQE-XVDJLSDJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>363.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>227.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>96.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Beta Oxidation of Very Long Chain Fatty Acids</name>
      <smpdb_id>SMP0087259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/10:0/14:0)</name>
      <smpdb_id>SMP0108477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/12:0/14:0)</name>
      <smpdb_id>SMP0108445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/13:0)</name>
      <smpdb_id>SMP0108534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/14:0)</name>
      <smpdb_id>SMP0108525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/15:0)</name>
      <smpdb_id>SMP0108522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/17:0)</name>
      <smpdb_id>SMP0108488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/18:0)</name>
      <smpdb_id>SMP0108489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/19:0)</name>
      <smpdb_id>SMP0108447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0108592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0108593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0108594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0108595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0108596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0108597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0108598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0108599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0108600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0108601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0108602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0108603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0108604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0108605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0108606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0108607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0108608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(10:0/16:0/14:0)</name>
      <smpdb_id>SMP0108468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/14:0)</name>
      <smpdb_id>SMP0072652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/14:1(9Z))</name>
      <smpdb_id>SMP0072653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/15:0)</name>
      <smpdb_id>SMP0072654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/16:0)</name>
      <smpdb_id>SMP0072655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/16:1(9Z))</name>
      <smpdb_id>SMP0072656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:0)</name>
      <smpdb_id>SMP0072657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:1(11Z))</name>
      <smpdb_id>SMP0072658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:1(9Z))</name>
      <smpdb_id>SMP0072659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:0)</name>
      <smpdb_id>SMP0072664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:1(11Z))</name>
      <smpdb_id>SMP0072665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:0)</name>
      <smpdb_id>SMP0072672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:1(13Z))</name>
      <smpdb_id>SMP0072673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/24:0)</name>
      <smpdb_id>SMP0072679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/24:1(15Z))</name>
      <smpdb_id>SMP0072680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0072681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0072682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0072683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0072684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0072685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/15:0)</name>
      <smpdb_id>SMP0072709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/16:0)</name>
      <smpdb_id>SMP0072710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/16:1(9Z))</name>
      <smpdb_id>SMP0072711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:0)</name>
      <smpdb_id>SMP0072712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:1(11Z))</name>
      <smpdb_id>SMP0072713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:1(9Z))</name>
      <smpdb_id>SMP0072714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:0)</name>
      <smpdb_id>SMP0072719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:1(11Z))</name>
      <smpdb_id>SMP0072720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:0)</name>
      <smpdb_id>SMP0072727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:1(13Z))</name>
      <smpdb_id>SMP0072728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/24:0)</name>
      <smpdb_id>SMP0072734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/24:1(15Z))</name>
      <smpdb_id>SMP0072735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/16:0)</name>
      <smpdb_id>SMP0072736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/16:1(9Z))</name>
      <smpdb_id>SMP0072737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:0)</name>
      <smpdb_id>SMP0072738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:1(11Z))</name>
      <smpdb_id>SMP0072739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:1(9Z))</name>
      <smpdb_id>SMP0072740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:0)</name>
      <smpdb_id>SMP0072745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:1(11Z))</name>
      <smpdb_id>SMP0072746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:0)</name>
      <smpdb_id>SMP0072753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:1(13Z))</name>
      <smpdb_id>SMP0072754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/24:0)</name>
      <smpdb_id>SMP0072760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/24:1(15Z))</name>
      <smpdb_id>SMP0072761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0072762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0072763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:0)</name>
      <smpdb_id>SMP0072787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:1(11Z))</name>
      <smpdb_id>SMP0072788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:1(9Z))</name>
      <smpdb_id>SMP0072789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:0)</name>
      <smpdb_id>SMP0072794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:1(11Z))</name>
      <smpdb_id>SMP0072795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:0)</name>
      <smpdb_id>SMP0072802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:1(13Z))</name>
      <smpdb_id>SMP0072803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/24:0)</name>
      <smpdb_id>SMP0072809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/24:1(15Z))</name>
      <smpdb_id>SMP0072810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0072811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0072817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0072825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0072832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0072834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0072839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0072847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072852</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0072854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0072856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0072860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072861</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072867</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0072868</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072869</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072870</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072871</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072872</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072873</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072874</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0072875</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072876</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0072877</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072878</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072879</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0072880</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072881</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072882</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072883</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072884</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072885</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072886</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072887</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0072888</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072889</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072890</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072891</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072892</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072893</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072894</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0072895</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072896</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072897</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072898</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0072899</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072900</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072901</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072902</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072903</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072904</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072905</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072906</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0072907</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072908</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072909</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072910</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072911</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072912</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072913</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0072914</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072915</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0072916</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0072917</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072918</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072919</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072920</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072921</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072922</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072923</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072924</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0072925</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072926</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072927</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072928</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072929</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072930</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072931</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0072932</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072933</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:0)</name>
      <smpdb_id>SMP0072934</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:1(11Z))</name>
      <smpdb_id>SMP0072935</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072936</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072937</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072938</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072939</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072940</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072941</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:0)</name>
      <smpdb_id>SMP0072942</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:1(13Z))</name>
      <smpdb_id>SMP0072943</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072944</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072945</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072946</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072947</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072948</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/24:0)</name>
      <smpdb_id>SMP0072949</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:0/24:1(15Z))</name>
      <smpdb_id>SMP0072950</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0072951</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072952</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072953</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072955</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072956</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072957</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0072958</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072959</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072960</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072961</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072962</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072963</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072964</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0072965</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072966</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0072967</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072968</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072969</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072971</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072972</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0072973</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072975</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072976</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072977</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072978</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072979</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0072980</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072981</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0072982</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072983</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072984</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072985</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072986</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0072987</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0072988</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0072989</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072990</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0072991</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072992</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0072993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0072994</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0072995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072996</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0072997</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072998</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0072999</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073000</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073001</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073002</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073003</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073004</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073005</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073006</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073007</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073008</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0073009</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073010</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0073012</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073013</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073014</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073015</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073016</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073017</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073018</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0073019</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073020</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073021</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073022</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073024</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073025</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073026</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073027</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073028</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073029</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073030</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073031</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0073032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0073033</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073034</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073035</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073036</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073038</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0073040</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073041</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:0)</name>
      <smpdb_id>SMP0073042</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:1(13Z))</name>
      <smpdb_id>SMP0073043</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073044</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073046</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073047</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/24:0)</name>
      <smpdb_id>SMP0073049</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:0/24:1(15Z))</name>
      <smpdb_id>SMP0073050</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0073051</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0073057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0073059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0073072</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073073</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073074</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0073075</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073076</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073077</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073078</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073079</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073080</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0073081</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0073082</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073083</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:0/24:0)</name>
      <smpdb_id>SMP0073084</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:0/24:1(15Z))</name>
      <smpdb_id>SMP0073085</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(14:0/24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0073086</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/21:0/14:0)</name>
      <smpdb_id>SMP0108266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/22:0/14:0)</name>
      <smpdb_id>SMP0108255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-21:0/14:0)</name>
      <smpdb_id>SMP0108970</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/a-25:0/14:0)</name>
      <smpdb_id>SMP0108995</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0109023</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0109045</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(19:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0109066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/10:0/14:0)</name>
      <smpdb_id>SMP0108290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/12:0)</name>
      <smpdb_id>SMP0108248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/13:0)</name>
      <smpdb_id>SMP0108295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/19:0)</name>
      <smpdb_id>SMP0108249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/21:0)</name>
      <smpdb_id>SMP0108271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109119</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109120</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109121</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109122</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109123</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109124</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109125</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109126</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109127</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109128</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109129</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109130</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109131</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109132</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109133</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109134</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109135</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/17:0/14:0)</name>
      <smpdb_id>SMP0108253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(20:0/8:0/14:0)</name>
      <smpdb_id>SMP0108246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/12:0/14:0)</name>
      <smpdb_id>SMP0108344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/10:0)</name>
      <smpdb_id>SMP0108347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/13:0)</name>
      <smpdb_id>SMP0108342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/14:0)</name>
      <smpdb_id>SMP0108338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/16:0)</name>
      <smpdb_id>SMP0108346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/17:0)</name>
      <smpdb_id>SMP0108352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/18:0)</name>
      <smpdb_id>SMP0108386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/22:0)</name>
      <smpdb_id>SMP0108334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/8:0)</name>
      <smpdb_id>SMP0108365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/15:0/14:0)</name>
      <smpdb_id>SMP0108375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(21:0/21:0/14:0)</name>
      <smpdb_id>SMP0108373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/12:0/14:0)</name>
      <smpdb_id>SMP0108414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/10:0)</name>
      <smpdb_id>SMP0108440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/13:0)</name>
      <smpdb_id>SMP0108422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0109794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0109795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0109796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0109797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0109798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0109799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0109800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0109801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0109802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0109803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0109804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0109805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0109806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0109807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0109808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0109809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0109810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/17:0/14:0)</name>
      <smpdb_id>SMP0108415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(22:0/8:0/14:0)</name>
      <smpdb_id>SMP0108418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/13:0/14:0)</name>
      <smpdb_id>SMP0108462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/10:0)</name>
      <smpdb_id>SMP0108455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/12:0)</name>
      <smpdb_id>SMP0108475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/14:0)</name>
      <smpdb_id>SMP0108532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/15:0)</name>
      <smpdb_id>SMP0108529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/17:0)</name>
      <smpdb_id>SMP0108491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/18:0)</name>
      <smpdb_id>SMP0108510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110100</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110101</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110102</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-21:0)</name>
      <smpdb_id>SMP0110103</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0110104</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110105</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110106</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110107</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110108</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110109</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110110</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110111</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110112</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110113</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110114</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110115</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110116</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/16:0/14:0)</name>
      <smpdb_id>SMP0108449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/19:0/14:0)</name>
      <smpdb_id>SMP0108497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(8:0/8:0/14:0)</name>
      <smpdb_id>SMP0108515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/12:0/14:0)</name>
      <smpdb_id>SMP0110369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/13:0/14:0)</name>
      <smpdb_id>SMP0110391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/14:0)</name>
      <smpdb_id>SMP0110412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/15:0)</name>
      <smpdb_id>SMP0110413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/16:0)</name>
      <smpdb_id>SMP0110414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/17:0)</name>
      <smpdb_id>SMP0110415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/18:0)</name>
      <smpdb_id>SMP0110416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/a-25:0)</name>
      <smpdb_id>SMP0110420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-21:0/a-21:0/14:0)</name>
      <smpdb_id>SMP0110553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/14:0)</name>
      <smpdb_id>SMP0110669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/14:0)</name>
      <smpdb_id>SMP0110690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/14:0)</name>
      <smpdb_id>SMP0110710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/15:0)</name>
      <smpdb_id>SMP0110711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/16:0)</name>
      <smpdb_id>SMP0110712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/17:0)</name>
      <smpdb_id>SMP0110713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/18:0)</name>
      <smpdb_id>SMP0110714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0110715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0110716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0110717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0110718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0110719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0110720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0110721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0110722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0110723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0110724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0110725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-20:0)</name>
      <smpdb_id>SMP0110726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0110727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0110728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0110729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(a-25:0/a-25:0/14:0)</name>
      <smpdb_id>SMP0110845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0110954</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0110974</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-19:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0110993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/12:0/14:0)</name>
      <smpdb_id>SMP0111011</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/13:0/14:0)</name>
      <smpdb_id>SMP0111032</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/14:0)</name>
      <smpdb_id>SMP0111052</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/15:0)</name>
      <smpdb_id>SMP0111053</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/16:0)</name>
      <smpdb_id>SMP0111054</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/17:0)</name>
      <smpdb_id>SMP0111055</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/18:0)</name>
      <smpdb_id>SMP0111056</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/19:0)</name>
      <smpdb_id>SMP0111057</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111058</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111059</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111060</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111061</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111062</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111063</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111064</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111065</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111066</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111067</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-19:0)</name>
      <smpdb_id>SMP0111068</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-21:0)</name>
      <smpdb_id>SMP0111069</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0111070</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111071</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-20:0/i-20:0/14:0)</name>
      <smpdb_id>SMP0111251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/12:0/14:0)</name>
      <smpdb_id>SMP0111278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/13:0/14:0)</name>
      <smpdb_id>SMP0111296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/14:0)</name>
      <smpdb_id>SMP0111313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/15:0)</name>
      <smpdb_id>SMP0111314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/16:0)</name>
      <smpdb_id>SMP0111315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/17:0)</name>
      <smpdb_id>SMP0111316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/18:0)</name>
      <smpdb_id>SMP0111317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-22:0)</name>
      <smpdb_id>SMP0111328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-21:0/i-21:0/14:0)</name>
      <smpdb_id>SMP0111465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/12:0/14:0)</name>
      <smpdb_id>SMP0111488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/13:0/14:0)</name>
      <smpdb_id>SMP0111505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/14:0)</name>
      <smpdb_id>SMP0111521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/15:0)</name>
      <smpdb_id>SMP0111522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/16:0)</name>
      <smpdb_id>SMP0111523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/17:0)</name>
      <smpdb_id>SMP0111524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/18:0)</name>
      <smpdb_id>SMP0111525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/14:0/i-24:0)</name>
      <smpdb_id>SMP0111536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-22:0/i-22:0/14:0)</name>
      <smpdb_id>SMP0111658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/12:0/14:0)</name>
      <smpdb_id>SMP0111678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/13:0/14:0)</name>
      <smpdb_id>SMP0111694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/14:0)</name>
      <smpdb_id>SMP0111709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/15:0)</name>
      <smpdb_id>SMP0111710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/16:0)</name>
      <smpdb_id>SMP0111711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/17:0)</name>
      <smpdb_id>SMP0111712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/18:0)</name>
      <smpdb_id>SMP0111713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-13:0)</name>
      <smpdb_id>SMP0111714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-15:0)</name>
      <smpdb_id>SMP0111715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/a-17:0)</name>
      <smpdb_id>SMP0111716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-12:0)</name>
      <smpdb_id>SMP0111717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-13:0)</name>
      <smpdb_id>SMP0111718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-14:0)</name>
      <smpdb_id>SMP0111719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-15:0)</name>
      <smpdb_id>SMP0111720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-16:0)</name>
      <smpdb_id>SMP0111721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-17:0)</name>
      <smpdb_id>SMP0111722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/14:0/i-18:0)</name>
      <smpdb_id>SMP0111723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>De Novo Triacylglycerol Biosynthesis TG(i-24:0/i-24:0/14:0)</name>
      <smpdb_id>SMP0111831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Elongation in Mitochondria</name>
      <smpdb_id>SMP0087194</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids</name>
      <smpdb_id>SMP0087267</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32257</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>58623</chemspider_id>
  <foodb_id>FDB031010</foodb_id>
  <kegg_id>C02593</kegg_id>
  <pubchem_compound_id>65113</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>15532</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>40154</bigg_id>
  <wikipedia_id/>
  <metlin_id>3707</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01079</protein_accession>
      <name>Glycylpeptide N-tetradecanoyltransferase</name>
      <uniprot_id>Q32LK5</uniprot_id>
      <gene_name>NMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01080</protein_accession>
      <name>Glycylpeptide N-tetradecanoyltransferase 1</name>
      <uniprot_id>P31717</uniprot_id>
      <gene_name>NMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01081</protein_accession>
      <name>Glycylpeptide N-tetradecanoyltransferase</name>
      <uniprot_id>Q8MKE3</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01082</protein_accession>
      <name>Glycylpeptide N-tetradecanoyltransferase</name>
      <uniprot_id>Q2KIZ5</uniprot_id>
      <gene_name>NMT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01083</protein_accession>
      <name>Glycylpeptide N-tetradecanoyltransferase</name>
      <uniprot_id>Q9GL39</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01084</protein_accession>
      <name>Glycylpeptide N-tetradecanoyltransferase 2</name>
      <uniprot_id>Q9N181</uniprot_id>
      <gene_name>NMT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:09 UTC</creation_date>
  <update_date>2020-04-15 22:15:24 UTC</update_date>
  <accession>BMDB0001522</accession>
  <secondary_accessions>
    <accession>BMDB01522</accession>
  </secondary_accessions>
  <name>Methylguanidine</name>
  <description/>
  <synonyms>
    <synonym>1-METHYLGUANIDINE</synonym>
    <synonym>Methylguanidin</synonym>
    <synonym>MGX</synonym>
    <synonym>Monomethyl guanidin</synonym>
    <synonym>Monomethylguanidine</synonym>
    <synonym>N-Methylguanidine</synonym>
    <synonym>N1-Methylguanidine</synonym>
  </synonyms>
  <chemical_formula>C2H7N3</chemical_formula>
  <average_molecular_weight>73.0971</average_molecular_weight>
  <monisotopic_moleculate_weight>73.063997239</monisotopic_moleculate_weight>
  <iupac_name>N-methylguanidine</iupac_name>
  <traditional_iupac>methylguanidine</traditional_iupac>
  <cas_registry_number>471-29-4</cas_registry_number>
  <smiles>CNC(N)=N</smiles>
  <inchi>InChI=1S/C2H7N3/c1-5-2(3)4/h1H3,(H4,3,4,5)</inchi>
  <inchikey>CHJJGSNFBQVOTG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Guanidines</sub_class>
    <direct_parent>Guanidines</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>guanidines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>1.78 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>12.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-methylguanidine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>73.0971</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>73.063997239</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CNC(N)=N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C2H7N3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C2H7N3/c1-5-2(3)4/h1H3,(H4,3,4,5)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CHJJGSNFBQVOTG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>61.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>7.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>309744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354248</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>354249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451898</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02294</kegg_id>
  <foodb_id>FDB005421</foodb_id>
  <drugbank_id/>
  <chemspider_id>9707</chemspider_id>
  <pdbe_id/>
  <chebi_id>16628</chebi_id>
  <pubchem_compound_id>10111</pubchem_compound_id>
  <meta_cyc_id>CPD-593</meta_cyc_id>
  <wikipedia_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>3768</metlin_id>
  <synthesis_reference>Philippi, E.; Morsch, K.  Preparation of methylguanidine according to Werner-Bell.    Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen  (1927),  60B  2120-2.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:11 UTC</creation_date>
  <update_date>2020-04-15 22:35:54 UTC</update_date>
  <accession>BMDB0001525</accession>
  <secondary_accessions>
    <accession>BMDB01525</accession>
  </secondary_accessions>
  <name>Imidazole</name>
  <description/>
  <synonyms>
    <synonym>1,3-Diaza-2,4-cyclopentadiene</synonym>
    <synonym>1,3-Diazole</synonym>
    <synonym>Glyoxaline</synonym>
    <synonym>Him</synonym>
    <synonym>IMD</synonym>
    <synonym>Imidazol</synonym>
    <synonym>Iminazole</synonym>
    <synonym>Miazole</synonym>
    <synonym>N,N'-1,2-ethenediylmethanimidamide</synonym>
    <synonym>N,N'-vinyleneformamidine</synonym>
    <synonym>Pyrro[b]monazole</synonym>
    <synonym>1H-Imidazole</synonym>
    <synonym>Glyoxalin</synonym>
    <synonym>Imutex</synonym>
    <synonym>Pyrro(b)monazole</synonym>
    <synonym>{Pyrro[b]monazole}</synonym>
    <synonym>Imidazole acetate</synonym>
    <synonym>Imidazole monophosphonate</synonym>
    <synonym>Imidazole sodium</synonym>
    <synonym>Imidazolium chloride</synonym>
    <synonym>Al-imidazole</synonym>
    <synonym>Imidazole citrate</synonym>
    <synonym>Cu-imidazole</synonym>
    <synonym>Imidazole conjugate monoacid</synonym>
    <synonym>Imidazole monohydrochloride</synonym>
    <synonym>Imidazole</synonym>
  </synonyms>
  <chemical_formula>C3H4N2</chemical_formula>
  <average_molecular_weight>68.0773</average_molecular_weight>
  <monisotopic_moleculate_weight>68.037448138</monisotopic_moleculate_weight>
  <iupac_name>1H-imidazole</iupac_name>
  <traditional_iupac>imidazole</traditional_iupac>
  <cas_registry_number>288-32-4</cas_registry_number>
  <smiles>N1C=CN=C1</smiles>
  <inchi>InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)</inchi>
  <inchikey>RAXXELZNTBOGNW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Azoles</class>
    <sub_class>Imidazoles</sub_class>
    <direct_parent>Imidazoles</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>an aromatic compound</external_descriptor>
      <external_descriptor>imidazole</external_descriptor>
      <external_descriptor>mancude organic heteromonocyclic parent</external_descriptor>
      <external_descriptor>monocyclic heteroarene</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>90.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.08</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1H-imidazole</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>68.0773</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>68.037448138</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N1C=CN=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H4N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RAXXELZNTBOGNW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>28.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>19.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>6.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6641</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1625</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452283</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR. Samples have been collected from 22 clinically normal, 6-12 month old Holstein–Friesian heifers and stored at -20 °C for between 2 and 15 years.</comment>
      <references>
        <reference>
          <reference_text>Trabi M, Keller MD, Johnsson NN. NMR-based metabonomics of bovine blood: an investigation into the effects of long term storage on plasma samples. Metabolomics (2013) 9:1041-1047   doi: 10.1007/s11306-013-0520-2</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>773</chemspider_id>
  <foodb_id>FDB012307</foodb_id>
  <kegg_id>C01589</kegg_id>
  <pubchem_compound_id>795</pubchem_compound_id>
  <drugbank_id>DB03366</drugbank_id>
  <chebi_id>16069</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Imidazole</wikipedia_id>
  <metlin_id>4190</metlin_id>
  <synthesis_reference>Lu, Zhongmin; Liu, Xinzheng.  Review of process for synthesis of imidazole.    Huagong Shikan  (1999),  13(2),  26-27.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:12 UTC</creation_date>
  <update_date>2020-03-13 16:28:37 UTC</update_date>
  <accession>BMDB0001526</accession>
  <secondary_accessions>
    <accession>BMDB01526</accession>
  </secondary_accessions>
  <name>S-Acetyldihydrolipoamide</name>
  <description/>
  <synonyms>
    <synonym>6-S-Acetyldihydrolipoamide</synonym>
    <synonym>6-Acetylsulfanyl-8-sulfanyl-octanamide</synonym>
    <synonym>S-[6-Amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioate</synonym>
    <synonym>S-[6-Amino-6-oxo-1-(2-sulfanylethyl)hexyl] ethanethioic acid</synonym>
  </synonyms>
  <chemical_formula>C10H19NO2S2</chemical_formula>
  <average_molecular_weight>249.393</average_molecular_weight>
  <monisotopic_moleculate_weight>249.085720237</monisotopic_moleculate_weight>
  <iupac_name>6-(acetylsulfanyl)-8-sulfanyloctanamide</iupac_name>
  <traditional_iupac>S(6)-acetyldihydrolipoamide</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC(=O)SC(CCS)CCCCC(N)=O</smiles>
  <inchi>InChI=1S/C10H19NO2S2/c1-8(12)15-9(6-7-14)4-2-3-5-10(11)13/h9,14H,2-7H2,1H3,(H2,11,13)</inchi>
  <inchikey>ARGXEXVCHMNAQU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty amides</sub_class>
    <direct_parent>Fatty amides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>S-substituted dihydrolipoamide</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6-(acetylsulfanyl)-8-sulfanyloctanamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>249.393</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>249.085720237</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)SC(CCS)CCCCC(N)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H19NO2S2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H19NO2S2/c1-8(12)15-9(6-7-14)4-2-3-5-10(11)13/h9,14H,2-7H2,1H3,(H2,11,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ARGXEXVCHMNAQU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>67.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>27.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36292</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>1046</chemspider_id>
  <foodb_id>FDB022671</foodb_id>
  <kegg_id>C01136</kegg_id>
  <pubchem_compound_id>1076</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>16807</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6299</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:13 UTC</creation_date>
  <update_date>2020-03-13 16:28:37 UTC</update_date>
  <accession>BMDB0001527</accession>
  <secondary_accessions>
    <accession>BMDB01527</accession>
  </secondary_accessions>
  <name>3-Methylthiopropionic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Methylthiopropanoic acid</synonym>
    <synonym>3-(Methylthio)propionic acid</synonym>
    <synonym>3-Methylthiopropionate</synonym>
    <synonym>3-(Methylsulfanyl)propanoate</synonym>
    <synonym>3-Methylthiopropanoate</synonym>
    <synonym>3-(Methylthio)propionate</synonym>
    <synonym>3-(Methylsulfanyl)propanoic acid</synonym>
    <synonym>3-(Methylsulphanyl)propanoate</synonym>
    <synonym>3-(Methylsulphanyl)propanoic acid</synonym>
    <synonym>4-Thiapentanoate</synonym>
    <synonym>4-Thiapentanoic acid</synonym>
    <synonym>3-Methylmercaptopropionate</synonym>
    <synonym>3-Methylthiopropionate sodium salt</synonym>
    <synonym>3-Methyl-thiopropionate</synonym>
    <synonym>3-Methylthiopropionic acid</synonym>
  </synonyms>
  <chemical_formula>C4H8O2S</chemical_formula>
  <average_molecular_weight>120.17</average_molecular_weight>
  <monisotopic_moleculate_weight>120.02450019</monisotopic_moleculate_weight>
  <iupac_name>3-(methylsulfanyl)propanoic acid</iupac_name>
  <traditional_iupac>3-methylthiopropionic acid</traditional_iupac>
  <cas_registry_number>646-01-5</cas_registry_number>
  <smiles>CSCCC(O)=O</smiles>
  <inchi>InChI=1S/C4H8O2S/c1-7-3-2-4(5)6/h2-3H2,1H3,(H,5,6)</inchi>
  <inchikey>CAOMCZAIALVUPA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Straight chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylthioethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thioether</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Thia fatty acids</external_descriptor>
      <external_descriptor>thia fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(methylsulfanyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>120.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>120.02450019</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CSCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O2S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O2S/c1-7-3-2-4(5)6/h2-3H2,1H3,(H,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CAOMCZAIALVUPA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>29.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23995</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38107</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>102843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>102844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>102845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>168726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>168727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>168728</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C08276</kegg_id>
  <foodb_id>FDB022672</foodb_id>
  <drugbank_id/>
  <chemspider_id>547</chemspider_id>
  <pubchem_compound_id>563</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>1438</chebi_id>
  <knapsack_id>C00001194</knapsack_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6300</metlin_id>
  <synthesis_reference>Whitehead, Ian M.; Ohleyer, Eric.  Process for the production of carboxylic acids from alcohols using Saccharomyces.    U.S.  (1997),     6 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:14 UTC</creation_date>
  <update_date>2020-03-18 18:42:15 UTC</update_date>
  <accession>BMDB0001529</accession>
  <secondary_accessions>
    <accession>BMDB01529</accession>
  </secondary_accessions>
  <name>Fenpropimorph</name>
  <description/>
  <synonyms>
    <synonym>(S)-(-)-Fenpropimorph</synonym>
    <synonym>(S)-cis-Fenpropimorph</synonym>
    <synonym>(2R,6S)-4-[(2S)-3-[4-(1,1-Dimethylethyl)phenyl]-2-methylpropyl]-2,6-dimethylmorpholine</synonym>
    <synonym>(S)-Fenpropimorph</synonym>
    <synonym>4-[3-[4-(1,1-Dimethylethyl)phenyl]-2-methylpropyl]-2,6-dimethylmorpholine</synonym>
    <synonym>Fenpropimorph</synonym>
    <synonym>cis-4-[3-(4-tert-Butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine</synonym>
    <synonym>cis-Fenpropimorph</synonym>
  </synonyms>
  <chemical_formula>C20H33NO</chemical_formula>
  <average_molecular_weight>303.49</average_molecular_weight>
  <monisotopic_moleculate_weight>303.256214687</monisotopic_moleculate_weight>
  <iupac_name>(2R,6S)-4-[(2S)-2-[(4-tert-butylphenyl)methyl]propyl]-2,6-dimethylmorpholine</iupac_name>
  <traditional_iupac>power task</traditional_iupac>
  <cas_registry_number/>
  <smiles>C[C@H](CN1C[C@H](C)O[C@H](C)C1)CC1=CC=C(C=C1)C(C)(C)C</smiles>
  <inchi>InChI=1S/C20H33NO/c1-15(12-21-13-16(2)22-17(3)14-21)11-18-7-9-19(10-8-18)20(4,5)6/h7-10,15-17H,11-14H2,1-6H3/t15-,16-,17+/m0/s1</inchi>
  <inchikey>RYAUSSKQMZRMAI-YESZJQIVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Phenylpropanes</sub_class>
    <direct_parent>Phenylpropanes</direct_parent>
    <alternative_parents>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Morpholines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Morpholine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxazinane</substituent>
      <substituent>Phenylpropane</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.19</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,6S)-4-[(2S)-2-[(4-tert-butylphenyl)methyl]propyl]-2,6-dimethylmorpholine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>303.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>303.256214687</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](CN1C[C@H](C)O[C@H](C)C1)CC1=CC=C(C=C1)C(C)(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H33NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H33NO/c1-15(12-21-13-16(2)22-17(3)14-21)11-18-7-9-19(10-8-18)20(4,5)6/h7-10,15-17H,11-14H2,1-6H3/t15-,16-,17+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RYAUSSKQMZRMAI-YESZJQIVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>12.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>95.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chebi_id>50146</chebi_id>
  <chemspider_id>10008267</chemspider_id>
  <pubchem_compound_id>11833620</pubchem_compound_id>
  <foodb_id>FDB016288</foodb_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <wikipedia_id>Fenpropimorph</wikipedia_id>
  <knapsack_id/>
  <bigg_id/>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference>Forsyth, Stewart A.; Gunaratne, H. Q. Nimal; Hardacre, Christopher; McKeown, Angela; Rooney, David W. One-Pot Multistep Synthetic Strategies for the Production of Fenpropimorph Using an Ionic Liquid Solvent. Organic Process Research &amp; Development (2006), </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:15 UTC</creation_date>
  <update_date>2020-03-13 16:28:38 UTC</update_date>
  <accession>BMDB0001530</accession>
  <secondary_accessions>
    <accession>BMDB01530</accession>
  </secondary_accessions>
  <name>Mannitol 1-phosphate</name>
  <description/>
  <synonyms>
    <synonym>Mannitol 1-phosphoric acid</synonym>
    <synonym>D-Mannitol-1-phosphate</synonym>
    <synonym>Mannitol-1-p</synonym>
    <synonym>Mannitol-1-phosphate</synonym>
    <synonym>D-Mannitol 1-phosphate</synonym>
    <synonym>D-Mannitol 6-phosphate</synonym>
    <synonym>Mannitol 1-phosphate</synonym>
  </synonyms>
  <chemical_formula>C6H15O9P</chemical_formula>
  <average_molecular_weight>262.1517</average_molecular_weight>
  <monisotopic_moleculate_weight>262.04536859</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>mannitol-1-phosphate</traditional_iupac>
  <cas_registry_number>15806-48-1</cas_registry_number>
  <smiles>OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O</smiles>
  <inchi>InChI=1S/C6H15O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3-11H,1-2H2,(H2,12,13,14)/t3-,4-,5-,6-/m1/s1</inchi>
  <inchikey>GACTWZZMVMUKNG-KVTDHHQDSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharide phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>alditol 1-phosphate</external_descriptor>
      <external_descriptor>hexitol phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>262.1517</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>262.04536859</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H15O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H15O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3-11H,1-2H2,(H2,12,13,14)/t3-,4-,5-,6-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GACTWZZMVMUKNG-KVTDHHQDSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>167.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>49.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11955</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446464</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00644</kegg_id>
  <foodb_id>FDB022673</foodb_id>
  <drugbank_id/>
  <chemspider_id/>
  <pubchem_compound_id>130418</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16298</chebi_id>
  <knapsack_id>C00019638</knapsack_id>
  <meta_cyc_id>MANNITOL-1P</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:17 UTC</creation_date>
  <update_date>2020-04-16 20:39:44 UTC</update_date>
  <accession>BMDB0001532</accession>
  <secondary_accessions>
    <accession>BMDB01532</accession>
  </secondary_accessions>
  <name>dATP</name>
  <description/>
  <synonyms>
    <synonym>2'-Deoxyadenosine 5'-triphosphate</synonym>
    <synonym>Deoxyadenosine 5'-triphosphate</synonym>
    <synonym>2'-Deoxyadenosine 5'-triphosphoric acid</synonym>
    <synonym>Deoxyadenosine 5'-triphosphoric acid</synonym>
    <synonym>Deoxyadenosine triphosphoric acid</synonym>
    <synonym>2'-Deoxy-5'-ATP</synonym>
    <synonym>2'-Deoxy-ATP</synonym>
    <synonym>2'-Deoxyadenosine triphosphate</synonym>
    <synonym>dATP</synonym>
    <synonym>Deoxy-ATP</synonym>
    <synonym>Deoxyadenosine-triphosphate</synonym>
    <synonym>2'-Deoxyadenosine triphosphate, 14C-labeled</synonym>
    <synonym>2'-Deoxyadenosine triphosphate, monomagnesium salt</synonym>
    <synonym>2'-Deoxyadenosine triphosphate, trisodium salt</synonym>
    <synonym>2'-Deoxyadenosine triphosphate, p'-(32)p-labeled</synonym>
    <synonym>dATP CPD</synonym>
  </synonyms>
  <chemical_formula>C10H16N5O12P3</chemical_formula>
  <average_molecular_weight>491.1816</average_molecular_weight>
  <monisotopic_moleculate_weight>491.000830537</monisotopic_moleculate_weight>
  <iupac_name>({[({[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</iupac_name>
  <traditional_iupac>dATP</traditional_iupac>
  <cas_registry_number>1927-31-7</cas_registry_number>
  <smiles>NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1</smiles>
  <inchi>InChI=1S/C10H16N5O12P3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(25-7)2-24-29(20,21)27-30(22,23)26-28(17,18)19/h3-7,16H,1-2H2,(H,20,21)(H,22,23)(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1</inchi>
  <inchikey>SUYVUBYJARFZHO-RRKCRQDMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate group  linked to the ribose moiety lacking a hydroxyl group at position 2.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine deoxyribonucleotides</sub_class>
    <direct_parent>Purine 2'-deoxyribonucleoside triphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine 2'-deoxyribonucleoside triphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2'-deoxyadenosine 5'-phosphate</external_descriptor>
      <external_descriptor>Deoxyribonucleotides</external_descriptor>
      <external_descriptor>purine 2'-deoxyribonucleoside 5'-triphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>({[({[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>491.1816</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>491.000830537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H16N5O12P3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H16N5O12P3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(25-7)2-24-29(20,21)27-30(22,23)26-28(17,18)19/h3-7,16H,1-2H2,(H,20,21)(H,22,23)(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SUYVUBYJARFZHO-RRKCRQDMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>258.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>94.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38109</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181478</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00131</kegg_id>
  <foodb_id>FDB022674</foodb_id>
  <drugbank_id>DB03222</drugbank_id>
  <chemspider_id>15194</chemspider_id>
  <pubchem_compound_id>15993</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16284</chebi_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>33969</bigg_id>
  <wikipedia_id>Deoxyadenosine triphosphate</wikipedia_id>
  <metlin_id>6303</metlin_id>
  <synthesis_reference>Munch-Petersen, Agnete.  Formation in vitro of deoxyadenosine triphosphate from deoxyadenosine in Ehrlich ascites cells.    Biochemical and Biophysical Research Communications  (1960),  3  392-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:18 UTC</creation_date>
  <update_date>2020-03-13 16:28:39 UTC</update_date>
  <accession>BMDB0001533</accession>
  <secondary_accessions>
    <accession>BMDB01533</accession>
  </secondary_accessions>
  <name>5,10-Methylene-THF</name>
  <description/>
  <synonyms>
    <synonym>(6R)-5,10-Methylenetetrahydrofolate</synonym>
    <synonym>(6R)-5,10-Methylenetetrahydrofolic acid</synonym>
    <synonym>5,10-Methenyltetrahydropteroylglutamate</synonym>
    <synonym>5,10-Methylene-6-hydrofolate</synonym>
    <synonym>5,10-Methylene-6-hydrofolic acid</synonym>
    <synonym>5,10-Methylenetetrahydrofolate</synonym>
    <synonym>5,10-Methylenetetrahydrofolic acid</synonym>
    <synonym>N5&gt;,N10-methylenetetrahydrofolate</synonym>
    <synonym>5,10-Methylene-5,6,7,8-tetrahydrofolate</synonym>
    <synonym>Tetrahydromethylenefolate</synonym>
    <synonym>5,10-Methylenetetrahydrofolate, (D-glu)-isomer</synonym>
    <synonym>CH2H4Folate</synonym>
    <synonym>5,10-Methylenetetrahydrofolate monohydrochloride, (L-glu)-isomer</synonym>
    <synonym>5,10-Methylenetetrahydrofolate, (L-glu)-(S)-isomer</synonym>
  </synonyms>
  <chemical_formula>C20H23N7O6</chemical_formula>
  <average_molecular_weight>457.4399</average_molecular_weight>
  <monisotopic_moleculate_weight>457.170981503</monisotopic_moleculate_weight>
  <iupac_name>2-({4-[(6aR)-3-amino-1-oxo-1H,2H,5H,6H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid</iupac_name>
  <traditional_iupac>2-({4-[(6aR)-3-amino-1-oxo-2H,5H,6H,6aH,7H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid</traditional_iupac>
  <cas_registry_number>31690-11-6</cas_registry_number>
  <smiles>[H][C@@]12CN(CN1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)NC(CCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13?/m1/s1</inchi>
  <inchikey>QYNUQALWYRSVHF-PZORYLMUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Tetrahydrofolic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylarylamines</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Glutamic acid and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hippuric acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazopyrazines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylimidazolidines</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzamide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoic acid or derivatives</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkylarylamine</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hippuric acid</substituent>
      <substituent>Hippuric acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazolidine</substituent>
      <substituent>Imidazopyrazine</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylimidazolidine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tetrahydrofolic acid</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-({4-[(6aR)-3-amino-1-oxo-1H,2H,5H,6H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>457.4399</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>457.170981503</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CN(CN1C1=C(NC2)N=C(N)NC1=O)C1=CC=C(C=C1)C(=O)NC(CCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H23N7O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QYNUQALWYRSVHF-PZORYLMUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>189.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>123.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178926</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178928</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181253</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00143</kegg_id>
  <foodb_id>FDB022675</foodb_id>
  <drugbank_id/>
  <chemspider_id>388320</chemspider_id>
  <pubchem_compound_id>439175</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15636</chebi_id>
  <knapsack_id>C00007250</knapsack_id>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>34022</bigg_id>
  <wikipedia_id/>
  <metlin_id>6304</metlin_id>
  <synthesis_reference>Agrawal, Nitish; Mihai, Cornelia; Kohen, Amnon.  Microscale synthesis of isotopically labeled R-[6-xH]N5,N10-methylene-5,6,7,8-tetrahydrofolate as a cofactor for thymidylate synthase.    Analytical Biochemistry  (2004),  328(1),  44-50.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00083</protein_accession>
      <name>Serine hydroxymethyltransferase, mitochondrial</name>
      <uniprot_id>Q3SZ20</uniprot_id>
      <gene_name>SHMT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00087</protein_accession>
      <name>Serine hydroxymethyltransferase, cytosolic</name>
      <uniprot_id>Q5E9P9</uniprot_id>
      <gene_name>SHMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00374</protein_accession>
      <name>Bifunctional methylenetetrahydrofolate dehydrogenase/cyclohydrolase, mitochondrial</name>
      <uniprot_id>Q0P5C2</uniprot_id>
      <gene_name>MTHFD2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00536</protein_accession>
      <name>Thymidylate synthase</name>
      <uniprot_id>Q2TA32</uniprot_id>
      <gene_name>TYMS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:19 UTC</creation_date>
  <update_date>2020-03-13 16:28:40 UTC</update_date>
  <accession>BMDB0001534</accession>
  <secondary_accessions>
    <accession>BMDB01534</accession>
  </secondary_accessions>
  <name>5-Formiminotetrahydrofolic acid</name>
  <description>5-Formiminotetrahydrofolic acid belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. 5-Formiminotetrahydrofolic acid is possibly soluble (in water) and a very strong basic compound (based on its pKa). 5-Formiminotetrahydrofolic acid can be converted into 5,10-methenyltetrahydrofolic acid through its interaction with the enzyme formimidoyltransferase-cyclodeaminase. In cattle, 5-formiminotetrahydrofolic acid is involved in the metabolic pathway called the folate metabolism pathway.</description>
  <synonyms>
    <synonym>5-Formimidoyltetrahydrofolate</synonym>
    <synonym>5-Formimidoyltetrahydrofolic acid</synonym>
    <synonym>5-Formiminotetrahydrofolate</synonym>
  </synonyms>
  <chemical_formula>C20H24N8O6</chemical_formula>
  <average_molecular_weight>472.4546</average_molecular_weight>
  <monisotopic_moleculate_weight>472.18188054</monisotopic_moleculate_weight>
  <iupac_name>2-[(4-{[(2-amino-5-carboximidoyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</iupac_name>
  <traditional_iupac>2-[(4-{[(2-amino-5-carboximidoyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</traditional_iupac>
  <cas_registry_number>2311-81-1</cas_registry_number>
  <smiles>NC1=NC2=C(N(C=N)C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)CN2)C(=O)N1</smiles>
  <inchi>InChI=1S/C20H24N8O6/c21-9-28-12(8-24-16-15(28)18(32)27-20(22)26-16)7-23-11-3-1-10(2-4-11)17(31)25-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,21,23H,5-8H2,(H,25,31)(H,29,30)(H,33,34)(H4,22,24,26,27,32)</inchi>
  <inchikey>YCWUVLPMLLBDCU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as imidazoles. Imidazoles are compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Azoles</class>
    <sub_class>Imidazoles</sub_class>
    <direct_parent>Imidazoles</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>an aromatic compound</external_descriptor>
      <external_descriptor>imidazole</external_descriptor>
      <external_descriptor>mancude organic heteromonocyclic parent</external_descriptor>
      <external_descriptor>monocyclic heteroarene</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>6.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4-{[(2-amino-5-carboximidoyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>472.4546</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>472.18188054</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N(C=N)C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)CN2)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H24N8O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H24N8O6/c21-9-28-12(8-24-16-15(28)18(32)27-20(22)26-16)7-23-11-3-1-10(2-4-11)17(31)25-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,21,23H,5-8H2,(H,25,31)(H,29,30)(H,33,34)(H4,22,24,26,27,32)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YCWUVLPMLLBDCU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>222.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>139.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>312387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>357630</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00664</kegg_id>
  <foodb_id>FDB022676</foodb_id>
  <drugbank_id/>
  <chemspider_id>11267158</chemspider_id>
  <pubchem_compound_id>530</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15639</chebi_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>35643</bigg_id>
  <wikipedia_id>5-Formiminotetrahydrofolate</wikipedia_id>
  <metlin_id>6305</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:20 UTC</creation_date>
  <update_date>2020-04-15 21:57:14 UTC</update_date>
  <accession>BMDB0001536</accession>
  <secondary_accessions>
    <accession>BMDB01536</accession>
  </secondary_accessions>
  <name>Formamide</name>
  <description/>
  <synonyms>
    <synonym>Ameisensaeureamid</synonym>
    <synonym>Carbamaldehyde</synonym>
    <synonym>Formamid</synonym>
    <synonym>Formimidic acid</synonym>
    <synonym>Methanamid</synonym>
    <synonym>Methanamide</synonym>
    <synonym>Formimidate</synonym>
  </synonyms>
  <chemical_formula>CH3NO</chemical_formula>
  <average_molecular_weight>45.0406</average_molecular_weight>
  <monisotopic_moleculate_weight>45.021463723</monisotopic_moleculate_weight>
  <iupac_name>formamide</iupac_name>
  <traditional_iupac>formamide</traditional_iupac>
  <cas_registry_number>75-12-7</cas_registry_number>
  <smiles>NC=O</smiles>
  <inchi>InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3)</inchi>
  <inchikey>ZHNUHDYFZUAESO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboximidic acids and derivatives</class>
    <sub_class>Carboximidic acids</sub_class>
    <direct_parent>Carboximidic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>carboximidic acid</external_descriptor>
      <external_descriptor>one-carbon compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>2.55 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.51</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>16.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>formamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>45.0406</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>45.021463723</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>CH3NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZHNUHDYFZUAESO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>43.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>9.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>3.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9297</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>83520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>83521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>83522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>145139</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00488</kegg_id>
  <foodb_id>FDB022677</foodb_id>
  <drugbank_id/>
  <chemspider_id>693</chemspider_id>
  <pubchem_compound_id>713</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16397</chebi_id>
  <knapsack_id/>
  <meta_cyc_id>FORMAMIDE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Formamide</wikipedia_id>
  <metlin_id>4182</metlin_id>
  <synthesis_reference>Magill, P. L. Formamide. Journal of Industrial and Engineering Chemistry (Washington, D. C.) (1934), 26 611-14.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:21 UTC</creation_date>
  <update_date>2020-04-15 23:55:52 UTC</update_date>
  <accession>BMDB0001537</accession>
  <secondary_accessions>
    <accession>BMDB01537</accession>
  </secondary_accessions>
  <name>6-Hydroxydopamine</name>
  <description/>
  <synonyms>
    <synonym>2,4,5-Trihydroxyphenethylamine</synonym>
    <synonym>6-OHDA</synonym>
    <synonym>Hydroxydopamine</synonym>
    <synonym>Oxidopamina</synonym>
    <synonym>Oxidopaminum</synonym>
    <synonym>Topamine</synonym>
    <synonym>5-(2-Aminoethyl)-1,2,4-benzenetriol</synonym>
    <synonym>6-Hydroxy-dopamine</synonym>
    <synonym>Oxidopamine hydrochloride</synonym>
    <synonym>Oxidopamine hydrobromide</synonym>
    <synonym>6 Hydroxydopamine</synonym>
    <synonym>Hydrochloride, oxidopamine</synonym>
    <synonym>Hydrobromide, oxidopamine</synonym>
    <synonym>6-Hydroxydopamine</synonym>
    <synonym>Oxidopamine</synonym>
  </synonyms>
  <chemical_formula>C8H11NO3</chemical_formula>
  <average_molecular_weight>169.1778</average_molecular_weight>
  <monisotopic_moleculate_weight>169.073893223</monisotopic_moleculate_weight>
  <iupac_name>5-(2-aminoethyl)benzene-1,2,4-triol</iupac_name>
  <traditional_iupac>hydroxydopamine</traditional_iupac>
  <cas_registry_number>1199-18-4</cas_registry_number>
  <smiles>NCCC1=C(O)C=C(O)C(O)=C1</smiles>
  <inchi>InChI=1S/C8H11NO3/c9-2-1-5-3-7(11)8(12)4-6(5)10/h3-4,10-12H,1-2,9H2</inchi>
  <inchikey>DIVDFFZHCJEHGG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as catecholamines and derivatives. Catecholamines and derivatives are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Benzenediols</sub_class>
    <direct_parent>Catecholamines and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>2-arylethylamines</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxyquinols and derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenethylamines</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>2-arylethylamine</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Catecholamine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyquinol derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenethylamine</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>benzenetriol</external_descriptor>
      <external_descriptor>catecholamine</external_descriptor>
      <external_descriptor>primary amino compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>232 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>5-(2-aminoethyl)benzene-1,2,4-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>169.1778</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>169.073893223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCC1=C(O)C=C(O)C(O)=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H11NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H11NO3/c9-2-1-5-3-7(11)8(12)4-6(5)10/h3-4,10-12H,1-2,9H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DIVDFFZHCJEHGG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>86.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343878</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022678</foodb_id>
  <kegg_id/>
  <drugbank_id/>
  <chemspider_id>4463</chemspider_id>
  <pubchem_compound_id>4624</pubchem_compound_id>
  <chebi_id>78741</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-7666</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Oxidopamine</wikipedia_id>
  <metlin_id>6307</metlin_id>
  <synthesis_reference>Napolitano, Alessandra; Crescenzi, Orlando; Pezzella, Alessandro; Prota, Giuseppe. Generation of the Neurotoxin 6-Hydroxydopamine by Peroxidase/H2O2 Oxidation of Dopamine. Journal of Medicinal Chemistry (1995), 38(6), 917-22.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:22 UTC</creation_date>
  <update_date>2020-03-13 16:28:41 UTC</update_date>
  <accession>BMDB0001538</accession>
  <secondary_accessions>
    <accession>BMDB01538</accession>
  </secondary_accessions>
  <name>3-Pyridylacetic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Pyridylacetate</synonym>
    <synonym>2-(3-Pyridyl)acetate</synonym>
    <synonym>2-(3-Pyridyl)acetic acid</synonym>
    <synonym>2-(Pyridin-3-yl)acetate</synonym>
    <synonym>2-(Pyridin-3-yl)acetic acid</synonym>
    <synonym>3-Carboxymethylpyridine</synonym>
    <synonym>a-(3-Pyridyl)acetate</synonym>
    <synonym>a-(3-Pyridyl)acetic acid</synonym>
    <synonym>alpha-(3-Pyridyl)acetate</synonym>
    <synonym>alpha-(3-Pyridyl)acetic acid</synonym>
    <synonym>Coletin</synonym>
    <synonym>Lessterol</synonym>
    <synonym>Lioxone</synonym>
    <synonym>Minedil</synonym>
    <synonym>Piridil</synonym>
    <synonym>Piristerol</synonym>
    <synonym>Pyridin-3-ylacetate</synonym>
    <synonym>Pyridin-3-ylacetic acid</synonym>
    <synonym>Toneon</synonym>
    <synonym>2-(3-Pyridine)acetic acid</synonym>
    <synonym>3-Pyridineacetic acid</synonym>
  </synonyms>
  <chemical_formula>C7H7NO2</chemical_formula>
  <average_molecular_weight>137.136</average_molecular_weight>
  <monisotopic_moleculate_weight>137.047678473</monisotopic_moleculate_weight>
  <iupac_name>2-(pyridin-3-yl)acetic acid</iupac_name>
  <traditional_iupac>3-pyridylacetic acid</traditional_iupac>
  <cas_registry_number>501-81-5</cas_registry_number>
  <smiles>OC(=O)CC1=CN=CC=C1</smiles>
  <inchi>InChI=1S/C7H7NO2/c9-7(10)4-6-2-1-3-8-5-6/h1-3,5H,4H2,(H,9,10)</inchi>
  <inchikey>WGNUNYPERJMVRM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class/>
    <direct_parent>Pyridines and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyridine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>monocarboxylic acid</external_descriptor>
      <external_descriptor>pyridines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(pyridin-3-yl)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>137.136</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>137.047678473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CC1=CN=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H7NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H7NO2/c9-7(10)4-6-2-1-3-8-5-6/h1-3,5H,4H2,(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WGNUNYPERJMVRM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>50.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288251</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327309</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022679</foodb_id>
  <kegg_id/>
  <drugbank_id/>
  <chemspider_id>106</chemspider_id>
  <pubchem_compound_id>108</pubchem_compound_id>
  <chebi_id>86390</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6308</metlin_id>
  <synthesis_reference>aquet, Andre; Marison, Ian W.; Meyer, Hans Peter; Von Stockar, Urs.  Choice of a method for in situ recovery of 3-pyridylacetic acid formed by biotransformation with Pseudomonas oleovorans.    Chimia  (1996),  50(9), 426-427.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:23 UTC</creation_date>
  <update_date>2020-04-15 22:10:21 UTC</update_date>
  <accession>BMDB0001539</accession>
  <secondary_accessions>
    <accession>BMDB01539</accession>
  </secondary_accessions>
  <name>Dimethyl-L-arginine</name>
  <description>Asymmetric dimethylarginine, also known as N(g),N(g)-dimethylarginine or guanidino-N,N-dimethylarginine, belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Asymmetric dimethylarginine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Asymmetric dimethylarginine exists in all eukaryotes, ranging from yeast to humans. Asymmetric dimethylarginine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>ADMA</synonym>
    <synonym>Guanidino-N,N-dimethylarginine</synonym>
    <synonym>N,N-Dimethylarginine</synonym>
    <synonym>N(5)-((Dimethylamino)iminomethyl)-L-ornithine</synonym>
    <synonym>NG,NG-Dimethyl-L-arginine</synonym>
    <synonym>N(g),N(g)-Dimethylarginine</synonym>
    <synonym>N(g)-Dimethylarginine</synonym>
    <synonym>N(g1),N(g1)-Dimethylarginine</synonym>
    <synonym>Nomega,nomega-dimethyl-L-arginine</synonym>
    <synonym>2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoate</synonym>
    <synonym>2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoic acid</synonym>
    <synonym>Dimethyl-L-arginine</synonym>
    <synonym>N(Omega),N(omega)-dimethyl-L-arginine</synonym>
    <synonym>NG,NG-Dimethylarginine</synonym>
    <synonym>NG-Dimethylarginine</synonym>
    <synonym>Nomega,nomega'-dimethyl-L-arginine</synonym>
    <synonym>Asymmetric dimethylarginine</synonym>
  </synonyms>
  <chemical_formula>C8H18N4O2</chemical_formula>
  <average_molecular_weight>202.2541</average_molecular_weight>
  <monisotopic_moleculate_weight>202.14297584</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid</iupac_name>
  <traditional_iupac>asymmetric dimethylarginine</traditional_iupac>
  <cas_registry_number>30315-93-6</cas_registry_number>
  <smiles>N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O</smiles>
  <inchi>InChI=1S/C8H18N4O2/c1-12(2)8(10)11-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14)/t6-/m0/s1</inchi>
  <inchikey>YDGMGEXADBMOMJ-LURJTMIESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Arginine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Guanidines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Arginine or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-arginine derivative</external_descriptor>
      <external_descriptor>dimethylarginine</external_descriptor>
      <external_descriptor>guanidines</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>12.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>202.2541</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>202.14297584</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H18N4O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H18N4O2/c1-12(2)8(10)11-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14)/t6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YDGMGEXADBMOMJ-LURJTMIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>104.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>53.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>85719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>85720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>85721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>147858</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>147859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>147860</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1.1+/-0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>1.3-2.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By HPLC</comment>
      <references>
        <reference>
          <reference_text>Chan JR, Boger RH, Bode-Boger SM, Tangphao O, Tsao PS, Blaschke TF, Cooke JP: Asymmetric dimethylarginine increases mononuclear cell adhesiveness in hypercholesterolemic humans. Arterioscler Thromb Vasc Biol. 2000 Apr;20(4):1040-6. doi: 10.1161/01.atv.20.4.1040.</reference_text>
          <pubmed_id>10764670</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>1+/-1</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>0.8+/-0.2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.08 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.09 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.1 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.10 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk by LC-HRMS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>4+/-3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>0.33 +/- 0.14</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>0.9+/-0.2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>0.8+/-0.2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB000508</foodb_id>
  <kegg_id>C03626</kegg_id>
  <drugbank_id>DB01686</drugbank_id>
  <chemspider_id>110375</chemspider_id>
  <pubchem_compound_id>123831</pubchem_compound_id>
  <chebi_id>17929</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Asymmetric dimethylarginine</wikipedia_id>
  <metlin_id>6309</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:25 UTC</creation_date>
  <update_date>2020-03-13 16:28:42 UTC</update_date>
  <accession>BMDB0001541</accession>
  <secondary_accessions>
    <accession>BMDB01541</accession>
  </secondary_accessions>
  <name>Guanosine hexaphosphate adenosine</name>
  <description/>
  <synonyms>
    <synonym>Guanosine hexaphosphoric acid adenosine</synonym>
    <synonym>{[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinate</synonym>
  </synonyms>
  <chemical_formula>C20H30N10O26P6</chemical_formula>
  <average_molecular_weight>1012.3462</average_molecular_weight>
  <monisotopic_moleculate_weight>1011.975840254</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphinic acid</traditional_iupac>
  <cas_registry_number>204376-34-1</cas_registry_number>
  <smiles>NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C20H30N10O26P6/c21-14-8-15(24-3-23-14)29(4-25-8)18-12(33)10(31)6(50-18)1-48-57(36,37)52-59(40,41)54-61(44,45)56-62(46,47)55-60(42,43)53-58(38,39)49-2-7-11(32)13(34)19(51-7)30-5-26-9-16(30)27-20(22)28-17(9)35/h3-7,10-13,18-19,31-34H,1-2H2,(H,36,37)(H,38,39)(H,40,41)(H,42,43)(H,44,45)(H,46,47)(H2,21,23,24)(H3,22,27,28,35)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1</inchi>
  <inchikey>QESDWYZADJGZRW-INFSMZHSSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside polyphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside polyphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1012.3462</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1011.975840254</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H30N10O26P6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H30N10O26P6/c21-14-8-15(24-3-23-14)29(4-25-8)18-12(33)10(31)6(50-18)1-48-57(36,37)52-59(40,41)54-61(44,45)56-62(46,47)55-60(42,43)53-58(38,39)49-2-7-11(32)13(34)19(51-7)30-5-26-9-16(30)27-20(22)28-17(9)35/h3-7,10-13,18-19,31-34H,1-2H2,(H,36,37)(H,38,39)(H,40,41)(H,42,43)(H,44,45)(H,46,47)(H2,21,23,24)(H3,22,27,28,35)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QESDWYZADJGZRW-INFSMZHSSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>542.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>188.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>77.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367164</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022680</foodb_id>
  <kegg_id/>
  <drugbank_id/>
  <chemspider_id>13167072</chemspider_id>
  <pubchem_compound_id>16038493</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:26 UTC</creation_date>
  <update_date>2020-04-15 22:33:01 UTC</update_date>
  <accession>BMDB0001542</accession>
  <secondary_accessions>
    <accession>BMDB01542</accession>
  </secondary_accessions>
  <name>N-Acetyllactosamine</name>
  <description/>
  <synonyms>
    <synonym>beta-D-Galactosyl-1,4-N-acetyl-D-glucosamine</synonym>
    <synonym>Galb1-4glcnacb</synonym>
    <synonym>Galbeta1-4glcnacbeta</synonym>
    <synonym>LacNAc</synonym>
    <synonym>N-Acetyl-beta-lactosamine</synonym>
    <synonym>beta-D-Galactosyl-1,4-N-acetyl-beta-D-glucosamine</synonym>
    <synonym>b-D-Galactosyl-1,4-N-acetyl-D-glucosamine</synonym>
    <synonym>Β-D-galactosyl-1,4-N-acetyl-D-glucosamine</synonym>
    <synonym>N-Acetyl-b-lactosamine</synonym>
    <synonym>N-Acetyl-β-lactosamine</synonym>
    <synonym>b-D-Galactosyl-1,4-N-acetyl-b-D-glucosamine</synonym>
    <synonym>Β-D-galactosyl-1,4-N-acetyl-β-D-glucosamine</synonym>
    <synonym>beta-delta-Galactosyl-1,4-N-acetyl-beta-delta-glucosamine</synonym>
    <synonym>beta-delta-Galactosyl-1,4-N-acetyl-delta-glucosamine</synonym>
    <synonym>D-Galactopyranosyl</synonym>
    <synonym>delta-Galactopyranosyl</synonym>
    <synonym>N-Acetyl-lactosamine</synonym>
    <synonym>ACETYL lactosamine</synonym>
  </synonyms>
  <chemical_formula>C14H25NO11</chemical_formula>
  <average_molecular_weight>383.3484</average_molecular_weight>
  <monisotopic_moleculate_weight>383.142760647</monisotopic_moleculate_weight>
  <iupac_name>N-[(2R,3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide</iupac_name>
  <traditional_iupac>N-acetyllactosamine</traditional_iupac>
  <cas_registry_number>32181-59-2</cas_registry_number>
  <smiles>CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C14H25NO11/c1-4(18)15-7-9(20)12(6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8+,9-,10+,11-,12-,13-,14+/m1/s1</inchi>
  <inchikey>KFEUJDWYNGMDBV-LODBTCKLSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Acylaminosugars</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Disaccharides</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Acylaminosugar</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>beta-D-galactopyranosyl-(1-&gt;4)-N-acetyl-D-glucosamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-[(2R,3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>383.3484</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>383.142760647</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H25NO11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H25NO11/c1-4(18)15-7-9(20)12(6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8+,9-,10+,11-,12-,13-,14+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KFEUJDWYNGMDBV-LODBTCKLSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>198.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>35.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1637</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1668</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB019860</foodb_id>
  <kegg_id>C00611</kegg_id>
  <drugbank_id/>
  <chemspider_id>388404</chemspider_id>
  <pubchem_compound_id>439271</pubchem_compound_id>
  <chebi_id>16153</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>N-Acetyllactosamine</wikipedia_id>
  <metlin_id>4231</metlin_id>
  <synthesis_reference>Dekany, Gyula; Agoston, Karoly; Bajza, Istvan; Boejstrup, Marie; Kroeger, Lars.  Process for the large-scale preparation of N-acetyllactosamine, lactosamine, lactosamine salts and lactosamine-containing oligosaccharides.    PCT Int. Appl.  (2007),     44pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00604</protein_accession>
      <name>Beta-1,4-galactosyltransferase 1</name>
      <uniprot_id>P08037</uniprot_id>
      <gene_name>B4GALT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00640</protein_accession>
      <name>Beta-1,4-galactosyltransferase 3</name>
      <uniprot_id>Q5EA87</uniprot_id>
      <gene_name>B4GALT3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00790</protein_accession>
      <name>Beta-galactoside alpha-2,6-sialyltransferase 2</name>
      <uniprot_id>A5D7T4</uniprot_id>
      <gene_name>ST6GAL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:27 UTC</creation_date>
  <update_date>2020-03-13 16:28:43 UTC</update_date>
  <accession>BMDB0001543</accession>
  <secondary_accessions>
    <accession>BMDB01543</accession>
  </secondary_accessions>
  <name>Diguanosine hexaphosphate</name>
  <description/>
  <synonyms>
    <synonym>Diguanosine hexaphosphoric acid</synonym>
    <synonym>Guanosine 5'-(heptahydrogen hexaphosphate) p-&gt;5'-ester with guanosine</synonym>
    <synonym>Bis({[({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinate</synonym>
  </synonyms>
  <chemical_formula>C20H31N10O30P7</chemical_formula>
  <average_molecular_weight>1108.3255</average_molecular_weight>
  <monisotopic_moleculate_weight>1107.937085286</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxyphosphinic acid</traditional_iupac>
  <cas_registry_number>83269-95-8</cas_registry_number>
  <smiles>NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=C(N)NC4=O)[C@@H](O)[C@H]2O)C(=O)N1</smiles>
  <inchi>InChI=1S/C20H31N10O30P7/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(53-17)1-51-61(37,38)55-63(41,42)57-65(45,46)59-67(49,50)60-66(47,48)58-64(43,44)56-62(39,40)52-2-6-10(32)12(34)18(54-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H,47,48)(H,49,50)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1</inchi>
  <inchikey>SUBCCLLJUFUQFC-MHARETSRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as (5'-&gt;5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'-&gt;5')-phosphodiester linkage.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>(5'-&gt;5')-dinucleotides</class>
    <sub_class/>
    <direct_parent>(5'-&gt;5')-dinucleotides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Purine nucleotide sugars</alternative_parent>
      <alternative_parent>Purine ribonucleoside monophosphates</alternative_parent>
      <alternative_parent>Purine ribonucleoside polyphosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>(5'-&gt;5')-dinucleotide</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleotide sugar</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purine ribonucleoside polyphosphate</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-7.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1108.3255</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1107.937085286</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=C(N)NC4=O)[C@@H](O)[C@H]2O)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H31N10O30P7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H31N10O30P7/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(53-17)1-51-61(37,38)55-63(41,42)57-65(45,46)59-67(49,50)60-66(47,48)58-64(43,44)56-62(39,40)52-2-6-10(32)12(34)18(54-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H,47,48)(H,49,50)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SUBCCLLJUFUQFC-MHARETSRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>604.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>201.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>82.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>20</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>308601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>352821</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022681</foodb_id>
  <kegg_id/>
  <drugbank_id/>
  <chemspider_id/>
  <pubchem_compound_id>53477734</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Schluter, Hartmut; Gross, Isolde; Bachmann, Jurgen; Kaufmann, Raimund; Van Der Giet, Marcus; Tepel, Martin; Nofer, Jerzy-Roch; Assmann, Gerd; Karas, Michael; Jankowski, Joachim; Zidek, Walter.  Adenosine(5') oligophospho-(5') guanosines and guanosine(5') oligophospho-(5') guanosines in human platelets.    Journal of Clinical Investigation  (1998),  101(3),  682-688.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:28 UTC</creation_date>
  <update_date>2020-04-15 22:26:30 UTC</update_date>
  <accession>BMDB0001545</accession>
  <secondary_accessions>
    <accession>BMDB01545</accession>
  </secondary_accessions>
  <name>Pyridoxal</name>
  <description>Pyridoxal, also known as pyridoxaldehyde, belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively. Pyridoxal exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Pyridoxal exists in all living species, ranging from bacteria to humans. In cattle, pyridoxal is involved in the metabolic pathway called the glycine and serine metabolism pathway. Pyridoxal is a potentially toxic compound.</description>
  <synonyms>
    <synonym>3-HYDROXY-5-(hydroxymethyl)-2-methylisonicotinaldehyde</synonym>
    <synonym>Pyridoxaldehyde</synonym>
    <synonym>3-Hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carboxaldehyde</synonym>
  </synonyms>
  <chemical_formula>C8H9NO3</chemical_formula>
  <average_molecular_weight>167.162</average_molecular_weight>
  <monisotopic_moleculate_weight>167.058243159</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde</iupac_name>
  <traditional_iupac>pyridoxal</traditional_iupac>
  <cas_registry_number>66-72-8</cas_registry_number>
  <smiles>CC1=NC=C(CO)C(C=O)=C1O</smiles>
  <inchi>InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3</inchi>
  <inchikey>RADKZDMFGJYCBB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyridine carboxaldehydes</sub_class>
    <direct_parent>Pyridoxals and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Aryl-aldehydes</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyridines</alternative_parent>
      <alternative_parent>Methylpyridines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Aryl-aldehyde</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyridine</substituent>
      <substituent>Methylpyridine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyridoxal</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Water-soluble vitamins</external_descriptor>
      <external_descriptor>a vitamin B6</external_descriptor>
      <external_descriptor>hydroxymethylpyridine</external_descriptor>
      <external_descriptor>methylpyridines</external_descriptor>
      <external_descriptor>monohydroxypyridine</external_descriptor>
      <external_descriptor>pyridinecarbaldehyde</external_descriptor>
      <external_descriptor>vitamin B6</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>165 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>500.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>167.162</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>167.058243159</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=NC=C(CO)C(C=O)=C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H9NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RADKZDMFGJYCBB-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>70.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin B6 Metabolism</name>
      <smpdb_id>SMP0087240</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4881</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1645</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5387</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5392</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438240</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438241</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438243</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38117</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.763 +/- 0.19</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Coburn SP, Mahuren JD, Pauly TA, Ericson KL, Townsend DW: Alkaline phosphatase activity and pyridoxal phosphate concentrations in the milk of various species. J Nutr. 1992 Dec;122(12):2348-53. doi: 10.1093/jn/122.12.2348.</reference_text>
          <pubmed_id>1453218</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>16.185 - 52.601</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309.</reference_text>
          <pubmed_id>17558655</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.541 - 0.763</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Coburn SP, Mahuren JD, Pauly TA, Ericson KL, Townsend DW: Alkaline phosphatase activity and pyridoxal phosphate concentrations in the milk of various species. J Nutr. 1992 Dec;122(12):2348-53. doi: 10.1093/jn/122.12.2348.</reference_text>
          <pubmed_id>1453218</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.619 - 1.740</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
          <pubmed_id>22081685</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.699</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00250</kegg_id>
  <drugbank_id>DB00147</drugbank_id>
  <foodb_id>FDB011169</foodb_id>
  <chemspider_id>1021</chemspider_id>
  <pubchem_compound_id>1050</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17310</chebi_id>
  <knapsack_id>C00007509</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>34393</bigg_id>
  <wikipedia_id>Pyridoxal</wikipedia_id>
  <metlin_id>6312</metlin_id>
  <meta_cyc_id>PYRIDOXAL</meta_cyc_id>
  <synthesis_reference>Fujimoto, Yasuo.  Pyridoxal.    Jpn. Tokkyo Koho  (1971),     2 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Coburn SP, Mahuren JD, Pauly TA, Ericson KL, Townsend DW: Alkaline phosphatase activity and pyridoxal phosphate concentrations in the milk of various species. J Nutr. 1992 Dec;122(12):2348-53. doi: 10.1093/jn/122.12.2348.</reference_text>
      <pubmed_id>1453218</pubmed_id>
    </reference>
    <reference>
      <reference_text>Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309.</reference_text>
      <pubmed_id>17558655</pubmed_id>
    </reference>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S.</reference_text>
      <pubmed_id>22081685</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113   doi: 10.1016/j.smallrumres.2006.09.013</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:29 UTC</creation_date>
  <update_date>2020-03-13 16:28:44 UTC</update_date>
  <accession>BMDB0001546</accession>
  <secondary_accessions>
    <accession>BMDB01546</accession>
  </secondary_accessions>
  <name>CDP</name>
  <description/>
  <synonyms>
    <synonym>5'-CDP</synonym>
    <synonym>Cytidine 5'-diphosphate</synonym>
    <synonym>Cytidine 5'-diphosphoric acid</synonym>
    <synonym>Cytidine 5'-pyrophosphate</synonym>
    <synonym>Cytidine diphosphate</synonym>
    <synonym>Cytidine, 5'-(trihydrogen pyrophosphate)</synonym>
    <synonym>CYTIDINE-5'-diphosphATE</synonym>
    <synonym>Cytidine 5'-pyrophosphoric acid</synonym>
    <synonym>Cytidine diphosphoric acid</synonym>
    <synonym>Cytidine, 5'-(trihydrogen pyrophosphoric acid)</synonym>
    <synonym>CYTIDINE-5'-diphosphoric acid</synonym>
    <synonym>Cytidine-diphosphate</synonym>
    <synonym>Diphosphate, cytidine</synonym>
  </synonyms>
  <chemical_formula>C9H15N3O11P2</chemical_formula>
  <average_molecular_weight>403.1764</average_molecular_weight>
  <monisotopic_moleculate_weight>403.018181361</monisotopic_moleculate_weight>
  <iupac_name>[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</iupac_name>
  <traditional_iupac>CDP</traditional_iupac>
  <cas_registry_number>63-38-7</cas_registry_number>
  <smiles>NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C9H15N3O11P2/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1</inchi>
  <inchikey>ZWIADYZPOWUWEW-XVFCMESISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group  linked to the ribose moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine ribonucleotides</sub_class>
    <direct_parent>Pyrimidine ribonucleoside diphosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidine ribonucleoside diphosphate</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ribonucleotides</external_descriptor>
      <external_descriptor>cytidine 5'-phosphate</external_descriptor>
      <external_descriptor>pyrimidine ribonucleoside 5'-diphosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>logp</kind>
      <value>2.44</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.033</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>403.1764</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>403.018181361</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H15N3O11P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H15N3O11P2/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZWIADYZPOWUWEW-XVFCMESISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>221.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>76.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27626</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27627</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447999</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00112</kegg_id>
  <drugbank_id>DB04555</drugbank_id>
  <foodb_id>FDB022683</foodb_id>
  <chemspider_id>5902</chemspider_id>
  <pubchem_compound_id>6132</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17239</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>33901</bigg_id>
  <wikipedia_id>CDP</wikipedia_id>
  <metlin_id>6313</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference>Chambers, Robert Warner; Shapiro, Philip; Kurkov, Viktor.  Synthesis of cytidine 5'-diphosphate and guanosine 5'-diphosphate.    Journal of the American Chemical Society  (1960),  82  970-5.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00078</protein_accession>
      <name>CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase, mitochondrial</name>
      <uniprot_id>Q2KJ28</uniprot_id>
      <gene_name>PGS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00079</protein_accession>
      <name>Phosphatidate cytidylyltransferase 2</name>
      <uniprot_id>A0JNC1</uniprot_id>
      <gene_name>CDS2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00133</protein_accession>
      <name>Manganese-dependent ADP-ribose/CDP-alcohol diphosphatase</name>
      <uniprot_id>A7YY53</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00390</protein_accession>
      <name>Cholinephosphotransferase 1</name>
      <uniprot_id>Q1LZE6</uniprot_id>
      <gene_name>CHPT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00391</protein_accession>
      <name>Ethanolaminephosphotransferase 1</name>
      <uniprot_id>Q17QM4</uniprot_id>
      <gene_name>SELI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00392</protein_accession>
      <name>Ethanolamine-phosphate cytidylyltransferase</name>
      <uniprot_id>Q5EA75</uniprot_id>
      <gene_name>PCYT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00393</protein_accession>
      <name>Dolichol kinase</name>
      <uniprot_id>Q58CR4</uniprot_id>
      <gene_name>DOLK</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:31 UTC</creation_date>
  <update_date>2020-04-16 20:40:42 UTC</update_date>
  <accession>BMDB0001547</accession>
  <secondary_accessions>
    <accession>BMDB01547</accession>
  </secondary_accessions>
  <name>Corticosterone</name>
  <description>Corticosterone, also known as Corticosterone, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, corticosterone is considered to be a steroid lipid molecule. Corticosterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Corticosterone participates in a number of enzymatic reactions, within cattle. In particular, Corticosterone can be converted into 18-hydroxycorticosterone through its interaction with the enzyme cytochrome P450 11B1. In addition, Corticosterone can be biosynthesized from 11b-hydroxyprogesterone; which is catalyzed by the enzyme steroid 21-hydroxylase. In cattle, corticosterone is involved in the metabolic pathway called the steroidogenesis pathway. Corticosterone is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(11beta)-11,21-Dihydroxypregn-4-ene-3,20-dione</synonym>
    <synonym>11beta,21-Dihydroxy-4-pregnene-3,20-dione</synonym>
    <synonym>11beta,21-Dihydroxyprogesterone</synonym>
    <synonym>17-Deoxycortisol</synonym>
    <synonym>Kendall's compound b</synonym>
    <synonym>Reichstein's substance H</synonym>
    <synonym>(11b)-11,21-Dihydroxypregn-4-ene-3,20-dione</synonym>
    <synonym>(11Β)-11,21-dihydroxypregn-4-ene-3,20-dione</synonym>
    <synonym>11b,21-Dihydroxy-4-pregnene-3,20-dione</synonym>
    <synonym>11Β,21-dihydroxy-4-pregnene-3,20-dione</synonym>
    <synonym>11b,21-Dihydroxyprogesterone</synonym>
    <synonym>11Β,21-dihydroxyprogesterone</synonym>
    <synonym>11,21-Dihydroxypregn-4-ene-3,20-dione</synonym>
    <synonym>11,21-Dihydroxyprogesterone</synonym>
    <synonym>11-Hydroxycorticoaldosterone</synonym>
    <synonym>4-Pregnene-11 corticosteron</synonym>
  </synonyms>
  <chemical_formula>C21H30O4</chemical_formula>
  <average_molecular_weight>346.4605</average_molecular_weight>
  <monisotopic_moleculate_weight>346.214409448</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10S,11S,14S,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10S,11S,14S,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</traditional_iupac>
  <cas_registry_number>50-22-6</cas_registry_number>
  <smiles>[H]OC([H])([H])C(=O)[C@@]1([H])C([H])([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])C([H])([H])C4=C([H])C(=O)C([H])([H])C([H])([H])[C@]4(C([H])([H])[H])[C@@]3([H])[C@@]([H])(O[H])C([H])([H])[C@]12C([H])([H])[H]</smiles>
  <inchi>InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1</inchi>
  <inchikey>OMFXVFTZEKFJBZ-HJTSIMOOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Hydroxysteroids</sub_class>
    <direct_parent>21-hydroxysteroids</direct_parent>
    <alternative_parents>
      <alternative_parent>11-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Gluco/mineralocorticoids, progestogins and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>11-beta-hydroxysteroid</substituent>
      <substituent>11-hydroxysteroid</substituent>
      <substituent>20-oxosteroid</substituent>
      <substituent>21-hydroxysteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Pregnane-skeleton</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Progestogin-skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>11beta-hydroxy steroid</external_descriptor>
      <external_descriptor>20-oxo steroid</external_descriptor>
      <external_descriptor>21-hydroxy steroid</external_descriptor>
      <external_descriptor>3-oxo steroid</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
      <external_descriptor>C21-steroid</external_descriptor>
      <external_descriptor>Mineralocorticoids</external_descriptor>
      <external_descriptor>Pregnane and derivatives [Fig]</external_descriptor>
      <external_descriptor>glucocorticoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>179 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.199 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.94</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10S,11S,14S,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>346.4605</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>346.214409448</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]OC([H])([H])C(=O)[C@@]1([H])C([H])([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])C([H])([H])C4=C([H])C(=O)C([H])([H])C([H])([H])[C@]4(C([H])([H])[H])[C@@]3([H])[C@@]([H])(O[H])C([H])([H])[C@]12C([H])([H])[H]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H30O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OMFXVFTZEKFJBZ-HJTSIMOOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroidogenesis</name>
      <smpdb_id>SMP0087238</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>37</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2276</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13260</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38119</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1646</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1647</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>246096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>246097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>246098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>266040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>266041</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>266042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443903</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C02140</kegg_id>
  <drugbank_id>DB04652</drugbank_id>
  <foodb_id>FDB022684</foodb_id>
  <chemspider_id>5550</chemspider_id>
  <pubchem_compound_id>5753</pubchem_compound_id>
  <chebi_id>16827</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>CORTICOSTERONE</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>39187</bigg_id>
  <wikipedia_id>Corticosterone</wikipedia_id>
  <metlin_id>6314</metlin_id>
  <synthesis_reference>Oliveto, Eugene P.; Smith, Herbert Q.; Gerold, Corinne; Rausser, Richard; Hershberg, E. B.  11-Oxygenated steroids. XIV. New syntheses of corticosterone.    Journal of the American Chemical Society  (1956),  78  1414-16.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:32 UTC</creation_date>
  <update_date>2020-03-13 16:28:46 UTC</update_date>
  <accession>BMDB0001548</accession>
  <secondary_accessions>
    <accession>BMDB01548</accession>
  </secondary_accessions>
  <name>D-Ribose 5-phosphate</name>
  <description>D-Ribose 5-phosphate, also known as D-ribose-5-P, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. D-Ribose 5-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). D-Ribose 5-phosphate exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>5-O-Phosphono-alpha-D-ribofuranose</synonym>
    <synonym>alpha-D-Ribose 5-phosphate</synonym>
    <synonym>5-O-Phosphono-a-D-ribofuranose</synonym>
    <synonym>5-O-Phosphono-α-D-ribofuranose</synonym>
    <synonym>a-D-Ribose 5-phosphate</synonym>
    <synonym>a-D-Ribose 5-phosphoric acid</synonym>
    <synonym>alpha-D-Ribose 5-phosphoric acid</synonym>
    <synonym>Α-D-ribose 5-phosphate</synonym>
    <synonym>Α-D-ribose 5-phosphoric acid</synonym>
    <synonym>D-Ribose 5-phosphoric acid</synonym>
    <synonym>D-Ribofuranose 5-phosphate</synonym>
    <synonym>R-5-p</synonym>
    <synonym>Ribose 5-(dihydrogen phosphate)</synonym>
    <synonym>Ribose 5-monophosphate</synonym>
    <synonym>Ribose 5-phosphate</synonym>
    <synonym>alpha-D-Ribose-5-phosphate</synonym>
    <synonym>Α-D-ribose-5-phosphate</synonym>
    <synonym>D-Ribose 5-phosphate</synonym>
  </synonyms>
  <chemical_formula>C5H11O8P</chemical_formula>
  <average_molecular_weight>230.1098</average_molecular_weight>
  <monisotopic_moleculate_weight>230.01915384</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>α-D-ribose 5-phosphate</traditional_iupac>
  <cas_registry_number>34980-65-9</cas_registry_number>
  <smiles>O[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O</smiles>
  <inchi>InChI=1S/C5H11O8P/c6-3-2(1-12-14(9,10)11)13-5(8)4(3)7/h2-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5+/m1/s1</inchi>
  <inchikey>KTVPXOYAKDPRHY-AIHAYLRMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentose phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D-ribofuranose 5-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5S)-3,4,5-trihydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>230.1098</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>230.01915384</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H11O8P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H11O8P/c6-3-2(1-12-14(9,10)11)13-5(8)4(3)7/h2-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KTVPXOYAKDPRHY-AIHAYLRMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>136.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102812</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>102819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2069</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448567</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1448577</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By GC-MS and LC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Characterization of the biochemical variability of bovine milk using metabolomics</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>This is a duplicate concentration of concentration_id 8150, unpexported by An Chi on Aug 20, 2018</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C03736</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB001615</foodb_id>
  <chemspider_id>389102</chemspider_id>
  <pubchem_compound_id>440101</pubchem_compound_id>
  <chebi_id>18189</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>RIBOSE-5P</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
    <reference>
      <reference_text>Characterization of the biochemical variability of bovine milk using metabolomics</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00355</protein_accession>
      <name>Ribose-5-phosphate isomerase</name>
      <uniprot_id>Q3T186</uniprot_id>
      <gene_name>RPIA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00478</protein_accession>
      <name>Ribose-phosphate pyrophosphokinase</name>
      <uniprot_id>A6QQ58</uniprot_id>
      <gene_name>LOC504248</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00482</protein_accession>
      <name>Ribose-phosphate pyrophosphokinase 1</name>
      <uniprot_id>Q2HJ58</uniprot_id>
      <gene_name>PRPS1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00607</protein_accession>
      <name>Transketolase-like protein 1</name>
      <uniprot_id>Q2NL26</uniprot_id>
      <gene_name>TKTL1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00608</protein_accession>
      <name>Transketolase-like protein 2</name>
      <uniprot_id>Q2NKZ4</uniprot_id>
      <gene_name>TKTL2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00609</protein_accession>
      <name>Transketolase</name>
      <uniprot_id>Q6B855</uniprot_id>
      <gene_name>TKT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:33 UTC</creation_date>
  <update_date>2020-03-13 16:28:46 UTC</update_date>
  <accession>BMDB0001550</accession>
  <secondary_accessions>
    <accession>BMDB01550</accession>
  </secondary_accessions>
  <name>S-Formylglutathione</name>
  <description/>
  <synonyms>
    <synonym>N-(S-(Formyl-N-L-gamma-glutamyl)-L-cysteinyl)glycine</synonym>
    <synonym>N-(S-(Formyl-N-L-g-glutamyl)-L-cysteinyl)glycine</synonym>
    <synonym>N-(S-(Formyl-N-L-γ-glutamyl)-L-cysteinyl)glycine</synonym>
    <synonym>L-gamma-Glutamyl-S-formyl-L-cysteinylglycine</synonym>
    <synonym>L-γ-Glutamyl-S-formyl-L-cysteinylglycine</synonym>
    <synonym>S-Formylglutathione</synonym>
  </synonyms>
  <chemical_formula>C11H17N3O7S</chemical_formula>
  <average_molecular_weight>335.334</average_molecular_weight>
  <monisotopic_moleculate_weight>335.078720603</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(formylsulfanyl)ethyl]carbamoyl}butanoic acid</iupac_name>
  <traditional_iupac>S-formylglutathione</traditional_iupac>
  <cas_registry_number>50409-81-9</cas_registry_number>
  <smiles>N[C@@H](CCC(=O)N[C@@H](CSC=O)C(=O)NCC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C11H17N3O7S/c12-6(11(20)21)1-2-8(16)14-7(4-22-5-15)10(19)13-3-9(17)18/h5-7H,1-4,12H2,(H,13,19)(H,14,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1</inchi>
  <inchikey>FHXAGOICBFGEBF-BQBZGAKWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Oligopeptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha amino acid amides</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carbothioic S-esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cysteine and derivatives</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Fatty acids and conjugates</alternative_parent>
      <alternative_parent>Gamma-glutamyl peptides</alternative_parent>
      <alternative_parent>Glutamine and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>S-acylglutathiones</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
      <alternative_parent>Thioesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-oligopeptide</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carbothioic s-ester</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Cysteine or derivatives</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Gamma-glutamyl alpha peptide</substituent>
      <substituent>Glutamine or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-substituted-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>S-acylglutathione</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thiocarboxylic acid ester</substituent>
      <substituent>Thiocarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>S-acylglutathione</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(formylsulfanyl)ethyl]carbamoyl}butanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>335.334</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>335.078720603</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CCC(=O)N[C@@H](CSC=O)C(=O)NCC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H17N3O7S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H17N3O7S/c12-6(11(20)21)1-2-8(16)14-7(4-22-5-15)10(19)13-3-9(17)18/h5-7H,1-4,12H2,(H,13,19)(H,14,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FHXAGOICBFGEBF-BQBZGAKWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>175.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>74.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38121</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>29566</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>36124</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01031</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022685</foodb_id>
  <chemspider_id>164320</chemspider_id>
  <pubchem_compound_id>189122</pubchem_compound_id>
  <chebi_id>16225</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>CPD-548</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>1485290</bigg_id>
  <wikipedia_id/>
  <metlin_id>3469</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00117</protein_accession>
      <name>S-formylglutathione hydrolase</name>
      <uniprot_id>Q08E20</uniprot_id>
      <gene_name>ESD</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:34 UTC</creation_date>
  <update_date>2020-03-13 16:28:47 UTC</update_date>
  <accession>BMDB0001551</accession>
  <secondary_accessions>
    <accession>BMDB01551</accession>
  </secondary_accessions>
  <name>Palmitaldehyde</name>
  <description/>
  <synonyms>
    <synonym>1-Hexadecanal</synonym>
    <synonym>16-Hexadecanal</synonym>
    <synonym>N-Hexadecanal</synonym>
    <synonym>Palmitoyl aldehyde</synonym>
    <synonym>Hexadecanal</synonym>
  </synonyms>
  <chemical_formula>C16H32O</chemical_formula>
  <average_molecular_weight>240.4247</average_molecular_weight>
  <monisotopic_moleculate_weight>240.245315646</monisotopic_moleculate_weight>
  <iupac_name>hexadecanal</iupac_name>
  <traditional_iupac>palmitoyl</traditional_iupac>
  <cas_registry_number>629-80-1</cas_registry_number>
  <smiles>CCCCCCCCCCCCCCCC=O</smiles>
  <inchi>InChI=1S/C16H32O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h16H,2-15H2,1H3</inchi>
  <inchikey>NIOYUNMRJMEDGI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as fatty aldehydes. These are long chain aldehydes with a chain of at least 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty aldehydes</sub_class>
    <direct_parent>Fatty aldehydes</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydrogen aldehydes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydrogen aldehyde</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Fatty aldehyde</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2,3-saturated fatty aldehyde</external_descriptor>
      <external_descriptor>Fatty aldehydes</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>long-chain fatty aldehyde</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>35 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-6.61</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>6.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>hexadecanal</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>240.4247</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>240.245315646</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCCCCCCCCC=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H32O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H32O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h16H,2-15H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NIOYUNMRJMEDGI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>76.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>18346</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00517</kegg_id>
  <drugbank_id>DB03381</drugbank_id>
  <foodb_id>FDB031083</foodb_id>
  <chemspider_id>959</chemspider_id>
  <pubchem_compound_id>984</pubchem_compound_id>
  <chebi_id>17600</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007542</knapsack_id>
  <bigg_id>35223</bigg_id>
  <wikipedia_id/>
  <metlin_id>6317</metlin_id>
  <synthesis_reference>Vignais, Pierce V.; Zabin, Irving.  Formation of palmitaldehyde in rat brain.    Biochem. Lipids Proc. 5th Intern. Conf. Vienna  (1960),  Volume Date 1958,     78-84.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:35 UTC</creation_date>
  <update_date>2020-03-13 16:28:47 UTC</update_date>
  <accession>BMDB0001552</accession>
  <secondary_accessions>
    <accession>BMDB01552</accession>
  </secondary_accessions>
  <name>2-Keto-glutaramic acid</name>
  <description>2-Keto-glutaramic acid, also known as 2-ketoglutaramate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Keto-glutaramic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Keto-glutaramic acid exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>2-Ketoglutaramate</synonym>
    <synonym>alpha-Ketoglutaramate</synonym>
    <synonym>2-Oxoglutaramic acid</synonym>
    <synonym>2-Ketoglutaramic acid</synonym>
    <synonym>a-Ketoglutaramate</synonym>
    <synonym>a-Ketoglutaramic acid</synonym>
    <synonym>alpha-Ketoglutaramic acid</synonym>
    <synonym>Α-ketoglutaramate</synonym>
    <synonym>Α-ketoglutaramic acid</synonym>
    <synonym>2-Oxoglutaramate</synonym>
    <synonym>2-Keto-glutaramate</synonym>
  </synonyms>
  <chemical_formula>C5H7NO4</chemical_formula>
  <average_molecular_weight>145.1134</average_molecular_weight>
  <monisotopic_moleculate_weight>145.037507717</monisotopic_moleculate_weight>
  <iupac_name>4-carbamoyl-2-oxobutanoic acid</iupac_name>
  <traditional_iupac>2-keto-glutaramate</traditional_iupac>
  <cas_registry_number>18465-19-5</cas_registry_number>
  <smiles>NC(=O)CCC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H7NO4/c6-4(8)2-1-3(7)5(9)10/h1-2H2,(H2,6,8)(H,9,10)</inchi>
  <inchikey>COJBGNAUUSNXHX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Short-chain keto acids and derivatives</sub_class>
    <direct_parent>Short-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Fatty amides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary carboxylic acid amide</substituent>
      <substituent>Short-chain keto acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-carbamoyl-2-oxobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>145.1134</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>145.037507717</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(=O)CCC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H7NO4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H7NO4/c6-4(8)2-1-3(7)5(9)10/h1-2H2,(H2,6,8)(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>COJBGNAUUSNXHX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13978</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23649</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>23650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>30448</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By GC-TOFMS and UPLC-QTOFMS</comment>
      <references>
        <reference>
          <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
          <pubmed_id>27999311</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00940</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022686</foodb_id>
  <chemspider_id>47</chemspider_id>
  <pubchem_compound_id>48</pubchem_compound_id>
  <chebi_id>30882</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6318</metlin_id>
  <synthesis_reference>Lalonde, James J.  Synthesis of 2-oxoglutaramate from L-glutamine.    U.S. Pat. Appl. Publ.  (2003),     7 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128.</reference_text>
      <pubmed_id>27999311</pubmed_id>
    </reference>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:36 UTC</creation_date>
  <update_date>2020-03-13 16:28:48 UTC</update_date>
  <accession>BMDB0001553</accession>
  <secondary_accessions>
    <accession>BMDB01553</accession>
  </secondary_accessions>
  <name>2-Oxo-4-methylthiobutanoic acid</name>
  <description>4-Methylthio-2-oxobutanoate, also known as 2-keto-4-methylthiobutyrate or 2-oxomethionine, belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain. 4-Methylthio-2-oxobutanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Methylthio-2-oxobutanoate exists in all living species, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>2-Keto-4-methylthiobutyric acid</synonym>
    <synonym>2-oxo-4-Methylthiobutanoate</synonym>
    <synonym>2-Oxomethionine</synonym>
    <synonym>4-(METHYLsulfanyl)-2-oxobutanoIC ACID</synonym>
    <synonym>4-Methylthio-2-oxobutanoate</synonym>
    <synonym>alpha-oxo-gamma-Methylthiobutyric acid</synonym>
    <synonym>4-(Methylsulfanyl)-2-oxobutanoate</synonym>
    <synonym>2-Keto-4-methylthiobutyrate</synonym>
    <synonym>4-(METHYLsulphanyl)-2-oxobutanoate</synonym>
    <synonym>4-(METHYLsulphanyl)-2-oxobutanoic acid</synonym>
    <synonym>4-Methylthio-2-oxobutanoic acid</synonym>
    <synonym>a-oxo-g-Methylthiobutyrate</synonym>
    <synonym>a-oxo-g-Methylthiobutyric acid</synonym>
    <synonym>alpha-oxo-gamma-Methylthiobutyrate</synonym>
    <synonym>Α-oxo-γ-methylthiobutyrate</synonym>
    <synonym>Α-oxo-γ-methylthiobutyric acid</synonym>
    <synonym>2-Ketomethiobutyrate</synonym>
    <synonym>4-Methylthio-2-ketobutanoate</synonym>
    <synonym>4-Methylthio-2-ketobutanoic acid</synonym>
    <synonym>4-Methylthio-2-ketobutyrate</synonym>
    <synonym>4-Methylthio-2-oxobutyrate</synonym>
    <synonym>alpha-Keto-methiolbutyric acid</synonym>
    <synonym>Keto-4-methylthiobutyrate</synonym>
    <synonym>Ketomethiobutyrate</synonym>
    <synonym>Ketomethiobutyric acid</synonym>
    <synonym>KMTB</synonym>
    <synonym>Methylthiobutyrate</synonym>
    <synonym>Methylthiobutyric acid</synonym>
    <synonym>2-Keto-4-methylthiobutanoic acid</synonym>
    <synonym>2-Keto-4-thiomethylbutyrate</synonym>
    <synonym>2-oxo-4-Thiomethylbutyric acid</synonym>
    <synonym>alpha-Keto-gamma-methiolbutyrate</synonym>
    <synonym>alpha-Ketomethionine</synonym>
    <synonym>alpha-Oxomethionine</synonym>
    <synonym>2-Keto-4-methylthiobutyric acid, monosodium salt</synonym>
    <synonym>2-Ketothiomethylbutyric acid</synonym>
    <synonym>4-Methylthio-2-oxobutyric acid</synonym>
    <synonym>S-Methyl-alpha-ketobutyric acid</synonym>
    <synonym>2-Keto-4-methylthiobutyric acid, calcium salt</synonym>
    <synonym>4-Methylthio-2-ketobutyric acid</synonym>
    <synonym>gamma-Methiol-keto-butyric acid</synonym>
    <synonym>4-Methylmercapto-2-oxobutyrate</synonym>
    <synonym>2-oxo-4-Methylthiobutanoic acid</synonym>
  </synonyms>
  <chemical_formula>C5H8O3S</chemical_formula>
  <average_molecular_weight>148.18</average_molecular_weight>
  <monisotopic_moleculate_weight>148.019414812</monisotopic_moleculate_weight>
  <iupac_name>4-(methylsulfanyl)-2-oxobutanoic acid</iupac_name>
  <traditional_iupac>2-oxo-4-thiomethylbutyric acid</traditional_iupac>
  <cas_registry_number>583-92-6</cas_registry_number>
  <smiles>CSCCC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)</inchi>
  <inchikey>SXFSQZDSUWACKX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as thia fatty acids. These are fatty acid derivatives obtained by insertion of a sulfur atom at specific positions in the chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Thia fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkylthioethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Short-chain keto acids and derivatives</alternative_parent>
      <alternative_parent>Sulfenyl compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkylthioether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Keto acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Short-chain keto acid</substituent>
      <substituent>Sulfenyl compound</substituent>
      <substituent>Thia fatty acid</substituent>
      <substituent>Thioether</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>Oxo fatty acids</external_descriptor>
      <external_descriptor>Oxo fatty acids</external_descriptor>
      <external_descriptor>sulfur-containing carboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-(methylsulfanyl)-2-oxobutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>148.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>148.019414812</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CSCCC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SXFSQZDSUWACKX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22051</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01180</kegg_id>
  <drugbank_id>DB02238</drugbank_id>
  <foodb_id>FDB030353</foodb_id>
  <chemspider_id>460</chemspider_id>
  <pubchem_compound_id>473</pubchem_compound_id>
  <chebi_id>33574</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007474</knapsack_id>
  <bigg_id>228408</bigg_id>
  <wikipedia_id/>
  <metlin_id>6319</metlin_id>
  <synthesis_reference>Brodelius, P.; Hagerdal, B.; Mosbach, K.  Immobilized whole cells of the yeast Trigonopsis variabilis containing D-amino acid oxidase for the production of a-keto acids.    Enzyme Engineering  (1980),  5  383-7.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
      <pubmed_id>23438684</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:37 UTC</creation_date>
  <update_date>2020-03-13 16:28:48 UTC</update_date>
  <accession>BMDB0001554</accession>
  <secondary_accessions>
    <accession>BMDB01554</accession>
  </secondary_accessions>
  <name>Xanthylic acid</name>
  <description/>
  <synonyms>
    <synonym>(9-D-Ribosylxanthine)-5'-phosphate</synonym>
    <synonym>Xanthosine 5'-phosphate</synonym>
    <synonym>Xanthosine monophosphate</synonym>
    <synonym>XMP</synonym>
    <synonym>(9-D-Ribosylxanthine)-5'-phosphoric acid</synonym>
    <synonym>Xanthosine 5'-phosphoric acid</synonym>
    <synonym>Xanthosine monophosphoric acid</synonym>
    <synonym>Xanthylate</synonym>
    <synonym>5'-Xanthonylate monophosphate</synonym>
    <synonym>Xanthosine-5'-p</synonym>
    <synonym>Xanthosine-5'-phosphate</synonym>
    <synonym>Xanthosine monophosphate, 8-(14)C-labeled</synonym>
  </synonyms>
  <chemical_formula>C10H13N4O9P</chemical_formula>
  <average_molecular_weight>364.2054</average_molecular_weight>
  <monisotopic_moleculate_weight>364.042014546</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>xanthosine monophosphate</traditional_iupac>
  <cas_registry_number>523-98-8</cas_registry_number>
  <smiles>O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O</smiles>
  <inchi>InChI=1S/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1</inchi>
  <inchikey>DCTLYFZHFGENCW-UUOKFMHZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Purine ribonucleotides</sub_class>
    <direct_parent>Purine ribonucleoside monophosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
      <alternative_parent>Xanthines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine ribonucleoside monophosphate</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
      <substituent>Xanthine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Purine alkaloids</external_descriptor>
      <external_descriptor>purine ribonucleoside 5'-monophosphate</external_descriptor>
      <external_descriptor>xanthosine 5'-phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.069</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>364.2054</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>364.042014546</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H13N4O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DCTLYFZHFGENCW-UUOKFMHZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>192.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>73.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38124</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448073</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00655</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB031254</foodb_id>
  <chemspider_id>66054</chemspider_id>
  <pubchem_compound_id>73323</pubchem_compound_id>
  <chebi_id>15652</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00007396</knapsack_id>
  <bigg_id>35623</bigg_id>
  <wikipedia_id>Xanthosine monophosphate</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Hattori, Kyoji; Kawahara, Shin; Hagiwara, Takeshige.  5'-Xanthylic acid.    Jpn. Kokai Tokkyo Koho  (1985),     3 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01002</protein_accession>
      <name>Inosine-5'-monophosphate dehydrogenase 2</name>
      <uniprot_id>Q3SWY3</uniprot_id>
      <gene_name>IMPDH2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01003</protein_accession>
      <name>Inosine-5'-monophosphate dehydrogenase</name>
      <uniprot_id>A0JNA3</uniprot_id>
      <gene_name>IMPDH1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:38 UTC</creation_date>
  <update_date>2020-03-13 16:28:49 UTC</update_date>
  <accession>BMDB0001555</accession>
  <secondary_accessions>
    <accession>BMDB01555</accession>
  </secondary_accessions>
  <name>Pyridoxamine 5'-phosphate</name>
  <description>Pyridoxamine 5'-phosphate, also known as pyridoxamine phosphoric acid or pyridoxamine-p, belongs to the class of organic compounds known as pyridoxamine 5'-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5'-position. Pyridoxamine 5'-phosphate is possibly soluble (in water) and a very strong basic compound (based on its pKa). Pyridoxamine 5'-phosphate exists in all living species, ranging from bacteria to humans. Pyridoxamine 5'-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Pyridoxamine 5'-phosphate can be biosynthesized from pyridoxamine; which is catalyzed by the enzyme pyridoxal kinase. In addition, Pyridoxamine 5'-phosphate can be converted into pyridoxal 5'-phosphate through the action of the enzyme pyridoxine-5'-phosphate oxidase. In cattle, pyridoxamine 5'-phosphate is involved in the metabolic pathway called the vitamin B6 metabolism pathway.</description>
  <synonyms>
    <synonym>4'-DEOXY-4'-aminopyridoxal-5'-phosphATE</synonym>
    <synonym>Pyridoxamine 5'-(dihydrogen phosphate)</synonym>
    <synonym>Pyridoxamine 5'-phosphoric acid</synonym>
    <synonym>Pyridoxamine 5-phosphate</synonym>
    <synonym>Pyridoxamine 5-phosphoric acid</synonym>
    <synonym>Pyridoxamine phosphate</synonym>
    <synonym>4'-DEOXY-4'-aminopyridoxal-5'-phosphoric acid</synonym>
    <synonym>Pyridoxamine 5'-(dihydrogen phosphoric acid)</synonym>
    <synonym>Pyridoxamine phosphoric acid</synonym>
    <synonym>Pyridoxamine-p</synonym>
    <synonym>Pyridoxamine phosphate hydrochloride</synonym>
  </synonyms>
  <chemical_formula>C8H13N2O5P</chemical_formula>
  <average_molecular_weight>248.173</average_molecular_weight>
  <monisotopic_moleculate_weight>248.056208048</monisotopic_moleculate_weight>
  <iupac_name>{[4-(aminomethyl)-5-hydroxy-6-methylpyridin-3-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>pyridoxamine-5'-phosphate</traditional_iupac>
  <cas_registry_number>529-96-4</cas_registry_number>
  <smiles>CC1=NC=C(COP(O)(O)=O)C(CN)=C1O</smiles>
  <inchi>InChI=1S/C8H13N2O5P/c1-5-8(11)7(2-9)6(3-10-5)4-15-16(12,13)14/h3,11H,2,4,9H2,1H3,(H2,12,13,14)</inchi>
  <inchikey>ZMJGSOSNSPKHNH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyridoxamine 5'-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5'-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyridoxamines</sub_class>
    <direct_parent>Pyridoxamine 5'-phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyridines</alternative_parent>
      <alternative_parent>Methylpyridines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyridine</substituent>
      <substituent>Methylpyridine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyridoxamine 5'-phosphate</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aminoalkylpyridine</external_descriptor>
      <external_descriptor>methylpyridines</external_descriptor>
      <external_descriptor>monohydroxypyridine</external_descriptor>
      <external_descriptor>vitamin B6 phosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.57</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[4-(aminomethyl)-5-hydroxy-6-methylpyridin-3-yl]methoxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>248.173</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>248.056208048</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=NC=C(COP(O)(O)=O)C(CN)=C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H13N2O5P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H13N2O5P/c1-5-8(11)7(2-9)6(3-10-5)4-15-16(12,13)14/h3,11H,2,4,9H2,1H3,(H2,12,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZMJGSOSNSPKHNH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>125.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>56.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Vitamin B6 Metabolism</name>
      <smpdb_id>SMP0087240</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4885</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2381</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>28837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>35395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446870</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446871</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447263</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.191 +/- 0.178</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk from Holstein cows</comment>
      <references>
        <reference>
          <reference_text>Coburn SP, Mahuren JD, Pauly TA, Ericson KL, Townsend DW: Alkaline phosphatase activity and pyridoxal phosphate concentrations in the milk of various species. J Nutr. 1992 Dec;122(12):2348-53. doi: 10.1093/jn/122.12.2348.</reference_text>
          <pubmed_id>1453218</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB021821</foodb_id>
  <chemspider_id>1024</chemspider_id>
  <kegg_id>C00647</kegg_id>
  <pubchem_compound_id>1053</pubchem_compound_id>
  <drugbank_id>DB02142</drugbank_id>
  <chebi_id>18335</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id>C00007506</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>35609</bigg_id>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Katsunishi, Masatoshi; Kondo, Osamu.  Pyridoxamine-5'-phosphate.    Jpn. Tokkyo Koho  (1972),     2 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Coburn SP, Mahuren JD, Pauly TA, Ericson KL, Townsend DW: Alkaline phosphatase activity and pyridoxal phosphate concentrations in the milk of various species. J Nutr. 1992 Dec;122(12):2348-53. doi: 10.1093/jn/122.12.2348.</reference_text>
      <pubmed_id>1453218</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00214</protein_accession>
      <name>Pyridoxine-5'-phosphate oxidase</name>
      <uniprot_id>Q5E9K3</uniprot_id>
      <gene_name>PNPO</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:40 UTC</creation_date>
  <update_date>2020-03-13 16:28:49 UTC</update_date>
  <accession>BMDB0001557</accession>
  <secondary_accessions>
    <accession>BMDB01557</accession>
  </secondary_accessions>
  <name>Riboflavin reduced</name>
  <description/>
  <synonyms>
    <synonym>4a,5-Dihydroriboflavin</synonym>
    <synonym>4a,5-Dihydroriboflavine</synonym>
    <synonym>7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-4a,5-dihydroisoalloxazine</synonym>
    <synonym>7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-5,10-dihydrobenzo[g]pteridine-2,4(3H,4ah)-dione</synonym>
    <synonym>Reduced riboflavin</synonym>
  </synonyms>
  <chemical_formula>C15H16N4O6</chemical_formula>
  <average_molecular_weight>348.3107</average_molecular_weight>
  <monisotopic_moleculate_weight>348.106984264</monisotopic_moleculate_weight>
  <iupac_name>10-[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione</iupac_name>
  <traditional_iupac>10-[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]-3H-benzo[g]pteridine-2,4-dione</traditional_iupac>
  <cas_registry_number>101652-10-2</cas_registry_number>
  <smiles>OC[C@@H](O)[C@H](O)[C@H](O)CN1C2=CC=CC=C2N=C2C(=O)NC(=O)N=C12</smiles>
  <inchi>InChI=1S/C15H16N4O6/c20-6-10(22)12(23)9(21)5-19-8-4-2-1-3-7(8)16-11-13(19)17-15(25)18-14(11)24/h1-4,9-10,12,20-23H,5-6H2,(H,18,24,25)/t9-,10-,12-/m1/s1</inchi>
  <inchikey>ATANIONNQLTUND-CKYFFXLPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alloxazines and isoalloxazines. These are organic compounds comprising the (iso)alloxazine structure (Benzo[g]pteridine-2,4-dione).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Alloxazines and isoalloxazines</sub_class>
    <direct_parent>Alloxazines and isoalloxazines</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrazines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Quinoxalines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Diazanaphthalene</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Isoalloxazine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrazine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Quinoxaline</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>6.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>0.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>10-[(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>348.3107</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>348.106984264</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)[C@H](O)[C@H](O)CN1C2=CC=CC=C2N=C2C(=O)NC(=O)N=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H16N4O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H16N4O6/c20-6-10(22)12(23)9(21)5-19-8-4-2-1-3-7(8)16-11-13(19)17-15(25)18-14(11)24/h1-4,9-10,12,20-23H,5-6H2,(H,18,24,25)/t9-,10-,12-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ATANIONNQLTUND-CKYFFXLPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>155.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>33.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>11922</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38126</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>292257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>332409</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022688</foodb_id>
  <chemspider_id>17216138</chemspider_id>
  <kegg_id>C01007</kegg_id>
  <pubchem_compound_id>22833571</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6322</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00585</protein_accession>
      <name>Flavin reductase</name>
      <uniprot_id>P52556</uniprot_id>
      <gene_name>BLVRB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:41 UTC</creation_date>
  <update_date>2020-04-15 23:45:59 UTC</update_date>
  <accession>BMDB0001562</accession>
  <secondary_accessions>
    <accession>BMDB01562</accession>
  </secondary_accessions>
  <name>N5-Formyl-H4F</name>
  <description>N5-Formyl-THF, also known as n5-formyl-thf or n5-formyl-thf, calcium, belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. N5-Formyl-THF exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. N5-Formyl-THF exists in all living species, ranging from bacteria to humans. N5-Formyl-THF participates in a number of enzymatic reactions, within cattle. In particular, N5-Formyl-THF and L-glutamic acid can be converted into tetrahydrofolic acid and N-formyl-L-glutamic acid; which is mediated by the enzyme formimidoyltransferase-cyclodeaminase. In addition, N5-Formyl-THF can be converted into 5,10-methenyltetrahydrofolic acid; which is catalyzed by the enzyme N5-formyl-thf cyclo-ligase. In cattle, N5-formyl-THF is involved in the metabolic pathway called the folate metabolism pathway.</description>
  <synonyms>
    <synonym>Leucovorin</synonym>
    <synonym>5-Formyltetrahydrofolate</synonym>
    <synonym>L(-)-5-Formyl-5,6,7,8-tetrahydrofolic acid</synonym>
    <synonym>Rescuvolin</synonym>
    <synonym>5-Formyltetrahydrofolic acid</synonym>
    <synonym>L(-)-5-Formyl-5,6,7,8-tetrahydrofolate</synonym>
    <synonym>(6R,S)-5-Formyltetrahydrofolate</synonym>
    <synonym>10-Formyl-7,8-dihydrofolate</synonym>
    <synonym>10-Formyl-7,8-dihydrofolic acid</synonym>
    <synonym>5-Formyl-5,6,7,8-tetrahydrofolate</synonym>
    <synonym>5-Formyl-5,6,7,8-tetrahydrofolic acid</synonym>
    <synonym>5-Formyltetrahydropteroylglutamate</synonym>
    <synonym>5-Formyltetrahydropteroylglutamic acid</synonym>
    <synonym>Folinate</synonym>
    <synonym>Folinic acid</synonym>
    <synonym>Folinic acid-SF</synonym>
    <synonym>L-Leucovorin</synonym>
    <synonym>L-N-[P-[[(2-amino-5-Formyl-5,6,7,8-tetrahydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-glutamic acid</synonym>
    <synonym>Leucal</synonym>
    <synonym>Levoleucovorin</synonym>
    <synonym>N5-Formyl-5,6,7,8-tetrahydrofolate</synonym>
    <synonym>N5-Formyl-5,6,7,8-tetrahydrofolic acid</synonym>
    <synonym>N5-Formyltetrahydrofolate</synonym>
    <synonym>N5-Formyltetrahydrofolic acid</synonym>
    <synonym>Welcovorin</synonym>
    <synonym>Acid, folinic</synonym>
    <synonym>Folinate, calcium</synonym>
    <synonym>Leucovorin, (D)-isomer</synonym>
    <synonym>Leucovorin, (DL)-isomer</synonym>
    <synonym>Leucovorin, calcium (1:1) salt</synonym>
    <synonym>5 Formyltetrahydrofolate</synonym>
    <synonym>Citrovorum factor</synonym>
    <synonym>Factor, citrovorum</synonym>
    <synonym>Folinic acid SF</synonym>
    <synonym>Leucovorin, calcium (1:1) salt, pentahydrate</synonym>
    <synonym>Leukovorin</synonym>
    <synonym>N(5)-Formyltetrahydrofolate</synonym>
    <synonym>Leucovorin, (R)-isomer</synonym>
    <synonym>Leucovorin, calcium (1:1) salt, (DL)-isomer</synonym>
    <synonym>Leukovorum</synonym>
    <synonym>Monosodium salt leucovorin</synonym>
    <synonym>Wellcovorin</synonym>
    <synonym>5 Formyltetrahydropteroylglutamate</synonym>
    <synonym>Calcium folinate</synonym>
    <synonym>Calcium leucovorin</synonym>
    <synonym>Leucovorin, calcium</synonym>
    <synonym>Leucovorin, monosodium salt</synonym>
  </synonyms>
  <chemical_formula>C20H23N7O7</chemical_formula>
  <average_molecular_weight>473.4393</average_molecular_weight>
  <monisotopic_moleculate_weight>473.165896125</monisotopic_moleculate_weight>
  <iupac_name>2-[(4-{[(2-amino-5-formyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</iupac_name>
  <traditional_iupac>2-[(4-{[(2-amino-5-formyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</traditional_iupac>
  <cas_registry_number>58-05-9</cas_registry_number>
  <smiles>OC(=O)CCC(NC(=O)C1=CC=C(NCC2CNC3=C(N2C=O)C(O)=NC(=N)N3)C=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)</inchi>
  <inchikey>VVIAGPKUTFNRDU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Tetrahydrofolic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminobenzamides</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Glutamic acid and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hippuric acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalkylamines</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tertiary carboxylic acid amides</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminobenzamide</substituent>
      <substituent>Aminobenzoic acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzamide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoic acid or derivatives</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hippuric acid</substituent>
      <substituent>Hippuric acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylalkylamine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
      <substituent>Tetrahydrofolic acid</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4-{[(2-amino-5-formyl-4-oxo-3,4,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>473.4393</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>473.165896125</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CCC(NC(=O)C1=CC=C(NCC2CNC3=C(N2C=O)C(O)=NC(=N)N3)C=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H23N7O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VVIAGPKUTFNRDU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>215.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>126.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>46.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38127</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26221</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32779</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C03479</kegg_id>
  <chemspider_id/>
  <pubchem_compound_id>143</pubchem_compound_id>
  <drugbank_id/>
  <foodb_id>FDB022689</foodb_id>
  <chebi_id/>
  <pdbe_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Zakrzewski, Sigmund F.; Sansone, Annette M.  Preparation of folinic acid (N5-formyltetrahydro folic acid).    Methods Enzymol.  (1971),  18(Pt. B),  731-3. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:42 UTC</creation_date>
  <update_date>2020-03-13 16:28:50 UTC</update_date>
  <accession>BMDB0001563</accession>
  <secondary_accessions>
    <accession>BMDB01563</accession>
  </secondary_accessions>
  <name>1-Methylguanosine</name>
  <description>1-Methylguanosine, also known as M1G or TRMD protein, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. 1-Methylguanosine is possibly soluble (in water) and a moderately basic compound (based on its pKa).</description>
  <synonyms>
    <synonym>m1g</synonym>
    <synonym>N1-Methylguanosine</synonym>
    <synonym>1-Methyl-guanosine</synonym>
    <synonym>Methylguanosine</synonym>
    <synonym>TRMD Protein</synonym>
    <synonym>N-Methylguanosine</synonym>
  </synonyms>
  <chemical_formula>C11H15N5O5</chemical_formula>
  <average_molecular_weight>297.2673</average_molecular_weight>
  <monisotopic_moleculate_weight>297.107318615</monisotopic_moleculate_weight>
  <iupac_name>2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methyl-6,9-dihydro-1H-purin-6-one</iupac_name>
  <traditional_iupac>1-methylguanosine</traditional_iupac>
  <cas_registry_number>2140-65-0</cas_registry_number>
  <smiles>CN1C(N)=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=O</smiles>
  <inchi>InChI=1S/C11H15N5O5/c1-15-9(20)5-8(14-11(15)12)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>UTAIYTHAJQNQDW-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleosides</class>
    <sub_class/>
    <direct_parent>Purine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleoside</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>methylguanosine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methyl-6,9-dihydro-1H-purin-6-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>297.2673</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>297.107318615</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C(N)=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H15N5O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H15N5O5/c1-15-9(20)5-8(14-11(15)12)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UTAIYTHAJQNQDW-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>146.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>69.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>47718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>47719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>47720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146669</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022690</foodb_id>
  <chemspider_id>86996</chemspider_id>
  <kegg_id>C04545</kegg_id>
  <pubchem_compound_id>96373</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>19062</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>CPD0-1043</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>7-Methylguanosine</wikipedia_id>
  <metlin_id>6324</metlin_id>
  <synthesis_reference>Ermolinsky Boris S; Efimtseva Ekaterina V; Alexeev Cyrill S; Mikhailov Sergey N; Balzarini Jan; De Clercq Erik  Dinucleoside monophosphates containing AZT and 1-methyladenosine or 7-methylguanosine.    Nucleosides, nucleotides &amp; nucleic acids  (2003),  22(5-8),  853-5.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00942</protein_accession>
      <name>Protein argonaute-2</name>
      <uniprot_id>Q6QME8</uniprot_id>
      <gene_name>EIF2C2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:43 UTC</creation_date>
  <update_date>2020-04-15 22:07:37 UTC</update_date>
  <accession>BMDB0001564</accession>
  <secondary_accessions>
    <accession>BMDB01564</accession>
  </secondary_accessions>
  <name>CDP-Ethanolamine</name>
  <description/>
  <synonyms>
    <synonym>CDP Ethanolamine</synonym>
    <synonym>Cytidine 5'-(trihydrogen diphosphate), p'-(2-aminoethyl) ester</synonym>
    <synonym>Cytidine diphosphate ethanolamine</synonym>
    <synonym>Cytidine 5'-(trihydrogen diphosphoric acid), p'-(2-aminoethyl) ester</synonym>
    <synonym>Cytidine diphosphoric acid ethanolamine</synonym>
    <synonym>CDPethanolamine</synonym>
    <synonym>CDP Ethanolamine, p'-(32)p-labeled</synonym>
    <synonym>Cytidine 5'-diphosphate ethanolamine</synonym>
    <synonym>Cytidine 5'-diphosphoethanolamine</synonym>
    <synonym>Cytidine 5’-diphosphate ethanolamine</synonym>
    <synonym>Cytidine 5’-diphosphoethanolamine</synonym>
    <synonym>Cytidine diphosphoethanolamine</synonym>
    <synonym>CDP-ethanolamine</synonym>
  </synonyms>
  <chemical_formula>C11H20N4O11P2</chemical_formula>
  <average_molecular_weight>446.2442</average_molecular_weight>
  <monisotopic_moleculate_weight>446.060380526</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2-aminoethoxy)(hydroxy)phosphoryl]oxy})phosphinic acid</iupac_name>
  <traditional_iupac>cdp ethanolamine</traditional_iupac>
  <cas_registry_number>3036-18-8</cas_registry_number>
  <smiles>NCCOP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O</smiles>
  <inchi>InChI=1S/C11H20N4O11P2/c12-2-4-23-27(19,20)26-28(21,22)24-5-6-8(16)9(17)10(25-6)15-3-1-7(13)14-11(15)18/h1,3,6,8-10,16-17H,2,4-5,12H2,(H,19,20)(H,21,22)(H2,13,14,18)/t6-,8-,9-,10-/m1/s1</inchi>
  <inchikey>WVIMUEUQJFPNDK-PEBGCTIMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cdp-ethanolamines. These are phosphoethanolamines that consist of an ethanolamine having a cytidine 5'-diphosphate moiety attached to the oxygen.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Pyrimidine nucleotides</class>
    <sub_class>Pyrimidine ribonucleotides</sub_class>
    <direct_parent>CDP-ethanolamines</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic pyrophosphates</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Phosphoethanolamines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Cdp-ethanolamine</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic pyrophosphate</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Pentose-5-phosphate</substituent>
      <substituent>Phosphoethanolamine</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>nucleotide-(amino alcohol)s</external_descriptor>
      <external_descriptor>phosphoethanolamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2-aminoethoxy)(hydroxy)phosphoryl]oxy})phosphinic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>446.2442</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>446.060380526</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCOP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H20N4O11P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H20N4O11P2/c12-2-4-23-27(19,20)26-28(21,22)24-5-6-8(16)9(17)10(25-6)15-3-1-7(13)14-11(15)18/h1,3,6,8-10,16-17H,2,4-5,12H2,(H,19,20)(H,21,22)(H2,13,14,18)/t6-,8-,9-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WVIMUEUQJFPNDK-PEBGCTIMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>236.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>88.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis</name>
      <smpdb_id>SMP0072037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:0)</name>
      <smpdb_id>SMP0080430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0080431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/15:0)</name>
      <smpdb_id>SMP0080432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:0)</name>
      <smpdb_id>SMP0080433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0080434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:0)</name>
      <smpdb_id>SMP0080435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0080436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0080437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:0)</name>
      <smpdb_id>SMP0080442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0080443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:0)</name>
      <smpdb_id>SMP0080450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0080451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:0)</name>
      <smpdb_id>SMP0080457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0080458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0080459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0080460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0080461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/15:0)</name>
      <smpdb_id>SMP0080487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:0)</name>
      <smpdb_id>SMP0080488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0080489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:0)</name>
      <smpdb_id>SMP0080490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0080491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0080492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:0)</name>
      <smpdb_id>SMP0080497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0080498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:0)</name>
      <smpdb_id>SMP0080505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0080506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:0)</name>
      <smpdb_id>SMP0080512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0080513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:0)</name>
      <smpdb_id>SMP0080514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0080515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:0)</name>
      <smpdb_id>SMP0080516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0080517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0080518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:0)</name>
      <smpdb_id>SMP0080523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0080524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:0)</name>
      <smpdb_id>SMP0080531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0080532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:0)</name>
      <smpdb_id>SMP0080538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0080539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:0)</name>
      <smpdb_id>SMP0080565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0080566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0080567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:0)</name>
      <smpdb_id>SMP0080572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0080573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:0)</name>
      <smpdb_id>SMP0080580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0080581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:0)</name>
      <smpdb_id>SMP0080587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0080588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0080595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:0)</name>
      <smpdb_id>SMP0080712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0080713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:0)</name>
      <smpdb_id>SMP0080720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0080721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:0)</name>
      <smpdb_id>SMP0080727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0080728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0080765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0080772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:0)</name>
      <smpdb_id>SMP0080820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0080821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:0)</name>
      <smpdb_id>SMP0080827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0080828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0080835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:0)</name>
      <smpdb_id>SMP0080864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0080865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis</name>
      <smpdb_id>SMP0072048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:0)</name>
      <smpdb_id>SMP0082233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0082234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/15:0)</name>
      <smpdb_id>SMP0082235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:0)</name>
      <smpdb_id>SMP0082236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0082237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:0)</name>
      <smpdb_id>SMP0082238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0082239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0082240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:0)</name>
      <smpdb_id>SMP0082245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0082246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:0)</name>
      <smpdb_id>SMP0082253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0082254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:0)</name>
      <smpdb_id>SMP0082260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0082261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0082262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0082263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0082264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/15:0)</name>
      <smpdb_id>SMP0082290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:0)</name>
      <smpdb_id>SMP0082291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0082292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:0)</name>
      <smpdb_id>SMP0082293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0082294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0082295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:0)</name>
      <smpdb_id>SMP0082300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0082301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:0)</name>
      <smpdb_id>SMP0082308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0082309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:0)</name>
      <smpdb_id>SMP0082315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0082316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:0)</name>
      <smpdb_id>SMP0082317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0082318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:0)</name>
      <smpdb_id>SMP0082319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0082320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0082321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:0)</name>
      <smpdb_id>SMP0082326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0082327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:0)</name>
      <smpdb_id>SMP0082334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0082335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:0)</name>
      <smpdb_id>SMP0082341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0082342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:0)</name>
      <smpdb_id>SMP0082368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0082369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0082370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:0)</name>
      <smpdb_id>SMP0082375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0082376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:0)</name>
      <smpdb_id>SMP0082383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0082384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:0)</name>
      <smpdb_id>SMP0082390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0082391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0082398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:0)</name>
      <smpdb_id>SMP0082520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0082521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:0)</name>
      <smpdb_id>SMP0082528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0082529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:0)</name>
      <smpdb_id>SMP0082535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0082536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0082574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0082581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:0)</name>
      <smpdb_id>SMP0082629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0082630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:0)</name>
      <smpdb_id>SMP0082636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0082637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0082644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:0)</name>
      <smpdb_id>SMP0082671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0082672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Plasmalogen Synthesis</name>
      <smpdb_id>SMP0087264</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180893</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022691</foodb_id>
  <chemspider_id>110296</chemspider_id>
  <kegg_id>C00570</kegg_id>
  <pubchem_compound_id>123727</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>16732</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id>35382</bigg_id>
  <wikipedia_id/>
  <metlin_id>3538</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00391</protein_accession>
      <name>Ethanolaminephosphotransferase 1</name>
      <uniprot_id>Q17QM4</uniprot_id>
      <gene_name>SELI</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00392</protein_accession>
      <name>Ethanolamine-phosphate cytidylyltransferase</name>
      <uniprot_id>Q5EA75</uniprot_id>
      <gene_name>PCYT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:44 UTC</creation_date>
  <update_date>2020-04-16 20:39:27 UTC</update_date>
  <accession>BMDB0001565</accession>
  <secondary_accessions>
    <accession>BMDB01565</accession>
  </secondary_accessions>
  <name>Phosphorylcholine</name>
  <description>Phosphorylcholine, also known as choline phosphate or CHOP, belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. Phosphorylcholine is possibly soluble (in water) and a moderately acidic compound (based on its pKa). Phosphorylcholine exists in all living species, ranging from bacteria to humans. Phosphorylcholine participates in a number of enzymatic reactions, within cattle. In particular, Cytidine triphosphate and phosphorylcholine can be converted into CDP-choline; which is catalyzed by the enzyme choline-phosphate cytidylyltransferase. In addition, Phosphorylcholine can be biosynthesized from choline; which is mediated by the enzyme choline/ethanolamine kinase. In cattle, phosphorylcholine is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(16:0/16:0) pathway.</description>
  <synonyms>
    <synonym>Choline phosphate</synonym>
    <synonym>CHOP</synonym>
    <synonym>N-Trimethyl-2-aminoethylphosphonate</synonym>
    <synonym>O-Phosphocholine</synonym>
    <synonym>Phosphoryl-choline</synonym>
    <synonym>Trimethyl(2-(phosphonooxy)ethyl)ammonium</synonym>
    <synonym>Phosphocholine</synonym>
    <synonym>Choline phosphoric acid</synonym>
    <synonym>N-Trimethyl-2-aminoethylphosphonic acid</synonym>
    <synonym>Chloride, phosphorylcholine</synonym>
    <synonym>Phosphate, choline</synonym>
    <synonym>Phosphorylcholine chloride</synonym>
    <synonym>Phosphate chloride, choline</synonym>
    <synonym>Chloride, choline phosphate</synonym>
    <synonym>Choline chloride dihydrogen phosphate</synonym>
    <synonym>Choline phosphate chloride</synonym>
  </synonyms>
  <chemical_formula>C5H15NO4P</chemical_formula>
  <average_molecular_weight>184.1507</average_molecular_weight>
  <monisotopic_moleculate_weight>184.073869485</monisotopic_moleculate_weight>
  <iupac_name>[2-(trimethylazaniumyl)ethoxy]phosphonic acid</iupac_name>
  <traditional_iupac>ChoP</traditional_iupac>
  <cas_registry_number>3616-04-4</cas_registry_number>
  <smiles>C[N+](C)(C)CCOP(O)(O)=O</smiles>
  <inchi>InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1</inchi>
  <inchikey>YHHSONZFOIEMCP-UHFFFAOYSA-O</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Quaternary ammonium salts</sub_class>
    <direct_parent>Phosphocholines</direct_parent>
    <alternative_parents>
      <alternative_parent>Amines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Amine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphocholine</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>phosphocholines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[2-(trimethylazaniumyl)ethoxy]phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>184.1507</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>184.073869485</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)CCOP(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H15NO4P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YHHSONZFOIEMCP-UHFFFAOYSA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>53.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis</name>
      <smpdb_id>SMP0072037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:0)</name>
      <smpdb_id>SMP0080430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0080431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/15:0)</name>
      <smpdb_id>SMP0080432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:0)</name>
      <smpdb_id>SMP0080433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0080434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:0)</name>
      <smpdb_id>SMP0080435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0080436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0080437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:0)</name>
      <smpdb_id>SMP0080442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0080443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:0)</name>
      <smpdb_id>SMP0080450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0080451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:0)</name>
      <smpdb_id>SMP0080457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0080458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0080459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0080460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0080461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/15:0)</name>
      <smpdb_id>SMP0080487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:0)</name>
      <smpdb_id>SMP0080488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0080489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:0)</name>
      <smpdb_id>SMP0080490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0080491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0080492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:0)</name>
      <smpdb_id>SMP0080497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0080498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:0)</name>
      <smpdb_id>SMP0080505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0080506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:0)</name>
      <smpdb_id>SMP0080512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0080513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:0)</name>
      <smpdb_id>SMP0080514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0080515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:0)</name>
      <smpdb_id>SMP0080516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0080517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0080518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:0)</name>
      <smpdb_id>SMP0080523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0080524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:0)</name>
      <smpdb_id>SMP0080531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0080532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:0)</name>
      <smpdb_id>SMP0080538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0080539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:0)</name>
      <smpdb_id>SMP0080565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0080566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0080567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:0)</name>
      <smpdb_id>SMP0080572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0080573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:0)</name>
      <smpdb_id>SMP0080580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0080581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:0)</name>
      <smpdb_id>SMP0080587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0080588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0080595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:0)</name>
      <smpdb_id>SMP0080712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0080713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:0)</name>
      <smpdb_id>SMP0080720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0080721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:0)</name>
      <smpdb_id>SMP0080727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0080728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0080765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0080772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:0)</name>
      <smpdb_id>SMP0080820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0080821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:0)</name>
      <smpdb_id>SMP0080827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0080828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0080835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:0)</name>
      <smpdb_id>SMP0080864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0080865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phospholipid Biosynthesis</name>
      <smpdb_id>SMP0087228</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1651</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1652</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1653</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448186</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>1658+/-593</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from 20 healthy Holstein Friesian dairy cows </comment>
      <references>
        <reference>
          <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
          <pubmed_id>23738862</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples from Danish Holstein-Friesian (n = 456) and Jersey cows (n = 436)</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
          <pubmed_id>23182357</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>72.12 +/- 59.74</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>143 - 1355</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>183 - 941</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30.83 +/- 34.97</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>44.14 +/- 32.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>122 +/- 8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>123 +/- 7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>116 +/- 7</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>120 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>1058+/-234</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB031111</foodb_id>
  <chemspider_id>989</chemspider_id>
  <kegg_id>C00588</kegg_id>
  <pubchem_compound_id>1014</pubchem_compound_id>
  <drugbank_id>DB03945</drugbank_id>
  <chebi_id>18132</chebi_id>
  <pdbe_id/>
  <meta_cyc_id>PHOSPHORYL-CHOLINE</meta_cyc_id>
  <knapsack_id>C00007299</knapsack_id>
  <phenol_explorer_compound_id/>
  <bigg_id>48308</bigg_id>
  <wikipedia_id>Phosphorylcholine</wikipedia_id>
  <metlin_id>6326</metlin_id>
  <synthesis_reference>Vijeeta, T.; Reddy, J. R. C.; Rao, B. V. S. K.; Karuna, M. S. L.; Prasad, R. B. N. Phospholipase-mediated preparation of 1-ricinoleoyl-2-acyl-sn- glycero-3-phosphocholine from soya and egg phosphatidylcholine. Biotechnology Letters (2004), 26(13), 1077-10</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22.</reference_text>
      <pubmed_id>23182357</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5.</reference_text>
      <pubmed_id>23738862</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00130</protein_accession>
      <name>Sphingomyelin phosphodiesterase</name>
      <uniprot_id>Q0VD19</uniprot_id>
      <gene_name>SMPD1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00133</protein_accession>
      <name>Manganese-dependent ADP-ribose/CDP-alcohol diphosphatase</name>
      <uniprot_id>A7YY53</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:45 UTC</creation_date>
  <update_date>2020-03-13 16:28:52 UTC</update_date>
  <accession>BMDB0001566</accession>
  <secondary_accessions>
    <accession>BMDB01566</accession>
  </secondary_accessions>
  <name>3-Methylguanine</name>
  <description/>
  <synonyms>
    <synonym>N(3)-Methylguanine</synonym>
    <synonym>2-Amino-3,7-dihydro-3-methyl-6H-purin-6-one</synonym>
    <synonym>3-Methyl-guanine</synonym>
    <synonym>7-Dihydro-3-methyl-2-amino-3-6H-purin-6-one</synonym>
    <synonym>7-Dihydro-3-methyl-2-amino-3-6H-purin-6-one (9ci)</synonym>
    <synonym>N3-Methylguanine</synonym>
    <synonym>3-Methylguanine</synonym>
  </synonyms>
  <chemical_formula>C6H7N5O</chemical_formula>
  <average_molecular_weight>165.1527</average_molecular_weight>
  <monisotopic_moleculate_weight>165.065059871</monisotopic_moleculate_weight>
  <iupac_name>2-amino-3-methyl-6,7-dihydro-3H-purin-6-one</iupac_name>
  <traditional_iupac>N(3)-methylguanine</traditional_iupac>
  <cas_registry_number>2958-98-7</cas_registry_number>
  <smiles>CN1C2=C(NC=N2)C(=O)N=C1N</smiles>
  <inchi>InChI=1S/C6H7N5O/c1-11-4-3(8-2-9-4)5(12)10-6(11)7/h2H,1H3,(H,8,9)(H2,7,10,12)</inchi>
  <inchikey>XHBSBNYEHDQRCP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Purines and purine derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Purine</substituent>
      <substituent>Pyrimidine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-methylguanine</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.90</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-3-methyl-6,7-dihydro-3H-purin-6-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>165.1527</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>165.065059871</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C2=C(NC=N2)C(=O)N=C1N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H7N5O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H7N5O/c1-11-4-3(8-2-9-4)5(12)10-6(11)7/h2H,1H3,(H,8,9)(H2,7,10,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XHBSBNYEHDQRCP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>87.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326570</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>446519</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022693</foodb_id>
  <chemspider_id>68771</chemspider_id>
  <kegg_id>C02230</kegg_id>
  <pubchem_compound_id>76292</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>27564</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Methylguanine</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Itaya, Taisuke; Shioyama, Chieko; Kagatani, Seiya.  Improved synthesis of 3-methylguanine.    Chemical &amp; Pharmaceutical Bulletin  (1982),  30(9),  3392-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:47 UTC</creation_date>
  <update_date>2020-03-13 16:28:52 UTC</update_date>
  <accession>BMDB0001568</accession>
  <secondary_accessions>
    <accession>BMDB01568</accession>
  </secondary_accessions>
  <name>trans-2-Octenoic acid</name>
  <description>trans-2-Octenoic acid, also known as trans-2-octenoic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. trans-2-Octenoic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. trans-2-Octenoic acid exists in all eukaryotes, ranging from yeast to humans. trans-2-Octenoic acid participates in a number of enzymatic reactions, within cattle. In particular, trans-2-Octenoic acid can be biosynthesized from (R)-3-hydroxyoctanoic acid; which is mediated by the enzyme fatty acid synthase. dyhydrase domain. In addition, trans-2-Octenoic acid can be converted into caprylic acid through its interaction with the enzyme fatty acid synthase. enoyl reductase domain. In cattle, trans-2-octenoic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway.</description>
  <synonyms>
    <synonym>(e)-2-Octenoic acid</synonym>
    <synonym>2-Octenoic acid</synonym>
    <synonym>trans-alpha-Octenoic acid</synonym>
    <synonym>(e)-2-Octenoate</synonym>
    <synonym>2-Octenoate</synonym>
    <synonym>trans-a-Octenoate</synonym>
    <synonym>trans-a-Octenoic acid</synonym>
    <synonym>trans-alpha-Octenoate</synonym>
    <synonym>trans-Α-octenoate</synonym>
    <synonym>trans-Α-octenoic acid</synonym>
    <synonym>trans-2-Octenoate</synonym>
    <synonym>(e)-Oct-2-enoate</synonym>
    <synonym>(e)-Oct-2-enoic acid</synonym>
    <synonym>(2E)-2-Octenoic acid</synonym>
    <synonym>(2E)-Oct-2-enoic acid</synonym>
    <synonym>trans-2-Octenoic acid</synonym>
  </synonyms>
  <chemical_formula>C8H14O2</chemical_formula>
  <average_molecular_weight>142.1956</average_molecular_weight>
  <monisotopic_moleculate_weight>142.099379692</monisotopic_moleculate_weight>
  <iupac_name>(2E)-oct-2-enoic acid</iupac_name>
  <traditional_iupac>trans-2-octenoic acid</traditional_iupac>
  <cas_registry_number>1871-67-6</cas_registry_number>
  <smiles>CCCCC\C=C\C(O)=O</smiles>
  <inchi>InChI=1S/C8H14O2/c1-2-3-4-5-6-7-8(9)10/h6-7H,2-5H2,1H3,(H,9,10)/b7-6+</inchi>
  <inchikey>CWMPPVPFLSZGCY-VOTSOKGWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
      <external_descriptor>medium-chain fatty acid</external_descriptor>
      <external_descriptor>monounsaturated fatty acid</external_descriptor>
      <external_descriptor>olefinic fatty acid</external_descriptor>
      <external_descriptor>straight-chain fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>5 - 6 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.9</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-oct-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>142.1956</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>142.099379692</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC\C=C\C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H14O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H14O2/c1-2-3-4-5-6-7-8(9)10/h6-7H,2-5H2,1H3,(H,9,10)/b7-6+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CWMPPVPFLSZGCY-VOTSOKGWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1655</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183213</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183214</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183215</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB001088</foodb_id>
  <chemspider_id>4445841</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>5282714</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>86544</chebi_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6328</metlin_id>
  <synthesis_reference>Kameda, Kenji; Chikaki, Mariko; Morimoto, Chie; Jiang, Ming; Okuda, Hiromichi.  Insulin-like actions of trans-10-hydroxy-2-decanoic acid and its related substances.    Wakan Iyakugaku Zasshi  (1996),  13(4),  456-457.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:48 UTC</creation_date>
  <update_date>2020-03-13 16:28:53 UTC</update_date>
  <accession>BMDB0001569</accession>
  <secondary_accessions>
    <accession>BMDB01569</accession>
  </secondary_accessions>
  <name>Epi-coprostanol</name>
  <description/>
  <synonyms>
    <synonym>(3-alpha,5-alpha)-Cholestan-3-ol</synonym>
    <synonym>3alpha-Hydroxy-5alpha-cholestane</synonym>
    <synonym>5alpha-Cholestan-3alpha-ol</synonym>
    <synonym>Epi-cholestanol</synonym>
    <synonym>Epicholestanol</synonym>
    <synonym>Epidehydrocholesterin</synonym>
    <synonym>Presteron</synonym>
    <synonym>Dihydrin</synonym>
    <synonym>(3-a,5-a)-Cholestan-3-ol</synonym>
    <synonym>(3-Α,5-α)-cholestan-3-ol</synonym>
    <synonym>3a-Hydroxy-5a-cholestane</synonym>
    <synonym>3Α-hydroxy-5α-cholestane</synonym>
    <synonym>5a-Cholestan-3a-ol</synonym>
    <synonym>5Α-cholestan-3α-ol</synonym>
    <synonym>5b-Cholestan-3a-ol</synonym>
    <synonym>5b-Cholestane-3a-ol</synonym>
    <synonym>5b-Cholestanol</synonym>
    <synonym>5beta-Cholestan-3alpha-ol</synonym>
    <synonym>5beta-Cholestane-3alpha-ol</synonym>
    <synonym>5beta-Cholestanol</synonym>
    <synonym>a-Coprostanol</synonym>
    <synonym>alpha-Coprostanol</synonym>
    <synonym>Epi-coprosterol</synonym>
    <synonym>Epicoprostanol</synonym>
    <synonym>Epicoprosterol</synonym>
  </synonyms>
  <chemical_formula>C27H48O</chemical_formula>
  <average_molecular_weight>388.6694</average_molecular_weight>
  <monisotopic_moleculate_weight>388.370516158</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol</iupac_name>
  <traditional_iupac>(1S,2S,5R,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol</traditional_iupac>
  <cas_registry_number>516-95-0</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</smiles>
  <inchi>InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20+,21-,22+,23-,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>QYIXCDOBOSTCEI-FBVYSKEZSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Cholestane steroids</sub_class>
    <direct_parent>Cholesterols and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alpha-hydroxysteroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cholesterol</substituent>
      <substituent>Cholesterol-skeleton</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3alpha-sterol</external_descriptor>
      <external_descriptor>5alpha-cholestane</external_descriptor>
      <external_descriptor>Cholesterol and derivatives</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>113 - 114 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>388.6694</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>388.370516158</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H48O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20+,21-,22+,23-,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QYIXCDOBOSTCEI-FBVYSKEZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>119.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46293</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46294</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>46295</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>116856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>116857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>116858</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>59456</chemspider_id>
  <foodb_id>FDB022694</foodb_id>
  <kegg_id>C12978</kegg_id>
  <pubchem_compound_id>66066</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>31542</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6329</metlin_id>
  <synthesis_reference>Ruzicka, L.; Brungger, H.; Eichenberger, E.; Meyer, Jules.  Polyterpenes and polyterpenoids. XCI. Preparation of coprosterol, epicoprosterol and epihydrocholesterol. Spatial position of the hydroxyl group in the sterols.    Helvetica Chimica Acta  (1934),  17  1407-16.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:49 UTC</creation_date>
  <update_date>2020-03-13 16:28:53 UTC</update_date>
  <accession>BMDB0001570</accession>
  <secondary_accessions>
    <accession>BMDB01570</accession>
  </secondary_accessions>
  <name>Thymidine 3',5'-cyclic monophosphate</name>
  <description/>
  <synonyms>
    <synonym>Thymidine 3',5'-cyclic monophosphoric acid</synonym>
    <synonym>3',5'-Cyclic thymidine monophosphate</synonym>
    <synonym>3',5'-Cyclic TMP</synonym>
    <synonym>4H-Furo[3,2-D]-1,3,2-dioxaphosphorin thymidine deriv.</synonym>
    <synonym>CTMP</synonym>
    <synonym>Cyclic 3',5'-dTMP</synonym>
    <synonym>Cyclic 3',5'-thymidylate</synonym>
    <synonym>Cyclic 3',5'-thymidylic acid</synonym>
    <synonym>Cyclic TMP</synonym>
    <synonym>Thymidine 3,5-cyclic monophosphate sodium salt</synonym>
    <synonym>Thymidine cyclic 3',5'-phosphate</synonym>
    <synonym>Thymidine cyclophosphate</synonym>
    <synonym>Thymidine phosphate (cyclic)</synonym>
    <synonym>3',5'-Cyclic dTMP</synonym>
    <synonym>Cyclic 3',5'-thymidine monophosphate</synonym>
  </synonyms>
  <chemical_formula>C10H13N2O7P</chemical_formula>
  <average_molecular_weight>304.1932</average_molecular_weight>
  <monisotopic_moleculate_weight>304.046037292</monisotopic_moleculate_weight>
  <iupac_name>1-[(6R)-2-hydroxy-2-oxo-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione</iupac_name>
  <traditional_iupac>1-[(6R)-2-hydroxy-2-oxo-tetrahydro-4H-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-5-methyl-3H-pyrimidine-2,4-dione</traditional_iupac>
  <cas_registry_number>6453-60-7</cas_registry_number>
  <smiles>CC1=CN([C@H]2CC3OP(O)(=O)OCC3O2)C(=O)NC1=O</smiles>
  <inchi>InChI=1S/C10H13N2O7P/c1-5-3-12(10(14)11-9(5)13)8-2-6-7(18-8)4-17-20(15,16)19-6/h3,6-8H,2,4H2,1H3,(H,15,16)(H,11,13,14)/t6?,7?,8-/m1/s1</inchi>
  <inchikey>QSJFDOVQWZVUQG-KAVNDROISA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Diazines</class>
    <sub_class>Pyrimidines and pyrimidine derivatives</sub_class>
    <direct_parent>Pyrimidones</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydropyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic phosphoric acids and derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydropyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[(6R)-2-hydroxy-2-oxo-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>304.1932</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>304.046037292</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CN([C@H]2CC3OP(O)(=O)OCC3O2)C(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H13N2O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H13N2O7P/c1-5-3-12(10(14)11-9(5)13)8-2-6-7(18-8)4-17-20(15,16)19-6/h3,6-8H,2,4H2,1H3,(H,15,16)(H,11,13,14)/t6?,7?,8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QSJFDOVQWZVUQG-KAVNDROISA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>114.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>62.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24291</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319792</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367017</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1677</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id/>
  <foodb_id>FDB022695</foodb_id>
  <kegg_id>C00364</kegg_id>
  <pubchem_compound_id>53477735</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17013</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Khorana, H. G.; Vizsolyi, J. P.  Studies on polynucleotides. VIII. Experiments on the polymerization of mononucleotides. Improved preparation and separation of linear thymidine polynucleotides. Synthesis of corresponding members terminated in deoxycytidine residues.    Journal of the American Chemical Society  (1961),  83  675-85.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:50 UTC</creation_date>
  <update_date>2020-04-16 20:39:07 UTC</update_date>
  <accession>BMDB0001586</accession>
  <secondary_accessions>
    <accession>BMDB01586</accession>
  </secondary_accessions>
  <name>Glucose 1-phosphate</name>
  <description>Galactose 1-phosphate, also known as delta-glucose 1-phosphate or cori ester, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Galactose 1-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Galactose 1-phosphate exists in all living species, ranging from bacteria to humans. Galactose 1-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Uridine diphosphate glucose and galactose 1-phosphate can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate through its interaction with the enzyme galactose-1-phosphate uridylyltransferase. Furthermore, Galactose 1-phosphate can be biosynthesized from D-galactose through the action of the enzyme galactokinase. Finally, Uridine diphosphate glucose and galactose 1-phosphate can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate; which is mediated by the enzyme galactose-1-phosphate uridylyltransferase. In cattle, galactose 1-phosphate is involved in a couple of metabolic pathways, which include the nucleotide sugars metabolism pathway and lactose synthesis pathway. Galactose 1-phosphate is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-O-Phosphono-D-glucopyranose</synonym>
    <synonym>Cori ester</synonym>
    <synonym>D-Glucose 1-phosphate</synonym>
    <synonym>GLC-1-p</synonym>
    <synonym>D-Glucose 1-phosphoric acid</synonym>
    <synonym>Glucose 1-phosphoric acid</synonym>
    <synonym>a-D-Glucopyranosyl phosphate</synonym>
    <synonym>a-D-Glucose 1-phosphate</synonym>
    <synonym>alpha-D-Glucopyranosyl phosphate</synonym>
    <synonym>alpha-D-Glucose 1-phosphate</synonym>
    <synonym>alpha-D-Glucose-1-phosphate</synonym>
    <synonym>alpha-delta-Glucopyranosyl phosphate</synonym>
    <synonym>alpha-delta-Glucose 1-phosphate</synonym>
    <synonym>alpha-delta-Glucose-1-phosphate</synonym>
    <synonym>D-Glucopyranose 1-phosphate</synonym>
    <synonym>D-Glucose-1-p</synonym>
    <synonym>D-Glucose-1-phosphate</synonym>
    <synonym>delta-Glucopyranose 1-phosphate</synonym>
    <synonym>delta-Glucose 1-phosphate</synonym>
    <synonym>delta-Glucose-1-p</synonym>
    <synonym>delta-Glucose-1-phosphate</synonym>
    <synonym>Glucose monophosphate</synonym>
    <synonym>Glucose-1-phosphate</synonym>
    <synonym>Glucose-1P</synonym>
    <synonym>Galactose 1-phosphoric acid</synonym>
  </synonyms>
  <chemical_formula>C6H13O9P</chemical_formula>
  <average_molecular_weight>260.1358</average_molecular_weight>
  <monisotopic_moleculate_weight>260.029718526</monisotopic_moleculate_weight>
  <iupac_name>{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid</iupac_name>
  <traditional_iupac>glucose 1-phosphate</traditional_iupac>
  <cas_registry_number>59-56-3</cas_registry_number>
  <smiles>OC[C@H]1OC(OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1</inchi>
  <inchikey>HXXFSFRBOHSIMQ-GASJEMHNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharide phosphates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D-glucose monophosphate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>1000.0 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>260.1358</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>260.029718526</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1OC(OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13O9P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HXXFSFRBOHSIMQ-GASJEMHNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>156.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.65</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Galactose Metabolism</name>
      <smpdb_id>SMP0087225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycolysis</name>
      <smpdb_id>SMP0087222</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lactose Synthesis</name>
      <smpdb_id>SMP0087229</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Starch and Sucrose Metabolism</name>
      <smpdb_id>SMP0087252</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1657</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1658</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1659</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179634</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>179636</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181968</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181969</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181970</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38132</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>184+/-58</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>52.60 +/- 27.92</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.844</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>MCGEOWN MG, MALPRESS FH: Studies on the synthesis of lactose by the mammary gland. II. The sugar-phosphate esters of milk. Biochem J. 1952 Dec;52(4):606-11.</reference_text>
          <pubmed_id>13018287</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>58 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>43 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>43 +/- 11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>55 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>55 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>58 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>86.70 +/- 128.89</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>43 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>43 +/- 11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>28.31 +/- 27.81</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>363-1178</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By CE-TOFMS</comment>
      <references>
        <reference>
          <reference_text>Muroya S, Oe M, Ojima K, Watanabe A: Metabolomic approach to key metabolites characterizing postmortem aged loin muscle of Japanese Black (Wagyu) cattle. Asian-Australas J Anim Sci. 2019 Aug;32(8):1172-1185. doi: 10.5713/ajas.18.0648.  Epub 2019 Jan 4.</reference_text>
          <pubmed_id>30744349</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value>120</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Kim YH, Kemp R, Samuelsson LM: Effects of dry-aging on meat quality attributes and metabolite profiles of beef loins. Meat Sci. 2016 Jan;111:168-76. doi: 10.1016/j.meatsci.2015.09.008. Epub 2015 Sep  26.</reference_text>
          <pubmed_id>26437054</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>175+/-48</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>388311</chemspider_id>
  <foodb_id>FDB001159</foodb_id>
  <kegg_id>C00103</kegg_id>
  <pubchem_compound_id>439165</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16077</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>D-glucose-1-phosphates</meta_cyc_id>
  <bigg_id>33865</bigg_id>
  <wikipedia_id>Glucose-1-phosphate</wikipedia_id>
  <metlin_id>6331</metlin_id>
  <synthesis_reference>Weinhausel, Andreas; Nidetzky, Bernd; Kysela, Christian; Kulbe, Klaus D. Application of Escherichia coli maltodextrin-phosphorylase for the continuous production of glucose-1-phosphate. Enzyme and Microbial Technology (1995), 17(2), 140-6.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
      <pubmed_id>23497994</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00161</protein_accession>
      <name>Phosphorylase</name>
      <uniprot_id>B0JYK6</uniprot_id>
      <gene_name>PYGM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00446</protein_accession>
      <name>Phosphoglucomutase-1</name>
      <uniprot_id>Q08DP0</uniprot_id>
      <gene_name>PGM1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00957</protein_accession>
      <name>Galactose-1-phosphate uridylyltransferase</name>
      <uniprot_id>Q0V7N7</uniprot_id>
      <gene_name>GALT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00959</protein_accession>
      <name>Galactose-1-phosphate uridylyltransferase</name>
      <uniprot_id>Q58CX1</uniprot_id>
      <gene_name>GALT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00960</protein_accession>
      <name>UTP--glucose-1-phosphate uridylyltransferase</name>
      <uniprot_id>Q07130</uniprot_id>
      <gene_name>UGP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01172</protein_accession>
      <name>Glycogen phosphorylase, brain form</name>
      <uniprot_id>Q3B7M9</uniprot_id>
      <gene_name>PYGB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01208</protein_accession>
      <name>Glycogen phosphorylase, liver form</name>
      <uniprot_id>Q0VCM4</uniprot_id>
      <gene_name>PYGL</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01247</protein_accession>
      <name>Glycogen phosphorylase, muscle form</name>
      <uniprot_id>P79334</uniprot_id>
      <gene_name>PYGM</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:51 UTC</creation_date>
  <update_date>2020-03-13 16:28:55 UTC</update_date>
  <accession>BMDB0001587</accession>
  <secondary_accessions>
    <accession>BMDB01587</accession>
  </secondary_accessions>
  <name>Phenylglyoxylic acid</name>
  <description/>
  <synonyms>
    <synonym>2-oxo-2-Phenylacetate</synonym>
    <synonym>2-oxo-2-Phenylacetic acid</synonym>
    <synonym>2-Phenylethanoic acid</synonym>
    <synonym>alpha-Ketophenylacetic acid</synonym>
    <synonym>alpha-oxo-Benzeneacetic acid</synonym>
    <synonym>Benzeneglyoxylic acid</synonym>
    <synonym>BENZOYL-formIC ACID</synonym>
    <synonym>Benzoylformate</synonym>
    <synonym>Benzoylformic acid</synonym>
    <synonym>Phenylglyoxylate</synonym>
    <synonym>2-Phenylethanoate</synonym>
    <synonym>a-Ketophenylacetate</synonym>
    <synonym>a-Ketophenylacetic acid</synonym>
    <synonym>alpha-Ketophenylacetate</synonym>
    <synonym>Α-ketophenylacetate</synonym>
    <synonym>Α-ketophenylacetic acid</synonym>
    <synonym>a-oxo-Benzeneacetate</synonym>
    <synonym>a-oxo-Benzeneacetic acid</synonym>
    <synonym>alpha-oxo-Benzeneacetate</synonym>
    <synonym>Α-oxo-benzeneacetate</synonym>
    <synonym>Α-oxo-benzeneacetic acid</synonym>
    <synonym>Benzeneglyoxylate</synonym>
    <synonym>BENZOYL-formate</synonym>
    <synonym>a-Oxobenzeneacetic acid</synonym>
    <synonym>alpha-Oxobenzeneacetic acid</synonym>
    <synonym>Oxophenylacetic acid</synonym>
    <synonym>Phenylgloxylic acid</synonym>
    <synonym>Phenyloxoacetic acid</synonym>
    <synonym>Phenylglyoxilic acid</synonym>
    <synonym>Phenylglyoxylic acid, calcium salt</synonym>
    <synonym>Phenylglyoxylic acid, potassium salt</synonym>
    <synonym>Phenylglyoxylic acid, sodium salt</synonym>
    <synonym>Phenylglyoxylic hydrochloride</synonym>
    <synonym>Phenylglyoxylic acid</synonym>
  </synonyms>
  <chemical_formula>C8H6O3</chemical_formula>
  <average_molecular_weight>150.1314</average_molecular_weight>
  <monisotopic_moleculate_weight>150.031694058</monisotopic_moleculate_weight>
  <iupac_name>2-oxo-2-phenylacetic acid</iupac_name>
  <traditional_iupac>benzoylformic acid</traditional_iupac>
  <cas_registry_number>611-73-4</cas_registry_number>
  <smiles>OC(=O)C(=O)C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)</inchi>
  <inchikey>FAQJJMHZNSSFSM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoyl derivatives</sub_class>
    <direct_parent>Benzoyl derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Aryl ketones</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl ketone</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Keto acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>66 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>920.0 mg/mL at 0 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-oxo-2-phenylacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>150.1314</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>150.031694058</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)C(=O)C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H6O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FAQJJMHZNSSFSM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1660</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269070</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437359</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>11421</chemspider_id>
  <foodb_id>FDB022696</foodb_id>
  <kegg_id>C02137</kegg_id>
  <pubchem_compound_id>11915</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18280</chebi_id>
  <drugbank_id>DB02279</drugbank_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>PHENYLGLYOXYLATE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Phenylglyoxylic_acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Hurd, Charles D.; McNamee, R. W.; Green, Frank O. Benzoylformic acid from styrene. Journal of the American Chemical Society (1939), 61 2979-80.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:52 UTC</creation_date>
  <update_date>2020-03-13 16:28:55 UTC</update_date>
  <accession>BMDB0001624</accession>
  <secondary_accessions>
    <accession>BMDB01624</accession>
  </secondary_accessions>
  <name>2-Hydroxycaproic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Hydroxycaproate</synonym>
    <synonym>DL-2-Hydroxy caproate</synonym>
    <synonym>2-Hydroxyhexanoate</synonym>
    <synonym>2-Hydroxyhexanoic acid</synonym>
    <synonym>DL-2-Hydroxycaproate</synonym>
    <synonym>DL-2-Hydroxycaproic acid</synonym>
    <synonym>DL-2-Hydroxyhexanoate</synonym>
    <synonym>DL-2-Hydroxyhexanoic acid</synonym>
    <synonym>DL-2-Hydroxyhexanoic acidhydroxyhexanoate</synonym>
    <synonym>DL-2-Hydroxyhexanoic acidhydroxyhexanoic acid</synonym>
    <synonym>DL-Hydroxycaproate</synonym>
    <synonym>DL-Hydroxycaproic acid</synonym>
    <synonym>Hydroxy-N-caproate</synonym>
    <synonym>Hydroxy-N-caproic acid</synonym>
    <synonym>Hydroxycaproate</synonym>
    <synonym>Hydroxycaproic acid</synonym>
    <synonym>Hydroxyhexanoate</synonym>
    <synonym>Hydroxyhexanoic acid</synonym>
    <synonym>2-Hydroxycaproic acid</synonym>
  </synonyms>
  <chemical_formula>C6H12O3</chemical_formula>
  <average_molecular_weight>132.1577</average_molecular_weight>
  <monisotopic_moleculate_weight>132.07864425</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxyhexanoic acid</iupac_name>
  <traditional_iupac>hydroxyhexanoate</traditional_iupac>
  <cas_registry_number>6064-63-7</cas_registry_number>
  <smiles>CCCCC(O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H12O3/c1-2-3-4-5(7)6(8)9/h5,7H,2-4H2,1H3,(H,8,9)</inchi>
  <inchikey>NYHNVHGFPZAZGA-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
      <external_descriptor>hydroxy fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>55 - 58 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.86</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxyhexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.1577</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.07864425</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC(O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H12O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H12O3/c1-2-3-4-5(7)6(8)9/h5,7H,2-4H2,1H3,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NYHNVHGFPZAZGA-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16040</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437847</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437849</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>90191</chemspider_id>
  <foodb_id>FDB022697</foodb_id>
  <kegg_id/>
  <pubchem_compound_id>99824</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>86542</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6332</metlin_id>
  <synthesis_reference>Abderhalden, Emil; Weil, Arthur.  A New Amino Acid of the Composition C6H13NO3, Obtained by the Total Hydrolysis of Nerve Proteins.    Z. physiol. Chem.  (1913),  84  39-59.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:53 UTC</creation_date>
  <update_date>2020-04-15 22:00:48 UTC</update_date>
  <accession>BMDB0001644</accession>
  <secondary_accessions>
    <accession>BMDB01644</accession>
  </secondary_accessions>
  <name>D-Xylulose</name>
  <description/>
  <synonyms>
    <synonym>D-Lyxulose</synonym>
    <synonym>D-Threo-pentulose</synonym>
    <synonym>D-Xul</synonym>
    <synonym>Lyxulose</synonym>
    <synonym>Xylulose, (D-threo)-isomer</synonym>
    <synonym>Xylulose</synonym>
    <synonym>Xylulose, (L-threo)-isomer</synonym>
  </synonyms>
  <chemical_formula>C5H10O5</chemical_formula>
  <average_molecular_weight>150.1299</average_molecular_weight>
  <monisotopic_moleculate_weight>150.05282343</monisotopic_moleculate_weight>
  <iupac_name>(3S,4R)-1,3,4,5-tetrahydroxypentan-2-one</iupac_name>
  <traditional_iupac>D-xylulose</traditional_iupac>
  <cas_registry_number>551-84-8</cas_registry_number>
  <smiles>OC[C@@H](O)[C@H](O)C(=O)CO</smiles>
  <inchi>InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m1/s1</inchi>
  <inchikey>ZAQJHHRNXZUBTE-WUJLRWPWSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Acyloins</alternative_parent>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyloin</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>xylulose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3S,4R)-1,3,4,5-tetrahydroxypentan-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>150.1299</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>150.05282343</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@@H](O)[C@H](O)C(=O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZAQJHHRNXZUBTE-WUJLRWPWSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38135</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180467</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <foodb_id>FDB022698</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id>5289590</pubchem_compound_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>17140</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>D-XYLULOSE</meta_cyc_id>
  <knapsack_id>C00019684</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Xylulose</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Takeuchi, Sonoko; Tonouchi, Naoto; Yokozeki, Kenzo.  Production of xylitol or D-xylulose by fermentation of glucose with Gluconobacter, Acetobacter, and Frateuria.    Eur. Pat. Appl.  (2000),     10 pp. </synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:54 UTC</creation_date>
  <update_date>2020-04-15 22:35:55 UTC</update_date>
  <accession>BMDB0001645</accession>
  <secondary_accessions>
    <accession>BMDB01645</accession>
  </secondary_accessions>
  <name>L-Norleucine</name>
  <description>Norleucine, also known as L-aminohexanoate or caprine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Thus, norleucine is considered to be a fatty acid lipid molecule. Norleucine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Norleucine exists in all eukaryotes, ranging from yeast to humans.</description>
  <synonyms>
    <synonym>(S)-2-Aminohexanoic acid</synonym>
    <synonym>2-Aminocaproic acid</synonym>
    <synonym>2-Aminohexanoic acid</synonym>
    <synonym>alpha-Aminocaproic acid</synonym>
    <synonym>Caprine</synonym>
    <synonym>Glycoleucine</synonym>
    <synonym>L(+)-Norleucine</synonym>
    <synonym>L-(+)-Norleucine</synonym>
    <synonym>L-2-Aminohexanoate</synonym>
    <synonym>L-2-Aminohexanoic acid</synonym>
    <synonym>L-Aminohexanoate</synonym>
    <synonym>L-Aminohexanoic acid</synonym>
    <synonym>Nle</synonym>
    <synonym>Norleucine</synonym>
    <synonym>(S)-2-Aminohexanoate</synonym>
    <synonym>2-Aminocaproate</synonym>
    <synonym>2-Aminohexanoate</synonym>
    <synonym>a-Aminocaproate</synonym>
    <synonym>a-Aminocaproic acid</synonym>
    <synonym>alpha-Aminocaproate</synonym>
    <synonym>Α-aminocaproate</synonym>
    <synonym>Α-aminocaproic acid</synonym>
    <synonym>(S)-2-Amino-hexanoate</synonym>
    <synonym>(S)-2-Amino-hexanoic acid</synonym>
    <synonym>(S)-Aminohexanoate</synonym>
    <synonym>(S)-Aminohexanoic acid</synonym>
    <synonym>(S)-Norleucine</synonym>
    <synonym>L-Isomer norleucine</synonym>
    <synonym>Norleucine, L isomer</synonym>
    <synonym>Norleucine, L-isomer</synonym>
    <synonym>2S-Amino-hexanoate</synonym>
  </synonyms>
  <chemical_formula>C6H13NO2</chemical_formula>
  <average_molecular_weight>131.1729</average_molecular_weight>
  <monisotopic_moleculate_weight>131.094628665</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-aminohexanoic acid</iupac_name>
  <traditional_iupac>caprine</traditional_iupac>
  <cas_registry_number>327-57-1</cas_registry_number>
  <smiles>CCCC[C@H](N)C(O)=O</smiles>
  <inchi>InChI=1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1</inchi>
  <inchikey>LRQKBLKVPFOOQJ-YFKPBYRVSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-aminohexanoic acid</external_descriptor>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>12 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.53</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-aminohexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>131.1729</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>131.094628665</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCC[C@H](N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LRQKBLKVPFOOQJ-YFKPBYRVSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1239</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30063</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30796</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38136</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5424</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5429</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5430</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438206</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440112</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Raw milk, by GC-TOF/MS</comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
          <pubmed_id>29197344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>19964</chemspider_id>
  <foodb_id>FDB022699</foodb_id>
  <kegg_id>C01933</kegg_id>
  <pubchem_compound_id>21236</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>18347</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>L-2-AMINOHEXANOATE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Norleucine</wikipedia_id>
  <metlin_id>6334</metlin_id>
  <synthesis_reference>Chibata, Ichiro; Kizumi, Masahiko; Sugiura, Masataka.  Fermentative production of L-norleucine.    Jpn. Kokai Tokkyo Koho  (1977),  4 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.</reference_text>
      <pubmed_id>29197344</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:56 UTC</creation_date>
  <update_date>2020-04-16 20:39:27 UTC</update_date>
  <accession>BMDB0001659</accession>
  <secondary_accessions>
    <accession>BMDB01659</accession>
  </secondary_accessions>
  <name>Acetone</name>
  <description>Acetone, also known as dimethyl ketone or 2-propanone, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, acetone is considered to be an oxygenated hydrocarbon lipid molecule. Acetone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Acetone exists in all living organisms, ranging from bacteria to humans. Acetone is a potentially toxic compound.</description>
  <synonyms>
    <synonym>2-Propanone</synonym>
    <synonym>Aceton</synonym>
    <synonym>Azeton</synonym>
    <synonym>beta-Ketopropane</synonym>
    <synonym>Dimethyl ketone</synonym>
    <synonym>Dimethylcetone</synonym>
    <synonym>Dimethylketon</synonym>
    <synonym>Dimethylketone</synonym>
    <synonym>Methyl ketone</synonym>
    <synonym>Propanon</synonym>
    <synonym>Propanone</synonym>
    <synonym>Pyroacetic ether</synonym>
    <synonym>b-Ketopropane</synonym>
    <synonym>Β-ketopropane</synonym>
    <synonym>Dimethylformaldehyde</synonym>
  </synonyms>
  <chemical_formula>C3H6O</chemical_formula>
  <average_molecular_weight>58.0791</average_molecular_weight>
  <monisotopic_moleculate_weight>58.041864814</monisotopic_moleculate_weight>
  <iupac_name>propan-2-one</iupac_name>
  <traditional_iupac>acetone</traditional_iupac>
  <cas_registry_number>67-64-1</cas_registry_number>
  <smiles>CC(C)=O</smiles>
  <inchi>InChI=1S/C3H6O/c1-3(2)4/h1-2H3</inchi>
  <inchikey>CSCPPACGZOOCGX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as ketones. These are organic compounds  in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Ketones</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Oxygenated hydrocarbons</external_descriptor>
      <external_descriptor>a methyl-ethyl-ketone</external_descriptor>
      <external_descriptor>ketone body</external_descriptor>
      <external_descriptor>methyl ketone</external_descriptor>
      <external_descriptor>propanone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-94.8 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.24</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>19.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>propan-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>58.0791</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>58.041864814</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H6O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H6O/c1-3(2)4/h1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CSCPPACGZOOCGX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>16.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>6.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ketone Body Metabolism</name>
      <smpdb_id>SMP0087202</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29318</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99704</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5441</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17623</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>70+/-22</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in lactating Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in multiparous-early lactation Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Sun LW, Zhang HY, Wu L, Shu S, Xia C, Xu C, Zheng JS: (1)H-Nuclear magnetic resonance-based plasma metabolic profiling of dairy cows with clinical and subclinical ketosis. J Dairy Sci. 2014 Mar;97(3):1552-62. doi: 10.3168/jds.2013-6757. Epub 2014 Jan 17.</reference_text>
          <pubmed_id>24440255</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>177-356</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-FID</comment>
      <references>
        <reference>
          <reference_text>Enjalbert F, Nicot MC, Bayourthe C, Moncoulon R: Ketone bodies in milk and blood of dairy cows: relationship between concentrations and utilization for detection of subclinical ketosis. J Dairy Sci. 2001 Mar;84(3):583-9. doi: 10.3168/jds.S0022-0302(01)74511-0.</reference_text>
          <pubmed_id>11286410</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>69-328</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-MS</comment>
      <references>
        <reference>
          <reference_text>Raun BM, Kristensen NB: Metabolic effects of feeding ethanol or propanol to postpartum transition Holstein cows. J Dairy Sci. 2011 May;94(5):2566-80. doi: 10.3168/jds.2010-3999.</reference_text>
          <pubmed_id>21524548</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>80-990</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By GC-FID</comment>
      <references>
        <reference>
          <reference_text>Sato H: Increased blood concentration of isopropanol in ketotic dairy cows and isopropanol production from acetone in the rumen. Anim Sci J. 2009 Aug;80(4):381-6. doi: 10.1111/j.1740-0929.2009.00649.x.</reference_text>
          <pubmed_id>20163597</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>407 Milk samples from Swedish Red cows</comment>
      <references>
        <reference>
          <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
          <pubmed_id>25087032</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13.20 +/- 3.88</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>22 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>22 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>20 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>12 - 661</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
          <pubmed_id>20338431</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17 - 497</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>17 - 40</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
          <pubmed_id>22098372</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>191.82 +/- 63.7</concentration_value>
      <concentration_units>mg/100g dry matter content</concentration_units>
      <comment>Italian raw milk</comment>
      <references>
        <reference>
          <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>244.13 +/- 123.34</concentration_value>
      <concentration_units>mg/100g dry matter content</concentration_units>
      <comment>Slovenian raw milk</comment>
      <references>
        <reference>
          <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>184 +/- 11</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Enjalbert F, Nicot MC, Bayourthe C, Moncoulon R: Ketone bodies in milk and blood of dairy cows: relationship between concentrations and utilization for detection of subclinical ketosis. J Dairy Sci. 2001 Mar;84(3):583-9. doi: 10.3168/jds.S0022-0302(01)74511-0.</reference_text>
          <pubmed_id>11286410</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.885 +/- 1.601</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>In raw milk samples for diets based on grass silage</comment>
      <references>
        <reference>
          <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
          <pubmed_id>12463694</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.891 +/- 0.698</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>In raw milk samples for diets based on maize silage</comment>
      <references>
        <reference>
          <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
          <pubmed_id>12463694</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.610 +/- 1.138</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>In raw milk samples for diets based on hay</comment>
      <references>
        <reference>
          <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
          <pubmed_id>12463694</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>11.66 +/- 1.22</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>18.85 +/- 3.54</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>66+/-40</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>5-19</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <chemspider_id>175</chemspider_id>
  <foodb_id>FDB008301</foodb_id>
  <kegg_id>C00207</kegg_id>
  <pubchem_compound_id>180</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>15347</chebi_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id>C00048304 C00048954</knapsack_id>
  <meta_cyc_id>ACETONE</meta_cyc_id>
  <bigg_id>34257</bigg_id>
  <wikipedia_id>Acetone</wikipedia_id>
  <metlin_id>3745</metlin_id>
  <synthesis_reference>Ishizaki, Fumiaki.  Acetone and butanol fermentation.    Baiomasu Handobukku  (2002),     166-175.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Enjalbert F, Nicot MC, Bayourthe C, Moncoulon R: Ketone bodies in milk and blood of dairy cows: relationship between concentrations and utilization for detection of subclinical ketosis. J Dairy Sci. 2001 Mar;84(3):583-9. doi: 10.3168/jds.S0022-0302(01)74511-0.</reference_text>
      <pubmed_id>11286410</pubmed_id>
    </reference>
    <reference>
      <reference_text>Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.</reference_text>
      <pubmed_id>12463694</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563.</reference_text>
      <pubmed_id>20338431</pubmed_id>
    </reference>
    <reference>
      <reference_text>Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9.</reference_text>
      <pubmed_id>22098372</pubmed_id>
    </reference>
    <reference>
      <reference_text>Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.</reference_text>
      <pubmed_id>25087032</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:57 UTC</creation_date>
  <update_date>2020-03-13 16:28:57 UTC</update_date>
  <accession>BMDB0001713</accession>
  <secondary_accessions>
    <accession>BMDB01713</accession>
  </secondary_accessions>
  <name>m-Coumaric acid</name>
  <description/>
  <synonyms>
    <synonym>(2E)-3-(3-Hydroxyphenyl)-2-propenoic acid</synonym>
    <synonym>(2E)-3-(3-Hydroxyphenyl)acrylic acid</synonym>
    <synonym>(e)-3-(3-Hydroxyphenyl)-2-propenoic acid</synonym>
    <synonym>3-Coumaric acid</synonym>
    <synonym>m-Hydroxycinnamic acid</synonym>
    <synonym>trans-3-Hydroxycinnamate</synonym>
    <synonym>trans-3-Hydroxycinnamic acid</synonym>
    <synonym>(2E)-3-(3-Hydroxyphenyl)prop-2-enoate</synonym>
    <synonym>(2E)-3-(3-Hydroxyphenyl)-2-propenoate</synonym>
    <synonym>(2E)-3-(3-Hydroxyphenyl)acrylate</synonym>
    <synonym>(e)-3-(3-Hydroxyphenyl)-2-propenoate</synonym>
    <synonym>3-Coumarate</synonym>
    <synonym>m-Hydroxycinnamate</synonym>
    <synonym>(2E)-3-(3-Hydroxyphenyl)prop-2-enoic acid</synonym>
    <synonym>m-Coumarate</synonym>
    <synonym>3'-Hydroxycinnamate</synonym>
    <synonym>3'-Hydroxycinnamic acid</synonym>
    <synonym>3-(3-Hydroxyphenyl)-2-propenoate</synonym>
    <synonym>3-(3-Hydroxyphenyl)-2-propenoic acid</synonym>
    <synonym>3-(3-Hydroxyphenyl)acrylate</synonym>
    <synonym>3-(3-Hydroxyphenyl)acrylic acid</synonym>
    <synonym>3-(3-Hydroxyphenyl)acrylsaeure</synonym>
    <synonym>3-(3-Hydroxyphenyl)prop-2-enoate</synonym>
    <synonym>3-(3-Hydroxyphenyl)prop-2-enoic acid</synonym>
    <synonym>3-Hydroxycinnamate</synonym>
    <synonym>3-Hydroxycinnamic acid</synonym>
    <synonym>m-Hydroxy-cinnamate</synonym>
    <synonym>m-Hydroxy-cinnamic acid</synonym>
    <synonym>trans-3-Coumaric acid</synonym>
    <synonym>3-Coumaric acid, (e)-isomer</synonym>
    <synonym>Meta-coumaric acid</synonym>
    <synonym>(e)-3-(3-Hydroxyphenyl)acrylic acid</synonym>
    <synonym>(e)-3-Hydroxycinnamic acid</synonym>
    <synonym>trans-3-(m-Hydroxyphenyl)-2-propenoic acid</synonym>
    <synonym>trans-m-Coumaric acid</synonym>
    <synonym>trans-m-Hydroxycinnamic acid</synonym>
    <synonym>trans-3-Coumarate</synonym>
    <synonym>m-Coumaric acid</synonym>
  </synonyms>
  <chemical_formula>C9H8O3</chemical_formula>
  <average_molecular_weight>164.158</average_molecular_weight>
  <monisotopic_moleculate_weight>164.047344122</monisotopic_moleculate_weight>
  <iupac_name>(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid</iupac_name>
  <traditional_iupac>m-coumaric acid</traditional_iupac>
  <cas_registry_number>14755-02-3</cas_registry_number>
  <smiles>OC(=O)\C=C\C1=CC(O)=CC=C1</smiles>
  <inchi>InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+</inchi>
  <inchikey>KKSDGJDHHZEWEP-SNAWJCMRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Cinnamic acids and derivatives</class>
    <sub_class>Hydroxycinnamic acids and derivatives</sub_class>
    <direct_parent>Hydroxycinnamic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cinnamic acids</alternative_parent>
      <alternative_parent>Coumaric acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cinnamic acid</substituent>
      <substituent>Coumaric acid</substituent>
      <substituent>Coumaric acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxycinnamic acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Styrene</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-coumaric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>192 - 194 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>164.158</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>164.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)\C=C\C1=CC(O)=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KKSDGJDHHZEWEP-SNAWJCMRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>45.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6004</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38137</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1086</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5442</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5443</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>241516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>241517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>241518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>243571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>243572</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>243573</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439203</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439204</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C12621</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB002590</foodb_id>
  <pubchem_compound_id>637541</pubchem_compound_id>
  <chemspider_id>553147</chemspider_id>
  <pdbe_id/>
  <chebi_id>32357</chebi_id>
  <phenol_explorer_compound_id>463</phenol_explorer_compound_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>M-coumaric_acid</wikipedia_id>
  <metlin_id>305</metlin_id>
  <synthesis_reference>Neish, A. C.  Formation of m- and p-coumaric acids by enzymic deamination of the corresponding isomers of tyrosine.    Phytochemistry (Elsevier)  (1961),  1  1-24.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:58 UTC</creation_date>
  <update_date>2020-04-15 22:35:57 UTC</update_date>
  <accession>BMDB0001721</accession>
  <secondary_accessions>
    <accession>BMDB01721</accession>
  </secondary_accessions>
  <name>DL-O-Phosphoserine</name>
  <description/>
  <synonyms>
    <synonym>2-Amino-3-(phosphonooxy)propanoic acid</synonym>
    <synonym>DL-Serine dihydrogen phosphate</synonym>
    <synonym>DL-Serine, dihydrogen phosphate (ester)</synonym>
    <synonym>Phosphoserine</synonym>
    <synonym>2-Amino-3-(phosphonooxy)propanoate</synonym>
    <synonym>DL-Serine dihydrogen phosphoric acid</synonym>
    <synonym>DL-Serine, dihydrogen phosphoric acid (ester)</synonym>
    <synonym>3-Phospho-1-serine</synonym>
    <synonym>3-Phospho-serine</synonym>
    <synonym>3-Phosphoserine</synonym>
    <synonym>DL-O-Phosphorylserine</synonym>
    <synonym>DL-O-Serine phosphate</synonym>
    <synonym>DL-Serine monophosphorate</synonym>
    <synonym>DL-Serine monophosphoric acid</synonym>
    <synonym>Energoserina</synonym>
    <synonym>O-Phospho-DL-serine</synonym>
    <synonym>O-Phospho-L-serine</synonym>
    <synonym>O-Phosphonoserine</synonym>
    <synonym>p-Serine</synonym>
    <synonym>Phosphorylserine</synonym>
    <synonym>Serine phosphate</synonym>
    <synonym>Serine-3-phosphate</synonym>
    <synonym>Serophen</synonym>
    <synonym>Phosphate, seryl</synonym>
    <synonym>Seryl phosphate</synonym>
    <synonym>Phosphate, serine</synonym>
  </synonyms>
  <chemical_formula>C3H8NO6P</chemical_formula>
  <average_molecular_weight>185.0725</average_molecular_weight>
  <monisotopic_moleculate_weight>185.008923505</monisotopic_moleculate_weight>
  <iupac_name>2-amino-3-(phosphonooxy)propanoic acid</iupac_name>
  <traditional_iupac>P-serine</traditional_iupac>
  <cas_registry_number>17885-08-4</cas_registry_number>
  <smiles>NC(COP(O)(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)</inchi>
  <inchikey>BZQFBWGGLXLEPQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkyl phosphates</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phosphoethanolamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkyl phosphate</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monoalkyl phosphate</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phosphoethanolamine</substituent>
      <substituent>Phosphoric acid ester</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>O-phosphoamino acid</external_descriptor>
      <external_descriptor>non-proteinogenic alpha-amino acid</external_descriptor>
      <external_descriptor>serine derivative</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>228 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-3-(phosphonooxy)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>185.0725</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>185.008923505</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(COP(O)(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H8NO6P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BZQFBWGGLXLEPQ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>130.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180012</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180013</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182346</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182348</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451905</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451928</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01005</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022700</foodb_id>
  <pubchem_compound_id>106</pubchem_compound_id>
  <chemspider_id>104</chemspider_id>
  <pdbe_id/>
  <chebi_id>37712</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id>36594</bigg_id>
  <wikipedia_id>Phosphoserine</wikipedia_id>
  <metlin_id>6338</metlin_id>
  <synthesis_reference>Lacombe J M; Andriamanampisoa F; Pavia A A  Solid-phase synthesis of peptides containing phosphoserine using phosphate tert.-butyl protecting group.    International journal of peptide and protein research  (1990),  36(3),  275-80.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00240</protein_accession>
      <name>14-3-3 protein zeta/delta</name>
      <uniprot_id>P63103</uniprot_id>
      <gene_name>YWHAZ</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00241</protein_accession>
      <name>14-3-3 protein eta</name>
      <uniprot_id>P68509</uniprot_id>
      <gene_name>YWHAH</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00242</protein_accession>
      <name>14-3-3 protein gamma</name>
      <uniprot_id>P68252</uniprot_id>
      <gene_name>YWHAG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00243</protein_accession>
      <name>14-3-3 protein beta/alpha</name>
      <uniprot_id>P68250</uniprot_id>
      <gene_name>YWHAB</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00855</protein_accession>
      <name>Phosphoserine aminotransferase</name>
      <uniprot_id>A6QR28</uniprot_id>
      <gene_name>PSAT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01419</protein_accession>
      <name>14-3-3 protein theta</name>
      <uniprot_id>Q3SZI4</uniprot_id>
      <gene_name>YWHAQ</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01420</protein_accession>
      <name>14-3-3 protein epsilon</name>
      <uniprot_id>P62261</uniprot_id>
      <gene_name>YWHAE</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01421</protein_accession>
      <name>14-3-3 protein sigma</name>
      <uniprot_id>Q0VC36</uniprot_id>
      <gene_name>SFN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:59 UTC</creation_date>
  <update_date>2020-03-13 16:28:58 UTC</update_date>
  <accession>BMDB0001786</accession>
  <secondary_accessions>
    <accession>BMDB01786</accession>
  </secondary_accessions>
  <name>Ethenodeoxyadenosine</name>
  <description/>
  <synonyms>
    <synonym>1,N(6)-Ethenodeoxyadenosine</synonym>
    <synonym>1,N6-Etheno-2'-deoxyadenosine</synonym>
    <synonym>1,N6-Etheno-da</synonym>
    <synonym>1,N6-Ethenodeoxyadenosine</synonym>
    <synonym>N1,N6-Etheno-2'-deoxyadenosine</synonym>
    <synonym>1,N2-Etheno-2'-deoxyguanosine</synonym>
    <synonym>2'-Deoxy-2-deuteroethenoadenosine</synonym>
    <synonym>1,N(6)-Deoxyethenoadenosine</synonym>
  </synonyms>
  <chemical_formula>C12H13N5O3</chemical_formula>
  <average_molecular_weight>275.2633</average_molecular_weight>
  <monisotopic_moleculate_weight>275.101839307</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,5R)-2-(hydroxymethyl)-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-3-ol</iupac_name>
  <traditional_iupac>ethenodeoxyadenosine</traditional_iupac>
  <cas_registry_number>68498-25-9</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CN1C=CN=C21</smiles>
  <inchi>InChI=1S/C12H13N5O3/c18-4-8-7(19)3-9(20-8)17-6-14-10-11-13-1-2-16(11)5-15-12(10)17/h1-2,5-9,18-19H,3-4H2/t7-,8+,9+/m0/s1</inchi>
  <inchikey>XQQIMTUYVDUWKJ-DJLDLDEBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Purines and purine derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidines and pyrimidine derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Purine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R,3S,5R)-2-(hydroxymethyl)-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-3-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>275.2633</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>275.101839307</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CN1C=CN=C21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H13N5O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H13N5O3/c18-4-8-7(19)3-9(20-8)17-6-14-10-11-13-1-2-16(11)5-15-12(10)17/h1-2,5-9,18-19H,3-4H2/t7-,8+,9+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XQQIMTUYVDUWKJ-DJLDLDEBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>68.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>27.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38139</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327931</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>327933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>288723</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB022701</foodb_id>
  <pubchem_compound_id>10945668</pubchem_compound_id>
  <chemspider_id>9120894</chemspider_id>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6339</metlin_id>
  <synthesis_reference>Schmid K; Nair J; Winde G; Velic I; Bartsch H  Increased levels of promutagenic etheno-DNA adducts in colonic polyps of FAP patients.    International journal of cancer. Journal international du cancer  (2000),  87(1),  1-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:00 UTC</creation_date>
  <update_date>2020-04-15 23:56:33 UTC</update_date>
  <accession>BMDB0001830</accession>
  <secondary_accessions>
    <accession>BMDB01830</accession>
  </secondary_accessions>
  <name>Progesterone</name>
  <description>Progesterone, also known as gesterol or corlutin, belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Thus, progesterone is considered to be a steroid lipid molecule. Progesterone is a drug which is used for progesterone supplementation or replacement as part of an assisted reproductive technology (art) treatment for infertile women with progesterone deficiency and for the treatment of secondary amenorrhea. also used for the reduction of the incidence of endometrial hyperplasia and the attendant risk of endometrial carcinoma in postmenopausal women receiving estrogen replacement therapy, as well as treatment of abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology such as fibroids or uterine cancer. Progesterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Progesterone exists in all living organisms, ranging from bacteria to humans. Progesterone participates in a number of enzymatic reactions, within cattle. In particular, Progesterone can be converted into deoxycorticosterone; which is mediated by the enzyme steroid 21-hydroxylase. In addition, Progesterone can be biosynthesized from pregnenolone; which is mediated by the enzyme 3-beta-HSD 1. In cattle, progesterone is involved in the metabolic pathway called the steroidogenesis pathway. Progesterone is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(S)-4-Pregnene-3,20-dione</synonym>
    <synonym>(S)-Pregn-4-en-3,20-dione</synonym>
    <synonym>(S)-Progesterone</synonym>
    <synonym>17alpha-Progesterone</synonym>
    <synonym>4-Pregnene-3,20-dione</synonym>
    <synonym>Agolutin</synonym>
    <synonym>Akrolutin</synonym>
    <synonym>Corpus luteum hormone</synonym>
    <synonym>Crinone</synonym>
    <synonym>Delta(4)-Pregnene-3,20-dione</synonym>
    <synonym>Gelbkoerperhormon</synonym>
    <synonym>Luteohormone</synonym>
    <synonym>Progesteron</synonym>
    <synonym>Prometrium</synonym>
    <synonym>17a-Progesterone</synonym>
    <synonym>17Α-progesterone</synonym>
    <synonym>Δ(4)-pregnene-3,20-dione</synonym>
    <synonym>3,20-Pregnene-4</synonym>
    <synonym>4-Pregnen-3,20-dione</synonym>
    <synonym>beta-Progesterone</synonym>
    <synonym>Bio-luton</synonym>
    <synonym>CIDR</synonym>
    <synonym>Colprosterone</synonym>
    <synonym>Corlutin</synonym>
    <synonym>Corlutina</synonym>
    <synonym>Corluvite</synonym>
    <synonym>Corporin</synonym>
    <synonym>Crinone progesterone gel</synonym>
    <synonym>Curretab</synonym>
    <synonym>Cyclogest</synonym>
    <synonym>Cyclogesterin</synonym>
    <synonym>D4-Pregnene-3,20-dione</synonym>
    <synonym>Delalutin</synonym>
    <synonym>Duraprogen</synonym>
    <synonym>Estima</synonym>
    <synonym>Flavolutan</synonym>
    <synonym>Fologenon</synonym>
    <synonym>Gesterol</synonym>
    <synonym>Gesterol 100</synonym>
    <synonym>Gesterol 50</synonym>
    <synonym>Gestiron</synonym>
    <synonym>Gestone</synonym>
    <synonym>Gestormone</synonym>
    <synonym>Gestron</synonym>
    <synonym>Glanducorpin</synonym>
    <synonym>Gynlutin</synonym>
    <synonym>Gynoluton</synonym>
    <synonym>Gynolutone</synonym>
    <synonym>Hormoflaveine</synonym>
    <synonym>Hormoluton</synonym>
    <synonym>Hydroxyprogesterone caproate</synonym>
    <synonym>Hydroxyprogesterone caproic acid</synonym>
    <synonym>Lingusorbs</synonym>
    <synonym>Lipo-lutin</synonym>
    <synonym>Lucorteum</synonym>
    <synonym>Lucorteum sol</synonym>
    <synonym>Lugesteron</synonym>
    <synonym>Luteal hormone</synonym>
    <synonym>Luteocrin normale</synonym>
    <synonym>Luteodyn</synonym>
    <synonym>Luteogan</synonym>
    <synonym>Luteol</synonym>
    <synonym>Luteopur</synonym>
    <synonym>Luteosan</synonym>
    <synonym>Luteostab</synonym>
    <synonym>Luteovis</synonym>
    <synonym>Luteum</synonym>
    <synonym>Lutex</synonym>
    <synonym>Lutidon</synonym>
    <synonym>Lutociclina</synonym>
    <synonym>Lutocuclin m</synonym>
    <synonym>Lutocyclin</synonym>
    <synonym>Lutocyclin m</synonym>
    <synonym>Lutocylin</synonym>
    <synonym>Lutocylol</synonym>
    <synonym>Lutoform</synonym>
    <synonym>Lutogyl</synonym>
    <synonym>Lutren</synonym>
    <synonym>Lutromone</synonym>
    <synonym>Membrettes</synonym>
    <synonym>Methylpregnone</synonym>
    <synonym>MPA</synonym>
    <synonym>Nalutron</synonym>
    <synonym>Percutacrine</synonym>
    <synonym>Percutacrine luteinique</synonym>
    <synonym>Piaponon</synonym>
    <synonym>Pranone</synonym>
    <synonym>Pregn-4-en-3,20-dione</synonym>
    <synonym>Pregn-4-ene-3,20-dione</synonym>
    <synonym>Pregnene-3,20-dione</synonym>
    <synonym>Pregnenedione</synonym>
    <synonym>Primolut</synonym>
    <synonym>Prochieve</synonym>
    <synonym>Progeffik</synonym>
    <synonym>Progekan</synonym>
    <synonym>Progestan</synonym>
    <synonym>Progestasert</synonym>
    <synonym>Progesterol</synonym>
    <synonym>Progesteronum</synonym>
    <synonym>Progestin</synonym>
    <synonym>Progestogel</synonym>
    <synonym>Progestol</synonym>
    <synonym>Progeston</synonym>
    <synonym>Progestone</synonym>
    <synonym>Progestosol</synonym>
    <synonym>Progestron</synonym>
    <synonym>Progestronol</synonym>
    <synonym>Projestaject</synonym>
    <synonym>Prolets</synonym>
    <synonym>Prolidon</synonym>
    <synonym>Prolutin</synonym>
    <synonym>Proluton</synonym>
    <synonym>Prolutone</synonym>
    <synonym>Prontogest</synonym>
    <synonym>Protormone</synonym>
    <synonym>Syngesterone</synonym>
    <synonym>Syngestrets</synonym>
    <synonym>Synovex S</synonym>
    <synonym>Syntolutan</synonym>
    <synonym>Utrogest</synonym>
    <synonym>Utrogestan</synonym>
    <synonym>Vitarrine</synonym>
    <synonym>Progesterone, (13 alpha,17 alpha)-(+-)-isomer</synonym>
    <synonym>Progesterone, (17 alpha)-isomer</synonym>
    <synonym>Progesterone, (9 beta,10 alpha)-isomer</synonym>
  </synonyms>
  <chemical_formula>C21H30O2</chemical_formula>
  <average_molecular_weight>314.4617</average_molecular_weight>
  <monisotopic_moleculate_weight>314.224580204</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</iupac_name>
  <traditional_iupac>(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</traditional_iupac>
  <cas_registry_number>57-83-0</cas_registry_number>
  <smiles>[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1</inchi>
  <inchikey>RJKFOVLPORLFTN-LEKSSAKUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Pregnane steroids</sub_class>
    <direct_parent>Gluco/mineralocorticoids, progestogins and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>20-oxosteroids</alternative_parent>
      <alternative_parent>3-oxo delta-4-steroids</alternative_parent>
      <alternative_parent>Cyclohexenones</alternative_parent>
      <alternative_parent>Delta-4-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>20-oxosteroid</substituent>
      <substituent>3-oxo-delta-4-steroid</substituent>
      <substituent>3-oxosteroid</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclohexenone</substituent>
      <substituent>Delta-4-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Progestogin-skeleton</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>20-oxo steroid</external_descriptor>
      <external_descriptor>3-oxo Delta(4)-steroid</external_descriptor>
      <external_descriptor>C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives</external_descriptor>
      <external_descriptor>C21-steroid hormone</external_descriptor>
      <external_descriptor>Pregnane and derivatives [Fig]</external_descriptor>
      <external_descriptor>Progestagens</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>121 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.00881 mg/mL at 25 °C</value>
      <source>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.87</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.58</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>314.4617</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>314.224580204</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C21H30O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RJKFOVLPORLFTN-LEKSSAKUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>34.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>92.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Steroidogenesis</name>
      <smpdb_id>SMP0087238</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2212</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2217</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5444</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5445</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374962</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440852</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444006</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444010</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.0922</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS in Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>0.000594</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Detected by HPLC-MS/MS</comment>
      <references>
        <reference>
          <reference_text>Regal P, Nebot C, Diaz-Bao M, Barreiro R, Cepeda A, Fente C: Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: a screening approach to detect forbidden treatments. Steroids. 2011 Mar;76(4):365-75. doi: 10.1016/j.steroids.2010.12.005. Epub 2010 Dec 21.</reference_text>
          <pubmed_id>21172370</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0541 - 0.143</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. range during estrous cycle</comment>
      <references>
        <reference>
          <reference_text>Narendran R, Hacker RR, Smith VG, Lun A: Estrogen and progesterone concentrations in bovine milk during the estrous cycle. Theriogenology. 1979 Jul;12(1):19-25.</reference_text>
          <pubmed_id>16725427</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0312</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw whole milk</comment>
      <references>
        <reference>
          <reference_text>Colazo MG, Ambrose DJ, Kastelic JP, Small JA: Comparison of 2 enzyme immunoassays and a radioimmunoassay for measurement of progesterone concentrations in bovine plasma, skim milk, and whole milk. Can J Vet Res. 2008 Jan;72(1):32-6.</reference_text>
          <pubmed_id>18214159</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00410</kegg_id>
  <drugbank_id>DB00396</drugbank_id>
  <foodb_id>FDB001871</foodb_id>
  <pubchem_compound_id>5994</pubchem_compound_id>
  <chemspider_id>5773</chemspider_id>
  <pdbe_id/>
  <chebi_id>17026</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>PROGESTERONE</meta_cyc_id>
  <knapsack_id>C00034649</knapsack_id>
  <bigg_id>34898</bigg_id>
  <wikipedia_id>Progesterone</wikipedia_id>
  <metlin_id>402</metlin_id>
  <synthesis_reference>Vasquez, L.; Alarcon, J.; Zunza, H.; Becerra, J.; Silva, M.  Chemical-microbiological synthesis of progesterone.    Boletin de la Sociedad Chilena de Quimica  (2001),  46(1),  29-31.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Narendran R, Hacker RR, Smith VG, Lun A: Estrogen and progesterone concentrations in bovine milk during the estrous cycle. Theriogenology. 1979 Jul;12(1):19-25.</reference_text>
      <pubmed_id>16725427</pubmed_id>
    </reference>
    <reference>
      <reference_text>Colazo MG, Ambrose DJ, Kastelic JP, Small JA: Comparison of 2 enzyme immunoassays and a radioimmunoassay for measurement of progesterone concentrations in bovine plasma, skim milk, and whole milk. Can J Vet Res. 2008 Jan;72(1):32-6.</reference_text>
      <pubmed_id>18214159</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00551</protein_accession>
      <name>Prostaglandin E synthase 3</name>
      <uniprot_id>Q3ZBF7</uniprot_id>
      <gene_name>PTGES3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01473</protein_accession>
      <name>Membrane-associated progesterone receptor component 1</name>
      <uniprot_id>Q17QC0</uniprot_id>
      <gene_name>PGRMC1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01624</protein_accession>
      <name>Progesterone receptor</name>
      <uniprot_id>O18972</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01625</protein_accession>
      <name>Progesterone receptor</name>
      <uniprot_id>Q8MIL9</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01626</protein_accession>
      <name>Progestin and adipoQ receptor family member VI</name>
      <uniprot_id>Q2KHW1</uniprot_id>
      <gene_name>PAQR6</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01627</protein_accession>
      <name>Progesterone receptor</name>
      <uniprot_id>Q690N0</uniprot_id>
      <gene_name>PGR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01628</protein_accession>
      <name>Progestin and adipoQ receptor family member IX</name>
      <uniprot_id>Q0II88</uniprot_id>
      <gene_name>PAQR9</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01629</protein_accession>
      <name>Prostaglandin F2-alpha receptor</name>
      <uniprot_id>P37289</uniprot_id>
      <gene_name>PTGFR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01630</protein_accession>
      <name>Progesterone receptor</name>
      <uniprot_id>Q863K6</uniprot_id>
      <gene_name>pr</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01631</protein_accession>
      <name>Transforming growth factor beta-1-induced transcript 1 protein</name>
      <uniprot_id>Q3MHZ4</uniprot_id>
      <gene_name>TGFB1I1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01632</protein_accession>
      <name>Progestin and adipoQ receptor family member VII</name>
      <uniprot_id>Q2T9S9</uniprot_id>
      <gene_name>PAQR7</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:02 UTC</creation_date>
  <update_date>2020-04-15 22:33:03 UTC</update_date>
  <accession>BMDB0001833</accession>
  <secondary_accessions>
    <accession>BMDB01833</accession>
  </secondary_accessions>
  <name>Aminopterin</name>
  <description/>
  <synonyms>
    <synonym>4-Amino-4-deoxypteroylglutamate</synonym>
    <synonym>4-Amino-pga</synonym>
    <synonym>4-Aminofolate</synonym>
    <synonym>4-Aminofolic acid</synonym>
    <synonym>4-Aminopteroylglutamate</synonym>
    <synonym>4-Aminopteroylglutamic acid</synonym>
    <synonym>Aminopterine</synonym>
    <synonym>APGA</synonym>
    <synonym>L-N-[p-[[(2,4-Diamino-6-pteridinyl)methyl]amino]benzoyl]-glutamic acid</synonym>
    <synonym>Pteramina</synonym>
    <synonym>Aminopterin, disodium salt</synonym>
    <synonym>Disodium salt aminopterin</synonym>
    <synonym>Sodium, aminopterin</synonym>
    <synonym>Aminopterin sodium</synonym>
    <synonym>2-[(4-{[(4-amino-2-imino-2,3-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioate</synonym>
    <synonym>Aminopterin</synonym>
  </synonyms>
  <chemical_formula>C19H20N8O5</chemical_formula>
  <average_molecular_weight>440.4127</average_molecular_weight>
  <monisotopic_moleculate_weight>440.15566579</monisotopic_moleculate_weight>
  <iupac_name>2-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</iupac_name>
  <traditional_iupac>aminopterin</traditional_iupac>
  <cas_registry_number>54-62-6</cas_registry_number>
  <smiles>NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)C=N2)C(N)=N1</smiles>
  <inchi>InChI=1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)</inchi>
  <inchikey>TVZGACDUOSZQKY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as folic acids. These are heterocyclic compounds based on the 4-[(pteridin-6-ylmethyl)amino]benzoic acid skeleton conjugated with one or more L-glutamate units.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pteridines and derivatives</class>
    <sub_class>Pterins and derivatives</sub_class>
    <direct_parent>Folic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminobenzamides</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Glutamic acid and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hippuric acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalkylamines</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrazines</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminobenzamide</substituent>
      <substituent>Aminobenzoic acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzamide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoic acid or derivatives</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Folic acid</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hippuric acid</substituent>
      <substituent>Hippuric acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylalkylamine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyrazine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4-{[(2,4-diaminopteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>440.4127</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>440.15566579</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)C=N2)C(N)=N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H20N8O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>TVZGACDUOSZQKY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>219.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>114.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>44.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>287823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326758</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>326760</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>D02527</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022702</foodb_id>
  <pubchem_compound_id>2154</pubchem_compound_id>
  <chemspider_id>2069</chemspider_id>
  <pdbe_id/>
  <chebi_id>108080</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Aminopterin</wikipedia_id>
  <metlin_id>6341</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:03 UTC</creation_date>
  <update_date>2020-04-16 17:51:43 UTC</update_date>
  <accession>BMDB0001842</accession>
  <secondary_accessions>
    <accession>BMDB01842</accession>
  </secondary_accessions>
  <name>Guanidine</name>
  <description/>
  <synonyms>
    <synonym>Aminomethanamidine</synonym>
    <synonym>Gu</synonym>
    <synonym>Guanidin</synonym>
    <synonym>H2N-C(=nh)-NH2</synonym>
    <synonym>Iminourea</synonym>
    <synonym>Carbamidine</synonym>
    <synonym>(4-Aminobutyl) guanidine</synonym>
    <synonym>Aminoformamidine</synonym>
    <synonym>Carbamamidine</synonym>
    <synonym>Imidourea</synonym>
    <synonym>Guanidine hydrochloride</synonym>
    <synonym>Guanidine monohydrate</synonym>
    <synonym>Guanidine monohydrochloride</synonym>
    <synonym>Guanidine sulfate</synonym>
    <synonym>Guanidium chloride</synonym>
    <synonym>Chloride, guanidinium</synonym>
    <synonym>Guanidine monohydroiodine</synonym>
    <synonym>Guanidine sulfate (1:1)</synonym>
    <synonym>Guanidine sulfate (2:1)</synonym>
    <synonym>Guanidine sulfite (1:1)</synonym>
    <synonym>Guanidinium</synonym>
    <synonym>Hydrochloride, guanidine</synonym>
    <synonym>Monohydrobromide, guanidine</synonym>
    <synonym>Monohydrochloride, guanidine</synonym>
    <synonym>Phosphate, guanidine</synonym>
    <synonym>Guanidine monohydrobromide</synonym>
    <synonym>Guanidine phosphate</synonym>
    <synonym>Monohydroiodine, guanidine</synonym>
    <synonym>Nitrate, guanidine</synonym>
    <synonym>Chloride, guanidium</synonym>
    <synonym>Guanidine nitrate</synonym>
    <synonym>Guanidinium chloride</synonym>
    <synonym>Monohydrate, guanidine</synonym>
    <synonym>Sulfate, guanidine</synonym>
  </synonyms>
  <chemical_formula>CH5N3</chemical_formula>
  <average_molecular_weight>59.0705</average_molecular_weight>
  <monisotopic_moleculate_weight>59.048347175</monisotopic_moleculate_weight>
  <iupac_name>guanidine</iupac_name>
  <traditional_iupac>guanidine</traditional_iupac>
  <cas_registry_number>113-00-8</cas_registry_number>
  <smiles>NC(N)=N</smiles>
  <inchi>InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)</inchi>
  <inchikey>ZRALSGWEFCBTJO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Guanidines</sub_class>
    <direct_parent>Guanidines</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>carboxamidine</external_descriptor>
      <external_descriptor>guanidines</external_descriptor>
      <external_descriptor>one-carbon compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>182.3 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>829 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>12.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>guanidine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>59.0705</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>59.048347175</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(N)=N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>CH5N3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZRALSGWEFCBTJO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>75.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>5.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16864</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C17349</kegg_id>
  <drugbank_id>DB00536</drugbank_id>
  <foodb_id>FDB005416</foodb_id>
  <chemspider_id>3400</chemspider_id>
  <pubchem_compound_id>3520</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>42820</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Guanidine</wikipedia_id>
  <metlin_id>6342</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00213</protein_accession>
      <name>Ribonuclease pancreatic</name>
      <uniprot_id>P61823</uniprot_id>
      <gene_name>RNASE1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01355</protein_accession>
      <name>Solute carrier family 22 member 1</name>
      <uniprot_id>A7MBE0</uniprot_id>
      <gene_name>SLC22A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:04 UTC</creation_date>
  <update_date>2020-03-13 16:29:00 UTC</update_date>
  <accession>BMDB0001843</accession>
  <secondary_accessions>
    <accession>BMDB01843</accession>
  </secondary_accessions>
  <name>N-Acryloylglycine</name>
  <description/>
  <synonyms>
    <synonym>1-Aminopropenal acetic acid</synonym>
    <synonym>N-(1-oxo-2-Propenyl)-glycine</synonym>
    <synonym>N-Acryloyl-glycine</synonym>
    <synonym>APAA</synonym>
    <synonym>2-[(1-Hydroxyprop-2-en-1-ylidene)amino]acetate</synonym>
  </synonyms>
  <chemical_formula>C5H7NO3</chemical_formula>
  <average_molecular_weight>129.114</average_molecular_weight>
  <monisotopic_moleculate_weight>129.042593095</monisotopic_moleculate_weight>
  <iupac_name>2-(prop-2-enamido)acetic acid</iupac_name>
  <traditional_iupac>N-acryloylglycine</traditional_iupac>
  <cas_registry_number>24599-25-5</cas_registry_number>
  <smiles>OC(=O)CNC(=O)C=C</smiles>
  <inchi>InChI=1S/C5H7NO3/c1-2-4(7)6-3-5(8)9/h2H,1,3H2,(H,6,7)(H,8,9)</inchi>
  <inchikey>LZCXCXDOGAEFQX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Acrylic acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acrylic acid or derivatives</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.31</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(prop-2-enamido)acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>129.114</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>129.042593095</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)CNC(=O)C=C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H7NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H7NO3/c1-2-4(7)6-3-5(8)9/h2H,1,3H2,(H,6,7)(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LZCXCXDOGAEFQX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>30.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38141</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1693</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1695</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342753</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB022703</foodb_id>
  <pubchem_compound_id>100321</pubchem_compound_id>
  <chemspider_id>90657</chemspider_id>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6343</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:05 UTC</creation_date>
  <update_date>2020-03-13 16:29:01 UTC</update_date>
  <accession>BMDB0001844</accession>
  <secondary_accessions>
    <accession>BMDB01844</accession>
  </secondary_accessions>
  <name>Methylsuccinic acid</name>
  <description/>
  <synonyms>
    <synonym>Methylsuccinate</synonym>
    <synonym>2-Methylbutanedioic acid</synonym>
    <synonym>Methylsuccinic acid, (+-)-isomer</synonym>
    <synonym>(S)-2-Hydroxy-2-methylsuccinate</synonym>
    <synonym>(S)-2-Hydroxy-2-methylsuccinic acid</synonym>
    <synonym>(S)-Citramalate</synonym>
    <synonym>(S)-Citramalic acid</synonym>
    <synonym>2-Methylbutanedioate</synonym>
    <synonym>2-Methylsuccinate</synonym>
    <synonym>2-Methylsuccinic acid</synonym>
    <synonym>Methyl succinate</synonym>
    <synonym>Methyl succinic acid</synonym>
    <synonym>Methylbutanedioate</synonym>
    <synonym>Methylbutanedioic acid</synonym>
    <synonym>MEZ</synonym>
    <synonym>Pyrotartarate</synonym>
    <synonym>Pyrotartaric acid</synonym>
  </synonyms>
  <chemical_formula>C5H8O4</chemical_formula>
  <average_molecular_weight>132.1146</average_molecular_weight>
  <monisotopic_moleculate_weight>132.042258744</monisotopic_moleculate_weight>
  <iupac_name>2-methylbutanedioic acid</iupac_name>
  <traditional_iupac>methylsuccinic acid</traditional_iupac>
  <cas_registry_number>498-21-5</cas_registry_number>
  <smiles>CC(CC(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)</inchi>
  <inchikey>WXUAQHNMJWJLTG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Methyl-branched fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Dicarboxylic acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>117.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>516.5 mg/mL</value>
      <source>Human Metabolome Project</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.13</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-methylbutanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>132.1146</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>132.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(CC(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WXUAQHNMJWJLTG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>74.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30125</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>304665</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347932</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347933</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>347934</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439226</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C08645</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022704</foodb_id>
  <pubchem_compound_id>10349</pubchem_compound_id>
  <chemspider_id>9922</chemspider_id>
  <pdbe_id/>
  <chebi_id>91315</chebi_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>DIETHYL-2R3R-2-METHYL-3-HYDROXYSUCCIN</meta_cyc_id>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>2-Methylsuccinic acid</wikipedia_id>
  <metlin_id>6344</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:06 UTC</creation_date>
  <update_date>2020-04-16 20:40:07 UTC</update_date>
  <accession>BMDB0001846</accession>
  <secondary_accessions>
    <accession>BMDB01846</accession>
  </secondary_accessions>
  <name>Tetrahydrofolic acid</name>
  <description>Tetrahydrofolic acid, also known as tetrahydrofolic acid, belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit. Tetrahydrofolic acid is possibly soluble (in water) and a strong basic compound (based on its pKa). Tetrahydrofolic acid exists in all eukaryotes, ranging from yeast to humans. Tetrahydrofolic acid participates in a number of enzymatic reactions, within cattle. In particular, Tetrahydrofolic acid can be converted into dihydrofolic acid through its interaction with the enzyme dihydrofolate reductase. In addition, Tetrahydrofolic acid and formic acid can be converted into 10-formyltetrahydrofolic acid; which is mediated by the enzyme C-1-tetrahydrofolic acid synthase, cytoplasmic. In cattle, tetrahydrofolic acid is involved in the metabolic pathway called the folate metabolism pathway.</description>
  <synonyms>
    <synonym>Tetrahydrofolate</synonym>
    <synonym>(6S)-Tetrahydrofolate</synonym>
    <synonym>(6S)-Tetrahydrofolic acid</synonym>
    <synonym>5,6,7,8-Tetrahydrofolate</synonym>
    <synonym>5,6,7,8-Tetrahydrofolic acid</synonym>
    <synonym>Tetra-H-folate</synonym>
    <synonym>Tetrahydrafolate</synonym>
    <synonym>Tetrahydropteroyl mono-L-glutamate</synonym>
    <synonym>Tetrahydropteroylglutamate</synonym>
  </synonyms>
  <chemical_formula>C19H23N7O6</chemical_formula>
  <average_molecular_weight>445.4292</average_molecular_weight>
  <monisotopic_moleculate_weight>445.170981503</monisotopic_moleculate_weight>
  <iupac_name>2-{[4-({[(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid</iupac_name>
  <traditional_iupac>2-{[4-({[(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid</traditional_iupac>
  <cas_registry_number>135-16-0</cas_registry_number>
  <smiles>NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)N2)N1</smiles>
  <inchi>InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11-,12?/m0/s1</inchi>
  <inchikey>MSTNYGQPCMXVAQ-PXYINDEMSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Xanthines</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Lactam</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
      <substituent>Xanthine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Purine alkaloids</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>purine alkaloid</external_descriptor>
      <external_descriptor>trimethylxanthine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.22</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-{[4-({[(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>445.4292</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>445.170981503</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)NC(CCC(O)=O)C(O)=O)N2)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H23N7O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t11-,12?/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MSTNYGQPCMXVAQ-PXYINDEMSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>207.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>121.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>43.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>45504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>45505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>45506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>167301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>167302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>167303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218133</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218134</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218135</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>82572</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB022705</foodb_id>
  <pdbe_id/>
  <kegg_id>C00101</kegg_id>
  <chebi_id>20506</chebi_id>
  <pubchem_compound_id>91443</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>33856</bigg_id>
  <wikipedia_id>Tetrahydrofolic acid</wikipedia_id>
  <metlin_id>714</metlin_id>
  <meta_cyc_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00083</protein_accession>
      <name>Serine hydroxymethyltransferase, mitochondrial</name>
      <uniprot_id>Q3SZ20</uniprot_id>
      <gene_name>SHMT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00087</protein_accession>
      <name>Serine hydroxymethyltransferase, cytosolic</name>
      <uniprot_id>Q5E9P9</uniprot_id>
      <gene_name>SHMT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00118</protein_accession>
      <name>Monofunctional C1-tetrahydrofolate synthase, mitochondrial</name>
      <uniprot_id>Q0VCR7</uniprot_id>
      <gene_name>MTHFD1L</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00414</protein_accession>
      <name>Methionine synthase</name>
      <uniprot_id>Q4JIJ3</uniprot_id>
      <gene_name>MTR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00598</protein_accession>
      <name>Bifunctional purine biosynthesis protein PURH</name>
      <uniprot_id>Q0VCK0</uniprot_id>
      <gene_name>ATIC</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00599</protein_accession>
      <name>Methionyl-tRNA formyltransferase, mitochondrial</name>
      <uniprot_id>O77480</uniprot_id>
      <gene_name>MTFMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00600</protein_accession>
      <name>Trifunctional purine biosynthetic protein adenosine-3</name>
      <uniprot_id>Q59A32</uniprot_id>
      <gene_name>GART</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00787</protein_accession>
      <name>Aminomethyltransferase, mitochondrial</name>
      <uniprot_id>P25285</uniprot_id>
      <gene_name>AMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00821</protein_accession>
      <name>Dihydrofolate reductase</name>
      <uniprot_id>P00376</uniprot_id>
      <gene_name>DHFR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:07 UTC</creation_date>
  <update_date>2020-04-16 17:54:18 UTC</update_date>
  <accession>BMDB0001847</accession>
  <secondary_accessions>
    <accession>BMDB01847</accession>
  </secondary_accessions>
  <name>Caffeine</name>
  <description>Caffeine, also known as caffeine or caffeine, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Caffeine is a drug which is used for management of fatigue, orthostatic hypotension, and for the short term treatment of apnea of prematurity in infants. Caffeine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Caffeine participates in a number of enzymatic reactions, within cattle. In particular, Caffeine can be converted into paraxanthine and formaldehyde through its interaction with the enzyme cytochrome P450 1A2. In addition, Caffeine can be converted into theobromine and formaldehyde; which is mediated by the enzymes cytochrome P450 1A2 and cytochrome P450 2E1. In cattle, caffeine is involved in the metabolic pathway called the caffeine metabolism pathway. Caffeine is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1,3,7-Trimethyl-2,6-dioxopurine</synonym>
    <synonym>1,3,7-Trimethylpurine-2,6-dione</synonym>
    <synonym>1,3,7-Trimethylxanthine</synonym>
    <synonym>1-Methyltheobromine</synonym>
    <synonym>3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion</synonym>
    <synonym>7-Methyltheophylline</synonym>
    <synonym>Anhydrous caffeine</synonym>
    <synonym>Cafeina</synonym>
    <synonym>Cafeine</synonym>
    <synonym>Coffein</synonym>
    <synonym>Guaranine</synonym>
    <synonym>Koffein</synonym>
    <synonym>Mateina</synonym>
    <synonym>Methyltheobromine</synonym>
    <synonym>Teina</synonym>
    <synonym>Thein</synonym>
    <synonym>Theine</synonym>
    <synonym>Respia</synonym>
    <synonym>1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione</synonym>
    <synonym>1-Methyl-theobromine</synonym>
    <synonym>3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione</synonym>
    <synonym>7-Methyl theophylline</synonym>
    <synonym>Anhydrous caffeine (JP15)</synonym>
    <synonym>Hycomine</synonym>
    <synonym>Lanorinal</synonym>
    <synonym>Methyltheobromide</synonym>
    <synonym>Methylxanthine theophylline</synonym>
    <synonym>Monohydrate caffeine</synonym>
    <synonym>Propoxyphene</synonym>
    <synonym>Merck dura brand OF caffeine</synonym>
    <synonym>Thompson brand 1 OF caffeine</synonym>
    <synonym>Bristol-myers squibb brand OF caffeine</synonym>
    <synonym>Caffedrine</synonym>
    <synonym>Dexitac</synonym>
    <synonym>Percoffedrinol N</synonym>
    <synonym>Pierre fabre brand OF caffeine</synonym>
    <synonym>Republic drug brand OF caffeine</synonym>
    <synonym>Thompson brand 2 OF caffeine</synonym>
    <synonym>Vivarin</synonym>
    <synonym>Coffeinum N</synonym>
    <synonym>Coffeinum purrum</synonym>
    <synonym>Durvitan</synonym>
    <synonym>GlaxoSmithKline brand OF caffeine</synonym>
    <synonym>No doz</synonym>
    <synonym>Percutaféine</synonym>
    <synonym>Quick-pep</synonym>
    <synonym>Seid brand OF caffeine</synonym>
    <synonym>Berlin-chemie brand OF caffeine</synonym>
    <synonym>Passauer brand OF caffeine</synonym>
    <synonym>Quick pep</synonym>
    <synonym>QuickPep</synonym>
  </synonyms>
  <chemical_formula>C8H10N4O2</chemical_formula>
  <average_molecular_weight>194.1906</average_molecular_weight>
  <monisotopic_moleculate_weight>194.080375584</monisotopic_moleculate_weight>
  <iupac_name>1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione</iupac_name>
  <traditional_iupac>caffeine</traditional_iupac>
  <cas_registry_number>58-08-2</cas_registry_number>
  <smiles>CN1C=NC2=C1C(=O)N(C)C(=O)N2C</smiles>
  <inchi>InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3</inchi>
  <inchikey>RYYVLZVUVIJVGH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Xanthines</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Lactam</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
      <substituent>Xanthine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Purine alkaloids</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>purine alkaloid</external_descriptor>
      <external_descriptor>trimethylxanthine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>238 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>21.6 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.07</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>194.1906</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>194.080375584</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C=NC2=C1C(=O)N(C)C(=O)N2C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H10N4O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RYYVLZVUVIJVGH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>58.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>49.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Caffeine Metabolism</name>
      <smpdb_id>SMP0087186</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>937</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>5869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27428</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1704</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5451</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5457</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22901</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22902</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22903</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442074</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C07481</kegg_id>
  <drugbank_id>DB00201</drugbank_id>
  <foodb_id>FDB002100</foodb_id>
  <chemspider_id>2424</chemspider_id>
  <pubchem_compound_id>2519</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>27732</chebi_id>
  <knapsack_id>C00001492</knapsack_id>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>1-3-7-TRIMETHYLXANTHINE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Caffeine</wikipedia_id>
  <metlin_id>1455</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:08 UTC</creation_date>
  <update_date>2020-03-13 16:29:03 UTC</update_date>
  <accession>BMDB0001851</accession>
  <secondary_accessions>
    <accession>BMDB01851</accession>
  </secondary_accessions>
  <name>L-Arabitol</name>
  <description/>
  <synonyms>
    <synonym>L-Arabinol</synonym>
    <synonym>L-Lyxitol</synonym>
    <synonym>L-Arabinitol</synonym>
    <synonym>Arabitol, (D)-isomer</synonym>
    <synonym>D-Arabinitol</synonym>
    <synonym>D-Arabitol</synonym>
    <synonym>DL-Arabitol</synonym>
    <synonym>Arabino-pentitol</synonym>
    <synonym>Arabitol</synonym>
    <synonym>(+--)-Arabitol</synonym>
    <synonym>Arabitol, (L)-isomer</synonym>
    <synonym>Lyxitol</synonym>
    <synonym>L(-)-Arabitol</synonym>
    <synonym>1,2,3,4,5-Pentahydroxypentane</synonym>
    <synonym>Adonite adonitol</synonym>
    <synonym>Arabinitol</synonym>
    <synonym>L-(+)-Arabitol</synonym>
    <synonym>L-(-)-Arabinitol</synonym>
    <synonym>L-(-)-Arabitol</synonym>
    <synonym>L-Arabitol</synonym>
  </synonyms>
  <chemical_formula>C5H12O5</chemical_formula>
  <average_molecular_weight>152.1458</average_molecular_weight>
  <monisotopic_moleculate_weight>152.068473494</monisotopic_moleculate_weight>
  <iupac_name>(2S,4S)-pentane-1,2,3,4,5-pentol</iupac_name>
  <traditional_iupac>arabinitol</traditional_iupac>
  <cas_registry_number>7643-75-6</cas_registry_number>
  <smiles>OC[C@H](O)C(O)[C@@H](O)CO</smiles>
  <inchi>InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m0/s1</inchi>
  <inchikey>HEBKCHPVOIAQTA-IMJSIDKUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Sugar alcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Sugar alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>arabinitol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>101 - 104 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.64</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,4S)-pentane-1,2,3,4,5-pentol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>152.1458</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>152.068473494</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H](O)C(O)[C@@H](O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H12O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HEBKCHPVOIAQTA-IMJSIDKUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>101.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>32.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38145</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178943</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181266</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181267</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181268</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4922</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1695</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>388391</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB022709</foodb_id>
  <pdbe_id/>
  <kegg_id>C00532</kegg_id>
  <chebi_id>18403</chebi_id>
  <pubchem_compound_id>439255</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>35268</bigg_id>
  <wikipedia_id>Arabitol</wikipedia_id>
  <metlin_id>141</metlin_id>
  <meta_cyc_id>L-ARABITOL</meta_cyc_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:09 UTC</creation_date>
  <update_date>2020-04-16 20:40:07 UTC</update_date>
  <accession>BMDB0001852</accession>
  <secondary_accessions>
    <accession>BMDB01852</accession>
  </secondary_accessions>
  <name>Retinoic acid</name>
  <description>all-trans-All-trans-all-all-trans-retinoic acid, also known as all-all-trans-retinoic acid or all-trans-retinoic acid, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. all-trans-All-trans-all-all-trans-retinoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. all-trans-All-trans-all-all-trans-retinoic acid participates in a number of enzymatic reactions, within cattle. In particular, all-trans-All-trans-all-all-trans-retinoic acid can be biosynthesized from vitamin a through the action of the enzyme retinal dehydrogenase 1. In addition, all-trans-All-trans-all-all-trans-retinoic acid can be biosynthesized from vitamin a; which is mediated by the enzyme retinal dehydrogenase 2. In cattle, all-trans-all-all-trans-retinoic acid is involved in the metabolic pathway called the retinol metabolism pathway. all-trans-All-trans-all-all-trans-retinoic acid is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid</synonym>
    <synonym>3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ecl)</synonym>
    <synonym>AGN 100335</synonym>
    <synonym>all-(e)-Retinoic acid</synonym>
    <synonym>all-trans-beta-Retinoic acid</synonym>
    <synonym>all-trans-Tretinoin</synonym>
    <synonym>all-trans-Vitamin a acid</synonym>
    <synonym>all-trans-Vitamin a1 acid</synonym>
    <synonym>beta-Retinoic acid</synonym>
    <synonym>Eudyna</synonym>
    <synonym>Renova</synonym>
    <synonym>Retin-a</synonym>
    <synonym>Retinoic acid</synonym>
    <synonym>Retisol-a</synonym>
    <synonym>Ro 1-5488</synonym>
    <synonym>Solage</synonym>
    <synonym>Stieva-a</synonym>
    <synonym>trans-Retinoic acid</synonym>
    <synonym>Tretin m</synonym>
    <synonym>Tretinoin</synonym>
    <synonym>Vesanoid</synonym>
    <synonym>Vitamin a acid</synonym>
    <synonym>Vitinoin</synonym>
    <synonym>all-trans-Retinoate</synonym>
    <synonym>Avita</synonym>
    <synonym>Retin a</synonym>
    <synonym>(all-e)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate</synonym>
    <synonym>3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoate (ecl)</synonym>
    <synonym>all-(e)-Retinoate</synonym>
    <synonym>all-trans-b-Retinoate</synonym>
    <synonym>all-trans-b-Retinoic acid</synonym>
    <synonym>all-trans-beta-Retinoate</synonym>
    <synonym>all-trans-Β-retinoate</synonym>
    <synonym>all-trans-Β-retinoic acid</synonym>
    <synonym>b-Retinoate</synonym>
    <synonym>b-Retinoic acid</synonym>
    <synonym>beta-Retinoate</synonym>
    <synonym>Β-retinoate</synonym>
    <synonym>Β-retinoic acid</synonym>
    <synonym>Retinoate</synonym>
    <synonym>trans-Retinoate</synonym>
    <synonym>(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate</synonym>
    <synonym>Tretinoin zinc salt</synonym>
    <synonym>trans Retinoic acid</synonym>
    <synonym>Acid, all-trans-retinoic</synonym>
    <synonym>Salt, tretinoin sodium</synonym>
    <synonym>beta all trans Retinoic acid</synonym>
    <synonym>beta-all-trans-Retinoic acid</synonym>
    <synonym>Acid, vitamin a</synonym>
    <synonym>Potassium salt, tretinoin</synonym>
    <synonym>Sodium salt, tretinoin</synonym>
    <synonym>Acid, beta-all-trans-retinoic</synonym>
    <synonym>Tretinoin potassium salt</synonym>
    <synonym>Zinc salt, tretinoin</synonym>
    <synonym>Acid, retinoic</synonym>
    <synonym>Acid, trans-retinoic</synonym>
    <synonym>Salt, tretinoin potassium</synonym>
    <synonym>Salt, tretinoin zinc</synonym>
    <synonym>Tretinoin sodium salt</synonym>
    <synonym>all trans Retinoic acid</synonym>
    <synonym>Retin-a micro</synonym>
    <synonym>Atralin</synonym>
    <synonym>Tretin-X</synonym>
    <synonym>all-trans-Retinoic acid</synonym>
  </synonyms>
  <chemical_formula>C20H28O2</chemical_formula>
  <average_molecular_weight>300.442</average_molecular_weight>
  <monisotopic_moleculate_weight>300.208930142</monisotopic_moleculate_weight>
  <iupac_name>(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid</iupac_name>
  <traditional_iupac>tretinoin</traditional_iupac>
  <cas_registry_number>302-79-4</cas_registry_number>
  <smiles>C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O</smiles>
  <inchi>InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+</inchi>
  <inchikey>SHGAZHPCJJPHSC-YCNIQYBTSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Retinoids</sub_class>
    <direct_parent>Retinoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Diterpenoids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Diterpenoid</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Retinoic acid</substituent>
      <substituent>Retinoid skeleton</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Retinoids</external_descriptor>
      <external_descriptor>Retinoids</external_descriptor>
      <external_descriptor>retinoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>5.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>300.442</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>300.208930142</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H28O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SHGAZHPCJJPHSC-YCNIQYBTSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>97.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>36.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Retinol Metabolism</name>
      <smpdb_id>SMP0087260</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>91895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>2031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>95708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>160026</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>160027</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>160028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218342</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>392618</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB022710</foodb_id>
  <pdbe_id/>
  <kegg_id>C00777</kegg_id>
  <chebi_id>15367</chebi_id>
  <pubchem_compound_id>444795</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Tretinoin</wikipedia_id>
  <metlin_id/>
  <meta_cyc_id/>
  <synthesis_reference>Solladie, Guy; Girardin, Andre. Highly stereoselective synthesis of vitamin A and all-trans retinoic acid by low-valent titanium induced reductive elimination. Tetrahedron Letters (1988), 29(2), 213-16.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00102</protein_accession>
      <name>Prostaglandin-H2 D-isomerase</name>
      <uniprot_id>O02853</uniprot_id>
      <gene_name>PTGDS</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP00601</protein_accession>
      <name>Retinal dehydrogenase 1</name>
      <uniprot_id>P48644</uniprot_id>
      <gene_name>ALDH1A1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01877</protein_accession>
      <name>Polycomb group RING finger protein 1</name>
      <uniprot_id>Q2YDF9</uniprot_id>
      <gene_name>PCGF1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01878</protein_accession>
      <name>Retinoic acid receptor responder (Tazarotene induced) 1</name>
      <uniprot_id>Q0P5D6</uniprot_id>
      <gene_name>RARRES1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01879</protein_accession>
      <name>Retinoic acid receptor beta</name>
      <uniprot_id>Q45UD6</uniprot_id>
      <gene_name/>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01880</protein_accession>
      <name>Retinoic acid receptor responder protein 2</name>
      <uniprot_id>Q29RS5</uniprot_id>
      <gene_name>RARRES2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01881</protein_accession>
      <name>Retinoic acid receptor, alpha</name>
      <uniprot_id>Q58DG3</uniprot_id>
      <gene_name>RARA</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01882</protein_accession>
      <name>RARG protein</name>
      <uniprot_id>Q08DD4</uniprot_id>
      <gene_name>RARG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01883</protein_accession>
      <name>Peroxisome proliferator-activated receptor gamma</name>
      <uniprot_id>O18971</uniprot_id>
      <gene_name>PPARG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01884</protein_accession>
      <name>Fatty acid-binding protein, adipocyte</name>
      <uniprot_id>P48035</uniprot_id>
      <gene_name>FABP4</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01885</protein_accession>
      <name>Cellular retinoic acid-binding protein 1</name>
      <uniprot_id>P62964</uniprot_id>
      <gene_name>CRABP1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01886</protein_accession>
      <name>LOC100138545 protein</name>
      <uniprot_id>A6QQE3</uniprot_id>
      <gene_name>LOC100138545</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01887</protein_accession>
      <name>Retinoic acid receptor RXR-gamma</name>
      <uniprot_id>Q0VC20</uniprot_id>
      <gene_name>RXRG</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01888</protein_accession>
      <name>Cellular retinoic acid-binding protein 2</name>
      <uniprot_id>Q5PXY7</uniprot_id>
      <gene_name>CRABP2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:11 UTC</creation_date>
  <update_date>2020-03-13 16:29:04 UTC</update_date>
  <accession>BMDB0001854</accession>
  <secondary_accessions>
    <accession>BMDB01854</accession>
  </secondary_accessions>
  <name>Tellurium</name>
  <description>Tellurium, also known as tellur or aurum paradoxum, belongs to the class of inorganic compounds known as homogeneous metalloid compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a metalloid atom. Tellurium exists as a solid, possibly soluble (in water), and possibly neutral molecule.</description>
  <synonyms>
    <synonym>Aurum paradoxum</synonym>
    <synonym>Telloy</synonym>
    <synonym>Tellur</synonym>
    <synonym>Tellurium atom</synonym>
    <synonym>Tellurium element</synonym>
  </synonyms>
  <chemical_formula>Te</chemical_formula>
  <average_molecular_weight>127.6</average_molecular_weight>
  <monisotopic_moleculate_weight>129.906222753</monisotopic_moleculate_weight>
  <iupac_name>λ⁴-tellanetetraylium</iupac_name>
  <traditional_iupac>λ⁴-tellanetetraylium</traditional_iupac>
  <cas_registry_number>13494-80-9</cas_registry_number>
  <smiles>[Te+4]</smiles>
  <inchi>InChI=1S/Te/q+4</inchi>
  <inchikey>LHBANKJAFPUZQV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous metalloid compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a metalloid atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous metalloid compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous metalloid compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous metalloid</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>449.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>λ⁴-tellanetetraylium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>127.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>129.906222753</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Te+4]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Te</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Te/q+4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LHBANKJAFPUZQV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.010 +/- 0.004</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0462 +/- 0.00392</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.03 +/- 0.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00486 +/- 0.000392</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.03 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0478 +/- 0.00313</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS.  Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.01 +/- 0.01</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00572 +/- 0.000392</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00940 +/- 0.000784</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB003718</foodb_id>
  <chemspider_id>103035</chemspider_id>
  <pubchem_compound_id>115151</pubchem_compound_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <bigg_id/>
  <wikipedia_id>Tellurium</wikipedia_id>
  <metlin_id/>
  <chebi_id>30452</chebi_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Detty, Michael R.; Luss, Henry R.; McKelvey, John M.; Geer, Susan M. 12-Te-5 pertelluranes from 1,2-oxatellurolyl-1-ium halides.  Synthesis, structure, and reactivity.  The quest for delocalization in 10-Te-3 telluranes and 12-Te-5 pertelluranes of thiathiophthene structure. J. Org. Chem. 1986(51) p.1692-1700</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:12 UTC</creation_date>
  <update_date>2020-03-13 16:29:04 UTC</update_date>
  <accession>BMDB0001855</accession>
  <secondary_accessions>
    <accession>BMDB01855</accession>
  </secondary_accessions>
  <name>5-Hydroxytryptophol</name>
  <description/>
  <synonyms>
    <synonym>5-HTOL</synonym>
    <synonym>5-Hydroxy-1H-indole-3-ethanol</synonym>
    <synonym>5-Hydroxy-1H-indole-3-ethanol(9ci)</synonym>
    <synonym>5-Hydroxy-3-indole</synonym>
    <synonym>5-Hydroxy-3-indoleacetic acid</synonym>
    <synonym>5-Hydroxy-indole-acetic acid</synonym>
    <synonym>5-Hydroxyindoacetic acid</synonym>
    <synonym>5-Hydroxyindol</synonym>
    <synonym>5-Hydroxyindolacetate</synonym>
    <synonym>5-Hydroxyindolacetic acid</synonym>
    <synonym>5-Hydroxyindole-3-ethanol</synonym>
    <synonym>5-Hydroxyindole-acetic acid</synonym>
    <synonym>Hydroxyindoleacetic acid</synonym>
    <synonym>Hydroxytryptophol</synonym>
  </synonyms>
  <chemical_formula>C10H11NO2</chemical_formula>
  <average_molecular_weight>177.1998</average_molecular_weight>
  <monisotopic_moleculate_weight>177.078978601</monisotopic_moleculate_weight>
  <iupac_name>3-(2-hydroxyethyl)-1H-indol-5-ol</iupac_name>
  <traditional_iupac>hydroxytryptophol</traditional_iupac>
  <cas_registry_number>154-02-9</cas_registry_number>
  <smiles>OCCC1=CNC2=CC=C(O)C=C12</smiles>
  <inchi>InChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2</inchi>
  <inchikey>KQROHCSYOGBQGJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Hydroxyindoles</sub_class>
    <direct_parent>Hydroxyindoles</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>3-alkylindoles</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-alkylindole</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxyindole</substituent>
      <substituent>Indole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(2-hydroxyethyl)-1H-indol-5-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>177.1998</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>177.078978601</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCCC1=CNC2=CC=C(O)C=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H11NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KQROHCSYOGBQGJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>56.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21302</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21304</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22853</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22855</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022711</foodb_id>
  <chemspider_id>8708</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>9061</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5730</metlin_id>
  <synthesis_reference>Da Prada, M.; Bartholini, G.; Pletscher, A.  Formation of 5-hydroxytryptophol by blood platelets after thrombin and reserpine.    Experientia  (1965),  21(3),  135-6.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:13 UTC</creation_date>
  <update_date>2020-04-14 22:49:21 UTC</update_date>
  <accession>BMDB0001857</accession>
  <secondary_accessions>
    <accession>BMDB01857</accession>
  </secondary_accessions>
  <name>1,3-Dimethyluric acid</name>
  <description/>
  <synonyms>
    <synonym>Oxytheophylline</synonym>
    <synonym>1,3-Dimethylate</synonym>
    <synonym>1,3-Dimethylic acid</synonym>
    <synonym>1,3-Dimethylurate</synonym>
  </synonyms>
  <chemical_formula>C7H8N4O3</chemical_formula>
  <average_molecular_weight>196.1634</average_molecular_weight>
  <monisotopic_moleculate_weight>196.059640142</monisotopic_moleculate_weight>
  <iupac_name>1,3-dimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione</iupac_name>
  <traditional_iupac>1,3-dimethyluric acid</traditional_iupac>
  <cas_registry_number>944-73-0</cas_registry_number>
  <smiles>CN1C2=C(NC(=O)N2)C(=O)N(C)C1=O</smiles>
  <inchi>InChI=1S/C7H8N4O3/c1-10-4-3(8-6(13)9-4)5(12)11(2)7(10)14/h1-2H3,(H2,8,9,13)</inchi>
  <inchikey>OTSBKHHWSQYEHK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Xanthines</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
      <substituent>Xanthine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>oxopurine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>408 - 410 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.52 mg/mL at 18 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.52</value>
      <source>GASPARI,F &amp; BONATI,M (1987)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-5.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1,3-dimethyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>196.1634</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>196.059640142</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C2=C(NC(=O)N2)C(=O)N(C)C1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H8N4O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H8N4O3/c1-10-4-3(8-6(13)9-4)5(12)11(2)7(10)14/h1-2H3,(H2,8,9,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OTSBKHHWSQYEHK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>81.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>55.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.74</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1759</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>302406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345130</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345131</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>345132</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022712</foodb_id>
  <chemspider_id>63527</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>70346</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>68447</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD-14118</meta_cyc_id>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>2822</metlin_id>
  <synthesis_reference>Taylor, Edward C.; Sowinski, Frank.  Reaction of 6-amino- and 6-hydrazinopyrimidines with diethyl azodicarboxylate.  New method for C-5 functionalization of pyrimidines.    Journal of Organic Chemistry  (1974),  39(7),  907-10.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:14 UTC</creation_date>
  <update_date>2020-04-15 22:00:52 UTC</update_date>
  <accession>BMDB0001858</accession>
  <secondary_accessions>
    <accession>BMDB01858</accession>
  </secondary_accessions>
  <name>p-Cresol</name>
  <description>p-Cresol, also known as 4-methylphenol or paracresol, belongs to the class of organic compounds known as para cresols. Para cresols are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4. p-Cresol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. p-Cresol exists in all living species, ranging from bacteria to humans. p-Cresol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>1-Hydroxy-4-methylbenzene</synonym>
    <synonym>4-Cresol</synonym>
    <synonym>4-Hydroxytoluene</synonym>
    <synonym>4-Methylphenol</synonym>
    <synonym>p-Kresol</synonym>
    <synonym>p-Methylphenol</synonym>
    <synonym>p-Tolyl alcohol</synonym>
    <synonym>Paracresol</synonym>
    <synonym>1-Methyl-4-hydroxybenzene</synonym>
    <synonym>4-(Pentafluorosulfanyl)phenol</synonym>
    <synonym>4-Methyl phenol</synonym>
    <synonym>4-Methyl-phenol</synonym>
    <synonym>p-Cresylate</synonym>
    <synonym>p-Cresylic acid</synonym>
    <synonym>p-Hydroxytoluene</synonym>
    <synonym>p-Methyl phenol</synonym>
    <synonym>p-Methylhydroxybenzene</synonym>
    <synonym>p-Oxytoluene</synonym>
    <synonym>p-Toluol</synonym>
    <synonym>Paramethyl phenol</synonym>
    <synonym>4-Cresol, potassium salt</synonym>
    <synonym>m-Cresol</synonym>
    <synonym>4-Cresol, aluminum salt</synonym>
    <synonym>4-Cresol, sodium salt</synonym>
    <synonym>Para-cresol</synonym>
  </synonyms>
  <chemical_formula>C7H8O</chemical_formula>
  <average_molecular_weight>108.1378</average_molecular_weight>
  <monisotopic_moleculate_weight>108.057514878</monisotopic_moleculate_weight>
  <iupac_name>4-methylphenol</iupac_name>
  <traditional_iupac>P-cresol</traditional_iupac>
  <cas_registry_number>106-44-5</cas_registry_number>
  <smiles>CC1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3</inchi>
  <inchikey>IWDCLRJOBJJRNH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as para cresols. Para cresols are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Cresols</sub_class>
    <direct_parent>Para cresols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Toluenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>P-cresol</substituent>
      <substituent>Toluene</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a methylphenol</external_descriptor>
      <external_descriptor>cresol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>35.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>21.5 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.94</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-5.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-methylphenol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>108.1378</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>108.057514878</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CC=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H8O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IWDCLRJOBJJRNH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>33.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.93</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>129</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1700</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3422</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26989</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99710</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5496</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182483</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13.87 +/- 11.56</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>13.39 +/- 10.02</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>9.36 +/- 2.04</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB008789</foodb_id>
  <chemspider_id>13839082</chemspider_id>
  <kegg_id>C01468</kegg_id>
  <pubchem_compound_id>2879</pubchem_compound_id>
  <drugbank_id>DB01688</drugbank_id>
  <chebi_id>17847</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD-108</meta_cyc_id>
  <knapsack_id>C00002645</knapsack_id>
  <bigg_id/>
  <wikipedia_id>P-cresol</wikipedia_id>
  <metlin_id>4236</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:15 UTC</creation_date>
  <update_date>2020-04-15 20:48:03 UTC</update_date>
  <accession>BMDB0001859</accession>
  <secondary_accessions>
    <accession>BMDB01859</accession>
  </secondary_accessions>
  <name>Acetaminophen</name>
  <description>Acetaminophen, also known as paracetamol or apap, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Acetaminophen is a drug which is used for temporary relief of fever, minor aches, and pains. Acetaminophen exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Acetaminophen is a potentially toxic compound.</description>
  <synonyms>
    <synonym>4'-Hydroxyacetanilide</synonym>
    <synonym>4-(Acetylamino)phenol</synonym>
    <synonym>4-Acetamidophenol</synonym>
    <synonym>Acenol</synonym>
    <synonym>Acetaminofen</synonym>
    <synonym>Acetaminophene</synonym>
    <synonym>APAP</synonym>
    <synonym>N-Acetyl-p-aminophenol</synonym>
    <synonym>p-Acetamidophenol</synonym>
    <synonym>p-Acetaminophenol</synonym>
    <synonym>p-Acetylaminophenol</synonym>
    <synonym>p-Hydroxyacetanilide</synonym>
    <synonym>p-Hydroxyphenolacetamide</synonym>
    <synonym>Panadol</synonym>
    <synonym>Paracetamolum</synonym>
    <synonym>Tylenol</synonym>
    <synonym>Paracetamol</synonym>
    <synonym>4-Acetaminophenol</synonym>
    <synonym>4-Hydroxyacetanilide</synonym>
    <synonym>4-Hydroxyanilid kyseliny octove</synonym>
    <synonym>a-Per</synonym>
    <synonym>A.F. anacin</synonym>
    <synonym>Abenol</synonym>
    <synonym>Abensanil</synonym>
    <synonym>Abrol</synonym>
    <synonym>Abrolet</synonym>
    <synonym>Acamol</synonym>
    <synonym>Accu-tap</synonym>
    <synonym>Acephen</synonym>
    <synonym>Acertol</synonym>
    <synonym>Aceta elixir</synonym>
    <synonym>Aceta tablets</synonym>
    <synonym>Acetagesic</synonym>
    <synonym>Acetalgin</synonym>
    <synonym>Acetaminophen uniserts</synonym>
    <synonym>Acetamol</synonym>
    <synonym>Acetofen</synonym>
    <synonym>Actamin</synonym>
    <synonym>Actamin extra</synonym>
    <synonym>Actamin super</synonym>
    <synonym>Actifed plus</synonym>
    <synonym>Actimol chewable tablets</synonym>
    <synonym>Actimol children's suspension</synonym>
    <synonym>Actimol infants' suspension</synonym>
    <synonym>Actimol junior strength caplets</synonym>
    <synonym>Actron</synonym>
    <synonym>Afebrin</synonym>
    <synonym>Afebryl</synonym>
    <synonym>Aferadol</synonym>
    <synonym>Algesidal</synonym>
    <synonym>Algina</synonym>
    <synonym>Algomol</synonym>
    <synonym>Algotropyl</synonym>
    <synonym>Allay</synonym>
    <synonym>alpha-Per</synonym>
    <synonym>Alpiny</synonym>
    <synonym>Alpinyl</synonym>
    <synonym>Alvedon</synonym>
    <synonym>Amadil</synonym>
    <synonym>Aminofen</synonym>
    <synonym>Aminofen max</synonym>
    <synonym>Anacin-3</synonym>
    <synonym>Anacin-3 extra strength</synonym>
    <synonym>Anadin dla dzieci</synonym>
    <synonym>Anaflon</synonym>
    <synonym>Analter</synonym>
    <synonym>Anapap</synonym>
    <synonym>Andox</synonym>
    <synonym>Anelix</synonym>
    <synonym>Anexsia</synonym>
    <synonym>Anexsia 10/660</synonym>
    <synonym>Anexsia 5/325</synonym>
    <synonym>Anexsia 7.5/325</synonym>
    <synonym>Anexsia 7.5/650</synonym>
    <synonym>Anhiba</synonym>
    <synonym>Anoquan</synonym>
    <synonym>Anti-algos</synonym>
    <synonym>Antidol</synonym>
    <synonym>Apacet</synonym>
    <synonym>Apacet capsules</synonym>
    <synonym>Apacet elixir</synonym>
    <synonym>Apacet extra strength caplets</synonym>
    <synonym>Apacet extra strength tablets</synonym>
    <synonym>Apacet regular strength tablets</synonym>
    <synonym>Apadon</synonym>
    <synonym>Apamid</synonym>
    <synonym>Apamide</synonym>
    <synonym>Apitrelal</synonym>
    <synonym>Apo-acetaminophen</synonym>
    <synonym>Arfen</synonym>
    <synonym>Asetam</synonym>
    <synonym>Asomal</synonym>
    <synonym>Aspac</synonym>
    <synonym>Aspirin free anacin maximum strength caplets</synonym>
    <synonym>Aspirin free anacin maximum strength gel caplets</synonym>
    <synonym>Aspirin free anacin maximum strength tablets</synonym>
    <synonym>Aspirin-free anacin</synonym>
    <synonym>Aspirin-free excedrin caplets</synonym>
    <synonym>Asplin</synonym>
    <synonym>Atasol caplets</synonym>
    <synonym>Atasol drops</synonym>
    <synonym>Atasol forte caplets</synonym>
    <synonym>Atasol forte tablets</synonym>
    <synonym>Atasol oral solution</synonym>
    <synonym>Atasol tablets</synonym>
    <synonym>Atralidon</synonym>
    <synonym>Babikan</synonym>
    <synonym>Bacetamol</synonym>
    <synonym>Bancap</synonym>
    <synonym>Bancap HC</synonym>
    <synonym>Banesin</synonym>
    <synonym>Bayer select allergy-sinus</synonym>
    <synonym>Bayer select head cold</synonym>
    <synonym>Bayer select headache pain</synonym>
    <synonym>Bayer select maximum strength headache pain relief formula</synonym>
    <synonym>Bayer select menstrual multi-symptom</synonym>
    <synonym>Bayer select sinus pain relief</synonym>
    <synonym>Ben-u-ron</synonym>
    <synonym>Benmyo</synonym>
    <synonym>Bickie-mol</synonym>
    <synonym>Biocetamol</synonym>
    <synonym>Bucet</synonym>
    <synonym>Butalbital</synonym>
    <synonym>Butapap</synonym>
    <synonym>Cadafen</synonym>
    <synonym>Calapol</synonym>
    <synonym>Calmanticold</synonym>
    <synonym>Calpol</synonym>
    <synonym>Capital with codeine</synonym>
    <synonym>Captin</synonym>
    <synonym>Causalon</synonym>
    <synonym>Cefalex</synonym>
    <synonym>Cetadol</synonym>
    <synonym>Children'S acetaminophen elixir drops</synonym>
    <synonym>Children'S acetaminophen oral solution</synonym>
    <synonym>Children'S tylenol chewable</synonym>
    <synonym>Claradol codeine</synonym>
    <synonym>Clixodyne</synonym>
    <synonym>CO-Gesic</synonym>
    <synonym>COD-Acamol forte</synonym>
    <synonym>Codabrol</synonym>
    <synonym>Codalgin</synonym>
    <synonym>Codapane</synonym>
    <synonym>Codicet</synonym>
    <synonym>Codisal</synonym>
    <synonym>Codisal forte</synonym>
    <synonym>Codoliprane</synonym>
    <synonym>Codral pain relief</synonym>
    <synonym>Cofamol</synonym>
    <synonym>Conacetol</synonym>
    <synonym>Contac cough &amp; sore throat formula</synonym>
    <synonym>Contra-schmerz p</synonym>
    <synonym>Coricidin</synonym>
    <synonym>Coricidin D</synonym>
    <synonym>Coricidin sinus</synonym>
    <synonym>Cosutone</synonym>
    <synonym>Croix blanche</synonym>
    <synonym>Cuponol</synonym>
    <synonym>Curadon</synonym>
    <synonym>Curpol</synonym>
    <synonym>Custodial</synonym>
    <synonym>Dapa X-S</synonym>
    <synonym>Darocet</synonym>
    <synonym>Darvocet</synonym>
    <synonym>Darvocet-N 50</synonym>
    <synonym>Datril</synonym>
    <synonym>Datril extra-strength</synonym>
    <synonym>Daygrip</synonym>
    <synonym>Demilets</synonym>
    <synonym>Deminofen</synonym>
    <synonym>Democyl</synonym>
    <synonym>Demogripal</synonym>
    <synonym>Desfebre</synonym>
    <synonym>Dhamol</synonym>
    <synonym>DHC Plus</synonym>
    <synonym>Dial-a-gesic</synonym>
    <synonym>Dial-alpha-gesic</synonym>
    <synonym>Dimindol</synonym>
    <synonym>Dirox</synonym>
    <synonym>Disprol</synonym>
    <synonym>Dol-stop</synonym>
    <synonym>Dolcor</synonym>
    <synonym>Dolefin</synonym>
    <synonym>Dolegrippin</synonym>
    <synonym>Dolene ap-65</synonym>
    <synonym>Dolgesic</synonym>
    <synonym>Doliprane</synonym>
    <synonym>Dolko</synonym>
    <synonym>Dolofugin</synonym>
    <synonym>Doloreduct</synonym>
    <synonym>Dolorfug</synonym>
    <synonym>Dolorol forte</synonym>
    <synonym>Dolorstop</synonym>
    <synonym>Dolotec</synonym>
    <synonym>Dolprone</synonym>
    <synonym>Dorocoff</synonym>
    <synonym>Dresan</synonym>
    <synonym>Dristan cold no drowsiness</synonym>
    <synonym>Dristancito</synonym>
    <synonym>Duracetamol</synonym>
    <synonym>Duradyne DHC</synonym>
    <synonym>Durapan</synonym>
    <synonym>Dymadon</synonym>
    <synonym>Dymadon co</synonym>
    <synonym>Dymadon forte</synonym>
    <synonym>Dypap</synonym>
    <synonym>Ecosetol</synonym>
    <synonym>Elixodyne</synonym>
    <synonym>Empracet</synonym>
    <synonym>Endecon</synonym>
    <synonym>Enelfa</synonym>
    <synonym>Eneril</synonym>
    <synonym>Esgic</synonym>
    <synonym>Esgic-plus</synonym>
    <synonym>Eu-med</synonym>
    <synonym>Excedrin</synonym>
    <synonym>Excedrin caplets</synonym>
    <synonym>Excedrin extra strength caplets</synonym>
    <synonym>Excipain</synonym>
    <synonym>Exdol</synonym>
    <synonym>Exdol strong</synonym>
    <synonym>Fanalgic</synonym>
    <synonym>Farmadol</synonym>
    <synonym>Febranine</synonym>
    <synonym>Febrectal</synonym>
    <synonym>Febrectol</synonym>
    <synonym>Febrex</synonym>
    <synonym>Febricet</synonym>
    <synonym>Febridol</synonym>
    <synonym>Febrilix</synonym>
    <synonym>Febrin</synonym>
    <synonym>Febrinol</synonym>
    <synonym>Febro-gesic</synonym>
    <synonym>Febrolin</synonym>
    <synonym>Femcet</synonym>
    <synonym>Fendon</synonym>
    <synonym>Fensum</synonym>
    <synonym>Fepanil</synonym>
    <synonym>Feverall junior strength</synonym>
    <synonym>Feverall sprinkle caps junior strength</synonym>
    <synonym>Fevor</synonym>
    <synonym>Finimal</synonym>
    <synonym>Finiweh</synonym>
    <synonym>Fioricet</synonym>
    <synonym>Fluparmol</synonym>
    <synonym>Fortalidon p</synonym>
    <synonym>Freka-cetamol</synonym>
    <synonym>Gattaphen T</synonym>
    <synonym>Gelocatil</synonym>
    <synonym>Geluprane</synonym>
    <synonym>Genapap children's elixir</synonym>
    <synonym>Genapap children's tablets</synonym>
    <synonym>Genapap extra strength caplets</synonym>
    <synonym>Genapap extra strength tablets</synonym>
    <synonym>Genapap regular strength tablets</synonym>
    <synonym>Genebs extra strength caplets</synonym>
    <synonym>Genebs regular strength tablets</synonym>
    <synonym>Genebs X-tra</synonym>
    <synonym>Geralgine-p</synonym>
    <synonym>Gripin bebe</synonym>
    <synonym>Grippostad</synonym>
    <synonym>Gynospasmine</synonym>
    <synonym>Hedex</synonym>
    <synonym>Helon N</synonym>
    <synonym>Homoolan</synonym>
    <synonym>Hy-phen</synonym>
    <synonym>Hycomine compound</synonym>
    <synonym>Hydrocet</synonym>
    <synonym>Ildamol</synonym>
    <synonym>Inalgex</synonym>
    <synonym>Infadrops</synonym>
    <synonym>Infants' feverall</synonym>
    <synonym>Influbene N</synonym>
    <synonym>Injectapap</synonym>
    <synonym>Intensin</synonym>
    <synonym>Janupap</synonym>
    <synonym>Junior disprol</synonym>
    <synonym>Kataprin</synonym>
    <synonym>Kinder finimal</synonym>
    <synonym>Korum</synonym>
    <synonym>Kratofin simplex</synonym>
    <synonym>Labamol</synonym>
    <synonym>Lekadol</synonym>
    <synonym>Lemgrip</synonym>
    <synonym>Lemsip</synonym>
    <synonym>Lestemp</synonym>
    <synonym>Liquagesic</synonym>
    <synonym>Liquigesic co</synonym>
    <synonym>Liquiprin</synonym>
    <synonym>Liquiprin children's elixir</synonym>
    <synonym>Liquiprin infants" drops</synonym>
    <synonym>Lonarid</synonym>
    <synonym>Lonarid mono</synonym>
    <synonym>Lorcet-HD</synonym>
    <synonym>Lortab</synonym>
    <synonym>Lupocet</synonym>
    <synonym>Lyteca</synonym>
    <synonym>Lyteca syrup</synonym>
    <synonym>Magnidol</synonym>
    <synonym>Malex N</synonym>
    <synonym>Malgis</synonym>
    <synonym>Malidens</synonym>
    <synonym>Maxadol</synonym>
    <synonym>Medigesic plus</synonym>
    <synonym>Medinol paediatric</synonym>
    <synonym>Medocodene</synonym>
    <synonym>Melabon infantil</synonym>
    <synonym>Mexalen</synonym>
    <synonym>Midol maximum strength</synonym>
    <synonym>Midol PM night time formula</synonym>
    <synonym>Midol regular strength</synonym>
    <synonym>Midol teen formula</synonym>
    <synonym>Migraleve yellow</synonym>
    <synonym>Minafen</synonym>
    <synonym>Minoset</synonym>
    <synonym>Miralgin</synonym>
    <synonym>Momentum</synonym>
    <synonym>mono Praecimed</synonym>
    <synonym>Multin</synonym>
    <synonym>N-(4-Hydroxyphenyl)acetamide</synonym>
    <synonym>N-Acetyl-4-aminophenol</synonym>
    <synonym>Naldegesic</synonym>
    <synonym>NAPA</synonym>
    <synonym>Napafen</synonym>
    <synonym>Napap</synonym>
    <synonym>Naprinol</synonym>
    <synonym>Nealgyl</synonym>
    <synonym>Nebs</synonym>
    <synonym>Neo-fepramol</synonym>
    <synonym>NeoCitran</synonym>
    <synonym>Neodol</synonym>
    <synonym>Neodolito</synonym>
    <synonym>Neopap</synonym>
    <synonym>Neotrend</synonym>
    <synonym>Neuridon</synonym>
    <synonym>New cortal for children</synonym>
    <synonym>NilnOcen</synonym>
    <synonym>Nina</synonym>
    <synonym>NO-Febril</synonym>
    <synonym>Nobedon</synonym>
    <synonym>Nodolex</synonym>
    <synonym>Noral</synonym>
    <synonym>Norcet</synonym>
    <synonym>Norco</synonym>
    <synonym>O-Acetaminophenol</synonym>
    <synonym>Oltyl</synonym>
    <synonym>Oralgan</synonym>
    <synonym>Oraphen-PD</synonym>
    <synonym>Ortensan</synonym>
    <synonym>Oxycet</synonym>
    <synonym>Oxycocet</synonym>
    <synonym>Oxycodone 2.5/apap 500</synonym>
    <synonym>Oxycodone 5/apap 500</synonym>
    <synonym>p-(Acetylamino)phenol</synonym>
    <synonym>Paceco</synonym>
    <synonym>Pacemo</synonym>
    <synonym>Pacemol</synonym>
    <synonym>Pacet</synonym>
    <synonym>Pacimol</synonym>
    <synonym>Paedialgon</synonym>
    <synonym>Paedol</synonym>
    <synonym>Painex</synonym>
    <synonym>Paldesic</synonym>
    <synonym>Pamol</synonym>
    <synonym>Panacete</synonym>
    <synonym>Panadeine</synonym>
    <synonym>Panadeine co</synonym>
    <synonym>Panadiene</synonym>
    <synonym>Panado-co</synonym>
    <synonym>Panado-co caplets</synonym>
    <synonym>Panadol extra strength</synonym>
    <synonym>Panadol junior strength caplets</synonym>
    <synonym>Panadol maximum strength caplets</synonym>
    <synonym>Panadol maximum strength tablets</synonym>
    <synonym>Panaleve</synonym>
    <synonym>Panamax</synonym>
    <synonym>Panasorb</synonym>
    <synonym>Panasorbe</synonym>
    <synonym>Panets</synonym>
    <synonym>Panex</synonym>
    <synonym>Panodil</synonym>
    <synonym>Panofen</synonym>
    <synonym>Pantalgin</synonym>
    <synonym>Papa-deine #3</synonym>
    <synonym>Papa-deine #4</synonym>
    <synonym>Para-suppo</synonym>
    <synonym>Para-tabs</synonym>
    <synonym>Paracemol</synonym>
    <synonym>Paracenol</synonym>
    <synonym>Paracet</synonym>
    <synonym>Paracetamol al</synonym>
    <synonym>Paracetamol antipanin p</synonym>
    <synonym>Paracetamol basics</synonym>
    <synonym>Paracetamol BC</synonym>
    <synonym>Paracetamol DC</synonym>
    <synonym>Paracetamol dr. schmidgall</synonym>
    <synonym>Paracetamol fecofar</synonym>
    <synonym>Paracetamol genericon</synonym>
    <synonym>Paracetamol hanseler</synonym>
    <synonym>Paracetamol harkley</synonym>
    <synonym>Paracetamol heumann</synonym>
    <synonym>Paracetamol hexal</synonym>
    <synonym>Paracetamol italfarmaco</synonym>
    <synonym>Paracetamol nycomed</synonym>
    <synonym>Paracetamol PB</synonym>
    <synonym>Paracetamol raffo</synonym>
    <synonym>Paracetamol ratiopharm</synonym>
    <synonym>Paracetamol rosch</synonym>
    <synonym>Paracetamol saar</synonym>
    <synonym>Paracetamol smithkline beecham</synonym>
    <synonym>Paracetamol stada</synonym>
    <synonym>Paracetamol von CT</synonym>
    <synonym>Paracetamol winthrop</synonym>
    <synonym>Paracetamole</synonym>
    <synonym>Paracetamolo</synonym>
    <synonym>Paracetanol</synonym>
    <synonym>Paracetol</synonym>
    <synonym>Paracin</synonym>
    <synonym>Paracod</synonym>
    <synonym>Paracodol</synonym>
    <synonym>Parador</synonym>
    <synonym>Paradrops</synonym>
    <synonym>Parakapton</synonym>
    <synonym>Parake</synonym>
    <synonym>Paralen</synonym>
    <synonym>Paralief</synonym>
    <synonym>Paralink</synonym>
    <synonym>Paralyoc</synonym>
    <synonym>Paramol</synonym>
    <synonym>Paramolan</synonym>
    <synonym>Paranox</synonym>
    <synonym>Parapan</synonym>
    <synonym>Parasedol</synonym>
    <synonym>Parasin</synonym>
    <synonym>Paraspen</synonym>
    <synonym>Parcetol</synonym>
    <synonym>Parelan</synonym>
    <synonym>Parmol</synonym>
    <synonym>Parogal</synonym>
    <synonym>Paroma</synonym>
    <synonym>Pasolind</synonym>
    <synonym>Pasolind N</synonym>
    <synonym>PCM Paracetamol lichtenstein</synonym>
    <synonym>Pe-tam</synonym>
    <synonym>Pediapirin</synonym>
    <synonym>Pediatrix</synonym>
    <synonym>Pedric</synonym>
    <synonym>Percocet</synonym>
    <synonym>Percocet-5</synonym>
    <synonym>Percocet-demi</synonym>
    <synonym>Percogesic with codeine</synonym>
    <synonym>Perdolan mono</synonym>
    <synonym>Phenaphen</synonym>
    <synonym>Phenaphen caplets</synonym>
    <synonym>Phenaphen w/codeine</synonym>
    <synonym>Phendon</synonym>
    <synonym>Phenipirin</synonym>
    <synonym>Phogoglandin</synonym>
    <synonym>Phrenilin</synonym>
    <synonym>Phrenilin forte</synonym>
    <synonym>Pinex</synonym>
    <synonym>Piramin</synonym>
    <synonym>Pirinasol</synonym>
    <synonym>Plicet</synonym>
    <synonym>Polmofen</synonym>
    <synonym>Predimol</synonym>
    <synonym>Predualito</synonym>
    <synonym>Prestwick_13</synonym>
    <synonym>Prodol</synonym>
    <synonym>Prompt</synonym>
    <synonym>Prontina</synonym>
    <synonym>Propacet</synonym>
    <synonym>Propacet 100</synonym>
    <synonym>Proval #3</synonym>
    <synonym>Puernol</synonym>
    <synonym>Pulmofen</synonym>
    <synonym>Pyregesic-C</synonym>
    <synonym>Pyrigesic</synonym>
    <synonym>Pyrinazine</synonym>
    <synonym>Pyromed</synonym>
    <synonym>Quiet world</synonym>
    <synonym>Redutemp</synonym>
    <synonym>Reliv</synonym>
    <synonym>Remedol</synonym>
    <synonym>Rhinex D-lay tablets</synonym>
    <synonym>Rivalgyl</synonym>
    <synonym>Robigesic</synonym>
    <synonym>Robitussin night relief</synonym>
    <synonym>Rockamol plus</synonym>
    <synonym>Rounox</synonym>
    <synonym>Roxicet</synonym>
    <synonym>Roxicet 5/500</synonym>
    <synonym>Roxilox</synonym>
    <synonym>RubieMol</synonym>
    <synonym>Rubophen</synonym>
    <synonym>Rupemol</synonym>
    <synonym>Salzone</synonym>
    <synonym>Sanicet</synonym>
    <synonym>Sanicopyrine</synonym>
    <synonym>Scanol</synonym>
    <synonym>Scentalgyl</synonym>
    <synonym>Scherzatabletten rezeptur 534</synonym>
    <synonym>Schmerzex</synonym>
    <synonym>Sedalito</synonym>
    <synonym>Sedapap</synonym>
    <synonym>Semolacin</synonym>
    <synonym>Servigesic</synonym>
    <synonym>Seskamol</synonym>
    <synonym>Setakop</synonym>
    <synonym>Setamol</synonym>
    <synonym>Setol</synonym>
    <synonym>Sifenol</synonym>
    <synonym>Sinaspril</synonym>
    <synonym>Sine-OFF sinus medicine caplets</synonym>
    <synonym>Sinedol</synonym>
    <synonym>Sinmol</synonym>
    <synonym>Sinubid</synonym>
    <synonym>SK-Apap</synonym>
    <synonym>Snaplets-FR</synonym>
    <synonym>Spalt fur die nacht</synonym>
    <synonym>Spalt N</synonym>
    <synonym>ST Joseph aspirin-free</synonym>
    <synonym>ST Joseph aspirin-free for children</synonym>
    <synonym>St. joseph cold tablets for children</synonym>
    <synonym>St. joseph fever reducer</synonym>
    <synonym>Stanback</synonym>
    <synonym>Stopain</synonym>
    <synonym>Sudafed severe cold formula</synonym>
    <synonym>Sudafed sinus</synonym>
    <synonym>Sunetheton</synonym>
    <synonym>Supac</synonym>
    <synonym>Supadol mono</synonym>
    <synonym>Supofen</synonym>
    <synonym>Suppap</synonym>
    <synonym>Suppap-120</synonym>
    <synonym>Suppap-325</synonym>
    <synonym>Suppap-650</synonym>
    <synonym>Supramol-m</synonym>
    <synonym>Synalgos-DC-a</synonym>
    <synonym>Tabalgin</synonym>
    <synonym>Tachiprina</synonym>
    <synonym>Talacen</synonym>
    <synonym>Tapanol extra strength caplets</synonym>
    <synonym>Tapanol extra strength tablets</synonym>
    <synonym>Tapar</synonym>
    <synonym>Tavist allergy/sinus/headache</synonym>
    <synonym>Tazamol</synonym>
    <synonym>Temlo</synonym>
    <synonym>Tempanal</synonym>
    <synonym>Tempra</synonym>
    <synonym>Tempra caplets</synonym>
    <synonym>Tempra chewable tablets</synonym>
    <synonym>Tempra d.s</synonym>
    <synonym>Tempra drops</synonym>
    <synonym>Tempra syrup</synonym>
    <synonym>Tencon</synonym>
    <synonym>Termacet</synonym>
    <synonym>Termalgin</synonym>
    <synonym>Termalgine</synonym>
    <synonym>Termofren</synonym>
    <synonym>TheraFlu</synonym>
    <synonym>Tibinide</synonym>
    <synonym>Tibizide</synonym>
    <synonym>Tiffy</synonym>
    <synonym>Tisin</synonym>
    <synonym>Tisiodrazida</synonym>
    <synonym>Titralgan</synonym>
    <synonym>Tizide</synonym>
    <synonym>Tocris-1706</synonym>
    <synonym>Toximer p</synonym>
    <synonym>Tralgon</synonym>
    <synonym>Treupel mon</synonym>
    <synonym>Treupel N</synonym>
    <synonym>Treuphadol</synonym>
    <synonym>Triad</synonym>
    <synonym>Triaminic sore throat formula</synonym>
    <synonym>Triaprin</synonym>
    <synonym>Tricoton</synonym>
    <synonym>Tussapap</synonym>
    <synonym>Tycolet</synonym>
    <synonym>TYL</synonym>
    <synonym>Tylenol allergy sinus</synonym>
    <synonym>Tylenol arthritis extended relief</synonym>
    <synonym>Tylenol caplets</synonym>
    <synonym>Tylenol children's chewable tablets</synonym>
    <synonym>Tylenol children's elixir</synonym>
    <synonym>Tylenol children's suspension liquid</synonym>
    <synonym>Tylenol drops</synonym>
    <synonym>Tylenol elixir</synonym>
    <synonym>Tylenol extra strength adult liquid pain reliever</synonym>
    <synonym>Tylenol extra strength caplets</synonym>
    <synonym>Tylenol extra strength gelcaps</synonym>
    <synonym>Tylenol extra strength tablets</synonym>
    <synonym>Tylenol gelcaps</synonym>
    <synonym>Tylenol infants drops</synonym>
    <synonym>Tylenol infants" suspension drops</synonym>
    <synonym>Tylenol junior strength caplets</synonym>
    <synonym>Tylenol junior strength chewable tablets</synonym>
    <synonym>Tylenol regular strength caplets</synonym>
    <synonym>Tylenol regular strength tablets</synonym>
    <synonym>Tylenol tablets</synonym>
    <synonym>Tylex</synonym>
    <synonym>Tylex CD</synonym>
    <synonym>Tylol</synonym>
    <synonym>Tylox</synonym>
    <synonym>Tylox-325</synonym>
    <synonym>Tymol</synonym>
    <synonym>Ultracet</synonym>
    <synonym>Upsanol</synonym>
    <synonym>Utragin</synonym>
    <synonym>Valadol</synonym>
    <synonym>Valgesic</synonym>
    <synonym>Valorin</synonym>
    <synonym>Valorin extra</synonym>
    <synonym>Vanquish</synonym>
    <synonym>Veralgina</synonym>
    <synonym>Vermidon</synonym>
    <synonym>Verpol</synonym>
    <synonym>Viclor richet</synonym>
    <synonym>Vicodin</synonym>
    <synonym>Vicodin es</synonym>
    <synonym>Vicodin HP</synonym>
    <synonym>Vips</synonym>
    <synonym>Viruflu</synonym>
    <synonym>Vivimed</synonym>
    <synonym>Volpan</synonym>
    <synonym>Wygesic</synonym>
    <synonym>Zatinol</synonym>
    <synonym>Zolben</synonym>
    <synonym>Acetaco</synonym>
    <synonym>Anacin3</synonym>
    <synonym>N-(4-Hydroxyphenyl)acetanilide</synonym>
    <synonym>Acetominophen</synonym>
    <synonym>Hydroxyacetanilide</synonym>
    <synonym>Acetamidophenol</synonym>
    <synonym>Anacin 3</synonym>
  </synonyms>
  <chemical_formula>C8H9NO2</chemical_formula>
  <average_molecular_weight>151.1626</average_molecular_weight>
  <monisotopic_moleculate_weight>151.063328537</monisotopic_moleculate_weight>
  <iupac_name>N-(4-hydroxyphenyl)acetamide</iupac_name>
  <traditional_iupac>acetaminophen</traditional_iupac>
  <cas_registry_number>103-90-2</cas_registry_number>
  <smiles>CC(=O)NC1=CC=C(O)C=C1</smiles>
  <inchi>InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)</inchi>
  <inchikey>RZVAJINKPMORJF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>1-hydroxy-2-unsubstituted benzenoids</sub_class>
    <direct_parent>1-hydroxy-2-unsubstituted benzenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>acetamides</external_descriptor>
      <external_descriptor>phenols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>170 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>14 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.46</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-(4-hydroxyphenyl)acetamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>151.1626</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>151.063328537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)NC1=CC=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H9NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RZVAJINKPMORJF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>49.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27419</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31356</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38150</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5499</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261696</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261697</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261698</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281630</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435688</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>435689</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022713</foodb_id>
  <chemspider_id>1906</chemspider_id>
  <kegg_id>C06804</kegg_id>
  <pubchem_compound_id>1983</pubchem_compound_id>
  <drugbank_id>DB00316</drugbank_id>
  <chebi_id>46195</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD-7669</meta_cyc_id>
  <knapsack_id>C00044491</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Acetaminophen</wikipedia_id>
  <metlin_id>6353</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01130</protein_accession>
      <name>Histidine triad nucleotide-binding protein 2</name>
      <uniprot_id>Q8SQ21</uniprot_id>
      <gene_name>HINT2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01132</protein_accession>
      <name>Histidine triad nucleotide-binding protein 3</name>
      <uniprot_id>Q2YDJ4</uniprot_id>
      <gene_name>HINT3</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP01134</protein_accession>
      <name>Histidine triad nucleotide-binding protein 1</name>
      <uniprot_id>P62958</uniprot_id>
      <gene_name>HINT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
    <protein>
      <protein_accession>BMDBP02581</protein_accession>
      <name>Histidine triad nucleotide binding protein 1</name>
      <uniprot_id>A1XEA3</uniprot_id>
      <gene_name>HINT1</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:16 UTC</creation_date>
  <update_date>2020-04-14 22:49:23 UTC</update_date>
  <accession>BMDB0001860</accession>
  <secondary_accessions>
    <accession>BMDB01860</accession>
  </secondary_accessions>
  <name>Paraxanthine</name>
  <description>Paraxanthine, also known as Paraxanthine, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Paraxanthine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Paraxanthine exists in all living organisms, ranging from bacteria to humans. Paraxanthine participates in a number of enzymatic reactions, within cattle. In particular, Paraxanthine and formaldehyde can be biosynthesized from caffeine through its interaction with the enzyme cytochrome P450 1A2. In addition, Paraxanthine and acetyl-CoA can be converted into 5-acetylamino-6-formylamino-3-methyluracil; which is mediated by the enzyme arylamine N-acetyltransferase 2. In cattle, paraxanthine is involved in the metabolic pathway called the caffeine metabolism pathway.</description>
  <synonyms>
    <synonym>3,7-Dihydro-1,7-dimethyl-1H-purine-2,6-dione</synonym>
    <synonym>p-Xanthine</synonym>
    <synonym>1,7-Dimethyl-xanthine</synonym>
    <synonym>1,7-Dimethylxanthine</synonym>
  </synonyms>
  <chemical_formula>C7H8N4O2</chemical_formula>
  <average_molecular_weight>180.164</average_molecular_weight>
  <monisotopic_moleculate_weight>180.06472552</monisotopic_moleculate_weight>
  <iupac_name>1,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione</iupac_name>
  <traditional_iupac>paraxanthine</traditional_iupac>
  <cas_registry_number>611-59-6</cas_registry_number>
  <smiles>CN1C=NC2=C1C(=O)N(C)C(=O)N2</smiles>
  <inchi>InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)</inchi>
  <inchikey>QUNWUDVFRNGTCO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Xanthines</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Lactam</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Xanthine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Purine alkaloids</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>dimethylxanthine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>351 - 352 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>180.164</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>180.06472552</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C=NC2=C1C(=O)N(C)C(=O)N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H8N4O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QUNWUDVFRNGTCO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>67.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Caffeine Metabolism</name>
      <smpdb_id>SMP0087186</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5501</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5502</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439252</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439956</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450237</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450238</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451896</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022714</foodb_id>
  <chemspider_id>4525</chemspider_id>
  <kegg_id>C13747</kegg_id>
  <pubchem_compound_id>4687</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>25858</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>1-7-DIMETHYLXANTHINE</meta_cyc_id>
  <knapsack_id>C00039930</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Paraxanthine</wikipedia_id>
  <metlin_id>1457</metlin_id>
  <synthesis_reference>Mueller, Christa E.; Deters, Dirk; Dominik, Andreas; Pawlowski, Maciej.  Synthesis of paraxanthine and isoparaxanthine analogs (1,7- and 1,9-substituted xanthine derivatives).    Synthesis  (1998),   (10),  1428-1436.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:17 UTC</creation_date>
  <update_date>2020-03-13 16:29:07 UTC</update_date>
  <accession>BMDB0001861</accession>
  <secondary_accessions>
    <accession>BMDB01861</accession>
  </secondary_accessions>
  <name>3-Methylhistamine</name>
  <description/>
  <synonyms>
    <synonym>L-Histamine deriv. 1</synonym>
    <synonym>N(T)-Methylhistamine</synonym>
    <synonym>N(Tau)-methylhistamine</synonym>
    <synonym>N-Tau-methylhistamine</synonym>
    <synonym>Tau-methylhistamine</synonym>
    <synonym>3-Methylhistamine dihydrochloride</synonym>
    <synonym>3-Methylhistamine</synonym>
  </synonyms>
  <chemical_formula>C6H11N3</chemical_formula>
  <average_molecular_weight>125.1716</average_molecular_weight>
  <monisotopic_moleculate_weight>125.095297367</monisotopic_moleculate_weight>
  <iupac_name>2-(1-methyl-1H-imidazol-5-yl)ethan-1-amine</iupac_name>
  <traditional_iupac>3-methylhistamine</traditional_iupac>
  <cas_registry_number>644-42-8</cas_registry_number>
  <smiles>CN1C=NC=C1CCN</smiles>
  <inchi>InChI=1S/C6H11N3/c1-9-5-8-4-6(9)2-3-7/h4-5H,2-3,7H2,1H3</inchi>
  <inchikey>CPAGZVLINCPJEH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 2-arylethylamines. These are primary amines that have the general formula RCCNH2, where R is an organic group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Amines</sub_class>
    <direct_parent>2-arylethylamines</direct_parent>
    <alternative_parents>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>2-arylethylamine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(1-methyl-1H-imidazol-5-yl)ethan-1-amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>125.1716</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>125.095297367</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C=NC=C1CCN</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H11N3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H11N3/c1-9-5-8-4-6(9)2-3-7/h4-5H,2-3,7H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CPAGZVLINCPJEH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>43.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344272</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344273</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>344274</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451951</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022715</foodb_id>
  <chemspider_id>62725</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>69520</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>114444</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Methylhistamine</wikipedia_id>
  <metlin_id>6355</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00122</protein_accession>
      <name>Histamine N-methyltransferase</name>
      <uniprot_id>Q58DV7</uniprot_id>
      <gene_name>HNMT</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:18 UTC</creation_date>
  <update_date>2020-03-13 16:29:07 UTC</update_date>
  <accession>BMDB0001862</accession>
  <secondary_accessions>
    <accession>BMDB01862</accession>
  </secondary_accessions>
  <name>2-Ethylacrylic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Ethyl-2-propenoic acid</synonym>
    <synonym>2-Ethylpropenoic acid</synonym>
    <synonym>alpha-Methylene-butanoic acid</synonym>
    <synonym>2-Ethyl-2-propenoate</synonym>
    <synonym>2-Ethylpropenoate</synonym>
    <synonym>a-Methylene-butanoate</synonym>
    <synonym>a-Methylene-butanoic acid</synonym>
    <synonym>alpha-Methylene-butanoate</synonym>
    <synonym>Α-methylene-butanoate</synonym>
    <synonym>Α-methylene-butanoic acid</synonym>
    <synonym>2-Ethylacrylate</synonym>
    <synonym>2-Methylene-6ci,7ci,8ci)-butyrate</synonym>
    <synonym>2-Methylene-6ci,7ci,8ci)-butyric acid</synonym>
    <synonym>2-Methylenebutyrate</synonym>
    <synonym>2-Methylenebutyric acid</synonym>
    <synonym>Ethacrylate</synonym>
    <synonym>Ethacrylic acid</synonym>
    <synonym>Poly(2-ethylacrylic acid)</synonym>
    <synonym>2-Ethyl acrylate</synonym>
  </synonyms>
  <chemical_formula>C5H8O2</chemical_formula>
  <average_molecular_weight>100.1158</average_molecular_weight>
  <monisotopic_moleculate_weight>100.0524295</monisotopic_moleculate_weight>
  <iupac_name>2-methylidenebutanoic acid</iupac_name>
  <traditional_iupac>ethacrylic acid</traditional_iupac>
  <cas_registry_number>3586-58-1</cas_registry_number>
  <smiles>CCC(=C)C(O)=O</smiles>
  <inchi>InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h2-3H2,1H3,(H,6,7)</inchi>
  <inchikey>WROUWQQRXUBECT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Branched fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Branched fatty acids</external_descriptor>
      <external_descriptor>alpha,beta-unsaturated monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-methylidenebutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>100.1158</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>100.0524295</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC(=C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h2-3H2,1H3,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WROUWQQRXUBECT-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>26.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38151</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1704</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366774</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022716</foodb_id>
  <chemspider_id>18085</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>19166</pubchem_compound_id>
  <drugbank_id/>
  <chebi_id>84978</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>4141</metlin_id>
  <synthesis_reference>Wang, Yan-jun; Wang, Yu-xia; Tang, Xiang-yang; Zhao, Wen-tao; Qi, Xin.  Synthesis and characterization of 2-ethylacrylic acid.    Shiyou Huagong  (2003),  32(3),  251-253.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:20 UTC</creation_date>
  <update_date>2020-03-13 16:29:08 UTC</update_date>
  <accession>BMDB0001863</accession>
  <secondary_accessions>
    <accession>BMDB01863</accession>
  </secondary_accessions>
  <name>2-Hydroxyvaleric acid</name>
  <description/>
  <synonyms>
    <synonym>alpha-Hydroxy-N-valeric acid</synonym>
    <synonym>alpha-Hydroxyvaleric acid</synonym>
    <synonym>a-Hydroxy-N-valerate</synonym>
    <synonym>a-Hydroxy-N-valeric acid</synonym>
    <synonym>alpha-Hydroxy-N-valerate</synonym>
    <synonym>Α-hydroxy-N-valerate</synonym>
    <synonym>Α-hydroxy-N-valeric acid</synonym>
    <synonym>a-Hydroxyvalerate</synonym>
    <synonym>a-Hydroxyvaleric acid</synonym>
    <synonym>alpha-Hydroxyvalerate</synonym>
    <synonym>Α-hydroxyvalerate</synonym>
    <synonym>Α-hydroxyvaleric acid</synonym>
    <synonym>2-Hydroxyvalerate</synonym>
    <synonym>(+-)-2-Hydroxypentanoate</synonym>
    <synonym>(+-)-2-Hydroxypentanoic acid</synonym>
    <synonym>(S)-2-Hydroxyvaleric acid</synonym>
    <synonym>2-Hydroxy-pentanoate</synonym>
    <synonym>2-Hydroxy-pentanoic acid</synonym>
    <synonym>2-Hydroxypentanoate</synonym>
    <synonym>2-Hydroxypentanoic acid</synonym>
    <synonym>DL-2-Hydroxy valeric acid</synonym>
    <synonym>DL-2-Hydroxy valerate</synonym>
    <synonym>2-Hydroxyvaleric acid</synonym>
  </synonyms>
  <chemical_formula>C5H10O3</chemical_formula>
  <average_molecular_weight>118.1311</average_molecular_weight>
  <monisotopic_moleculate_weight>118.062994186</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxypentanoic acid</iupac_name>
  <traditional_iupac>pentanoic acid, 2-hydroxy-</traditional_iupac>
  <cas_registry_number>617-31-2</cas_registry_number>
  <smiles>CCCC(O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H10O3/c1-2-3-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)</inchi>
  <inchikey>JRHWHSJDIILJAT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Hydroxy fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>34 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.45</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.26</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxypentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>118.1311</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>118.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCC(O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H10O3/c1-2-3-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>JRHWHSJDIILJAT-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>27.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38152</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>57153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>57154</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>57155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>112737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>112738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>112739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439242</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id>88482</chemspider_id>
  <foodb_id>FDB022717</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>98009</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <chebi_id>60647</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>D'yakonov, I. A.; Vinogradova, N. B.  Reactions of aliphatic diazo compounds with unsaturated compounds. VIII. Reaction of diazoacetic ester with allyl bromide.    Zhurnal Obshchei Khimii  (1951),  21  851-60.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:21 UTC</creation_date>
  <update_date>2020-03-13 16:29:08 UTC</update_date>
  <accession>BMDB0001864</accession>
  <secondary_accessions>
    <accession>BMDB01864</accession>
  </secondary_accessions>
  <name>2-Ketohexanoic acid</name>
  <description/>
  <synonyms>
    <synonym>2-Keto-N-caproic acid</synonym>
    <synonym>2-oxo 6:0</synonym>
    <synonym>2-oxo C6:0</synonym>
    <synonym>2-Oxohexanoate</synonym>
    <synonym>alpha-Ketocaproic acid</synonym>
    <synonym>alpha-Ketohexanoic acid</synonym>
    <synonym>2-Keto-N-caproate</synonym>
    <synonym>2-Oxohexanoic acid</synonym>
    <synonym>a-Ketocaproate</synonym>
    <synonym>a-Ketocaproic acid</synonym>
    <synonym>alpha-Ketocaproate</synonym>
    <synonym>Α-ketocaproate</synonym>
    <synonym>Α-ketocaproic acid</synonym>
    <synonym>a-Ketohexanoate</synonym>
    <synonym>a-Ketohexanoic acid</synonym>
    <synonym>alpha-Ketohexanoate</synonym>
    <synonym>Α-ketohexanoate</synonym>
    <synonym>Α-ketohexanoic acid</synonym>
    <synonym>2-Ketohexanoate</synonym>
    <synonym>2-Ketocaproate</synonym>
    <synonym>2-Ketocaproic acid</synonym>
    <synonym>2-oxo-Hexanoate</synonym>
    <synonym>2-oxo-Hexanoic acid</synonym>
    <synonym>alpha-Ketocaproic acid, sodium salt</synonym>
    <synonym>2-Ketohexanoic acid</synonym>
  </synonyms>
  <chemical_formula>C6H10O3</chemical_formula>
  <average_molecular_weight>130.1418</average_molecular_weight>
  <monisotopic_moleculate_weight>130.062994186</monisotopic_moleculate_weight>
  <iupac_name>2-oxohexanoic acid</iupac_name>
  <traditional_iupac>2-oxohexanoic acid</traditional_iupac>
  <cas_registry_number>2492-75-3</cas_registry_number>
  <smiles>CCCCC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H10O3/c1-2-3-4-5(7)6(8)9/h2-4H2,1H3,(H,8,9)</inchi>
  <inchikey>XNIHZNNZJHYHLC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12  carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Medium-chain keto acids and derivatives</sub_class>
    <direct_parent>Medium-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Medium-chain keto acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>Oxo fatty acids</external_descriptor>
      <external_descriptor>Oxo fatty acids</external_descriptor>
      <external_descriptor>medium-chain fatty acid</external_descriptor>
      <external_descriptor>oxo fatty acid</external_descriptor>
      <external_descriptor>straight-chain fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-oxohexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>130.1418</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>130.062994186</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H10O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H10O3/c1-2-3-4-5(7)6(8)9/h2-4H2,1H3,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XNIHZNNZJHYHLC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>31.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22081</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38153</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315028</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>315030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360898</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360899</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>360900</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1705</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00902</kegg_id>
  <chemspider_id>140384</chemspider_id>
  <foodb_id>FDB022718</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>159664</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <chebi_id>17308</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>4144</metlin_id>
  <synthesis_reference>Igarashi, Minoru; Midorikawa, Hiroshi. Synthesis of a-oxo acids from diethyl alkylidenemalonates. Journal of Organic Chemistry (1964), 29(7), 2080-2.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:22 UTC</creation_date>
  <update_date>2020-04-16 17:52:26 UTC</update_date>
  <accession>BMDB0001865</accession>
  <secondary_accessions>
    <accession>BMDB01865</accession>
  </secondary_accessions>
  <name>2-Oxovaleric acid</name>
  <description/>
  <synonyms>
    <synonym>2-Ketopentanoic acid</synonym>
    <synonym>2-Oxovalerate</synonym>
    <synonym>alpha-Ketovaleric acid</synonym>
    <synonym>2-Oxopentanoate</synonym>
    <synonym>2-Ketopentanoate</synonym>
    <synonym>a-Ketovalerate</synonym>
    <synonym>a-Ketovaleric acid</synonym>
    <synonym>alpha-Ketovalerate</synonym>
    <synonym>Α-ketovalerate</synonym>
    <synonym>Α-ketovaleric acid</synonym>
    <synonym>2-Oxopentanoic acid</synonym>
    <synonym>.alpha.-keto-N-valeric acid</synonym>
    <synonym>2-Keto valeric acid</synonym>
    <synonym>2-Keto-N-valeric acid</synonym>
    <synonym>2-Ketovaleric acid</synonym>
    <synonym>2-oxo-N-Valeric acid</synonym>
    <synonym>2-oxo-Pentanoate</synonym>
    <synonym>2-oxo-Pentanoic acid</synonym>
    <synonym>2-oxo-Valeric acid</synonym>
    <synonym>a-Keto-valeric acid</synonym>
    <synonym>a-oxo-N-Valeric acid</synonym>
    <synonym>a-Oxopentanoate</synonym>
    <synonym>a-Oxopentanoic acid</synonym>
    <synonym>a-Oxovaleric acid</synonym>
    <synonym>alpha-Keto-valeric acid</synonym>
    <synonym>alpha-oxo-N-Valeric acid</synonym>
    <synonym>alpha-Oxopentanoate</synonym>
    <synonym>alpha-Oxopentanoic acid</synonym>
    <synonym>alpha-Oxovaleric acid</synonym>
    <synonym>2-Ketopentanoic acid, sodium salt</synonym>
    <synonym>2-Ketovalerate</synonym>
    <synonym>2-Keto valerate</synonym>
    <synonym>2-Oxovaleric acid</synonym>
  </synonyms>
  <chemical_formula>C5H8O3</chemical_formula>
  <average_molecular_weight>116.1152</average_molecular_weight>
  <monisotopic_moleculate_weight>116.047344122</monisotopic_moleculate_weight>
  <iupac_name>2-oxopentanoic acid</iupac_name>
  <traditional_iupac>α-oxopentanoic acid</traditional_iupac>
  <cas_registry_number>1821-02-9</cas_registry_number>
  <smiles>CCCC(=O)C(O)=O</smiles>
  <inchi>InChI=1S/C5H8O3/c1-2-3-4(6)5(7)8/h2-3H2,1H3,(H,7,8)</inchi>
  <inchikey>KDVFRMMRZOCFLS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Keto acids and derivatives</class>
    <sub_class>Short-chain keto acids and derivatives</sub_class>
    <direct_parent>Short-chain keto acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Alpha-keto acids and derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methyl-branched fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Alpha-keto acid</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Short-chain keto acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-oxo monocarboxylic acid</external_descriptor>
      <external_descriptor>Oxo fatty acids</external_descriptor>
      <external_descriptor>Oxo fatty acids</external_descriptor>
      <external_descriptor>oxopentanoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>6.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.35</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-9.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-oxopentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>116.1152</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>116.047344122</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCC(=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O3/c1-2-3-4(6)5(7)8/h2-3H2,1H3,(H,7,8)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KDVFRMMRZOCFLS-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>54.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>27.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>11.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>6500</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372953</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>372954</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439249</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>925</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>947</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26397</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31357</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31964</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31965</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38154</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>S. F. Graham, T. Kennedy, O. Chevallier, A. Gordon, L. Farmer, C. Elliott, B. Moss. The application of NMR to study changes in polar metabolite concentrations in beef longissimus dorsi stored for different periods post mortem. Metabolomics (2010) 6:395-404   doi: 10.1007/s11306-010-0206-y</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C06255</kegg_id>
  <chemspider_id>67142</chemspider_id>
  <foodb_id>FDB003366</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>74563</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <chebi_id>33033</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Lieberman, Irving; Barker, H. A.  b-Keto acid formation and decomposition by preparations of Clostridium kluyveri.    Journal of Bacteriology  (1954),  68  329-33.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:23 UTC</creation_date>
  <update_date>2020-04-15 22:20:54 UTC</update_date>
  <accession>BMDB0001866</accession>
  <secondary_accessions>
    <accession>BMDB01866</accession>
  </secondary_accessions>
  <name>3,4-Dihydroxymandelic acid</name>
  <description>3,4-3,4-3,4-dihydroxymandelic acid, also known as 3,4-dihydroxymandelic acid or 3,4-dihydroxymandelic acid, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-3,4-3,4-dihydroxymandelic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-3,4-3,4-dihydroxymandelic acid exists in all living organisms, ranging from bacteria to humans. 3,4-3,4-3,4-dihydroxymandelic acid participates in a number of enzymatic reactions, within cattle. In particular, 3,4-3,4-3,4-dihydroxymandelic acid can be biosynthesized from 3,4-dihydroxymandelaldehyde; which is mediated by the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In addition, 3,4-3,4-3,4-dihydroxymandelic acid and guaiacol can be converted into vanillylmandelic acid and pyrocatechol through the action of the enzyme catechol O-methyltransferase. In cattle, 3,4-3,4-dihydroxymandelic acid is involved in the metabolic pathway called the tyrosine metabolism pathway.</description>
  <synonyms>
    <synonym>(3,4-Dihydroxyphenyl)(hydroxy)acetic acid</synonym>
    <synonym>3,4-Dihydroxymandelate</synonym>
    <synonym>3,4-Dihydroxyphenylglycolic acid</synonym>
    <synonym>Dihydroxymandelic acid</synonym>
    <synonym>DOMA</synonym>
    <synonym>(3,4-Dihydroxyphenyl)(hydroxy)acetate</synonym>
    <synonym>3,4-Dihydroxyphenylglycolate</synonym>
    <synonym>Dihydroxymandelate</synonym>
    <synonym>3,4 Dihydroxymandelate</synonym>
    <synonym>3,4 Dihydroxymandelic acid</synonym>
    <synonym>3,4-Dihydroxymandelic acid, (S)-isomer</synonym>
    <synonym>3,4-Dihydroxymandelic acid, ion(1-)</synonym>
    <synonym>3,4-Dihydroxymandelic acid, monosodium salt</synonym>
    <synonym>DHMA</synonym>
    <synonym>3,4-Dihydroxymandelic acid, (+-)-isomer</synonym>
  </synonyms>
  <chemical_formula>C8H8O5</chemical_formula>
  <average_molecular_weight>184.1461</average_molecular_weight>
  <monisotopic_moleculate_weight>184.037173366</monisotopic_moleculate_weight>
  <iupac_name>2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid</iupac_name>
  <traditional_iupac>dihydroxymandelic acid</traditional_iupac>
  <cas_registry_number>775-01-9</cas_registry_number>
  <smiles>OC(C(O)=O)C1=CC=C(O)C(O)=C1</smiles>
  <inchi>InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)</inchi>
  <inchikey>RGHMISIYKIHAJW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Benzenediols</sub_class>
    <direct_parent>Catechols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Catechol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>a catechol</external_descriptor>
      <external_descriptor>catechols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.72</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.24</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>184.1461</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>184.037173366</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(C(O)=O)C1=CC=C(O)C(O)=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H8O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RGHMISIYKIHAJW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>42.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5503</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5504</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5505</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5506</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5507</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5509</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370393</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370394</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>370395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439254</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440155</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448194</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C05580</kegg_id>
  <chemspider_id>77371</chemspider_id>
  <foodb_id>FDB030383</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>85782</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <chebi_id>27637</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-11879</meta_cyc_id>
  <bigg_id>46062</bigg_id>
  <wikipedia_id>3,4-Dihydroxymandelic_acid</wikipedia_id>
  <metlin_id>696</metlin_id>
  <synthesis_reference>Joray, Marcel; Breuninger, Manfred.  Process for the preparation of phenolic compounds.    PCT Int. Appl.  (2007),     15pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:24 UTC</creation_date>
  <update_date>2020-04-15 22:24:49 UTC</update_date>
  <accession>BMDB0001867</accession>
  <secondary_accessions>
    <accession>BMDB01867</accession>
  </secondary_accessions>
  <name>4-Aminohippuric acid</name>
  <description/>
  <synonyms>
    <synonym>Aminohippuric acid</synonym>
    <synonym>N-(p-Aminobenzoyl)aminoacetic acid</synonym>
    <synonym>N-(p-Aminobenzoyl)glycine</synonym>
    <synonym>N-(Para-aminobenzoyl)glycine</synonym>
    <synonym>p-Aminohippurate</synonym>
    <synonym>PAH</synonym>
    <synonym>Paha</synonym>
    <synonym>Para-aminohippuric acid</synonym>
    <synonym>Paraaminohippuric acid</synonym>
    <synonym>p-Aminohippuric acid</synonym>
    <synonym>Aminohippate</synonym>
    <synonym>Aminohippic acid</synonym>
    <synonym>N-(p-Aminobenzoyl)aminoacetate</synonym>
    <synonym>Para-aminohippate</synonym>
    <synonym>Para-aminohippic acid</synonym>
    <synonym>Paraaminohippate</synonym>
    <synonym>Paraaminohippic acid</synonym>
    <synonym>p-Aminohippate</synonym>
    <synonym>p-Aminohippic acid</synonym>
    <synonym>4-Aminohippate</synonym>
    <synonym>4-Aminohippic acid</synonym>
    <synonym>4-Aminohippurate</synonym>
    <synonym>Aminohippurate</synonym>
    <synonym>Chlorphentermine</synonym>
    <synonym>N-(4-Aminobenzoyl)glycine</synonym>
    <synonym>Nefrotest</synonym>
    <synonym>Para-aminohippurate</synonym>
    <synonym>Aminohippurate sodium</synonym>
    <synonym>Sodium para-aminohippurate</synonym>
    <synonym>Sodium, aminohippurate</synonym>
    <synonym>p Aminohippurate</synonym>
    <synonym>Para-aminohippurate, sodium</synonym>
    <synonym>Para aminohippuric acid</synonym>
    <synonym>4 Aminohippuric acid</synonym>
    <synonym>Nephrotest</synonym>
    <synonym>Sodium para aminohippurate</synonym>
    <synonym>p Aminohippuric acid</synonym>
    <synonym>4-Aminohippuric acid</synonym>
  </synonyms>
  <chemical_formula>C9H10N2O3</chemical_formula>
  <average_molecular_weight>194.1873</average_molecular_weight>
  <monisotopic_moleculate_weight>194.069142196</monisotopic_moleculate_weight>
  <iupac_name>2-[(4-aminophenyl)formamido]acetic acid</iupac_name>
  <traditional_iupac>aminohippurate</traditional_iupac>
  <cas_registry_number>61-78-9</cas_registry_number>
  <smiles>NC1=CC=C(C=C1)C(=O)NCC(O)=O</smiles>
  <inchi>InChI=1S/C9H10N2O3/c10-7-3-1-6(2-4-7)9(14)11-5-8(12)13/h1-4H,5,10H2,(H,11,14)(H,12,13)</inchi>
  <inchikey>HSMNQINEKMPTIC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>Hippuric acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminobenzamides</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminobenzamide</substituent>
      <substituent>Aminobenzoic acid or derivatives</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hippuric acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>N-acylglycine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>198.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>13 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.89</value>
      <source>FLECK,C &amp; BRAUNLICH,H (1990)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(4-aminophenyl)formamido]acetic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>194.1873</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>194.069142196</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=CC=C(C=C1)C(=O)NCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10N2O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10N2O3/c10-7-3-1-6(2-4-7)9(14)11-5-8(12)13/h1-4H,5,10H2,(H,11,14)(H,12,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>HSMNQINEKMPTIC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>92.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1750</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>262112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282042</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>282044</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>D06890 </kegg_id>
  <chemspider_id>2063</chemspider_id>
  <foodb_id>FDB022720</foodb_id>
  <drugbank_id>DB00345</drugbank_id>
  <pubchem_compound_id>2148</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <chebi_id>104011</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Aminohippuric_Acid</wikipedia_id>
  <metlin_id>6359</metlin_id>
  <synthesis_reference>Barnabei, Ottavio; Cocito, Carlo.  Synthesis of p-aminohippuric acid in presence of thyroxine and a hepatic factor.    Ricerca sci.  (1955),  25  3329-32.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:25 UTC</creation_date>
  <update_date>2020-04-15 22:30:30 UTC</update_date>
  <accession>BMDB0001868</accession>
  <secondary_accessions>
    <accession>BMDB01868</accession>
  </secondary_accessions>
  <name>5-Methoxysalicylic acid</name>
  <description/>
  <synonyms>
    <synonym>5-Methoxysalicylate</synonym>
    <synonym>2-Hydroxy-5-methoxybenzoate</synonym>
    <synonym>2-Hydroxy-5-methoxybenzoic acid</synonym>
    <synonym>5-Methoxy-2-hydroxybenzoate</synonym>
    <synonym>5-Methoxy-2-hydroxybenzoic acid</synonym>
    <synonym>6-Hydroxy-m-anisate</synonym>
    <synonym>6-Hydroxy-m-anisic acid</synonym>
    <synonym>6-Methoxy-m-anisate</synonym>
    <synonym>6-Methoxy-m-anisic acid</synonym>
    <synonym>5-Methoxysalicylic acid, sodium salt</synonym>
    <synonym>5-Methoxysalicylic acid</synonym>
  </synonyms>
  <chemical_formula>C8H8O4</chemical_formula>
  <average_molecular_weight>168.1467</average_molecular_weight>
  <monisotopic_moleculate_weight>168.042258744</monisotopic_moleculate_weight>
  <iupac_name>2-hydroxy-5-methoxybenzoic acid</iupac_name>
  <traditional_iupac>5-methoxysalicylic acid</traditional_iupac>
  <cas_registry_number>2612-02-4</cas_registry_number>
  <smiles>COC1=CC(C(O)=O)=C(O)C=C1</smiles>
  <inchi>InChI=1S/C8H8O4/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4,9H,1H3,(H,10,11)</inchi>
  <inchikey>IZZIWIAOVZOBLF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids  in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>M-methoxybenzoic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>4-alkoxyphenols</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Methoxyphenols</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Salicylic acids</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>4-alkoxyphenol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxybenzoic acid</substituent>
      <substituent>M-methoxybenzoic acid or derivatives</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Methoxyphenol</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Salicylic acid</substituent>
      <substituent>Salicylic acid or derivatives</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>142 - 146 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>9 mg/mL</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-hydroxy-5-methoxybenzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>168.1467</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>168.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC(C(O)=O)=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H8O4/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4,9H,1H3,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IZZIWIAOVZOBLF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>16822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1753</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1755</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>285582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>303171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>346062</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440222</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440223</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id>68296</chemspider_id>
  <foodb_id>FDB011959</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>75787</pubchem_compound_id>
  <phenol_explorer_compound_id/>
  <chebi_id>545920</chebi_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>5-Methoxysalicylic acid</wikipedia_id>
  <metlin_id>4164</metlin_id>
  <synthesis_reference>Nagasawa, Masaaki; Nishioka, Hiroyasu; Suzuki, Takanori; Nagano, Eiichi; Ishii, Katsuyuki; Nakao, Ryu.  Preparation of salicylic acids from 2-methoxybenzoic acids.    Jpn. Kokai Tokkyo Koho  (2000),     6 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:27 UTC</creation_date>
  <update_date>2020-04-15 22:00:53 UTC</update_date>
  <accession>BMDB0001873</accession>
  <secondary_accessions>
    <accession>BMDB01873</accession>
  </secondary_accessions>
  <name>Isobutyric acid</name>
  <description>Isobutanoic acid, also known as isobutyrate or 2,2-dimethylacetate, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Isobutanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Isobutanoic acid exists in all living species, ranging from bacteria to humans. Isobutanoic acid has been found to be associated with several diseases known as nonalcoholic fatty liver disease, eosinophilic esophagitis, crohn's disease, and early preeclampsia; also isobutanoic acid has been linked to the inborn metabolic disorders including celiac disease.</description>
  <synonyms>
    <synonym>2,2-Dimethylacetic acid</synonym>
    <synonym>2-METHYL-propionIC ACID</synonym>
    <synonym>2-Methylpropanoate</synonym>
    <synonym>2-Methylpropanoic acid</synonym>
    <synonym>2-Methylpropionsaeure</synonym>
    <synonym>alpha-Isobutyric acid</synonym>
    <synonym>alpha-Methylpropanoic acid</synonym>
    <synonym>alpha-Methylpropionic acid</synonym>
    <synonym>Dimethylacetic acid</synonym>
    <synonym>Iso-butyric acid</synonym>
    <synonym>Iso-C3H7COOH</synonym>
    <synonym>Isobutanoate</synonym>
    <synonym>Isobutanoic acid</synonym>
    <synonym>Isobuttersaeure</synonym>
    <synonym>Isobutyrate</synonym>
    <synonym>Isopropylformic acid</synonym>
    <synonym>2,2-Dimethylacetate</synonym>
    <synonym>2-METHYL-propionate</synonym>
    <synonym>a-Isobutyrate</synonym>
    <synonym>a-Isobutyric acid</synonym>
    <synonym>alpha-Isobutyrate</synonym>
    <synonym>Α-isobutyrate</synonym>
    <synonym>Α-isobutyric acid</synonym>
    <synonym>a-Methylpropanoate</synonym>
    <synonym>a-Methylpropanoic acid</synonym>
    <synonym>alpha-Methylpropanoate</synonym>
    <synonym>Α-methylpropanoate</synonym>
    <synonym>Α-methylpropanoic acid</synonym>
    <synonym>a-Methylpropionate</synonym>
    <synonym>a-Methylpropionic acid</synonym>
    <synonym>alpha-Methylpropionate</synonym>
    <synonym>Α-methylpropionate</synonym>
    <synonym>Α-methylpropionic acid</synonym>
    <synonym>Dimethylacetate</synonym>
    <synonym>Iso-butyrate</synonym>
    <synonym>Isopropylformate</synonym>
    <synonym>2-Methylpropionate</synonym>
    <synonym>2-Methylpropionic acid</synonym>
    <synonym>I-butyrate</synonym>
    <synonym>I-butyric acid</synonym>
    <synonym>Ammonium isobutyrate</synonym>
    <synonym>Isobutyric acid, ammonium salt</synonym>
    <synonym>Isobutyric acid, sodium salt</synonym>
    <synonym>2-Methpropanoic acid</synonym>
    <synonym>Isobutyric acid, hemiammoniate</synonym>
    <synonym>Sodium isobutyrate</synonym>
    <synonym>Isobutyric acid, calcium salt</synonym>
    <synonym>Isobutyric acid, nickel salt</synonym>
    <synonym>Isobutyric acid, potassium salt</synonym>
    <synonym>Isobutyric acid, sodium salt, 11C-labeled</synonym>
    <synonym>Isobutyric acid, sodium salt, 14C-labeled</synonym>
    <synonym>Isobutyric acid</synonym>
  </synonyms>
  <chemical_formula>C4H8O2</chemical_formula>
  <average_molecular_weight>88.1051</average_molecular_weight>
  <monisotopic_moleculate_weight>88.0524295</monisotopic_moleculate_weight>
  <iupac_name>2-methylpropanoic acid</iupac_name>
  <traditional_iupac>isobutyric acid</traditional_iupac>
  <cas_registry_number>79-31-2</cas_registry_number>
  <smiles>CC(C)C(O)=O</smiles>
  <inchi>InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)</inchi>
  <inchikey>KQNPFQTWMSNSAP-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Carboxylic acids</sub_class>
    <direct_parent>Carboxylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Branched fatty acids</external_descriptor>
      <external_descriptor>branched-chain saturated fatty acid</external_descriptor>
      <external_descriptor>methyl-branched fatty acid</external_descriptor>
      <external_descriptor>short-chain fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-46 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>167 mg/mL at 20 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.94</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-methylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>88.1051</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>88.0524295</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H8O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KQNPFQTWMSNSAP-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>21.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>9.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38160</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3986</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4270</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1648</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437945</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437946</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437947</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in lactating Holstein cows.</comment>
      <references>
        <reference>
          <reference_text>Tian H, Wang W, Zheng N, Cheng J, Li S, Zhang Y, Wang J: Identification of diagnostic biomarkers and metabolic pathway shifts of heat-stressed lactating dairy cows. J Proteomics. 2015 Jul 1;125:17-28. doi: 10.1016/j.jprot.2015.04.014. Epub 2015 Apr 22.</reference_text>
          <pubmed_id>25913299</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>15.87 +/- 20.47</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk samples collected from 456 Danish Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15.</reference_text>
          <pubmed_id>23497994</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.3 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.0 +/- 0.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.3 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.2 +/- 0.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>5.10 +/- 4.79</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>14.45 +/- 15.29</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1420</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>719+/-226</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1100-4100</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1429.07 +/- 228.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>708-1100</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR in bovines in growth and fattening stages.</comment>
      <references>
        <reference>
          <reference_text>Lee HJ, Jung JY, Oh YK, Lee SS, Madsen EL, Jeon CO: Comparative survey of rumen microbial communities and metabolites across one caprine and three bovine groups, using bar-coded pyrosequencing and (1)H nuclear magnetic resonance spectroscopy. Appl Environ Microbiol. 2012 Sep;78(17):5983-93. doi: 10.1128/AEM.00104-12. Epub  2012 Jun 15.</reference_text>
          <pubmed_id>22706048</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1283</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1216</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1430</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>590 +/- 50</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>O'Grady L, Doherty ML, Mulligan FJ: Subacute ruminal acidosis (SARA) in grazing Irish dairy cows. Vet J. 2008 Apr;176(1):44-9. doi: 10.1016/j.tvjl.2007.12.017. Epub 2008 Mar 6.</reference_text>
          <pubmed_id>18328751</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1280</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1450 +/- 180</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1670 +/- 530</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1815 +/- 194</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1430 +/- 228</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1450</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1670</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>1810</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB02531</drugbank_id>
  <foodb_id>FDB003277</foodb_id>
  <kegg_id>C02632</kegg_id>
  <phenol_explorer_compound_id/>
  <chemspider_id>6341</chemspider_id>
  <pubchem_compound_id>6590</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16135</chebi_id>
  <knapsack_id>C00029462</knapsack_id>
  <meta_cyc_id>ISOBUTYRATE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Isobutyric_acid</wikipedia_id>
  <metlin_id>106</metlin_id>
  <synthesis_reference>Wang, Hengxiu; Chen, Weibin; Zhao, Dehua; Zhang, Jianbin.  Preparation of isobutyric acid.    Faming Zhuanli Shenqing Gongkai Shuomingshu  (2003),     5 pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
      <pubmed_id>25599412</pubmed_id>
    </reference>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:28 UTC</creation_date>
  <update_date>2020-03-13 16:29:12 UTC</update_date>
  <accession>BMDB0001874</accession>
  <secondary_accessions>
    <accession>BMDB01874</accession>
  </secondary_accessions>
  <name>D-threo-Isocitric acid</name>
  <description/>
  <synonyms>
    <synonym>(+)-Threo-isocitric acid</synonym>
    <synonym>ISOCITRIC ACID</synonym>
    <synonym>(+)-Threo-isocitrate</synonym>
    <synonym>ISOCITRate</synonym>
    <synonym>D-Threo-isocitrate</synonym>
    <synonym>(1R,2S)-1-Hydroxypropane-1,2,3-tricarboxylate</synonym>
    <synonym>(1R,2S)-1-Hydroxypropane-1,2,3-tricarboxylic acid</synonym>
    <synonym>(2R,3S)-Isocitrate</synonym>
    <synonym>3-Carboxy-2,3-dideoxy-L-threo-pentaric acid</synonym>
    <synonym>D-(+)-Threo-isocitric acid(2R,3S)-isocitric acid</synonym>
    <synonym>DS-Threo-isocitrate</synonym>
    <synonym>DS-Threo-isocitric acid</synonym>
    <synonym>ICI</synonym>
    <synonym>ICT</synonym>
    <synonym>Threo-D-(+)-isocitrate</synonym>
    <synonym>Threo-D-(+)-isocitric acid</synonym>
    <synonym>Threo-DS(+)-isocitrate</synonym>
    <synonym>Threo-DS(+)-isocitric acid</synonym>
    <synonym>Threo-isocitrate</synonym>
    <synonym>Isocitric acid, trisodium salt</synonym>
    <synonym>Isocitric acid, (11)C-labeled</synonym>
    <synonym>Isocitric acid, disodium salt</synonym>
    <synonym>Isocitric acid, calcium salt</synonym>
    <synonym>Isocitric acid, potassium salt</synonym>
    <synonym>Isocitric acid, sodium salt</synonym>
  </synonyms>
  <chemical_formula>C6H8O7</chemical_formula>
  <average_molecular_weight>192.1235</average_molecular_weight>
  <monisotopic_moleculate_weight>192.02700261</monisotopic_moleculate_weight>
  <iupac_name>(1R,2S)-1-hydroxypropane-1,2,3-tricarboxylic acid</iupac_name>
  <traditional_iupac>threo-DS(+)-isocitrate</traditional_iupac>
  <cas_registry_number>6061-97-8</cas_registry_number>
  <smiles>O[C@H]([C@H](CC(O)=O)C(O)=O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)/t2-,4+/m0/s1</inchi>
  <inchikey>ODBLHEXUDAPZAU-ZAFYKAAXSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Tricarboxylic acids and derivatives</sub_class>
    <direct_parent>Tricarboxylic acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tricarboxylic acid or derivatives</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>isocitric acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.35</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1R,2S)-1-hydroxypropane-1,2,3-tricarboxylic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>192.1235</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>192.02700261</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O[C@H]([C@H](CC(O)=O)C(O)=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H8O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)/t2-,4+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ODBLHEXUDAPZAU-ZAFYKAAXSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>132.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>35.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32007</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38161</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1767</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>182744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>183092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5150</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB012771</foodb_id>
  <kegg_id>C00451</kegg_id>
  <phenol_explorer_compound_id/>
  <chemspider_id>4477081</chemspider_id>
  <pubchem_compound_id>5318532</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>151</chebi_id>
  <knapsack_id>C00001188</knapsack_id>
  <meta_cyc_id>THREO-DS-ISO-CITRATE</meta_cyc_id>
  <bigg_id>34579</bigg_id>
  <wikipedia_id/>
  <metlin_id>3328</metlin_id>
  <synthesis_reference>Wong, Chi Huey; Whitesides, George M.  Enzyme-catalyzed transhydrogenation between nicotinamide cofactors and its application in organic synthesis.    Journal of the American Chemical Society  (1982),  104(12),  3542-4.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:29 UTC</creation_date>
  <update_date>2020-04-16 20:40:08 UTC</update_date>
  <accession>BMDB0001875</accession>
  <secondary_accessions>
    <accession>BMDB01875</accession>
  </secondary_accessions>
  <name>Methanol</name>
  <description>Methanol, also known as columbian spirit or methyl alcohol, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl). Methanol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Methanol exists in all living organisms, ranging from bacteria to humans. Methanol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>Carbinol</synonym>
    <synonym>CH3OH</synonym>
    <synonym>MeOH</synonym>
    <synonym>Methyl alcohol</synonym>
    <synonym>Methylalkohol</synonym>
    <synonym>Spirit OF wood</synonym>
    <synonym>Wood alcohol</synonym>
    <synonym>Wood naphtha</synonym>
    <synonym>Wood spirit</synonym>
    <synonym>Alcool methylique</synonym>
    <synonym>Alcool metilico</synonym>
    <synonym>Colonial spirit</synonym>
    <synonym>Columbian spirit</synonym>
    <synonym>Columbian spirits</synonym>
    <synonym>Hydroxymethane</synonym>
    <synonym>Metanolo</synonym>
    <synonym>Methanol-water mixture</synonym>
    <synonym>Methyl hydroxide</synonym>
    <synonym>Methylol</synonym>
    <synonym>Metylowy alkohol</synonym>
    <synonym>Monohydroxymethane</synonym>
    <synonym>Pyro alcohol</synonym>
    <synonym>Pyroxylic spirit</synonym>
    <synonym>Alcohol, methyl</synonym>
    <synonym>Methoxide, sodium</synonym>
    <synonym>Sodium methoxide</synonym>
    <synonym>Alcohol, wood</synonym>
  </synonyms>
  <chemical_formula>CH4O</chemical_formula>
  <average_molecular_weight>32.0419</average_molecular_weight>
  <monisotopic_moleculate_weight>32.02621475</monisotopic_moleculate_weight>
  <iupac_name>methanol</iupac_name>
  <traditional_iupac>methanol</traditional_iupac>
  <cas_registry_number>67-56-1</cas_registry_number>
  <smiles>CO</smiles>
  <inchi>InChI=1S/CH4O/c1-2/h2H,1H3</inchi>
  <inchikey>OKKJLVBELUTLKV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>Primary alcohols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a short-chain alcohol</external_descriptor>
      <external_descriptor>alkyl alcohol</external_descriptor>
      <external_descriptor>one-carbon compound</external_descriptor>
      <external_descriptor>primary alcohol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-97.6 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.77</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>methanol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>32.0419</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>32.02621475</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>CH4O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/CH4O/c1-2/h2H,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OKKJLVBELUTLKV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>8.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>3.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3271</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20569</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29321</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38162</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22043</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22044</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22045</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value>32+/-4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Blood</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected by NMR</comment>
      <references>
        <reference>
          <reference_text>De Buck J, Shaykhutdinov R, Barkema HW, Vogel HJ: Metabolomic profiling in cattle experimentally infected with Mycobacterium avium subsp. paratuberculosis. PLoS One. 2014 Nov 5;9(11):e111872. doi: 10.1371/journal.pone.0111872. eCollection 2014.</reference_text>
          <pubmed_id>25372282</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>27.43 +/- 15.84</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of total mixed ration (TMR), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>4.63 +/- 6.42</concentration_value>
      <concentration_units>mg/100g dry matter content</concentration_units>
      <comment>Italian raw milk</comment>
      <references>
        <reference>
          <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.46 +/- 3.28</concentration_value>
      <concentration_units>mg/100g dry matter content</concentration_units>
      <comment>Slovenian raw milk</comment>
      <references>
        <reference>
          <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>23.64 +/- 7.16</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass (GRS), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32 +/- 1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>30 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>32 +/- 4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by NMR</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>29.85 +/- 19.30</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk metabolite measured during mid-lactation from cows fed diets consisting of perennial ryegrass and white clover (CLV), by 1H-NMR</comment>
      <references>
        <reference>
          <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
          <pubmed_id>29642378</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>22.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>28</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>71.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>24.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB008124</foodb_id>
  <kegg_id>C00132</kegg_id>
  <phenol_explorer_compound_id/>
  <chemspider_id>864</chemspider_id>
  <pubchem_compound_id>887</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17790</chebi_id>
  <knapsack_id/>
  <meta_cyc_id>METOH</meta_cyc_id>
  <bigg_id>33974</bigg_id>
  <wikipedia_id>Methanol</wikipedia_id>
  <metlin_id>4201</metlin_id>
  <synthesis_reference>Cummings, Donald Ray.  Process for production of methanol from a methane gas stream.    PCT Int. Appl.  (2007),     21pp.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.</reference_text>
      <pubmed_id>29642378</pubmed_id>
    </reference>
    <reference>
      <reference_text>Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:30 UTC</creation_date>
  <update_date>2020-04-14 22:49:24 UTC</update_date>
  <accession>BMDB0001876</accession>
  <secondary_accessions>
    <accession>BMDB01876</accession>
  </secondary_accessions>
  <name>Epinephrine sulfate</name>
  <description/>
  <synonyms>
    <synonym>Epinephrine sulfuric acid</synonym>
    <synonym>Epinephrine sulphate</synonym>
    <synonym>Epinephrine sulphuric acid</synonym>
    <synonym>(R)-4-[1-Hydroxy-2-(methylamino)ethyl]-2-benzenediol mono(hydrogen sulfate) (ester)</synonym>
    <synonym>(R)-4-[1-Hydroxy-2-(methylamino)ethyl]-2-benzenediol mono(hydrogen sulphate) (ester)</synonym>
    <synonym>Adrenaline sulfate</synonym>
    <synonym>Adrenaline sulphate</synonym>
    <synonym>Epinephrine sulfoconjugate</synonym>
    <synonym>Epinephrine-3-O-sulfate</synonym>
    <synonym>{2-hydroxy-4-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenyl}oxidanesulfonate</synonym>
    <synonym>{2-hydroxy-4-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenyl}oxidanesulphonate</synonym>
    <synonym>{2-hydroxy-4-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenyl}oxidanesulphonic acid</synonym>
    <synonym>Epinephrine sulfate</synonym>
  </synonyms>
  <chemical_formula>C9H13NO6S</chemical_formula>
  <average_molecular_weight>263.268</average_molecular_weight>
  <monisotopic_moleculate_weight>263.046357843</monisotopic_moleculate_weight>
  <iupac_name>{2-hydroxy-4-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenyl}oxidanesulfonic acid</iupac_name>
  <traditional_iupac>epinephrine sulfoconjugate</traditional_iupac>
  <cas_registry_number>77469-50-2</cas_registry_number>
  <smiles>CNC[C@H](O)C1=CC(O)=C(OS(O)(=O)=O)C=C1</smiles>
  <inchi>InChI=1S/C9H13NO6S/c1-10-5-8(12)6-2-3-9(7(11)4-6)16-17(13,14)15/h2-4,8,10-12H,5H2,1H3,(H,13,14,15)/t8-/m0/s1</inchi>
  <inchikey>AELFRHHZGTVYGJ-QMMMGPOBSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic sulfuric acids and derivatives</class>
    <sub_class>Arylsulfates</sub_class>
    <direct_parent>Phenylsulfates</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenylsulfate</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.62</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.01</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>-2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>{2-hydroxy-4-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenyl}oxidanesulfonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>263.268</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>263.046357843</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CNC[C@H](O)C1=CC(O)=C(OS(O)(=O)=O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13NO6S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13NO6S/c1-10-5-8(12)6-2-3-9(7(11)4-6)16-17(13,14)15/h2-4,8,10-12H,5H2,1H3,(H,13,14,15)/t8-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AELFRHHZGTVYGJ-QMMMGPOBSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>116.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>59.22</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>72018</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>72019</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>72020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>130809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>130810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>130811</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022721</foodb_id>
  <kegg_id/>
  <phenol_explorer_compound_id/>
  <chemspider_id>2299690</chemspider_id>
  <pubchem_compound_id>3035453</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>89878</chebi_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Lernhardt U; Strobel G; Schell H; Werle E; Weicker H  Modified syntheses of dopamine-4-sulfate, epinephrine-3-sulfate, and norepinephrine-3-sulfate: determination of the position of the sulfate group by 1H-NMR spectroscopy.    International journal of sports medicine  (1988),  9 Suppl 2 S89-92.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:32 UTC</creation_date>
  <update_date>2020-04-15 22:15:31 UTC</update_date>
  <accession>BMDB0001877</accession>
  <secondary_accessions>
    <accession>BMDB01877</accession>
  </secondary_accessions>
  <name>Valproic acid</name>
  <description/>
  <synonyms>
    <synonym>2-N-Propyl-N-valeric acid</synonym>
    <synonym>2-PROPYL-pentanoIC ACID</synonym>
    <synonym>2-Propylpentanoic acid</synonym>
    <synonym>2-Propylvaleric acid</synonym>
    <synonym>4-Heptanecarboxylic acid</synonym>
    <synonym>Acide valproique</synonym>
    <synonym>Acido valproico</synonym>
    <synonym>Acidum valproicum</synonym>
    <synonym>Depakene</synonym>
    <synonym>Di-N-propylacetic acid</synonym>
    <synonym>Di-N-propylessigsaeure</synonym>
    <synonym>Dipropylacetic acid</synonym>
    <synonym>DPA</synonym>
    <synonym>N-DPA</synonym>
    <synonym>Valproinsaeure</synonym>
    <synonym>VPA</synonym>
    <synonym>2-N-Propyl-N-valerate</synonym>
    <synonym>2-PROPYL-pentanoate</synonym>
    <synonym>2-Propylpentanoate</synonym>
    <synonym>2-Propylvalerate</synonym>
    <synonym>4-Heptanecarboxylate</synonym>
    <synonym>Di-N-propylacetate</synonym>
    <synonym>Dipropylacetate</synonym>
    <synonym>Valproate</synonym>
    <synonym>(N-C3H7)2chcooh</synonym>
    <synonym>(S)-2-Propyl-4-pentanoate</synonym>
    <synonym>(S)-2-Propyl-4-pentanoic acid</synonym>
    <synonym>Alti-valproic</synonym>
    <synonym>Apo-divalproex</synonym>
    <synonym>Apo-valproic</synonym>
    <synonym>Apo-valproic syrup</synonym>
    <synonym>Avugane</synonym>
    <synonym>Baceca</synonym>
    <synonym>Convulex</synonym>
    <synonym>Delepsine</synonym>
    <synonym>Depakin</synonym>
    <synonym>Depakin chrono</synonym>
    <synonym>Depakine</synonym>
    <synonym>Depakine chrono</synonym>
    <synonym>Deproic</synonym>
    <synonym>Di-N-propylessigsaure</synonym>
    <synonym>Divalproex</synonym>
    <synonym>DOM-divalproex</synonym>
    <synonym>Dom-valproate</synonym>
    <synonym>DOM-valproic</synonym>
    <synonym>Dom-valproic acid</synonym>
    <synonym>DOM-valproic acid e.c.</synonym>
    <synonym>Dom-valproic acid syrup</synonym>
    <synonym>Epiject i.v.</synonym>
    <synonym>Epilex</synonym>
    <synonym>Epilim</synonym>
    <synonym>Epival</synonym>
    <synonym>Epival er</synonym>
    <synonym>Ergenyl</synonym>
    <synonym>Gen-divalproex</synonym>
    <synonym>Kyselina 2-propylvalerova</synonym>
    <synonym>Med valproic</synonym>
    <synonym>Mylproin</synonym>
    <synonym>Myproate</synonym>
    <synonym>Myproic acid</synonym>
    <synonym>N-Dipropylacetic acid</synonym>
    <synonym>Novo-divalproex</synonym>
    <synonym>Novo-valproic</synonym>
    <synonym>Novo-valproic - ecc</synonym>
    <synonym>Novo-valproic soft gel cap</synonym>
    <synonym>Nu-valproic</synonym>
    <synonym>PEAC</synonym>
    <synonym>Penta-valproic</synonym>
    <synonym>PHL-Valproate</synonym>
    <synonym>PHL-Valproic acid</synonym>
    <synonym>PHL-Valproic acid e.c.</synonym>
    <synonym>PMS-Divalproex</synonym>
    <synonym>PMS-Valproate</synonym>
    <synonym>PMS-Valproic acid</synonym>
    <synonym>PMS-Valproic acid e.c.</synonym>
    <synonym>Propylvaleric acid</synonym>
    <synonym>Ratio-valproic - ecc</synonym>
    <synonym>S(-)-4-En-valproate</synonym>
    <synonym>S(-)-4-En-valproic acid</synonym>
    <synonym>S-2-N-Propyl-4-pentenoate</synonym>
    <synonym>S-2-N-Propyl-4-pentenoic acid</synonym>
    <synonym>Sandoz valproic</synonym>
    <synonym>Savicol</synonym>
    <synonym>Sprinkle</synonym>
    <synonym>Valcote</synonym>
    <synonym>Valparin</synonym>
    <synonym>Valproic acid usp</synonym>
    <synonym>Dipropyl acetate</synonym>
    <synonym>Valproate, sodium</synonym>
    <synonym>Calcium, valproate</synonym>
    <synonym>Convulsofin</synonym>
    <synonym>Semisodium valproate</synonym>
    <synonym>Sodium valproate</synonym>
    <synonym>Valproate calcium</synonym>
    <synonym>Valproate, calcium</synonym>
    <synonym>Valproic acid, sodium salt (2:1)</synonym>
    <synonym>Acetate, dipropyl</synonym>
    <synonym>Depakote</synonym>
    <synonym>Divalproex sodium</synonym>
    <synonym>Magnesium valproate</synonym>
    <synonym>Sodium, divalproex</synonym>
    <synonym>Sodium, valproate</synonym>
    <synonym>Vupral</synonym>
    <synonym>2 Propylpentanoic acid</synonym>
    <synonym>Acid, propylisopropylacetic</synonym>
    <synonym>Acid, valproic</synonym>
    <synonym>Calcium valproate</synonym>
    <synonym>Propylisopropylacetic acid</synonym>
    <synonym>Valproate sodium</synonym>
    <synonym>Valproate, magnesium</synonym>
    <synonym>Valproate, semisodium</synonym>
  </synonyms>
  <chemical_formula>C8H16O2</chemical_formula>
  <average_molecular_weight>144.2114</average_molecular_weight>
  <monisotopic_moleculate_weight>144.115029756</monisotopic_moleculate_weight>
  <iupac_name>2-propylpentanoic acid</iupac_name>
  <traditional_iupac>valproic acid</traditional_iupac>
  <cas_registry_number>99-66-1</cas_registry_number>
  <smiles>CCCC(CCC)C(O)=O</smiles>
  <inchi>InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)</inchi>
  <inchikey>NIJJYAXOARWZEE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Methyl-branched fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methyl-branched fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Branched fatty acids</external_descriptor>
      <external_descriptor>branched-chain fatty acid</external_descriptor>
      <external_descriptor>branched-chain saturated fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>boiling_point</kind>
      <value>222 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>2 mg/mL at 20 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.75</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.54</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>5.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-propylpentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>144.2114</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>144.115029756</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCC(CCC)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NIJJYAXOARWZEE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3439</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261364</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>261365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>281300</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438594</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438595</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439969</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB00313</drugbank_id>
  <foodb_id>FDB022722</foodb_id>
  <kegg_id>C07185</kegg_id>
  <phenol_explorer_compound_id/>
  <chemspider_id>3009</chemspider_id>
  <pubchem_compound_id>3121</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>39867</chebi_id>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Valproic_Acid</wikipedia_id>
  <metlin_id>2986</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:33 UTC</creation_date>
  <update_date>2020-04-15 22:28:42 UTC</update_date>
  <accession>BMDB0001879</accession>
  <secondary_accessions>
    <accession>BMDB01879</accession>
  </secondary_accessions>
  <name>Aspirin</name>
  <description/>
  <synonyms>
    <synonym>2-(ACETYLOXY)benzoIC ACID</synonym>
    <synonym>2-Acetoxybenzenecarboxylic acid</synonym>
    <synonym>2-Acetoxybenzoic acid</synonym>
    <synonym>Acetylsalicylate</synonym>
    <synonym>Acetylsalicylsaeure</synonym>
    <synonym>Acide 2-(acetyloxy)benzoique</synonym>
    <synonym>Acide acetylsalicylique</synonym>
    <synonym>Acido acetilsalicilico</synonym>
    <synonym>Acidum acetylsalicylicum</synonym>
    <synonym>ASA</synonym>
    <synonym>Azetylsalizylsaeure</synonym>
    <synonym>Easprin</synonym>
    <synonym>O-Acetoxybenzoic acid</synonym>
    <synonym>O-Acetylsalicylic acid</synonym>
    <synonym>O-Carboxyphenyl acetate</synonym>
    <synonym>Salicylic acid acetate</synonym>
    <synonym>Acetylsalicylic acid</synonym>
    <synonym>Aspalon</synonym>
    <synonym>Durlaza</synonym>
    <synonym>2-(ACETYLOXY)benzoate</synonym>
    <synonym>2-Acetoxybenzenecarboxylate</synonym>
    <synonym>2-Acetoxybenzoate</synonym>
    <synonym>O-Acetoxybenzoate</synonym>
    <synonym>O-Acetylsalicylate</synonym>
    <synonym>O-Carboxyphenyl acetic acid</synonym>
    <synonym>Salicylate acetate</synonym>
    <synonym>Salicylic acid acetic acid</synonym>
    <synonym>2-Carboxyphenyl acetate</synonym>
    <synonym>Acenterine</synonym>
    <synonym>Acetard</synonym>
    <synonym>Aceticyl</synonym>
    <synonym>Acetol</synonym>
    <synonym>Acetonyl</synonym>
    <synonym>Acetophen</synonym>
    <synonym>Acetosal</synonym>
    <synonym>Acetosalin</synonym>
    <synonym>Acetylin</synonym>
    <synonym>Acetyonyl</synonym>
    <synonym>Acetysal</synonym>
    <synonym>Acetysalicylic acid</synonym>
    <synonym>Acylpyrin</synonym>
    <synonym>Asatard</synonym>
    <synonym>Aspergum</synonym>
    <synonym>Aspirdrops</synonym>
    <synonym>Benaspir</synonym>
    <synonym>Bialpirinia</synonym>
    <synonym>Bufferin</synonym>
    <synonym>Caprin</synonym>
    <synonym>Cardioaspirina</synonym>
    <synonym>Ecolen</synonym>
    <synonym>Ecotrin</synonym>
    <synonym>Empirin</synonym>
    <synonym>Endosprin</synonym>
    <synonym>Endydol</synonym>
    <synonym>O-(Acetyloxy)benzoate</synonym>
    <synonym>O-(Acetyloxy)benzoic acid</synonym>
    <synonym>Persistin</synonym>
    <synonym>Pharmacin</synonym>
    <synonym>Polopiryna</synonym>
    <synonym>Premaspin</synonym>
    <synonym>Rheumintabletten</synonym>
    <synonym>Rhodine</synonym>
    <synonym>Salcetogen</synonym>
    <synonym>Saletin</synonym>
    <synonym>Salospir</synonym>
    <synonym>Solprin</synonym>
    <synonym>Solprin acid</synonym>
    <synonym>Solpyron</synonym>
    <synonym>Tasprin</synonym>
    <synonym>Temperal</synonym>
    <synonym>Toldex</synonym>
    <synonym>Triaminicin</synonym>
    <synonym>Magnecyl</synonym>
    <synonym>Polopirin</synonym>
    <synonym>Solupsan</synonym>
    <synonym>Zorprin</synonym>
    <synonym>Dispril</synonym>
    <synonym>Aloxiprimum</synonym>
    <synonym>Colfarit</synonym>
    <synonym>Micristin</synonym>
    <synonym>Acid, acetylsalicylic</synonym>
  </synonyms>
  <chemical_formula>C9H8O4</chemical_formula>
  <average_molecular_weight>180.1574</average_molecular_weight>
  <monisotopic_moleculate_weight>180.042258744</monisotopic_moleculate_weight>
  <iupac_name>2-(acetyloxy)benzoic acid</iupac_name>
  <traditional_iupac>aspirin</traditional_iupac>
  <cas_registry_number>50-78-2</cas_registry_number>
  <smiles>CC(=O)OC1=CC=CC=C1C(O)=O</smiles>
  <inchi>InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)</inchi>
  <inchikey>BSYNRYMUTXBXSQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acylsalicylic acids. These are o-acylated derivatives of salicylic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>Acylsalicylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Phenol esters</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acylsalicylic acid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol ester</substituent>
      <substituent>Phenoxy compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>acetate ester</external_descriptor>
      <external_descriptor>benzoic acids</external_descriptor>
      <external_descriptor>salicylates</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>135 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.19</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.24</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(acetyloxy)benzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>180.1574</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>180.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)OC1=CC=CC=C1C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>BSYNRYMUTXBXSQ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>44.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1776</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>628</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1003</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7757</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27421</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32298</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255762</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>255764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275704</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>275705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>436687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444378</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C01405</kegg_id>
  <drugbank_id>DB00945</drugbank_id>
  <foodb_id>FDB000894</foodb_id>
  <pubchem_compound_id>2244</pubchem_compound_id>
  <chemspider_id>2157</chemspider_id>
  <pdbe_id/>
  <chebi_id>15365</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD-524</meta_cyc_id>
  <bigg_id>45400</bigg_id>
  <wikipedia_id>Aspirin</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Chen, Hong; Long, Xiang; Huang, Siqing.  Synthesis of aspirin with vitamin C as catalyst.    Huaxue Shijie  (2004),  45(12),  642-643.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:34 UTC</creation_date>
  <update_date>2020-04-16 20:39:28 UTC</update_date>
  <accession>BMDB0001881</accession>
  <secondary_accessions>
    <accession>BMDB01881</accession>
  </secondary_accessions>
  <name>Propylene glycol</name>
  <description/>
  <synonyms>
    <synonym>1,2-Dihydroxypropane</synonym>
    <synonym>1,2-Propanediol</synonym>
    <synonym>1,2-Propylenglykol</synonym>
    <synonym>2-Hydroxypropanol</synonym>
    <synonym>alpha-Propyleneglycol</synonym>
    <synonym>CH3CH(OH)CH2OH</synonym>
    <synonym>HOCH2CH(OH)CH3</synonym>
    <synonym>HOCH2CH(OH)Me</synonym>
    <synonym>Isopropylene glycol</synonym>
    <synonym>MeCH(OH)CH2OH</synonym>
    <synonym>Methyl glycol</synonym>
    <synonym>Methylethyl glycol</synonym>
    <synonym>Methylethylene glycol</synonym>
    <synonym>Monopropylene glycol</synonym>
    <synonym>PPD</synonym>
    <synonym>a-Propyleneglycol</synonym>
    <synonym>Α-propyleneglycol</synonym>
    <synonym>(RS)-1,2-Propanediol</synonym>
    <synonym>1,2-(RS)-Propanediol</synonym>
    <synonym>1,2-Propylene glycol</synonym>
    <synonym>2,3-Propanediol</synonym>
    <synonym>a-Propylene glycol</synonym>
    <synonym>Aliphatic alcohol</synonym>
    <synonym>alpha-Propylene glycol</synonym>
    <synonym>Chilisa fe</synonym>
    <synonym>DL-1,2-Propanediol</synonym>
    <synonym>DL-Propylene glycol</synonym>
    <synonym>Dowfrost</synonym>
    <synonym>Glycol</synonym>
    <synonym>Ilexan p</synonym>
    <synonym>Inhibited 1,2-propylene glycol</synonym>
    <synonym>Prolugen</synonym>
    <synonym>Propane-1,2-diol</synonym>
    <synonym>Propanediol</synonym>
    <synonym>Propylene glycol usp</synonym>
    <synonym>Propylenglycol</synonym>
    <synonym>Sentry propylene glycol</synonym>
    <synonym>Sirlene</synonym>
    <synonym>Solar winter ban</synonym>
    <synonym>Solargard p</synonym>
    <synonym>Trimethyl glycol</synonym>
    <synonym>Ucar 35</synonym>
    <synonym>Propan-1,2-diol</synonym>
    <synonym>Monohydrate, propylene glycol</synonym>
    <synonym>Propylene glycol, (R)-isomer</synonym>
    <synonym>Propylene glycol, (S)-isomer</synonym>
    <synonym>1,2 Propanediol</synonym>
    <synonym>Glycol, propylene</synonym>
    <synonym>Propylene glycol, (+-)-isomer</synonym>
    <synonym>Propylene glycol monohydrate</synonym>
    <synonym>Propylene glycol sodium salt</synonym>
  </synonyms>
  <chemical_formula>C3H8O2</chemical_formula>
  <average_molecular_weight>76.0944</average_molecular_weight>
  <monisotopic_moleculate_weight>76.0524295</monisotopic_moleculate_weight>
  <iupac_name>propane-1,2-diol</iupac_name>
  <traditional_iupac>1,2-propanediol</traditional_iupac>
  <cas_registry_number>57-55-6</cas_registry_number>
  <smiles>CC(O)CO</smiles>
  <inchi>InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3</inchi>
  <inchikey>DNIAPMSPPWPWGF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1,2-diols. These are polyols containing an alcohol group at two adjacent positions.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Alcohols and polyols</sub_class>
    <direct_parent>1,2-diols</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>DL-12-Propanediol</external_descriptor>
      <external_descriptor>glycol</external_descriptor>
      <external_descriptor>propane-1,2-diols</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-60 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000 mg/mL at 20 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.92</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>propane-1,2-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>76.0944</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>76.0524295</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H8O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DNIAPMSPPWPWGF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>40.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>18.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>42</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1717</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1777</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5033</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>892</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29431</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38167</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1782</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178701</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178702</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181020</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>181022</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB01839</drugbank_id>
  <foodb_id>FDB008274</foodb_id>
  <kegg_id>C00583</kegg_id>
  <phenol_explorer_compound_id/>
  <chemspider_id>13835224</chemspider_id>
  <pubchem_compound_id>1030</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>16997</chebi_id>
  <knapsack_id>C00007410</knapsack_id>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Propylene_glycol</wikipedia_id>
  <metlin_id>3220</metlin_id>
  <synthesis_reference>Tuck, Michael William Marshall.  Preparation of propylene glycol by hydrogenation of glycerol.    PCT Int. Appl.  (2008),     20pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:35 UTC</creation_date>
  <update_date>2020-04-16 17:51:44 UTC</update_date>
  <accession>BMDB0001882</accession>
  <secondary_accessions>
    <accession>BMDB01882</accession>
  </secondary_accessions>
  <name>Dihydroxyacetone</name>
  <description>Dihydroxyacetone, also known as chromelin or DHA, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. Dihydroxyacetone exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Dihydroxyacetone exists in all living species, ranging from bacteria to humans. In cattle, dihydroxyacetone is involved in the metabolic pathway called the mitochondrial electron transport chain pathway.</description>
  <synonyms>
    <synonym>1,3-Dihydroxy-2-propanone</synonym>
    <synonym>1,3-Dihydroxyacetone</synonym>
    <synonym>1,3-Dihydroxydimethyl ketone</synonym>
    <synonym>1,3-Dihydroxypropan-2-one</synonym>
    <synonym>1,3-Dihydroxypropanone</synonym>
    <synonym>1,3-Propanediol-2-one</synonym>
    <synonym>alpha,Alpha'-dihydroxyacetone</synonym>
    <synonym>Bis(hydroxymethyl) ketone</synonym>
    <synonym>DHA</synonym>
    <synonym>Glycerone</synonym>
    <synonym>Chromelin</synonym>
    <synonym>a,Alpha'-dihydroxyacetone</synonym>
    <synonym>Α,alpha'-dihydroxyacetone</synonym>
    <synonym>a,A'-dihydroxyacetone</synonym>
    <synonym>Aliphatic ketone</synonym>
    <synonym>Dihydroxy-acetone</synonym>
    <synonym>Dihyxal</synonym>
    <synonym>Ketochromin</synonym>
    <synonym>Otan</synonym>
    <synonym>Oxantin</synonym>
    <synonym>Oxatone</synonym>
    <synonym>Protosol</synonym>
    <synonym>Soleal</synonym>
    <synonym>Triulose</synonym>
    <synonym>Viticolor</synonym>
    <synonym>1,3 Dihydroxy 2 propanone</synonym>
    <synonym>Summers brand OF dihydroxyacetone</synonym>
    <synonym>ICN brand OF dihydroxyacetone</synonym>
    <synonym>Vitadye</synonym>
  </synonyms>
  <chemical_formula>C3H6O3</chemical_formula>
  <average_molecular_weight>90.0779</average_molecular_weight>
  <monisotopic_moleculate_weight>90.031694058</monisotopic_moleculate_weight>
  <iupac_name>1,3-dihydroxypropan-2-one</iupac_name>
  <traditional_iupac>dihydroxyacetone</traditional_iupac>
  <cas_registry_number>96-26-4</cas_registry_number>
  <smiles>OCC(=O)CO</smiles>
  <inchi>InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2</inchi>
  <inchikey>RXKJFZQQPQGTFL-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Monosaccharides</direct_parent>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxy ketones</alternative_parent>
      <alternative_parent>Glycerone and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxy ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Glycerone or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Primary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Ketoses</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>ketotriose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>90 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.97</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1,3-dihydroxypropan-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>90.0779</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>90.031694058</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OCC(=O)CO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H6O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RXKJFZQQPQGTFL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>19.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>979</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30146</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1778</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4727</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21330</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22880</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22881</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>22882</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Milk from Friesuan Holstein cows (n=1035)</comment>
      <references>
        <reference>
          <reference_text>Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.</reference_text>
          <pubmed_id>23438684</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>16.56 +/- 4.22</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>6.5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (15% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>6.8</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (30% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>6.3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Daily cows fed barley grains (45% of diet dry matter) (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>16.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. No barley grains in diet (n=8)</comment>
      <references>
        <reference>
          <reference_text>Saleem F, Ametaj BN, Bouatra S, Mandal R, Zebeli Q, Dunn SM, Wishart DS: A metabolomics approach to uncover the effects of grain diets on rumen health in dairy cows. J Dairy Sci. 2012 Nov;95(11):6606-23. doi: 10.3168/jds.2012-5403. Epub 2012 Sep 7.</reference_text>
          <pubmed_id>22959937</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>7.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (15% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>7.9</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (30% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>6.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows fed barley grains (45% of diet dry matter)</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>15.6</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By NMR. Primiparous Holstein cows, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Burim NA, Qendrim Z, Fozia S, Psychogios N, Michael JL, Dunn SM, Jianguo X, Wishart DS. Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Metabolomics. 2010;6(4):583-594   doi: 10.1007/s11306-010-0227-6</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>7 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (15% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>7 +/- 3</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (30% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>7 +/- 2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow fed barley grains (45% of diet dry matter). </comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>17 +/- 5</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet.</comment>
      <references>
        <reference>
          <reference_text>Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C00184</kegg_id>
  <drugbank_id>DB01775</drugbank_id>
  <foodb_id>FDB030826</foodb_id>
  <pubchem_compound_id>670</pubchem_compound_id>
  <chemspider_id>650</chemspider_id>
  <pdbe_id/>
  <chebi_id>16016</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>DIHYDROXYACETONE</meta_cyc_id>
  <bigg_id>34170</bigg_id>
  <wikipedia_id>Dihydroxyacetone</wikipedia_id>
  <metlin_id>6368</metlin_id>
  <synthesis_reference>Hochuli, Erich; Taylor, Keith E.; Dutler, Hans. Dihydroxyacetone reductase from Mucor javanicus. 2. Identification of the physiological substrate and reactivity towards related compounds. European Journal of Biochemistry (1977), 75(2), 433-9.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:36 UTC</creation_date>
  <update_date>2020-04-15 22:23:55 UTC</update_date>
  <accession>BMDB0001885</accession>
  <secondary_accessions>
    <accession>BMDB01885</accession>
  </secondary_accessions>
  <name>3-Chlorotyrosine</name>
  <description/>
  <synonyms>
    <synonym>3-Chloro-L-tyrosine</synonym>
    <synonym>Chlorotyrosine</synonym>
    <synonym>L-(8CI)-3-chloro-tyrosine</synonym>
    <synonym>Monochlorotyrosine</synonym>
    <synonym>3-Chlorotyrosine, (L)-isomer</synonym>
    <synonym>3-Chlorotyrosine hydrochloride, (L)-isomer</synonym>
    <synonym>2-Amino-3-(3-chloro-4-hydroxyphenyl)propanoate</synonym>
  </synonyms>
  <chemical_formula>C9H10ClNO3</chemical_formula>
  <average_molecular_weight>215.634</average_molecular_weight>
  <monisotopic_moleculate_weight>215.034920898</monisotopic_moleculate_weight>
  <iupac_name>2-amino-3-(3-chloro-4-hydroxyphenyl)propanoic acid</iupac_name>
  <traditional_iupac>monochlorotyrosine</traditional_iupac>
  <cas_registry_number>7423-93-0</cas_registry_number>
  <smiles>NC(CC1=CC(Cl)=C(O)C=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C9H10ClNO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)</inchi>
  <inchikey>ACWBBAGYTKWBCD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Tyrosine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alpha amino acids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aryl chlorides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Chlorobenzenes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>O-chlorophenols</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalanine and derivatives</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>2-chlorophenol</substituent>
      <substituent>2-halophenol</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl chloride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Chlorobenzene</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Tyrosine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.56</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-3-(3-chloro-4-hydroxyphenyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>215.634</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>215.034920898</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC(CC1=CC(Cl)=C(O)C=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10ClNO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10ClNO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ACWBBAGYTKWBCD-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>83.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>51.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1779</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>18285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>306537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350218</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>350220</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022723</foodb_id>
  <pubchem_compound_id>119226</pubchem_compound_id>
  <chemspider_id>106510</chemspider_id>
  <kegg_id/>
  <chebi_id/>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6369</metlin_id>
  <synthesis_reference>Bouchilloux, Simone.  Chlorination of L-tyrosine.    Bulletin de la Societe de Chimie Biologique  (1955),  37  255-8.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:37 UTC</creation_date>
  <update_date>2020-04-14 22:49:25 UTC</update_date>
  <accession>BMDB0001886</accession>
  <secondary_accessions>
    <accession>BMDB01886</accession>
  </secondary_accessions>
  <name>3-Methylxanthine</name>
  <description/>
  <synonyms>
    <synonym>2-oxo-3-Methylhypoxanthine</synonym>
    <synonym>3 MX</synonym>
    <synonym>3,9-Dihydro-3-methyl-1H-purine-2,6-dione</synonym>
    <synonym>3-Methyl-3,7(9)-dihydro-purine-2,6-dione</synonym>
    <synonym>3-Methyl-3,9-dihydro-2H,6H-purine-2,6-dione</synonym>
    <synonym>3-Methylxanthine, methyl-(13)C-labeled</synonym>
    <synonym>3-Methylxanthine, monosodium salt</synonym>
    <synonym>3-Methylxanthine, monopotassium salt</synonym>
    <synonym>2,6-Dihydroxy-3-methylpurine</synonym>
    <synonym>3-Methyl xanthine</synonym>
    <synonym>3-Methyl-3,9-dihydro-purine-2,6-dione</synonym>
    <synonym>Purine analog</synonym>
    <synonym>3-Methylxanthine</synonym>
  </synonyms>
  <chemical_formula>C6H6N4O2</chemical_formula>
  <average_molecular_weight>166.1374</average_molecular_weight>
  <monisotopic_moleculate_weight>166.049075456</monisotopic_moleculate_weight>
  <iupac_name>3-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione</iupac_name>
  <traditional_iupac>3-methylxanthine</traditional_iupac>
  <cas_registry_number>1076-22-8</cas_registry_number>
  <smiles>CN1C2=C(NC=N2)C(=O)NC1=O</smiles>
  <inchi>InChI=1S/C6H6N4O2/c1-10-4-3(7-2-8-4)5(11)9-6(10)12/h2H,1H3,(H,7,8)(H,9,11,12)</inchi>
  <inchikey>GMSNIKWWOQHZGF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Xanthines</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxypyrimidines</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Purinones</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxypyrimidine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Xanthine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-methylxanthine</external_descriptor>
      <external_descriptor>Purine alkaloids</external_descriptor>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>&gt; 300 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.5</value>
      <source>GASPARI,F &amp; BONATI,M (1987)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>166.1374</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>166.049075456</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C2=C(NC=N2)C(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H6N4O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H6N4O2/c1-10-4-3(7-2-8-4)5(11)9-6(10)12/h2H,1H3,(H,7,8)(H,9,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GMSNIKWWOQHZGF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>78.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1780</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5549</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5550</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10310</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16983</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16984</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439253</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448193</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022724</foodb_id>
  <pubchem_compound_id>70639</pubchem_compound_id>
  <chemspider_id>63805</chemspider_id>
  <kegg_id>C16357</kegg_id>
  <chebi_id>62207</chebi_id>
  <drugbank_id/>
  <pdbe_id/>
  <knapsack_id>C00043196</knapsack_id>
  <meta_cyc_id>RXN-11546</meta_cyc_id>
  <wikipedia_id>Xanthine</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>2820</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:38 UTC</creation_date>
  <update_date>2020-03-13 16:29:16 UTC</update_date>
  <accession>BMDB0001888</accession>
  <secondary_accessions>
    <accession>BMDB01888</accession>
  </secondary_accessions>
  <name>N,N-Dimethylformamide</name>
  <description/>
  <synonyms>
    <synonym>Dimethylformamide</synonym>
    <synonym>DMF</synonym>
    <synonym>N,N-Dimethylmethanamide</synonym>
    <synonym>N-Formyldimethylamine</synonym>
    <synonym>Dimethyl formamide</synonym>
    <synonym>Dimethyl-formamide</synonym>
    <synonym>Dimethylamid kyseliny mravenci</synonym>
    <synonym>Dimethylforamide</synonym>
    <synonym>Dimethylformamid</synonym>
    <synonym>Dimetilformamide</synonym>
    <synonym>Dimetylformamidu</synonym>
    <synonym>Dwumetyloformamid</synonym>
    <synonym>Formyldimethylamine</synonym>
    <synonym>N,N- Dimethyl formamide</synonym>
    <synonym>N,N- Dimethylformamide</synonym>
    <synonym>N,N-Dimethyl-formamide</synonym>
    <synonym>N,N Dimethylformamide</synonym>
  </synonyms>
  <chemical_formula>C3H7NO</chemical_formula>
  <average_molecular_weight>73.0938</average_molecular_weight>
  <monisotopic_moleculate_weight>73.052763851</monisotopic_moleculate_weight>
  <iupac_name>N,N-dimethylformamide</iupac_name>
  <traditional_iupac>dimethylformamide</traditional_iupac>
  <cas_registry_number>68-12-2</cas_registry_number>
  <smiles>CN(C)C=O</smiles>
  <inchi>InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3</inchi>
  <inchikey>ZMXDDKWLCZADIW-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tertiary carboxylic acid amides. Tertiary carboxylic acid amides are compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Carboxylic acid derivatives</sub_class>
    <direct_parent>Tertiary carboxylic acid amides</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Tertiary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>formamides</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-60.4 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1000000 mg/L at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.01</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>1.00</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N,N-dimethylformamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>73.0938</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>73.052763851</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN(C)C=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C3H7NO</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZMXDDKWLCZADIW-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>20.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>19.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>7.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2580</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5029</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>5030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>699</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5551</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>178538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180855</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180856</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>180857</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>448201</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB004724</foodb_id>
  <pubchem_compound_id>6228</pubchem_compound_id>
  <chemspider_id>5993</chemspider_id>
  <kegg_id>C03134</kegg_id>
  <chebi_id>17741</chebi_id>
  <drugbank_id>DB01844</drugbank_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-581</meta_cyc_id>
  <wikipedia_id>Dimethylformamide</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:39 UTC</creation_date>
  <update_date>2020-04-16 17:53:24 UTC</update_date>
  <accession>BMDB0001890</accession>
  <secondary_accessions>
    <accession>BMDB01890</accession>
  </secondary_accessions>
  <name>Acetylcysteine</name>
  <description>Acetylcysteine, also known as NAC or (R)-mercaptate, belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. Acetylcysteine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. In cattle, acetylcysteine is involved in the metabolic pathway called the cysteine metabolism pathway.</description>
  <synonyms>
    <synonym>(2R)-2-Acetylamino-3-sulfanylpropanoic acid</synonym>
    <synonym>(R)-2-Acetylamino-3-mercaptopropanoic acid</synonym>
    <synonym>(R)-Mercapturic acid</synonym>
    <synonym>Acetilcisteina</synonym>
    <synonym>Acetylcysteinum</synonym>
    <synonym>L-Acetylcysteine</synonym>
    <synonym>L-alpha-Acetamido-beta-mercaptopropionic acid</synonym>
    <synonym>Mercapturic acid</synonym>
    <synonym>N-Acetyl-L-(+)-cysteine</synonym>
    <synonym>N-Acetylcysteine</synonym>
    <synonym>NAC</synonym>
    <synonym>(2R)-2-Acetylamino-3-sulfanylpropanoate</synonym>
    <synonym>(2R)-2-Acetylamino-3-sulphanylpropanoate</synonym>
    <synonym>(2R)-2-Acetylamino-3-sulphanylpropanoic acid</synonym>
    <synonym>(R)-2-Acetylamino-3-mercaptopropanoate</synonym>
    <synonym>(R)-Mercaptate</synonym>
    <synonym>(R)-Mercaptic acid</synonym>
    <synonym>L-a-Acetamido-b-mercaptopropionate</synonym>
    <synonym>L-a-Acetamido-b-mercaptopropionic acid</synonym>
    <synonym>L-alpha-Acetamido-beta-mercaptopropionate</synonym>
    <synonym>L-Α-acetamido-β-mercaptopropionate</synonym>
    <synonym>L-Α-acetamido-β-mercaptopropionic acid</synonym>
    <synonym>Mercaptate</synonym>
    <synonym>Mercaptic acid</synonym>
    <synonym>Acetadote</synonym>
    <synonym>Flumucetin</synonym>
    <synonym>2-Acetylamino-3-mercapto-propionate</synonym>
    <synonym>2-Acetylamino-3-mercapto-propionic acid</synonym>
    <synonym>Fluimicil infantil</synonym>
    <synonym>Fluimucetin</synonym>
    <synonym>Fluprowit</synonym>
    <synonym>N-Acety-L-cysteine</synonym>
    <synonym>N-Acetyl-3-mercaptoalanine</synonym>
    <synonym>Sodium 2-acetamido-3-mercaptopropionate</synonym>
    <synonym>Acemuc</synonym>
    <synonym>Acetylcysteine alcon brand</synonym>
    <synonym>Acetylcysteine betapharm brand</synonym>
    <synonym>Acetylcysteine bouchara brand</synonym>
    <synonym>Acetylcysteine farmasan brand</synonym>
    <synonym>Acetylcysteine fresenius brand</synonym>
    <synonym>Acetylcysteine inpharzam brand</synonym>
    <synonym>Acetylcysteine klinge brand</synonym>
    <synonym>Acetylcysteine lindopharm brand</synonym>
    <synonym>Acetylcysteine pharbita brand</synonym>
    <synonym>Acetylcysteine whitehall brand</synonym>
    <synonym>Acetylcysteine, monosodium salt</synonym>
    <synonym>Acétylcystéine GNR</synonym>
    <synonym>Allen and hanburys brand OF acetylcysteine</synonym>
    <synonym>Bioiberica brand OF acetylcysteine</synonym>
    <synonym>Bristol myers squibb brand OF acetylcysteine</synonym>
    <synonym>Bromuc</synonym>
    <synonym>Dey brand OF acetylcysteine sodium salt</synonym>
    <synonym>Eurespiran</synonym>
    <synonym>Exomuc</synonym>
    <synonym>Fresenius brand OF acetylcysteine</synonym>
    <synonym>GNR Pharma brand OF acetylcysteine</synonym>
    <synonym>GNR-Pharma brand OF acetylcysteine</synonym>
    <synonym>Genac</synonym>
    <synonym>Génévrier brand OF acetylcysteine</synonym>
    <synonym>Hermes brand OF acetylcysteine</synonym>
    <synonym>Heumann brand OF acetylcysteine</synonym>
    <synonym>Monosodium salt acetylcysteine</synonym>
    <synonym>Mucosil</synonym>
    <synonym>NAC al</synonym>
    <synonym>NAC, bisolvon</synonym>
    <synonym>Oberlin brand OF acetylcysteine</synonym>
    <synonym>Pfleger brand OF acetylcysteine</synonym>
    <synonym>Produpharm lappe brand OF acetylcysteine</synonym>
    <synonym>Roberts brand OF acetylcysteine</synonym>
    <synonym>Roche nicholas brand OF acetylcysteine</synonym>
    <synonym>Siran</synonym>
    <synonym>Sodium, acetylcysteine</synonym>
    <synonym>Temmler brand OF acetylcysteine</synonym>
    <synonym>Teva brand OF acetylcysteine</synonym>
    <synonym>Zambon brand OF acetylcysteine</synonym>
    <synonym>Zambon, nac</synonym>
    <synonym>Acetylcystein atid</synonym>
    <synonym>Acetylcystein, mentopin</synonym>
    <synonym>Acetylcysteine azupharma brand</synonym>
    <synonym>Acetylcysteine centrafarm brand</synonym>
    <synonym>Acetylcysteine hermes brand</synonym>
    <synonym>Acetylcysteine krewel brand</synonym>
    <synonym>Acetylcysteine temmler brand</synonym>
    <synonym>Acetylcysteine teva brand</synonym>
    <synonym>Acetylcysteine upsa brand</synonym>
    <synonym>Acetylcysteine zyma brand</synonym>
    <synonym>Acetylcysteine, (DL)-isomer</synonym>
    <synonym>Betapharm brand OF acetylcysteine</synonym>
    <synonym>Bristol myers squibb brand OF acetylcysteine sodium salt</synonym>
    <synonym>Disphar brand OF acetylcysteine</synonym>
    <synonym>Farmasan brand OF acetylcysteine</synonym>
    <synonym>Fluimucil</synonym>
    <synonym>Jenapharm</synonym>
    <synonym>Klinge brand OF acetylcysteine</synonym>
    <synonym>Lindopharm brand OF acetylcysteine</synonym>
    <synonym>MPectil</synonym>
    <synonym>Merck brand OF acetylcysteine</synonym>
    <synonym>Mucosol</synonym>
    <synonym>NAC zambon</synonym>
    <synonym>Siccoral</synonym>
    <synonym>Trommsdorff brand OF acetylcysteine</synonym>
    <synonym>Zyma brand OF acetylcysteine</synonym>
    <synonym>Mentopin acetylcystein</synonym>
    <synonym>Acetylcystein al</synonym>
    <synonym>Acetylcystein heumann</synonym>
    <synonym>Acetylcystein trom</synonym>
    <synonym>Acetylcysteine aluid brand</synonym>
    <synonym>Acetylcysteine disphar brand</synonym>
    <synonym>Acetylcysteine GNR-pharma brand</synonym>
    <synonym>Acetylcysteine lichtenstein brand</synonym>
    <synonym>Acetylcysteine merck brand</synonym>
    <synonym>Acetylcysteine oberlin brand</synonym>
    <synonym>Acetylcysteine roberts brand</synonym>
    <synonym>Acetylcysteine sodium</synonym>
    <synonym>Acetylcysteine thiemann brand</synonym>
    <synonym>Acetylcysteine zinc</synonym>
    <synonym>Acetylcysteine, monoammonium salt</synonym>
    <synonym>Acetyst</synonym>
    <synonym>Acid, mercapturic</synonym>
    <synonym>Airbron</synonym>
    <synonym>Alcon brand OF acetylcysteine</synonym>
    <synonym>Aluid brand OF acetylcysteine</synonym>
    <synonym>Alveolex</synonym>
    <synonym>Atid brand OF acetylcysteine</synonym>
    <synonym>Azubronchin</synonym>
    <synonym>Boehringer ingelheim brand OF acetylcysteine</synonym>
    <synonym>Bristol-myers squibb brand OF acetylcysteine sodium salt</synonym>
    <synonym>Broncho fips</synonym>
    <synonym>Broncholysin</synonym>
    <synonym>Centrafarm brand OF acetylcysteine</synonym>
    <synonym>Codotussyl</synonym>
    <synonym>Cystamucil</synonym>
    <synonym>Dampo mucopect</synonym>
    <synonym>Hoestil</synonym>
    <synonym>Hustengetränk, optipect</synonym>
    <synonym>Inpharzam brand OF acetylcysteine</synonym>
    <synonym>Intra brand OF acetylcysteine</synonym>
    <synonym>Larylin nac</synonym>
    <synonym>Lindocetyl</synonym>
    <synonym>m Pectil</synonym>
    <synonym>Mucopect, dampo</synonym>
    <synonym>Mucosolvin</synonym>
    <synonym>Optipect hustengetränk</synonym>
    <synonym>Sanigen, muco</synonym>
    <synonym>Solmucol</synonym>
    <synonym>Thiemann brand OF acetylcysteine</synonym>
    <synonym>Whitehall brand OF acetylcysteine</synonym>
    <synonym>Zinc, acetylcysteine</synonym>
    <synonym>Acebraus</synonym>
    <synonym>Durabronchal</synonym>
    <synonym>Acetabs</synonym>
    <synonym>Acetylcysteine atid brand</synonym>
    <synonym>Acetylcysteine bioiberica brand</synonym>
    <synonym>Acetylcysteine guerbet brand</synonym>
    <synonym>Acetylcysteine génévrier brand</synonym>
    <synonym>Acetylcysteine heumann brand</synonym>
    <synonym>Acetylcysteine hydrochloride</synonym>
    <synonym>Acetylcysteine intra brand</synonym>
    <synonym>Acetylcysteine pfleger brand</synonym>
    <synonym>Acetylcysteine trommsdorff brand</synonym>
    <synonym>Acetylcysteine zambon brand</synonym>
    <synonym>Acetylcysteine ac-pharma brand</synonym>
    <synonym>Acetylcysteine, (D)-isomer</synonym>
    <synonym>Acetylin</synonym>
    <synonym>Azupharma brand OF acetylcysteine</synonym>
    <synonym>Bisolvon nac</synonym>
    <synonym>Bouchara brand OF acetylcysteine</synonym>
    <synonym>Bristol-myers squibb brand OF acetylcysteine</synonym>
    <synonym>Broncho-fips</synonym>
    <synonym>BronchoFips</synonym>
    <synonym>Broncoclar</synonym>
    <synonym>Fabrol</synonym>
    <synonym>Frekatuss</synonym>
    <synonym>Guerbet brand OF acetylcysteine</synonym>
    <synonym>Hydrochloride, acetylcysteine</synonym>
    <synonym>Ilube</synonym>
    <synonym>Jenacystein</synonym>
    <synonym>Krewel brand OF acetylcysteine</synonym>
    <synonym>Lantamed</synonym>
    <synonym>Lichtenstein brand OF acetylcysteine</synonym>
    <synonym>m-Pectil</synonym>
    <synonym>Monoammonium salt acetylcysteine</synonym>
    <synonym>Muciteran</synonym>
    <synonym>Muco sanigen</synonym>
    <synonym>Mucomyst</synonym>
    <synonym>N Acetyl L cysteine</synonym>
    <synonym>N Acetylcysteine</synonym>
    <synonym>Pharbita brand OF acetylcysteine</synonym>
    <synonym>UPSA brand OF acetylcysteine</synonym>
    <synonym>Ac pharma brand OF acetylcysteine</synonym>
    <synonym>Ac-pharma brand OF acetylcysteine</synonym>
    <synonym>Acetylcysteine</synonym>
  </synonyms>
  <chemical_formula>C5H9NO3S</chemical_formula>
  <average_molecular_weight>163.195</average_molecular_weight>
  <monisotopic_moleculate_weight>163.030313849</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2-acetamido-3-sulfanylpropanoic acid</iupac_name>
  <traditional_iupac>acetylcysteine</traditional_iupac>
  <cas_registry_number>616-91-1</cas_registry_number>
  <smiles>CC(=O)N[C@@H](CS)C(O)=O</smiles>
  <inchi>InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m0/s1</inchi>
  <inchikey>PWKSKIMOESPYIA-BYPYZUCNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>N-acyl-L-alpha-amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alkylthiols</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cysteine and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetamide</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alkylthiol</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Cysteine or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>L-cysteine derivative</external_descriptor>
      <external_descriptor>N-acetyl-L-amino acid</external_descriptor>
      <external_descriptor>acetylcysteine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>109.5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2-acetamido-3-sulfanylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>163.195</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>163.030313849</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(=O)N[C@@H](CS)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H9NO3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>PWKSKIMOESPYIA-BYPYZUCNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>37.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1723</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1331</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1796</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258876</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258877</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258878</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278816</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>By UPLC-Q-TOF</comment>
      <references>
        <reference>
          <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
          <pubmed_id>29565828</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB06151</drugbank_id>
  <foodb_id>FDB002281</foodb_id>
  <kegg_id>C06809</kegg_id>
  <chemspider_id>11540</chemspider_id>
  <pubchem_compound_id>12035</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28939</chebi_id>
  <meta_cyc_id>CPD-9175</meta_cyc_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Acetylcysteine</wikipedia_id>
  <metlin_id>784</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735.</reference_text>
      <pubmed_id>29565828</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:41 UTC</creation_date>
  <update_date>2020-03-13 16:29:18 UTC</update_date>
  <accession>BMDB0001891</accession>
  <secondary_accessions>
    <accession>BMDB01891</accession>
  </secondary_accessions>
  <name>m-Aminobenzoic acid</name>
  <description>m-Aminobenzoic acid, also known as 3-aminobenzoesaeure or 3-carboxyaniline, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. m-Aminobenzoic acid exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule.</description>
  <synonyms>
    <synonym>3-Aminobenzoesaeure</synonym>
    <synonym>3-Carboxyaniline</synonym>
    <synonym>m-Aminobenzoesaeure</synonym>
    <synonym>m-Carboxyaniline</synonym>
    <synonym>MABA</synonym>
    <synonym>m-Aminobenzoate</synonym>
    <synonym>Aniline-3-carboxylate</synonym>
    <synonym>3-Aminobenzoate</synonym>
    <synonym>3-Aminobenzoic acid</synonym>
    <synonym>Aniline-3-carboxylic acid</synonym>
    <synonym>m-Amonibenzoate</synonym>
    <synonym>m-Amonibenzoic acid</synonym>
    <synonym>3-Aminobenzoic acid, monosodium salt</synonym>
    <synonym>Meta-aminobenzoic acid</synonym>
    <synonym>m-Aminobenzoic acid</synonym>
  </synonyms>
  <chemical_formula>C7H7NO2</chemical_formula>
  <average_molecular_weight>137.136</average_molecular_weight>
  <monisotopic_moleculate_weight>137.047678473</monisotopic_moleculate_weight>
  <iupac_name>3-aminobenzoic acid</iupac_name>
  <traditional_iupac>gabaculine</traditional_iupac>
  <cas_registry_number>99-05-8</cas_registry_number>
  <smiles>NC1=CC=CC(=C1)C(O)=O</smiles>
  <inchi>InChI=1S/C7H7NO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,8H2,(H,9,10)</inchi>
  <inchikey>XFDUHJPVQKIXHO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>Aminobenzoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminobenzoic acid</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aminobenzoic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>173 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>5.9 mg/mL at 15 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.65</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.93</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.33</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>3.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-aminobenzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>137.136</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>137.047678473</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=CC=CC(=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H7NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H7NO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,8H2,(H,9,10)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XFDUHJPVQKIXHO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>38.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>13.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29656</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1724</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1798</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1799</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447304</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB022725</foodb_id>
  <pubchem_compound_id>7419</pubchem_compound_id>
  <chemspider_id>7141</chemspider_id>
  <kegg_id/>
  <chebi_id>42682</chebi_id>
  <drugbank_id>DB02054</drugbank_id>
  <pdbe_id/>
  <knapsack_id/>
  <meta_cyc_id>HMDB01891</meta_cyc_id>
  <wikipedia_id>3-Aminobenzoic_acid</wikipedia_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id>6374</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:42 UTC</creation_date>
  <update_date>2020-04-15 22:30:09 UTC</update_date>
  <accession>BMDB0001892</accession>
  <secondary_accessions>
    <accession>BMDB01892</accession>
  </secondary_accessions>
  <name>Menadione</name>
  <description/>
  <synonyms>
    <synonym>2-Methyl-1,4-naphthalenedione</synonym>
    <synonym>2-Methyl-1,4-naphthochinon</synonym>
    <synonym>2-Methyl-1,4-naphthoquinone</synonym>
    <synonym>Vitamin K3</synonym>
    <synonym>Kappaxin</synonym>
    <synonym>2-Methyl-1,4-naftochinon</synonym>
    <synonym>2-Methyl-1,4-naphthalendione</synonym>
    <synonym>2-Methyl-1,4-naphthodione</synonym>
    <synonym>2-Methylnaphthoquinone</synonym>
    <synonym>3-Methyl-1,4-naphthoquinone</synonym>
    <synonym>Aquakay</synonym>
    <synonym>Aquinone</synonym>
    <synonym>Hemodal</synonym>
    <synonym>Juva-K</synonym>
    <synonym>K-Thrombyl</synonym>
    <synonym>K-Vitan</synonym>
    <synonym>Kaergona</synonym>
    <synonym>Kanone</synonym>
    <synonym>Kappaxan</synonym>
    <synonym>Karcon</synonym>
    <synonym>Kareon</synonym>
    <synonym>Kativ-g</synonym>
    <synonym>Kayklot</synonym>
    <synonym>Kaykot</synonym>
    <synonym>Kaynone</synonym>
    <synonym>Kayquinone</synonym>
    <synonym>Kipca</synonym>
    <synonym>Kipca-oil soluble</synonym>
    <synonym>Klottone</synonym>
    <synonym>Koaxin</synonym>
    <synonym>Kolklot</synonym>
    <synonym>Menadion</synonym>
    <synonym>Menaphthene</synonym>
    <synonym>Menaphthon</synonym>
    <synonym>Menaphthone</synonym>
    <synonym>Menaphtone</synonym>
    <synonym>Menaquinone</synonym>
    <synonym>Menaquinone O</synonym>
    <synonym>Mitenon</synonym>
    <synonym>Mitenone</synonym>
    <synonym>MNQ</synonym>
    <synonym>Panosine</synonym>
    <synonym>Prokayvit</synonym>
    <synonym>Synkay</synonym>
    <synonym>Thyloquinone</synonym>
    <synonym>Vitamin K0</synonym>
    <synonym>Vitamin K2</synonym>
    <synonym>Vitamin K3: 1,4-dihydro-1,4-dioxo-2-methylnaphthalene</synonym>
    <synonym>Bisulfite, menadione</synonym>
    <synonym>Vicasol</synonym>
    <synonym>Bisulfite, menadione sodium</synonym>
    <synonym>Menadione sodium bisulfite</synonym>
    <synonym>Vikasol</synonym>
    <synonym>Vitamin K 3</synonym>
    <synonym>Menadione sodium bisulfite, trihydrate</synonym>
    <synonym>Vitamin K3 sodium bisulfite</synonym>
    <synonym>Menadione bisulfite</synonym>
    <synonym>Sodium bisulfite, menadione</synonym>
  </synonyms>
  <chemical_formula>C11H8O2</chemical_formula>
  <average_molecular_weight>172.18</average_molecular_weight>
  <monisotopic_moleculate_weight>172.0524295</monisotopic_moleculate_weight>
  <iupac_name>2-methyl-1,4-dihydronaphthalene-1,4-dione</iupac_name>
  <traditional_iupac>menadione</traditional_iupac>
  <cas_registry_number>58-27-5</cas_registry_number>
  <smiles>CC1=CC(=O)C2=CC=CC=C2C1=O</smiles>
  <inchi>InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3</inchi>
  <inchikey>MJVAVZPDRWSRRC-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Naphthalenes</class>
    <sub_class>Naphthoquinones</sub_class>
    <direct_parent>Naphthoquinones</direct_parent>
    <alternative_parents>
      <alternative_parent>Aryl ketones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Quinones</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Aryl ketone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketone</substituent>
      <substituent>Naphthoquinone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Quinone</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fat-soluble vitamins</external_descriptor>
      <external_descriptor>a vitamin K</external_descriptor>
      <external_descriptor>naphthoquinone</external_descriptor>
      <external_descriptor>vitamin K</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>107 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.160 mg/mL at 30 °C</value>
      <source>YALKOWSKY,SH &amp; DANNENFELSER,RM (1992)</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.2</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.94</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-methyl-1,4-dihydronaphthalene-1,4-dione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>172.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>172.0524295</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CC(=O)C2=CC=CC=C2C1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H8O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MJVAVZPDRWSRRC-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>34.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2498</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1725</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1423</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13996</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29011</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31366</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31367</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31368</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5575</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19897</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21447</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21448</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450779</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB00170</drugbank_id>
  <foodb_id>FDB000953</foodb_id>
  <kegg_id>C05377</kegg_id>
  <chemspider_id>3915</chemspider_id>
  <pubchem_compound_id>4055</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>28869</chebi_id>
  <meta_cyc_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>Menadione</wikipedia_id>
  <metlin_id>3910</metlin_id>
  <synthesis_reference>Minami, Ryohei; Nishizaki, Tadao; Kumagai, Yoshitoshi.  Menadione.    Jpn. Kokai Tokkyo Koho  (1986),     4 pp.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:43 UTC</creation_date>
  <update_date>2020-04-16 20:39:29 UTC</update_date>
  <accession>BMDB0001893</accession>
  <secondary_accessions>
    <accession>BMDB01893</accession>
  </secondary_accessions>
  <name>Alpha-Tocopherol</name>
  <description>Alpha-Tocopherol, also known as D-α-tocopherol or vitamin e, belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. Thus, Alpha-tocopherol is considered to be a quinone lipid molecule. Alpha-Tocopherol exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Alpha-Tocopherol exists in all living organisms, ranging from bacteria to humans. Alpha-Tocopherol is a potentially toxic compound. Alpha-Tocopherol has been found to be associated with several diseases known as parkinson's disease, thyroid cancer, cerebrotendinous xanthomatosis, and vitamin e deficiency; also alpha-tocopherol has been linked to the inborn metabolic disorders including abetalipoproteinemia.</description>
  <synonyms>
    <synonym>(2R,4'r,8'r)-alpha-Tocopherol</synonym>
    <synonym>(R,R,R)-alpha-Tocopherol</synonym>
    <synonym>5,7,8-Trimethyltocol</synonym>
    <synonym>D-alpha-Tocopherol</synonym>
    <synonym>Vitamin e</synonym>
    <synonym>(2R,4'r,8'r)-a-Tocopherol</synonym>
    <synonym>(2R,4'r,8'r)-Α-tocopherol</synonym>
    <synonym>(R,R,R)-a-Tocopherol</synonym>
    <synonym>(R,R,R)-Α-tocopherol</synonym>
    <synonym>D-a-Tocopherol</synonym>
    <synonym>D-Α-tocopherol</synonym>
    <synonym>a-Tocopherol</synonym>
    <synonym>Α-tocopherol</synonym>
    <synonym>(+)-a-Tocopherol</synonym>
    <synonym>(+)-alpha-Tocopherol</synonym>
    <synonym>(2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol</synonym>
    <synonym>a-D-Tocopherol</synonym>
    <synonym>alpha-delta-Tocopherol</synonym>
    <synonym>delta-alpha-Tocopherol</synonym>
    <synonym>Denamone</synonym>
    <synonym>Eprolin</synonym>
    <synonym>Phytogermin</synonym>
    <synonym>Phytogermine</synonym>
    <synonym>RRR-alpha-Tocopherol</synonym>
    <synonym>RRR-alpha-Tocopheryl</synonym>
    <synonym>Vitamin ea</synonym>
    <synonym>alpha-Tocopherol</synonym>
  </synonyms>
  <chemical_formula>C29H50O2</chemical_formula>
  <average_molecular_weight>430.7061</average_molecular_weight>
  <monisotopic_moleculate_weight>430.381080844</monisotopic_moleculate_weight>
  <iupac_name>(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol</iupac_name>
  <traditional_iupac>VitaE</traditional_iupac>
  <cas_registry_number>59-02-9</cas_registry_number>
  <smiles>CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1</smiles>
  <inchi>InChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1</inchi>
  <inchikey>GVJHHUAWPYXKBD-IEOSBIPESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Quinone and hydroquinone lipids</sub_class>
    <direct_parent>Tocopherols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-benzopyrans</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Diterpenoids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-benzopyran</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzopyran</substituent>
      <substituent>Chromane</substituent>
      <substituent>Diterpenoid</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Tocopherol</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fat-soluble vitamins</external_descriptor>
      <external_descriptor>Vitamin E</external_descriptor>
      <external_descriptor>alpha-tocopherol</external_descriptor>
      <external_descriptor>vitamin E</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>8.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>10.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>430.7061</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>430.381080844</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C29H50O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GVJHHUAWPYXKBD-IEOSBIPESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>29.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>135.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>55.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>1143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1786</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1726</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>19764</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30334</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1804</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5576</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269804</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Whole milk</comment>
      <references>
        <reference>
          <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
          <pubmed_id>11913692</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.161 - 7.685</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Commercial milk</comment>
      <references>
        <reference>
          <reference_text>Delgado Zamarreno MM, Sanchez Perez A, Gomez Perez C, Hernandez Mendez J: High-performance liquid chromatography with electrochemical detection for the simultaneous determination of vitamin A, D3 and E in milk. J Chromatogr. 1992 Oct 9;623(1):69-74.</reference_text>
          <pubmed_id>1333471</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.509</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Diet: low hay diet</comment>
      <references>
        <reference>
          <reference_text>Noziere P, Grolier P, Durand D, Ferlay A, Pradel P, Martin B: Variations in carotenoids, fat-soluble micronutrients, and color in cows' plasma and milk following changes in forage and feeding level. J Dairy Sci. 2006 Jul;89(7):2634-48. doi: 10.3168/jds.S0022-0302(06)72340-2.</reference_text>
          <pubmed_id>16772583</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.37 - 1.69</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw conventional milk</comment>
      <references>
        <reference>
          <reference_text>Chotyakul N, Pateiro-Moure M, Saraiva JA, Torres JA, Pérez-Lamela C. 2014. Simultaneous HPLC–DAD quantification of vitamins A and E content in raw, pasteurized, and UHT cow’s milk and their changes during storage. European Food Research and Technology. 238(4):535–547 </reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.16 - 0.21</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>UHT skim milk </comment>
      <references>
        <reference>
          <reference_text>Chotyakul N, Pateiro-Moure M, Saraiva JA, Torres JA, Pérez-Lamela C. 2014. Simultaneous HPLC–DAD quantification of vitamins A and E content in raw, pasteurized, and UHT cow’s milk and their changes during storage. European Food Research and Technology. 238(4):535–547 </reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.0183</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, filled, fluid, with lauric acid oil</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.232</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, 1% fat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.232</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, fluid, nonfat, calcium fortified (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.857</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, low sodium, fluid</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.232</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, lowfat, fluid, 1% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.232</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added nonfat milk solids, vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.232</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, with added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.232</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, nonfat, fluid, without added vitamin A and vitamin D (fat free or skim)</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.929</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, protein fortified, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.697</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, with added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.697</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, reduced fat, fluid, 2% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.871 +/- 0.0279</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Diet: corn silage with concentrates; Breed: Holstein</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.983 +/- 0.0720</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk. Diet: grass silage with concentates; Breed: Holstein</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.625</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, with added vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.625</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.25% milkfat, without added vitamin A and vitamin D</comment>
      <references>
        <reference>
          <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.120 +/- 0.100</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Spanish commercial milk; low-fat 1.5%</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.0800 +/- 0.830</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Spanish commercial milk; low-fat 3.6%</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.950 +/- 0.490</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Spanish commercial milk; skim 0.3% fat</comment>
      <references>
        <reference>
          <reference_text>International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.697</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, conventional (not organic), 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.929</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, partly skim, organic, 1.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.232</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.302</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, 0.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.232</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, skim, organic</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.0896</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, 3.5, (UHT), % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.393</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, conventional (not organic), 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.974</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Milk, whole, organic, 3.5 % fat</comment>
      <references>
        <reference>
          <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.90 - 2.16</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Chotyakul N, Pateiro-Moure M, Saraiva JA, Torres JA, Pérez-Lamela C. 2014. Simultaneous HPLC–DAD quantification of vitamins A and E content in raw, pasteurized, and UHT cow’s milk and their changes during storage. European Food Research and Technology. 238(4):535–547 </reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.464 - 2.322</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Graulet B: Improving the level of vitamins in milk. In Griffiths MW (ed):‘‘Improving the Safety and Quality of Milk: Improving Quality in Milk Products,’’vol. 2. Boca Raton, FL: CRC Press, pp 229–251, 2010.</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial, conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.464 - 4.179</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Oste R, Jagerstad M, Anderson I: Vitamins in milk and milk products. In Fox PF (ed):‘‘Advanced Dairy Chemistry: Lactose, Water, Salts and Vitamins,’’vol 3, 2nd ed. London: Chapman &amp; Hall, pp 347–402, 1997</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.5 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 1% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.8 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 2% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.9 +/- 0.2</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in 3.25% milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.5 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Quantified by LC-MS/MS in skim milk</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Muscle</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples have been collected from Heifer cows.</comment>
      <references>
        <reference>
          <reference_text>Osorio MT, Downey G, Moloney AP, Rohrle FT, Luciano G, Schmidt O, Monahan FJ: Beef authentication using dietary markers: chemometric selection and modelling of significant beef biomarkers using concatenated data from multiple analytical methods. Food Chem. 2013 Dec 1;141(3):2795-801. doi: 10.1016/j.foodchem.2013.05.118. Epub  2013 Jun 5.</reference_text>
          <pubmed_id>23871026</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id>FDB000565</foodb_id>
  <chemspider_id>14265</chemspider_id>
  <pubchem_compound_id>14985</pubchem_compound_id>
  <drugbank_id>DB00163</drugbank_id>
  <kegg_id>C02477</kegg_id>
  <chebi_id>18145</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id>C00007366</knapsack_id>
  <bigg_id>2296507</bigg_id>
  <wikipedia_id>Alpha-Tocopherol</wikipedia_id>
  <metlin_id>6376</metlin_id>
  <synthesis_reference>Matsui, Makoto.  Synthesis of a-tocopherol for the next century.    Nihon Yukagakkaishi  (1996),  45(9),  821-831. </synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Delgado Zamarreno MM, Sanchez Perez A, Gomez Perez C, Hernandez Mendez J: High-performance liquid chromatography with electrochemical detection for the simultaneous determination of vitamin A, D3 and E in milk. J Chromatogr. 1992 Oct 9;623(1):69-74.</reference_text>
      <pubmed_id>1333471</pubmed_id>
    </reference>
    <reference>
      <reference_text>Noziere P, Grolier P, Durand D, Ferlay A, Pradel P, Martin B: Variations in carotenoids, fat-soluble micronutrients, and color in cows' plasma and milk following changes in forage and feeding level. J Dairy Sci. 2006 Jul;89(7):2634-48. doi: 10.3168/jds.S0022-0302(06)72340-2.</reference_text>
      <pubmed_id>16772583</pubmed_id>
    </reference>
    <reference>
      <reference_text>Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4.</reference_text>
      <pubmed_id>11913692</pubmed_id>
    </reference>
    <reference>
      <reference_text>International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570</reference_text>
    </reference>
    <reference>
      <reference_text>International Dairy Journal; Volume 15, Issue 5, May 2005, Pages 521-526</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Chotyakul N, Pateiro-Moure M, Saraiva JA, Torres JA, Pérez-Lamela C. 2014. Simultaneous HPLC–DAD quantification of vitamins A and E content in raw, pasteurized, and UHT cow’s milk and their changes during storage. European Food Research and Technology. 238(4):535–547 </reference_text>
    </reference>
    <reference>
      <reference_text>Graulet B: Improving the level of vitamins in milk. In Griffiths MW (ed):‘‘Improving the Safety and Quality of Milk: Improving Quality in Milk Products,’’vol. 2. Boca Raton, FL: CRC Press, pp 229–251, 2010.</reference_text>
    </reference>
    <reference>
      <reference_text>Oste R, Jagerstad M, Anderson I: Vitamins in milk and milk products. In Fox PF (ed):‘‘Advanced Dairy Chemistry: Lactose, Water, Salts and Vitamins,’’vol 3, 2nd ed. London: Chapman &amp; Hall, pp 347–402, 1997</reference_text>
    </reference>
    <reference>
      <reference_text>USDA Food Composition Databases: https://ndb.nal.usda.gov/ndb/</reference_text>
    </reference>
    <reference>
      <reference_text>Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/QueryFood.php?fn=milk&amp;lang=en</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:44 UTC</creation_date>
  <update_date>2020-03-13 16:29:19 UTC</update_date>
  <accession>BMDB0001896</accession>
  <secondary_accessions>
    <accession>BMDB01896</accession>
  </secondary_accessions>
  <name>5-Methoxytryptophol</name>
  <description/>
  <synonyms>
    <synonym>5-Methoxy-1H-indole-3-ethanol</synonym>
    <synonym>5-Methoxyindole-3-ethanol</synonym>
    <synonym>Methoxytryptophol</synonym>
    <synonym>5-Methoxytryptophol</synonym>
  </synonyms>
  <chemical_formula>C11H13NO2</chemical_formula>
  <average_molecular_weight>191.2264</average_molecular_weight>
  <monisotopic_moleculate_weight>191.094628665</monisotopic_moleculate_weight>
  <iupac_name>2-(5-methoxy-1H-indol-3-yl)ethan-1-ol</iupac_name>
  <traditional_iupac>methoxytryptophol</traditional_iupac>
  <cas_registry_number>712-09-4</cas_registry_number>
  <smiles>COC1=CC=C2NC=C(CCO)C2=C1</smiles>
  <inchi>InChI=1S/C11H13NO2/c1-14-9-2-3-11-10(6-9)8(4-5-13)7-12-11/h2-3,6-7,12-13H,4-5H2,1H3</inchi>
  <inchikey>QLWKTGDEPLRFAT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Indoles</sub_class>
    <direct_parent>3-alkylindoles</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alkylindole</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Ether</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(5-methoxy-1H-indol-3-yl)ethan-1-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>191.2264</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>191.094628665</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC=C2NC=C(CCO)C2=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H13NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H13NO2/c1-14-9-2-3-11-10(6-9)8(4-5-13)7-12-11/h2-3,6-7,12-13H,4-5H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QLWKTGDEPLRFAT-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>45.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>55.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300142</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300143</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>300144</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>342345</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022726</foodb_id>
  <chemspider_id>12305</chemspider_id>
  <pubchem_compound_id>12835</pubchem_compound_id>
  <drugbank_id/>
  <kegg_id/>
  <chebi_id>114833</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Tryptophol</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Taborsky, Robert G.; Delvigs, Peter. Synthesis of some substituted tryptophols of possible physiological importance and a study with 3-(2-acetoxyethyl)-5-methoxyindole (5-methoxytryptophol O-acetate) on sexual maturation.  J. Med. Chem., 1966, 9 (2), pp 251–254  DOI: 10.1021/jm00320a028</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:46 UTC</creation_date>
  <update_date>2020-03-13 16:29:20 UTC</update_date>
  <accession>BMDB0001897</accession>
  <secondary_accessions>
    <accession>BMDB01897</accession>
  </secondary_accessions>
  <name>Substance P</name>
  <description/>
  <synonyms>
    <synonym>Arg-pro-lys-pro-GLN-GLN-phe-phe-gly-leu-met-NH2</synonym>
    <synonym>(2S)-2-{[(2R)-2-({[(2S)-1-[(2S)-6-amino-2-({[(2R)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)hexanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-N-[(1R)-1-{[(1R)-1-[({[(1R)-1-{[(1S)-1-(C-hydroxycarbonimidoyl)-3-(methylsulfanyl)propyl]-C-hydroxycarbonimidoyl}-3-methylbutyl]-C-hydroxycarbonimidoyl}methyl)-C-hydroxycarbonimidoyl]-2-phenylethyl]-C-hydroxycarbonimidoyl}-2-phenylethyl]pentanediimidate</synonym>
    <synonym>(2S)-2-{[(2R)-2-({[(2S)-1-[(2S)-6-amino-2-({[(2R)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)hexanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-N-[(1R)-1-{[(1R)-1-[({[(1R)-1-{[(1S)-1-(C-hydroxycarbonimidoyl)-3-(methylsulphanyl)propyl]-C-hydroxycarbonimidoyl}-3-methylbutyl]-C-hydroxycarbonimidoyl}methyl)-C-hydroxycarbonimidoyl]-2-phenylethyl]-C-hydroxycarbonimidoyl}-2-phenylethyl]pentanediimidate</synonym>
    <synonym>(2S)-2-{[(2R)-2-({[(2S)-1-[(2S)-6-amino-2-({[(2R)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)hexanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-N-[(1R)-1-{[(1R)-1-[({[(1R)-1-{[(1S)-1-(C-hydroxycarbonimidoyl)-3-(methylsulphanyl)propyl]-C-hydroxycarbonimidoyl}-3-methylbutyl]-C-hydroxycarbonimidoyl}methyl)-C-hydroxycarbonimidoyl]-2-phenylethyl]-C-hydroxycarbonimidoyl}-2-phenylethyl]pentanediimidic acid</synonym>
  </synonyms>
  <chemical_formula>C63H98N18O13S</chemical_formula>
  <average_molecular_weight>1347.63</average_molecular_weight>
  <monisotopic_moleculate_weight>1346.728146002</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-[(2R)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2R)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-4-carbamoylbutanamido]-N-[(1R)-1-{[(1R)-1-[({[(1R)-1-{[(1S)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-phenylethyl]carbamoyl}-2-phenylethyl]pentanediamide</iupac_name>
  <traditional_iupac>(2S)-2-[(2R)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2R)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-4-carbamoylbutanamido]-N-[(1R)-1-{[(1R)-1-[({[(1R)-1-{[(1S)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-phenylethyl]carbamoyl}-2-phenylethyl]pentanediamide</traditional_iupac>
  <cas_registry_number>33507-63-0</cas_registry_number>
  <smiles>CSCC[C@H](NC(=O)[C@@H](CC(C)C)NC(=O)CNC(=O)[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CCC(N)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCNC(N)=N)C(N)=O</smiles>
  <inchi>InChI=1S/C63H98N18O13S/c1-37(2)33-45(57(89)74-41(53(68)85)27-32-95-3)73-52(84)36-72-54(86)46(34-38-15-6-4-7-16-38)78-58(90)47(35-39-17-8-5-9-18-39)79-56(88)42(23-25-50(66)82)75-55(87)43(24-26-51(67)83)76-59(91)49-22-14-31-81(49)62(94)44(20-10-11-28-64)77-60(92)48-21-13-30-80(48)61(93)40(65)19-12-29-71-63(69)70/h4-9,15-18,37,40-49H,10-14,19-36,64-65H2,1-3H3,(H2,66,82)(H2,67,83)(H2,68,85)(H,72,86)(H,73,84)(H,74,89)(H,75,87)(H,76,91)(H,77,92)(H,78,90)(H,79,88)(H4,69,70,71)/t40-,41-,42-,43+,44-,45+,46+,47+,48+,49-/m0/s1</inchi>
  <inchikey>ADNPLDHMAVUMIW-SGTHPBLKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Quinone and hydroquinone lipids</sub_class>
    <direct_parent>Tocopherols</direct_parent>
    <alternative_parents>
      <alternative_parent>1-benzopyrans</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Diterpenoids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-benzopyran</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzopyran</substituent>
      <substituent>Chromane</substituent>
      <substituent>Diterpenoid</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Tocopherol</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Fat-soluble vitamins</external_descriptor>
      <external_descriptor>Vitamin E</external_descriptor>
      <external_descriptor>alpha-tocopherol</external_descriptor>
      <external_descriptor>vitamin E</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>148 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.15</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-5.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>11.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-[(2R)-2-{[(2S)-1-[(2S)-6-amino-2-{[(2R)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]formamido}hexanoyl]pyrrolidin-2-yl]formamido}-4-carbamoylbutanamido]-N-[(1R)-1-{[(1R)-1-[({[(1R)-1-{[(1S)-1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-phenylethyl]carbamoyl}-2-phenylethyl]pentanediamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>1347.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>1346.728146002</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CSCC[C@H](NC(=O)[C@@H](CC(C)C)NC(=O)CNC(=O)[C@@H](CC1=CC=CC=C1)NC(=O)[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CCC(N)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCNC(N)=N)C(N)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C63H98N18O13S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C63H98N18O13S/c1-37(2)33-45(57(89)74-41(53(68)85)27-32-95-3)73-52(84)36-72-54(86)46(34-38-15-6-4-7-16-38)78-58(90)47(35-39-17-8-5-9-18-39)79-56(88)42(23-25-50(66)82)75-55(87)43(24-26-51(67)83)76-59(91)49-22-14-31-81(49)62(94)44(20-10-11-28-64)77-60(92)48-21-13-30-80(48)61(93)40(65)19-12-29-71-63(69)70/h4-9,15-18,37,40-49H,10-14,19-36,64-65H2,1-3H3,(H2,66,82)(H2,67,83)(H2,68,85)(H,72,86)(H,73,84)(H,74,89)(H,75,87)(H,76,91)(H,77,92)(H,78,90)(H,79,88)(H4,69,70,71)/t40-,41-,42-,43+,44-,45+,46+,47+,48+,49-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ADNPLDHMAVUMIW-SGTHPBLKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>516.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>362.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>141.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>65454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>65455</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>65456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122859</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122860</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>122861</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB002259</foodb_id>
  <chemspider_id>23215821</chemspider_id>
  <pubchem_compound_id>44359816</pubchem_compound_id>
  <drugbank_id/>
  <kegg_id/>
  <chebi_id>332416</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Substance P</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Egorova, S. V.; Akhrem, A. A.  Synthesis of substance P.    Vestsi Akademii Navuk BSSR, Seryya Khimichnykh Navuk  (1989),   (1),  46-51.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:47 UTC</creation_date>
  <update_date>2020-03-13 16:29:20 UTC</update_date>
  <accession>BMDB0001898</accession>
  <secondary_accessions>
    <accession>BMDB01898</accession>
  </secondary_accessions>
  <name>Mesobilirubinogen</name>
  <description/>
  <synonyms>
    <synonym>2,17-Diethyl-1,4,5,10,15,16,19,22,23,24-decahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acid</synonym>
    <synonym>8,12-Bis(2-carboxyethyl)-3,18-diethyl-2,7,13,17-tetramethylbilane-1,19(4H,16H)-dione</synonym>
    <synonym>I-urobilinogen</synonym>
    <synonym>Mesobilirubinogen ixalpha</synonym>
    <synonym>Urobilinogen ixalpha</synonym>
    <synonym>Urobilinogen</synonym>
    <synonym>2,17-Diethyl-1,4,5,10,15,16,19,22,23,24-decahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoate</synonym>
    <synonym>2,17-Diethyl-1,4,5,10,15,16,19,22,23,24-decahydro-3,7,13,18-tetramethyl-1,19-dioxo-biline-8,12-dipropionic acid</synonym>
    <synonym>Mesobilirubinogen ixα</synonym>
    <synonym>Urobilinogen ixα</synonym>
    <synonym>Mesobilirubinogen</synonym>
  </synonyms>
  <chemical_formula>C33H44N4O6</chemical_formula>
  <average_molecular_weight>592.7257</average_molecular_weight>
  <monisotopic_moleculate_weight>592.32608516</monisotopic_moleculate_weight>
  <iupac_name>3-(2-{[3-(2-carboxyethyl)-5-[(4-ethyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(3-ethyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid</iupac_name>
  <traditional_iupac>urobilinogen</traditional_iupac>
  <cas_registry_number>14684-37-8</cas_registry_number>
  <smiles>CCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(CC3NC(=O)C(CC)=C3C)N2)N1</smiles>
  <inchi>InChI=1S/C33H44N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h26-27,34-35H,7-15H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)</inchi>
  <inchikey>OBHRVMZSZIDDEK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Bilirubins</sub_class>
    <direct_parent>Bilirubins</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrrolines</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Bilirubin skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboxylic acid or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Pyrroline</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>bilanes</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>logp</kind>
      <value>1.969</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.11</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.018</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(2-{[3-(2-carboxyethyl)-5-[(4-ethyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(3-ethyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>592.7257</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>592.32608516</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(CC3NC(=O)C(CC)=C3C)N2)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C33H44N4O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C33H44N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h26-27,34-35H,7-15H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OBHRVMZSZIDDEK-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>164.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>166.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>67.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>10927</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290059</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>290061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>329664</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438663</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022727</foodb_id>
  <chemspider_id>24980</chemspider_id>
  <pubchem_compound_id>26818</pubchem_compound_id>
  <drugbank_id/>
  <kegg_id>C05790</kegg_id>
  <chebi_id>29026</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Urobilinogen</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Watson, C. J.; Lightner, D. A.; Moscowitz, A.; Davis, E.; Petryka, Z. J.; Weimer, M.  A natural crystalline urobilinogen composed of d- and l-components of differing molecular weight.    Proceedings of the National Academy of Sciences of the United States of America  (1968),  61(1),  223-8</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:48 UTC</creation_date>
  <update_date>2020-03-13 16:29:21 UTC</update_date>
  <accession>BMDB0001900</accession>
  <secondary_accessions>
    <accession>BMDB01900</accession>
  </secondary_accessions>
  <name>Ribonolactone</name>
  <description/>
  <synonyms>
    <synonym>D-(+)-Ribonic acid gamma-lactone</synonym>
    <synonym>D-Ribonic acid-1,4-lactone</synonym>
    <synonym>D-Ribono-gamma-lactone</synonym>
    <synonym>D-Ribonolactone</synonym>
    <synonym>D-Ribopentono-1,4-lactone</synonym>
    <synonym>Ribono-gamma-lactone</synonym>
    <synonym>D-(+)-Ribonate g-lactone</synonym>
    <synonym>D-(+)-Ribonate gamma-lactone</synonym>
    <synonym>D-(+)-Ribonate γ-lactone</synonym>
    <synonym>D-(+)-Ribonic acid g-lactone</synonym>
    <synonym>D-(+)-Ribonic acid γ-lactone</synonym>
    <synonym>D-Ribonate-1,4-lactone</synonym>
    <synonym>D-Ribono-g-lactone</synonym>
    <synonym>D-Ribono-γ-lactone</synonym>
    <synonym>Ribono-g-lactone</synonym>
    <synonym>Ribono-γ-lactone</synonym>
    <synonym>D(+)-Ribonic acid gamma-lactone</synonym>
    <synonym>D-(+)-Ribonone-1.4-lactone</synonym>
    <synonym>D-Ribono-1,4-lactone</synonym>
    <synonym>delta-(+)-Ribonic acid g-lactone</synonym>
    <synonym>delta-(+)-Ribonic acid gamma-lactone</synonym>
    <synonym>delta-(+)-Ribonone-1.4-lactone</synonym>
    <synonym>delta-Ribono-1,4-lactone</synonym>
    <synonym>delta-Ribono-gamma-lactone</synonym>
    <synonym>delta-Ribonolactone</synonym>
    <synonym>delta-Ribopentono-1,4-lactone</synonym>
    <synonym>Deoxyribonolactone</synonym>
    <synonym>gamma-Lactone OF ribonate</synonym>
    <synonym>gamma-Lactone OF ribonic acid</synonym>
    <synonym>gamma-Lactone-ribonate</synonym>
    <synonym>gamma-Lactone-ribonic acid</synonym>
    <synonym>Ribonolactone</synonym>
  </synonyms>
  <chemical_formula>C5H8O5</chemical_formula>
  <average_molecular_weight>148.114</average_molecular_weight>
  <monisotopic_moleculate_weight>148.037173366</monisotopic_moleculate_weight>
  <iupac_name>(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one</iupac_name>
  <traditional_iupac>D-ribosone</traditional_iupac>
  <cas_registry_number>5336-08-3</cas_registry_number>
  <smiles>OC[C@H]1OC(=O)[C@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3-,4-/m1/s1</inchi>
  <inchikey>CUOKHACJLGPRHD-BXXZVTAOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Pentoses</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Gamma butyrolactones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Gamma butyrolactone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Lactone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>butan-4-olide</external_descriptor>
      <external_descriptor>ribonolactone</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>83 - 85 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>148.114</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>148.037173366</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC[C@H]1OC(=O)[C@H](O)[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C5H8O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3-,4-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CUOKHACJLGPRHD-BXXZVTAOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>86.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>28.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>12.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1355</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31883</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305564</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305565</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348997</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>348999</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022728</foodb_id>
  <chemspider_id>99702</chemspider_id>
  <pubchem_compound_id>111064</pubchem_compound_id>
  <drugbank_id/>
  <kegg_id>C02674</kegg_id>
  <chebi_id>74168</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD-13413</meta_cyc_id>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6380</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:49 UTC</creation_date>
  <update_date>2020-04-16 17:54:20 UTC</update_date>
  <accession>BMDB0001901</accession>
  <secondary_accessions>
    <accession>BMDB01901</accession>
  </secondary_accessions>
  <name>Aminocaproic acid</name>
  <description/>
  <synonyms>
    <synonym>6-Aminocaproic acid</synonym>
    <synonym>Acide aminocaproque</synonym>
    <synonym>Acido aminocaproico</synonym>
    <synonym>Acidum aminocaproicum</synonym>
    <synonym>Ahx</synonym>
    <synonym>Amicar</synonym>
    <synonym>Amikar</synonym>
    <synonym>AMINOCAPROIC</synonym>
    <synonym>Aminohexanoic acid</synonym>
    <synonym>Capralense</synonym>
    <synonym>Capramol</synonym>
    <synonym>Caproamin</synonym>
    <synonym>Caprocid</synonym>
    <synonym>Caprolisin</synonym>
    <synonym>EACA</synonym>
    <synonym>Epsamon</synonym>
    <synonym>Epsicaprom</synonym>
    <synonym>Epsicapron</synonym>
    <synonym>Epsikapron</synonym>
    <synonym>Epsilcapramin</synonym>
    <synonym>Epsilcapramine</synonym>
    <synonym>Epsilon S</synonym>
    <synonym>epsilon-Ahx</synonym>
    <synonym>epsilon-Amino-N-hexanoic acid</synonym>
    <synonym>epsilon-Aminocaproic acid</synonym>
    <synonym>epsilon-Aminohexanoic acid</synonym>
    <synonym>epsilon-Leucine</synonym>
    <synonym>epsilon-Norleucine</synonym>
    <synonym>Omega-aminocaproic acid</synonym>
    <synonym>Omega-aminohexanoic acid</synonym>
    <synonym>Respramin</synonym>
    <synonym>Z</synonym>
    <synonym>6-Aminohexanoic acid</synonym>
    <synonym>6-Aminocaproate</synonym>
    <synonym>Aminohexanoate</synonym>
    <synonym>epsilon-Amino-N-hexanoate</synonym>
    <synonym>epsilon-Aminocaproate</synonym>
    <synonym>epsilon-Aminohexanoate</synonym>
    <synonym>Omega-aminocaproate</synonym>
    <synonym>Omega-aminohexanoate</synonym>
    <synonym>6-Aminohexanoate</synonym>
    <synonym>Aminocaproate</synonym>
    <synonym>6-Amino-hexanoate</synonym>
    <synonym>6-Amino-hexanoic acid</synonym>
    <synonym>6-Amino-N-hexanoate</synonym>
    <synonym>6-Amino-N-hexanoic acid</synonym>
    <synonym>Acepramin</synonym>
    <synonym>Acepramine</synonym>
    <synonym>Acikaprin</synonym>
    <synonym>Afibrin</synonym>
    <synonym>Aminokapron</synonym>
    <synonym>Atsemin</synonym>
    <synonym>Caplamin</synonym>
    <synonym>Capracid</synonym>
    <synonym>Capranol</synonym>
    <synonym>e-Amino-N-hexanoate</synonym>
    <synonym>e-Amino-N-hexanoic acid</synonym>
    <synonym>e-Aminocaproate</synonym>
    <synonym>e-Aminocaproic acid</synonym>
    <synonym>e-Aminocaproic acid usp</synonym>
    <synonym>e-Aminohexanoate</synonym>
    <synonym>e-Aminohexanoic acid</synonym>
    <synonym>e-Leucine</synonym>
    <synonym>e-Norleucine</synonym>
    <synonym>Epsillon-aminocaproate</synonym>
    <synonym>Epsillon-aminocaproic acid</synonym>
    <synonym>Epsillon-aminocaproic acid' epsilcapramin</synonym>
    <synonym>epsilon-Aminocaproic acid usp</synonym>
    <synonym>epsilon-S</synonym>
    <synonym>H-6-Ahx-OH</synonym>
    <synonym>H-EAhx-OH</synonym>
    <synonym>H-epsilon-Acp-OH</synonym>
    <synonym>Hemocaprol</synonym>
    <synonym>Hemopar</synonym>
    <synonym>Hepin</synonym>
    <synonym>Ipsilon</synonym>
    <synonym>W-Aminocaproate</synonym>
    <synonym>W-Aminocaproic acid</synonym>
    <synonym>W-Aminohexanoate</synonym>
    <synonym>W-Aminohexanoic acid</synonym>
    <synonym>Pharmachemie brand OF aminocaproic acid</synonym>
    <synonym>Delagrange brand OF aminocaproic acid</synonym>
    <synonym>Hexalense</synonym>
    <synonym>epsilon Aminocaproic acid</synonym>
    <synonym>6 Aminocaproic acid</synonym>
    <synonym>Leurquin brand OF aminocaproic acid</synonym>
    <synonym>Rottapharm brand OF aminocaproic acid</synonym>
    <synonym>6 Aminohexanoic acid</synonym>
    <synonym>Caprolest</synonym>
    <synonym>Sanofi winthrop brand OF aminocaproic acid</synonym>
  </synonyms>
  <chemical_formula>C6H13NO2</chemical_formula>
  <average_molecular_weight>131.1729</average_molecular_weight>
  <monisotopic_moleculate_weight>131.094628665</monisotopic_moleculate_weight>
  <iupac_name>6-aminohexanoic acid</iupac_name>
  <traditional_iupac>aminocaproic acid</traditional_iupac>
  <cas_registry_number>60-32-2</cas_registry_number>
  <smiles>NCCCCCC(O)=O</smiles>
  <inchi>InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)</inchi>
  <inchikey>SLXKOJJOQWFEFD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Medium-chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Straight chain fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Straight chain fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>Amino fatty acids</external_descriptor>
      <external_descriptor>epsilon-amino acid</external_descriptor>
      <external_descriptor>omega-amino fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>205 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>505.0 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.95</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.46</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.73</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6-aminohexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>131.1729</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>131.094628665</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H13NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H13NO2/c7-5-3-1-2-4-6(8)9/h1-5,7H2,(H,8,9)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SLXKOJJOQWFEFD-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>34.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>790</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30242</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30919</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31372</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5585</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5586</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5587</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5589</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5590</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5591</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5592</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5593</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5596</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277801</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437163</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437164</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437165</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437166</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437167</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022729</foodb_id>
  <chemspider_id>548</chemspider_id>
  <pubchem_compound_id>564</pubchem_compound_id>
  <drugbank_id>DB00513</drugbank_id>
  <kegg_id>C02378</kegg_id>
  <chebi_id>16586</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CPD-884</meta_cyc_id>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Aminocaproic_acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:50 UTC</creation_date>
  <update_date>2020-03-13 16:29:22 UTC</update_date>
  <accession>BMDB0001902</accession>
  <secondary_accessions>
    <accession>BMDB01902</accession>
  </secondary_accessions>
  <name>Pteroyltriglutamic acid</name>
  <description/>
  <synonyms>
    <synonym>Pteroyltriglutamate</synonym>
    <synonym>N-[N-(N-Pteroyl-L-gamma-glutamyl)-L-gamma-glutamyl]-glutamic acid</synonym>
    <synonym>Folic acid diglutamate</synonym>
    <synonym>N-[4-[[(2-Amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-gamma-glutamyl-L-gamma-glutamyl-L-glutamic acid</synonym>
    <synonym>N-[N-[N-[4-[[(2-Amino-1,4-dihydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-.gamma.-glutamyl]-L-.gamma.-glutamyl]- L-glutamic acid</synonym>
    <synonym>Pteropterin</synonym>
    <synonym>Pteroyl-gamma-triglutamic acid</synonym>
    <synonym>Pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid</synonym>
    <synonym>Pteroyltri-gamma-L-glutamic acid</synonym>
    <synonym>Teropterin</synonym>
    <synonym>Pteropterin, sodium salt</synonym>
    <synonym>Pteroyl-gamma-glutamyl-gamma-glutamylglutamic acid</synonym>
    <synonym>2-{[4-carboxy-4-({4-carboxy-1-hydroxy-4-[(4-{[(4-hydroxy-2-imino-1,2-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]butylidene}amino)-1-hydroxybutylidene]amino}pentanedioate</synonym>
    <synonym>Pteroyltriglutamic acid</synonym>
  </synonyms>
  <chemical_formula>C29H33N9O12</chemical_formula>
  <average_molecular_weight>699.6254</average_molecular_weight>
  <monisotopic_moleculate_weight>699.224867565</monisotopic_moleculate_weight>
  <iupac_name>2-(4-{4-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid</iupac_name>
  <traditional_iupac>2-(4-{4-[(4-{[(2-amino-4-oxo-1H-pteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid</traditional_iupac>
  <cas_registry_number>89-38-3</cas_registry_number>
  <smiles>NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)=CN=C2N1</smiles>
  <inchi>InChI=1S/C29H33N9O12/c30-29-37-23-22(25(44)38-29)33-15(12-32-23)11-31-14-3-1-13(2-4-14)24(43)36-18(28(49)50)6-9-20(40)34-16(26(45)46)5-8-19(39)35-17(27(47)48)7-10-21(41)42/h1-4,12,16-18,31H,5-11H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H3,30,32,37,38,44)</inchi>
  <inchikey>WOLQREOUPKZMEX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Oligopeptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminobenzamides</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Gamma-glutamyl amino acids</alternative_parent>
      <alternative_parent>Glutamic acid and derivatives</alternative_parent>
      <alternative_parent>Glutamine and derivatives</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hippuric acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalkylamines</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pterins and derivatives</alternative_parent>
      <alternative_parent>Pyrazines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tetracarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Alpha-oligopeptide</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminobenzamide</substituent>
      <substituent>Aminobenzoic acid or derivatives</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzamide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzoic acid or derivatives</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Gamma-glutamyl alpha-amino acid</substituent>
      <substituent>Glutamic acid or derivatives</substituent>
      <substituent>Glutamine or derivatives</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hippuric acid</substituent>
      <substituent>Hippuric acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylalkylamine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pteridine</substituent>
      <substituent>Pterin</substituent>
      <substituent>Pyrazine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tetracarboxylic acid or derivatives</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>0.1 mg/mL at 5 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.91</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>2.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(4-{4-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>699.6254</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>699.224867565</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)=CN=C2N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C29H33N9O12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C29H33N9O12/c30-29-37-23-22(25(44)38-29)33-15(12-32-23)11-31-14-3-1-13(2-4-14)24(43)36-18(28(49)50)6-9-20(40)34-16(26(45)46)5-8-19(39)35-17(27(47)48)7-10-21(41)42/h1-4,12,16-18,31H,5-11H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H3,30,32,37,38,44)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WOLQREOUPKZMEX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>341.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>167.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>67.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>12542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>293610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334114</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334116</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1792</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022730</foodb_id>
  <chemspider_id>6702</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>6968</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>554079</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6381</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:51 UTC</creation_date>
  <update_date>2020-04-16 20:40:49 UTC</update_date>
  <accession>BMDB0001903</accession>
  <secondary_accessions>
    <accession>BMDB01903</accession>
  </secondary_accessions>
  <name>Calcitriol</name>
  <description>Calcitriol, also known as 1a,25(OH)2D3 or calcitriol-nefro, belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. Thus, calcitriol is considered to be a secosteroid lipid molecule. Calcitriol is a drug which is used to treat vitamin d deficiency or insufficiency, refractory rickets (vitamin d resistant rickets), familial hypophosphatemia and hypoparathyroidism, and in the management of hypocalcemia and renal osteodystrophy in patients with chronic renal failure undergoing dialysis. also used in conjunction with calcium in the management and prevention of primary or corticosteroid-induced osteoporosis. Calcitriol exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Calcitriol is a potentially toxic compound.</description>
  <synonyms>
    <synonym>(1alpha,3beta,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol</synonym>
    <synonym>(1S,3R,5Z,7E)-9,10-Secocholesta-5,7,10-triene-1,3,25-triol</synonym>
    <synonym>(5Z,7E)-(1S,3R)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol</synonym>
    <synonym>1,25-DHCC</synonym>
    <synonym>1-alpha-25-Dihydroxyvitamin D3</synonym>
    <synonym>1alpha,25(OH)2D3</synonym>
    <synonym>1alpha,25-Dihydroxycholecalciferol</synonym>
    <synonym>1alpha,25-Dihydroxyvitamin D3</synonym>
    <synonym>5-{2-[1-(5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ylidene]-ethylidene}-4-methylene-cyclohexane-1,3-diol</synonym>
    <synonym>Calcijex</synonym>
    <synonym>Calcitriolum</synonym>
    <synonym>Decostriol</synonym>
    <synonym>Rocaltrol</synonym>
    <synonym>(1S,3R,5Z,7E)-9,10-Seco-5,7,10(19)-cholestatriene-1,3,25-triol</synonym>
    <synonym>(1a,3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol</synonym>
    <synonym>(1Α,3β,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol</synonym>
    <synonym>1-a-25-Dihydroxyvitamin D3</synonym>
    <synonym>1-Α-25-dihydroxyvitamin D3</synonym>
    <synonym>1a,25(OH)2D3</synonym>
    <synonym>1Α,25(OH)2D3</synonym>
    <synonym>1a,25-Dihydroxycholecalciferol</synonym>
    <synonym>1Α,25-dihydroxycholecalciferol</synonym>
    <synonym>1a,25-Dihydroxyvitamin D3</synonym>
    <synonym>1Α,25-dihydroxyvitamin D3</synonym>
    <synonym>(3b,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trienetriol</synonym>
    <synonym>1,25 Dihydroxycholecalciferol</synonym>
    <synonym>1,25-Dihydroxycholecalciferol</synonym>
    <synonym>1,25-Dihydroxyvitamin D</synonym>
    <synonym>1,25-Dihydroxyvitamin D3</synonym>
    <synonym>1-alpha,25-Dihydroxyvitamin D3</synonym>
    <synonym>1a,25-(OH)2D3</synonym>
    <synonym>25-Dihydroxycholecalciferol</synonym>
    <synonym>Dihydroxyvitamin D3</synonym>
    <synonym>Ro 21-5535</synonym>
    <synonym>Silkis</synonym>
    <synonym>Soltriol</synonym>
    <synonym>Topitriol</synonym>
    <synonym>Toptriol</synonym>
    <synonym>1 alpha, 25-Dihydroxy-20-epi-vitamin D3</synonym>
    <synonym>1 alpha,25-Dihydroxycholecalciferol</synonym>
    <synonym>1,25(OH)2-20EPi-D3</synonym>
    <synonym>Bocatriol</synonym>
    <synonym>Calcitriol alphapharm brand</synonym>
    <synonym>Calcitriol kyramed</synonym>
    <synonym>Calcitriol-nefro</synonym>
    <synonym>Hoffmann-la roche brand OF calcitriol</synonym>
    <synonym>KyraMed, calcitriol</synonym>
    <synonym>Tirocal</synonym>
    <synonym>alpha,25-Dihydroxyvitamin D3, 1</synonym>
    <synonym>1,25-Dihydroxy-20-epi-vitamin D3</synonym>
    <synonym>20 Epi 1alpha,25 dihydroxycholecaliferol</synonym>
    <synonym>Abbott brand OF calcitriol</synonym>
    <synonym>Calcitriol galderma brand</synonym>
    <synonym>Calcitriol jenapharm brand</synonym>
    <synonym>Calcitriol leo brand</synonym>
    <synonym>Cryopharma brand OF calcitriol</synonym>
    <synonym>Medice brand OF calcitriol</synonym>
    <synonym>Renatriol</synonym>
    <synonym>Roche brand OF calcitriol</synonym>
    <synonym>1 alpha,25 Dihydroxycholecalciferol</synonym>
    <synonym>1 alpha,25-Dihydroxyvitamin D3</synonym>
    <synonym>20-Epi-1alpha,25-dihydroxycholecaliferol</synonym>
    <synonym>Calcitriol gry brand</synonym>
    <synonym>Calcitriol kyramed brand</synonym>
    <synonym>Calcitriol medice brand</synonym>
    <synonym>Calcitriol nefro</synonym>
    <synonym>Calcitriol renacare brand</synonym>
    <synonym>Calcitriol roche brand</synonym>
    <synonym>D3, 1,25-Dihydroxyvitamin</synonym>
    <synonym>D3, 1,25-Dihydroxy-20-epi-vitamin</synonym>
    <synonym>Galderma brand OF calcitriol</synonym>
    <synonym>Hoffmann la roche brand OF calcitriol</synonym>
    <synonym>KyraMed brand OF calcitriol</synonym>
    <synonym>Leo brand OF calcitriol</synonym>
    <synonym>RenaCare brand OF calcitriol</synonym>
    <synonym>Sitriol</synonym>
    <synonym>1 alpha, 25 Dihydroxy 20 epi vitamin D3</synonym>
    <synonym>1 alpha,25 Dihydroxyvitamin D3</synonym>
    <synonym>1,25 Dihydroxyvitamin D3</synonym>
    <synonym>1,25 Dihydroxy 20 epi vitamin D3</synonym>
    <synonym>Alphapharm brand OF calcitriol</synonym>
    <synonym>Calcitriol abbott brand</synonym>
    <synonym>Calcitriol cryopharma brand</synonym>
    <synonym>CalcitriolNefro</synonym>
    <synonym>D3, 1 alpha,25-Dihydroxyvitamin</synonym>
    <synonym>Gry brand OF calcitriol</synonym>
    <synonym>Jenapharm brand OF calcitriol</synonym>
    <synonym>Osteotriol</synonym>
    <synonym>1a,25-Dihydroxyvitamin D3 / 1a,25-dihydroxycholecalciferol / calcitriol</synonym>
    <synonym>1Α,25-dihydroxyvitamin D3 / 1α,25-dihydroxycholecalciferol / calcitriol</synonym>
    <synonym>Calcitriol</synonym>
  </synonyms>
  <chemical_formula>C27H44O3</chemical_formula>
  <average_molecular_weight>416.6365</average_molecular_weight>
  <monisotopic_moleculate_weight>416.329045274</monisotopic_moleculate_weight>
  <iupac_name>(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol</iupac_name>
  <traditional_iupac>calcitriol</traditional_iupac>
  <cas_registry_number>32222-06-3</cas_registry_number>
  <smiles>C[C@H](CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C</smiles>
  <inchi>InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1</inchi>
  <inchikey>GMRQFYUYWCNGIN-NKMMMXOESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Vitamin D and derivatives</sub_class>
    <direct_parent>Vitamin D and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Triterpenoids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Triterpenoid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>D3 vitamins</external_descriptor>
      <external_descriptor>Steroid hormones</external_descriptor>
      <external_descriptor>Vitamin D3 and derivatives</external_descriptor>
      <external_descriptor>hydroxycalciol</external_descriptor>
      <external_descriptor>triol</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>113 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>4.35</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>416.6365</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>416.329045274</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@H](CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H44O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GMRQFYUYWCNGIN-NKMMMXOESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>126.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>51.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>81324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>81325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>81326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>142415</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.00001296 +/- 0.00000288</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Raw milk</comment>
      <references>
        <reference>
          <reference_text>Hollis BW, Roos BA, Draper HH, Lambert PW: Vitamin D and its metabolites in human and bovine milk. J Nutr. 1981 Jul;111(7):1240-8. doi: 10.1093/jn/111.7.1240.</reference_text>
          <pubmed_id>6788913</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB00136</drugbank_id>
  <foodb_id>FDB021822</foodb_id>
  <chemspider_id>4444108</chemspider_id>
  <kegg_id>C01673</kegg_id>
  <pubchem_compound_id>5280453</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>17823</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CALCITRIOL</meta_cyc_id>
  <bigg_id>2289241</bigg_id>
  <wikipedia_id>Calcitriol</wikipedia_id>
  <metlin_id>6382</metlin_id>
  <synthesis_reference>Chen, Yang-sheng; Zhai, Cui-yun; Ren, Li.  Synthesis of calcitriol.    Zhongguo Xinyao Zazhi  (2005),  14(1),  69-72.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Hollis BW, Roos BA, Draper HH, Lambert PW: Vitamin D and its metabolites in human and bovine milk. J Nutr. 1981 Jul;111(7):1240-8. doi: 10.1093/jn/111.7.1240.</reference_text>
      <pubmed_id>6788913</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP01912</protein_accession>
      <name>Vitamin D3 receptor</name>
      <uniprot_id>Q28037</uniprot_id>
      <gene_name>VDR</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:53 UTC</creation_date>
  <update_date>2020-04-16 20:37:38 UTC</update_date>
  <accession>BMDB0001904</accession>
  <secondary_accessions>
    <accession>BMDB01904</accession>
  </secondary_accessions>
  <name>3-Nitrotyrosine</name>
  <description/>
  <synonyms>
    <synonym>(2S)-2-Amino-3-(4-hydroxy-3-nitrophenyl)propanoic acid</synonym>
    <synonym>L-3-Nitrotyrosine</synonym>
    <synonym>META-nitro-tyrosine</synonym>
    <synonym>(2S)-2-Amino-3-(4-hydroxy-3-nitrophenyl)propanoate</synonym>
    <synonym>5-Nitrotyrosine</synonym>
    <synonym>m-Nitrotyrosine</synonym>
    <synonym>3-Mononitrotyrosine</synonym>
    <synonym>3-Nitrotyrosine, (L)-isomer</synonym>
    <synonym>Nitrotyrosine</synonym>
    <synonym>3-Nitrotyrosine, (DL)-isomer</synonym>
    <synonym>Nitro-tyrosine</synonym>
    <synonym>3-Nitrotyrosine</synonym>
  </synonyms>
  <chemical_formula>C9H10N2O5</chemical_formula>
  <average_molecular_weight>226.1861</average_molecular_weight>
  <monisotopic_moleculate_weight>226.05897144</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-amino-3-(4-hydroxy-3-nitrophenyl)propanoic acid</iupac_name>
  <traditional_iupac>nitrotyrosine</traditional_iupac>
  <cas_registry_number>3604-79-3</cas_registry_number>
  <smiles>N[C@@H](CC1=CC=C(O)C(=C1)[N+]([O-])=O)C(O)=O</smiles>
  <inchi>InChI=1S/C9H10N2O5/c10-6(9(13)14)3-5-1-2-8(12)7(4-5)11(15)16/h1-2,4,6,12H,3,10H2,(H,13,14)/t6-/m0/s1</inchi>
  <inchikey>FBTSQILOGYXGMD-LURJTMIESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Tyrosine and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>L-alpha-amino acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Nitroaromatic compounds</alternative_parent>
      <alternative_parent>Nitrobenzenes</alternative_parent>
      <alternative_parent>Nitrophenols</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic oxoazanium compounds</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylalanine and derivatives</alternative_parent>
      <alternative_parent>Phenylpropanoic acids</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Allyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>C-nitro compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>L-alpha-amino acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Nitroaromatic compound</substituent>
      <substituent>Nitrobenzene</substituent>
      <substituent>Nitrophenol</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitro compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxoazanium</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylalanine or derivatives</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Tyrosine or derivatives</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-nitrotyrosine</external_descriptor>
      <external_descriptor>L-tyrosine derivative</external_descriptor>
      <external_descriptor>non-proteinogenic L-alpha-amino acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>1.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-amino-3-(4-hydroxy-3-nitrophenyl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>226.1861</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>226.05897144</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>N[C@@H](CC1=CC=C(O)C(=C1)[N+]([O-])=O)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H10N2O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H10N2O5/c10-6(9(13)14)3-5-1-2-8(12)7(4-5)11(15)16/h1-2,4,6,12H,3,10H2,(H,13,14)/t6-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FBTSQILOGYXGMD-LURJTMIESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>126.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>53.42</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>20.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1793</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7998</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31373</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>257159</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>277097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440092</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB03867</drugbank_id>
  <foodb_id>FDB022731</foodb_id>
  <chemspider_id>58633</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>65124</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>44454</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Nitrotyrosine</wikipedia_id>
  <metlin_id>6383</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:54 UTC</creation_date>
  <update_date>2020-04-14 22:49:25 UTC</update_date>
  <accession>BMDB0001906</accession>
  <secondary_accessions>
    <accession>BMDB01906</accession>
  </secondary_accessions>
  <name>2-Aminoisobutyric acid</name>
  <description>2-Aminoisobutyric acid, also known as alpha-methylalanine or alpha-aminoisobutyrate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 2-Aminoisobutyric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 2-Aminoisobutyric acid exists in all living organisms, ranging from bacteria to humans.</description>
  <synonyms>
    <synonym>2,2-Dimethylglycine</synonym>
    <synonym>2-Amino-2-methylpropanoate</synonym>
    <synonym>2-Amino-2-methylpropionic acid</synonym>
    <synonym>2-Methylalanine</synonym>
    <synonym>2MA</synonym>
    <synonym>AIB</synonym>
    <synonym>alpha,alpha-Dimethylglycine</synonym>
    <synonym>alpha-Aminoisobutanoic acid</synonym>
    <synonym>alpha-Aminoisobutyric acid</synonym>
    <synonym>alpha-Methylalanine</synonym>
    <synonym>2-Amino-2-methylpropanoic acid</synonym>
    <synonym>2-Amino-2-methylpropionate</synonym>
    <synonym>a,a-Dimethylglycine</synonym>
    <synonym>Α,α-dimethylglycine</synonym>
    <synonym>a-Aminoisobutanoate</synonym>
    <synonym>a-Aminoisobutanoic acid</synonym>
    <synonym>alpha-Aminoisobutanoate</synonym>
    <synonym>Α-aminoisobutanoate</synonym>
    <synonym>Α-aminoisobutanoic acid</synonym>
    <synonym>a-Aminoisobutyrate</synonym>
    <synonym>a-Aminoisobutyric acid</synonym>
    <synonym>alpha-Aminoisobutyrate</synonym>
    <synonym>Α-aminoisobutyrate</synonym>
    <synonym>Α-aminoisobutyric acid</synonym>
    <synonym>a-Methylalanine</synonym>
    <synonym>Α-methylalanine</synonym>
    <synonym>2-Aminoisobutyrate</synonym>
    <synonym>2-Aminoisobutyric acid, 11C-labeled</synonym>
    <synonym>2-Aminoisobutyric acid, 14C-labeled</synonym>
    <synonym>2-Amino-isobutyrate</synonym>
    <synonym>2-Aminoisobutyric acid</synonym>
  </synonyms>
  <chemical_formula>C4H9NO2</chemical_formula>
  <average_molecular_weight>103.1198</average_molecular_weight>
  <monisotopic_moleculate_weight>103.063328537</monisotopic_moleculate_weight>
  <iupac_name>2-amino-2-methylpropanoic acid</iupac_name>
  <traditional_iupac>α-aminoisobutyric acid</traditional_iupac>
  <cas_registry_number>62-57-7</cas_registry_number>
  <smiles>CC(C)(N)C(O)=O</smiles>
  <inchi>InChI=1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7)</inchi>
  <inchikey>FUOOLUPWFVMBKG-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2,2-dialkylglycine</external_descriptor>
      <external_descriptor>Amino fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>335 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>181 mg/mL at 25 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.58</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-2-methylpropanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>103.1198</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>103.063328537</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)(N)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H9NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>FUOOLUPWFVMBKG-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>63.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>25.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>10.33</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>792</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6982</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30420</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1794</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5597</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5605</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5606</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251034</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251036</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>270977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437156</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437157</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>439123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440108</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445581</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445582</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>445583</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial whole milk with 3.25% fat</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
          <pubmed_id>29291809</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <drugbank_id>DB02952</drugbank_id>
  <foodb_id>FDB022732</foodb_id>
  <chemspider_id>5891</chemspider_id>
  <kegg_id>C03665</kegg_id>
  <pubchem_compound_id>6119</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>27971</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>2-Aminoisobutyric acid</wikipedia_id>
  <metlin_id>37</metlin_id>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14.</reference_text>
      <pubmed_id>29291809</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:55 UTC</creation_date>
  <update_date>2020-03-13 16:29:24 UTC</update_date>
  <accession>BMDB0001908</accession>
  <secondary_accessions>
    <accession>BMDB01908</accession>
  </secondary_accessions>
  <name>19-Hydroxy-PGE2</name>
  <description/>
  <synonyms>
    <synonym>19(R)-Hydroxy-pge2</synonym>
    <synonym>19(R)-Hydroxy-prostaglandin e2</synonym>
    <synonym>19R-19-Hydroxy pge-2</synonym>
    <synonym>9-oxo-11R,15S,19R-Trihydroxy-5Z,13E-prostadienoate</synonym>
    <synonym>9-oxo-11R,15S,19R-Trihydroxy-5Z,13E-prostadienoic acid</synonym>
    <synonym>Eganoprost</synonym>
    <synonym>19-Hydroxyprostaglandin e2</synonym>
    <synonym>19-Hydroxy-pge2</synonym>
  </synonyms>
  <chemical_formula>C20H32O6</chemical_formula>
  <average_molecular_weight>368.4645</average_molecular_weight>
  <monisotopic_moleculate_weight>368.219888756</monisotopic_moleculate_weight>
  <iupac_name>(5Z)-7-[(1R,2R,3R)-2-[(1E,3S,7R)-3,7-dihydroxyoct-1-en-1-yl]-3-hydroxy-5-oxocyclopentyl]hept-5-enoic acid</iupac_name>
  <traditional_iupac>19-hydroxy-PGE2</traditional_iupac>
  <cas_registry_number>55123-68-7</cas_registry_number>
  <smiles>C[C@@H](O)CCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H32O6/c1-14(21)7-6-8-15(22)11-12-17-16(18(23)13-19(17)24)9-4-2-3-5-10-20(25)26/h2,4,11-12,14-17,19,21-22,24H,3,5-10,13H2,1H3,(H,25,26)/b4-2-,12-11+/t14-,15+,16-,17-,19-/m1/s1</inchi>
  <inchikey>WTJYDBMHYPQFNJ-ZUVVJKHESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Prostaglandins and related compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclic ketones</alternative_parent>
      <alternative_parent>Cyclopentanols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclic ketone</substituent>
      <substituent>Cyclopentanol</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Prostaglandin skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Prostaglandins</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5Z)-7-[(1R,2R,3R)-2-[(1E,3S,7R)-3,7-dihydroxyoct-1-en-1-yl]-3-hydroxy-5-oxocyclopentyl]hept-5-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>368.4645</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>368.219888756</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](O)CCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H32O6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H32O6/c1-14(21)7-6-8-15(22)11-12-17-16(18(23)13-19(17)24)9-4-2-3-5-10-20(25)26/h2,4,11-12,14-17,19,21-22,24H,3,5-10,13H2,1H3,(H,25,26)/b4-2-,12-11+/t14-,15+,16-,17-,19-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WTJYDBMHYPQFNJ-ZUVVJKHESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>115.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>101.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>41.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25335</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369890</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322085</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322086</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022733</foodb_id>
  <chemspider_id>4446165</chemspider_id>
  <kegg_id/>
  <pubchem_compound_id>5283038</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:56 UTC</creation_date>
  <update_date>2020-03-13 16:29:24 UTC</update_date>
  <accession>BMDB0001913</accession>
  <secondary_accessions>
    <accession>BMDB01913</accession>
  </secondary_accessions>
  <name>Omeprazole</name>
  <description/>
  <synonyms>
    <synonym>Prilosec</synonym>
    <synonym>( -)-Omeprazole</synonym>
    <synonym>(-)-Omeprazole</synonym>
    <synonym>(S)-(-)-Omeprazole</synonym>
    <synonym>(S)-Omeprazole</synonym>
    <synonym>2,3,5-Trimethylpyridine/Omeprazole</synonym>
    <synonym>Antra</synonym>
    <synonym>Antra mups</synonym>
    <synonym>Audazol</synonym>
    <synonym>Aulcer</synonym>
    <synonym>Belmazol</synonym>
    <synonym>Ceprandal</synonym>
    <synonym>Danlox</synonym>
    <synonym>Demeprazol</synonym>
    <synonym>Desec</synonym>
    <synonym>Dizprazol</synonym>
    <synonym>Dudencer</synonym>
    <synonym>Elgam</synonym>
    <synonym>Emeproton</synonym>
    <synonym>Epirazole</synonym>
    <synonym>Erbolin</synonym>
    <synonym>Esomeprazole</synonym>
    <synonym>Esomperazole</synonym>
    <synonym>Exter</synonym>
    <synonym>Gasec</synonym>
    <synonym>Gastrimut</synonym>
    <synonym>Gastroloc</synonym>
    <synonym>Gibancer</synonym>
    <synonym>Indurgan</synonym>
    <synonym>Inhibitron</synonym>
    <synonym>Inhipump</synonym>
    <synonym>Lensor</synonym>
    <synonym>Logastric</synonym>
    <synonym>Lomac</synonym>
    <synonym>Losec</synonym>
    <synonym>Mepral</synonym>
    <synonym>Miol</synonym>
    <synonym>Miracid</synonym>
    <synonym>Mopral</synonym>
    <synonym>Morecon</synonym>
    <synonym>Nexiam</synonym>
    <synonym>Nexium</synonym>
    <synonym>Nexium IV</synonym>
    <synonym>Nilsec</synonym>
    <synonym>Nopramin</synonym>
    <synonym>Nuclosina</synonym>
    <synonym>Ocid</synonym>
    <synonym>Olexin</synonym>
    <synonym>Omapren</synonym>
    <synonym>Omebeta 20</synonym>
    <synonym>Omed</synonym>
    <synonym>Omegast</synonym>
    <synonym>OMEP</synonym>
    <synonym>Omepradex</synonym>
    <synonym>Omepral</synonym>
    <synonym>Omeprazol</synonym>
    <synonym>Omeprazole pellets</synonym>
    <synonym>Omeprazolum</synonym>
    <synonym>Omeprazon</synonym>
    <synonym>Omeprol</synonym>
    <synonym>Omesek</synonym>
    <synonym>Omez</synonym>
    <synonym>Omezol</synonym>
    <synonym>Omezolan</synonym>
    <synonym>Omid</synonym>
    <synonym>Omisec</synonym>
    <synonym>Omizac</synonym>
    <synonym>Ompanyt</synonym>
    <synonym>OMZ</synonym>
    <synonym>Ortanol</synonym>
    <synonym>Osiren</synonym>
    <synonym>Ozoken</synonym>
    <synonym>Paprazol</synonym>
    <synonym>Parizac</synonym>
    <synonym>Pepticum</synonym>
    <synonym>Pepticus</synonym>
    <synonym>Peptilcer</synonym>
    <synonym>Prazentol</synonym>
    <synonym>Prazidec</synonym>
    <synonym>Prazolit</synonym>
    <synonym>Prestwick_808</synonym>
    <synonym>Prilosec otc</synonym>
    <synonym>Procelac</synonym>
    <synonym>Proclor</synonym>
    <synonym>Prysma</synonym>
    <synonym>Ramezol</synonym>
    <synonym>Regulacid</synonym>
    <synonym>Result</synonym>
    <synonym>Sanamidol</synonym>
    <synonym>Secrepina</synonym>
    <synonym>Tedec ulceral</synonym>
    <synonym>Ulceral</synonym>
    <synonym>Ulcesep</synonym>
    <synonym>Ulcometion</synonym>
    <synonym>Ulcozol</synonym>
    <synonym>Ulcsep</synonym>
    <synonym>Ulsen</synonym>
    <synonym>Ultop</synonym>
    <synonym>Ulzol</synonym>
    <synonym>Victrix</synonym>
    <synonym>Zefxon</synonym>
    <synonym>Zegerid</synonym>
    <synonym>Zepral</synonym>
    <synonym>Zimor</synonym>
    <synonym>Zoltum</synonym>
    <synonym>Magnesium, omeprazole</synonym>
    <synonym>Omeprazole magnesium</synonym>
    <synonym>Omeprazole sodium</synonym>
    <synonym>Sodium, omeprazole</synonym>
  </synonyms>
  <chemical_formula>C17H19N3O3S</chemical_formula>
  <average_molecular_weight>345.416</average_molecular_weight>
  <monisotopic_moleculate_weight>345.114712179</monisotopic_moleculate_weight>
  <iupac_name>6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole</iupac_name>
  <traditional_iupac>omeprazole</traditional_iupac>
  <cas_registry_number>73590-58-6</cas_registry_number>
  <smiles>COC1=CC2=C(C=C1)N=C(N2)S(=O)CC1=NC=C(C)C(OC)=C1C</smiles>
  <inchi>InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)</inchi>
  <inchikey>SUBDBMMJDZJVOS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Benzimidazoles</class>
    <sub_class>Sulfinylbenzimidazoles</sub_class>
    <direct_parent>Sulfinylbenzimidazoles</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Methylpyridines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Sulfinyl compounds</alternative_parent>
      <alternative_parent>Sulfoxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Ether</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Methylpyridine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Sulfinyl compound</substituent>
      <substituent>Sulfinylbenzimidazole</substituent>
      <substituent>Sulfoxide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>aromatic ether</external_descriptor>
      <external_descriptor>benzimidazoles</external_descriptor>
      <external_descriptor>pyridines</external_descriptor>
      <external_descriptor>sulfoxide</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>156 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.5 mg/mL</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.23</value>
      <source>SANGSTER (1994)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.29</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>345.416</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>345.114712179</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC2=C(C=C1)N=C(N2)S(=O)CC1=NC=C(C)C(OC)=C1C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C17H19N3O3S</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SUBDBMMJDZJVOS-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>93.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>37.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1795</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>44361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>44362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>44363</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>143610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>143611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>143612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440588</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440907</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>440911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450644</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>452319</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB00338</drugbank_id>
  <foodb_id>FDB021863</foodb_id>
  <chemspider_id>4433</chemspider_id>
  <kegg_id>C07324</kegg_id>
  <pubchem_compound_id>4594</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>77260</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id>2299956</bigg_id>
  <wikipedia_id>Omeprazole</wikipedia_id>
  <metlin_id>1632</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00939</protein_accession>
      <name>Prothrombin</name>
      <uniprot_id>P00735</uniprot_id>
      <gene_name>F2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:57 UTC</creation_date>
  <update_date>2020-04-15 22:30:11 UTC</update_date>
  <accession>BMDB0001915</accession>
  <secondary_accessions>
    <accession>BMDB01915</accession>
  </secondary_accessions>
  <name>Alendronic acid</name>
  <description/>
  <synonyms>
    <synonym>(4-Amino-1-hydroxybutylidene)bisphosphonic acid</synonym>
    <synonym>Acide alendronique</synonym>
    <synonym>Acido alendronico</synonym>
    <synonym>Acidum alendronicum</synonym>
    <synonym>Alendronate</synonym>
    <synonym>(4-Amino-1-hydroxybutylidene)bisphosphonate</synonym>
    <synonym>Alendronate sodium</synonym>
    <synonym>Alendronate sodium hydrate</synonym>
    <synonym>Fosamax</synonym>
    <synonym>Sodium, alendronate</synonym>
    <synonym>4-Amino-1-hydroxybutylidene 1,1-biphosphonate</synonym>
    <synonym>Aminohydroxybutane bisphosphonate</synonym>
    <synonym>4 Amino 1 hydroxybutylidene 1,1 biphosphonate</synonym>
    <synonym>Alendronate monosodium salt, trihydrate</synonym>
    <synonym>Bisphosphonate, aminohydroxybutane</synonym>
  </synonyms>
  <chemical_formula>C4H13NO7P2</chemical_formula>
  <average_molecular_weight>249.096</average_molecular_weight>
  <monisotopic_moleculate_weight>249.016724799</monisotopic_moleculate_weight>
  <iupac_name>(4-amino-1-hydroxy-1-phosphonobutyl)phosphonic acid</iupac_name>
  <traditional_iupac>alendronate</traditional_iupac>
  <cas_registry_number>66376-36-1</cas_registry_number>
  <smiles>NCCCC(O)(P(O)(O)=O)P(O)(O)=O</smiles>
  <inchi>InChI=1S/C4H13NO7P2/c5-3-1-2-4(6,13(7,8)9)14(10,11)12/h6H,1-3,5H2,(H2,7,8,9)(H2,10,11,12)</inchi>
  <inchikey>OGSPWJRAVKPPFI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Organic phosphonic acids and derivatives</class>
    <sub_class>Bisphosphonates</sub_class>
    <direct_parent>Bisphosphonates</direct_parent>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic phosphonic acids</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organophosphorus compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Bisphosphonate</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organophosphonic acid</substituent>
      <substituent>Organophosphorus compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>1,1-bis(phosphonic acid)</external_descriptor>
      <external_descriptor>primary amino compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.34</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>0.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(4-amino-1-hydroxy-1-phosphonobutyl)phosphonic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>249.096</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>249.016724799</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCC(O)(P(O)(O)=O)P(O)(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H13NO7P2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H13NO7P2/c5-3-1-2-4(6,13(7,8)9)14(10,11)12/h6H,1-3,5H2,(H2,7,8,9)(H2,10,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OGSPWJRAVKPPFI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>161.31</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>19.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>7115</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251787</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251788</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>251789</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271728</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271729</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>271730</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB00630</drugbank_id>
  <foodb_id>FDB022734</foodb_id>
  <chemspider_id>2004</chemspider_id>
  <kegg_id>C07752</kegg_id>
  <pubchem_compound_id>2088</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>2567</chebi_id>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>ALENDRONATE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Alendronic_acid</wikipedia_id>
  <metlin_id>818</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:48:58 UTC</creation_date>
  <update_date>2020-04-15 22:31:51 UTC</update_date>
  <accession>BMDB0001917</accession>
  <secondary_accessions>
    <accession>BMDB01917</accession>
  </secondary_accessions>
  <name>Digoxin</name>
  <description/>
  <synonyms>
  </synonyms>
  <chemical_formula>C41H64O14</chemical_formula>
  <average_molecular_weight>780.9385</average_molecular_weight>
  <monisotopic_moleculate_weight>780.429606756</monisotopic_moleculate_weight>
  <iupac_name>4-[(1S,2S,5S,7R,10R,11S,15S,16R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one</iupac_name>
  <traditional_iupac>digitek</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H]C1(CC[C@]2(O)[C@]3([H])CC[C@]4([H])C[C@]([H])(CC[C@]4(C)[C@@]3([H])C[C@@]([H])(O)[C@]12C)O[C@@]1([H])C[C@]([H])(O)[C@]([H])(O[C@@]2([H])C[C@]([H])(O)[C@]([H])(O[C@@]3([H])C[C@]([H])(O)[C@]([H])(O)[C@@]([H])(C)O3)[C@@]([H])(C)O2)[C@@]([H])(C)O1)C1=CC(=O)OC1</smiles>
  <inchi>InChI=1S/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25?,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1</inchi>
  <inchikey>LTMHDMANZUZIPE-YUICGFAKSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Steroid lactones</sub_class>
    <direct_parent>Cardenolide glycosides and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>12-hydroxysteroids</alternative_parent>
      <alternative_parent>14-hydroxysteroids</alternative_parent>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Butenolides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Enoate esters</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactones</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Oligosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Steroidal glycosides</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>12-hydroxysteroid</substituent>
      <substituent>14-hydroxysteroid</substituent>
      <substituent>2-furanone</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Alpha,beta-unsaturated carboxylic ester</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Cardanolide-glycoside</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Dihydrofuran</substituent>
      <substituent>Enoate ester</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Lactone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Oligosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Steroidal glycoside</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-[(1S,2S,5S,7R,10R,11S,15S,16R)-5-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl]oxy}-11,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>780.9385</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>780.429606756</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H]C1(CC[C@]2(O)[C@]3([H])CC[C@]4([H])C[C@]([H])(CC[C@]4(C)[C@@]3([H])C[C@@]([H])(O)[C@]12C)O[C@@]1([H])C[C@]([H])(O)[C@]([H])(O[C@@]2([H])C[C@]([H])(O)[C@]([H])(O[C@@]3([H])C[C@]([H])(O)[C@]([H])(O)[C@@]([H])(C)O3)[C@@]([H])(C)O2)[C@@]([H])(C)O1)C1=CC(=O)OC1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C41H64O14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25?,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LTMHDMANZUZIPE-YUICGFAKSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>203.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>193.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>84.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1797</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1286938</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1286939</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1286940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1401730</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1401731</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1401732</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id/>
  <drugbank_id/>
  <foodb_id/>
  <pubchem_compound_id>30322</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Digoxin</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:00 UTC</creation_date>
  <update_date>2020-04-16 17:54:21 UTC</update_date>
  <accession>BMDB0001923</accession>
  <secondary_accessions>
    <accession>BMDB01923</accession>
  </secondary_accessions>
  <name>Naproxen</name>
  <description/>
  <synonyms>
    <synonym>(+)-(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid</synonym>
    <synonym>(+)-(S)-Naproxen</synonym>
    <synonym>(+)-2-(6-Methoxy-2-naphthyl)propionic acid</synonym>
    <synonym>(+)-2-(Methoxy-2-naphthyl)-propionic acid</synonym>
    <synonym>(+)-2-(Methoxy-2-naphthyl)-propionsaeure</synonym>
    <synonym>(+)-Naproxen</synonym>
    <synonym>(S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid</synonym>
    <synonym>(S)-(+)-Naproxen</synonym>
    <synonym>(S)-2-(6-Methoxy-2-naphthyl)propanoic acid</synonym>
    <synonym>(S)-2-(6-Methoxy-2-naphthyl)propionic acid</synonym>
    <synonym>(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid</synonym>
    <synonym>(S)-Naproxen</synonym>
    <synonym>Naproxene</synonym>
    <synonym>Naproxeno</synonym>
    <synonym>Naproxenum</synonym>
    <synonym>Naprosyn</synonym>
    <synonym>(+)-(S)-6-Methoxy-a-methyl-2-naphthaleneacetate</synonym>
    <synonym>(+)-(S)-6-Methoxy-a-methyl-2-naphthaleneacetic acid</synonym>
    <synonym>(+)-(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetate</synonym>
    <synonym>(+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetate</synonym>
    <synonym>(+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acid</synonym>
    <synonym>(+)-2-(6-Methoxy-2-naphthyl)propionate</synonym>
    <synonym>(+)-2-(Methoxy-2-naphthyl)-propionate</synonym>
    <synonym>(S)-(+)-2-(6-Methoxy-2-naphthyl)propionate</synonym>
    <synonym>(S)-2-(6-Methoxy-2-naphthyl)propanoate</synonym>
    <synonym>(S)-2-(6-Methoxy-2-naphthyl)propionate</synonym>
    <synonym>(S)-6-Methoxy-a-methyl-2-naphthaleneacetate</synonym>
    <synonym>(S)-6-Methoxy-a-methyl-2-naphthaleneacetic acid</synonym>
    <synonym>(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetate</synonym>
    <synonym>(S)-6-Methoxy-α-methyl-2-naphthaleneacetate</synonym>
    <synonym>(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acid</synonym>
    <synonym>2-(6-Methoxy-2-naphthyl)propionic acid</synonym>
    <synonym>Acusprain</synonym>
    <synonym>Anexopen</synonym>
    <synonym>Apronax</synonym>
    <synonym>Artagen</synonym>
    <synonym>Arthrisil</synonym>
    <synonym>Artrixen</synonym>
    <synonym>Artroxen</synonym>
    <synonym>Atiflan</synonym>
    <synonym>Axer</synonym>
    <synonym>Bipronyl</synonym>
    <synonym>Calosen</synonym>
    <synonym>Clinosyn</synonym>
    <synonym>Congex</synonym>
    <synonym>D-Naproxen</synonym>
    <synonym>Danaprox</synonym>
    <synonym>Daprox</synonym>
    <synonym>Diocodal</synonym>
    <synonym>DL Naproxen</synonym>
    <synonym>DL-Naproxen</synonym>
    <synonym>Duk</synonym>
    <synonym>Dysmenalgit</synonym>
    <synonym>Dysmenalgit N</synonym>
    <synonym>Ec-naprosyn</synonym>
    <synonym>Equiproxen</synonym>
    <synonym>Flexipen</synonym>
    <synonym>Floginax</synonym>
    <synonym>Fuxen</synonym>
    <synonym>Genoxen</synonym>
    <synonym>Lefaine</synonym>
    <synonym>Leniartil</synonym>
    <synonym>Nafasol</synonym>
    <synonym>Naixan</synonym>
    <synonym>Nalyxan</synonym>
    <synonym>Napflam</synonym>
    <synonym>Napmel</synonym>
    <synonym>Naposin</synonym>
    <synonym>Naprosyne</synonym>
    <synonym>Naproxen sodium</synonym>
    <synonym>Novonaprox</synonym>
    <synonym>Nycopren</synonym>
    <synonym>Opipramol</synonym>
    <synonym>Anaprox</synonym>
    <synonym>Methoxypropiocin</synonym>
    <synonym>Naprosin</synonym>
    <synonym>Proxen</synonym>
    <synonym>Aleve</synonym>
    <synonym>Sodium, naproxen</synonym>
    <synonym>MNPA</synonym>
    <synonym>Synflex</synonym>
    <synonym>Naproxenate, sodium</synonym>
    <synonym>Sodium naproxenate</synonym>
  </synonyms>
  <chemical_formula>C14H14O3</chemical_formula>
  <average_molecular_weight>230.2592</average_molecular_weight>
  <monisotopic_moleculate_weight>230.094294314</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid</iupac_name>
  <traditional_iupac>naproxen</traditional_iupac>
  <cas_registry_number>22204-53-1</cas_registry_number>
  <smiles>COC1=CC2=C(C=C1)C=C(C=C2)[C@H](C)C(O)=O</smiles>
  <inchi>InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1</inchi>
  <inchikey>CMWTZPSULFXXJA-VIFPVBQESA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Naphthalenes</class>
    <sub_class/>
    <direct_parent>Naphthalenes</direct_parent>
    <alternative_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Naphthalene</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>methoxynaphthalene</external_descriptor>
      <external_descriptor>monocarboxylic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>153 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.0159 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.18</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.29</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>230.2592</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>230.094294314</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC2=C(C=C1)C=C(C=C2)[C@H](C)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H14O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CMWTZPSULFXXJA-VIFPVBQESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>46.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>64.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>24.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1802</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1851</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5612</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5614</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5616</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438207</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438208</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438209</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438210</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438211</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5617</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5618</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>447250</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278490</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>278492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258552</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>258554</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB00788</drugbank_id>
  <foodb_id>FDB022741</foodb_id>
  <chemspider_id>137720</chemspider_id>
  <pubchem_compound_id>156391</pubchem_compound_id>
  <pdbe_id/>
  <kegg_id>C01517</kegg_id>
  <chebi_id>7476</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Naproxen</wikipedia_id>
  <metlin_id>1461</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:01 UTC</creation_date>
  <update_date>2020-03-13 16:29:27 UTC</update_date>
  <accession>BMDB0001931</accession>
  <secondary_accessions>
    <accession>BMDB01931</accession>
  </secondary_accessions>
  <name>Gamma-CEHC</name>
  <description/>
  <synonyms>
    <synonym>g-CEHC</synonym>
    <synonym>Γ-cehc</synonym>
    <synonym>3-(6-Hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoate</synonym>
    <synonym>S-LLU-alpha</synonym>
    <synonym>LLU-alpha</synonym>
    <synonym>3-(2,7,8-Trimethyl-3,4-dihydro-2H-chromen-2-yl)propanoate</synonym>
    <synonym>(±)-llu-α</synonym>
    <synonym>(±)-llu-alpha</synonym>
    <synonym>2,7,8-Trimethyl-2-(β-carboxyethyl)-6-hydroxychroman</synonym>
    <synonym>2,7,8-Trimethyl-2-(beta-carboxyethyl)-6-hydroxychroman</synonym>
    <synonym>γ-Carboxyethyl hydroxychroman</synonym>
    <synonym>γ-Carboxyethyl-hydroxychroman</synonym>
    <synonym>gamma-Carboxyethyl hydroxychroman</synonym>
    <synonym>gamma-Carboxyethyl-hydroxychroman</synonym>
    <synonym>3'-Carboxychromanol</synonym>
    <synonym>gamma-CEHC</synonym>
  </synonyms>
  <chemical_formula>C15H20O4</chemical_formula>
  <average_molecular_weight>264.321</average_molecular_weight>
  <monisotopic_moleculate_weight>264.136159124</monisotopic_moleculate_weight>
  <iupac_name>3-(6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoic acid</iupac_name>
  <traditional_iupac>3-(6-hydroxy-2,7,8-trimethyl-3,4-dihydro-1-benzopyran-2-yl)propanoic acid</traditional_iupac>
  <cas_registry_number>178167-75-4</cas_registry_number>
  <smiles>CC1=C(O)C=C2CCC(C)(CCC(O)=O)OC2=C1C</smiles>
  <inchi>InChI=1S/C15H20O4/c1-9-10(2)14-11(8-12(9)16)4-6-15(3,19-14)7-5-13(17)18/h8,16H,4-7H2,1-3H3,(H,17,18)</inchi>
  <inchikey>VMJQLPNCUPGMNQ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Benzopyrans</class>
    <sub_class>1-benzopyrans</sub_class>
    <direct_parent>1-benzopyrans</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-benzopyran</substituent>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.16</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-(6-hydroxy-2,7,8-trimethyl-3,4-dihydro-2H-1-benzopyran-2-yl)propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>264.321</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>264.136159124</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(O)C=C2CCC(C)(CCC(O)=O)OC2=C1C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H20O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H20O4/c1-9-10(2)14-11(8-12(9)16)4-6-15(3,19-14)7-5-13(17)18/h8,16H,4-7H2,1-3H3,(H,17,18)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VMJQLPNCUPGMNQ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>66.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1218360</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022748</foodb_id>
  <chemspider_id>117455</chemspider_id>
  <pubchem_compound_id>15887183</pubchem_compound_id>
  <kegg_id/>
  <chebi_id/>
  <pdbe_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <wikipedia_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:02 UTC</creation_date>
  <update_date>2020-04-15 22:15:35 UTC</update_date>
  <accession>BMDB0001952</accession>
  <secondary_accessions>
    <accession>BMDB01952</accession>
  </secondary_accessions>
  <name>Hexacarboxylporphyrin III</name>
  <description/>
  <synonyms>
    <synonym>Hexacarboxylic acid porphyrin III</synonym>
    <synonym>Hexacarboxyporphyrin III</synonym>
    <synonym>3-[9,14,20-Tris(2-carboxyethyl)-10,19-bis(carboxymethyl)-5,15-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C38H38N4O12</chemical_formula>
  <average_molecular_weight>742.7279</average_molecular_weight>
  <monisotopic_moleculate_weight>742.2486227</monisotopic_moleculate_weight>
  <iupac_name>3-[9,14,20-tris(2-carboxyethyl)-10,19-bis(carboxymethyl)-5,15-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>hexacarboxylporphyrin III</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4CC(O)=O)/C(CC(O)=O)=C3CCC(O)=O</smiles>
  <inchi>InChI=1S/C38H38N4O12/c1-17-19(3-7-33(43)44)27-15-30-22(6-10-36(49)50)23(11-37(51)52)31(42-30)14-26-18(2)20(4-8-34(45)46)28(40-26)16-32-24(12-38(53)54)21(5-9-35(47)48)29(41-32)13-25(17)39-27/h13-16,39-40H,3-12H2,1-2H3,(H,43,44)(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)/b25-13-,26-14-,27-15-,28-16-,29-13-,30-15-,31-14-,32-16-</inchi>
  <inchikey>NTILFDFSYFWZAA-CYRUMZLOSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
    </substituents>
    <molecular_framework name="" source="BMDB" kind=""/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[9,14,20-tris(2-carboxyethyl)-10,19-bis(carboxymethyl)-5,15-dimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>742.7279</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>742.2486227</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4CC(O)=O)/C(CC(O)=O)=C3CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C38H38N4O12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C38H38N4O12/c1-17-19(3-7-33(43)44)27-15-30-22(6-10-36(49)50)23(11-37(51)52)31(42-30)14-26-18(2)20(4-8-34(45)46)28(40-26)16-32-24(12-38(53)54)21(5-9-35(47)48)29(41-32)13-25(17)39-27/h13-16,39-40H,3-12H2,1-2H3,(H,43,44)(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)/b25-13-,26-14-,27-15-,28-16-,29-13-,30-15-,31-14-,32-16-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NTILFDFSYFWZAA-CYRUMZLOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>281.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>188.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>79.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311873</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>311874</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356980</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356981</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>356982</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <pubchem_compound_id/>
  <drugbank_id/>
  <foodb_id>FDB022760</foodb_id>
  <chemspider_id>13628279</chemspider_id>
  <pdbe_id/>
  <chebi_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6396</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:03 UTC</creation_date>
  <update_date>2020-04-14 22:49:26 UTC</update_date>
  <accession>BMDB0001954</accession>
  <secondary_accessions>
    <accession>BMDB01954</accession>
  </secondary_accessions>
  <name>3-Hydroxyoctanoic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Hydroxy-octanoic acid</synonym>
    <synonym>3-Hydroxycaprylic acid</synonym>
    <synonym>3-OH Octanoic acid</synonym>
    <synonym>3-OH-Caprylic acid</synonym>
    <synonym>3HO</synonym>
    <synonym>beta-Hydroxycaprylic acid</synonym>
    <synonym>beta-Hydroxyoctanoic acid</synonym>
    <synonym>beta-OH-Caprylic acid</synonym>
    <synonym>beta-OH-Octanoic acid</synonym>
    <synonym>3-Hydroxy-octanoate</synonym>
    <synonym>3-Hydroxycaprylate</synonym>
    <synonym>3-OH Octanoate</synonym>
    <synonym>3-OH-Caprylate</synonym>
    <synonym>b-Hydroxycaprylate</synonym>
    <synonym>b-Hydroxycaprylic acid</synonym>
    <synonym>beta-Hydroxycaprylate</synonym>
    <synonym>Β-hydroxycaprylate</synonym>
    <synonym>Β-hydroxycaprylic acid</synonym>
    <synonym>b-Hydroxyoctanoate</synonym>
    <synonym>b-Hydroxyoctanoic acid</synonym>
    <synonym>beta-Hydroxyoctanoate</synonym>
    <synonym>Β-hydroxyoctanoate</synonym>
    <synonym>Β-hydroxyoctanoic acid</synonym>
    <synonym>b-OH-Caprylate</synonym>
    <synonym>b-OH-Caprylic acid</synonym>
    <synonym>beta-OH-Caprylate</synonym>
    <synonym>Β-OH-caprylate</synonym>
    <synonym>Β-OH-caprylic acid</synonym>
    <synonym>b-OH-Octanoate</synonym>
    <synonym>b-OH-Octanoic acid</synonym>
    <synonym>beta-OH-Octanoate</synonym>
    <synonym>Β-OH-octanoate</synonym>
    <synonym>Β-OH-octanoic acid</synonym>
    <synonym>3-Hydroxyoctanoate</synonym>
    <synonym>(+/-)-3-hydroxyoctanoate</synonym>
    <synonym>(+/-)-3-hydroxyoctanoic acid</synonym>
    <synonym>3-Hydroxy caprylic acid</synonym>
    <synonym>3-Hydroxyoctanoic acid homopolymer</synonym>
    <synonym>8:0(3-OH)</synonym>
    <synonym>Poly-3-hydroxyoctanoate</synonym>
    <synonym>Poly-3-hydroxyoctanoic acid</synonym>
    <synonym>3-Hydroxyoctanoic acid, (S)-isomer</synonym>
    <synonym>3-Hydroxy caprylate</synonym>
    <synonym>3-Hydroxyoctanoic acid</synonym>
  </synonyms>
  <chemical_formula>C8H16O3</chemical_formula>
  <average_molecular_weight>160.2108</average_molecular_weight>
  <monisotopic_moleculate_weight>160.109944378</monisotopic_moleculate_weight>
  <iupac_name>3-hydroxyoctanoic acid</iupac_name>
  <traditional_iupac>(+/-)-3-hydroxyoctanoic acid</traditional_iupac>
  <cas_registry_number>14292-27-4</cas_registry_number>
  <smiles>CCCCCC(O)CC(O)=O</smiles>
  <inchi>InChI=1S/C8H16O3/c1-2-3-4-5-7(9)6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)</inchi>
  <inchikey>NDPLAKGOSZHTPH-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Hydroxy acids and derivatives</class>
    <sub_class>Medium-chain hydroxy acids and derivatives</sub_class>
    <direct_parent>Medium-chain hydroxy acids and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>3-hydroxy fatty acid</external_descriptor>
      <external_descriptor>3-hydroxy monocarboxylic acid</external_descriptor>
      <external_descriptor>Hydroxy fatty acids</external_descriptor>
      <external_descriptor>medium-chain fatty acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.44</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.47</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-2.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-hydroxyoctanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>160.2108</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>160.109944378</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCC(O)CC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H16O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H16O3/c1-2-3-4-5-7(9)6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NDPLAKGOSZHTPH-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>41.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>20345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>12379</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19049</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19050</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>19051</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id>24791</chemspider_id>
  <drugbank_id/>
  <foodb_id>FDB022761</foodb_id>
  <pubchem_compound_id>26613</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>37098</chebi_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>3-Hydroxyoctanoic acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference>Tahara, Satoshi; Suzuki, Yumiko; Mizutani, Junya. Fungal metabolism of a,b-unsaturated carboxylic acids. Part III. Fungal metabolism of trans-2-octenoic acid. Agricultural and Biological Chemistry (1977), 41(9), 1643-50.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:04 UTC</creation_date>
  <update_date>2020-03-13 16:29:28 UTC</update_date>
  <accession>BMDB0001955</accession>
  <secondary_accessions>
    <accession>BMDB01955</accession>
  </secondary_accessions>
  <name>3-Phenylbutyric acid</name>
  <description/>
  <synonyms>
    <synonym>3-Phenylbutyrate</synonym>
    <synonym>3-Phenylbutiric acid</synonym>
    <synonym>3-Phenylbutirate</synonym>
    <synonym>(RS)-3-Phenylbutanoate</synonym>
    <synonym>(RS)-3-Phenylbutanoic acid</synonym>
    <synonym>3-Phenylbutanoate</synonym>
    <synonym>3-Phenylbutanoic acid</synonym>
    <synonym>b-Methylbenzenepropanoate</synonym>
    <synonym>b-Methylbenzenepropanoic acid</synonym>
    <synonym>b-Methylhydrocinnamate</synonym>
    <synonym>b-Methylhydrocinnamic acid</synonym>
    <synonym>b-Phenyl-N-butyrate</synonym>
    <synonym>b-Phenyl-N-butyric acid</synonym>
    <synonym>b-Phenylbutyrate</synonym>
    <synonym>b-Phenylbutyric acid</synonym>
    <synonym>beta-Methylbenzenepropanoate</synonym>
    <synonym>beta-Methylbenzenepropanoic acid</synonym>
    <synonym>beta-Methylhydrocinnamate</synonym>
    <synonym>beta-Methylhydrocinnamic acid</synonym>
    <synonym>beta-Phenyl-N-butyrate</synonym>
    <synonym>beta-Phenyl-N-butyric acid</synonym>
    <synonym>beta-Phenylbutyrate</synonym>
    <synonym>beta-Phenylbutyric acid</synonym>
    <synonym>3-PB</synonym>
    <synonym>3-Phenylbutyric acid</synonym>
  </synonyms>
  <chemical_formula>C10H12O2</chemical_formula>
  <average_molecular_weight>164.2011</average_molecular_weight>
  <monisotopic_moleculate_weight>164.083729628</monisotopic_moleculate_weight>
  <iupac_name>3-phenylbutanoic acid</iupac_name>
  <traditional_iupac>β-phenylbutyric acid</traditional_iupac>
  <cas_registry_number>4593-90-2</cas_registry_number>
  <smiles>CC(CC(O)=O)C1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C10H12O2/c1-8(7-10(11)12)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,11,12)</inchi>
  <inchikey>ZZEWMYILWXCRHZ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Phenylpropanoic acids</class>
    <sub_class/>
    <direct_parent>Phenylpropanoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Benzene and substituted derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-phenylpropanoic-acid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>39 - 37 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.18</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.48</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-phenylbutanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>164.2011</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>164.083729628</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(CC(O)=O)C1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H12O2/c1-8(7-10(11)12)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZZEWMYILWXCRHZ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>46.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1763</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24060</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1908</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1909</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1910</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366383</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>366384</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <pubchem_compound_id>20724</pubchem_compound_id>
  <drugbank_id/>
  <foodb_id>FDB022762</foodb_id>
  <chemspider_id>19513</chemspider_id>
  <pdbe_id/>
  <chebi_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Sodium phenylbutyrate</wikipedia_id>
  <metlin_id>6399</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:06 UTC</creation_date>
  <update_date>2020-04-15 22:15:36 UTC</update_date>
  <accession>BMDB0001956</accession>
  <secondary_accessions>
    <accession>BMDB01956</accession>
  </secondary_accessions>
  <name>Heptacarboxylporphyrin III</name>
  <description/>
  <synonyms>
    <synonym>Heptacarboxylic acid prophyrin III</synonym>
    <synonym>Heptacarboxyporphyrin III</synonym>
    <synonym>3-[9,10,14,19-Tetrakis(2-carboxyethyl)-15,20-bis(carboxymethyl)-5-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C40H40N4O14</chemical_formula>
  <average_molecular_weight>800.764</average_molecular_weight>
  <monisotopic_moleculate_weight>800.254102008</monisotopic_moleculate_weight>
  <iupac_name>3-[9,10,14,19-tetrakis(2-carboxyethyl)-15,20-bis(carboxymethyl)-5-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[9,10,14,19-tetrakis(2-carboxyethyl)-15,20-bis(carboxymethyl)-5-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(CCC(O)=O)=C5CCC(O)=O)C(CCC(O)=O)=C4CC(O)=O)C(CCC(O)=O)=C3CC(O)=O)=C1CCC(O)=O</smiles>
  <inchi>InChI=1S/C40H40N4O14/c1-18-19(2-7-34(45)46)27-15-32-24(12-39(55)56)23(6-11-38(53)54)31(44-32)17-33-25(13-40(57)58)22(5-10-37(51)52)30(43-33)16-29-21(4-9-36(49)50)20(3-8-35(47)48)28(42-29)14-26(18)41-27/h14-17,41,43H,2-13H2,1H3,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)/b26-14-,27-15-,28-14-,29-16-,30-16-,31-17-,32-15-,33-17-</inchi>
  <inchikey>UXXBQPAQUFNNGY-FLBNTIIFSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Porphyrin</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>208 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.20</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.38</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>5.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[9,10,14,19-tetrakis(2-carboxyethyl)-15,20-bis(carboxymethyl)-5-methyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>800.764</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>800.254102008</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(CCC(O)=O)=C5CCC(O)=O)C(CCC(O)=O)=C4CC(O)=O)C(CCC(O)=O)=C3CC(O)=O)=C1CCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C40H40N4O14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C40H40N4O14/c1-18-19(2-7-34(45)46)27-15-32-24(12-39(55)56)23(6-11-38(53)54)31(44-32)17-33-25(13-40(57)58)22(5-10-37(51)52)30(43-33)16-29-21(4-9-36(49)50)20(3-8-35(47)48)28(42-29)14-26(18)41-27/h14-17,41,43H,2-13H2,1H3,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)/b26-14-,27-15-,28-14-,29-16-,30-16-,31-17-,32-15-,33-17-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UXXBQPAQUFNNGY-FLBNTIIFSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>318.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>199.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>84.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>313353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>358833</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022763</foodb_id>
  <chemspider_id/>
  <pubchem_compound_id/>
  <chebi_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6400</metlin_id>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:07 UTC</creation_date>
  <update_date>2020-03-13 16:29:29 UTC</update_date>
  <accession>BMDB0001957</accession>
  <secondary_accessions>
    <accession>BMDB01957</accession>
  </secondary_accessions>
  <name>Pentacarboxyl porphyrinogen III</name>
  <description/>
  <synonyms>
    <synonym>Pentacarboxylporphyrinogen III</synonym>
    <synonym>Pentacarboxyporphyrinogen III</synonym>
    <synonym>3-[10,14,19-Tris(2-carboxyethyl)-15-(carboxymethyl)-5,9,20-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3,5,9,11(23),12,14,16,18(21),19-decaen-4-yl]propanoate</synonym>
  </synonyms>
  <chemical_formula>C37H40N4O10</chemical_formula>
  <average_molecular_weight>700.7343</average_molecular_weight>
  <monisotopic_moleculate_weight>700.27444352</monisotopic_moleculate_weight>
  <iupac_name>3-[(12Z,17Z)-10,15,20-tris(2-carboxyethyl)-19-(carboxymethyl)-5,9,14-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),4,8,10,12,14,16(22),17,19-decaen-4-yl]propanoic acid</iupac_name>
  <traditional_iupac>3-[(12Z,17Z)-10,15,20-tris(2-carboxyethyl)-19-(carboxymethyl)-5,9,14-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),4,8,10,12,14,16(22),17,19-decaen-4-yl]propanoic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>CC1=C(CCC(O)=O)C2=NC1CC1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N=C(/C=C3\N\C(=C/2)C(CCC(O)=O)=C3CC(O)=O)C(CCC(O)=O)=C1C</smiles>
  <inchi>InChI=1S/C37H40N4O10/c1-17-20(4-8-33(42)43)28-14-27-19(3)22(6-10-35(46)47)30(40-27)16-32-24(12-37(50)51)23(7-11-36(48)49)31(41-32)15-29-21(5-9-34(44)45)18(2)26(39-29)13-25(17)38-28/h14-16,26,38,41H,4-13H2,1-3H3,(H,42,43)(H,44,45)(H,46,47)(H,48,49)(H,50,51)/b27-14-,31-15-,32-16-</inchi>
  <inchikey>QDDLLFZOMVJQEQ-XJTMSCLRSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Tetrapyrroles and derivatives</class>
    <sub_class>Porphyrins</sub_class>
    <direct_parent>Porphyrins</direct_parent>
    <alternative_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dipyrrins</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketimines</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pentacarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dipyrrin</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Ketimine</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pentacarboxylic acid or derivatives</substituent>
      <substituent>Porphyrin</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.32</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(12Z,17Z)-10,15,20-tris(2-carboxyethyl)-19-(carboxymethyl)-5,9,14-trimethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1,3(24),4,8,10,12,14,16(22),17,19-decaen-4-yl]propanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>700.7343</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>700.27444352</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=C(CCC(O)=O)C2=NC1CC1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N=C(/C=C3\N\C(=C/2)C(CCC(O)=O)=C3CC(O)=O)C(CCC(O)=O)=C1C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C37H40N4O10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C37H40N4O10/c1-17-20(4-8-33(42)43)28-14-27-19(3)22(6-10-35(46)47)30(40-27)16-32-24(12-37(50)51)23(7-11-36(48)49)31(41-32)15-29-21(5-9-34(44)45)18(2)26(39-29)13-25(17)38-28/h14-16,26,38,41H,4-13H2,1-3H3,(H,42,43)(H,44,45)(H,46,47)(H,48,49)(H,50,51)/b27-14-,31-15-,32-16-</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QDDLLFZOMVJQEQ-XJTMSCLRSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>239.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>189.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>77.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>70889</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294082</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294083</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294084</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334708</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334709</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>334710</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <drugbank_id/>
  <foodb_id>FDB022764</foodb_id>
  <chemspider_id>13628281</chemspider_id>
  <pubchem_compound_id>21252264</pubchem_compound_id>
  <chebi_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6401</metlin_id>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:08 UTC</creation_date>
  <update_date>2020-03-13 16:29:30 UTC</update_date>
  <accession>BMDB0001958</accession>
  <secondary_accessions>
    <accession>BMDB01958</accession>
  </secondary_accessions>
  <name>Pristanal</name>
  <description>Pristanal belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, pristanal is considered to be an isoprenoid lipid molecule. Pristanal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Pristanal can be converted into pristanic acid through the action of the enzyme fatty aldehyde dehydrogenase. In cattle, pristanal is involved in the metabolic pathway called the phytanic Acid peroxisomal oxidation pathway.</description>
  <synonyms>
    <synonym>2,6,10,14-Tetramethylpentadecanal</synonym>
    <synonym>(2R)-Pristanal</synonym>
    <synonym>(2R,6R,10R)-2,6,10,14-Tetramethylpentadecanal</synonym>
    <synonym>(2S)-Pristanal</synonym>
    <synonym>(2S,6R,10R)-2,6,10,14-Tetramethylpentadecanal</synonym>
    <synonym>2(R)-Pristanal</synonym>
    <synonym>2(S)-Pristanal</synonym>
    <synonym>2RPR-Al (2R,6R,10R,14)-tetramethylpentadecanal</synonym>
    <synonym>2SPR-Al</synonym>
  </synonyms>
  <chemical_formula>C19H38O</chemical_formula>
  <average_molecular_weight>282.5044</average_molecular_weight>
  <monisotopic_moleculate_weight>282.292265838</monisotopic_moleculate_weight>
  <iupac_name>2,6,10,14-tetramethylpentadecanal</iupac_name>
  <traditional_iupac>pristanal</traditional_iupac>
  <cas_registry_number>105373-75-9</cas_registry_number>
  <smiles>CC(C)CCCC(C)CCCC(C)CCCC(C)C=O</smiles>
  <inchi>InChI=1S/C19H38O/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20/h15-19H,6-14H2,1-5H3</inchi>
  <inchikey>IZJRIIWUSIGEAJ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Diterpenoids</sub_class>
    <direct_parent>Acyclic diterpenoids</direct_parent>
    <alternative_parents>
      <alternative_parent>Aldehydes</alternative_parent>
      <alternative_parent>Fatty aldehydes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acyclic diterpenoid</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty aldehyde</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-methyl-branched fatty aldehyde</external_descriptor>
      <external_descriptor>Acyclic diterpenoids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>7.79</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-7.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>7.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>16.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2,6,10,14-tetramethylpentadecanal</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>282.5044</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>282.292265838</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)CCCC(C)CCCC(C)CCCC(C)C=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H38O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H38O/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20/h15-19H,6-14H2,1-5H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IZJRIIWUSIGEAJ-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>89.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>38.06</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>26497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>324747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373228</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373229</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>373230</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <pubchem_compound_id>14671060</pubchem_compound_id>
  <drugbank_id/>
  <foodb_id>FDB022765</foodb_id>
  <chemspider_id>13628282</chemspider_id>
  <pdbe_id/>
  <chebi_id>49189</chebi_id>
  <kegg_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id>2364547</bigg_id>
  <wikipedia_id/>
  <metlin_id>6402</metlin_id>
  <synthesis_reference>Jung, Michael E.; Liu, Ching Yang. Efficient synthesis of a head-to-head isoprenoid geochemical biomarker from phytol. Journal of Organic Chemistry (1986), 51(26), 5446-7.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:09 UTC</creation_date>
  <update_date>2020-03-13 16:29:30 UTC</update_date>
  <accession>BMDB0001959</accession>
  <secondary_accessions>
    <accession>BMDB01959</accession>
  </secondary_accessions>
  <name>Gamma-Aminobutyryl-lysine</name>
  <description/>
  <synonyms>
    <synonym>g-Aminobutyryl-lysine</synonym>
    <synonym>Γ-aminobutyryl-lysine</synonym>
    <synonym>L-N2-(4-Aminobutyryl)-lysine</synonym>
    <synonym>N2-(4-Aminobutyryl)-lysine</synonym>
    <synonym>Na-(g-aminobutyryl)-L-lysine</synonym>
    <synonym>Na-(g-aminobutyryl)lysine</synonym>
    <synonym>Na-(gamma-aminobutyryl)-L-lysine</synonym>
    <synonym>Na-(gamma-aminobutyryl)lysine</synonym>
    <synonym>Nalpha-(g-aminobutyryl)-L-lysine</synonym>
    <synonym>Nalpha-(g-aminobutyryl)lysine</synonym>
    <synonym>Nalpha-(gamma-aminobutyryl)-L-lysine</synonym>
    <synonym>Nalpha-(gamma-aminobutyryl)lysine</synonym>
    <synonym>6-Amino-2-[(4-amino-1-hydroxybutylidene)amino]hexanoate</synonym>
  </synonyms>
  <chemical_formula>C10H21N3O3</chemical_formula>
  <average_molecular_weight>231.292</average_molecular_weight>
  <monisotopic_moleculate_weight>231.158291553</monisotopic_moleculate_weight>
  <iupac_name>6-amino-2-(4-aminobutanamido)hexanoic acid</iupac_name>
  <traditional_iupac>6-amino-2-(4-aminobutanamido)hexanoic acid</traditional_iupac>
  <cas_registry_number>22468-02-6</cas_registry_number>
  <smiles>NCCCCC(NC(=O)CCCN)C(O)=O</smiles>
  <inchi>InChI=1S/C10H21N3O3/c11-6-2-1-4-8(10(15)16)13-9(14)5-3-7-12/h8H,1-7,11-12H2,(H,13,14)(H,15,16)</inchi>
  <inchikey>OCBQYJFUZHJRIU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Peptidomimetics</class>
    <sub_class>Hybrid peptides</sub_class>
    <direct_parent>Hybrid peptides</direct_parent>
    <alternative_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amino fatty acids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Gamma amino acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-alpha amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Amino fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Gamma amino acid or derivatives</substituent>
      <substituent>Hybrid peptide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.25</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-3.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6-amino-2-(4-aminobutanamido)hexanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>231.292</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>231.158291553</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCCCCC(NC(=O)CCCN)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H21N3O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H21N3O3/c11-6-2-1-4-8(10(15)16)13-9(14)5-3-7-12/h8H,1-7,11-12H2,(H,13,14)(H,15,16)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>OCBQYJFUZHJRIU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>118.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>14169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297244</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297245</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>297246</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>338721</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB022766</foodb_id>
  <chemspider_id>16267810</chemspider_id>
  <pubchem_compound_id>23208897</pubchem_compound_id>
  <chebi_id>89308</chebi_id>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>6403</metlin_id>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:10 UTC</creation_date>
  <update_date>2020-03-13 16:29:31 UTC</update_date>
  <accession>BMDB0001960</accession>
  <secondary_accessions>
    <accession>BMDB01960</accession>
  </secondary_accessions>
  <name>Tin</name>
  <description>Tin, also known as sn(4+) or tin, ion (sn4+), belongs to the class of inorganic compounds known as homogeneous post-transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a post-transition metal atom. Tin is possibly soluble (in water) and a weakly acidic compound (based on its pKa). Tin is a potentially toxic compound.</description>
  <synonyms>
    <synonym>sn(4+)</synonym>
    <synonym>Tin, ion (sn4+)</synonym>
    <synonym>Innohep</synonym>
    <synonym>2 Propenoic acid, 3 phenyl</synonym>
    <synonym>Tinzaparin</synonym>
    <synonym>3-Phenyl- 2-propenoic acid</synonym>
    <synonym>Tinzaparin sodium</synonym>
  </synonyms>
  <chemical_formula>Sn</chemical_formula>
  <average_molecular_weight>118.71</average_molecular_weight>
  <monisotopic_moleculate_weight>119.900002251</monisotopic_moleculate_weight>
  <iupac_name>tin(4+) ion</iupac_name>
  <traditional_iupac>tin(4+) ion</traditional_iupac>
  <cas_registry_number>22537-50-4</cas_registry_number>
  <smiles>[Sn+4]</smiles>
  <inchi>InChI=1S/Sn/q+4</inchi>
  <inchikey>SYRHIZPPCHMRIT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous post-transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a post-transition metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous post-transition metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous post-transition metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous post-transition metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>elemental tin</external_descriptor>
      <external_descriptor>monoatomic tetracation</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>tin(4+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>118.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>119.900002251</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Sn+4]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Sn</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Sn/q+4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SYRHIZPPCHMRIT-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>57621</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>57622</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>57623</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>113352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>113353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>113354</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0699 +/- 0.00337</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0430 +/- 0.000842</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0665 +/- 0.00168</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS.  Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0455 +/- 0.00168</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0531 +/- 0.00421</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.0371 +/- 0.00253</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <foodb_id/>
  <chemspider_id/>
  <pubchem_compound_id>4077523</pubchem_compound_id>
  <chebi_id>30476</chebi_id>
  <kegg_id/>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Tin</wikipedia_id>
  <metlin_id/>
  <pdbe_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:11 UTC</creation_date>
  <update_date>2020-03-13 16:29:31 UTC</update_date>
  <accession>BMDB0001961</accession>
  <secondary_accessions>
    <accession>BMDB01961</accession>
  </secondary_accessions>
  <name>1,7-Dimethylguanosine</name>
  <description/>
  <synonyms>
    <synonym>1,7-Dimethylguanosine</synonym>
  </synonyms>
  <chemical_formula>C12H17N5O5</chemical_formula>
  <average_molecular_weight>311.2939</average_molecular_weight>
  <monisotopic_moleculate_weight>311.122968679</monisotopic_moleculate_weight>
  <iupac_name>2-amino-9-[(2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-oxidooxolan-2-yl]-1,7-dimethyl-6-oxo-6,7-dihydro-1H-9λ⁵-purin-9-ylium</iupac_name>
  <traditional_iupac>2-amino-9-[(2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-oxidooxolan-2-yl]-1,7-dimethyl-6-oxo-9λ⁵-purin-9-ylium</traditional_iupac>
  <cas_registry_number>69453-64-1</cas_registry_number>
  <smiles>CN1C=[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2[O-])C2=C1C(=O)N(C)C(N)=N2</smiles>
  <inchi>InChI=1S/C12H17N5O5/c1-15-4-17(11-8(20)7(19)5(3-18)22-11)9-6(15)10(21)16(2)12(13)14-9/h4-5,7-8,11,18-19H,3H2,1-2H3,(H2,13,14)/t5-,7-,8-,11-/m1/s1</inchi>
  <inchikey>AISVAXNALHBFPC-IOSLPCCCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleosides</class>
    <sub_class/>
    <direct_parent>Purine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Alkoxides</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic zwitterions</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkoxide</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic zwitterion</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleoside</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>11.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-9-[(2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-oxidooxolan-2-yl]-1,7-dimethyl-6-oxo-6,7-dihydro-1H-9λ⁵-purin-9-ylium</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>311.2939</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>311.122968679</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C=[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2[O-])C2=C1C(=O)N(C)C(N)=N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H17N5O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H17N5O5/c1-15-4-17(11-8(20)7(19)5(3-18)22-11)9-6(15)10(21)16(2)12(13)14-9/h4-5,7-8,11,18-19H,3H2,1-2H3,(H2,13,14)/t5-,7-,8-,11-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AISVAXNALHBFPC-IOSLPCCCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>140.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>85.26</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>30.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>22850</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316721</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>316722</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363052</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363054</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id>140757</chemspider_id>
  <foodb_id>FDB022767</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>160130</pubchem_compound_id>
  <chebi_id/>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:13 UTC</creation_date>
  <update_date>2020-04-15 22:34:26 UTC</update_date>
  <accession>BMDB0001964</accession>
  <secondary_accessions>
    <accession>BMDB01964</accession>
  </secondary_accessions>
  <name>Caffeic acid</name>
  <description>Caffeic acid, also known as caffeate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Caffeic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Caffeic acid exists in all living species, ranging from bacteria to humans. Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.</description>
  <synonyms>
    <synonym>3,4-Dihydroxy-trans-cinnamate</synonym>
    <synonym>3,4-Dihydroxycinnamic acid</synonym>
    <synonym>trans-Caffeate</synonym>
    <synonym>3,4-Dihydroxy-trans-cinnamic acid</synonym>
    <synonym>3,4-Dihydroxycinnamate</synonym>
    <synonym>trans-Caffeic acid</synonym>
    <synonym>Caffeate</synonym>
    <synonym>Caffeic acid, monosodium salt</synonym>
    <synonym>Caffeic acid, (e)-isomer</synonym>
    <synonym>Sodium caffeate</synonym>
    <synonym>(2E)-(3,4-Dihydroxyphenyl)-2-propenoic acid</synonym>
    <synonym>(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid</synonym>
    <synonym>(e)-3,4-Dihydroxycinnamic acid</synonym>
    <synonym>(e)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid</synonym>
    <synonym>(e)-3-(3,4-Dihydroxyphenyl)acrylic acid</synonym>
    <synonym>(e)-Caffeic acid</synonym>
    <synonym>3,4-Dihydroxybenzeneacrylic acid</synonym>
    <synonym>3-(3,4-Dihydroxyphenyl)-2-propenoic acid</synonym>
    <synonym>3-(3,4-Dihydroxyphenyl)propenoic acid</synonym>
    <synonym>4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene</synonym>
    <synonym>4-(2-Carboxyethenyl)-1,2-dihydroxybenzene</synonym>
    <synonym>4-(2’-carboxyvinyl)-1,2-dihydroxybenzene</synonym>
    <synonym>DHCA</synonym>
    <synonym>trans-3,4-Dihydroxycinnamic acid</synonym>
    <synonym>CAFFEIC ACID</synonym>
    <synonym>Caffeic acid</synonym>
  </synonyms>
  <chemical_formula>C9H8O4</chemical_formula>
  <average_molecular_weight>180.1574</average_molecular_weight>
  <monisotopic_moleculate_weight>180.042258744</monisotopic_moleculate_weight>
  <iupac_name>(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid</iupac_name>
  <traditional_iupac>caffeic acid</traditional_iupac>
  <cas_registry_number>501-16-6</cas_registry_number>
  <smiles>OC(=O)\C=C\C1=CC(O)=C(O)C=C1</smiles>
  <inchi>InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+</inchi>
  <inchikey>QAIPRVGONGVQAS-DUXPYHPUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Phenylpropanoids and polyketides</super_class>
    <class>Cinnamic acids and derivatives</class>
    <sub_class>Hydroxycinnamic acids and derivatives</sub_class>
    <direct_parent>Hydroxycinnamic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Catechols</alternative_parent>
      <alternative_parent>Cinnamic acids</alternative_parent>
      <alternative_parent>Coumaric acids and derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Styrenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Catechol</substituent>
      <substituent>Cinnamic acid</substituent>
      <substituent>Coumaric acid or derivatives</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxycinnamic acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Styrene</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Caffeate derivatives</external_descriptor>
      <external_descriptor>caffeic acid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>225 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.15</value>
      <source>SANGSTER (1993)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.67</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>180.1574</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>180.042258744</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>OC(=O)\C=C\C1=CC(O)=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H8O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QAIPRVGONGVQAS-DUXPYHPUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>77.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>17.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2354</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>28715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30492</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38615</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107598</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107599</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107600</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>174609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>174610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>174611</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374048</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Commercial milk, by CIL LC-MS</comment>
      <references>
        <reference>
          <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
          <pubmed_id>28306241</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Urine</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Samples collected from 16 multiparous Holstein cows </comment>
      <references>
        <reference>
          <reference_text>Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28.</reference_text>
          <pubmed_id>25599412</pubmed_id>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C01481</kegg_id>
  <chemspider_id/>
  <foodb_id>FDB002559</foodb_id>
  <drugbank_id>DB01880</drugbank_id>
  <pubchem_compound_id>689043</pubchem_compound_id>
  <chebi_id>16433</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id>C00000615</knapsack_id>
  <bigg_id/>
  <wikipedia_id>Caffeic_acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28.</reference_text>
      <pubmed_id>28306241</pubmed_id>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:14 UTC</creation_date>
  <update_date>2020-03-13 16:29:33 UTC</update_date>
  <accession>BMDB0001965</accession>
  <secondary_accessions>
    <accession>BMDB01965</accession>
  </secondary_accessions>
  <name>Troxilin B3</name>
  <description/>
  <synonyms>
    <synonym>(5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoic acid</synonym>
    <synonym>(5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoic acid</synonym>
    <synonym>10,11S,12R-TriOH all-cis-5,8,14-20:3</synonym>
    <synonym>10,11S,12R-TriOH all-cis-5,8,14-C20:3</synonym>
    <synonym>(5Z,8Z,14Z)-(11R,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoic acid</synonym>
    <synonym>(5Z,8Z,14Z)-(11R,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoic acid</synonym>
    <synonym>(5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoate</synonym>
    <synonym>(5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoate</synonym>
    <synonym>(5Z,8Z,14Z)-(11R,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoate</synonym>
    <synonym>(5Z,8Z,14Z)-(11R,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoate</synonym>
    <synonym>(5Z,8Z,11S,12R,14Z)-10,11,12-Trihydroxyicosa-5,8,14-trienoate</synonym>
    <synonym>(5Z,8Z,11S,12R,14Z)-10,11,12-Trihydroxyicosa-5,8,14-trienoic acid</synonym>
    <synonym>(5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoicacid</synonym>
    <synonym>10,11S,12R-Trihydroxy-5Z,8Z,14Z-eicosatrienoate</synonym>
    <synonym>10,11S,12R-Trihydroxy-5Z,8Z,14Z-eicosatrienoic acid</synonym>
    <synonym>TRXB(3)</synonym>
    <synonym>Trioxilin b3</synonym>
    <synonym>Troxilin b3</synonym>
  </synonyms>
  <chemical_formula>C20H34O5</chemical_formula>
  <average_molecular_weight>354.481</average_molecular_weight>
  <monisotopic_moleculate_weight>354.240624198</monisotopic_moleculate_weight>
  <iupac_name>(5Z,8Z,11S,12R,14Z)-10,11,12-trihydroxyicosa-5,8,14-trienoic acid</iupac_name>
  <traditional_iupac>trioxilin B3</traditional_iupac>
  <cas_registry_number/>
  <smiles>CCCCC\C=C/C[C@@H](O)[C@H](O)C(O)\C=C/C\C=C/CCCC(O)=O</smiles>
  <inchi>InChI=1S/C20H34O5/c1-2-3-4-5-8-11-14-17(21)20(25)18(22)15-12-9-6-7-10-13-16-19(23)24/h6-8,11-12,15,17-18,20-22,25H,2-5,9-10,13-14,16H2,1H3,(H,23,24)/b7-6-,11-8-,15-12-/t17-,18?,20+/m1/s1</inchi>
  <inchikey>GOHNIXDAQODZKP-OZPSOFALSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Hydroxyeicosatrienoic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Hydroxyeicosatrienoic acid</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Hepoxilins</external_descriptor>
      <external_descriptor>Hepoxilins</external_descriptor>
      <external_descriptor>trioxilin</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-3.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(5Z,8Z,11S,12R,14Z)-10,11,12-trihydroxyicosa-5,8,14-trienoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>354.481</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>354.240624198</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCC\C=C/C[C@@H](O)[C@H](O)C(O)\C=C/C\C=C/CCCC(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C20H34O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C20H34O5/c1-2-3-4-5-8-11-14-17(21)20(25)18(22)15-12-9-6-7-10-13-16-19(23)24/h6-8,11-12,15,17-18,20-22,25H,2-5,9-10,13-14,16H2,1H3,(H,23,24)/b7-6-,11-8-,15-12-/t17-,18?,20+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GOHNIXDAQODZKP-OZPSOFALSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>97.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>103.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>40.34</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>319869</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>367104</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38203</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C14811</kegg_id>
  <chemspider_id>4446331</chemspider_id>
  <foodb_id>FDB022768</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>5283210</pubchem_compound_id>
  <chebi_id>35032</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:15 UTC</creation_date>
  <update_date>2020-04-14 21:15:21 UTC</update_date>
  <accession>BMDB0001966</accession>
  <secondary_accessions>
    <accession>BMDB01966</accession>
  </secondary_accessions>
  <name>Titanium</name>
  <description>Titanium, also known as titanium alloy or EBT, belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom. Titanium exists as a solid, possibly soluble (in water), and possibly neutral molecule.</description>
  <synonyms>
    <synonym>Titanium alloy</synonym>
    <synonym>Alpaste rta 030</synonym>
    <synonym>ATI 24</synonym>
    <synonym>C.P. titanium</synonym>
    <synonym>Contimet 30</synonym>
    <synonym>CP Titanium</synonym>
    <synonym>DAT 1</synonym>
    <synonym>DAT 5E</synonym>
    <synonym>Dentcraft titan ingot</synonym>
    <synonym>EBT</synonym>
    <synonym>EBT (metal)</synonym>
    <synonym>Oremet</synonym>
    <synonym>PTKH 2</synonym>
    <synonym>Smelloff-cutter titanium</synonym>
    <synonym>Titan</synonym>
    <synonym>Titan VT 1-1</synonym>
    <synonym>Titanate</synonym>
    <synonym>Titanium element</synonym>
    <synonym>Titanium fulleride (tic20)</synonym>
    <synonym>Titanium hydride</synonym>
    <synonym>Titanium VT1</synonym>
    <synonym>Titanium(II) hydride</synonym>
    <synonym>Titanium-125</synonym>
    <synonym>Tiunite</synonym>
  </synonyms>
  <chemical_formula>Ti</chemical_formula>
  <average_molecular_weight>47.867</average_molecular_weight>
  <monisotopic_moleculate_weight>47.947947053</monisotopic_moleculate_weight>
  <iupac_name>titanium(4+) ion</iupac_name>
  <traditional_iupac>titanium(4+) ion</traditional_iupac>
  <cas_registry_number>7440-32-6</cas_registry_number>
  <smiles>[Ti+4]</smiles>
  <inchi>InChI=1S/Ti/q+4</inchi>
  <inchikey>LCKIEQZJEYYRIY-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous metal compounds</super_class>
    <class>Homogeneous transition metal compounds</class>
    <sub_class/>
    <direct_parent>Homogeneous transition metal compounds</direct_parent>
    <alternative_parents>
    </alternative_parents>
    <substituents>
      <substituent>Homogeneous transition metal</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>1668 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>titanium(4+) ion</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>47.867</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>47.947947053</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[Ti+4]</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>Ti</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/Ti/q+4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LCKIEQZJEYYRIY-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>1.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>77601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>77602</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>77603</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>137769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>137770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>137771</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Liver</biospecimen>
      <concentration_value>2.2+/-0.4</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Longissimus thoracis muscle</biospecimen>
      <concentration_value>1.2+/-0.2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.128 - 2.173</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.73</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.5 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>1% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.4 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>2% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.5 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>3.25% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.4 +/- 0.1</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204.</reference_text>
          <pubmed_id>30994344</pubmed_id>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.402 +/- 0.313</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.859 +/- 0.0418</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were sonicated inside an ultrasound water bath for 10 min. </comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>3.217 +/- 0.334</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS.  Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.588 +/- 0.0836</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS. Samples were analyzed after a microwave-assisted digestion</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>2.298 +/- 0.334</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>full cream, 3.8% milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>1.316 +/- 0.0836</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>Skim milk by ICP-MS</comment>
      <references>
        <reference>
          <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value>0.836 - 3.969</concentration_value>
      <concentration_units>uM</concentration_units>
      <references>
        <reference>
          <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Rumen</biospecimen>
      <concentration_value>2.5+/-0.4</concentration_value>
      <concentration_units>uM</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Semimembranosus muscle</biospecimen>
      <concentration_value>1.3+/-0.2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Testis</biospecimen>
      <concentration_value>1+/-0.2</concentration_value>
      <concentration_units>nmol/g of tissue</concentration_units>
      <comment>By ICP-MS</comment>
      <references>
        <reference>
          <reference_text>The Bovine Metabolome Database: Quantitative, Comprehensive Metabolite Data for Multiple Bovine Biofluids and Tissues (in preparation)</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id/>
  <chemspider_id>102881</chemspider_id>
  <foodb_id>FDB003789</foodb_id>
  <drugbank_id/>
  <pubchem_compound_id>114942</pubchem_compound_id>
  <chebi_id>33341</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Titanium</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
    <reference>
      <reference_text>Semaghiul Birghila, Simona Dobrinas, Gabriela Stanciu and Alina Soceanu. Determination of major and minor elements in milk through ICP-AES. Environmental Engineering and Management Journal. November/December 2008, Vol.7, No.6, 805-808</reference_text>
    </reference>
    <reference>
      <reference_text>A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)</reference_text>
    </reference>
    <reference>
      <reference_text>Patricia Cava-Montesinos, M. Luisa Cervera Agustín Pastor Miguel de la Guardia. 2005. Room temperature acid sonication ICP-MS multielemental analysis of milk.Analytica Chimica Acta Volume 531, Issue 1, Pages 111-123</reference_text>
    </reference>
    <reference>
      <reference_text>Z. Dobrzański, R. Kołacz, H. Górecka, K. Chojnacka, A. Bartkowiak. 2005. The Content of Microelements and Trace Elements in Raw Milk from Cows in the Silesian Region. Pol. J. Environ. Stud. 14(5):685–689</reference_text>
    </reference>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:16 UTC</creation_date>
  <update_date>2020-04-14 22:49:27 UTC</update_date>
  <accession>BMDB0001967</accession>
  <secondary_accessions>
    <accession>BMDB01967</accession>
  </secondary_accessions>
  <name>Carbon dioxide</name>
  <description/>
  <synonyms>
    <synonym>[CO2]</synonym>
    <synonym>Carbonic anhydride</synonym>
    <synonym>CO2</synonym>
    <synonym>e 290</synonym>
    <synonym>e-290</synonym>
    <synonym>e290</synonym>
    <synonym>R-744</synonym>
    <synonym>Carbon oxide</synonym>
    <synonym>Carbon-12 dioxide</synonym>
    <synonym>Carbonic acid anhydride</synonym>
    <synonym>Carbonic acid gas</synonym>
    <synonym>Anhydride, carbonic</synonym>
    <synonym>Dioxide, carbon</synonym>
  </synonyms>
  <chemical_formula>CO2</chemical_formula>
  <average_molecular_weight>44.0095</average_molecular_weight>
  <monisotopic_moleculate_weight>43.989829244</monisotopic_moleculate_weight>
  <iupac_name>methanedione</iupac_name>
  <traditional_iupac>carbon dioxide</traditional_iupac>
  <cas_registry_number>124-38-9</cas_registry_number>
  <smiles>O=C=O</smiles>
  <inchi>InChI=1S/CO2/c2-1-3</inchi>
  <inchikey>CURLTUGMZLYLDI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of inorganic compounds known as other non-metal oxides. These are inorganic compounds containing an oxygen atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen belongs to the class of 'other non-metals'.</description>
    <kingdom>Inorganic compounds</kingdom>
    <super_class>Homogeneous non-metal compounds</super_class>
    <class>Other non-metal organides</class>
    <sub_class>Other non-metal oxides</sub_class>
    <direct_parent>Other non-metal oxides</direct_parent>
    <alternative_parents>
      <alternative_parent>Inorganic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Inorganic oxide</substituent>
      <substituent>Other non-metal oxide</substituent>
    </substituents>
    <molecular_framework/>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>carbon oxide</external_descriptor>
      <external_descriptor>one-carbon compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Liquid</state>
    <property>
      <kind>melting_point</kind>
      <value>-56.5 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>1.48 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.83</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>methanedione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>44.0095</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>43.989829244</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>O=C=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>CO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/CO2/c2-1-3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>CURLTUGMZLYLDI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>34.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>6.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>2.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Ammonia Recycling</name>
      <smpdb_id>SMP0087177</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Arginine and Proline Metabolism</name>
      <smpdb_id>SMP0087178</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Aspartate Metabolism</name>
      <smpdb_id>SMP0087165</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>beta-Alanine Metabolism</name>
      <smpdb_id>SMP0087180</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Carnitine Synthesis</name>
      <smpdb_id>SMP0087187</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Citric Acid Cycle</name>
      <smpdb_id>SMP0087163</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Fatty Acid Metabolism</name>
      <smpdb_id>SMP0087172</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Folate Metabolism</name>
      <smpdb_id>SMP0087196</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gastric Acid Production</name>
      <smpdb_id>SMP0119381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Gluconeogenesis</name>
      <smpdb_id>SMP0087223</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glutamate Metabolism</name>
      <smpdb_id>SMP0087169</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Glycine and Serine Metabolism</name>
      <smpdb_id>SMP0087245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Histidine Metabolism</name>
      <smpdb_id>SMP0087219</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Ketone Body Metabolism</name>
      <smpdb_id>SMP0087202</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Lysine Degradation</name>
      <smpdb_id>SMP0087203</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methionine Metabolism</name>
      <smpdb_id>SMP0087249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nicotinate and Nicotinamide Metabolism</name>
      <smpdb_id>SMP0087241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Nucleotide Sugars Metabolism</name>
      <smpdb_id>SMP0087205</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Oxidation of Branched-Chain Fatty Acids</name>
      <smpdb_id>SMP0087255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pantothenate and CoA Biosynthesis</name>
      <smpdb_id>SMP0087207</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pentose Phosphate Pathway</name>
      <smpdb_id>SMP0087246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylalanine and Tyrosine Metabolism</name>
      <smpdb_id>SMP0087218</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis</name>
      <smpdb_id>SMP0072037</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:0)</name>
      <smpdb_id>SMP0080430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0080431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/15:0)</name>
      <smpdb_id>SMP0080432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:0)</name>
      <smpdb_id>SMP0080433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0080434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:0)</name>
      <smpdb_id>SMP0080435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0080436</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0080437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:0)</name>
      <smpdb_id>SMP0080442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0080443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:0)</name>
      <smpdb_id>SMP0080450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0080451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:0)</name>
      <smpdb_id>SMP0080457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0080458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0080459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0080460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0080461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080467</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/15:0)</name>
      <smpdb_id>SMP0080487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:0)</name>
      <smpdb_id>SMP0080488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0080489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:0)</name>
      <smpdb_id>SMP0080490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0080491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0080492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:0)</name>
      <smpdb_id>SMP0080497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0080498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:0)</name>
      <smpdb_id>SMP0080505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0080506</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:0)</name>
      <smpdb_id>SMP0080512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0080513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:0)</name>
      <smpdb_id>SMP0080514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0080515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:0)</name>
      <smpdb_id>SMP0080516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0080517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0080518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080519</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:0)</name>
      <smpdb_id>SMP0080523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0080524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:0)</name>
      <smpdb_id>SMP0080531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0080532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:0)</name>
      <smpdb_id>SMP0080538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0080539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0080540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0080541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080560</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:0)</name>
      <smpdb_id>SMP0080565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0080566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0080567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:0)</name>
      <smpdb_id>SMP0080572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0080573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:0)</name>
      <smpdb_id>SMP0080580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0080581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:0)</name>
      <smpdb_id>SMP0080587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0080588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0080589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0080595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0080612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0080617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0080625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0080632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0080634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0080655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0080658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0080666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0080673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080674</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080675</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080676</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080677</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080678</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080679</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080680</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080681</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080682</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080683</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080684</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080685</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080686</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080687</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080689</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080690</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080691</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080692</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080693</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0080694</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0080695</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080696</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080697</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080698</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080699</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080700</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080701</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080702</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0080703</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080704</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080705</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080706</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080707</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080708</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080709</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0080710</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:0)</name>
      <smpdb_id>SMP0080712</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0080713</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080714</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080715</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080716</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080717</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080718</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080719</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:0)</name>
      <smpdb_id>SMP0080720</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0080721</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080722</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080723</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080724</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080725</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080726</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:0)</name>
      <smpdb_id>SMP0080727</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0080728</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0080729</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080730</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080731</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080732</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080733</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080734</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080735</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0080736</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080737</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080738</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080739</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080740</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080741</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080742</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0080743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080744</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0080745</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080746</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080747</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080748</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080749</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080751</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080752</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080753</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080754</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080755</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080756</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080757</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080758</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080759</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0080760</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080761</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080762</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080763</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080764</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0080765</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080766</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080767</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080768</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080769</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080770</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0080772</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080773</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080774</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080775</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080776</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080777</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080778</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080779</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080780</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080781</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080782</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080783</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080784</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080785</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080786</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0080787</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080788</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080789</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0080790</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080791</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080792</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080793</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080794</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080795</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080796</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0080797</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080798</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080799</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080800</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080801</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080802</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080803</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080804</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080805</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080806</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080807</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080808</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080809</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0080810</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0080811</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080812</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080813</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080814</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080815</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080816</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080817</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0080818</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080819</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:0)</name>
      <smpdb_id>SMP0080820</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0080821</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080822</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080823</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080824</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080825</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080826</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:0)</name>
      <smpdb_id>SMP0080827</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0080828</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0080829</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080830</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080831</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080832</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080833</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080834</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0080835</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080836</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0080837</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080838</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080839</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080841</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080842</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080843</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080844</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080845</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080846</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080847</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080848</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080849</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0080850</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080851</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080853</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0080854</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080855</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080856</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080857</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080858</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080859</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0080860</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0080862</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080863</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:0)</name>
      <smpdb_id>SMP0080864</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0080865</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylcholine Biosynthesis PC(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0080866</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis</name>
      <smpdb_id>SMP0072048</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:0)</name>
      <smpdb_id>SMP0082233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/14:1(9Z))</name>
      <smpdb_id>SMP0082234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/15:0)</name>
      <smpdb_id>SMP0082235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:0)</name>
      <smpdb_id>SMP0082236</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/16:1(9Z))</name>
      <smpdb_id>SMP0082237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:0)</name>
      <smpdb_id>SMP0082238</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(11Z))</name>
      <smpdb_id>SMP0082239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:1(9Z))</name>
      <smpdb_id>SMP0082240</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082241</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082244</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:0)</name>
      <smpdb_id>SMP0082245</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:1(11Z))</name>
      <smpdb_id>SMP0082246</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082249</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082250</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082251</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082252</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:0)</name>
      <smpdb_id>SMP0082253</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:1(13Z))</name>
      <smpdb_id>SMP0082254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082255</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082256</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082257</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082258</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082259</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:0)</name>
      <smpdb_id>SMP0082260</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:0/24:1(15Z))</name>
      <smpdb_id>SMP0082261</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/14:1(9Z))</name>
      <smpdb_id>SMP0082262</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/15:0)</name>
      <smpdb_id>SMP0082263</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:0)</name>
      <smpdb_id>SMP0082264</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082266</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082267</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082268</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082269</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082270</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082271</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082272</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082273</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082274</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082275</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082276</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082277</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082278</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082279</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082280</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082281</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082282</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082283</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082284</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082285</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082286</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082287</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082288</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(14:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082289</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/15:0)</name>
      <smpdb_id>SMP0082290</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:0)</name>
      <smpdb_id>SMP0082291</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/16:1(9Z))</name>
      <smpdb_id>SMP0082292</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:0)</name>
      <smpdb_id>SMP0082293</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(11Z))</name>
      <smpdb_id>SMP0082294</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:1(9Z))</name>
      <smpdb_id>SMP0082295</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082296</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082297</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082298</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082299</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:0)</name>
      <smpdb_id>SMP0082300</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:1(11Z))</name>
      <smpdb_id>SMP0082301</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082303</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082304</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082305</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082306</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:0)</name>
      <smpdb_id>SMP0082308</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:1(13Z))</name>
      <smpdb_id>SMP0082309</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082310</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082311</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082312</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082313</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082314</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:0)</name>
      <smpdb_id>SMP0082315</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(15:0/24:1(15Z))</name>
      <smpdb_id>SMP0082316</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:0)</name>
      <smpdb_id>SMP0082317</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/16:1(9Z))</name>
      <smpdb_id>SMP0082318</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:0)</name>
      <smpdb_id>SMP0082319</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(11Z))</name>
      <smpdb_id>SMP0082320</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:1(9Z))</name>
      <smpdb_id>SMP0082321</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082322</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082323</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082325</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:0)</name>
      <smpdb_id>SMP0082326</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:1(11Z))</name>
      <smpdb_id>SMP0082327</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082328</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082329</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082330</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082331</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082332</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082333</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:0)</name>
      <smpdb_id>SMP0082334</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:1(13Z))</name>
      <smpdb_id>SMP0082335</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082336</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082337</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082338</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082339</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082340</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:0)</name>
      <smpdb_id>SMP0082341</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:0/24:1(15Z))</name>
      <smpdb_id>SMP0082342</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/16:1(9Z))</name>
      <smpdb_id>SMP0082343</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:0)</name>
      <smpdb_id>SMP0082344</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082345</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082346</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082347</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082348</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082349</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082350</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082351</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082352</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082353</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082354</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082355</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082356</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082357</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082358</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082359</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082360</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082361</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082362</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082363</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082364</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082365</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082366</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(16:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082367</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:0)</name>
      <smpdb_id>SMP0082368</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(11Z))</name>
      <smpdb_id>SMP0082369</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:1(9Z))</name>
      <smpdb_id>SMP0082370</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082371</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082372</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082373</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082374</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:0)</name>
      <smpdb_id>SMP0082375</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:1(11Z))</name>
      <smpdb_id>SMP0082376</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082377</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082378</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082379</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082380</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082381</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082382</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:0)</name>
      <smpdb_id>SMP0082383</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:1(13Z))</name>
      <smpdb_id>SMP0082384</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082385</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082386</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082387</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082388</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082389</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:0)</name>
      <smpdb_id>SMP0082390</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:0/24:1(15Z))</name>
      <smpdb_id>SMP0082391</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(11Z))</name>
      <smpdb_id>SMP0082392</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082393</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082394</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082395</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082396</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082397</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:0)</name>
      <smpdb_id>SMP0082398</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082399</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082400</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082402</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082403</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082404</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082405</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082406</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082408</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082409</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082410</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082411</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082412</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082413</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082414</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082415</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(9Z))</name>
      <smpdb_id>SMP0082416</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082417</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082418</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082420</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:0)</name>
      <smpdb_id>SMP0082421</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082422</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082423</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082424</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082425</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082426</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082427</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082428</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:0)</name>
      <smpdb_id>SMP0082429</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082430</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082431</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082432</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082433</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082434</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082435</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:0)</name>
      <smpdb_id>SMP0082437</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082438</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:2(9Z,12Z))</name>
      <smpdb_id>SMP0082439</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082440</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082441</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082442</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082443</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082444</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082445</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082446</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082447</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082448</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082449</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082450</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082451</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082452</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082453</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082454</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082455</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082456</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082457</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082458</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:2(9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082459</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(6Z,9Z,12Z))</name>
      <smpdb_id>SMP0082460</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082461</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082462</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:0)</name>
      <smpdb_id>SMP0082463</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082464</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082465</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082466</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082468</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082469</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082470</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082471</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:0)</name>
      <smpdb_id>SMP0082472</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082473</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082474</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082475</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082476</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082477</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082478</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:0)</name>
      <smpdb_id>SMP0082479</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(6Z,9Z,12Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082480</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082481</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082482</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082483</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082484</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082485</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082486</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082487</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082488</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082489</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082490</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082491</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082492</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082493</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082494</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082495</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082496</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082497</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082498</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:3(9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082499</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))</name>
      <smpdb_id>SMP0082500</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:0)</name>
      <smpdb_id>SMP0082501</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082502</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082503</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082504</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082505</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082507</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082508</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082509</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:0)</name>
      <smpdb_id>SMP0082510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082511</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082512</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082513</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082514</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082515</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082516</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:0)</name>
      <smpdb_id>SMP0082517</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(18:4(6Z,9Z,12Z,15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082518</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:0)</name>
      <smpdb_id>SMP0082520</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:1(11Z))</name>
      <smpdb_id>SMP0082521</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082522</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082523</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082524</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082525</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082526</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082527</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:0)</name>
      <smpdb_id>SMP0082528</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:1(13Z))</name>
      <smpdb_id>SMP0082529</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082530</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082531</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082532</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082533</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082534</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:0)</name>
      <smpdb_id>SMP0082535</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:0/24:1(15Z))</name>
      <smpdb_id>SMP0082536</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:1(11Z))</name>
      <smpdb_id>SMP0082537</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082538</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082539</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082540</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082541</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082542</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082543</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0)</name>
      <smpdb_id>SMP0082544</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082545</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082546</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082547</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082548</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082549</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082550</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:0)</name>
      <smpdb_id>SMP0082551</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082552</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:2(11Z,14Z))</name>
      <smpdb_id>SMP0082553</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082554</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082555</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082556</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082557</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082558</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082559</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082561</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082562</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082563</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082564</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082565</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082566</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082567</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:2(11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082568</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(5Z,8Z,11Z))</name>
      <smpdb_id>SMP0082569</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082570</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082571</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082572</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082573</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:0)</name>
      <smpdb_id>SMP0082574</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082575</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082576</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082577</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082578</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082579</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082580</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:0)</name>
      <smpdb_id>SMP0082581</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(5Z,8Z,11Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082582</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:3(8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082583</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082584</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082585</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082586</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082587</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082588</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082589</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082590</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082591</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082592</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082593</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082594</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:3(8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082595</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))</name>
      <smpdb_id>SMP0082596</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082597</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082598</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:0)</name>
      <smpdb_id>SMP0082599</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082600</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082601</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082602</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082603</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082604</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082605</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:0)</name>
      <smpdb_id>SMP0082606</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(5Z,8Z,11Z,14Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082607</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:4(8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082608</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082609</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082610</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082611</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082612</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082613</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082614</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082615</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082616</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082617</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:4(8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082618</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/20:5(5Z,8Z,11Z,14Z,17Z))</name>
      <smpdb_id>SMP0082619</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:0)</name>
      <smpdb_id>SMP0082620</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082621</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082622</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082623</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082624</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082625</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082626</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:0)</name>
      <smpdb_id>SMP0082627</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(20:5(5Z,8Z,11Z,14Z,17Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082628</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:0)</name>
      <smpdb_id>SMP0082629</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:1(13Z))</name>
      <smpdb_id>SMP0082630</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082631</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082632</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082633</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082634</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082635</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:0)</name>
      <smpdb_id>SMP0082636</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:0/24:1(15Z))</name>
      <smpdb_id>SMP0082637</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:1(13Z))</name>
      <smpdb_id>SMP0082638</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082639</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082640</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082641</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082642</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082643</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:0)</name>
      <smpdb_id>SMP0082644</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:1(13Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082645</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:2(13Z,16Z))</name>
      <smpdb_id>SMP0082646</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082647</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082648</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082649</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082651</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:2(13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082652</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:4(7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082653</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082654</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082655</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082656</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082657</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:4(7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082658</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z))</name>
      <smpdb_id>SMP0082659</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082660</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082661</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:0)</name>
      <smpdb_id>SMP0082662</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(4Z,7Z,10Z,13Z,16Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082663</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082664</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082665</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082666</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:5(7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082667</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))</name>
      <smpdb_id>SMP0082668</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:0)</name>
      <smpdb_id>SMP0082669</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082670</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:0)</name>
      <smpdb_id>SMP0082671</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:0/24:1(15Z))</name>
      <smpdb_id>SMP0082672</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phosphatidylethanolamine Biosynthesis PE(24:1(15Z)/24:1(15Z))</name>
      <smpdb_id>SMP0082673</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phytanic Acid Peroxisomal Oxidation</name>
      <smpdb_id>SMP0087217</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Porphyrin Metabolism</name>
      <smpdb_id>SMP0087243</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propanoate Metabolism</name>
      <smpdb_id>SMP0087248</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Purine Metabolism</name>
      <smpdb_id>SMP0087239</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyrimidine Metabolism</name>
      <smpdb_id>SMP0087247</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Pyruvate Metabolism</name>
      <smpdb_id>SMP0087231</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Spermidine and Spermine Biosynthesis</name>
      <smpdb_id>SMP0087213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Steroid Biosynthesis</name>
      <smpdb_id>SMP0087233</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Taurine and Hypotaurine Metabolism</name>
      <smpdb_id>SMP0087214</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Transfer of Acetyl Groups into Mitochondria</name>
      <smpdb_id>SMP0087254</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tryptophan Metabolism</name>
      <smpdb_id>SMP0087237</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tyrosine Metabolism</name>
      <smpdb_id>SMP0087235</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Urea Cycle</name>
      <smpdb_id>SMP0087224</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Valine, Leucine, and Isoleucine Degradation</name>
      <smpdb_id>SMP0087234</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Vitamin K Metabolism</name>
      <smpdb_id>SMP0087227</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Warburg Effect</name>
      <smpdb_id>SMP0087270</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>973</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20289</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>20290</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>21841</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <kegg_id>C00011</kegg_id>
  <chemspider_id>274</chemspider_id>
  <foodb_id>FDB014084</foodb_id>
  <drugbank_id>DB09157</drugbank_id>
  <pubchem_compound_id>280</pubchem_compound_id>
  <chebi_id>16526</chebi_id>
  <pdbe_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id>CARBON-DIOXIDE</meta_cyc_id>
  <knapsack_id/>
  <bigg_id>33506</bigg_id>
  <wikipedia_id>Carbon_dioxide</wikipedia_id>
  <metlin_id>3199</metlin_id>
  <synthesis_reference>Callahan, Richard A.  Process and apparatus for producing liquid carbon dioxide.  U.S.  (1993),  Patent US5233837 (https://patents.google.com/patent/US5233837)</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:17 UTC</creation_date>
  <update_date>2020-03-13 16:29:34 UTC</update_date>
  <accession>BMDB0001968</accession>
  <secondary_accessions>
    <accession>BMDB01968</accession>
  </secondary_accessions>
  <name>5b-Cholestane-3a,7a,12a,23-Tetrol</name>
  <description/>
  <synonyms>
    <synonym>6,15-Dioxo-9S,11R-dihydroxy-13E-prostenoic acid</synonym>
    <synonym>6,15DK,13,14DH-PGF1a</synonym>
    <synonym>6,15-Dioxo-9S,11R-dihydroxy-13E-prostenoate</synonym>
    <synonym>6,15-Diketo,13,14-dihydro-PGF1alpha</synonym>
    <synonym>6,15-Diketo-13,14-dihydro-PGF1a</synonym>
    <synonym>6,15-Diketo,13,14-dihydroprostaglandin F1a</synonym>
    <synonym>6,15-Diketo,13,14-dihydroprostaglandin F1α</synonym>
    <synonym>(3a,5b,7a,12a)-Cholestane-3,7,12,23-tetrol</synonym>
  </synonyms>
  <chemical_formula>C27H48O4</chemical_formula>
  <average_molecular_weight>436.6676</average_molecular_weight>
  <monisotopic_moleculate_weight>436.355260024</monisotopic_moleculate_weight>
  <iupac_name>(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-4-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol</iupac_name>
  <traditional_iupac>(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-4-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol</traditional_iupac>
  <cas_registry_number>63446-59-3</cas_registry_number>
  <smiles>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CC(O)CC(C)C</smiles>
  <inchi>InChI=1S/C27H48O4/c1-15(2)10-19(29)11-16(3)20-6-7-21-25-22(14-24(31)27(20,21)5)26(4)9-8-18(28)12-17(26)13-23(25)30/h15-25,28-31H,6-14H2,1-5H3/t16-,17+,18-,19?,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1</inchi>
  <inchikey>VGCSSPQIZFVVCH-UVBCEDGCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Eicosanoids</sub_class>
    <direct_parent>Prostaglandins and related compounds</direct_parent>
    <alternative_parents>
      <alternative_parent>Acryloyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Cyclopentanols</alternative_parent>
      <alternative_parent>Enones</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Keto fatty acids</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Long-chain fatty acids</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acryloyl-group</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homomonocyclic compound</substituent>
      <substituent>Alpha,beta-unsaturated ketone</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclopentanol</substituent>
      <substituent>Enone</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Keto fatty acid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Long-chain fatty acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Prostaglandin skeleton</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Prostaglandins</external_descriptor>
      <external_descriptor>prostaglandins Falpha</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.47</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-4.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>18.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-0.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-14-[(2R)-4-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,9,16-triol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>436.6676</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>436.355260024</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CC(O)CC(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C27H48O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C27H48O4/c1-15(2)10-19(29)11-16(3)20-6-7-21-25-22(14-24(31)27(20,21)5)26(4)9-8-18(28)12-17(26)13-23(25)30/h15-25,28-31H,6-14H2,1-5H3/t16-,17+,18-,19?,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VGCSSPQIZFVVCH-UVBCEDGCSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>80.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>124.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>53.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38204</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301087</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>301089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>343530</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <chemspider_id>4446160</chemspider_id>
  <foodb_id>FDB022777</foodb_id>
  <drugbank_id/>
  <pdbe_id/>
  <chebi_id>72595</chebi_id>
  <pubchem_compound_id>5283033</pubchem_compound_id>
  <kegg_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:19 UTC</creation_date>
  <update_date>2020-04-14 22:49:28 UTC</update_date>
  <accession>BMDB0001970</accession>
  <secondary_accessions>
    <accession>BMDB01970</accession>
  </secondary_accessions>
  <name>3-Methyluric acid</name>
  <description/>
  <synonyms>
    <synonym>3-Methylate</synonym>
    <synonym>3-Methylic acid</synonym>
    <synonym>3-Methyl-2,6,8-trioxopurine</synonym>
    <synonym>3-Methyl-7,9-dihydro-3H-purine-2,6,8-trione</synonym>
    <synonym>3-Methylurate</synonym>
    <synonym>4,9-Dihydro-3-methyl-1H-purine-2,6,8(3H)-trione</synonym>
  </synonyms>
  <chemical_formula>C6H6N4O3</chemical_formula>
  <average_molecular_weight>182.1368</average_molecular_weight>
  <monisotopic_moleculate_weight>182.043990078</monisotopic_moleculate_weight>
  <iupac_name>3-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione</iupac_name>
  <traditional_iupac>3-methyluric acid</traditional_iupac>
  <cas_registry_number>605-99-2</cas_registry_number>
  <smiles>CN1C2=C(NC(=O)N2)C(=O)NC1=O</smiles>
  <inchi>InChI=1S/C6H6N4O3/c1-10-3-2(7-5(12)8-3)4(11)9-6(10)13/h1H3,(H2,7,8,12)(H,9,11,13)</inchi>
  <inchikey>ODCYDGXXCHTFIR-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Xanthines</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazoles</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Lactam</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
      <substituent>Xanthine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>&gt; 350 °C</value>
      <source/>
    </property>
    <property>
      <kind>water_solubility</kind>
      <value>0.054 mg/mL at 25 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.08</value>
      <source>GASPARI,F &amp; BONATI,M (1987)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.04</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.68</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.66</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>182.1368</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>182.043990078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C2=C(NC(=O)N2)C(=O)NC1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H6N4O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H6N4O3/c1-10-3-2(7-5(12)8-3)4(11)9-6(10)13/h1H3,(H2,7,8,12)(H,9,11,13)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ODCYDGXXCHTFIR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>90.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>15950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62577</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62578</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>62579</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>119328</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>119329</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>119330</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022770</foodb_id>
  <chemspider_id>11311</chemspider_id>
  <pubchem_compound_id>11804</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>149031</chebi_id>
  <kegg_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Biltz, Heinrich; Heyn, Myron.  3-Methyluric acid.    Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen  (1919),  52B  768-84.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:20 UTC</creation_date>
  <update_date>2020-03-13 16:29:35 UTC</update_date>
  <accession>BMDB0001972</accession>
  <secondary_accessions>
    <accession>BMDB01972</accession>
  </secondary_accessions>
  <name>3-Aminosalicylic acid</name>
  <description/>
  <synonyms>
    <synonym>3-Aminosalicylate</synonym>
    <synonym>3-Amino salicylate</synonym>
    <synonym>3-Amino salicylic acid</synonym>
    <synonym>3-Amino-(8ci)salicylate</synonym>
    <synonym>3-Amino-(8ci)salicylic acid</synonym>
    <synonym>3-Amino-2-hydroxy-(9ci)benzoate</synonym>
    <synonym>3-Amino-2-hydroxy-(9ci)benzoic acid</synonym>
    <synonym>3-Amino-2-hydroxy-benzoate</synonym>
    <synonym>3-Amino-2-hydroxy-benzoic acid</synonym>
    <synonym>3-Amino-2-hydroxybenzoate</synonym>
    <synonym>3-Amino-2-hydroxybenzoic acid</synonym>
    <synonym>3-Amino-salicylate</synonym>
    <synonym>3-Amino-salicylic acid</synonym>
    <synonym>Desacetyleupaserrin</synonym>
    <synonym>Parasal</synonym>
    <synonym>Paser</synonym>
  </synonyms>
  <chemical_formula>C7H7NO3</chemical_formula>
  <average_molecular_weight>153.1354</average_molecular_weight>
  <monisotopic_moleculate_weight>153.042593095</monisotopic_moleculate_weight>
  <iupac_name>3-amino-2-hydroxybenzoic acid</iupac_name>
  <traditional_iupac>3-aminosalicylic acid</traditional_iupac>
  <cas_registry_number>570-23-0</cas_registry_number>
  <smiles>NC1=CC=CC(C(O)=O)=C1O</smiles>
  <inchi>InChI=1S/C7H7NO3/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,9H,8H2,(H,10,11)</inchi>
  <inchikey>IQGMRVWUTCYCST-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as aminosalicylic acids. These are salicylic acids carrying an amino group on the benzene ring.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>Aminosalicylic acids</direct_parent>
    <alternative_parents>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>3-aminosalicylic acids</alternative_parent>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Aminobenzoic acids</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Benzoic acids</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Salicylic acids</alternative_parent>
      <alternative_parent>Vinylogous acids</alternative_parent>
      <alternative_parent>o-Aminophenols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>3-aminosalicylic acid</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminobenzoic acid</substituent>
      <substituent>Aminobenzoic acid or derivatives</substituent>
      <substituent>Aminophenol</substituent>
      <substituent>Aminosalicylic acid</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzoic acid</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>O-aminophenol</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Salicylic acid</substituent>
      <substituent>Vinylogous acid</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.84</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.27</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-amino-2-hydroxybenzoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>153.1354</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>153.042593095</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=CC=CC(C(O)=O)=C1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C7H7NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C7H7NO3/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,9H,8H2,(H,10,11)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IQGMRVWUTCYCST-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>83.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>40</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>14.21</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13051</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38205</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1765</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1914</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1916</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294661</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294662</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>294663</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335449</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335450</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>335451</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id/>
  <foodb_id>FDB022771</foodb_id>
  <chemspider_id>61723</chemspider_id>
  <pubchem_compound_id>68443</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>1162549</chebi_id>
  <kegg_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id>Aminosalicylic acid</wikipedia_id>
  <metlin_id>6409</metlin_id>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:21 UTC</creation_date>
  <update_date>2020-04-14 22:49:28 UTC</update_date>
  <accession>BMDB0001973</accession>
  <secondary_accessions>
    <accession>BMDB01973</accession>
  </secondary_accessions>
  <name>9-Methyluric acid</name>
  <description/>
  <synonyms>
    <synonym>9-Methylate</synonym>
    <synonym>9-Methylic acid</synonym>
    <synonym>7,9-Dihydro-9-methyl-1H-purine-2,6,8(3H)-trione</synonym>
    <synonym>9-Methyl-2,6,8-trihydroxypurine</synonym>
    <synonym>MUA</synonym>
    <synonym>9-Methyl urate</synonym>
    <synonym>9-Methyluric acid</synonym>
  </synonyms>
  <chemical_formula>C6H6N4O3</chemical_formula>
  <average_molecular_weight>182.1368</average_molecular_weight>
  <monisotopic_moleculate_weight>182.043990078</monisotopic_moleculate_weight>
  <iupac_name>9-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione</iupac_name>
  <traditional_iupac>9-methyl uric acid</traditional_iupac>
  <cas_registry_number>55441-71-9</cas_registry_number>
  <smiles>CN1C(=O)NC2=C1NC(=O)NC2=O</smiles>
  <inchi>InChI=1S/C6H6N4O3/c1-10-3-2(7-6(10)13)4(11)9-5(12)8-3/h1H3,(H,7,13)(H2,8,9,11,12)</inchi>
  <inchikey>XJEJWDFDVPDMAS-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Imidazopyrimidines</class>
    <sub_class>Purines and purine derivatives</sub_class>
    <direct_parent>Xanthines</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Alkaloids and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Ureas</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alkaloid or derivatives</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Lactam</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Urea</substituent>
      <substituent>Vinylogous amide</substituent>
      <substituent>Xanthine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>water_solubility</kind>
      <value>0.021 mg/mL at 25 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>7.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>9-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>182.1368</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>182.043990078</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C(=O)NC2=C1NC(=O)NC2=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H6N4O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H6N4O3/c1-10-3-2(7-6(10)13)4(11)9-5(12)8-3/h1H3,(H,7,13)(H2,8,9,11,12)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XJEJWDFDVPDMAS-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>90.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>15.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1766</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>8638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1917</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1919</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>260840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>280775</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB03293</drugbank_id>
  <foodb_id>FDB022772</foodb_id>
  <chemspider_id>97755</chemspider_id>
  <pubchem_compound_id>108714</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id/>
  <kegg_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference>Biilman, Einar; Bjerrum, Johanne.  Methyl- and ethyluric acids.    Journal of the Chemical Society, Abstracts  (1917),  112(I),  588-9.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:49:22 UTC</creation_date>
  <update_date>2020-03-13 16:29:36 UTC</update_date>
  <accession>BMDB0001974</accession>
  <secondary_accessions>
    <accession>BMDB01974</accession>
  </secondary_accessions>
  <name>Dihydroxycoprostanoic acid</name>
  <description/>
  <synonyms>
    <synonym>Dihydroxycoprostanoate</synonym>
    <synonym>5'-Norneplanocin a</synonym>
    <synonym>5'-DHCA</synonym>
    <synonym>9-(2',3'-Dihydroxycyclopent-4'-enyl)adenine</synonym>
    <synonym>9-(2',3'-Dihydroxycyclopent-4'-enyl)adenine, 1S-(1alpha,2alpha,5beta) isomer</synonym>
    <synonym>9-(2',trans-3'-Dihydroxycyclopent-4'-enyl)adenine</synonym>
  </synonyms>
  <chemical_formula>C10H11N5O2</chemical_formula>
  <average_molecular_weight>233.231</average_molecular_weight>
  <monisotopic_moleculate_weight>233.091274614</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5R)-5-(6-amino-9H-purin-9-yl)cyclopent-3-ene-1,2-diol</iupac_name>
  <traditional_iupac>OHCA</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@@]1(O)C=C[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]1([H])O</smiles>
  <inchi>InChI=1S/C10H11N5O2/c11-9-7-10(13-3-12-9)15(4-14-7)5-1-2-6(16)8(5)17/h1-6,8,16-17H,(H2,11,12,13)/t5-,6-,8+/m1/s1</inchi>
  <inchikey>RQPALADHFYHEHK-JKMUOGBPSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Nucleoside and nucleotide analogues</class>
    <sub_class>Cyclopentyl nucleosides</sub_class>
    <direct_parent>1,3-substituted cyclopentyl purine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>6-aminopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>1,3-substituted cyclopentyl purine nucleoside</substituent>
      <substituent>6-aminopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-1.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>4.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5R)-5-(6-amino-9H-purin-9-yl)cyclopent-3-ene-1,2-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>233.231</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>233.091274614</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(O)C=C[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]1([H])O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H11N5O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H11N5O2/c11-9-7-10(13-3-12-9)15(4-14-7)5-1-2-6(16)8(5)17/h1-6,8,16-17H,(H2,11,12,13)/t5-,6-,8+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>RQPALADHFYHEHK-JKMUOGBPSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>110.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>61.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.39</value>
      <source>ChemAxon</source>
    </property>
    <